# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1922255'
loop_
_audit_author_name
_audit_author_address
'Dr. Ray J. Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N4 O2'
_chemical_formula_sum            'C18 H16 N4 O2'
_chemical_formula_weight         320.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   20.266(2)
_cell_length_b                   20.266(2)
_cell_length_c                   20.0904(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7145.9(15)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1726
_cell_measurement_theta_min      4.0360
_cell_measurement_theta_max      28.7490

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             3024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            17444
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             8026
_reflns_number_gt                3560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.862

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'Shelxt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   3.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8026
_refine_ls_number_parameters     652
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2135
_refine_ls_R_factor_gt           0.1351
_refine_ls_wR_factor_ref         0.3987
_refine_ls_wR_factor_gt          0.3388
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.003
_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
O1A O 1.0927(5) 0.7213(5) 0.0911(5) 0.054(2) Uani 1 1 d . . . . .
O2A O 0.6902(7) 0.5431(7) 0.0732(5) 0.065(3) Uani 1 1 d . . . . .
N1A N 1.1506(5) 0.8517(5) 0.0860(5) 0.034(2) Uani 1 1 d . . . . .
H1AA H 1.1960 0.8559 0.0867 0.041 Uiso 1 1 calc R U . . .
N2A N 0.8772(9) 0.6918(9) 0.0829(6) 0.073(4) Uani 1 1 d . . . . .
N3A N 0.8192(6) 0.6209(6) 0.0794(6) 0.045(3) Uani 1 1 d . . . . .
H3AB H 0.8274 0.5822 0.0798 0.054 Uiso 1 1 calc R U . . .
N4A N 0.7385(5) 0.6721(6) 0.0809(6) 0.044(3) Uani 1 1 d . . . . .
H4AA H 0.7815 0.7153 0.0866 0.052 Uiso 1 1 calc R U . . .
C1A C 1.0867(10) 0.7794(8) 0.0877(7) 0.052(4) Uani 1 1 d . . . . .
C2A C 1.0142(7) 0.7748(9) 0.0859(7) 0.056(4) Uani 1 1 d . . . . .
C3A C 1.0095(9) 0.8420(10) 0.0835(8) 0.056(4) Uani 1 1 d . . . . .
H3AA H 0.9613 0.8391 0.0838 0.067 Uiso 1 1 calc R U . . .
C4A C 1.0762(8) 0.9126(10) 0.0807(6) 0.053(4) Uani 1 1 d . . . . .
C5A C 1.0738(9) 0.9834(9) 0.0794(7) 0.053(4) Uani 1 1 d . . . . .
H5AA H 1.0268 0.9830 0.0822 0.063 Uiso 1 1 calc R U . . .
C6A C 1.1413(9) 1.0503(11) 0.0743(7) 0.065(4) Uani 1 1 d . . . . .
C7A C 1.2105(9) 1.0540(10) 0.0767(7) 0.064(4) Uani 1 1 d . . . . .
H7AA H 1.2564 1.1019 0.0761 0.076 Uiso 1 1 calc R U . . .
C8A C 1.2126(7) 0.9873(8) 0.0801(7) 0.047(3) Uani 1 1 d . . . . .
H8AA H 1.2601 0.9886 0.0803 0.057 Uiso 1 1 calc R U . . .
C9A C 1.1460(7) 0.9188(8) 0.0833(6) 0.039(3) Uani 1 1 d . . . . .
C10A C 1.1419(10) 1.1304(10) 0.0682(9) 0.076(5) Uani 1 1 d . . . . .
H10A H 1.0894 1.1207 0.0695 0.114 Uiso 1 1 calc R U . . .
H10B H 1.1658 1.1552 0.0261 0.114 Uiso 1 1 calc R U . . .
H10C H 1.1707 1.1636 0.1054 0.114 Uiso 1 1 calc R U . . .
C11A C 0.9446(8) 0.6997(10) 0.0854(7) 0.057(4) Uani 1 1 d . . . . .
H11A H 0.9493 0.6554 0.0869 0.069 Uiso 1 1 calc R U . . .
C12A C 0.7462(9) 0.6087(10) 0.0753(8) 0.063(4) Uani 1 1 d . . . . .
C13A C 0.6751(7) 0.6783(7) 0.0791(8) 0.049(3) Uani 1 1 d . . . . .
C14A C 0.6041(9) 0.6215(9) 0.0494(7) 0.057(4) Uani 1 1 d . . . . .
H14A H 0.6001 0.5768 0.0302 0.068 Uiso 1 1 calc R U . . .
C15A C 0.5429(9) 0.6326(10) 0.0492(8) 0.069(4) Uani 1 1 d . . . . .
H15A H 0.4967 0.5952 0.0294 0.082 Uiso 1 1 calc R U . . .
C16A C 0.5462(11) 0.6945(12) 0.0762(10) 0.076(5) Uani 1 1 d . . . . .
H16A H 0.5020 0.6996 0.0765 0.092 Uiso 1 1 calc R U . . .
C17A C 0.6111(15) 0.7493(12) 0.1028(10) 0.090(6) Uani 1 1 d . . . . .
H17A H 0.6120 0.7923 0.1227 0.108 Uiso 1 1 calc R U . . .
C18A C 0.6794(9) 0.7447(9) 0.1021(8) 0.063(4) Uani 1 1 d . . . . .
H18A H 0.7264 0.7861 0.1169 0.075 Uiso 1 1 calc R U . . .
O1B O 0.8314(5) 0.4878(5) 0.0777(5) 0.053(2) Uani 1 1 d . . . . .
O2B O 1.0073(6) 0.2546(6) 0.0918(7) 0.071(3) Uani 1 1 d . . . . .
N1B N 0.7011(6) 0.4102(7) 0.0847(5) 0.045(3) Uani 1 1 d . . . . .
H1BA H 0.6968 0.4514 0.0846 0.054 Uiso 1 1 calc R U . . .
N2B N 0.8592(6) 0.2990(7) 0.0847(6) 0.053(3) Uani 1 1 d . . . . .
N3B N 0.9306(6) 0.3076(6) 0.0868(6) 0.051(3) Uani 1 1 d . . . . .
H3BB H 0.9706 0.3538 0.0878 0.061 Uiso 1 1 calc R U . . .
N4B N 0.8788(8) 0.1819(8) 0.0908(7) 0.077(4) Uani 1 1 d . . . . .
H4BA H 0.8378 0.1845 0.1005 0.092 Uiso 1 1 calc R U . . .
C1B C 0.7715(8) 0.4216(9) 0.0818(7) 0.049(3) Uani 1 1 d . . . . .
C2B C 0.7771(7) 0.3523(7) 0.0829(6) 0.038(3) Uani 1 1 d . . . . .
C3B C 0.7140(9) 0.2858(8) 0.0831(6) 0.047(3) Uani 1 1 d . . . . .
H3BA H 0.7192 0.2417 0.0823 0.057 Uiso 1 1 calc R U . . .
C4B C 0.6386(7) 0.2742(8) 0.0845(7) 0.052(4) Uani 1 1 d . . . . .
C5B C 0.5684(9) 0.2033(9) 0.0862(7) 0.057(4) Uani 1 1 d . . . . .
H5BA H 0.5699 0.1572 0.0839 0.068 Uiso 1 1 calc R U . . .
C6B C 0.4994(7) 0.1996(8) 0.0909(7) 0.048(3) Uani 1 1 d . . . . .
C7B C 0.4993(9) 0.2705(9) 0.0930(7) 0.057(4) Uani 1 1 d . . . . .
H7BA H 0.4514 0.2684 0.0953 0.068 Uiso 1 1 calc R U . . .
C8B C 0.5622(8) 0.3393(9) 0.0918(8) 0.061(4) Uani 1 1 d . . . . .
H8BA H 0.5585 0.3842 0.0936 0.073 Uiso 1 1 calc R U . . .
C9B C 0.6367(8) 0.3445(9) 0.0879(6) 0.047(3) Uani 1 1 d . . . . .
C10B C 0.4270(12) 0.1240(11) 0.0958(9) 0.081(5) Uani 1 1 d . . . . .
H10D H 0.4364 0.0836 0.0804 0.122 Uiso 1 1 calc R U . . .
H10E H 0.3877 0.1248 0.0680 0.122 Uiso 1 1 calc R U . . .
H10F H 0.4098 0.1145 0.1422 0.122 Uiso 1 1 calc R U . . .
C11B C 0.8531(8) 0.3628(10) 0.0836(7) 0.054(4) Uani 1 1 d . . . . .
H11B H 0.8969 0.4122 0.0833 0.065 Uiso 1 1 calc R U . . .
C12B C 0.9412(7) 0.2455(10) 0.0874(8) 0.057(4) Uani 1 1 d . . . . .
C13B C 0.8675(7) 0.1066(9) 0.0808(7) 0.053(4) Uani 1 1 d . . . . .
C14B C 0.9198(10) 0.0880(11) 0.0550(8) 0.069(5) Uani 1 1 d . . . . .
H14B H 0.9710 0.1272 0.0479 0.083 Uiso 1 1 calc R U . . .
C15B C 0.8983(12) 0.0128(12) 0.0393(8) 0.074(5) Uani 1 1 d . . . . .
H15B H 0.9352 0.0035 0.0187 0.089 Uiso 1 1 calc R U . . .
C16B C 0.8276(14) -0.0487(12) 0.0515(9) 0.084(6) Uani 1 1 d . . . . .
H16B H 0.8156 -0.0994 0.0417 0.100 Uiso 1 1 calc R U . . .
C17B C 0.7754(11) -0.0326(11) 0.0787(11) 0.083(5) Uani 1 1 d . . . . .
H17B H 0.7249 -0.0727 0.0867 0.099 Uiso 1 1 calc R U . . .
C18B C 0.7957(13) 0.0432(10) 0.0949(11) 0.089(6) Uani 1 1 d . . . . .
H18B H 0.7589 0.0517 0.1164 0.107 Uiso 1 1 calc R U . . .
O1C O 1.0669(5) 0.4544(6) 0.0959(6) 0.070(3) Uani 1 1 d . . . . .
O2C O 1.2891(6) 0.8583(6) 0.0924(6) 0.060(3) Uani 1 1 d . . . . .
N1C N 1.1373(7) 0.3991(7) 0.0882(6) 0.063(3) Uani 1 1 d . . . . .
H1CA H 1.0950 0.3547 0.0861 0.075 Uiso 1 1 calc R U . . .
N2C N 1.2514(7) 0.6704(7) 0.0914(6) 0.058(3) Uani 1 1 d . . . . .
N3C N 1.2389(8) 0.7303(7) 0.0933(6) 0.056(3) Uani 1 1 d . . . . .
H3CB H 1.1920 0.7221 0.0963 0.067 Uiso 1 1 calc R U . . .
N4C N 1.3669(7) 0.8074(8) 0.0892(6) 0.057(3) Uani 1 1 d . . . . .
H4CA H 1.3656 0.7634 0.0875 0.069 Uiso 1 1 calc R U . . .
C1C C 1.1316(11) 0.4652(11) 0.0911(8) 0.065(5) Uani 1 1 d . . . . .
C2C C 1.1976(7) 0.5359(8) 0.0899(7) 0.041(3) Uani 1 1 d . . . . .
C3C C 1.2667(10) 0.5387(8) 0.0908(7) 0.055(4) Uani 1 1 d . . . . .
H3CA H 1.3116 0.5873 0.0922 0.066 Uiso 1 1 calc R U . . .
C4C C 1.2750(7) 0.4744(7) 0.0898(7) 0.041(3) Uani 1 1 d . . . . .
C5C C 1.3467(9) 0.4791(11) 0.0922(7) 0.068(4) Uani 1 1 d . . . . .
H5CA H 1.3922 0.5272 0.0928 0.081 Uiso 1 1 calc R U . . .
C6C C 1.3501(9) 0.4070(9) 0.0938(7) 0.053(4) Uani 1 1 d . . . . .
C7C C 1.2815(11) 0.3417(12) 0.0907(9) 0.075(5) Uani 1 1 d . . . . .
H7CA H 1.2831 0.2956 0.0913 0.090 Uiso 1 1 calc R U . . .
C8C C 1.2105(9) 0.3339(9) 0.0870(8) 0.059(4) Uani 1 1 d . . . . .
H8CA H 1.1657 0.2855 0.0835 0.070 Uiso 1 1 calc R U . . .
C9C C 1.2083(8) 0.4004(7) 0.0885(6) 0.042(3) Uani 1 1 d . . . . .
C10C C 1.4238(11) 0.4131(12) 0.1015(10) 0.084(6) Uani 1 1 d . . . . .
H10G H 1.4175 0.3664 0.1221 0.127 Uiso 1 1 calc R U . . .
H10H H 1.4561 0.4568 0.1300 0.127 Uiso 1 1 calc R U . . .
H10I H 1.4478 0.4200 0.0578 0.127 Uiso 1 1 calc R U . . .
C11C C 1.1869(8) 0.5992(9) 0.0925(7) 0.054(4) Uani 1 1 d . . . . .
H11C H 1.1374 0.5932 0.0949 0.064 Uiso 1 1 calc R U . . .
C12C C 1.2991(9) 0.8037(10) 0.0906(7) 0.057(4) Uani 1 1 d . . . . .
C13C C 1.4405(9) 0.8728(7) 0.0901(8) 0.057(4) Uani 1 1 d . . . . .
C14C C 1.4533(9) 0.9409(9) 0.1222(8) 0.061(4) Uani 1 1 d . . . . .
H14C H 1.4114 0.9417 0.1423 0.074 Uiso 1 1 calc R U . . .
C15C C 1.5222(9) 1.0038(9) 0.1253(8) 0.065(4) Uani 1 1 d . . . . .
H15C H 1.5277 1.0483 0.1462 0.078 Uiso 1 1 calc R U . . .
C16C C 1.5867(14) 1.0045(16) 0.0976(11) 0.105(8) Uani 1 1 d . . . . .
H16C H 1.6366 1.0473 0.1009 0.126 Uiso 1 1 calc R U . . .
C17C C 1.5711(11) 0.9359(14) 0.0643(9) 0.087(6) Uani 1 1 d . . . . .
H17C H 1.6129 0.9347 0.0441 0.104 Uiso 1 1 calc R U . . .
C18C C 1.4982(11) 0.8692(16) 0.0588(8) 0.096(7) Uani 1 1 d . . . . .
H18D H 1.4903 0.8254 0.0351 0.115 Uiso 1 1 calc R U . . .


_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
O1A C1A 1.243(14) . ?
O2A C12A 1.244(18) . ?
N1A C1A 1.389(18) . ?
N1A C9A 1.411(15) . ?
N1A H1AA 0.8800 . ?
N2A C11A 1.295(18) . ?
N2A N3A 1.326(17) . ?
N3A C12A 1.375(19) . ?
N3A H3AB 0.8800 . ?
N4A C13A 1.354(15) . ?
N4A C12A 1.37(2) . ?
N4A H4AA 0.8800 . ?
C1A C2A 1.43(2) . ?
C2A C3A 1.41(2) . ?
C2A C11A 1.47(2) . ?
C3A C4A 1.39(2) . ?
C3A H3AA 0.9500 . ?
C4A C9A 1.356(16) . ?
C4A C5A 1.46(2) . ?
C5A C6A 1.37(2) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.37(2) . ?
C6A C10A 1.62(2) . ?
C7A C8A 1.38(2) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.370(18) . ?
C8A H8AA 0.9500 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9500 . ?
C13A C18A 1.38(2) . ?
C13A C14A 1.45(2) . ?
C14A C15A 1.37(2) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.34(2) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.34(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.43(3) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
O1B C1B 1.284(17) . ?
O2B C12B 1.260(15) . ?
N1B C9B 1.320(18) . ?
N1B C1B 1.329(16) . ?
N1B H1BA 0.8800 . ?
N2B C11B 1.359(18) . ?
N2B N3B 1.370(14) . ?
N3B C12B 1.379(18) . ?
N3B H3BB 0.8800 . ?
N4B C12B 1.279(19) . ?
N4B C13B 1.44(2) . ?
N4B H4BA 0.8800 . ?
C1B C2B 1.465(18) . ?
C2B C3B 1.315(18) . ?
C2B C11B 1.444(16) . ?
C3B C4B 1.426(19) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.43(2) . ?
C4B C9B 1.45(2) . ?
C5B C6B 1.368(18) . ?
C5B H5BA 0.9500 . ?
C6B C7B 1.44(2) . ?
C6B C10B 1.50(2) . ?
C7B C8B 1.34(2) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.462(19) . ?
C8B H8BA 0.9500 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11B 0.9500 . ?
C13B C14B 1.39(2) . ?
C13B C18B 1.41(2) . ?
C14B C15B 1.40(2) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.37(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.37(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.42(2) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
O1C C1C 1.222(17) . ?
O2C C12C 1.222(17) . ?
N1C C1C 1.402(19) . ?
N1C C9C 1.425(17) . ?
N1C H1CA 0.8800 . ?
N2C N3C 1.360(16) . ?
N2C C11C 1.381(18) . ?
N3C C12C 1.374(19) . ?
N3C H3CB 0.8800 . ?
N4C C12C 1.339(17) . ?
N4C C13C 1.415(18) . ?
N4C H4CA 0.8800 . ?
C1C C2C 1.39(2) . ?
C2C C3C 1.375(18) . ?
C2C C11C 1.404(19) . ?
C3C C4C 1.394(18) . ?
C3C H3CA 0.9500 . ?
C4C C5C 1.410(19) . ?
C4C C9C 1.432(18) . ?
C5C C6C 1.50(2) . ?
C5C H5CA 0.9500 . ?
C6C C7C 1.36(2) . ?
C6C C10C 1.45(2) . ?
C7C C8C 1.37(2) . ?
C7C H7CA 0.9500 . ?
C8C C9C 1.371(18) . ?
C8C H8CA 0.9500 . ?
C10C H10G 0.9800 . ?
C10C H10H 0.9800 . ?
C10C H10I 0.9800 . ?
C11C H11C 0.9500 . ?
C13C C18C 1.36(2) . ?
C13C C14C 1.42(2) . ?
C14C C15C 1.34(2) . ?
C14C H14C 0.9500 . ?
C15C C16C 1.41(3) . ?
C15C H15C 0.9500 . ?
C16C C17C 1.43(3) . ?
C16C H16C 0.9500 . ?
C17C C18C 1.42(3) . ?
C17C H17C 0.9500 . ?
C18C H18D 0.9500 . ?

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
C1A N1A C9A 122.8(9) . . ?
C1A N1A H1AA 118.6 . . ?
C9A N1A H1AA 118.6 . . ?
C11A N2A N3A 116.5(13) . . ?
N2A N3A C12A 119.3(12) . . ?
N2A N3A H3AB 120.3 . . ?
C12A N3A H3AB 120.3 . . ?
C13A N4A C12A 129.9(12) . . ?
C13A N4A H4AA 115.0 . . ?
C12A N4A H4AA 115.0 . . ?
O1A C1A N1A 121.3(13) . . ?
O1A C1A C2A 121.7(15) . . ?
N1A C1A C2A 117.0(11) . . ?
C3A C2A C1A 120.1(13) . . ?
C3A C2A C11A 120.4(12) . . ?
C1A C2A C11A 119.5(14) . . ?
C4A C3A C2A 119.5(12) . . ?
C4A C3A H3AA 120.2 . . ?
C2A C3A H3AA 120.2 . . ?
C9A C4A C3A 121.7(14) . . ?
C9A C4A C5A 117.0(14) . . ?
C3A C4A C5A 121.2(12) . . ?
C6A C5A C4A 117.9(13) . . ?
C6A C5A H5AA 121.1 . . ?
C4A C5A H5AA 121.1 . . ?
C5A C6A C7A 122.9(16) . . ?
C5A C6A C10A 120.1(13) . . ?
C7A C6A C10A 117.0(15) . . ?
C6A C7A C8A 118.8(15) . . ?
C6A C7A H7AA 120.6 . . ?
C8A C7A H7AA 120.6 . . ?
C9A C8A C7A 119.9(12) . . ?
C9A C8A H8AA 120.1 . . ?
C7A C8A H8AA 120.1 . . ?
C4A C9A C8A 123.1(12) . . ?
C4A C9A N1A 118.7(12) . . ?
C8A C9A N1A 118.0(10) . . ?
C6A C10A H10A 109.5 . . ?
C6A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C6A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N2A C11A C2A 122.4(14) . . ?
N2A C11A H11A 118.8 . . ?
C2A C11A H11A 118.8 . . ?
O2A C12A N3A 121.3(16) . . ?
O2A C12A N4A 122.2(15) . . ?
N3A C12A N4A 116.1(13) . . ?
N4A C13A C18A 118.7(13) . . ?
N4A C13A C14A 123.3(13) . . ?
C18A C13A C14A 117.8(13) . . ?
C15A C14A C13A 119.5(14) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C16A C15A C14A 122.0(16) . . ?
C16A C15A H15A 119.0 . . ?
C14A C15A H15A 119.0 . . ?
C17A C16A C15A 120.5(17) . . ?
C17A C16A H16A 119.8 . . ?
C15A C16A H16A 119.8 . . ?
C16A C17A C18A 121.5(16) . . ?
C16A C17A H17A 119.2 . . ?
C18A C17A H17A 119.2 . . ?
C13A C18A C17A 118.3(14) . . ?
C13A C18A H18A 120.9 . . ?
C17A C18A H18A 120.9 . . ?
C9B N1B C1B 127.7(12) . . ?
C9B N1B H1BA 116.2 . . ?
C1B N1B H1BA 116.2 . . ?
C11B N2B N3B 118.2(11) . . ?
N2B N3B C12B 121.4(11) . . ?
N2B N3B H3BB 119.3 . . ?
C12B N3B H3BB 119.3 . . ?
C12B N4B C13B 127.8(15) . . ?
C12B N4B H4BA 116.1 . . ?
C13B N4B H4BA 116.1 . . ?
O1B C1B N1B 123.8(12) . . ?
O1B C1B C2B 121.1(12) . . ?
N1B C1B C2B 115.1(13) . . ?
C3B C2B C11B 124.7(12) . . ?
C3B C2B C1B 118.7(11) . . ?
C11B C2B C1B 116.6(12) . . ?
C2B C3B C4B 125.7(12) . . ?
C2B C3B H3BA 117.2 . . ?
C4B C3B H3BA 117.2 . . ?
C3B C4B C5B 127.8(14) . . ?
C3B C4B C9B 113.1(12) . . ?
C5B C4B C9B 119.1(12) . . ?
C6B C5B C4B 122.2(13) . . ?
C6B C5B H5BA 118.9 . . ?
C4B C5B H5BA 118.9 . . ?
C5B C6B C7B 117.4(13) . . ?
C5B C6B C10B 120.7(13) . . ?
C7B C6B C10B 121.9(13) . . ?
C8B C7B C6B 124.3(14) . . ?
C8B C7B H7BA 117.9 . . ?
C6B C7B H7BA 117.9 . . ?
C7B C8B C9B 119.2(15) . . ?
C7B C8B H8BA 120.4 . . ?
C9B C8B H8BA 120.4 . . ?
N1B C9B C4B 119.5(11) . . ?
N1B C9B C8B 122.6(13) . . ?
C4B C9B C8B 117.8(13) . . ?
C6B C10B H10D 109.5 . . ?
C6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N2B C11B C2B 117.2(13) . . ?
N2B C11B H11B 121.4 . . ?
C2B C11B H11B 121.4 . . ?
O2B C12B N4B 126.0(16) . . ?
O2B C12B N3B 120.4(14) . . ?
N4B C12B N3B 113.2(13) . . ?
C14B C13B C18B 114.1(15) . . ?
C14B C13B N4B 126.9(14) . . ?
C18B C13B N4B 118.9(13) . . ?
C13B C14B C15B 121.1(17) . . ?
C13B C14B H14B 119.4 . . ?
C15B C14B H14B 119.4 . . ?
C16B C15B C14B 124.4(17) . . ?
C16B C15B H15B 117.8 . . ?
C14B C15B H15B 117.8 . . ?
C17B C16B C15B 115.9(18) . . ?
C17B C16B H16B 122.1 . . ?
C15B C16B H16B 122.1 . . ?
C16B C17B C18B 120.8(19) . . ?
C16B C17B H17B 119.6 . . ?
C18B C17B H17B 119.6 . . ?
C13B C18B C17B 123.5(18) . . ?
C13B C18B H18B 118.3 . . ?
C17B C18B H18B 118.3 . . ?
C1C N1C C9C 123.1(13) . . ?
C1C N1C H1CA 118.5 . . ?
C9C N1C H1CA 118.5 . . ?
N3C N2C C11C 115.5(12) . . ?
N2C N3C C12C 120.3(12) . . ?
N2C N3C H3CB 119.9 . . ?
C12C N3C H3CB 119.9 . . ?
C12C N4C C13C 128.6(13) . . ?
C12C N4C H4CA 115.7 . . ?
C13C N4C H4CA 115.7 . . ?
O1C C1C C2C 125.4(14) . . ?
O1C C1C N1C 115.3(17) . . ?
C2C C1C N1C 119.3(13) . . ?
C3C C2C C1C 118.5(12) . . ?
C3C C2C C11C 125.6(13) . . ?
C1C C2C C11C 115.7(12) . . ?
C2C C3C C4C 123.9(14) . . ?
C2C C3C H3CA 118.0 . . ?
C4C C3C H3CA 118.0 . . ?
C3C C4C C5C 122.6(14) . . ?
C3C C4C C9C 119.2(11) . . ?
C5C C4C C9C 118.2(12) . . ?
C4C C5C C6C 118.9(15) . . ?
C4C C5C H5CA 120.5 . . ?
C6C C5C H5CA 120.5 . . ?
C7C C6C C10C 126.7(15) . . ?
C7C C6C C5C 115.3(12) . . ?
C10C C6C C5C 118.0(15) . . ?
C6C C7C C8C 128.2(16) . . ?
C6C C7C H7CA 115.9 . . ?
C8C C7C H7CA 115.9 . . ?
C7C C8C C9C 115.8(15) . . ?
C7C C8C H8CA 122.1 . . ?
C9C C8C H8CA 122.1 . . ?
C8C C9C N1C 120.7(13) . . ?
C8C C9C C4C 123.5(12) . . ?
N1C C9C C4C 115.8(10) . . ?
C6C C10C H10G 109.5 . . ?
C6C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
C6C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
N2C C11C C2C 117.1(12) . . ?
N2C C11C H11C 121.4 . . ?
C2C C11C H11C 121.4 . . ?
O2C C12C N4C 125.5(16) . . ?
O2C C12C N3C 121.3(13) . . ?
N4C C12C N3C 113.1(13) . . ?
C18C C13C N4C 118.4(16) . . ?
C18C C13C C14C 120.9(17) . . ?
N4C C13C C14C 120.6(14) . . ?
C15C C14C C13C 122.8(15) . . ?
C15C C14C H14C 118.6 . . ?
C13C C14C H14C 118.6 . . ?
C14C C15C C16C 120.6(18) . . ?
C14C C15C H15C 119.7 . . ?
C16C C15C H15C 119.7 . . ?
C15C C16C C17C 115(2) . . ?
C15C C16C H16C 122.6 . . ?
C17C C16C H16C 122.6 . . ?
C18C C17C C16C 125.4(19) . . ?
C18C C17C H17C 117.3 . . ?
C16C C17C H17C 117.3 . . ?
C13C C18C C17C 115(2) . . ?
C13C C18C H18D 122.4 . . ?
C17C C18C H18D 122.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11A N2A N3A C12A -178.6(12) . . . . ?
C9A N1A C1A O1A -178.9(12) . . . . ?
C9A N1A C1A C2A 0.6(18) . . . . ?
O1A C1A C2A C3A 178.6(13) . . . . ?
N1A C1A C2A C3A -1(2) . . . . ?
O1A C1A C2A C11A -2(2) . . . . ?
N1A C1A C2A C11A 178.1(11) . . . . ?
C1A C2A C3A C4A 2(2) . . . . ?
C11A C2A C3A C4A -176.8(12) . . . . ?
C2A C3A C4A C9A -3(2) . . . . ?
C2A C3A C4A C5A -178.8(13) . . . . ?
C9A C4A C5A C6A 6.4(18) . . . . ?
C3A C4A C5A C6A -177.7(13) . . . . ?
C4A C5A C6A C7A -7(2) . . . . ?
C4A C5A C6A C10A 176.4(12) . . . . ?
C5A C6A C7A C8A 4(2) . . . . ?
C10A C6A C7A C8A -178.4(13) . . . . ?
C6A C7A C8A C9A -2(2) . . . . ?
C3A C4A C9A C8A 179.5(13) . . . . ?
C5A C4A C9A C8A -4.6(19) . . . . ?
C3A C4A C9A N1A 3(2) . . . . ?
C5A C4A C9A N1A 178.6(11) . . . . ?
C7A C8A C9A C4A 3(2) . . . . ?
C7A C8A C9A N1A 179.3(12) . . . . ?
C1A N1A C9A C4A -1.5(18) . . . . ?
C1A N1A C9A C8A -178.4(11) . . . . ?
N3A N2A C11A C2A 176.8(12) . . . . ?
C3A C2A C11A N2A 0(2) . . . . ?
C1A C2A C11A N2A -179.1(13) . . . . ?
N2A N3A C12A O2A -178.6(13) . . . . ?
N2A N3A C12A N4A -6(2) . . . . ?
C13A N4A C12A O2A -7(2) . . . . ?
C13A N4A C12A N3A -179.7(13) . . . . ?
C12A N4A C13A C18A 164.2(15) . . . . ?
C12A N4A C13A C14A -21(2) . . . . ?
N4A C13A C14A C15A -179.4(13) . . . . ?
C18A C13A C14A C15A -5(2) . . . . ?
C13A C14A C15A C16A 0(2) . . . . ?
C14A C15A C16A C17A 2(3) . . . . ?
C15A C16A C17A C18A 1(3) . . . . ?
N4A C13A C18A C17A -177.2(14) . . . . ?
C14A C13A C18A C17A 8(2) . . . . ?
C16A C17A C18A C13A -6(3) . . . . ?
C11B N2B N3B C12B -179.3(13) . . . . ?
C9B N1B C1B O1B 178.8(13) . . . . ?
C9B N1B C1B C2B -1(2) . . . . ?
O1B C1B C2B C3B -176.0(12) . . . . ?
N1B C1B C2B C3B 3.5(19) . . . . ?
O1B C1B C2B C11B 4.0(19) . . . . ?
N1B C1B C2B C11B -176.5(11) . . . . ?
C11B C2B C3B C4B 177.9(13) . . . . ?
C1B C2B C3B C4B -2(2) . . . . ?
C2B C3B C4B C5B -178.6(14) . . . . ?
C2B C3B C4B C9B -1.9(19) . . . . ?
C3B C4B C5B C6B 176.5(13) . . . . ?
C9B C4B C5B C6B 0(2) . . . . ?
C4B C5B C6B C7B 1(2) . . . . ?
C4B C5B C6B C10B -177.1(13) . . . . ?
C5B C6B C7B C8B -1(2) . . . . ?
C10B C6B C7B C8B 176.9(15) . . . . ?
C6B C7B C8B C9B 0(2) . . . . ?
C1B N1B C9B C4B -4(2) . . . . ?
C1B N1B C9B C8B 179.2(13) . . . . ?
C3B C4B C9B N1B 4.6(17) . . . . ?
C5B C4B C9B N1B -178.4(12) . . . . ?
C3B C4B C9B C8B -178.0(12) . . . . ?
C5B C4B C9B C8B -1.0(18) . . . . ?
C7B C8B C9B N1B 178.1(13) . . . . ?
C7B C8B C9B C4B 1(2) . . . . ?
N3B N2B C11B C2B -178.7(12) . . . . ?
C3B C2B C11B N2B 0(2) . . . . ?
C1B C2B C11B N2B 179.9(11) . . . . ?
C13B N4B C12B O2B -20(3) . . . . ?
C13B N4B C12B N3B 168.1(14) . . . . ?
N2B N3B C12B O2B -177.3(14) . . . . ?
N2B N3B C12B N4B -5(2) . . . . ?
C12B N4B C13B C14B -11(3) . . . . ?
C12B N4B C13B C18B 172.3(17) . . . . ?
C18B C13B C14B C15B 6(2) . . . . ?
N4B C13B C14B C15B -171.1(14) . . . . ?
C13B C14B C15B C16B -5(2) . . . . ?
C14B C15B C16B C17B 3(3) . . . . ?
C15B C16B C17B C18B -2(3) . . . . ?
C14B C13B C18B C17B -6(3) . . . . ?
N4B C13B C18B C17B 171.4(16) . . . . ?
C16B C17B C18B C13B 4(3) . . . . ?
C11C N2C N3C C12C -178.2(12) . . . . ?
C9C N1C C1C O1C -174.2(13) . . . . ?
C9C N1C C1C C2C 4(2) . . . . ?
O1C C1C C2C C3C 173.7(15) . . . . ?
N1C C1C C2C C3C -5(2) . . . . ?
O1C C1C C2C C11C -2(2) . . . . ?
N1C C1C C2C C11C 179.6(12) . . . . ?
C1C C2C C3C C4C 3(2) . . . . ?
C11C C2C C3C C4C 178.4(13) . . . . ?
C2C C3C C4C C5C -178.6(14) . . . . ?
C2C C3C C4C C9C -1(2) . . . . ?
C3C C4C C5C C6C 177.4(13) . . . . ?
C9C C4C C5C C6C -0.4(19) . . . . ?
C4C C5C C6C C7C 2(2) . . . . ?
C4C C5C C6C C10C -175.2(14) . . . . ?
C10C C6C C7C C8C 176.2(17) . . . . ?
C5C C6C C7C C8C -1(3) . . . . ?
C6C C7C C8C C9C -2(3) . . . . ?
C7C C8C C9C N1C -176.9(14) . . . . ?
C7C C8C C9C C4C 4(2) . . . . ?
C1C N1C C9C C8C 178.6(13) . . . . ?
C1C N1C C9C C4C -2(2) . . . . ?
C3C C4C C9C C8C 179.6(13) . . . . ?
C5C C4C C9C C8C -3(2) . . . . ?
C3C C4C C9C N1C 0.2(19) . . . . ?
C5C C4C C9C N1C 178.1(11) . . . . ?
N3C N2C C11C C2C 179.4(11) . . . . ?
C3C C2C C11C N2C 5(2) . . . . ?
C1C C2C C11C N2C -180.0(12) . . . . ?
C13C N4C C12C O2C 1(3) . . . . ?
C13C N4C C12C N3C -176.2(13) . . . . ?
N2C N3C C12C O2C -179.8(13) . . . . ?
N2C N3C C12C N4C -2.9(19) . . . . ?
C12C N4C C13C C18C -150.0(16) . . . . ?
C12C N4C C13C C14C 29(2) . . . . ?
C18C C13C C14C C15C -2(2) . . . . ?
N4C C13C C14C C15C 178.9(14) . . . . ?
C13C C14C C15C C16C -2(2) . . . . ?
C14C C15C C16C C17C 3(3) . . . . ?
C15C C16C C17C C18C -2(3) . . . . ?
N4C C13C C18C C17C -177.3(14) . . . . ?
C14C C13C C18C C17C 3(2) . . . . ?
C16C C17C C18C C13C -2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1AA O2C 0.88 1.87 2.744(13) 175.7 .
N3A H3AB O1B 0.88 1.96 2.830(14) 172.4 .
C14A H14A O2A 0.95 2.41 2.928(18) 114.1 .
N1B H1BA O2A 0.88 1.94 2.818(16) 173.3 .
N3B H3BB O1C 0.88 2.00 2.880(15) 174.1 .
N4B H4BA N2B 0.88 2.16 2.60(2) 110.1 .
C14B H14B O2B 0.95 2.47 3.02(2) 116.7 .
N1C H1CA O2B 0.88 1.92 2.794(17) 172.7 .
N3C H3CB O1A 0.88 2.01 2.876(16) 168.6 .
N4C H4CA N2C 0.88 2.13 2.587(18) 111.4 .
C14C H14C O2C 0.95 2.41 2.944(19) 115.2 .

_refine_diff_density_max         0.914
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.094



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1922256'
loop_
_audit_author_name
_audit_author_address
'Ray Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2021-05-03 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_shelx               
;
PROBLEM: D-H Bond Without Acceptor  O1W      --H1W2     .     Please Check 
RESPONSE: A search was made for a more suitable position for H1W2 but
none was found. H1W2 is in close proximity to Cl1 (2.905 Ang, O-H...Cl1 
angle of 110.4 Deg)
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C18 H16 Cl2 Cu N4 O2, C19 H20 Cl Cu N4 O3, Cl, 2(H2 O)
;
_chemical_formula_sum            'C37 H40 Cl4 Cu2 N8 O7'
_chemical_formula_weight         977.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3350(3)
_cell_length_b                   54.757(2)
_cell_length_c                   10.2586(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.497(4)
_cell_angle_gamma                90
_cell_volume                     3970.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4850
_cell_measurement_theta_min      4.5310
_cell_measurement_theta_max      75.8900

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.308
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            15292
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       68
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.545
_diffrn_reflns_theta_max         76.838
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8041
_reflns_number_gt                7023
_reflns_threshold_expression     'I > 2σ(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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'Shelxt (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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/[σ²(Fo²)+29.5221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8041
_refine_ls_number_parameters     545
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.167
_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
Cu1 Cu 0.16681(12) 0.40975(2) 0.57365(8) 0.02070(19) Uani 1 1 d . . . . .
Cl1 Cl 0.2503(3) 0.43576(3) 0.74486(14) 0.0354(4) Uani 1 1 d . . . . .
Cl2 Cl 0.49939(19) 0.38662(2) 0.59893(12) 0.0217(3) Uani 1 1 d . . . . .
O1A O 0.0612(6) 0.38587(7) 0.6780(4) 0.0218(8) Uani 1 1 d . . . . .
O2A O 0.2126(6) 0.43334(7) 0.4376(4) 0.0228(8) Uani 1 1 d . . . . .
N1A N -0.0717(6) 0.35165(8) 0.7280(4) 0.0187(9) Uani 1 1 d . . . . .
H1AA H -0.039566 0.356687 0.812556 0.022 Uiso 1 1 calc R U . . .
N2A N 0.0532(6) 0.39135(8) 0.4049(4) 0.0184(9) Uani 1 1 d . . . . .
N3A N 0.0895(7) 0.40255(8) 0.2944(5) 0.0214(9) Uani 1 1 d . . . . .
H3AB H 0.066116 0.395478 0.214630 0.026 Uiso 1 1 calc R U . . .
N4A N 0.1837(7) 0.43762(9) 0.2108(5) 0.0235(10) Uani 1 1 d . . . . .
H4A H 0.155(11) 0.4326(14) 0.140(8) 0.04(2) Uiso 1 1 d . . . . .
C1A C -0.0278(8) 0.36628(10) 0.6363(5) 0.0182(10) Uani 1 1 d . . . . .
C2A C -0.0843(8) 0.35786(10) 0.4964(5) 0.0189(10) Uani 1 1 d . . . . .
C3A C -0.1831(8) 0.33646(10) 0.4664(6) 0.0212(11) Uani 1 1 d . . . . .
H3AA H -0.227485 0.331664 0.374321 0.025 Uiso 1 1 calc R U . . .
C4A C -0.2219(7) 0.32119(10) 0.5672(5) 0.0173(10) Uani 1 1 d . . . . .
C5A C -0.3055(7) 0.29786(10) 0.5394(5) 0.0185(10) Uani 1 1 d . . . . .
H5AA H -0.347729 0.292502 0.448211 0.022 Uiso 1 1 calc R U . . .
C6A C -0.3273(8) 0.28279(10) 0.6406(6) 0.0212(11) Uani 1 1 d . . . . .
C7A C -0.2703(8) 0.29174(10) 0.7754(6) 0.0240(12) Uani 1 1 d . . . . .
H7AA H -0.288092 0.281722 0.846659 0.029 Uiso 1 1 calc R U . . .
C8A C -0.1897(9) 0.31457(10) 0.8062(6) 0.0248(12) Uani 1 1 d . . . . .
H8AA H -0.152973 0.320145 0.897224 0.030 Uiso 1 1 calc R U . . .
C9A C -0.1631(8) 0.32928(10) 0.7023(5) 0.0187(10) Uani 1 1 d . . . . .
C10A C -0.4040(8) 0.25737(10) 0.6126(6) 0.0236(12) Uani 1 1 d . . . . .
H10A H -0.423191 0.253605 0.516490 0.035 Uiso 1 1 calc R U . . .
H10B H -0.524953 0.256165 0.635732 0.035 Uiso 1 1 calc R U . . .
H10C H -0.313866 0.245723 0.667343 0.035 Uiso 1 1 calc R U . . .
C11A C -0.0377(7) 0.37113(9) 0.3884(5) 0.0172(10) Uani 1 1 d . . . . .
H11A H -0.076791 0.364484 0.299768 0.021 Uiso 1 1 calc R U . . .
C12A C 0.1641(8) 0.42529(10) 0.3177(5) 0.0211(11) Uani 1 1 d . . . . .
C13A C 0.2549(18) 0.46132(16) 0.2048(10) 0.0251(18) Uani 0.603(8) 1 d G U P A 1
C14A C 0.2670(13) 0.46922(12) 0.0787(8) 0.032(2) Uani 0.603(8) 1 d G U P A 1
H14A H 0.229173 0.458715 0.002516 0.038 Uiso 0.603(8) 1 calc R U P A 1
C15A C 0.3345(14) 0.49250(14) 0.0639(7) 0.046(3) Uani 0.603(8) 1 d G U P A 1
H15A H 0.342782 0.497898 -0.022287 0.055 Uiso 0.603(8) 1 calc R U P A 1
C16A C 0.3898(13) 0.50787(13) 0.1754(10) 0.043(3) Uani 0.603(8) 1 d G U P A 1
H16A H 0.435965 0.523774 0.165312 0.052 Uiso 0.603(8) 1 calc R U P A 1
C17A C 0.3777(19) 0.5000(2) 0.3016(8) 0.0366(16) Uani 0.603(8) 1 d G U P A 1
H17A H 0.415540 0.510468 0.377715 0.044 Uiso 0.603(8) 1 calc R U P A 1
C18A C 0.310(2) 0.4767(2) 0.3163(7) 0.029(2) Uani 0.603(8) 1 d G U P A 1
H18A H 0.301931 0.471286 0.402521 0.034 Uiso 0.603(8) 1 calc R U P A 1
C13C C 0.233(3) 0.4634(2) 0.2112(15) 0.0251(18) Uani 0.397(8) 1 d G . P A 2
C14C C 0.1600(19) 0.4753(2) 0.0888(12) 0.032(2) Uani 0.397(8) 1 d G . P A 2
H14B H 0.087100 0.466587 0.012717 0.038 Uiso 0.397(8) 1 calc R U P A 2
C15C C 0.194(2) 0.5001(2) 0.0778(12) 0.046(3) Uani 0.397(8) 1 d G . P A 2
H15B H 0.144485 0.508310 -0.005813 0.055 Uiso 0.397(8) 1 calc R U P A 2
C16C C 0.301(2) 0.5129(2) 0.1892(15) 0.043(3) Uani 0.397(8) 1 d G . P A 2
H16B H 0.323997 0.529882 0.181691 0.052 Uiso 0.397(8) 1 calc R U P A 2
C17C C 0.373(3) 0.5010(3) 0.3116(12) 0.0366(16) Uani 0.397(8) 1 d G . P A 2
H17B H 0.446126 0.509732 0.387726 0.044 Uiso 0.397(8) 1 calc R U P A 2
C18C C 0.339(4) 0.4762(4) 0.3226(12) 0.029(2) Uani 0.397(8) 1 d G . P A 2
H18B H 0.388743 0.468008 0.406258 0.034 Uiso 0.397(8) 1 calc R U P A 2
Cu2 Cu 0.40990(12) 0.33731(2) 1.07677(7) 0.01872(18) Uani 1 1 d . . . . .
Cl3 Cl 0.36318(19) 0.30821(2) 1.21515(12) 0.0206(3) Uani 1 1 d . . . . .
Cl4 Cl 0.0177(2) 0.36514(3) 1.04234(13) 0.0272(3) Uani 1 1 d . . . . .
O1B O 0.4786(5) 0.36275(6) 1.2160(3) 0.0177(7) Uani 1 1 d . . . . .
O2B O 0.3205(6) 0.31619(7) 0.9149(4) 0.0220(8) Uani 1 1 d . . . . .
O3B O 0.7423(6) 0.32842(8) 1.1218(4) 0.0278(9) Uani 1 1 d . . . . .
H3B H 0.837(16) 0.340(2) 1.104(11) 0.10(4) Uiso 1 1 d . . . . .
N1B N 0.5774(6) 0.39876(8) 1.3129(4) 0.0166(9) Uani 1 1 d . . . . .
H1BA H 0.562395 0.392629 1.388674 0.020 Uiso 1 1 calc R U . . .
N2B N 0.4424(6) 0.36031(8) 0.9368(4) 0.0158(8) Uani 1 1 d . . . . .
N3B N 0.4022(7) 0.34944(8) 0.8111(4) 0.0188(9) Uani 1 1 d . . . . .
H3BB H 0.418607 0.356938 0.739161 0.023 Uiso 1 1 calc R U . . .
N4B N 0.2843(6) 0.31548(8) 0.6857(4) 0.0172(9) Uani 1 1 d . . . . .
H4BA H 0.301884 0.324144 0.617783 0.021 Uiso 1 1 calc R U . . .
C1B C 0.5278(7) 0.38450(9) 1.2012(5) 0.0168(10) Uani 1 1 d . . . . .
C2B C 0.5415(8) 0.39555(10) 1.0752(5) 0.0191(11) Uani 1 1 d . . . . .
C3B C 0.6046(8) 0.41909(10) 1.0770(5) 0.0216(11) Uani 1 1 d . . . . .
H3BA H 0.609783 0.426400 0.994040 0.026 Uiso 1 1 calc R U . . .
C4B C 0.6623(8) 0.43299(10) 1.1971(6) 0.0213(11) Uani 1 1 d . . . . .
C5B C 0.7361(9) 0.45679(10) 1.2010(6) 0.0249(12) Uani 1 1 d . . . . .
H5BA H 0.747061 0.464137 1.119556 0.030 Uiso 1 1 calc R U . . .
C6B C 0.7929(8) 0.46963(11) 1.3203(6) 0.0255(12) Uani 1 1 d . . . . .
C7B C 0.7833(8) 0.45777(10) 1.4398(6) 0.0240(12) Uani 1 1 d . . . . .
H7BA H 0.828655 0.466074 1.523553 0.029 Uiso 1 1 calc R U . . .
C8B C 0.7110(8) 0.43461(10) 1.4403(5) 0.0216(11) Uani 1 1 d . . . . .
H8BA H 0.703115 0.427241 1.522476 0.026 Uiso 1 1 calc R U . . .
C9B C 0.6496(8) 0.42216(9) 1.3178(5) 0.0182(10) Uani 1 1 d . . . . .
C10B C 0.8658(10) 0.49542(12) 1.3241(7) 0.0347(15) Uani 1 1 d . . . . .
H10D H 0.874670 0.500094 1.233786 0.052 Uiso 1 1 calc R U . . .
H10E H 0.991294 0.496430 1.388339 0.052 Uiso 1 1 calc R U . . .
H10F H 0.778890 0.506508 1.352632 0.052 Uiso 1 1 calc R U . . .
C11B C 0.4939(8) 0.38277(10) 0.9466(5) 0.0216(11) Uani 1 1 d . . . . .
H11B H 0.501007 0.391277 0.867374 0.026 Uiso 1 1 calc R U . . .
C12B C 0.3351(7) 0.32613(9) 0.8069(5) 0.0160(10) Uani 1 1 d . . . . .
C13B C 0.2055(7) 0.29188(9) 0.6527(5) 0.0174(10) Uani 1 1 d . . . . .
C14B C 0.1775(8) 0.27503(9) 0.7469(5) 0.0181(10) Uani 1 1 d . . . . .
H14C H 0.211015 0.279009 0.840437 0.022 Uiso 1 1 calc R U . . .
C15B C 0.1004(8) 0.25236(10) 0.7034(6) 0.0202(11) Uani 1 1 d . . . . .
H15C H 0.084398 0.240727 0.768110 0.024 Uiso 1 1 calc R U . . .
C16B C 0.0462(8) 0.24634(10) 0.5667(6) 0.0231(12) Uani 1 1 d . . . . .
H16C H -0.008856 0.230893 0.537743 0.028 Uiso 1 1 calc R U . . .
C17B C 0.0738(8) 0.26331(10) 0.4734(5) 0.0224(11) Uani 1 1 d . . . . .
H17C H 0.037345 0.259484 0.379661 0.027 Uiso 1 1 calc R U . . .
C18B C 0.1542(8) 0.28577(10) 0.5161(5) 0.0205(11) Uani 1 1 d . . . . .
H18C H 0.174622 0.297140 0.451462 0.025 Uiso 1 1 calc R U . . .
C19B C 0.8413(10) 0.30594(12) 1.1598(7) 0.0342(14) Uani 1 1 d . . . . .
H19A H 0.973934 0.309363 1.206030 0.051 Uiso 1 1 calc R U . . .
H19B H 0.834620 0.296151 1.078676 0.051 Uiso 1 1 calc R U . . .
H19C H 0.783108 0.296886 1.220692 0.051 Uiso 1 1 calc R U . . .
O1W O -0.0044(9) 0.42005(10) 0.9504(5) 0.0450(13) Uani 1 1 d D . . . .
H1W1 H 0.05(2) 0.4076(16) 0.936(13) 0.16(7) Uiso 1 1 d D . . . .
H1W2 H -0.05(2) 0.426(2) 0.876(6) 0.16(7) Uiso 1 1 d D . . . .
O2W O 0.3055(6) 0.34039(7) 0.4546(4) 0.0241(8) Uani 1 1 d D . . . .
H2W1 H 0.328(9) 0.3344(10) 0.389(4) 0.026(18) Uiso 1 1 d D . . . .
H2W2 H 0.371(9) 0.3525(8) 0.473(6) 0.03(2) Uiso 1 1 d D . . . .


_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
Cu1 O1A 1.974(4) . ?
Cu1 N2A 1.984(4) . ?
Cu1 O2A 1.995(4) . ?
Cu1 Cl1 2.2169(15) . ?
Cu1 Cl2 2.6990(16) . ?
O1A C1A 1.269(7) . ?
O2A C12A 1.265(7) . ?
N1A C1A 1.339(7) . ?
N1A C9A 1.387(7) . ?
N1A H1AA 0.8800 . ?
N2A C11A 1.280(7) . ?
N2A N3A 1.376(6) . ?
N3A C12A 1.356(7) . ?
N3A H3AB 0.8800 . ?
N4A C12A 1.328(7) . ?
N4A C13A 1.406(9) . ?
N4A C13C 1.455(13) . ?
N4A H4A 0.75(8) . ?
C1A C2A 1.458(7) . ?
C2A C3A 1.369(8) . ?
C2A C11A 1.440(7) . ?
C3A C4A 1.416(7) . ?
C3A H3AA 0.9500 . ?
C4A C9A 1.408(7) . ?
C4A C5A 1.413(7) . ?
C5A C6A 1.368(8) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.421(8) . ?
C6A C10A 1.500(8) . ?
C7A C8A 1.383(8) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.391(8) . ?
C8A H8AA 0.9500 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A C18A 1.3900 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3900 . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C13C C14C 1.3900 . ?
C13C C18C 1.3900 . ?
C14C C15C 1.3900 . ?
C14C H14B 0.9500 . ?
C15C C16C 1.3900 . ?
C15C H15B 0.9500 . ?
C16C C17C 1.3900 . ?
C16C H16B 0.9500 . ?
C17C C18C 1.3900 . ?
C17C H17B 0.9500 . ?
C18C H18B 0.9500 . ?
Cu2 O1B 1.962(4) . ?
Cu2 N2B 1.971(4) . ?
Cu2 O2B 1.986(4) . ?
Cu2 Cl3 2.2209(14) . ?
Cu2 O3B 2.407(4) . ?
Cu2 Cl4 3.1906(18) . ?
O1B C1B 1.265(6) . ?
O2B C12B 1.264(6) . ?
O3B C19B 1.429(7) . ?
O3B H3B 0.98(12) . ?
N1B C1B 1.354(6) . ?
N1B C9B 1.382(7) . ?
N1B H1BA 0.8800 . ?
N2B C11B 1.282(7) . ?
N2B N3B 1.380(6) . ?
N3B C12B 1.365(7) . ?
N3B H3BB 0.8800 . ?
N4B C12B 1.334(6) . ?
N4B C13B 1.419(6) . ?
N4B H4BA 0.8800 . ?
C1B C2B 1.454(7) . ?
C2B C3B 1.368(7) . ?
C2B C11B 1.452(7) . ?
C3B C4B 1.414(7) . ?
C3B H3BA 0.9500 . ?
C4B C9B 1.398(8) . ?
C4B C5B 1.408(7) . ?
C5B C6B 1.376(8) . ?
C5B H5BA 0.9500 . ?
C6B C7B 1.405(8) . ?
C6B C10B 1.507(8) . ?
C7B C8B 1.375(8) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.394(7) . ?
C8B H8BA 0.9500 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11B 0.9500 . ?
C13B C14B 1.390(7) . ?
C13B C18B 1.391(7) . ?
C14B C15B 1.388(7) . ?
C14B H14C 0.9500 . ?
C15B C16B 1.391(8) . ?
C15B H15C 0.9500 . ?
C16B C17B 1.387(8) . ?
C16B H16C 0.9500 . ?
C17B C18B 1.384(8) . ?
C17B H17C 0.9500 . ?
C18B H18C 0.9500 . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
O1W H1W1 0.81(2) . ?
O1W H1W2 0.82(2) . ?
O2W H2W1 0.811(19) . ?
O2W H2W2 0.81(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
O1A Cu1 N2A 90.15(17) . . ?
O1A Cu1 O2A 166.37(17) . . ?
N2A Cu1 O2A 80.12(17) . . ?
O1A Cu1 Cl1 93.53(12) . . ?
N2A Cu1 Cl1 168.66(14) . . ?
O2A Cu1 Cl1 94.33(12) . . ?
O1A Cu1 Cl2 96.46(12) . . ?
N2A Cu1 Cl2 90.20(13) . . ?
O2A Cu1 Cl2 93.11(12) . . ?
Cl1 Cu1 Cl2 100.02(6) . . ?
C1A O1A Cu1 128.2(3) . . ?
C12A O2A Cu1 113.5(4) . . ?
C1A N1A C9A 126.1(4) . . ?
C1A N1A H1AA 117.0 . . ?
C9A N1A H1AA 117.0 . . ?
C11A N2A N3A 119.1(4) . . ?
C11A N2A Cu1 129.6(4) . . ?
N3A N2A Cu1 111.3(3) . . ?
C12A N3A N2A 115.0(4) . . ?
C12A N3A H3AB 122.5 . . ?
N2A N3A H3AB 122.5 . . ?
C12A N4A C13A 128.9(6) . . ?
C12A N4A C13C 124.8(8) . . ?
C12A N4A H4A 123(6) . . ?
C13A N4A H4A 108(6) . . ?
C13C N4A H4A 111(6) . . ?
O1A C1A N1A 117.9(5) . . ?
O1A C1A C2A 125.7(5) . . ?
N1A C1A C2A 116.4(5) . . ?
C3A C2A C11A 118.6(5) . . ?
C3A C2A C1A 119.1(5) . . ?
C11A C2A C1A 122.3(5) . . ?
C2A C3A C4A 122.6(5) . . ?
C2A C3A H3AA 118.7 . . ?
C4A C3A H3AA 118.7 . . ?
C9A C4A C5A 119.0(5) . . ?
C9A C4A C3A 117.7(5) . . ?
C5A C4A C3A 123.2(5) . . ?
C6A C5A C4A 121.7(5) . . ?
C6A C5A H5AA 119.2 . . ?
C4A C5A H5AA 119.2 . . ?
C5A C6A C7A 117.8(5) . . ?
C5A C6A C10A 121.9(5) . . ?
C7A C6A C10A 120.3(5) . . ?
C8A C7A C6A 122.0(5) . . ?
C8A C7A H7AA 119.0 . . ?
C6A C7A H7AA 119.0 . . ?
C7A C8A C9A 119.1(5) . . ?
C7A C8A H8AA 120.4 . . ?
C9A C8A H8AA 120.4 . . ?
N1A C9A C8A 121.6(5) . . ?
N1A C9A C4A 118.0(5) . . ?
C8A C9A C4A 120.3(5) . . ?
C6A C10A H10A 109.5 . . ?
C6A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C6A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N2A C11A C2A 123.9(5) . . ?
N2A C11A H11A 118.1 . . ?
C2A C11A H11A 118.1 . . ?
O2A C12A N4A 124.2(5) . . ?
O2A C12A N3A 119.1(5) . . ?
N4A C12A N3A 116.7(5) . . ?
C14A C13A C18A 120.0 . . ?
C14A C13A N4A 116.4(7) . . ?
C18A C13A N4A 123.6(7) . . ?
C13A C14A C15A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A C13A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C13A C18A H18A 120.0 . . ?
C14C C13C C18C 120.0 . . ?
C14C C13C N4A 114.8(10) . . ?
C18C C13C N4A 125.2(10) . . ?
C15C C14C C13C 120.0 . . ?
C15C C14C H14B 120.0 . . ?
C13C C14C H14B 120.0 . . ?
C14C C15C C16C 120.0 . . ?
C14C C15C H15B 120.0 . . ?
C16C C15C H15B 120.0 . . ?
C17C C16C C15C 120.0 . . ?
C17C C16C H16B 120.0 . . ?
C15C C16C H16B 120.0 . . ?
C16C C17C C18C 120.0 . . ?
C16C C17C H17B 120.0 . . ?
C18C C17C H17B 120.0 . . ?
C17C C18C C13C 120.0 . . ?
C17C C18C H18B 120.0 . . ?
C13C C18C H18B 120.0 . . ?
O1B Cu2 N2B 91.09(16) . . ?
O1B Cu2 O2B 170.22(16) . . ?
N2B Cu2 O2B 80.81(16) . . ?
O1B Cu2 Cl3 95.60(11) . . ?
N2B Cu2 Cl3 173.31(13) . . ?
O2B Cu2 Cl3 92.51(11) . . ?
O1B Cu2 O3B 87.34(16) . . ?
N2B Cu2 O3B 87.46(16) . . ?
O2B Cu2 O3B 97.70(16) . . ?
Cl3 Cu2 O3B 93.06(11) . . ?
O1B Cu2 Cl4 77.90(12) . . ?
N2B Cu2 Cl4 83.99(13) . . ?
O2B Cu2 Cl4 95.69(13) . . ?
Cl3 Cu2 Cl4 97.17(5) . . ?
O3B Cu2 Cl4 162.75(11) . . ?
C1B O1B Cu2 127.3(3) . . ?
C12B O2B Cu2 113.3(3) . . ?
C19B O3B Cu2 129.9(4) . . ?
C19B O3B H3B 105(7) . . ?
Cu2 O3B H3B 125(7) . . ?
C1B N1B C9B 125.4(4) . . ?
C1B N1B H1BA 117.3 . . ?
C9B N1B H1BA 117.3 . . ?
C11B N2B N3B 118.1(4) . . ?
C11B N2B Cu2 130.3(4) . . ?
N3B N2B Cu2 111.6(3) . . ?
C12B N3B N2B 114.7(4) . . ?
C12B N3B H3BB 122.7 . . ?
N2B N3B H3BB 122.7 . . ?
C12B N4B C13B 127.9(5) . . ?
C12B N4B H4BA 116.0 . . ?
C13B N4B H4BA 116.0 . . ?
O1B C1B N1B 117.5(5) . . ?
O1B C1B C2B 126.0(5) . . ?
N1B C1B C2B 116.5(5) . . ?
C3B C2B C11B 117.7(5) . . ?
C3B C2B C1B 118.9(5) . . ?
C11B C2B C1B 123.4(5) . . ?
C2B C3B C4B 122.7(5) . . ?
C2B C3B H3BA 118.7 . . ?
C4B C3B H3BA 118.7 . . ?
C9B C4B C5B 118.9(5) . . ?
C9B C4B C3B 117.9(5) . . ?
C5B C4B C3B 123.1(5) . . ?
C6B C5B C4B 121.4(5) . . ?
C6B C5B H5BA 119.3 . . ?
C4B C5B H5BA 119.3 . . ?
C5B C6B C7B 117.8(5) . . ?
C5B C6B C10B 121.5(5) . . ?
C7B C6B C10B 120.7(5) . . ?
C8B C7B C6B 122.6(5) . . ?
C8B C7B H7BA 118.7 . . ?
C6B C7B H7BA 118.7 . . ?
C7B C8B C9B 118.7(5) . . ?
C7B C8B H8BA 120.7 . . ?
C9B C8B H8BA 120.7 . . ?
N1B C9B C8B 121.0(5) . . ?
N1B C9B C4B 118.5(5) . . ?
C8B C9B C4B 120.6(5) . . ?
C6B C10B H10D 109.5 . . ?
C6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N2B C11B C2B 121.8(5) . . ?
N2B C11B H11B 119.1 . . ?
C2B C11B H11B 119.1 . . ?
O2B C12B N4B 124.1(5) . . ?
O2B C12B N3B 119.3(5) . . ?
N4B C12B N3B 116.5(4) . . ?
C14B C13B C18B 119.4(5) . . ?
C14B C13B N4B 124.4(5) . . ?
C18B C13B N4B 116.2(5) . . ?
C15B C14B C13B 119.5(5) . . ?
C15B C14B H14C 120.2 . . ?
C13B C14B H14C 120.2 . . ?
C14B C15B C16B 121.2(5) . . ?
C14B C15B H15C 119.4 . . ?
C16B C15B H15C 119.4 . . ?
C17B C16B C15B 118.8(5) . . ?
C17B C16B H16C 120.6 . . ?
C15B C16B H16C 120.6 . . ?
C18B C17B C16B 120.4(5) . . ?
C18B C17B H17C 119.8 . . ?
C16B C17B H17C 119.8 . . ?
C17B C18B C13B 120.7(5) . . ?
C17B C18B H18C 119.7 . . ?
C13B C18B H18C 119.7 . . ?
O3B C19B H19A 109.5 . . ?
O3B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
O3B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
H1W1 O1W H1W2 105(3) . . ?
H2W1 O2W H2W2 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11A N2A N3A C12A 171.7(5) . . . . ?
Cu1 N2A N3A C12A -10.7(6) . . . . ?
Cu1 O1A C1A N1A 174.0(4) . . . . ?
Cu1 O1A C1A C2A -4.7(8) . . . . ?
C9A N1A C1A O1A -178.0(5) . . . . ?
C9A N1A C1A C2A 0.8(8) . . . . ?
O1A C1A C2A C3A -178.8(5) . . . . ?
N1A C1A C2A C3A 2.5(8) . . . . ?
O1A C1A C2A C11A 1.9(9) . . . . ?
N1A C1A C2A C11A -176.7(5) . . . . ?
C11A C2A C3A C4A 174.7(5) . . . . ?
C1A C2A C3A C4A -4.5(8) . . . . ?
C2A C3A C4A C9A 3.2(8) . . . . ?
C2A C3A C4A C5A -173.0(5) . . . . ?
C9A C4A C5A C6A -1.3(8) . . . . ?
C3A C4A C5A C6A 174.7(5) . . . . ?
C4A C5A C6A C7A 2.7(8) . . . . ?
C4A C5A C6A C10A -175.8(5) . . . . ?
C5A C6A C7A C8A -2.0(9) . . . . ?
C10A C6A C7A C8A 176.5(5) . . . . ?
C6A C7A C8A C9A -0.1(9) . . . . ?
C1A N1A C9A C8A 175.1(5) . . . . ?
C1A N1A C9A C4A -2.1(8) . . . . ?
C7A C8A C9A N1A -175.7(5) . . . . ?
C7A C8A C9A C4A 1.5(9) . . . . ?
C5A C4A C9A N1A 176.4(5) . . . . ?
C3A C4A C9A N1A 0.1(8) . . . . ?
C5A C4A C9A C8A -0.8(8) . . . . ?
C3A C4A C9A C8A -177.1(5) . . . . ?
N3A N2A C11A C2A -179.7(5) . . . . ?
Cu1 N2A C11A C2A 3.2(8) . . . . ?
C3A C2A C11A N2A 179.7(5) . . . . ?
C1A C2A C11A N2A -1.1(8) . . . . ?
Cu1 O2A C12A N4A -179.0(4) . . . . ?
Cu1 O2A C12A N3A 0.0(6) . . . . ?
C13A N4A C12A O2A -1.4(11) . . . . ?
C13C N4A C12A O2A -11.0(13) . . . . ?
C13A N4A C12A N3A 179.6(8) . . . . ?
C13C N4A C12A N3A 170.0(11) . . . . ?
N2A N3A C12A O2A 7.4(7) . . . . ?
N2A N3A C12A N4A -173.6(5) . . . . ?
C12A N4A C13A C14A 177.1(6) . . . . ?
C12A N4A C13A C18A -3.4(11) . . . . ?
C18A C13A C14A C15A 0.0 . . . . ?
N4A C13A C14A C15A 179.5(9) . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A C13A 0.0 . . . . ?
C14A C13A C18A C17A 0.0 . . . . ?
N4A C13A C18A C17A -179.4(10) . . . . ?
C12A N4A C13C C14C -150.2(9) . . . . ?
C12A N4A C13C C18C 28.5(14) . . . . ?
C18C C13C C14C C15C 0.0 . . . . ?
N4A C13C C14C C15C 178.7(15) . . . . ?
C13C C14C C15C C16C 0.0 . . . . ?
C14C C15C C16C C17C 0.0 . . . . ?
C15C C16C C17C C18C 0.0 . . . . ?
C16C C17C C18C C13C 0.0 . . . . ?
C14C C13C C18C C17C 0.0 . . . . ?
N4A C13C C18C C17C -178.5(16) . . . . ?
C11B N2B N3B C12B -175.4(5) . . . . ?
Cu2 N2B N3B C12B 4.9(5) . . . . ?
Cu2 O1B C1B N1B -177.2(3) . . . . ?
Cu2 O1B C1B C2B 0.9(8) . . . . ?
C9B N1B C1B O1B 174.3(5) . . . . ?
C9B N1B C1B C2B -4.0(8) . . . . ?
O1B C1B C2B C3B -177.3(5) . . . . ?
N1B C1B C2B C3B 0.8(8) . . . . ?
O1B C1B C2B C11B 1.9(9) . . . . ?
N1B C1B C2B C11B 180.0(5) . . . . ?
C11B C2B C3B C4B -177.4(5) . . . . ?
C1B C2B C3B C4B 1.8(9) . . . . ?
C2B C3B C4B C9B -1.5(9) . . . . ?
C2B C3B C4B C5B 176.8(6) . . . . ?
C9B C4B C5B C6B -1.0(9) . . . . ?
C3B C4B C5B C6B -179.2(6) . . . . ?
C4B C5B C6B C7B 3.0(9) . . . . ?
C4B C5B C6B C10B -177.9(6) . . . . ?
C5B C6B C7B C8B -3.5(9) . . . . ?
C10B C6B C7B C8B 177.4(6) . . . . ?
C6B C7B C8B C9B 1.8(9) . . . . ?
C1B N1B C9B C8B -174.6(5) . . . . ?
C1B N1B C9B C4B 4.5(8) . . . . ?
C7B C8B C9B N1B 179.4(5) . . . . ?
C7B C8B C9B C4B 0.3(8) . . . . ?
C5B C4B C9B N1B -179.8(5) . . . . ?
C3B C4B C9B N1B -1.5(8) . . . . ?
C5B C4B C9B C8B -0.7(9) . . . . ?
C3B C4B C9B C8B 177.6(5) . . . . ?
N3B N2B C11B C2B -179.1(5) . . . . ?
Cu2 N2B C11B C2B 0.6(9) . . . . ?
C3B C2B C11B N2B 176.6(6) . . . . ?
C1B C2B C11B N2B -2.6(9) . . . . ?
Cu2 O2B C12B N4B 179.9(4) . . . . ?
Cu2 O2B C12B N3B -1.8(6) . . . . ?
C13B N4B C12B O2B 0.5(9) . . . . ?
C13B N4B C12B N3B -177.9(5) . . . . ?
N2B N3B C12B O2B -2.2(7) . . . . ?
N2B N3B C12B N4B 176.3(4) . . . . ?
C12B N4B C13B C14B -3.9(9) . . . . ?
C12B N4B C13B C18B 176.1(5) . . . . ?
C18B C13B C14B C15B 0.5(8) . . . . ?
N4B C13B C14B C15B -179.5(5) . . . . ?
C13B C14B C15B C16B -1.6(8) . . . . ?
C14B C15B C16B C17B 1.3(9) . . . . ?
C15B C16B C17B C18B 0.1(9) . . . . ?
C16B C17B C18B C13B -1.1(9) . . . . ?
C14B C13B C18B C17B 0.8(8) . . . . ?
N4B C13B C18B C17B -179.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1AA Cl4 0.88 2.33 3.200(4) 171.3 . yes
N3A H3AB Cl4 0.88 2.38 3.230(5) 161.9 1_554 yes
N4A H4A O1W 0.75(8) 2.10(8) 2.828(7) 163(8) 1_554 yes
C8A H8AA Cl4 0.95 2.98 3.725(6) 136.7 . yes
C8A H8AA O3B 0.95 2.66 3.488(7) 146.7 1_455 yes
C11A H11A Cl4 0.95 2.90 3.695(5) 141.4 1_554 yes
C14A^a H14A^a Cl1 0.95 2.97 3.857(8) 156.3 1_554 yes
C18A^a H18A^a O2A 0.95 2.24 2.859(11) 122.3 . yes
C18C^b H18B^b O2A 0.95 2.37 2.889(18) 114.2 . yes
O3B H3B Cl4 0.98(12) 2.13(12) 3.109(5) 173(10) 1_655 yes
N1B H1BA Cl2 0.88 2.35 3.205(4) 165.2 1_556 yes
N3B H3BB Cl2 0.88 2.35 3.196(4) 161.7 . yes
N4B H4BA O2W 0.88 1.90 2.775(6) 171.1 . yes
C8B H8BA Cl2 0.95 2.90 3.649(6) 136.3 1_556 yes
C11B H11B Cl2 0.95 2.76 3.584(5) 145.1 . yes
C14B H14C O2B 0.95 2.25 2.861(6) 121.6 . yes
C18B H18C O2W 0.95 2.55 3.308(7) 136.7 . yes
C19B H19A Cl3 0.98 2.83 3.719(7) 150.9 1_655 yes
O1W H1W1 Cl4 0.81(2) 2.60(12) 3.142(6) 125(12) . yes
O2W H2W1 Cl3 0.811(19) 2.35(2) 3.142(4) 166(6) 1_554 yes
O2W H2W2 Cl2 0.81(2) 2.32(3) 3.082(4) 156(5) . yes

_refine_diff_density_max         0.791
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1922257'
loop_
_audit_author_name
_audit_author_address
'Ray Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2021-05-03 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu N6 O9, H2 O'
_chemical_formula_sum            'C19 H22 Cu N6 O10'
_chemical_formula_weight         557.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7584(3)
_cell_length_b                   11.3260(4)
_cell_length_c                   25.7631(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2263.85(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5527
_cell_measurement_theta_min      3.9170
_cell_measurement_theta_max      37.4250

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             1148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    1.034
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            20963
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.539
_diffrn_reflns_theta_max         41.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             13555
_reflns_number_gt                10088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     0.808
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'Shelxt (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 20185b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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/[σ²(Fo²)+(0.0290P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         13555
_refine_ls_number_parameters     376
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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
Cu Cu 0.61871(4) 0.59517(2) 0.30025(2) 0.01541(6) Uani 1 1 d . . . . .
O1 O 0.7522(2) 0.51501(16) 0.24838(7) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.4756(2) 0.69004(15) 0.34688(7) 0.0175(3) Uani 1 1 d . . . . .
N5A N 0.949(3) 0.537(2) 0.3660(8) 0.0198(17) Uani 0.26(4) 1 d D U P A 2
O3A O 0.823(3) 0.605(2) 0.3635(10) 0.0209(18) Uani 0.26(4) 1 d D U P A 2
O4A O 1.062(3) 0.537(2) 0.3309(8) 0.026(3) Uani 0.26(4) 1 d D U P A 2
O5A O 0.968(3) 0.4687(16) 0.4031(6) 0.031(3) Uani 0.26(4) 1 d D U P A 2
N5 N 0.9375(9) 0.5371(7) 0.3662(3) 0.0206(8) Uani 0.74(4) 1 d D U P A 1
O3 O 0.8367(11) 0.6215(7) 0.3602(4) 0.0242(9) Uani 0.74(4) 1 d D U P A 1
O4 O 1.0780(13) 0.5343(9) 0.3418(6) 0.043(2) Uani 0.74(4) 1 d D . P A 1
O5 O 0.904(3) 0.4549(8) 0.3963(5) 0.056(3) Uani 0.74(4) 1 d D . P A 1
O6 O 0.5317(3) 0.44518(16) 0.32690(7) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.587(5) 0.393(3) 0.3201(14) 0.039(11) Uiso 1 1 d . . . . .
O7 O 0.3105(2) 0.74922(15) 0.20384(8) 0.0218(4) Uani 1 1 d . . . . .
O8 O 0.3448(3) 0.56949(16) 0.23015(7) 0.0238(4) Uani 1 1 d . . . . .
O9 O 0.4691(3) 0.62760(17) 0.15888(7) 0.0210(4) Uani 1 1 d . . . . .
O1W O 0.9035(3) 0.25899(17) 0.20820(8) 0.0249(4) Uani 1 1 d D . . . .
H1W1 H 0.918(5) 0.195(2) 0.1963(14) 0.049(12) Uiso 1 1 d D . . . .
H1W2 H 0.842(4) 0.251(3) 0.2342(10) 0.022(9) Uiso 1 1 d D . . . .
N1 N 0.9318(3) 0.48797(18) 0.18175(8) 0.0161(4) Uani 1 1 d . . . . .
H1A H 0.933148 0.412740 0.190280 0.019 Uiso 1 1 calc R U . . .
N2 N 0.6629(3) 0.74922(17) 0.26889(8) 0.0142(3) Uani 1 1 d . . . . .
N3 N 0.5853(3) 0.83741(16) 0.29696(8) 0.0170(4) Uani 1 1 d . . . . .
H3B H 0.596207 0.912646 0.289082 0.020 Uiso 1 1 calc R U . . .
N4 N 0.4202(3) 0.88367(17) 0.36760(8) 0.0162(4) Uani 1 1 d . . . . .
H4A H 0.436611 0.957058 0.357535 0.019 Uiso 1 1 calc R U . . .
N6 N 0.3762(3) 0.64843(16) 0.19710(8) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.8386(3) 0.5611(2) 0.21169(9) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.8441(3) 0.68623(18) 0.19881(9) 0.0140(3) Uani 1 1 d . . . . .
C3 C 0.9353(3) 0.7218(2) 0.15605(9) 0.0169(4) Uani 1 1 d . . . . .
H3A H 0.937450 0.803368 0.147480 0.020 Uiso 1 1 calc R U . . .
C4 C 1.0264(3) 0.6414(2) 0.12417(9) 0.0171(4) Uani 1 1 d . . . . .
C5 C 1.1176(4) 0.6761(2) 0.07911(9) 0.0205(4) Uani 1 1 d . . . . .
H5A H 1.119273 0.756907 0.069175 0.025 Uiso 1 1 calc R U . . .
C6 C 1.2040(3) 0.5937(3) 0.04948(9) 0.0230(5) Uani 1 1 d . . . . .
C7 C 1.2028(4) 0.4744(3) 0.06537(10) 0.0230(5) Uani 1 1 d . . . . .
H7A H 1.263066 0.417689 0.045147 0.028 Uiso 1 1 calc R U . . .
C8 C 1.1165(3) 0.4375(2) 0.10946(9) 0.0198(4) Uani 1 1 d . . . . .
H8A H 1.118749 0.357028 0.119780 0.024 Uiso 1 1 calc R U . . .
C9 C 1.0257(3) 0.5215(2) 0.13857(10) 0.0164(4) Uani 1 1 d . . . . .
C10 C 1.2975(4) 0.6302(3) 0.00039(11) 0.0332(7) Uani 1 1 d . . . . .
H10A H 1.242429 0.700566 -0.014219 0.050 Uiso 1 1 calc R U . . .
H10B H 1.292471 0.565675 -0.024936 0.050 Uiso 1 1 calc R U . . .
H10C H 1.418182 0.647792 0.008563 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7571(3) 0.7755(2) 0.22944(9) 0.0154(4) Uani 1 1 d . . . . .
H11A H 0.769975 0.856132 0.220067 0.019 Uiso 1 1 calc R U . . .
C12 C 0.4901(3) 0.7990(2) 0.33798(9) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.3221(3) 0.8669(2) 0.41367(9) 0.0160(4) Uani 1 1 d . . . . .
C14 C 0.2287(3) 0.7645(2) 0.42414(10) 0.0190(4) Uani 1 1 d . . . . .
H14A H 0.229394 0.700553 0.400300 0.023 Uiso 1 1 calc R U . . .
C15 C 0.1345(4) 0.7573(2) 0.46990(10) 0.0239(5) Uani 1 1 d . . . . .
H15A H 0.068704 0.688407 0.476978 0.029 Uiso 1 1 calc R U . . .
C16 C 0.1355(4) 0.8496(3) 0.50547(10) 0.0278(6) Uani 1 1 d . . . . .
H16A H 0.073647 0.842791 0.537160 0.033 Uiso 1 1 calc R U . . .
C17 C 0.2269(4) 0.9516(3) 0.49449(11) 0.0277(6) Uani 1 1 d . . . . .
H17A H 0.226674 1.015117 0.518559 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3190(4) 0.9614(3) 0.44840(10) 0.0224(5) Uani 1 1 d . . . . .
H18A H 0.379518 1.032105 0.440588 0.027 Uiso 1 1 calc R U . . .
C19 C 0.4700(4) 0.4315(2) 0.37941(10) 0.0262(6) Uani 1 1 d . . . . .
H19A H 0.446199 0.347947 0.386205 0.039 Uiso 1 1 calc R U . . .
H19B H 0.363963 0.477428 0.383948 0.039 Uiso 1 1 calc R U . . .
H19C H 0.557799 0.459884 0.403741 0.039 Uiso 1 1 calc R U . . .


_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
Cu O1 1.9190(18) . ?
Cu O6 1.9525(18) . ?
Cu N2 1.953(2) . ?
Cu O2 1.9571(17) . ?
Cu O3A 2.28(2) . ?
Cu O3 2.309(9) . ?
Cu O8 2.804(2) . ?
O1 C1 1.271(3) . ?
O2 C12 1.260(3) . ?
N5A O5A 1.239(6) . ?
N5A O3A 1.245(4) . ?
N5A O4A 1.258(5) . ?
N5 O5 1.240(5) . ?
N5 O3 1.244(4) . ?
N5 O4 1.259(4) . ?
O6 C19 1.444(3) . ?
O6 H6 0.75(4) . ?
O7 N6 1.262(2) . ?
O8 N6 1.259(3) . ?
O9 N6 1.243(3) . ?
O1W H1W1 0.79(2) . ?
O1W H1W2 0.83(2) . ?
N1 C1 1.343(3) . ?
N1 C9 1.383(3) . ?
N1 H1A 0.8800 . ?
N2 C11 1.287(3) . ?
N2 N3 1.372(3) . ?
N3 C12 1.361(3) . ?
N3 H3B 0.8800 . ?
N4 C12 1.340(3) . ?
N4 C13 1.423(3) . ?
N4 H4A 0.8800 . ?
C1 C2 1.457(3) . ?
C2 C3 1.370(3) . ?
C2 C11 1.449(3) . ?
C3 C4 1.416(3) . ?
C3 H3A 0.9500 . ?
C4 C9 1.408(3) . ?
C4 C5 1.415(3) . ?
C5 C6 1.380(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.412(4) . ?
C6 C10 1.515(4) . ?
C7 C8 1.383(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.401(3) . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9500 . ?
C13 C14 1.393(4) . ?
C13 C18 1.395(4) . ?
C14 C15 1.390(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.390(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O1 Cu O6 91.13(8) . . ?
O1 Cu N2 92.29(8) . . ?
O6 Cu N2 169.52(9) . . ?
O1 Cu O2 173.37(8) . . ?
O6 Cu O2 93.77(8) . . ?
N2 Cu O2 82.12(8) . . ?
O1 Cu O3A 98.3(5) . . ?
O6 Cu O3A 91.8(6) . . ?
N2 Cu O3A 97.5(6) . . ?
O2 Cu O3A 86.0(5) . . ?
O1 Cu O3 97.6(2) . . ?
O6 Cu O3 97.5(3) . . ?
N2 Cu O3 91.9(2) . . ?
O2 Cu O3 86.2(2) . . ?
O1 Cu O8 84.92(7) . . ?
O6 Cu O8 82.78(7) . . ?
N2 Cu O8 87.66(7) . . ?
O2 Cu O8 91.27(7) . . ?
O3A Cu O8 173.7(6) . . ?
O3 Cu O8 177.5(2) . . ?
C1 O1 Cu 127.48(16) . . ?
C12 O2 Cu 112.04(16) . . ?
O5A N5A O3A 121.2(6) . . ?
O5A N5A O4A 118.3(6) . . ?
O3A N5A O4A 120.4(6) . . ?
N5A O3A Cu 123.5(19) . . ?
O5 N5 O3 121.5(4) . . ?
O5 N5 O4 118.4(4) . . ?
O3 N5 O4 120.1(4) . . ?
N5 O3 Cu 116.4(7) . . ?
C19 O6 Cu 122.52(16) . . ?
C19 O6 H6 109(3) . . ?
Cu O6 H6 114(3) . . ?
N6 O8 Cu 102.42(15) . . ?
H1W1 O1W H1W2 107(3) . . ?
C1 N1 C9 125.2(2) . . ?
C1 N1 H1A 117.4 . . ?
C9 N1 H1A 117.4 . . ?
C11 N2 N3 119.8(2) . . ?
C11 N2 Cu 129.27(17) . . ?
N3 N2 Cu 110.81(14) . . ?
C12 N3 N2 114.48(18) . . ?
C12 N3 H3B 122.8 . . ?
N2 N3 H3B 122.8 . . ?
C12 N4 C13 126.6(2) . . ?
C12 N4 H4A 116.7 . . ?
C13 N4 H4A 116.7 . . ?
O9 N6 O8 120.9(2) . . ?
O9 N6 O7 121.0(2) . . ?
O8 N6 O7 118.1(2) . . ?
O1 C1 N1 117.3(2) . . ?
O1 C1 C2 125.7(2) . . ?
N1 C1 C2 117.0(2) . . ?
C3 C2 C11 118.3(2) . . ?
C3 C2 C1 119.0(2) . . ?
C11 C2 C1 122.8(2) . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
C9 C4 C5 119.1(2) . . ?
C9 C4 C3 117.8(2) . . ?
C5 C4 C3 123.1(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 C10 120.7(3) . . ?
C7 C6 C10 120.4(3) . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
C7 C8 C9 118.6(2) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
N1 C9 C8 120.6(2) . . ?
N1 C9 C4 118.6(2) . . ?
C8 C9 C4 120.8(2) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C2 122.2(2) . . ?
N2 C11 H11A 118.9 . . ?
C2 C11 H11A 118.9 . . ?
O2 C12 N4 124.1(2) . . ?
O2 C12 N3 120.2(2) . . ?
N4 C12 N3 115.7(2) . . ?
C14 C13 C18 120.3(2) . . ?
C14 C13 N4 123.4(2) . . ?
C18 C13 N4 116.2(2) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 H18A 120.2 . . ?
C13 C18 H18A 120.2 . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5A N5A O3A Cu -117(3) . . . . ?
O4A N5A O3A Cu 64(3) . . . . ?
O5 N5 O3 Cu -85.2(16) . . . . ?
O4 N5 O3 Cu 95.5(16) . . . . ?
C11 N2 N3 C12 -179.5(2) . . . . ?
Cu N2 N3 C12 -2.9(2) . . . . ?
Cu O8 N6 O9 88.6(2) . . . . ?
Cu O8 N6 O7 -91.5(2) . . . . ?
Cu O1 C1 N1 175.80(16) . . . . ?
Cu O1 C1 C2 -5.0(3) . . . . ?
C9 N1 C1 O1 176.3(2) . . . . ?
C9 N1 C1 C2 -3.0(3) . . . . ?
O1 C1 C2 C3 -176.0(2) . . . . ?
N1 C1 C2 C3 3.2(3) . . . . ?
O1 C1 C2 C11 4.1(4) . . . . ?
N1 C1 C2 C11 -176.7(2) . . . . ?
C11 C2 C3 C4 179.1(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C9 -1.9(4) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
C9 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C6 -179.9(2) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C4 C5 C6 C10 178.3(3) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C10 C6 C7 C8 -178.9(3) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C1 N1 C9 C8 -179.0(2) . . . . ?
C1 N1 C9 C4 0.3(4) . . . . ?
C7 C8 C9 N1 177.4(2) . . . . ?
C7 C8 C9 C4 -1.9(4) . . . . ?
C5 C4 C9 N1 -178.0(2) . . . . ?
C3 C4 C9 N1 2.2(3) . . . . ?
C5 C4 C9 C8 1.2(4) . . . . ?
C3 C4 C9 C8 -178.5(2) . . . . ?
N3 N2 C11 C2 179.1(2) . . . . ?
Cu N2 C11 C2 3.2(4) . . . . ?
C3 C2 C11 N2 177.1(2) . . . . ?
C1 C2 C11 N2 -3.1(4) . . . . ?
Cu O2 C12 N4 -172.89(19) . . . . ?
Cu O2 C12 N3 5.3(3) . . . . ?
C13 N4 C12 O2 1.2(4) . . . . ?
C13 N4 C12 N3 -177.1(2) . . . . ?
N2 N3 C12 O2 -1.6(3) . . . . ?
N2 N3 C12 N4 176.7(2) . . . . ?
C12 N4 C13 C14 -25.9(4) . . . . ?
C12 N4 C13 C18 155.9(3) . . . . ?
C18 C13 C14 C15 -0.9(4) . . . . ?
N4 C13 C14 C15 -179.0(2) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C15 C16 C17 2.0(5) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C13 -1.4(4) . . . . ?
C14 C13 C18 C17 2.2(4) . . . . ?
N4 C13 C18 C17 -179.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 O7 0.75(4) 1.91(4) 2.656(3) 169(4) 3_645 yes
O1W H1W1 N5A^b 0.79(2) 2.62(3) 3.360(17) 156(3) 3_745 yes
O1W H1W1 O4A^b 0.79(2) 1.93(3) 2.72(2) 176(4) 3_745 yes
O1W H1W1 O3^a 0.79(2) 2.54(3) 3.098(11) 129(3) 3_745 yes
O1W H1W1 O4^a 0.79(2) 2.07(2) 2.856(11) 171(4) 3_745 yes
O1W H1W2 O7 0.83(2) 1.99(2) 2.811(3) 174(3) 3_645 yes
N1 H1A O1W 0.88 1.82 2.691(3) 172.0 . yes
N3 H3B O8 0.88 1.90 2.773(3) 171.3 3_655 yes
N4 H4A O9 0.88 2.11 2.972(3) 167.1 3_655 yes
C14 H14A O2 0.95 2.36 2.888(3) 114.9 . yes
C19 H19B O4^a 0.98 2.55 3.398(13) 144.3 1_455 yes

_refine_diff_density_max         0.770
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.104



