# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_hd_wql24
_database_code_depnum_ccdc_archive 'CCDC 1944631'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-01 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_formula_moiety 'C38 H42 Br N5 O3, 2(C H4 O)'
_chemical_formula_sum 'C40 H50 Br N5 O5'
_chemical_formula_iupac ?
_chemical_formula_weight 760.76
_chemical_melting_point ?
_space_group_crystal_system monoclinic
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.9227(3)
_cell_length_b 17.3502(4)
_cell_length_c 17.7857(4)
_cell_angle_alpha 90
_cell_angle_beta 90.6110(10)
_cell_angle_gamma 90
_cell_volume 3678.96(15)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9922
_cell_measurement_theta_min 3.5589
_cell_measurement_theta_max 72.3720
_cell_measurement_temperature 100.(2)
_exptl_crystal_description prism
_exptl_crystal_colour 'translucent light yellow'
_exptl_crystal_size_max 0.200
_exptl_crystal_size_mid 0.100
_exptl_crystal_size_min 0.050
_exptl_crystal_density_diffrn 1.374
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1600
_exptl_absorpt_coefficient_mu 1.937
_exptl_absorpt_correction_type Multi-Scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min 0.32
_exptl_absorpt_correction_T_max 0.91
_exptl_special_details
;
;
_diffrn_ambient_temperature 100.(2)
_diffrn_source 'Ius Diamond'
_diffrn_source_type Microfocus
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_monochromator 'Helixos MX multilayer Optic'
_diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number 36068
_diffrn_reflns_av_R_equivalents 0.0503
_diffrn_reflns_av_unetI/netI 0.0316
_diffrn_reflns_theta_min 3.56
_diffrn_reflns_theta_max 72.36
_diffrn_reflns_theta_full 72.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_refine_special_details
;
;
_reflns_number_total 7252
_reflns_number_gt 6204
_reflns_threshold_expression 'I > 2\s(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0897
_refine_ls_R_factor_gt 0.0814
_refine_ls_wR_factor_gt 0.2343
_refine_ls_wR_factor_ref 0.2467
_refine_ls_goodness_of_fit_ref 1.027
_refine_ls_restrained_S_all 1.027
_refine_ls_number_reflns 7252
_refine_ls_number_parameters 468
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1618P)^2^+4.8126P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 1.901
_refine_diff_density_min -1.272
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.05262(4) 0.91737(3) 0.51741(3) 0.0642(2) Uani d . . . 1 . .
O O1 0.5143(2) 0.75815(15) 0.10367(15) 0.0411(6) Uani d . . . 1 . .
H H25 0.531535 0.804587 0.110485 0.062 Uiso calc U . R 1 . .
O O2 0.1960(2) 0.64175(18) 0.19320(15) 0.0471(6) Uani d . . . 1 . .
H H26 0.130501 0.648956 0.208597 0.071 Uiso calc U . R 1 . .
O O3 0.4582(2) 0.40598(16) 0.36178(16) 0.0449(6) Uani d . . . 1 . .
O O4 -0.1760(3) 0.7530(3) 0.1455(2) 0.0753(10) Uani d . . . 1 . .
H H44 -0.229159 0.723439 0.156344 0.113 Uiso calc U . R 1 . .
N N1 0.3216(2) 0.66081(18) 0.37545(15) 0.0359(6) Uani d . . . 1 . .
N N2 0.4910(2) 0.70979(17) 0.31365(16) 0.0344(6) Uani d . . . 1 . .
N N3 0.5984(3) 0.51914(19) 0.16670(17) 0.0415(7) Uani d . . . 1 . .
N N4 0.5909(3) 0.71019(18) 0.14400(16) 0.0379(6) Uani d . . . 1 . .
N N5 0.2534(3) 0.58881(18) 0.24266(17) 0.0380(6) Uani d . . . 1 . .
H H42 0.223264 0.548812 0.265186 0.046 Uiso calc U . R 1 . .
O O5 -0.0203(3) 0.6738(4) 0.2376(2) 0.1006(19) Uani d . . . 1 . .
H H45 -0.064529 0.698225 0.209296 0.151 Uiso calc U . R 1 . .
C C1 0.1292(3) 0.8332(2) 0.4750(2) 0.0442(8) Uani d . . . 1 . .
C C2 0.2168(3) 0.8013(2) 0.5156(2) 0.0436(8) Uani d . . . 1 . .
H H2 0.233095 0.818349 0.565311 0.052 Uiso calc U . R 1 . .
C C3 0.2804(3) 0.7443(2) 0.4830(2) 0.0419(8) Uani d . . . 1 . .
H H3 0.341758 0.722352 0.5099 0.05 Uiso calc U . R 1 . .
C C4 0.2547(3) 0.7186(2) 0.41046(19) 0.0368(7) Uani d . . . 1 . .
C C5 0.3770(3) 0.6828(2) 0.30317(18) 0.0344(7) Uani d . . . 1 . .
H H12 0.33248 0.72574 0.280059 0.041 Uiso calc U . R 1 . .
C C6 0.5700(3) 0.6499(2) 0.3404(2) 0.0376(7) Uani d . . . 1 . .
H H4 0.553341 0.637064 0.393328 0.045 Uiso calc U . R 1 . .
H H27 0.647487 0.670197 0.338519 0.045 Uiso calc U . R 1 . .
C C7 0.5620(3) 0.5767(2) 0.29268(19) 0.0358(7) Uani d . . . 1 . .
H H28 0.608 0.535575 0.317459 0.043 Uiso calc U . R 1 . .
C C8 0.6086(3) 0.5911(2) 0.2130(2) 0.0383(7) Uani d . . . 1 . .
H H15 0.689081 0.606952 0.216693 0.046 Uiso calc U . R 1 . .
C C9 0.7078(3) 0.4854(2) 0.1500(2) 0.0472(9) Uani d . . . 1 . .
H H17 0.759145 0.526655 0.133263 0.057 Uiso calc U . R 1 . .
H H16 0.699064 0.448175 0.10813 0.057 Uiso calc U . R 1 . .
C C10 0.7597(3) 0.4445(2) 0.2171(2) 0.0457(8) Uani d . . . 1 . .
C C11 0.8757(4) 0.4477(3) 0.2299(3) 0.0567(11) Uani d . . . 1 . .
H H21 0.920961 0.480596 0.200263 0.068 Uiso calc U . R 1 . .
C C12 0.9250(4) 0.4026(4) 0.2862(3) 0.0686(14) Uani d . . . 1 . .
H H20 1.003824 0.404713 0.294271 0.082 Uiso calc U . R 1 . .
C C13 0.8605(5) 0.3551(4) 0.3300(3) 0.0669(14) Uani d . . . 1 . .
H H1 0.895111 0.323715 0.367392 0.08 Uiso calc U . R 1 . .
C C14 0.3306(3) 0.5876(2) 0.40244(19) 0.0378(7) Uani d . . . 1 . .
C C15 0.3897(3) 0.5322(2) 0.36442(19) 0.0379(7) Uani d . . . 1 . .
C C16 0.4388(3) 0.5491(2) 0.28799(18) 0.0356(7) Uani d . . . 1 . .
H H29 0.434939 0.501349 0.256525 0.043 Uiso calc U . R 1 . .
C C17 0.4976(3) 0.7779(2) 0.3626(2) 0.0392(7) Uani d . . . 1 . .
H H11 0.484808 0.761656 0.415177 0.047 Uiso calc U . R 1 . .
H H5 0.437008 0.814128 0.348231 0.047 Uiso calc U . R 1 . .
C C18 0.6087(3) 0.8193(2) 0.3587(2) 0.0402(8) Uani d . . . 1 . .
C C19 0.6615(3) 0.8442(3) 0.4250(2) 0.0486(9) Uani d . . . 1 . .
H H6 0.629995 0.831952 0.472317 0.058 Uiso calc U . R 1 . .
C C20 0.7608(4) 0.8872(3) 0.4216(3) 0.0564(11) Uani d . . . 1 . .
H H10 0.794981 0.905639 0.466588 0.068 Uiso calc U . R 1 . .
C C21 0.8087(3) 0.9028(3) 0.3539(3) 0.0522(10) Uani d . . . 1 . .
H H7 0.876626 0.93133 0.351886 0.063 Uiso calc U . R 1 . .
C C22 0.7578(4) 0.8769(3) 0.2880(3) 0.0504(9) Uani d . . . 1 . .
H H9 0.791785 0.887077 0.240965 0.061 Uiso calc U . R 1 . .
C C23 0.6582(3) 0.8365(2) 0.2905(2) 0.0466(8) Uani d . . . 1 . .
H H8 0.623174 0.820171 0.244963 0.056 Uiso calc U . R 1 . .
C C24 0.3712(3) 0.6132(2) 0.24896(18) 0.0337(7) Uani d . . . 1 . .
C C25 0.4193(3) 0.6332(2) 0.17008(18) 0.0345(7) Uani d . . . 1 . .
H H24 0.376341 0.677192 0.147585 0.041 Uiso calc U . R 1 . .
C C26 0.4149(3) 0.5623(2) 0.1155(2) 0.0412(8) Uani d . . . 1 . .
H H14 0.369495 0.520998 0.138608 0.049 Uiso calc U . R 1 . .
H H13 0.377268 0.577833 0.068015 0.049 Uiso calc U . R 1 . .
C C27 0.5309(3) 0.5306(2) 0.0978(2) 0.0426(8) Uani d . . . 1 . .
H H23 0.52291 0.480884 0.07107 0.051 Uiso calc U . R 1 . .
H H22 0.570145 0.566983 0.064236 0.051 Uiso calc U . R 1 . .
C C28 0.5412(3) 0.6536(2) 0.17528(19) 0.0368(7) Uani d . . . 1 . .
C C29 0.7462(4) 0.3528(3) 0.3197(3) 0.0543(10) Uani d . . . 1 . .
H H18 0.701108 0.320845 0.3505 0.065 Uiso calc U . R 1 . .
C C30 0.6968(3) 0.3983(2) 0.2632(2) 0.0443(8) Uani d . . . 1 . .
H H19 0.617666 0.397205 0.25665 0.053 Uiso calc U . R 1 . .
C C31 0.4021(3) 0.4557(2) 0.3941(2) 0.0399(8) Uani d . . . 1 . .
C C32 0.3452(3) 0.4364(2) 0.4673(2) 0.0447(8) Uani d . . . 1 . .
H H31 0.398458 0.4459 0.509436 0.054 Uiso calc U . R 1 . .
H H30 0.326046 0.380896 0.467573 0.054 Uiso calc U . R 1 . .
C C33 0.2388(3) 0.4832(2) 0.4803(2) 0.0446(8) Uani d . . . 1 . .
C C34 0.1478(4) 0.4637(3) 0.4213(2) 0.0532(10) Uani d . . . 1 . .
H H32 0.175413 0.475948 0.370983 0.08 Uiso calc U . R 1 . .
H H34 0.080231 0.494067 0.431238 0.08 Uiso calc U . R 1 . .
H H33 0.129744 0.408681 0.42407 0.08 Uiso calc U . R 1 . .
C C35 0.1934(4) 0.4658(3) 0.5585(2) 0.0514(10) Uani d . . . 1 . .
H H35 0.172305 0.411345 0.561513 0.077 Uiso calc U . R 1 . .
H H37 0.127324 0.49799 0.567739 0.077 Uiso calc U . R 1 . .
H H36 0.251295 0.477072 0.596451 0.077 Uiso calc U . R 1 . .
C C36 0.2703(3) 0.5688(2) 0.4750(2) 0.0406(8) Uani d . . . 1 . .
H H39 0.201281 0.600354 0.478008 0.049 Uiso calc U . R 1 . .
H H38 0.319171 0.582567 0.518263 0.049 Uiso calc U . R 1 . .
C C37 0.1645(3) 0.7506(2) 0.37098(19) 0.0376(7) Uani d . . . 1 . .
H H41 0.146463 0.732815 0.321808 0.045 Uiso calc U . R 1 . .
C C38 0.1012(3) 0.8083(2) 0.4034(2) 0.0427(8) Uani d . . . 1 . .
H H40 0.039592 0.830449 0.376899 0.051 Uiso calc U . R 1 . .
C C40 -0.0758(4) 0.6523(4) 0.3026(3) 0.0710(14) Uani d . . . 1 . .
H H47 -0.020898 0.635663 0.340617 0.107 Uiso calc U . R 1 . .
H H46 -0.127365 0.609843 0.291187 0.107 Uiso calc U . R 1 . .
H H43 -0.118245 0.696385 0.321774 0.107 Uiso calc U . R 1 . .
C C41 -0.1423(5) 0.7385(4) 0.0748(4) 0.0752(15) Uani d . . . 1 . .
H H50 -0.189244 0.767426 0.039171 0.113 Uiso calc U . R 1 . .
H H49 -0.149209 0.683203 0.064469 0.113 Uiso calc U . R 1 . .
H H48 -0.063828 0.754236 0.069447 0.113 Uiso calc U . R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0549(3) 0.0649(4) 0.0728(4) 0.0082(2) -0.0031(2) -0.0219(2)
O1 0.0433(13) 0.0367(12) 0.0429(13) -0.0005(10) -0.0082(10) 0.0037(10)
O2 0.0386(13) 0.0612(17) 0.0414(13) 0.0021(12) -0.0076(10) 0.0116(12)
O3 0.0469(15) 0.0425(14) 0.0452(14) 0.0031(11) -0.0045(11) 0.0045(11)
O4 0.057(2) 0.096(3) 0.073(2) -0.0078(19) -0.0007(17) 0.004(2)
N1 0.0342(14) 0.0420(15) 0.0313(13) 0.0017(12) -0.0029(11) 0.0007(11)
N2 0.0319(13) 0.0362(14) 0.0351(13) -0.0008(11) -0.0051(10) -0.0010(11)
N3 0.0438(16) 0.0438(16) 0.0368(15) 0.0068(13) -0.0015(12) -0.0026(12)
N4 0.0379(15) 0.0417(16) 0.0341(14) 0.0005(12) -0.0025(11) -0.0004(12)
N5 0.0356(15) 0.0435(16) 0.0348(14) -0.0036(12) -0.0077(11) 0.0058(12)
O5 0.0424(17) 0.185(6) 0.075(2) 0.011(2) 0.0018(16) 0.062(3)
C1 0.0424(19) 0.0436(19) 0.0467(19) -0.0014(16) 0.0074(15) -0.0076(15)
C2 0.0414(18) 0.051(2) 0.0380(17) -0.0057(16) -0.0014(14) -0.0058(15)
C3 0.0382(17) 0.056(2) 0.0317(16) -0.0015(16) -0.0032(13) -0.0014(15)
C4 0.0347(16) 0.0421(18) 0.0337(16) 0.0002(14) -0.0034(13) 0.0000(13)
C5 0.0327(15) 0.0392(17) 0.0312(15) 0.0016(13) -0.0048(12) 0.0027(13)
C6 0.0350(16) 0.0416(18) 0.0361(16) 0.0022(14) -0.0068(13) -0.0013(14)
C7 0.0343(17) 0.0397(18) 0.0334(16) 0.0031(13) -0.0050(13) 0.0011(13)
C8 0.0351(17) 0.0417(18) 0.0379(17) 0.0004(14) -0.0017(13) -0.0003(14)
C9 0.048(2) 0.047(2) 0.047(2) 0.0074(17) 0.0060(16) -0.0014(16)
C10 0.0436(19) 0.045(2) 0.049(2) 0.0085(16) -0.0030(16) -0.0115(16)
C11 0.041(2) 0.074(3) 0.055(2) 0.000(2) 0.0022(17) -0.020(2)
C12 0.044(2) 0.101(4) 0.061(3) 0.016(2) -0.011(2) -0.024(3)
C13 0.066(3) 0.083(3) 0.052(2) 0.027(3) -0.011(2) -0.005(2)
C14 0.0362(17) 0.0470(19) 0.0301(16) -0.0035(14) -0.0075(13) 0.0051(13)
C15 0.0368(16) 0.0440(19) 0.0327(16) -0.0009(14) -0.0053(13) 0.0044(14)
C16 0.0374(16) 0.0391(17) 0.0303(15) 0.0017(14) -0.0052(12) 0.0018(13)
C17 0.0396(17) 0.0418(18) 0.0361(16) 0.0003(15) -0.0032(13) -0.0047(14)
C18 0.0376(17) 0.0384(17) 0.0445(18) 0.0015(14) -0.0069(14) -0.0054(14)
C19 0.044(2) 0.055(2) 0.047(2) 0.0005(17) -0.0096(16) -0.0078(17)
C20 0.047(2) 0.062(3) 0.060(2) -0.004(2) -0.0161(19) -0.011(2)
C21 0.0344(18) 0.047(2) 0.075(3) 0.0017(16) -0.0087(18) -0.0042(19)
C22 0.045(2) 0.051(2) 0.056(2) -0.0036(17) 0.0028(17) 0.0034(18)
C23 0.047(2) 0.049(2) 0.0436(19) -0.0052(17) -0.0050(16) -0.0010(16)
C24 0.0321(16) 0.0378(17) 0.0311(15) -0.0001(13) -0.0049(12) 0.0016(13)
C25 0.0354(16) 0.0380(17) 0.0301(15) 0.0001(13) -0.0044(12) 0.0008(12)
C26 0.047(2) 0.0435(18) 0.0325(16) -0.0021(16) -0.0057(14) -0.0023(14)
C27 0.050(2) 0.0427(18) 0.0345(16) 0.0012(16) -0.0025(14) -0.0024(14)
C28 0.0353(16) 0.0424(18) 0.0325(15) 0.0005(14) -0.0018(12) -0.0032(13)
C29 0.066(3) 0.047(2) 0.050(2) 0.010(2) -0.0072(19) -0.0062(17)
C30 0.047(2) 0.0415(18) 0.0443(19) 0.0057(16) -0.0056(16) -0.0058(15)
C31 0.0395(17) 0.0430(19) 0.0370(17) -0.0019(15) -0.0093(14) 0.0063(14)
C32 0.045(2) 0.047(2) 0.0417(19) -0.0010(16) -0.0027(15) 0.0098(16)
C33 0.0410(19) 0.054(2) 0.0388(18) -0.0036(16) -0.0036(14) 0.0083(16)
C34 0.0406(19) 0.067(3) 0.052(2) -0.0089(19) -0.0069(16) 0.004(2)
C35 0.047(2) 0.065(3) 0.043(2) -0.0089(19) 0.0029(16) 0.0107(18)
C36 0.0374(17) 0.051(2) 0.0332(16) 0.0000(15) 0.0001(13) 0.0052(14)
C37 0.0357(17) 0.0438(18) 0.0330(16) -0.0008(14) -0.0033(13) -0.0001(13)
C38 0.0379(17) 0.0463(19) 0.0438(18) 0.0024(15) -0.0014(14) 0.0014(15)
C40 0.056(3) 0.095(4) 0.062(3) -0.024(3) -0.003(2) 0.016(3)
C41 0.060(3) 0.087(4) 0.079(3) 0.009(3) 0.004(3) -0.009(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.884(4) ?
O1 N4 . 1.424(4) ?
O1 H25 . 0.84 ?
O2 N5 . 1.440(4) ?
O2 H26 . 0.84 ?
O3 C31 . 1.237(5) ?
O4 C41 . 1.347(7) ?
O4 H44 . 0.84 ?
N1 C14 . 1.362(5) ?
N1 C4 . 1.428(5) ?
N1 C5 . 1.501(4) ?
N2 C5 . 1.448(4) ?
N2 C17 . 1.469(5) ?
N2 C6 . 1.478(4) ?
N3 C9 . 1.464(5) ?
N3 C27 . 1.472(5) ?
N3 C8 . 1.499(5) ?
N4 C28 . 1.277(5) ?
N5 C24 . 1.469(4) ?
N5 H42 . 0.88 ?
O5 C40 . 1.388(6) ?
O5 H45 . 0.84 ?
C1 C2 . 1.379(6) ?
C1 C38 . 1.383(6) ?
C2 C3 . 1.378(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.395(5) ?
C3 H3 . 0.95 ?
C4 C37 . 1.394(5) ?
C5 C24 . 1.546(5) ?
C5 H12 . 1.0 ?
C6 C7 . 1.528(5) ?
C6 H4 . 0.99 ?
C6 H27 . 0.99 ?
C7 C16 . 1.546(5) ?
C7 C8 . 1.547(5) ?
C7 H28 . 1.0 ?
C8 C28 . 1.504(5) ?
C8 H15 . 1.0 ?
C9 C10 . 1.515(6) ?
C9 H17 . 0.99 ?
C9 H16 . 0.99 ?
C10 C30 . 1.375(6) ?
C10 C11 . 1.400(6) ?
C11 C12 . 1.394(8) ?
C11 H21 . 0.95 ?
C12 C13 . 1.375(9) ?
C12 H20 . 0.95 ?
C13 C29 . 1.374(7) ?
C13 H1 . 0.95 ?
C14 C15 . 1.374(6) ?
C14 C36 . 1.519(5) ?
C15 C31 . 1.434(5) ?
C15 C16 . 1.515(5) ?
C16 C24 . 1.536(5) ?
C16 H29 . 1.0 ?
C17 C18 . 1.510(5) ?
C17 H11 . 0.99 ?
C17 H5 . 0.99 ?
C18 C23 . 1.386(6) ?
C18 C19 . 1.399(5) ?
C19 C20 . 1.402(6) ?
C19 H6 . 0.95 ?
C20 C21 . 1.364(7) ?
C20 H10 . 0.95 ?
C21 C22 . 1.388(7) ?
C21 H7 . 0.95 ?
C22 C23 . 1.381(6) ?
C22 H9 . 0.95 ?
C23 H8 . 0.95 ?
C24 C25 . 1.561(5) ?
C25 C28 . 1.497(5) ?
C25 C26 . 1.568(5) ?
C25 H24 . 1.0 ?
C26 C27 . 1.524(6) ?
C26 H14 . 0.99 ?
C26 H13 . 0.99 ?
C27 H23 . 0.99 ?
C27 H22 . 0.99 ?
C29 C30 . 1.402(6) ?
C29 H18 . 0.95 ?
C30 H19 . 0.95 ?
C31 C32 . 1.513(5) ?
C32 C33 . 1.526(6) ?
C32 H31 . 0.99 ?
C32 H30 . 0.99 ?
C33 C35 . 1.528(5) ?
C33 C36 . 1.534(6) ?
C33 C34 . 1.539(5) ?
C34 H32 . 0.98 ?
C34 H34 . 0.98 ?
C34 H33 . 0.98 ?
C35 H35 . 0.98 ?
C35 H37 . 0.98 ?
C35 H36 . 0.98 ?
C36 H39 . 0.99 ?
C36 H38 . 0.99 ?
C37 C38 . 1.383(5) ?
C37 H41 . 0.95 ?
C38 H40 . 0.95 ?
C40 H47 . 0.98 ?
C40 H46 . 0.98 ?
C40 H43 . 0.98 ?
C41 H50 . 0.98 ?
C41 H49 . 0.98 ?
C41 H48 . 0.98 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 O1 H25 . . 109.5 ?
N5 O2 H26 . . 109.5 ?
C41 O4 H44 . . 109.5 ?
C14 N1 C4 . . 122.9(3) ?
C14 N1 C5 . . 120.4(3) ?
C4 N1 C5 . . 116.6(3) ?
C5 N2 C17 . . 112.4(3) ?
C5 N2 C6 . . 114.1(3) ?
C17 N2 C6 . . 110.2(3) ?
C9 N3 C27 . . 111.5(3) ?
C9 N3 C8 . . 112.2(3) ?
C27 N3 C8 . . 112.6(3) ?
C28 N4 O1 . . 111.7(3) ?
O2 N5 C24 . . 108.1(3) ?
O2 N5 H42 . . 126.0 ?
C24 N5 H42 . . 126.0 ?
C40 O5 H45 . . 109.5 ?
C2 C1 C38 . . 122.1(4) ?
C2 C1 Br1 . . 118.0(3) ?
C38 C1 Br1 . . 119.8(3) ?
C3 C2 C1 . . 119.0(3) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C37 C4 C3 . . 119.9(3) ?
C37 C4 N1 . . 119.4(3) ?
C3 C4 N1 . . 120.6(3) ?
N2 C5 N1 . . 113.1(3) ?
N2 C5 C24 . . 111.6(3) ?
N1 C5 C24 . . 108.6(3) ?
N2 C5 H12 . . 107.8 ?
N1 C5 H12 . . 107.8 ?
C24 C5 H12 . . 107.8 ?
N2 C6 C7 . . 111.7(3) ?
N2 C6 H4 . . 109.3 ?
C7 C6 H4 . . 109.3 ?
N2 C6 H27 . . 109.3 ?
C7 C6 H27 . . 109.3 ?
H4 C6 H27 . . 107.9 ?
C6 C7 C16 . . 109.9(3) ?
C6 C7 C8 . . 110.7(3) ?
C16 C7 C8 . . 110.5(3) ?
C6 C7 H28 . . 108.5 ?
C16 C7 H28 . . 108.5 ?
C8 C7 H28 . . 108.5 ?
N3 C8 C28 . . 108.4(3) ?
N3 C8 C7 . . 110.0(3) ?
C28 C8 C7 . . 109.2(3) ?
N3 C8 H15 . . 109.7 ?
C28 C8 H15 . . 109.7 ?
C7 C8 H15 . . 109.7 ?
N3 C9 C10 . . 112.6(3) ?
N3 C9 H17 . . 109.1 ?
C10 C9 H17 . . 109.1 ?
N3 C9 H16 . . 109.1 ?
C10 C9 H16 . . 109.1 ?
H17 C9 H16 . . 107.8 ?
C30 C10 C11 . . 118.0(4) ?
C30 C10 C9 . . 121.5(4) ?
C11 C10 C9 . . 120.3(4) ?
C12 C11 C10 . . 120.2(5) ?
C12 C11 H21 . . 119.9 ?
C10 C11 H21 . . 119.9 ?
C13 C12 C11 . . 120.6(5) ?
C13 C12 H20 . . 119.7 ?
C11 C12 H20 . . 119.7 ?
C29 C13 C12 . . 120.1(5) ?
C29 C13 H1 . . 120.0 ?
C12 C13 H1 . . 120.0 ?
N1 C14 C15 . . 121.2(3) ?
N1 C14 C36 . . 117.6(3) ?
C15 C14 C36 . . 121.2(3) ?
C14 C15 C31 . . 121.2(3) ?
C14 C15 C16 . . 120.8(3) ?
C31 C15 C16 . . 118.0(3) ?
C15 C16 C24 . . 109.8(3) ?
C15 C16 C7 . . 112.8(3) ?
C24 C16 C7 . . 107.0(3) ?
C15 C16 H29 . . 109.0 ?
C24 C16 H29 . . 109.0 ?
C7 C16 H29 . . 109.0 ?
N2 C17 C18 . . 113.4(3) ?
N2 C17 H11 . . 108.9 ?
C18 C17 H11 . . 108.9 ?
N2 C17 H5 . . 108.9 ?
C18 C17 H5 . . 108.9 ?
H11 C17 H5 . . 107.7 ?
C23 C18 C19 . . 118.7(4) ?
C23 C18 C17 . . 121.6(3) ?
C19 C18 C17 . . 119.7(4) ?
C18 C19 C20 . . 120.0(4) ?
C18 C19 H6 . . 120.0 ?
C20 C19 H6 . . 120.0 ?
C21 C20 C19 . . 120.4(4) ?
C21 C20 H10 . . 119.8 ?
C19 C20 H10 . . 119.8 ?
C20 C21 C22 . . 119.8(4) ?
C20 C21 H7 . . 120.1 ?
C22 C21 H7 . . 120.1 ?
C23 C22 C21 . . 120.4(4) ?
C23 C22 H9 . . 119.8 ?
C21 C22 H9 . . 119.8 ?
C22 C23 C18 . . 120.7(4) ?
C22 C23 H8 . . 119.6 ?
C18 C23 H8 . . 119.6 ?
N5 C24 C16 . . 108.8(3) ?
N5 C24 C5 . . 108.0(3) ?
C16 C24 C5 . . 105.3(3) ?
N5 C24 C25 . . 110.9(3) ?
C16 C24 C25 . . 111.8(3) ?
C5 C24 C25 . . 111.9(3) ?
C28 C25 C24 . . 111.3(3) ?
C28 C25 C26 . . 104.5(3) ?
C24 C25 C26 . . 111.8(3) ?
C28 C25 H24 . . 109.7 ?
C24 C25 H24 . . 109.7 ?
C26 C25 H24 . . 109.7 ?
C27 C26 C25 . . 112.7(3) ?
C27 C26 H14 . . 109.0 ?
C25 C26 H14 . . 109.0 ?
C27 C26 H13 . . 109.0 ?
C25 C26 H13 . . 109.0 ?
H14 C26 H13 . . 107.8 ?
N3 C27 C26 . . 111.5(3) ?
N3 C27 H23 . . 109.3 ?
C26 C27 H23 . . 109.3 ?
N3 C27 H22 . . 109.3 ?
C26 C27 H22 . . 109.3 ?
H23 C27 H22 . . 108.0 ?
N4 C28 C25 . . 127.5(3) ?
N4 C28 C8 . . 120.1(3) ?
C25 C28 C8 . . 111.7(3) ?
C13 C29 C30 . . 119.2(5) ?
C13 C29 H18 . . 120.4 ?
C30 C29 H18 . . 120.4 ?
C10 C30 C29 . . 121.9(4) ?
C10 C30 H19 . . 119.1 ?
C29 C30 H19 . . 119.1 ?
O3 C31 C15 . . 121.9(3) ?
O3 C31 C32 . . 119.7(3) ?
C15 C31 C32 . . 118.4(3) ?
C31 C32 C33 . . 113.2(3) ?
C31 C32 H31 . . 108.9 ?
C33 C32 H31 . . 108.9 ?
C31 C32 H30 . . 108.9 ?
C33 C32 H30 . . 108.9 ?
H31 C32 H30 . . 107.8 ?
C32 C33 C35 . . 109.6(3) ?
C32 C33 C36 . . 107.5(3) ?
C35 C33 C36 . . 109.6(3) ?
C32 C33 C34 . . 111.2(4) ?
C35 C33 C34 . . 108.8(3) ?
C36 C33 C34 . . 110.0(3) ?
C33 C34 H32 . . 109.5 ?
C33 C34 H34 . . 109.5 ?
H32 C34 H34 . . 109.5 ?
C33 C34 H33 . . 109.5 ?
H32 C34 H33 . . 109.5 ?
H34 C34 H33 . . 109.5 ?
C33 C35 H35 . . 109.5 ?
C33 C35 H37 . . 109.5 ?
H35 C35 H37 . . 109.5 ?
C33 C35 H36 . . 109.5 ?
H35 C35 H36 . . 109.5 ?
H37 C35 H36 . . 109.5 ?
C14 C36 C33 . . 112.2(3) ?
C14 C36 H39 . . 109.2 ?
C33 C36 H39 . . 109.2 ?
C14 C36 H38 . . 109.2 ?
C33 C36 H38 . . 109.2 ?
H39 C36 H38 . . 107.9 ?
C38 C37 C4 . . 120.0(3) ?
C38 C37 H41 . . 120.0 ?
C4 C37 H41 . . 120.0 ?
C37 C38 C1 . . 118.9(3) ?
C37 C38 H40 . . 120.6 ?
C1 C38 H40 . . 120.6 ?
O5 C40 H47 . . 109.5 ?
O5 C40 H46 . . 109.5 ?
H47 C40 H46 . . 109.5 ?
O5 C40 H43 . . 109.5 ?
H47 C40 H43 . . 109.5 ?
H46 C40 H43 . . 109.5 ?
O4 C41 H50 . . 109.5 ?
O4 C41 H49 . . 109.5 ?
H50 C41 H49 . . 109.5 ?
O4 C41 H48 . . 109.5 ?
H50 C41 H48 . . 109.5 ?
H49 C41 H48 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C38 C1 C2 C3 . . . . 1.8(6) ?
Br1 C1 C2 C3 . . . . -174.3(3) ?
C1 C2 C3 C4 . . . . -1.1(6) ?
C2 C3 C4 C37 . . . . -0.1(6) ?
C2 C3 C4 N1 . . . . 178.5(3) ?
C14 N1 C4 C37 . . . . -117.7(4) ?
C5 N1 C4 C37 . . . . 58.3(4) ?
C14 N1 C4 C3 . . . . 63.7(5) ?
C5 N1 C4 C3 . . . . -120.3(4) ?
C17 N2 C5 N1 . . . . -59.5(4) ?
C6 N2 C5 N1 . . . . 66.8(4) ?
C17 N2 C5 C24 . . . . 177.7(3) ?
C6 N2 C5 C24 . . . . -56.0(4) ?
C14 N1 C5 N2 . . . . -89.1(4) ?
C4 N1 C5 N2 . . . . 94.8(3) ?
C14 N1 C5 C24 . . . . 35.4(4) ?
C4 N1 C5 C24 . . . . -140.7(3) ?
C5 N2 C6 C7 . . . . 50.2(4) ?
C17 N2 C6 C7 . . . . 177.6(3) ?
N2 C6 C7 C16 . . . . -52.9(4) ?
N2 C6 C7 C8 . . . . 69.5(4) ?
C9 N3 C8 C28 . . . . 128.9(3) ?
C27 N3 C8 C28 . . . . 2.2(4) ?
C9 N3 C8 C7 . . . . -111.7(3) ?
C27 N3 C8 C7 . . . . 121.5(3) ?
C6 C7 C8 N3 . . . . -179.1(3) ?
C16 C7 C8 N3 . . . . -57.0(4) ?
C6 C7 C8 C28 . . . . -60.3(4) ?
C16 C7 C8 C28 . . . . 61.8(4) ?
C27 N3 C9 C10 . . . . -157.5(3) ?
C8 N3 C9 C10 . . . . 75.2(4) ?
N3 C9 C10 C30 . . . . 42.4(5) ?
N3 C9 C10 C11 . . . . -143.2(4) ?
C30 C10 C11 C12 . . . . 2.4(6) ?
C9 C10 C11 C12 . . . . -172.2(4) ?
C10 C11 C12 C13 . . . . -0.5(7) ?
C11 C12 C13 C29 . . . . -1.4(8) ?
C4 N1 C14 C15 . . . . 175.6(3) ?
C5 N1 C14 C15 . . . . -0.2(5) ?
C4 N1 C14 C36 . . . . -2.8(5) ?
C5 N1 C14 C36 . . . . -178.7(3) ?
N1 C14 C15 C31 . . . . 178.0(3) ?
C36 C14 C15 C31 . . . . -3.7(5) ?
N1 C14 C15 C16 . . . . -5.1(5) ?
C36 C14 C15 C16 . . . . 173.3(3) ?
C14 C15 C16 C24 . . . . -25.8(4) ?
C31 C15 C16 C24 . . . . 151.3(3) ?
C14 C15 C16 C7 . . . . 93.6(4) ?
C31 C15 C16 C7 . . . . -89.4(4) ?
C6 C7 C16 C15 . . . . -58.9(4) ?
C8 C7 C16 C15 . . . . 178.6(3) ?
C6 C7 C16 C24 . . . . 62.0(3) ?
C8 C7 C16 C24 . . . . -60.5(4) ?
C5 N2 C17 C18 . . . . -165.0(3) ?
C6 N2 C17 C18 . . . . 66.5(4) ?
N2 C17 C18 C23 . . . . 46.9(5) ?
N2 C17 C18 C19 . . . . -135.8(4) ?
C23 C18 C19 C20 . . . . 1.6(6) ?
C17 C18 C19 C20 . . . . -175.7(4) ?
C18 C19 C20 C21 . . . . -2.3(7) ?
C19 C20 C21 C22 . . . . 1.0(7) ?
C20 C21 C22 C23 . . . . 1.0(7) ?
C21 C22 C23 C18 . . . . -1.6(7) ?
C19 C18 C23 C22 . . . . 0.3(6) ?
C17 C18 C23 C22 . . . . 177.6(4) ?
O2 N5 C24 C16 . . . . -168.6(3) ?
O2 N5 C24 C5 . . . . 77.5(3) ?
O2 N5 C24 C25 . . . . -45.3(4) ?
C15 C16 C24 N5 . . . . -57.8(4) ?
C7 C16 C24 N5 . . . . 179.4(3) ?
C15 C16 C24 C5 . . . . 57.8(3) ?
C7 C16 C24 C5 . . . . -65.0(3) ?
C15 C16 C24 C25 . . . . 179.5(3) ?
C7 C16 C24 C25 . . . . 56.7(3) ?
N2 C5 C24 N5 . . . . 179.0(3) ?
N1 C5 C24 N5 . . . . 53.6(3) ?
N2 C5 C24 C16 . . . . 62.8(3) ?
N1 C5 C24 C16 . . . . -62.5(3) ?
N2 C5 C24 C25 . . . . -58.8(3) ?
N1 C5 C24 C25 . . . . 175.9(3) ?
N5 C24 C25 C28 . . . . -176.6(3) ?
C16 C24 C25 C28 . . . . -55.0(4) ?
C5 C24 C25 C28 . . . . 62.8(4) ?
N5 C24 C25 C26 . . . . -60.2(4) ?
C16 C24 C25 C26 . . . . 61.4(4) ?
C5 C24 C25 C26 . . . . 179.2(3) ?
C28 C25 C26 C27 . . . . 9.6(4) ?
C24 C25 C26 C27 . . . . -110.9(3) ?
C9 N3 C27 C26 . . . . 177.3(3) ?
C8 N3 C27 C26 . . . . -55.5(4) ?
C25 C26 C27 N3 . . . . 48.9(4) ?
O1 N4 C28 C25 . . . . 3.1(5) ?
O1 N4 C28 C8 . . . . 172.8(3) ?
C24 C25 C28 N4 . . . . -134.5(4) ?
C26 C25 C28 N4 . . . . 104.7(4) ?
C24 C25 C28 C8 . . . . 55.0(4) ?
C26 C25 C28 C8 . . . . -65.8(3) ?
N3 C8 C28 N4 . . . . -109.7(4) ?
C7 C8 C28 N4 . . . . 130.4(3) ?
N3 C8 C28 C25 . . . . 61.5(4) ?
C7 C8 C28 C25 . . . . -58.3(4) ?
C12 C13 C29 C30 . . . . 1.2(7) ?
C11 C10 C30 C29 . . . . -2.6(6) ?
C9 C10 C30 C29 . . . . 171.9(4) ?
C13 C29 C30 C10 . . . . 0.8(6) ?
C14 C15 C31 O3 . . . . -177.5(3) ?
C16 C15 C31 O3 . . . . 5.4(5) ?
C14 C15 C31 C32 . . . . 2.0(5) ?
C16 C15 C31 C32 . . . . -175.1(3) ?
O3 C31 C32 C33 . . . . -151.4(4) ?
C15 C31 C32 C33 . . . . 29.1(5) ?
C31 C32 C33 C35 . . . . -174.5(3) ?
C31 C32 C33 C36 . . . . -55.4(4) ?
C31 C32 C33 C34 . . . . 65.1(4) ?
N1 C14 C36 C33 . . . . 153.0(3) ?
C15 C14 C36 C33 . . . . -25.4(5) ?
C32 C33 C36 C14 . . . . 53.1(4) ?
C35 C33 C36 C14 . . . . 172.2(3) ?
C34 C33 C36 C14 . . . . -68.1(4) ?
C3 C4 C37 C38 . . . . 0.7(6) ?
N1 C4 C37 C38 . . . . -178.0(3) ?
C4 C37 C38 C1 . . . . 0.0(6) ?
C2 C1 C38 C37 . . . . -1.3(6) ?
Br1 C1 C38 C37 . . . . 174.8(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H25 O3 2_655 0.84 1.83 2.657(4) 167.5 ?
O2 H26 O5 . 0.84 1.93 2.763(5) 174.6 ?
O4 H44 N4 1_455 0.84 2.17 2.877(5) 142.2 ?
O5 H45 O4 . 0.84 1.98 2.821(6) 176.7 ?
C2 H2 O2 4_576 0.95 2.42 3.321(5) 157.6 ?
C3 H3 O1 4_576 0.95 2.66 3.502(4) 148.6 ?
C41 H49 Br1 4_575 0.98 3.09 3.715(6) 122.6 ?
_shelx_res_file
;
TITL hd_wql24_0m_a.res in P2(1)/c
hd_wql24_0m.res
created by SHELXL-2017/1 at 12:31:58 on 30-Jul-2019
CELL 1.54178 11.9227 17.3502 17.7857 90.000 90.611 90.000
ZERR 4.00 0.0003 0.0004 0.0004 0.000 0.001 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O BR
UNIT 160 200 20 20 4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173.150
SIZE 0.050 0.100 0.200
ACTA
EQIV $1 -x+1, y+1/2, -z+1/2
HTAB O1 O3_$1
HTAB O2 O5
EQIV $2 x-1, y, z
HTAB O4 N4_$2
HTAB O5 O4
EQIV $3 x, -y+3/2, z+1/2
HTAB C2 O2_$3
HTAB C3 O1_$3
EQIV $4 x, -y+3/2, z-1/2
HTAB C41 Br1_$4
L.S. 4
FMAP 2
PLAN -5 0 0.00
HTAB
BOND $H
CONF
WGHT 0.161800 4.812600
FVAR 0.27217
BR1 5 0.052623 0.917367 0.517413 11.00000 0.05493 0.06486 =
0.07277 -0.02193 -0.00310 0.00821
O1 4 0.514311 0.758146 0.103665 11.00000 0.04331 0.03673 =
0.04293 0.00366 -0.00815 -0.00049
AFIX 147
H25 2 0.531535 0.804587 0.110485 11.00000 -1.50000
AFIX 0
O2 4 0.196030 0.641751 0.193197 11.00000 0.03865 0.06119 =
0.04142 0.01165 -0.00761 0.00207
AFIX 147
H26 2 0.130501 0.648956 0.208597 11.00000 -1.50000
AFIX 0
O3 4 0.458215 0.405979 0.361778 11.00000 0.04693 0.04251 =
0.04523 0.00449 -0.00451 0.00314
O4 4 -0.175988 0.753041 0.145481 11.00000 0.05698 0.09560 =
0.07337 0.00377 -0.00067 -0.00776
AFIX 147
H44 2 -0.229159 0.723439 0.156344 11.00000 -1.50000
AFIX 0
N1 3 0.321582 0.660813 0.375449 11.00000 0.03425 0.04201 =
0.03132 0.00070 -0.00288 0.00168
N2 3 0.491024 0.709787 0.313651 11.00000 0.03188 0.03616 =
0.03510 -0.00105 -0.00509 -0.00081
N3 3 0.598390 0.519137 0.166703 11.00000 0.04378 0.04378 =
0.03683 -0.00261 -0.00152 0.00678
N4 3 0.590893 0.710195 0.143999 11.00000 0.03794 0.04169 =
0.03406 -0.00042 -0.00253 0.00047
N5 3 0.253425 0.588808 0.242662 11.00000 0.03556 0.04351 =
0.03484 0.00580 -0.00768 -0.00360
AFIX 43
H42 2 0.223264 0.548812 0.265186 11.00000 -1.20000
AFIX 0
O5 4 -0.020333 0.673802 0.237635 11.00000 0.04241 0.18451 =
0.07489 0.06167 0.00183 0.01061
AFIX 147
H45 2 -0.064529 0.698225 0.209296 11.00000 -1.50000
AFIX 0
C1 1 0.129246 0.833224 0.475029 11.00000 0.04242 0.04358 =
0.04666 -0.00756 0.00742 -0.00136
C2 1 0.216818 0.801297 0.515623 11.00000 0.04138 0.05146 =
0.03801 -0.00575 -0.00141 -0.00573
AFIX 43
H2 2 0.233095 0.818349 0.565311 11.00000 -1.20000
AFIX 0
C3 1 0.280353 0.744257 0.482961 11.00000 0.03817 0.05587 =
0.03169 -0.00141 -0.00315 -0.00145
AFIX 43
H3 2 0.341758 0.722352 0.509900 11.00000 -1.20000
AFIX 0
C4 1 0.254722 0.718613 0.410462 11.00000 0.03469 0.04206 =
0.03368 -0.00004 -0.00339 0.00021
C5 1 0.376952 0.682817 0.303166 11.00000 0.03271 0.03918 =
0.03121 0.00271 -0.00485 0.00155
AFIX 13
H12 2 0.332480 0.725740 0.280059 11.00000 -1.20000
AFIX 0
C6 1 0.569987 0.649853 0.340360 11.00000 0.03497 0.04165 =
0.03612 -0.00130 -0.00679 0.00221
AFIX 23
H4 2 0.553341 0.637064 0.393328 11.00000 -1.20000
H27 2 0.647487 0.670197 0.338519 11.00000 -1.20000
AFIX 0
C7 1 0.562014 0.576747 0.292677 11.00000 0.03426 0.03972 =
0.03343 0.00105 -0.00498 0.00309
AFIX 13
H28 2 0.608000 0.535575 0.317459 11.00000 -1.20000
AFIX 0
C8 1 0.608591 0.591050 0.213009 11.00000 0.03512 0.04174 =
0.03793 -0.00031 -0.00172 0.00045
AFIX 13
H15 2 0.689081 0.606952 0.216693 11.00000 -1.20000
AFIX 0
C9 1 0.707814 0.485369 0.149995 11.00000 0.04770 0.04710 =
0.04705 -0.00136 0.00600 0.00737
AFIX 23
H17 2 0.759145 0.526655 0.133263 11.00000 -1.20000
H16 2 0.699064 0.448175 0.108130 11.00000 -1.20000
AFIX 0
C10 1 0.759742 0.444517 0.217124 11.00000 0.04357 0.04468 =
0.04876 -0.01147 -0.00304 0.00848
C11 1 0.875714 0.447655 0.229949 11.00000 0.04106 0.07396 =
0.05520 -0.01987 0.00221 0.00031
AFIX 43
H21 2 0.920961 0.480596 0.200263 11.00000 -1.20000
AFIX 0
C12 1 0.924999 0.402572 0.286168 11.00000 0.04360 0.10116 =
0.06073 -0.02364 -0.01051 0.01638
AFIX 43
H20 2 1.003824 0.404713 0.294271 11.00000 -1.20000
AFIX 0
C13 1 0.860545 0.355053 0.329975 11.00000 0.06596 0.08267 =
0.05177 -0.00509 -0.01125 0.02651
AFIX 43
H1 2 0.895111 0.323715 0.367392 11.00000 -1.20000
AFIX 0
C14 1 0.330554 0.587555 0.402437 11.00000 0.03624 0.04702 =
0.03008 0.00510 -0.00751 -0.00345
C15 1 0.389669 0.532174 0.364424 11.00000 0.03681 0.04397 =
0.03270 0.00442 -0.00529 -0.00088
C16 1 0.438850 0.549060 0.287988 11.00000 0.03739 0.03909 =
0.03031 0.00182 -0.00519 0.00171
AFIX 13
H29 2 0.434939 0.501349 0.256525 11.00000 -1.20000
AFIX 0
C17 1 0.497649 0.777857 0.362595 11.00000 0.03957 0.04184 =
0.03612 -0.00465 -0.00319 0.00034
AFIX 23
H11 2 0.484808 0.761656 0.415177 11.00000 -1.20000
H5 2 0.437008 0.814128 0.348231 11.00000 -1.20000
AFIX 0
C18 1 0.608750 0.819342 0.358665 11.00000 0.03763 0.03836 =
0.04453 -0.00536 -0.00688 0.00147
C19 1 0.661497 0.844218 0.424961 11.00000 0.04384 0.05497 =
0.04664 -0.00776 -0.00965 0.00055
AFIX 43
H6 2 0.629995 0.831952 0.472317 11.00000 -1.20000
AFIX 0
C20 1 0.760818 0.887238 0.421551 11.00000 0.04675 0.06213 =
0.05996 -0.01150 -0.01607 -0.00424
AFIX 43
H10 2 0.794981 0.905639 0.466588 11.00000 -1.20000
AFIX 0
C21 1 0.808692 0.902827 0.353906 11.00000 0.03440 0.04720 =
0.07492 -0.00422 -0.00868 0.00175
AFIX 43
H7 2 0.876626 0.931330 0.351886 11.00000 -1.20000
AFIX 0
C22 1 0.757837 0.876913 0.288018 11.00000 0.04485 0.05082 =
0.05572 0.00343 0.00281 -0.00358
AFIX 43
H9 2 0.791785 0.887077 0.240965 11.00000 -1.20000
AFIX 0
C23 1 0.658203 0.836453 0.290483 11.00000 0.04709 0.04905 =
0.04361 -0.00099 -0.00497 -0.00519
AFIX 43
H8 2 0.623174 0.820171 0.244963 11.00000 -1.20000
AFIX 0
C24 1 0.371163 0.613231 0.248960 11.00000 0.03208 0.03784 =
0.03112 0.00156 -0.00489 -0.00013
C25 1 0.419329 0.633238 0.170083 11.00000 0.03537 0.03797 =
0.03014 0.00078 -0.00436 0.00008
AFIX 13
H24 2 0.376341 0.677192 0.147585 11.00000 -1.20000
AFIX 0
C26 1 0.414925 0.562295 0.115522 11.00000 0.04741 0.04347 =
0.03255 -0.00232 -0.00567 -0.00214
AFIX 23
H14 2 0.369495 0.520998 0.138608 11.00000 -1.20000
H13 2 0.377268 0.577833 0.068015 11.00000 -1.20000
AFIX 0
C27 1 0.530885 0.530638 0.097848 11.00000 0.05050 0.04270 =
0.03450 -0.00244 -0.00250 0.00116
AFIX 23
H23 2 0.522910 0.480884 0.071070 11.00000 -1.20000
H22 2 0.570145 0.566983 0.064236 11.00000 -1.20000
AFIX 0
C28 1 0.541189 0.653626 0.175277 11.00000 0.03529 0.04243 =
0.03255 -0.00322 -0.00183 0.00045
C29 1 0.746165 0.352821 0.319712 11.00000 0.06571 0.04739 =
0.04968 -0.00618 -0.00724 0.00970
AFIX 43
H18 2 0.701108 0.320845 0.350500 11.00000 -1.20000
AFIX 0
C30 1 0.696825 0.398318 0.263244 11.00000 0.04697 0.04147 =
0.04431 -0.00581 -0.00555 0.00565
AFIX 43
H19 2 0.617666 0.397205 0.256650 11.00000 -1.20000
AFIX 0
C31 1 0.402116 0.455732 0.394081 11.00000 0.03946 0.04301 =
0.03700 0.00633 -0.00925 -0.00192
C32 1 0.345227 0.436412 0.467348 11.00000 0.04543 0.04692 =
0.04167 0.00982 -0.00274 -0.00103
AFIX 23
H31 2 0.398458 0.445900 0.509436 11.00000 -1.20000
H30 2 0.326046 0.380896 0.467573 11.00000 -1.20000
AFIX 0
C33 1 0.238799 0.483226 0.480297 11.00000 0.04102 0.05382 =
0.03878 0.00825 -0.00356 -0.00364
C34 1 0.147778 0.463707 0.421286 11.00000 0.04065 0.06718 =
0.05153 0.00433 -0.00693 -0.00891
AFIX 137
H32 2 0.175413 0.475948 0.370983 11.00000 -1.50000
H34 2 0.080231 0.494067 0.431238 11.00000 -1.50000
H33 2 0.129744 0.408681 0.424070 11.00000 -1.50000
AFIX 0
C35 1 0.193354 0.465850 0.558516 11.00000 0.04680 0.06452 =
0.04295 0.01070 0.00293 -0.00894
AFIX 137
H35 2 0.172305 0.411345 0.561513 11.00000 -1.50000
H37 2 0.127324 0.497990 0.567739 11.00000 -1.50000
H36 2 0.251295 0.477072 0.596451 11.00000 -1.50000
AFIX 0
C36 1 0.270252 0.568782 0.474992 11.00000 0.03744 0.05116 =
0.03317 0.00518 0.00006 -0.00005
AFIX 23
H39 2 0.201281 0.600354 0.478008 11.00000 -1.20000
H38 2 0.319171 0.582567 0.518263 11.00000 -1.20000
AFIX 0
C37 1 0.164498 0.750624 0.370978 11.00000 0.03574 0.04381 =
0.03303 -0.00010 -0.00329 -0.00076
AFIX 43
H41 2 0.146463 0.732815 0.321808 11.00000 -1.20000
AFIX 0
C38 1 0.101243 0.808308 0.403391 11.00000 0.03792 0.04631 =
0.04379 0.00135 -0.00141 0.00237
AFIX 43
H40 2 0.039592 0.830449 0.376899 11.00000 -1.20000
AFIX 0
C40 1 -0.075784 0.652347 0.302574 11.00000 0.05608 0.09461 =
0.06231 0.01597 -0.00261 -0.02396
AFIX 137
H47 2 -0.020898 0.635663 0.340617 11.00000 -1.50000
H46 2 -0.127365 0.609843 0.291187 11.00000 -1.50000
H43 2 -0.118245 0.696385 0.321774 11.00000 -1.50000
AFIX 0
C41 1 -0.142269 0.738484 0.074826 11.00000 0.05983 0.08695 =
0.07881 -0.00899 0.00350 0.00941
AFIX 137
H50 2 -0.189244 0.767426 0.039171 11.00000 -1.50000
H49 2 -0.149209 0.683203 0.064469 11.00000 -1.50000
H48 2 -0.063828 0.754236 0.069447 11.00000 -1.50000
REM #####
REM #####
AFIX 0
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM hd_wql24_0m_a.res in P2(1)/c
REM R1 = 0.0814 for 6204 Fo > 4sig(Fo) and 0.0897 for all 7252 data
REM 468 parameters refined using 0 restraints
END
WGHT 0.1618 4.8109
REM Instructions for potential hydrogen bonds
HTAB O1 O3_$1
HTAB O2 O5
HTAB O4 N4_$2
HTAB O5 O4
HTAB C2 O2_$3
HTAB C3 O1_$3
HTAB C41 Br1_$4
REM Highest difference peak 1.901, deepest hole -1.272, 1-sigma level 0.115
Q1 1 -0.1776 0.6891 0.1210 11.00000 0.05 1.90
Q2 1 0.0058 0.8837 0.5384 11.00000 0.05 1.73
Q3 1 0.0256 0.9591 0.5043 11.00000 0.05 1.10
Q4 1 0.2516 0.5432 0.2193 11.00000 0.05 0.69
Q5 1 0.0933 0.8608 0.4947 11.00000 0.05 0.59
;
_shelx_res_checksum 88460
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_201809377
_database_code_depnum_ccdc_archive 'CCDC 1947690'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-17 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C29 H27 Cl N2 O'
_chemical_formula_sum 'C29 H27 Cl N2 O'
_chemical_formula_weight 454.97
_chemical_melting_point ?
_chemical_oxdiff_formula C15H15O3N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.8554(2)
_cell_length_b 18.2505(2)
_cell_length_c 12.2873(2)
_cell_angle_alpha 90
_cell_angle_beta 105.0100(10)
_cell_angle_gamma 90
_cell_volume 2351.26(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6504
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.8490
_cell_measurement_theta_min 4.4320
_shelx_estimated_absorpt_T_max 0.855
_shelx_estimated_absorpt_T_min 0.793
_exptl_absorpt_coefficient_mu 1.619
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.92914
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.285
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 960
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0306
_diffrn_reflns_av_unetI/netI 0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 17116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 67.066
_diffrn_reflns_theta_max 67.066
_diffrn_reflns_theta_min 4.217
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -68.00 -42.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -120.0000 52
#__ type_ start__ end____ width___ exp.time_
2 omega -108.00 -75.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -120.0000 66
#__ type_ start__ end____ width___ exp.time_
3 omega -77.00 -51.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 60.0000 52
#__ type_ start__ end____ width___ exp.time_
4 omega -100.00 -66.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -77.0000 -60.0000 68
#__ type_ start__ end____ width___ exp.time_
5 omega 50.00 77.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 30.0000 54
#__ type_ start__ end____ width___ exp.time_
6 omega 58.00 83.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -180.0000 50
#__ type_ start__ end____ width___ exp.time_
7 omega -33.00 57.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -37.0000 -150.0000 180
#__ type_ start__ end____ width___ exp.time_
8 omega -33.00 3.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 150.0000 72
#__ type_ start__ end____ width___ exp.time_
9 omega 19.00 55.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 -120.0000 72
#__ type_ start__ end____ width___ exp.time_
10 omega -33.00 55.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 -180.0000 176
#__ type_ start__ end____ width___ exp.time_
11 omega 8.00 37.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 -150.0000 58
#__ type_ start__ end____ width___ exp.time_
12 omega -3.00 25.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 30.0000 56
#__ type_ start__ end____ width___ exp.time_
13 omega -31.00 26.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 60.0000 114
#__ type_ start__ end____ width___ exp.time_
14 omega 58.00 108.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -150.0000 100
#__ type_ start__ end____ width___ exp.time_
15 omega 76.00 102.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -90.0000 52
#__ type_ start__ end____ width___ exp.time_
16 omega 59.00 101.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 -150.0000 84
#__ type_ start__ end____ width___ exp.time_
17 omega 40.00 65.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 60.0000 50
#__ type_ start__ end____ width___ exp.time_
18 omega 23.00 68.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 30.0000 90
#__ type_ start__ end____ width___ exp.time_
19 omega -1.00 52.00 0.5000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -57.0000 -180.0000 106
#__ type_ start__ end____ width___ exp.time_
20 omega 38.00 85.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 90.0000 94
#__ type_ start__ end____ width___ exp.time_
21 omega 40.00 67.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -180.0000 54
#__ type_ start__ end____ width___ exp.time_
22 omega 65.00 99.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 120.0000 68
#__ type_ start__ end____ width___ exp.time_
23 omega 70.00 109.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 150.0000 78
#__ type_ start__ end____ width___ exp.time_
24 omega 107.00 144.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 178.0000 120.0000 74
#__ type_ start__ end____ width___ exp.time_
25 omega 61.00 97.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 178.0000 120.0000 72
#__ type_ start__ end____ width___ exp.time_
26 omega 45.00 153.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -15.0000 0.0000 216
#__ type_ start__ end____ width___ exp.time_
27 omega 55.00 111.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 90.0000 112
#__ type_ start__ end____ width___ exp.time_
28 omega 49.00 95.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -150.0000 92
#__ type_ start__ end____ width___ exp.time_
29 omega 49.00 115.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -90.0000 132
#__ type_ start__ end____ width___ exp.time_
30 omega 44.00 131.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -77.0000 -30.0000 174
#__ type_ start__ end____ width___ exp.time_
31 omega 41.00 124.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -61.0000 60.0000 166
#__ type_ start__ end____ width___ exp.time_
32 omega 96.00 137.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 0.0000 82
#__ type_ start__ end____ width___ exp.time_
33 omega 43.00 91.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -120.0000 96
#__ type_ start__ end____ width___ exp.time_
34 omega 37.00 87.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -30.0000 100
#__ type_ start__ end____ width___ exp.time_
35 omega 43.00 151.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -15.0000 120.0000 216
#__ type_ start__ end____ width___ exp.time_
36 omega 79.00 137.00 0.5000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -77.0000 -120.0000 116
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0226261000
_diffrn_orient_matrix_UB_12 -0.0808169000
_diffrn_orient_matrix_UB_13 -0.0252511000
_diffrn_orient_matrix_UB_21 0.0588653000
_diffrn_orient_matrix_UB_22 -0.0138223000
_diffrn_orient_matrix_UB_23 0.1264910000
_diffrn_orient_matrix_UB_31 -0.1327522000
_diffrn_orient_matrix_UB_32 -0.0199418000
_diffrn_orient_matrix_UB_33 0.0146024000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3540
_reflns_number_total 4192
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.296
_refine_diff_density_min -0.356
_refine_diff_density_rms 0.048
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 299
_refine_ls_number_reflns 4192
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0555
_refine_ls_R_factor_gt 0.0474
_refine_ls_restrained_S_all 1.044
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.3819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1290
_refine_ls_wR_factor_ref 0.1396
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C20(H20), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C21(H21A,H21B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C16(H16), C17(H17), C25(H25),
C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42105(17) 0.36319(9) 0.65974(15) 0.0495(4) Uani 1 1 d . . . . .
C2 C 0.29308(18) 0.40142(11) 0.63079(17) 0.0597(5) Uani 1 1 d . . . . .
H2A H 0.2450 0.3858 0.6831 0.072 Uiso 1 1 calc R . . . .
H2B H 0.3064 0.4539 0.6397 0.072 Uiso 1 1 calc R . . . .
C3 C 0.21633(17) 0.38546(12) 0.51183(18) 0.0635(5) Uani 1 1 d . . . . .
H3A H 0.1388 0.4144 0.4947 0.076 Uiso 1 1 calc R . . . .
H3B H 0.1925 0.3341 0.5052 0.076 Uiso 1 1 calc R . . . .
C4 C 0.29354(16) 0.40352(11) 0.42864(16) 0.0577(4) Uani 1 1 d . . . . .
H4A H 0.2464 0.3889 0.3535 0.069 Uiso 1 1 calc R . . . .
H4B H 0.3075 0.4560 0.4281 0.069 Uiso 1 1 calc R . . . .
C5 C 0.42025(15) 0.36459(9) 0.45978(14) 0.0451(4) Uani 1 1 d . . . . .
C6 C 0.47689(15) 0.34495(8) 0.56893(14) 0.0451(4) Uani 1 1 d . . . . .
C7 C 0.43059(14) 0.37969(9) 0.26479(14) 0.0462(4) Uani 1 1 d . . . . .
C8 C 0.43820(17) 0.45425(10) 0.24890(16) 0.0554(4) Uani 1 1 d . . . . .
H8 H 0.4708 0.4847 0.3103 0.066 Uiso 1 1 calc R . . . .
C9 C 0.3975(2) 0.48372(12) 0.14196(18) 0.0645(5) Uani 1 1 d . . . . .
H9 H 0.4024 0.5341 0.1324 0.077 Uiso 1 1 calc R . . . .
C10 C 0.34956(18) 0.43986(13) 0.04899(17) 0.0651(5) Uani 1 1 d . . . . .
C11 C 0.34273(19) 0.36506(13) 0.06613(17) 0.0665(5) Uani 1 1 d . . . . .
H11 H 0.3110 0.3345 0.0047 0.080 Uiso 1 1 calc R . . . .
C12 C 0.38214(17) 0.33494(11) 0.17281(16) 0.0565(4) Uani 1 1 d . . . . .
H12 H 0.3761 0.2847 0.1827 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3059(3) 0.4724(2) -0.0678(2) 0.0989(9) Uani 1 1 d . . . . .
H13A H 0.3191 0.5245 -0.0637 0.148 Uiso 1 1 calc GR . . . .
H13B H 0.2170 0.4622 -0.0986 0.148 Uiso 1 1 calc GR . . . .
H13C H 0.3541 0.4513 -0.1153 0.148 Uiso 1 1 calc GR . . . .
C14 C 0.77009(17) 0.38566(11) 0.71735(15) 0.0554(4) Uani 1 1 d . . . . .
H14 H 0.7364 0.3739 0.7774 0.066 Uiso 1 1 calc R . . . .
C15 C 0.87433(18) 0.43174(12) 0.73463(18) 0.0636(5) Uani 1 1 d . . . . .
C16 C 0.92816(18) 0.44753(11) 0.6480(2) 0.0652(5) Uani 1 1 d . . . . .
H16 H 1.0005 0.4769 0.6607 0.078 Uiso 1 1 calc R . . . .
C17 C 0.87458(17) 0.41959(11) 0.54219(18) 0.0588(4) Uani 1 1 d . . . . .
H17 H 0.9118 0.4302 0.4838 0.071 Uiso 1 1 calc R . . . .
C18 C 0.76530(15) 0.37553(9) 0.52058(14) 0.0472(4) Uani 1 1 d . . . . .
C19 C 0.71521(15) 0.35683(9) 0.61195(14) 0.0464(4) Uani 1 1 d . . . . .
C20 C 0.60264(16) 0.30481(9) 0.59503(14) 0.0474(4) Uani 1 1 d . . . . .
H20 H 0.6114 0.2752 0.6631 0.057 Uiso 1 1 calc R . . . .
C21 C 0.60263(17) 0.25474(9) 0.49588(15) 0.0521(4) Uani 1 1 d . . . . .
H21A H 0.6803 0.2259 0.5113 0.063 Uiso 1 1 calc R . . . .
H21B H 0.5303 0.2216 0.4817 0.063 Uiso 1 1 calc R . . . .
C22 C 0.59410(15) 0.30409(9) 0.39571(14) 0.0479(4) Uani 1 1 d . . . . .
H22 H 0.5892 0.2732 0.3295 0.057 Uiso 1 1 calc R . . . .
C23 C 0.75242(18) 0.36991(11) 0.31662(16) 0.0578(4) Uani 1 1 d . . . . .
H23A H 0.7730 0.4217 0.3225 0.069 Uiso 1 1 calc R . . . .
H23B H 0.6831 0.3632 0.2494 0.069 Uiso 1 1 calc R . . . .
C24 C 0.86749(16) 0.32859(11) 0.30102(16) 0.0556(4) Uani 1 1 d . . . . .
C25 C 0.9206(3) 0.34975(17) 0.2156(2) 0.0854(7) Uani 1 1 d . . . . .
H25 H 0.8871 0.3897 0.1706 0.103 Uiso 1 1 calc R . . . .
C26 C 1.0229(3) 0.3121(3) 0.1962(3) 0.1198(12) Uani 1 1 d . . . . .
H26 H 1.0580 0.3269 0.1383 0.144 Uiso 1 1 calc R . . . .
C27 C 1.0730(3) 0.2535(2) 0.2611(4) 0.1167(13) Uani 1 1 d . . . . .
H27 H 1.1415 0.2280 0.2470 0.140 Uiso 1 1 calc R . . . .
C28 C 1.0226(2) 0.23220(15) 0.3469(3) 0.0959(9) Uani 1 1 d . . . . .
H28 H 1.0572 0.1924 0.3919 0.115 Uiso 1 1 calc R . . . .
C29 C 0.91991(19) 0.26976(12) 0.3672(2) 0.0712(6) Uani 1 1 d . . . . .
H29 H 0.8861 0.2552 0.4260 0.085 Uiso 1 1 calc R . . . .
Cl1 Cl 0.93898(6) 0.46743(5) 0.86881(6) 0.0994(3) Uani 1 1 d . . . . .
N1 N 0.47546(13) 0.34828(8) 0.37505(12) 0.0485(3) Uani 1 1 d . . . . .
N2 N 0.70744(14) 0.34915(9) 0.41348(13) 0.0538(4) Uani 1 1 d . . . . .
O1 O 0.47421(15) 0.34895(8) 0.75889(11) 0.0654(4) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0559(10) 0.0430(8) 0.0531(10) -0.0049(7) 0.0202(8) -0.0080(7)
C2 0.0558(10) 0.0621(10) 0.0679(11) -0.0086(9) 0.0281(9) -0.0015(8)
C3 0.0420(9) 0.0774(12) 0.0744(12) -0.0082(10) 0.0207(9) -0.0012(8)
C4 0.0396(8) 0.0738(12) 0.0591(10) -0.0029(9) 0.0118(7) 0.0075(8)
C5 0.0383(8) 0.0467(8) 0.0512(9) -0.0052(6) 0.0132(7) -0.0026(6)
C6 0.0435(8) 0.0435(8) 0.0500(9) -0.0017(6) 0.0150(7) -0.0043(6)
C7 0.0366(8) 0.0562(9) 0.0455(8) -0.0031(7) 0.0102(6) 0.0038(6)
C8 0.0527(10) 0.0582(10) 0.0560(10) -0.0076(8) 0.0152(8) -0.0042(7)
C9 0.0617(11) 0.0668(11) 0.0688(12) 0.0103(9) 0.0235(9) 0.0062(9)
C10 0.0471(10) 0.0964(15) 0.0541(11) 0.0095(10) 0.0172(8) 0.0165(9)
C11 0.0533(10) 0.0917(14) 0.0493(10) -0.0162(10) 0.0039(8) 0.0100(9)
C12 0.0497(9) 0.0599(10) 0.0564(10) -0.0109(8) 0.0077(8) 0.0052(7)
C13 0.0817(17) 0.153(3) 0.0623(14) 0.0276(16) 0.0186(12) 0.0237(17)
C14 0.0462(9) 0.0666(10) 0.0501(9) -0.0003(8) 0.0068(7) 0.0065(8)
C15 0.0468(10) 0.0726(12) 0.0632(11) -0.0138(9) -0.0005(8) 0.0042(8)
C16 0.0410(9) 0.0668(11) 0.0846(14) -0.0075(10) 0.0106(9) -0.0044(8)
C17 0.0430(9) 0.0649(10) 0.0702(12) 0.0028(9) 0.0178(8) 0.0007(8)
C18 0.0365(8) 0.0525(8) 0.0519(9) 0.0041(7) 0.0102(7) 0.0071(6)
C19 0.0387(8) 0.0501(8) 0.0481(9) 0.0044(7) 0.0073(7) 0.0080(6)
C20 0.0486(9) 0.0461(8) 0.0479(9) 0.0067(7) 0.0130(7) 0.0017(7)
C21 0.0506(9) 0.0449(8) 0.0611(10) -0.0006(7) 0.0147(8) 0.0044(7)
C22 0.0426(8) 0.0522(9) 0.0490(9) -0.0062(7) 0.0123(7) 0.0057(7)
C23 0.0503(9) 0.0748(11) 0.0506(9) 0.0082(8) 0.0170(8) 0.0080(8)
C24 0.0442(9) 0.0651(10) 0.0589(10) -0.0137(8) 0.0155(8) -0.0057(7)
C25 0.0796(15) 0.1117(19) 0.0765(15) -0.0049(13) 0.0407(13) 0.0023(13)
C26 0.096(2) 0.168(4) 0.119(3) -0.034(3) 0.070(2) 0.004(2)
C27 0.0732(17) 0.125(3) 0.162(3) -0.068(3) 0.049(2) 0.0085(17)
C28 0.0618(13) 0.0714(14) 0.149(3) -0.0291(16) 0.0180(16) 0.0070(11)
C29 0.0534(11) 0.0663(12) 0.0935(16) -0.0078(11) 0.0181(10) 0.0015(9)
Cl1 0.0706(4) 0.1349(6) 0.0807(4) -0.0434(4) -0.0018(3) -0.0132(3)
N1 0.0412(7) 0.0577(8) 0.0460(7) -0.0036(6) 0.0102(6) 0.0054(6)
N2 0.0423(7) 0.0723(9) 0.0479(8) 0.0022(7) 0.0137(6) 0.0002(6)
O1 0.0826(9) 0.0667(8) 0.0505(7) 0.0002(6) 0.0239(7) 0.0047(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.512(3) . ?
C1 C6 1.440(2) . ?
C1 O1 1.233(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(2) . ?
C5 C6 1.370(2) . ?
C5 N1 1.362(2) . ?
C6 C20 1.509(2) . ?
C7 C8 1.380(3) . ?
C7 C12 1.383(2) . ?
C7 N1 1.435(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 C11 1.386(3) . ?
C10 C13 1.512(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C14 C19 1.382(2) . ?
C15 C16 1.371(3) . ?
C15 Cl1 1.742(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(3) . ?
C18 C19 1.410(2) . ?
C18 N2 1.389(2) . ?
C19 C20 1.519(2) . ?
C20 H20 0.9800 . ?
C20 C21 1.523(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(2) . ?
C22 H22 0.9800 . ?
C22 N1 1.485(2) . ?
C22 N2 1.449(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.513(2) . ?
C23 N2 1.449(2) . ?
C24 C25 1.377(3) . ?
C24 C29 1.378(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.361(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.385(3) . ?
C29 H29 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.02(16) . . ?
O1 C1 C2 119.73(16) . . ?
O1 C1 C6 122.25(17) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 112.41(15) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.34(15) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.72(16) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C6 C5 C4 121.37(15) . . ?
N1 C5 C4 117.54(15) . . ?
N1 C5 C6 121.07(14) . . ?
C1 C6 C20 119.14(15) . . ?
C5 C6 C1 121.71(15) . . ?
C5 C6 C20 119.14(14) . . ?
C8 C7 C12 119.37(17) . . ?
C8 C7 N1 120.61(15) . . ?
C12 C7 N1 120.00(16) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.13(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.33(19) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 117.93(19) . . ?
C9 C10 C13 121.0(2) . . ?
C11 C10 C13 121.0(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.32(19) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.91(18) . . ?
C11 C12 H12 120.0 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C19 120.87(18) . . ?
C19 C14 H14 119.6 . . ?
C14 C15 Cl1 119.09(17) . . ?
C16 C15 C14 120.37(18) . . ?
C16 C15 Cl1 120.52(16) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.63(18) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.42(18) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 118.06(16) . . ?
N2 C18 C17 122.11(16) . . ?
N2 C18 C19 119.82(15) . . ?
C14 C19 C18 119.50(16) . . ?
C14 C19 C20 120.18(15) . . ?
C18 C19 C20 120.32(15) . . ?
C6 C20 C19 112.17(13) . . ?
C6 C20 H20 109.4 . . ?
C6 C20 C21 107.98(14) . . ?
C19 C20 H20 109.4 . . ?
C19 C20 C21 108.54(14) . . ?
C21 C20 H20 109.4 . . ?
C20 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 C20 106.35(13) . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C21 C22 H22 108.2 . . ?
N1 C22 C21 109.33(13) . . ?
N1 C22 H22 108.2 . . ?
N2 C22 C21 110.22(14) . . ?
N2 C22 H22 108.2 . . ?
N2 C22 N1 112.50(14) . . ?
H23A C23 H23B 107.4 . . ?
C24 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
N2 C23 H23A 108.3 . . ?
N2 C23 H23B 108.3 . . ?
N2 C23 C24 116.01(16) . . ?
C25 C24 C23 118.6(2) . . ?
C25 C24 C29 118.6(2) . . ?
C29 C24 C23 122.81(18) . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.5(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.8(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.5(3) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C5 N1 C7 121.69(13) . . ?
C5 N1 C22 121.47(14) . . ?
C7 N1 C22 116.47(13) . . ?
C18 N2 C22 119.84(14) . . ?
C18 N2 C23 121.44(15) . . ?
C22 N2 C23 118.58(15) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -54.1(2) . . . . ?
C1 C6 C20 C19 -93.62(17) . . . . ?
C1 C6 C20 C21 146.83(15) . . . . ?
C2 C1 C6 C5 3.3(2) . . . . ?
C2 C1 C6 C20 -178.22(14) . . . . ?
C2 C3 C4 C5 54.0(2) . . . . ?
C3 C4 C5 C6 -26.5(2) . . . . ?
C3 C4 C5 N1 152.20(16) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
C4 C5 C6 C20 178.87(15) . . . . ?
C4 C5 N1 C7 12.9(2) . . . . ?
C4 C5 N1 C22 -174.31(15) . . . . ?
C5 C6 C20 C19 84.89(18) . . . . ?
C5 C6 C20 C21 -34.67(19) . . . . ?
C6 C1 C2 C3 25.6(2) . . . . ?
C6 C5 N1 C7 -168.35(15) . . . . ?
C6 C5 N1 C22 4.4(2) . . . . ?
C6 C20 C21 C22 63.22(17) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C7 N1 C5 64.0(2) . . . . ?
C8 C7 N1 C22 -109.08(18) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C13 -179.62(19) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C12 C7 N1 C5 -117.61(18) . . . . ?
C12 C7 N1 C22 69.27(19) . . . . ?
C13 C10 C11 C12 -179.82(19) . . . . ?
C14 C15 C16 C17 2.7(3) . . . . ?
C14 C19 C20 C6 87.95(18) . . . . ?
C14 C19 C20 C21 -152.82(15) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C15 C14 C19 C20 178.54(16) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -3.6(3) . . . . ?
C16 C17 C18 N2 177.61(17) . . . . ?
C17 C18 C19 C14 3.8(2) . . . . ?
C17 C18 C19 C20 -175.62(15) . . . . ?
C17 C18 N2 C22 -179.67(15) . . . . ?
C17 C18 N2 C23 -4.2(3) . . . . ?
C18 C19 C20 C6 -92.65(18) . . . . ?
C18 C19 C20 C21 26.58(19) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
C19 C14 C15 Cl1 179.32(14) . . . . ?
C19 C18 N2 C22 1.6(2) . . . . ?
C19 C18 N2 C23 177.07(15) . . . . ?
C19 C20 C21 C22 -58.60(17) . . . . ?
C20 C21 C22 N1 -59.31(17) . . . . ?
C20 C21 C22 N2 64.85(17) . . . . ?
C21 C22 N1 C5 26.6(2) . . . . ?
C21 C22 N1 C7 -160.30(14) . . . . ?
C21 C22 N2 C18 -36.4(2) . . . . ?
C21 C22 N2 C23 147.95(15) . . . . ?
C23 C24 C25 C26 -177.9(3) . . . . ?
C23 C24 C29 C28 177.7(2) . . . . ?
C24 C23 N2 C18 80.9(2) . . . . ?
C24 C23 N2 C22 -103.56(19) . . . . ?
C24 C25 C26 C27 0.0(5) . . . . ?
C25 C24 C29 C28 -0.9(3) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C27 C28 C29 0.6(5) . . . . ?
C27 C28 C29 C24 0.2(4) . . . . ?
C29 C24 C25 C26 0.8(4) . . . . ?
Cl1 C15 C16 C17 -179.12(15) . . . . ?
N1 C5 C6 C1 178.64(14) . . . . ?
N1 C5 C6 C20 0.2(2) . . . . ?
N1 C7 C8 C9 178.47(16) . . . . ?
N1 C7 C12 C11 -177.93(16) . . . . ?
N1 C22 N2 C18 85.89(18) . . . . ?
N1 C22 N2 C23 -89.74(18) . . . . ?
N2 C18 C19 C14 -177.39(15) . . . . ?
N2 C18 C19 C20 3.2(2) . . . . ?
N2 C22 N1 C5 -96.24(18) . . . . ?
N2 C22 N1 C7 76.89(18) . . . . ?
N2 C23 C24 C25 -175.0(2) . . . . ?
N2 C23 C24 C29 6.3(3) . . . . ?
O1 C1 C2 C3 -154.65(17) . . . . ?
O1 C1 C6 C5 -176.38(15) . . . . ?
O1 C1 C6 C20 2.1(2) . . . . ?
_iucr_refine_instructions_details
;
201809377.res created by SHELXL-2014/7
TITL 201809377_a.res in P2(1)/c
REM Old TITL 201809377 in P21/c #14
REM SHELXT solution in P2(1)/c
REM R1 0.204, Rweak 0.095, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C29 N2 O Cl
CELL 1.54184 10.8554 18.2505 12.2873 90 105.01 90
ZERR 4 0.0002 0.0002 0.0002 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 116 108 4 8 4
L.S. 10 0 0
PLAN 20
SIZE 0.1 0.12 0.15
MPLA C1 C2 C3 C4 C5 C6
MPLA C7 C8 C9 C10 C11 C12
MPLA C14 C15 C16 C17 C18 C19
MPLA C24 C25 C26 C27 C28 C29
MPLA C5 C6 N1 C20 C22
MPLA C20 C21 C22
MPLA C18 C19 C20 C22 N2
BOND $H
list 4
conf
fmap 2
acta
REM
REM
REM
WGHT 0.077900 0.381900
FVAR 0.53873
C1 1 0.421045 0.363190 0.659735 11.00000 0.05592 0.04300 =
0.05308 -0.00494 0.02017 -0.00803
C2 1 0.293083 0.401416 0.630792 11.00000 0.05583 0.06208 =
0.06788 -0.00858 0.02805 -0.00154
AFIX 23
H2A 2 0.244993 0.385764 0.683095 11.00000 -1.20000
H2B 2 0.306422 0.453864 0.639651 11.00000 -1.20000
AFIX 0
C3 1 0.216333 0.385459 0.511834 11.00000 0.04202 0.07742 =
0.07435 -0.00822 0.02072 -0.00116
AFIX 23
H3A 2 0.138767 0.414423 0.494675 11.00000 -1.20000
H3B 2 0.192541 0.334104 0.505227 11.00000 -1.20000
AFIX 0
C4 1 0.293542 0.403518 0.428639 11.00000 0.03964 0.07379 =
0.05911 -0.00294 0.01180 0.00746
AFIX 23
H4A 2 0.246374 0.388860 0.353519 11.00000 -1.20000
H4B 2 0.307456 0.456002 0.428063 11.00000 -1.20000
AFIX 0
C5 1 0.420248 0.364592 0.459781 11.00000 0.03833 0.04667 =
0.05118 -0.00518 0.01316 -0.00260
C6 1 0.476893 0.344949 0.568933 11.00000 0.04352 0.04351 =
0.05000 -0.00175 0.01505 -0.00426
C7 1 0.430585 0.379687 0.264788 11.00000 0.03658 0.05620 =
0.04550 -0.00310 0.01020 0.00376
C8 1 0.438197 0.454253 0.248896 11.00000 0.05271 0.05819 =
0.05598 -0.00756 0.01524 -0.00418
AFIX 43
H8 2 0.470792 0.484727 0.310264 11.00000 -1.20000
AFIX 0
C9 1 0.397471 0.483715 0.141961 11.00000 0.06167 0.06678 =
0.06877 0.01030 0.02353 0.00618
AFIX 43
H9 2 0.402425 0.534081 0.132400 11.00000 -1.20000
AFIX 0
C10 1 0.349557 0.439861 0.048994 11.00000 0.04708 0.09639 =
0.05410 0.00949 0.01723 0.01651
C11 1 0.342730 0.365062 0.066131 11.00000 0.05326 0.09166 =
0.04930 -0.01624 0.00386 0.00997
AFIX 43
H11 2 0.311017 0.334520 0.004668 11.00000 -1.20000
AFIX 0
C12 1 0.382136 0.334945 0.172809 11.00000 0.04971 0.05992 =
0.05645 -0.01092 0.00766 0.00524
AFIX 43
H12 2 0.376064 0.284675 0.182679 11.00000 -1.20000
AFIX 0
C13 1 0.305946 0.472423 -0.067809 11.00000 0.08172 0.15258 =
0.06235 0.02762 0.01860 0.02374
AFIX 137
H13A 2 0.319066 0.524476 -0.063695 11.00000 -1.50000
H13B 2 0.216962 0.462208 -0.098579 11.00000 -1.50000
H13C 2 0.354114 0.451264 -0.115329 11.00000 -1.50000
AFIX 0
C14 1 0.770086 0.385657 0.717348 11.00000 0.04623 0.06661 =
0.05011 -0.00028 0.00678 0.00652
AFIX 43
H14 2 0.736403 0.373881 0.777440 11.00000 -1.20000
AFIX 0
C15 1 0.874327 0.431742 0.734635 11.00000 0.04678 0.07260 =
0.06317 -0.01378 -0.00054 0.00415
C16 1 0.928162 0.447528 0.648033 11.00000 0.04095 0.06681 =
0.08461 -0.00746 0.01061 -0.00438
AFIX 43
H16 2 1.000455 0.476935 0.660657 11.00000 -1.20000
AFIX 0
C17 1 0.874575 0.419586 0.542186 11.00000 0.04300 0.06488 =
0.07019 0.00277 0.01782 0.00066
AFIX 43
H17 2 0.911778 0.430209 0.483827 11.00000 -1.20000
AFIX 0
C18 1 0.765297 0.375534 0.520580 11.00000 0.03647 0.05252 =
0.05191 0.00412 0.01024 0.00715
C19 1 0.715211 0.356827 0.611951 11.00000 0.03874 0.05015 =
0.04808 0.00443 0.00735 0.00801
C20 1 0.602641 0.304815 0.595030 11.00000 0.04858 0.04607 =
0.04792 0.00670 0.01302 0.00174
AFIX 13
H20 2 0.611377 0.275177 0.663118 11.00000 -1.20000
AFIX 0
C21 1 0.602626 0.254736 0.495880 11.00000 0.05059 0.04491 =
0.06106 -0.00062 0.01469 0.00440
AFIX 23
H21A 2 0.680298 0.225908 0.511273 11.00000 -1.20000
H21B 2 0.530282 0.221648 0.481711 11.00000 -1.20000
AFIX 0
C22 1 0.594098 0.304092 0.395711 11.00000 0.04261 0.05222 =
0.04900 -0.00621 0.01225 0.00574
AFIX 13
H22 2 0.589232 0.273205 0.329488 11.00000 -1.20000
AFIX 0
C23 1 0.752421 0.369908 0.316616 11.00000 0.05031 0.07484 =
0.05056 0.00821 0.01700 0.00802
AFIX 23
H23A 2 0.772989 0.421721 0.322503 11.00000 -1.20000
H23B 2 0.683077 0.363225 0.249446 11.00000 -1.20000
AFIX 0
C24 1 0.867486 0.328586 0.301017 11.00000 0.04417 0.06510 =
0.05888 -0.01368 0.01552 -0.00569
C25 1 0.920560 0.349750 0.215559 11.00000 0.07956 0.11167 =
0.07649 -0.00488 0.04071 0.00225
AFIX 43
H25 2 0.887096 0.389712 0.170619 11.00000 -1.20000
AFIX 0
C26 1 1.022908 0.312130 0.196166 11.00000 0.09579 0.16815 =
0.11893 -0.03351 0.07015 0.00362
AFIX 43
H26 2 1.058007 0.326929 0.138254 11.00000 -1.20000
AFIX 0
C27 1 1.073038 0.253483 0.261099 11.00000 0.07319 0.12477 =
0.16241 -0.06793 0.04917 0.00852
AFIX 43
H27 2 1.141463 0.227993 0.246989 11.00000 -1.20000
AFIX 0
C28 1 1.022626 0.232204 0.346927 11.00000 0.06178 0.07143 =
0.14940 -0.02911 0.01800 0.00702
AFIX 43
H28 2 1.057246 0.192449 0.391850 11.00000 -1.20000
AFIX 0
C29 1 0.919910 0.269764 0.367223 11.00000 0.05343 0.06629 =
0.09346 -0.00776 0.01811 0.00153
AFIX 43
H29 2 0.886078 0.255158 0.425999 11.00000 -1.20000
AFIX 0
CL1 3 0.938976 0.467429 0.868806 11.00000 0.07064 0.13489 =
0.08068 -0.04335 -0.00176 -0.01316
N1 4 0.475464 0.348283 0.375055 11.00000 0.04122 0.05767 =
0.04601 -0.00358 0.01022 0.00541
N2 4 0.707441 0.349145 0.413485 11.00000 0.04230 0.07233 =
0.04789 0.00217 0.01370 0.00018
O1 5 0.474213 0.348955 0.758890 11.00000 0.08259 0.06673 =
0.05046 0.00019 0.02389 0.00474
HKLF 4
REM 201809377_a.res in P2(1)/c
REM R1 = 0.0474 for 3540 Fo > 4sig(Fo) and 0.0555 for all 4192 data
REM 299 parameters refined using 0 restraints
END
WGHT 0.0779 0.3819
REM Highest difference peak 0.296, deepest hole -0.356, 1-sigma level 0.048
Q1 1 0.8960 0.4311 0.9052 11.00000 0.05 0.30
Q2 1 0.2633 0.4258 0.3479 11.00000 0.05 0.15
Q3 1 0.7121 0.3771 0.5613 11.00000 0.05 0.15
Q4 1 1.0240 0.4463 0.8620 11.00000 0.05 0.14
Q5 1 0.2176 0.5027 -0.0868 11.00000 0.05 0.14
Q6 1 0.7609 0.2372 0.5115 11.00000 0.05 0.14
Q7 1 0.6856 0.4672 0.3360 11.00000 0.05 0.13
Q8 1 0.3138 0.5298 0.4257 11.00000 0.05 0.13
Q9 1 0.3565 0.2678 0.2426 11.00000 0.05 0.13
Q10 1 0.8678 0.3534 0.1509 11.00000 0.05 0.12
Q11 1 0.6974 0.3937 0.7876 11.00000 0.05 0.12
Q12 1 0.4302 0.2143 0.4624 11.00000 0.05 0.12
Q13 1 0.3861 0.5102 -0.0863 11.00000 0.05 0.12
Q14 1 0.7869 0.2050 0.4142 11.00000 0.05 0.12
Q15 1 0.8938 0.1961 0.5259 11.00000 0.05 0.12
Q16 1 0.4592 0.3548 0.2025 11.00000 0.05 0.12
Q17 1 0.2541 0.4294 -0.1139 11.00000 0.05 0.12
Q18 1 0.8495 0.2363 0.3921 11.00000 0.05 0.12
Q19 1 0.9264 0.4170 0.7055 11.00000 0.05 0.12
Q20 1 0.5700 0.1541 0.5837 11.00000 0.05 0.11
REM The information below was added by Olex2.
REM
REM R1 = 0.0474 for 3540 Fo > 4sig(Fo) and 0.0555 for all 17447 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.30, deepest hole -0.36
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0555
REM R1_gt = 0.0474
REM wR_ref = 0.1396
REM GOOF = 1.044
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 17447
REM Reflections_gt = 3540
REM Parameters = n/a
REM Hole = -0.36
REM Peak = 0.30
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_201810415
_database_code_depnum_ccdc_archive 'CCDC 1947693'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-17 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C46 H42 Br N3 O'
_chemical_formula_sum 'C46 H42 Br N3 O'
_chemical_formula_weight 732.73
_chemical_melting_point ?
_chemical_oxdiff_formula C15H15O3N2Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 10.2078(3)
_cell_length_b 19.1520(5)
_cell_length_c 18.9514(4)
_cell_angle_alpha 90
_cell_angle_beta 94.804(2)
_cell_angle_gamma 90
_cell_volume 3691.96(16)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4592
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.8150
_cell_measurement_theta_min 4.6030
_shelx_estimated_absorpt_T_max 0.839
_shelx_estimated_absorpt_T_min 0.735
_exptl_absorpt_coefficient_mu 1.819
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.318
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 1528
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0612
_diffrn_reflns_av_unetI/netI 0.0582
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 14208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 67.077
_diffrn_reflns_theta_max 67.077
_diffrn_reflns_theta_min 4.618
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -43.00 20.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 37.0000 150.0000 63
#__ type_ start__ end____ width___ exp.time_
2 omega -103.00 -30.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -77.0000 -150.0000 73
#__ type_ start__ end____ width___ exp.time_
3 omega -57.00 -32.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -180.0000 25
#__ type_ start__ end____ width___ exp.time_
4 omega -108.00 -76.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -180.0000 32
#__ type_ start__ end____ width___ exp.time_
5 omega 58.00 109.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -90.0000 51
#__ type_ start__ end____ width___ exp.time_
6 omega -1.00 81.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 19.0000 30.0000 82
#__ type_ start__ end____ width___ exp.time_
7 omega 8.00 45.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 0.0000 37
#__ type_ start__ end____ width___ exp.time_
8 omega 1.00 39.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -60.0000 38
#__ type_ start__ end____ width___ exp.time_
9 omega 2.00 49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -120.0000 47
#__ type_ start__ end____ width___ exp.time_
10 omega 76.00 101.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 0.0000 25
#__ type_ start__ end____ width___ exp.time_
11 omega 75.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 150.0000 30
#__ type_ start__ end____ width___ exp.time_
12 omega 46.00 77.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -60.0000 31
#__ type_ start__ end____ width___ exp.time_
13 omega 40.00 84.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 90.0000 44
#__ type_ start__ end____ width___ exp.time_
14 omega 57.00 105.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 -30.0000 48
#__ type_ start__ end____ width___ exp.time_
15 omega 50.00 76.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 120.0000 26
#__ type_ start__ end____ width___ exp.time_
16 omega 124.00 157.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 -180.0000 33
#__ type_ start__ end____ width___ exp.time_
17 omega 45.00 92.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 60.0000 47
#__ type_ start__ end____ width___ exp.time_
18 omega 58.00 91.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -180.0000 33
#__ type_ start__ end____ width___ exp.time_
19 omega 44.00 89.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 150.0000 45
#__ type_ start__ end____ width___ exp.time_
20 omega 44.00 98.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -120.0000 54
#__ type_ start__ end____ width___ exp.time_
21 omega 38.00 98.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -60.0000 60
#__ type_ start__ end____ width___ exp.time_
22 omega 111.00 169.00 1.0000 7.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 -90.0000 58
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.1391169000
_diffrn_orient_matrix_UB_12 -0.0170584000
_diffrn_orient_matrix_UB_13 -0.0208177000
_diffrn_orient_matrix_UB_21 0.0501147000
_diffrn_orient_matrix_UB_22 -0.0040021000
_diffrn_orient_matrix_UB_23 0.0788750000
_diffrn_orient_matrix_UB_31 -0.0326649000
_diffrn_orient_matrix_UB_32 -0.0785198000
_diffrn_orient_matrix_UB_33 0.0005240000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5036
_reflns_number_total 6586
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 1.014
_refine_diff_density_min -0.541
_refine_diff_density_rms 0.077
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 473
_refine_ls_number_reflns 6586
_refine_ls_number_restraints 72
_refine_ls_R_factor_all 0.0870
_refine_ls_R_factor_gt 0.0701
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1123P)^2^+2.5906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1909
_refine_ls_wR_factor_ref 0.2129
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C45A) \\sim Ueq, Uanis(C44A) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C43A) \\sim Ueq,
Uanis(C42A) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C41)
\\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C40) = Uanis(C40A)
Uanis(C41) = Uanis(C41A)
Uanis(C46) = Uanis(C46A)
Uanis(C45) = Uanis(C45A)
Uanis(C44) = Uanis(C44A)
Uanis(C43) = Uanis(C43A)
Uanis(C42) = Uanis(C42A)
3. Others
Sof(C40A)=Sof(H40C)=Sof(H40D)=1-FVAR(1)
Sof(C40)=Sof(H40A)=Sof(H40B)=FVAR(1)
Sof(C41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=
Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(2)
Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=
Sof(H45)=Sof(C46)=Sof(H46)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
C15(H15), C22(H22), C23(H23), C31(H31)
4.b Secondary CH2 refined with riding coordinates:
C10(H10A,H10B), C12(H12A,H12B), C24(H24A,H24B), C40(H40A,H40B), C40A(H40C,H40D)
4.c Aromatic/amide H refined with riding coordinates:
C1(H1), C2(H2), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35),
C36(H36), C38(H38), C39(H39), C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A),
C46A(H46A), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
4.d Fitted hexagon refined as free rotating group:
C41A(C42A,C43A,C44A,C45A,C46A)
4.e Idealised Me refined as rotating group:
C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.36009(6) 0.90671(4) 0.70401(3) 0.0917(3) Uani 1 1 d . . . . .
C1 C -0.2227(3) 0.81395(19) 0.5282(2) 0.0452(8) Uani 1 1 d . . . . .
H1 H -0.2328 0.7709 0.5057 0.054 Uiso 1 1 calc R . . . .
C2 C -0.2848(4) 0.8266(2) 0.5890(2) 0.0533(9) Uani 1 1 d . . . . .
H2 H -0.3349 0.7919 0.6081 0.064 Uiso 1 1 calc R . . . .
C3 C -0.2721(4) 0.8904(2) 0.62096(19) 0.0513(9) Uani 1 1 d . . . . .
C4 C -0.1988(4) 0.9419(2) 0.5952(2) 0.0558(10) Uani 1 1 d . . . . .
H4 H -0.1922 0.9853 0.6171 0.067 Uiso 1 1 calc R . . . .
C5 C -0.1336(4) 0.9283(2) 0.5353(2) 0.0482(8) Uani 1 1 d . . . . .
H5 H -0.0805 0.9627 0.5180 0.058 Uiso 1 1 calc R . . . .
C6 C -0.1458(3) 0.86489(17) 0.50060(16) 0.0355(7) Uani 1 1 d . . . . .
C7 C -0.0690(3) 0.89101(18) 0.38386(18) 0.0403(7) Uani 1 1 d . . . . .
C8 C 0.0219(3) 0.87891(18) 0.33594(19) 0.0412(7) Uani 1 1 d . . . . .
C9 C 0.0198(4) 0.9169(2) 0.2705(2) 0.0639(12) Uani 1 1 d . . . . .
C10 C -0.0760(5) 0.9780(2) 0.2602(2) 0.0648(11) Uani 1 1 d . . . . .
H10A H -0.0329 1.0199 0.2791 0.078 Uiso 1 1 calc R . . . .
H10B H -0.0974 0.9851 0.2099 0.078 Uiso 1 1 calc R . . . .
C11 C -0.2014(3) 0.96785(18) 0.29516(18) 0.0422(7) Uani 1 1 d . . . . .
C12 C -0.1704(4) 0.9491(2) 0.3736(2) 0.0536(9) Uani 1 1 d . . . . .
H12A H -0.1376 0.9903 0.3992 0.064 Uiso 1 1 calc R . . . .
H12B H -0.2506 0.9346 0.3934 0.064 Uiso 1 1 calc R . . . .
C13 C -0.2833(5) 0.9083(3) 0.2594(3) 0.0747(14) Uani 1 1 d . . . . .
H13A H -0.3627 0.9025 0.2826 0.112 Uiso 1 1 calc GR . . . .
H13B H -0.2334 0.8658 0.2629 0.112 Uiso 1 1 calc GR . . . .
H13C H -0.3051 0.9195 0.2105 0.112 Uiso 1 1 calc GR . . . .
C14 C -0.2870(5) 1.0325(3) 0.2904(3) 0.0763(15) Uani 1 1 d . . . . .
H14A H -0.3675 1.0232 0.3115 0.115 Uiso 1 1 calc GR . . . .
H14B H -0.3063 1.0450 0.2416 0.115 Uiso 1 1 calc GR . . . .
H14C H -0.2415 1.0702 0.3151 0.115 Uiso 1 1 calc GR . . . .
C15 C 0.1226(3) 0.82176(17) 0.35197(16) 0.0351(7) Uani 1 1 d . . . . .
H15 H 0.1559 0.8059 0.3077 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2354(3) 0.84907(16) 0.40059(17) 0.0359(7) Uani 1 1 d . . . . .
C17 C 0.3363(4) 0.88669(19) 0.3727(2) 0.0475(8) Uani 1 1 d . . . . .
H17 H 0.3375 0.8911 0.3239 0.057 Uiso 1 1 calc R . . . .
C18 C 0.4345(4) 0.9175(2) 0.4168(3) 0.0569(10) Uani 1 1 d . . . . .
H18 H 0.5016 0.9419 0.3975 0.068 Uiso 1 1 calc R . . . .
C19 C 0.4332(4) 0.9122(2) 0.4892(3) 0.0579(11) Uani 1 1 d . . . . .
H19 H 0.4985 0.9335 0.5188 0.069 Uiso 1 1 calc R . . . .
C20 C 0.3335(4) 0.87467(18) 0.5176(2) 0.0479(8) Uani 1 1 d . . . . .
H20 H 0.3324 0.8716 0.5665 0.057 Uiso 1 1 calc R . . . .
C21 C 0.2354(3) 0.84162(16) 0.47442(17) 0.0371(7) Uani 1 1 d . . . . .
C22 C 0.1308(3) 0.79904(15) 0.50634(15) 0.0321(6) Uani 1 1 d . . . . .
H22 H 0.0986 0.8265 0.5450 0.038 Uiso 1 1 calc R . . . .
C23 C 0.0144(3) 0.78617(15) 0.45175(15) 0.0310(6) Uani 1 1 d . . . . .
H23 H -0.0385 0.7485 0.4698 0.037 Uiso 1 1 calc R . . . .
C24 C -0.0418(4) 0.72883(19) 0.33945(18) 0.0435(8) Uani 1 1 d . . . . .
H24A H -0.0115 0.7238 0.2926 0.052 Uiso 1 1 calc R . . . .
H24B H -0.1194 0.7583 0.3355 0.052 Uiso 1 1 calc R . . . .
C25 C -0.0773(3) 0.65819(18) 0.36675(17) 0.0400(7) Uani 1 1 d . . . . .
C26 C 0.0186(4) 0.60650(19) 0.37624(19) 0.0456(8) Uani 1 1 d . . . . .
H26 H 0.1041 0.6158 0.3654 0.055 Uiso 1 1 calc R . . . .
C27 C -0.0125(5) 0.5415(2) 0.4016(2) 0.0588(10) Uani 1 1 d . . . . .
H27 H 0.0521 0.5072 0.4075 0.071 Uiso 1 1 calc R . . . .
C28 C -0.1377(5) 0.5271(2) 0.4183(2) 0.0653(12) Uani 1 1 d . . . . .
H28 H -0.1581 0.4832 0.4353 0.078 Uiso 1 1 calc R . . . .
C29 C -0.2331(4) 0.5778(3) 0.4101(2) 0.0655(12) Uani 1 1 d . . . . .
H29 H -0.3179 0.5682 0.4219 0.079 Uiso 1 1 calc R . . . .
C30 C -0.2032(4) 0.6433(2) 0.3841(2) 0.0519(9) Uani 1 1 d . . . . .
H30 H -0.2683 0.6772 0.3783 0.062 Uiso 1 1 calc R . . . .
C31 C 0.1754(3) 0.72555(16) 0.53763(16) 0.0343(6) Uani 1 1 d . . . . .
H31 H 0.1763 0.6922 0.4985 0.041 Uiso 1 1 calc R . . . .
C32 C 0.0745(3) 0.70161(17) 0.58682(17) 0.0404(7) Uani 1 1 d . . . . .
C33 C -0.0290(4) 0.65703(18) 0.5660(2) 0.0477(8) Uani 1 1 d . . . . .
H33 H -0.0321 0.6354 0.5219 0.057 Uiso 1 1 calc R . . . .
C34 C -0.1281(5) 0.6444(2) 0.6104(3) 0.0667(12) Uani 1 1 d . . . . .
H34 H -0.1976 0.6150 0.5958 0.080 Uiso 1 1 calc R . . . .
C35 C -0.1231(5) 0.6753(3) 0.6754(3) 0.0771(15) Uani 1 1 d . . . . .
H35 H -0.1906 0.6678 0.7046 0.092 Uiso 1 1 calc R . . . .
C36 C -0.0178(6) 0.7181(3) 0.6985(2) 0.0741(14) Uani 1 1 d . . . . .
H36 H -0.0153 0.7386 0.7431 0.089 Uiso 1 1 calc R . . . .
C37 C 0.0843(4) 0.7305(2) 0.65525(19) 0.0528(9) Uani 1 1 d . . . . .
C38 C 0.2066(5) 0.7647(2) 0.6789(2) 0.0630(11) Uani 1 1 d . . . . .
H38 H 0.2118 0.7926 0.7191 0.076 Uiso 1 1 calc R . . . .
C39 C 0.3126(4) 0.7558(2) 0.6423(2) 0.0574(10) Uani 1 1 d . . . . .
H39 H 0.3941 0.7705 0.6624 0.069 Uiso 1 1 calc R . . . .
C40 C 0.4262(5) 0.7119(3) 0.5409(4) 0.0616(15) Uani 0.773(8) 1 d . . P A 1
H40A H 0.4945 0.6965 0.5761 0.074 Uiso 0.773(8) 1 calc R . P A 1
H40B H 0.4554 0.7552 0.5208 0.074 Uiso 0.773(8) 1 calc R . P A 1
C40A C 0.3876(17) 0.6662(10) 0.5679(12) 0.0616(15) Uani 0.227(8) 1 d . . P A 2
H40C H 0.3477 0.6255 0.5878 0.074 Uiso 0.227(8) 1 calc R . P A 2
H40D H 0.4719 0.6739 0.5944 0.074 Uiso 0.227(8) 1 calc R . P A 2
C41 C 0.4103(7) 0.6582(4) 0.4835(4) 0.0518(11) Uani 0.793(7) 1 d . U P A 1
C41A C 0.410(2) 0.6517(11) 0.4928(8) 0.0518(11) Uani 0.207(7) 1 d . U P A 2
C42A C 0.380(2) 0.5872(9) 0.4619(12) 0.0610(15) Uani 0.207(7) 1 d G U P A 2
H42A H 0.3524 0.5506 0.4893 0.073 Uiso 0.207(7) 1 calc R . P A 2
C43A C 0.391(2) 0.5774(9) 0.3900(12) 0.0703(17) Uani 0.207(7) 1 d G U P A 2
H43A H 0.3715 0.5343 0.3693 0.084 Uiso 0.207(7) 1 calc R . P A 2
C44A C 0.433(2) 0.6322(12) 0.3490(9) 0.0774(18) Uani 0.207(7) 1 d G U P A 2
H44A H 0.4403 0.6256 0.3009 0.093 Uiso 0.207(7) 1 calc R . P A 2
C45A C 0.4623(18) 0.6967(9) 0.3800(9) 0.082(2) Uani 0.207(7) 1 d G U P A 2
H45A H 0.4899 0.7333 0.3525 0.098 Uiso 0.207(7) 1 calc R . P A 2
C46A C 0.4509(19) 0.7064(8) 0.4519(10) 0.0700(17) Uani 0.207(7) 1 d G U P A 2
H46A H 0.4708 0.7496 0.4726 0.084 Uiso 0.207(7) 1 calc R . P A 2
C42 C 0.3903(6) 0.5886(3) 0.5000(4) 0.0610(15) Uani 0.793(7) 1 d . U P A 1
H42 H 0.3877 0.5749 0.5470 0.073 Uiso 0.793(7) 1 calc R . P A 1
C43 C 0.3741(6) 0.5399(3) 0.4459(4) 0.0703(17) Uani 0.793(7) 1 d . U P A 1
H43 H 0.3596 0.4934 0.4574 0.084 Uiso 0.793(7) 1 calc R . P A 1
C44 C 0.3788(7) 0.5575(4) 0.3767(4) 0.0774(18) Uani 0.793(7) 1 d . U P A 1
H44 H 0.3681 0.5238 0.3414 0.093 Uiso 0.793(7) 1 calc R . P A 1
C45 C 0.3995(7) 0.6255(5) 0.3604(4) 0.082(2) Uani 0.793(7) 1 d . U P A 1
H45 H 0.4034 0.6383 0.3133 0.098 Uiso 0.793(7) 1 calc R . P A 1
C46 C 0.4150(6) 0.6765(3) 0.4133(4) 0.0700(17) Uani 0.793(7) 1 d . U P A 1
H46 H 0.4285 0.7228 0.4011 0.084 Uiso 0.793(7) 1 calc R . P A 1
N1 N -0.0722(3) 0.84935(14) 0.44203(14) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.0611(2) 0.76250(13) 0.38629(13) 0.0329(5) Uani 1 1 d . . . . .
N3 N 0.3051(3) 0.72575(16) 0.57641(16) 0.0450(7) Uani 1 1 d . . . . .
O1 O 0.0948(4) 0.9028(2) 0.22473(19) 0.0924(14) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0830(4) 0.1458(6) 0.0506(3) 0.0005(3) 0.0310(3) 0.0306(4)
C1 0.0403(17) 0.0482(19) 0.049(2) 0.0044(16) 0.0164(15) -0.0019(15)
C2 0.048(2) 0.064(2) 0.051(2) 0.0167(18) 0.0199(17) 0.0016(18)
C3 0.0405(18) 0.081(3) 0.0336(17) 0.0030(17) 0.0100(14) 0.0158(18)
C4 0.052(2) 0.061(2) 0.054(2) -0.0123(19) 0.0091(18) 0.0063(18)
C5 0.0427(18) 0.0479(19) 0.056(2) 0.0026(17) 0.0138(16) -0.0018(15)
C6 0.0300(14) 0.0460(17) 0.0312(15) 0.0059(13) 0.0069(12) 0.0049(13)
C7 0.0377(16) 0.0459(17) 0.0383(17) 0.0121(14) 0.0086(14) 0.0068(14)
C8 0.0367(16) 0.0485(18) 0.0393(17) 0.0138(14) 0.0083(14) 0.0074(14)
C9 0.056(2) 0.084(3) 0.056(2) 0.034(2) 0.025(2) 0.023(2)
C10 0.071(3) 0.069(3) 0.055(2) 0.022(2) 0.009(2) 0.010(2)
C11 0.0421(17) 0.0451(18) 0.0389(17) 0.0065(14) -0.0008(14) 0.0092(15)
C12 0.052(2) 0.059(2) 0.050(2) 0.0152(18) 0.0110(17) 0.0158(18)
C13 0.072(3) 0.082(3) 0.068(3) -0.002(2) -0.014(2) 0.002(2)
C14 0.086(3) 0.081(3) 0.064(3) 0.031(2) 0.017(2) 0.038(3)
C15 0.0345(15) 0.0427(16) 0.0293(15) 0.0035(12) 0.0092(12) 0.0047(13)
C16 0.0351(15) 0.0342(15) 0.0394(16) 0.0031(13) 0.0084(13) 0.0043(12)
C17 0.0409(18) 0.0505(19) 0.053(2) 0.0070(16) 0.0162(16) 0.0026(15)
C18 0.0417(19) 0.051(2) 0.079(3) 0.0101(19) 0.0113(19) -0.0088(16)
C19 0.045(2) 0.050(2) 0.076(3) 0.0041(19) -0.012(2) -0.0112(17)
C20 0.051(2) 0.0413(18) 0.049(2) 0.0037(15) -0.0082(16) -0.0044(15)
C21 0.0405(17) 0.0334(15) 0.0375(16) 0.0019(13) 0.0037(13) 0.0014(13)
C22 0.0358(15) 0.0346(15) 0.0259(14) 0.0004(12) 0.0029(12) 0.0008(12)
C23 0.0311(14) 0.0343(14) 0.0277(14) 0.0059(11) 0.0042(11) 0.0034(12)
C24 0.0486(19) 0.0499(19) 0.0306(15) 0.0007(14) -0.0048(14) -0.0024(15)
C25 0.0431(17) 0.0468(18) 0.0290(15) -0.0062(13) -0.0025(13) -0.0060(14)
C26 0.0418(18) 0.054(2) 0.0412(18) -0.0076(15) 0.0038(15) -0.0021(15)
C27 0.068(3) 0.046(2) 0.061(2) -0.0016(18) -0.002(2) 0.0001(19)
C28 0.077(3) 0.056(2) 0.061(3) 0.006(2) -0.006(2) -0.025(2)
C29 0.053(2) 0.086(3) 0.057(3) 0.005(2) 0.0027(19) -0.028(2)
C30 0.0403(18) 0.068(2) 0.046(2) -0.0028(18) -0.0027(15) -0.0065(17)
C31 0.0361(15) 0.0357(15) 0.0302(15) -0.0005(12) -0.0026(12) 0.0014(12)
C32 0.0475(18) 0.0404(16) 0.0334(16) 0.0100(13) 0.0034(14) 0.0061(14)
C33 0.052(2) 0.0425(18) 0.049(2) 0.0111(15) 0.0041(16) -0.0017(15)
C34 0.061(3) 0.064(2) 0.076(3) 0.027(2) 0.013(2) -0.007(2)
C35 0.074(3) 0.094(4) 0.066(3) 0.037(3) 0.028(3) 0.007(3)
C36 0.099(4) 0.087(3) 0.039(2) 0.016(2) 0.018(2) 0.017(3)
C37 0.072(3) 0.055(2) 0.0318(17) 0.0063(15) 0.0064(17) 0.0080(19)
C38 0.097(3) 0.060(2) 0.0298(17) -0.0039(16) -0.007(2) 0.003(2)
C39 0.068(3) 0.057(2) 0.043(2) 0.0055(17) -0.0255(19) -0.0060(19)
C40 0.038(2) 0.051(3) 0.095(4) -0.002(3) -0.002(2) 0.000(2)
C40A 0.038(2) 0.051(3) 0.095(4) -0.002(3) -0.002(2) 0.000(2)
C41 0.0323(16) 0.051(2) 0.073(3) 0.004(2) 0.0082(19) 0.0088(16)
C41A 0.0323(16) 0.051(2) 0.073(3) 0.004(2) 0.0082(19) 0.0088(16)
C42A 0.057(3) 0.053(2) 0.073(4) 0.000(3) 0.012(3) 0.001(2)
C43A 0.059(3) 0.059(3) 0.095(4) -0.012(3) 0.015(3) 0.001(2)
C44A 0.058(3) 0.087(4) 0.088(4) -0.027(3) 0.010(3) 0.006(3)
C45A 0.062(4) 0.113(5) 0.071(4) 0.005(4) 0.017(3) 0.014(3)
C46A 0.054(3) 0.071(3) 0.086(4) 0.016(3) 0.015(3) 0.006(3)
C42 0.057(3) 0.053(2) 0.073(4) 0.000(3) 0.012(3) 0.001(2)
C43 0.059(3) 0.059(3) 0.095(4) -0.012(3) 0.015(3) 0.001(2)
C44 0.058(3) 0.087(4) 0.088(4) -0.027(3) 0.010(3) 0.006(3)
C45 0.062(4) 0.113(5) 0.071(4) 0.005(4) 0.017(3) 0.014(3)
C46 0.054(3) 0.071(3) 0.086(4) 0.016(3) 0.015(3) 0.006(3)
N1 0.0346(13) 0.0416(14) 0.0347(14) 0.0092(11) 0.0106(11) 0.0069(11)
N2 0.0342(13) 0.0386(13) 0.0258(12) 0.0014(10) 0.0021(10) 0.0008(10)
N3 0.0425(15) 0.0489(16) 0.0416(15) 0.0022(13) -0.0084(12) 0.0019(13)
O1 0.089(2) 0.130(3) 0.065(2) 0.056(2) 0.0492(19) 0.055(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.902(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(5) . ?
C1 C6 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(6) . ?
C3 C4 1.354(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(5) . ?
C6 N1 1.423(4) . ?
C7 C8 1.372(5) . ?
C7 C12 1.521(5) . ?
C7 N1 1.363(4) . ?
C8 C9 1.436(5) . ?
C8 C15 1.515(4) . ?
C9 C10 1.527(6) . ?
C9 O1 1.234(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(6) . ?
C11 C12 1.537(5) . ?
C11 C13 1.537(6) . ?
C11 C14 1.513(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.507(5) . ?
C15 N2 1.474(4) . ?
C16 C17 1.396(5) . ?
C16 C21 1.406(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(5) . ?
C21 C22 1.510(4) . ?
C22 H22 0.9800 . ?
C22 C23 1.529(4) . ?
C22 C31 1.580(4) . ?
C23 H23 0.9800 . ?
C23 N1 1.501(4) . ?
C23 N2 1.439(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.504(5) . ?
C24 N2 1.467(4) . ?
C25 C26 1.394(5) . ?
C25 C30 1.383(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.371(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.391(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9800 . ?
C31 C32 1.517(5) . ?
C31 N3 1.459(4) . ?
C32 C33 1.390(5) . ?
C32 C37 1.406(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.390(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.364(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.392(8) . ?
C36 H36 0.9300 . ?
C36 C37 1.399(6) . ?
C37 C38 1.446(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.344(7) . ?
C39 H39 0.9300 . ?
C39 N3 1.371(5) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.496(9) . ?
C40 N3 1.481(6) . ?
C40A H40C 0.9700 . ?
C40A H40D 0.9700 . ?
C40A C41A 1.49(3) . ?
C40A N3 1.436(18) . ?
C41 C42 1.387(8) . ?
C41 C46 1.380(10) . ?
C41A C42A 1.3900 . ?
C41A C46A 1.3900 . ?
C42A H42A 0.9300 . ?
C42A C43A 1.3900 . ?
C43A H43A 0.9300 . ?
C43A C44A 1.3900 . ?
C44A H44A 0.9300 . ?
C44A C45A 1.3900 . ?
C45A H45A 0.9300 . ?
C45A C46A 1.3900 . ?
C46A H46A 0.9300 . ?
C42 H42 0.9300 . ?
C42 C43 1.387(9) . ?
C43 H43 0.9300 . ?
C43 C44 1.359(11) . ?
C44 H44 0.9300 . ?
C44 C45 1.359(11) . ?
C45 H45 0.9300 . ?
C45 C46 1.400(11) . ?
C46 H46 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 Br1 118.7(3) . . ?
C4 C3 Br1 119.5(3) . . ?
C4 C3 C2 121.8(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 N1 120.1(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 N1 121.5(3) . . ?
C8 C7 C12 122.0(3) . . ?
N1 C7 C8 120.0(3) . . ?
N1 C7 C12 118.0(3) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 C15 118.4(3) . . ?
C9 C8 C15 120.0(3) . . ?
C8 C9 C10 117.4(3) . . ?
O1 C9 C8 122.1(4) . . ?
O1 C9 C10 120.5(4) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.9(3) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 C12 110.0(3) . . ?
C10 C11 C13 110.7(4) . . ?
C10 C11 C14 112.1(3) . . ?
C12 C11 C13 108.3(3) . . ?
C14 C11 C12 108.7(3) . . ?
C14 C11 C13 106.9(4) . . ?
C7 C12 C11 112.2(3) . . ?
C7 C12 H12A 109.2 . . ?
C7 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15 109.3 . . ?
C16 C15 C8 110.0(3) . . ?
C16 C15 H15 109.3 . . ?
N2 C15 C8 109.7(3) . . ?
N2 C15 H15 109.3 . . ?
N2 C15 C16 109.2(2) . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 C21 119.4(3) . . ?
C21 C16 C15 120.6(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(4) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C22 120.8(3) . . ?
C20 C21 C16 118.6(3) . . ?
C20 C21 C22 120.6(3) . . ?
C21 C22 H22 107.6 . . ?
C21 C22 C23 110.6(2) . . ?
C21 C22 C31 116.1(3) . . ?
C23 C22 H22 107.6 . . ?
C23 C22 C31 107.1(2) . . ?
C31 C22 H22 107.6 . . ?
C22 C23 H23 107.5 . . ?
N1 C23 C22 111.7(2) . . ?
N1 C23 H23 107.5 . . ?
N2 C23 C22 109.8(2) . . ?
N2 C23 H23 107.5 . . ?
N2 C23 N1 112.5(2) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
N2 C24 H24A 109.3 . . ?
N2 C24 H24B 109.3 . . ?
N2 C24 C25 111.6(3) . . ?
C26 C25 C24 119.8(3) . . ?
C30 C25 C24 121.5(3) . . ?
C30 C25 C26 118.7(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.9(4) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(4) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 120.4(4) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C22 C31 H31 108.5 . . ?
C32 C31 C22 108.1(2) . . ?
C32 C31 H31 108.5 . . ?
N3 C31 C22 114.1(3) . . ?
N3 C31 H31 108.5 . . ?
N3 C31 C32 109.0(3) . . ?
C33 C32 C31 123.4(3) . . ?
C33 C32 C37 119.9(3) . . ?
C37 C32 C31 116.6(3) . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.5(4) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(5) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.5(4) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 119.7 . . ?
C35 C36 C37 120.7(4) . . ?
C37 C36 H36 119.7 . . ?
C32 C37 C38 117.2(4) . . ?
C36 C37 C32 118.3(4) . . ?
C36 C37 C38 124.1(4) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 118.7 . . ?
C38 C39 N3 122.5(4) . . ?
N3 C39 H39 118.7 . . ?
H40A C40 H40B 107.6 . . ?
C41 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
N3 C40 H40A 108.7 . . ?
N3 C40 H40B 108.7 . . ?
N3 C40 C41 114.2(5) . . ?
H40C C40A H40D 107.8 . . ?
C41A C40A H40C 108.9 . . ?
C41A C40A H40D 108.9 . . ?
N3 C40A H40C 108.9 . . ?
N3 C40A H40D 108.9 . . ?
N3 C40A C41A 113.2(17) . . ?
C42 C41 C40 120.3(7) . . ?
C46 C41 C40 121.0(6) . . ?
C46 C41 C42 118.6(7) . . ?
C42A C41A C40A 121.6(14) . . ?
C42A C41A C46A 120.0 . . ?
C46A C41A C40A 118.1(14) . . ?
C41A C42A H42A 120.0 . . ?
C43A C42A C41A 120.0 . . ?
C43A C42A H42A 120.0 . . ?
C42A C43A H43A 120.0 . . ?
C42A C43A C44A 120.0 . . ?
C44A C43A H43A 120.0 . . ?
C43A C44A H44A 120.0 . . ?
C45A C44A C43A 120.0 . . ?
C45A C44A H44A 120.0 . . ?
C44A C45A H45A 120.0 . . ?
C46A C45A C44A 120.0 . . ?
C46A C45A H45A 120.0 . . ?
C41A C46A H46A 120.0 . . ?
C45A C46A C41A 120.0 . . ?
C45A C46A H46A 120.0 . . ?
C41 C42 H42 120.3 . . ?
C43 C42 C41 119.3(7) . . ?
C43 C42 H42 120.3 . . ?
C42 C43 H43 118.8 . . ?
C44 C43 C42 122.3(6) . . ?
C44 C43 H43 118.8 . . ?
C43 C44 H44 120.8 . . ?
C43 C44 C45 118.5(7) . . ?
C45 C44 H44 120.8 . . ?
C44 C45 H45 119.5 . . ?
C44 C45 C46 121.0(7) . . ?
C46 C45 H45 119.5 . . ?
C41 C46 C45 120.2(6) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C6 N1 C23 114.6(2) . . ?
C7 N1 C6 123.9(3) . . ?
C7 N1 C23 121.2(3) . . ?
C23 N2 C15 108.8(2) . . ?
C23 N2 C24 112.8(3) . . ?
C24 N2 C15 112.4(2) . . ?
C31 N3 C40 121.8(3) . . ?
C39 N3 C31 116.0(3) . . ?
C39 N3 C40 120.3(4) . . ?
C39 N3 C40A 116.6(9) . . ?
C40A N3 C31 117.2(8) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 178.9(3) . . . . ?
C1 C2 C3 Br1 179.3(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C6 N1 C7 133.2(4) . . . . ?
C1 C6 N1 C23 -52.6(4) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 N1 174.0(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 2.2(6) . . . . ?
C4 C5 C6 C1 -1.6(6) . . . . ?
C4 C5 C6 N1 -175.7(3) . . . . ?
C5 C6 N1 C7 -52.7(5) . . . . ?
C5 C6 N1 C23 121.4(3) . . . . ?
C6 C1 C2 C3 1.4(6) . . . . ?
C7 C8 C9 C10 7.8(7) . . . . ?
C7 C8 C9 O1 -174.4(5) . . . . ?
C7 C8 C15 C16 -83.0(4) . . . . ?
C7 C8 C15 N2 37.3(4) . . . . ?
C8 C7 C12 C11 26.1(5) . . . . ?
C8 C7 N1 C6 168.3(3) . . . . ?
C8 C7 N1 C23 -5.5(5) . . . . ?
C8 C9 C10 C11 -32.9(6) . . . . ?
C8 C15 C16 C17 -82.3(4) . . . . ?
C8 C15 C16 C21 92.9(3) . . . . ?
C8 C15 N2 C23 -61.0(3) . . . . ?
C8 C15 N2 C24 64.7(3) . . . . ?
C9 C8 C15 C16 99.6(4) . . . . ?
C9 C8 C15 N2 -140.1(4) . . . . ?
C9 C10 C11 C12 52.8(5) . . . . ?
C9 C10 C11 C13 -66.8(5) . . . . ?
C9 C10 C11 C14 173.9(4) . . . . ?
C10 C11 C12 C7 -48.7(5) . . . . ?
C12 C7 C8 C9 -5.1(6) . . . . ?
C12 C7 C8 C15 177.6(3) . . . . ?
C12 C7 N1 C6 -13.1(5) . . . . ?
C12 C7 N1 C23 173.1(3) . . . . ?
C13 C11 C12 C7 72.4(4) . . . . ?
C14 C11 C12 C7 -171.8(4) . . . . ?
C15 C8 C9 C10 -174.8(4) . . . . ?
C15 C8 C9 O1 3.0(8) . . . . ?
C15 C16 C17 C18 174.2(3) . . . . ?
C15 C16 C21 C20 -172.6(3) . . . . ?
C15 C16 C21 C22 7.1(4) . . . . ?
C16 C15 N2 C23 59.7(3) . . . . ?
C16 C15 N2 C24 -174.6(3) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C16 C21 C22 C23 -16.1(4) . . . . ?
C16 C21 C22 C31 106.1(3) . . . . ?
C17 C16 C21 C20 2.7(5) . . . . ?
C17 C16 C21 C22 -177.7(3) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C19 C20 C21 C16 -2.5(5) . . . . ?
C19 C20 C21 C22 177.8(3) . . . . ?
C20 C21 C22 C23 163.5(3) . . . . ?
C20 C21 C22 C31 -74.2(4) . . . . ?
C21 C16 C17 C18 -1.1(5) . . . . ?
C21 C22 C23 N1 -77.7(3) . . . . ?
C21 C22 C23 N2 47.8(3) . . . . ?
C21 C22 C31 C32 162.1(3) . . . . ?
C21 C22 C31 N3 40.7(4) . . . . ?
C22 C23 N1 C6 -70.3(3) . . . . ?
C22 C23 N1 C7 104.0(3) . . . . ?
C22 C23 N2 C15 -72.3(3) . . . . ?
C22 C23 N2 C24 162.2(2) . . . . ?
C22 C31 C32 C33 95.9(4) . . . . ?
C22 C31 C32 C37 -80.0(3) . . . . ?
C22 C31 N3 C39 74.6(4) . . . . ?
C22 C31 N3 C40 -90.0(4) . . . . ?
C22 C31 N3 C40A -141.2(11) . . . . ?
C23 C22 C31 C32 -73.8(3) . . . . ?
C23 C22 C31 N3 164.8(3) . . . . ?
C24 C25 C26 C27 179.6(3) . . . . ?
C24 C25 C30 C29 -179.2(4) . . . . ?
C25 C24 N2 C15 164.4(3) . . . . ?
C25 C24 N2 C23 -72.2(4) . . . . ?
C25 C26 C27 C28 -0.5(6) . . . . ?
C26 C25 C30 C29 -0.3(5) . . . . ?
C26 C27 C28 C29 -0.2(7) . . . . ?
C27 C28 C29 C30 0.7(7) . . . . ?
C28 C29 C30 C25 -0.4(6) . . . . ?
C30 C25 C26 C27 0.8(5) . . . . ?
C31 C22 C23 N1 154.9(2) . . . . ?
C31 C22 C23 N2 -79.6(3) . . . . ?
C31 C32 C33 C34 -171.3(3) . . . . ?
C31 C32 C37 C36 170.5(3) . . . . ?
C31 C32 C37 C38 -16.1(5) . . . . ?
C32 C31 N3 C39 -46.3(4) . . . . ?
C32 C31 N3 C40 149.1(4) . . . . ?
C32 C31 N3 C40A 97.9(11) . . . . ?
C32 C33 C34 C35 -0.8(6) . . . . ?
C32 C37 C38 C39 -13.2(6) . . . . ?
C33 C32 C37 C36 -5.5(5) . . . . ?
C33 C32 C37 C38 167.8(3) . . . . ?
C33 C34 C35 C36 -1.6(7) . . . . ?
C34 C35 C36 C37 0.4(7) . . . . ?
C35 C36 C37 C32 3.2(7) . . . . ?
C35 C36 C37 C38 -169.7(4) . . . . ?
C36 C37 C38 C39 159.7(4) . . . . ?
C37 C32 C33 C34 4.4(5) . . . . ?
C37 C38 C39 N3 11.9(6) . . . . ?
C38 C39 N3 C31 20.2(5) . . . . ?
C38 C39 N3 C40 -175.0(4) . . . . ?
C38 C39 N3 C40A -124.2(10) . . . . ?
C40 C41 C42 C43 179.2(6) . . . . ?
C40 C41 C46 C45 -179.8(6) . . . . ?
C40A C41A C42A C43A 175(2) . . . . ?
C40A C41A C46A C45A -175(2) . . . . ?
C41 C40 N3 C31 -36.5(6) . . . . ?
C41 C40 N3 C39 159.6(5) . . . . ?
C41 C42 C43 C44 0.8(10) . . . . ?
C41A C40A N3 C31 55.8(17) . . . . ?
C41A C40A N3 C39 -160.2(12) . . . . ?
C41A C42A C43A C44A 0.0 . . . . ?
C42A C41A C46A C45A 0.0 . . . . ?
C42A C43A C44A C45A 0.0 . . . . ?
C43A C44A C45A C46A 0.0 . . . . ?
C44A C45A C46A C41A 0.0 . . . . ?
C46A C41A C42A C43A 0.0 . . . . ?
C42 C41 C46 C45 0.1(9) . . . . ?
C42 C43 C44 C45 -0.3(11) . . . . ?
C43 C44 C45 C46 -0.3(10) . . . . ?
C44 C45 C46 C41 0.4(10) . . . . ?
C46 C41 C42 C43 -0.7(9) . . . . ?
N1 C7 C8 C9 173.5(4) . . . . ?
N1 C7 C8 C15 -3.9(5) . . . . ?
N1 C7 C12 C11 -152.4(3) . . . . ?
N1 C23 N2 C15 52.7(3) . . . . ?
N1 C23 N2 C24 -72.7(3) . . . . ?
N2 C15 C16 C17 157.2(3) . . . . ?
N2 C15 C16 C21 -27.6(4) . . . . ?
N2 C23 N1 C6 165.7(3) . . . . ?
N2 C23 N1 C7 -20.1(4) . . . . ?
N2 C24 C25 C26 -59.6(4) . . . . ?
N2 C24 C25 C30 119.3(4) . . . . ?
N3 C31 C32 C33 -139.6(3) . . . . ?
N3 C31 C32 C37 44.4(4) . . . . ?
N3 C40 C41 C42 -69.0(8) . . . . ?
N3 C40 C41 C46 110.9(7) . . . . ?
N3 C40A C41A C42A -124.0(15) . . . . ?
N3 C40A C41A C46A 51(2) . . . . ?
O1 C9 C10 C11 149.3(5) . . . . ?
_iucr_refine_instructions_details
;
201810415.res created by SHELXL-2014/7
TITL CF solution in P21/n
CELL 1.54184 10.207758 19.151985 18.951385 90 94.8036 90
ZERR 4 0.000263 0.000509 0.000437 0 0.0024 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Br N O
UNIT 184 168 4 12 4
ISOR 0.01 0.02 C45A C44A C44 C45 C46 C43 C43A C42A C42 C41A C41 C46A
EADP C40 C40A
EADP C41 C41A
EADP C46 C46A
EADP C45 C45A
EADP C44 C44A
EADP C43 C43A
EADP C42 C42A
L.S. 4 0 0
PLAN 20
SIZE 0.1 0.14 0.18
MPLA C1 C2 C3 C4 C5 C6
MPLA C16 C17 C18 C19 C20 C21
MPLA C25 C26 C27 C28 C29 C30
MPLA C32 C33 C34 C35 C36 C37
MPLA C41 C42 C43 C44 C45 C46
BOND $h
conf
fmap 2
acta
REM
REM
REM
WGHT 0.112300 2.590600
FVAR 3.99491 0.77255 0.79264
BR1 3 -0.360094 0.906709 0.704012 11.00000 0.08302 0.14582 =
0.05055 0.00046 0.03099 0.03061
C1 1 -0.222698 0.813952 0.528179 11.00000 0.04026 0.04816 =
0.04945 0.00438 0.01635 -0.00191
AFIX 43
H1 2 -0.232754 0.770895 0.505688 11.00000 -1.20000
AFIX 0
C2 1 -0.284787 0.826616 0.589033 11.00000 0.04801 0.06386 =
0.05064 0.01671 0.01994 0.00159
AFIX 43
H2 2 -0.334857 0.791877 0.608069 11.00000 -1.20000
AFIX 0
C3 1 -0.272126 0.890384 0.620964 11.00000 0.04047 0.08093 =
0.03362 0.00301 0.00999 0.01580
C4 1 -0.198769 0.941887 0.595178 11.00000 0.05238 0.06131 =
0.05440 -0.01226 0.00907 0.00631
AFIX 43
H4 2 -0.192197 0.985329 0.617115 11.00000 -1.20000
AFIX 0
C5 1 -0.133633 0.928325 0.535258 11.00000 0.04268 0.04795 =
0.05558 0.00263 0.01382 -0.00182
AFIX 43
H5 2 -0.080523 0.962746 0.518019 11.00000 -1.20000
AFIX 0
C6 1 -0.145815 0.864889 0.500596 11.00000 0.02997 0.04599 =
0.03123 0.00591 0.00693 0.00486
C7 1 -0.069033 0.891014 0.383857 11.00000 0.03767 0.04590 =
0.03830 0.01206 0.00859 0.00679
C8 1 0.021912 0.878911 0.335944 11.00000 0.03668 0.04847 =
0.03931 0.01384 0.00834 0.00741
C9 1 0.019826 0.916893 0.270507 11.00000 0.05571 0.08356 =
0.05581 0.03371 0.02537 0.02293
C10 1 -0.076042 0.977977 0.260249 11.00000 0.07124 0.06895 =
0.05498 0.02244 0.00912 0.00954
AFIX 23
H10A 2 -0.032937 1.019940 0.279108 11.00000 -1.20000
H10B 2 -0.097389 0.985103 0.209925 11.00000 -1.20000
AFIX 0
C11 1 -0.201446 0.967848 0.295163 11.00000 0.04206 0.04507 =
0.03889 0.00648 -0.00078 0.00921
C12 1 -0.170364 0.949116 0.373620 11.00000 0.05207 0.05946 =
0.05032 0.01515 0.01100 0.01582
AFIX 23
H12A 2 -0.137588 0.990270 0.399193 11.00000 -1.20000
H12B 2 -0.250636 0.934590 0.393407 11.00000 -1.20000
AFIX 0
C13 1 -0.283346 0.908308 0.259425 11.00000 0.07165 0.08151 =
0.06776 -0.00200 -0.01371 0.00157
AFIX 137
H13A 2 -0.362683 0.902450 0.282635 11.00000 -1.50000
H13B 2 -0.233414 0.865789 0.262854 11.00000 -1.50000
H13C 2 -0.305087 0.919503 0.210466 11.00000 -1.50000
AFIX 0
C14 1 -0.287004 1.032470 0.290399 11.00000 0.08570 0.08075 =
0.06439 0.03098 0.01714 0.03780
AFIX 137
H14A 2 -0.367521 1.023166 0.311464 11.00000 -1.50000
H14B 2 -0.306309 1.045030 0.241595 11.00000 -1.50000
H14C 2 -0.241464 1.070216 0.315114 11.00000 -1.50000
AFIX 0
C15 1 0.122632 0.821761 0.351968 11.00000 0.03453 0.04272 =
0.02927 0.00346 0.00920 0.00465
AFIX 13
H15 2 0.155863 0.805895 0.307654 11.00000 -1.20000
AFIX 0
C16 1 0.235430 0.849075 0.400590 11.00000 0.03506 0.03418 =
0.03943 0.00313 0.00836 0.00429
C17 1 0.336342 0.886687 0.372714 11.00000 0.04089 0.05051 =
0.05327 0.00702 0.01621 0.00255
AFIX 43
H17 2 0.337523 0.891055 0.323897 11.00000 -1.20000
AFIX 0
C18 1 0.434463 0.917491 0.416815 11.00000 0.04171 0.05107 =
0.07886 0.01014 0.01133 -0.00884
AFIX 43
H18 2 0.501649 0.941909 0.397512 11.00000 -1.20000
AFIX 0
C19 1 0.433193 0.912192 0.489172 11.00000 0.04466 0.05036 =
0.07578 0.00411 -0.01193 -0.01121
AFIX 43
H19 2 0.498504 0.933539 0.518838 11.00000 -1.20000
AFIX 0
C20 1 0.333499 0.874673 0.517585 11.00000 0.05141 0.04131 =
0.04877 0.00375 -0.00819 -0.00440
AFIX 43
H20 2 0.332386 0.871605 0.566506 11.00000 -1.20000
AFIX 0
C21 1 0.235373 0.841622 0.474417 11.00000 0.04050 0.03341 =
0.03749 0.00190 0.00369 0.00135
C22 1 0.130757 0.799035 0.506342 11.00000 0.03578 0.03464 =
0.02587 0.00038 0.00292 0.00075
AFIX 13
H22 2 0.098585 0.826492 0.544966 11.00000 -1.20000
AFIX 0
C23 1 0.014362 0.786172 0.451747 11.00000 0.03107 0.03433 =
0.02774 0.00589 0.00418 0.00344
AFIX 13
H23 2 -0.038469 0.748478 0.469831 11.00000 -1.20000
AFIX 0
C24 1 -0.041814 0.728835 0.339450 11.00000 0.04859 0.04990 =
0.03056 0.00071 -0.00478 -0.00244
AFIX 23
H24A 2 -0.011479 0.723809 0.292560 11.00000 -1.20000
H24B 2 -0.119430 0.758257 0.335500 11.00000 -1.20000
AFIX 0
C25 1 -0.077302 0.658189 0.366750 11.00000 0.04310 0.04679 =
0.02904 -0.00621 -0.00253 -0.00598
C26 1 0.018638 0.606497 0.376238 11.00000 0.04179 0.05397 =
0.04116 -0.00763 0.00384 -0.00214
AFIX 43
H26 2 0.104091 0.615819 0.365404 11.00000 -1.20000
AFIX 0
C27 1 -0.012464 0.541485 0.401644 11.00000 0.06790 0.04628 =
0.06100 -0.00164 -0.00205 0.00012
AFIX 43
H27 2 0.052077 0.507211 0.407457 11.00000 -1.20000
AFIX 0
C28 1 -0.137720 0.527116 0.418348 11.00000 0.07681 0.05573 =
0.06142 0.00564 -0.00646 -0.02470
AFIX 43
H28 2 -0.158095 0.483189 0.435257 11.00000 -1.20000
AFIX 0
C29 1 -0.233145 0.577765 0.410056 11.00000 0.05256 0.08633 =
0.05736 0.00487 0.00269 -0.02802
AFIX 43
H29 2 -0.317936 0.568223 0.421850 11.00000 -1.20000
AFIX 0
C30 1 -0.203205 0.643268 0.384062 11.00000 0.04034 0.06793 =
0.04641 -0.00284 -0.00265 -0.00647
AFIX 43
H30 2 -0.268305 0.677248 0.378290 11.00000 -1.20000
AFIX 0
C31 1 0.175419 0.725547 0.537634 11.00000 0.03614 0.03575 =
0.03020 -0.00050 -0.00256 0.00142
AFIX 13
H31 2 0.176292 0.692164 0.498486 11.00000 -1.20000
AFIX 0
C32 1 0.074455 0.701612 0.586820 11.00000 0.04747 0.04037 =
0.03336 0.00997 0.00342 0.00609
C33 1 -0.029035 0.657026 0.565951 11.00000 0.05204 0.04245 =
0.04859 0.01110 0.00415 -0.00172
AFIX 43
H33 2 -0.032060 0.635435 0.521890 11.00000 -1.20000
AFIX 0
C34 1 -0.128076 0.644440 0.610416 11.00000 0.06126 0.06360 =
0.07629 0.02737 0.01269 -0.00703
AFIX 43
H34 2 -0.197612 0.615010 0.595849 11.00000 -1.20000
AFIX 0
C35 1 -0.123090 0.675331 0.675444 11.00000 0.07440 0.09446 =
0.06610 0.03684 0.02825 0.00658
AFIX 43
H35 2 -0.190568 0.667767 0.704619 11.00000 -1.20000
AFIX 0
C36 1 -0.017766 0.718096 0.698482 11.00000 0.09867 0.08723 =
0.03851 0.01558 0.01782 0.01704
AFIX 43
H36 2 -0.015268 0.738616 0.743051 11.00000 -1.20000
AFIX 0
C37 1 0.084338 0.730502 0.655245 11.00000 0.07214 0.05483 =
0.03181 0.00628 0.00637 0.00795
C38 1 0.206559 0.764677 0.678889 11.00000 0.09722 0.05994 =
0.02981 -0.00392 -0.00705 0.00265
AFIX 43
H38 2 0.211772 0.792635 0.719149 11.00000 -1.20000
AFIX 0
C39 1 0.312568 0.755757 0.642284 11.00000 0.06756 0.05673 =
0.04289 0.00546 -0.02551 -0.00604
AFIX 43
H39 2 0.394097 0.770509 0.662425 11.00000 -1.20000
AFIX 0
PART 1
C40 1 0.426220 0.711873 0.540876 21.00000 0.03778 0.05076 =
0.09481 -0.00227 -0.00232 0.00034
AFIX 23
H40A 2 0.494537 0.696544 0.576133 21.00000 -1.20000
H40B 2 0.455394 0.755185 0.520775 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C40A 1 0.387642 0.666179 0.567898 -21.00000 0.03778 0.05076 =
0.09481 -0.00227 -0.00232 0.00034
AFIX 23
H40C 2 0.347668 0.625503 0.587767 -21.00000 -1.20000
H40D 2 0.471909 0.673874 0.594361 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C41 1 0.410345 0.658174 0.483491 31.00000 0.03232 0.05078 =
0.07298 0.00375 0.00817 0.00877
PART 0
PART 2
AFIX 66
C41A 1 0.409700 0.651723 0.492810 -31.00000 0.03232 0.05078 =
0.07298 0.00375 0.00817 0.00877
C42A 1 0.379978 0.587223 0.461869 -31.00000 0.05731 0.05329 =
0.07337 -0.00040 0.01163 0.00146
AFIX 43
H42A 2 0.352433 0.550611 0.489273 -31.00000 -1.20000
AFIX 65
C43A 1 0.391425 0.577443 0.389969 -31.00000 0.05909 0.05878 =
0.09451 -0.01220 0.01452 0.00134
AFIX 43
H43A 2 0.371538 0.534287 0.369268 -31.00000 -1.20000
AFIX 65
C44A 1 0.432594 0.632163 0.349010 -31.00000 0.05817 0.08663 =
0.08799 -0.02679 0.01000 0.00590
AFIX 43
H44A 2 0.440252 0.625619 0.300904 -31.00000 -1.20000
AFIX 65
C45A 1 0.462316 0.696664 0.379950 -31.00000 0.06237 0.11303 =
0.07112 0.00456 0.01686 0.01379
AFIX 43
H45A 2 0.489861 0.733275 0.352546 -31.00000 -1.20000
AFIX 65
C46A 1 0.450870 0.706445 0.451850 -31.00000 0.05376 0.07128 =
0.08643 0.01559 0.01483 0.00629
AFIX 43
H46A 2 0.470756 0.749600 0.472551 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C42 1 0.390297 0.588629 0.500045 31.00000 0.05731 0.05329 =
0.07337 -0.00040 0.01163 0.00146
AFIX 43
H42 2 0.387716 0.574859 0.546967 31.00000 -1.20000
AFIX 0
C43 1 0.374143 0.539850 0.445928 31.00000 0.05909 0.05878 =
0.09451 -0.01220 0.01452 0.00134
AFIX 43
H43 2 0.359607 0.493436 0.457403 31.00000 -1.20000
AFIX 0
C44 1 0.378806 0.557477 0.376742 31.00000 0.05817 0.08663 =
0.08799 -0.02679 0.01000 0.00590
AFIX 43
H44 2 0.368105 0.523788 0.341388 31.00000 -1.20000
AFIX 0
C45 1 0.399466 0.625470 0.360376 31.00000 0.06237 0.11303 =
0.07112 0.00456 0.01686 0.01379
AFIX 43
H45 2 0.403352 0.638300 0.313269 31.00000 -1.20000
AFIX 0
C46 1 0.414984 0.676480 0.413300 31.00000 0.05376 0.07128 =
0.08643 0.01559 0.01483 0.00629
AFIX 43
H46 2 0.428454 0.722819 0.401146 31.00000 -1.20000
AFIX 0
PART 0
N1 4 -0.072209 0.849353 0.442026 11.00000 0.03462 0.04160 =
0.03469 0.00922 0.01059 0.00688
N2 4 0.061131 0.762496 0.386287 11.00000 0.03420 0.03861 =
0.02578 0.00143 0.00207 0.00077
N3 4 0.305081 0.725753 0.576414 11.00000 0.04250 0.04889 =
0.04158 0.00218 -0.00843 0.00192
O1 5 0.094773 0.902757 0.224728 11.00000 0.08878 0.13029 =
0.06544 0.05559 0.04918 0.05488
HKLF 4
REM CF solution in P21/n
REM R1 = 0.0701 for 5036 Fo > 4sig(Fo) and 0.0870 for all 6586 data
REM 473 parameters refined using 72 restraints
END
WGHT 0.1123 2.5907
REM Highest difference peak 1.014, deepest hole -0.541, 1-sigma level 0.077
Q1 1 -0.1357 0.9301 0.2319 11.00000 0.05 1.01
Q2 1 -0.2861 0.9315 0.6978 11.00000 0.05 0.95
Q3 1 -0.1014 1.0303 0.3157 11.00000 0.05 0.89
Q4 1 -0.2204 0.9123 0.3484 11.00000 0.05 0.74
Q5 1 -0.3412 0.9863 0.2622 11.00000 0.05 0.69
Q6 1 -0.0247 0.8834 0.2450 11.00000 0.05 0.50
Q7 1 -0.2978 0.8663 0.7122 11.00000 0.05 0.36
Q8 1 -0.1013 0.8622 0.3569 11.00000 0.05 0.33
Q9 1 0.2353 0.8467 0.4365 11.00000 0.05 0.31
Q10 1 0.0399 0.7774 0.4198 11.00000 0.05 0.28
Q11 1 -0.4537 0.9438 0.6991 11.00000 0.05 0.27
Q12 1 0.3046 0.8896 0.3786 11.00000 0.05 0.27
Q13 1 -0.1429 0.6628 0.3867 11.00000 0.05 0.26
Q14 1 0.0762 0.7918 0.4814 11.00000 0.05 0.26
Q15 1 0.1624 0.8285 0.4883 11.00000 0.05 0.26
Q16 1 0.3450 0.9087 0.3961 11.00000 0.05 0.26
Q17 1 -0.1364 0.8472 0.4589 11.00000 0.05 0.25
Q18 1 -0.3835 0.8616 0.6806 11.00000 0.05 0.25
Q19 1 0.4123 0.5975 0.3713 11.00000 0.05 0.25
Q20 1 0.2694 0.8786 0.4946 11.00000 0.05 0.25
REM The information below was added by Olex2.
REM
REM R1 = 0.0701 for 5036 Fo > 4sig(Fo) and 0.0870 for all 14498 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 1.01, deepest hole -0.54
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0870
REM R1_gt = 0.0701
REM wR_ref = 0.2129
REM GOOF = 1.044
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 14498
REM Reflections_gt = 5036
REM Parameters = n/a
REM Hole = -0.54
REM Peak = 1.01
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_201810620
_database_code_depnum_ccdc_archive 'CCDC 1947688'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-17 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2018-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C28 H29 N3 O'
_chemical_formula_sum 'C28 H29 N3 O'
_chemical_formula_weight 423.54
_chemical_melting_point ?
_chemical_oxdiff_formula C15H15O3N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.0448(4)
_cell_length_b 14.0503(6)
_cell_length_c 18.8685(6)
_cell_angle_alpha 90
_cell_angle_beta 102.053(4)
_cell_angle_gamma 90
_cell_volume 2344.99(18)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2345
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.8790
_cell_measurement_theta_min 3.9340
_shelx_estimated_absorpt_T_max 0.929
_shelx_estimated_absorpt_T_min 0.879
_exptl_absorpt_coefficient_mu 0.573
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour yellow
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.200
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 904
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.13
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0370
_diffrn_reflns_av_unetI/netI 0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 9364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 67.065
_diffrn_reflns_theta_max 67.065
_diffrn_reflns_theta_min 3.954
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -46.00 8.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 37.0000 -60.0000 54
#__ type_ start__ end____ width___ exp.time_
2 omega -41.00 -13.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 77.0000 0.0000 28
#__ type_ start__ end____ width___ exp.time_
3 omega 10.00 36.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 77.0000 0.0000 26
#__ type_ start__ end____ width___ exp.time_
4 omega 38.00 96.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 37.0000 -30.0000 58
#__ type_ start__ end____ width___ exp.time_
5 omega 9.00 67.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 60.0000 58
#__ type_ start__ end____ width___ exp.time_
6 omega -30.00 2.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 -90.0000 32
#__ type_ start__ end____ width___ exp.time_
7 omega 32.00 64.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -180.0000 32
#__ type_ start__ end____ width___ exp.time_
8 omega 78.00 108.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -180.0000 30
#__ type_ start__ end____ width___ exp.time_
9 omega 14.00 63.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -77.0000 -90.0000 49
#__ type_ start__ end____ width___ exp.time_
10 omega 71.00 103.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -180.0000 32
#__ type_ start__ end____ width___ exp.time_
11 omega 57.00 82.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -30.0000 25
#__ type_ start__ end____ width___ exp.time_
12 omega 58.00 87.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -120.0000 29
#__ type_ start__ end____ width___ exp.time_
13 omega 42.00 83.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 90.0000 41
#__ type_ start__ end____ width___ exp.time_
14 omega 103.00 173.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 60.0000 70
#__ type_ start__ end____ width___ exp.time_
15 omega 90.00 177.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 -120.0000 87
#__ type_ start__ end____ width___ exp.time_
16 omega 38.00 89.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 120.0000 51
#__ type_ start__ end____ width___ exp.time_
17 omega 134.00 175.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 120.0000 41
#__ type_ start__ end____ width___ exp.time_
18 omega 91.00 130.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 120.0000 39
#__ type_ start__ end____ width___ exp.time_
19 omega 42.00 98.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 30.0000 56
#__ type_ start__ end____ width___ exp.time_
20 omega 74.00 109.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 30.0000 35
#__ type_ start__ end____ width___ exp.time_
21 omega 60.00 86.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
22 omega 45.00 132.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -77.0000 90.0000 87
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0012261000
_diffrn_orient_matrix_UB_12 0.0977823000
_diffrn_orient_matrix_UB_13 -0.0370444000
_diffrn_orient_matrix_UB_21 0.0409898000
_diffrn_orient_matrix_UB_22 0.0483960000
_diffrn_orient_matrix_UB_23 0.0748410000
_diffrn_orient_matrix_UB_31 0.1692540000
_diffrn_orient_matrix_UB_32 -0.0109986000
_diffrn_orient_matrix_UB_33 -0.0004882000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2936
_reflns_number_total 4187
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.200
_refine_diff_density_min -0.134
_refine_diff_density_rms 0.033
_refine_ls_extinction_coef 0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 293
_refine_ls_number_reflns 4187
_refine_ls_number_restraints 13
_refine_ls_R_factor_all 0.0727
_refine_ls_R_factor_gt 0.0527
_refine_ls_restrained_S_all 1.034
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.1694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1432
_refine_ls_wR_factor_ref 0.1669
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Rigid bond restraints
C27, C26
with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C27) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
C17(H17), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
C4(H4A,H4B), C6(H6A,H6B), C20(H20A,H20B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11), C13(H13), C14(H14), C19(H19), C24(H24), C25(H25),
C26(H26), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0096(3) 0.44952(17) 0.14264(12) 0.0663(6) Uani 1 1 d . . . . .
C2 C 0.0095(2) 0.39449(15) 0.20890(11) 0.0572(5) Uani 1 1 d . . . . .
C3 C 0.1502(2) 0.36338(15) 0.24288(10) 0.0527(5) Uani 1 1 d . . . . .
C4 C 0.2850(2) 0.37319(17) 0.20841(11) 0.0610(5) Uani 1 1 d . . . . .
H4A H 0.3471 0.3166 0.2190 0.073 Uiso 1 1 calc R . . . .
H4B H 0.3451 0.4270 0.2301 0.073 Uiso 1 1 calc R . . . .
C5 C 0.2437(3) 0.38733(18) 0.12599(12) 0.0696(6) Uani 1 1 d . . . . .
C6 C 0.1277(3) 0.46740(19) 0.11073(12) 0.0763(7) Uani 1 1 d . . . . .
H6A H 0.1753 0.5263 0.1304 0.092 Uiso 1 1 calc R . . . .
H6B H 0.0956 0.4753 0.0587 0.092 Uiso 1 1 calc R . . . .
C7 C 0.1784(3) 0.2964(2) 0.08724(14) 0.0886(8) Uani 1 1 d . . . . .
H7A H 0.2513 0.2460 0.0983 0.133 Uiso 1 1 calc GR . . . .
H7B H 0.1548 0.3071 0.0359 0.133 Uiso 1 1 calc GR . . . .
H7C H 0.0881 0.2788 0.1032 0.133 Uiso 1 1 calc GR . . . .
C8 C 0.3879(4) 0.4152(3) 0.10028(16) 0.1029(10) Uani 1 1 d . . . . .
H8A H 0.4334 0.4694 0.1272 0.154 Uiso 1 1 calc GR . . . .
H8B H 0.3630 0.4306 0.0496 0.154 Uiso 1 1 calc GR . . . .
H8C H 0.4577 0.3628 0.1079 0.154 Uiso 1 1 calc GR . . . .
C9 C 0.3130(2) 0.28953(15) 0.35154(10) 0.0520(5) Uani 1 1 d . . . . .
C10 C 0.3315(3) 0.19723(16) 0.37695(11) 0.0615(5) Uani 1 1 d . . . . .
H10 H 0.2528 0.1537 0.3649 0.074 Uiso 1 1 calc R . . . .
C11 C 0.4678(3) 0.1698(2) 0.42045(12) 0.0766(7) Uani 1 1 d . . . . .
H11 H 0.4790 0.1077 0.4380 0.092 Uiso 1 1 calc R . . . .
C12 C 0.5880(3) 0.2327(2) 0.43845(12) 0.0808(8) Uani 1 1 d . . . . .
C13 C 0.5669(3) 0.3247(2) 0.41306(13) 0.0759(7) Uani 1 1 d . . . . .
H13 H 0.6461 0.3680 0.4244 0.091 Uiso 1 1 calc R . . . .
C14 C 0.4302(2) 0.35394(18) 0.37100(11) 0.0631(6) Uani 1 1 d . . . . .
H14 H 0.4171 0.4169 0.3558 0.076 Uiso 1 1 calc R . . . .
C15 C 0.7385(4) 0.2006(3) 0.48356(17) 0.1312(16) Uani 1 1 d . . . . .
H15A H 0.7967 0.1704 0.4528 0.197 Uiso 1 1 calc GR . . . .
H15B H 0.7215 0.1564 0.5198 0.197 Uiso 1 1 calc GR . . . .
H15C H 0.7928 0.2548 0.5067 0.197 Uiso 1 1 calc GR . . . .
C16 C 0.1136(3) 0.4325(2) 0.44500(13) 0.0794(7) Uani 1 1 d . . . . .
C17 C 0.0357(2) 0.31558(17) 0.34279(11) 0.0592(5) Uani 1 1 d . . . . .
H17 H 0.0527 0.2668 0.3808 0.071 Uiso 1 1 calc R . . . .
C18 C 0.0146(2) 0.41061(19) 0.37683(11) 0.0658(6) Uani 1 1 d . . . . .
C19 C -0.0904(3) 0.47289(19) 0.34621(13) 0.0709(6) Uani 1 1 d . . . . .
H19 H -0.1014 0.5295 0.3702 0.085 Uiso 1 1 calc R . . . .
C20 C -0.1908(3) 0.45382(19) 0.27427(13) 0.0712(6) Uani 1 1 d . . . . .
H20A H -0.1959 0.5100 0.2439 0.085 Uiso 1 1 calc R . . . .
H20B H -0.2922 0.4396 0.2806 0.085 Uiso 1 1 calc R . . . .
C21 C -0.1305(2) 0.37038(17) 0.23762(12) 0.0616(5) Uani 1 1 d . . . . .
H21 H -0.2097 0.3495 0.1969 0.074 Uiso 1 1 calc R . . . .
C22 C -0.0889(2) 0.19810(17) 0.25761(14) 0.0691(6) Uani 1 1 d . . . . .
H22A H -0.0487 0.1523 0.2952 0.083 Uiso 1 1 calc R . . . .
H22B H -0.0199 0.2015 0.2246 0.083 Uiso 1 1 calc R . . . .
C23 C -0.2416(2) 0.16519(16) 0.21696(12) 0.0600(5) Uani 1 1 d . . . . .
C24 C -0.3624(3) 0.16116(18) 0.25149(13) 0.0682(6) Uani 1 1 d . . . . .
H24 H -0.3488 0.1797 0.2997 0.082 Uiso 1 1 calc R . . . .
C25 C -0.5019(3) 0.13024(19) 0.21552(15) 0.0750(7) Uani 1 1 d . . . . .
H25 H -0.5814 0.1274 0.2397 0.090 Uiso 1 1 calc R . . . .
C26 C -0.5248(3) 0.10363(19) 0.14476(15) 0.0791(7) Uani 1 1 d . U . . .
H26 H -0.6196 0.0829 0.1206 0.095 Uiso 1 1 calc R . . . .
C27 C -0.4071(3) 0.1075(2) 0.10918(14) 0.0834(7) Uani 1 1 d . U . . .
H27 H -0.4226 0.0899 0.0607 0.100 Uiso 1 1 calc R . . . .
C28 C -0.2650(3) 0.13762(19) 0.14543(13) 0.0741(7) Uani 1 1 d . . . . .
H28 H -0.1853 0.1392 0.1213 0.089 Uiso 1 1 calc R . . . .
N1 N 0.17020(18) 0.31888(13) 0.30858(9) 0.0555(4) Uani 1 1 d . . . . .
N2 N 0.1918(3) 0.4500(2) 0.49875(12) 0.1054(9) Uani 1 1 d . . . . .
N3 N -0.09900(19) 0.29201(14) 0.29061(10) 0.0612(5) Uani 1 1 d . . . . .
O1 O -0.1332(2) 0.48328(14) 0.11377(9) 0.0904(6) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0814(14) 0.0610(13) 0.0517(11) -0.0003(10) 0.0031(10) 0.0144(11)
C2 0.0633(11) 0.0569(12) 0.0486(10) -0.0025(9) 0.0049(9) 0.0045(10)
C3 0.0579(11) 0.0528(11) 0.0458(10) -0.0007(8) 0.0072(8) 0.0005(9)
C4 0.0624(12) 0.0656(14) 0.0549(11) 0.0023(10) 0.0123(9) -0.0003(10)
C5 0.0835(15) 0.0754(15) 0.0526(12) 0.0053(11) 0.0206(11) 0.0051(12)
C6 0.1021(18) 0.0736(16) 0.0527(12) 0.0128(11) 0.0151(12) 0.0101(14)
C7 0.103(2) 0.092(2) 0.0680(15) -0.0175(14) 0.0113(14) 0.0181(16)
C8 0.113(2) 0.127(3) 0.0807(18) 0.0185(19) 0.0463(17) 0.000(2)
C9 0.0524(10) 0.0584(12) 0.0446(9) -0.0004(8) 0.0086(8) 0.0055(9)
C10 0.0723(13) 0.0629(13) 0.0499(11) 0.0028(10) 0.0145(9) 0.0076(11)
C11 0.0958(18) 0.0846(18) 0.0494(12) 0.0076(11) 0.0155(12) 0.0369(15)
C12 0.0729(15) 0.116(2) 0.0479(12) -0.0151(13) 0.0006(11) 0.0334(16)
C13 0.0580(12) 0.106(2) 0.0604(13) -0.0191(14) 0.0043(10) -0.0002(13)
C14 0.0604(12) 0.0709(14) 0.0561(12) -0.0070(10) 0.0078(9) -0.0011(10)
C15 0.102(2) 0.188(4) 0.086(2) -0.029(2) -0.0215(17) 0.074(2)
C16 0.0733(14) 0.107(2) 0.0579(13) -0.0102(13) 0.0145(12) 0.0050(14)
C17 0.0504(10) 0.0746(14) 0.0521(11) 0.0080(10) 0.0094(8) 0.0003(10)
C18 0.0592(12) 0.0882(17) 0.0508(11) -0.0058(11) 0.0135(9) -0.0008(12)
C19 0.0671(13) 0.0818(17) 0.0645(13) -0.0116(12) 0.0156(11) 0.0060(12)
C20 0.0608(12) 0.0802(16) 0.0701(14) -0.0070(12) 0.0078(10) 0.0145(12)
C21 0.0520(11) 0.0706(14) 0.0572(11) -0.0048(10) 0.0002(9) 0.0054(10)
C22 0.0584(12) 0.0643(14) 0.0842(16) 0.0021(12) 0.0141(11) -0.0004(10)
C23 0.0595(11) 0.0585(13) 0.0618(12) 0.0017(10) 0.0122(9) -0.0015(10)
C24 0.0666(13) 0.0745(15) 0.0651(13) -0.0090(11) 0.0171(10) -0.0060(11)
C25 0.0587(12) 0.0752(17) 0.0917(17) -0.0118(13) 0.0168(12) -0.0052(11)
C26 0.0714(13) 0.0677(15) 0.0878(17) -0.0014(13) -0.0069(10) -0.0052(12)
C27 0.1083(18) 0.0800(17) 0.0566(13) -0.0001(12) 0.0051(12) -0.0058(15)
C28 0.0835(16) 0.0757(16) 0.0673(14) -0.0003(12) 0.0248(12) -0.0067(13)
N1 0.0506(9) 0.0658(11) 0.0488(9) 0.0065(8) 0.0074(7) 0.0002(8)
N2 0.0942(16) 0.153(3) 0.0607(13) -0.0246(14) -0.0019(12) 0.0166(17)
N3 0.0508(9) 0.0659(12) 0.0652(10) -0.0004(9) 0.0084(8) -0.0007(8)
O1 0.0974(13) 0.0954(14) 0.0700(10) 0.0131(10) -0.0018(9) 0.0357(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.449(3) . ?
C1 C6 1.510(3) . ?
C1 O1 1.232(3) . ?
C2 C3 1.372(3) . ?
C2 C21 1.516(3) . ?
C3 C4 1.503(3) . ?
C3 N1 1.366(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.535(3) . ?
C5 C6 1.524(3) . ?
C5 C7 1.529(4) . ?
C5 C8 1.535(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.381(3) . ?
C9 C14 1.384(3) . ?
C9 N1 1.434(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C12 C13 1.377(4) . ?
C12 C15 1.516(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.439(3) . ?
C16 N2 1.136(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.511(3) . ?
C17 N1 1.492(2) . ?
C17 N3 1.436(3) . ?
C18 C19 1.331(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.491(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.519(3) . ?
C21 H21 0.9800 . ?
C21 N3 1.475(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.506(3) . ?
C22 N3 1.470(3) . ?
C23 C24 1.385(3) . ?
C23 C28 1.377(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(4) . ?
C28 H28 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.23(19) . . ?
O1 C1 C2 121.3(2) . . ?
O1 C1 C6 120.4(2) . . ?
C1 C2 C21 118.03(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 C21 121.63(18) . . ?
C2 C3 C4 121.73(18) . . ?
N1 C3 C2 120.25(19) . . ?
N1 C3 C4 117.97(17) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.72(18) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 C8 108.1(2) . . ?
C6 C5 C4 107.43(19) . . ?
C6 C5 C7 110.2(2) . . ?
C6 C5 C8 110.4(2) . . ?
C7 C5 C4 111.4(2) . . ?
C7 C5 C8 109.3(2) . . ?
C1 C6 C5 113.1(2) . . ?
C1 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 N1 119.73(19) . . ?
C14 C9 N1 120.75(19) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C15 120.9(3) . . ?
C13 C12 C11 117.9(2) . . ?
C13 C12 C15 121.1(3) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 120.1(2) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C18 179.8(4) . . ?
C18 C17 H17 108.7 . . ?
N1 C17 H17 108.7 . . ?
N1 C17 C18 110.08(18) . . ?
N3 C17 H17 108.7 . . ?
N3 C17 C18 109.31(18) . . ?
N3 C17 N1 111.23(16) . . ?
C16 C18 C17 117.3(2) . . ?
C19 C18 C16 120.1(2) . . ?
C19 C18 C17 122.6(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C19 C20 C21 110.16(19) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C2 C21 C20 113.4(2) . . ?
C2 C21 H21 108.3 . . ?
C20 C21 H21 108.3 . . ?
N3 C21 C2 110.61(16) . . ?
N3 C21 C20 107.73(19) . . ?
N3 C21 H21 108.3 . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
N3 C22 H22A 109.4 . . ?
N3 C22 H22B 109.4 . . ?
N3 C22 C23 111.07(18) . . ?
C24 C23 C22 120.2(2) . . ?
C28 C23 C22 121.5(2) . . ?
C28 C23 C24 118.3(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 120.3(2) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C3 N1 C9 125.25(16) . . ?
C3 N1 C17 116.19(16) . . ?
C9 N1 C17 117.76(15) . . ?
C17 N3 C21 107.98(17) . . ?
C17 N3 C22 112.23(18) . . ?
C22 N3 C21 113.78(18) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -8.3(3) . . . . ?
C1 C2 C3 N1 174.19(19) . . . . ?
C1 C2 C21 C20 -76.1(2) . . . . ?
C1 C2 C21 N3 162.79(19) . . . . ?
C2 C1 C6 C5 30.8(3) . . . . ?
C2 C3 C4 C5 -19.8(3) . . . . ?
C2 C3 N1 C9 -175.26(19) . . . . ?
C2 C3 N1 C17 -5.8(3) . . . . ?
C2 C21 N3 C17 50.4(2) . . . . ?
C2 C21 N3 C22 -74.9(2) . . . . ?
C3 C2 C21 C20 105.7(2) . . . . ?
C3 C2 C21 N3 -15.4(3) . . . . ?
C3 C4 C5 C6 50.2(3) . . . . ?
C3 C4 C5 C7 -70.6(3) . . . . ?
C3 C4 C5 C8 169.3(2) . . . . ?
C4 C3 N1 C9 7.2(3) . . . . ?
C4 C3 N1 C17 176.63(18) . . . . ?
C4 C5 C6 C1 -55.5(3) . . . . ?
C6 C1 C2 C3 2.7(3) . . . . ?
C6 C1 C2 C21 -175.5(2) . . . . ?
C7 C5 C6 C1 66.0(3) . . . . ?
C8 C5 C6 C1 -173.2(2) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C9 C14 C13 2.8(3) . . . . ?
C10 C9 N1 C3 -128.6(2) . . . . ?
C10 C9 N1 C17 62.1(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C15 -177.5(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C9 -2.3(3) . . . . ?
C14 C9 C10 C11 -1.2(3) . . . . ?
C14 C9 N1 C3 54.8(3) . . . . ?
C14 C9 N1 C17 -114.5(2) . . . . ?
C15 C12 C13 C14 179.1(2) . . . . ?
C16 C18 C19 C20 177.7(2) . . . . ?
C17 C18 C19 C20 -2.4(4) . . . . ?
C18 C17 N1 C3 -78.0(2) . . . . ?
C18 C17 N1 C9 92.3(2) . . . . ?
C18 C17 N3 C21 56.4(2) . . . . ?
C18 C17 N3 C22 -177.44(18) . . . . ?
C18 C19 C20 C21 -13.1(3) . . . . ?
C19 C20 C21 C2 -73.4(3) . . . . ?
C19 C20 C21 N3 49.3(3) . . . . ?
C20 C21 N3 C17 -74.0(2) . . . . ?
C20 C21 N3 C22 160.73(18) . . . . ?
C21 C2 C3 C4 169.81(19) . . . . ?
C21 C2 C3 N1 -7.7(3) . . . . ?
C22 C23 C24 C25 -179.2(2) . . . . ?
C22 C23 C28 C27 180.0(2) . . . . ?
C23 C22 N3 C17 166.70(18) . . . . ?
C23 C22 N3 C21 -70.3(2) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C24 C23 C28 C27 0.6(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 0.6(4) . . . . ?
C26 C27 C28 C23 -1.0(4) . . . . ?
C28 C23 C24 C25 0.2(4) . . . . ?
N1 C3 C4 C5 157.7(2) . . . . ?
N1 C9 C10 C11 -177.85(18) . . . . ?
N1 C9 C14 C13 179.41(19) . . . . ?
N1 C17 C18 C16 -76.9(2) . . . . ?
N1 C17 C18 C19 103.1(2) . . . . ?
N1 C17 N3 C21 -65.4(2) . . . . ?
N1 C17 N3 C22 60.8(2) . . . . ?
N3 C17 C18 C16 160.6(2) . . . . ?
N3 C17 C18 C19 -19.4(3) . . . . ?
N3 C17 N1 C3 43.3(3) . . . . ?
N3 C17 N1 C9 -146.42(19) . . . . ?
N3 C22 C23 C24 -54.5(3) . . . . ?
N3 C22 C23 C28 126.1(2) . . . . ?
O1 C1 C2 C3 -175.3(2) . . . . ?
O1 C1 C2 C21 6.5(3) . . . . ?
O1 C1 C6 C5 -151.1(2) . . . . ?
_iucr_refine_instructions_details
;
201810620.res created by SHELXL-2014/7
TITL 201810620 in P21/c #14
REM reset to P21/c #14
CELL 1.54184 9.044821 14.050282 18.868499 90 102.0528 90
ZERR 4 0.000448 0.000616 0.000629 0 0.0037 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 112 116 12 4
DELU 0.001 0.001 C27 C26
ISOR 0.01 0.02 C27 C26
L.S. 4 0 0
PLAN 20
SIZE 0.13 0.16 0.23
MPLA C1 C2 C3 C4 C6
MPLA C4 C5 C6
MPLA C9 C10 C11 C12 C13 C14
MPLA C23 C24 C25 C26 C27 C28
bond $h
conf
fmap 2
acta
REM
REM
REM
WGHT 0.074900 0.169400
EXTI 0.001603
FVAR 6.54905
C1 1 -0.009598 0.449525 0.142636 11.00000 0.08138 0.06096 =
0.05173 -0.00031 0.00314 0.01440
C2 1 0.009460 0.394493 0.208903 11.00000 0.06325 0.05692 =
0.04861 -0.00245 0.00495 0.00448
C3 1 0.150224 0.363378 0.242883 11.00000 0.05787 0.05283 =
0.04576 -0.00068 0.00715 0.00055
C4 1 0.285038 0.373192 0.208411 11.00000 0.06244 0.06563 =
0.05490 0.00226 0.01232 -0.00025
AFIX 23
H4A 2 0.347083 0.316568 0.218976 11.00000 -1.20000
H4B 2 0.345079 0.427006 0.230067 11.00000 -1.20000
AFIX 0
C5 1 0.243681 0.387327 0.125992 11.00000 0.08352 0.07538 =
0.05259 0.00527 0.02059 0.00506
C6 1 0.127745 0.467400 0.110732 11.00000 0.10212 0.07364 =
0.05273 0.01280 0.01514 0.01010
AFIX 23
H6A 2 0.175289 0.526287 0.130434 11.00000 -1.20000
H6B 2 0.095620 0.475322 0.058719 11.00000 -1.20000
AFIX 0
C7 1 0.178384 0.296369 0.087239 11.00000 0.10264 0.09226 =
0.06795 -0.01748 0.01127 0.01809
AFIX 137
H7A 2 0.251260 0.245991 0.098296 11.00000 -1.50000
H7B 2 0.154812 0.307143 0.035868 11.00000 -1.50000
H7C 2 0.088070 0.278847 0.103215 11.00000 -1.50000
AFIX 0
C8 1 0.387946 0.415158 0.100283 11.00000 0.11264 0.12686 =
0.08065 0.01848 0.04629 0.00009
AFIX 137
H8A 2 0.433393 0.469431 0.127224 11.00000 -1.50000
H8B 2 0.362951 0.430611 0.049626 11.00000 -1.50000
H8C 2 0.457738 0.362840 0.107917 11.00000 -1.50000
AFIX 0
C9 1 0.312970 0.289528 0.351535 11.00000 0.05243 0.05842 =
0.04459 -0.00037 0.00858 0.00555
C10 1 0.331499 0.197233 0.376945 11.00000 0.07230 0.06292 =
0.04993 0.00278 0.01451 0.00760
AFIX 43
H10 2 0.252822 0.153681 0.364914 11.00000 -1.20000
AFIX 0
C11 1 0.467792 0.169757 0.420445 11.00000 0.09584 0.08457 =
0.04940 0.00763 0.01551 0.03691
AFIX 43
H11 2 0.478974 0.107736 0.437965 11.00000 -1.20000
AFIX 0
C12 1 0.587965 0.232723 0.438448 11.00000 0.07292 0.11625 =
0.04793 -0.01506 0.00056 0.03341
C13 1 0.566902 0.324689 0.413059 11.00000 0.05801 0.10582 =
0.06038 -0.01912 0.00434 -0.00015
AFIX 43
H13 2 0.646073 0.368003 0.424381 11.00000 -1.20000
AFIX 0
C14 1 0.430164 0.353941 0.371001 11.00000 0.06043 0.07087 =
0.05612 -0.00703 0.00778 -0.00111
AFIX 43
H14 2 0.417099 0.416925 0.355831 11.00000 -1.20000
AFIX 0
C15 1 0.738518 0.200647 0.483558 11.00000 0.10171 0.18827 =
0.08562 -0.02880 -0.02147 0.07425
AFIX 137
H15A 2 0.796671 0.170422 0.452788 11.00000 -1.50000
H15B 2 0.721471 0.156362 0.519764 11.00000 -1.50000
H15C 2 0.792759 0.254843 0.506690 11.00000 -1.50000
AFIX 0
C16 1 0.113563 0.432477 0.444999 11.00000 0.07334 0.10724 =
0.05790 -0.01021 0.01451 0.00496
C17 1 0.035704 0.315579 0.342792 11.00000 0.05040 0.07456 =
0.05207 0.00800 0.00940 0.00033
AFIX 13
H17 2 0.052651 0.266837 0.380780 11.00000 -1.20000
AFIX 0
C18 1 0.014568 0.410608 0.376830 11.00000 0.05924 0.08815 =
0.05081 -0.00578 0.01354 -0.00079
C19 1 -0.090439 0.472894 0.346211 11.00000 0.06711 0.08181 =
0.06449 -0.01159 0.01556 0.00601
AFIX 43
H19 2 -0.101420 0.529463 0.370182 11.00000 -1.20000
AFIX 0
C20 1 -0.190820 0.453823 0.274267 11.00000 0.06081 0.08024 =
0.07014 -0.00703 0.00783 0.01445
AFIX 23
H20A 2 -0.195872 0.509953 0.243923 11.00000 -1.20000
H20B 2 -0.292182 0.439589 0.280629 11.00000 -1.20000
AFIX 0
C21 1 -0.130478 0.370382 0.237620 11.00000 0.05200 0.07059 =
0.05723 -0.00477 0.00023 0.00543
AFIX 13
H21 2 -0.209691 0.349521 0.196868 11.00000 -1.20000
AFIX 0
C22 1 -0.088862 0.198102 0.257610 11.00000 0.05838 0.06425 =
0.08422 0.00213 0.01412 -0.00038
AFIX 23
H22A 2 -0.048681 0.152324 0.295188 11.00000 -1.20000
H22B 2 -0.019939 0.201547 0.224606 11.00000 -1.20000
AFIX 0
C23 1 -0.241604 0.165191 0.216959 11.00000 0.05951 0.05855 =
0.06185 0.00168 0.01218 -0.00150
C24 1 -0.362408 0.161165 0.251487 11.00000 0.06658 0.07453 =
0.06511 -0.00902 0.01714 -0.00599
AFIX 43
H24 2 -0.348802 0.179688 0.299737 11.00000 -1.20000
AFIX 0
C25 1 -0.501866 0.130236 0.215518 11.00000 0.05874 0.07517 =
0.09168 -0.01181 0.01684 -0.00524
AFIX 43
H25 2 -0.581388 0.127447 0.239735 11.00000 -1.20000
AFIX 0
C26 1 -0.524792 0.103626 0.144762 11.00000 0.07145 0.06767 =
0.08778 -0.00139 -0.00687 -0.00525
AFIX 43
H26 2 -0.619636 0.082915 0.120618 11.00000 -1.20000
AFIX 0
C27 1 -0.407125 0.107512 0.109177 11.00000 0.10829 0.08002 =
0.05658 -0.00006 0.00507 -0.00581
AFIX 43
H27 2 -0.422560 0.089947 0.060665 11.00000 -1.20000
AFIX 0
C28 1 -0.264971 0.137621 0.145434 11.00000 0.08348 0.07565 =
0.06726 -0.00028 0.02478 -0.00670
AFIX 43
H28 2 -0.185283 0.139154 0.121278 11.00000 -1.20000
AFIX 0
N1 3 0.170199 0.318875 0.308580 11.00000 0.05058 0.06583 =
0.04883 0.00650 0.00735 0.00020
N2 3 0.191835 0.450017 0.498750 11.00000 0.09419 0.15337 =
0.06074 -0.02462 -0.00194 0.01657
N3 3 -0.099002 0.292006 0.290613 11.00000 0.05085 0.06588 =
0.06525 -0.00035 0.00843 -0.00072
O1 4 -0.133210 0.483283 0.113774 11.00000 0.09740 0.09542 =
0.07003 0.01312 -0.00180 0.03571
HKLF 4
REM 201810620 in P21/c #14
REM R1 = 0.0527 for 2936 Fo > 4sig(Fo) and 0.0727 for all 4187 data
REM 293 parameters refined using 13 restraints
END
WGHT 0.0749 0.1695
REM Highest difference peak 0.200, deepest hole -0.134, 1-sigma level 0.033
Q1 1 0.7364 0.2159 0.5332 11.00000 0.05 0.20
Q2 1 0.0202 0.4138 0.1910 11.00000 0.05 0.15
Q3 1 -0.3185 0.1992 0.2193 11.00000 0.05 0.14
Q4 1 0.2651 0.3820 0.1700 11.00000 0.05 0.14
Q5 1 0.0788 0.3463 0.2073 11.00000 0.05 0.14
Q6 1 -0.2345 0.1084 0.1911 11.00000 0.05 0.14
Q7 1 0.0538 0.4104 0.2265 11.00000 0.05 0.14
Q8 1 -0.0321 0.4210 0.2370 11.00000 0.05 0.13
Q9 1 0.1657 0.2807 0.2678 11.00000 0.05 0.13
Q10 1 -0.1945 0.2793 0.3217 11.00000 0.05 0.13
Q11 1 0.1614 0.3352 0.2790 11.00000 0.05 0.13
Q12 1 -0.2548 0.1806 0.1824 11.00000 0.05 0.13
Q13 1 0.1094 0.4032 0.5011 11.00000 0.05 0.12
Q14 1 0.7387 0.1168 0.4757 11.00000 0.05 0.12
Q15 1 -0.5613 0.0902 0.2723 11.00000 0.05 0.12
Q16 1 0.7072 0.1030 0.5021 11.00000 0.05 0.11
Q17 1 -0.4987 0.1341 0.1713 11.00000 0.05 0.11
Q18 1 -0.4742 0.1359 0.1199 11.00000 0.05 0.11
Q19 1 -0.1372 0.3998 0.2583 11.00000 0.05 0.10
Q20 1 0.2346 0.3923 0.2201 11.00000 0.05 0.10
REM The information below was added by Olex2.
REM
REM R1 = 0.0527 for 2936 Fo > 4sig(Fo) and 0.0727 for all 9661 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.20, deepest hole -0.13
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0727
REM R1_gt = 0.0527
REM wR_ref = 0.1669
REM GOOF = 1.032
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 9661
REM Reflections_gt = 2936
REM Parameters = n/a
REM Hole = -0.13
REM Peak = 0.20
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_20190484
_database_code_depnum_ccdc_archive 'CCDC 1947691'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-17 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2019-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C31 H31 Br N2 O'
_chemical_formula_sum 'C31 H31 Br N2 O'
_chemical_formula_weight 527.49
_chemical_melting_point ?
_chemical_oxdiff_formula C20H20N4O4Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 14.4850(5)
_cell_length_b 10.8239(5)
_cell_length_c 16.4134(7)
_cell_angle_alpha 90
_cell_angle_beta 90.869(3)
_cell_angle_gamma 90
_cell_volume 2573.07(18)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3325
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.7610
_cell_measurement_theta_min 4.0450
_shelx_estimated_absorpt_T_max 0.797
_shelx_estimated_absorpt_T_min 0.689
_exptl_absorpt_coefficient_mu 2.372
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.90797
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.362
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 1096
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0341
_diffrn_reflns_av_unetI/netI 0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 10451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 67.055
_diffrn_reflns_theta_max 67.055
_diffrn_reflns_theta_min 4.040
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -101.00 -17.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -57.0000 0.0000 84
#__ type_ start__ end____ width___ exp.time_
2 omega -108.00 -75.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 30.0000 33
#__ type_ start__ end____ width___ exp.time_
3 omega -3.00 22.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -180.0000 25
#__ type_ start__ end____ width___ exp.time_
4 omega 58.00 85.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -180.0000 27
#__ type_ start__ end____ width___ exp.time_
5 omega 18.00 58.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -37.0000 30.0000 40
#__ type_ start__ end____ width___ exp.time_
6 omega 45.00 71.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -150.0000 26
#__ type_ start__ end____ width___ exp.time_
7 omega -31.00 21.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -57.0000 -60.0000 52
#__ type_ start__ end____ width___ exp.time_
8 omega 0.00 26.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -150.0000 26
#__ type_ start__ end____ width___ exp.time_
9 omega -33.00 -7.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -37.0000 -150.0000 26
#__ type_ start__ end____ width___ exp.time_
10 omega 13.00 59.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -37.0000 -150.0000 46
#__ type_ start__ end____ width___ exp.time_
11 omega -31.00 -5.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -37.0000 30.0000 26
#__ type_ start__ end____ width___ exp.time_
12 omega 1.00 38.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 90.0000 37
#__ type_ start__ end____ width___ exp.time_
13 omega 52.00 77.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 90.0000 25
#__ type_ start__ end____ width___ exp.time_
14 omega 38.00 71.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 -180.0000 33
#__ type_ start__ end____ width___ exp.time_
15 omega 58.00 87.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -150.0000 29
#__ type_ start__ end____ width___ exp.time_
16 omega 60.00 91.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 120.0000 31
#__ type_ start__ end____ width___ exp.time_
17 omega 41.00 106.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 30.0000 65
#__ type_ start__ end____ width___ exp.time_
18 omega 42.00 97.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 90.0000 55
#__ type_ start__ end____ width___ exp.time_
19 omega 67.00 113.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -180.0000 46
#__ type_ start__ end____ width___ exp.time_
20 omega 38.00 72.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 -30.0000 34
#__ type_ start__ end____ width___ exp.time_
21 omega 47.00 78.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 -150.0000 31
#__ type_ start__ end____ width___ exp.time_
22 omega 134.00 175.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 -150.0000 41
#__ type_ start__ end____ width___ exp.time_
23 omega 103.00 129.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 -150.0000 26
#__ type_ start__ end____ width___ exp.time_
24 omega 57.00 99.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 30.0000 42
#__ type_ start__ end____ width___ exp.time_
25 omega 67.00 109.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 90.0000 42
#__ type_ start__ end____ width___ exp.time_
26 omega 87.00 174.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 108.0000 30.0000 -90.0000 87
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0560458000
_diffrn_orient_matrix_UB_12 -0.0882394000
_diffrn_orient_matrix_UB_13 -0.0553746000
_diffrn_orient_matrix_UB_21 -0.0365383000
_diffrn_orient_matrix_UB_22 0.1112162000
_diffrn_orient_matrix_UB_23 -0.0494024000
_diffrn_orient_matrix_UB_31 0.0826638000
_diffrn_orient_matrix_UB_32 -0.0106723000
_diffrn_orient_matrix_UB_33 -0.0574768000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3531
_reflns_number_total 4590
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.269
_refine_diff_density_min -0.450
_refine_diff_density_rms 0.058
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 319
_refine_ls_number_reflns 4590
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0603
_refine_ls_R_factor_gt 0.0444
_refine_ls_restrained_S_all 1.015
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.5371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1123
_refine_ls_wR_factor_ref 0.1261
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
C10(H10A,H10B), C20(H20A,H20B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
C16(H16), C26(H26), C27(H27), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.04757(2) -0.01860(4) 0.37544(2) 0.06148(16) Uani 1 1 d . . . . .
C1 C 0.0167(2) 0.1485(3) 0.2134(2) 0.0582(9) Uani 1 1 d . . . . .
H1 H -0.0273 0.1965 0.2394 0.070 Uiso 1 1 calc R . . . .
C2 C 0.0205(3) 0.1495(4) 0.1293(2) 0.0659(10) Uani 1 1 d . . . . .
H2 H -0.0220 0.1952 0.0988 0.079 Uiso 1 1 calc R . . . .
C3 C 0.0885(2) 0.0815(3) 0.0911(2) 0.0572(9) Uani 1 1 d . . . . .
H3 H 0.0919 0.0820 0.0345 0.069 Uiso 1 1 calc R . . . .
C4 C 0.1509(2) 0.0133(3) 0.1365(2) 0.0468(7) Uani 1 1 d . . . . .
H4 H 0.1970 -0.0304 0.1103 0.056 Uiso 1 1 calc R . . . .
C5 C 0.14571(19) 0.0089(3) 0.22141(18) 0.0389(6) Uani 1 1 d . . . . .
C6 C 0.07751(19) 0.0770(3) 0.25988(19) 0.0433(7) Uani 1 1 d . . . . .
C7 C 0.06853(18) 0.0706(3) 0.35069(19) 0.0429(7) Uani 1 1 d . . . . .
H7 H 0.0648 0.1547 0.3724 0.051 Uiso 1 1 calc R . . . .
C8 C 0.14755(19) 0.0017(3) 0.39456(18) 0.0387(6) Uani 1 1 d . . . . .
H8 H 0.1255 -0.0259 0.4477 0.046 Uiso 1 1 calc R . . . .
C9 C 0.21534(18) -0.0645(3) 0.27126(17) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.2342 -0.1372 0.2400 0.046 Uiso 1 1 calc R . . . .
C10 C 0.2308(2) -0.1942(3) 0.39255(19) 0.0465(7) Uani 1 1 d . . . . .
H10A H 0.2878 -0.1537 0.4089 0.056 Uiso 1 1 calc R . . . .
H10B H 0.2463 -0.2621 0.3567 0.056 Uiso 1 1 calc R . . . .
C11 C 0.1842(2) -0.2452(3) 0.46757(18) 0.0431(7) Uani 1 1 d . . . . .
C12 C 0.2328(2) -0.2509(3) 0.5408(2) 0.0529(8) Uani 1 1 d . . . . .
H12 H 0.2932 -0.2218 0.5438 0.063 Uiso 1 1 calc R . . . .
C13 C 0.1926(3) -0.2993(4) 0.6094(2) 0.0658(10) Uani 1 1 d . . . . .
H13 H 0.2264 -0.3035 0.6579 0.079 Uiso 1 1 calc R . . . .
C14 C 0.1041(3) -0.3410(3) 0.6068(2) 0.0627(10) Uani 1 1 d . . . . .
H14 H 0.0773 -0.3722 0.6537 0.075 Uiso 1 1 calc R . . . .
C15 C 0.0541(2) -0.3370(3) 0.5350(2) 0.0593(9) Uani 1 1 d . . . . .
H15 H -0.0061 -0.3667 0.5328 0.071 Uiso 1 1 calc R . . . .
C16 C 0.0942(2) -0.2882(3) 0.4653(2) 0.0532(8) Uani 1 1 d . . . . .
H16 H 0.0602 -0.2845 0.4169 0.064 Uiso 1 1 calc R . . . .
C17 C 0.3757(2) 0.0158(3) 0.23299(18) 0.0443(7) Uani 1 1 d . . . . .
C18 C 0.29941(19) 0.0150(3) 0.28901(17) 0.0379(6) Uani 1 1 d . . . . .
C19 C 0.30071(18) 0.0868(3) 0.35691(17) 0.0371(6) Uani 1 1 d . . . . .
C20 C 0.38062(19) 0.1692(3) 0.37915(18) 0.0441(7) Uani 1 1 d . . . . .
H20A H 0.3909 0.1652 0.4376 0.053 Uiso 1 1 calc R . . . .
H20B H 0.3643 0.2537 0.3656 0.053 Uiso 1 1 calc R . . . .
C21 C 0.47084(19) 0.1367(3) 0.33685(18) 0.0451(7) Uani 1 1 d . . . . .
C22 C 0.4486(2) 0.1124(3) 0.24721(18) 0.0499(8) Uani 1 1 d . . . . .
H22A H 0.4284 0.1890 0.2221 0.060 Uiso 1 1 calc R . . . .
H22B H 0.5047 0.0866 0.2204 0.060 Uiso 1 1 calc R . . . .
C23 C 0.5155(3) 0.0230(4) 0.3754(3) 0.0699(11) Uani 1 1 d . . . . .
H23A H 0.4731 -0.0451 0.3727 0.105 Uiso 1 1 calc GR . . . .
H23B H 0.5310 0.0401 0.4314 0.105 Uiso 1 1 calc GR . . . .
H23C H 0.5705 0.0023 0.3466 0.105 Uiso 1 1 calc GR . . . .
C24 C 0.5361(2) 0.2485(4) 0.3442(2) 0.0673(11) Uani 1 1 d . . . . .
H24A H 0.5934 0.2297 0.3184 0.101 Uiso 1 1 calc GR . . . .
H24B H 0.5474 0.2668 0.4007 0.101 Uiso 1 1 calc GR . . . .
H24C H 0.5081 0.3188 0.3180 0.101 Uiso 1 1 calc GR . . . .
C25 C 0.22780(18) 0.1601(3) 0.48138(16) 0.0373(6) Uani 1 1 d . . . . .
C26 C 0.2034(2) 0.2837(3) 0.47661(17) 0.0433(7) Uani 1 1 d . . . . .
H26 H 0.1829 0.3173 0.4274 0.052 Uiso 1 1 calc R . . . .
C27 C 0.2097(2) 0.3566(3) 0.54552(19) 0.0486(7) Uani 1 1 d . . . . .
H27 H 0.1938 0.4397 0.5418 0.058 Uiso 1 1 calc R . . . .
C28 C 0.2391(2) 0.3099(3) 0.61995(18) 0.0452(7) Uani 1 1 d . . . . .
C29 C 0.2601(2) 0.1848(3) 0.62389(18) 0.0496(8) Uani 1 1 d . . . . .
H29 H 0.2781 0.1502 0.6735 0.060 Uiso 1 1 calc R . . . .
C30 C 0.2546(2) 0.1108(3) 0.55546(18) 0.0467(7) Uani 1 1 d . . . . .
H30 H 0.2691 0.0273 0.5594 0.056 Uiso 1 1 calc R . . . .
C31 C 0.2489(3) 0.3919(4) 0.6939(2) 0.0652(10) Uani 1 1 d . . . . .
H31A H 0.1897 0.4255 0.7072 0.098 Uiso 1 1 calc GR . . . .
H31B H 0.2909 0.4581 0.6824 0.098 Uiso 1 1 calc GR . . . .
H31C H 0.2723 0.3444 0.7390 0.098 Uiso 1 1 calc GR . . . .
N1 N 0.17235(16) -0.1058(2) 0.34771(14) 0.0388(5) Uani 1 1 d . . . . .
N2 N 0.22716(15) 0.0859(2) 0.40841(14) 0.0400(6) Uani 1 1 d . . . . .
O1 O 0.37940(16) -0.0556(3) 0.17501(14) 0.0657(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03193(19) 0.0869(3) 0.0658(3) -0.0033(2) 0.00724(15) -0.00322(17)
C1 0.0434(17) 0.063(2) 0.068(2) 0.0006(19) -0.0036(15) 0.0080(16)
C2 0.058(2) 0.070(2) 0.069(2) 0.017(2) -0.0140(18) 0.0060(19)
C3 0.065(2) 0.063(2) 0.0436(18) 0.0087(17) -0.0083(16) -0.0128(19)
C4 0.0476(17) 0.0494(18) 0.0435(17) -0.0015(14) 0.0027(13) -0.0079(14)
C5 0.0324(14) 0.0415(16) 0.0428(16) -0.0016(13) -0.0015(11) -0.0056(12)
C6 0.0325(14) 0.0458(17) 0.0516(17) -0.0049(15) -0.0011(12) -0.0003(13)
C7 0.0291(13) 0.0471(17) 0.0524(17) -0.0087(15) 0.0022(12) -0.0008(13)
C8 0.0303(13) 0.0479(17) 0.0379(15) -0.0031(13) 0.0048(11) 0.0000(12)
C9 0.0340(13) 0.0418(15) 0.0381(15) -0.0068(13) 0.0022(11) 0.0018(12)
C10 0.0368(15) 0.0513(18) 0.0514(18) 0.0043(15) 0.0049(13) 0.0079(14)
C11 0.0431(16) 0.0427(17) 0.0437(16) 0.0002(14) 0.0033(12) 0.0031(13)
C12 0.0554(19) 0.0498(19) 0.0532(19) 0.0019(16) -0.0086(15) 0.0005(16)
C13 0.098(3) 0.056(2) 0.0425(18) 0.0034(17) -0.0086(18) 0.003(2)
C14 0.084(3) 0.051(2) 0.054(2) 0.0035(17) 0.0222(19) 0.009(2)
C15 0.0508(19) 0.057(2) 0.070(2) -0.0015(19) 0.0179(17) 0.0008(17)
C16 0.0469(17) 0.067(2) 0.0459(17) -0.0029(17) 0.0002(13) 0.0013(16)
C17 0.0333(14) 0.061(2) 0.0382(16) -0.0024(15) 0.0031(12) 0.0049(14)
C18 0.0295(13) 0.0479(17) 0.0362(15) -0.0024(13) 0.0019(11) 0.0033(12)
C19 0.0286(13) 0.0438(16) 0.0387(15) -0.0012(13) 0.0006(11) 0.0057(12)
C20 0.0337(14) 0.0560(19) 0.0427(16) -0.0055(15) -0.0009(12) 0.0014(14)
C21 0.0325(14) 0.060(2) 0.0424(16) -0.0042(15) 0.0000(12) 0.0011(14)
C22 0.0364(15) 0.069(2) 0.0449(17) -0.0034(16) 0.0089(13) -0.0003(15)
C23 0.051(2) 0.087(3) 0.071(3) 0.006(2) -0.0075(18) 0.020(2)
C24 0.0358(17) 0.092(3) 0.075(2) -0.017(2) 0.0039(16) -0.0143(18)
C25 0.0290(12) 0.0475(17) 0.0354(14) -0.0046(13) 0.0056(10) 0.0005(12)
C26 0.0456(16) 0.0495(17) 0.0348(15) 0.0022(14) -0.0006(12) 0.0085(14)
C27 0.0575(19) 0.0432(17) 0.0451(17) -0.0023(14) 0.0016(14) 0.0112(15)
C28 0.0438(16) 0.0536(19) 0.0382(15) -0.0067(14) 0.0029(12) 0.0026(14)
C29 0.0556(18) 0.059(2) 0.0342(15) 0.0022(15) -0.0040(13) 0.0076(16)
C30 0.0490(17) 0.0434(17) 0.0475(18) 0.0012(14) -0.0003(13) 0.0093(14)
C31 0.086(3) 0.067(2) 0.0425(18) -0.0088(18) -0.0042(17) 0.011(2)
N1 0.0364(12) 0.0421(13) 0.0380(12) -0.0011(11) 0.0046(9) 0.0020(11)
N2 0.0322(11) 0.0493(14) 0.0384(13) -0.0075(11) 0.0028(9) 0.0006(11)
O1 0.0511(13) 0.0952(19) 0.0514(14) -0.0307(14) 0.0170(11) -0.0104(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.986(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(5) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(4) . ?
C5 C6 1.391(4) . ?
C5 C9 1.514(4) . ?
C6 C7 1.500(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.536(4) . ?
C8 H8 0.9800 . ?
C8 N1 1.443(4) . ?
C8 N2 1.484(4) . ?
C9 H9 0.9800 . ?
C9 C18 1.516(4) . ?
C9 N1 1.478(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(4) . ?
C10 N1 1.468(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.448(4) . ?
C17 C22 1.502(4) . ?
C17 O1 1.228(4) . ?
C18 C19 1.359(4) . ?
C19 C20 1.502(4) . ?
C19 N2 1.370(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.530(4) . ?
C21 C22 1.524(4) . ?
C21 C23 1.524(5) . ?
C21 C24 1.539(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.386(4) . ?
C25 C30 1.379(4) . ?
C25 N2 1.442(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(4) . ?
C28 C29 1.389(5) . ?
C28 C31 1.509(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.1(3) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C9 120.8(3) . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 C9 120.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 120.0(3) . . ?
Br1 C7 H7 109.0 . . ?
C6 C7 Br1 108.2(2) . . ?
C6 C7 H7 109.0 . . ?
C6 C7 C8 114.4(2) . . ?
C8 C7 Br1 107.2(2) . . ?
C8 C7 H7 109.0 . . ?
C7 C8 H8 108.3 . . ?
N1 C8 C7 109.3(2) . . ?
N1 C8 H8 108.3 . . ?
N1 C8 N2 112.2(2) . . ?
N2 C8 C7 110.2(2) . . ?
N2 C8 H8 108.3 . . ?
C5 C9 H9 109.1 . . ?
C5 C9 C18 109.4(2) . . ?
C18 C9 H9 109.1 . . ?
N1 C9 C5 109.3(2) . . ?
N1 C9 H9 109.1 . . ?
N1 C9 C18 110.8(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
N1 C10 C11 112.6(2) . . ?
C12 C11 C10 119.6(3) . . ?
C16 C11 C10 122.1(3) . . ?
C16 C11 C12 118.3(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C22 116.6(3) . . ?
O1 C17 C18 122.1(3) . . ?
O1 C17 C22 121.3(3) . . ?
C17 C18 C9 120.0(2) . . ?
C19 C18 C9 118.9(2) . . ?
C19 C18 C17 121.1(3) . . ?
C18 C19 C20 122.7(2) . . ?
C18 C19 N2 120.1(3) . . ?
N2 C19 C20 117.3(2) . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C19 C20 C21 114.4(2) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 C24 108.2(3) . . ?
C22 C21 C20 108.0(2) . . ?
C22 C21 C24 109.4(3) . . ?
C23 C21 C20 110.9(3) . . ?
C23 C21 C22 110.1(3) . . ?
C23 C21 C24 110.3(3) . . ?
C17 C22 C21 114.1(3) . . ?
C17 C22 H22A 108.7 . . ?
C17 C22 H22B 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N2 119.5(3) . . ?
C30 C25 C26 119.5(3) . . ?
C30 C25 N2 121.0(3) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.0 . . ?
C26 C27 C28 122.0(3) . . ?
C28 C27 H27 119.0 . . ?
C27 C28 C29 117.5(3) . . ?
C27 C28 C31 121.2(3) . . ?
C29 C28 C31 121.2(3) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.2(3) . . ?
C30 C29 H29 119.4 . . ?
C25 C30 C29 120.3(3) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C8 N1 C9 108.7(2) . . ?
C8 N1 C10 113.9(2) . . ?
C10 N1 C9 112.0(2) . . ?
C19 N2 C8 121.3(2) . . ?
C19 N2 C25 120.9(2) . . ?
C25 N2 C8 117.7(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 N1 79.6(2) . . . . ?
Br1 C7 C8 N2 -156.63(18) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C1 C6 C7 Br1 68.0(3) . . . . ?
C1 C6 C7 C8 -172.6(3) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
C2 C1 C6 C7 -176.1(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C4 C5 C9 -179.0(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C4 C5 C9 C18 86.3(3) . . . . ?
C4 C5 C9 N1 -152.2(3) . . . . ?
C5 C6 C7 Br1 -110.5(3) . . . . ?
C5 C6 C7 C8 8.9(4) . . . . ?
C5 C9 C18 C17 -89.7(3) . . . . ?
C5 C9 C18 C19 88.8(3) . . . . ?
C5 C9 N1 C8 -62.7(3) . . . . ?
C5 C9 N1 C10 170.6(2) . . . . ?
C6 C1 C2 C3 -2.4(6) . . . . ?
C6 C5 C9 C18 -91.3(3) . . . . ?
C6 C5 C9 N1 30.3(4) . . . . ?
C6 C7 C8 N1 -40.3(3) . . . . ?
C6 C7 C8 N2 83.4(3) . . . . ?
C7 C8 N1 C9 68.3(3) . . . . ?
C7 C8 N1 C10 -166.0(2) . . . . ?
C7 C8 N2 C19 -97.8(3) . . . . ?
C7 C8 N2 C25 86.8(3) . . . . ?
C9 C5 C6 C1 177.0(3) . . . . ?
C9 C5 C6 C7 -4.4(4) . . . . ?
C9 C18 C19 C20 -179.6(3) . . . . ?
C9 C18 C19 N2 0.5(4) . . . . ?
C10 C11 C12 C13 -178.6(3) . . . . ?
C10 C11 C16 C15 178.6(3) . . . . ?
C11 C10 N1 C8 60.8(3) . . . . ?
C11 C10 N1 C9 -175.3(2) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C11 C16 C15 -0.6(5) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C14 C15 C16 C11 0.9(6) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C17 C18 C19 N2 179.0(3) . . . . ?
C18 C9 N1 C8 58.0(3) . . . . ?
C18 C9 N1 C10 -68.7(3) . . . . ?
C18 C17 C22 C21 38.1(4) . . . . ?
C18 C19 C20 C21 -18.7(4) . . . . ?
C18 C19 N2 C8 3.8(4) . . . . ?
C18 C19 N2 C25 179.1(3) . . . . ?
C19 C20 C21 C22 44.7(4) . . . . ?
C19 C20 C21 C23 -76.0(3) . . . . ?
C19 C20 C21 C24 162.9(3) . . . . ?
C20 C19 N2 C8 -176.1(3) . . . . ?
C20 C19 N2 C25 -0.8(4) . . . . ?
C20 C21 C22 C17 -54.9(4) . . . . ?
C22 C17 C18 C9 169.9(3) . . . . ?
C22 C17 C18 C19 -8.6(4) . . . . ?
C23 C21 C22 C17 66.3(4) . . . . ?
C24 C21 C22 C17 -172.4(3) . . . . ?
C25 C26 C27 C28 -0.6(5) . . . . ?
C26 C25 C30 C29 -2.1(4) . . . . ?
C26 C25 N2 C8 -101.9(3) . . . . ?
C26 C25 N2 C19 82.7(3) . . . . ?
C26 C27 C28 C29 -1.6(5) . . . . ?
C26 C27 C28 C31 177.7(3) . . . . ?
C27 C28 C29 C30 2.0(5) . . . . ?
C28 C29 C30 C25 -0.1(5) . . . . ?
C30 C25 C26 C27 2.5(4) . . . . ?
C30 C25 N2 C8 79.8(3) . . . . ?
C30 C25 N2 C19 -95.6(3) . . . . ?
C31 C28 C29 C30 -177.4(3) . . . . ?
N1 C8 N2 C19 24.3(4) . . . . ?
N1 C8 N2 C25 -151.1(2) . . . . ?
N1 C9 C18 C17 149.6(3) . . . . ?
N1 C9 C18 C19 -31.9(4) . . . . ?
N1 C10 C11 C12 -133.8(3) . . . . ?
N1 C10 C11 C16 47.0(4) . . . . ?
N2 C8 N1 C9 -54.2(3) . . . . ?
N2 C8 N1 C10 71.4(3) . . . . ?
N2 C19 C20 C21 161.2(3) . . . . ?
N2 C25 C26 C27 -175.9(3) . . . . ?
N2 C25 C30 C29 176.2(3) . . . . ?
O1 C17 C18 C9 -7.6(5) . . . . ?
O1 C17 C18 C19 173.9(3) . . . . ?
O1 C17 C22 C21 -144.3(3) . . . . ?
_iucr_refine_instructions_details
;
20190484.res created by SHELXL-2014/7
TITL 20190484 in P21/n #14
REM reset to P21/n #14
CELL 1.54184 14.485048 10.823856 16.41343 90 90.869 90
ZERR 4 0.00045 0.000535 0.000653 0 0.0031 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Br N O
UNIT 124 124 4 8 4
L.S. 9 0 0
PLAN 20
SIZE 0.1 0.13 0.17
MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9
MPLA C8 C9 N1
MPLA C11 C12 C13 C14 C15 C16
MPLA C17 C18 C19 C20 C22
MPLA C20 C21 C22
MPLA C25 C26 C27 C28 C29 C30
bond $h
conf
fmap 2
acta
REM
REM
REM
WGHT 0.061600 0.537100
FVAR 4.85720
BR1 3 -0.047574 -0.018605 0.375438 11.00000 0.03193 0.08687 =
0.06585 -0.00330 0.00724 -0.00322
C1 1 0.016671 0.148547 0.213411 11.00000 0.04338 0.06258 =
0.06845 0.00060 -0.00357 0.00800
AFIX 43
H1 2 -0.027286 0.196503 0.239391 11.00000 -1.20000
AFIX 0
C2 1 0.020492 0.149545 0.129334 11.00000 0.05845 0.07001 =
0.06888 0.01744 -0.01405 0.00605
AFIX 43
H2 2 -0.021971 0.195245 0.098795 11.00000 -1.20000
AFIX 0
C3 1 0.088451 0.081537 0.091056 11.00000 0.06510 0.06275 =
0.04362 0.00872 -0.00832 -0.01277
AFIX 43
H3 2 0.091900 0.082000 0.034524 11.00000 -1.20000
AFIX 0
C4 1 0.150858 0.013305 0.136495 11.00000 0.04755 0.04941 =
0.04347 -0.00146 0.00265 -0.00788
AFIX 43
H4 2 0.197042 -0.030407 0.110305 11.00000 -1.20000
AFIX 0
C5 1 0.145708 0.008879 0.221415 11.00000 0.03237 0.04152 =
0.04276 -0.00155 -0.00149 -0.00565
C6 1 0.077513 0.076963 0.259875 11.00000 0.03251 0.04581 =
0.05156 -0.00486 -0.00107 -0.00029
C7 1 0.068530 0.070594 0.350692 11.00000 0.02915 0.04711 =
0.05242 -0.00870 0.00218 -0.00080
AFIX 13
H7 2 0.064771 0.154738 0.372435 11.00000 -1.20000
AFIX 0
C8 1 0.147554 0.001745 0.394561 11.00000 0.03032 0.04793 =
0.03788 -0.00307 0.00484 -0.00002
AFIX 13
H8 2 0.125486 -0.025945 0.447672 11.00000 -1.20000
AFIX 0
C9 1 0.215340 -0.064547 0.271265 11.00000 0.03396 0.04183 =
0.03810 -0.00680 0.00224 0.00178
AFIX 13
H9 2 0.234195 -0.137186 0.239996 11.00000 -1.20000
AFIX 0
C10 1 0.230758 -0.194191 0.392545 11.00000 0.03681 0.05130 =
0.05144 0.00429 0.00488 0.00793
AFIX 23
H10A 2 0.287825 -0.153707 0.408932 11.00000 -1.20000
H10B 2 0.246275 -0.262075 0.356682 11.00000 -1.20000
AFIX 0
C11 1 0.184215 -0.245218 0.467572 11.00000 0.04306 0.04271 =
0.04375 0.00020 0.00329 0.00311
C12 1 0.232850 -0.250930 0.540823 11.00000 0.05539 0.04980 =
0.05320 0.00191 -0.00856 0.00049
AFIX 43
H12 2 0.293221 -0.221839 0.543764 11.00000 -1.20000
AFIX 0
C13 1 0.192612 -0.299311 0.609367 11.00000 0.09828 0.05617 =
0.04253 0.00336 -0.00860 0.00284
AFIX 43
H13 2 0.226417 -0.303470 0.657915 11.00000 -1.20000
AFIX 0
C14 1 0.104087 -0.341025 0.606847 11.00000 0.08407 0.05091 =
0.05364 0.00354 0.02216 0.00946
AFIX 43
H14 2 0.077330 -0.372248 0.653702 11.00000 -1.20000
AFIX 0
C15 1 0.054117 -0.337027 0.534973 11.00000 0.05080 0.05726 =
0.07041 -0.00149 0.01785 0.00075
AFIX 43
H15 2 -0.006113 -0.366743 0.532843 11.00000 -1.20000
AFIX 0
C16 1 0.094206 -0.288213 0.465345 11.00000 0.04689 0.06691 =
0.04589 -0.00291 0.00023 0.00130
AFIX 43
H16 2 0.060154 -0.284490 0.416915 11.00000 -1.20000
AFIX 0
C17 1 0.375653 0.015810 0.232991 11.00000 0.03331 0.06150 =
0.03824 -0.00236 0.00310 0.00491
C18 1 0.299410 0.014982 0.289006 11.00000 0.02954 0.04792 =
0.03617 -0.00236 0.00189 0.00326
C19 1 0.300706 0.086835 0.356907 11.00000 0.02864 0.04378 =
0.03874 -0.00121 0.00059 0.00574
C20 1 0.380618 0.169209 0.379146 11.00000 0.03373 0.05598 =
0.04268 -0.00552 -0.00091 0.00143
AFIX 23
H20A 2 0.390863 0.165202 0.437625 11.00000 -1.20000
H20B 2 0.364281 0.253733 0.365593 11.00000 -1.20000
AFIX 0
C21 1 0.470845 0.136729 0.336852 11.00000 0.03248 0.06023 =
0.04243 -0.00423 -0.00004 0.00113
C22 1 0.448623 0.112390 0.247211 11.00000 0.03638 0.06864 =
0.04494 -0.00337 0.00887 -0.00031
AFIX 23
H22A 2 0.428355 0.189019 0.222058 11.00000 -1.20000
H22B 2 0.504668 0.086618 0.220431 11.00000 -1.20000
AFIX 0
C23 1 0.515485 0.022974 0.375447 11.00000 0.05108 0.08703 =
0.07120 0.00624 -0.00750 0.02047
AFIX 137
H23A 2 0.473073 -0.045104 0.372690 11.00000 -1.50000
H23B 2 0.530983 0.040080 0.431392 11.00000 -1.50000
H23C 2 0.570515 0.002297 0.346570 11.00000 -1.50000
AFIX 0
C24 1 0.536067 0.248507 0.344177 11.00000 0.03583 0.09152 =
0.07479 -0.01699 0.00390 -0.01432
AFIX 137
H24A 2 0.593444 0.229680 0.318423 11.00000 -1.50000
H24B 2 0.547355 0.266832 0.400681 11.00000 -1.50000
H24C 2 0.508097 0.318752 0.317996 11.00000 -1.50000
AFIX 0
C25 1 0.227803 0.160139 0.481375 11.00000 0.02902 0.04753 =
0.03537 -0.00465 0.00564 0.00046
C26 1 0.203401 0.283726 0.476610 11.00000 0.04560 0.04952 =
0.03481 0.00219 -0.00058 0.00850
AFIX 43
H26 2 0.182929 0.317311 0.427411 11.00000 -1.20000
AFIX 0
C27 1 0.209729 0.356633 0.545525 11.00000 0.05755 0.04321 =
0.04513 -0.00233 0.00161 0.01123
AFIX 43
H27 2 0.193775 0.439688 0.541783 11.00000 -1.20000
AFIX 0
C28 1 0.239083 0.309851 0.619949 11.00000 0.04378 0.05356 =
0.03818 -0.00675 0.00289 0.00256
C29 1 0.260068 0.184760 0.623889 11.00000 0.05564 0.05896 =
0.03415 0.00219 -0.00396 0.00757
AFIX 43
H29 2 0.278120 0.150220 0.673506 11.00000 -1.20000
AFIX 0
C30 1 0.254608 0.110779 0.555460 11.00000 0.04904 0.04344 =
0.04753 0.00117 -0.00026 0.00934
AFIX 43
H30 2 0.269081 0.027258 0.559363 11.00000 -1.20000
AFIX 0
C31 1 0.248887 0.391928 0.693873 11.00000 0.08579 0.06703 =
0.04252 -0.00885 -0.00417 0.01051
AFIX 137
H31A 2 0.189682 0.425533 0.707237 11.00000 -1.50000
H31B 2 0.290888 0.458064 0.682387 11.00000 -1.50000
H31C 2 0.272330 0.344410 0.739032 11.00000 -1.50000
AFIX 0
N1 4 0.172349 -0.105767 0.347706 11.00000 0.03643 0.04207 =
0.03801 -0.00112 0.00465 0.00204
N2 4 0.227159 0.085928 0.408414 11.00000 0.03220 0.04931 =
0.03845 -0.00748 0.00284 0.00056
O1 5 0.379400 -0.055597 0.175007 11.00000 0.05106 0.09516 =
0.05143 -0.03069 0.01701 -0.01037
HKLF 4
REM 20190484 in P21/n #14
REM R1 = 0.0444 for 3531 Fo > 4sig(Fo) and 0.0603 for all 4590 data
REM 319 parameters refined using 0 restraints
END
WGHT 0.0616 0.5371
REM Highest difference peak 0.269, deepest hole -0.450, 1-sigma level 0.058
Q1 1 0.1781 -0.0206 0.2476 11.00000 0.05 0.27
Q2 1 0.2243 0.4636 0.6788 11.00000 0.05 0.23
Q3 1 0.3333 0.0143 0.2632 11.00000 0.05 0.23
Q4 1 0.2201 0.3231 0.7551 11.00000 0.05 0.22
Q5 1 0.3086 0.3877 0.7243 11.00000 0.05 0.21
Q6 1 0.1999 -0.2092 0.5010 11.00000 0.05 0.21
Q7 1 0.1327 0.0785 0.2419 11.00000 0.05 0.20
Q8 1 -0.0216 -0.0830 0.4085 11.00000 0.05 0.20
Q9 1 0.3159 0.0172 0.3328 11.00000 0.05 0.20
Q10 1 0.3547 0.5818 0.7135 11.00000 0.05 0.20
Q11 1 0.4756 0.0731 0.3583 11.00000 0.05 0.20
Q12 1 0.2024 -0.2220 0.4353 11.00000 0.05 0.20
Q13 1 -0.0633 0.1420 0.2541 11.00000 0.05 0.19
Q14 1 0.2750 0.0628 0.7387 11.00000 0.05 0.18
Q15 1 0.0842 -0.0068 0.0053 11.00000 0.05 0.18
Q16 1 0.2622 -0.0303 0.2857 11.00000 0.05 0.18
Q17 1 0.4227 0.1517 0.3498 11.00000 0.05 0.18
Q18 1 -0.0159 -0.1030 0.3519 11.00000 0.05 0.18
Q19 1 0.1877 0.2250 0.4867 11.00000 0.05 0.18
Q20 1 0.0979 0.0977 0.3092 11.00000 0.05 0.17
REM The information below was added by Olex2.
REM
REM R1 = 0.0444 for 3531 Fo > 4sig(Fo) and 0.0603 for all 10942 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.27, deepest hole -0.45
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0603
REM R1_gt = 0.0444
REM wR_ref = 0.1261
REM GOOF = 1.015
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 10942
REM Reflections_gt = 3531
REM Parameters = n/a
REM Hole = -0.45
REM Peak = 0.27
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_201803150_tw
_database_code_depnum_ccdc_archive 'CCDC 1944660'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-01 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2018-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C39 H39 N5 O5'
_chemical_formula_sum 'C39 H39 N5 O5'
_chemical_formula_weight 657.75
_chemical_melting_point ?
_chemical_oxdiff_formula C40H30N3O5Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.80408(14)
_cell_length_b 18.74504(18)
_cell_length_c 31.2581(4)
_cell_angle_alpha 90
_cell_angle_beta 79.1361(11)
_cell_angle_gamma 90
_cell_volume 6792.46(13)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 13858
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.6640
_cell_measurement_theta_min 3.7250
_shelx_estimated_absorpt_T_max 0.934
_shelx_estimated_absorpt_T_min 0.879
_exptl_absorpt_coefficient_mu 0.697
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.84160
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour yellow
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.286
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 2784
_exptl_crystal_size_max 0.19
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents ?
_diffrn_reflns_av_unetI/netI 0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 37
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 11515
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full 67.096
_diffrn_reflns_theta_max 67.096
_diffrn_reflns_theta_min 3.722
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -74.00 -16.80 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 -19.0000 60.0000 143
#__ type_ start__ end____ width___ exp.time_
2 omega -94.00 -62.80 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 90.0000 78
#__ type_ start__ end____ width___ exp.time_
3 omega 24.00 50.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 -60.0000 65
#__ type_ start__ end____ width___ exp.time_
4 omega 2.00 37.20 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 90.0000 88
#__ type_ start__ end____ width___ exp.time_
5 omega -6.00 68.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -97.0000 -153.0000 185
#__ type_ start__ end____ width___ exp.time_
6 omega 0.00 26.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 19.0000 90.0000 65
#__ type_ start__ end____ width___ exp.time_
7 omega 50.00 103.20 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -90.0000 133
#__ type_ start__ end____ width___ exp.time_
8 omega -16.00 52.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -57.0000 90.0000 170
#__ type_ start__ end____ width___ exp.time_
9 omega 61.00 93.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -150.0000 80
#__ type_ start__ end____ width___ exp.time_
10 omega 45.00 74.20 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 90.0000 73
#__ type_ start__ end____ width___ exp.time_
11 omega 46.00 72.00 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 19.0000 90.0000 65
#__ type_ start__ end____ width___ exp.time_
12 omega 60.00 103.20 0.4000 16.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 77.0000 -60.0000 108
#__ type_ start__ end____ width___ exp.time_
13 omega 74.00 100.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -97.0000 -153.0000 65
#__ type_ start__ end____ width___ exp.time_
14 omega 100.80 178.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 -60.0000 193
#__ type_ start__ end____ width___ exp.time_
15 omega 46.00 85.20 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 30.0000 98
#__ type_ start__ end____ width___ exp.time_
16 omega 38.00 113.20 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -60.0000 188
#__ type_ start__ end____ width___ exp.time_
17 omega 42.00 108.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 90.0000 165
#__ type_ start__ end____ width___ exp.time_
18 omega 83.00 175.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 77.0000 -120.0000 230
#__ type_ start__ end____ width___ exp.time_
19 omega 40.00 90.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 120.0000 125
#__ type_ start__ end____ width___ exp.time_
20 omega 56.00 82.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 150.0000 65
#__ type_ start__ end____ width___ exp.time_
21 omega 111.00 169.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 15.0000 -180.0000 145
#__ type_ start__ end____ width___ exp.time_
22 omega 45.00 73.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 -180.0000 70
#__ type_ start__ end____ width___ exp.time_
23 omega 68.00 94.00 0.4000 52.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 15.0000 -180.0000 65
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.1220333000
_diffrn_orient_matrix_UB_12 0.0177796000
_diffrn_orient_matrix_UB_13 -0.0076587000
_diffrn_orient_matrix_UB_21 0.0513503000
_diffrn_orient_matrix_UB_22 0.0252290000
_diffrn_orient_matrix_UB_23 -0.0465206000
_diffrn_orient_matrix_UB_31 -0.0115330000
_diffrn_orient_matrix_UB_32 -0.0761516000
_diffrn_orient_matrix_UB_33 -0.0172119000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 9893
_reflns_number_total 11515
_reflns_odcompleteness_completeness 94.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max 0.381
_refine_diff_density_min -0.274
_refine_diff_density_rms 0.041
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.038
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 890
_refine_ls_number_reflns 11515
_refine_ls_number_restraints 44
_refine_ls_R_factor_all 0.0596
_refine_ls_R_factor_gt 0.0516
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0903P)^2^+0.7126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1400
_refine_ls_wR_factor_ref 0.1465
_refine_special_details
;
Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.6569(10)
0.3431(10)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
3. Rigid bond restraints
C36', C37'
with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
C24, C25
with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C36') \\sim Ueq, Uanis(C37') \\sim Ueq, Uanis(C38') \\sim Ueq,
Uanis(C39') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C33') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
C16(H16), C18(H18), C19(H19), C20(H20), C28(H28), C30(H30), C16'(H16'),
C18'(H18'), C19'(H19'), C20'(H20'), C28'(H28'), C30'(H30')
5.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C4(H4A,H4B), C21(H21A,H21B), C33(H33A,H33B), C2'(H2'A,H2'B),
C4'(H4'A,H4'B), C21'(H21C,H21D), C33'(H33C,H33D)
5.c Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11), C13(H13), C14(H14), C23(H23), C24(H24), C25(H25),
C26(H26), C27(H27), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38),
C39(H39), C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'), C23'(H23'),
C24'(H24'), C25'(H25'), C26'(H26'), C27'(H27'), C31'(H31'), C32'(H32'),
C35'(H35'), C36'(H36'), C37'(H37'), C38'(H38'), C39'(H39')
5.d Idealised Me refined as rotating group:
C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C7'(H7'A,H7'B,H7'C),
C8'(H8'A,H8'B,H8'C), C15'(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3358(2) 0.83578(13) 0.45512(8) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.3112(3) 0.75714(14) 0.45657(8) 0.0580(7) Uani 1 1 d . . . . .
H2A H 0.2297 0.7500 0.4567 0.070 Uiso 1 1 calc R . . . .
H2B H 0.3275 0.7379 0.4836 0.070 Uiso 1 1 calc R . . . .
C3 C 0.3809(3) 0.71575(14) 0.41858(9) 0.0567(7) Uani 1 1 d . . . . .
C4 C 0.3596(3) 0.75061(13) 0.37664(8) 0.0542(6) Uani 1 1 d . . . . .
H4A H 0.4129 0.7303 0.3522 0.065 Uiso 1 1 calc R . . . .
H4B H 0.2821 0.7389 0.3729 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3732(2) 0.83036(12) 0.37536(7) 0.0428(5) Uani 1 1 d . . . . .
C6 C 0.3679(2) 0.86930(12) 0.41277(7) 0.0415(5) Uani 1 1 d . . . . .
C7 C 0.5086(3) 0.71839(19) 0.42136(11) 0.0738(9) Uani 1 1 d . . . . .
H7A H 0.5522 0.6907 0.3981 0.111 Uiso 1 1 calc GR . . . .
H7B H 0.5190 0.6992 0.4488 0.111 Uiso 1 1 calc GR . . . .
H7C H 0.5348 0.7670 0.4189 0.111 Uiso 1 1 calc GR . . . .
C8 C 0.3377(4) 0.63923(15) 0.41979(11) 0.0842(11) Uani 1 1 d . . . . .
H8A H 0.2566 0.6391 0.4193 0.126 Uiso 1 1 calc GR . . . .
H8B H 0.3509 0.6165 0.4459 0.126 Uiso 1 1 calc GR . . . .
H8C H 0.3783 0.6139 0.3949 0.126 Uiso 1 1 calc GR . . . .
C9 C 0.3821(2) 0.82946(13) 0.29595(8) 0.0459(5) Uani 1 1 d . . . . .
C10 C 0.2775(3) 0.79860(15) 0.29218(10) 0.0577(6) Uani 1 1 d . . . . .
H10 H 0.2171 0.7981 0.3160 0.069 Uiso 1 1 calc R . . . .
C11 C 0.2629(3) 0.76909(15) 0.25380(10) 0.0664(8) Uani 1 1 d . . . . .
H11 H 0.1929 0.7476 0.2521 0.080 Uiso 1 1 calc R . . . .
C12 C 0.3495(4) 0.77032(16) 0.21753(11) 0.0759(10) Uani 1 1 d . . . . .
C13 C 0.4539(4) 0.80253(16) 0.22095(10) 0.0736(9) Uani 1 1 d . . . . .
H13 H 0.5131 0.8046 0.1967 0.088 Uiso 1 1 calc R . . . .
C14 C 0.4701(2) 0.83126(14) 0.25989(8) 0.0560(6) Uani 1 1 d . . . . .
H14 H 0.5406 0.8519 0.2619 0.067 Uiso 1 1 calc R . . . .
C15 C 0.3324(6) 0.7392(3) 0.17446(14) 0.125(2) Uani 1 1 d . . . . .
H15A H 0.3455 0.6886 0.1744 0.188 Uiso 1 1 calc GR . . . .
H15B H 0.3858 0.7608 0.1511 0.188 Uiso 1 1 calc GR . . . .
H15C H 0.2549 0.7483 0.1706 0.188 Uiso 1 1 calc GR . . . .
C16 C 0.40285(19) 0.94158(12) 0.33341(7) 0.0413(5) Uani 1 1 d . . . . .
H16 H 0.4465 0.9559 0.3049 0.050 Uiso 1 1 calc R . . . .
C17 C 0.46427(19) 0.97049(12) 0.36860(7) 0.0410(5) Uani 1 1 d . . . . .
C18 C 0.39490(19) 0.94762(12) 0.41232(7) 0.0409(5) Uani 1 1 d . . . . .
H18 H 0.4396 0.9578 0.4351 0.049 Uiso 1 1 calc R . . . .
C19 C 0.2860(2) 0.99488(12) 0.41981(7) 0.0430(5) Uani 1 1 d . . . . .
H19 H 0.2186 0.9746 0.4391 0.052 Uiso 1 1 calc R . . . .
C20 C 0.2640(2) 1.02219(12) 0.37527(7) 0.0436(5) Uani 1 1 d . . . . .
H20 H 0.1862 1.0421 0.3781 0.052 Uiso 1 1 calc R . . . .
C21 C 0.2581(2) 0.99893(15) 0.29805(8) 0.0533(6) Uani 1 1 d . . . . .
H21A H 0.2762 0.9620 0.2761 0.064 Uiso 1 1 calc R . . . .
H21B H 0.3055 1.0401 0.2881 0.064 Uiso 1 1 calc R . . . .
C22 C 0.1336(2) 1.01912(14) 0.30223(8) 0.0521(6) Uani 1 1 d . . . . .
C23 C 0.1029(3) 1.08333(18) 0.28504(11) 0.0734(9) Uani 1 1 d . . . . .
H23 H 0.1595 1.1150 0.2719 0.088 Uiso 1 1 calc R . . . .
C24 C -0.0133(4) 1.0996(2) 0.28770(14) 0.0930(10) Uani 1 1 d . U . . .
H24 H -0.0338 1.1421 0.2758 0.112 Uiso 1 1 calc R . . . .
C25 C -0.0972(4) 1.0547(3) 0.30735(13) 0.0940(11) Uani 1 1 d . U . . .
H25 H -0.1744 1.0669 0.3092 0.113 Uiso 1 1 calc R . . . .
C26 C -0.0689(3) 0.9920(2) 0.32435(14) 0.0874(11) Uani 1 1 d . . . . .
H26 H -0.1265 0.9613 0.3379 0.105 Uiso 1 1 calc R . . . .
C27 C 0.0466(3) 0.97405(17) 0.32145(11) 0.0692(8) Uani 1 1 d . . . . .
H27 H 0.0654 0.9307 0.3327 0.083 Uiso 1 1 calc R . . . .
C28 C 0.3155(2) 1.07382(12) 0.42990(8) 0.0481(5) Uani 1 1 d . . . . .
H28 H 0.2441 1.1007 0.4397 0.058 Uiso 1 1 calc R . . . .
C29 C 0.3532(2) 1.08160(12) 0.38060(8) 0.0466(5) Uani 1 1 d . . . . .
C30 C 0.4758(2) 1.05334(13) 0.36568(8) 0.0471(5) Uani 1 1 d . . . . .
H30 H 0.5048 1.0676 0.3354 0.057 Uiso 1 1 calc R . . . .
C31 C 0.5537(2) 1.08213(13) 0.39440(9) 0.0535(6) Uani 1 1 d . . . . .
H31 H 0.6310 1.0907 0.3828 0.064 Uiso 1 1 calc R . . . .
C32 C 0.5129(2) 1.09560(13) 0.43647(9) 0.0560(6) Uani 1 1 d . . . . .
H32 H 0.5658 1.1085 0.4537 0.067 Uiso 1 1 calc R . . . .
C33 C 0.3682(3) 1.07306(16) 0.50303(9) 0.0653(7) Uani 1 1 d . . . . .
H33A H 0.4237 1.0949 0.5182 0.078 Uiso 1 1 calc R . . . .
H33B H 0.3739 1.0218 0.5061 0.078 Uiso 1 1 calc R . . . .
C34 C 0.2497(3) 1.09646(16) 0.52399(9) 0.0620(7) Uani 1 1 d . . . . .
C35 C 0.1641(4) 1.0466(2) 0.53381(13) 0.0910(11) Uani 1 1 d . . . . .
H35 H 0.1805 0.9988 0.5273 0.109 Uiso 1 1 calc R . . . .
C36 C 0.0531(5) 1.0664(3) 0.55332(19) 0.1263(18) Uani 1 1 d . . . . .
H36 H -0.0042 1.0319 0.5596 0.152 Uiso 1 1 calc R . . . .
C37 C 0.0274(6) 1.1358(4) 0.56341(18) 0.136(2) Uani 1 1 d . . . . .
H37 H -0.0470 1.1490 0.5765 0.163 Uiso 1 1 calc R . . . .
C38 C 0.1124(6) 1.1856(3) 0.55410(18) 0.128(2) Uani 1 1 d . . . . .
H38 H 0.0959 1.2332 0.5609 0.154 Uiso 1 1 calc R . . . .
C39 C 0.2242(5) 1.1658(2) 0.53439(13) 0.0968(12) Uani 1 1 d . . . . .
H39 H 0.2816 1.2003 0.5283 0.116 Uiso 1 1 calc R . . . .
N1 N 0.39904(18) 0.86378(10) 0.33543(6) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.58617(17) 0.94048(11) 0.35991(7) 0.0494(5) Uani 1 1 d . . . . .
N3 N 0.28837(16) 0.97298(10) 0.33917(6) 0.0430(4) Uani 1 1 d . . . . .
N4 N 0.3385(2) 1.15339(12) 0.36133(8) 0.0596(6) Uani 1 1 d . . . . .
N5 N 0.3983(2) 1.09185(11) 0.45629(7) 0.0523(5) Uani 1 1 d . . . . .
O1 O 0.3265(2) 0.87118(10) 0.48858(5) 0.0620(5) Uani 1 1 d . . . . .
O2 O 0.62199(18) 0.91108(12) 0.38897(7) 0.0710(6) Uani 1 1 d . . . . .
O3 O 0.64289(18) 0.94943(14) 0.32353(7) 0.0757(6) Uani 1 1 d . . . . .
O4 O 0.2916(3) 1.19973(12) 0.38431(9) 0.1025(9) Uani 1 1 d . . . . .
O5 O 0.3707(3) 1.16153(13) 0.32282(9) 0.1080(11) Uani 1 1 d . . . . .
C1' C 0.9313(2) 0.33785(15) 0.45155(9) 0.0543(6) Uani 1 1 d . . . . .
C2' C 0.9609(3) 0.26051(15) 0.45474(8) 0.0588(7) Uani 1 1 d . . . . .
H2'A H 0.9151 0.2410 0.4812 0.071 Uiso 1 1 calc R . . . .
H2'B H 1.0414 0.2565 0.4571 0.071 Uiso 1 1 calc R . . . .
C3' C 0.9403(2) 0.21610(14) 0.41615(9) 0.0548(6) Uani 1 1 d . . . . .
C4' C 1.0094(3) 0.25073(14) 0.37467(8) 0.0556(6) Uani 1 1 d . . . . .
H4'A H 1.0908 0.2414 0.3734 0.067 Uiso 1 1 calc R . . . .
H4'B H 0.9874 0.2285 0.3494 0.067 Uiso 1 1 calc R . . . .
C5' C 0.9913(2) 0.33048(13) 0.37239(8) 0.0466(5) Uani 1 1 d . . . . .
C6' C 0.9511(2) 0.36994(13) 0.40829(8) 0.0471(5) Uani 1 1 d . . . . .
C7' C 0.8129(3) 0.21323(17) 0.41472(10) 0.0664(7) Uani 1 1 d . . . . .
H7'A H 0.7716 0.1931 0.4414 0.100 Uiso 1 1 calc GR . . . .
H7'B H 0.8013 0.1841 0.3906 0.100 Uiso 1 1 calc GR . . . .
H7'C H 0.7851 0.2606 0.4112 0.100 Uiso 1 1 calc GR . . . .
C8' C 0.9841(3) 0.13981(16) 0.42009(11) 0.0752(9) Uani 1 1 d . . . . .
H8'A H 1.0646 0.1411 0.4216 0.113 Uiso 1 1 calc GR . . . .
H8'B H 0.9736 0.1126 0.3951 0.113 Uiso 1 1 calc GR . . . .
H8'C H 0.9417 0.1181 0.4460 0.113 Uiso 1 1 calc GR . . . .
C9' C 1.0732(2) 0.32673(13) 0.29332(8) 0.0475(5) Uani 1 1 d . . . . .
C10' C 1.1807(2) 0.29679(15) 0.29265(10) 0.0579(7) Uani 1 1 d . . . . .
H10' H 1.2121 0.2950 0.3178 0.070 Uiso 1 1 calc R . . . .
C11' C 1.2411(3) 0.26929(15) 0.25325(11) 0.0722(9) Uani 1 1 d . . . . .
H11' H 1.3119 0.2472 0.2528 0.087 Uiso 1 1 calc R . . . .
C12' C 1.1993(3) 0.27380(16) 0.21539(11) 0.0732(9) Uani 1 1 d . . . . .
C13' C 1.0914(4) 0.30329(17) 0.21714(10) 0.0749(9) Uani 1 1 d . . . . .
H13' H 1.0609 0.3058 0.1918 0.090 Uiso 1 1 calc R . . . .
C14' C 1.0278(2) 0.32906(14) 0.25537(9) 0.0580(6) Uani 1 1 d . . . . .
H14' H 0.9547 0.3480 0.2559 0.070 Uiso 1 1 calc R . . . .
C15' C 1.2717(5) 0.2478(2) 0.17299(13) 0.1177(18) Uani 1 1 d . . . . .
H15D H 1.2832 0.1973 0.1746 0.177 Uiso 1 1 calc GR . . . .
H15E H 1.3450 0.2716 0.1681 0.177 Uiso 1 1 calc GR . . . .
H15F H 1.2326 0.2582 0.1494 0.177 Uiso 1 1 calc GR . . . .
C16' C 1.0069(2) 0.43910(13) 0.32823(8) 0.0452(5) Uani 1 1 d . . . . .
H16' H 0.9970 0.4516 0.2987 0.054 Uiso 1 1 calc R . . . .
C17' C 0.9048(2) 0.46824(13) 0.36057(8) 0.0458(5) Uani 1 1 d . . . . .
C18' C 0.9214(2) 0.44732(13) 0.40592(8) 0.0474(5) Uani 1 1 d . . . . .
H18' H 0.8500 0.4570 0.4268 0.057 Uiso 1 1 calc R . . . .
C19' C 1.0176(2) 0.49751(14) 0.41562(8) 0.0515(6) Uani 1 1 d . . . . .
H19' H 1.0611 0.4795 0.4372 0.062 Uiso 1 1 calc R . . . .
C20' C 1.0926(2) 0.52330(13) 0.37206(8) 0.0501(6) Uani 1 1 d . . . . .
H20' H 1.1652 0.5443 0.3769 0.060 Uiso 1 1 calc R . . . .
C21' C 1.1856(2) 0.49913(16) 0.29586(9) 0.0595(7) Uani 1 1 d . . . . .
H21C H 1.1484 0.5402 0.2856 0.071 Uiso 1 1 calc R . . . .
H21D H 1.1907 0.4622 0.2739 0.071 Uiso 1 1 calc R . . . .
C22' C 1.3055(2) 0.51989(15) 0.30071(9) 0.0577(7) Uani 1 1 d . . . . .
C23' C 1.3523(3) 0.58307(19) 0.28255(12) 0.0795(9) Uani 1 1 d . . . . .
H23' H 1.3072 0.6138 0.2694 0.095 Uiso 1 1 calc R . . . .
C24' C 1.4657(4) 0.6011(3) 0.28369(15) 0.1033(15) Uani 1 1 d . . . . .
H24' H 1.4962 0.6437 0.2713 0.124 Uiso 1 1 calc R . . . .
C25' C 1.5332(3) 0.5561(3) 0.30315(14) 0.0995(14) Uani 1 1 d . . . . .
H25' H 1.6098 0.5674 0.3035 0.119 Uiso 1 1 calc R . . . .
C26' C 1.4861(3) 0.4954(3) 0.32172(16) 0.0989(13) Uani 1 1 d . . . . .
H26' H 1.5308 0.4652 0.3354 0.119 Uiso 1 1 calc R . . . .
C27' C 1.3735(3) 0.47696(19) 0.32103(13) 0.0800(10) Uani 1 1 d . . . . .
H27' H 1.3432 0.4350 0.3344 0.096 Uiso 1 1 calc R . . . .
C28' C 0.9742(3) 0.57570(14) 0.42292(9) 0.0557(6) Uani 1 1 d . . . . .
H28' H 1.0304 0.6043 0.4348 0.067 Uiso 1 1 calc R . . . .
C29' C 0.9972(2) 0.58162(13) 0.37338(9) 0.0523(6) Uani 1 1 d . . . . .
C30' C 0.8960(2) 0.55103(13) 0.35516(8) 0.0504(6) Uani 1 1 d . . . . .
H30' H 0.9043 0.5632 0.3242 0.060 Uiso 1 1 calc R . . . .
C31' C 0.7839(3) 0.57992(15) 0.38006(9) 0.0586(7) Uani 1 1 d . . . . .
H31' H 0.7224 0.5874 0.3659 0.070 Uiso 1 1 calc R . . . .
C32' C 0.7722(3) 0.59495(17) 0.42234(10) 0.0681(8) Uani 1 1 d . . . . .
H32' H 0.6995 0.6086 0.4371 0.082 Uiso 1 1 calc R . . . .
C33' C 0.8398(4) 0.5800(3) 0.49234(13) 0.1177(16) Uani 1 1 d . U . . .
H33C H 0.8983 0.6059 0.5041 0.141 Uiso 1 1 calc R . . . .
H33D H 0.8504 0.5296 0.4976 0.141 Uiso 1 1 calc R . . . .
C34' C 0.7252(4) 0.6017(2) 0.51652(11) 0.0844(10) Uani 1 1 d . . . . .
C35' C 0.6977(5) 0.6706(3) 0.52943(15) 0.1081(14) Uani 1 1 d . . . . .
H35' H 0.7552 0.7050 0.5230 0.130 Uiso 1 1 calc R . . . .
C36' C 0.5918(6) 0.6919(3) 0.55101(19) 0.137(2) Uani 1 1 d . U . . .
H36' H 0.5774 0.7392 0.5591 0.164 Uiso 1 1 calc R . . . .
C37' C 0.5110(7) 0.6432(5) 0.5599(2) 0.167(3) Uani 1 1 d . U . . .
H37' H 0.4387 0.6573 0.5748 0.200 Uiso 1 1 calc R . . . .
C38' C 0.5263(7) 0.5743(4) 0.5489(3) 0.181(3) Uani 1 1 d . U . . .
H38' H 0.4660 0.5419 0.5557 0.217 Uiso 1 1 calc R . . . .
C39' C 0.6372(7) 0.5518(3) 0.5265(2) 0.149(2) Uani 1 1 d . U . . .
H39' H 0.6504 0.5043 0.5186 0.179 Uiso 1 1 calc R . . . .
N1' N 1.01108(18) 0.36099(10) 0.33169(6) 0.0456(4) Uani 1 1 d . . . . .
N2' N 0.79671(19) 0.43673(12) 0.34870(8) 0.0550(5) Uani 1 1 d . . . . .
N3' N 1.11258(17) 0.47298(11) 0.33659(7) 0.0474(5) Uani 1 1 d . . . . .
N4' N 1.0344(2) 0.65298(12) 0.35376(9) 0.0645(6) Uani 1 1 d . . . . .
N5' N 0.8592(2) 0.59173(13) 0.44557(8) 0.0609(6) Uani 1 1 d . . . . .
O1' O 0.8950(2) 0.37354(11) 0.48405(6) 0.0718(6) Uani 1 1 d . . . . .
O2' O 0.7287(2) 0.40624(14) 0.37631(8) 0.0832(7) Uani 1 1 d . . . . .
O3' O 0.7832(2) 0.44481(14) 0.31100(8) 0.0791(6) Uani 1 1 d . . . . .
O4' O 1.0620(3) 0.69826(14) 0.37696(10) 0.1136(11) Uani 1 1 d . . . . .
O5' O 1.0419(4) 0.66117(14) 0.31531(9) 0.1131(11) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0493(13) 0.0465(13) 0.0445(13) 0.0012(10) -0.0014(10) -0.0037(11)
C2 0.0683(17) 0.0501(14) 0.0496(14) 0.0047(11) 0.0041(12) -0.0085(12)
C3 0.0674(17) 0.0457(13) 0.0520(15) 0.0042(10) 0.0013(12) -0.0004(12)
C4 0.0663(17) 0.0447(13) 0.0507(13) -0.0049(10) -0.0089(12) -0.0018(12)
C5 0.0416(11) 0.0448(12) 0.0412(11) -0.0028(9) -0.0058(9) -0.0010(10)
C6 0.0422(11) 0.0425(12) 0.0388(11) -0.0003(9) -0.0051(9) -0.0007(10)
C7 0.073(2) 0.078(2) 0.0668(19) 0.0147(15) -0.0047(16) 0.0192(16)
C8 0.130(3) 0.0447(15) 0.071(2) 0.0002(13) 0.001(2) -0.0078(18)
C9 0.0520(13) 0.0439(12) 0.0442(13) -0.0036(9) -0.0151(10) 0.0025(10)
C10 0.0515(15) 0.0602(16) 0.0645(17) -0.0051(12) -0.0194(13) -0.0016(12)
C11 0.0740(18) 0.0560(15) 0.080(2) -0.0061(14) -0.0412(17) 0.0013(13)
C12 0.119(3) 0.0547(16) 0.0641(19) -0.0120(13) -0.045(2) 0.0080(18)
C13 0.108(3) 0.0609(17) 0.0470(15) -0.0107(12) -0.0015(16) 0.0049(18)
C14 0.0619(15) 0.0549(14) 0.0500(14) -0.0061(11) -0.0073(12) 0.0019(12)
C15 0.206(6) 0.105(3) 0.082(3) -0.031(2) -0.071(3) 0.000(3)
C16 0.0399(11) 0.0475(12) 0.0364(11) -0.0003(9) -0.0070(9) -0.0030(10)
C17 0.0361(11) 0.0439(12) 0.0433(12) 0.0020(9) -0.0085(9) -0.0022(9)
C18 0.0417(11) 0.0444(12) 0.0385(11) -0.0005(9) -0.0126(9) -0.0028(9)
C19 0.0419(12) 0.0473(12) 0.0402(11) -0.0047(9) -0.0084(9) -0.0010(10)
C20 0.0417(12) 0.0457(12) 0.0458(12) -0.0018(9) -0.0145(10) 0.0029(10)
C21 0.0566(15) 0.0651(16) 0.0407(12) 0.0052(11) -0.0157(11) -0.0029(12)
C22 0.0588(15) 0.0569(15) 0.0464(13) -0.0064(11) -0.0250(12) 0.0037(12)
C23 0.088(2) 0.074(2) 0.0653(19) 0.0045(14) -0.0320(17) 0.0125(17)
C24 0.109(3) 0.092(2) 0.088(2) -0.0065(18) -0.044(2) 0.0442(18)
C25 0.075(2) 0.122(3) 0.096(3) -0.027(2) -0.0444(19) 0.0352(17)
C26 0.0542(17) 0.102(3) 0.110(3) -0.019(2) -0.0268(19) -0.0037(18)
C27 0.0582(17) 0.0646(18) 0.090(2) -0.0045(15) -0.0270(16) -0.0018(14)
C28 0.0517(13) 0.0445(12) 0.0511(13) -0.0052(10) -0.0173(11) 0.0058(10)
C29 0.0549(14) 0.0394(12) 0.0494(13) 0.0027(9) -0.0200(11) -0.0022(10)
C30 0.0502(13) 0.0429(12) 0.0499(13) 0.0049(10) -0.0137(10) -0.0064(10)
C31 0.0491(13) 0.0494(13) 0.0650(16) 0.0053(11) -0.0185(12) -0.0122(11)
C32 0.0617(16) 0.0465(13) 0.0672(17) -0.0016(11) -0.0309(13) -0.0068(12)
C33 0.080(2) 0.0643(17) 0.0568(17) 0.0015(12) -0.0252(14) 0.0024(15)
C34 0.0788(19) 0.0629(16) 0.0470(14) -0.0071(11) -0.0189(13) 0.0045(15)
C35 0.096(3) 0.080(2) 0.092(3) -0.0002(19) -0.005(2) -0.003(2)
C36 0.083(3) 0.144(5) 0.139(4) 0.020(4) 0.014(3) -0.007(3)
C37 0.115(4) 0.164(6) 0.109(4) 0.023(4) 0.027(3) 0.052(4)
C38 0.156(5) 0.104(4) 0.113(4) -0.014(3) 0.007(4) 0.053(4)
C39 0.121(3) 0.076(2) 0.090(3) -0.0102(19) -0.011(2) 0.010(2)
N1 0.0488(10) 0.0462(10) 0.0375(10) -0.0032(8) -0.0070(8) -0.0029(9)
N2 0.0379(10) 0.0539(12) 0.0563(12) 0.0001(9) -0.0091(9) -0.0041(9)
N3 0.0400(10) 0.0505(11) 0.0401(10) -0.0024(8) -0.0120(8) -0.0013(8)
N4 0.0701(15) 0.0451(12) 0.0696(15) 0.0050(10) -0.0287(12) 0.0005(11)
N5 0.0610(13) 0.0497(12) 0.0511(12) -0.0073(9) -0.0227(10) -0.0009(10)
O1 0.0890(14) 0.0573(10) 0.0383(9) -0.0020(7) -0.0086(9) -0.0100(10)
O2 0.0542(11) 0.0885(15) 0.0738(13) 0.0093(11) -0.0211(10) 0.0156(11)
O3 0.0472(10) 0.1083(17) 0.0671(13) 0.0081(11) 0.0007(10) 0.0035(11)
O4 0.151(3) 0.0538(13) 0.1031(19) 0.0021(12) -0.0252(19) 0.0335(16)
O5 0.165(3) 0.0726(15) 0.0837(18) 0.0288(13) -0.0154(19) 0.0219(17)
C1' 0.0554(14) 0.0594(15) 0.0485(14) 0.0058(11) -0.0106(11) -0.0044(12)
C2' 0.0628(16) 0.0646(16) 0.0497(14) 0.0139(12) -0.0127(12) -0.0034(13)
C3' 0.0581(15) 0.0526(14) 0.0524(15) 0.0120(11) -0.0072(12) -0.0017(12)
C4' 0.0600(15) 0.0497(14) 0.0533(15) 0.0068(11) -0.0007(12) 0.0022(12)
C5' 0.0423(12) 0.0492(13) 0.0469(13) 0.0076(10) -0.0049(10) -0.0012(10)
C6' 0.0466(12) 0.0483(13) 0.0444(12) 0.0045(10) -0.0037(10) -0.0028(10)
C7' 0.0664(18) 0.0657(17) 0.0664(18) 0.0134(13) -0.0108(14) -0.0134(14)
C8' 0.093(2) 0.0552(16) 0.074(2) 0.0163(14) -0.0063(18) 0.0063(16)
C9' 0.0439(12) 0.0463(12) 0.0481(13) 0.0038(10) 0.0025(10) -0.0020(10)
C10' 0.0467(14) 0.0582(16) 0.0649(17) 0.0074(12) -0.0001(12) -0.0003(12)
C11' 0.0559(16) 0.0560(15) 0.092(2) 0.0022(16) 0.0195(17) 0.0042(13)
C12' 0.089(2) 0.0580(17) 0.0617(19) -0.0097(13) 0.0152(17) -0.0027(17)
C13' 0.102(3) 0.0680(19) 0.0555(17) -0.0093(14) -0.0156(17) -0.0033(19)
C14' 0.0608(15) 0.0557(14) 0.0571(15) -0.0012(12) -0.0103(13) -0.0016(12)
C15' 0.148(4) 0.093(3) 0.087(3) -0.023(2) 0.040(3) 0.002(3)
C16' 0.0437(12) 0.0486(13) 0.0433(12) 0.0055(9) -0.0080(10) 0.0018(10)
C17' 0.0396(11) 0.0498(13) 0.0482(13) 0.0029(10) -0.0087(10) 0.0020(10)
C18' 0.0439(12) 0.0505(13) 0.0459(13) 0.0022(10) -0.0035(10) 0.0022(10)
C19' 0.0508(13) 0.0565(14) 0.0488(13) 0.0023(11) -0.0138(11) 0.0018(11)
C20' 0.0428(12) 0.0520(14) 0.0565(14) 0.0045(11) -0.0122(11) -0.0018(11)
C21' 0.0503(14) 0.0635(16) 0.0619(16) 0.0112(13) -0.0040(13) -0.0026(12)
C22' 0.0483(14) 0.0579(15) 0.0612(16) -0.0021(12) 0.0046(12) -0.0009(12)
C23' 0.077(2) 0.079(2) 0.078(2) 0.0117(16) -0.0020(18) -0.0200(18)
C24' 0.092(3) 0.114(3) 0.095(3) 0.002(2) 0.005(2) -0.056(3)
C25' 0.0542(19) 0.142(4) 0.095(3) -0.028(3) 0.003(2) -0.026(2)
C26' 0.0546(19) 0.120(3) 0.124(3) -0.017(3) -0.020(2) 0.015(2)
C27' 0.0551(17) 0.0690(19) 0.116(3) 0.0037(18) -0.0155(18) 0.0054(15)
C28' 0.0583(15) 0.0514(14) 0.0594(15) -0.0040(11) -0.0158(12) 0.0007(12)
C29' 0.0517(13) 0.0444(13) 0.0609(15) 0.0047(11) -0.0110(12) 0.0010(11)
C30' 0.0517(13) 0.0481(13) 0.0520(14) 0.0043(10) -0.0117(11) 0.0053(11)
C31' 0.0557(15) 0.0604(16) 0.0609(16) 0.0016(12) -0.0137(12) 0.0160(13)
C32' 0.0602(16) 0.0752(19) 0.0678(18) -0.0070(14) -0.0095(14) 0.0229(15)
C33' 0.106(3) 0.182(5) 0.064(2) -0.009(2) -0.013(2) 0.031(3)
C34' 0.094(3) 0.096(2) 0.0571(18) -0.0038(16) -0.0001(18) 0.005(2)
C35' 0.120(4) 0.094(3) 0.106(3) -0.016(2) -0.009(3) -0.017(3)
C36' 0.144(4) 0.125(4) 0.129(4) -0.043(3) 0.004(3) 0.020(3)
C37' 0.137(5) 0.184(6) 0.150(5) -0.034(5) 0.045(4) -0.001(4)
C38' 0.156(5) 0.172(6) 0.189(6) 0.027(5) 0.036(5) -0.069(5)
C39' 0.183(6) 0.097(3) 0.158(5) 0.014(3) -0.008(4) -0.027(4)
N1' 0.0457(10) 0.0453(10) 0.0437(10) 0.0030(8) -0.0031(8) 0.0016(9)
N2' 0.0432(11) 0.0606(13) 0.0611(14) -0.0001(10) -0.0094(10) 0.0016(10)
N3' 0.0410(10) 0.0507(11) 0.0494(11) 0.0076(9) -0.0052(8) -0.0013(9)
N4' 0.0672(15) 0.0479(13) 0.0764(17) 0.0027(11) -0.0086(12) -0.0009(11)
N5' 0.0660(14) 0.0601(13) 0.0562(13) -0.0072(10) -0.0105(11) 0.0075(11)
O1' 0.0964(16) 0.0698(13) 0.0450(10) 0.0023(9) -0.0025(10) 0.0017(11)
O2' 0.0561(12) 0.1036(17) 0.0874(16) 0.0136(13) -0.0070(11) -0.0223(12)
O3' 0.0622(12) 0.1094(18) 0.0705(14) -0.0002(12) -0.0250(11) -0.0095(12)
O4' 0.163(3) 0.0634(15) 0.111(2) -0.0072(14) -0.016(2) -0.0332(18)
O5' 0.181(3) 0.0764(16) 0.0826(18) 0.0286(13) -0.028(2) -0.0359(19)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.502(3) . ?
C1 C6 1.450(3) . ?
C1 O1 1.226(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.524(4) . ?
C3 C4 1.527(4) . ?
C3 C7 1.527(5) . ?
C3 C8 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.503(3) . ?
C5 C6 1.370(3) . ?
C5 N1 1.378(3) . ?
C6 C18 1.502(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.388(4) . ?
C9 C14 1.382(4) . ?
C9 N1 1.439(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.361(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 C13 1.394(6) . ?
C12 C15 1.516(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.526(3) . ?
C16 N1 1.460(3) . ?
C16 N3 1.454(3) . ?
C17 C18 1.517(3) . ?
C17 C30 1.560(3) . ?
C17 N2 1.521(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.542(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.550(3) . ?
C19 C28 1.566(3) . ?
C20 H20 0.9800 . ?
C20 C29 1.563(3) . ?
C20 N3 1.444(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.500(4) . ?
C21 N3 1.480(3) . ?
C22 C23 1.394(4) . ?
C22 C27 1.377(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.355(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9800 . ?
C28 C29 1.528(3) . ?
C28 N5 1.433(3) . ?
C29 C30 1.529(4) . ?
C29 N4 1.498(3) . ?
C30 H30 0.9800 . ?
C30 C31 1.501(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.336(4) . ?
C32 H32 0.9300 . ?
C32 N5 1.380(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.495(4) . ?
C33 N5 1.479(4) . ?
C34 C35 1.368(5) . ?
C34 C39 1.359(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.387(7) . ?
C36 H36 0.9300 . ?
C36 C37 1.359(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.361(9) . ?
C38 H38 0.9300 . ?
C38 C39 1.397(7) . ?
C39 H39 0.9300 . ?
N2 O2 1.205(3) . ?
N2 O3 1.218(3) . ?
N4 O4 1.195(3) . ?
N4 O5 1.202(3) . ?
C1' C2' 1.499(4) . ?
C1' C6' 1.458(3) . ?
C1' O1' 1.224(3) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' C3' 1.522(4) . ?
C3' C4' 1.540(3) . ?
C3' C7' 1.513(4) . ?
C3' C8' 1.534(4) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' C5' 1.514(3) . ?
C5' C6' 1.353(3) . ?
C5' N1' 1.374(3) . ?
C6' C18' 1.497(3) . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C9' C10' 1.384(4) . ?
C9' C14' 1.391(4) . ?
C9' N1' 1.434(3) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.400(4) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.368(5) . ?
C12' C13' 1.381(6) . ?
C12' C15' 1.515(4) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.373(4) . ?
C14' H14' 0.9300 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16' H16' 0.9800 . ?
C16' C17' 1.521(3) . ?
C16' N1' 1.470(3) . ?
C16' N3' 1.467(3) . ?
C17' C18' 1.519(3) . ?
C17' C30' 1.567(3) . ?
C17' N2' 1.514(3) . ?
C18' H18' 0.9800 . ?
C18' C19' 1.549(4) . ?
C19' H19' 0.9800 . ?
C19' C20' 1.555(3) . ?
C19' C28' 1.556(4) . ?
C20' H20' 0.9800 . ?
C20' C29' 1.565(4) . ?
C20' N3' 1.441(3) . ?
C21' H21C 0.9700 . ?
C21' H21D 0.9700 . ?
C21' C22' 1.504(4) . ?
C21' N3' 1.480(3) . ?
C22' C23' 1.383(4) . ?
C22' C27' 1.374(5) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.387(6) . ?
C24' H24' 0.9300 . ?
C24' C25' 1.378(7) . ?
C25' H25' 0.9300 . ?
C25' C26' 1.349(6) . ?
C26' H26' 0.9300 . ?
C26' C27' 1.377(5) . ?
C27' H27' 0.9300 . ?
C28' H28' 0.9800 . ?
C28' C29' 1.525(4) . ?
C28' N5' 1.439(4) . ?
C29' C30' 1.528(4) . ?
C29' N4' 1.502(3) . ?
C30' H30' 0.9800 . ?
C30' C31' 1.504(4) . ?
C31' H31' 0.9300 . ?
C31' C32' 1.333(4) . ?
C32' H32' 0.9300 . ?
C32' N5' 1.366(4) . ?
C33' H33C 0.9700 . ?
C33' H33D 0.9700 . ?
C33' C34' 1.478(6) . ?
C33' N5' 1.453(5) . ?
C34' C35' 1.373(6) . ?
C34' C39' 1.388(7) . ?
C35' H35' 0.9300 . ?
C35' C36' 1.364(8) . ?
C36' H36' 0.9300 . ?
C36' C37' 1.312(9) . ?
C37' H37' 0.9300 . ?
C37' C38' 1.340(9) . ?
C38' H38' 0.9300 . ?
C38' C39' 1.427(10) . ?
C39' H39' 0.9300 . ?
N2' O2' 1.206(3) . ?
N2' O3' 1.228(3) . ?
N4' O4' 1.200(4) . ?
N4' O5' 1.198(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.0(2) . . ?
O1 C1 C2 121.3(2) . . ?
O1 C1 C6 120.7(2) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.8(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 C7 109.5(3) . . ?
C7 C3 C4 111.0(2) . . ?
C8 C3 C2 109.4(2) . . ?
C8 C3 C4 108.4(3) . . ?
C8 C3 C7 111.0(3) . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.5(2) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 N1 119.8(2) . . ?
N1 C5 C4 118.7(2) . . ?
C1 C6 C18 116.8(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C18 122.5(2) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 121.9(2) . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 N1 118.9(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 C15 121.5(4) . . ?
C13 C12 C15 120.2(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16 108.6 . . ?
N1 C16 H16 108.6 . . ?
N1 C16 C17 109.77(18) . . ?
N3 C16 H16 108.6 . . ?
N3 C16 C17 108.88(18) . . ?
N3 C16 N1 112.26(18) . . ?
C16 C17 C30 111.06(19) . . ?
C18 C17 C16 107.45(18) . . ?
C18 C17 C30 111.12(19) . . ?
C18 C17 N2 112.85(19) . . ?
N2 C17 C16 107.58(18) . . ?
N2 C17 C30 106.76(18) . . ?
C6 C18 C17 111.23(18) . . ?
C6 C18 H18 109.0 . . ?
C6 C18 C19 113.00(19) . . ?
C17 C18 H18 109.0 . . ?
C17 C18 C19 105.51(18) . . ?
C19 C18 H18 109.0 . . ?
C18 C19 H19 115.3 . . ?
C18 C19 C20 109.22(18) . . ?
C18 C19 C28 111.25(19) . . ?
C20 C19 H19 115.3 . . ?
C20 C19 C28 87.14(17) . . ?
C28 C19 H19 115.3 . . ?
C19 C20 H20 111.0 . . ?
C19 C20 C29 84.79(17) . . ?
C29 C20 H20 111.0 . . ?
N3 C20 C19 116.64(19) . . ?
N3 C20 H20 111.0 . . ?
N3 C20 C29 120.0(2) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
N3 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
N3 C21 C22 113.6(2) . . ?
C23 C22 C21 120.4(3) . . ?
C27 C22 C21 121.4(3) . . ?
C27 C22 C23 118.1(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(4) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(4) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.7(4) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 121.4(3) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C19 C28 H28 109.7 . . ?
C29 C28 C19 85.46(17) . . ?
C29 C28 H28 109.7 . . ?
N5 C28 C19 122.7(2) . . ?
N5 C28 H28 109.7 . . ?
N5 C28 C29 117.2(2) . . ?
C28 C29 C20 88.01(18) . . ?
C28 C29 C30 110.7(2) . . ?
C30 C29 C20 109.79(19) . . ?
N4 C29 C20 117.7(2) . . ?
N4 C29 C28 117.2(2) . . ?
N4 C29 C30 111.3(2) . . ?
C17 C30 H30 109.7 . . ?
C29 C30 C17 105.06(19) . . ?
C29 C30 H30 109.7 . . ?
C31 C30 C17 112.3(2) . . ?
C31 C30 C29 110.1(2) . . ?
C31 C30 H30 109.7 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 117.5 . . ?
C31 C32 N5 125.0(2) . . ?
N5 C32 H32 117.5 . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
N5 C33 H33A 108.9 . . ?
N5 C33 H33B 108.9 . . ?
N5 C33 C34 113.2(2) . . ?
C35 C34 C33 119.2(3) . . ?
C39 C34 C33 122.1(3) . . ?
C39 C34 C35 118.6(4) . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.8(4) . . ?
C36 C35 H35 119.6 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.6(5) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 120.5 . . ?
C36 C37 C38 118.9(5) . . ?
C38 C37 H37 120.5 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(5) . . ?
C39 C38 H38 119.7 . . ?
C34 C39 C38 120.5(5) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C5 N1 C9 122.06(19) . . ?
C5 N1 C16 119.54(18) . . ?
C9 N1 C16 114.67(18) . . ?
O2 N2 C17 119.3(2) . . ?
O2 N2 O3 123.9(2) . . ?
O3 N2 C17 116.8(2) . . ?
C16 N3 C21 113.36(19) . . ?
C20 N3 C16 113.53(18) . . ?
C20 N3 C21 115.06(19) . . ?
O4 N4 C29 119.1(3) . . ?
O4 N4 O5 122.2(3) . . ?
O5 N4 C29 118.6(2) . . ?
C28 N5 C33 116.7(2) . . ?
C32 N5 C28 118.1(2) . . ?
C32 N5 C33 119.2(2) . . ?
C6' C1' C2' 117.5(2) . . ?
O1' C1' C2' 121.5(2) . . ?
O1' C1' C6' 120.9(3) . . ?
C1' C2' H2'A 108.8 . . ?
C1' C2' H2'B 108.8 . . ?
C1' C2' C3' 113.7(2) . . ?
H2'A C2' H2'B 107.7 . . ?
C3' C2' H2'A 108.8 . . ?
C3' C2' H2'B 108.8 . . ?
C2' C3' C4' 107.4(2) . . ?
C2' C3' C8' 109.8(2) . . ?
C7' C3' C2' 110.5(3) . . ?
C7' C3' C4' 111.2(2) . . ?
C7' C3' C8' 108.8(3) . . ?
C8' C3' C4' 109.1(2) . . ?
C3' C4' H4'A 108.9 . . ?
C3' C4' H4'B 108.9 . . ?
H4'A C4' H4'B 107.7 . . ?
C5' C4' C3' 113.5(2) . . ?
C5' C4' H4'A 108.9 . . ?
C5' C4' H4'B 108.9 . . ?
C6' C5' C4' 122.1(2) . . ?
C6' C5' N1' 120.8(2) . . ?
N1' C5' C4' 117.0(2) . . ?
C1' C6' C18' 116.6(2) . . ?
C5' C6' C1' 120.9(2) . . ?
C5' C6' C18' 122.5(2) . . ?
C3' C7' H7'A 109.5 . . ?
C3' C7' H7'B 109.5 . . ?
C3' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C3' C8' H8'A 109.5 . . ?
C3' C8' H8'B 109.5 . . ?
C3' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C10' C9' C14' 120.0(2) . . ?
C10' C9' N1' 121.1(2) . . ?
C14' C9' N1' 118.7(2) . . ?
C9' C10' H10' 120.8 . . ?
C9' C10' C11' 118.4(3) . . ?
C11' C10' H10' 120.8 . . ?
C10' C11' H11' 118.9 . . ?
C12' C11' C10' 122.1(3) . . ?
C12' C11' H11' 118.9 . . ?
C11' C12' C13' 118.1(3) . . ?
C11' C12' C15' 120.1(4) . . ?
C13' C12' C15' 121.8(4) . . ?
C12' C13' H13' 119.2 . . ?
C14' C13' C12' 121.6(3) . . ?
C14' C13' H13' 119.2 . . ?
C9' C14' H14' 120.1 . . ?
C13' C14' C9' 119.7(3) . . ?
C13' C14' H14' 120.1 . . ?
C12' C15' H15D 109.5 . . ?
C12' C15' H15E 109.5 . . ?
C12' C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C17' C16' H16' 108.7 . . ?
N1' C16' H16' 108.7 . . ?
N1' C16' C17' 110.02(19) . . ?
N3' C16' H16' 108.7 . . ?
N3' C16' C17' 108.7(2) . . ?
N3' C16' N1' 112.12(19) . . ?
C16' C17' C30' 110.12(19) . . ?
C18' C17' C16' 107.6(2) . . ?
C18' C17' C30' 112.3(2) . . ?
N2' C17' C16' 107.2(2) . . ?
N2' C17' C18' 113.0(2) . . ?
N2' C17' C30' 106.5(2) . . ?
C6' C18' C17' 111.6(2) . . ?
C6' C18' H18' 109.1 . . ?
C6' C18' C19' 113.0(2) . . ?
C17' C18' H18' 109.1 . . ?
C17' C18' C19' 104.74(19) . . ?
C19' C18' H18' 109.1 . . ?
C18' C19' H19' 115.1 . . ?
C18' C19' C20' 109.6(2) . . ?
C18' C19' C28' 111.5(2) . . ?
C20' C19' H19' 115.1 . . ?
C20' C19' C28' 87.31(19) . . ?
C28' C19' H19' 115.1 . . ?
C19' C20' H20' 111.1 . . ?
C19' C20' C29' 84.60(19) . . ?
C29' C20' H20' 111.1 . . ?
N3' C20' C19' 117.0(2) . . ?
N3' C20' H20' 111.1 . . ?
N3' C20' C29' 119.3(2) . . ?
H21C C21' H21D 107.7 . . ?
C22' C21' H21C 108.8 . . ?
C22' C21' H21D 108.8 . . ?
N3' C21' H21C 108.8 . . ?
N3' C21' H21D 108.8 . . ?
N3' C21' C22' 113.9(2) . . ?
C23' C22' C21' 119.4(3) . . ?
C27' C22' C21' 122.6(3) . . ?
C27' C22' C23' 118.0(3) . . ?
C22' C23' H23' 119.7 . . ?
C22' C23' C24' 120.7(4) . . ?
C24' C23' H23' 119.7 . . ?
C23' C24' H24' 119.9 . . ?
C25' C24' C23' 120.2(4) . . ?
C25' C24' H24' 119.9 . . ?
C24' C25' H25' 120.6 . . ?
C26' C25' C24' 118.7(4) . . ?
C26' C25' H25' 120.6 . . ?
C25' C26' H26' 119.2 . . ?
C25' C26' C27' 121.7(4) . . ?
C27' C26' H26' 119.2 . . ?
C22' C27' C26' 120.7(4) . . ?
C22' C27' H27' 119.7 . . ?
C26' C27' H27' 119.7 . . ?
C19' C28' H28' 110.0 . . ?
C29' C28' C19' 85.92(19) . . ?
C29' C28' H28' 110.0 . . ?
N5' C28' C19' 121.6(2) . . ?
N5' C28' H28' 110.0 . . ?
N5' C28' C29' 117.1(2) . . ?
C28' C29' C20' 88.0(2) . . ?
C28' C29' C30' 110.4(2) . . ?
C30' C29' C20' 109.7(2) . . ?
N4' C29' C20' 117.2(2) . . ?
N4' C29' C28' 117.5(2) . . ?
N4' C29' C30' 111.8(2) . . ?
C17' C30' H30' 109.9 . . ?
C29' C30' C17' 105.0(2) . . ?
C29' C30' H30' 109.9 . . ?
C31' C30' C17' 111.7(2) . . ?
C31' C30' C29' 110.2(2) . . ?
C31' C30' H30' 109.9 . . ?
C30' C31' H31' 119.8 . . ?
C32' C31' C30' 120.4(3) . . ?
C32' C31' H31' 119.8 . . ?
C31' C32' H32' 117.6 . . ?
C31' C32' N5' 124.7(3) . . ?
N5' C32' H32' 117.6 . . ?
H33C C33' H33D 107.5 . . ?
C34' C33' H33C 108.4 . . ?
C34' C33' H33D 108.4 . . ?
N5' C33' H33C 108.4 . . ?
N5' C33' H33D 108.4 . . ?
N5' C33' C34' 115.3(4) . . ?
C35' C34' C33' 123.5(5) . . ?
C35' C34' C39' 116.3(5) . . ?
C39' C34' C33' 120.2(5) . . ?
C34' C35' H35' 117.8 . . ?
C36' C35' C34' 124.3(5) . . ?
C36' C35' H35' 117.8 . . ?
C35' C36' H36' 121.2 . . ?
C37' C36' C35' 117.6(6) . . ?
C37' C36' H36' 121.2 . . ?
C36' C37' H37' 118.1 . . ?
C36' C37' C38' 123.9(7) . . ?
C38' C37' H37' 118.1 . . ?
C37' C38' H38' 120.7 . . ?
C37' C38' C39' 118.6(6) . . ?
C39' C38' H38' 120.7 . . ?
C34' C39' C38' 119.3(6) . . ?
C34' C39' H39' 120.4 . . ?
C38' C39' H39' 120.4 . . ?
C5' N1' C9' 124.0(2) . . ?
C5' N1' C16' 118.73(19) . . ?
C9' N1' C16' 113.81(18) . . ?
O2' N2' C17' 119.2(2) . . ?
O2' N2' O3' 123.8(3) . . ?
O3' N2' C17' 117.0(2) . . ?
C16' N3' C21' 111.5(2) . . ?
C20' N3' C16' 113.54(19) . . ?
C20' N3' C21' 115.4(2) . . ?
O4' N4' C29' 118.3(3) . . ?
O5' N4' C29' 119.0(3) . . ?
O5' N4' O4' 122.6(3) . . ?
C28' N5' C33' 114.7(3) . . ?
C32' N5' C28' 118.8(2) . . ?
C32' N5' C33' 123.4(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -54.7(3) . . . . ?
C1 C2 C3 C7 65.9(3) . . . . ?
C1 C2 C3 C8 -172.2(3) . . . . ?
C1 C6 C18 C17 160.8(2) . . . . ?
C1 C6 C18 C19 -80.7(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 C18 -178.5(2) . . . . ?
C2 C3 C4 C5 49.0(3) . . . . ?
C3 C4 C5 C6 -19.8(4) . . . . ?
C3 C4 C5 N1 155.9(2) . . . . ?
C4 C5 C6 C1 -7.2(4) . . . . ?
C4 C5 C6 C18 172.6(2) . . . . ?
C4 C5 N1 C9 17.7(3) . . . . ?
C4 C5 N1 C16 174.8(2) . . . . ?
C5 C6 C18 C17 -18.9(3) . . . . ?
C5 C6 C18 C19 99.5(3) . . . . ?
C6 C1 C2 C3 31.4(4) . . . . ?
C6 C5 N1 C9 -166.6(2) . . . . ?
C6 C5 N1 C16 -9.5(3) . . . . ?
C6 C18 C19 C20 -98.7(2) . . . . ?
C6 C18 C19 C28 166.79(19) . . . . ?
C7 C3 C4 C5 -70.7(3) . . . . ?
C8 C3 C4 C5 167.0(3) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C10 C9 N1 C5 52.1(3) . . . . ?
C10 C9 N1 C16 -106.0(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C10 C11 C12 C15 -178.4(3) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C9 -1.0(5) . . . . ?
C14 C9 C10 C11 1.5(4) . . . . ?
C14 C9 N1 C5 -132.0(3) . . . . ?
C14 C9 N1 C16 69.8(3) . . . . ?
C15 C12 C13 C14 179.7(3) . . . . ?
C16 C17 C18 C6 49.5(2) . . . . ?
C16 C17 C18 C19 -73.4(2) . . . . ?
C16 C17 C30 C29 70.5(2) . . . . ?
C16 C17 C30 C31 -169.8(2) . . . . ?
C16 C17 N2 O2 -128.3(2) . . . . ?
C16 C17 N2 O3 53.3(3) . . . . ?
C17 C16 N1 C5 42.5(3) . . . . ?
C17 C16 N1 C9 -158.82(19) . . . . ?
C17 C16 N3 C20 0.5(3) . . . . ?
C17 C16 N3 C21 134.2(2) . . . . ?
C17 C18 C19 C20 23.1(2) . . . . ?
C17 C18 C19 C28 -71.5(2) . . . . ?
C17 C30 C31 C32 -84.7(3) . . . . ?
C18 C17 C30 C29 -49.1(2) . . . . ?
C18 C17 C30 C31 70.6(3) . . . . ?
C18 C17 N2 O2 -9.9(3) . . . . ?
C18 C17 N2 O3 171.7(2) . . . . ?
C18 C19 C20 C29 -83.7(2) . . . . ?
C18 C19 C20 N3 37.4(3) . . . . ?
C18 C19 C28 C29 81.0(2) . . . . ?
C18 C19 C28 N5 -38.7(3) . . . . ?
C19 C20 C29 C28 -28.60(17) . . . . ?
C19 C20 C29 C30 82.7(2) . . . . ?
C19 C20 C29 N4 -148.5(2) . . . . ?
C19 C20 N3 C16 -51.5(3) . . . . ?
C19 C20 N3 C21 175.6(2) . . . . ?
C19 C28 C29 C20 28.26(17) . . . . ?
C19 C28 C29 C30 -82.2(2) . . . . ?
C19 C28 C29 N4 148.7(2) . . . . ?
C19 C28 N5 C32 85.4(3) . . . . ?
C19 C28 N5 C33 -67.3(3) . . . . ?
C20 C19 C28 C29 -28.54(17) . . . . ?
C20 C19 C28 N5 -148.2(2) . . . . ?
C20 C29 C30 C17 -21.7(2) . . . . ?
C20 C29 C30 C31 -142.9(2) . . . . ?
C20 C29 N4 O4 98.2(3) . . . . ?
C20 C29 N4 O5 -79.1(4) . . . . ?
C21 C22 C23 C24 177.3(3) . . . . ?
C21 C22 C27 C26 -178.4(3) . . . . ?
C22 C21 N3 C16 169.6(2) . . . . ?
C22 C21 N3 C20 -57.4(3) . . . . ?
C22 C23 C24 C25 1.1(6) . . . . ?
C23 C22 C27 C26 -0.9(5) . . . . ?
C23 C24 C25 C26 -1.0(6) . . . . ?
C24 C25 C26 C27 -0.1(6) . . . . ?
C25 C26 C27 C22 1.1(6) . . . . ?
C27 C22 C23 C24 -0.2(5) . . . . ?
C28 C19 C20 C29 27.87(17) . . . . ?
C28 C19 C20 N3 148.9(2) . . . . ?
C28 C29 C30 C17 73.8(2) . . . . ?
C28 C29 C30 C31 -47.3(3) . . . . ?
C28 C29 N4 O4 -4.9(4) . . . . ?
C28 C29 N4 O5 177.8(3) . . . . ?
C29 C20 N3 C16 48.4(3) . . . . ?
C29 C20 N3 C21 -84.5(3) . . . . ?
C29 C28 N5 C32 -17.6(3) . . . . ?
C29 C28 N5 C33 -170.2(2) . . . . ?
C29 C30 C31 C32 32.0(3) . . . . ?
C30 C17 C18 C6 171.17(19) . . . . ?
C30 C17 C18 C19 48.3(2) . . . . ?
C30 C17 N2 O2 112.5(2) . . . . ?
C30 C17 N2 O3 -65.9(3) . . . . ?
C30 C29 N4 O4 -133.8(3) . . . . ?
C30 C29 N4 O5 48.9(4) . . . . ?
C30 C31 C32 N5 -6.8(4) . . . . ?
C31 C32 N5 C28 -1.5(4) . . . . ?
C31 C32 N5 C33 150.4(3) . . . . ?
C33 C34 C35 C36 179.9(4) . . . . ?
C33 C34 C39 C38 -179.8(4) . . . . ?
C34 C33 N5 C28 -49.0(3) . . . . ?
C34 C33 N5 C32 158.7(2) . . . . ?
C34 C35 C36 C37 -0.6(8) . . . . ?
C35 C34 C39 C38 -0.9(6) . . . . ?
C35 C36 C37 C38 -0.1(10) . . . . ?
C36 C37 C38 C39 0.2(10) . . . . ?
C37 C38 C39 C34 0.3(8) . . . . ?
C39 C34 C35 C36 1.1(6) . . . . ?
N1 C5 C6 C1 177.2(2) . . . . ?
N1 C5 C6 C18 -3.0(4) . . . . ?
N1 C9 C10 C11 177.3(2) . . . . ?
N1 C9 C14 C13 -176.2(3) . . . . ?
N1 C16 C17 C18 -61.4(2) . . . . ?
N1 C16 C17 C30 176.87(18) . . . . ?
N1 C16 C17 N2 60.4(2) . . . . ?
N1 C16 N3 C20 122.3(2) . . . . ?
N1 C16 N3 C21 -104.0(2) . . . . ?
N2 C17 C18 C6 -69.0(2) . . . . ?
N2 C17 C18 C19 168.17(18) . . . . ?
N2 C17 C30 C29 -172.54(18) . . . . ?
N2 C17 C30 C31 -52.8(3) . . . . ?
N3 C16 C17 C18 61.9(2) . . . . ?
N3 C16 C17 C30 -59.9(2) . . . . ?
N3 C16 C17 N2 -176.37(18) . . . . ?
N3 C16 N1 C5 -78.8(3) . . . . ?
N3 C16 N1 C9 79.9(2) . . . . ?
N3 C20 C29 C28 -146.5(2) . . . . ?
N3 C20 C29 C30 -35.1(3) . . . . ?
N3 C20 C29 N4 93.6(3) . . . . ?
N3 C21 C22 C23 133.0(3) . . . . ?
N3 C21 C22 C27 -49.6(3) . . . . ?
N4 C29 C30 C17 -153.9(2) . . . . ?
N4 C29 C30 C31 85.0(2) . . . . ?
N5 C28 C29 C20 152.9(2) . . . . ?
N5 C28 C29 C30 42.5(3) . . . . ?
N5 C28 C29 N4 -86.7(3) . . . . ?
N5 C33 C34 C35 106.0(3) . . . . ?
N5 C33 C34 C39 -75.1(4) . . . . ?
O1 C1 C2 C3 -150.4(3) . . . . ?
O1 C1 C6 C5 -177.0(3) . . . . ?
O1 C1 C6 C18 3.2(4) . . . . ?
C1' C2' C3' C4' 55.8(3) . . . . ?
C1' C2' C3' C7' -65.6(3) . . . . ?
C1' C2' C3' C8' 174.3(3) . . . . ?
C1' C6' C18' C17' -160.0(2) . . . . ?
C1' C6' C18' C19' 82.2(3) . . . . ?
C2' C1' C6' C5' 1.9(4) . . . . ?
C2' C1' C6' C18' -179.8(2) . . . . ?
C2' C3' C4' C5' -48.8(3) . . . . ?
C3' C4' C5' C6' 20.5(4) . . . . ?
C3' C4' C5' N1' -155.7(2) . . . . ?
C4' C5' C6' C1' 4.6(4) . . . . ?
C4' C5' C6' C18' -173.6(2) . . . . ?
C4' C5' N1' C9' -15.9(4) . . . . ?
C4' C5' N1' C16' -173.4(2) . . . . ?
C5' C6' C18' C17' 18.3(3) . . . . ?
C5' C6' C18' C19' -99.5(3) . . . . ?
C6' C1' C2' C3' -33.9(4) . . . . ?
C6' C5' N1' C9' 167.8(2) . . . . ?
C6' C5' N1' C16' 10.3(4) . . . . ?
C6' C18' C19' C20' 97.5(2) . . . . ?
C6' C18' C19' C28' -167.5(2) . . . . ?
C7' C3' C4' C5' 72.2(3) . . . . ?
C8' C3' C4' C5' -167.8(3) . . . . ?
C9' C10' C11' C12' 2.7(4) . . . . ?
C10' C9' C14' C13' -1.7(4) . . . . ?
C10' C9' N1' C5' -50.8(3) . . . . ?
C10' C9' N1' C16' 107.7(3) . . . . ?
C10' C11' C12' C13' -3.4(5) . . . . ?
C10' C11' C12' C15' 175.8(3) . . . . ?
C11' C12' C13' C14' 1.5(5) . . . . ?
C12' C13' C14' C9' 1.1(5) . . . . ?
C14' C9' C10' C11' -0.1(4) . . . . ?
C14' C9' N1' C5' 134.4(3) . . . . ?
C14' C9' N1' C16' -67.1(3) . . . . ?
C15' C12' C13' C14' -177.7(3) . . . . ?
C16' C17' C18' C6' -48.2(3) . . . . ?
C16' C17' C18' C19' 74.4(2) . . . . ?
C16' C17' C30' C29' -71.8(2) . . . . ?
C16' C17' C30' C31' 168.8(2) . . . . ?
C16' C17' N2' O2' 126.7(3) . . . . ?
C16' C17' N2' O3' -54.2(3) . . . . ?
C17' C16' N1' C5' -42.7(3) . . . . ?
C17' C16' N1' C9' 157.6(2) . . . . ?
C17' C16' N3' C20' 0.0(3) . . . . ?
C17' C16' N3' C21' -132.5(2) . . . . ?
C17' C18' C19' C20' -24.3(3) . . . . ?
C17' C18' C19' C28' 70.7(2) . . . . ?
C17' C30' C31' C32' 83.7(3) . . . . ?
C18' C17' C30' C29' 48.1(3) . . . . ?
C18' C17' C30' C31' -71.4(3) . . . . ?
C18' C17' N2' O2' 8.3(3) . . . . ?
C18' C17' N2' O3' -172.5(2) . . . . ?
C18' C19' C20' C29' 84.5(2) . . . . ?
C18' C19' C20' N3' -35.8(3) . . . . ?
C18' C19' C28' C29' -81.9(2) . . . . ?
C18' C19' C28' N5' 37.6(3) . . . . ?
C19' C20' C29' C28' 28.01(19) . . . . ?
C19' C20' C29' C30' -83.0(2) . . . . ?
C19' C20' C29' N4' 148.1(2) . . . . ?
C19' C20' N3' C16' 50.2(3) . . . . ?
C19' C20' N3' C21' -179.2(2) . . . . ?
C19' C28' C29' C20' -27.94(19) . . . . ?
C19' C28' C29' C30' 82.4(2) . . . . ?
C19' C28' C29' N4' -147.8(2) . . . . ?
C19' C28' N5' C32' -87.9(3) . . . . ?
C19' C28' N5' C33' 72.8(4) . . . . ?
C20' C19' C28' C29' 28.15(19) . . . . ?
C20' C19' C28' N5' 147.6(3) . . . . ?
C20' C29' C30' C17' 22.7(3) . . . . ?
C20' C29' C30' C31' 143.2(2) . . . . ?
C20' C29' N4' O4' -91.2(4) . . . . ?
C20' C29' N4' O5' 84.5(4) . . . . ?
C21' C22' C23' C24' -175.2(3) . . . . ?
C21' C22' C27' C26' 174.8(4) . . . . ?
C22' C21' N3' C16' -167.5(2) . . . . ?
C22' C21' N3' C20' 61.0(3) . . . . ?
C22' C23' C24' C25' -0.2(7) . . . . ?
C23' C22' C27' C26' -2.4(5) . . . . ?
C23' C24' C25' C26' -1.4(7) . . . . ?
C24' C25' C26' C27' 1.1(7) . . . . ?
C25' C26' C27' C22' 0.8(7) . . . . ?
C27' C22' C23' C24' 2.1(5) . . . . ?
C28' C19' C20' C29' -27.43(19) . . . . ?
C28' C19' C20' N3' -147.7(2) . . . . ?
C28' C29' C30' C17' -72.7(2) . . . . ?
C28' C29' C30' C31' 47.8(3) . . . . ?
C28' C29' N4' O4' 11.7(4) . . . . ?
C28' C29' N4' O5' -172.6(3) . . . . ?
C29' C20' N3' C16' -49.3(3) . . . . ?
C29' C20' N3' C21' 81.3(3) . . . . ?
C29' C28' N5' C32' 14.9(4) . . . . ?
C29' C28' N5' C33' 175.5(3) . . . . ?
C29' C30' C31' C32' -32.7(4) . . . . ?
C30' C17' C18' C6' -169.6(2) . . . . ?
C30' C17' C18' C19' -46.9(3) . . . . ?
C30' C17' N2' O2' -115.4(3) . . . . ?
C30' C17' N2' O3' 63.7(3) . . . . ?
C30' C29' N4' O4' 140.9(3) . . . . ?
C30' C29' N4' O5' -43.4(4) . . . . ?
C30' C31' C32' N5' 5.7(5) . . . . ?
C31' C32' N5' C28' 4.4(5) . . . . ?
C31' C32' N5' C33' -154.5(4) . . . . ?
C33' C34' C35' C36' 178.7(5) . . . . ?
C33' C34' C39' C38' -178.4(6) . . . . ?
C34' C33' N5' C28' 175.2(4) . . . . ?
C34' C33' N5' C32' -25.2(6) . . . . ?
C34' C35' C36' C37' 0.0(11) . . . . ?
C35' C34' C39' C38' 0.0(9) . . . . ?
C35' C36' C37' C38' -0.5(13) . . . . ?
C36' C37' C38' C39' 0.7(15) . . . . ?
C37' C38' C39' C34' -0.5(12) . . . . ?
C39' C34' C35' C36' 0.2(8) . . . . ?
N1' C5' C6' C1' -179.3(2) . . . . ?
N1' C5' C6' C18' 2.5(4) . . . . ?
N1' C9' C10' C11' -174.9(2) . . . . ?
N1' C9' C14' C13' 173.2(2) . . . . ?
N1' C16' C17' C18' 60.5(3) . . . . ?
N1' C16' C17' C30' -176.86(19) . . . . ?
N1' C16' C17' N2' -61.4(2) . . . . ?
N1' C16' N3' C20' -121.8(2) . . . . ?
N1' C16' N3' C21' 105.7(2) . . . . ?
N2' C17' C18' C6' 69.9(3) . . . . ?
N2' C17' C18' C19' -167.43(19) . . . . ?
N2' C17' C30' C29' 172.32(19) . . . . ?
N2' C17' C30' C31' 52.8(3) . . . . ?
N3' C16' C17' C18' -62.6(2) . . . . ?
N3' C16' C17' C30' 60.0(3) . . . . ?
N3' C16' C17' N2' 175.53(18) . . . . ?
N3' C16' N1' C5' 78.3(3) . . . . ?
N3' C16' N1' C9' -81.4(3) . . . . ?
N3' C20' C29' C28' 146.0(2) . . . . ?
N3' C20' C29' C30' 35.0(3) . . . . ?
N3' C20' C29' N4' -93.8(3) . . . . ?
N3' C21' C22' C23' -134.7(3) . . . . ?
N3' C21' C22' C27' 48.1(4) . . . . ?
N4' C29' C30' C17' 154.5(2) . . . . ?
N4' C29' C30' C31' -85.0(3) . . . . ?
N5' C28' C29' C20' -151.5(2) . . . . ?
N5' C28' C29' C30' -41.2(3) . . . . ?
N5' C28' C29' N4' 88.6(3) . . . . ?
N5' C33' C34' C35' -82.4(6) . . . . ?
N5' C33' C34' C39' 96.0(6) . . . . ?
O1' C1' C2' C3' 148.1(3) . . . . ?
O1' C1' C6' C5' 179.9(3) . . . . ?
O1' C1' C6' C18' -1.8(4) . . . . ?
_iucr_refine_instructions_details
;
201803150_tw.res created by SHELXL-2014/7
TITL CF solution in P21/c
CELL 1.54184 11.804083 18.745044 31.258102 90 79.1361 90
ZERR 8 0.000141 0.000181 0.00037 0 0.0011 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 312 312 40 40
DELU 0.001 0.001 C36' C37'
DELU 0.001 0.001 C24 C25
ISOR 0.01 0.02 C36' C37' C38' C39'
ISOR 0.01 0.02 C24 C25
ISOR 0.01 0.02 C33'
L.S. 15 0 0
PLAN 20
SIZE 0.1 0.17 0.19
MPLA C9 C10 C11 C12 C13 C14
MPLA C22 C23 C24 C25 C26 C27
MPLA C34 C35 C36 C37 C38 C39
MPLA C9' C10' C11' C12' C13' C14'
MPLA C22' C23' C24' C25' C26' C27'
MPLA C34' C35' C36' C37' C38' C39'
BOND $h
CONF
fmap 2
acta
MERG 0
REM
REM
REM
WGHT 0.090300 0.712600
BASF 0.34305
FVAR 3.04874
C1 1 0.335790 0.835778 0.455122 11.00000 0.04929 0.04654 =
0.04448 0.00117 -0.00136 -0.00370
C2 1 0.311167 0.757139 0.456575 11.00000 0.06831 0.05009 =
0.04956 0.00473 0.00412 -0.00848
AFIX 23
H2A 2 0.229718 0.749964 0.456711 11.00000 -1.20000
H2B 2 0.327468 0.737899 0.483580 11.00000 -1.20000
AFIX 0
C3 1 0.380911 0.715752 0.418581 11.00000 0.06743 0.04567 =
0.05197 0.00419 0.00134 -0.00041
C4 1 0.359633 0.750605 0.376639 11.00000 0.06628 0.04470 =
0.05066 -0.00494 -0.00888 -0.00182
AFIX 23
H4A 2 0.412874 0.730276 0.352246 11.00000 -1.20000
H4B 2 0.282071 0.738925 0.372860 11.00000 -1.20000
AFIX 0
C5 1 0.373225 0.830358 0.375357 11.00000 0.04157 0.04481 =
0.04123 -0.00279 -0.00582 -0.00095
C6 1 0.367908 0.869304 0.412766 11.00000 0.04216 0.04251 =
0.03885 -0.00028 -0.00508 -0.00073
C7 1 0.508582 0.718391 0.421358 11.00000 0.07291 0.07849 =
0.06682 0.01465 -0.00468 0.01923
AFIX 137
H7A 2 0.552168 0.690702 0.398101 11.00000 -1.50000
H7B 2 0.519039 0.699176 0.448817 11.00000 -1.50000
H7C 2 0.534826 0.766955 0.418903 11.00000 -1.50000
AFIX 0
C8 1 0.337725 0.639233 0.419794 11.00000 0.12956 0.04466 =
0.07067 0.00015 0.00077 -0.00775
AFIX 137
H8A 2 0.256634 0.639064 0.419338 11.00000 -1.50000
H8B 2 0.350926 0.616458 0.445923 11.00000 -1.50000
H8C 2 0.378347 0.613860 0.394886 11.00000 -1.50000
AFIX 0
C9 1 0.382101 0.829462 0.295950 11.00000 0.05198 0.04393 =
0.04425 -0.00360 -0.01509 0.00246
C10 1 0.277550 0.798599 0.292180 11.00000 0.05153 0.06023 =
0.06454 -0.00510 -0.01942 -0.00164
AFIX 43
H10 2 0.217078 0.798076 0.316032 11.00000 -1.20000
AFIX 0
C11 1 0.262948 0.769092 0.253802 11.00000 0.07398 0.05602 =
0.07971 -0.00608 -0.04115 0.00134
AFIX 43
H11 2 0.192931 0.747633 0.252053 11.00000 -1.20000
AFIX 0
C12 1 0.349543 0.770323 0.217531 11.00000 0.11949 0.05470 =
0.06406 -0.01201 -0.04454 0.00798
C13 1 0.453921 0.802528 0.220948 11.00000 0.10766 0.06094 =
0.04703 -0.01069 -0.00148 0.00486
AFIX 43
H13 2 0.513142 0.804631 0.196702 11.00000 -1.20000
AFIX 0
C14 1 0.470148 0.831257 0.259895 11.00000 0.06192 0.05487 =
0.05001 -0.00607 -0.00727 0.00192
AFIX 43
H14 2 0.540556 0.851925 0.261938 11.00000 -1.20000
AFIX 0
C15 1 0.332369 0.739161 0.174458 11.00000 0.20600 0.10483 =
0.08172 -0.03088 -0.07123 -0.00034
AFIX 137
H15A 2 0.345452 0.688612 0.174410 11.00000 -1.50000
H15B 2 0.385839 0.760801 0.151118 11.00000 -1.50000
H15C 2 0.254940 0.748335 0.170569 11.00000 -1.50000
AFIX 0
C16 1 0.402847 0.941575 0.333407 11.00000 0.03991 0.04754 =
0.03641 -0.00029 -0.00698 -0.00303
AFIX 13
H16 2 0.446519 0.955873 0.304860 11.00000 -1.20000
AFIX 0
C17 1 0.464271 0.970487 0.368599 11.00000 0.03613 0.04387 =
0.04327 0.00201 -0.00851 -0.00220
C18 1 0.394901 0.947621 0.412322 11.00000 0.04173 0.04442 =
0.03852 -0.00047 -0.01257 -0.00278
AFIX 13
H18 2 0.439580 0.957778 0.435051 11.00000 -1.20000
AFIX 0
C19 1 0.285981 0.994881 0.419811 11.00000 0.04190 0.04727 =
0.04022 -0.00466 -0.00843 -0.00104
AFIX 13
H19 2 0.218604 0.974634 0.439136 11.00000 -1.20000
AFIX 0
C20 1 0.263984 1.022186 0.375270 11.00000 0.04173 0.04573 =
0.04581 -0.00177 -0.01450 0.00287
AFIX 13
H20 2 0.186163 1.042090 0.378067 11.00000 -1.20000
AFIX 0
C21 1 0.258114 0.998933 0.298055 11.00000 0.05655 0.06511 =
0.04066 0.00520 -0.01567 -0.00290
AFIX 23
H21A 2 0.276184 0.961992 0.276097 11.00000 -1.20000
H21B 2 0.305464 1.040141 0.288057 11.00000 -1.20000
AFIX 0
C22 1 0.133571 1.019120 0.302235 11.00000 0.05879 0.05690 =
0.04641 -0.00637 -0.02504 0.00372
C23 1 0.102870 1.083328 0.285044 11.00000 0.08810 0.07352 =
0.06534 0.00450 -0.03196 0.01250
AFIX 43
H23 2 0.159501 1.115026 0.271916 11.00000 -1.20000
AFIX 0
C24 1 -0.013348 1.099607 0.287696 11.00000 0.10901 0.09153 =
0.08839 -0.00647 -0.04372 0.04417
AFIX 43
H24 2 -0.033791 1.142073 0.275765 11.00000 -1.20000
AFIX 0
C25 1 -0.097207 1.054701 0.307346 11.00000 0.07507 0.12195 =
0.09611 -0.02723 -0.04441 0.03524
AFIX 43
H25 2 -0.174352 1.066872 0.309178 11.00000 -1.20000
AFIX 0
C26 1 -0.068935 0.992048 0.324348 11.00000 0.05418 0.10189 =
0.11044 -0.01861 -0.02678 -0.00373
AFIX 43
H26 2 -0.126502 0.961276 0.337873 11.00000 -1.20000
AFIX 0
C27 1 0.046563 0.974054 0.321454 11.00000 0.05818 0.06455 =
0.09001 -0.00448 -0.02702 -0.00175
AFIX 43
H27 2 0.065443 0.930674 0.332737 11.00000 -1.20000
AFIX 0
C28 1 0.315518 1.073823 0.429895 11.00000 0.05174 0.04447 =
0.05107 -0.00519 -0.01733 0.00576
AFIX 13
H28 2 0.244118 1.100664 0.439739 11.00000 -1.20000
AFIX 0
C29 1 0.353233 1.081605 0.380601 11.00000 0.05494 0.03944 =
0.04939 0.00268 -0.02000 -0.00219
C30 1 0.475823 1.053339 0.365680 11.00000 0.05022 0.04288 =
0.04990 0.00495 -0.01366 -0.00643
AFIX 13
H30 2 0.504770 1.067559 0.335425 11.00000 -1.20000
AFIX 0
C31 1 0.553689 1.082129 0.394397 11.00000 0.04911 0.04942 =
0.06504 0.00534 -0.01846 -0.01223
AFIX 43
H31 2 0.630994 1.090672 0.382812 11.00000 -1.20000
AFIX 0
C32 1 0.512917 1.095596 0.436468 11.00000 0.06173 0.04654 =
0.06721 -0.00159 -0.03093 -0.00682
AFIX 43
H32 2 0.565829 1.108471 0.453690 11.00000 -1.20000
AFIX 0
C33 1 0.368196 1.073056 0.503026 11.00000 0.07965 0.06432 =
0.05675 0.00154 -0.02522 0.00236
AFIX 23
H33A 2 0.423739 1.094910 0.518228 11.00000 -1.20000
H33B 2 0.373901 1.021751 0.506066 11.00000 -1.20000
AFIX 0
C34 1 0.249667 1.096460 0.523987 11.00000 0.07878 0.06293 =
0.04698 -0.00711 -0.01892 0.00451
C35 1 0.164075 1.046573 0.533812 11.00000 0.09552 0.08012 =
0.09229 -0.00019 -0.00494 -0.00263
AFIX 43
H35 2 0.180494 0.998824 0.527333 11.00000 -1.20000
AFIX 0
C36 1 0.053138 1.066372 0.553317 11.00000 0.08307 0.14373 =
0.13852 0.02030 0.01423 -0.00657
AFIX 43
H36 2 -0.004194 1.031855 0.559550 11.00000 -1.20000
AFIX 0
C37 1 0.027437 1.135778 0.563408 11.00000 0.11469 0.16410 =
0.10914 0.02315 0.02650 0.05215
AFIX 43
H37 2 -0.047003 1.149011 0.576457 11.00000 -1.20000
AFIX 0
C38 1 0.112426 1.185591 0.554105 11.00000 0.15579 0.10362 =
0.11306 -0.01360 0.00700 0.05294
AFIX 43
H38 2 0.095946 1.233222 0.560932 11.00000 -1.20000
AFIX 0
C39 1 0.224206 1.165782 0.534387 11.00000 0.12124 0.07572 =
0.09011 -0.01017 -0.01131 0.00999
AFIX 43
H39 2 0.281615 1.200281 0.528334 11.00000 -1.20000
AFIX 0
N1 3 0.399042 0.863779 0.335434 11.00000 0.04881 0.04624 =
0.03746 -0.00318 -0.00699 -0.00294
N2 3 0.586171 0.940482 0.359913 11.00000 0.03792 0.05392 =
0.05630 0.00014 -0.00906 -0.00410
N3 3 0.288368 0.972975 0.339170 11.00000 0.04000 0.05049 =
0.04012 -0.00240 -0.01195 -0.00128
N4 3 0.338520 1.153387 0.361325 11.00000 0.07014 0.04513 =
0.06960 0.00502 -0.02875 0.00051
N5 3 0.398269 1.091848 0.456293 11.00000 0.06099 0.04967 =
0.05108 -0.00735 -0.02272 -0.00088
O1 4 0.326469 0.871177 0.488578 11.00000 0.08899 0.05730 =
0.03835 -0.00195 -0.00858 -0.00999
O2 4 0.621991 0.911083 0.388974 11.00000 0.05416 0.08850 =
0.07378 0.00927 -0.02106 0.01558
O3 4 0.642892 0.949427 0.323533 11.00000 0.04716 0.10831 =
0.06710 0.00810 0.00067 0.00354
O4 4 0.291586 1.199732 0.384315 11.00000 0.15099 0.05382 =
0.10306 0.00209 -0.02524 0.03349
O5 4 0.370659 1.161534 0.322816 11.00000 0.16454 0.07263 =
0.08371 0.02883 -0.01543 0.02186
C1' 1 0.931337 0.337846 0.451548 11.00000 0.05544 0.05935 =
0.04855 0.00584 -0.01059 -0.00435
C2' 1 0.960876 0.260506 0.454743 11.00000 0.06281 0.06460 =
0.04972 0.01390 -0.01270 -0.00345
AFIX 23
H2'A 2 0.915121 0.240982 0.481193 11.00000 -1.20000
H2'B 2 1.041435 0.256548 0.457055 11.00000 -1.20000
AFIX 0
C3' 1 0.940256 0.216104 0.416150 11.00000 0.05814 0.05259 =
0.05242 0.01197 -0.00716 -0.00165
C4' 1 1.009437 0.250726 0.374668 11.00000 0.06003 0.04966 =
0.05331 0.00680 -0.00075 0.00222
AFIX 23
H4'A 2 1.090847 0.241413 0.373370 11.00000 -1.20000
H4'B 2 0.987402 0.228529 0.349421 11.00000 -1.20000
AFIX 0
C5' 1 0.991324 0.330476 0.372387 11.00000 0.04232 0.04917 =
0.04687 0.00764 -0.00489 -0.00119
C6' 1 0.951063 0.369936 0.408292 11.00000 0.04656 0.04830 =
0.04439 0.00453 -0.00366 -0.00276
C7' 1 0.812926 0.213234 0.414717 11.00000 0.06642 0.06566 =
0.06642 0.01337 -0.01084 -0.01342
AFIX 137
H7'A 2 0.771594 0.193138 0.441388 11.00000 -1.50000
H7'B 2 0.801270 0.184143 0.390644 11.00000 -1.50000
H7'C 2 0.785126 0.260601 0.411212 11.00000 -1.50000
AFIX 0
C8' 1 0.984143 0.139811 0.420094 11.00000 0.09255 0.05516 =
0.07425 0.01629 -0.00632 0.00631
AFIX 137
H8'A 2 1.064606 0.141064 0.421591 11.00000 -1.50000
H8'B 2 0.973625 0.112564 0.395131 11.00000 -1.50000
H8'C 2 0.941665 0.118056 0.446027 11.00000 -1.50000
AFIX 0
C9' 1 1.073213 0.326726 0.293315 11.00000 0.04391 0.04633 =
0.04805 0.00382 0.00245 -0.00203
C10' 1 1.180694 0.296788 0.292647 11.00000 0.04671 0.05816 =
0.06488 0.00740 -0.00006 -0.00031
AFIX 43
H10' 2 1.212053 0.294978 0.317779 11.00000 -1.20000
AFIX 0
C11' 1 1.241107 0.269289 0.253248 11.00000 0.05585 0.05598 =
0.09174 0.00224 0.01949 0.00421
AFIX 43
H11' 2 1.311903 0.247248 0.252806 11.00000 -1.20000
AFIX 0
C12' 1 1.199348 0.273800 0.215386 11.00000 0.08854 0.05800 =
0.06173 -0.00974 0.01517 -0.00273
C13' 1 1.091362 0.303292 0.217140 11.00000 0.10165 0.06798 =
0.05551 -0.00931 -0.01561 -0.00333
AFIX 43
H13' 2 1.060939 0.305763 0.191815 11.00000 -1.20000
AFIX 0
C14' 1 1.027794 0.329062 0.255368 11.00000 0.06085 0.05569 =
0.05711 -0.00125 -0.01029 -0.00157
AFIX 43
H14' 2 0.954718 0.347988 0.255888 11.00000 -1.20000
AFIX 0
C15' 1 1.271652 0.247820 0.172993 11.00000 0.14830 0.09322 =
0.08739 -0.02282 0.03962 0.00171
AFIX 137
H15D 2 1.283176 0.197268 0.174609 11.00000 -1.50000
H15E 2 1.345028 0.271554 0.168086 11.00000 -1.50000
H15F 2 1.232566 0.258175 0.149420 11.00000 -1.50000
AFIX 0
C16' 1 1.006874 0.439104 0.328227 11.00000 0.04369 0.04858 =
0.04333 0.00551 -0.00804 0.00185
AFIX 13
H16' 2 0.997020 0.451640 0.298711 11.00000 -1.20000
AFIX 0
C17' 1 0.904754 0.468240 0.360570 11.00000 0.03962 0.04980 =
0.04823 0.00290 -0.00873 0.00199
C18' 1 0.921358 0.447316 0.405923 11.00000 0.04389 0.05053 =
0.04590 0.00216 -0.00352 0.00216
AFIX 13
H18' 2 0.850019 0.457036 0.426780 11.00000 -1.20000
AFIX 0
C19' 1 1.017649 0.497514 0.415625 11.00000 0.05084 0.05653 =
0.04875 0.00227 -0.01378 0.00180
AFIX 13
H19' 2 1.061065 0.479546 0.437184 11.00000 -1.20000
AFIX 0
C20' 1 1.092633 0.523302 0.372060 11.00000 0.04280 0.05199 =
0.05650 0.00452 -0.01217 -0.00180
AFIX 13
H20' 2 1.165204 0.544339 0.376867 11.00000 -1.20000
AFIX 0
C21' 1 1.185569 0.499132 0.295865 11.00000 0.05033 0.06352 =
0.06192 0.01116 -0.00396 -0.00257
AFIX 23
H21C 2 1.148406 0.540167 0.285569 11.00000 -1.20000
H21D 2 1.190736 0.462162 0.273868 11.00000 -1.20000
AFIX 0
C22' 1 1.305542 0.519885 0.300714 11.00000 0.04832 0.05789 =
0.06117 -0.00213 0.00458 -0.00090
C23' 1 1.352268 0.583074 0.282553 11.00000 0.07719 0.07868 =
0.07777 0.01175 -0.00204 -0.02001
AFIX 43
H23' 2 1.307227 0.613817 0.269440 11.00000 -1.20000
AFIX 0
C24' 1 1.465660 0.601088 0.283689 11.00000 0.09225 0.11375 =
0.09505 0.00158 0.00497 -0.05639
AFIX 43
H24' 2 1.496203 0.643671 0.271279 11.00000 -1.20000
AFIX 0
C25' 1 1.533204 0.556094 0.303148 11.00000 0.05418 0.14228 =
0.09527 -0.02827 0.00322 -0.02645
AFIX 43
H25' 2 1.609765 0.567374 0.303465 11.00000 -1.20000
AFIX 0
C26' 1 1.486121 0.495388 0.321723 11.00000 0.05460 0.11960 =
0.12375 -0.01748 -0.02013 0.01472
AFIX 43
H26' 2 1.530827 0.465199 0.335350 11.00000 -1.20000
AFIX 0
C27' 1 1.373526 0.476959 0.321026 11.00000 0.05510 0.06901 =
0.11563 0.00369 -0.01545 0.00537
AFIX 43
H27' 2 1.343230 0.435033 0.334443 11.00000 -1.20000
AFIX 0
C28' 1 0.974154 0.575703 0.422919 11.00000 0.05832 0.05139 =
0.05935 -0.00403 -0.01579 0.00069
AFIX 13
H28' 2 1.030408 0.604294 0.434844 11.00000 -1.20000
AFIX 0
C29' 1 0.997210 0.581615 0.373380 11.00000 0.05173 0.04443 =
0.06092 0.00474 -0.01095 0.00101
C30' 1 0.896028 0.551030 0.355162 11.00000 0.05170 0.04814 =
0.05204 0.00429 -0.01165 0.00534
AFIX 13
H30' 2 0.904283 0.563203 0.324238 11.00000 -1.20000
AFIX 0
C31' 1 0.783945 0.579921 0.380055 11.00000 0.05569 0.06039 =
0.06088 0.00158 -0.01369 0.01596
AFIX 43
H31' 2 0.722437 0.587351 0.365859 11.00000 -1.20000
AFIX 0
C32' 1 0.772203 0.594948 0.422340 11.00000 0.06022 0.07522 =
0.06780 -0.00701 -0.00950 0.02288
AFIX 43
H32' 2 0.699540 0.608610 0.437096 11.00000 -1.20000
AFIX 0
C33' 1 0.839846 0.579963 0.492336 11.00000 0.10576 0.18200 =
0.06416 -0.00922 -0.01285 0.03073
AFIX 23
H33C 2 0.898264 0.605852 0.504071 11.00000 -1.20000
H33D 2 0.850374 0.529604 0.497565 11.00000 -1.20000
AFIX 0
C34' 1 0.725188 0.601713 0.516519 11.00000 0.09441 0.09610 =
0.05713 -0.00380 -0.00013 0.00520
C35' 1 0.697735 0.670583 0.529433 11.00000 0.11959 0.09399 =
0.10607 -0.01625 -0.00940 -0.01728
AFIX 43
H35' 2 0.755194 0.704993 0.523041 11.00000 -1.20000
AFIX 0
C36' 1 0.591823 0.691875 0.551007 11.00000 0.14440 0.12487 =
0.12891 -0.04299 0.00411 0.02035
AFIX 43
H36' 2 0.577405 0.739235 0.559102 11.00000 -1.20000
AFIX 0
C37' 1 0.510951 0.643168 0.559944 11.00000 0.13748 0.18414 =
0.15047 -0.03386 0.04489 -0.00084
AFIX 43
H37' 2 0.438681 0.657287 0.574842 11.00000 -1.20000
AFIX 0
C38' 1 0.526337 0.574325 0.548879 11.00000 0.15565 0.17169 =
0.18915 0.02701 0.03563 -0.06921
AFIX 43
H38' 2 0.466026 0.541875 0.555665 11.00000 -1.20000
AFIX 0
C39' 1 0.637230 0.551820 0.526456 11.00000 0.18282 0.09741 =
0.15794 0.01431 -0.00837 -0.02720
AFIX 43
H39' 2 0.650427 0.504266 0.518589 11.00000 -1.20000
AFIX 0
N1' 3 1.011077 0.360994 0.331686 11.00000 0.04567 0.04531 =
0.04366 0.00299 -0.00311 0.00159
N2' 3 0.796714 0.436730 0.348704 11.00000 0.04321 0.06055 =
0.06108 -0.00011 -0.00937 0.00155
N3' 3 1.112581 0.472980 0.336586 11.00000 0.04097 0.05072 =
0.04936 0.00757 -0.00525 -0.00130
N4' 3 1.034409 0.652983 0.353760 11.00000 0.06724 0.04785 =
0.07642 0.00269 -0.00859 -0.00087
N5' 3 0.859179 0.591731 0.445569 11.00000 0.06602 0.06008 =
0.05618 -0.00723 -0.01052 0.00750
O1' 4 0.895045 0.373539 0.484050 11.00000 0.09640 0.06975 =
0.04497 0.00230 -0.00246 0.00171
O2' 4 0.728674 0.406245 0.376314 11.00000 0.05608 0.10362 =
0.08740 0.01356 -0.00696 -0.02234
O3' 4 0.783217 0.444812 0.311004 11.00000 0.06223 0.10941 =
0.07046 -0.00018 -0.02499 -0.00948
O4' 4 1.061959 0.698259 0.376960 11.00000 0.16260 0.06344 =
0.11105 -0.00718 -0.01639 -0.03324
O5' 4 1.041888 0.661171 0.315305 11.00000 0.18140 0.07639 =
0.08263 0.02858 -0.02809 -0.03593
HKLF 5
REM CF solution in P21/c
REM R1 = 0.0516 for 9893 Fo > 4sig(Fo) and 0.0596 for all 11515 data
REM 890 parameters refined using 44 restraints
END
WGHT 0.0903 0.7125
REM Highest difference peak 0.381, deepest hole -0.274, 1-sigma level 0.041
Q1 1 0.8535 0.6388 0.4869 11.00000 0.05 0.38
Q2 1 0.6930 0.5675 0.3645 11.00000 0.05 0.30
Q3 1 0.5740 0.5633 0.5880 11.00000 0.05 0.24
Q4 1 0.5618 0.6228 0.5886 11.00000 0.05 0.24
Q5 1 0.6574 1.0777 0.3762 11.00000 0.05 0.23
Q6 1 0.4335 0.8060 0.2835 11.00000 0.05 0.23
Q7 1 0.1724 1.1305 0.5085 11.00000 0.05 0.23
Q8 1 1.5155 0.4409 0.3304 11.00000 0.05 0.22
Q9 1 1.0966 0.3619 0.1660 11.00000 0.05 0.21
Q10 1 1.6920 0.5019 0.2978 11.00000 0.05 0.21
Q11 1 1.3088 0.4394 0.3543 11.00000 0.05 0.21
Q12 1 -0.0909 0.9409 0.3315 11.00000 0.05 0.20
Q13 1 0.3864 0.8057 0.2098 11.00000 0.05 0.20
Q14 1 0.0829 0.9404 0.3577 11.00000 0.05 0.19
Q15 1 -0.2228 1.0183 0.3725 11.00000 0.05 0.19
Q16 1 -0.2036 0.9718 0.3356 11.00000 0.05 0.18
Q17 1 1.1224 0.3328 0.1269 11.00000 0.05 0.18
Q18 1 0.5010 0.6640 0.6269 11.00000 0.05 0.18
Q19 1 0.3804 1.1413 0.4903 11.00000 0.05 0.18
Q20 1 1.6126 0.4739 0.3379 11.00000 0.05 0.18
REM The information below was added by Olex2.
REM
REM R1 = 0.0516 for 9893 Fo > 4sig(Fo) and 0.0596 for all 11515 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.38, deepest hole -0.27
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0596
REM R1_gt = 0.0516
REM wR_ref = 0.1465
REM GOOF = 1.038
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 11515
REM Reflections_gt = 9893
REM Parameters = n/a
REM Hole = -0.27
REM Peak = 0.38
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6569(10)
2 0.3431(10)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_201809362
_database_code_depnum_ccdc_archive 'CCDC 1947689'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record
;
2019-08-17 deposited with the CCDC. 2019-12-17 downloaded from the CCDC.
;
_audit_creation_date 2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C45 H39 Cl2 N3 O'
_chemical_formula_sum 'C45 H39 Cl2 N3 O'
_chemical_formula_weight 708.69
_chemical_melting_point ?
_chemical_oxdiff_formula C15H15O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 13.58053(11)
_cell_length_b 20.7753(2)
_cell_length_c 29.2921(3)
_cell_angle_alpha 90
_cell_angle_beta 102.8973(9)
_cell_angle_gamma 90
_cell_volume 8055.96(13)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 11310
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.8680
_cell_measurement_theta_min 3.9470
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 1.725
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.80582
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.169
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_F_000 2976
_exptl_crystal_size_max ?
_exptl_crystal_size_mid ?
_exptl_crystal_size_min ?
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0322
_diffrn_reflns_av_unetI/netI 0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 37627
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 67.075
_diffrn_reflns_theta_max 67.075
_diffrn_reflns_theta_min 3.352
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -86.00 -33.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -180.0000 106
#__ type_ start__ end____ width___ exp.time_
2 omega -92.00 -66.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -30.0000 52
#__ type_ start__ end____ width___ exp.time_
3 omega -24.00 35.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 57.0000 -180.0000 118
#__ type_ start__ end____ width___ exp.time_
4 omega -87.00 -34.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- -33.5000 178.0000 -60.0000 106
#__ type_ start__ end____ width___ exp.time_
5 omega -1.00 109.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 19.0000 -150.0000 220
#__ type_ start__ end____ width___ exp.time_
6 omega -14.00 34.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -57.0000 60.0000 96
#__ type_ start__ end____ width___ exp.time_
7 omega 77.00 103.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 90.0000 52
#__ type_ start__ end____ width___ exp.time_
8 omega 59.00 93.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 0.0000 68
#__ type_ start__ end____ width___ exp.time_
9 omega 23.00 71.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -90.0000 96
#__ type_ start__ end____ width___ exp.time_
10 omega 58.00 101.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 150.0000 86
#__ type_ start__ end____ width___ exp.time_
11 omega 82.00 109.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 120.0000 54
#__ type_ start__ end____ width___ exp.time_
12 omega 39.00 67.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 -99.0000 0.0000 56
#__ type_ start__ end____ width___ exp.time_
13 omega 74.00 110.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 178.0000 -30.0000 72
#__ type_ start__ end____ width___ exp.time_
14 omega 77.00 104.00 0.5000 4.5000
omega____ theta____ kappa____ phi______ frames
- 36.4734 57.0000 -90.0000 54
#__ type_ start__ end____ width___ exp.time_
15 omega 97.00 156.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 45.0000 150.0000 118
#__ type_ start__ end____ width___ exp.time_
16 omega 39.00 98.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -60.0000 118
#__ type_ start__ end____ width___ exp.time_
17 omega 65.00 108.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -94.0000 30.0000 86
#__ type_ start__ end____ width___ exp.time_
18 omega 117.00 157.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 111.0000 90.0000 80
#__ type_ start__ end____ width___ exp.time_
19 omega 42.00 80.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -30.0000 120.0000 76
#__ type_ start__ end____ width___ exp.time_
20 omega 53.00 79.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 -180.0000 52
#__ type_ start__ end____ width___ exp.time_
21 omega 94.00 160.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 61.0000 90.0000 132
#__ type_ start__ end____ width___ exp.time_
22 omega 41.00 99.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -45.0000 0.0000 116
#__ type_ start__ end____ width___ exp.time_
23 omega 74.00 164.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 15.0000 60.0000 180
#__ type_ start__ end____ width___ exp.time_
24 omega 37.00 109.00 0.5000 27.5000
omega____ theta____ kappa____ phi______ frames
- 108.0000 -111.0000 -30.0000 144
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0564917000
_diffrn_orient_matrix_UB_12 -0.0647875000
_diffrn_orient_matrix_UB_13 0.0041741000
_diffrn_orient_matrix_UB_21 -0.0773419000
_diffrn_orient_matrix_UB_22 -0.0255756000
_diffrn_orient_matrix_UB_23 -0.0428702000
_diffrn_orient_matrix_UB_31 0.0661083000
_diffrn_orient_matrix_UB_32 0.0254026000
_diffrn_orient_matrix_UB_33 -0.0325096000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 10018
_reflns_number_total 14381
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 3.290
_refine_diff_density_min -0.339
_refine_diff_density_rms 0.170
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.431
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 929
_refine_ls_number_reflns 14381
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1448
_refine_ls_R_factor_gt 0.1225
_refine_ls_restrained_S_all 1.431
_refine_ls_shift/su_max 0.546
_refine_ls_shift/su_mean 0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.3481
_refine_ls_wR_factor_ref 0.3780
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C36) = Uanis(C36A)
Uanis(C36') = Uanis(C1A)
3. Others
Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(H37C)=Sof(H37D)=1-FVAR(1)
Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H37A)=Sof(H37B)=FVAR(1)
Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H35G)=Sof(H35H)=Sof(H37G)=Sof(H37H)=1-FVAR(2)
Sof(H35E)=Sof(H35F)=Sof(C36')=Sof(H36E)=Sof(H36F)=Sof(H37E)=Sof(H37F)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C25(H25), C7'(H7'), C8'(H8'), C9'(H9'), C25'(H25')
4.b Secondary CH2 refined with riding coordinates:
C10(H10A,H10B), C26(H26A,H26B), C35(H35A,H35B), C35(H35C,H35D), C36(H36A,
H36B), C36A(H36C,H36D), C37(H37A,H37B), C37(H37C,H37D), C1A(H1AA,H1AB),
C10'(H10C,H10D), C26'(H26C,H26D), C35'(H35E,H35F), C35'(H35G,H35H), C36'(H36E,
H36F), C37'(H37E,H37F), C37'(H37G,H37H)
4.c Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
C31(H31), C32(H32), C40(H40), C41(H41), C43(H43), C44(H44), C2'(H2'),
C3'(H3'), C5'(H5'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16'),
C18'(H18'), C19'(H19'), C21'(H21'), C23'(H23'), C24'(H24'), C28'(H28'),
C29'(H29'), C30'(H30'), C31'(H31'), C32'(H32'), C40'(H40'), C41'(H41'),
C43'(H43'), C44'(H44')
4.d Idealised Me refined as rotating group:
C45(H45A,H45B,H45C), C45'(H45D,H45E,H45F)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1882(2) 0.7234(2) 0.42867(13) 0.0486(8) Uani 1 1 d . . . . .
C2 C 0.1256(3) 0.6859(2) 0.45040(14) 0.0581(10) Uani 1 1 d . . . . .
H2 H 0.0788 0.7061 0.4644 0.070 Uiso 1 1 calc R . . . .
C3 C 0.1324(3) 0.6212(3) 0.45124(16) 0.0650(12) Uani 1 1 d . . . . .
H3 H 0.0911 0.5971 0.4661 0.078 Uiso 1 1 calc R . . . .
C4 C 0.2011(3) 0.5905(2) 0.42992(16) 0.0629(11) Uani 1 1 d . . . . .
C5 C 0.2655(3) 0.6260(2) 0.40923(14) 0.0531(9) Uani 1 1 d . . . . .
H5 H 0.3127 0.6052 0.3957 0.064 Uiso 1 1 calc R . . . .
C6 C 0.2597(3) 0.6925(2) 0.40866(13) 0.0476(8) Uani 1 1 d . . . . .
C7 C 0.3289(2) 0.73337(18) 0.38660(13) 0.0456(8) Uani 1 1 d . . . . .
H7 H 0.3539 0.7079 0.3634 0.055 Uiso 1 1 calc R . . . .
C8 C 0.2700(3) 0.7912(2) 0.36276(14) 0.0510(9) Uani 1 1 d . . . . .
H8 H 0.3172 0.8183 0.3504 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2380(3) 0.8289(2) 0.40182(14) 0.0528(9) Uani 1 1 d . . . . .
H9 H 0.1965 0.8654 0.3877 0.063 Uiso 1 1 calc R . . . .
C10 C 0.1253(3) 0.8247(3) 0.45684(16) 0.0623(11) Uani 1 1 d . . . . .
H10A H 0.1506 0.8684 0.4608 0.075 Uiso 1 1 calc R . . . .
H10B H 0.1407 0.8043 0.4874 0.075 Uiso 1 1 calc R . . . .
C11 C 0.0116(3) 0.8271(2) 0.43948(14) 0.0515(9) Uani 1 1 d . . . . .
C12 C -0.0386(3) 0.8024(3) 0.39712(16) 0.0683(12) Uani 1 1 d . . . . .
H12 H -0.0020 0.7831 0.3776 0.082 Uiso 1 1 calc R . . . .
C13 C -0.1426(3) 0.8060(3) 0.38309(17) 0.0787(15) Uani 1 1 d . . . . .
H13 H -0.1748 0.7890 0.3543 0.094 Uiso 1 1 calc R . . . .
C14 C -0.1984(3) 0.8339(3) 0.41079(18) 0.0741(14) Uani 1 1 d . . . . .
H14 H -0.2682 0.8368 0.4009 0.089 Uiso 1 1 calc R . . . .
C15 C -0.1501(4) 0.8576(3) 0.45338(19) 0.0737(13) Uani 1 1 d . . . . .
H15 H -0.1876 0.8759 0.4730 0.088 Uiso 1 1 calc R . . . .
C16 C -0.0448(3) 0.8548(2) 0.46777(16) 0.0620(10) Uani 1 1 d . . . . .
H16 H -0.0127 0.8717 0.4967 0.074 Uiso 1 1 calc R . . . .
C17 C 0.2678(3) 0.7747(2) 0.25646(14) 0.0572(10) Uani 1 1 d . . . . .
C18 C 0.3335(4) 0.7466(3) 0.23233(16) 0.0702(12) Uani 1 1 d . . . . .
H18 H 0.3426 0.7022 0.2337 0.084 Uiso 1 1 calc R . . . .
C19 C 0.3864(4) 0.7837(3) 0.20598(17) 0.0730(13) Uani 1 1 d . . . . .
H19 H 0.4313 0.7644 0.1904 0.088 Uiso 1 1 calc R . . . .
C20 C 0.3710(4) 0.8491(3) 0.20344(16) 0.0700(12) Uani 1 1 d . . . . .
C21 C 0.3022(4) 0.8778(2) 0.22416(15) 0.0647(11) Uani 1 1 d . . . . .
H21 H 0.2904 0.9218 0.2205 0.078 Uiso 1 1 calc R . . . .
C22 C 0.2492(3) 0.8417(2) 0.25086(15) 0.0591(10) Uani 1 1 d . . . . .
C23 C 0.1668(4) 0.8681(3) 0.26950(17) 0.0735(13) Uani 1 1 d . . . . .
H23 H 0.1405 0.9082 0.2593 0.088 Uiso 1 1 calc R . . . .
C24 C 0.1286(4) 0.8364(3) 0.30056(17) 0.0745(14) Uani 1 1 d . . . . .
H24 H 0.0709 0.8512 0.3093 0.089 Uiso 1 1 calc R . . . .
C25 C 0.1808(3) 0.7752(2) 0.32171(15) 0.0601(10) Uani 1 1 d . . . . .
H25 H 0.1322 0.7482 0.3331 0.072 Uiso 1 1 calc R . . . .
C26 C 0.2138(4) 0.6709(2) 0.28448(17) 0.0753(14) Uani 1 1 d . . . . .
H26A H 0.2050 0.6567 0.3148 0.090 Uiso 1 1 calc R . . . .
H26B H 0.2789 0.6552 0.2809 0.090 Uiso 1 1 calc R . . . .
C27 C 0.1329(3) 0.6401(2) 0.24730(15) 0.0589(10) Uani 1 1 d . . . . .
C28 C 0.0629(3) 0.6740(3) 0.21513(16) 0.0653(11) Uani 1 1 d . . . . .
H28 H 0.0664 0.7187 0.2145 0.078 Uiso 1 1 calc R . . . .
C29 C -0.0135(4) 0.6419(3) 0.18333(18) 0.0792(15) Uani 1 1 d . . . . .
H29 H -0.0606 0.6655 0.1619 0.095 Uiso 1 1 calc R . . . .
C30 C -0.0196(5) 0.5775(4) 0.1835(2) 0.0980(19) Uani 1 1 d . . . . .
H30 H -0.0697 0.5561 0.1620 0.118 Uiso 1 1 calc R . . . .
C31 C 0.0494(8) 0.5440(4) 0.2157(3) 0.153(4) Uani 1 1 d . . . . .
H31 H 0.0464 0.4993 0.2163 0.184 Uiso 1 1 calc R . . . .
C32 C 0.1235(6) 0.5757(3) 0.2476(3) 0.110(3) Uani 1 1 d . . . . .
H32 H 0.1683 0.5518 0.2699 0.132 Uiso 1 1 calc R . . . .
C33 C 0.4173(2) 0.75825(19) 0.42350(12) 0.0455(8) Uani 1 1 d . . . . .
C34 C 0.4106(3) 0.81615(19) 0.44367(14) 0.0480(8) Uani 1 1 d . . . . .
C35 C 0.4957(3) 0.8468(2) 0.47827(16) 0.0568(10) Uani 1 1 d . . . . .
H35A H 0.4691 0.8717 0.5008 0.068 Uiso 0.703(8) 1 calc R . P A 1
H35B H 0.5328 0.8756 0.4622 0.068 Uiso 0.703(8) 1 calc R . P A 1
H35C H 0.4968 0.8925 0.4717 0.068 Uiso 0.297(8) 1 calc R . P A 2
H35D H 0.4835 0.8418 0.5095 0.068 Uiso 0.297(8) 1 calc R . P A 2
C36 C 0.5666(4) 0.7939(3) 0.5036(2) 0.0603(14) Uani 0.703(8) 1 d . . P A 1
H36A H 0.6266 0.8138 0.5225 0.072 Uiso 0.703(8) 1 calc R . P A 1
H36B H 0.5329 0.7708 0.5245 0.072 Uiso 0.703(8) 1 calc R . P A 1
C36A C 0.5948(10) 0.8191(8) 0.4773(5) 0.0603(14) Uani 0.297(8) 1 d . . P A 2
H36C H 0.6418 0.8303 0.5064 0.072 Uiso 0.297(8) 1 calc R . P A 2
H36D H 0.6190 0.8391 0.4520 0.072 Uiso 0.297(8) 1 calc R . P A 2
C37 C 0.5968(3) 0.7481(2) 0.47138(17) 0.0648(11) Uani 1 1 d . . . . .
H37A H 0.6325 0.7128 0.4894 0.078 Uiso 0.703(8) 1 calc R . P A 1
H37B H 0.6437 0.7694 0.4557 0.078 Uiso 0.703(8) 1 calc R . P A 1
H37C H 0.5958 0.7280 0.5012 0.078 Uiso 0.297(8) 1 calc R . P A 2
H37D H 0.6599 0.7364 0.4633 0.078 Uiso 0.297(8) 1 calc R . P A 2
C38 C 0.5110(2) 0.72096(19) 0.43465(13) 0.0459(8) Uani 1 1 d . . . . .
C39 C 0.6033(3) 0.6312(2) 0.42094(15) 0.0543(9) Uani 1 1 d . . . . .
C40 C 0.6880(3) 0.6513(2) 0.40529(18) 0.0647(11) Uani 1 1 d . . . . .
H40 H 0.6875 0.6909 0.3904 0.078 Uiso 1 1 calc R . . . .
C41 C 0.7730(3) 0.6125(2) 0.41173(19) 0.0674(12) Uani 1 1 d . . . . .
H41 H 0.8285 0.6261 0.4006 0.081 Uiso 1 1 calc R . . . .
C42 C 0.7767(3) 0.5536(2) 0.43460(17) 0.0626(11) Uani 1 1 d . . . . .
C43 C 0.6932(4) 0.5342(2) 0.44894(18) 0.0652(11) Uani 1 1 d . . . . .
H43 H 0.6940 0.4944 0.4636 0.078 Uiso 1 1 calc R . . . .
C44 C 0.6061(3) 0.5717(2) 0.44250(17) 0.0628(10) Uani 1 1 d . . . . .
H44 H 0.5500 0.5568 0.4526 0.075 Uiso 1 1 calc R . . . .
C45 C 0.8714(4) 0.5131(3) 0.4430(2) 0.0850(16) Uani 1 1 d . . . . .
H45A H 0.8994 0.5141 0.4156 0.127 Uiso 1 1 calc GR . . . .
H45B H 0.8552 0.4695 0.4493 0.127 Uiso 1 1 calc GR . . . .
H45C H 0.9199 0.5299 0.4693 0.127 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.20434(12) 0.50672(7) 0.42801(6) 0.0917(5) Uani 1 1 d . . . . .
Cl2 Cl 0.43871(13) 0.89581(10) 0.17151(6) 0.1064(6) Uani 1 1 d . . . . .
N1 N 0.1793(2) 0.79045(18) 0.42646(12) 0.0541(8) Uani 1 1 d . . . . .
N2 N 0.2166(3) 0.74060(19) 0.28452(13) 0.0652(9) Uani 1 1 d . . . . .
N3 N 0.5136(2) 0.66830(17) 0.41288(13) 0.0554(8) Uani 1 1 d . . . . .
O1 O 0.32815(19) 0.85427(13) 0.43418(11) 0.0553(7) Uani 1 1 d . . . . .
C1' C 0.7417(3) 0.2261(2) 0.41564(13) 0.0494(9) Uani 1 1 d . . . . .
C1A C 1.1279(5) 0.3045(4) 0.4818(3) 0.0604(15) Uani 0.532(8) 1 d . . P B 2
H1AA H 1.1886 0.3267 0.4979 0.072 Uiso 0.532(8) 1 calc R . P B 2
H1AB H 1.1015 0.2810 0.5051 0.072 Uiso 0.532(8) 1 calc R . P B 2
C2' C 0.6810(3) 0.1880(3) 0.43842(14) 0.0606(11) Uani 1 1 d . . . . .
H2' H 0.6320 0.2078 0.4512 0.073 Uiso 1 1 calc R . . . .
C3' C 0.6928(4) 0.1233(3) 0.44201(18) 0.0724(13) Uani 1 1 d . . . . .
H3' H 0.6529 0.0989 0.4575 0.087 Uiso 1 1 calc R . . . .
C4' C 0.7643(4) 0.0942(3) 0.4226(2) 0.0745(13) Uani 1 1 d . . . . .
C5' C 0.8246(3) 0.1290(2) 0.39930(16) 0.0591(10) Uani 1 1 d . . . . .
H5' H 0.8717 0.1082 0.3858 0.071 Uiso 1 1 calc R . . . .
C6' C 0.8140(3) 0.19493(19) 0.39634(12) 0.0466(8) Uani 1 1 d . . . . .
C7' C 0.8804(2) 0.23546(18) 0.37202(12) 0.0438(8) Uani 1 1 d . . . . .
H7' H 0.9042 0.2092 0.3488 0.053 Uiso 1 1 calc R . . . .
C8' C 0.8186(3) 0.29239(19) 0.34774(13) 0.0464(8) Uani 1 1 d . . . . .
H8' H 0.8644 0.3196 0.3345 0.056 Uiso 1 1 calc R . . . .
C9' C 0.7879(3) 0.33055(18) 0.38656(14) 0.0486(8) Uani 1 1 d . . . . .
H9' H 0.7453 0.3665 0.3722 0.058 Uiso 1 1 calc R . . . .
C10' C 0.6816(3) 0.3281(3) 0.44364(15) 0.0611(11) Uani 1 1 d . . . . .
H10C H 0.7141 0.3698 0.4497 0.073 Uiso 1 1 calc R . . . .
H10D H 0.6925 0.3053 0.4732 0.073 Uiso 1 1 calc R . . . .
C11' C 0.5682(3) 0.3388(2) 0.42596(14) 0.0520(9) Uani 1 1 d . . . . .
C12' C 0.5134(3) 0.3115(3) 0.38499(17) 0.0702(13) Uani 1 1 d . . . . .
H12' H 0.5454 0.2855 0.3669 0.084 Uiso 1 1 calc R . . . .
C13' C 0.4107(4) 0.3233(4) 0.37109(19) 0.0873(18) Uani 1 1 d . . . . .
H13' H 0.3738 0.3043 0.3438 0.105 Uiso 1 1 calc R . . . .
C14' C 0.3635(4) 0.3619(4) 0.3965(2) 0.100(2) Uani 1 1 d . . . . .
H14' H 0.2949 0.3703 0.3864 0.120 Uiso 1 1 calc R . . . .
C15' C 0.4171(4) 0.3886(4) 0.4373(2) 0.100(2) Uani 1 1 d . . . . .
H15' H 0.3847 0.4152 0.4549 0.120 Uiso 1 1 calc R . . . .
C16' C 0.5189(3) 0.3762(3) 0.45250(17) 0.0712(13) Uani 1 1 d . . . . .
H16' H 0.5544 0.3932 0.4808 0.085 Uiso 1 1 calc R . . . .
C17' C 0.8120(3) 0.2712(2) 0.24199(13) 0.0532(9) Uani 1 1 d . . . . .
C18' C 0.8756(3) 0.2415(2) 0.21716(15) 0.0619(11) Uani 1 1 d . . . . .
H18' H 0.8837 0.1971 0.2191 0.074 Uiso 1 1 calc R . . . .
C19' C 0.9274(3) 0.2764(3) 0.18958(16) 0.0671(12) Uani 1 1 d . . . . .
H19' H 0.9707 0.2557 0.1738 0.081 Uiso 1 1 calc R . . . .
C20' C 0.9138(3) 0.3423(3) 0.18587(16) 0.0658(11) Uani 1 1 d . . . . .
C21' C 0.8485(4) 0.3726(2) 0.20744(15) 0.0624(11) Uani 1 1 d . . . . .
H21' H 0.8391 0.4168 0.2038 0.075 Uiso 1 1 calc R . . . .
C22' C 0.7951(3) 0.3381(2) 0.23512(14) 0.0551(9) Uani 1 1 d . . . . .
C23' C 0.7141(3) 0.3662(2) 0.25418(16) 0.0632(11) Uani 1 1 d . . . . .
H23' H 0.6882 0.4062 0.2433 0.076 Uiso 1 1 calc R . . . .
C24' C 0.6769(3) 0.3367(2) 0.28613(15) 0.0627(11) Uani 1 1 d . . . . .
H24' H 0.6208 0.3529 0.2956 0.075 Uiso 1 1 calc R . . . .
C25' C 0.7282(3) 0.2749(2) 0.30739(14) 0.0531(9) Uani 1 1 d . . . . .
H25' H 0.6797 0.2491 0.3198 0.064 Uiso 1 1 calc R . . . .
C26' C 0.7615(4) 0.1687(2) 0.27271(15) 0.0640(11) Uani 1 1 d . . . . .
H26C H 0.7446 0.1557 0.3019 0.077 Uiso 1 1 calc R . . . .
H26D H 0.8295 0.1538 0.2735 0.077 Uiso 1 1 calc R . . . .
C27' C 0.6894(3) 0.1353(2) 0.23251(14) 0.0570(10) Uani 1 1 d . . . . .
C28' C 0.6096(3) 0.1659(3) 0.20398(15) 0.0637(11) Uani 1 1 d . . . . .
H28' H 0.6018 0.2101 0.2067 0.076 Uiso 1 1 calc R . . . .
C29' C 0.5398(4) 0.1314(3) 0.17080(18) 0.0760(14) Uani 1 1 d . . . . .
H29' H 0.4852 0.1527 0.1520 0.091 Uiso 1 1 calc R . . . .
C30' C 0.5505(5) 0.0669(3) 0.1656(2) 0.0901(17) Uani 1 1 d . . . . .
H30' H 0.5035 0.0441 0.1436 0.108 Uiso 1 1 calc R . . . .
C31' C 0.6319(6) 0.0360(3) 0.1933(3) 0.108(2) Uani 1 1 d . . . . .
H31' H 0.6404 -0.0080 0.1899 0.130 Uiso 1 1 calc R . . . .
C32' C 0.7013(5) 0.0702(3) 0.2265(2) 0.0854(16) Uani 1 1 d . . . . .
H32' H 0.7564 0.0489 0.2449 0.103 Uiso 1 1 calc R . . . .
C33' C 0.9702(2) 0.26284(18) 0.40722(13) 0.0445(8) Uani 1 1 d . . . . .
C34' C 0.9633(3) 0.32076(19) 0.42639(13) 0.0471(8) Uani 1 1 d . . . . .
C35' C 1.0489(3) 0.3550(2) 0.45845(16) 0.0574(10) Uani 1 1 d . . . . .
H35E H 1.0442 0.4007 0.4514 0.069 Uiso 0.468(8) 1 calc R . P B 1
H35F H 1.0425 0.3496 0.4905 0.069 Uiso 0.468(8) 1 calc R . P B 1
H35G H 1.0240 0.3785 0.4822 0.069 Uiso 0.532(8) 1 calc R . P B 2
H35H H 1.0796 0.3856 0.4408 0.069 Uiso 0.532(8) 1 calc R . P B 2
C36' C 1.1487(6) 0.3315(5) 0.4543(4) 0.0604(15) Uani 0.468(8) 1 d . . P B 1
H36E H 1.1986 0.3450 0.4817 0.072 Uiso 0.468(8) 1 calc R . P B 1
H36F H 1.1659 0.3513 0.4271 0.072 Uiso 0.468(8) 1 calc R . P B 1
C37' C 1.1543(3) 0.2595(2) 0.44972(19) 0.0678(12) Uani 1 1 d . . . . .
H37E H 1.1622 0.2408 0.4807 0.081 Uiso 0.468(8) 1 calc R . P B 1
H37F H 1.2147 0.2493 0.4387 0.081 Uiso 0.468(8) 1 calc R . P B 1
H37G H 1.1970 0.2265 0.4674 0.081 Uiso 0.532(8) 1 calc R . P B 2
H37H H 1.1937 0.2817 0.4307 0.081 Uiso 0.532(8) 1 calc R . P B 2
C38' C 1.0654(2) 0.22712(19) 0.41750(13) 0.0461(8) Uani 1 1 d . . . . .
C39' C 1.1577(3) 0.1347(2) 0.40687(15) 0.0556(9) Uani 1 1 d . . . . .
C40' C 1.2353(4) 0.1504(2) 0.38543(18) 0.0685(12) Uani 1 1 d . . . . .
H40' H 1.2310 0.1878 0.3676 0.082 Uiso 1 1 calc R . . . .
C41' C 1.3195(4) 0.1111(3) 0.3903(2) 0.0740(13) Uani 1 1 d . . . . .
H41' H 1.3707 0.1225 0.3754 0.089 Uiso 1 1 calc R . . . .
C42' C 1.3293(4) 0.0556(2) 0.41653(19) 0.0691(12) Uani 1 1 d . . . . .
C43' C 1.2517(4) 0.0406(2) 0.4377(2) 0.0750(13) Uani 1 1 d . . . . .
H43' H 1.2566 0.0036 0.4560 0.090 Uiso 1 1 calc R . . . .
C44' C 1.1662(4) 0.0790(2) 0.43273(17) 0.0660(11) Uani 1 1 d . . . . .
H44' H 1.1144 0.0669 0.4470 0.079 Uiso 1 1 calc R . . . .
C45' C 1.4205(5) 0.0131(3) 0.4213(3) 0.098(2) Uani 1 1 d . . . . .
H45D H 1.4002 -0.0282 0.4079 0.147 Uiso 1 1 calc GR . . . .
H45E H 1.4520 0.0081 0.4539 0.147 Uiso 1 1 calc GR . . . .
H45F H 1.4675 0.0324 0.4053 0.147 Uiso 1 1 calc GR . . . .
Cl1' Cl 0.77804(19) 0.01046(8) 0.42643(9) 0.1316(8) Uani 1 1 d . . . . .
Cl2' Cl 0.97913(12) 0.38586(9) 0.15117(5) 0.0950(5) Uani 1 1 d . . . . .
N1' N 0.7306(2) 0.29241(17) 0.41224(11) 0.0514(8) Uani 1 1 d . . . . .
N2' N 0.7606(3) 0.23861(17) 0.27039(12) 0.0574(8) Uani 1 1 d . . . . .
N3' N 1.0670(2) 0.17100(18) 0.39946(13) 0.0556(8) Uani 1 1 d . . . . .
O1' O 0.87776(19) 0.35725(13) 0.41761(11) 0.0557(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0337(15) 0.064(2) 0.0424(18) 0.0039(17) -0.0023(13) -0.0006(15)
C2 0.0410(18) 0.078(3) 0.052(2) 0.007(2) 0.0042(16) -0.0003(18)
C3 0.047(2) 0.086(3) 0.057(2) 0.022(2) 0.0030(17) -0.008(2)
C4 0.058(2) 0.060(2) 0.061(2) 0.016(2) -0.0073(19) -0.0056(19)
C5 0.0457(18) 0.058(2) 0.051(2) 0.0056(18) -0.0007(16) 0.0005(16)
C6 0.0374(16) 0.059(2) 0.0415(17) 0.0043(16) -0.0023(13) -0.0012(15)
C7 0.0346(15) 0.0519(19) 0.0472(19) 0.0017(16) 0.0025(14) 0.0007(14)
C8 0.0393(17) 0.058(2) 0.052(2) 0.0110(18) 0.0031(15) 0.0017(15)
C9 0.0384(17) 0.056(2) 0.058(2) 0.0049(18) -0.0022(16) 0.0055(15)
C10 0.0442(19) 0.081(3) 0.058(2) -0.014(2) 0.0049(17) -0.0018(19)
C11 0.0409(18) 0.058(2) 0.052(2) 0.0021(17) 0.0050(15) 0.0046(15)
C12 0.048(2) 0.097(4) 0.058(2) -0.011(2) 0.0063(18) 0.009(2)
C13 0.049(2) 0.118(4) 0.060(3) -0.005(3) -0.008(2) 0.004(3)
C14 0.045(2) 0.100(4) 0.074(3) 0.016(3) 0.005(2) 0.016(2)
C15 0.054(2) 0.093(4) 0.076(3) 0.007(3) 0.018(2) 0.020(2)
C16 0.055(2) 0.075(3) 0.054(2) -0.003(2) 0.0069(18) 0.007(2)
C17 0.060(2) 0.060(2) 0.0424(19) -0.0011(18) -0.0093(17) 0.0031(18)
C18 0.081(3) 0.068(3) 0.053(2) -0.005(2) -0.003(2) 0.013(2)
C19 0.070(3) 0.091(4) 0.053(2) -0.007(2) 0.004(2) 0.010(3)
C20 0.064(3) 0.092(4) 0.048(2) 0.002(2) 0.0011(19) -0.007(2)
C21 0.073(3) 0.061(2) 0.052(2) 0.003(2) -0.002(2) 0.002(2)
C22 0.059(2) 0.064(2) 0.047(2) 0.0060(18) -0.0044(17) 0.0081(19)
C23 0.076(3) 0.079(3) 0.060(3) 0.020(2) 0.004(2) 0.028(3)
C24 0.054(2) 0.103(4) 0.061(3) 0.016(3) 0.000(2) 0.025(2)
C25 0.049(2) 0.074(3) 0.051(2) 0.013(2) -0.0015(17) 0.0004(19)
C26 0.084(3) 0.068(3) 0.059(3) 0.015(2) -0.016(2) -0.004(2)
C27 0.059(2) 0.065(3) 0.049(2) -0.0005(19) 0.0043(18) -0.0018(19)
C28 0.057(2) 0.077(3) 0.057(2) -0.006(2) 0.0031(19) 0.005(2)
C29 0.052(2) 0.119(5) 0.061(3) -0.008(3) 0.000(2) 0.008(3)
C30 0.091(4) 0.098(4) 0.093(4) -0.012(4) -0.003(3) -0.031(3)
C31 0.189(9) 0.078(4) 0.145(7) -0.002(5) -0.064(6) -0.041(5)
C32 0.131(6) 0.067(3) 0.102(5) 0.008(3) -0.040(4) -0.007(3)
C33 0.0313(15) 0.058(2) 0.0450(18) 0.0008(16) 0.0034(13) 0.0003(14)
C34 0.0356(16) 0.053(2) 0.054(2) 0.0049(17) 0.0064(15) 0.0017(15)
C35 0.0433(18) 0.057(2) 0.066(2) -0.0048(19) 0.0031(17) -0.0028(16)
C36 0.044(3) 0.075(4) 0.054(3) -0.007(3) -0.004(2) 0.004(2)
C36A 0.044(3) 0.075(4) 0.054(3) -0.007(3) -0.004(2) 0.004(2)
C37 0.0388(18) 0.068(3) 0.077(3) -0.007(2) -0.0102(18) 0.0081(18)
C38 0.0356(16) 0.054(2) 0.0461(18) 0.0050(16) 0.0055(14) 0.0002(14)
C39 0.0470(19) 0.059(2) 0.055(2) -0.0036(18) 0.0074(16) 0.0081(17)
C40 0.059(2) 0.055(2) 0.083(3) 0.018(2) 0.022(2) 0.0137(19)
C41 0.055(2) 0.064(3) 0.088(3) 0.006(2) 0.024(2) 0.0110(19)
C42 0.060(2) 0.052(2) 0.073(3) -0.003(2) 0.008(2) 0.0120(18)
C43 0.067(3) 0.052(2) 0.075(3) 0.010(2) 0.011(2) 0.0049(19)
C44 0.057(2) 0.060(2) 0.072(3) 0.007(2) 0.016(2) 0.0016(19)
C45 0.068(3) 0.061(3) 0.120(5) -0.003(3) 0.008(3) 0.022(2)
Cl1 0.0928(9) 0.0617(7) 0.1148(11) 0.0223(7) 0.0108(8) -0.0043(6)
Cl2 0.0960(10) 0.1346(15) 0.0923(10) 0.0169(10) 0.0289(8) -0.0199(10)
N1 0.0376(14) 0.064(2) 0.0594(19) -0.0037(16) 0.0078(13) -0.0006(14)
N2 0.073(2) 0.063(2) 0.0518(19) 0.0035(17) -0.0021(17) -0.0069(18)
N3 0.0422(16) 0.060(2) 0.0605(19) -0.0033(16) 0.0039(14) 0.0091(14)
O1 0.0399(13) 0.0493(14) 0.0726(18) -0.0030(13) 0.0041(12) 0.0029(11)
C1' 0.0352(15) 0.067(2) 0.0410(17) -0.0032(17) -0.0016(13) -0.0024(15)
C1A 0.041(3) 0.065(4) 0.067(4) -0.009(3) -0.006(3) -0.002(3)
C2' 0.0431(19) 0.089(3) 0.048(2) 0.003(2) 0.0066(16) -0.0043(19)
C3' 0.064(3) 0.088(3) 0.063(3) 0.016(3) 0.010(2) -0.014(2)
C4' 0.077(3) 0.063(3) 0.081(3) 0.011(2) 0.012(3) -0.011(2)
C5' 0.056(2) 0.056(2) 0.064(2) 0.0010(19) 0.0090(18) -0.0021(18)
C6' 0.0407(16) 0.053(2) 0.0425(18) -0.0024(15) 0.0009(14) -0.0017(15)
C7' 0.0349(15) 0.0500(19) 0.0444(18) -0.0033(15) 0.0048(13) 0.0022(14)
C8' 0.0385(16) 0.053(2) 0.0461(19) 0.0011(16) 0.0056(14) 0.0040(14)
C9' 0.0366(16) 0.0488(19) 0.056(2) -0.0026(17) 0.0014(15) 0.0059(14)
C10' 0.0406(18) 0.083(3) 0.056(2) -0.022(2) 0.0035(16) 0.0029(18)
C11' 0.0389(17) 0.068(2) 0.0473(19) -0.0004(18) 0.0049(15) 0.0057(16)
C12' 0.049(2) 0.096(4) 0.061(2) -0.019(2) 0.0025(18) 0.010(2)
C13' 0.051(2) 0.137(5) 0.065(3) -0.007(3) -0.006(2) 0.013(3)
C14' 0.050(2) 0.171(7) 0.073(3) 0.002(4) 0.000(2) 0.038(3)
C15' 0.068(3) 0.146(6) 0.089(4) -0.010(4) 0.024(3) 0.050(4)
C16' 0.056(2) 0.096(4) 0.058(2) -0.009(2) 0.0054(19) 0.016(2)
C17' 0.0510(19) 0.060(2) 0.0410(18) -0.0093(17) -0.0054(15) 0.0021(17)
C18' 0.065(2) 0.065(3) 0.051(2) -0.012(2) 0.0044(19) 0.006(2)
C19' 0.059(2) 0.086(3) 0.054(2) -0.012(2) 0.0067(19) 0.003(2)
C20' 0.058(2) 0.081(3) 0.054(2) -0.010(2) 0.0041(19) -0.011(2)
C21' 0.071(3) 0.064(3) 0.047(2) 0.0008(19) 0.0032(19) -0.003(2)
C22' 0.053(2) 0.061(2) 0.047(2) -0.0003(18) 0.0007(16) 0.0031(18)
C23' 0.060(2) 0.067(3) 0.058(2) 0.006(2) 0.0043(19) 0.018(2)
C24' 0.048(2) 0.080(3) 0.055(2) 0.004(2) 0.0006(17) 0.020(2)
C25' 0.0438(18) 0.063(2) 0.048(2) 0.0017(18) 0.0009(15) -0.0010(16)
C26' 0.071(3) 0.060(2) 0.051(2) 0.0024(19) -0.0076(19) -0.005(2)
C27' 0.057(2) 0.064(2) 0.048(2) -0.0017(19) 0.0069(17) -0.0100(19)
C28' 0.057(2) 0.076(3) 0.054(2) -0.008(2) 0.0044(18) 0.002(2)
C29' 0.054(2) 0.102(4) 0.065(3) -0.004(3) -0.002(2) -0.004(2)
C30' 0.078(3) 0.096(4) 0.086(4) -0.012(3) -0.004(3) -0.032(3)
C31' 0.122(5) 0.066(3) 0.115(5) -0.015(3) -0.018(4) -0.022(3)
C32' 0.091(4) 0.061(3) 0.088(4) -0.006(3) -0.015(3) 0.000(3)
C33' 0.0342(15) 0.052(2) 0.0461(18) -0.0046(15) 0.0054(14) 0.0009(14)
C34' 0.0355(16) 0.054(2) 0.0504(19) -0.0052(16) 0.0064(14) 0.0009(14)
C35' 0.0437(19) 0.059(2) 0.065(2) -0.012(2) 0.0033(17) -0.0035(17)
C36' 0.041(3) 0.065(4) 0.067(4) -0.009(3) -0.006(3) -0.002(3)
C37' 0.0378(18) 0.067(3) 0.088(3) -0.008(2) -0.0088(19) 0.0056(18)
C38' 0.0358(16) 0.054(2) 0.0474(19) -0.0013(16) 0.0061(14) 0.0022(14)
C39' 0.0469(19) 0.059(2) 0.060(2) -0.0024(19) 0.0097(17) 0.0098(17)
C40' 0.063(3) 0.065(3) 0.081(3) 0.020(2) 0.024(2) 0.020(2)
C41' 0.060(2) 0.076(3) 0.094(3) 0.012(3) 0.036(3) 0.016(2)
C42' 0.061(2) 0.061(3) 0.086(3) 0.003(2) 0.018(2) 0.021(2)
C43' 0.081(3) 0.061(3) 0.086(3) 0.018(2) 0.023(3) 0.017(2)
C44' 0.064(2) 0.064(3) 0.074(3) 0.010(2) 0.023(2) 0.009(2)
C45' 0.081(3) 0.073(3) 0.143(6) 0.012(4) 0.029(4) 0.035(3)
Cl1' 0.1658(19) 0.0641(9) 0.179(2) 0.0325(11) 0.0690(17) -0.0029(10)
Cl2' 0.0943(10) 0.1171(12) 0.0797(9) -0.0076(8) 0.0327(7) -0.0311(9)
N1' 0.0380(14) 0.064(2) 0.0513(17) -0.0092(15) 0.0069(12) 0.0045(13)
N2' 0.065(2) 0.0540(19) 0.0489(18) -0.0024(15) 0.0043(15) -0.0016(16)
N3' 0.0423(16) 0.061(2) 0.0609(19) -0.0048(16) 0.0052(14) 0.0115(14)
O1' 0.0387(12) 0.0517(15) 0.0722(18) -0.0163(13) 0.0027(12) 0.0050(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.407(6) . ?
C1 C6 1.398(5) . ?
C1 N1 1.398(6) . ?
C2 C3 1.347(7) . ?
C3 C4 1.388(7) . ?
C4 C5 1.383(6) . ?
C4 Cl1 1.742(5) . ?
C5 C6 1.384(6) . ?
C6 C7 1.515(5) . ?
C7 C8 1.524(5) . ?
C7 C33 1.516(5) . ?
C8 C9 1.527(6) . ?
C8 C25 1.541(5) . ?
C9 N1 1.432(5) . ?
C9 O1 1.469(4) . ?
C10 C11 1.515(5) . ?
C10 N1 1.458(5) . ?
C11 C12 1.374(6) . ?
C11 C16 1.374(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.358(7) . ?
C14 C15 1.365(8) . ?
C15 C16 1.399(6) . ?
C17 C18 1.385(7) . ?
C17 C22 1.418(6) . ?
C17 N2 1.384(6) . ?
C18 C19 1.397(8) . ?
C19 C20 1.375(8) . ?
C20 C21 1.359(7) . ?
C20 Cl2 1.745(5) . ?
C21 C22 1.394(7) . ?
C22 C23 1.457(7) . ?
C23 C24 1.320(7) . ?
C24 C25 1.518(7) . ?
C25 N2 1.475(6) . ?
C26 C27 1.507(6) . ?
C26 N2 1.448(6) . ?
C27 C28 1.374(6) . ?
C27 C32 1.344(8) . ?
C28 C29 1.399(7) . ?
C29 C30 1.341(9) . ?
C30 C31 1.364(11) . ?
C31 C32 1.377(9) . ?
C33 C34 1.352(6) . ?
C33 C38 1.462(5) . ?
C34 C35 1.498(5) . ?
C34 O1 1.349(4) . ?
C35 C36 1.538(7) . ?
C35 C36A 1.470(14) . ?
C36 C37 1.462(8) . ?
C36A C37 1.486(17) . ?
C37 C38 1.508(5) . ?
C38 N3 1.271(5) . ?
C39 C40 1.394(6) . ?
C39 C44 1.386(6) . ?
C39 N3 1.416(5) . ?
C40 C41 1.386(6) . ?
C41 C42 1.391(7) . ?
C42 C43 1.356(7) . ?
C42 C45 1.510(6) . ?
C43 C44 1.393(6) . ?
C1' C2' 1.413(6) . ?
C1' C6' 1.397(5) . ?
C1' N1' 1.387(6) . ?
C1A C35' 1.548(9) . ?
C1A C37' 1.426(10) . ?
C2' C3' 1.357(8) . ?
C3' C4' 1.370(8) . ?
C4' C5' 1.382(7) . ?
C4' Cl1' 1.750(5) . ?
C5' C6' 1.378(6) . ?
C6' C7' 1.521(5) . ?
C7' C8' 1.530(5) . ?
C7' C33' 1.521(5) . ?
C8' C9' 1.519(5) . ?
C8' C25' 1.546(5) . ?
C9' N1' 1.435(5) . ?
C9' O1' 1.459(4) . ?
C10' C11' 1.527(5) . ?
C10' N1' 1.454(5) . ?
C11' C12' 1.384(6) . ?
C11' C16' 1.374(6) . ?
C12' C13' 1.385(6) . ?
C13' C14' 1.350(8) . ?
C14' C15' 1.371(9) . ?
C15' C16' 1.379(7) . ?
C17' C18' 1.392(6) . ?
C17' C22' 1.417(6) . ?
C17' N2' 1.377(6) . ?
C18' C19' 1.388(7) . ?
C19' C20' 1.382(7) . ?
C20' C21' 1.353(7) . ?
C20' Cl2' 1.745(5) . ?
C21' C22' 1.400(6) . ?
C22' C23' 1.462(6) . ?
C23' C24' 1.311(7) . ?
C24' C25' 1.524(6) . ?
C25' N2' 1.467(5) . ?
C26' C27' 1.520(6) . ?
C26' N2' 1.454(6) . ?
C27' C28' 1.369(6) . ?
C27' C32' 1.377(7) . ?
C28' C29' 1.395(7) . ?
C29' C30' 1.359(9) . ?
C30' C31' 1.376(9) . ?
C31' C32' 1.389(8) . ?
C33' C34' 1.340(5) . ?
C33' C38' 1.463(5) . ?
C34' C35' 1.501(5) . ?
C34' O1' 1.363(4) . ?
C35' C36' 1.471(10) . ?
C36' C37' 1.505(11) . ?
C37' C38' 1.514(5) . ?
C38' N3' 1.282(5) . ?
C39' C40' 1.380(6) . ?
C39' C44' 1.374(7) . ?
C39' N3' 1.420(5) . ?
C40' C41' 1.388(6) . ?
C41' C42' 1.375(7) . ?
C42' C43' 1.373(7) . ?
C42' C45' 1.501(6) . ?
C43' C44' 1.389(7) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.7(4) . . ?
C6 C1 N1 120.1(3) . . ?
N1 C1 C2 121.2(4) . . ?
C3 C2 C1 121.0(4) . . ?
C2 C3 C4 120.1(4) . . ?
C3 C4 Cl1 119.9(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 Cl1 119.7(4) . . ?
C4 C5 C6 119.8(4) . . ?
C1 C6 C7 118.4(4) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 C7 121.7(4) . . ?
C6 C7 C8 109.0(3) . . ?
C6 C7 C33 110.8(3) . . ?
C33 C7 C8 108.0(3) . . ?
C7 C8 C9 105.6(3) . . ?
C7 C8 C25 115.3(4) . . ?
C9 C8 C25 113.0(3) . . ?
N1 C9 C8 112.1(3) . . ?
N1 C9 O1 110.7(3) . . ?
O1 C9 C8 109.4(3) . . ?
N1 C10 C11 115.1(3) . . ?
C12 C11 C10 123.6(4) . . ?
C12 C11 C16 118.0(4) . . ?
C16 C11 C10 118.3(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C13 C12 121.0(5) . . ?
C13 C14 C15 118.8(4) . . ?
C14 C15 C16 120.7(4) . . ?
C11 C16 C15 120.4(4) . . ?
C18 C17 C22 118.2(4) . . ?
N2 C17 C18 123.6(4) . . ?
N2 C17 C22 118.1(4) . . ?
C17 C18 C19 121.2(5) . . ?
C20 C19 C18 119.0(5) . . ?
C19 C20 Cl2 119.1(4) . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 Cl2 119.5(4) . . ?
C20 C21 C22 120.4(5) . . ?
C17 C22 C23 117.3(4) . . ?
C21 C22 C17 119.5(4) . . ?
C21 C22 C23 122.9(4) . . ?
C24 C23 C22 121.5(4) . . ?
C23 C24 C25 118.7(4) . . ?
C24 C25 C8 110.6(4) . . ?
N2 C25 C8 110.5(3) . . ?
N2 C25 C24 107.9(4) . . ?
N2 C26 C27 116.2(4) . . ?
C28 C27 C26 123.9(4) . . ?
C32 C27 C26 118.3(4) . . ?
C32 C27 C28 117.6(5) . . ?
C27 C28 C29 120.6(5) . . ?
C30 C29 C28 120.7(5) . . ?
C29 C30 C31 118.5(6) . . ?
C30 C31 C32 120.7(7) . . ?
C27 C32 C31 121.9(6) . . ?
C34 C33 C7 119.7(3) . . ?
C34 C33 C38 120.9(3) . . ?
C38 C33 C7 119.3(3) . . ?
C33 C34 C35 123.8(3) . . ?
O1 C34 C33 124.5(3) . . ?
O1 C34 C35 111.7(3) . . ?
C34 C35 C36 109.2(4) . . ?
C36A C35 C34 113.1(7) . . ?
C37 C36 C35 112.8(5) . . ?
C35 C36A C37 115.5(11) . . ?
C36 C37 C38 114.9(4) . . ?
C36A C37 C38 115.1(6) . . ?
C33 C38 C37 117.1(3) . . ?
N3 C38 C33 117.6(3) . . ?
N3 C38 C37 125.2(3) . . ?
C40 C39 N3 121.7(4) . . ?
C44 C39 C40 118.4(4) . . ?
C44 C39 N3 119.8(4) . . ?
C41 C40 C39 120.3(4) . . ?
C40 C41 C42 121.1(4) . . ?
C41 C42 C45 120.4(5) . . ?
C43 C42 C41 117.9(4) . . ?
C43 C42 C45 121.7(5) . . ?
C42 C43 C44 122.4(4) . . ?
C39 C44 C43 119.8(4) . . ?
C1 N1 C9 121.7(3) . . ?
C1 N1 C10 120.5(4) . . ?
C9 N1 C10 116.6(4) . . ?
C17 N2 C25 118.8(4) . . ?
C17 N2 C26 121.8(4) . . ?
C26 N2 C25 118.3(4) . . ?
C38 N3 C39 120.2(3) . . ?
C34 O1 C9 117.1(3) . . ?
C6' C1' C2' 117.9(4) . . ?
N1' C1' C2' 121.6(4) . . ?
N1' C1' C6' 120.4(4) . . ?
C37' C1A C35' 113.9(6) . . ?
C3' C2' C1' 121.4(4) . . ?
C2' C3' C4' 119.2(4) . . ?
C3' C4' C5' 121.8(5) . . ?
C3' C4' Cl1' 119.1(4) . . ?
C5' C4' Cl1' 119.1(4) . . ?
C6' C5' C4' 119.1(4) . . ?
C1' C6' C7' 118.4(3) . . ?
C5' C6' C1' 120.5(4) . . ?
C5' C6' C7' 121.0(3) . . ?
C6' C7' C8' 109.0(3) . . ?
C33' C7' C6' 111.0(3) . . ?
C33' C7' C8' 107.4(3) . . ?
C7' C8' C25' 115.7(3) . . ?
C9' C8' C7' 105.6(3) . . ?
C9' C8' C25' 113.0(3) . . ?
N1' C9' C8' 112.1(3) . . ?
N1' C9' O1' 111.0(3) . . ?
O1' C9' C8' 109.5(3) . . ?
N1' C10' C11' 115.4(3) . . ?
C12' C11' C10' 122.8(4) . . ?
C16' C11' C10' 118.1(4) . . ?
C16' C11' C12' 119.1(4) . . ?
C11' C12' C13' 119.6(5) . . ?
C14' C13' C12' 120.9(5) . . ?
C13' C14' C15' 119.8(4) . . ?
C14' C15' C16' 120.3(5) . . ?
C11' C16' C15' 120.3(5) . . ?
C18' C17' C22' 117.4(4) . . ?
N2' C17' C18' 123.7(4) . . ?
N2' C17' C22' 118.7(4) . . ?
C19' C18' C17' 121.8(5) . . ?
C20' C19' C18' 119.1(4) . . ?
C19' C20' Cl2' 118.9(4) . . ?
C21' C20' C19' 121.0(5) . . ?
C21' C20' Cl2' 120.1(4) . . ?
C20' C21' C22' 120.6(5) . . ?
C17' C22' C23' 116.7(4) . . ?
C21' C22' C17' 119.8(4) . . ?
C21' C22' C23' 123.3(4) . . ?
C24' C23' C22' 121.8(4) . . ?
C23' C24' C25' 118.2(4) . . ?
C24' C25' C8' 109.1(3) . . ?
N2' C25' C8' 111.6(3) . . ?
N2' C25' C24' 108.4(3) . . ?
N2' C26' C27' 115.0(4) . . ?
C28' C27' C26' 123.1(4) . . ?
C28' C27' C32' 118.5(4) . . ?
C32' C27' C26' 118.2(4) . . ?
C27' C28' C29' 120.6(5) . . ?
C30' C29' C28' 120.8(5) . . ?
C29' C30' C31' 119.1(5) . . ?
C30' C31' C32' 120.3(6) . . ?
C27' C32' C31' 120.7(5) . . ?
C34' C33' C7' 120.0(3) . . ?
C34' C33' C38' 120.7(3) . . ?
C38' C33' C7' 119.2(3) . . ?
C33' C34' C35' 124.9(3) . . ?
C33' C34' O1' 123.8(3) . . ?
O1' C34' C35' 111.3(3) . . ?
C34' C35' C1A 108.5(4) . . ?
C36' C35' C34' 112.9(5) . . ?
C35' C36' C37' 113.8(7) . . ?
C1A C37' C38' 114.8(4) . . ?
C36' C37' C38' 116.6(4) . . ?
C33' C38' C37' 116.6(3) . . ?
N3' C38' C33' 118.1(3) . . ?
N3' C38' C37' 125.3(3) . . ?
C40' C39' N3' 121.9(4) . . ?
C44' C39' C40' 118.2(4) . . ?
C44' C39' N3' 119.7(4) . . ?
C39' C40' C41' 120.6(4) . . ?
C42' C41' C40' 121.7(4) . . ?
C41' C42' C45' 121.3(5) . . ?
C43' C42' C41' 117.1(4) . . ?
C43' C42' C45' 121.6(5) . . ?
C42' C43' C44' 122.0(5) . . ?
C39' C44' C43' 120.4(4) . . ?
C1' N1' C9' 121.5(3) . . ?
C1' N1' C10' 121.3(4) . . ?
C9' N1' C10' 115.4(3) . . ?
C17' N2' C25' 118.0(3) . . ?
C17' N2' C26' 121.3(4) . . ?
C26' N2' C25' 118.7(4) . . ?
C38' N3' C39' 120.9(3) . . ?
C34' O1' C9' 117.7(3) . . ?
_iucr_refine_instructions_details
;
201809362.res created by SHELXL-2014/7
TITL CF solution in P21/n
CELL 1.54184 13.580532 20.775304 29.292081 90 102.8973 90
ZERR 8 0.000113 0.000212 0.00028 0 0.0009 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 360 312 16 24 8
EADP C36 C36A
EADP C36' C1A
L.S. 4 0 0
PLAN 20
MPLA C1 C2 C3 C4 C5 C6
MPLA C11 C12 C13 C14 C15 C16
MPLA C17 C18 C19 C20 C21 C22
MPLA C27 C28 C29 C30 C31 C32
MPLA C39 C40 C41 C42 C43 C44
fmap 2
acta
REM
REM
REM
WGHT 0.200000
FVAR 1.11832 0.70314 0.46756
C1 1 0.188234 0.723448 0.428665 11.00000 0.03375 0.06449 =
0.04242 0.00391 -0.00234 -0.00062
C2 1 0.125600 0.685906 0.450400 11.00000 0.04101 0.07837 =
0.05209 0.00694 0.00419 -0.00031
AFIX 43
H2 2 0.078762 0.706065 0.464409 11.00000 -1.20000
AFIX 0
C3 1 0.132409 0.621232 0.451239 11.00000 0.04743 0.08646 =
0.05696 0.02201 0.00298 -0.00838
AFIX 43
H3 2 0.091071 0.597133 0.466115 11.00000 -1.20000
AFIX 0
C4 1 0.201081 0.590494 0.429918 11.00000 0.05774 0.05991 =
0.06146 0.01552 -0.00734 -0.00560
C5 1 0.265534 0.625958 0.409226 11.00000 0.04571 0.05759 =
0.05061 0.00563 -0.00067 0.00046
AFIX 43
H5 2 0.312656 0.605174 0.395740 11.00000 -1.20000
AFIX 0
C6 1 0.259677 0.692452 0.408656 11.00000 0.03742 0.05867 =
0.04152 0.00428 -0.00225 -0.00123
C7 1 0.328892 0.733372 0.386596 11.00000 0.03461 0.05188 =
0.04717 0.00173 0.00245 0.00072
AFIX 13
H7 2 0.353902 0.707877 0.363404 11.00000 -1.20000
AFIX 0
C8 1 0.269967 0.791227 0.362759 11.00000 0.03931 0.05784 =
0.05246 0.01100 0.00310 0.00166
AFIX 13
H8 2 0.317166 0.818273 0.350428 11.00000 -1.20000
AFIX 0
C9 1 0.238016 0.828869 0.401819 11.00000 0.03843 0.05586 =
0.05798 0.00489 -0.00221 0.00552
AFIX 13
H9 2 0.196539 0.865386 0.387670 11.00000 -1.20000
AFIX 0
C10 1 0.125316 0.824672 0.456840 11.00000 0.04425 0.08128 =
0.05833 -0.01389 0.00491 -0.00179
AFIX 23
H10A 2 0.150642 0.868444 0.460807 11.00000 -1.20000
H10B 2 0.140669 0.804313 0.487410 11.00000 -1.20000
AFIX 0
C11 1 0.011605 0.827057 0.439476 11.00000 0.04091 0.05846 =
0.05245 0.00212 0.00499 0.00458
C12 1 -0.038589 0.802437 0.397119 11.00000 0.04768 0.09708 =
0.05761 -0.01098 0.00627 0.00929
AFIX 43
H12 2 -0.001957 0.783065 0.377560 11.00000 -1.20000
AFIX 0
C13 1 -0.142563 0.805975 0.383095 11.00000 0.04862 0.11753 =
0.06048 -0.00482 -0.00788 0.00447
AFIX 43
H13 2 -0.174803 0.788979 0.354256 11.00000 -1.20000
AFIX 0
C14 1 -0.198364 0.833896 0.410788 11.00000 0.04473 0.09998 =
0.07366 0.01556 0.00486 0.01623
AFIX 43
H14 2 -0.268225 0.836810 0.400924 11.00000 -1.20000
AFIX 0
C15 1 -0.150079 0.857621 0.453383 11.00000 0.05363 0.09332 =
0.07588 0.00679 0.01846 0.02044
AFIX 43
H15 2 -0.187569 0.875869 0.473029 11.00000 -1.20000
AFIX 0
C16 1 -0.044765 0.854753 0.467768 11.00000 0.05473 0.07476 =
0.05393 -0.00272 0.00693 0.00748
AFIX 43
H16 2 -0.012733 0.871700 0.496656 11.00000 -1.20000
AFIX 0
C17 1 0.267809 0.774684 0.256463 11.00000 0.05987 0.05972 =
0.04239 -0.00110 -0.00925 0.00310
C18 1 0.333521 0.746597 0.232332 11.00000 0.08114 0.06773 =
0.05312 -0.00549 -0.00308 0.01291
AFIX 43
H18 2 0.342621 0.702213 0.233689 11.00000 -1.20000
AFIX 0
C19 1 0.386409 0.783686 0.205984 11.00000 0.07029 0.09104 =
0.05293 -0.00659 0.00367 0.00952
AFIX 43
H19 2 0.431342 0.764417 0.190413 11.00000 -1.20000
AFIX 0
C20 1 0.370963 0.849125 0.203444 11.00000 0.06407 0.09226 =
0.04841 0.00155 0.00110 -0.00666
C21 1 0.302202 0.877801 0.224160 11.00000 0.07326 0.06111 =
0.05224 0.00310 -0.00222 0.00214
AFIX 43
H21 2 0.290448 0.921801 0.220503 11.00000 -1.20000
AFIX 0
C22 1 0.249180 0.841687 0.250855 11.00000 0.05939 0.06367 =
0.04653 0.00595 -0.00442 0.00809
C23 1 0.166799 0.868088 0.269503 11.00000 0.07623 0.07888 =
0.06016 0.01955 0.00389 0.02811
AFIX 43
H23 2 0.140513 0.908229 0.259275 11.00000 -1.20000
AFIX 0
C24 1 0.128629 0.836367 0.300563 11.00000 0.05367 0.10265 =
0.06110 0.01617 0.00014 0.02515
AFIX 43
H24 2 0.070919 0.851197 0.309327 11.00000 -1.20000
AFIX 0
C25 1 0.180759 0.775200 0.321706 11.00000 0.04930 0.07372 =
0.05137 0.01304 -0.00151 0.00040
AFIX 13
H25 2 0.132153 0.748171 0.333087 11.00000 -1.20000
AFIX 0
C26 1 0.213797 0.670937 0.284476 11.00000 0.08433 0.06766 =
0.05911 0.01470 -0.01580 -0.00393
AFIX 23
H26A 2 0.204956 0.656681 0.314840 11.00000 -1.20000
H26B 2 0.278876 0.655175 0.280885 11.00000 -1.20000
AFIX 0
C27 1 0.132881 0.640058 0.247302 11.00000 0.05860 0.06534 =
0.04905 -0.00048 0.00433 -0.00185
C28 1 0.062937 0.673992 0.215127 11.00000 0.05749 0.07662 =
0.05725 -0.00575 0.00311 0.00472
AFIX 43
H28 2 0.066415 0.718679 0.214476 11.00000 -1.20000
AFIX 0
C29 1 -0.013477 0.641884 0.183334 11.00000 0.05173 0.11920 =
0.06084 -0.00840 -0.00014 0.00799
AFIX 43
H29 2 -0.060559 0.665485 0.161876 11.00000 -1.20000
AFIX 0
C30 1 -0.019586 0.577460 0.183457 11.00000 0.09120 0.09805 =
0.09333 -0.01197 -0.00339 -0.03122
AFIX 43
H30 2 -0.069745 0.556088 0.162006 11.00000 -1.20000
AFIX 0
C31 1 0.049406 0.543972 0.215744 11.00000 0.18868 0.07833 =
0.14510 -0.00203 -0.06366 -0.04071
AFIX 43
H31 2 0.046375 0.499265 0.216265 11.00000 -1.20000
AFIX 0
C32 1 0.123488 0.575658 0.247574 11.00000 0.13089 0.06695 =
0.10208 0.00786 -0.03985 -0.00738
AFIX 43
H32 2 0.168288 0.551831 0.269888 11.00000 -1.20000
AFIX 0
C33 1 0.417341 0.758252 0.423496 11.00000 0.03129 0.05774 =
0.04497 0.00076 0.00339 0.00028
C34 1 0.410623 0.816155 0.443665 11.00000 0.03561 0.05322 =
0.05360 0.00488 0.00637 0.00166
C35 1 0.495690 0.846771 0.478271 11.00000 0.04330 0.05694 =
0.06593 -0.00476 0.00315 -0.00284
PART 1
AFIX 23
H35A 2 0.469120 0.871654 0.500838 21.00000 -1.20000
H35B 2 0.532753 0.875648 0.462193 21.00000 -1.20000
AFIX 23
PART 0
PART 2
H35C 2 0.496760 0.892492 0.471688 -21.00000 -1.20000
H35D 2 0.483547 0.841792 0.509480 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C36 1 0.566599 0.793889 0.503635 21.00000 0.04426 0.07544 =
0.05402 -0.00706 -0.00438 0.00439
AFIX 23
H36A 2 0.626590 0.813841 0.522543 21.00000 -1.20000
H36B 2 0.532892 0.770758 0.524548 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C36A 1 0.594823 0.819113 0.477349 -21.00000 0.04426 0.07544 =
0.05402 -0.00706 -0.00438 0.00439
AFIX 23
H36C 2 0.641758 0.830310 0.506364 -21.00000 -1.20000
H36D 2 0.619032 0.839053 0.451981 -21.00000 -1.20000
AFIX 0
PART 0
C37 1 0.596771 0.748145 0.471378 11.00000 0.03880 0.06824 =
0.07655 -0.00739 -0.01018 0.00814
PART 1
AFIX 23
H37A 2 0.632470 0.712766 0.489448 21.00000 -1.20000
H37B 2 0.643701 0.769383 0.455744 21.00000 -1.20000
AFIX 23
PART 0
PART 2
H37C 2 0.595823 0.728044 0.501166 -21.00000 -1.20000
H37D 2 0.659941 0.736448 0.463329 -21.00000 -1.20000
AFIX 0
PART 0
C38 1 0.510975 0.720962 0.434652 11.00000 0.03560 0.05416 =
0.04614 0.00500 0.00553 0.00019
C39 1 0.603317 0.631225 0.420944 11.00000 0.04697 0.05865 =
0.05540 -0.00364 0.00744 0.00809
C40 1 0.688003 0.651280 0.405287 11.00000 0.05940 0.05501 =
0.08251 0.01835 0.02178 0.01370
AFIX 43
H40 2 0.687467 0.690889 0.390441 11.00000 -1.20000
AFIX 0
C41 1 0.772999 0.612497 0.411729 11.00000 0.05456 0.06363 =
0.08773 0.00561 0.02403 0.01102
AFIX 43
H41 2 0.828504 0.626096 0.400568 11.00000 -1.20000
AFIX 0
C42 1 0.776733 0.553584 0.434599 11.00000 0.05970 0.05154 =
0.07337 -0.00308 0.00787 0.01199
C43 1 0.693166 0.534174 0.448944 11.00000 0.06654 0.05192 =
0.07466 0.00970 0.01052 0.00493
AFIX 43
H43 2 0.694020 0.494409 0.463607 11.00000 -1.20000
AFIX 0
C44 1 0.606109 0.571675 0.442497 11.00000 0.05693 0.06039 =
0.07213 0.00682 0.01639 0.00158
AFIX 43
H44 2 0.550025 0.556782 0.452632 11.00000 -1.20000
AFIX 0
C45 1 0.871435 0.513081 0.442974 11.00000 0.06827 0.06071 =
0.12004 -0.00349 0.00841 0.02153
AFIX 137
H45A 2 0.899405 0.514100 0.415640 11.00000 -1.50000
H45B 2 0.855236 0.469492 0.449342 11.00000 -1.50000
H45C 2 0.919854 0.529911 0.469264 11.00000 -1.50000
AFIX 0
CL1 3 0.204344 0.506718 0.428005 11.00000 0.09284 0.06172 =
0.11484 0.02235 0.01084 -0.00435
CL2 3 0.438708 0.895812 0.171512 11.00000 0.09595 0.13457 =
0.09231 0.01689 0.02891 -0.01985
N1 4 0.179272 0.790454 0.426457 11.00000 0.03758 0.06387 =
0.05940 -0.00374 0.00784 -0.00061
N2 4 0.216608 0.740600 0.284519 11.00000 0.07335 0.06282 =
0.05184 0.00350 -0.00213 -0.00691
N3 4 0.513557 0.668297 0.412880 11.00000 0.04222 0.05973 =
0.06054 -0.00326 0.00390 0.00909
O1 5 0.328153 0.854275 0.434175 11.00000 0.03992 0.04931 =
0.07256 -0.00302 0.00406 0.00289
C1' 1 0.741709 0.226116 0.415638 11.00000 0.03519 0.06728 =
0.04102 -0.00324 -0.00160 -0.00238
PART 2
C1A 1 1.127940 0.304453 0.481785 -31.00000 0.04095 0.06528 =
0.06653 -0.00921 -0.00582 -0.00240
AFIX 23
H1AA 2 1.188591 0.326656 0.497926 -31.00000 -1.20000
H1AB 2 1.101463 0.281038 0.505076 -31.00000 -1.20000
AFIX 0
PART 0
C2' 1 0.681028 0.188045 0.438419 11.00000 0.04310 0.08890 =
0.04807 0.00276 0.00659 -0.00428
AFIX 43
H2' 2 0.631952 0.207802 0.451223 11.00000 -1.20000
AFIX 0
C3' 1 0.692841 0.123269 0.442011 11.00000 0.06416 0.08793 =
0.06331 0.01602 0.01012 -0.01432
AFIX 43
H3' 2 0.652914 0.098902 0.457469 11.00000 -1.20000
AFIX 0
C4' 1 0.764303 0.094182 0.422592 11.00000 0.07735 0.06309 =
0.08058 0.01069 0.01210 -0.01065
C5' 1 0.824598 0.128993 0.399297 11.00000 0.05559 0.05554 =
0.06418 0.00105 0.00903 -0.00211
AFIX 43
H5' 2 0.871685 0.108206 0.385790 11.00000 -1.20000
AFIX 0
C6' 1 0.814036 0.194935 0.396343 11.00000 0.04074 0.05276 =
0.04247 -0.00242 0.00093 -0.00170
C7' 1 0.880360 0.235456 0.372021 11.00000 0.03492 0.04998 =
0.04444 -0.00329 0.00475 0.00222
AFIX 13
H7' 2 0.904184 0.209248 0.348837 11.00000 -1.20000
AFIX 0
C8' 1 0.818643 0.292394 0.347738 11.00000 0.03850 0.05268 =
0.04609 0.00114 0.00561 0.00404
AFIX 13
H8' 2 0.864358 0.319555 0.334542 11.00000 -1.20000
AFIX 0
C9' 1 0.787899 0.330549 0.386559 11.00000 0.03662 0.04877 =
0.05632 -0.00255 0.00141 0.00591
AFIX 13
H9' 2 0.745341 0.366482 0.372159 11.00000 -1.20000
AFIX 0
C10' 1 0.681566 0.328113 0.443638 11.00000 0.04062 0.08332 =
0.05587 -0.02224 0.00354 0.00292
AFIX 23
H10C 2 0.714080 0.369787 0.449657 11.00000 -1.20000
H10D 2 0.692542 0.305326 0.473248 11.00000 -1.20000
AFIX 0
C11' 1 0.568212 0.338752 0.425957 11.00000 0.03885 0.06770 =
0.04734 -0.00040 0.00491 0.00568
C12' 1 0.513442 0.311527 0.384985 11.00000 0.04899 0.09644 =
0.06064 -0.01930 0.00247 0.01024
AFIX 43
H12' 2 0.545432 0.285498 0.366890 11.00000 -1.20000
AFIX 0
C13' 1 0.410735 0.323265 0.371087 11.00000 0.05099 0.13681 =
0.06548 -0.00674 -0.00556 0.01332
AFIX 43
H13' 2 0.373765 0.304308 0.343849 11.00000 -1.20000
AFIX 0
C14' 1 0.363528 0.361853 0.396534 11.00000 0.04957 0.17104 =
0.07321 0.00164 -0.00049 0.03834
AFIX 43
H14' 2 0.294855 0.370273 0.386402 11.00000 -1.20000
AFIX 0
C15' 1 0.417107 0.388582 0.437344 11.00000 0.06774 0.14579 =
0.08890 -0.01049 0.02391 0.05002
AFIX 43
H15' 2 0.384672 0.415203 0.454883 11.00000 -1.20000
AFIX 0
C16' 1 0.518917 0.376155 0.452495 11.00000 0.05599 0.09610 =
0.05806 -0.00947 0.00537 0.01550
AFIX 43
H16' 2 0.554360 0.393150 0.480783 11.00000 -1.20000
AFIX 0
C17' 1 0.811970 0.271206 0.241992 11.00000 0.05104 0.06018 =
0.04104 -0.00927 -0.00543 0.00210
C18' 1 0.875628 0.241516 0.217159 11.00000 0.06532 0.06521 =
0.05124 -0.01191 0.00439 0.00582
AFIX 43
H18' 2 0.883679 0.197074 0.219110 11.00000 -1.20000
AFIX 0
C19' 1 0.927408 0.276375 0.189576 11.00000 0.05913 0.08572 =
0.05378 -0.01249 0.00673 0.00296
AFIX 43
H19' 2 0.970695 0.255696 0.173801 11.00000 -1.20000
AFIX 0
C20' 1 0.913761 0.342260 0.185868 11.00000 0.05825 0.08112 =
0.05396 -0.01028 0.00410 -0.01122
C21' 1 0.848539 0.372641 0.207437 11.00000 0.07092 0.06411 =
0.04744 0.00083 0.00324 -0.00259
AFIX 43
H21' 2 0.839130 0.416847 0.203834 11.00000 -1.20000
AFIX 0
C22' 1 0.795089 0.338150 0.235124 11.00000 0.05329 0.06056 =
0.04660 -0.00027 0.00067 0.00307
C23' 1 0.714099 0.366248 0.254183 11.00000 0.06032 0.06694 =
0.05815 0.00581 0.00431 0.01773
AFIX 43
H23' 2 0.688194 0.406237 0.243345 11.00000 -1.20000
AFIX 0
C24' 1 0.676944 0.336655 0.286132 11.00000 0.04755 0.08032 =
0.05502 0.00405 0.00056 0.02042
AFIX 43
H24' 2 0.620833 0.352896 0.295567 11.00000 -1.20000
AFIX 0
C25' 1 0.728166 0.274934 0.307392 11.00000 0.04384 0.06346 =
0.04756 0.00165 0.00089 -0.00098
AFIX 13
H25' 2 0.679718 0.249094 0.319816 11.00000 -1.20000
AFIX 0
C26' 1 0.761453 0.168673 0.272708 11.00000 0.07116 0.05981 =
0.05094 0.00238 -0.00761 -0.00480
AFIX 23
H26C 2 0.744619 0.155696 0.301853 11.00000 -1.20000
H26D 2 0.829502 0.153779 0.273488 11.00000 -1.20000
AFIX 0
C27' 1 0.689424 0.135290 0.232507 11.00000 0.05691 0.06381 =
0.04804 -0.00167 0.00691 -0.00996
C28' 1 0.609564 0.165905 0.203979 11.00000 0.05698 0.07642 =
0.05385 -0.00782 0.00435 0.00166
AFIX 43
H28' 2 0.601779 0.210109 0.206740 11.00000 -1.20000
AFIX 0
C29' 1 0.539759 0.131370 0.170803 11.00000 0.05420 0.10159 =
0.06476 -0.00438 -0.00246 -0.00401
AFIX 43
H29' 2 0.485242 0.152695 0.152038 11.00000 -1.20000
AFIX 0
C30' 1 0.550508 0.066946 0.165596 11.00000 0.07802 0.09595 =
0.08572 -0.01171 -0.00416 -0.03188
AFIX 43
H30' 2 0.503538 0.044070 0.143584 11.00000 -1.20000
AFIX 0
C31' 1 0.631851 0.036028 0.193342 11.00000 0.12173 0.06646 =
0.11538 -0.01465 -0.01815 -0.02156
AFIX 43
H31' 2 0.640392 -0.007976 0.189860 11.00000 -1.20000
AFIX 0
C32' 1 0.701298 0.070216 0.226537 11.00000 0.09076 0.06084 =
0.08804 -0.00604 -0.01548 -0.00029
AFIX 43
H32' 2 0.756374 0.048941 0.244918 11.00000 -1.20000
AFIX 0
C33' 1 0.970181 0.262836 0.407219 11.00000 0.03415 0.05156 =
0.04608 -0.00456 0.00544 0.00090
C34' 1 0.963329 0.320764 0.426394 11.00000 0.03555 0.05373 =
0.05044 -0.00517 0.00644 0.00094
C35' 1 1.048932 0.355040 0.458448 11.00000 0.04367 0.05892 =
0.06539 -0.01181 0.00335 -0.00347
PART 1
AFIX 23
H35E 2 1.044247 0.400698 0.451372 31.00000 -1.20000
H35F 2 1.042451 0.349586 0.490534 31.00000 -1.20000
AFIX 23
PART 0
PART 2
H35G 2 1.024050 0.378461 0.482220 -31.00000 -1.20000
H35H 2 1.079634 0.385589 0.440777 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C36' 1 1.148682 0.331475 0.454302 31.00000 0.04095 0.06528 =
0.06653 -0.00921 -0.00582 -0.00240
AFIX 23
H36E 2 1.198643 0.345018 0.481710 31.00000 -1.20000
H36F 2 1.165936 0.351287 0.427134 31.00000 -1.20000
AFIX 0
PART 0
C37' 1 1.154288 0.259508 0.449717 11.00000 0.03781 0.06668 =
0.08809 -0.00755 -0.00880 0.00557
PART 1
AFIX 23
H37E 2 1.162160 0.240831 0.480673 31.00000 -1.20000
H37F 2 1.214732 0.249256 0.438723 31.00000 -1.20000
AFIX 23
PART 0
PART 2
H37G 2 1.197043 0.226542 0.467429 -31.00000 -1.20000
H37H 2 1.193668 0.281693 0.430721 -31.00000 -1.20000
AFIX 0
PART 0
C38' 1 1.065438 0.227122 0.417496 11.00000 0.03580 0.05361 =
0.04744 -0.00128 0.00614 0.00218
C39' 1 1.157736 0.134687 0.406872 11.00000 0.04692 0.05854 =
0.06033 -0.00238 0.00972 0.00985
C40' 1 1.235259 0.150431 0.385432 11.00000 0.06322 0.06533 =
0.08102 0.02045 0.02446 0.01998
AFIX 43
H40' 2 1.230987 0.187763 0.367577 11.00000 -1.20000
AFIX 0
C41' 1 1.319510 0.111078 0.390269 11.00000 0.06021 0.07635 =
0.09430 0.01155 0.03634 0.01646
AFIX 43
H41' 2 1.370668 0.122495 0.375366 11.00000 -1.20000
AFIX 0
C42' 1 1.329301 0.055633 0.416530 11.00000 0.06110 0.06071 =
0.08610 0.00251 0.01762 0.02128
C43' 1 1.251734 0.040602 0.437718 11.00000 0.08073 0.06064 =
0.08569 0.01838 0.02296 0.01663
AFIX 43
H43' 2 1.256581 0.003610 0.455965 11.00000 -1.20000
AFIX 0
C44' 1 1.166209 0.078970 0.432732 11.00000 0.06406 0.06410 =
0.07361 0.01033 0.02338 0.00874
AFIX 43
H44' 2 1.114354 0.066865 0.446990 11.00000 -1.20000
AFIX 0
C45' 1 1.420460 0.013148 0.421334 11.00000 0.08076 0.07261 =
0.14298 0.01218 0.02930 0.03503
AFIX 137
H45D 2 1.400213 -0.028226 0.407868 11.00000 -1.50000
H45E 2 1.452000 0.008081 0.453889 11.00000 -1.50000
H45F 2 1.467461 0.032421 0.405315 11.00000 -1.50000
AFIX 0
CL1' 3 0.778037 0.010457 0.426433 11.00000 0.16578 0.06405 =
0.17925 0.03252 0.06895 -0.00288
CL2' 3 0.979133 0.385859 0.151171 11.00000 0.09430 0.11709 =
0.07975 -0.00755 0.03273 -0.03115
N1' 4 0.730622 0.292412 0.412239 11.00000 0.03802 0.06355 =
0.05129 -0.00916 0.00694 0.00454
N2' 4 0.760565 0.238608 0.270386 11.00000 0.06527 0.05401 =
0.04885 -0.00240 0.00428 -0.00160
N3' 4 1.066951 0.170998 0.399460 11.00000 0.04233 0.06071 =
0.06092 -0.00479 0.00521 0.01152
O1' 5 0.877760 0.357252 0.417608 11.00000 0.03873 0.05167 =
0.07220 -0.01631 0.00272 0.00499
HKLF 4
REM CF solution in P21/n
REM R1 = 0.1225 for 10018 Fo > 4sig(Fo) and 0.1448 for all 14381 data
REM 929 parameters refined using 0 restraints
END
WGHT 0.2000 0.0000
REM Highest difference peak 3.290, deepest hole -0.339, 1-sigma level 0.170
Q1 1 0.4514 0.5261 0.3330 11.00000 0.05 3.29
Q2 1 1.0029 0.0213 0.3182 11.00000 0.05 2.68
Q3 1 0.9820 0.0140 0.2609 11.00000 0.05 1.99
Q4 1 0.5370 0.5039 0.3256 11.00000 0.05 1.63
Q5 1 -0.0283 1.0188 0.1818 11.00000 0.05 1.61
Q6 1 0.4685 0.5949 0.2575 11.00000 0.05 1.58
Q7 1 0.1338 1.0106 0.2040 11.00000 0.05 0.97
Q8 1 0.2569 0.4986 0.4190 11.00000 0.05 0.61
Q9 1 0.7984 0.0041 0.4011 11.00000 0.05 0.59
Q10 1 1.4330 0.0183 0.4328 11.00000 0.05 0.52
Q11 1 0.3952 0.9250 0.1777 11.00000 0.05 0.43
Q12 1 0.9432 0.5415 0.4391 11.00000 0.05 0.39
Q13 1 0.0241 0.5389 0.2171 11.00000 0.05 0.37
Q14 1 0.6589 0.3224 0.4437 11.00000 0.05 0.35
Q15 1 -0.1754 0.8557 0.4135 11.00000 0.05 0.34
Q16 1 1.1057 0.1608 0.4074 11.00000 0.05 0.34
Q17 1 0.7184 0.2961 0.3002 11.00000 0.05 0.33
Q18 1 0.4371 0.8679 0.1765 11.00000 0.05 0.32
Q19 1 1.0437 0.2159 0.4221 11.00000 0.05 0.31
Q20 1 0.8458 0.2136 0.3845 11.00000 0.05 0.30
REM The information below was added by Olex2.
REM
REM R1 = 0.1225 for 10018 Fo > 4sig(Fo) and 0.1448 for all 38541 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 3.29, deepest hole -0.34
REM Mean Shift 0.01, Max Shift -0.546.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.1448
REM R1_gt = 0.1225
REM wR_ref = 0.3780
REM GOOF = 1.431
REM Shift_max = -0.546
REM Shift_mean = 0.01
REM Reflections_all = 38541
REM Reflections_gt = 10018
REM Parameters = n/a
REM Hole = -0.34
REM Peak = 3.29
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'