# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021
#######################################################################
#
# 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.
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data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1993726'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H17 N3 O, H2 O'
_chemical_formula_sum 'C14 H19 N3 O2'
_chemical_formula_weight 261.32
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 8.1323(2)
_cell_length_b 8.1695(2)
_cell_length_c 19.3253(4)
_cell_angle_alpha 90
_cell_angle_beta 90.8030(10)
_cell_angle_gamma 90
_cell_volume 1283.79(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 4478
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 27.884
_cell_measurement_theta_min 2.707
_shelx_estimated_absorpt_T_max 0.966
_shelx_estimated_absorpt_T_min 0.956
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6403
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0480 before and 0.0355 after correction. The Ratio of minimum to maximum transmission is 0.8588. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.352
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 560
_exptl_crystal_size_max 0.492
_exptl_crystal_size_mid 0.406
_exptl_crystal_size_min 0.373
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0225
_diffrn_reflns_av_unetI/netI 0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 11411
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.902
_diffrn_reflns_theta_min 2.505
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2749
_reflns_number_total 3068
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection 'Bruker Apex suite'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.453
_refine_diff_density_min -0.349
_refine_diff_density_rms 0.050
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.119
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 181
_refine_ls_number_reflns 3068
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0507
_refine_ls_R_factor_gt 0.0448
_refine_ls_restrained_S_all 1.119
_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^)+(0.0339P)^2^+1.0698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1036
_refine_ls_wR_factor_ref 0.1067
_refine_special_details
;
The NH hydrogen atom was located in the difference map however
restraints were applied to the NH distance as it appears that
it and the H2O hydrogen atoms are probably disordered.
;
_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, All O(H,H) groups
2. Restrained distances
N3-H3
0.87 with sigma of 0.01
3.a Free rotating group:
O2(H2A,H2B)
3.b Secondary CH2 refined with riding coordinates:
C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
C11(H11), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.80261(14) 0.21176(13) 0.55608(5) 0.0183(2) Uani 1 1 d . . . . .
N1 N 0.78348(15) 0.40200(14) 0.46810(6) 0.0124(2) Uani 1 1 d . . . . .
N2 N 0.87075(15) 0.15080(14) 0.44225(6) 0.0126(2) Uani 1 1 d . . . . .
N3 N 0.91686(15) 0.17789(17) 0.32251(7) 0.0173(3) Uani 1 1 d D . . . .
C1 C 0.81628(17) 0.25350(18) 0.49566(7) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.78538(16) 0.39918(16) 0.39192(7) 0.0107(3) Uani 1 1 d . . . . .
C3 C 0.86769(16) 0.23468(17) 0.37923(7) 0.0109(3) Uani 1 1 d . . . . .
C4 C 0.60864(16) 0.38842(17) 0.36160(7) 0.0107(3) Uani 1 1 d . . . . .
C5 C 0.50272(16) 0.25212(17) 0.37226(7) 0.0115(3) Uani 1 1 d . . . . .
C6 C 0.52754(17) 0.10581(17) 0.42119(7) 0.0130(3) Uani 1 1 d . . . . .
H6A H 0.418661 0.053929 0.427234 0.016 Uiso 1 1 calc R . . . .
H6B H 0.561388 0.150273 0.466862 0.016 Uiso 1 1 calc R . . . .
C7 C 0.65060(18) -0.03238(17) 0.40307(7) 0.0143(3) Uani 1 1 d . . . . .
H7A H 0.599437 -0.139360 0.413523 0.017 Uiso 1 1 calc R . . . .
H7B H 0.671579 -0.029026 0.352756 0.017 Uiso 1 1 calc R . . . .
C8 C 0.81542(18) -0.02052(17) 0.44227(7) 0.0141(3) Uani 1 1 d . . . . .
H8A H 0.802393 -0.059109 0.490443 0.017 Uiso 1 1 calc R . . . .
H8B H 0.898177 -0.090561 0.419626 0.017 Uiso 1 1 calc R . . . .
C9 C 0.72580(18) 0.53969(18) 0.50809(8) 0.0164(3) Uani 1 1 d . . . . .
H9A H 0.697195 0.502676 0.554635 0.025 Uiso 1 1 calc GR . . . .
H9B H 0.628458 0.587083 0.485325 0.025 Uiso 1 1 calc GR . . . .
H9C H 0.812666 0.622572 0.511408 0.025 Uiso 1 1 calc GR . . . .
C10 C 0.88878(18) 0.53922(17) 0.36398(8) 0.0147(3) Uani 1 1 d . . . . .
H10A H 0.838538 0.643907 0.376578 0.022 Uiso 1 1 calc GR . . . .
H10B H 0.894238 0.530813 0.313482 0.022 Uiso 1 1 calc GR . . . .
H10C H 1.000076 0.533034 0.383917 0.022 Uiso 1 1 calc GR . . . .
C11 C 0.55290(18) 0.51790(18) 0.32040(7) 0.0144(3) Uani 1 1 d . . . . .
H11 H 0.623296 0.609117 0.313571 0.017 Uiso 1 1 calc R . . . .
C12 C 0.39834(18) 0.51813(19) 0.28904(7) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.362178 0.609942 0.262776 0.021 Uiso 1 1 calc R . . . .
C13 C 0.29777(18) 0.3833(2) 0.29649(7) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.193524 0.379414 0.273742 0.021 Uiso 1 1 calc R . . . .
C14 C 0.35041(17) 0.25357(18) 0.33753(7) 0.0148(3) Uani 1 1 d . . . . .
H14 H 0.279968 0.161608 0.342268 0.018 Uiso 1 1 calc R . . . .
O2 O 0.90250(15) 0.12550(14) 0.69510(6) 0.0212(3) Uani 1 1 d . . . . .
H2A H 0.959060 0.039565 0.683613 0.032 Uiso 1 1 d G . . . .
H2B H 0.863022 0.162658 0.656094 0.032 Uiso 1 1 d G . . . .
H3 H 0.910(4) 0.239(3) 0.2861(11) 0.085(11) Uiso 1 1 d D . . A 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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0247(6) 0.0192(5) 0.0109(5) 0.0013(4) -0.0028(4) 0.0024(4)
N1 0.0159(6) 0.0118(6) 0.0094(5) -0.0016(4) -0.0014(4) 0.0021(4)
N2 0.0147(6) 0.0105(5) 0.0125(5) -0.0004(4) -0.0017(4) 0.0016(5)
N3 0.0131(6) 0.0209(7) 0.0182(6) -0.0066(5) 0.0025(5) -0.0037(5)
C1 0.0120(6) 0.0144(6) 0.0134(6) -0.0009(5) -0.0035(5) 0.0008(5)
C2 0.0120(6) 0.0100(6) 0.0102(6) -0.0012(5) -0.0003(5) -0.0003(5)
C3 0.0083(6) 0.0101(6) 0.0143(6) 0.0000(5) -0.0021(5) -0.0011(5)
C4 0.0107(6) 0.0117(6) 0.0098(6) -0.0014(5) 0.0005(5) 0.0009(5)
C5 0.0123(6) 0.0119(6) 0.0104(6) -0.0012(5) 0.0013(5) 0.0011(5)
C6 0.0128(6) 0.0123(6) 0.0141(6) 0.0018(5) 0.0013(5) -0.0016(5)
C7 0.0177(7) 0.0096(6) 0.0154(6) 0.0008(5) -0.0004(5) -0.0012(5)
C8 0.0182(7) 0.0092(6) 0.0150(6) 0.0014(5) 0.0002(5) 0.0022(5)
C9 0.0193(7) 0.0141(7) 0.0157(7) -0.0047(5) -0.0007(5) 0.0036(6)
C10 0.0146(6) 0.0112(6) 0.0182(7) -0.0005(5) 0.0002(5) -0.0025(5)
C11 0.0164(7) 0.0131(6) 0.0137(6) 0.0014(5) 0.0010(5) 0.0001(5)
C12 0.0182(7) 0.0193(7) 0.0142(7) 0.0032(6) -0.0016(5) 0.0058(6)
C13 0.0130(6) 0.0251(8) 0.0138(6) -0.0017(6) -0.0021(5) 0.0033(6)
C14 0.0125(6) 0.0175(7) 0.0145(6) -0.0030(5) 0.0006(5) -0.0012(5)
O2 0.0304(6) 0.0177(5) 0.0156(5) 0.0001(4) -0.0023(4) 0.0077(5)
_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
O1 C1 1.2229(17) . ?
N1 C1 1.3500(18) . ?
N1 C2 1.4727(17) . ?
N1 C9 1.4466(18) . ?
N2 C1 1.4066(18) . ?
N2 C3 1.3974(17) . ?
N2 C8 1.4701(18) . ?
N3 C3 1.2605(19) . ?
N3 H3 0.862(10) . ?
C2 C3 1.5227(19) . ?
C2 C4 1.5471(18) . ?
C2 C10 1.5232(19) . ?
C4 C5 1.4244(19) . ?
C4 C11 1.3959(19) . ?
C5 C6 1.5357(19) . ?
C5 C14 1.4005(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5519(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
O2 H2A 0.8699 . ?
O2 H2B 0.8699 . ?
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
C1 N1 C2 112.06(11) . . ?
C1 N1 C9 123.49(12) . . ?
C9 N1 C2 123.66(11) . . ?
C1 N2 C8 117.92(12) . . ?
C3 N2 C1 110.19(11) . . ?
C3 N2 C8 117.73(11) . . ?
C3 N3 H3 119(2) . . ?
O1 C1 N1 127.38(13) . . ?
O1 C1 N2 124.62(13) . . ?
N1 C1 N2 108.00(12) . . ?
N1 C2 C3 100.70(10) . . ?
N1 C2 C4 110.90(11) . . ?
N1 C2 C10 110.87(11) . . ?
C3 C2 C4 107.28(11) . . ?
C3 C2 C10 111.08(11) . . ?
C10 C2 C4 115.02(11) . . ?
N2 C3 C2 107.15(11) . . ?
N3 C3 N2 125.13(13) . . ?
N3 C3 C2 127.62(13) . . ?
C5 C4 C2 123.38(12) . . ?
C11 C4 C2 117.74(12) . . ?
C11 C4 C5 118.86(12) . . ?
C4 C5 C6 128.53(12) . . ?
C14 C5 C4 117.17(12) . . ?
C14 C5 C6 114.17(12) . . ?
C5 C6 H6A 107.2 . . ?
C5 C6 H6B 107.2 . . ?
C5 C6 C7 120.46(11) . . ?
H6A C6 H6B 106.8 . . ?
C7 C6 H6A 107.2 . . ?
C7 C6 H6B 107.2 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.87(11) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N2 C8 C7 108.99(11) . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 118.8 . . ?
C12 C11 C4 122.34(13) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.19(13) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.37(13) . . ?
C14 C13 H13 120.3 . . ?
C5 C14 H14 118.5 . . ?
C13 C14 C5 122.95(14) . . ?
C13 C14 H14 118.5 . . ?
H2A O2 H2B 104.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A N3 0.87 2.05 2.9037(17) 167.9 3_756 yes
O2 H2B O1 0.87 2.03 2.8834(15) 167.6 . yes
N3 H3 O2 0.862(10) 2.080(10) 2.9407(18) 176(3) 4_565 yes
_shelx_res_file
;
TITL testm1_a.res in P2(1)/c
testm1.res
created by SHELXL-2017/1 at 15:03:00 on 05-Sep-2018
REM Old TITL testm1 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.113, Rweak 0.006, Alpha 0.026, Orientation as input
REM Formula found by SHELXT: C14 N2 O3
CELL 0.71073 8.1323 8.1695 19.3253 90 90.803 90
ZERR 4 0.0002 0.0002 0.0004 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 56 76 12 8
EQIV $1 +X,0.5-Y,-0.5+Z
EQIV $2 2-X,-Y,1-Z
DFIX 0.87 0.01 N3 H3
L.S. 4 0 0
PLAN 5
SIZE 0.373 0.406 0.492
TEMP -173(2)
HTAB O2 O1
HTAB N3 O2_$1
HTAB O2 N3_$2
BOND $H
list 4
fmap 2 53
ACTA
OMIT 0 0 2
REM
REM
REM
WGHT 0.033900 1.069800
FVAR 0.81106
O1 4 0.802605 0.211761 0.556076 11.00000 0.02473 0.01916 =
0.01091 0.00126 -0.00282 0.00244
N1 3 0.783482 0.402001 0.468104 11.00000 0.01593 0.01177 =
0.00942 -0.00160 -0.00139 0.00214
N2 3 0.870749 0.150795 0.442250 11.00000 0.01474 0.01051 =
0.01249 -0.00044 -0.00171 0.00162
N3 3 0.916863 0.177893 0.322510 11.00000 0.01306 0.02086 =
0.01817 -0.00657 0.00246 -0.00369
C1 1 0.816283 0.253504 0.495663 11.00000 0.01201 0.01443 =
0.01338 -0.00091 -0.00355 0.00080
C2 1 0.785383 0.399177 0.391923 11.00000 0.01203 0.01005 =
0.01016 -0.00119 -0.00028 -0.00029
C3 1 0.867691 0.234682 0.379230 11.00000 0.00832 0.01010 =
0.01434 -0.00004 -0.00206 -0.00112
C4 1 0.608635 0.388416 0.361601 11.00000 0.01069 0.01171 =
0.00981 -0.00138 0.00045 0.00086
C5 1 0.502720 0.252122 0.372258 11.00000 0.01232 0.01188 =
0.01037 -0.00116 0.00132 0.00108
C6 1 0.527535 0.105806 0.421187 11.00000 0.01278 0.01230 =
0.01406 0.00177 0.00134 -0.00164
AFIX 23
H6A 2 0.418661 0.053929 0.427234 11.00000 -1.20000
H6B 2 0.561388 0.150273 0.466862 11.00000 -1.20000
AFIX 0
C7 1 0.650600 -0.032378 0.403075 11.00000 0.01769 0.00964 =
0.01542 0.00083 -0.00044 -0.00121
AFIX 23
H7A 2 0.599437 -0.139360 0.413523 11.00000 -1.20000
H7B 2 0.671579 -0.029026 0.352756 11.00000 -1.20000
AFIX 0
C8 1 0.815416 -0.020523 0.442268 11.00000 0.01821 0.00921 =
0.01497 0.00143 0.00023 0.00220
AFIX 23
H8A 2 0.802393 -0.059109 0.490443 11.00000 -1.20000
H8B 2 0.898177 -0.090561 0.419626 11.00000 -1.20000
AFIX 0
C9 1 0.725799 0.539685 0.508093 11.00000 0.01934 0.01414 =
0.01574 -0.00470 -0.00070 0.00357
AFIX 137
H9A 2 0.697195 0.502676 0.554635 11.00000 -1.50000
H9B 2 0.628458 0.587083 0.485325 11.00000 -1.50000
H9C 2 0.812666 0.622572 0.511408 11.00000 -1.50000
AFIX 0
C10 1 0.888777 0.539218 0.363984 11.00000 0.01460 0.01118 =
0.01825 -0.00049 0.00025 -0.00252
AFIX 137
H10A 2 0.838538 0.643907 0.376578 11.00000 -1.50000
H10B 2 0.894238 0.530813 0.313482 11.00000 -1.50000
H10C 2 1.000076 0.533034 0.383917 11.00000 -1.50000
AFIX 0
C11 1 0.552905 0.517901 0.320395 11.00000 0.01641 0.01307 =
0.01370 0.00135 0.00097 0.00014
AFIX 43
H11 2 0.623296 0.609117 0.313571 11.00000 -1.20000
AFIX 0
C12 1 0.398340 0.518135 0.289043 11.00000 0.01815 0.01934 =
0.01422 0.00317 -0.00164 0.00576
AFIX 43
H12 2 0.362178 0.609942 0.262776 11.00000 -1.20000
AFIX 0
C13 1 0.297769 0.383330 0.296489 11.00000 0.01303 0.02511 =
0.01377 -0.00175 -0.00212 0.00331
AFIX 43
H13 2 0.193524 0.379414 0.273742 11.00000 -1.20000
AFIX 0
C14 1 0.350412 0.253571 0.337526 11.00000 0.01253 0.01746 =
0.01448 -0.00302 0.00061 -0.00118
AFIX 43
H14 2 0.279968 0.161608 0.342268 11.00000 -1.20000
AFIX 6
O2 4 0.902500 0.125504 0.695103 11.00000 0.03041 0.01766 =
0.01557 0.00012 -0.00226 0.00773
H2A 2 0.959060 0.039565 0.683613 11.00000 -1.50000
H2B 2 0.863022 0.162658 0.656094 11.00000 -1.50000
AFIX 0
PART 1
H3 2 0.909715 0.238661 0.286143 11.00000 0.08452
HKLF 4
REM testm1_a.res in P2(1)/c
REM R1 = 0.0448 for 2749 Fo > 4sig(Fo) and 0.0507 for all 3068 data
REM 181 parameters refined using 1 restraints
END
WGHT 0.0339 1.0699
REM Highest difference peak 0.453, deepest hole -0.349, 1-sigma level 0.050
Q1 1 0.9584 0.0819 0.3191 11.00000 0.05 0.45
Q2 1 0.4423 0.2388 0.3429 11.00000 0.05 0.32
Q3 1 0.8830 0.1840 0.7353 11.00000 0.05 0.31
Q4 1 0.8310 0.3183 0.3842 11.00000 0.05 0.30
Q5 1 0.8366 0.4655 0.3779 11.00000 0.05 0.29
;
_shelx_res_checksum 85935
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
#######################################################################
#
# 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_mm121
_database_code_depnum_ccdc_archive 'CCDC 1993728'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2019-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number 2013-4
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C13 H15 N3 O2, H2 O'
_chemical_formula_sum 'C13 H17 N3 O3'
_chemical_formula_weight 263.29
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 8.0314(2)
_cell_length_b 8.1488(2)
_cell_length_c 19.2027(5)
_cell_angle_alpha 90
_cell_angle_beta 90.5479(17)
_cell_angle_gamma 90
_cell_volume 1256.69(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7467
_cell_measurement_temperature 100
_cell_measurement_theta_max 30.04
_cell_measurement_theta_min 2.54
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_correction_T_min 0.6753
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0543 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.9052. The \l/2 correction factor is Not present.'
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.392
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
_exptl_crystal_size_max 0.394
_exptl_crystal_size_mid 0.347
_exptl_crystal_size_min 0.144
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0329
_diffrn_reflns_av_unetI/netI 0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 26526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.573
_diffrn_reflns_theta_min 2.121
_diffrn_ambient_temperature 99.97
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3045
_reflns_number_total 3522
_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 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_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 0.398
_refine_diff_density_min -0.218
_refine_diff_density_rms 0.046
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 186
_refine_ls_number_reflns 3522
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0449
_refine_ls_R_factor_gt 0.0378
_refine_ls_restrained_S_all 1.049
_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^)+(0.0473P)^2^+0.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0952
_refine_ls_wR_factor_ref 0.0998
_refine_special_details
;
Hydrogen atoms on heteroatoms were found by difference map after all other
atoms had been refined. All other hydrogen atoms were placed geometrically
and refined using a riding model.
;
_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 Secondary CH2 refined with riding coordinates:
C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens mixed
_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 0.39242(12) 0.37161(12) 0.36451(5) 0.01294(19) Uani 1 1 d . . . . .
C2 C 0.45075(13) 0.48908(14) 0.31790(5) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.3824 0.5806 0.3065 0.022 Uiso 1 1 calc R . . . .
C3 C 0.60714(14) 0.47510(15) 0.28766(6) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.6460 0.5587 0.2574 0.027 Uiso 1 1 calc R . . . .
C4 C 0.70591(14) 0.33961(16) 0.30166(6) 0.0225(2) Uani 1 1 d . . . . .
H4 H 0.8101 0.3273 0.2793 0.027 Uiso 1 1 calc R . . . .
C5 C 0.65212(13) 0.22155(14) 0.34861(6) 0.0193(2) Uani 1 1 d . . . . .
H5 H 0.7203 0.1291 0.3587 0.023 Uiso 1 1 calc R . . . .
C6 C 0.49853(12) 0.23863(13) 0.38079(5) 0.01404(19) Uani 1 1 d . . . . .
C7 C 0.38052(14) -0.02555(13) 0.41410(6) 0.0177(2) Uani 1 1 d . . . . .
H7A H 0.4504 -0.1192 0.4293 0.021 Uiso 1 1 calc R . . . .
H7B H 0.3654 -0.0317 0.3629 0.021 Uiso 1 1 calc R . . . .
C8 C 0.21058(14) -0.03146(13) 0.45028(6) 0.0182(2) Uani 1 1 d . . . . .
H8A H 0.1366 -0.1110 0.4263 0.022 Uiso 1 1 calc R . . . .
H8B H 0.2250 -0.0668 0.4993 0.022 Uiso 1 1 calc R . . . .
C9 C 0.19255(12) 0.24363(13) 0.49966(5) 0.0158(2) Uani 1 1 d . . . . .
C10 C 0.21447(12) 0.38285(12) 0.39380(5) 0.01253(18) Uani 1 1 d . . . . .
C11 C 0.13605(12) 0.21356(12) 0.38314(5) 0.01304(19) Uani 1 1 d . . . . .
C12 C 0.27259(14) 0.53428(13) 0.50865(6) 0.0185(2) Uani 1 1 d . . . . .
H12A H 0.3695 0.5819 0.4855 0.028 Uiso 1 1 calc GR . . . .
H12B H 0.3036 0.5017 0.5562 0.028 Uiso 1 1 calc GR . . . .
H12C H 0.1830 0.6158 0.5103 0.028 Uiso 1 1 calc GR . . . .
C13 C 0.10940(13) 0.51961(13) 0.36226(6) 0.0173(2) Uani 1 1 d . . . . .
H13A H -0.0022 0.5171 0.3824 0.026 Uiso 1 1 calc GR . . . .
H13B H 0.1009 0.5042 0.3117 0.026 Uiso 1 1 calc GR . . . .
H13C H 0.1617 0.6258 0.3723 0.026 Uiso 1 1 calc GR . . . .
N1 N 0.13668(11) 0.13337(11) 0.44766(4) 0.01526(18) Uani 1 1 d . . . . .
N2 N 0.21594(11) 0.39175(11) 0.47018(4) 0.01463(18) Uani 1 1 d . . . . .
N3 N 0.08841(11) 0.14745(12) 0.32689(5) 0.01800(19) Uani 1 1 d . . . . .
H3A H 0.095(2) 0.207(2) 0.2931(9) 0.036(4) Uiso 1 1 d . . . . .
O1 O 0.45937(9) 0.12820(9) 0.43333(4) 0.01589(16) Uani 1 1 d . . . . .
O2 O 0.21082(11) 0.20726(11) 0.56102(4) 0.02251(18) Uani 1 1 d . . . . .
O3 O 0.08826(12) 0.15247(11) 0.69733(4) 0.02492(19) Uani 1 1 d . . . . .
H3B H 0.135(2) 0.185(2) 0.6604(10) 0.039(5) Uiso 1 1 d . . . . .
H3C H 0.029(3) 0.054(3) 0.6867(12) 0.071(7) Uiso 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 0.0127(4) 0.0151(4) 0.0110(4) -0.0011(3) 0.0004(3) -0.0014(3)
C2 0.0190(5) 0.0197(5) 0.0151(5) 0.0021(4) -0.0004(4) -0.0033(4)
C3 0.0214(5) 0.0309(6) 0.0149(5) 0.0019(4) 0.0029(4) -0.0096(4)
C4 0.0146(5) 0.0360(7) 0.0170(5) -0.0057(4) 0.0033(4) -0.0051(4)
C5 0.0138(5) 0.0252(6) 0.0188(5) -0.0060(4) -0.0002(4) 0.0012(4)
C6 0.0139(4) 0.0158(5) 0.0124(4) -0.0019(3) -0.0005(3) -0.0011(4)
C7 0.0226(5) 0.0126(5) 0.0179(5) -0.0001(4) -0.0008(4) 0.0021(4)
C8 0.0238(5) 0.0126(5) 0.0183(5) 0.0022(4) 0.0006(4) -0.0015(4)
C9 0.0152(4) 0.0175(5) 0.0147(4) -0.0010(4) 0.0039(3) -0.0002(4)
C10 0.0134(4) 0.0129(4) 0.0113(4) -0.0011(3) 0.0008(3) 0.0006(3)
C11 0.0103(4) 0.0129(4) 0.0159(4) 0.0001(3) 0.0021(3) 0.0008(3)
C12 0.0223(5) 0.0167(5) 0.0165(5) -0.0046(4) 0.0006(4) -0.0016(4)
C13 0.0181(5) 0.0148(5) 0.0190(5) -0.0004(4) -0.0014(4) 0.0035(4)
N1 0.0180(4) 0.0139(4) 0.0139(4) 0.0005(3) 0.0021(3) -0.0021(3)
N2 0.0183(4) 0.0141(4) 0.0116(4) -0.0022(3) 0.0015(3) -0.0007(3)
N3 0.0160(4) 0.0203(5) 0.0178(4) -0.0035(4) -0.0010(3) 0.0012(3)
O1 0.0181(4) 0.0151(4) 0.0144(3) 0.0009(3) -0.0015(3) 0.0002(3)
O2 0.0311(4) 0.0245(4) 0.0120(3) 0.0013(3) 0.0038(3) -0.0019(3)
O3 0.0361(5) 0.0218(4) 0.0169(4) -0.0008(3) 0.0054(3) -0.0071(4)
_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 1.3946(14) . ?
C1 C6 1.4118(14) . ?
C1 C10 1.5437(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3935(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3844(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3901(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3919(14) . ?
C6 O1 1.3902(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5381(15) . ?
C7 O1 1.4500(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N1 1.4691(14) . ?
C9 N1 1.4132(13) . ?
C9 N2 1.3471(14) . ?
C9 O2 1.2224(13) . ?
C10 C11 1.5294(14) . ?
C10 C13 1.5202(14) . ?
C10 N2 1.4685(12) . ?
C11 N1 1.4007(13) . ?
C11 N3 1.2631(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 N2 1.4475(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N3 H3A 0.813(18) . ?
O3 H3B 0.848(19) . ?
O3 H3C 0.95(2) . ?
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 117.60(9) . . ?
C2 C1 C10 120.73(9) . . ?
C6 C1 C10 121.59(9) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.40(10) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.09(10) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.79(10) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(10) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.93(9) . . ?
O1 C6 C1 121.15(9) . . ?
O1 C6 C5 117.71(9) . . ?
H7A C7 H7B 108.5 . . ?
C8 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
O1 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
O1 C7 C8 107.42(8) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N1 C8 C7 108.41(8) . . ?
N1 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
N2 C9 N1 108.51(9) . . ?
O2 C9 N1 124.14(10) . . ?
O2 C9 N2 127.33(10) . . ?
C11 C10 C1 106.21(8) . . ?
C13 C10 C1 114.25(8) . . ?
C13 C10 C11 112.43(8) . . ?
N2 C10 C1 111.61(8) . . ?
N2 C10 C11 100.23(8) . . ?
N2 C10 C13 111.16(8) . . ?
N1 C11 C10 107.72(8) . . ?
N3 C11 C10 128.32(9) . . ?
N3 C11 N1 123.78(10) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
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 . . ?
C9 N1 C8 115.57(8) . . ?
C11 N1 C8 117.05(8) . . ?
C11 N1 C9 109.07(8) . . ?
C9 N2 C10 112.06(8) . . ?
C9 N2 C12 123.29(9) . . ?
C12 N2 C10 123.29(8) . . ?
C11 N3 H3A 113.9(12) . . ?
C6 O1 C7 118.41(8) . . ?
H3B O3 H3C 107.9(18) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O3 0.813(18) 2.167(18) 2.9746(13) 172.7(17) 4_565
O3 H3B O2 0.848(19) 2.016(19) 2.8407(11) 163.7(17) .
O3 H3C N3 0.95(2) 1.91(2) 2.8618(13) 176(2) 3_556
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 2.35(16) . . . . ?
C1 C6 O1 C7 97.59(11) . . . . ?
C1 C10 C11 N1 103.54(9) . . . . ?
C1 C10 C11 N3 -71.73(12) . . . . ?
C1 C10 N2 C9 -96.33(10) . . . . ?
C1 C10 N2 C12 70.76(12) . . . . ?
C2 C1 C6 C5 -3.22(14) . . . . ?
C2 C1 C6 O1 171.53(9) . . . . ?
C2 C1 C10 C11 130.04(10) . . . . ?
C2 C1 C10 C13 5.51(13) . . . . ?
C2 C1 C10 N2 -121.66(10) . . . . ?
C2 C3 C4 C5 -3.15(16) . . . . ?
C3 C4 C5 C6 0.76(16) . . . . ?
C4 C5 C6 C1 2.47(15) . . . . ?
C4 C5 C6 O1 -172.45(9) . . . . ?
C5 C6 O1 C7 -87.50(11) . . . . ?
C6 C1 C2 C3 0.82(15) . . . . ?
C6 C1 C10 C11 -46.59(11) . . . . ?
C6 C1 C10 C13 -171.12(9) . . . . ?
C6 C1 C10 N2 61.71(12) . . . . ?
C7 C8 N1 C9 -82.32(10) . . . . ?
C7 C8 N1 C11 48.30(12) . . . . ?
C8 C7 O1 C6 -119.52(9) . . . . ?
C10 C1 C2 C3 -175.94(9) . . . . ?
C10 C1 C6 C5 173.51(9) . . . . ?
C10 C1 C6 O1 -11.74(14) . . . . ?
C10 C11 N1 C8 -127.46(9) . . . . ?
C10 C11 N1 C9 6.13(10) . . . . ?
C11 C10 N2 C9 15.80(10) . . . . ?
C11 C10 N2 C12 -177.12(9) . . . . ?
C13 C10 C11 N1 -130.82(9) . . . . ?
C13 C10 C11 N3 53.91(13) . . . . ?
C13 C10 N2 C9 134.85(9) . . . . ?
C13 C10 N2 C12 -58.06(12) . . . . ?
N1 C9 N2 C10 -13.14(11) . . . . ?
N1 C9 N2 C12 179.78(9) . . . . ?
N2 C9 N1 C8 138.29(9) . . . . ?
N2 C9 N1 C11 3.95(11) . . . . ?
N2 C10 C11 N1 -12.70(9) . . . . ?
N2 C10 C11 N3 172.02(10) . . . . ?
N3 C11 N1 C8 48.08(14) . . . . ?
N3 C11 N1 C9 -178.33(9) . . . . ?
O1 C7 C8 N1 39.31(11) . . . . ?
O2 C9 N1 C8 -43.49(14) . . . . ?
O2 C9 N1 C11 -177.83(10) . . . . ?
O2 C9 N2 C10 168.72(10) . . . . ?
O2 C9 N2 C12 1.64(17) . . . . ?
_shelx_res_file
;
TITL testm1 in P2(1)/c
CELL 0.71073 8.0314 8.1488 19.2027 90 90.5479 90
ZERR 4 0.0002 0.0002 0.0005 0 0.0017 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 52 68 12 12
EQIV $1 -X,-Y,1-Z
EQIV $2 +X,0.5-Y,-0.5+Z
L.S. 8
PLAN 5
TEMP -173.18
HTAB O3 N3_$1
HTAB O3 O2
HTAB N3 O3_$2
BOND $H
CONF
fmap 2 53
acta
REM
REM
REM
WGHT 0.047300 0.477100
FVAR 0.23227
C1 1 0.392424 0.371608 0.364509 11.00000 0.01274 0.01507 =
0.01102 -0.00112 0.00041 -0.00141
C2 1 0.450745 0.489076 0.317899 11.00000 0.01897 0.01972 =
0.01510 0.00205 -0.00036 -0.00333
AFIX 43
H2 2 0.382406 0.580565 0.306522 11.00000 -1.20000
AFIX 0
C3 1 0.607143 0.475100 0.287656 11.00000 0.02135 0.03095 =
0.01488 0.00187 0.00292 -0.00962
AFIX 43
H3 2 0.646036 0.558660 0.257389 11.00000 -1.20000
AFIX 0
C4 1 0.705909 0.339607 0.301661 11.00000 0.01461 0.03597 =
0.01701 -0.00571 0.00328 -0.00509
AFIX 43
H4 2 0.810120 0.327344 0.279255 11.00000 -1.20000
AFIX 0
C5 1 0.652120 0.221551 0.348614 11.00000 0.01381 0.02518 =
0.01875 -0.00595 -0.00021 0.00118
AFIX 43
H5 2 0.720254 0.129127 0.358748 11.00000 -1.20000
AFIX 0
C6 1 0.498531 0.238631 0.380793 11.00000 0.01390 0.01583 =
0.01237 -0.00186 -0.00052 -0.00111
C7 1 0.380518 -0.025546 0.414104 11.00000 0.02263 0.01257 =
0.01792 -0.00013 -0.00083 0.00213
AFIX 23
H7A 2 0.450440 -0.119202 0.429325 11.00000 -1.20000
H7B 2 0.365419 -0.031740 0.362944 11.00000 -1.20000
AFIX 0
C8 1 0.210584 -0.031464 0.450279 11.00000 0.02375 0.01257 =
0.01835 0.00218 0.00058 -0.00148
AFIX 23
H8A 2 0.136561 -0.111027 0.426328 11.00000 -1.20000
H8B 2 0.225003 -0.066835 0.499289 11.00000 -1.20000
AFIX 0
C9 1 0.192551 0.243630 0.499661 11.00000 0.01523 0.01751 =
0.01474 -0.00104 0.00393 -0.00016
C10 1 0.214467 0.382850 0.393801 11.00000 0.01345 0.01287 =
0.01127 -0.00109 0.00076 0.00061
C11 1 0.136053 0.213555 0.383143 11.00000 0.01033 0.01289 =
0.01593 0.00011 0.00205 0.00077
C12 1 0.272594 0.534279 0.508654 11.00000 0.02233 0.01667 =
0.01646 -0.00459 0.00063 -0.00156
AFIX 137
H12A 2 0.369496 0.581895 0.485508 11.00000 -1.50000
H12B 2 0.303649 0.501661 0.556152 11.00000 -1.50000
H12C 2 0.182992 0.615775 0.510348 11.00000 -1.50000
AFIX 0
C13 1 0.109400 0.519607 0.362257 11.00000 0.01813 0.01475 =
0.01898 -0.00044 -0.00140 0.00353
AFIX 137
H13A 2 -0.002207 0.517051 0.382418 11.00000 -1.50000
H13B 2 0.100941 0.504174 0.311735 11.00000 -1.50000
H13C 2 0.161735 0.625756 0.372286 11.00000 -1.50000
AFIX 0
N1 3 0.136677 0.133366 0.447664 11.00000 0.01803 0.01385 =
0.01393 0.00048 0.00206 -0.00205
N2 3 0.215943 0.391751 0.470183 11.00000 0.01830 0.01406 =
0.01156 -0.00221 0.00154 -0.00068
N3 3 0.088413 0.147446 0.326893 11.00000 0.01596 0.02025 =
0.01776 -0.00348 -0.00095 0.00118
H3A 2 0.095489 0.206937 0.293092 11.00000 0.03554
O1 4 0.459369 0.128200 0.433331 11.00000 0.01812 0.01510 =
0.01440 0.00085 -0.00151 0.00025
O2 4 0.210819 0.207256 0.561017 11.00000 0.03110 0.02448 =
0.01201 0.00127 0.00380 -0.00193
O3 4 0.088257 0.152466 0.697330 11.00000 0.03612 0.02181 =
0.01691 -0.00080 0.00537 -0.00706
H3B 2 0.135143 0.184773 0.660380 11.00000 0.03932
H3C 2 0.028879 0.053931 0.686745 11.00000 0.07089
HKLF 4
REM testm1 in P2(1)/c
REM R1 = 0.0378 for 3045 Fo > 4sig(Fo) and 0.0449 for all 3522 data
REM 186 parameters refined using 0 restraints
END
WGHT 0.0473 0.4767
REM Highest difference peak 0.398, deepest hole -0.218, 1-sigma level 0.046
Q1 1 0.3044 0.3764 0.3777 11.00000 0.05 0.40
Q2 1 0.5719 0.2269 0.3640 11.00000 0.05 0.39
Q3 1 0.1729 0.2985 0.3846 11.00000 0.05 0.38
Q4 1 0.4531 0.3176 0.3806 11.00000 0.05 0.38
Q5 1 0.1637 0.4514 0.3786 11.00000 0.05 0.37
;
_shelx_res_checksum 24006
_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_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_testo1
_database_code_depnum_ccdc_archive 'CCDC 1993733'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2019-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H15 N3 O2'
_chemical_formula_sum 'C13 H15 N3 O2'
_chemical_formula_weight 245.28
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 orthorhombic
_space_group_IT_number 61
_space_group_name_H-M_alt 'P b c a'
_space_group_name_Hall '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 13.4226(6)
_cell_length_b 7.6316(4)
_cell_length_c 22.4832(11)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2303.09(19)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 3972
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 27.91
_cell_measurement_theta_min 2.36
_shelx_estimated_absorpt_T_max 0.977
_shelx_estimated_absorpt_T_min 0.956
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6538
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0631 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8769. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.415
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1040
_exptl_crystal_size_max 0.461
_exptl_crystal_size_mid 0.284
_exptl_crystal_size_min 0.24
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0432
_diffrn_reflns_av_unetI/netI 0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 19730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.985
_diffrn_reflns_theta_min 1.812
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2249
_reflns_number_total 2763
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection 'Bruker Apex suite'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.334
_refine_diff_density_min -0.253
_refine_diff_density_rms 0.049
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.047
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 169
_refine_ls_number_reflns 2763
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0543
_refine_ls_R_factor_gt 0.0413
_refine_ls_restrained_S_all 1.047
_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^)+(0.0440P)^2^+1.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0977
_refine_ls_wR_factor_ref 0.1046
_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 Secondary CH2 refined with riding coordinates:
C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.62233(8) 0.38847(14) 0.57578(5) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.41715(9) 0.84783(14) 0.52343(5) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.55111(9) 0.65604(15) 0.55036(5) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.46241(8) 0.46118(14) 0.60307(5) 0.0138(2) Uani 1 1 d . . . . .
N3 N 0.49515(9) 0.87081(15) 0.61624(5) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.55124(10) 0.49086(17) 0.57724(6) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.39337(10) 0.61036(17) 0.59920(6) 0.0134(3) Uani 1 1 d . . . . .
C3 C 0.46196(10) 0.74963(17) 0.56927(6) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.43345(11) 0.29033(18) 0.62549(7) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.392753 0.230051 0.595634 0.032 Uiso 1 1 calc GR . . . .
H4B H 0.394788 0.304708 0.662139 0.032 Uiso 1 1 calc GR . . . .
H4C H 0.493232 0.220831 0.633822 0.032 Uiso 1 1 calc GR . . . .
C5 C 0.29887(11) 0.56377(19) 0.56585(6) 0.0191(3) Uani 1 1 d . . . . .
H5A H 0.316171 0.507605 0.528037 0.029 Uiso 1 1 calc GR . . . .
H5B H 0.260478 0.670565 0.558059 0.029 Uiso 1 1 calc GR . . . .
H5C H 0.258848 0.483024 0.589890 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.37617(10) 0.69054(17) 0.66026(6) 0.0143(3) Uani 1 1 d . . . . .
C7 C 0.31261(10) 0.63799(18) 0.70515(6) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.266990 0.544535 0.699039 0.022 Uiso 1 1 calc R . . . .
C8 C 0.31680(11) 0.72513(19) 0.75974(6) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.273641 0.691072 0.791171 0.026 Uiso 1 1 calc R . . . .
C9 C 0.38390(11) 0.86143(19) 0.76817(6) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.386623 0.918278 0.805727 0.025 Uiso 1 1 calc R . . . .
C10 C 0.44739(11) 0.91681(18) 0.72279(6) 0.0190(3) Uani 1 1 d . . . . .
H10 H 0.493008 1.010308 0.728819 0.023 Uiso 1 1 calc R . . . .
C11 C 0.44164(10) 0.83049(17) 0.66838(6) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.60436(12) 0.8770(2) 0.61734(7) 0.0269(4) Uani 1 1 d . . . . .
H12A H 0.630709 0.821087 0.653830 0.032 Uiso 1 1 calc R . . . .
H12B H 0.628536 0.999416 0.615471 0.032 Uiso 1 1 calc R . . . .
C13 C 0.63584(11) 0.7739(2) 0.56151(7) 0.0238(3) Uani 1 1 d . . . . .
H13A H 0.646765 0.853659 0.527390 0.029 Uiso 1 1 calc R . . . .
H13B H 0.697628 0.706522 0.568902 0.029 Uiso 1 1 calc R . . . .
H2 H 0.4041(14) 0.773(3) 0.4902(9) 0.038(5) Uiso 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
O1 0.0178(5) 0.0225(5) 0.0230(5) 0.0024(4) 0.0029(4) 0.0075(4)
O2 0.0328(6) 0.0199(5) 0.0165(5) 0.0028(4) -0.0024(4) 0.0066(4)
N1 0.0175(6) 0.0144(5) 0.0163(6) 0.0010(4) 0.0041(4) 0.0004(4)
N2 0.0145(6) 0.0112(5) 0.0156(5) 0.0012(4) 0.0008(4) 0.0017(4)
N3 0.0217(7) 0.0144(5) 0.0152(6) -0.0012(4) 0.0026(5) -0.0017(5)
C1 0.0171(7) 0.0158(6) 0.0114(6) -0.0014(5) 0.0006(5) 0.0009(5)
C2 0.0136(6) 0.0119(6) 0.0147(6) 0.0003(5) -0.0007(5) 0.0025(5)
C3 0.0201(7) 0.0123(6) 0.0126(6) 0.0001(5) 0.0008(5) 0.0022(5)
C4 0.0206(8) 0.0134(6) 0.0309(8) 0.0041(6) -0.0015(6) -0.0018(5)
C5 0.0163(7) 0.0216(7) 0.0193(7) -0.0043(5) -0.0033(5) 0.0029(5)
C6 0.0145(7) 0.0144(6) 0.0140(6) 0.0000(5) -0.0010(5) 0.0041(5)
C7 0.0146(7) 0.0194(6) 0.0199(7) 0.0020(5) 0.0010(5) 0.0026(5)
C8 0.0205(7) 0.0272(7) 0.0164(7) 0.0036(6) 0.0045(6) 0.0086(6)
C9 0.0251(8) 0.0251(7) 0.0127(6) -0.0037(5) -0.0026(6) 0.0105(6)
C10 0.0210(7) 0.0172(6) 0.0186(7) -0.0027(5) -0.0035(5) 0.0023(5)
C11 0.0157(7) 0.0139(6) 0.0142(6) 0.0009(5) 0.0003(5) 0.0033(5)
C12 0.0230(8) 0.0279(8) 0.0296(8) -0.0083(6) 0.0084(6) -0.0104(6)
C13 0.0228(8) 0.0221(7) 0.0265(8) -0.0016(6) 0.0090(6) -0.0064(6)
_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
O1 C1 1.2338(16) . ?
O2 C3 1.4091(16) . ?
O2 H2 0.96(2) . ?
N1 C1 1.3979(17) . ?
N1 C3 1.4570(17) . ?
N1 C13 1.4717(18) . ?
N2 C1 1.3454(17) . ?
N2 C2 1.4706(16) . ?
N2 C4 1.4509(17) . ?
N3 C3 1.4727(17) . ?
N3 C11 1.4089(17) . ?
N3 C12 1.467(2) . ?
C2 C3 1.5588(18) . ?
C2 C5 1.5159(19) . ?
C2 C6 1.5207(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3810(19) . ?
C6 C11 1.3951(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3915(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.540(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
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
C3 O2 H2 109.3(12) . . ?
C1 N1 C3 108.48(10) . . ?
C1 N1 C13 118.47(12) . . ?
C3 N1 C13 106.58(11) . . ?
C1 N2 C2 113.74(11) . . ?
C1 N2 C4 122.60(11) . . ?
C4 N2 C2 123.19(11) . . ?
C11 N3 C3 107.77(11) . . ?
C11 N3 C12 120.16(12) . . ?
C12 N3 C3 109.56(11) . . ?
O1 C1 N1 124.09(12) . . ?
O1 C1 N2 126.17(13) . . ?
N2 C1 N1 109.72(11) . . ?
N2 C2 C3 100.44(10) . . ?
N2 C2 C5 112.03(11) . . ?
N2 C2 C6 110.72(10) . . ?
C5 C2 C3 116.14(11) . . ?
C5 C2 C6 114.45(11) . . ?
C6 C2 C3 101.83(10) . . ?
O2 C3 N1 113.45(11) . . ?
O2 C3 N3 108.64(10) . . ?
O2 C3 C2 115.23(11) . . ?
N1 C3 N3 105.58(11) . . ?
N1 C3 C2 106.07(10) . . ?
N3 C3 C2 107.30(10) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 129.55(13) . . ?
C7 C6 C11 121.05(12) . . ?
C11 C6 C2 109.30(11) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.62(13) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.17(14) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.55(13) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.76(13) . . ?
C11 C10 H10 121.1 . . ?
C6 C11 N3 112.30(12) . . ?
C10 C11 N3 126.86(13) . . ?
C10 C11 C6 120.82(13) . . ?
N3 C12 H12A 110.9 . . ?
N3 C12 H12B 110.9 . . ?
N3 C12 C13 104.12(12) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
N1 C13 C12 103.82(11) . . ?
N1 C13 H13A 111.0 . . ?
N1 C13 H13B 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.96(2) 1.96(2) 2.9169(15) 177.8(18) 5_666 yes
_shelx_res_file
;
TITL testo1_a.res in Pbca
testo1.res
created by SHELXL-2017/1 at 14:35:00 on 30-Jan-2019
REM Old TITL testo1 in Pbca
REM SHELXT solution in Pbca
REM R1 0.120, Rweak 0.003, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C13 N3 O2
CELL 0.71073 13.4226 7.6316 22.4832 90 90 90
ZERR 8 0.0006 0.0004 0.0011 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 104 120 24 16
EQIV $1 1-X,1-Y,1-Z
L.S. 4 0 0
PLAN 5
SIZE 0.24 0.284 0.461
TEMP -173(2)
HTAB O2 O1_$1
BOND $H
list 4
fmap 2 53
ACTA
REM
REM
REM
WGHT 0.044000 1.290500
FVAR 0.41730
O1 4 0.622327 0.388474 0.575776 11.00000 0.01777 0.02247 =
0.02305 0.00243 0.00288 0.00755
O2 4 0.417147 0.847833 0.523431 11.00000 0.03284 0.01991 =
0.01654 0.00279 -0.00237 0.00664
N1 3 0.551110 0.656037 0.550364 11.00000 0.01746 0.01444 =
0.01628 0.00096 0.00413 0.00039
N2 3 0.462415 0.461178 0.603072 11.00000 0.01445 0.01123 =
0.01558 0.00125 0.00076 0.00165
N3 3 0.495153 0.870805 0.616237 11.00000 0.02172 0.01441 =
0.01517 -0.00117 0.00259 -0.00173
C1 1 0.551238 0.490863 0.577241 11.00000 0.01707 0.01579 =
0.01136 -0.00141 0.00064 0.00088
C2 1 0.393373 0.610358 0.599199 11.00000 0.01356 0.01192 =
0.01466 0.00026 -0.00068 0.00247
C3 1 0.461957 0.749627 0.569272 11.00000 0.02011 0.01230 =
0.01256 0.00010 0.00077 0.00221
C4 1 0.433446 0.290329 0.625485 11.00000 0.02062 0.01342 =
0.03085 0.00411 -0.00151 -0.00184
AFIX 137
H4A 2 0.392753 0.230051 0.595634 11.00000 -1.50000
H4B 2 0.394788 0.304708 0.662139 11.00000 -1.50000
H4C 2 0.493232 0.220831 0.633822 11.00000 -1.50000
AFIX 0
C5 1 0.298866 0.563771 0.565849 11.00000 0.01627 0.02160 =
0.01935 -0.00435 -0.00329 0.00289
AFIX 137
H5A 2 0.316171 0.507605 0.528037 11.00000 -1.50000
H5B 2 0.260478 0.670565 0.558059 11.00000 -1.50000
H5C 2 0.258848 0.483024 0.589890 11.00000 -1.50000
AFIX 0
C6 1 0.376167 0.690536 0.660262 11.00000 0.01447 0.01443 =
0.01403 0.00005 -0.00104 0.00408
C7 1 0.312608 0.637990 0.705153 11.00000 0.01455 0.01943 =
0.01986 0.00205 0.00102 0.00265
AFIX 43
H7 2 0.266990 0.544535 0.699039 11.00000 -1.20000
AFIX 0
C8 1 0.316796 0.725128 0.759739 11.00000 0.02045 0.02724 =
0.01636 0.00364 0.00453 0.00859
AFIX 43
H8 2 0.273641 0.691072 0.791171 11.00000 -1.20000
AFIX 0
C9 1 0.383898 0.861432 0.768172 11.00000 0.02513 0.02505 =
0.01267 -0.00370 -0.00263 0.01048
AFIX 43
H9 2 0.386623 0.918278 0.805727 11.00000 -1.20000
AFIX 0
C10 1 0.447386 0.916813 0.722785 11.00000 0.02101 0.01724 =
0.01865 -0.00267 -0.00345 0.00233
AFIX 43
H10 2 0.493008 1.010308 0.728819 11.00000 -1.20000
AFIX 0
C11 1 0.441637 0.830492 0.668379 11.00000 0.01568 0.01391 =
0.01419 0.00087 0.00032 0.00325
C12 1 0.604355 0.876986 0.617342 11.00000 0.02304 0.02793 =
0.02962 -0.00831 0.00841 -0.01036
AFIX 23
H12A 2 0.630709 0.821087 0.653830 11.00000 -1.20000
H12B 2 0.628536 0.999416 0.615471 11.00000 -1.20000
AFIX 0
C13 1 0.635842 0.773933 0.561508 11.00000 0.02275 0.02210 =
0.02648 -0.00165 0.00905 -0.00636
AFIX 23
H13A 2 0.646765 0.853659 0.527390 11.00000 -1.20000
H13B 2 0.697628 0.706522 0.568902 11.00000 -1.20000
AFIX 0
H2 2 0.404078 0.772821 0.490182 11.00000 0.03783
HKLF 4
REM testo1_a.res in Pbca
REM R1 = 0.0413 for 2249 Fo > 4sig(Fo) and 0.0543 for all 2763 data
REM 169 parameters refined using 0 restraints
END
WGHT 0.0440 1.2905
REM Highest difference peak 0.334, deepest hole -0.253, 1-sigma level 0.049
Q1 1 0.4207 0.6816 0.5814 11.00000 0.05 0.33
Q2 1 0.4751 0.9551 0.5172 11.00000 0.05 0.29
Q3 1 0.4797 0.8027 0.5975 11.00000 0.05 0.27
Q4 1 0.3343 0.6584 0.7395 11.00000 0.05 0.25
Q5 1 0.5046 0.6930 0.5582 11.00000 0.05 0.24
;
_shelx_res_checksum 66374
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3:Et2O'
#######################################################################
#
# 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_mm102_1
_database_code_depnum_ccdc_archive 'CCDC 1993732'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number 2013-4
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C18 H23 N3 O, 1.5(H2 O)'
_chemical_formula_sum 'C18 H26 N3 O2.50'
_chemical_formula_weight 324.42
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.6118(2)
_cell_length_b 9.3656(3)
_cell_length_c 12.1634(4)
_cell_angle_alpha 93.7306(19)
_cell_angle_beta 95.390(2)
_cell_angle_gamma 108.1269(18)
_cell_volume 816.35(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5942
_cell_measurement_temperature 100
_cell_measurement_theta_max 31.13
_cell_measurement_theta_min 2.30
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_T_max 0.7462
_exptl_absorpt_correction_T_min 0.6445
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0582 before and 0.0412 after correction. The Ratio of minimum to maximum transmission is 0.8637. The \l/2 correction factor is Not present.'
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.320
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 350
_exptl_crystal_size_max 0.534
_exptl_crystal_size_mid 0.264
_exptl_crystal_size_min 0.196
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0296
_diffrn_reflns_av_unetI/netI 0.0292
_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 -10
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 18692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 30.507
_diffrn_reflns_theta_min 1.690
_diffrn_ambient_temperature 100.01
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4047
_reflns_number_total 4993
_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 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_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 0.409
_refine_diff_density_min -0.365
_refine_diff_density_rms 0.052
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 232
_refine_ls_number_reflns 4993
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0557
_refine_ls_R_factor_gt 0.0428
_refine_ls_restrained_S_all 1.039
_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^)+(0.0567P)^2^+0.2838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1072
_refine_ls_wR_factor_ref 0.1150
_refine_special_details
;
The hydrogen atoms on the nitrogen and full occupancy oxygen atom were found by
difference map. All other hydrogens were placed geometrically and refined using
a riding model.
;
_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 O(H,H) groups
2. Others
Fixed Sof: O3(0.5) H3C(0.5) H3D(0.5)
3.a Free rotating group:
O3(H3C,H3D)
3.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B),
C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
C13(H13), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens mixed
_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 0.07429(14) 0.60387(11) 0.30322(9) 0.01097(19) Uani 1 1 d . . . . .
C2 C 0.06715(16) 0.70562(12) 0.40665(9) 0.0153(2) Uani 1 1 d . . . . .
H2A H 0.0131 0.6410 0.4642 0.018 Uiso 1 1 calc R . . . .
H2B H 0.1957 0.7675 0.4369 0.018 Uiso 1 1 calc R . . . .
C3 C -0.04792(17) 0.81066(14) 0.38213(10) 0.0190(2) Uani 1 1 d . . . . .
H3A H -0.0530 0.8691 0.4519 0.023 Uiso 1 1 calc R . . . .
H3B H 0.0128 0.8829 0.3306 0.023 Uiso 1 1 calc R . . . .
C4 C -0.24526(17) 0.72042(14) 0.33067(10) 0.0192(2) Uani 1 1 d . . . . .
H4A H -0.3100 0.6543 0.3846 0.023 Uiso 1 1 calc R . . . .
H4B H -0.3157 0.7903 0.3122 0.023 Uiso 1 1 calc R . . . .
C5 C -0.23882(15) 0.62483(12) 0.22597(9) 0.0147(2) Uani 1 1 d . . . . .
H5A H -0.3661 0.5579 0.1978 0.018 Uiso 1 1 calc R . . . .
H5B H -0.1919 0.6914 0.1680 0.018 Uiso 1 1 calc R . . . .
C6 C -0.18135(14) 0.38405(12) 0.25919(9) 0.01196(19) Uani 1 1 d . . . . .
C7 C -0.03777(15) 0.18306(12) 0.29679(10) 0.0151(2) Uani 1 1 d . . . . .
H7A H -0.1461 0.1221 0.3309 0.018 Uiso 1 1 calc R . . . .
H7B H 0.0763 0.1749 0.3384 0.018 Uiso 1 1 calc R . . . .
C8 C -0.05235(15) 0.11922(12) 0.17537(10) 0.0162(2) Uani 1 1 d . . . . .
H8A H -0.1452 0.1528 0.1308 0.019 Uiso 1 1 calc R . . . .
H8B H -0.1010 0.0077 0.1715 0.019 Uiso 1 1 calc R . . . .
C9 C 0.12880(16) 0.16319(12) 0.12075(10) 0.0179(2) Uani 1 1 d . . . . .
H9A H 0.2100 0.1085 0.1534 0.021 Uiso 1 1 calc R . . . .
H9B H 0.0972 0.1268 0.0409 0.021 Uiso 1 1 calc R . . . .
C10 C 0.24128(14) 0.33139(12) 0.13093(9) 0.0141(2) Uani 1 1 d . . . . .
H10A H 0.3511 0.3444 0.0903 0.017 Uiso 1 1 calc R . . . .
H10B H 0.2875 0.3656 0.2101 0.017 Uiso 1 1 calc R . . . .
C11 C 0.13229(14) 0.43336(12) 0.08624(9) 0.01217(19) Uani 1 1 d . . . . .
H11A H 0.1140 0.4178 0.0041 0.015 Uiso 1 1 calc R . . . .
H11B H 0.0078 0.4029 0.1124 0.015 Uiso 1 1 calc R . . . .
C12 C 0.22953(14) 0.59962(12) 0.12245(9) 0.01158(19) Uani 1 1 d . . . . .
C13 C 0.35422(15) 0.67831(13) 0.05279(9) 0.0153(2) Uani 1 1 d . . . . .
H13 H 0.3681 0.6261 -0.0137 0.018 Uiso 1 1 calc R . . . .
C14 C 0.45842(15) 0.82972(13) 0.07704(10) 0.0182(2) Uani 1 1 d . . . . .
H14 H 0.5419 0.8796 0.0279 0.022 Uiso 1 1 calc R . . . .
C15 C 0.43914(15) 0.90691(13) 0.17364(10) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.5099 1.0104 0.1917 0.022 Uiso 1 1 calc R . . . .
C16 C 0.31517(15) 0.83183(12) 0.24420(10) 0.0151(2) Uani 1 1 d . . . . .
H16 H 0.3029 0.8857 0.3104 0.018 Uiso 1 1 calc R . . . .
C17 C 0.20805(14) 0.67957(11) 0.22084(9) 0.01110(19) Uani 1 1 d . . . . .
C18 C 0.12029(14) 0.46617(12) 0.34229(9) 0.01149(19) Uani 1 1 d . . . . .
N1 N -0.11771(12) 0.53358(10) 0.24885(8) 0.01142(17) Uani 1 1 d . . . . .
N2 N -0.03201(12) 0.34146(10) 0.30576(8) 0.01219(18) Uani 1 1 d . . . . .
N3 N 0.26689(13) 0.46207(11) 0.40019(8) 0.01535(19) Uani 1 1 d . . . . .
H3 H 0.344(2) 0.5532(19) 0.4197(13) 0.024(4) Uiso 1 1 d . . . . .
O1 O -0.33932(11) 0.29648(9) 0.23195(7) 0.01649(17) Uani 1 1 d . . . . .
O2 O 0.53881(15) 0.75445(13) 0.57580(9) 0.0316(2) Uani 1 1 d . . . . .
H2C H 0.490(3) 0.752(2) 0.637(2) 0.055(6) Uiso 1 1 d . . . . .
H2D H 0.608(3) 0.695(2) 0.5820(17) 0.048(6) Uiso 1 1 d . . . . .
O3 O 0.3814(3) -0.0038(2) 0.53501(18) 0.0301(4) Uani 0.5 1 d . . P A -1
H3C H 0.4353 0.0702 0.4975 0.045 Uiso 0.5 1 d G . P A -1
H3D H 0.3769 0.0314 0.6022 0.045 Uiso 0.5 1 d G . P A -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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0115(4) 0.0108(4) 0.0107(4) 0.0008(3) 0.0012(3) 0.0037(3)
C2 0.0204(5) 0.0156(5) 0.0115(5) -0.0008(4) 0.0011(4) 0.0085(4)
C3 0.0260(6) 0.0185(5) 0.0164(5) -0.0019(4) 0.0019(4) 0.0134(5)
C4 0.0205(5) 0.0236(6) 0.0189(5) 0.0012(4) 0.0046(4) 0.0142(5)
C5 0.0142(5) 0.0169(5) 0.0160(5) 0.0029(4) 0.0013(4) 0.0092(4)
C6 0.0117(4) 0.0145(5) 0.0109(4) 0.0025(4) 0.0034(4) 0.0052(4)
C7 0.0164(5) 0.0102(5) 0.0191(5) 0.0043(4) 0.0027(4) 0.0041(4)
C8 0.0164(5) 0.0105(5) 0.0207(5) 0.0003(4) 0.0019(4) 0.0028(4)
C9 0.0189(5) 0.0129(5) 0.0232(6) -0.0002(4) 0.0050(4) 0.0067(4)
C10 0.0115(4) 0.0139(5) 0.0177(5) 0.0002(4) 0.0032(4) 0.0052(4)
C11 0.0119(4) 0.0125(5) 0.0118(4) 0.0005(4) 0.0021(4) 0.0035(4)
C12 0.0098(4) 0.0128(5) 0.0125(5) 0.0027(4) 0.0006(4) 0.0039(3)
C13 0.0143(5) 0.0176(5) 0.0152(5) 0.0049(4) 0.0047(4) 0.0053(4)
C14 0.0132(5) 0.0188(5) 0.0237(6) 0.0103(4) 0.0056(4) 0.0041(4)
C15 0.0130(5) 0.0126(5) 0.0275(6) 0.0051(4) 0.0007(4) 0.0018(4)
C16 0.0135(5) 0.0118(5) 0.0194(5) 0.0004(4) 0.0002(4) 0.0037(4)
C17 0.0101(4) 0.0106(4) 0.0127(5) 0.0025(4) 0.0009(4) 0.0034(3)
C18 0.0131(4) 0.0125(5) 0.0099(4) 0.0019(3) 0.0037(4) 0.0048(4)
N1 0.0097(4) 0.0120(4) 0.0133(4) 0.0014(3) 0.0014(3) 0.0045(3)
N2 0.0120(4) 0.0108(4) 0.0140(4) 0.0029(3) 0.0014(3) 0.0038(3)
N3 0.0139(4) 0.0157(4) 0.0163(4) 0.0025(3) -0.0001(3) 0.0049(4)
O1 0.0112(3) 0.0170(4) 0.0195(4) 0.0022(3) 0.0021(3) 0.0017(3)
O2 0.0335(5) 0.0454(6) 0.0302(5) 0.0167(5) 0.0133(4) 0.0276(5)
O3 0.0341(10) 0.0231(9) 0.0322(11) 0.0022(8) 0.0055(9) 0.0074(8)
_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 1.5436(15) . ?
C1 C17 1.5421(14) . ?
C1 C18 1.5301(14) . ?
C1 N1 1.4730(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5327(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5254(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5219(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N1 1.4597(13) . ?
C6 N1 1.3505(14) . ?
C6 N2 1.4010(13) . ?
C6 O1 1.2265(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5375(16) . ?
C7 N2 1.4671(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5384(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5315(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5399(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5162(14) . ?
C12 C13 1.3996(14) . ?
C12 C17 1.4199(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3888(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3830(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3926(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3997(14) . ?
C18 N2 1.3779(13) . ?
C18 N3 1.2748(14) . ?
N3 H3 0.874(17) . ?
O2 H2C 0.86(2) . ?
O2 H2D 0.89(2) . ?
O3 H3C 0.8699 . ?
O3 H3D 0.8695 . ?
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
C17 C1 C2 116.21(9) . . ?
C18 C1 C2 108.23(8) . . ?
C18 C1 C17 110.37(8) . . ?
N1 C1 C2 107.76(8) . . ?
N1 C1 C17 111.92(8) . . ?
N1 C1 C18 101.25(8) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 113.05(9) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.81(10) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.93(9) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C5 C4 110.55(9) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C6 N2 107.90(9) . . ?
O1 C6 N1 127.90(10) . . ?
O1 C6 N2 124.19(10) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 111.85(9) . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 C9 116.37(9) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C8 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C8 116.84(9) . . ?
C10 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.57(9) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 113.09(9) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C13 C12 C11 116.05(9) . . ?
C13 C12 C17 118.13(10) . . ?
C17 C12 C11 125.81(9) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 C12 122.64(11) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.16(10) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.49(10) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.19(11) . . ?
C17 C16 H16 118.9 . . ?
C12 C17 C1 122.36(9) . . ?
C16 C17 C1 119.24(9) . . ?
C16 C17 C12 118.39(10) . . ?
N2 C18 C1 107.00(8) . . ?
N3 C18 C1 128.49(10) . . ?
N3 C18 N2 124.48(10) . . ?
C5 N1 C1 120.70(8) . . ?
C6 N1 C1 111.94(8) . . ?
C6 N1 C5 123.65(9) . . ?
C6 N2 C7 121.21(9) . . ?
C18 N2 C6 111.06(9) . . ?
C18 N2 C7 126.98(9) . . ?
C18 N3 H3 110.8(11) . . ?
H2C O2 H2D 105.3(19) . . ?
H3C O3 H3D 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2C O1 0.86(2) 2.05(2) 2.8918(14) 168(2) 2_566
O2 H2D N3 0.89(2) 1.99(2) 2.8717(14) 172.1(19) 2_666
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 56.24(13) . . . . ?
C1 C18 N2 C6 -7.42(11) . . . . ?
C1 C18 N2 C7 162.74(10) . . . . ?
C2 C1 C17 C12 179.73(9) . . . . ?
C2 C1 C17 C16 0.90(14) . . . . ?
C2 C1 C18 N2 115.53(9) . . . . ?
C2 C1 C18 N3 -62.67(14) . . . . ?
C2 C1 N1 C5 49.11(12) . . . . ?
C2 C1 N1 C6 -109.94(10) . . . . ?
C2 C3 C4 C5 -56.73(13) . . . . ?
C3 C4 C5 N1 52.76(12) . . . . ?
C4 C5 N1 C1 -52.45(13) . . . . ?
C4 C5 N1 C6 104.06(12) . . . . ?
C7 C8 C9 C10 -50.31(14) . . . . ?
C8 C7 N2 C6 62.30(13) . . . . ?
C8 C7 N2 C18 -106.95(12) . . . . ?
C8 C9 C10 C11 -56.43(14) . . . . ?
C9 C10 C11 C12 165.81(9) . . . . ?
C10 C11 C12 C13 89.20(11) . . . . ?
C10 C11 C12 C17 -89.21(12) . . . . ?
C11 C12 C13 C14 -177.65(10) . . . . ?
C11 C12 C17 C1 -1.72(16) . . . . ?
C11 C12 C17 C16 177.12(10) . . . . ?
C12 C13 C14 C15 -0.05(17) . . . . ?
C13 C12 C17 C1 179.91(9) . . . . ?
C13 C12 C17 C16 -1.26(15) . . . . ?
C13 C14 C15 C16 -0.38(17) . . . . ?
C14 C15 C16 C17 -0.04(17) . . . . ?
C15 C16 C17 C1 179.74(9) . . . . ?
C15 C16 C17 C12 0.87(16) . . . . ?
C17 C1 C2 C3 77.61(12) . . . . ?
C17 C1 C18 N2 -116.28(9) . . . . ?
C17 C1 C18 N3 65.52(14) . . . . ?
C17 C1 N1 C5 -79.85(11) . . . . ?
C17 C1 N1 C6 121.10(9) . . . . ?
C17 C12 C13 C14 0.88(16) . . . . ?
C18 C1 C2 C3 -157.60(9) . . . . ?
C18 C1 C17 C12 56.04(12) . . . . ?
C18 C1 C17 C16 -122.78(10) . . . . ?
C18 C1 N1 C5 162.60(9) . . . . ?
C18 C1 N1 C6 3.55(11) . . . . ?
N1 C1 C2 C3 -48.87(12) . . . . ?
N1 C1 C17 C12 -55.90(12) . . . . ?
N1 C1 C17 C16 125.27(10) . . . . ?
N1 C1 C18 N2 2.39(10) . . . . ?
N1 C1 C18 N3 -175.80(11) . . . . ?
N1 C6 N2 C7 -161.00(9) . . . . ?
N1 C6 N2 C18 9.81(12) . . . . ?
N2 C6 N1 C1 -8.12(11) . . . . ?
N2 C6 N1 C5 -166.44(9) . . . . ?
N2 C7 C8 C9 78.32(12) . . . . ?
N3 C18 N2 C6 170.87(10) . . . . ?
N3 C18 N2 C7 -18.97(17) . . . . ?
O1 C6 N1 C1 173.12(10) . . . . ?
O1 C6 N1 C5 14.80(17) . . . . ?
O1 C6 N2 C7 17.82(16) . . . . ?
O1 C6 N2 C18 -171.37(10) . . . . ?
_shelx_res_file
;
TITL test1 in P-1
CELL 0.71073 7.6118 9.3656 12.1634 93.7306 95.3896 108.1269
ZERR 2 0.0002 0.0003 0.0004 0.0019 0.002 0.0018
LATT 1
SFAC C H N O
UNIT 36 52 6 5
EQIV $1 1-X,1-Y,1-Z
EQIV $2 -X,1-Y,1-Z
L.S. 8
PLAN 5
TEMP -173.14
HTAB O2 N3_$1
HTAB O2 O1_$2
BOND $H
CONF
fmap 2 53
acta
REM
REM
REM
WGHT 0.056700 0.283800
FVAR 0.32139
C1 1 0.074290 0.603870 0.303219 11.00000 0.01146 0.01076 =
0.01074 0.00080 0.00118 0.00374
C2 1 0.067153 0.705622 0.406645 11.00000 0.02041 0.01557 =
0.01149 -0.00078 0.00106 0.00852
AFIX 23
H2A 2 0.013135 0.641023 0.464227 11.00000 -1.20000
H2B 2 0.195706 0.767458 0.436862 11.00000 -1.20000
AFIX 0
C3 1 -0.047924 0.810656 0.382134 11.00000 0.02596 0.01849 =
0.01641 -0.00191 0.00190 0.01340
AFIX 23
H3A 2 -0.053012 0.869143 0.451877 11.00000 -1.20000
H3B 2 0.012754 0.882931 0.330565 11.00000 -1.20000
AFIX 0
C4 1 -0.245256 0.720417 0.330668 11.00000 0.02053 0.02356 =
0.01891 0.00120 0.00461 0.01421
AFIX 23
H4A 2 -0.309983 0.654264 0.384572 11.00000 -1.20000
H4B 2 -0.315660 0.790264 0.312223 11.00000 -1.20000
AFIX 0
C5 1 -0.238824 0.624829 0.225968 11.00000 0.01421 0.01689 =
0.01596 0.00289 0.00126 0.00922
AFIX 23
H5A 2 -0.366050 0.557933 0.197771 11.00000 -1.20000
H5B 2 -0.191950 0.691426 0.167968 11.00000 -1.20000
AFIX 0
C6 1 -0.181353 0.384051 0.259187 11.00000 0.01173 0.01451 =
0.01093 0.00247 0.00340 0.00522
C7 1 -0.037771 0.183058 0.296789 11.00000 0.01642 0.01023 =
0.01906 0.00429 0.00269 0.00409
AFIX 23
H7A 2 -0.146098 0.122102 0.330896 11.00000 -1.20000
H7B 2 0.076332 0.174932 0.338423 11.00000 -1.20000
AFIX 0
C8 1 -0.052353 0.119217 0.175372 11.00000 0.01636 0.01048 =
0.02065 0.00030 0.00192 0.00283
AFIX 23
H8A 2 -0.145221 0.152754 0.130842 11.00000 -1.20000
H8B 2 -0.101034 0.007689 0.171546 11.00000 -1.20000
AFIX 0
C9 1 0.128801 0.163187 0.120750 11.00000 0.01890 0.01289 =
0.02325 -0.00019 0.00495 0.00669
AFIX 23
H9A 2 0.210049 0.108491 0.153405 11.00000 -1.20000
H9B 2 0.097205 0.126836 0.040860 11.00000 -1.20000
AFIX 0
C10 1 0.241278 0.331389 0.130929 11.00000 0.01149 0.01386 =
0.01773 0.00025 0.00321 0.00520
AFIX 23
H10A 2 0.351146 0.344402 0.090330 11.00000 -1.20000
H10B 2 0.287464 0.365571 0.210119 11.00000 -1.20000
AFIX 0
C11 1 0.132292 0.433356 0.086245 11.00000 0.01189 0.01252 =
0.01185 0.00051 0.00209 0.00347
AFIX 23
H11A 2 0.113974 0.417829 0.004147 11.00000 -1.20000
H11B 2 0.007817 0.402899 0.112356 11.00000 -1.20000
AFIX 0
C12 1 0.229528 0.599622 0.122447 11.00000 0.00979 0.01276 =
0.01247 0.00273 0.00064 0.00391
C13 1 0.354221 0.678311 0.052790 11.00000 0.01434 0.01764 =
0.01521 0.00493 0.00467 0.00529
AFIX 43
H13 2 0.368132 0.626055 -0.013746 11.00000 -1.20000
AFIX 0
C14 1 0.458425 0.829719 0.077037 11.00000 0.01317 0.01877 =
0.02370 0.01034 0.00556 0.00411
AFIX 43
H14 2 0.541896 0.879637 0.027890 11.00000 -1.20000
AFIX 0
C15 1 0.439139 0.906906 0.173639 11.00000 0.01295 0.01259 =
0.02745 0.00514 0.00066 0.00178
AFIX 43
H15 2 0.509917 1.010352 0.191721 11.00000 -1.20000
AFIX 0
C16 1 0.315172 0.831826 0.244201 11.00000 0.01347 0.01182 =
0.01936 0.00044 0.00019 0.00375
AFIX 43
H16 2 0.302901 0.885739 0.310395 11.00000 -1.20000
AFIX 0
C17 1 0.208049 0.679572 0.220843 11.00000 0.01009 0.01061 =
0.01275 0.00253 0.00094 0.00338
C18 1 0.120290 0.466168 0.342285 11.00000 0.01308 0.01251 =
0.00993 0.00187 0.00371 0.00477
N1 3 -0.117711 0.533576 0.248854 11.00000 0.00969 0.01200 =
0.01333 0.00144 0.00142 0.00452
N2 3 -0.032008 0.341465 0.305758 11.00000 0.01203 0.01081 =
0.01404 0.00295 0.00138 0.00381
N3 3 0.266887 0.462072 0.400190 11.00000 0.01393 0.01566 =
0.01634 0.00250 -0.00006 0.00493
H3 2 0.343838 0.553212 0.419684 11.00000 0.02401
O1 4 -0.339319 0.296477 0.231951 11.00000 0.01117 0.01700 =
0.01948 0.00219 0.00211 0.00174
O2 4 0.538815 0.754448 0.575804 11.00000 0.03346 0.04544 =
0.03017 0.01669 0.01326 0.02758
H2C 2 0.489539 0.752216 0.636624 11.00000 0.05489
H2D 2 0.608412 0.694559 0.581973 11.00000 0.04847
PART -1
AFIX 6
O3 4 0.381414 -0.003845 0.535007 10.50000 0.03406 0.02312 =
0.03216 0.00223 0.00549 0.00743
H3C 2 0.435268 0.070240 0.497519 10.50000 -1.50000
H3D 2 0.376906 0.031441 0.602225 10.50000 -1.50000
AFIX 0
HKLF 4
REM test1 in P-1
REM R1 = 0.0428 for 4047 Fo > 4sig(Fo) and 0.0557 for all 4993 data
REM 232 parameters refined using 0 restraints
END
WGHT 0.0567 0.2838
REM Highest difference peak 0.409, deepest hole -0.365, 1-sigma level 0.052
Q1 1 0.3075 0.6400 0.0931 11.00000 0.05 0.41
Q2 1 0.1449 0.6402 0.2599 11.00000 0.05 0.41
Q3 1 0.0745 0.6577 0.3541 11.00000 0.05 0.36
Q4 1 0.1079 0.5364 0.3247 11.00000 0.05 0.36
Q5 1 -0.1030 0.3612 0.2825 11.00000 0.05 0.36
;
_shelx_res_checksum 81872
_olex2_exptl_crystal_mounting_method 'Oil on pip'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
#######################################################################
#
# 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_testt1
_database_code_depnum_ccdc_archive 'CCDC 1993729'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H19 N3 O, H2 O'
_chemical_formula_sum 'C15 H21 N3 O2'
_chemical_formula_weight 275.35
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.1405(3)
_cell_length_b 8.5770(4)
_cell_length_c 11.9704(6)
_cell_angle_alpha 73.957(3)
_cell_angle_beta 88.399(3)
_cell_angle_gamma 78.976(3)
_cell_volume 691.32(6)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4230
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 27.820
_cell_measurement_theta_min 2.517
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6479
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0607 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.8690. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.323
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 296
_exptl_crystal_size_max 0.382
_exptl_crystal_size_mid 0.326
_exptl_crystal_size_min 0.149
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0270
_diffrn_reflns_av_unetI/netI 0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 12697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.928
_diffrn_reflns_theta_min 1.771
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2810
_reflns_number_total 3308
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection 'Bruker Apex suite'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.415
_refine_diff_density_min -0.227
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 196
_refine_ls_number_reflns 3308
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0471
_refine_ls_R_factor_gt 0.0395
_refine_ls_restrained_S_all 1.045
_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^)+(0.0508P)^2^+0.2370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0994
_refine_ls_wR_factor_ref 0.1040
_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. Restrained distances
O2-H2A \\sim O2-H2B
with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
C8(H8)
3.b Secondary CH2 refined with riding coordinates:
C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
C11(H11), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.16614(12) 0.68735(11) 0.73994(8) 0.0192(2) Uani 1 1 d . . . . .
N1 N 0.35734(14) 0.42970(12) 0.79373(9) 0.0153(2) Uani 1 1 d . . . . .
N2 N 0.47949(14) 0.64342(12) 0.81087(8) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.76486(16) 0.50686(15) 0.91416(9) 0.0220(2) Uani 1 1 d . . . . .
H3 H 0.835(3) 0.415(2) 0.9382(16) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.31772(17) 0.59465(15) 0.77638(10) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.55519(16) 0.35622(14) 0.83376(10) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.61643(17) 0.50275(14) 0.86101(10) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.67973(16) 0.31452(14) 0.73434(10) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.70212(16) 0.43352(14) 0.62796(10) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.61165(17) 0.61710(15) 0.59056(10) 0.0160(2) Uani 1 1 d . . . . .
H6A H 0.475909 0.627163 0.604302 0.019 Uiso 1 1 calc R . . . .
H6B H 0.626266 0.657743 0.507342 0.019 Uiso 1 1 calc R . . . .
C7 C 0.68901(17) 0.73257(15) 0.64964(10) 0.0166(2) Uani 1 1 d . . . . .
H7A H 0.811085 0.675490 0.687477 0.020 Uiso 1 1 calc R . . . .
H7B H 0.710875 0.829581 0.590051 0.020 Uiso 1 1 calc R . . . .
C8 C 0.55536(17) 0.78885(14) 0.74011(10) 0.0161(2) Uani 1 1 d . . . . .
H8 H 0.632486 0.823293 0.792077 0.019 Uiso 1 1 calc R . . . .
C9 C 0.21769(18) 0.33488(16) 0.77712(11) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.098845 0.408317 0.749669 0.030 Uiso 1 1 calc GR . . . .
H9B H 0.199113 0.257490 0.849708 0.030 Uiso 1 1 calc GR . . . .
H9C H 0.262720 0.276122 0.721015 0.030 Uiso 1 1 calc GR . . . .
C10 C 0.56141(19) 0.21261(15) 0.94296(11) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.479645 0.248063 0.999856 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.689873 0.175970 0.973884 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.518644 0.123288 0.923958 0.029 Uiso 1 1 calc GR . . . .
C11 C 0.77711(17) 0.15172(15) 0.75120(11) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.765726 0.074502 0.821678 0.020 Uiso 1 1 calc R . . . .
C12 C 0.89007(17) 0.10103(16) 0.66676(11) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.951848 -0.008519 0.680349 0.024 Uiso 1 1 calc R . . . .
C13 C 0.90973(17) 0.21500(16) 0.56237(11) 0.0199(3) Uani 1 1 d . . . . .
H13 H 0.983249 0.182902 0.504291 0.024 Uiso 1 1 calc R . . . .
C14 C 0.81843(17) 0.37797(16) 0.54525(10) 0.0176(2) Uani 1 1 d . . . . .
H14 H 0.835267 0.454240 0.475314 0.021 Uiso 1 1 calc R . . . .
C15 C 0.39931(18) 0.93528(15) 0.68485(12) 0.0217(3) Uani 1 1 d . . . . .
H15A H 0.332112 0.909927 0.625769 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.455238 1.030242 0.650620 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.311870 0.958292 0.743218 0.033 Uiso 1 1 calc GR . . . .
O2 O 0.95041(13) 0.77029(12) 0.93200(8) 0.0226(2) Uani 1 1 d D . . . .
H2A H 1.025(2) 0.767(2) 0.8682(15) 0.043(5) Uiso 1 1 d D . . . .
H2B H 0.883(3) 0.690(3) 0.928(2) 0.080(8) Uiso 1 1 d 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
O1 0.0138(4) 0.0201(4) 0.0224(5) -0.0051(4) 0.0012(3) -0.0012(3)
N1 0.0134(5) 0.0162(5) 0.0175(5) -0.0058(4) 0.0025(4) -0.0042(4)
N2 0.0154(5) 0.0129(5) 0.0145(5) -0.0030(4) 0.0012(4) -0.0036(4)
N3 0.0219(6) 0.0260(6) 0.0165(5) -0.0014(4) -0.0027(4) -0.0073(5)
C1 0.0158(6) 0.0179(6) 0.0125(5) -0.0047(4) 0.0039(4) -0.0046(4)
C2 0.0147(5) 0.0147(5) 0.0131(5) -0.0036(4) 0.0018(4) -0.0034(4)
C3 0.0172(6) 0.0146(5) 0.0110(5) -0.0024(4) 0.0033(4) -0.0041(4)
C4 0.0130(5) 0.0167(6) 0.0137(5) -0.0050(4) 0.0010(4) -0.0045(4)
C5 0.0128(5) 0.0173(6) 0.0142(5) -0.0044(4) -0.0002(4) -0.0050(4)
C6 0.0168(6) 0.0177(6) 0.0119(5) -0.0013(4) 0.0009(4) -0.0038(4)
C7 0.0161(6) 0.0157(6) 0.0164(6) -0.0008(4) 0.0011(4) -0.0049(4)
C8 0.0176(6) 0.0134(5) 0.0174(6) -0.0028(4) 0.0001(5) -0.0055(4)
C9 0.0189(6) 0.0209(6) 0.0218(6) -0.0066(5) 0.0020(5) -0.0087(5)
C10 0.0268(6) 0.0161(6) 0.0146(6) -0.0021(4) 0.0044(5) -0.0060(5)
C11 0.0161(6) 0.0162(6) 0.0180(6) -0.0039(4) 0.0004(4) -0.0037(4)
C12 0.0157(6) 0.0195(6) 0.0255(6) -0.0099(5) 0.0011(5) -0.0024(5)
C13 0.0148(6) 0.0269(7) 0.0215(6) -0.0122(5) 0.0045(5) -0.0050(5)
C14 0.0164(6) 0.0239(6) 0.0139(5) -0.0054(5) 0.0019(4) -0.0074(5)
C15 0.0202(6) 0.0144(6) 0.0284(7) -0.0028(5) 0.0005(5) -0.0028(5)
O2 0.0228(5) 0.0225(5) 0.0219(5) -0.0048(4) -0.0005(4) -0.0044(4)
_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
O1 C1 1.2246(15) . ?
N1 C1 1.3463(15) . ?
N1 C2 1.4674(15) . ?
N1 C9 1.4511(15) . ?
N2 C1 1.4094(15) . ?
N2 C3 1.3977(15) . ?
N2 C8 1.4885(14) . ?
N3 H3 0.828(18) . ?
N3 C3 1.2624(16) . ?
C2 C3 1.5238(16) . ?
C2 C4 1.5458(16) . ?
C2 C10 1.5232(16) . ?
C4 C5 1.4218(16) . ?
C4 C11 1.3981(16) . ?
C5 C6 1.5279(16) . ?
C5 C14 1.4002(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5506(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5401(17) . ?
C8 H8 0.9800 . ?
C8 C15 1.5177(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.3873(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3799(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3862(18) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2 H2A 0.922(15) . ?
O2 H2B 0.928(16) . ?
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
C1 N1 C2 112.72(9) . . ?
C1 N1 C9 123.44(10) . . ?
C9 N1 C2 123.83(10) . . ?
C1 N2 C8 122.92(9) . . ?
C3 N2 C1 109.17(9) . . ?
C3 N2 C8 115.63(9) . . ?
C3 N3 H3 113.0(12) . . ?
O1 C1 N1 126.44(11) . . ?
O1 C1 N2 125.21(11) . . ?
N1 C1 N2 108.33(10) . . ?
N1 C2 C3 100.23(9) . . ?
N1 C2 C4 111.53(9) . . ?
N1 C2 C10 110.66(9) . . ?
C3 C2 C4 107.72(9) . . ?
C10 C2 C3 111.09(9) . . ?
C10 C2 C4 114.63(10) . . ?
N2 C3 C2 107.57(10) . . ?
N3 C3 N2 123.22(11) . . ?
N3 C3 C2 129.15(11) . . ?
C5 C4 C2 123.35(10) . . ?
C11 C4 C2 117.97(10) . . ?
C11 C4 C5 118.67(11) . . ?
C4 C5 C6 127.97(10) . . ?
C14 C5 C4 117.18(11) . . ?
C14 C5 C6 114.84(10) . . ?
C5 C6 H6A 107.9 . . ?
C5 C6 H6B 107.9 . . ?
C5 C6 C7 117.54(10) . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 H6A 107.9 . . ?
C7 C6 H6B 107.9 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.11(9) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N2 C8 C7 108.05(9) . . ?
N2 C8 H8 107.7 . . ?
N2 C8 C15 112.98(10) . . ?
C7 C8 H8 107.7 . . ?
C15 C8 C7 112.46(10) . . ?
C15 C8 H8 107.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 118.8 . . ?
C12 C11 C4 122.48(11) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.25(12) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.11(11) . . ?
C14 C13 H13 120.4 . . ?
C5 C14 H14 118.4 . . ?
C13 C14 C5 123.29(11) . . ?
C13 C14 H14 118.4 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H2A O2 H2B 97.3(19) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O2 0.828(18) 2.265(19) 3.0194(15) 151.6(16) 2_767 yes
O2 H2A O1 0.922(15) 2.017(16) 2.9071(13) 161.8(17) 1_655 yes
O2 H2B N3 0.928(16) 1.962(16) 2.8868(15) 174(2) . yes
_shelx_res_file
;
TITL testt1_a.res in P-1
testt1.res
created by SHELXL-2017/1 at 14:46:48 on 05-Sep-2018
REM Old TITL testt1 in P-1
REM SHELXT solution in P-1
REM R1 0.110, Rweak 0.005, Alpha 0.029, Orientation as input
REM Formula found by SHELXT: C14 N2 O3
CELL 0.71073 7.1405 8.577 11.9704 73.957 88.399 78.976
ZERR 2 0.0003 0.0004 0.0006 0.003 0.003 0.003
LATT 1
SFAC C H N O
UNIT 30 42 6 4
EQIV $1 2-X,1-Y,2-Z
EQIV $2 1+X,+Y,+Z
SADI 0.01 O2 H2a O2 H2b
L.S. 4 0 0
PLAN 5
TEMP 23
HTAB N3 O2_$1
HTAB O2 O1_$2
HTAB O2 N3
BOND $H
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.050800 0.237000
FVAR 1.20473
O1 4 0.166138 0.687346 0.739938 11.00000 0.01376 0.02014 =
0.02245 -0.00513 0.00117 -0.00116
N1 3 0.357340 0.429696 0.793726 11.00000 0.01342 0.01618 =
0.01746 -0.00580 0.00254 -0.00422
N2 3 0.479485 0.643416 0.810866 11.00000 0.01545 0.01293 =
0.01451 -0.00298 0.00120 -0.00359
N3 3 0.764855 0.506857 0.914161 11.00000 0.02195 0.02603 =
0.01650 -0.00135 -0.00269 -0.00727
H3 2 0.834540 0.414875 0.938191 11.00000 0.03281
C1 1 0.317724 0.594648 0.776385 11.00000 0.01583 0.01788 =
0.01249 -0.00473 0.00394 -0.00462
C2 1 0.555193 0.356217 0.833762 11.00000 0.01474 0.01470 =
0.01305 -0.00356 0.00179 -0.00343
C3 1 0.616429 0.502748 0.861012 11.00000 0.01719 0.01463 =
0.01103 -0.00236 0.00326 -0.00413
C4 1 0.679729 0.314518 0.734342 11.00000 0.01296 0.01675 =
0.01368 -0.00505 0.00098 -0.00453
C5 1 0.702116 0.433520 0.627965 11.00000 0.01276 0.01730 =
0.01418 -0.00445 -0.00025 -0.00499
C6 1 0.611649 0.617096 0.590560 11.00000 0.01677 0.01772 =
0.01189 -0.00125 0.00089 -0.00382
AFIX 23
H6A 2 0.475909 0.627163 0.604302 11.00000 -1.20000
H6B 2 0.626266 0.657743 0.507342 11.00000 -1.20000
AFIX 0
C7 1 0.689014 0.732567 0.649636 11.00000 0.01611 0.01568 =
0.01641 -0.00085 0.00111 -0.00487
AFIX 23
H7A 2 0.811085 0.675490 0.687477 11.00000 -1.20000
H7B 2 0.710875 0.829581 0.590051 11.00000 -1.20000
AFIX 0
C8 1 0.555359 0.788848 0.740115 11.00000 0.01757 0.01343 =
0.01741 -0.00284 0.00008 -0.00551
AFIX 13
H8 2 0.632486 0.823293 0.792077 11.00000 -1.20000
AFIX 0
C9 1 0.217689 0.334885 0.777125 11.00000 0.01894 0.02088 =
0.02175 -0.00662 0.00201 -0.00873
AFIX 137
H9A 2 0.098845 0.408317 0.749669 11.00000 -1.50000
H9B 2 0.199113 0.257490 0.849708 11.00000 -1.50000
H9C 2 0.262720 0.276122 0.721015 11.00000 -1.50000
AFIX 0
C10 1 0.561414 0.212610 0.942959 11.00000 0.02684 0.01606 =
0.01465 -0.00206 0.00444 -0.00600
AFIX 137
H10A 2 0.479645 0.248063 0.999856 11.00000 -1.50000
H10B 2 0.689873 0.175970 0.973884 11.00000 -1.50000
H10C 2 0.518644 0.123288 0.923958 11.00000 -1.50000
AFIX 0
C11 1 0.777107 0.151721 0.751201 11.00000 0.01607 0.01623 =
0.01801 -0.00391 0.00036 -0.00370
AFIX 43
H11 2 0.765726 0.074502 0.821678 11.00000 -1.20000
AFIX 0
C12 1 0.890072 0.101029 0.666759 11.00000 0.01573 0.01948 =
0.02548 -0.00993 0.00110 -0.00241
AFIX 43
H12 2 0.951848 -0.008519 0.680349 11.00000 -1.20000
AFIX 0
C13 1 0.909730 0.215000 0.562373 11.00000 0.01484 0.02695 =
0.02148 -0.01222 0.00452 -0.00496
AFIX 43
H13 2 0.983249 0.182902 0.504291 11.00000 -1.20000
AFIX 0
C14 1 0.818427 0.377974 0.545246 11.00000 0.01643 0.02388 =
0.01387 -0.00544 0.00194 -0.00739
AFIX 43
H14 2 0.835267 0.454240 0.475314 11.00000 -1.20000
AFIX 0
C15 1 0.399309 0.935279 0.684854 11.00000 0.02023 0.01435 =
0.02839 -0.00279 0.00046 -0.00280
AFIX 137
H15A 2 0.332112 0.909927 0.625769 11.00000 -1.50000
H15B 2 0.455238 1.030242 0.650620 11.00000 -1.50000
H15C 2 0.311870 0.958292 0.743218 11.00000 -1.50000
AFIX 0
O2 4 0.950414 0.770294 0.931995 11.00000 0.02277 0.02250 =
0.02188 -0.00483 -0.00048 -0.00442
H2A 2 1.024636 0.766819 0.868171 11.00000 0.04341
H2B 2 0.882834 0.689679 0.927857 11.00000 0.08020
HKLF 4
REM testt1_a.res in P-1
REM R1 = 0.0395 for 2810 Fo > 4sig(Fo) and 0.0471 for all 3308 data
REM 196 parameters refined using 1 restraints
END
WGHT 0.0508 0.2370
REM Highest difference peak 0.415, deepest hole -0.227, 1-sigma level 0.045
Q1 1 0.9129 -0.0242 1.0459 11.00000 0.05 0.41
Q2 1 0.5944 0.4248 0.8474 11.00000 0.05 0.35
Q3 1 0.6206 0.3419 0.7833 11.00000 0.05 0.33
Q4 1 0.7473 0.4026 0.5845 11.00000 0.05 0.33
Q5 1 0.7199 0.2349 0.7328 11.00000 0.05 0.31
;
_shelx_res_checksum 11661
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
#######################################################################
#
# 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_testt1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1993731'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C17 H21 N3 O'
_chemical_formula_sum 'C17 H21 N3 O'
_chemical_formula_weight 283.37
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.0488(2)
_cell_length_b 8.6329(3)
_cell_length_c 12.6463(5)
_cell_angle_alpha 88.989(2)
_cell_angle_beta 74.751(2)
_cell_angle_gamma 77.777(2)
_cell_volume 725.03(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5830
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.09
_cell_measurement_theta_min 2.42
_shelx_estimated_absorpt_T_max 0.974
_shelx_estimated_absorpt_T_min 0.965
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6845
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0487 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.9181. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.298
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 304
_exptl_crystal_size_max 0.428
_exptl_crystal_size_mid 0.329
_exptl_crystal_size_min 0.322
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0223
_diffrn_reflns_av_unetI/netI 0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 13480
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.115
_diffrn_reflns_theta_min 1.670
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device 'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3130
_reflns_number_total 3531
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.331
_refine_diff_density_min -0.222
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 194
_refine_ls_number_reflns 3531
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0433
_refine_ls_R_factor_gt 0.0378
_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^)+(0.0422P)^2^+0.3184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0899
_refine_ls_wR_factor_ref 0.0940
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,
H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.12507(11) 0.12693(9) 0.71185(7) 0.01657(17) Uani 1 1 d . . . . .
N1 N 0.41384(13) 0.22290(10) 0.64479(7) 0.01133(18) Uani 1 1 d . . . . .
N2 N 0.38359(13) 0.08916(10) 0.79757(7) 0.01189(18) Uani 1 1 d . . . . .
N3 N 0.69614(14) 0.07318(11) 0.83444(8) 0.01488(19) Uani 1 1 d . . . . .
C1 C 0.29027(15) 0.14514(12) 0.71581(8) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.59986(14) 0.22295(12) 0.67559(8) 0.0104(2) Uani 1 1 d . . . . .
C3 C 0.57521(15) 0.12120(12) 0.77671(8) 0.0112(2) Uani 1 1 d . . . . .
C4 C 0.38437(16) 0.28672(13) 0.54192(9) 0.0147(2) Uani 1 1 d . . . . .
H4A H 0.372270 0.403050 0.544287 0.018 Uiso 1 1 calc R . . . .
H4B H 0.258093 0.265429 0.530986 0.018 Uiso 1 1 calc R . . . .
C5 C 0.56136(16) 0.21095(14) 0.44673(9) 0.0163(2) Uani 1 1 d . . . . .
H5A H 0.552577 0.269020 0.379375 0.020 Uiso 1 1 calc R . . . .
H5B H 0.554144 0.099874 0.433671 0.020 Uiso 1 1 calc R . . . .
C6 C 0.76227(16) 0.21353(13) 0.47038(9) 0.0149(2) Uani 1 1 d . . . . .
H6A H 0.778524 0.324507 0.472144 0.018 Uiso 1 1 calc R . . . .
H6B H 0.873512 0.154175 0.410637 0.018 Uiso 1 1 calc R . . . .
C7 C 0.77493(15) 0.13952(12) 0.58015(8) 0.0123(2) Uani 1 1 d . . . . .
H7A H 0.904266 0.147279 0.594335 0.015 Uiso 1 1 calc R . . . .
H7B H 0.771875 0.025718 0.575863 0.015 Uiso 1 1 calc R . . . .
C8 C 0.61186(15) 0.38974(12) 0.71246(8) 0.0116(2) Uani 1 1 d . . . . .
C9 C 0.79066(16) 0.44193(13) 0.67156(9) 0.0154(2) Uani 1 1 d . . . . .
H9 H 0.897178 0.377409 0.617924 0.018 Uiso 1 1 calc R . . . .
C10 C 0.81784(17) 0.58534(13) 0.70683(10) 0.0180(2) Uani 1 1 d . . . . .
H10 H 0.941464 0.617469 0.677512 0.022 Uiso 1 1 calc R . . . .
C11 C 0.66433(18) 0.68114(13) 0.78474(9) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.680970 0.779471 0.809416 0.021 Uiso 1 1 calc R . . . .
C12 C 0.48606(17) 0.63102(13) 0.82605(9) 0.0164(2) Uani 1 1 d . . . . .
H12 H 0.380759 0.697163 0.879367 0.020 Uiso 1 1 calc R . . . .
C13 C 0.45428(16) 0.48711(12) 0.79266(8) 0.0128(2) Uani 1 1 d . . . . .
C14 C 0.25326(16) 0.44768(12) 0.85048(9) 0.0142(2) Uani 1 1 d . . . . .
H14A H 0.211356 0.386390 0.798494 0.017 Uiso 1 1 calc R . . . .
H14B H 0.151043 0.547850 0.871038 0.017 Uiso 1 1 calc R . . . .
C15 C 0.25629(16) 0.35088(13) 0.95532(9) 0.0161(2) Uani 1 1 d . . . . .
H15A H 0.398017 0.304607 0.953953 0.019 Uiso 1 1 calc R . . . .
H15B H 0.198133 0.424408 1.020460 0.019 Uiso 1 1 calc R . . . .
C16 C 0.14021(16) 0.21636(13) 0.96814(9) 0.0170(2) Uani 1 1 d . . . . .
H16A H 0.093374 0.196429 1.047094 0.020 Uiso 1 1 calc R . . . .
H16B H 0.019715 0.251199 0.940378 0.020 Uiso 1 1 calc R . . . .
C17 C 0.26576(16) 0.06065(13) 0.90710(9) 0.0150(2) Uani 1 1 d . . . . .
H17A H 0.357737 0.006185 0.949852 0.018 Uiso 1 1 calc R . . . .
H17B H 0.174974 -0.009825 0.900682 0.018 Uiso 1 1 calc R . . . .
H3 H 0.813(3) 0.1051(19) 0.8065(14) 0.032(4) Uiso 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
O1 0.0107(3) 0.0213(4) 0.0190(4) 0.0000(3) -0.0045(3) -0.0051(3)
N1 0.0092(4) 0.0143(4) 0.0110(4) 0.0015(3) -0.0035(3) -0.0026(3)
N2 0.0105(4) 0.0138(4) 0.0118(4) 0.0017(3) -0.0024(3) -0.0043(3)
N3 0.0131(4) 0.0170(4) 0.0159(4) 0.0034(3) -0.0052(3) -0.0045(3)
C1 0.0110(4) 0.0115(4) 0.0123(5) -0.0022(4) -0.0020(4) -0.0012(4)
C2 0.0091(4) 0.0115(4) 0.0110(5) 0.0011(4) -0.0031(4) -0.0024(3)
C3 0.0118(4) 0.0097(4) 0.0113(5) -0.0010(4) -0.0013(4) -0.0029(4)
C4 0.0134(5) 0.0179(5) 0.0127(5) 0.0028(4) -0.0050(4) -0.0014(4)
C5 0.0169(5) 0.0207(5) 0.0108(5) 0.0015(4) -0.0034(4) -0.0031(4)
C6 0.0139(5) 0.0162(5) 0.0123(5) 0.0015(4) -0.0005(4) -0.0021(4)
C7 0.0103(4) 0.0125(4) 0.0130(5) 0.0005(4) -0.0019(4) -0.0015(4)
C8 0.0130(5) 0.0110(4) 0.0121(5) 0.0024(4) -0.0051(4) -0.0031(4)
C9 0.0139(5) 0.0156(5) 0.0167(5) 0.0023(4) -0.0036(4) -0.0040(4)
C10 0.0182(5) 0.0183(5) 0.0215(6) 0.0058(4) -0.0081(4) -0.0092(4)
C11 0.0264(6) 0.0137(5) 0.0179(5) 0.0029(4) -0.0112(4) -0.0077(4)
C12 0.0218(5) 0.0138(5) 0.0135(5) 0.0003(4) -0.0053(4) -0.0024(4)
C13 0.0144(5) 0.0129(5) 0.0116(5) 0.0025(4) -0.0045(4) -0.0026(4)
C14 0.0134(5) 0.0137(5) 0.0136(5) -0.0018(4) -0.0013(4) -0.0012(4)
C15 0.0171(5) 0.0183(5) 0.0119(5) -0.0006(4) -0.0009(4) -0.0051(4)
C16 0.0156(5) 0.0196(5) 0.0138(5) 0.0008(4) 0.0005(4) -0.0051(4)
C17 0.0149(5) 0.0166(5) 0.0131(5) 0.0035(4) -0.0011(4) -0.0061(4)
_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
O1 C1 1.2214(13) . ?
N1 C1 1.3531(13) . ?
N1 C2 1.4628(12) . ?
N1 C4 1.4517(13) . ?
N2 C1 1.3931(13) . ?
N2 C3 1.3923(13) . ?
N2 C17 1.4623(13) . ?
N3 C3 1.2644(14) . ?
N3 H3 0.907(17) . ?
C2 C3 1.5314(14) . ?
C2 C7 1.5392(14) . ?
C2 C8 1.5472(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5251(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5270(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5340(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3958(14) . ?
C8 C13 1.4182(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3904(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3837(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3842(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3992(15) . ?
C13 C14 1.5194(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5572(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5396(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5362(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
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
C1 N1 C2 112.67(8) . . ?
C1 N1 C4 126.06(9) . . ?
C4 N1 C2 120.95(8) . . ?
C1 N2 C17 121.12(8) . . ?
C3 N2 C1 111.51(8) . . ?
C3 N2 C17 123.26(9) . . ?
C3 N3 H3 110.1(10) . . ?
O1 C1 N1 127.40(10) . . ?
O1 C1 N2 124.85(10) . . ?
N1 C1 N2 107.74(9) . . ?
N1 C2 C3 101.41(8) . . ?
N1 C2 C7 106.86(8) . . ?
N1 C2 C8 112.67(8) . . ?
C3 C2 C7 111.28(8) . . ?
C3 C2 C8 107.68(8) . . ?
C7 C2 C8 116.01(8) . . ?
N2 C3 C2 106.34(8) . . ?
N3 C3 N2 123.87(9) . . ?
N3 C3 C2 129.78(9) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
N1 C4 C5 110.16(8) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.35(9) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.48(8) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C2 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 C2 111.56(8) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C2 118.79(9) . . ?
C9 C8 C13 118.34(9) . . ?
C13 C8 C2 122.68(9) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.10(10) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.82(10) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.76(10) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 118.6 . . ?
C11 C12 C13 122.83(10) . . ?
C13 C12 H12 118.6 . . ?
C8 C13 C14 126.12(9) . . ?
C12 C13 C8 118.16(10) . . ?
C12 C13 C14 115.68(9) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.05(9) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.48(9) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.50(9) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
N2 C17 C16 111.45(9) . . ?
N2 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
_shelx_res_file
;
TITL testt1_a.res in P-1
testt1.res
created by SHELXL-2017/1 at 14:16:24 on 08-Oct-2019
REM Old TITL testt1 in P-1
REM SHELXT solution in P-1
REM R1 0.107, Rweak 0.005, Alpha 0.033, Orientation as input
REM Formula found by SHELXT: C17 N2 O2
CELL 0.71073 7.0488 8.6329 12.6463 88.989 74.751 77.777
ZERR 2 0.0002 0.0003 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H N O
UNIT 34 42 6 2
L.S. 4
PLAN 5
SIZE 0.322 0.329 0.428
TEMP -173(2)
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.042200 0.318400
FVAR 1.07537
O1 4 0.125067 0.126925 0.711851 11.00000 0.01065 0.02125 =
0.01897 -0.00005 -0.00451 -0.00515
N1 3 0.413842 0.222902 0.644787 11.00000 0.00917 0.01435 =
0.01096 0.00146 -0.00352 -0.00260
N2 3 0.383589 0.089164 0.797568 11.00000 0.01046 0.01385 =
0.01178 0.00166 -0.00240 -0.00428
N3 3 0.696142 0.073180 0.834437 11.00000 0.01311 0.01697 =
0.01589 0.00338 -0.00525 -0.00453
C1 1 0.290267 0.145143 0.715813 11.00000 0.01102 0.01153 =
0.01229 -0.00220 -0.00197 -0.00123
C2 1 0.599861 0.222949 0.675589 11.00000 0.00905 0.01149 =
0.01097 0.00106 -0.00305 -0.00243
C3 1 0.575206 0.121201 0.776707 11.00000 0.01179 0.00973 =
0.01134 -0.00096 -0.00127 -0.00286
C4 1 0.384369 0.286724 0.541919 11.00000 0.01339 0.01786 =
0.01271 0.00280 -0.00503 -0.00136
AFIX 23
H4A 2 0.372270 0.403050 0.544287 11.00000 -1.20000
H4B 2 0.258093 0.265429 0.530986 11.00000 -1.20000
AFIX 0
C5 1 0.561363 0.210954 0.446726 11.00000 0.01685 0.02072 =
0.01081 0.00147 -0.00338 -0.00306
AFIX 23
H5A 2 0.552577 0.269020 0.379375 11.00000 -1.20000
H5B 2 0.554144 0.099874 0.433671 11.00000 -1.20000
AFIX 0
C6 1 0.762268 0.213529 0.470379 11.00000 0.01389 0.01622 =
0.01226 0.00153 -0.00051 -0.00212
AFIX 23
H6A 2 0.778524 0.324507 0.472144 11.00000 -1.20000
H6B 2 0.873512 0.154175 0.410637 11.00000 -1.20000
AFIX 0
C7 1 0.774928 0.139524 0.580153 11.00000 0.01027 0.01253 =
0.01298 0.00050 -0.00193 -0.00154
AFIX 23
H7A 2 0.904266 0.147279 0.594335 11.00000 -1.20000
H7B 2 0.771875 0.025718 0.575863 11.00000 -1.20000
AFIX 0
C8 1 0.611863 0.389741 0.712457 11.00000 0.01301 0.01098 =
0.01208 0.00241 -0.00507 -0.00314
C9 1 0.790657 0.441931 0.671564 11.00000 0.01389 0.01561 =
0.01669 0.00226 -0.00358 -0.00404
AFIX 43
H9 2 0.897178 0.377409 0.617924 11.00000 -1.20000
AFIX 0
C10 1 0.817838 0.585343 0.706829 11.00000 0.01817 0.01832 =
0.02153 0.00585 -0.00813 -0.00922
AFIX 43
H10 2 0.941464 0.617469 0.677512 11.00000 -1.20000
AFIX 0
C11 1 0.664330 0.681140 0.784739 11.00000 0.02637 0.01372 =
0.01789 0.00295 -0.01116 -0.00772
AFIX 43
H11 2 0.680970 0.779471 0.809416 11.00000 -1.20000
AFIX 0
C12 1 0.486061 0.631015 0.826051 11.00000 0.02179 0.01380 =
0.01349 0.00026 -0.00534 -0.00243
AFIX 43
H12 2 0.380759 0.697163 0.879367 11.00000 -1.20000
AFIX 0
C13 1 0.454283 0.487114 0.792663 11.00000 0.01440 0.01290 =
0.01160 0.00247 -0.00451 -0.00264
C14 1 0.253264 0.447681 0.850482 11.00000 0.01342 0.01370 =
0.01359 -0.00182 -0.00131 -0.00118
AFIX 23
H14A 2 0.211356 0.386390 0.798494 11.00000 -1.20000
H14B 2 0.151043 0.547850 0.871038 11.00000 -1.20000
AFIX 0
C15 1 0.256286 0.350883 0.955325 11.00000 0.01710 0.01830 =
0.01185 -0.00064 -0.00091 -0.00508
AFIX 23
H15A 2 0.398017 0.304607 0.953953 11.00000 -1.20000
H15B 2 0.198133 0.424408 1.020460 11.00000 -1.20000
AFIX 0
C16 1 0.140210 0.216363 0.968142 11.00000 0.01560 0.01962 =
0.01383 0.00083 0.00051 -0.00511
AFIX 23
H16A 2 0.093374 0.196429 1.047094 11.00000 -1.20000
H16B 2 0.019715 0.251199 0.940378 11.00000 -1.20000
AFIX 0
C17 1 0.265760 0.060647 0.907096 11.00000 0.01490 0.01664 =
0.01314 0.00353 -0.00110 -0.00612
AFIX 23
H17A 2 0.357737 0.006185 0.949852 11.00000 -1.20000
H17B 2 0.174974 -0.009825 0.900682 11.00000 -1.20000
AFIX 0
H3 2 0.813321 0.105095 0.806462 11.00000 0.03164
HKLF 4
REM testt1_a.res in P-1
REM R1 = 0.0378 for 3130 Fo > 4sig(Fo) and 0.0433 for all 3531 data
REM 194 parameters refined using 0 restraints
END
WGHT 0.0422 0.3183
REM Highest difference peak 0.331, deepest hole -0.222, 1-sigma level 0.045
Q1 1 0.5929 0.1706 0.7250 11.00000 0.05 0.33
Q2 1 0.5989 0.3098 0.6986 11.00000 0.05 0.33
Q3 1 0.3617 0.4664 0.8231 11.00000 0.05 0.32
Q4 1 0.4713 0.2468 0.4959 11.00000 0.05 0.31
Q5 1 0.2023 0.2797 0.9549 11.00000 0.05 0.31
;
_shelx_res_checksum 65439
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
#######################################################################
#
# 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_testt1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1993730'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2020-02-18
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C16 H19 N3 O'
_chemical_formula_sum 'C16 H19 N3 O'
_chemical_formula_weight 269.34
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.9675(12)
_cell_length_b 8.6877(14)
_cell_length_c 12.0676(19)
_cell_angle_alpha 87.020(11)
_cell_angle_beta 74.121(11)
_cell_angle_gamma 77.399(12)
_cell_volume 685.7(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1931
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 25.23
_cell_measurement_theta_min 2.96
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.084
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.5989
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0990 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8032.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.305
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 288
_exptl_crystal_size_max 0.352
_exptl_crystal_size_mid 0.352
_exptl_crystal_size_min 0.185
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0625
_diffrn_reflns_av_unetI/netI 0.0578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 12669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.187
_diffrn_reflns_theta_min 2.402
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_current 30.0
_diffrn_source_power 1.35
_diffrn_source_voltage 45.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2293
_reflns_number_total 3290
_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 'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.226
_refine_diff_density_min -0.243
_refine_diff_density_rms 0.048
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 185
_refine_ls_number_reflns 3290
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0735
_refine_ls_R_factor_gt 0.0466
_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^)+(0.0463P)^2^+0.0656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1020
_refine_ls_wR_factor_ref 0.1140
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B),
C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.15533(17) 0.11992(13) 0.68181(10) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.43144(19) 0.23999(14) 0.62269(11) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.39649(19) 0.09957(15) 0.78475(11) 0.0229(3) Uani 1 1 d . . . . .
N3 N 0.7100(2) 0.07936(16) 0.82717(13) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.3117(2) 0.15051(17) 0.69371(14) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.6189(2) 0.23632(17) 0.65905(13) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.5911(2) 0.13084(17) 0.76450(13) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.4692(3) 0.2403(2) 0.49647(14) 0.0296(4) Uani 1 1 d . . . . .
H4A H 0.386310 0.335663 0.470635 0.035 Uiso 1 1 calc R U . . .
H4B H 0.437845 0.145465 0.469296 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6973(3) 0.2398(2) 0.45293(14) 0.0319(4) Uani 1 1 d . . . . .
H5A H 0.760574 0.176997 0.381006 0.038 Uiso 1 1 calc R U . . .
H5B H 0.720265 0.348423 0.438635 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7835(2) 0.16382(19) 0.55121(14) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.916189 0.190785 0.547096 0.032 Uiso 1 1 calc R U . . .
H6B H 0.801395 0.047649 0.549848 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6309(2) 0.39953(17) 0.69842(13) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.8142(2) 0.45045(18) 0.65898(14) 0.0264(4) Uani 1 1 d . . . . .
H8 H 0.926376 0.385801 0.606454 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8368(3) 0.59366(19) 0.69471(15) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.963505 0.625373 0.666970 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6759(3) 0.68918(19) 0.77006(15) 0.0331(4) Uani 1 1 d . . . . .
H10 H 0.689561 0.787772 0.794001 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4939(3) 0.63966(19) 0.81050(15) 0.0311(4) Uani 1 1 d . . . . .
H11 H 0.383118 0.706403 0.862438 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4656(2) 0.49581(18) 0.77840(13) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.2618(2) 0.45395(18) 0.83738(14) 0.0267(4) Uani 1 1 d . . . . .
H13A H 0.222858 0.394545 0.782166 0.032 Uiso 1 1 calc R U . . .
H13B H 0.157054 0.552751 0.857490 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2598(3) 0.3543(2) 0.94839(14) 0.0307(4) Uani 1 1 d . . . . .
H14A H 0.402588 0.307679 0.948720 0.037 Uiso 1 1 calc R U . . .
H14B H 0.198381 0.425502 1.016160 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1421(3) 0.2209(2) 0.96143(15) 0.0336(4) Uani 1 1 d . . . . .
H15A H 0.091705 0.198483 1.044365 0.040 Uiso 1 1 calc R U . . .
H15B H 0.021803 0.256971 0.930843 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2713(3) 0.06766(19) 0.89881(14) 0.0298(4) Uani 1 1 d . . . . .
H16A H 0.361024 0.011001 0.945484 0.036 Uiso 1 1 calc R U . . .
H16B H 0.179935 -0.001245 0.890599 0.036 Uiso 1 1 calc R U . . .
H3 H 0.835(3) 0.112(2) 0.7968(17) 0.048(6) Uiso 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
O1 0.0226(6) 0.0347(7) 0.0418(7) -0.0020(5) -0.0119(5) -0.0101(5)
N1 0.0206(7) 0.0232(6) 0.0234(7) -0.0002(5) -0.0093(5) -0.0050(5)
N2 0.0197(7) 0.0231(6) 0.0269(7) 0.0029(5) -0.0061(5) -0.0072(5)
N3 0.0277(8) 0.0295(8) 0.0365(8) 0.0074(6) -0.0158(7) -0.0090(6)
C1 0.0194(8) 0.0202(7) 0.0302(9) -0.0033(6) -0.0077(7) -0.0029(6)
C2 0.0175(7) 0.0213(7) 0.0249(8) 0.0004(6) -0.0079(6) -0.0043(6)
C3 0.0213(8) 0.0177(7) 0.0267(8) -0.0011(6) -0.0068(6) -0.0054(6)
C4 0.0344(10) 0.0329(9) 0.0250(9) 0.0010(7) -0.0121(7) -0.0097(7)
C5 0.0346(10) 0.0359(9) 0.0250(9) -0.0033(7) -0.0041(7) -0.0113(8)
C6 0.0221(8) 0.0261(8) 0.0303(9) -0.0056(7) -0.0039(7) -0.0054(6)
C7 0.0237(8) 0.0185(7) 0.0227(8) 0.0040(6) -0.0101(6) -0.0049(6)
C8 0.0262(9) 0.0255(8) 0.0289(9) 0.0044(6) -0.0087(7) -0.0081(7)
C9 0.0346(10) 0.0320(9) 0.0381(10) 0.0089(8) -0.0182(8) -0.0175(8)
C10 0.0494(12) 0.0217(8) 0.0356(10) 0.0021(7) -0.0190(9) -0.0142(8)
C11 0.0399(10) 0.0227(8) 0.0316(9) -0.0033(7) -0.0119(8) -0.0048(7)
C12 0.0256(8) 0.0216(7) 0.0243(8) 0.0022(6) -0.0090(7) -0.0047(6)
C13 0.0255(9) 0.0234(8) 0.0283(9) -0.0043(6) -0.0036(7) -0.0024(6)
C14 0.0300(9) 0.0330(9) 0.0268(9) -0.0044(7) -0.0021(7) -0.0080(7)
C15 0.0298(9) 0.0371(10) 0.0313(10) 0.0039(7) -0.0013(7) -0.0114(8)
C16 0.0283(9) 0.0298(9) 0.0318(9) 0.0074(7) -0.0056(7) -0.0122(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
O1 C1 1.2224(18) . ?
N1 C1 1.363(2) . ?
N1 C2 1.4813(19) . ?
N1 C4 1.473(2) . ?
N2 C1 1.3937(19) . ?
N2 C3 1.3945(19) . ?
N2 C16 1.463(2) . ?
N3 C3 1.2665(19) . ?
N3 H3 0.95(2) . ?
C2 C3 1.522(2) . ?
C2 C6 1.536(2) . ?
C2 C7 1.545(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.395(2) . ?
C7 C12 1.419(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(2) . ?
C12 C13 1.516(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.555(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.538(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.537(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
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
C1 N1 C2 110.83(12) . . ?
C1 N1 C4 123.26(13) . . ?
C4 N1 C2 112.53(12) . . ?
C1 N2 C3 111.29(13) . . ?
C1 N2 C16 122.00(13) . . ?
C3 N2 C16 123.84(13) . . ?
C3 N3 H3 109.5(12) . . ?
O1 C1 N1 126.76(15) . . ?
O1 C1 N2 124.93(15) . . ?
N1 C1 N2 108.31(13) . . ?
N1 C2 C3 102.37(12) . . ?
N1 C2 C6 100.63(12) . . ?
N1 C2 C7 112.80(11) . . ?
C3 C2 C6 115.73(12) . . ?
C3 C2 C7 107.64(12) . . ?
C6 C2 C7 116.67(13) . . ?
N2 C3 C2 106.15(12) . . ?
N3 C3 N2 123.52(14) . . ?
N3 C3 C2 130.31(14) . . ?
N1 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
N1 C4 C5 103.32(12) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 C4 103.65(13) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C2 C6 H6A 111.2 . . ?
C2 C6 H6B 111.2 . . ?
C5 C6 C2 102.86(13) . . ?
C5 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C2 118.90(14) . . ?
C8 C7 C12 118.68(14) . . ?
C12 C7 C2 122.32(14) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.60(16) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.03(16) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.97(15) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 118.5 . . ?
C10 C11 C12 122.90(16) . . ?
C12 C11 H11 118.5 . . ?
C7 C12 C13 125.97(14) . . ?
C11 C12 C7 117.78(15) . . ?
C11 C12 C13 116.19(14) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.49(13) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.59(13) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.43(14) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N2 C16 C15 111.45(13) . . ?
N2 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
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
N1 C2 C3 N2 -5.65(14) . . . . ?
N1 C2 C3 N3 175.67(15) . . . . ?
N1 C2 C6 C5 38.19(14) . . . . ?
N1 C2 C7 C8 -134.56(14) . . . . ?
N1 C2 C7 C12 49.08(18) . . . . ?
N1 C4 C5 C6 25.49(16) . . . . ?
C1 N1 C2 C3 -0.49(15) . . . . ?
C1 N1 C2 C6 119.08(13) . . . . ?
C1 N1 C2 C7 -115.88(14) . . . . ?
C1 N1 C4 C5 -138.15(14) . . . . ?
C1 N2 C3 N3 -171.15(14) . . . . ?
C1 N2 C3 C2 10.06(16) . . . . ?
C1 N2 C16 C15 -71.49(18) . . . . ?
C2 N1 C1 O1 -174.09(14) . . . . ?
C2 N1 C1 N2 6.52(16) . . . . ?
C2 N1 C4 C5 -1.06(16) . . . . ?
C2 C7 C8 C9 -177.59(14) . . . . ?
C2 C7 C12 C11 178.42(13) . . . . ?
C2 C7 C12 C13 1.5(2) . . . . ?
C3 N2 C1 O1 169.99(14) . . . . ?
C3 N2 C1 N1 -10.61(16) . . . . ?
C3 N2 C16 C15 87.65(18) . . . . ?
C3 C2 C6 C5 147.60(13) . . . . ?
C3 C2 C7 C8 113.26(15) . . . . ?
C3 C2 C7 C12 -63.10(17) . . . . ?
C4 N1 C1 O1 -36.4(2) . . . . ?
C4 N1 C1 N2 144.23(14) . . . . ?
C4 N1 C2 C3 -142.97(12) . . . . ?
C4 N1 C2 C6 -23.40(15) . . . . ?
C4 N1 C2 C7 101.65(14) . . . . ?
C4 C5 C6 C2 -40.24(15) . . . . ?
C6 C2 C3 N2 -114.03(14) . . . . ?
C6 C2 C3 N3 67.3(2) . . . . ?
C6 C2 C7 C8 -18.77(19) . . . . ?
C6 C2 C7 C12 164.87(14) . . . . ?
C7 C2 C3 N2 113.43(13) . . . . ?
C7 C2 C3 N3 -65.3(2) . . . . ?
C7 C2 C6 C5 -84.18(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C7 C12 C13 C14 84.78(19) . . . . ?
C8 C7 C12 C11 2.0(2) . . . . ?
C8 C7 C12 C13 -174.92(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 -1.6(2) . . . . ?
C10 C11 C12 C13 175.63(15) . . . . ?
C11 C12 C13 C14 -92.23(17) . . . . ?
C12 C7 C8 C9 -1.1(2) . . . . ?
C12 C13 C14 C15 -138.81(14) . . . . ?
C13 C14 C15 C16 85.39(18) . . . . ?
C14 C15 C16 N2 -42.42(19) . . . . ?
C16 N2 C1 O1 -28.5(2) . . . . ?
C16 N2 C1 N1 150.88(13) . . . . ?
C16 N2 C3 N3 27.8(2) . . . . ?
C16 N2 C3 C2 -151.03(13) . . . . ?
_shelx_res_file
;
TITL testt1_a.res in P-1
testt1.res
created by SHELXL-2017/1 at 10:34:52 on 18-Feb-2020
REM Old TITL testt1 in P-1
REM SHELXT solution in P-1
REM R1 0.136, Rweak 0.008, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C16 N2 O2
CELL 0.71073 6.9675 8.6877 12.0676 87.02 74.121 77.399
ZERR 2 0.0012 0.0014 0.0019 0.011 0.011 0.012
LATT 1
SFAC C H N O
UNIT 32 38 6 2
L.S. 4
PLAN 5
TEMP -173.12
CONF
BOND $H
list 4
fmap 2 53
MORE -1
ACTA
REM
REM
REM
WGHT 0.046300 0.065600
FVAR 1.11910
O1 4 0.155328 0.119915 0.681809 11.00000 0.02260 0.03470 =
0.04179 -0.00202 -0.01192 -0.01010
N1 3 0.431444 0.239991 0.622686 11.00000 0.02058 0.02323 =
0.02341 -0.00018 -0.00927 -0.00501
N2 3 0.396492 0.099567 0.784749 11.00000 0.01967 0.02311 =
0.02691 0.00294 -0.00615 -0.00716
N3 3 0.709993 0.079361 0.827168 11.00000 0.02775 0.02954 =
0.03650 0.00744 -0.01584 -0.00902
C1 1 0.311695 0.150505 0.693709 11.00000 0.01943 0.02016 =
0.03017 -0.00332 -0.00767 -0.00291
C2 1 0.618941 0.236318 0.659053 11.00000 0.01745 0.02127 =
0.02493 0.00043 -0.00794 -0.00427
C3 1 0.591104 0.130839 0.764504 11.00000 0.02126 0.01765 =
0.02675 -0.00111 -0.00681 -0.00536
C4 1 0.469219 0.240305 0.496469 11.00000 0.03438 0.03295 =
0.02502 0.00102 -0.01211 -0.00970
AFIX 23
H4A 2 0.386310 0.335663 0.470635 11.00000 -1.20000
H4B 2 0.437845 0.145465 0.469296 11.00000 -1.20000
AFIX 0
C5 1 0.697324 0.239774 0.452933 11.00000 0.03455 0.03589 =
0.02500 -0.00332 -0.00409 -0.01127
AFIX 23
H5A 2 0.760574 0.176997 0.381006 11.00000 -1.20000
H5B 2 0.720265 0.348423 0.438635 11.00000 -1.20000
AFIX 0
C6 1 0.783511 0.163818 0.551210 11.00000 0.02209 0.02608 =
0.03025 -0.00560 -0.00387 -0.00543
AFIX 23
H6A 2 0.916189 0.190785 0.547096 11.00000 -1.20000
H6B 2 0.801395 0.047649 0.549848 11.00000 -1.20000
AFIX 0
C7 1 0.630864 0.399531 0.698416 11.00000 0.02373 0.01845 =
0.02271 0.00405 -0.01007 -0.00488
C8 1 0.814200 0.450452 0.658979 11.00000 0.02620 0.02553 =
0.02890 0.00438 -0.00868 -0.00810
AFIX 43
H8 2 0.926376 0.385801 0.606454 11.00000 -1.20000
AFIX 0
C9 1 0.836769 0.593662 0.694709 11.00000 0.03465 0.03203 =
0.03811 0.00892 -0.01820 -0.01752
AFIX 43
H9 2 0.963505 0.625373 0.666970 11.00000 -1.20000
AFIX 0
C10 1 0.675893 0.689184 0.770063 11.00000 0.04939 0.02175 =
0.03563 0.00207 -0.01901 -0.01425
AFIX 43
H10 2 0.689561 0.787772 0.794001 11.00000 -1.20000
AFIX 0
C11 1 0.493887 0.639660 0.810502 11.00000 0.03995 0.02267 =
0.03159 -0.00332 -0.01185 -0.00476
AFIX 43
H11 2 0.383118 0.706403 0.862438 11.00000 -1.20000
AFIX 0
C12 1 0.465563 0.495811 0.778400 11.00000 0.02560 0.02161 =
0.02425 0.00218 -0.00903 -0.00471
C13 1 0.261850 0.453945 0.837382 11.00000 0.02551 0.02339 =
0.02826 -0.00428 -0.00359 -0.00243
AFIX 23
H13A 2 0.222858 0.394545 0.782166 11.00000 -1.20000
H13B 2 0.157054 0.552751 0.857490 11.00000 -1.20000
AFIX 0
C14 1 0.259797 0.354310 0.948390 11.00000 0.03001 0.03300 =
0.02676 -0.00435 -0.00209 -0.00798
AFIX 23
H14A 2 0.402588 0.307679 0.948720 11.00000 -1.20000
H14B 2 0.198381 0.425502 1.016160 11.00000 -1.20000
AFIX 0
C15 1 0.142135 0.220852 0.961426 11.00000 0.02985 0.03714 =
0.03129 0.00387 -0.00135 -0.01137
AFIX 23
H15A 2 0.091705 0.198483 1.044365 11.00000 -1.20000
H15B 2 0.021803 0.256971 0.930843 11.00000 -1.20000
AFIX 0
C16 1 0.271274 0.067658 0.898814 11.00000 0.02835 0.02976 =
0.03185 0.00739 -0.00563 -0.01225
AFIX 23
H16A 2 0.361024 0.011001 0.945484 11.00000 -1.20000
H16B 2 0.179935 -0.001245 0.890599 11.00000 -1.20000
AFIX 0
H3 2 0.834962 0.112230 0.796796 11.00000 0.04773
HKLF 4
REM testt1_a.res in P-1
REM R1 = 0.0466 for 2293 Fo > 4sig(Fo) and 0.0735 for all 3290 data
REM 185 parameters refined using 0 restraints
END
WGHT 0.0463 0.0656
REM Highest difference peak 0.226, deepest hole -0.243, 1-sigma level 0.048
Q1 1 0.7063 0.4467 0.6608 11.00000 0.05 0.23
Q2 1 0.6127 0.3159 0.6797 11.00000 0.05 0.22
Q3 1 0.8369 0.5030 0.6958 11.00000 0.05 0.19
Q4 1 0.9486 0.1429 0.5313 11.00000 0.05 0.18
Q5 1 0.2469 -0.0365 0.8606 11.00000 0.05 0.17
;
_shelx_res_checksum 84192
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3:n-pentane'
#######################################################################
#
# 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_testh1
_database_code_depnum_ccdc_archive 'CCDC 1993727'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2018-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C15 H19 N3 O'
_chemical_formula_sum 'C15 H19 N3 O'
_chemical_formula_weight 257.33
_chemical_absolute_configuration unk
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 trigonal
_space_group_IT_number 144
_space_group_name_H-M_alt 'P 31'
_space_group_name_Hall 'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
_cell_length_a 22.0392(6)
_cell_length_b 22.0392(6)
_cell_length_c 7.1184(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 2994.36(18)
_cell_formula_units_Z 9
_cell_measurement_reflns_used 3052
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 21.898
_cell_measurement_theta_min 2.824
_shelx_estimated_absorpt_T_max 0.981
_shelx_estimated_absorpt_T_min 0.968
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6470
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0897 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8678. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.284
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1242
_exptl_crystal_size_max 0.389
_exptl_crystal_size_mid 0.323
_exptl_crystal_size_min 0.234
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0614
_diffrn_reflns_av_unetI/netI 0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 22901
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.681
_diffrn_reflns_theta_min 1.848
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.982
_reflns_Friedel_fraction_full 0.985
_reflns_Friedel_fraction_max 0.982
_reflns_number_gt 6127
_reflns_number_total 7518
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection 'Bruker Apex suite'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.162
_refine_diff_density_min -0.206
_refine_diff_density_rms 0.043
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 532
_refine_ls_number_reflns 7518
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0623
_refine_ls_R_factor_gt 0.0444
_refine_ls_restrained_S_all 1.023
_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^)+(0.0361P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0831
_refine_ls_wR_factor_ref 0.0905
_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 Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
H17B), C18(H18A,H18B), C19(H19A,H19B), C31(H31A,H31B), C32(H32A,H32B),
C33(H33A,H33B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
C10(H10), C11(H11), C12(H12), C13(H13), C25(H25), C26(H26), C27(H27),
C28(H28), C40(H40), C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
H30C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.24540(14) 0.07713(13) 0.5564(3) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.20341(16) 0.02602(16) 0.2653(4) 0.0167(7) Uani 1 1 d . . . . .
N2 N 0.29261(16) 0.13514(16) 0.2788(4) 0.0153(7) Uani 1 1 d . . . . .
N3 N 0.18668(18) 0.00504(17) -0.0578(4) 0.0224(8) Uani 1 1 d . . . . .
C1 C 0.1347(2) -0.0295(2) 0.3280(5) 0.0242(10) Uani 1 1 d . . . . .
H1A H 0.140043 -0.050055 0.445978 0.029 Uiso 1 1 calc R . . . .
H1B H 0.114619 -0.066960 0.231971 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0843(2) -0.0016(2) 0.3610(6) 0.0302(10) Uani 1 1 d . . . . .
H2A H 0.094336 0.021344 0.485597 0.036 Uiso 1 1 calc R . . . .
H2B H 0.035795 -0.041693 0.363727 0.036 Uiso 1 1 calc R . . . .
C3 C 0.0891(2) 0.0515(2) 0.2098(6) 0.0279(10) Uani 1 1 d . . . . .
H3A H 0.098907 0.037411 0.086464 0.034 Uiso 1 1 calc R . . . .
H3B H 0.043177 0.049111 0.200911 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1465(2) 0.1283(2) 0.2509(5) 0.0230(9) Uani 1 1 d . . . . .
H4A H 0.123643 0.152664 0.308607 0.028 Uiso 1 1 calc R . . . .
H4B H 0.179167 0.127619 0.345110 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1893(2) 0.1714(2) 0.0824(5) 0.0185(8) Uani 1 1 d . . . . .
C6 C 0.24776(19) 0.16996(19) 0.0029(5) 0.0152(8) Uani 1 1 d . . . . .
C7 C 0.27559(19) 0.12309(19) 0.0766(5) 0.0144(8) Uani 1 1 d . . . . .
C8 C 0.2180(2) 0.0461(2) 0.0776(5) 0.0177(8) Uani 1 1 d . . . . .
C9 C 0.24805(19) 0.0805(2) 0.3846(5) 0.0157(8) Uani 1 1 d . . . . .
C10 C 0.1691(2) 0.2165(2) 0.0042(5) 0.0233(9) Uani 1 1 d . . . . .
H10 H 0.130139 0.217925 0.056427 0.028 Uiso 1 1 calc R . . . .
C11 C 0.2040(2) 0.2596(2) -0.1477(5) 0.0243(9) Uani 1 1 d . . . . .
H11 H 0.188421 0.289131 -0.199694 0.029 Uiso 1 1 calc R . . . .
C12 C 0.2613(2) 0.2591(2) -0.2220(5) 0.0243(9) Uani 1 1 d . . . . .
H12 H 0.286308 0.289154 -0.323802 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2823(2) 0.2145(2) -0.1474(5) 0.0191(8) Uani 1 1 d . . . . .
H13 H 0.321701 0.214255 -0.200641 0.023 Uiso 1 1 calc R . . . .
C14 C 0.3390(2) 0.1296(2) -0.0306(5) 0.0189(9) Uani 1 1 d . . . . .
H14A H 0.377574 0.178115 -0.024848 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.326031 0.116056 -0.162038 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.353796 0.098607 0.026616 0.028 Uiso 1 1 calc GR . . . .
C15 C 0.3355(2) 0.2052(2) 0.3557(5) 0.0192(9) Uani 1 1 d . . . . .
H15A H 0.377184 0.231555 0.277076 0.029 Uiso 1 1 calc GR . . . .
H15B H 0.349908 0.201852 0.483764 0.029 Uiso 1 1 calc GR . . . .
H15C H 0.308367 0.229348 0.358048 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.46454(14) 0.36564(13) 0.4810(3) 0.0217(6) Uani 1 1 d . . . . .
N4 N 0.47625(16) 0.32386(15) 0.7695(4) 0.0157(7) Uani 1 1 d . . . . .
N5 N 0.47001(16) 0.42173(16) 0.7594(4) 0.0152(7) Uani 1 1 d . . . . .
N6 N 0.48676(17) 0.30973(17) 1.0926(4) 0.0200(7) Uani 1 1 d . . . . .
C16 C 0.5064(2) 0.2826(2) 0.6988(5) 0.0202(9) Uani 1 1 d . . . . .
H16A H 0.479148 0.255032 0.588659 0.024 Uiso 1 1 calc R . . . .
H16B H 0.503099 0.249323 0.797139 0.024 Uiso 1 1 calc R . . . .
C17 C 0.5832(2) 0.3289(2) 0.6418(5) 0.0214(9) Uani 1 1 d . . . . .
H17A H 0.585069 0.350852 0.518956 0.026 Uiso 1 1 calc R . . . .
H17B H 0.604484 0.298911 0.625079 0.026 Uiso 1 1 calc R . . . .
C18 C 0.6273(2) 0.3869(2) 0.7839(5) 0.0201(9) Uani 1 1 d . . . . .
H18A H 0.676658 0.398016 0.774378 0.024 Uiso 1 1 calc R . . . .
H18B H 0.610708 0.368878 0.912155 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6247(2) 0.45581(19) 0.7562(5) 0.0170(8) Uani 1 1 d . . . . .
H19A H 0.668081 0.490535 0.691403 0.020 Uiso 1 1 calc R . . . .
H19B H 0.584710 0.445791 0.673317 0.020 Uiso 1 1 calc R . . . .
C20 C 0.61750(19) 0.48811(19) 0.9378(5) 0.0142(8) Uani 1 1 d . . . . .
C21 C 0.55424(18) 0.47132(18) 1.0298(5) 0.0136(8) Uani 1 1 d . . . . .
C22 C 0.48207(18) 0.41414(19) 0.9591(5) 0.0146(8) Uani 1 1 d . . . . .
C23 C 0.48166(18) 0.34426(19) 0.9566(5) 0.0151(8) Uani 1 1 d . . . . .
C24 C 0.46957(19) 0.37087(19) 0.6528(5) 0.0160(8) Uani 1 1 d . . . . .
C25 C 0.6804(2) 0.53864(19) 1.0191(5) 0.0178(8) Uani 1 1 d . . . . .
H25 H 0.723218 0.550722 0.957497 0.021 Uiso 1 1 calc R . . . .
C26 C 0.6825(2) 0.57176(19) 1.1867(5) 0.0187(9) Uani 1 1 d . . . . .
H26 H 0.726096 0.606043 1.238245 0.022 Uiso 1 1 calc R . . . .
C27 C 0.6208(2) 0.55445(19) 1.2775(5) 0.0182(9) Uani 1 1 d . . . . .
H27 H 0.621445 0.576213 1.393285 0.022 Uiso 1 1 calc R . . . .
C28 C 0.5580(2) 0.50519(19) 1.1990(5) 0.0167(8) Uani 1 1 d . . . . .
H28 H 0.515652 0.493903 1.262272 0.020 Uiso 1 1 calc R . . . .
C29 C 0.41971(19) 0.4067(2) 1.0733(5) 0.0190(8) Uani 1 1 d . . . . .
H29A H 0.419891 0.451289 1.071826 0.028 Uiso 1 1 calc GR . . . .
H29B H 0.423410 0.394188 1.203141 0.028 Uiso 1 1 calc GR . . . .
H29C H 0.375968 0.369989 1.017780 0.028 Uiso 1 1 calc GR . . . .
C30 C 0.4793(2) 0.48619(19) 0.6803(5) 0.0196(9) Uani 1 1 d . . . . .
H30A H 0.461278 0.507633 0.768040 0.029 Uiso 1 1 calc GR . . . .
H30B H 0.453787 0.476196 0.561187 0.029 Uiso 1 1 calc GR . . . .
H30C H 0.529299 0.518469 0.657901 0.029 Uiso 1 1 calc GR . . . .
O3 O 0.54098(14) 0.64260(14) 0.4905(3) 0.0212(6) Uani 1 1 d . . . . .
N7 N 0.48681(15) 0.61875(16) 0.1996(4) 0.0156(7) Uani 1 1 d . . . . .
N8 N 0.60072(16) 0.69453(15) 0.2171(4) 0.0152(7) Uani 1 1 d . . . . .
N9 N 0.46384(17) 0.61416(17) -0.1223(5) 0.0183(7) Uani 1 1 d . . . . .
C31 C 0.41516(19) 0.5920(2) 0.2681(5) 0.0195(9) Uani 1 1 d . . . . .
H31A H 0.406570 0.560393 0.376142 0.023 Uiso 1 1 calc R . . . .
H31B H 0.381598 0.564358 0.167513 0.023 Uiso 1 1 calc R . . . .
C32 C 0.4026(2) 0.6511(2) 0.3284(5) 0.0222(9) Uani 1 1 d . . . . .
H32A H 0.424980 0.669070 0.452078 0.027 Uiso 1 1 calc R . . . .
H32B H 0.351577 0.632194 0.343735 0.027 Uiso 1 1 calc R . . . .
C33 C 0.4313(2) 0.7124(2) 0.1875(5) 0.0205(9) Uani 1 1 d . . . . .
H33A H 0.403010 0.735696 0.196635 0.025 Uiso 1 1 calc R . . . .
H33B H 0.425731 0.693309 0.058714 0.025 Uiso 1 1 calc R . . . .
C34 C 0.5101(2) 0.7682(2) 0.2193(5) 0.0195(9) Uani 1 1 d . . . . .
H34A H 0.512368 0.808667 0.286110 0.023 Uiso 1 1 calc R . . . .
H34B H 0.531073 0.747625 0.302493 0.023 Uiso 1 1 calc R . . . .
C35 C 0.55474(19) 0.79509(19) 0.0413(5) 0.0185(8) Uani 1 1 d . . . . .
C36 C 0.59120(19) 0.76531(19) -0.0465(5) 0.0167(8) Uani 1 1 d . . . . .
C37 C 0.58395(19) 0.69500(19) 0.0166(5) 0.0151(8) Uani 1 1 d . . . . .
C38 C 0.5062(2) 0.63928(19) 0.0148(5) 0.0160(8) Uani 1 1 d . . . . .
C39 C 0.54403(19) 0.65197(19) 0.3202(5) 0.0160(8) Uani 1 1 d . . . . .
C40 C 0.5606(2) 0.8558(2) -0.0377(6) 0.0250(9) Uani 1 1 d . . . . .
H40 H 0.536426 0.876376 0.020146 0.030 Uiso 1 1 calc R . . . .
C41 C 0.6000(2) 0.8871(2) -0.1957(6) 0.0270(10) Uani 1 1 d . . . . .
H41 H 0.601652 0.927769 -0.246849 0.032 Uiso 1 1 calc R . . . .
C42 C 0.6367(2) 0.8592(2) -0.2784(6) 0.0282(10) Uani 1 1 d . . . . .
H42 H 0.664815 0.880910 -0.386027 0.034 Uiso 1 1 calc R . . . .
C43 C 0.6325(2) 0.7989(2) -0.2036(5) 0.0223(9) Uani 1 1 d . . . . .
H43 H 0.658392 0.779989 -0.260887 0.027 Uiso 1 1 calc R . . . .
C44 C 0.62552(19) 0.6702(2) -0.1026(5) 0.0179(8) Uani 1 1 d . . . . .
H44A H 0.675637 0.704497 -0.093907 0.027 Uiso 1 1 calc GR . . . .
H44B H 0.610444 0.665484 -0.233878 0.027 Uiso 1 1 calc GR . . . .
H44C H 0.617004 0.624742 -0.055955 0.027 Uiso 1 1 calc GR . . . .
C45 C 0.6692(2) 0.7389(2) 0.2986(5) 0.0223(9) Uani 1 1 d . . . . .
H45A H 0.704258 0.733017 0.229041 0.033 Uiso 1 1 calc GR . . . .
H45B H 0.668861 0.725739 0.430272 0.033 Uiso 1 1 calc GR . . . .
H45C H 0.680710 0.787925 0.291746 0.033 Uiso 1 1 calc GR . . . .
H9 H 0.484(2) 0.631(2) -0.226(5) 0.017(11) Uiso 1 1 d . . . . .
H6 H 0.491(2) 0.333(2) 1.202(5) 0.028(12) Uiso 1 1 d . . . . .
H3 H 0.203(2) 0.024(2) -0.170(6) 0.023(11) Uiso 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
O1 0.0293(16) 0.0277(16) 0.0125(14) 0.0021(12) 0.0007(11) 0.0167(14)
N1 0.0180(17) 0.0164(17) 0.0134(15) 0.0021(13) 0.0002(13) 0.0070(14)
N2 0.0181(17) 0.0174(17) 0.0111(15) 0.0002(13) 0.0004(13) 0.0095(15)
N3 0.027(2) 0.0206(19) 0.0137(17) 0.0009(15) 0.0000(15) 0.0078(16)
C1 0.021(2) 0.020(2) 0.023(2) 0.0048(17) 0.0033(18) 0.0031(19)
C2 0.019(2) 0.034(3) 0.032(2) 0.014(2) 0.0094(19) 0.009(2)
C3 0.016(2) 0.035(3) 0.032(2) 0.008(2) 0.0032(18) 0.012(2)
C4 0.022(2) 0.035(3) 0.019(2) 0.0011(18) 0.0018(17) 0.019(2)
C5 0.017(2) 0.021(2) 0.0174(19) -0.0020(16) -0.0018(16) 0.0095(18)
C6 0.018(2) 0.0144(19) 0.0141(18) -0.0025(15) -0.0050(15) 0.0088(17)
C7 0.014(2) 0.019(2) 0.0097(17) 0.0005(15) 0.0011(15) 0.0082(17)
C8 0.019(2) 0.022(2) 0.0147(19) 0.0028(17) 0.0014(16) 0.0124(18)
C9 0.016(2) 0.022(2) 0.014(2) -0.0009(16) -0.0006(16) 0.0134(18)
C10 0.022(2) 0.025(2) 0.027(2) -0.0035(18) -0.0036(18) 0.0141(19)
C11 0.028(2) 0.023(2) 0.027(2) 0.0002(18) -0.0084(19) 0.016(2)
C12 0.031(3) 0.021(2) 0.020(2) 0.0048(17) -0.0007(18) 0.013(2)
C13 0.020(2) 0.021(2) 0.0168(18) -0.0017(16) 0.0000(16) 0.0103(18)
C14 0.019(2) 0.023(2) 0.0160(19) 0.0008(16) 0.0017(16) 0.0115(18)
C15 0.020(2) 0.020(2) 0.0185(19) -0.0017(16) -0.0022(16) 0.0101(18)
O2 0.0289(16) 0.0222(15) 0.0135(14) -0.0033(11) -0.0015(12) 0.0124(13)
N4 0.0180(18) 0.0144(17) 0.0133(15) 0.0000(13) 0.0017(13) 0.0070(14)
N5 0.0200(18) 0.0159(17) 0.0105(15) 0.0000(13) -0.0012(13) 0.0096(15)
N6 0.0226(19) 0.0183(18) 0.0143(16) 0.0003(15) 0.0009(14) 0.0067(16)
C16 0.028(2) 0.016(2) 0.020(2) -0.0006(17) 0.0011(17) 0.0138(19)
C17 0.026(2) 0.022(2) 0.0204(19) -0.0027(17) 0.0031(17) 0.0148(19)
C18 0.018(2) 0.023(2) 0.022(2) -0.0020(17) 0.0011(17) 0.0122(19)
C19 0.016(2) 0.017(2) 0.0169(19) 0.0012(16) 0.0037(16) 0.0072(17)
C20 0.015(2) 0.0124(19) 0.0145(18) 0.0024(15) -0.0008(15) 0.0068(17)
C21 0.015(2) 0.0110(19) 0.0155(18) 0.0021(15) 0.0007(15) 0.0074(16)
C22 0.014(2) 0.016(2) 0.0105(18) 0.0017(15) -0.0001(15) 0.0051(17)
C23 0.0092(19) 0.014(2) 0.0172(19) -0.0016(16) -0.0001(15) 0.0017(16)
C24 0.015(2) 0.016(2) 0.0141(19) 0.0011(16) 0.0007(16) 0.0054(17)
C25 0.017(2) 0.018(2) 0.0181(19) 0.0021(16) 0.0007(16) 0.0090(18)
C26 0.015(2) 0.018(2) 0.022(2) -0.0022(17) -0.0094(16) 0.0080(18)
C27 0.028(2) 0.017(2) 0.0126(18) -0.0015(16) -0.0030(16) 0.0133(18)
C28 0.021(2) 0.016(2) 0.0133(18) 0.0018(15) -0.0012(16) 0.0095(18)
C29 0.016(2) 0.023(2) 0.0165(19) 0.0008(16) 0.0015(16) 0.0088(18)
C30 0.024(2) 0.021(2) 0.0160(19) -0.0018(16) -0.0026(17) 0.0133(19)
O3 0.0256(16) 0.0282(16) 0.0102(13) 0.0018(11) 0.0013(11) 0.0138(13)
N7 0.0143(17) 0.0198(17) 0.0130(15) 0.0008(13) 0.0010(13) 0.0088(15)
N8 0.0145(17) 0.0170(17) 0.0125(15) 0.0001(13) -0.0003(13) 0.0067(15)
N9 0.0183(18) 0.0211(19) 0.0159(17) -0.0017(15) -0.0010(15) 0.0103(16)
C31 0.018(2) 0.022(2) 0.0157(19) 0.0022(16) 0.0021(16) 0.0080(18)
C32 0.017(2) 0.026(2) 0.021(2) 0.0009(17) 0.0055(17) 0.0090(19)
C33 0.018(2) 0.023(2) 0.026(2) -0.0020(17) 0.0009(17) 0.0145(19)
C34 0.024(2) 0.019(2) 0.0208(19) -0.0031(16) 0.0023(17) 0.0143(19)
C35 0.015(2) 0.016(2) 0.022(2) 0.0008(16) -0.0019(16) 0.0059(17)
C36 0.017(2) 0.016(2) 0.0172(19) -0.0012(16) -0.0054(16) 0.0086(17)
C37 0.018(2) 0.017(2) 0.0100(17) -0.0003(15) 0.0005(15) 0.0086(17)
C38 0.019(2) 0.015(2) 0.0169(19) -0.0004(16) 0.0001(16) 0.0107(17)
C39 0.018(2) 0.014(2) 0.019(2) -0.0016(16) -0.0001(17) 0.0108(18)
C40 0.026(2) 0.018(2) 0.032(2) -0.0008(19) -0.0036(19) 0.0117(19)
C41 0.030(3) 0.017(2) 0.030(2) 0.0050(19) -0.008(2) 0.009(2)
C42 0.033(3) 0.022(2) 0.022(2) 0.0055(18) 0.0001(19) 0.008(2)
C43 0.025(2) 0.023(2) 0.0180(19) -0.0006(17) 0.0002(17) 0.0110(19)
C44 0.020(2) 0.021(2) 0.0155(19) -0.0005(16) -0.0002(16) 0.0126(18)
C45 0.020(2) 0.024(2) 0.0181(19) -0.0011(17) -0.0023(17) 0.0082(18)
_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
O1 C9 1.224(4) . ?
N1 C1 1.462(5) . ?
N1 C8 1.393(4) . ?
N1 C9 1.396(5) . ?
N2 C7 1.477(4) . ?
N2 C9 1.342(5) . ?
N2 C15 1.455(5) . ?
N3 C8 1.265(5) . ?
N3 H3 0.89(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.530(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.553(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.553(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.528(5) . ?
C5 C6 1.422(5) . ?
C5 C10 1.394(5) . ?
C6 C7 1.534(5) . ?
C6 C13 1.393(5) . ?
C7 C8 1.529(5) . ?
C7 C14 1.535(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C24 1.228(4) . ?
N4 C16 1.459(5) . ?
N4 C23 1.392(4) . ?
N4 C24 1.392(5) . ?
N5 C22 1.471(4) . ?
N5 C24 1.350(4) . ?
N5 C30 1.444(4) . ?
N6 C23 1.270(5) . ?
N6 H6 0.91(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.536(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.561(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(5) . ?
C20 C21 1.412(5) . ?
C20 C25 1.398(5) . ?
C21 C22 1.539(5) . ?
C21 C28 1.397(5) . ?
C22 C23 1.536(5) . ?
C22 C29 1.534(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.376(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(5) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O3 C39 1.226(4) . ?
N7 C31 1.466(5) . ?
N7 C38 1.387(4) . ?
N7 C39 1.393(5) . ?
N8 C37 1.476(4) . ?
N8 C39 1.345(4) . ?
N8 C45 1.447(5) . ?
N9 C38 1.271(5) . ?
N9 H9 0.85(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.524(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.541(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.562(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.530(5) . ?
C35 C36 1.412(5) . ?
C35 C40 1.396(5) . ?
C36 C37 1.543(5) . ?
C36 C43 1.398(5) . ?
C37 C38 1.529(5) . ?
C37 C44 1.536(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.376(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.371(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.393(6) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
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
C8 N1 C1 122.4(3) . . ?
C8 N1 C9 111.0(3) . . ?
C9 N1 C1 121.6(3) . . ?
C9 N2 C7 112.3(3) . . ?
C9 N2 C15 122.5(3) . . ?
C15 N2 C7 121.9(3) . . ?
C8 N3 H3 114(3) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.6(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C6 C5 C4 125.8(3) . . ?
C10 C5 C4 116.0(3) . . ?
C10 C5 C6 118.2(3) . . ?
C5 C6 C7 123.4(3) . . ?
C13 C6 C5 118.2(3) . . ?
C13 C6 C7 118.4(3) . . ?
N2 C7 C6 111.3(3) . . ?
N2 C7 C8 101.0(3) . . ?
N2 C7 C14 109.3(3) . . ?
C6 C7 C14 114.8(3) . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 C14 108.5(3) . . ?
N1 C8 C7 106.8(3) . . ?
N3 C8 N1 123.1(3) . . ?
N3 C8 C7 130.1(3) . . ?
O1 C9 N1 124.3(3) . . ?
O1 C9 N2 127.3(3) . . ?
N2 C9 N1 108.4(3) . . ?
C5 C10 H10 118.9 . . ?
C11 C10 C5 122.2(4) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C6 C13 H13 118.8 . . ?
C12 C13 C6 122.4(4) . . ?
C12 C13 H13 118.8 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 N4 C16 122.7(3) . . ?
C23 N4 C24 110.8(3) . . ?
C24 N4 C16 120.6(3) . . ?
C24 N5 C22 112.1(3) . . ?
C24 N5 C30 122.4(3) . . ?
C30 N5 C22 123.0(3) . . ?
C23 N6 H6 109(3) . . ?
N4 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
N4 C16 C17 111.9(3) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.1(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.2(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.3(3) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C21 C20 C19 126.3(3) . . ?
C25 C20 C19 115.5(3) . . ?
C25 C20 C21 118.2(3) . . ?
C20 C21 C22 122.9(3) . . ?
C28 C21 C20 118.3(3) . . ?
C28 C21 C22 118.7(3) . . ?
N5 C22 C21 113.2(3) . . ?
N5 C22 C23 101.1(3) . . ?
N5 C22 C29 108.7(3) . . ?
C23 C22 C21 108.1(3) . . ?
C29 C22 C21 114.7(3) . . ?
C29 C22 C23 110.1(3) . . ?
N4 C23 C22 106.9(3) . . ?
N6 C23 N4 123.7(3) . . ?
N6 C23 C22 129.3(3) . . ?
O2 C24 N4 124.2(3) . . ?
O2 C24 N5 126.9(3) . . ?
N5 C24 N4 108.8(3) . . ?
C20 C25 H25 118.8 . . ?
C26 C25 C20 122.3(4) . . ?
C26 C25 H25 118.8 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.3(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C21 C28 H28 118.8 . . ?
C27 C28 C21 122.5(4) . . ?
C27 C28 H28 118.8 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C38 N7 C31 122.8(3) . . ?
C38 N7 C39 111.2(3) . . ?
C39 N7 C31 121.1(3) . . ?
C39 N8 C37 112.6(3) . . ?
C39 N8 C45 122.9(3) . . ?
C45 N8 C37 124.3(3) . . ?
C38 N9 H9 111(3) . . ?
N7 C31 H31A 109.3 . . ?
N7 C31 H31B 109.3 . . ?
N7 C31 C32 111.7(3) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C31 C32 C33 113.2(3) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C32 C33 C34 113.8(3) . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C33 C34 H34A 108.4 . . ?
C33 C34 H34B 108.4 . . ?
H34A C34 H34B 107.5 . . ?
C35 C34 C33 115.6(3) . . ?
C35 C34 H34A 108.4 . . ?
C35 C34 H34B 108.4 . . ?
C36 C35 C34 126.3(3) . . ?
C40 C35 C34 116.0(3) . . ?
C40 C35 C36 117.7(3) . . ?
C35 C36 C37 122.7(3) . . ?
C43 C36 C35 118.7(3) . . ?
C43 C36 C37 118.5(3) . . ?
N8 C37 C36 112.8(3) . . ?
N8 C37 C38 100.7(3) . . ?
N8 C37 C44 109.6(3) . . ?
C38 C37 C36 108.4(3) . . ?
C38 C37 C44 109.7(3) . . ?
C44 C37 C36 114.6(3) . . ?
N7 C38 C37 107.0(3) . . ?
N9 C38 N7 123.1(3) . . ?
N9 C38 C37 129.8(3) . . ?
O3 C39 N7 124.2(3) . . ?
O3 C39 N8 127.7(3) . . ?
N8 C39 N7 108.1(3) . . ?
C35 C40 H40 118.5 . . ?
C41 C40 C35 123.0(4) . . ?
C41 C40 H40 118.5 . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.4(4) . . ?
C42 C41 H41 120.3 . . ?
C41 C42 H42 120.3 . . ?
C41 C42 C43 119.5(4) . . ?
C43 C42 H42 120.3 . . ?
C36 C43 H43 119.1 . . ?
C42 C43 C36 121.8(4) . . ?
C42 C43 H43 119.1 . . ?
C37 C44 H44A 109.5 . . ?
C37 C44 H44B 109.5 . . ?
C37 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C45 H45A 109.5 . . ?
N8 C45 H45B 109.5 . . ?
N8 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
_shelx_res_file
;
TITL testh1_a.res in P3(1)
testh1.res
created by SHELXL-2017/1 at 14:25:45 on 23-Aug-2018
REM Old TITL testh1 in P3(2)
REM SHELXT solution in P3(1)
REM R1 0.093, Rweak 0.035, Alpha 0.003, Orientation as input
REM Flack x = -0.095 ( 0.688 ) from Parsons' quotients
REM Formula found by SHELXT: C45 N8 O3
CELL 0.71073 22.0392 22.0392 7.1184 90 90 120
ZERR 9 0.0006 0.0006 0.0002 0 0 0
LATT -1
SYMM -Y,+X-Y,0.333+Z
SYMM +Y-X,-X,0.667+Z
SFAC C H N O
UNIT 135 171 27 9
L.S. 4 0 14
PLAN 5
SIZE 0.234 0.323 0.389
TEMP -173.11
BOND $H
list 4
fmap 2 53
acta
SHEL 9999 0.82
REM
REM
REM
WGHT 0.036100
FVAR 0.63725
O1 4 0.245403 0.077129 0.556358 11.00000 0.02933 0.02769 =
0.01248 0.00212 0.00066 0.01674
N1 3 0.203407 0.026017 0.265269 11.00000 0.01803 0.01642 =
0.01342 0.00212 0.00021 0.00703
N2 3 0.292610 0.135138 0.278775 11.00000 0.01813 0.01740 =
0.01114 0.00024 0.00039 0.00948
N3 3 0.186684 0.005042 -0.057792 11.00000 0.02749 0.02059 =
0.01366 0.00095 0.00005 0.00783
C1 1 0.134654 -0.029451 0.327950 11.00000 0.02055 0.02020 =
0.02255 0.00475 0.00327 0.00314
AFIX 23
H1A 2 0.140043 -0.050055 0.445978 11.00000 -1.20000
H1B 2 0.114619 -0.066960 0.231971 11.00000 -1.20000
AFIX 0
C2 1 0.084336 -0.001616 0.360973 11.00000 0.01926 0.03371 =
0.03160 0.01450 0.00942 0.00873
AFIX 23
H2A 2 0.094336 0.021344 0.485597 11.00000 -1.20000
H2B 2 0.035795 -0.041693 0.363727 11.00000 -1.20000
AFIX 0
C3 1 0.089130 0.051456 0.209829 11.00000 0.01635 0.03484 =
0.03161 0.00784 0.00320 0.01206
AFIX 23
H3A 2 0.098907 0.037411 0.086464 11.00000 -1.20000
H3B 2 0.043177 0.049111 0.200911 11.00000 -1.20000
AFIX 0
C4 1 0.146468 0.128303 0.250906 11.00000 0.02209 0.03474 =
0.01851 0.00107 0.00177 0.01888
AFIX 23
H4A 2 0.123643 0.152664 0.308607 11.00000 -1.20000
H4B 2 0.179167 0.127619 0.345110 11.00000 -1.20000
AFIX 0
C5 1 0.189313 0.171365 0.082443 11.00000 0.01688 0.02111 =
0.01740 -0.00195 -0.00176 0.00952
C6 1 0.247764 0.169959 0.002866 11.00000 0.01784 0.01444 =
0.01411 -0.00250 -0.00502 0.00877
C7 1 0.275592 0.123089 0.076631 11.00000 0.01413 0.01928 =
0.00968 0.00054 0.00107 0.00818
C8 1 0.217992 0.046102 0.077593 11.00000 0.01947 0.02188 =
0.01467 0.00277 0.00144 0.01242
C9 1 0.248054 0.080464 0.384615 11.00000 0.01620 0.02172 =
0.01437 -0.00085 -0.00065 0.01338
C10 1 0.169092 0.216534 0.004194 11.00000 0.02186 0.02458 =
0.02662 -0.00348 -0.00358 0.01407
AFIX 43
H10 2 0.130139 0.217925 0.056427 11.00000 -1.20000
AFIX 0
C11 1 0.204025 0.259604 -0.147705 11.00000 0.02761 0.02301 =
0.02706 0.00022 -0.00837 0.01617
AFIX 43
H11 2 0.188421 0.289131 -0.199694 11.00000 -1.20000
AFIX 0
C12 1 0.261289 0.259114 -0.221996 11.00000 0.03144 0.02109 =
0.01965 0.00477 -0.00067 0.01258
AFIX 43
H12 2 0.286308 0.289154 -0.323802 11.00000 -1.20000
AFIX 0
C13 1 0.282296 0.214488 -0.147372 11.00000 0.01999 0.02073 =
0.01677 -0.00168 -0.00002 0.01032
AFIX 43
H13 2 0.321701 0.214255 -0.200641 11.00000 -1.20000
AFIX 0
C14 1 0.338976 0.129551 -0.030600 11.00000 0.01943 0.02259 =
0.01603 0.00078 0.00168 0.01154
AFIX 137
H14A 2 0.377574 0.178115 -0.024848 11.00000 -1.50000
H14B 2 0.326031 0.116056 -0.162038 11.00000 -1.50000
H14C 2 0.353796 0.098607 0.026616 11.00000 -1.50000
AFIX 0
C15 1 0.335521 0.205193 0.355696 11.00000 0.01956 0.01982 =
0.01849 -0.00170 -0.00222 0.01010
AFIX 137
H15A 2 0.377184 0.231555 0.277076 11.00000 -1.50000
H15B 2 0.349908 0.201852 0.483764 11.00000 -1.50000
H15C 2 0.308367 0.229348 0.358048 11.00000 -1.50000
AFIX 0
O2 4 0.464537 0.365640 0.480991 11.00000 0.02891 0.02222 =
0.01346 -0.00333 -0.00146 0.01245
N4 3 0.476247 0.323863 0.769526 11.00000 0.01801 0.01445 =
0.01332 0.00001 0.00171 0.00702
N5 3 0.470011 0.421726 0.759441 11.00000 0.01998 0.01588 =
0.01047 0.00003 -0.00116 0.00955
N6 3 0.486762 0.309731 1.092603 11.00000 0.02260 0.01833 =
0.01428 0.00033 0.00086 0.00672
C16 1 0.506449 0.282617 0.698762 11.00000 0.02829 0.01592 =
0.01996 -0.00064 0.00106 0.01383
AFIX 23
H16A 2 0.479148 0.255032 0.588659 11.00000 -1.20000
H16B 2 0.503099 0.249323 0.797139 11.00000 -1.20000
AFIX 0
C17 1 0.583242 0.328915 0.641763 11.00000 0.02591 0.02180 =
0.02042 -0.00275 0.00305 0.01481
AFIX 23
H17A 2 0.585069 0.350852 0.518956 11.00000 -1.20000
H17B 2 0.604484 0.298911 0.625079 11.00000 -1.20000
AFIX 0
C18 1 0.627330 0.386895 0.783887 11.00000 0.01781 0.02309 =
0.02195 -0.00200 0.00109 0.01222
AFIX 23
H18A 2 0.676658 0.398016 0.774378 11.00000 -1.20000
H18B 2 0.610708 0.368878 0.912155 11.00000 -1.20000
AFIX 0
C19 1 0.624731 0.455808 0.756201 11.00000 0.01597 0.01680 =
0.01693 0.00116 0.00366 0.00725
AFIX 23
H19A 2 0.668081 0.490535 0.691403 11.00000 -1.20000
H19B 2 0.584710 0.445791 0.673317 11.00000 -1.20000
AFIX 0
C20 1 0.617496 0.488114 0.937755 11.00000 0.01534 0.01243 =
0.01454 0.00237 -0.00079 0.00684
C21 1 0.554244 0.471318 1.029829 11.00000 0.01524 0.01101 =
0.01553 0.00212 0.00066 0.00739
C22 1 0.482070 0.414140 0.959099 11.00000 0.01383 0.01623 =
0.01053 0.00168 -0.00009 0.00507
C23 1 0.481664 0.344258 0.956624 11.00000 0.00919 0.01352 =
0.01716 -0.00157 -0.00013 0.00169
C24 1 0.469573 0.370867 0.652822 11.00000 0.01509 0.01560 =
0.01414 0.00107 0.00071 0.00540
C25 1 0.680404 0.538642 1.019126 11.00000 0.01701 0.01840 =
0.01809 0.00206 0.00065 0.00901
AFIX 43
H25 2 0.723218 0.550722 0.957497 11.00000 -1.20000
AFIX 0
C26 1 0.682508 0.571762 1.186697 11.00000 0.01541 0.01812 =
0.02214 -0.00221 -0.00942 0.00803
AFIX 43
H26 2 0.726096 0.606043 1.238245 11.00000 -1.20000
AFIX 0
C27 1 0.620801 0.554451 1.277520 11.00000 0.02751 0.01740 =
0.01263 -0.00152 -0.00304 0.01334
AFIX 43
H27 2 0.621445 0.576213 1.393285 11.00000 -1.20000
AFIX 0
C28 1 0.557961 0.505193 1.198959 11.00000 0.02095 0.01618 =
0.01328 0.00179 -0.00116 0.00948
AFIX 43
H28 2 0.515652 0.493903 1.262272 11.00000 -1.20000
AFIX 0
C29 1 0.419707 0.406733 1.073264 11.00000 0.01642 0.02264 =
0.01655 0.00076 0.00155 0.00883
AFIX 137
H29A 2 0.419891 0.451289 1.071826 11.00000 -1.50000
H29B 2 0.423410 0.394188 1.203141 11.00000 -1.50000
H29C 2 0.375968 0.369989 1.017780 11.00000 -1.50000
AFIX 0
C30 1 0.479344 0.486186 0.680281 11.00000 0.02384 0.02148 =
0.01603 -0.00176 -0.00260 0.01327
AFIX 137
H30A 2 0.461278 0.507633 0.768040 11.00000 -1.50000
H30B 2 0.453787 0.476196 0.561187 11.00000 -1.50000
H30C 2 0.529299 0.518469 0.657901 11.00000 -1.50000
AFIX 0
O3 4 0.540978 0.642600 0.490518 11.00000 0.02556 0.02823 =
0.01025 0.00178 0.00126 0.01384
N7 3 0.486807 0.618754 0.199609 11.00000 0.01430 0.01981 =
0.01304 0.00077 0.00099 0.00879
N8 3 0.600718 0.694531 0.217092 11.00000 0.01446 0.01697 =
0.01250 0.00011 -0.00027 0.00666
N9 3 0.463845 0.614156 -0.122320 11.00000 0.01833 0.02113 =
0.01588 -0.00172 -0.00103 0.01028
C31 1 0.415156 0.591980 0.268108 11.00000 0.01824 0.02191 =
0.01569 0.00219 0.00205 0.00804
AFIX 23
H31A 2 0.406570 0.560393 0.376142 11.00000 -1.20000
H31B 2 0.381598 0.564358 0.167513 11.00000 -1.20000
AFIX 0
C32 1 0.402569 0.651125 0.328400 11.00000 0.01687 0.02607 =
0.02137 0.00092 0.00552 0.00896
AFIX 23
H32A 2 0.424980 0.669070 0.452078 11.00000 -1.20000
H32B 2 0.351577 0.632194 0.343735 11.00000 -1.20000
AFIX 0
C33 1 0.431346 0.712355 0.187508 11.00000 0.01842 0.02295 =
0.02571 -0.00198 0.00087 0.01450
AFIX 23
H33A 2 0.403010 0.735696 0.196635 11.00000 -1.20000
H33B 2 0.425731 0.693309 0.058714 11.00000 -1.20000
AFIX 0
C34 1 0.510073 0.768179 0.219263 11.00000 0.02390 0.01865 =
0.02078 -0.00306 0.00227 0.01430
AFIX 23
H34A 2 0.512368 0.808667 0.286110 11.00000 -1.20000
H34B 2 0.531073 0.747625 0.302493 11.00000 -1.20000
AFIX 0
C35 1 0.554736 0.795090 0.041303 11.00000 0.01495 0.01632 =
0.02172 0.00078 -0.00189 0.00585
C36 1 0.591203 0.765313 -0.046467 11.00000 0.01684 0.01646 =
0.01719 -0.00122 -0.00537 0.00863
C37 1 0.583946 0.694999 0.016606 11.00000 0.01823 0.01687 =
0.00997 -0.00031 0.00050 0.00857
C38 1 0.506239 0.639282 0.014823 11.00000 0.01931 0.01478 =
0.01694 -0.00039 0.00013 0.01073
C39 1 0.544026 0.651972 0.320222 11.00000 0.01822 0.01436 =
0.01889 -0.00159 -0.00014 0.01078
C40 1 0.560644 0.855790 -0.037711 11.00000 0.02611 0.01811 =
0.03169 -0.00081 -0.00363 0.01173
AFIX 43
H40 2 0.536426 0.876376 0.020146 11.00000 -1.20000
AFIX 0
C41 1 0.599975 0.887149 -0.195659 11.00000 0.02974 0.01694 =
0.03037 0.00498 -0.00801 0.00861
AFIX 43
H41 2 0.601652 0.927769 -0.246849 11.00000 -1.20000
AFIX 0
C42 1 0.636707 0.859239 -0.278442 11.00000 0.03294 0.02185 =
0.02192 0.00550 0.00012 0.00767
AFIX 43
H42 2 0.664815 0.880910 -0.386027 11.00000 -1.20000
AFIX 0
C43 1 0.632500 0.798869 -0.203601 11.00000 0.02450 0.02307 =
0.01804 -0.00056 0.00021 0.01095
AFIX 43
H43 2 0.658392 0.779989 -0.260887 11.00000 -1.20000
AFIX 0
C44 1 0.625520 0.670185 -0.102569 11.00000 0.02011 0.02112 =
0.01551 -0.00052 -0.00019 0.01263
AFIX 137
H44A 2 0.675637 0.704497 -0.093907 11.00000 -1.50000
H44B 2 0.610444 0.665484 -0.233878 11.00000 -1.50000
H44C 2 0.617004 0.624742 -0.055955 11.00000 -1.50000
AFIX 0
C45 1 0.669156 0.738879 0.298612 11.00000 0.02046 0.02432 =
0.01806 -0.00114 -0.00228 0.00820
AFIX 137
H45A 2 0.704258 0.733017 0.229041 11.00000 -1.50000
H45B 2 0.668861 0.725739 0.430272 11.00000 -1.50000
H45C 2 0.680710 0.787925 0.291746 11.00000 -1.50000
AFIX 0
H9 2 0.484325 0.631472 -0.226408 11.00000 0.01673
H6 2 0.491121 0.333015 1.201707 11.00000 0.02770
H3 2 0.202685 0.024082 -0.170179 11.00000 0.02343
HKLF 4
REM testh1_a.res in P3(1)
REM R1 = 0.0444 for 6127 Fo > 4sig(Fo) and 0.0623 for all 7518 data
REM 532 parameters refined using 1 restraints
END
WGHT 0.0361 0.0000
REM Highest difference peak 0.162, deepest hole -0.206, 1-sigma level 0.043
Q1 1 0.5004 0.7004 0.5743 11.00000 0.05 0.16
Q2 1 0.4135 0.2356 -0.1504 11.00000 0.05 0.15
Q3 1 0.2757 0.3388 -0.0544 11.00000 0.05 0.15
Q4 1 -0.0228 -0.1622 0.3502 11.00000 0.05 0.15
Q5 1 0.5205 0.4427 0.9962 11.00000 0.05 0.15
;
_shelx_res_checksum 5635
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
#######################################################################
#
# 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_mm151
_database_code_depnum_ccdc_archive 'CCDC 1993735'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2019-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number 2013-4
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C15 H18 N2 O2'
_chemical_formula_sum 'C15 H18 N2 O2'
_chemical_formula_weight 258.31
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 9.6859(2)
_cell_length_b 8.2156(2)
_cell_length_c 16.9618(3)
_cell_angle_alpha 90
_cell_angle_beta 106.1200(10)
_cell_angle_gamma 90
_cell_volume 1296.67(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 5451
_cell_measurement_temperature 100
_cell_measurement_theta_max 29.98
_cell_measurement_theta_min 2.20
_shelx_estimated_absorpt_T_max 0.986
_shelx_estimated_absorpt_T_min 0.953
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_correction_T_min 0.5929
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0696 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.7948. The \l/2 correction factor is Not present.'
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.323
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 552
_exptl_crystal_size_max 0.543
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.163
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0423
_diffrn_reflns_av_unetI/netI 0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 26574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 30.058
_diffrn_reflns_theta_min 2.199
_diffrn_ambient_temperature 100.01
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3110
_reflns_number_total 3801
_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 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_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 0.410
_refine_diff_density_min -0.212
_refine_diff_density_rms 0.049
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.014
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 175
_refine_ls_number_reflns 3801
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0530
_refine_ls_R_factor_gt 0.0396
_refine_ls_restrained_S_all 1.014
_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^)+(0.0516P)^2^+0.4417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0968
_refine_ls_wR_factor_ref 0.1047
_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:
C14(H14)
2.b Secondary CH2 refined with riding coordinates:
C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C)
;
_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 0.42675(11) 0.45628(13) 0.40261(6) 0.0138(2) Uani 1 1 d . . . . .
C2 C 0.65054(11) 0.38918(12) 0.38605(6) 0.0129(2) Uani 1 1 d . . . . .
C3 C 0.59359(11) 0.25210(13) 0.42850(6) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.55045(13) 0.68257(13) 0.35903(7) 0.0189(2) Uani 1 1 d . . . . .
H4A H 0.5097 0.6770 0.2994 0.028 Uiso 1 1 calc GR . . . .
H4B H 0.6491 0.7240 0.3718 0.028 Uiso 1 1 calc GR . . . .
H4C H 0.4922 0.7557 0.3824 0.028 Uiso 1 1 calc GR . . . .
C5 C 0.80716(11) 0.42557(14) 0.43068(7) 0.0177(2) Uani 1 1 d . . . . .
H5A H 0.8382 0.5233 0.4071 0.027 Uiso 1 1 calc GR . . . .
H5B H 0.8672 0.3331 0.4245 0.027 Uiso 1 1 calc GR . . . .
H5C H 0.8167 0.4437 0.4891 0.027 Uiso 1 1 calc GR . . . .
C6 C 0.61961(11) 0.35126(12) 0.29308(6) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.68920(12) 0.45350(13) 0.24993(7) 0.0166(2) Uani 1 1 d . . . . .
H7 H 0.7620 0.5249 0.2800 0.020 Uiso 1 1 calc R . . . .
C8 C 0.65543(12) 0.45405(13) 0.16481(7) 0.0175(2) Uani 1 1 d . . . . .
H8 H 0.7052 0.5237 0.1373 0.021 Uiso 1 1 calc R . . . .
C9 C 0.54810(12) 0.35158(13) 0.12058(7) 0.0172(2) Uani 1 1 d . . . . .
H9 H 0.5208 0.3534 0.0623 0.021 Uiso 1 1 calc R . . . .
C10 C 0.48091(12) 0.24629(13) 0.16217(7) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.4086 0.1755 0.1311 0.019 Uiso 1 1 calc R . . . .
C11 C 0.51494(11) 0.23961(12) 0.24827(7) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.44012(12) 0.10052(13) 0.28073(7) 0.0161(2) Uani 1 1 d . . . . .
H12A H 0.5129 0.0481 0.3264 0.019 Uiso 1 1 calc R . . . .
H12B H 0.4105 0.0186 0.2364 0.019 Uiso 1 1 calc R . . . .
C13 C 0.30748(12) 0.13825(14) 0.31160(7) 0.0175(2) Uani 1 1 d . . . . .
H13A H 0.2600 0.2374 0.2835 0.021 Uiso 1 1 calc R . . . .
H13B H 0.2383 0.0472 0.2958 0.021 Uiso 1 1 calc R . . . .
C14 C 0.34176(11) 0.16413(13) 0.40442(7) 0.0156(2) Uani 1 1 d . . . . .
H14 H 0.3851 0.0610 0.4317 0.019 Uiso 1 1 calc R . . . .
C15 C 0.20903(12) 0.20006(15) 0.43250(8) 0.0218(2) Uani 1 1 d . . . . .
H15A H 0.2379 0.2259 0.4912 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.1460 0.1045 0.4227 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.1576 0.2930 0.4017 0.033 Uiso 1 1 calc GR . . . .
N1 N 0.45348(9) 0.29210(11) 0.42635(6) 0.01342(18) Uani 1 1 d . . . . .
N2 N 0.55111(9) 0.52066(10) 0.39402(6) 0.01412(18) Uani 1 1 d . . . . .
O1 O 0.31367(8) 0.52727(10) 0.39409(5) 0.01948(18) Uani 1 1 d . . . . .
O2 O 0.65651(9) 0.12824(9) 0.45622(5) 0.01777(17) 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 0.0157(5) 0.0128(4) 0.0128(5) -0.0007(4) 0.0036(4) 0.0001(4)
C2 0.0124(4) 0.0120(4) 0.0145(5) 0.0008(4) 0.0042(4) 0.0005(3)
C3 0.0148(5) 0.0140(5) 0.0110(5) -0.0007(4) 0.0037(4) -0.0005(4)
C4 0.0223(5) 0.0110(5) 0.0228(6) 0.0027(4) 0.0051(4) -0.0007(4)
C5 0.0139(5) 0.0209(5) 0.0175(5) 0.0006(4) 0.0029(4) -0.0015(4)
C6 0.0129(4) 0.0128(4) 0.0146(5) 0.0013(4) 0.0051(4) 0.0013(4)
C7 0.0157(5) 0.0158(5) 0.0192(5) 0.0005(4) 0.0062(4) -0.0023(4)
C8 0.0189(5) 0.0171(5) 0.0191(5) 0.0039(4) 0.0097(4) 0.0005(4)
C9 0.0192(5) 0.0189(5) 0.0146(5) 0.0015(4) 0.0067(4) 0.0032(4)
C10 0.0156(5) 0.0160(5) 0.0161(5) -0.0020(4) 0.0045(4) -0.0007(4)
C11 0.0141(5) 0.0113(4) 0.0165(5) -0.0002(4) 0.0063(4) 0.0007(4)
C12 0.0206(5) 0.0125(4) 0.0163(5) -0.0020(4) 0.0069(4) -0.0038(4)
C13 0.0163(5) 0.0189(5) 0.0178(5) -0.0010(4) 0.0057(4) -0.0056(4)
C14 0.0164(5) 0.0145(5) 0.0172(5) 0.0002(4) 0.0066(4) -0.0039(4)
C15 0.0171(5) 0.0267(6) 0.0246(6) -0.0018(5) 0.0106(4) -0.0056(4)
N1 0.0132(4) 0.0122(4) 0.0153(4) 0.0010(3) 0.0048(3) 0.0000(3)
N2 0.0148(4) 0.0107(4) 0.0173(4) 0.0006(3) 0.0053(3) 0.0004(3)
O1 0.0158(4) 0.0188(4) 0.0238(4) 0.0013(3) 0.0054(3) 0.0044(3)
O2 0.0203(4) 0.0152(4) 0.0185(4) 0.0046(3) 0.0066(3) 0.0044(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4110(13) . ?
C1 N2 1.3598(13) . ?
C1 O1 1.2136(13) . ?
C2 C3 1.5204(14) . ?
C2 C5 1.5252(14) . ?
C2 C6 1.5527(15) . ?
C2 N2 1.4782(13) . ?
C3 N1 1.3869(13) . ?
C3 O2 1.2120(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N2 1.4560(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.4034(14) . ?
C6 C11 1.4209(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.3890(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3853(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3872(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4060(15) . ?
C11 C12 1.5348(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5474(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5310(15) . ?
C14 H14 1.0000 . ?
C14 C15 1.5188(15) . ?
C14 N1 1.4802(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
N2 C1 N1 107.73(9) . . ?
O1 C1 N1 125.55(10) . . ?
O1 C1 N2 126.68(10) . . ?
C3 C2 C5 110.60(9) . . ?
C3 C2 C6 109.83(8) . . ?
C5 C2 C6 115.36(9) . . ?
N2 C2 C3 99.59(8) . . ?
N2 C2 C5 113.26(9) . . ?
N2 C2 C6 107.02(8) . . ?
N1 C3 C2 107.05(8) . . ?
O2 C3 C2 126.60(9) . . ?
O2 C3 N1 126.30(10) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 115.11(9) . . ?
C7 C6 C11 118.81(10) . . ?
C11 C6 C2 125.49(9) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.38(10) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.06(10) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.41(10) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 123.00(10) . . ?
C11 C10 H10 118.5 . . ?
C6 C11 C12 128.79(10) . . ?
C10 C11 C6 117.20(9) . . ?
C10 C11 C12 113.81(9) . . ?
C11 C12 H12A 107.5 . . ?
C11 C12 H12B 107.5 . . ?
C11 C12 C13 119.43(9) . . ?
H12A C12 H12B 107.0 . . ?
C13 C12 H12A 107.5 . . ?
C13 C12 H12B 107.5 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.36(9) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14 107.6 . . ?
C15 C14 C13 112.88(9) . . ?
C15 C14 H14 107.6 . . ?
N1 C14 C13 106.96(8) . . ?
N1 C14 H14 107.6 . . ?
N1 C14 C15 113.99(9) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C14 122.95(9) . . ?
C3 N1 C1 109.55(8) . . ?
C3 N1 C14 118.69(9) . . ?
C1 N2 C2 110.16(8) . . ?
C1 N2 C4 119.69(9) . . ?
C4 N2 C2 124.02(9) . . ?
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
C2 C3 N1 C1 -12.54(11) . . . . ?
C2 C3 N1 C14 135.91(9) . . . . ?
C2 C6 C7 C8 -169.15(10) . . . . ?
C2 C6 C11 C10 166.80(9) . . . . ?
C2 C6 C11 C12 -18.58(17) . . . . ?
C3 C2 C6 C7 -169.06(9) . . . . ?
C3 C2 C6 C11 19.81(13) . . . . ?
C3 C2 N2 C1 -24.11(10) . . . . ?
C3 C2 N2 C4 -176.29(9) . . . . ?
C5 C2 C3 N1 140.91(9) . . . . ?
C5 C2 C3 O2 -41.67(14) . . . . ?
C5 C2 C6 C7 -43.27(13) . . . . ?
C5 C2 C6 C11 145.60(10) . . . . ?
C5 C2 N2 C1 -141.56(9) . . . . ?
C5 C2 N2 C4 66.26(13) . . . . ?
C6 C2 C3 N1 -90.63(9) . . . . ?
C6 C2 C3 O2 86.79(13) . . . . ?
C6 C2 N2 C1 90.19(10) . . . . ?
C6 C2 N2 C4 -61.99(12) . . . . ?
C6 C7 C8 C9 0.77(16) . . . . ?
C6 C11 C12 C13 83.06(14) . . . . ?
C7 C6 C11 C10 -4.03(14) . . . . ?
C7 C6 C11 C12 170.59(10) . . . . ?
C7 C8 C9 C10 -2.58(16) . . . . ?
C8 C9 C10 C11 1.01(16) . . . . ?
C9 C10 C11 C6 2.33(15) . . . . ?
C9 C10 C11 C12 -173.09(10) . . . . ?
C10 C11 C12 C13 -102.18(11) . . . . ?
C11 C6 C7 C8 2.61(16) . . . . ?
C11 C12 C13 C14 -95.32(12) . . . . ?
C12 C13 C14 C15 -179.73(9) . . . . ?
C12 C13 C14 N1 54.12(11) . . . . ?
C13 C14 N1 C1 68.85(12) . . . . ?
C13 C14 N1 C3 -75.17(11) . . . . ?
C15 C14 N1 C1 -56.64(13) . . . . ?
C15 C14 N1 C3 159.34(10) . . . . ?
N1 C1 N2 C2 18.08(11) . . . . ?
N1 C1 N2 C4 171.63(9) . . . . ?
N2 C1 N1 C3 -3.00(11) . . . . ?
N2 C1 N1 C14 -149.85(9) . . . . ?
N2 C2 C3 N1 21.48(10) . . . . ?
N2 C2 C3 O2 -161.10(10) . . . . ?
N2 C2 C6 C7 83.74(11) . . . . ?
N2 C2 C6 C11 -87.38(11) . . . . ?
O1 C1 N1 C3 179.10(10) . . . . ?
O1 C1 N1 C14 32.25(16) . . . . ?
O1 C1 N2 C2 -164.05(10) . . . . ?
O1 C1 N2 C4 -10.50(17) . . . . ?
O2 C3 N1 C1 170.03(10) . . . . ?
O2 C3 N1 C14 -41.52(15) . . . . ?
_shelx_res_file
;
TITL test1mp_a.res in P2(1)/n
REM Old TITL test1mp in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.109, Rweak 0.003, Alpha 0.023, Orientation as input
REM Formula found by SHELXT: C15 N2 O2
CELL 0.71073 9.6859 8.2156 16.9618 90 106.12 90
ZERR 4 0.0002 0.0002 0.0003 0 0.001 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 60 72 8 8
L.S. 4
PLAN 5
SIZE 0.163 0.24 0.543
TEMP -173.14
BOND $H
CONF
BOND $H
list 4
fmap 2
acta
REM
REM
REM
WGHT 0.051600 0.441700
FVAR 0.87806
C1 1 0.426748 0.456280 0.402605 11.00000 0.01566 0.01282 =
0.01279 -0.00068 0.00358 0.00013
C2 1 0.650542 0.389179 0.386048 11.00000 0.01242 0.01201 =
0.01447 0.00081 0.00419 0.00048
C3 1 0.593588 0.252105 0.428499 11.00000 0.01481 0.01404 =
0.01099 -0.00071 0.00371 -0.00046
C4 1 0.550450 0.682575 0.359028 11.00000 0.02228 0.01098 =
0.02279 0.00275 0.00513 -0.00066
AFIX 137
H4A 2 0.509675 0.677014 0.299360 11.00000 -1.50000
H4B 2 0.649080 0.723991 0.371816 11.00000 -1.50000
H4C 2 0.492151 0.755705 0.382352 11.00000 -1.50000
AFIX 0
C5 1 0.807165 0.425570 0.430682 11.00000 0.01386 0.02090 =
0.01745 0.00060 0.00294 -0.00152
AFIX 137
H5A 2 0.838158 0.523279 0.407147 11.00000 -1.50000
H5B 2 0.867243 0.333108 0.424516 11.00000 -1.50000
H5C 2 0.816731 0.443707 0.489062 11.00000 -1.50000
AFIX 0
C6 1 0.619612 0.351256 0.293084 11.00000 0.01293 0.01283 =
0.01456 0.00130 0.00505 0.00130
C7 1 0.689198 0.453496 0.249930 11.00000 0.01570 0.01577 =
0.01918 0.00051 0.00618 -0.00233
AFIX 43
H7 2 0.762034 0.524908 0.280024 11.00000 -1.20000
AFIX 0
C8 1 0.655426 0.454047 0.164813 11.00000 0.01889 0.01709 =
0.01908 0.00389 0.00971 0.00047
AFIX 43
H8 2 0.705218 0.523703 0.137317 11.00000 -1.20000
AFIX 0
C9 1 0.548101 0.351577 0.120583 11.00000 0.01921 0.01893 =
0.01457 0.00147 0.00667 0.00323
AFIX 43
H9 2 0.520762 0.353394 0.062293 11.00000 -1.20000
AFIX 0
C10 1 0.480910 0.246293 0.162171 11.00000 0.01560 0.01603 =
0.01607 -0.00197 0.00449 -0.00071
AFIX 43
H10 2 0.408594 0.175461 0.131058 11.00000 -1.20000
AFIX 0
C11 1 0.514939 0.239614 0.248267 11.00000 0.01408 0.01132 =
0.01647 -0.00016 0.00626 0.00068
C12 1 0.440119 0.100522 0.280728 11.00000 0.02061 0.01253 =
0.01630 -0.00201 0.00689 -0.00375
AFIX 23
H12A 2 0.512932 0.048100 0.326425 11.00000 -1.20000
H12B 2 0.410488 0.018609 0.236429 11.00000 -1.20000
AFIX 0
C13 1 0.307483 0.138246 0.311604 11.00000 0.01628 0.01885 =
0.01778 -0.00101 0.00567 -0.00556
AFIX 23
H13A 2 0.260000 0.237358 0.283496 11.00000 -1.20000
H13B 2 0.238345 0.047194 0.295834 11.00000 -1.20000
AFIX 0
C14 1 0.341761 0.164129 0.404423 11.00000 0.01638 0.01446 =
0.01717 0.00017 0.00664 -0.00392
AFIX 13
H14 2 0.385051 0.061026 0.431729 11.00000 -1.20000
AFIX 0
C15 1 0.209031 0.200063 0.432504 11.00000 0.01707 0.02666 =
0.02457 -0.00182 0.01058 -0.00558
AFIX 137
H15A 2 0.237888 0.225851 0.491223 11.00000 -1.50000
H15B 2 0.145986 0.104512 0.422746 11.00000 -1.50000
H15C 2 0.157577 0.293012 0.401662 11.00000 -1.50000
AFIX 0
N1 3 0.453477 0.292095 0.426353 11.00000 0.01323 0.01222 =
0.01527 0.00102 0.00475 0.00001
N2 3 0.551107 0.520655 0.394024 11.00000 0.01481 0.01074 =
0.01730 0.00064 0.00527 0.00044
O1 4 0.313669 0.527268 0.394091 11.00000 0.01584 0.01877 =
0.02377 0.00132 0.00537 0.00439
O2 4 0.656507 0.128236 0.456219 11.00000 0.02034 0.01521 =
0.01848 0.00455 0.00661 0.00439
HKLF 4
REM test1mp_a.res in P2(1)/n
REM R1 = 0.0396 for 3110 Fo > 4sig(Fo) and 0.0530 for all 3801 data
REM 175 parameters refined using 0 restraints
END
WGHT 0.0516 0.4417
REM Highest difference peak 0.410, deepest hole -0.212, 1-sigma level 0.049
Q1 1 0.6227 0.3209 0.4067 11.00000 0.05 0.41
Q2 1 0.6413 0.3709 0.3418 11.00000 0.05 0.38
Q3 1 0.5088 0.2477 0.2049 11.00000 0.05 0.36
Q4 1 0.3257 0.1484 0.3588 11.00000 0.05 0.35
Q5 1 0.2768 0.1914 0.4195 11.00000 0.05 0.35
;
_shelx_res_checksum 98470
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:n-hexane'
#######################################################################
#
# 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_testo1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1993734'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record
;
2020-03-30 deposited with the CCDC. 2020-12-11 downloaded from the CCDC.
;
_audit_creation_date 2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C18 H22 N6 O2, 2(H2 O)'
_chemical_formula_sum 'C18 H26 N6 O4'
_chemical_formula_weight 390.45
_chemical_absolute_configuration unk
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 8.3617(3)
_cell_length_b 13.8207(6)
_cell_length_c 16.0698(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1857.10(13)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3845
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 26.89
_cell_measurement_theta_min 2.53
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.6173
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0681 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.8279. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.396
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 832
_exptl_crystal_size_max 0.443
_exptl_crystal_size_mid 0.367
_exptl_crystal_size_min 0.154
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0451
_diffrn_reflns_av_unetI/netI 0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 17119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.969
_diffrn_reflns_theta_min 1.943
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device 'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type 'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.751
_reflns_Friedel_fraction_full 0.999
_reflns_Friedel_fraction_max 0.989
_reflns_number_gt 3893
_reflns_number_total 4432
_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 'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (Bruker, 2016)'
_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 0.246
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.041
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 281
_refine_ls_number_reflns 4432
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0444
_refine_ls_R_factor_gt 0.0355
_refine_ls_restrained_S_all 1.017
_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^)+(0.0354P)^2^+0.2721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0754
_refine_ls_wR_factor_ref 0.0800
_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. Restrained distances
O3-H3B \\sim O4-H4E \\sim O4-H4D \\sim O3-H3A
with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens mixed
_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
O1 O 0.40538(19) 0.29985(11) 0.74758(10) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.71944(18) 0.29063(10) 0.64921(9) 0.0189(3) Uani 1 1 d . . . . .
O4 O 0.4527(2) 0.66430(14) 0.46646(11) 0.0290(4) Uani 1 1 d D . . . .
N1 N 0.3492(2) 0.46067(13) 0.71828(11) 0.0143(4) Uani 1 1 d . . . . .
N2 N 0.4918(2) 0.42534(12) 0.83103(11) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.3097(2) 0.62813(14) 0.73124(12) 0.0168(4) Uani 1 1 d . . . . .
N4 N 0.6184(2) 0.44495(12) 0.62504(11) 0.0140(4) Uani 1 1 d . . . . .
N5 N 0.7959(2) 0.42354(13) 0.72649(11) 0.0148(4) Uani 1 1 d . . . . .
N6 N 0.5862(2) 0.61246(14) 0.62203(12) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.4157(2) 0.38514(15) 0.76572(14) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.4603(2) 0.52926(14) 0.83849(13) 0.0128(4) Uani 1 1 d . . . . .
C3 C 0.3692(2) 0.54971(15) 0.75722(13) 0.0130(4) Uani 1 1 d . . . . .
C4 C 0.5641(3) 0.36859(16) 0.89680(15) 0.0211(5) Uani 1 1 d . . . . .
H4A H 0.489682 0.363809 0.943747 0.032 Uiso 1 1 calc GR . . . .
H4B H 0.663039 0.399967 0.915222 0.032 Uiso 1 1 calc GR . . . .
H4C H 0.588426 0.303611 0.875945 0.032 Uiso 1 1 calc GR . . . .
C5 C 0.3356(2) 0.54388(16) 0.90841(14) 0.0191(5) Uani 1 1 d . . . . .
H5A H 0.242930 0.502119 0.898087 0.029 Uiso 1 1 calc GR . . . .
H5B H 0.301144 0.611654 0.909284 0.029 Uiso 1 1 calc GR . . . .
H5C H 0.383506 0.527121 0.962154 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.6177(2) 0.58724(14) 0.85067(13) 0.0130(4) Uani 1 1 d . . . . .
C7 C 0.6237(3) 0.64524(15) 0.92168(14) 0.0164(4) Uani 1 1 d . . . . .
H7 H 0.531021 0.648611 0.955752 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7569(3) 0.69827(16) 0.94548(14) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.754890 0.736384 0.994671 0.024 Uiso 1 1 calc R . . . .
C9 C 0.8916(3) 0.69482(16) 0.89694(14) 0.0199(5) Uani 1 1 d . . . . .
H9 H 0.984597 0.730098 0.912175 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8899(3) 0.63906(15) 0.82529(15) 0.0181(5) Uani 1 1 d . . . . .
H10 H 0.983561 0.637708 0.791875 0.022 Uiso 1 1 calc R . . . .
C11 C 0.7579(2) 0.58467(15) 0.79940(13) 0.0138(4) Uani 1 1 d . . . . .
C12 C 0.7834(2) 0.52933(15) 0.71676(13) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.6500(2) 0.53779(15) 0.65264(13) 0.0139(4) Uani 1 1 d . . . . .
C14 C 0.7136(2) 0.37647(15) 0.66634(13) 0.0145(4) Uani 1 1 d . . . . .
C15 C 0.9311(3) 0.56367(17) 0.66713(14) 0.0204(5) Uani 1 1 d . . . . .
H15A H 1.028598 0.547533 0.698036 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.925393 0.633865 0.659039 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.933141 0.531390 0.612845 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.9262(3) 0.37743(17) 0.77117(15) 0.0219(5) Uani 1 1 d . . . . .
H16A H 1.023227 0.379108 0.736971 0.033 Uiso 1 1 calc GR . . . .
H16B H 0.897909 0.310066 0.783226 0.033 Uiso 1 1 calc GR . . . .
H16C H 0.945488 0.411999 0.823464 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.4725(2) 0.41820(16) 0.58118(14) 0.0167(5) Uani 1 1 d . . . . .
H17A H 0.471298 0.347294 0.572435 0.020 Uiso 1 1 calc R . . . .
H17B H 0.471752 0.449645 0.525834 0.020 Uiso 1 1 calc R . . . .
C18 C 0.3197(3) 0.44827(16) 0.62963(14) 0.0168(4) Uani 1 1 d . . . . .
H18A H 0.278438 0.509731 0.606392 0.020 Uiso 1 1 calc R . . . .
H18B H 0.236411 0.398188 0.621720 0.020 Uiso 1 1 calc R . . . .
O3 O 0.1788(2) 0.68470(12) 0.56793(11) 0.0249(4) Uani 1 1 d D . . . .
H6 H 0.616(3) 0.6650(18) 0.6483(15) 0.020(6) Uiso 1 1 d . . . . .
H3 H 0.335(3) 0.674(2) 0.7648(17) 0.030(8) Uiso 1 1 d . . . . .
H4D H 0.515(3) 0.7152(19) 0.449(2) 0.058(11) Uiso 1 1 d D . . . .
H4E H 0.499(4) 0.639(2) 0.5139(16) 0.062(11) Uiso 1 1 d D . . . .
H3A H 0.258(3) 0.685(2) 0.5281(15) 0.044(9) Uiso 1 1 d D . . . .
H3B H 0.225(4) 0.667(3) 0.6176(16) 0.080(13) Uiso 1 1 d 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
O1 0.0270(8) 0.0133(7) 0.0255(9) -0.0029(6) 0.0028(7) -0.0017(7)
O2 0.0235(8) 0.0149(7) 0.0182(8) -0.0004(6) 0.0007(7) 0.0024(6)
O4 0.0299(10) 0.0364(11) 0.0206(10) 0.0018(8) -0.0001(8) -0.0043(9)
N1 0.0142(8) 0.0147(9) 0.0139(9) -0.0019(7) -0.0008(7) -0.0008(7)
N2 0.0155(9) 0.0121(8) 0.0161(9) 0.0016(7) 0.0003(7) 0.0000(7)
N3 0.0164(9) 0.0164(9) 0.0176(10) -0.0030(8) -0.0022(8) 0.0017(7)
N4 0.0139(8) 0.0134(8) 0.0146(9) -0.0004(7) -0.0011(7) 0.0008(7)
N5 0.0130(8) 0.0156(9) 0.0159(9) -0.0016(7) -0.0008(7) 0.0035(7)
N6 0.0193(9) 0.0149(9) 0.0182(10) 0.0013(8) 0.0001(8) -0.0002(8)
C1 0.0133(10) 0.0156(10) 0.0175(11) 0.0005(8) 0.0048(9) 0.0000(8)
C2 0.0133(10) 0.0121(10) 0.0130(10) -0.0004(8) 0.0016(8) 0.0008(8)
C3 0.0092(9) 0.0167(10) 0.0133(10) -0.0028(8) 0.0032(8) -0.0019(8)
C4 0.0243(12) 0.0191(11) 0.0199(12) 0.0049(9) 0.0006(10) 0.0015(9)
C5 0.0165(11) 0.0220(11) 0.0189(12) -0.0022(9) 0.0045(9) -0.0006(9)
C6 0.0138(10) 0.0117(9) 0.0136(10) 0.0020(8) -0.0030(8) -0.0002(8)
C7 0.0174(10) 0.0169(10) 0.0151(11) -0.0008(8) -0.0002(9) 0.0012(8)
C8 0.0250(12) 0.0173(11) 0.0166(11) -0.0024(9) -0.0071(9) 0.0008(9)
C9 0.0201(11) 0.0174(10) 0.0223(12) 0.0003(9) -0.0083(10) -0.0021(9)
C10 0.0148(10) 0.0188(11) 0.0208(12) 0.0007(9) -0.0006(9) -0.0009(9)
C11 0.0150(10) 0.0132(10) 0.0133(10) 0.0026(8) -0.0015(8) 0.0005(8)
C12 0.0111(9) 0.0161(10) 0.0154(11) 0.0006(8) 0.0007(8) -0.0009(8)
C13 0.0131(10) 0.0154(10) 0.0131(11) -0.0012(8) 0.0039(8) -0.0024(8)
C14 0.0139(10) 0.0169(10) 0.0126(10) 0.0025(8) 0.0047(8) 0.0009(8)
C15 0.0160(11) 0.0273(12) 0.0177(11) -0.0024(9) 0.0028(9) -0.0057(9)
C16 0.0188(11) 0.0251(12) 0.0218(12) 0.0023(10) -0.0023(10) 0.0065(9)
C17 0.0157(10) 0.0184(11) 0.0160(11) -0.0029(9) -0.0024(9) -0.0014(9)
C18 0.0153(10) 0.0181(10) 0.0171(11) -0.0052(9) -0.0027(9) -0.0011(9)
O3 0.0202(9) 0.0323(10) 0.0224(9) 0.0060(8) -0.0031(7) -0.0029(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
O1 C1 1.217(3) . ?
O2 C14 1.219(2) . ?
O4 H4D 0.920(19) . ?
O4 H4E 0.922(19) . ?
N1 C1 1.407(3) . ?
N1 C3 1.391(3) . ?
N1 C18 1.456(3) . ?
N2 C1 1.347(3) . ?
N2 C2 1.465(3) . ?
N2 C4 1.448(3) . ?
N3 C3 1.263(3) . ?
N3 H3 0.86(3) . ?
N4 C13 1.383(3) . ?
N4 C14 1.404(3) . ?
N4 C17 1.457(3) . ?
N5 C12 1.474(3) . ?
N5 C14 1.353(3) . ?
N5 C16 1.452(3) . ?
N6 C13 1.262(3) . ?
N6 H6 0.88(3) . ?
C2 C3 1.538(3) . ?
C2 C5 1.547(3) . ?
C2 C6 1.553(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.396(3) . ?
C6 C11 1.433(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(3) . ?
C11 C12 1.547(3) . ?
C12 C13 1.523(3) . ?
C12 C15 1.545(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.553(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O3 H3A 0.919(19) . ?
O3 H3B 0.920(19) . ?
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
H4D O4 H4E 108(3) . . ?
C1 N1 C18 120.65(18) . . ?
C3 N1 C1 111.42(18) . . ?
C3 N1 C18 124.39(18) . . ?
C1 N2 C2 112.54(17) . . ?
C1 N2 C4 122.84(18) . . ?
C4 N2 C2 123.09(18) . . ?
C3 N3 H3 109.3(18) . . ?
C13 N4 C14 111.44(17) . . ?
C13 N4 C17 123.41(17) . . ?
C14 N4 C17 122.18(17) . . ?
C14 N5 C12 111.41(17) . . ?
C14 N5 C16 121.59(18) . . ?
C16 N5 C12 122.74(18) . . ?
C13 N6 H6 111.7(16) . . ?
O1 C1 N1 124.1(2) . . ?
O1 C1 N2 128.3(2) . . ?
N2 C1 N1 107.62(17) . . ?
N2 C2 C3 101.51(16) . . ?
N2 C2 C5 107.97(17) . . ?
N2 C2 C6 111.36(16) . . ?
C3 C2 C5 104.98(16) . . ?
C3 C2 C6 115.60(16) . . ?
C5 C2 C6 114.38(17) . . ?
N1 C3 C2 106.20(17) . . ?
N3 C3 N1 124.3(2) . . ?
N3 C3 C2 129.28(19) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 115.45(18) . . ?
C7 C6 C11 117.07(19) . . ?
C11 C6 C2 127.43(18) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 C6 123.9(2) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 118.2 . . ?
C9 C10 C11 123.7(2) . . ?
C11 C10 H10 118.2 . . ?
C6 C11 C12 128.21(18) . . ?
C10 C11 C6 117.45(19) . . ?
C10 C11 C12 114.33(18) . . ?
N5 C12 C11 114.15(17) . . ?
N5 C12 C13 101.52(16) . . ?
N5 C12 C15 107.62(17) . . ?
C13 C12 C11 116.21(17) . . ?
C13 C12 C15 102.28(17) . . ?
C15 C12 C11 113.68(17) . . ?
N4 C13 C12 106.60(17) . . ?
N6 C13 N4 123.6(2) . . ?
N6 C13 C12 129.5(2) . . ?
O2 C14 N4 124.9(2) . . ?
O2 C14 N5 127.5(2) . . ?
N5 C14 N4 107.58(17) . . ?
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 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17A 109.2 . . ?
N4 C17 H17B 109.2 . . ?
N4 C17 C18 112.25(17) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
N1 C18 C17 112.50(17) . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
H3A O3 H3B 108(3) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4D O3 0.920(19) 1.97(2) 2.869(3) 167(3) 4_566 yes
O4 H4E N6 0.922(19) 1.92(2) 2.830(3) 168(3) . yes
O3 H3A O4 0.919(19) 1.93(2) 2.826(3) 164(3) . yes
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
N2 C2 C3 N1 4.18(19) . . . . ?
N2 C2 C3 N3 178.6(2) . . . . ?
N2 C2 C6 C7 -123.7(2) . . . . ?
N2 C2 C6 C11 53.6(3) . . . . ?
N4 C17 C18 N1 -22.5(3) . . . . ?
N5 C12 C13 N4 -8.1(2) . . . . ?
N5 C12 C13 N6 178.2(2) . . . . ?
C1 N1 C3 N3 -174.1(2) . . . . ?
C1 N1 C3 C2 0.6(2) . . . . ?
C1 N1 C18 C17 -55.8(3) . . . . ?
C1 N2 C2 C3 -8.1(2) . . . . ?
C1 N2 C2 C5 102.0(2) . . . . ?
C1 N2 C2 C6 -131.64(18) . . . . ?
C2 N2 C1 O1 -172.4(2) . . . . ?
C2 N2 C1 N1 8.8(2) . . . . ?
C2 C6 C7 C8 176.48(19) . . . . ?
C2 C6 C11 C10 -176.26(19) . . . . ?
C2 C6 C11 C12 4.4(3) . . . . ?
C3 N1 C1 O1 175.4(2) . . . . ?
C3 N1 C1 N2 -5.7(2) . . . . ?
C3 N1 C18 C17 101.1(2) . . . . ?
C3 C2 C6 C7 121.11(19) . . . . ?
C3 C2 C6 C11 -61.6(3) . . . . ?
C4 N2 C1 O1 -6.1(3) . . . . ?
C4 N2 C1 N1 175.12(18) . . . . ?
C4 N2 C2 C3 -174.33(18) . . . . ?
C4 N2 C2 C5 -64.3(2) . . . . ?
C4 N2 C2 C6 62.1(2) . . . . ?
C5 C2 C3 N1 -108.17(18) . . . . ?
C5 C2 C3 N3 66.3(3) . . . . ?
C5 C2 C6 C7 -1.0(3) . . . . ?
C5 C2 C6 C11 176.30(19) . . . . ?
C6 C2 C3 N1 124.82(18) . . . . ?
C6 C2 C3 N3 -60.8(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C11 C12 N5 -71.2(3) . . . . ?
C6 C11 C12 C13 46.5(3) . . . . ?
C6 C11 C12 C15 164.9(2) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
C7 C6 C11 C12 -178.32(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C10 C11 C12 179.21(19) . . . . ?
C10 C11 C12 N5 109.5(2) . . . . ?
C10 C11 C12 C13 -132.8(2) . . . . ?
C10 C11 C12 C15 -14.5(3) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C11 C12 C13 N4 -132.54(18) . . . . ?
C11 C12 C13 N6 53.8(3) . . . . ?
C12 N5 C14 O2 167.9(2) . . . . ?
C12 N5 C14 N4 -11.6(2) . . . . ?
C13 N4 C14 O2 -173.6(2) . . . . ?
C13 N4 C14 N5 5.9(2) . . . . ?
C13 N4 C17 C18 -53.4(3) . . . . ?
C14 N4 C13 N6 176.1(2) . . . . ?
C14 N4 C13 C12 1.9(2) . . . . ?
C14 N4 C17 C18 105.4(2) . . . . ?
C14 N5 C12 C11 137.99(18) . . . . ?
C14 N5 C12 C13 12.2(2) . . . . ?
C14 N5 C12 C15 -94.9(2) . . . . ?
C15 C12 C13 N4 103.04(18) . . . . ?
C15 C12 C13 N6 -70.6(3) . . . . ?
C16 N5 C12 C11 -64.9(3) . . . . ?
C16 N5 C12 C13 169.23(18) . . . . ?
C16 N5 C12 C15 62.2(2) . . . . ?
C16 N5 C14 O2 10.5(3) . . . . ?
C16 N5 C14 N4 -168.97(18) . . . . ?
C17 N4 C13 N6 -23.1(3) . . . . ?
C17 N4 C13 C12 162.73(18) . . . . ?
C17 N4 C14 O2 25.3(3) . . . . ?
C17 N4 C14 N5 -155.23(18) . . . . ?
C18 N1 C1 O1 -24.9(3) . . . . ?
C18 N1 C1 N2 153.93(18) . . . . ?
C18 N1 C3 N3 27.1(3) . . . . ?
C18 N1 C3 C2 -158.13(18) . . . . ?
_shelx_res_file
;
TITL testo1_a.res in P2(1)2(1)2(1)
testo1.res
created by SHELXL-2017/1 at 13:39:53 on 08-Jan-2020
REM Old TITL testo1 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.086, Rweak 0.019, Alpha 0.001, Orientation as input
REM Flack x = 0.317 ( 0.492 ) from Parsons' quotients
REM Formula found by SHELXT: C18 N4 O6
CELL 0.71073 8.3617 13.8207 16.0698 90 90 90
ZERR 4 0.0003 0.0006 0.0006 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 72 104 24 16
EQIV $1 0.5+X,1.5-Y,1-Z
SADI 0.01 O3 H3b O4 H4e O4 H4d O3 H3a
L.S. 4 0 0
PLAN 5
TEMP -173.12
HTAB O4 N6
HTAB O4 O3_$1
HTAB O3 O4
BOND $H
CONF
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.035400 0.272100
FVAR 0.61562
O1 4 0.405375 0.299848 0.747584 11.00000 0.02697 0.01329 =
0.02546 -0.00289 0.00283 -0.00172
O2 4 0.719439 0.290626 0.649209 11.00000 0.02347 0.01492 =
0.01818 -0.00041 0.00072 0.00242
O4 4 0.452737 0.664300 0.466456 11.00000 0.02990 0.03636 =
0.02061 0.00184 -0.00009 -0.00433
N1 3 0.349194 0.460667 0.718282 11.00000 0.01423 0.01475 =
0.01393 -0.00187 -0.00080 -0.00076
N2 3 0.491764 0.425337 0.831026 11.00000 0.01555 0.01214 =
0.01609 0.00155 0.00028 0.00000
N3 3 0.309719 0.628133 0.731244 11.00000 0.01639 0.01640 =
0.01756 -0.00301 -0.00224 0.00174
N4 3 0.618418 0.444952 0.625036 11.00000 0.01386 0.01344 =
0.01465 -0.00038 -0.00115 0.00077
N5 3 0.795911 0.423541 0.726487 11.00000 0.01301 0.01559 =
0.01593 -0.00163 -0.00076 0.00354
N6 3 0.586217 0.612457 0.622030 11.00000 0.01930 0.01489 =
0.01817 0.00127 0.00010 -0.00019
C1 1 0.415665 0.385138 0.765725 11.00000 0.01328 0.01555 =
0.01745 0.00048 0.00484 -0.00001
C2 1 0.460349 0.529263 0.838486 11.00000 0.01333 0.01214 =
0.01302 -0.00043 0.00158 0.00082
C3 1 0.369189 0.549712 0.757223 11.00000 0.00916 0.01667 =
0.01328 -0.00279 0.00325 -0.00186
C4 1 0.564074 0.368593 0.896803 11.00000 0.02432 0.01915 =
0.01993 0.00491 0.00064 0.00154
AFIX 137
H4A 2 0.489682 0.363809 0.943747 11.00000 -1.50000
H4B 2 0.663039 0.399967 0.915222 11.00000 -1.50000
H4C 2 0.588426 0.303611 0.875945 11.00000 -1.50000
AFIX 0
C5 1 0.335551 0.543878 0.908407 11.00000 0.01653 0.02197 =
0.01888 -0.00218 0.00450 -0.00059
AFIX 137
H5A 2 0.242930 0.502119 0.898087 11.00000 -1.50000
H5B 2 0.301144 0.611654 0.909284 11.00000 -1.50000
H5C 2 0.383506 0.527121 0.962154 11.00000 -1.50000
AFIX 0
C6 1 0.617730 0.587235 0.850666 11.00000 0.01377 0.01167 =
0.01361 0.00197 -0.00297 -0.00024
C7 1 0.623701 0.645238 0.921682 11.00000 0.01736 0.01686 =
0.01505 -0.00085 -0.00025 0.00117
AFIX 43
H7 2 0.531021 0.648611 0.955752 11.00000 -1.20000
AFIX 0
C8 1 0.756949 0.698272 0.945485 11.00000 0.02502 0.01732 =
0.01660 -0.00237 -0.00712 0.00078
AFIX 43
H8 2 0.754890 0.736384 0.994671 11.00000 -1.20000
AFIX 0
C9 1 0.891581 0.694825 0.896942 11.00000 0.02014 0.01737 =
0.02233 0.00035 -0.00833 -0.00213
AFIX 43
H9 2 0.984597 0.730098 0.912175 11.00000 -1.20000
AFIX 0
C10 1 0.889860 0.639064 0.825287 11.00000 0.01479 0.01876 =
0.02083 0.00072 -0.00064 -0.00088
AFIX 43
H10 2 0.983561 0.637708 0.791875 11.00000 -1.20000
AFIX 0
C11 1 0.757874 0.584667 0.799403 11.00000 0.01499 0.01317 =
0.01329 0.00255 -0.00151 0.00052
C12 1 0.783408 0.529334 0.716765 11.00000 0.01105 0.01614 =
0.01543 0.00062 0.00073 -0.00093
C13 1 0.650013 0.537786 0.652643 11.00000 0.01313 0.01538 =
0.01313 -0.00123 0.00395 -0.00237
C14 1 0.713610 0.376474 0.666340 11.00000 0.01391 0.01693 =
0.01261 0.00247 0.00467 0.00089
C15 1 0.931143 0.563670 0.667133 11.00000 0.01602 0.02732 =
0.01774 -0.00243 0.00278 -0.00567
AFIX 137
H15A 2 1.028598 0.547533 0.698036 11.00000 -1.50000
H15B 2 0.925393 0.633865 0.659039 11.00000 -1.50000
H15C 2 0.933141 0.531390 0.612845 11.00000 -1.50000
AFIX 0
C16 1 0.926229 0.377429 0.771170 11.00000 0.01878 0.02508 =
0.02183 0.00226 -0.00234 0.00646
AFIX 137
H16A 2 1.023227 0.379108 0.736971 11.00000 -1.50000
H16B 2 0.897909 0.310066 0.783226 11.00000 -1.50000
H16C 2 0.945488 0.411999 0.823464 11.00000 -1.50000
AFIX 0
C17 1 0.472458 0.418196 0.581185 11.00000 0.01570 0.01844 =
0.01600 -0.00291 -0.00242 -0.00140
AFIX 23
H17A 2 0.471298 0.347294 0.572435 11.00000 -1.20000
H17B 2 0.471752 0.449645 0.525834 11.00000 -1.20000
AFIX 0
C18 1 0.319689 0.448266 0.629633 11.00000 0.01528 0.01807 =
0.01709 -0.00522 -0.00273 -0.00114
AFIX 23
H18A 2 0.278438 0.509731 0.606392 11.00000 -1.20000
H18B 2 0.236411 0.398188 0.621720 11.00000 -1.20000
AFIX 0
O3 4 0.178794 0.684700 0.567935 11.00000 0.02015 0.03227 =
0.02235 0.00596 -0.00308 -0.00287
H6 2 0.616085 0.664953 0.648289 11.00000 0.01957
H3 2 0.334660 0.674026 0.764810 11.00000 0.03038
H4D 2 0.514740 0.715205 0.448547 11.00000 0.05813
H4E 2 0.499245 0.639368 0.513881 11.00000 0.06205
H3A 2 0.257617 0.684926 0.528086 11.00000 0.04402
H3B 2 0.225361 0.667390 0.617607 11.00000 0.08027
HKLF 4
REM testo1_a.res in P2(1)2(1)2(1)
REM R1 = 0.0355 for 3893 Fo > 4sig(Fo) and 0.0444 for all 4432 data
REM 281 parameters refined using 6 restraints
END
WGHT 0.0354 0.2721
REM Highest difference peak 0.246, deepest hole -0.176, 1-sigma level 0.041
Q1 1 0.4144 0.5431 0.7972 11.00000 0.05 0.25
Q2 1 0.8552 0.5408 0.6885 11.00000 0.05 0.18
Q3 1 0.6364 0.5847 0.9052 11.00000 0.05 0.17
Q4 1 0.7993 0.4774 0.7211 11.00000 0.05 0.16
Q5 1 0.3859 0.4215 0.6042 11.00000 0.05 0.16
;
_shelx_res_checksum 30249
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'