# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
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data_Complex-7
_database_code_depnum_ccdc_archive 'CCDC 1555235'
_audit_update_record
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT084_Complex-7
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.36 Report
RESPONSE: The crystals of this complex were small sized with poor X-ray
diffraction and repeated recrystallization under different environments
did not converged to better quality crystals. This alert is due to the
low quality of the diffraction data. The reported structure is the best
possible solution so far achieved after refinement with some constraints.
;
_vrf_PLAT201_Complex-7
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 2 Report
RESPONSE: Among 5 disordered atoms on one morpholine ring, the displacement
parameters of two carbon atoms (C19 and C21) became non-positive definit
during anisotropic refinement. Therefore these were refined isotropically
for disorder modelling.
;
_vrf_PLAT306_Complex-7
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O7 Check
RESPONSE: The hydrogen atoms associated with the solvate water molecules
could not be located in the difference density map.
;
_vrf_PLAT601_Complex-7
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of . 171 Ang3
RESPONSE: This may be associated to the large cavity formed by complex and
solvate water molecules. In order to highlight the contribution of solvent
molecules in crystallization, the PLATON/SQUEEZE option was not invoked.
;
_audit_creation_date 2017-08-06
_audit_creation_method SHELXL-2014/7
_shelx_SHELXL_version_number 2014/7
_chemical_name_systematic ?
_chemical_name_common none
_chemical_melting_point 'not measured'
_chemical_formula_moiety 'C22 H32 N16 Ni O4, 0.269(O2), 2(Cl), 2.462(O)'
_chemical_formula_sum 'C22 H32 Cl2 N16 Ni O7'
_chemical_formula_weight 762.23
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'
Cl Cl 0.1484 0.1585 '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'
Ni Ni 0.3393 1.1124 '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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 12.261(3)
_cell_length_b 12.784(4)
_cell_length_c 13.598(4)
_cell_angle_alpha 74.133(8)
_cell_angle_beta 70.006(8)
_cell_angle_gamma 64.470(7)
_cell_volume 1787.3(9)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9953
_cell_measurement_theta_min 3.053
_cell_measurement_theta_max 26.928
_exptl_crystal_description Needle
_exptl_crystal_colour colourless
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method none
_exptl_crystal_density_diffrn 1.416
_exptl_crystal_F_000 788
_exptl_transmission_factor_min 0.968
_exptl_transmission_factor_max 0.977
_exptl_crystal_size_max 0.288
_exptl_crystal_size_mid 0.156
_exptl_crystal_size_min 0.076
_exptl_absorpt_coefficient_mu 0.754
_shelx_estimated_absorpt_T_min 0.812
_shelx_estimated_absorpt_T_max 0.945
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.868
_exptl_absorpt_correction_T_max 0.944
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1185 before and 0.0752 after correction. The Ratio of minimum to maximum transmission is 0.9073. The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details
;
The crystal was mounted using Paratone-N oil (cryoprotectant)
on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic
head of goniometer directly into the cold gas stream of a
liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focused sealed tube'
_diffrn_measurement_device_type
;
Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method
;
\f and \w scans with 0.5 deg/frame and 20 seconds of
exposure time. Detector was at 50mm from crystal.
;
_diffrn_detector 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_radiation_monochromator 'Multi-layer X-ray mirror'
_diffrn_radiation_probe x-ray
_diffrn_reflns_number 68001
_diffrn_reflns_av_unetI/netI 0.1003
_diffrn_reflns_av_R_equivalents 0.1408
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.796
_diffrn_reflns_theta_max 27.310
_diffrn_reflns_theta_full 25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 7929
_reflns_number_gt 4657
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_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.
;
_computing_data_collection 'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement 'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution 'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics
;
ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material 'WinGX2014.1 (Farrugia, 2012)'
_refine_special_details ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1734P)^2^+12.0684P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary mixed
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 7929
_refine_ls_number_parameters 462
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1972
_refine_ls_R_factor_gt 0.1218
_refine_ls_wR_factor_ref 0.3581
_refine_ls_wR_factor_gt 0.3076
_refine_ls_goodness_of_fit_ref 1.099
_refine_ls_restrained_S_all 1.099
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
Cl1A Cl 0.35(6) -0.14(2) 0.72(3) 0.28(2) Uani 0.538(7) 1 d . . P A 1
O5A O 0.372(2) -0.0764(11) 0.5007(12) 0.108(6) Uani 0.538(7) 1 d . . P A 1
O6A O 0.4843(17) -0.0070(15) 0.9725(14) 0.068(3) Uiso 0.538(7) 1 d . . P A 1
C19A C 0.9358(14) 0.3345(15) 0.4244(12) 0.031(3) Uiso 0.538(7) 1 d . . P A 1
H19A H 0.9210 0.2851 0.3894 0.037 Uiso 0.538(7) 1 calc R U P A 1
H19B H 0.8888 0.4172 0.3989 0.037 Uiso 0.538(7) 1 calc R U P A 1
C20A C 1.0587(17) 0.317(2) 0.3895(13) 0.047(4) Uani 0.538(7) 1 d . . P A 1
H20A H 1.0685 0.3754 0.3257 0.056 Uiso 0.538(7) 1 calc R U P A 1
H20B H 1.1027 0.2389 0.3658 0.056 Uiso 0.538(7) 1 calc R U P A 1
C21A C 0.9689(14) 0.2667(16) 0.6030(12) 0.028(3) Uiso 0.538(7) 1 d . . P A 1
H21A H 0.9235 0.2622 0.6789 0.033 Uiso 0.538(7) 1 calc R U P A 1
H21B H 1.0300 0.1873 0.5890 0.033 Uiso 0.538(7) 1 calc R U P A 1
C22A C 1.0323(18) 0.3478(19) 0.5756(14) 0.048(4) Uani 0.538(7) 1 d . . P A 1
H22A H 1.0807 0.3321 0.6267 0.058 Uiso 0.538(7) 1 calc R U P A 1
H22B H 0.9720 0.4301 0.5731 0.058 Uiso 0.538(7) 1 calc R U P A 1
O4A O 1.1264(14) 0.3206(16) 0.4561(16) 0.038(4) Uani 0.538(7) 1 d . . P A 1
Cl1B Cl 0.34(7) -0.14(3) 0.72(3) 0.28(2) Uani 0.462(7) 1 d . . P A 2
O5B O 0.612(2) -0.1372(13) 0.5344(14) 0.108(6) Uani 0.462(7) 1 d . . P A 2
O6B O 0.5395(19) -0.0199(17) 0.9344(16) 0.068(3) Uiso 0.462(7) 1 d . . P A 2
C19B C 0.9190(17) 0.3856(18) 0.4306(14) 0.031(3) Uiso 0.462(7) 1 d . . P A 2
H19C H 0.9337 0.3412 0.3749 0.037 Uiso 0.462(7) 1 calc R U P A 2
H19D H 0.8442 0.4577 0.4245 0.037 Uiso 0.462(7) 1 calc R U P A 2
C20B C 0.996(2) 0.413(2) 0.4083(16) 0.047(4) Uani 0.462(7) 1 d . . P A 2
H20C H 0.9594 0.4997 0.4045 0.056 Uiso 0.462(7) 1 calc R U P A 2
H20D H 1.0417 0.3969 0.3351 0.056 Uiso 0.462(7) 1 calc R U P A 2
C21B C 0.9472(16) 0.3176(19) 0.6113(14) 0.027(4) Uiso 0.462(7) 1 d . . P A 2
H21C H 0.9225 0.2755 0.6828 0.032 Uiso 0.462(7) 1 calc R U P A 2
H21D H 0.9272 0.3998 0.6170 0.032 Uiso 0.462(7) 1 calc R U P A 2
C22B C 1.089(2) 0.256(2) 0.5586(17) 0.048(4) Uani 0.462(7) 1 d . . P A 2
H22C H 1.1090 0.1845 0.5306 0.058 Uiso 0.462(7) 1 calc R U P A 2
H22D H 1.1441 0.2400 0.6047 0.058 Uiso 0.462(7) 1 calc R U P A 2
O4B O 1.0874(17) 0.3698(19) 0.467(2) 0.038(4) Uani 0.462(7) 1 d . . P A 2
Ni1 Ni 0.36485(8) 0.29947(9) 0.72063(8) 0.0278(3) Uani 1 1 d . . . . .
O1 O -0.3353(5) 0.1717(6) 0.9873(5) 0.0433(15) Uani 1 1 d . . . . .
O2 O 0.2872(5) 0.4696(5) 0.7492(4) 0.0272(12) Uani 1 1 d . . . . .
O3 O 0.3200(5) 0.3508(5) 0.5794(4) 0.0344(13) Uani 1 1 d . . . . .
N1 N -0.1160(6) 0.2164(6) 0.9042(7) 0.045(2) Uani 1 1 d . . . . .
N2 N 0.0954(6) 0.1514(6) 0.8323(5) 0.0305(15) Uani 1 1 d . . . . .
N3 N -0.0200(6) 0.3475(6) 0.8714(6) 0.0343(16) Uani 1 1 d . . . . .
N4 N 0.1987(5) 0.2830(5) 0.7960(5) 0.0215(12) Uani 1 1 d . . . . .
N5 N -0.0277(6) 0.5553(6) 0.8811(5) 0.0300(15) Uani 1 1 d . . . . .
N6 N 0.0834(6) 0.4721(5) 0.8371(5) 0.0258(13) Uani 1 1 d . . . . .
N7 N 0.3032(6) 0.0968(6) 0.7539(5) 0.0295(15) Uani 1 1 d . . . . .
N8 N 0.4113(6) 0.1255(6) 0.7060(7) 0.0417(18) Uani 1 1 d . . . . .
H8A H 0.4392 0.1168 0.6364 0.050 Uiso 1 1 calc R U . . .
H8B H 0.4732 0.0768 0.7382 0.050 Uiso 1 1 calc R U . . .
N9 N 0.4418(6) 0.2459(6) 0.8501(5) 0.0308(15) Uani 1 1 d . . . . .
H9A H 0.3968 0.2980 0.8970 0.037 Uiso 1 1 calc R U . . .
H9B H 0.4399 0.1744 0.8838 0.037 Uiso 1 1 calc R U . . .
N10 N 0.5665(6) 0.2401(7) 0.8123(6) 0.0344(16) Uani 1 1 d . . . . .
N11 N 0.5340(6) 0.3064(6) 0.6472(5) 0.0253(13) Uani 1 1 d . . . . .
N12 N 0.7278(6) 0.2722(6) 0.6786(5) 0.0322(15) Uani 1 1 d . . . . .
N13 N 0.6972(6) 0.3415(6) 0.5031(5) 0.0290(15) Uani 1 1 d . . . . .
N14 N 0.8807(6) 0.3124(7) 0.5364(6) 0.0393(18) Uani 1 1 d . . . . .
N15 N 0.5090(5) 0.3744(6) 0.4765(5) 0.0248(13) Uani 1 1 d . . . . .
N16 N 0.5578(6) 0.4014(6) 0.3696(5) 0.0275(14) Uani 1 1 d . . . . .
C1 C -0.2172(8) 0.0760(9) 0.9815(9) 0.050(3) Uani 1 1 d . . . . .
H1A H -0.2242 0.0056 0.9712 0.061 Uiso 1 1 calc R U . . .
H1B H -0.1940 0.0580 1.0488 0.061 Uiso 1 1 calc R U . . .
C2 C -0.3301(8) 0.2724(9) 1.0053(9) 0.049(2) Uani 1 1 d . . . . .
H2A H -0.3083 0.2553 1.0733 0.059 Uiso 1 1 calc R U . . .
H2B H -0.4137 0.3361 1.0114 0.059 Uiso 1 1 calc R U . . .
C3 C -0.1190(9) 0.1044(8) 0.8934(9) 0.049(2) Uani 1 1 d . . . . .
H3A H -0.1363 0.1128 0.8251 0.059 Uiso 1 1 calc R U . . .
H3B H -0.0367 0.0403 0.8945 0.059 Uiso 1 1 calc R U . . .
C4 C -0.2394(8) 0.3116(8) 0.9216(8) 0.046(2) Uani 1 1 d . . . . .
H4A H -0.2335 0.3781 0.9406 0.055 Uiso 1 1 calc R U . . .
H4B H -0.2671 0.3393 0.8555 0.055 Uiso 1 1 calc R U . . .
C5 C -0.0111(7) 0.2378(7) 0.8683(7) 0.0341(19) Uani 1 1 d . . . . .
C6 C 0.1970(6) 0.1777(6) 0.7959(6) 0.0245(16) Uani 1 1 d . . . . .
C7 C 0.0879(7) 0.3609(6) 0.8355(6) 0.0236(15) Uani 1 1 d . . . . .
C8 C -0.1136(9) 0.7616(8) 0.9072(8) 0.044(2) Uani 1 1 d . . . . .
H8C H -0.1462 0.8127 0.8471 0.067 Uiso 1 1 calc R U . . .
H8D H -0.0830 0.8028 0.9363 0.067 Uiso 1 1 calc R U . . .
H8E H -0.1804 0.7406 0.9620 0.067 Uiso 1 1 calc R U . . .
C9 C -0.0091(8) 0.6534(7) 0.8712(6) 0.0336(18) Uani 1 1 d . . . . .
C10 C 0.1142(8) 0.6367(7) 0.8225(6) 0.0332(18) Uani 1 1 d . . . . .
H10A H 0.1513 0.6928 0.8082 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1756(7) 0.5226(7) 0.7978(6) 0.0268(16) Uani 1 1 d . . . . .
C12 C 0.3891(7) 0.3735(7) 0.4919(7) 0.0293(17) Uani 1 1 d . . . . .
C13 C 0.3686(7) 0.4050(8) 0.3905(6) 0.0319(18) Uani 1 1 d . . . . .
H13 H 0.2960 0.4125 0.3741 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4721(6) 0.4232(7) 0.3190(6) 0.0259(16) Uani 1 1 d . . . . .
C15 C 0.4987(7) 0.4590(8) 0.2027(6) 0.0341(19) Uani 1 1 d . . . . .
H15A H 0.4851 0.5426 0.1861 0.051 Uiso 1 1 calc R U . . .
H15B H 0.4428 0.4449 0.1752 0.051 Uiso 1 1 calc R U . . .
H15C H 0.5858 0.4132 0.1699 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5857(7) 0.3372(7) 0.5449(6) 0.0267(16) Uani 1 1 d . . . . .
C17 C 0.6126(7) 0.2726(7) 0.7087(7) 0.0310(18) Uani 1 1 d . . . . .
C18 C 0.7661(7) 0.3081(7) 0.5739(6) 0.0309(18) Uani 1 1 d . . . . .
Cl2 Cl -0.3090(2) 0.5947(2) 0.9630(2) 0.0513(7) Uani 1 1 d . . . . .
O7 O -0.4137(14) 0.7935(12) 0.7964(12) 0.142(5) Uani 1 1 d . . . . .
H7 H 0.300(7) 0.023(8) 0.750(7) 0.03(2) Uiso 1 1 d . . . . .
H10 H 0.605(8) 0.206(8) 0.864(7) 0.03(2) Uiso 1 1 d . . . . .
H16 H 0.615(8) 0.424(7) 0.359(6) 0.02(2) Uiso 1 1 d . . . . .
H5 H -0.101(8) 0.540(7) 0.907(7) 0.03(2) 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
Cl1A 0.52(6) 0.069(5) 0.128(8) -0.002(5) -0.029(19) -0.044(14)
O5A 0.175(14) 0.022(5) 0.046(7) -0.013(5) 0.047(8) -0.017(7)
C20A 0.047(9) 0.083(11) 0.029(7) 0.000(8) -0.005(6) -0.049(8)
C22A 0.048(9) 0.073(10) 0.042(8) 0.006(8) -0.027(7) -0.036(8)
O4A 0.015(9) 0.071(13) 0.031(6) -0.013(8) 0.001(7) -0.020(7)
Cl1B 0.52(6) 0.069(5) 0.128(8) -0.002(5) -0.029(19) -0.044(14)
O5B 0.175(14) 0.022(5) 0.046(7) -0.013(5) 0.047(8) -0.017(7)
C20B 0.047(9) 0.083(11) 0.029(7) 0.000(8) -0.005(6) -0.049(8)
C22B 0.048(9) 0.073(10) 0.042(8) 0.006(8) -0.027(7) -0.036(8)
O4B 0.015(9) 0.071(13) 0.031(6) -0.013(8) 0.001(7) -0.020(7)
Ni1 0.0183(5) 0.0340(6) 0.0312(6) -0.0070(4) -0.0003(4) -0.0132(4)
O1 0.030(3) 0.056(4) 0.046(4) -0.009(3) -0.014(3) -0.014(3)
O2 0.025(3) 0.036(3) 0.025(3) -0.007(2) -0.002(2) -0.018(2)
O3 0.025(3) 0.057(4) 0.031(3) -0.017(3) 0.001(2) -0.024(3)
N1 0.027(4) 0.037(4) 0.067(6) -0.009(4) -0.001(4) -0.016(3)
N2 0.024(3) 0.028(3) 0.037(4) -0.003(3) -0.002(3) -0.013(3)
N3 0.020(3) 0.030(4) 0.047(4) -0.009(3) 0.002(3) -0.011(3)
N4 0.022(3) 0.025(3) 0.018(3) -0.004(2) -0.005(2) -0.009(2)
N5 0.024(3) 0.031(4) 0.030(4) -0.009(3) 0.002(3) -0.010(3)
N6 0.023(3) 0.030(3) 0.024(3) -0.008(3) -0.002(3) -0.011(3)
N7 0.024(3) 0.023(3) 0.037(4) -0.004(3) -0.005(3) -0.008(3)
N8 0.019(3) 0.043(4) 0.057(5) -0.019(4) 0.008(3) -0.012(3)
N9 0.026(3) 0.034(4) 0.032(4) -0.001(3) -0.001(3) -0.018(3)
N10 0.019(3) 0.053(5) 0.027(4) 0.001(3) -0.007(3) -0.014(3)
N11 0.023(3) 0.032(3) 0.022(3) -0.004(3) -0.007(3) -0.011(3)
N12 0.027(3) 0.048(4) 0.028(4) -0.004(3) -0.007(3) -0.020(3)
N13 0.019(3) 0.043(4) 0.028(4) -0.010(3) 0.000(3) -0.016(3)
N14 0.022(3) 0.073(5) 0.030(4) -0.003(4) -0.007(3) -0.028(3)
N15 0.021(3) 0.035(3) 0.023(3) -0.010(3) -0.001(2) -0.014(3)
N16 0.025(3) 0.042(4) 0.023(3) -0.008(3) -0.004(3) -0.018(3)
C1 0.032(5) 0.047(6) 0.074(7) -0.006(5) -0.014(5) -0.018(4)
C2 0.025(4) 0.056(6) 0.070(7) -0.029(5) -0.013(4) -0.007(4)
C3 0.041(5) 0.039(5) 0.066(7) -0.016(5) 0.003(5) -0.020(4)
C4 0.034(5) 0.040(5) 0.058(6) -0.010(4) -0.011(4) -0.006(4)
C5 0.025(4) 0.032(4) 0.042(5) -0.005(4) -0.003(3) -0.012(3)
C6 0.020(3) 0.025(4) 0.028(4) -0.001(3) -0.009(3) -0.008(3)
C7 0.023(3) 0.031(4) 0.018(4) 0.000(3) -0.005(3) -0.013(3)
C8 0.051(5) 0.034(5) 0.045(6) -0.016(4) -0.004(4) -0.013(4)
C9 0.043(5) 0.031(4) 0.024(4) -0.005(3) -0.009(4) -0.011(4)
C10 0.039(4) 0.036(4) 0.029(4) -0.006(3) -0.006(4) -0.019(4)
C11 0.026(4) 0.036(4) 0.021(4) -0.004(3) -0.001(3) -0.017(3)
C12 0.017(3) 0.040(4) 0.037(5) -0.015(4) -0.001(3) -0.015(3)
C13 0.026(4) 0.050(5) 0.028(4) -0.013(4) -0.007(3) -0.018(4)
C14 0.019(3) 0.036(4) 0.026(4) -0.014(3) -0.004(3) -0.010(3)
C15 0.027(4) 0.052(5) 0.027(4) -0.009(4) -0.006(3) -0.017(4)
C16 0.029(4) 0.030(4) 0.027(4) -0.009(3) -0.007(3) -0.013(3)
C17 0.024(4) 0.031(4) 0.038(5) -0.008(4) -0.010(3) -0.008(3)
C18 0.025(4) 0.046(5) 0.025(4) -0.012(4) -0.006(3) -0.014(4)
Cl2 0.0270(11) 0.0544(14) 0.0649(17) -0.0200(12) 0.0002(10) -0.0109(10)
O7 0.146(11) 0.130(11) 0.153(12) 0.053(9) -0.062(10) -0.081(9)
_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
O6A O6A 1.03(3) 2_657 ?
C19A C20A 1.35(2) . ?
C19A N14 1.443(17) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A O4A 1.44(3) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A C22A 1.45(2) . ?
C21A N14 1.472(16) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A O4A 1.67(3) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
O6B O6B 1.81(4) 2_657 ?
C19B C20B 1.07(2) . ?
C19B N14 1.532(19) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B O4B 1.43(3) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B N14 1.535(18) . ?
C21B C22B 1.56(3) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B O4B 1.63(3) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
Ni1 N11 2.000(6) . ?
Ni1 N4 2.017(6) . ?
Ni1 O3 2.035(6) . ?
Ni1 O2 2.052(5) . ?
Ni1 N9 2.093(7) . ?
Ni1 N8 2.094(7) . ?
O1 C2 1.406(11) . ?
O1 C1 1.430(11) . ?
O2 C11 1.263(9) . ?
O3 C12 1.246(9) . ?
N1 C5 1.331(10) . ?
N1 C4 1.467(11) . ?
N1 C3 1.495(11) . ?
N2 C6 1.326(9) . ?
N2 C5 1.334(10) . ?
N3 C7 1.313(9) . ?
N3 C5 1.371(10) . ?
N4 C7 1.324(9) . ?
N4 C6 1.356(9) . ?
N5 C9 1.333(11) . ?
N5 N6 1.373(9) . ?
N5 H5 0.94(9) . ?
N6 C7 1.405(10) . ?
N6 C11 1.417(9) . ?
N7 C6 1.322(10) . ?
N7 N8 1.419(9) . ?
N7 H7 0.98(9) . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
N9 N10 1.412(9) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N10 C17 1.347(11) . ?
N10 H10 0.89(9) . ?
N11 C16 1.343(10) . ?
N11 C17 1.345(10) . ?
N12 C17 1.328(10) . ?
N12 C18 1.352(10) . ?
N13 C16 1.308(9) . ?
N13 C18 1.358(10) . ?
N14 C18 1.340(10) . ?
N15 N16 1.378(9) . ?
N15 C16 1.395(10) . ?
N15 C12 1.418(9) . ?
N16 C14 1.339(10) . ?
N16 H16 0.83(9) . ?
C1 C3 1.473(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.444(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.485(12) . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C9 C10 1.372(12) . ?
C10 C11 1.399(11) . ?
C10 H10A 0.9500 . ?
C12 C13 1.404(12) . ?
C13 C14 1.376(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.482(11) . ?
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
C20A C19A N14 119.4(13) . . ?
C20A C19A H19A 107.5 . . ?
N14 C19A H19A 107.5 . . ?
C20A C19A H19B 107.5 . . ?
N14 C19A H19B 107.5 . . ?
H19A C19A H19B 107.0 . . ?
C19A C20A O4A 121.9(16) . . ?
C19A C20A H20A 106.8 . . ?
O4A C20A H20A 106.8 . . ?
C19A C20A H20B 106.8 . . ?
O4A C20A H20B 106.8 . . ?
H20A C20A H20B 106.7 . . ?
C22A C21A N14 106.4(13) . . ?
C22A C21A H21A 110.4 . . ?
N14 C21A H21A 110.4 . . ?
C22A C21A H21B 110.4 . . ?
N14 C21A H21B 110.4 . . ?
H21A C21A H21B 108.6 . . ?
C21A C22A O4A 102.8(16) . . ?
C21A C22A H22A 111.2 . . ?
O4A C22A H22A 111.2 . . ?
C21A C22A H22B 111.2 . . ?
O4A C22A H22B 111.2 . . ?
H22A C22A H22B 109.1 . . ?
C20A O4A C22A 110.5(13) . . ?
C20B C19B N14 124.9(19) . . ?
C20B C19B H19C 106.1 . . ?
N14 C19B H19C 106.1 . . ?
C20B C19B H19D 106.1 . . ?
N14 C19B H19D 106.1 . . ?
H19C C19B H19D 106.3 . . ?
C19B C20B O4B 123(2) . . ?
C19B C20B H20C 106.6 . . ?
O4B C20B H20C 106.6 . . ?
C19B C20B H20D 106.6 . . ?
O4B C20B H20D 106.6 . . ?
H20C C20B H20D 106.6 . . ?
N14 C21B C22B 104.3(14) . . ?
N14 C21B H21C 110.9 . . ?
C22B C21B H21C 110.9 . . ?
N14 C21B H21D 110.9 . . ?
C22B C21B H21D 110.9 . . ?
H21C C21B H21D 108.9 . . ?
C21B C22B O4B 91.1(16) . . ?
C21B C22B H22C 113.4 . . ?
O4B C22B H22C 113.4 . . ?
C21B C22B H22D 113.4 . . ?
O4B C22B H22D 113.4 . . ?
H22C C22B H22D 110.7 . . ?
C20B O4B C22B 118.1(19) . . ?
N11 Ni1 N4 176.9(3) . . ?
N11 Ni1 O3 90.0(2) . . ?
N4 Ni1 O3 91.0(2) . . ?
N11 Ni1 O2 93.4(2) . . ?
N4 Ni1 O2 89.4(2) . . ?
O3 Ni1 O2 91.4(2) . . ?
N11 Ni1 N9 80.1(2) . . ?
N4 Ni1 N9 98.8(2) . . ?
O3 Ni1 N9 170.1(2) . . ?
O2 Ni1 N9 90.2(2) . . ?
N11 Ni1 N8 97.1(3) . . ?
N4 Ni1 N8 80.0(2) . . ?
O3 Ni1 N8 88.7(3) . . ?
O2 Ni1 N8 169.5(2) . . ?
N9 Ni1 N8 91.6(3) . . ?
C2 O1 C1 111.1(7) . . ?
C11 O2 Ni1 126.5(5) . . ?
C12 O3 Ni1 125.8(5) . . ?
C5 N1 C4 121.6(7) . . ?
C5 N1 C3 121.6(7) . . ?
C4 N1 C3 113.6(7) . . ?
C6 N2 C5 115.7(7) . . ?
C7 N3 C5 113.5(6) . . ?
C7 N4 C6 114.2(6) . . ?
C7 N4 Ni1 131.1(5) . . ?
C6 N4 Ni1 114.3(5) . . ?
C9 N5 N6 108.7(6) . . ?
C9 N5 H5 131(5) . . ?
N6 N5 H5 120(5) . . ?
N5 N6 C7 119.7(6) . . ?
N5 N6 C11 108.1(6) . . ?
C7 N6 C11 132.1(6) . . ?
C6 N7 N8 119.1(6) . . ?
C6 N7 H7 117(5) . . ?
N8 N7 H7 123(5) . . ?
N7 N8 Ni1 108.7(5) . . ?
N7 N8 H8A 109.9 . . ?
Ni1 N8 H8A 109.9 . . ?
N7 N8 H8B 109.9 . . ?
Ni1 N8 H8B 109.9 . . ?
H8A N8 H8B 108.3 . . ?
N10 N9 Ni1 108.2(5) . . ?
N10 N9 H9A 110.1 . . ?
Ni1 N9 H9A 110.1 . . ?
N10 N9 H9B 110.1 . . ?
Ni1 N9 H9B 110.1 . . ?
H9A N9 H9B 108.4 . . ?
C17 N10 N9 119.9(7) . . ?
C17 N10 H10 130(6) . . ?
N9 N10 H10 110(6) . . ?
C16 N11 C17 112.8(6) . . ?
C16 N11 Ni1 131.2(5) . . ?
C17 N11 Ni1 115.9(5) . . ?
C17 N12 C18 113.6(7) . . ?
C16 N13 C18 113.9(7) . . ?
C18 N14 C19A 121.7(8) . . ?
C18 N14 C21A 121.8(9) . . ?
C19A N14 C21A 114.9(10) . . ?
C18 N14 C19B 122.3(9) . . ?
C18 N14 C21B 120.5(9) . . ?
C19B N14 C21B 106.8(11) . . ?
N16 N15 C16 119.2(6) . . ?
N16 N15 C12 108.2(6) . . ?
C16 N15 C12 131.7(7) . . ?
C14 N16 N15 108.6(6) . . ?
C14 N16 H16 135(6) . . ?
N15 N16 H16 111(6) . . ?
O1 C1 C3 111.0(8) . . ?
O1 C1 H1A 109.4 . . ?
C3 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C3 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C4 112.2(8) . . ?
O1 C2 H2A 109.2 . . ?
C4 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C4 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C1 C3 N1 109.3(8) . . ?
C1 C3 H3A 109.8 . . ?
N1 C3 H3A 109.8 . . ?
C1 C3 H3B 109.8 . . ?
N1 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C2 C4 N1 110.9(8) . . ?
C2 C4 H4A 109.5 . . ?
N1 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 N2 118.1(7) . . ?
N1 C5 N3 117.4(7) . . ?
N2 C5 N3 124.5(7) . . ?
N7 C6 N2 117.6(7) . . ?
N7 C6 N4 117.8(6) . . ?
N2 C6 N4 124.6(7) . . ?
N3 C7 N4 127.5(7) . . ?
N3 C7 N6 115.6(6) . . ?
N4 C7 N6 116.9(6) . . ?
C9 C8 H8C 109.5 . . ?
C9 C8 H8D 109.5 . . ?
H8C C8 H8D 109.5 . . ?
C9 C8 H8E 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
N5 C9 C10 109.8(7) . . ?
N5 C9 C8 121.5(8) . . ?
C10 C9 C8 128.6(8) . . ?
C9 C10 C11 108.0(7) . . ?
C9 C10 H10A 126.0 . . ?
C11 C10 H10A 126.0 . . ?
O2 C11 C10 131.0(7) . . ?
O2 C11 N6 123.6(7) . . ?
C10 C11 N6 105.3(6) . . ?
O3 C12 C13 130.0(7) . . ?
O3 C12 N15 124.7(7) . . ?
C13 C12 N15 105.3(6) . . ?
C14 C13 C12 108.1(7) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
N16 C14 C13 109.6(7) . . ?
N16 C14 C15 119.9(7) . . ?
C13 C14 C15 130.5(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N13 C16 N11 127.5(7) . . ?
N13 C16 N15 116.4(7) . . ?
N11 C16 N15 116.0(6) . . ?
N12 C17 N11 126.8(8) . . ?
N12 C17 N10 117.3(7) . . ?
N11 C17 N10 115.8(7) . . ?
N14 C18 N12 117.9(7) . . ?
N14 C18 N13 116.9(7) . . ?
N12 C18 N13 125.2(7) . . ?
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
N8 H8A O5A 0.91 2.37 3.125(16) 139.8 2_656
N8 H8A O5B 0.91 2.52 3.33(2) 148.4 2_656
N9 H9A Cl2 0.91 2.33 3.225(7) 168.6 2_567
N9 H9B O6A 0.91 2.23 3.113(19) 164.5 .
N9 H9B O6A 0.91 2.55 3.324(19) 143.2 2_657
N9 H9B O6B 0.91 2.27 3.10(2) 150.8 .
N7 H7 Cl1A 0.98(9) 2.1(4) 3.0(4) 163(19) .
N7 H7 Cl1B 0.98(9) 2.1(5) 3.0(5) 165(21) .
N10 H10 O1 0.89(9) 1.93(10) 2.792(9) 165(8) 1_655
N16 H16 O2 0.83(9) 2.13(9) 2.844(8) 144(8) 2_666
N5 H5 Cl2 0.94(9) 2.23(9) 3.094(7) 152(7) .
_refine_diff_density_max 2.176
_refine_diff_density_min -1.198
_refine_diff_density_rms 0.202
_shelx_res_file
;
shelx.res created by SHELXL-2014/7
TITL AMakop13_0m_a.res in P-1
CELL 0.71073 12.2608 12.7844 13.598 74.133 70.006 64.47
ZERR 4 0.0034 0.0036 0.0038 0.008 0.008 0.007
LATT 1
SFAC C H Cl N Ni O
UNIT 44 64 4 32 2 14
EQIV $1 1-X,-Y,1-Z
EQIV $2 -X,1-Y,2-Z
EQIV $3 1-X,-Y,2-Z
EQIV $4 1-X,1-Y,1-Z
EQIV $5 1+X,+Y,+Z
EADP Cl1A Cl1B
EADP O5A O5B
EADP O6A O6B
EADP C19A C19B
EADP C20A C20B
EADP C22A C22B
EADP O4A O4B
L.S. 50
PLAN 50
SIZE 0.076 0.156 0.288
TEMP -173.16
HTAB N8 O5A_$1
HTAB N8 O5B_$1
HTAB N9 Cl2_$2
HTAB N9 O6A
HTAB N9 O6A_$3
HTAB N9 O6B
HTAB N7 Cl1A
HTAB N7 Cl1B
HTAB N10 O1_$5
HTAB N16 O2_$4
HTAB N5 Cl2
HTAB
BOND $H
LIST 4
fmap 2
acta 50
MERG 2
REM
REM
REM
WGHT 0.173400 12.068400
FVAR 0.39580 0.53812
PART 1
CL1A 3 0.345824 -0.141564 0.715010 21.00000 0.51932 0.06863 =
0.12788 -0.00225 -0.02889 -0.04391
O5A 6 0.372264 -0.076415 0.500741 21.00000 0.17517 0.02176 =
0.04600 -0.01275 0.04683 -0.01726
O6A 6 0.484289 -0.006982 0.972511 21.00000 0.06754
C19A 1 0.935764 0.334515 0.424391 21.00000 0.03064
AFIX 23
H19A 2 0.921005 0.285098 0.389398 21.00000 -1.20000
H19B 2 0.888807 0.417161 0.398861 21.00000 -1.20000
AFIX 0
C20A 1 1.058726 0.316769 0.389539 21.00000 0.04703 0.08347 =
0.02896 -0.00002 -0.00541 -0.04920
AFIX 23
H20A 2 1.068534 0.375375 0.325695 21.00000 -1.20000
H20B 2 1.102712 0.238906 0.365778 21.00000 -1.20000
AFIX 0
C21A 1 0.968884 0.266707 0.603019 21.00000 0.02769
AFIX 23
H21A 2 0.923473 0.262214 0.678892 21.00000 -1.20000
H21B 2 1.029953 0.187327 0.588989 21.00000 -1.20000
AFIX 0
C22A 1 1.032267 0.347829 0.575601 21.00000 0.04803 0.07349 =
0.04154 0.00575 -0.02692 -0.03634
AFIX 23
H22A 2 1.080712 0.332130 0.626743 21.00000 -1.20000
H22B 2 0.972024 0.430054 0.573108 21.00000 -1.20000
AFIX 0
O4A 6 1.126374 0.320629 0.456127 21.00000 0.01482 0.07058 =
0.03060 -0.01322 0.00115 -0.01999
PART 0
PART 2
CL1B 3 0.338050 -0.140254 0.716356 -21.00000 0.51932 0.06863 =
0.12788 -0.00225 -0.02889 -0.04391
O5B 6 0.611780 -0.137249 0.534380 -21.00000 0.17517 0.02176 =
0.04600 -0.01275 0.04683 -0.01726
O6B 6 0.539495 -0.019929 0.934442 -21.00000 0.06754
C19B 1 0.919015 0.385578 0.430578 -21.00000 0.03064
AFIX 23
H19C 2 0.933701 0.341243 0.374911 -21.00000 -1.20000
H19D 2 0.844165 0.457714 0.424526 -21.00000 -1.20000
AFIX 0
C20B 1 0.995642 0.413347 0.408258 -21.00000 0.04703 0.08347 =
0.02896 -0.00002 -0.00541 -0.04920
AFIX 23
H20C 2 0.959379 0.499679 0.404471 -21.00000 -1.20000
H20D 2 1.041714 0.396853 0.335136 -21.00000 -1.20000
AFIX 0
C21B 1 0.947153 0.317612 0.611282 -21.00000 0.02688
AFIX 23
H21C 2 0.922458 0.275465 0.682780 -21.00000 -1.20000
H21D 2 0.927166 0.399803 0.617028 -21.00000 -1.20000
AFIX 0
C22B 1 1.089500 0.256084 0.558640 -21.00000 0.04803 0.07349 =
0.04154 0.00575 -0.02692 -0.03634
AFIX 23
H22C 2 1.109022 0.184499 0.530580 -21.00000 -1.20000
H22D 2 1.144125 0.240014 0.604661 -21.00000 -1.20000
AFIX 0
O4B 6 1.087420 0.369785 0.467348 -21.00000 0.01482 0.07058 =
0.03060 -0.01322 0.00115 -0.01999
PART 0
NI1 5 0.364853 0.299474 0.720626 11.00000 0.01835 0.03403 =
0.03116 -0.00704 -0.00033 -0.01321
O1 6 -0.335301 0.171682 0.987336 11.00000 0.03034 0.05620 =
0.04557 -0.00950 -0.01394 -0.01389
O2 6 0.287191 0.469561 0.749184 11.00000 0.02507 0.03633 =
0.02511 -0.00658 -0.00211 -0.01793
O3 6 0.320042 0.350795 0.579447 11.00000 0.02480 0.05726 =
0.03078 -0.01687 0.00112 -0.02410
N1 4 -0.116043 0.216389 0.904187 11.00000 0.02705 0.03708 =
0.06749 -0.00868 -0.00113 -0.01624
N2 4 0.095442 0.151360 0.832278 11.00000 0.02374 0.02781 =
0.03738 -0.00317 -0.00188 -0.01281
N3 4 -0.019997 0.347550 0.871446 11.00000 0.02033 0.03030 =
0.04693 -0.00874 0.00199 -0.01102
N4 4 0.198676 0.283039 0.796010 11.00000 0.02154 0.02492 =
0.01806 -0.00398 -0.00453 -0.00871
N5 4 -0.027652 0.555325 0.881058 11.00000 0.02358 0.03088 =
0.03021 -0.00859 0.00229 -0.01004
N6 4 0.083411 0.472145 0.837115 11.00000 0.02308 0.03005 =
0.02426 -0.00792 -0.00150 -0.01124
N7 4 0.303215 0.096770 0.753935 11.00000 0.02376 0.02297 =
0.03738 -0.00390 -0.00453 -0.00756
N8 4 0.411262 0.125490 0.705959 11.00000 0.01896 0.04273 =
0.05690 -0.01943 0.00784 -0.01181
AFIX 23
H8A 2 0.439192 0.116765 0.636380 11.00000 -1.20000
H8B 2 0.473219 0.076766 0.738219 11.00000 -1.20000
AFIX 0
N9 4 0.441754 0.245935 0.850147 11.00000 0.02600 0.03400 =
0.03181 -0.00082 -0.00107 -0.01810
AFIX 23
H9A 2 0.396775 0.298026 0.896966 11.00000 -1.20000
H9B 2 0.439918 0.174400 0.883791 11.00000 -1.20000
AFIX 0
N10 4 0.566481 0.240075 0.812314 11.00000 0.01918 0.05301 =
0.02738 0.00124 -0.00711 -0.01366
N11 4 0.534012 0.306405 0.647199 11.00000 0.02285 0.03227 =
0.02175 -0.00366 -0.00662 -0.01074
N12 4 0.727824 0.272230 0.678573 11.00000 0.02650 0.04750 =
0.02837 -0.00435 -0.00663 -0.02008
N13 4 0.697208 0.341470 0.503094 11.00000 0.01902 0.04312 =
0.02793 -0.00951 -0.00016 -0.01626
N14 4 0.880655 0.312406 0.536439 11.00000 0.02190 0.07342 =
0.03020 -0.00311 -0.00658 -0.02762
N15 4 0.509040 0.374448 0.476489 11.00000 0.02109 0.03476 =
0.02265 -0.00985 -0.00088 -0.01435
N16 4 0.557827 0.401414 0.369560 11.00000 0.02492 0.04154 =
0.02344 -0.00844 -0.00432 -0.01843
C1 1 -0.217233 0.076020 0.981469 11.00000 0.03161 0.04735 =
0.07414 -0.00593 -0.01434 -0.01767
AFIX 23
H1A 2 -0.224200 0.005595 0.971244 11.00000 -1.20000
H1B 2 -0.193996 0.058010 1.048842 11.00000 -1.20000
AFIX 0
C2 1 -0.330098 0.272444 1.005339 11.00000 0.02505 0.05629 =
0.07021 -0.02853 -0.01268 -0.00713
AFIX 23
H2A 2 -0.308298 0.255330 1.073254 11.00000 -1.20000
H2B 2 -0.413703 0.336144 1.011417 11.00000 -1.20000
AFIX 0
C3 1 -0.118994 0.104443 0.893393 11.00000 0.04090 0.03861 =
0.06606 -0.01561 0.00256 -0.02028
AFIX 23
H3A 2 -0.136344 0.112812 0.825105 11.00000 -1.20000
H3B 2 -0.036750 0.040322 0.894485 11.00000 -1.20000
AFIX 0
C4 1 -0.239408 0.311568 0.921645 11.00000 0.03377 0.04023 =
0.05764 -0.01048 -0.01142 -0.00629
AFIX 23
H4A 2 -0.233526 0.378109 0.940551 11.00000 -1.20000
H4B 2 -0.267124 0.339303 0.855534 11.00000 -1.20000
AFIX 0
C5 1 -0.011052 0.237773 0.868295 11.00000 0.02465 0.03212 =
0.04232 -0.00538 -0.00268 -0.01241
C6 1 0.196959 0.177738 0.795907 11.00000 0.02036 0.02546 =
0.02755 -0.00126 -0.00924 -0.00766
C7 1 0.087872 0.360929 0.835540 11.00000 0.02303 0.03070 =
0.01830 0.00030 -0.00543 -0.01333
C8 1 -0.113553 0.761576 0.907218 11.00000 0.05106 0.03395 =
0.04481 -0.01625 -0.00448 -0.01268
AFIX 137
H8C 2 -0.146163 0.812667 0.847138 11.00000 -1.50000
H8D 2 -0.083024 0.802804 0.936346 11.00000 -1.50000
H8E 2 -0.180376 0.740596 0.961951 11.00000 -1.50000
AFIX 0
C9 1 -0.009108 0.653440 0.871170 11.00000 0.04260 0.03139 =
0.02436 -0.00515 -0.00906 -0.01080
C10 1 0.114172 0.636719 0.822529 11.00000 0.03861 0.03616 =
0.02866 -0.00607 -0.00573 -0.01905
AFIX 43
H10A 2 0.151262 0.692792 0.808161 11.00000 -1.20000
AFIX 0
C11 1 0.175649 0.522555 0.797812 11.00000 0.02593 0.03550 =
0.02143 -0.00403 -0.00137 -0.01741
C12 1 0.389103 0.373506 0.491860 11.00000 0.01689 0.04000 =
0.03692 -0.01507 -0.00068 -0.01503
C13 1 0.368635 0.405031 0.390476 11.00000 0.02627 0.05050 =
0.02812 -0.01270 -0.00745 -0.01823
AFIX 43
H13 2 0.295997 0.412544 0.374077 11.00000 -1.20000
AFIX 0
C14 1 0.472085 0.423161 0.318975 11.00000 0.01946 0.03606 =
0.02601 -0.01411 -0.00365 -0.00976
C15 1 0.498714 0.458991 0.202700 11.00000 0.02706 0.05204 =
0.02712 -0.00851 -0.00627 -0.01731
AFIX 137
H15A 2 0.485063 0.542567 0.186100 11.00000 -1.50000
H15B 2 0.442846 0.444865 0.175197 11.00000 -1.50000
H15C 2 0.585840 0.413234 0.169911 11.00000 -1.50000
AFIX 0
C16 1 0.585710 0.337168 0.544893 11.00000 0.02865 0.02991 =
0.02732 -0.00949 -0.00725 -0.01298
C17 1 0.612575 0.272565 0.708731 11.00000 0.02414 0.03125 =
0.03838 -0.00783 -0.01023 -0.00772
C18 1 0.766134 0.308071 0.573876 11.00000 0.02550 0.04587 =
0.02545 -0.01165 -0.00626 -0.01362
CL2 3 -0.308970 0.594729 0.962970 11.00000 0.02702 0.05438 =
0.06487 -0.01997 0.00022 -0.01086
O7 6 -0.413713 0.793500 0.796357 11.00000 0.14635 0.13048 =
0.15266 0.05293 -0.06217 -0.08101
H7 2 0.299750 0.023046 0.750138 11.00000 0.02952
H10 2 0.605201 0.205743 0.863760 11.00000 0.03231
H16 2 0.615406 0.423931 0.358829 11.00000 0.02498
H5 2 -0.101030 0.539524 0.906659 11.00000 0.02884
HKLF 4
REM AMakop13_0m_a.res in P-1
REM R1 = 0.1218 for 4657 Fo > 4sig(Fo) and 0.1972 for all 7929 data
REM 462 parameters refined using 0 restraints
END
WGHT 0.1734 12.0618
REM Instructions for potential hydrogen bonds
HTAB C19B O3_$4
EQIV $6 -x+2, -y+1, -z+1
HTAB C20B O4B_$6
HTAB N8 O5A_$1
HTAB N8 O5B_$1
HTAB N9 Cl2_$2
HTAB N9 O6A
HTAB N9 O6A_$3
HTAB N9 O6B
EQIV $7 -x, -y, -z+2
HTAB C2 Cl1A_$7
HTAB C4 Cl2
HTAB C8 Cl2
EQIV $8 x-1, y, z
HTAB C13 O4A_$8
HTAB C13 O4B_$8
HTAB C15 N10_$4
HTAB N7 Cl1A
HTAB N10 O1_$5
HTAB N16 O2_$4
HTAB N5 Cl2
REM Highest difference peak 2.176, deepest hole -1.198, 1-sigma level 0.202
Q1 1 0.5980 -0.0263 0.8147 11.00000 0.05 2.18
Q2 1 0.7173 -0.0230 0.7030 11.00000 0.05 2.02
Q3 1 0.0272 -0.0603 0.6785 11.00000 0.05 1.91
Q4 1 1.0011 0.0454 0.3636 11.00000 0.05 1.61
Q5 1 0.7123 -0.1579 0.6035 11.00000 0.05 1.53
Q6 1 1.2003 0.0121 0.3232 11.00000 0.05 1.44
Q7 1 0.4603 -0.0617 0.4951 11.00000 0.05 1.40
Q8 1 0.1181 -0.0764 0.6857 11.00000 0.05 1.08
Q9 1 1.1277 0.0038 0.3945 11.00000 0.05 1.07
Q10 1 -0.1106 0.0834 0.9850 11.00000 0.05 1.06
Q11 1 1.0399 -0.0007 0.4726 11.00000 0.05 1.04
Q12 1 -0.2134 0.2878 1.0191 11.00000 0.05 1.03
Q13 1 0.1598 -0.1183 0.7554 11.00000 0.05 1.03
Q14 1 -0.1038 0.1966 0.9787 11.00000 0.05 1.01
Q15 1 1.0373 -0.0223 0.5286 11.00000 0.05 0.98
Q16 1 1.0654 -0.0332 0.5442 11.00000 0.05 0.95
Q17 1 0.3190 -0.0557 0.4582 11.00000 0.05 0.93
Q18 1 0.4994 -0.0336 0.8835 11.00000 0.05 0.84
Q19 1 -0.1978 0.1074 0.9081 11.00000 0.05 0.84
Q20 1 0.3803 0.2242 0.7177 11.00000 0.05 0.82
Q21 1 -0.4037 0.8863 0.8221 11.00000 0.05 0.75
Q22 1 0.2033 -0.0591 0.5851 11.00000 0.05 0.73
Q23 1 0.3040 -0.0764 0.5109 11.00000 0.05 0.71
Q24 1 0.0069 0.2191 0.9264 11.00000 0.05 0.69
Q25 1 0.2421 -0.0424 0.5016 11.00000 0.05 0.68
Q26 1 0.2182 -0.0362 0.4105 11.00000 0.05 0.68
Q27 1 -0.2973 0.6475 0.9048 11.00000 0.05 0.66
Q28 1 0.2998 0.3604 0.7261 11.00000 0.05 0.58
Q29 1 0.9637 0.2812 0.4269 11.00000 0.05 0.57
Q30 1 0.6244 -0.1192 0.5012 11.00000 0.05 0.57
Q31 1 0.5931 -0.1018 0.5231 11.00000 0.05 0.51
Q32 1 -0.3173 0.1397 0.9968 11.00000 0.05 0.51
Q33 1 0.3753 0.3952 0.4418 11.00000 0.05 0.50
Q34 1 -0.0095 0.0352 0.9667 11.00000 0.05 0.47
Q35 1 0.2624 0.4380 0.7304 11.00000 0.05 0.46
Q36 1 0.5267 0.4062 0.1891 11.00000 0.05 0.46
Q37 1 -0.0073 0.3253 0.9286 11.00000 0.05 0.46
Q38 1 0.8687 0.3771 0.3884 11.00000 0.05 0.46
Q39 1 0.0624 0.1643 0.8822 11.00000 0.05 0.45
Q40 1 -0.2970 0.2018 0.9604 11.00000 0.05 0.45
Q41 1 0.2385 0.2799 0.7603 11.00000 0.05 0.44
Q42 1 0.3613 0.3964 0.7306 11.00000 0.05 0.43
Q43 1 0.5540 0.4911 0.1591 11.00000 0.05 0.43
Q44 1 0.2095 0.3012 0.8178 11.00000 0.05 0.43
Q45 1 0.5439 0.3162 0.6102 11.00000 0.05 0.43
Q46 1 0.7272 0.3385 0.4706 11.00000 0.05 0.42
Q47 1 -0.1216 0.1709 0.9006 11.00000 0.05 0.42
Q48 1 -0.0153 0.2989 0.8598 11.00000 0.05 0.42
Q49 1 1.0280 0.3995 0.3865 11.00000 0.05 0.42
Q50 1 0.3325 0.4027 0.5829 11.00000 0.05 0.42
;
_shelx_res_checksum 51093
#######################################################################
#
# 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_Complex-6
_database_code_depnum_ccdc_archive 'CCDC 1555236'
_audit_update_record
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_Complex-6
;
PROBLEM: D-H Without Acceptor O7 -- H7A ... Please Check
RESPONSE: This is due to the absence of clearly identified peripheral H-bond
acceptors to one of the solvate water molecule present in the structure.
;
_audit_creation_date 2017-08-06
_audit_creation_method SHELXL-2014/7
_shelx_SHELXL_version_number 2014/7
_chemical_name_systematic ?
_chemical_name_common none
_chemical_melting_point 'not measured'
_chemical_formula_moiety
'C11 H17 Cl Cu N8 O3, C11 H16 Cl2 Cu N8 O2, 3(H2 O), 0.5(O2)'
_chemical_formula_sum 'C22 H39 Cl3 Cu2 N16 O9'
_chemical_formula_weight 905.14
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 11.3979(6)
_cell_length_b 12.0551(7)
_cell_length_c 13.6836(7)
_cell_angle_alpha 97.586(2)
_cell_angle_beta 103.997(2)
_cell_angle_gamma 106.156(2)
_cell_volume 1711.75(16)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9886
_cell_measurement_theta_min 2.96
_cell_measurement_theta_max 27.82
_exptl_crystal_description Needle
_exptl_crystal_colour Blue
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method none
_exptl_crystal_density_diffrn 1.756
_exptl_crystal_F_000 928
_exptl_transmission_factor_min 0.956
_exptl_transmission_factor_max 0.972
_exptl_crystal_size_max 0.226
_exptl_crystal_size_mid 0.071
_exptl_crystal_size_min 0.045
_exptl_absorpt_coefficient_mu 1.551
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.876
_exptl_absorpt_correction_T_max 0.933
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0675 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.9303. The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details
;
The crystal was mounted using Paratone-N oil (cryoprotectant)
on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic
head of goniometer directly into the cold gas stream of a
liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focused sealed tube'
_diffrn_measurement_device_type
;
Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method
;
\f and \w scans with 0.5 deg/frame and 20 seconds of
exposure time. Detector was at 45mm from crystal.
;
_diffrn_detector 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_radiation_monochromator 'Multi-layer X-ray mirror'
_diffrn_radiation_probe x-ray
_diffrn_reflns_number 86344
_diffrn_reflns_av_unetI/netI 0.0325
_diffrn_reflns_av_R_equivalents 0.0597
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.959
_diffrn_reflns_theta_max 27.185
_diffrn_reflns_theta_full 25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 7595
_reflns_number_gt 6122
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_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.
;
_computing_data_collection 'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement 'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution 'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics
;
ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material 'WinGX2014.1 (Farrugia, 2012)'
_refine_special_details ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+4.0982P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary mixed
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 7595
_refine_ls_number_parameters 535
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0565
_refine_ls_R_factor_gt 0.0386
_refine_ls_wR_factor_ref 0.0886
_refine_ls_wR_factor_gt 0.0815
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
O8A O -0.1048(13) 0.1486(12) 0.9637(11) 0.0220(13) Uani 0.320(13) 1 d . . P A 1
O8B O -0.1301(6) 0.1818(6) 0.9643(4) 0.0220(13) Uani 0.680(13) 1 d . . P A 2
Cu1 Cu 0.21170(3) 0.48209(3) 0.60300(3) 0.01014(9) Uani 1 1 d . . . . .
Cl1 Cl 0.01984(6) 0.37010(6) 0.61341(5) 0.01473(15) Uani 1 1 d . . . . .
O1 O 0.93604(19) 1.02761(18) 0.69562(18) 0.0217(5) Uani 1 1 d . . . . .
O2 O 0.28242(18) 0.35955(17) 0.63154(16) 0.0136(4) Uani 1 1 d . . . . .
O3 O 0.1743(3) 0.4531(2) 0.42675(18) 0.0148(4) Uani 1 1 d . . . . .
H3A H 0.227(4) 0.476(3) 0.411(3) 0.016(11) Uiso 1 1 d . . . . .
H3B H 0.123(4) 0.450(4) 0.384(3) 0.036(14) Uiso 1 1 d . . . . .
N1 N 0.6980(2) 0.8466(2) 0.62572(19) 0.0131(5) Uani 1 1 d . . . . .
N2 N 0.4832(2) 0.7933(2) 0.61380(18) 0.0117(5) Uani 1 1 d . . . . .
N3 N 0.5965(2) 0.6517(2) 0.61923(17) 0.0104(5) Uani 1 1 d . . . . .
N4 N 0.3794(2) 0.5932(2) 0.61703(17) 0.0104(5) Uani 1 1 d . . . . .
N5 N 0.2717(2) 0.7266(2) 0.60688(19) 0.0130(5) Uani 1 1 d . . . . .
H5 H 0.260(3) 0.787(3) 0.602(3) 0.012(9) Uiso 1 1 d . . . . .
N6 N 0.1645(2) 0.6317(2) 0.6065(2) 0.0118(5) Uani 1 1 d . . . . .
H6A H 0.146(3) 0.652(3) 0.661(3) 0.017(9) Uiso 1 1 d . . . . .
H6B H 0.099(3) 0.622(3) 0.548(3) 0.022(9) Uiso 1 1 d . . . . .
N7 N 0.4924(2) 0.4603(2) 0.62478(18) 0.0106(5) Uani 1 1 d . . . . .
N8 N 0.6056(2) 0.4346(2) 0.62878(18) 0.0120(5) Uani 1 1 d . . . . .
C1 C 0.8223(3) 1.0520(3) 0.7030(3) 0.0217(7) Uani 1 1 d . . . . .
H1A H 0.8308 1.1343 0.6959 0.026 Uiso 1 1 calc R U . . .
H1B H 0.8120 1.0450 0.7719 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7042(3) 0.9682(2) 0.6206(2) 0.0167(6) Uani 1 1 d . . . . .
H2A H 0.6266 0.9825 0.6321 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7083 0.9820 0.5516 0.020 Uiso 1 1 calc R U . . .
C3 C 0.9274(3) 0.9092(3) 0.7053(2) 0.0180(6) Uani 1 1 d . . . . .
H3C H 0.9171 0.8986 0.7736 0.022 Uiso 1 1 calc R U . . .
H3D H 1.0073 0.8946 0.7006 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8154(3) 0.8215(3) 0.6214(2) 0.0159(6) Uani 1 1 d . . . . .
H4A H 0.8288 0.8273 0.5532 0.019 Uiso 1 1 calc R U . . .
H4B H 0.8082 0.7401 0.6311 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5891(3) 0.7624(2) 0.6188(2) 0.0111(5) Uani 1 1 d . . . . .
C6 C 0.4904(3) 0.5730(2) 0.6198(2) 0.0099(5) Uani 1 1 d . . . . .
C7 C 0.3823(3) 0.7054(2) 0.6127(2) 0.0105(5) Uani 1 1 d . . . . .
C8 C 0.3965(3) 0.3613(2) 0.6316(2) 0.0118(6) Uani 1 1 d . . . . .
C9 C 0.4517(3) 0.2739(3) 0.6403(2) 0.0132(6) Uani 1 1 d . . . . .
H9 H 0.4123 0.1956 0.6464 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5781(3) 0.3235(2) 0.6384(2) 0.0122(6) Uani 1 1 d . . . . .
C11 C 0.6780(3) 0.2647(3) 0.6473(2) 0.0170(6) Uani 1 1 d . . . . .
H11A H 0.7530 0.3158 0.6336 0.026 Uiso 1 1 calc R U . . .
H11B H 0.6442 0.1892 0.5972 0.026 Uiso 1 1 calc R U . . .
H11C H 0.7025 0.2505 0.7171 0.026 Uiso 1 1 calc R U . . .
Cu2 Cu 0.16990(3) 0.54084(3) 0.86307(3) 0.01019(9) Uani 1 1 d . . . . .
Cl2 Cl 0.04746(6) 0.65374(6) 0.80789(5) 0.01419(15) Uani 1 1 d . . . . .
Cl3 Cl 0.22168(6) 0.59455(6) 1.06032(5) 0.01359(14) Uani 1 1 d . . . . .
O4 O 0.4503(2) -0.06217(18) 0.84875(17) 0.0193(5) Uani 1 1 d . . . . .
O5 O 0.32180(18) 0.64979(17) 0.84679(15) 0.0121(4) Uani 1 1 d . . . . .
N9 N 0.3764(2) 0.1390(2) 0.89243(19) 0.0118(5) Uani 1 1 d . . . . .
N10 N 0.2101(2) 0.2151(2) 0.88459(18) 0.0111(5) Uani 1 1 d . . . . .
N11 N 0.2479(2) 0.4149(2) 0.86433(18) 0.0100(5) Uani 1 1 d . . . . .
N12 N 0.4180(2) 0.3346(2) 0.88393(18) 0.0100(5) Uani 1 1 d . . . . .
N13 N 0.0521(2) 0.3015(2) 0.86651(19) 0.0120(5) Uani 1 1 d . . . . .
H13 H 0.006(3) 0.249(3) 0.888(2) 0.011(8) Uiso 1 1 d . . . . .
N14 N 0.0157(2) 0.4027(2) 0.8513(2) 0.0120(5) Uani 1 1 d . . . . .
H14A H -0.030(3) 0.414(3) 0.891(3) 0.017(9) Uiso 1 1 d . . . . .
H14B H -0.032(4) 0.387(3) 0.787(3) 0.032(11) Uiso 1 1 d . . . . .
N15 N 0.4506(2) 0.5269(2) 0.86915(18) 0.0100(5) Uani 1 1 d . . . . .
N16 N 0.5766(2) 0.5399(2) 0.87559(18) 0.0111(5) Uani 1 1 d . . . . .
C12 C 0.5195(3) 0.0486(3) 0.8329(3) 0.0205(7) Uani 1 1 d . . . . .
H12A H 0.4847 0.0542 0.7607 0.025 Uiso 1 1 calc R U . . .
H12B H 0.6102 0.0539 0.8442 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3182(3) -0.0732(3) 0.8295(3) 0.0206(7) Uani 1 1 d . . . . .
H13A H 0.2711 -0.1514 0.8392 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2827 -0.0689 0.7571 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5111(3) 0.1503(3) 0.9052(2) 0.0164(6) Uani 1 1 d . . . . .
H14C H 0.5533 0.1497 0.9774 0.020 Uiso 1 1 calc R U . . .
H14D H 0.5554 0.2262 0.8900 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2988(3) 0.0232(2) 0.9010(2) 0.0166(6) Uani 1 1 d . . . . .
H15A H 0.2075 0.0175 0.8820 0.020 Uiso 1 1 calc R U . . .
H15B H 0.3243 0.0135 0.9730 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3332(3) 0.2303(2) 0.8870(2) 0.0100(5) Uani 1 1 d . . . . .
C17 C 0.1732(2) 0.3088(2) 0.8721(2) 0.0093(5) Uani 1 1 d . . . . .
C18 C 0.3683(3) 0.4186(2) 0.8724(2) 0.0089(5) Uani 1 1 d . . . . .
C19 C 0.4297(3) 0.6341(2) 0.8578(2) 0.0094(5) Uani 1 1 d . . . . .
C20 C 0.5477(3) 0.7113(2) 0.8584(2) 0.0108(5) Uani 1 1 d . . . . .
H20 H 0.5649 0.7917 0.8531 0.013 Uiso 1 1 calc R U . . .
C21 C 0.6341(3) 0.6502(2) 0.8681(2) 0.0106(5) Uani 1 1 d . . . . .
C22 C 0.7695(3) 0.6874(3) 0.8668(2) 0.0145(6) Uani 1 1 d . . . . .
H22A H 0.8152 0.6423 0.9064 0.022 Uiso 1 1 calc R U . . .
H22B H 0.8098 0.7719 0.8976 0.022 Uiso 1 1 calc R U . . .
H22C H 0.7726 0.6724 0.7954 0.022 Uiso 1 1 calc R U . . .
O6 O 1.1399(4) 1.1222(3) 0.6213(3) 0.0469(9) Uani 1 1 d . . . . .
H6C H 1.174(4) 1.190(4) 0.629(3) 0.030(11) Uiso 1 1 d . . . . .
H6D H 1.090(5) 1.114(4) 0.641(4) 0.048(16) Uiso 1 1 d . . . . .
O7 O 1.1530(3) 0.8984(3) 0.5567(2) 0.0242(5) Uani 1 1 d . . . . .
H7A H 1.091(5) 0.873(4) 0.513(4) 0.040(14) Uiso 1 1 d . . . . .
H7B H 1.157(5) 0.960(5) 0.568(4) 0.055(17) Uiso 1 1 d . . . . .
H8AA H -0.100(5) 0.199(4) 1.018(4) 0.041(16) Uiso 1 1 d . . . . .
H8AB H -0.158(6) 0.214(5) 0.955(5) 0.05(2) Uiso 1 1 d . . . . .
O10 O 0.0361(12) 0.0404(10) 0.9652(8) 0.271(5) Uani 1 1 d . . . . .
H16 H 0.609(3) 0.488(3) 0.885(3) 0.022(10) 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
O8A 0.026(3) 0.017(3) 0.0280(19) 0.006(2) 0.013(2) 0.009(2)
O8B 0.026(3) 0.017(3) 0.0280(19) 0.006(2) 0.013(2) 0.009(2)
Cu1 0.00638(16) 0.01121(17) 0.01214(17) 0.00312(13) 0.00267(13) 0.00150(13)
Cl1 0.0085(3) 0.0198(4) 0.0149(3) 0.0066(3) 0.0036(3) 0.0015(3)
O1 0.0106(10) 0.0129(11) 0.0388(14) 0.0027(10) 0.0059(10) 0.0017(8)
O2 0.0090(9) 0.0135(10) 0.0196(11) 0.0067(8) 0.0062(8) 0.0026(8)
O3 0.0093(11) 0.0197(12) 0.0148(12) 0.0036(9) 0.0044(10) 0.0028(9)
N1 0.0102(11) 0.0093(12) 0.0196(13) 0.0026(10) 0.0062(10) 0.0016(9)
N2 0.0111(11) 0.0097(11) 0.0132(12) 0.0018(9) 0.0028(9) 0.0023(9)
N3 0.0093(11) 0.0108(11) 0.0103(11) 0.0021(9) 0.0029(9) 0.0024(9)
N4 0.0087(11) 0.0118(12) 0.0102(11) 0.0021(9) 0.0025(9) 0.0026(9)
N5 0.0101(12) 0.0101(12) 0.0196(13) 0.0043(10) 0.0051(10) 0.0031(10)
N6 0.0080(11) 0.0150(13) 0.0116(12) 0.0029(10) 0.0033(10) 0.0018(10)
N7 0.0076(11) 0.0108(12) 0.0128(12) 0.0023(9) 0.0035(9) 0.0015(9)
N8 0.0083(11) 0.0144(12) 0.0143(12) 0.0024(10) 0.0039(9) 0.0050(10)
C1 0.0135(15) 0.0134(15) 0.0338(19) -0.0022(13) 0.0048(13) 0.0028(12)
C2 0.0132(14) 0.0116(14) 0.0247(16) 0.0049(12) 0.0059(12) 0.0021(12)
C3 0.0121(14) 0.0161(15) 0.0255(17) 0.0055(13) 0.0049(12) 0.0040(12)
C4 0.0111(14) 0.0116(14) 0.0256(16) 0.0019(12) 0.0091(12) 0.0023(11)
C5 0.0120(13) 0.0140(14) 0.0057(13) 0.0006(11) 0.0017(11) 0.0034(11)
C6 0.0095(13) 0.0132(14) 0.0050(12) 0.0004(10) 0.0007(10) 0.0026(11)
C7 0.0103(13) 0.0137(14) 0.0058(13) 0.0001(11) 0.0013(10) 0.0032(11)
C8 0.0105(13) 0.0130(14) 0.0090(13) 0.0026(11) 0.0014(11) 0.0005(11)
C9 0.0131(14) 0.0126(14) 0.0153(14) 0.0050(11) 0.0050(11) 0.0044(11)
C10 0.0138(14) 0.0131(14) 0.0105(13) 0.0040(11) 0.0034(11) 0.0051(11)
C11 0.0156(15) 0.0163(15) 0.0227(16) 0.0054(12) 0.0072(12) 0.0088(12)
Cu2 0.00749(16) 0.01105(17) 0.01516(18) 0.00520(13) 0.00545(13) 0.00491(13)
Cl2 0.0120(3) 0.0167(3) 0.0183(3) 0.0064(3) 0.0060(3) 0.0088(3)
Cl3 0.0103(3) 0.0180(3) 0.0140(3) 0.0034(3) 0.0050(3) 0.0058(3)
O4 0.0235(12) 0.0126(10) 0.0271(12) 0.0054(9) 0.0097(10) 0.0114(9)
O5 0.0091(9) 0.0125(10) 0.0194(11) 0.0071(8) 0.0070(8) 0.0066(8)
N9 0.0092(11) 0.0077(11) 0.0187(13) 0.0035(9) 0.0039(10) 0.0029(9)
N10 0.0094(11) 0.0101(12) 0.0129(12) 0.0011(9) 0.0027(9) 0.0027(9)
N11 0.0073(11) 0.0107(11) 0.0119(12) 0.0023(9) 0.0024(9) 0.0033(9)
N12 0.0102(11) 0.0085(11) 0.0122(12) 0.0026(9) 0.0037(9) 0.0037(9)
N13 0.0083(11) 0.0091(12) 0.0206(13) 0.0053(10) 0.0060(10) 0.0030(10)
N14 0.0091(11) 0.0152(13) 0.0153(13) 0.0042(10) 0.0064(11) 0.0066(10)
N15 0.0072(11) 0.0120(12) 0.0141(12) 0.0042(9) 0.0052(9) 0.0057(9)
N16 0.0062(11) 0.0140(12) 0.0159(12) 0.0040(10) 0.0044(9) 0.0060(10)
C12 0.0252(17) 0.0177(16) 0.0281(17) 0.0100(13) 0.0152(14) 0.0129(13)
C13 0.0214(16) 0.0128(15) 0.0251(17) 0.0020(13) 0.0013(13) 0.0070(13)
C14 0.0099(13) 0.0141(15) 0.0280(17) 0.0065(13) 0.0058(12) 0.0072(11)
C15 0.0141(14) 0.0102(14) 0.0266(16) 0.0059(12) 0.0070(12) 0.0039(12)
C16 0.0097(13) 0.0108(13) 0.0073(13) -0.0003(10) 0.0002(10) 0.0027(11)
C17 0.0091(13) 0.0114(13) 0.0062(12) 0.0001(10) 0.0023(10) 0.0026(11)
C18 0.0096(13) 0.0105(13) 0.0068(12) 0.0010(10) 0.0035(10) 0.0030(11)
C19 0.0128(13) 0.0098(13) 0.0078(13) 0.0033(10) 0.0043(11) 0.0051(11)
C20 0.0105(13) 0.0115(13) 0.0109(13) 0.0034(11) 0.0037(11) 0.0034(11)
C21 0.0109(13) 0.0111(14) 0.0087(13) 0.0010(11) 0.0033(11) 0.0018(11)
C22 0.0084(13) 0.0174(15) 0.0168(15) 0.0062(12) 0.0033(11) 0.0019(11)
O6 0.066(2) 0.0153(15) 0.072(2) 0.0057(14) 0.058(2) 0.0021(14)
O7 0.0263(14) 0.0190(14) 0.0252(14) 0.0038(11) 0.0014(11) 0.0096(11)
O10 0.331(14) 0.254(12) 0.222(11) 0.087(9) 0.134(10) 0.024(10)
_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
O8A H8AA 0.87(5) . ?
O8A H8AB 1.12(5) . ?
O8B H8AA 0.70(5) . ?
O8B H8AB 0.57(5) . ?
Cu1 O2 1.910(2) . ?
Cu1 N4 1.953(2) . ?
Cu1 N6 2.018(2) . ?
Cu1 Cl1 2.2767(7) . ?
Cu1 O3 2.306(2) . ?
O1 C3 1.429(4) . ?
O1 C1 1.430(4) . ?
O2 C8 1.294(3) . ?
O3 H3A 0.69(4) . ?
O3 H3B 0.71(5) . ?
N1 C5 1.341(4) . ?
N1 C2 1.459(4) . ?
N1 C4 1.465(3) . ?
N2 C7 1.324(4) . ?
N2 C5 1.348(4) . ?
N3 C6 1.315(4) . ?
N3 C5 1.361(4) . ?
N4 C6 1.345(3) . ?
N4 C7 1.354(4) . ?
N5 C7 1.341(4) . ?
N5 N6 1.421(3) . ?
N5 H5 0.79(3) . ?
N6 H6A 0.85(4) . ?
N6 H6B 0.92(4) . ?
N7 C6 1.376(4) . ?
N7 N8 1.398(3) . ?
N7 C8 1.408(4) . ?
N8 C10 1.319(4) . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.374(4) . ?
C9 C10 1.407(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.489(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Cu2 O5 1.9418(19) . ?
Cu2 N11 1.962(2) . ?
Cu2 N14 2.013(2) . ?
Cu2 Cl2 2.2778(7) . ?
Cu2 Cl3 2.5706(8) . ?
O4 C12 1.424(4) . ?
O4 C13 1.429(4) . ?
O5 C19 1.272(3) . ?
N9 C16 1.328(4) . ?
N9 C15 1.466(4) . ?
N9 C14 1.468(3) . ?
N10 C17 1.327(4) . ?
N10 C16 1.355(3) . ?
N11 C18 1.337(3) . ?
N11 C17 1.359(4) . ?
N12 C18 1.301(4) . ?
N12 C16 1.369(4) . ?
N13 C17 1.341(3) . ?
N13 N14 1.418(3) . ?
N13 H13 0.83(3) . ?
N14 H14A 0.86(4) . ?
N14 H14B 0.88(4) . ?
N15 N16 1.380(3) . ?
N15 C18 1.393(4) . ?
N15 C19 1.399(3) . ?
N16 C21 1.338(4) . ?
N16 H16 0.82(4) . ?
C12 C14 1.511(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.518(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 C20 1.404(4) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.488(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O6 H6C 0.78(4) . ?
O6 H6D 0.68(5) . ?
O7 H7A 0.76(5) . ?
O7 H7B 0.72(5) . ?
O10 O10 1.646(16) 2_557 ?
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
H8AA O8A H8AB 60(4) . . ?
H8AA O8B H8AB 106(7) . . ?
O2 Cu1 N4 91.94(9) . . ?
O2 Cu1 N6 166.42(10) . . ?
N4 Cu1 N6 81.45(10) . . ?
O2 Cu1 Cl1 90.43(6) . . ?
N4 Cu1 Cl1 170.32(7) . . ?
N6 Cu1 Cl1 94.23(7) . . ?
O2 Cu1 O3 100.56(9) . . ?
N4 Cu1 O3 87.85(9) . . ?
N6 Cu1 O3 91.09(9) . . ?
Cl1 Cu1 O3 100.94(7) . . ?
C3 O1 C1 110.9(2) . . ?
C8 O2 Cu1 125.16(18) . . ?
Cu1 O3 H3A 115(3) . . ?
Cu1 O3 H3B 136(4) . . ?
H3A O3 H3B 103(5) . . ?
C5 N1 C2 122.6(2) . . ?
C5 N1 C4 123.1(2) . . ?
C2 N1 C4 113.6(2) . . ?
C7 N2 C5 114.0(2) . . ?
C6 N3 C5 114.4(2) . . ?
C6 N4 C7 114.4(2) . . ?
C6 N4 Cu1 129.78(19) . . ?
C7 N4 Cu1 115.40(18) . . ?
C7 N5 N6 118.1(2) . . ?
C7 N5 H5 126(2) . . ?
N6 N5 H5 116(2) . . ?
N5 N6 Cu1 109.22(17) . . ?
N5 N6 H6A 105(2) . . ?
Cu1 N6 H6A 113(2) . . ?
N5 N6 H6B 109(2) . . ?
Cu1 N6 H6B 109(2) . . ?
H6A N6 H6B 111(3) . . ?
C6 N7 N8 119.1(2) . . ?
C6 N7 C8 129.9(2) . . ?
N8 N7 C8 110.9(2) . . ?
C10 N8 N7 104.2(2) . . ?
O1 C1 C2 112.1(2) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C1 109.0(2) . . ?
N1 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O1 C3 C4 110.7(2) . . ?
O1 C3 H3C 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O1 C3 H3D 109.5 . . ?
C4 C3 H3D 109.5 . . ?
H3C C3 H3D 108.1 . . ?
N1 C4 C3 109.4(2) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 N2 118.5(2) . . ?
N1 C5 N3 116.0(2) . . ?
N2 C5 N3 125.5(3) . . ?
N3 C6 N4 125.7(3) . . ?
N3 C6 N7 117.6(2) . . ?
N4 C6 N7 116.6(2) . . ?
N2 C7 N5 118.7(3) . . ?
N2 C7 N4 125.8(2) . . ?
N5 C7 N4 115.4(2) . . ?
O2 C8 C9 129.7(3) . . ?
O2 C8 N7 124.7(2) . . ?
C9 C8 N7 105.6(2) . . ?
C8 C9 C10 106.2(2) . . ?
C8 C9 H9 126.9 . . ?
C10 C9 H9 126.9 . . ?
N8 C10 C9 113.1(2) . . ?
N8 C10 C11 119.9(3) . . ?
C9 C10 C11 127.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 Cu2 N11 90.89(9) . . ?
O5 Cu2 N14 166.34(9) . . ?
N11 Cu2 N14 80.60(10) . . ?
O5 Cu2 Cl2 92.52(6) . . ?
N11 Cu2 Cl2 161.34(7) . . ?
N14 Cu2 Cl2 92.30(7) . . ?
O5 Cu2 Cl3 99.27(6) . . ?
N11 Cu2 Cl3 94.16(7) . . ?
N14 Cu2 Cl3 92.03(8) . . ?
Cl2 Cu2 Cl3 103.37(3) . . ?
C12 O4 C13 110.3(2) . . ?
C19 O5 Cu2 126.25(18) . . ?
C16 N9 C15 123.1(2) . . ?
C16 N9 C14 122.5(2) . . ?
C15 N9 C14 113.9(2) . . ?
C17 N10 C16 114.6(2) . . ?
C18 N11 C17 113.0(2) . . ?
C18 N11 Cu2 130.81(19) . . ?
C17 N11 Cu2 115.50(17) . . ?
C18 N12 C16 113.9(2) . . ?
C17 N13 N14 117.3(2) . . ?
C17 N13 H13 122(2) . . ?
N14 N13 H13 119(2) . . ?
N13 N14 Cu2 110.25(17) . . ?
N13 N14 H14A 109(2) . . ?
Cu2 N14 H14A 116(2) . . ?
N13 N14 H14B 107(3) . . ?
Cu2 N14 H14B 106(3) . . ?
H14A N14 H14B 108(3) . . ?
N16 N15 C18 120.2(2) . . ?
N16 N15 C19 108.5(2) . . ?
C18 N15 C19 131.3(2) . . ?
C21 N16 N15 108.6(2) . . ?
C21 N16 H16 127(3) . . ?
N15 N16 H16 124(3) . . ?
O4 C12 C14 111.2(2) . . ?
O4 C12 H12A 109.4 . . ?
C14 C12 H12A 109.4 . . ?
O4 C12 H12B 109.4 . . ?
C14 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O4 C13 C15 111.6(2) . . ?
O4 C13 H13A 109.3 . . ?
C15 C13 H13A 109.3 . . ?
O4 C13 H13B 109.3 . . ?
C15 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N9 C14 C12 109.4(2) . . ?
N9 C14 H14C 109.8 . . ?
C12 C14 H14C 109.8 . . ?
N9 C14 H14D 109.8 . . ?
C12 C14 H14D 109.8 . . ?
H14C C14 H14D 108.2 . . ?
N9 C15 C13 109.3(2) . . ?
N9 C15 H15A 109.8 . . ?
C13 C15 H15A 109.8 . . ?
N9 C15 H15B 109.8 . . ?
C13 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N9 C16 N10 118.9(2) . . ?
N9 C16 N12 116.7(2) . . ?
N10 C16 N12 124.4(2) . . ?
N10 C17 N13 119.0(2) . . ?
N10 C17 N11 125.8(2) . . ?
N13 C17 N11 115.2(2) . . ?
N12 C18 N11 128.2(3) . . ?
N12 C18 N15 116.3(2) . . ?
N11 C18 N15 115.5(2) . . ?
O5 C19 N15 123.8(2) . . ?
O5 C19 C20 130.6(3) . . ?
N15 C19 C20 105.6(2) . . ?
C21 C20 C19 108.1(2) . . ?
C21 C20 H20 126.0 . . ?
C19 C20 H20 126.0 . . ?
N16 C21 C20 109.2(2) . . ?
N16 C21 C22 120.4(2) . . ?
C20 C21 C22 130.3(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H6C O6 H6D 109(5) . . ?
H7A O7 H7B 101(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
O3 H3A N8 0.69(4) 2.15(4) 2.830(3) 173(4) 2_666
O3 H3B Cl2 0.71(5) 2.74(5) 3.395(3) 153(4) 2_566
N5 H5 O7 0.79(3) 2.10(4) 2.842(4) 156(3) 1_455
N6 H6A Cl2 0.85(4) 2.53(4) 3.351(3) 163(3) .
N6 H6B Cl1 0.92(4) 2.33(4) 3.220(3) 163(3) 2_566
N13 H13 O8A 0.83(3) 2.07(4) 2.887(14) 168(3) .
N13 H13 O8B 0.83(3) 2.12(3) 2.894(6) 155(3) .
N14 H14A Cl3 0.86(4) 2.41(4) 3.226(2) 158(3) 2_567
N14 H14B Cl1 0.88(4) 2.58(4) 3.240(3) 132(3) .
O6 H6C O2 0.78(4) 2.07(5) 2.835(4) 169(4) 1_665
O6 H6D O1 0.68(5) 2.13(5) 2.777(4) 160(5) .
O7 H7A Cl1 0.76(5) 2.95(5) 3.467(3) 127(4) 2_666
O7 H7B O6 0.72(5) 2.08(5) 2.783(4) 166(6) .
O8A H8AA Cl2 0.87(5) 2.61(5) 3.471(14) 171(4) 2_567
O8B H8AA Cl2 0.70(5) 2.61(5) 3.232(6) 148(5) 2_567
O8A H8AB Cl3 1.12(5) 2.63(6) 3.718(14) 165(5) 2_567
O8B H8AB Cl3 0.57(5) 2.63(6) 3.179(8) 164(7) 2_567
N16 H16 Cl3 0.82(4) 2.42(4) 3.187(2) 157(3) 2_667
_refine_diff_density_max 2.201
_refine_diff_density_min -1.005
_refine_diff_density_rms 0.097
_shelx_res_file
;
shelx.res created by SHELXL-2014/7
TITL AMakop10_0m_a.res in P-1
REM Old TITL AMakop10_0m in P-1
REM SHELXT solution in P-1
REM R1 0.106, Rweak 0.007, Alpha 0.058, Orientation as input
REM Formula found by SHELXT: C35 O1 Cu1 H6b Cl2
CELL 0.71073 11.3979 12.0551 13.6836 97.586 103.997 106.156
ZERR 4 0.0006 0.0007 0.0007 0.002 0.002 0.002
LATT 1
SFAC C H Cl Cu N O
UNIT 44 78 6 4 32 18
EQIV $1 1-X,1-Y,1-Z
EQIV $2 -X,1-Y,1-Z
EQIV $3 -1+X,+Y,+Z
EQIV $4 1+X,1+Y,+Z
EQIV $5 -X,1-Y,2-Z
EQIV $6 1-X,1-Y,2-Z
EADP O8A O8B
L.S. 50
PLAN 30
TEMP -173.15
HTAB O3 N8_$1
HTAB O3 Cl2_$2
HTAB N5 O7_$3
HTAB N6 Cl2
HTAB N6 Cl1_$2
HTAB N13 O8A
HTAB N13 O8B
HTAB N14 Cl3_$5
HTAB N14 Cl1
HTAB O6 O2_$4
HTAB O6 O1
HTAB O7 Cl1_$1
HTAB O7 O6
HTAB O8A Cl2_$5
HTAB O8B Cl2_$5
HTAB O8A Cl3_$5
HTAB O8B Cl3_$5
HTAB N16 Cl3_$6
BOND $H
LIST 4
HTAB
fmap 2
acta 50
REM
REM
REM
WGHT 0.032000 4.098200
FVAR 0.21880 0.32045
PART 1
O8A 6 -0.104788 0.148594 0.963748 21.00000 0.02616 0.01665 =
0.02796 0.00615 0.01275 0.00929
PART 0
PART 2
O8B 6 -0.130108 0.181802 0.964297 -21.00000 0.02616 0.01665 =
0.02796 0.00615 0.01275 0.00929
PART 0
CU1 4 0.211697 0.482089 0.603003 11.00000 0.00638 0.01121 =
0.01214 0.00312 0.00267 0.00150
CL1 3 0.019839 0.370105 0.613410 11.00000 0.00845 0.01981 =
0.01494 0.00664 0.00365 0.00148
O1 6 0.936039 1.027613 0.695618 11.00000 0.01056 0.01289 =
0.03876 0.00274 0.00595 0.00170
O2 6 0.282423 0.359547 0.631537 11.00000 0.00901 0.01348 =
0.01962 0.00670 0.00618 0.00259
O3 6 0.174318 0.453076 0.426754 11.00000 0.00935 0.01967 =
0.01476 0.00356 0.00442 0.00283
H3A 2 0.227215 0.475617 0.410952 11.00000 0.01628
H3B 2 0.122724 0.450146 0.383671 11.00000 0.03582
N1 5 0.698016 0.846619 0.625721 11.00000 0.01020 0.00933 =
0.01955 0.00256 0.00617 0.00157
N2 5 0.483222 0.793281 0.613799 11.00000 0.01106 0.00971 =
0.01321 0.00177 0.00283 0.00233
N3 5 0.596519 0.651673 0.619235 11.00000 0.00930 0.01083 =
0.01034 0.00211 0.00287 0.00236
N4 5 0.379424 0.593168 0.617025 11.00000 0.00866 0.01176 =
0.01022 0.00209 0.00245 0.00258
N5 5 0.271734 0.726632 0.606877 11.00000 0.01006 0.01006 =
0.01959 0.00431 0.00512 0.00310
H5 2 0.259513 0.787136 0.602093 11.00000 0.01238
N6 5 0.164547 0.631680 0.606509 11.00000 0.00799 0.01497 =
0.01158 0.00291 0.00325 0.00178
H6A 2 0.146037 0.652468 0.660900 11.00000 0.01746
H6B 2 0.098563 0.621980 0.548345 11.00000 0.02219
N7 5 0.492448 0.460324 0.624776 11.00000 0.00757 0.01078 =
0.01276 0.00234 0.00349 0.00149
N8 5 0.605558 0.434554 0.628784 11.00000 0.00828 0.01436 =
0.01433 0.00236 0.00388 0.00499
C1 1 0.822322 1.052038 0.702985 11.00000 0.01353 0.01339 =
0.03385 -0.00224 0.00479 0.00285
AFIX 23
H1A 2 0.830762 1.134350 0.695894 11.00000 -1.20000
H1B 2 0.811961 1.045028 0.771915 11.00000 -1.20000
AFIX 0
C2 1 0.704182 0.968186 0.620628 11.00000 0.01316 0.01157 =
0.02472 0.00493 0.00594 0.00208
AFIX 23
H2A 2 0.626645 0.982531 0.632050 11.00000 -1.20000
H2B 2 0.708344 0.981976 0.551627 11.00000 -1.20000
AFIX 0
C3 1 0.927426 0.909248 0.705286 11.00000 0.01210 0.01609 =
0.02550 0.00550 0.00486 0.00398
AFIX 23
H3C 2 0.917112 0.898612 0.773585 11.00000 -1.20000
H3D 2 1.007350 0.894556 0.700640 11.00000 -1.20000
AFIX 0
C4 1 0.815437 0.821454 0.621440 11.00000 0.01108 0.01164 =
0.02562 0.00186 0.00914 0.00231
AFIX 23
H4A 2 0.828773 0.827260 0.553194 11.00000 -1.20000
H4B 2 0.808194 0.740115 0.631082 11.00000 -1.20000
AFIX 0
C5 1 0.589120 0.762384 0.618818 11.00000 0.01204 0.01404 =
0.00567 0.00059 0.00166 0.00336
C6 1 0.490385 0.573027 0.619769 11.00000 0.00952 0.01323 =
0.00497 0.00044 0.00075 0.00256
C7 1 0.382338 0.705436 0.612686 11.00000 0.01026 0.01372 =
0.00584 0.00014 0.00128 0.00323
C8 1 0.396498 0.361311 0.631647 11.00000 0.01053 0.01301 =
0.00902 0.00262 0.00139 0.00050
C9 1 0.451681 0.273876 0.640334 11.00000 0.01305 0.01256 =
0.01530 0.00495 0.00497 0.00436
AFIX 43
H9 2 0.412327 0.195562 0.646410 11.00000 -1.20000
AFIX 0
C10 1 0.578142 0.323526 0.638433 11.00000 0.01376 0.01310 =
0.01053 0.00397 0.00336 0.00513
C11 1 0.677994 0.264726 0.647346 11.00000 0.01564 0.01634 =
0.02275 0.00539 0.00716 0.00885
AFIX 137
H11A 2 0.752981 0.315767 0.633580 11.00000 -1.50000
H11B 2 0.644204 0.189202 0.597180 11.00000 -1.50000
H11C 2 0.702514 0.250508 0.717143 11.00000 -1.50000
AFIX 0
CU2 4 0.169896 0.540841 0.863073 11.00000 0.00749 0.01105 =
0.01516 0.00520 0.00545 0.00491
CL2 3 0.047456 0.653735 0.807893 11.00000 0.01196 0.01668 =
0.01829 0.00640 0.00597 0.00879
CL3 3 0.221677 0.594546 1.060323 11.00000 0.01030 0.01803 =
0.01404 0.00345 0.00498 0.00581
O4 6 0.450314 -0.062169 0.848753 11.00000 0.02352 0.01262 =
0.02712 0.00538 0.00971 0.01141
O5 6 0.321799 0.649794 0.846793 11.00000 0.00909 0.01247 =
0.01942 0.00708 0.00696 0.00657
N9 5 0.376379 0.139028 0.892426 11.00000 0.00924 0.00770 =
0.01869 0.00353 0.00386 0.00293
N10 5 0.210059 0.215105 0.884590 11.00000 0.00938 0.01006 =
0.01293 0.00114 0.00266 0.00266
N11 5 0.247927 0.414866 0.864332 11.00000 0.00726 0.01073 =
0.01194 0.00230 0.00238 0.00331
N12 5 0.418039 0.334608 0.883932 11.00000 0.01016 0.00853 =
0.01217 0.00257 0.00370 0.00370
N13 5 0.052115 0.301535 0.866509 11.00000 0.00825 0.00908 =
0.02059 0.00534 0.00595 0.00305
H13 2 0.006222 0.249434 0.887917 11.00000 0.01122
N14 5 0.015684 0.402750 0.851275 11.00000 0.00914 0.01521 =
0.01534 0.00425 0.00635 0.00665
H14A 2 -0.030176 0.413693 0.890755 11.00000 0.01689
H14B 2 -0.032494 0.387043 0.786642 11.00000 0.03216
N15 5 0.450582 0.526943 0.869147 11.00000 0.00720 0.01200 =
0.01409 0.00422 0.00522 0.00569
N16 5 0.576615 0.539933 0.875592 11.00000 0.00621 0.01396 =
0.01594 0.00400 0.00442 0.00600
C12 1 0.519543 0.048623 0.832881 11.00000 0.02523 0.01775 =
0.02805 0.01001 0.01521 0.01288
AFIX 23
H12A 2 0.484717 0.054226 0.760719 11.00000 -1.20000
H12B 2 0.610240 0.053882 0.844214 11.00000 -1.20000
AFIX 0
C13 1 0.318163 -0.073206 0.829514 11.00000 0.02135 0.01280 =
0.02505 0.00204 0.00132 0.00697
AFIX 23
H13A 2 0.271078 -0.151393 0.839220 11.00000 -1.20000
H13B 2 0.282682 -0.068856 0.757088 11.00000 -1.20000
AFIX 0
C14 1 0.511092 0.150285 0.905236 11.00000 0.00987 0.01406 =
0.02802 0.00649 0.00579 0.00721
AFIX 23
H14C 2 0.553346 0.149682 0.977368 11.00000 -1.20000
H14D 2 0.555411 0.226177 0.889973 11.00000 -1.20000
AFIX 0
C15 1 0.298794 0.023243 0.900964 11.00000 0.01415 0.01024 =
0.02658 0.00592 0.00705 0.00392
AFIX 23
H15A 2 0.207479 0.017530 0.881996 11.00000 -1.20000
H15B 2 0.324264 0.013498 0.972972 11.00000 -1.20000
AFIX 0
C16 1 0.333196 0.230290 0.887021 11.00000 0.00969 0.01083 =
0.00725 -0.00034 0.00023 0.00274
C17 1 0.173190 0.308797 0.872106 11.00000 0.00912 0.01145 =
0.00622 0.00009 0.00232 0.00256
C18 1 0.368278 0.418642 0.872371 11.00000 0.00956 0.01050 =
0.00681 0.00096 0.00347 0.00300
C19 1 0.429672 0.634129 0.857813 11.00000 0.01276 0.00977 =
0.00781 0.00328 0.00434 0.00506
C20 1 0.547655 0.711335 0.858410 11.00000 0.01049 0.01152 =
0.01093 0.00337 0.00370 0.00337
AFIX 43
H20 2 0.564888 0.791718 0.853093 11.00000 -1.20000
AFIX 0
C21 1 0.634107 0.650180 0.868053 11.00000 0.01091 0.01108 =
0.00873 0.00099 0.00330 0.00184
C22 1 0.769494 0.687371 0.866755 11.00000 0.00844 0.01741 =
0.01683 0.00619 0.00327 0.00190
AFIX 137
H22A 2 0.815245 0.642296 0.906420 11.00000 -1.50000
H22B 2 0.809829 0.771940 0.897569 11.00000 -1.50000
H22C 2 0.772600 0.672376 0.795421 11.00000 -1.50000
AFIX 0
O6 6 1.139940 1.122246 0.621338 11.00000 0.06626 0.01535 =
0.07171 0.00574 0.05787 0.00213
H6C 2 1.173755 1.189587 0.629411 11.00000 0.03007
H6D 2 1.089630 1.114244 0.640753 11.00000 0.04767
O7 6 1.153008 0.898397 0.556748 11.00000 0.02628 0.01902 =
0.02517 0.00385 0.00141 0.00956
H7A 2 1.090909 0.873132 0.512780 11.00000 0.03957
H7B 2 1.156899 0.959536 0.567827 11.00000 0.05474
H8AA 2 -0.099579 0.198510 1.017788 11.00000 0.04146
H8AB 2 -0.158022 0.213795 0.955374 11.00000 0.04922
O10 6 0.036062 0.040431 0.965208 11.00000 0.33138 0.25403 =
0.22171 0.08717 0.13439 0.02395
H16 2 0.609243 0.488280 0.884663 11.00000 0.02234
HKLF 4
REM AMakop10_0m_a.res in P-1
REM R1 = 0.0386 for 6122 Fo > 4sig(Fo) and 0.0565 for all 7595 data
REM 535 parameters refined using 0 restraints
END
WGHT 0.0320 4.0984
REM Instructions for potential hydrogen bonds
HTAB O3 N8_$1
HTAB O3 Cl2_$2
HTAB N5 O7_$3
HTAB N6 Cl2
HTAB N6 Cl1_$2
HTAB C1 O8A_$4
EQIV $7 -x+2, -y+2, -z+1
HTAB C4 O6_$7
HTAB C4 O3_$1
HTAB N13 O8A
HTAB N13 O8B
HTAB N14 Cl3_$5
HTAB N14 Cl1
EQIV $8 x, y-1, z
HTAB C13 Cl2_$8
HTAB C13 O5_$8
HTAB C14 Cl3_$6
HTAB C15 O10
EQIV $9 x, y+1, z
HTAB C20 O4_$9
HTAB C22 Cl3_$6
HTAB C22 O10_$6
HTAB C22 N3
HTAB O6 O2_$4
HTAB O6 O1
HTAB O7 Cl1_$1
HTAB O7 O6
HTAB O8A Cl2_$5
HTAB O8B Cl2_$5
HTAB O8A Cl3_$5
HTAB O8B Cl3_$5
HTAB N16 Cl3_$6
REM Highest difference peak 2.201, deepest hole -1.005, 1-sigma level 0.097
Q1 1 0.6454 0.4260 0.8982 11.00000 0.05 0.45
Q2 1 0.5800 0.7015 0.6108 11.00000 0.05 0.44
Q3 1 0.5183 0.2960 0.6505 11.00000 0.05 0.44
Q4 1 0.4013 0.4652 0.8561 11.00000 0.05 0.42
Q5 1 0.3282 0.0768 0.8853 11.00000 0.05 0.42
Q6 1 0.4183 0.5799 0.6046 11.00000 0.05 0.41
Q7 1 0.3882 0.6397 0.6144 11.00000 0.05 0.39
Q8 1 0.3074 0.4178 0.8749 11.00000 0.05 0.38
Q9 1 0.4402 0.4133 0.6294 11.00000 0.05 0.38
Q10 1 0.5969 0.6884 0.8754 11.00000 0.05 0.38
Q11 1 -0.0128 0.3606 0.5367 11.00000 0.05 0.37
Q12 1 0.5024 0.5095 0.6419 11.00000 0.05 0.36
Q13 1 0.4806 0.3622 0.9034 11.00000 0.05 0.36
Q14 1 0.2172 0.3590 0.8569 11.00000 0.05 0.35
Q15 1 -0.0625 0.1193 1.0059 11.00000 0.05 0.35
Q16 1 0.3985 0.2992 0.6175 11.00000 0.05 0.35
Q17 1 0.5263 0.5310 0.8820 11.00000 0.05 0.35
Q18 1 0.9922 0.9031 0.7602 11.00000 0.05 0.34
Q19 1 0.2863 0.4154 0.6317 11.00000 0.05 0.34
Q20 1 0.8239 0.7351 0.9177 11.00000 0.05 0.34
Q21 1 0.5594 0.7509 0.8758 11.00000 0.05 0.34
Q22 1 0.7548 1.0033 0.6612 11.00000 0.05 0.33
Q23 1 0.4982 0.6848 0.8681 11.00000 0.05 0.33
Q24 1 0.2442 0.2015 0.8606 11.00000 0.05 0.33
Q25 1 0.7525 0.8351 0.6351 11.00000 0.05 0.32
Q26 1 0.7927 0.7869 0.8496 11.00000 0.05 0.32
Q27 1 0.3457 0.3648 0.6373 11.00000 0.05 0.32
Q28 1 0.1111 0.1161 0.9541 11.00000 0.05 0.32
Q29 1 0.1634 0.2229 0.8497 11.00000 0.05 0.31
Q30 1 0.6197 0.2860 0.6467 11.00000 0.05 0.31
;
_shelx_res_checksum 84755
#######################################################################
#
# 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_Complex-8
_database_code_depnum_ccdc_archive 'CCDC 1555237'
_audit_update_record
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_Complex-8
;
PROBLEM: Short Inter D...A Contact
RESPONSE: The crystals of this complex were small sized with poor X-ray
diffraction and repeated recrystallization under different environments
did not gave better quality crystals. These alerts arise
because of large number of disordered solvate water molecules with multiple
occupancies. Due to poor quality of X-ray diffraction data, most of solvent
disorders could not be modeled.
;
_vrf_PLAT306_Complex-8
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O6 Check
RESPONSE: The hydrogen atoms associated with the disordered solvate
water molecules with multiple occupancies could not be located
in the difference density map.
;
_vrf_PLAT430_B_Complex-8
;
PROBLEM: Short Inter D...A Contact
RESPONSE: These alerts arise because of large number of disordered solvate
water molecules with multiple occupancies. PLATON/SQUEEZE option was not used
because the total number of disorderd solvate molecules was not ascertained.
;
_vrf_PLAT431_Complex-8
;
PROBLEM: Short Inter HL..A Contact Cl2 .. O13B
RESPONSE: This is again due to the disordered solvate molecules.
;
_audit_creation_date 2017-08-06
_audit_creation_method SHELXL-2014/7
_shelx_SHELXL_version_number 2014/7
_chemical_name_systematic ?
_chemical_name_common none
_chemical_melting_point 'not measured'
_chemical_formula_moiety
'C22 H31 N16 O4 Zn, 0.497(O3), Cl, H2 O, 6.5(O)'
_chemical_formula_sum 'C22 H33 Cl N16 O13 Zn'
_chemical_formula_weight 830.48
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'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_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.
;
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 12.4036(8)
_cell_length_b 19.8086(13)
_cell_length_c 14.3748(9)
_cell_angle_alpha 90
_cell_angle_beta 91.559(2)
_cell_angle_gamma 90
_cell_volume 3530.6(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9902
_cell_measurement_theta_min 2.97
_cell_measurement_theta_max 26.40
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method none
_exptl_crystal_density_diffrn 1.562
_exptl_crystal_F_000 1712
_exptl_transmission_factor_min 0.961
_exptl_transmission_factor_max 0.974
_exptl_crystal_size_max 0.326
_exptl_crystal_size_mid 0.124
_exptl_crystal_size_min 0.105
_exptl_absorpt_coefficient_mu 0.855
_shelx_estimated_absorpt_T_min 0.768
_shelx_estimated_absorpt_T_max 0.916
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.881
_exptl_absorpt_correction_T_max 0.914
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0826 before and 0.0742 after correction. The Ratio of minimum to maximum transmission is 0.8679. The \l/2 correction factor is 0.00150.'
;
_exptl_absorpt_special_details
;
The crystal was mounted using Paratone-N oil (cryoprotectant)
on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic
head of goniometer directly into the cold gas stream of a
liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focused sealed tube'
_diffrn_measurement_device_type
;
Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method
;
\f and \w scans with 0.5 deg/frame and 20 seconds of
exposure time. Detector was at 50mm from crystal.
;
_diffrn_detector 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number 123887
_diffrn_reflns_av_unetI/netI 0.0587
_diffrn_reflns_av_R_equivalents 0.1068
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -25
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.968
_diffrn_reflns_theta_max 27.167
_diffrn_reflns_theta_full 25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total 7821
_reflns_number_gt 5705
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_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.
;
_computing_data_collection 'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement 'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution 'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics
;
ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material 'WinGX2014.1 (Farrugia, 2012)'
_refine_special_details ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0145P)^2^+24.9549P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary mixed
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 7821
_refine_ls_number_parameters 532
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.1249
_refine_ls_R_factor_gt 0.0864
_refine_ls_wR_factor_ref 0.1760
_refine_ls_wR_factor_gt 0.1627
_refine_ls_goodness_of_fit_ref 1.193
_refine_ls_restrained_S_all 1.193
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
O13A O 0.792(3) 0.2507(8) 0.9387(14) 0.160(7) Uani 0.497(7) 1 d . . P A 1
O13B O 0.817(2) 0.2731(8) 1.0269(12) 0.160(7) Uani 0.503(7) 1 d . . P A 2
Zn1 Zn 0.15124(5) 0.53094(3) 0.72352(4) 0.02037(17) Uani 1 1 d . . . . .
O1 O 0.8147(3) 0.4817(2) 0.9636(3) 0.0287(9) Uani 1 1 d . . . . .
O2 O 0.2147(3) 0.5628(2) 0.5996(3) 0.0240(9) Uani 1 1 d . . . . .
O3 O 0.1357(3) 0.43050(18) 0.6921(2) 0.0200(8) Uani 1 1 d . . . . .
O4 O -0.5234(3) 0.5966(2) 0.5149(3) 0.0338(10) Uani 1 1 d . . . . .
N1 N 0.6087(3) 0.4935(2) 0.8787(3) 0.0245(11) Uani 1 1 d . . . . .
N2 N 0.4595(3) 0.5592(2) 0.8500(3) 0.0207(10) Uani 1 1 d . . . . .
N3 N 0.3028(3) 0.5074(2) 0.7803(3) 0.0177(9) Uani 1 1 d . . . . .
N4 N 0.4575(3) 0.4406(2) 0.8159(3) 0.0198(10) Uani 1 1 d . . . . .
N5 N 0.3119(3) 0.6214(2) 0.8144(3) 0.0227(10) Uani 1 1 d . . . . .
N6 N 0.2050(4) 0.6290(3) 0.7777(4) 0.0256(11) Uani 1 1 d . . . . .
N7 N 0.3035(3) 0.3913(2) 0.7559(3) 0.0196(10) Uani 1 1 d . . . . .
N8 N 0.3562(4) 0.3289(2) 0.7675(4) 0.0288(11) Uani 1 1 d . . . . .
N9 N -0.3095(3) 0.5675(2) 0.5723(3) 0.0198(10) Uani 1 1 d . . . . .
N10 N -0.1285(3) 0.5779(2) 0.5423(3) 0.0170(9) Uani 1 1 d . . . . .
N11 N -0.1882(3) 0.5424(2) 0.6914(3) 0.0210(10) Uani 1 1 d . . . . .
N12 N -0.0002(3) 0.5512(2) 0.6622(3) 0.0172(9) Uani 1 1 d . . . . .
N13 N 0.0531(3) 0.5834(2) 0.5156(3) 0.0190(9) Uani 1 1 d . . . . .
N14 N 0.0276(3) 0.6112(2) 0.4290(3) 0.0193(10) Uani 1 1 d . . . . .
N15 N -0.0624(3) 0.5173(2) 0.8040(3) 0.0228(11) Uani 1 1 d . . . . .
N16 N 0.0455(3) 0.5168(3) 0.8399(3) 0.0221(10) Uani 1 1 d . . . . .
C1 C 0.7524(4) 0.4229(3) 0.9446(4) 0.0298(14) Uani 1 1 d . . . . .
H1A H 0.7115 0.4108 1.0003 0.036 Uiso 1 1 calc R U . . .
H1B H 0.8013 0.3848 0.9308 0.036 Uiso 1 1 calc R U . . .
C2 C 0.7457(4) 0.5372(3) 0.9852(4) 0.0290(13) Uani 1 1 d . . . . .
H2A H 0.7903 0.5773 1.0005 0.035 Uiso 1 1 calc R U . . .
H2B H 0.7035 0.5258 1.0405 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6691(4) 0.5538(3) 0.9046(4) 0.0250(13) Uani 1 1 d . . . . .
H3A H 0.6189 0.5900 0.9229 0.030 Uiso 1 1 calc R U . . .
H3B H 0.7103 0.5700 0.8510 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6739(4) 0.4334(3) 0.8622(4) 0.0257(13) Uani 1 1 d . . . . .
H4A H 0.7145 0.4391 0.8043 0.031 Uiso 1 1 calc R U . . .
H4B H 0.6265 0.3934 0.8547 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5047(4) 0.4978(3) 0.8471(4) 0.0193(11) Uani 1 1 d . . . . .
C6 C 0.3570(4) 0.4488(3) 0.7850(4) 0.0184(11) Uani 1 1 d . . . . .
C7 C 0.3587(4) 0.5607(3) 0.8146(3) 0.0185(11) Uani 1 1 d . . . . .
C8 C 0.1996(4) 0.3822(3) 0.7143(4) 0.0213(12) Uani 1 1 d . . . . .
C9 C 0.1896(4) 0.3136(3) 0.7014(4) 0.0297(14) Uani 1 1 d . . . . .
H9 H 0.1288 0.2908 0.6750 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2858(5) 0.2838(3) 0.7342(5) 0.0321(14) Uani 1 1 d . . . . .
C11 C 0.3120(6) 0.2104(3) 0.7354(6) 0.049(2) Uani 1 1 d . . . . .
H11A H 0.3895 0.2044 0.7266 0.074 Uiso 1 1 calc R U . . .
H11B H 0.2715 0.1877 0.6850 0.074 Uiso 1 1 calc R U . . .
H11C H 0.2923 0.1910 0.7952 0.074 Uiso 1 1 calc R U . . .
C12 C 0.1660(4) 0.5825(3) 0.5270(4) 0.0198(11) Uani 1 1 d . . . . .
C13 C 0.2069(4) 0.6090(3) 0.4446(4) 0.0201(11) Uani 1 1 d . . . . .
H13 H 0.2810 0.6150 0.4316 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1215(4) 0.6247(3) 0.3861(4) 0.0194(11) Uani 1 1 d . . . . .
C15 C 0.1209(4) 0.6539(3) 0.2915(4) 0.0246(12) Uani 1 1 d . . . . .
H15A H 0.0831 0.6232 0.2482 0.037 Uiso 1 1 calc R U . . .
H15B H 0.1953 0.6601 0.2719 0.037 Uiso 1 1 calc R U . . .
H15C H 0.0839 0.6976 0.2917 0.037 Uiso 1 1 calc R U . . .
C16 C -0.0292(4) 0.5705(3) 0.5763(4) 0.0162(11) Uani 1 1 d . . . . .
C17 C -0.0839(4) 0.5378(3) 0.7169(4) 0.0193(11) Uani 1 1 d . . . . .
C18 C -0.2065(4) 0.5622(3) 0.6036(4) 0.0175(11) Uani 1 1 d . . . . .
C19 C -0.3372(4) 0.5807(3) 0.4744(4) 0.0263(13) Uani 1 1 d . . . . .
H19A H -0.3518 0.5376 0.4416 0.032 Uiso 1 1 calc R U . . .
H19B H -0.2759 0.6032 0.4443 0.032 Uiso 1 1 calc R U . . .
C20 C -0.4355(4) 0.6253(4) 0.4677(5) 0.0393(17) Uani 1 1 d . . . . .
H20A H -0.4181 0.6700 0.4949 0.047 Uiso 1 1 calc R U . . .
H20B H -0.4564 0.6320 0.4013 0.047 Uiso 1 1 calc R U . . .
C21 C -0.4968(4) 0.5880(4) 0.6112(4) 0.0352(15) Uani 1 1 d . . . . .
H21A H -0.5592 0.5682 0.6428 0.042 Uiso 1 1 calc R U . . .
H21B H -0.4817 0.6327 0.6395 0.042 Uiso 1 1 calc R U . . .
C22 C -0.3998(4) 0.5429(3) 0.6262(4) 0.0306(14) Uani 1 1 d . . . . .
H22A H -0.3788 0.5421 0.6931 0.037 Uiso 1 1 calc R U . . .
H22B H -0.4182 0.4963 0.6068 0.037 Uiso 1 1 calc R U . . .
Cl2 Cl 0.0088(2) 0.32187(10) 1.10412(15) 0.0662(7) Uani 1 1 d . . . . .
O5 O 0.0468(4) 0.3766(3) 0.9002(4) 0.0470(13) Uani 1 1 d D . . . .
O6 O 0.3931(5) 0.1917(3) 0.4726(4) 0.0702(18) Uani 1 1 d . . . . .
O7 O 0.5790(5) 0.2250(3) 0.5782(4) 0.0627(16) Uani 1 1 d . . . . .
O8 O 0.5773(4) 0.2872(3) 0.7541(4) 0.0533(14) Uani 1 1 d . . . . .
O9A O 0.6707(19) 0.2186(11) 0.8935(14) 0.103(9) Uani 0.497(7) 1 d . . P A 1
O9B O 0.6611(10) 0.2388(12) 0.9277(12) 0.095(8) Uani 0.503(7) 1 d . . P A 2
O10A O 0.8890(11) 0.2427(7) 0.9196(10) 0.066(2) Uani 0.497(7) 1 d . . P A 1
O10B O 0.8350(10) 0.2288(7) 0.8700(9) 0.066(2) Uani 0.503(7) 1 d . . P A 2
O11 O 1.0475(6) 0.2116(4) 0.8313(5) 0.088(2) Uani 1 1 d . . . . .
O12 O 1.1909(6) 0.2444(4) 0.9733(5) 0.095(2) Uani 1 1 d . . . . .
H5 H 0.348(5) 0.658(3) 0.835(4) 0.028(17) Uiso 1 1 d . . . . .
H6A H 0.169(4) 0.649(3) 0.819(4) 0.014(15) Uiso 1 1 d . . . . .
H6B H 0.202(5) 0.658(4) 0.730(5) 0.04(2) Uiso 1 1 d . . . . .
H15 H -0.111(4) 0.510(3) 0.839(4) 0.014(14) Uiso 1 1 d . . . . .
H16A H 0.046(4) 0.550(3) 0.886(3) 0.003(12) Uiso 1 1 d . . . . .
H16B H 0.056(4) 0.479(3) 0.861(4) 0.018(16) Uiso 1 1 d . . . . .
H5A H 0.031(4) 0.364(3) 0.965(4) 0.019(15) Uiso 1 1 d D . . . .
H14 H -0.027(6) 0.598(4) 0.403(5) 0.05(2) Uiso 1 1 d . . . . .
H5B H 0.07(3) 0.334(5) 0.871(10) 0.7(3) 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
O13A 0.33(2) 0.055(7) 0.093(10) -0.008(7) -0.043(13) -0.003(11)
O13B 0.33(2) 0.055(7) 0.093(10) -0.008(7) -0.043(13) -0.003(11)
Zn1 0.0115(3) 0.0250(3) 0.0242(3) 0.0029(3) -0.0068(2) 0.0000(3)
O1 0.0148(18) 0.048(3) 0.023(2) 0.0031(19) -0.0078(15) -0.0006(18)
O2 0.0100(17) 0.039(2) 0.023(2) 0.0057(17) -0.0044(15) 0.0011(16)
O3 0.0145(17) 0.024(2) 0.0209(19) 0.0025(16) -0.0085(14) 0.0001(15)
O4 0.0083(18) 0.044(3) 0.049(3) 0.012(2) 0.0011(17) 0.0016(17)
N1 0.011(2) 0.031(3) 0.030(3) -0.006(2) -0.0104(18) 0.0008(19)
N2 0.013(2) 0.025(2) 0.023(2) 0.001(2) -0.0040(18) -0.0025(18)
N3 0.013(2) 0.022(2) 0.017(2) 0.0021(18) -0.0056(17) -0.0020(17)
N4 0.011(2) 0.027(2) 0.021(2) 0.0008(19) -0.0045(17) 0.0007(18)
N5 0.015(2) 0.026(3) 0.027(3) -0.002(2) -0.0055(19) -0.0009(19)
N6 0.016(2) 0.030(3) 0.031(3) 0.000(2) -0.002(2) 0.007(2)
N7 0.013(2) 0.020(2) 0.026(2) 0.0021(19) -0.0055(18) 0.0018(18)
N8 0.021(2) 0.023(2) 0.042(3) 0.003(2) -0.011(2) 0.002(2)
N9 0.0098(19) 0.035(3) 0.015(2) -0.001(2) -0.0006(16) 0.0009(19)
N10 0.0108(19) 0.025(2) 0.015(2) -0.0014(18) 0.0001(16) -0.0012(17)
N11 0.0110(19) 0.032(3) 0.020(2) 0.001(2) -0.0060(17) -0.0031(18)
N12 0.012(2) 0.023(2) 0.017(2) 0.0016(18) -0.0027(17) -0.0024(17)
N13 0.011(2) 0.025(2) 0.022(2) 0.0047(19) -0.0028(17) 0.0000(17)
N14 0.011(2) 0.027(3) 0.019(2) -0.0006(19) -0.0027(18) 0.0001(19)
N15 0.010(2) 0.037(3) 0.021(2) 0.007(2) -0.0003(19) -0.0001(19)
N16 0.015(2) 0.029(3) 0.023(3) 0.002(2) -0.0077(18) 0.001(2)
C1 0.015(3) 0.043(4) 0.031(3) 0.010(3) -0.003(2) -0.001(2)
C2 0.020(3) 0.044(4) 0.023(3) 0.005(3) -0.006(2) -0.004(3)
C3 0.015(2) 0.032(3) 0.027(3) -0.002(2) -0.005(2) -0.006(2)
C4 0.010(2) 0.036(3) 0.030(3) 0.002(3) -0.004(2) 0.004(2)
C5 0.010(2) 0.032(3) 0.016(3) 0.001(2) 0.0035(19) -0.003(2)
C6 0.016(2) 0.024(3) 0.015(3) 0.003(2) -0.002(2) -0.002(2)
C7 0.016(2) 0.027(3) 0.012(2) 0.004(2) -0.0013(19) 0.000(2)
C8 0.012(2) 0.032(3) 0.019(3) -0.001(2) -0.004(2) -0.006(2)
C9 0.020(3) 0.029(3) 0.040(4) 0.003(3) -0.012(2) -0.005(2)
C10 0.024(3) 0.027(3) 0.045(4) 0.003(3) -0.011(3) -0.003(2)
C11 0.039(4) 0.026(4) 0.081(6) 0.003(4) -0.023(4) 0.004(3)
C12 0.012(2) 0.021(3) 0.026(3) -0.005(2) -0.005(2) 0.001(2)
C13 0.011(2) 0.024(3) 0.026(3) -0.002(2) -0.003(2) 0.000(2)
C14 0.012(2) 0.026(3) 0.020(3) -0.004(2) 0.001(2) -0.003(2)
C15 0.017(3) 0.036(3) 0.021(3) 0.002(2) 0.001(2) -0.004(2)
C16 0.011(2) 0.016(3) 0.021(3) -0.001(2) -0.005(2) -0.0002(19)
C17 0.019(2) 0.017(3) 0.022(3) -0.001(2) -0.003(2) 0.000(2)
C18 0.017(2) 0.016(3) 0.019(3) -0.003(2) -0.004(2) -0.001(2)
C19 0.011(2) 0.044(4) 0.024(3) 0.003(3) 0.000(2) 0.003(2)
C20 0.014(3) 0.046(4) 0.057(4) 0.020(3) 0.001(3) 0.004(3)
C21 0.017(3) 0.050(4) 0.039(4) -0.016(3) 0.005(3) -0.003(3)
C22 0.010(2) 0.060(4) 0.022(3) 0.004(3) -0.001(2) -0.008(3)
Cl2 0.1089(18) 0.0397(11) 0.0515(12) 0.0112(9) 0.0314(12) 0.0282(11)
O5 0.054(3) 0.043(3) 0.043(3) 0.008(2) -0.016(2) -0.011(2)
O6 0.103(5) 0.063(4) 0.043(3) 0.012(3) -0.032(3) -0.023(3)
O7 0.075(4) 0.041(3) 0.070(4) 0.004(3) -0.032(3) 0.016(3)
O8 0.031(2) 0.060(3) 0.068(4) -0.008(3) -0.019(2) 0.006(2)
O9A 0.118(16) 0.087(11) 0.099(16) -0.056(11) -0.068(12) 0.052(10)
O9B 0.014(5) 0.22(2) 0.056(10) 0.075(13) -0.004(6) -0.017(10)
O10A 0.068(6) 0.068(6) 0.063(7) -0.004(5) -0.002(4) -0.018(5)
O10B 0.068(6) 0.068(6) 0.063(7) -0.004(5) -0.002(4) -0.018(5)
O11 0.089(5) 0.095(5) 0.080(5) 0.031(4) -0.017(4) -0.012(4)
O12 0.099(5) 0.107(6) 0.077(5) -0.028(4) -0.021(4) 0.030(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
O13A O10A 1.25(3) . ?
O13A O9A 1.74(3) . ?
Zn1 O3 2.048(4) . ?
Zn1 O2 2.066(4) . ?
Zn1 N3 2.082(4) . ?
Zn1 N12 2.092(4) . ?
Zn1 N16 2.172(5) . ?
Zn1 N6 2.191(5) . ?
O1 C1 1.421(7) . ?
O1 C2 1.432(7) . ?
O2 C12 1.253(6) . ?
O3 C8 1.277(6) . ?
O4 C20 1.418(7) . ?
O4 C21 1.425(7) . ?
N1 C5 1.358(6) . ?
N1 C3 1.454(7) . ?
N1 C4 1.462(7) . ?
N2 C7 1.338(6) . ?
N2 C5 1.340(7) . ?
N3 C6 1.343(7) . ?
N3 C7 1.348(7) . ?
N4 C6 1.322(6) . ?
N4 C5 1.347(7) . ?
N5 C7 1.334(7) . ?
N5 N6 1.421(6) . ?
N5 H5 0.89(6) . ?
N6 H6A 0.85(6) . ?
N6 H6B 0.90(7) . ?
N7 C6 1.378(7) . ?
N7 N8 1.405(6) . ?
N7 C8 1.417(6) . ?
N8 C10 1.331(7) . ?
N9 C18 1.346(6) . ?
N9 C22 1.463(7) . ?
N9 C19 1.463(7) . ?
N10 C16 1.321(6) . ?
N10 C18 1.363(7) . ?
N11 C18 1.336(7) . ?
N11 C17 1.338(6) . ?
N12 C16 1.332(6) . ?
N12 C17 1.345(7) . ?
N13 C16 1.385(7) . ?
N13 N14 1.390(6) . ?
N13 C12 1.406(6) . ?
N14 C14 1.360(7) . ?
N14 H14 0.81(7) . ?
N15 C17 1.336(7) . ?
N15 N16 1.422(6) . ?
N15 H15 0.81(6) . ?
N16 H16A 0.93(5) . ?
N16 H16B 0.81(6) . ?
C1 C4 1.527(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.514(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.377(8) . ?
C9 C10 1.402(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.488(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.403(8) . ?
C13 C14 1.371(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.477(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C19 C20 1.507(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.509(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O5 H5A 0.99(6) . ?
O5 H5B 0.99(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
O10A O13A O9A 134.2(17) . . ?
O3 Zn1 O2 98.17(15) . . ?
O3 Zn1 N3 87.01(15) . . ?
O2 Zn1 N3 92.59(15) . . ?
O3 Zn1 N12 90.89(15) . . ?
O2 Zn1 N12 86.38(15) . . ?
N3 Zn1 N12 177.51(18) . . ?
O3 Zn1 N16 89.43(18) . . ?
O2 Zn1 N16 162.92(16) . . ?
N3 Zn1 N16 103.11(17) . . ?
N12 Zn1 N16 78.19(16) . . ?
O3 Zn1 N6 165.00(15) . . ?
O2 Zn1 N6 85.21(19) . . ?
N3 Zn1 N6 78.21(17) . . ?
N12 Zn1 N6 103.94(17) . . ?
N16 Zn1 N6 91.4(2) . . ?
C1 O1 C2 110.3(4) . . ?
C12 O2 Zn1 128.8(3) . . ?
C8 O3 Zn1 128.2(3) . . ?
C20 O4 C21 110.6(4) . . ?
C5 N1 C3 120.8(5) . . ?
C5 N1 C4 121.5(4) . . ?
C3 N1 C4 115.3(4) . . ?
C7 N2 C5 113.4(4) . . ?
C6 N3 C7 114.0(4) . . ?
C6 N3 Zn1 131.2(3) . . ?
C7 N3 Zn1 114.7(3) . . ?
C6 N4 C5 113.9(4) . . ?
C7 N5 N6 119.9(5) . . ?
C7 N5 H5 121(4) . . ?
N6 N5 H5 119(4) . . ?
N5 N6 Zn1 108.0(3) . . ?
N5 N6 H6A 107(4) . . ?
Zn1 N6 H6A 120(4) . . ?
N5 N6 H6B 112(4) . . ?
Zn1 N6 H6B 107(4) . . ?
H6A N6 H6B 103(6) . . ?
C6 N7 N8 118.1(4) . . ?
C6 N7 C8 131.1(4) . . ?
N8 N7 C8 110.7(4) . . ?
C10 N8 N7 104.4(4) . . ?
C18 N9 C22 122.0(4) . . ?
C18 N9 C19 122.1(4) . . ?
C22 N9 C19 113.9(4) . . ?
C16 N10 C18 114.0(4) . . ?
C18 N11 C17 114.7(4) . . ?
C16 N12 C17 113.8(4) . . ?
C16 N12 Zn1 131.5(3) . . ?
C17 N12 Zn1 114.5(3) . . ?
C16 N13 N14 118.9(4) . . ?
C16 N13 C12 132.3(4) . . ?
N14 N13 C12 108.1(4) . . ?
C14 N14 N13 107.9(4) . . ?
C14 N14 H14 125(5) . . ?
N13 N14 H14 117(5) . . ?
C17 N15 N16 120.3(5) . . ?
C17 N15 H15 121(4) . . ?
N16 N15 H15 119(4) . . ?
N15 N16 Zn1 107.5(3) . . ?
N15 N16 H16A 104(3) . . ?
Zn1 N16 H16A 118(3) . . ?
N15 N16 H16B 107(4) . . ?
Zn1 N16 H16B 108(4) . . ?
H16A N16 H16B 113(5) . . ?
O1 C1 C4 111.7(5) . . ?
O1 C1 H1A 109.3 . . ?
C4 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C4 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C3 111.6(5) . . ?
O1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C2 109.0(5) . . ?
N1 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C1 109.3(5) . . ?
N1 C4 H4A 109.8 . . ?
C1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C1 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 N4 126.5(4) . . ?
N2 C5 N1 116.2(5) . . ?
N4 C5 N1 117.3(5) . . ?
N4 C6 N3 126.1(5) . . ?
N4 C6 N7 116.3(5) . . ?
N3 C6 N7 117.6(4) . . ?
N5 C7 N2 115.0(5) . . ?
N5 C7 N3 119.0(4) . . ?
N2 C7 N3 125.9(5) . . ?
O3 C8 C9 130.7(5) . . ?
O3 C8 N7 124.2(5) . . ?
C9 C8 N7 105.0(5) . . ?
C8 C9 C10 107.4(5) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
N8 C10 C9 112.4(5) . . ?
N8 C10 C11 120.7(5) . . ?
C9 C10 C11 126.8(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 129.9(5) . . ?
O2 C12 N13 123.9(5) . . ?
C13 C12 N13 106.2(4) . . ?
C14 C13 C12 108.2(4) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
N14 C14 C13 109.5(5) . . ?
N14 C14 C15 120.8(4) . . ?
C13 C14 C15 129.7(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N10 C16 N12 126.9(5) . . ?
N10 C16 N13 116.2(4) . . ?
N12 C16 N13 116.8(4) . . ?
N15 C17 N11 116.4(5) . . ?
N15 C17 N12 118.0(4) . . ?
N11 C17 N12 125.6(5) . . ?
N11 C18 N9 118.3(5) . . ?
N11 C18 N10 124.9(4) . . ?
N9 C18 N10 116.8(4) . . ?
N9 C19 C20 109.6(5) . . ?
N9 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
N9 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
O4 C20 C19 111.5(5) . . ?
O4 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
O4 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
O4 C21 C22 111.8(5) . . ?
O4 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
O4 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N9 C22 C21 110.3(5) . . ?
N9 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
N9 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
H5A O5 H5B 104(6) . . ?
_refine_diff_density_max 1.216
_refine_diff_density_min -1.062
_refine_diff_density_rms 0.112
_shelx_res_file
;
shelx.res created by SHELXL-2014/7
TITL Amakop14.res in P2(1)/c
CELL 0.71073 12.4036 19.8086 14.3748 90 91.559 90
ZERR 8 0.0008 0.0013 0.0009 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O Zn
UNIT 88 132 4 64 52 4
DFIX 0.982 O5 H5b
DANG 1.58 H5a H5b
EADP O10A O10B
EADP O13A O13B
L.S. 50
PLAN 20
SIZE 0.105 0.124 0.326
TEMP -173.17
BOND $H
LIST 4
fmap 2
acta 50
MERG 2
REM
REM
REM
WGHT 0.014500 24.954899
FVAR 0.26027 0.49668
PART 1
O13A 5 0.791972 0.250681 0.938732 21.00000 0.32963 0.05469 =
0.09258 -0.00803 -0.04346 -0.00262
PART 0
PART 2
O13B 5 0.817121 0.273143 1.026910 -21.00000 0.32963 0.05469 =
0.09258 -0.00803 -0.04346 -0.00262
PART 0
ZN1 6 0.151243 0.530941 0.723517 11.00000 0.01152 0.02500 =
0.02420 0.00287 -0.00678 0.00002
O1 5 0.814686 0.481723 0.963625 11.00000 0.01478 0.04784 =
0.02305 0.00313 -0.00783 -0.00058
O2 5 0.214691 0.562797 0.599577 11.00000 0.00999 0.03874 =
0.02305 0.00566 -0.00438 0.00108
O3 5 0.135719 0.430497 0.692065 11.00000 0.01451 0.02404 =
0.02089 0.00246 -0.00850 0.00011
O4 5 -0.523420 0.596594 0.514859 11.00000 0.00832 0.04418 =
0.04906 0.01217 0.00110 0.00162
N1 4 0.608725 0.493476 0.878676 11.00000 0.01129 0.03128 =
0.03047 -0.00589 -0.01044 0.00083
N2 4 0.459500 0.559166 0.850009 11.00000 0.01338 0.02508 =
0.02337 0.00058 -0.00396 -0.00252
N3 4 0.302834 0.507450 0.780299 11.00000 0.01294 0.02234 =
0.01740 0.00213 -0.00561 -0.00200
N4 4 0.457520 0.440605 0.815941 11.00000 0.01101 0.02708 =
0.02105 0.00080 -0.00454 0.00075
N5 4 0.311940 0.621359 0.814392 11.00000 0.01543 0.02572 =
0.02668 -0.00175 -0.00549 -0.00093
N6 4 0.205048 0.629039 0.777744 11.00000 0.01635 0.02958 =
0.03069 0.00037 -0.00221 0.00716
N7 4 0.303509 0.391287 0.755902 11.00000 0.01301 0.01960 =
0.02575 0.00207 -0.00546 0.00177
N8 4 0.356235 0.328942 0.767502 11.00000 0.02072 0.02321 =
0.04173 0.00265 -0.01110 0.00236
N9 4 -0.309472 0.567470 0.572263 11.00000 0.00979 0.03509 =
0.01461 -0.00109 -0.00059 0.00092
N10 4 -0.128464 0.577911 0.542256 11.00000 0.01078 0.02527 =
0.01503 -0.00142 0.00013 -0.00124
N11 4 -0.188162 0.542421 0.691409 11.00000 0.01099 0.03173 =
0.02005 0.00106 -0.00604 -0.00314
N12 4 -0.000180 0.551211 0.662210 11.00000 0.01160 0.02250 =
0.01733 0.00157 -0.00270 -0.00244
N13 4 0.053117 0.583353 0.515611 11.00000 0.01068 0.02469 =
0.02159 0.00465 -0.00276 0.00000
N14 4 0.027598 0.611197 0.429049 11.00000 0.01095 0.02728 =
0.01939 -0.00063 -0.00269 0.00013
N15 4 -0.062365 0.517290 0.803957 11.00000 0.01046 0.03682 =
0.02107 0.00727 -0.00033 -0.00011
N16 4 0.045548 0.516836 0.839923 11.00000 0.01463 0.02884 =
0.02252 0.00199 -0.00774 0.00114
C1 1 0.752445 0.422864 0.944557 11.00000 0.01546 0.04280 =
0.03090 0.01041 -0.00331 -0.00054
AFIX 23
H1A 2 0.711487 0.410779 1.000320 11.00000 -1.20000
H1B 2 0.801312 0.384846 0.930807 11.00000 -1.20000
AFIX 0
C2 1 0.745682 0.537208 0.985177 11.00000 0.02002 0.04425 =
0.02251 0.00499 -0.00596 -0.00444
AFIX 23
H2A 2 0.790297 0.577340 1.000504 11.00000 -1.20000
H2B 2 0.703538 0.525813 1.040535 11.00000 -1.20000
AFIX 0
C3 1 0.669127 0.553843 0.904606 11.00000 0.01526 0.03234 =
0.02715 -0.00171 -0.00457 -0.00609
AFIX 23
H3A 2 0.618918 0.590037 0.922921 11.00000 -1.20000
H3B 2 0.710319 0.570050 0.850965 11.00000 -1.20000
AFIX 0
C4 1 0.673918 0.433403 0.862195 11.00000 0.01040 0.03612 =
0.03041 0.00179 -0.00366 0.00410
AFIX 23
H4A 2 0.714454 0.439102 0.804334 11.00000 -1.20000
H4B 2 0.626540 0.393441 0.854711 11.00000 -1.20000
AFIX 0
C5 1 0.504742 0.497818 0.847118 11.00000 0.00972 0.03245 =
0.01594 0.00105 0.00353 -0.00274
C6 1 0.357048 0.448810 0.785045 11.00000 0.01621 0.02360 =
0.01521 0.00315 -0.00195 -0.00160
C7 1 0.358653 0.560710 0.814649 11.00000 0.01566 0.02736 =
0.01234 0.00361 -0.00128 0.00010
C8 1 0.199624 0.382244 0.714255 11.00000 0.01224 0.03207 =
0.01924 -0.00092 -0.00387 -0.00648
C9 1 0.189650 0.313636 0.701352 11.00000 0.01950 0.02916 =
0.03968 0.00335 -0.01203 -0.00495
AFIX 43
H9 2 0.128817 0.290760 0.675013 11.00000 -1.20000
AFIX 0
C10 1 0.285772 0.283753 0.734232 11.00000 0.02366 0.02720 =
0.04469 0.00263 -0.01098 -0.00336
C11 1 0.312014 0.210433 0.735351 11.00000 0.03887 0.02614 =
0.08112 0.00315 -0.02256 0.00427
AFIX 137
H11A 2 0.389494 0.204360 0.726612 11.00000 -1.50000
H11B 2 0.271529 0.187676 0.684954 11.00000 -1.50000
H11C 2 0.292299 0.190986 0.795225 11.00000 -1.50000
AFIX 0
C12 1 0.166015 0.582462 0.527034 11.00000 0.01183 0.02115 =
0.02606 -0.00472 -0.00508 0.00115
C13 1 0.206911 0.608991 0.444620 11.00000 0.01087 0.02350 =
0.02569 -0.00156 -0.00288 0.00014
AFIX 43
H13 2 0.280986 0.615008 0.431644 11.00000 -1.20000
AFIX 0
C14 1 0.121480 0.624725 0.386073 11.00000 0.01204 0.02583 =
0.02033 -0.00427 0.00077 -0.00290
C15 1 0.120899 0.653863 0.291487 11.00000 0.01677 0.03584 =
0.02116 0.00150 0.00057 -0.00418
AFIX 137
H15A 2 0.083109 0.623216 0.248153 11.00000 -1.50000
H15B 2 0.195287 0.660128 0.271870 11.00000 -1.50000
H15C 2 0.083917 0.697580 0.291676 11.00000 -1.50000
AFIX 0
C16 1 -0.029188 0.570489 0.576332 11.00000 0.01131 0.01614 =
0.02094 -0.00088 -0.00488 -0.00015
C17 1 -0.083883 0.537822 0.716853 11.00000 0.01850 0.01734 =
0.02179 -0.00134 -0.00310 -0.00048
C18 1 -0.206532 0.562246 0.603565 11.00000 0.01680 0.01623 =
0.01917 -0.00253 -0.00404 -0.00071
C19 1 -0.337175 0.580699 0.474391 11.00000 0.01107 0.04384 =
0.02400 0.00327 -0.00030 0.00299
AFIX 23
H19A 2 -0.351754 0.537558 0.441630 11.00000 -1.20000
H19B 2 -0.275944 0.603174 0.444293 11.00000 -1.20000
AFIX 0
C20 1 -0.435533 0.625254 0.467656 11.00000 0.01438 0.04619 =
0.05728 0.01953 0.00124 0.00367
AFIX 23
H20A 2 -0.418115 0.669963 0.494928 11.00000 -1.20000
H20B 2 -0.456373 0.632025 0.401342 11.00000 -1.20000
AFIX 0
C21 1 -0.496758 0.588040 0.611188 11.00000 0.01725 0.04983 =
0.03864 -0.01588 0.00529 -0.00341
AFIX 23
H21A 2 -0.559196 0.568195 0.642810 11.00000 -1.20000
H21B 2 -0.481661 0.632724 0.639511 11.00000 -1.20000
AFIX 0
C22 1 -0.399795 0.542924 0.626178 11.00000 0.01023 0.05963 =
0.02192 0.00378 -0.00116 -0.00836
AFIX 23
H22A 2 -0.378824 0.542129 0.693114 11.00000 -1.20000
H22B 2 -0.418225 0.496279 0.606799 11.00000 -1.20000
AFIX 0
CL2 3 0.008845 0.321873 1.104123 11.00000 0.10890 0.03966 =
0.05154 0.01117 0.03143 0.02823
O5 5 0.046810 0.376615 0.900233 11.00000 0.05429 0.04254 =
0.04327 0.00812 -0.01561 -0.01084
O6 5 0.393122 0.191745 0.472616 11.00000 0.10262 0.06340 =
0.04261 0.01238 -0.03158 -0.02259
O7 5 0.579021 0.224979 0.578186 11.00000 0.07467 0.04132 =
0.07031 0.00403 -0.03164 0.01641
O8 5 0.577321 0.287172 0.754146 11.00000 0.03096 0.06013 =
0.06760 -0.00813 -0.01851 0.00639
PART 1
O9A 5 0.670717 0.218585 0.893520 21.00000 0.11834 0.08687 =
0.09863 -0.05562 -0.06831 0.05214
PART 0
PART 2
O9B 5 0.661074 0.238845 0.927722 -21.00000 0.01394 0.21649 =
0.05564 0.07487 -0.00389 -0.01747
PART 0
PART 1
O10A 5 0.889041 0.242705 0.919624 21.00000 0.06758 0.06796 =
0.06315 -0.00433 -0.00233 -0.01849
PART 0
PART 2
O10B 5 0.835017 0.228769 0.870032 -21.00000 0.06758 0.06796 =
0.06315 -0.00433 -0.00233 -0.01849
PART 0
O11 5 1.047455 0.211608 0.831307 11.00000 0.08905 0.09457 =
0.07995 0.03139 -0.01715 -0.01173
O12 5 1.190854 0.244422 0.973271 11.00000 0.09926 0.10749 =
0.07746 -0.02831 -0.02134 0.02979
H5 2 0.347742 0.657555 0.835329 11.00000 0.02834
H6A 2 0.169342 0.648561 0.819352 11.00000 0.01434
H6B 2 0.201623 0.658291 0.729750 11.00000 0.03933
H15 2 -0.110839 0.509806 0.839266 11.00000 0.01354
H16A 2 0.046158 0.549746 0.886116 11.00000 0.00334
H16B 2 0.056474 0.479312 0.860524 11.00000 0.01764
H5A 2 0.031094 0.363962 0.964751 11.00000 0.01900
H14 2 -0.027115 0.598122 0.402785 11.00000 0.04652
H5B 2 0.068520 0.333909 0.870778 11.00000 0.67501
HKLF 4
REM Amakop14.res in P2(1)/c
REM R1 = 0.0864 for 5705 Fo > 4sig(Fo) and 0.1249 for all 7821 data
REM 532 parameters refined using 2 restraints
END
WGHT 0.0145 24.9550
REM Highest difference peak 1.216, deepest hole -1.062, 1-sigma level 0.112
Q1 1 0.4886 0.2109 0.4448 11.00000 0.05 0.83
Q2 1 0.1235 0.5292 0.7815 11.00000 0.05 0.77
Q3 1 0.1564 0.5752 0.7558 11.00000 0.05 0.67
Q4 1 0.9296 0.2227 0.8759 11.00000 0.05 0.60
Q5 1 0.1448 0.5393 0.6402 11.00000 0.05 0.59
Q6 1 0.1433 0.4789 0.7037 11.00000 0.05 0.50
Q7 1 -0.0167 0.3197 1.0977 11.00000 0.05 0.49
Q8 1 0.6163 0.2529 0.6819 11.00000 0.05 0.48
Q9 1 1.1167 0.2504 1.0209 11.00000 0.05 0.45
Q10 1 0.0390 0.3346 1.1753 11.00000 0.05 0.45
Q11 1 0.6903 0.2648 0.9107 11.00000 0.05 0.44
Q12 1 1.1903 0.2851 0.9496 11.00000 0.05 0.43
Q13 1 0.7455 0.2409 0.8720 11.00000 0.05 0.42
Q14 1 0.6450 0.2520 0.8466 11.00000 0.05 0.42
Q15 1 0.6241 0.2489 0.5137 11.00000 0.05 0.41
Q16 1 0.5179 0.3199 0.7593 11.00000 0.05 0.41
Q17 1 0.0447 0.5355 0.6827 11.00000 0.05 0.40
Q18 1 -0.0832 0.3424 1.0609 11.00000 0.05 0.40
Q19 1 0.0363 0.2888 1.1602 11.00000 0.05 0.39
Q20 1 0.0171 0.5953 0.6828 11.00000 0.05 0.39
;
_shelx_res_checksum 86169