# 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_D
_database_code_depnum_ccdc_archive 'CCDC 2044623'
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-02-08 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         'C21 H15 Cl2 Cu N3 O'
_chemical_formula_sum            'C21 H15 Cl2 Cu N3 O'
_chemical_formula_weight         459.80

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'
Cl Cl 0.1484 0.1585 '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                   7.8481(7)
_cell_length_b                   13.2640(13)
_cell_length_c                   18.1504(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.039(8)
_cell_angle_gamma                90
_cell_volume                     1870.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6565
_cell_measurement_theta_min      3.2690
_cell_measurement_theta_max      28.8090

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    1.471
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            12122
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         29.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4420
_reflns_number_gt                3510
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0432P)²+0.8412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4420
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.41165(3) 0.68739(2) 0.06315(2) 0.03909(10) Uani 1 1 d . . . . .
Cl1 Cl 0.54703(10) 0.75011(6) 0.16838(3) 0.0649(2) Uani 1 1 d . . . . .
Cl2 Cl 0.11008(8) 0.76451(5) 0.04919(3) 0.05578(18) Uani 1 1 d . . . . .
O1 O 0.1128(3) 0.64748(13) -0.29721(9) 0.0578(5) Uani 1 1 d . . . . .
H1A H 0.111694 0.666467 -0.340626 0.075(10) Uiso 1 1 d R . . . .
N1 N 0.3305(2) 0.55293(15) 0.10104(9) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.3505(2) 0.61492(13) -0.02987(9) 0.0330(4) Uani 1 1 d . . . . .
N3 N 0.5107(2) 0.78168(15) -0.01005(9) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.3355(3) 0.5251(2) 0.17217(13) 0.0521(6) Uani 1 1 d . . . . .
H1B H 0.385396 0.568296 0.209406 0.062 Uiso 1 1 calc R U . . .
C2 C 0.2692(4) 0.4345(2) 0.19204(15) 0.0604(8) Uani 1 1 d . . . . .
H2A H 0.274847 0.416620 0.241873 0.073 Uiso 1 1 calc R U . . .
C3 C 0.1952(3) 0.3714(2) 0.13749(17) 0.0594(7) Uani 1 1 d . . . . .
H3A H 0.149725 0.310012 0.149945 0.071 Uiso 1 1 calc R U . . .
C4 C 0.1877(3) 0.39900(19) 0.06299(14) 0.0483(6) Uani 1 1 d . . . . .
H4A H 0.136792 0.356931 0.025191 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2578(3) 0.49033(17) 0.04687(12) 0.0392(5) Uani 1 1 d . . . . .
C6 C 0.2639(3) 0.52835(16) -0.02991(11) 0.0337(4) Uani 1 1 d . . . . .
C7 C 0.1879(3) 0.48524(17) -0.09578(12) 0.0368(5) Uani 1 1 d . . . . .
H7A H 0.126270 0.425455 -0.094990 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2041(3) 0.53207(16) -0.16391(11) 0.0332(4) Uani 1 1 d . . . . .
C9 C 0.3046(3) 0.61923(16) -0.16162(11) 0.0332(4) Uani 1 1 d . . . . .
H9A H 0.325730 0.649643 -0.205615 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3724(3) 0.66013(16) -0.09386(11) 0.0313(4) Uani 1 1 d . . . . .
C11 C 0.4686(3) 0.75558(16) -0.08222(11) 0.0340(4) Uani 1 1 d . . . . .
C12 C 0.5139(3) 0.81467(17) -0.13876(12) 0.0417(5) Uani 1 1 d . . . . .
H12A H 0.482581 0.796155 -0.188218 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6065(3) 0.9017(2) -0.12088(14) 0.0536(6) Uani 1 1 d . . . . .
H13A H 0.638325 0.942632 -0.158278 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6515(4) 0.9275(2) -0.04759(15) 0.0595(7) Uani 1 1 d . . . . .
H14A H 0.714525 0.985812 -0.034630 0.071 Uiso 1 1 calc R U . . .
C15 C 0.6018(3) 0.8658(2) 0.00635(13) 0.0525(6) Uani 1 1 d . . . . .
H15A H 0.632576 0.883272 0.056062 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1132(3) 0.49030(16) -0.23461(11) 0.0350(4) Uani 1 1 d . . . . .
C17 C 0.0698(3) 0.54941(16) -0.29897(12) 0.0378(5) Uani 1 1 d . . . . .
C18 C -0.0212(3) 0.50756(19) -0.36353(12) 0.0453(5) Uani 1 1 d . . . . .
H18A H -0.046963 0.546961 -0.406009 0.054 Uiso 1 1 calc R U . . .
C19 C -0.0724(3) 0.4091(2) -0.36445(14) 0.0520(6) Uani 1 1 d . . . . .
H19A H -0.132681 0.381694 -0.407544 0.062 Uiso 1 1 calc R U . . .
C20 C -0.0349(3) 0.35047(19) -0.30178(15) 0.0513(6) Uani 1 1 d . . . . .
H20A H -0.072176 0.283889 -0.302220 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0578(3) 0.39024(17) -0.23835(13) 0.0436(5) Uani 1 1 d . . . . .
H21A H 0.084181 0.349170 -0.196788 0.052 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
Cu1 N2 1.9437(16) . ?
Cu1 N1 2.045(2) . ?
Cu1 N3 2.0550(19) . ?
Cu1 Cl1 2.2139(7) . ?
Cu1 Cl2 2.5582(7) . ?
O1 C17 1.343(3) . ?
O1 H1A 0.8261 . ?
N1 C1 1.338(3) . ?
N1 C5 1.351(3) . ?
N2 C6 1.334(3) . ?
N2 C10 1.339(3) . ?
N3 C15 1.336(3) . ?
N3 C11 1.350(3) . ?
C1 C2 1.378(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.489(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.406(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(3) . ?
C8 C16 1.485(3) . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.474(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.395(3) . ?
C16 C17 1.409(3) . ?
C17 C18 1.399(3) . ?
C18 C19 1.365(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 79.05(7) . . ?
N2 Cu1 N3 79.01(7) . . ?
N1 Cu1 N3 155.79(7) . . ?
N2 Cu1 Cl1 164.93(6) . . ?
N1 Cu1 Cl1 99.91(6) . . ?
N3 Cu1 Cl1 98.61(5) . . ?
N2 Cu1 Cl2 89.94(5) . . ?
N1 Cu1 Cl2 93.13(5) . . ?
N3 Cu1 Cl2 96.96(6) . . ?
Cl1 Cu1 Cl2 105.13(3) . . ?
C17 O1 H1A 107.7 . . ?
C1 N1 C5 119.0(2) . . ?
C1 N1 Cu1 126.64(19) . . ?
C5 N1 Cu1 114.27(14) . . ?
C6 N2 C10 120.79(17) . . ?
C6 N2 Cu1 119.35(13) . . ?
C10 N2 Cu1 119.05(14) . . ?
C15 N3 C11 118.75(19) . . ?
C15 N3 Cu1 127.10(15) . . ?
C11 N3 Cu1 114.06(14) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1B 118.9 . . ?
C2 C1 H1B 118.9 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 114.0(2) . . ?
C4 C5 C6 124.2(2) . . ?
N2 C6 C7 120.96(18) . . ?
N2 C6 C5 111.96(18) . . ?
C7 C6 C5 127.0(2) . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 117.38(18) . . ?
C9 C8 C16 122.37(18) . . ?
C7 C8 C16 120.23(19) . . ?
C10 C9 C8 119.82(18) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 121.08(19) . . ?
N2 C10 C11 112.68(17) . . ?
C9 C10 C11 126.22(18) . . ?
N3 C11 C12 121.6(2) . . ?
N3 C11 C10 114.21(18) . . ?
C12 C11 C10 124.23(19) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
N3 C15 C14 122.3(2) . . ?
N3 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C21 C16 C17 116.84(19) . . ?
C21 C16 C8 120.37(19) . . ?
C17 C16 C8 122.69(19) . . ?
O1 C17 C18 120.1(2) . . ?
O1 C17 C16 119.24(19) . . ?
C18 C17 C16 120.6(2) . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C16 122.0(2) . . ?
C20 C21 H21A 119.0 . . ?
C16 C21 H21A 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.1(3) . . . . ?
Cu1 N1 C1 C2 176.56(17) . . . . ?
N1 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
Cu1 N1 C5 C4 -176.39(16) . . . . ?
C1 N1 C5 C6 -178.51(18) . . . . ?
Cu1 N1 C5 C6 4.6(2) . . . . ?
C3 C4 C5 N1 -0.8(3) . . . . ?
C3 C4 C5 C6 178.1(2) . . . . ?
C10 N2 C6 C7 -2.9(3) . . . . ?
Cu1 N2 C6 C7 166.72(15) . . . . ?
C10 N2 C6 C5 178.89(17) . . . . ?
Cu1 N2 C6 C5 -11.5(2) . . . . ?
N1 C5 C6 N2 3.9(2) . . . . ?
C4 C5 C6 N2 -175.07(19) . . . . ?
N1 C5 C6 C7 -174.17(19) . . . . ?
C4 C5 C6 C7 6.9(3) . . . . ?
N2 C6 C7 C8 1.1(3) . . . . ?
C5 C6 C7 C8 178.99(19) . . . . ?
C6 C7 C8 C9 2.8(3) . . . . ?
C6 C7 C8 C16 -175.82(18) . . . . ?
C7 C8 C9 C10 -4.8(3) . . . . ?
C16 C8 C9 C10 173.70(19) . . . . ?
C6 N2 C10 C9 0.7(3) . . . . ?
Cu1 N2 C10 C9 -168.93(15) . . . . ?
C6 N2 C10 C11 179.02(17) . . . . ?
Cu1 N2 C10 C11 9.4(2) . . . . ?
C8 C9 C10 N2 3.2(3) . . . . ?
C8 C9 C10 C11 -174.80(19) . . . . ?
C15 N3 C11 C12 -1.5(3) . . . . ?
Cu1 N3 C11 C12 175.26(17) . . . . ?
C15 N3 C11 C10 178.4(2) . . . . ?
Cu1 N3 C11 C10 -4.9(2) . . . . ?
N2 C10 C11 N3 -2.4(3) . . . . ?
C9 C10 C11 N3 175.74(19) . . . . ?
N2 C10 C11 C12 177.4(2) . . . . ?
C9 C10 C11 C12 -4.4(3) . . . . ?
N3 C11 C12 C13 0.9(3) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C11 N3 C15 C14 1.1(4) . . . . ?
Cu1 N3 C15 C14 -175.1(2) . . . . ?
C13 C14 C15 N3 -0.2(4) . . . . ?
C9 C8 C16 C21 161.0(2) . . . . ?
C7 C8 C16 C21 -20.5(3) . . . . ?
C9 C8 C16 C17 -22.8(3) . . . . ?
C7 C8 C16 C17 155.7(2) . . . . ?
C21 C16 C17 O1 176.8(2) . . . . ?
C8 C16 C17 O1 0.5(3) . . . . ?
C21 C16 C17 C18 -1.5(3) . . . . ?
C8 C16 C17 C18 -177.7(2) . . . . ?
O1 C17 C18 C19 -176.9(2) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 C16 1.4(4) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C8 C16 C21 C20 176.5(2) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_D_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2044627'
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2021-02-08 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         'C22 H17 Cl2 Cu N3 O2 S'
_chemical_formula_sum            'C22 H17 Cl2 Cu N3 O2 S'
_chemical_formula_weight         521.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.6228(5)
_cell_length_b                   13.2678(4)
_cell_length_c                   14.8030(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.375(4)
_cell_angle_gamma                90
_cell_volume                     2110.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7199
_cell_measurement_theta_min      3.6050
_cell_measurement_theta_max      29.2010

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    1.413
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            12750
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         29.643
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5094
_reflns_number_gt                4423
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0397P)²+0.9343P] 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_number_reflns         5094
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.59712(2) 0.33374(2) 0.21817(2) 0.03014(8) Uani 1 1 d . . . . .
Cl1 Cl 0.73710(5) 0.45093(4) 0.29156(4) 0.04427(13) Uani 1 1 d . . . . .
Cl2 Cl 0.46616(4) 0.30047(4) 0.31978(3) 0.03558(11) Uani 1 1 d . . . . .
S1 S -0.03454(4) -0.23497(3) -0.19313(4) 0.03492(12) Uani 1 1 d . . . . .
O1 O 0.01904(15) -0.33102(10) -0.15621(13) 0.0529(4) Uani 1 1 d . . . . .
O2 O -0.07914(16) -0.21935(13) -0.29700(11) 0.0550(4) Uani 1 1 d . . . . .
N1 N 0.70478(14) 0.20953(12) 0.27240(11) 0.0306(3) Uani 1 1 d . . . . .
N2 N 0.50247(13) 0.23234(11) 0.12491(10) 0.0275(3) Uani 1 1 d . . . . .
N3 N 0.47116(14) 0.42254(11) 0.11476(11) 0.0301(3) Uani 1 1 d . . . . .
C1 C 0.81505(18) 0.20645(16) 0.34712(15) 0.0393(5) Uani 1 1 d . . . . .
H1B H 0.850747 0.266418 0.377435 0.047 Uiso 1 1 calc R U . . .
C2 C 0.87734(19) 0.11749(18) 0.38055(16) 0.0461(5) Uani 1 1 d . . . . .
H2B H 0.954007 0.117544 0.432591 0.055 Uiso 1 1 calc R U . . .
C3 C 0.82532(19) 0.02860(17) 0.33640(16) 0.0437(5) Uani 1 1 d . . . . .
H3A H 0.866521 -0.032161 0.358002 0.052 Uiso 1 1 calc R U . . .
C4 C 0.71007(18) 0.03036(15) 0.25881(14) 0.0344(4) Uani 1 1 d . . . . .
H4A H 0.672842 -0.028953 0.227938 0.041 Uiso 1 1 calc R U . . .
C5 C 0.65273(16) 0.12200(14) 0.22902(13) 0.0285(4) Uani 1 1 d . . . . .
C6 C 0.53166(16) 0.13538(13) 0.14568(12) 0.0269(3) Uani 1 1 d . . . . .
C7 C 0.45204(16) 0.05973(13) 0.09360(12) 0.0281(4) Uani 1 1 d . . . . .
H7A H 0.472089 -0.007557 0.109478 0.034 Uiso 1 1 calc R U . . .
C8 C 0.34049(16) 0.08570(13) 0.01642(12) 0.0262(3) Uani 1 1 d . . . . .
C9 C 0.31590(17) 0.18797(13) -0.00536(13) 0.0294(4) Uani 1 1 d . . . . .
H9A H 0.244818 0.207557 -0.057838 0.035 Uiso 1 1 calc R U . . .
C10 C 0.39776(16) 0.25986(13) 0.05151(12) 0.0281(4) Uani 1 1 d . . . . .
C11 C 0.38156(17) 0.37095(14) 0.04272(13) 0.0299(4) Uani 1 1 d . . . . .
C12 C 0.28825(19) 0.41920(15) -0.03175(14) 0.0382(4) Uani 1 1 d . . . . .
H12A H 0.227579 0.382320 -0.080116 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2860(2) 0.52402(16) -0.03361(15) 0.0420(5) Uani 1 1 d . . . . .
H13A H 0.223803 0.558323 -0.083209 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3776(2) 0.57627(15) 0.03929(15) 0.0393(4) Uani 1 1 d . . . . .
H14A H 0.378215 0.646362 0.039243 0.047 Uiso 1 1 calc R U . . .
C15 C 0.46789(19) 0.52350(14) 0.11202(14) 0.0342(4) Uani 1 1 d . . . . .
H15A H 0.529008 0.559213 0.161161 0.041 Uiso 1 1 calc R U . . .
C16 C 0.24973(16) 0.00676(13) -0.03781(12) 0.0264(3) Uani 1 1 d . . . . .
C17 C 0.27819(17) -0.09501(14) -0.02066(13) 0.0337(4) Uani 1 1 d . . . . .
H17A H 0.356381 -0.114013 0.023540 0.040 Uiso 1 1 calc R U . . .
C18 C 0.19216(17) -0.16819(13) -0.06821(14) 0.0329(4) Uani 1 1 d . . . . .
H18A H 0.212026 -0.236013 -0.055659 0.039 Uiso 1 1 calc R U . . .
C19 C 0.07616(16) -0.14019(14) -0.13468(13) 0.0300(4) Uani 1 1 d . . . . .
C20 C 0.04656(18) -0.04002(15) -0.15534(16) 0.0419(5) Uani 1 1 d . . . . .
H20A H -0.030539 -0.021629 -0.201661 0.050 Uiso 1 1 calc R U . . .
C21 C 0.13271(18) 0.03276(14) -0.10648(15) 0.0403(5) Uani 1 1 d . . . . .
H21A H 0.112393 0.100447 -0.119577 0.048 Uiso 1 1 calc R U . . .
C22 C -0.1572(2) -0.21212(19) -0.1544(2) 0.0584(7) Uani 1 1 d . . . . .
H22A H -0.194029 -0.147883 -0.178667 0.088 Uiso 1 1 calc R U . . .
H22B H -0.218802 -0.264058 -0.179042 0.088 Uiso 1 1 calc R U . . .
H22C H -0.125930 -0.211924 -0.084313 0.088 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
Cu1 N2 1.9416(14) . ?
Cu1 N1 2.0399(16) . ?
Cu1 N3 2.0416(15) . ?
Cu1 Cl1 2.2134(5) . ?
Cu1 Cl2 2.5528(5) . ?
S1 O1 1.4324(15) . ?
S1 O2 1.4384(16) . ?
S1 C22 1.754(2) . ?
S1 C19 1.7714(18) . ?
N1 C1 1.337(2) . ?
N1 C5 1.353(2) . ?
N2 C6 1.336(2) . ?
N2 C10 1.337(2) . ?
N3 C15 1.340(2) . ?
N3 C11 1.358(2) . ?
C1 C2 1.375(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2B 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.487(2) . ?
C6 C7 1.384(2) . ?
C7 C8 1.406(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.399(2) . ?
C8 C16 1.486(2) . ?
C9 C10 1.384(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.485(2) . ?
C11 C12 1.375(3) . ?
C12 C13 1.391(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.390(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.379(2) . ?
C17 H17A 0.9300 . ?
C18 C19 1.383(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(3) . ?
C20 C21 1.381(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 79.44(6) . . ?
N2 Cu1 N3 79.41(6) . . ?
N1 Cu1 N3 156.73(6) . . ?
N2 Cu1 Cl1 161.33(5) . . ?
N1 Cu1 Cl1 98.52(5) . . ?
N3 Cu1 Cl1 98.39(4) . . ?
N2 Cu1 Cl2 89.75(5) . . ?
N1 Cu1 Cl2 92.43(5) . . ?
N3 Cu1 Cl2 97.09(5) . . ?
Cl1 Cu1 Cl2 108.91(2) . . ?
O1 S1 O2 117.61(11) . . ?
O1 S1 C22 108.57(12) . . ?
O2 S1 C22 108.51(13) . . ?
O1 S1 C19 108.41(9) . . ?
O2 S1 C19 108.61(9) . . ?
C22 S1 C19 104.32(11) . . ?
C1 N1 C5 118.74(17) . . ?
C1 N1 Cu1 126.97(14) . . ?
C5 N1 Cu1 114.21(12) . . ?
C6 N2 C10 121.51(15) . . ?
C6 N2 Cu1 118.55(11) . . ?
C10 N2 Cu1 118.85(12) . . ?
C15 N3 C11 118.39(16) . . ?
C15 N3 Cu1 127.12(13) . . ?
C11 N3 Cu1 114.48(12) . . ?
N1 C1 C2 122.12(19) . . ?
N1 C1 H1B 118.9 . . ?
C2 C1 H1B 118.9 . . ?
C3 C2 C1 119.37(18) . . ?
C3 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C2 C3 C4 119.28(19) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C3 118.37(18) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
N1 C5 C4 122.12(16) . . ?
N1 C5 C6 113.71(16) . . ?
C4 C5 C6 124.14(16) . . ?
N2 C6 C7 120.85(16) . . ?
N2 C6 C5 112.52(15) . . ?
C7 C6 C5 126.62(16) . . ?
C6 C7 C8 119.29(16) . . ?
C6 C7 H7A 120.4 . . ?
C8 C7 H7A 120.4 . . ?
C9 C8 C7 117.99(15) . . ?
C9 C8 C16 121.22(15) . . ?
C7 C8 C16 120.76(15) . . ?
C10 C9 C8 119.71(16) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 120.57(16) . . ?
N2 C10 C11 112.83(15) . . ?
C9 C10 C11 126.58(16) . . ?
N3 C11 C12 121.99(17) . . ?
N3 C11 C10 113.43(15) . . ?
C12 C11 C10 124.55(16) . . ?
C11 C12 C13 118.97(18) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C14 C13 C12 118.94(19) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C15 C14 C13 119.22(18) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
N3 C15 C14 122.48(18) . . ?
N3 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C17 C16 C21 118.10(16) . . ?
C17 C16 C8 121.00(15) . . ?
C21 C16 C8 120.89(16) . . ?
C18 C17 C16 120.97(16) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 119.66(17) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
C20 C19 C18 120.69(17) . . ?
C20 C19 S1 120.19(14) . . ?
C18 C19 S1 119.12(14) . . ?
C19 C20 C21 119.23(17) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C20 C21 C16 121.31(17) . . ?
C20 C21 H21A 119.3 . . ?
C16 C21 H21A 119.3 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 N1 C1 C2 0.5(3) . . . . ?
Cu1 N1 C1 C2 177.01(16) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C1 N1 C5 C4 -0.6(3) . . . . ?
Cu1 N1 C5 C4 -177.47(15) . . . . ?
C1 N1 C5 C6 -178.78(17) . . . . ?
Cu1 N1 C5 C6 4.30(19) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C3 C4 C5 C6 178.20(18) . . . . ?
C10 N2 C6 C7 -2.1(3) . . . . ?
Cu1 N2 C6 C7 165.88(13) . . . . ?
C10 N2 C6 C5 179.21(16) . . . . ?
Cu1 N2 C6 C5 -12.8(2) . . . . ?
N1 C5 C6 N2 5.0(2) . . . . ?
C4 C5 C6 N2 -173.22(18) . . . . ?
N1 C5 C6 C7 -173.61(17) . . . . ?
C4 C5 C6 C7 8.2(3) . . . . ?
N2 C6 C7 C8 1.5(3) . . . . ?
C5 C6 C7 C8 179.97(16) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C16 -176.85(16) . . . . ?
C7 C8 C9 C10 -2.9(3) . . . . ?
C16 C8 C9 C10 174.92(16) . . . . ?
C6 N2 C10 C9 0.1(3) . . . . ?
Cu1 N2 C10 C9 -167.85(14) . . . . ?
C6 N2 C10 C11 178.40(16) . . . . ?
Cu1 N2 C10 C11 10.4(2) . . . . ?
C8 C9 C10 N2 2.5(3) . . . . ?
C8 C9 C10 C11 -175.58(17) . . . . ?
C15 N3 C11 C12 -0.4(3) . . . . ?
Cu1 N3 C11 C12 178.87(15) . . . . ?
C15 N3 C11 C10 177.77(17) . . . . ?
Cu1 N3 C11 C10 -3.0(2) . . . . ?
N2 C10 C11 N3 -4.4(2) . . . . ?
C9 C10 C11 N3 173.75(18) . . . . ?
N2 C10 C11 C12 173.70(18) . . . . ?
C9 C10 C11 C12 -8.1(3) . . . . ?
N3 C11 C12 C13 0.4(3) . . . . ?
C10 C11 C12 C13 -177.59(19) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C11 N3 C15 C14 0.0(3) . . . . ?
Cu1 N3 C15 C14 -179.17(14) . . . . ?
C13 C14 C15 N3 0.4(3) . . . . ?
C9 C8 C16 C17 175.45(18) . . . . ?
C7 C8 C16 C17 -6.7(3) . . . . ?
C9 C8 C16 C21 -5.5(3) . . . . ?
C7 C8 C16 C21 172.33(18) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C8 C16 C17 C18 177.44(17) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?
C17 C18 C19 S1 -178.60(16) . . . . ?
O1 S1 C19 C20 -178.28(18) . . . . ?
O2 S1 C19 C20 52.9(2) . . . . ?
C22 S1 C19 C20 -62.7(2) . . . . ?
O1 S1 C19 C18 1.6(2) . . . . ?
O2 S1 C19 C18 -127.21(17) . . . . ?
C22 S1 C19 C18 117.21(19) . . . . ?
C18 C19 C20 C21 -2.1(3) . . . . ?
S1 C19 C20 C21 177.80(18) . . . . ?
C19 C20 C21 C16 1.0(4) . . . . ?
C17 C16 C21 C20 0.8(3) . . . . ?
C8 C16 C21 C20 -178.3(2) . . . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_D_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2044625'
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2021-02-08 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         'C42 H30 Cl4 Cu2 F2 N6 O'
_chemical_formula_sum            'C42 H30 Cl4 Cu2 F2 N6 O'
_chemical_formula_weight         941.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.9712(4)
_cell_length_b                   11.3078(5)
_cell_length_c                   17.6171(6)
_cell_angle_alpha                79.386(3)
_cell_angle_beta                 76.853(3)
_cell_angle_gamma                86.680(3)
_cell_volume                     1900.93(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10065
_cell_measurement_theta_min      3.7310
_cell_measurement_theta_max      29.0550

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.455
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            18750
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         29.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8814
_reflns_number_gt                7190
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0433P)²+0.3707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         8814
_refine_ls_number_parameters     522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.14977(3) 0.35379(2) 0.51434(2) 0.03576(8) Uani 1 1 d . . . . .
Cu2 Cu 0.62762(3) 0.06412(2) 0.17279(2) 0.03831(8) Uani 1 1 d . . . . .
Cl1 Cl -0.05813(6) 0.32748(6) 0.59708(3) 0.04944(14) Uani 1 1 d . . . . .
Cl2 Cl 0.29908(6) 0.20770(5) 0.58306(3) 0.04852(14) Uani 1 1 d . . . . .
Cl3 Cl 0.80174(7) 0.14669(7) 0.20606(4) 0.06398(19) Uani 1 1 d . . . . .
Cl4 Cl 0.49014(6) 0.23679(5) 0.12713(3) 0.04649(14) Uani 1 1 d . . . . .
F1 F 0.9425(2) 0.6740(2) 0.04800(11) 0.0987(7) Uani 1 1 d . . . . .
F2 F 0.0886(2) -0.65836(16) 0.12594(11) 0.0884(6) Uani 1 1 d . . . . .
N1 N 0.12230(17) 0.25646(15) 0.43203(10) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.28640(17) 0.42485(14) 0.42169(10) 0.0329(4) Uani 1 1 d . . . . .
N6 N 0.72348(18) 0.03640(15) 0.06215(11) 0.0386(4) Uani 1 1 d . . . . .
N3 N 0.20832(19) 0.49814(16) 0.55293(10) 0.0386(4) Uani 1 1 d . . . . .
N4 N 0.50642(19) 0.02360(16) 0.28364(11) 0.0411(4) Uani 1 1 d . . . . .
N5 N 0.52315(17) -0.07117(15) 0.16240(10) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.0288(2) 0.1704(2) 0.44321(14) 0.0440(5) Uani 1 1 d . . . . .
H1A H -0.030145 0.151010 0.492689 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0172(2) 0.1100(2) 0.38399(15) 0.0497(6) Uani 1 1 d . . . . .
H2A H -0.048737 0.051122 0.393243 0.060 Uiso 1 1 calc R U . . .
C3 C 0.1044(2) 0.1382(2) 0.31119(15) 0.0487(6) Uani 1 1 d . . . . .
H3A H 0.097229 0.099062 0.270280 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2032(2) 0.2249(2) 0.29868(13) 0.0418(5) Uani 1 1 d . . . . .
H4A H 0.263859 0.243980 0.249754 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2098(2) 0.28247(18) 0.36037(12) 0.0340(4) Uani 1 1 d . . . . .
C6 C 0.3089(2) 0.37762(18) 0.35536(12) 0.0332(4) Uani 1 1 d . . . . .
C7 C 0.4145(2) 0.41899(18) 0.29142(12) 0.0363(4) Uani 1 1 d . . . . .
H7A H 0.429186 0.386175 0.245468 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4992(2) 0.51097(18) 0.29657(12) 0.0351(4) Uani 1 1 d . . . . .
C9 C 0.4693(2) 0.56050(18) 0.36556(12) 0.0364(4) Uani 1 1 d . . . . .
H9A H 0.521900 0.622929 0.370304 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3613(2) 0.51648(17) 0.42677(12) 0.0333(4) Uani 1 1 d . . . . .
C11 C 0.3131(2) 0.56077(18) 0.50255(12) 0.0345(4) Uani 1 1 d . . . . .
C12 C 0.3652(2) 0.6600(2) 0.52040(14) 0.0439(5) Uani 1 1 d . . . . .
H12A H 0.438809 0.701516 0.485611 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3050(3) 0.6960(2) 0.59134(15) 0.0531(6) Uani 1 1 d . . . . .
H13A H 0.336458 0.764140 0.603963 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1990(3) 0.6320(2) 0.64338(15) 0.0511(6) Uani 1 1 d . . . . .
H14A H 0.159359 0.654782 0.691751 0.061 Uiso 1 1 calc R U . . .
C15 C 0.1535(3) 0.5337(2) 0.62207(13) 0.0468(5) Uani 1 1 d . . . . .
H15A H 0.081609 0.489886 0.656921 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6175(2) 0.55361(19) 0.23085(13) 0.0379(5) Uani 1 1 d . . . . .
C17 C 0.6817(2) 0.6610(2) 0.22778(14) 0.0458(5) Uani 1 1 d . . . . .
H17A H 0.650849 0.705782 0.267861 0.055 Uiso 1 1 calc R U . . .
C18 C 0.7904(3) 0.7020(2) 0.16618(17) 0.0577(7) Uani 1 1 d . . . . .
H18A H 0.832255 0.774335 0.164021 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8351(3) 0.6341(3) 0.10858(17) 0.0646(7) Uani 1 1 d . . . . .
C20 C 0.7793(3) 0.5258(3) 0.11026(16) 0.0659(7) Uani 1 1 d . . . . .
H20A H 0.814542 0.479670 0.071402 0.079 Uiso 1 1 calc R U . . .
C21 C 0.6685(3) 0.4868(2) 0.17161(15) 0.0524(6) Uani 1 1 d . . . . .
H21A H 0.627578 0.414343 0.173102 0.063 Uiso 1 1 calc R U . . .
C31 C 0.5066(3) 0.0799(2) 0.34347(14) 0.0527(6) Uani 1 1 d . . . . .
H31A H 0.570024 0.140559 0.335809 0.063 Uiso 1 1 calc R U . . .
C32 C 0.4178(3) 0.0530(2) 0.41605(15) 0.0510(6) Uani 1 1 d . . . . .
H32A H 0.420627 0.094478 0.456586 0.061 Uiso 1 1 calc R U . . .
C33 C 0.3249(3) -0.0367(2) 0.42718(13) 0.0464(5) Uani 1 1 d . . . . .
H33A H 0.263897 -0.057322 0.475825 0.056 Uiso 1 1 calc R U . . .
C34 C 0.3224(2) -0.0966(2) 0.36555(13) 0.0429(5) Uani 1 1 d . . . . .
H34A H 0.259978 -0.157660 0.372252 0.051 Uiso 1 1 calc R U . . .
C35 C 0.4138(2) -0.06402(18) 0.29452(12) 0.0351(4) Uani 1 1 d . . . . .
C36 C 0.4233(2) -0.11880(17) 0.22331(12) 0.0333(4) Uani 1 1 d . . . . .
C37 C 0.3445(2) -0.21186(18) 0.21675(12) 0.0357(4) Uani 1 1 d . . . . .
H37A H 0.275150 -0.244400 0.259151 0.043 Uiso 1 1 calc R U . . .
C38 C 0.3703(2) -0.25621(17) 0.14594(12) 0.0340(4) Uani 1 1 d . . . . .
C39 C 0.4746(2) -0.20388(18) 0.08321(12) 0.0358(4) Uani 1 1 d . . . . .
H39A H 0.492635 -0.230630 0.034969 0.043 Uiso 1 1 calc R U . . .
C40 C 0.5504(2) -0.11194(17) 0.09377(12) 0.0336(4) Uani 1 1 d . . . . .
C41 C 0.6679(2) -0.05043(18) 0.03562(12) 0.0361(4) Uani 1 1 d . . . . .
C42 C 0.7191(2) -0.0770(2) -0.03875(14) 0.0467(5) Uani 1 1 d . . . . .
H42A H 0.680544 -0.137369 -0.055876 0.056 Uiso 1 1 calc R U . . .
C43 C 0.8288(3) -0.0124(2) -0.08746(15) 0.0557(6) Uani 1 1 d . . . . .
H43A H 0.865927 -0.029568 -0.137722 0.067 Uiso 1 1 calc R U . . .
C44 C 0.8827(3) 0.0772(2) -0.06135(15) 0.0552(6) Uani 1 1 d . . . . .
H44A H 0.955110 0.122837 -0.094192 0.066 Uiso 1 1 calc R U . . .
C45 C 0.8287(2) 0.0991(2) 0.01385(15) 0.0488(6) Uani 1 1 d . . . . .
H45A H 0.866550 0.159204 0.031667 0.059 Uiso 1 1 calc R U . . .
C46 C 0.2924(2) -0.35987(18) 0.13850(12) 0.0347(4) Uani 1 1 d . . . . .
C47 C 0.3474(2) -0.4336(2) 0.08412(16) 0.0511(6) Uani 1 1 d . . . . .
H47A H 0.432490 -0.415515 0.050130 0.061 Uiso 1 1 calc R U . . .
C48 C 0.2785(3) -0.5336(2) 0.07923(18) 0.0579(7) Uani 1 1 d . . . . .
H48A H 0.316222 -0.582451 0.042364 0.069 Uiso 1 1 calc R U . . .
C49 C 0.1554(3) -0.5588(2) 0.12918(16) 0.0555(7) Uani 1 1 d . . . . .
C50 C 0.0950(3) -0.4879(3) 0.18245(16) 0.0712(9) Uani 1 1 d . . . . .
H50A H 0.008946 -0.506509 0.215174 0.085 Uiso 1 1 calc R U . . .
C51 C 0.1640(3) -0.3871(3) 0.18724(15) 0.0574(7) Uani 1 1 d . . . . .
H51A H 0.123873 -0.337749 0.223320 0.069 Uiso 1 1 calc R U . . .
O1 O 0.9612(4) -0.1077(3) 0.2567(2) 0.1039(10) Uani 1 1 d . . . . .
H01E H 0.892(5) -0.065(4) 0.254(3) 0.12(2) Uiso 1 1 d . . . . .
H01F H 0.942(5) -0.147(4) 0.301(3) 0.138(19) Uiso 1 1 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 N2 1.9488(17) . ?
Cu1 N3 2.0415(18) . ?
Cu1 N1 2.0475(17) . ?
Cu1 Cl1 2.2467(6) . ?
Cu1 Cl2 2.4919(6) . ?
Cu2 N5 1.9579(16) . ?
Cu2 N4 2.0359(19) . ?
Cu2 N6 2.0382(18) . ?
Cu2 Cl3 2.2543(6) . ?
Cu2 Cl4 2.4396(6) . ?
F1 C19 1.360(3) . ?
F2 C49 1.357(3) . ?
N1 C1 1.344(3) . ?
N1 C5 1.354(3) . ?
N2 C10 1.339(3) . ?
N2 C6 1.341(3) . ?
N6 C45 1.336(3) . ?
N6 C41 1.356(3) . ?
N3 C15 1.340(3) . ?
N3 C11 1.346(3) . ?
N4 C31 1.329(3) . ?
N4 C35 1.352(3) . ?
N5 C40 1.338(3) . ?
N5 C36 1.340(3) . ?
C1 C2 1.376(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.370(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.480(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.405(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.395(3) . ?
C8 C16 1.484(3) . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.480(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.381(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.387(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.367(4) . ?
C20 C21 1.386(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C31 C32 1.373(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.370(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.387(3) . ?
C33 H33A 0.9300 . ?
C34 C35 1.372(3) . ?
C34 H34A 0.9300 . ?
C35 C36 1.480(3) . ?
C36 C37 1.386(3) . ?
C37 C38 1.394(3) . ?
C37 H37A 0.9300 . ?
C38 C39 1.400(3) . ?
C38 C46 1.484(3) . ?
C39 C40 1.383(3) . ?
C39 H39A 0.9300 . ?
C40 C41 1.480(3) . ?
C41 C42 1.375(3) . ?
C42 C43 1.378(3) . ?
C42 H42A 0.9300 . ?
C43 C44 1.369(4) . ?
C43 H43A 0.9300 . ?
C44 C45 1.374(4) . ?
C44 H44A 0.9300 . ?
C45 H45A 0.9300 . ?
C46 C47 1.384(3) . ?
C46 C51 1.385(3) . ?
C47 C48 1.382(3) . ?
C47 H47A 0.9300 . ?
C48 C49 1.349(4) . ?
C48 H48A 0.9300 . ?
C49 C50 1.360(4) . ?
C50 C51 1.390(4) . ?
C50 H50A 0.9300 . ?
C51 H51A 0.9300 . ?
O1 H01E 0.82(4) . ?
O1 H01F 0.81(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 79.03(7) . . ?
N2 Cu1 N1 78.76(7) . . ?
N3 Cu1 N1 155.85(7) . . ?
N2 Cu1 Cl1 157.19(5) . . ?
N3 Cu1 Cl1 97.98(6) . . ?
N1 Cu1 Cl1 98.81(5) . . ?
N2 Cu1 Cl2 99.94(5) . . ?
N3 Cu1 Cl2 94.18(5) . . ?
N1 Cu1 Cl2 98.85(5) . . ?
Cl1 Cu1 Cl2 102.84(2) . . ?
N5 Cu2 N4 78.57(7) . . ?
N5 Cu2 N6 79.07(7) . . ?
N4 Cu2 N6 156.64(7) . . ?
N5 Cu2 Cl3 153.85(5) . . ?
N4 Cu2 Cl3 97.47(5) . . ?
N6 Cu2 Cl3 99.61(5) . . ?
N5 Cu2 Cl4 102.08(5) . . ?
N4 Cu2 Cl4 96.09(5) . . ?
N6 Cu2 Cl4 95.11(5) . . ?
Cl3 Cu2 Cl4 104.04(3) . . ?
C1 N1 C5 118.55(19) . . ?
C1 N1 Cu1 126.34(15) . . ?
C5 N1 Cu1 115.10(13) . . ?
C10 N2 C6 121.03(17) . . ?
C10 N2 Cu1 119.18(14) . . ?
C6 N2 Cu1 119.70(13) . . ?
C45 N6 C41 118.8(2) . . ?
C45 N6 Cu2 126.08(16) . . ?
C41 N6 Cu2 115.00(14) . . ?
C15 N3 C11 118.92(19) . . ?
C15 N3 Cu1 126.33(16) . . ?
C11 N3 Cu1 114.75(14) . . ?
C31 N4 C35 118.5(2) . . ?
C31 N4 Cu2 125.49(16) . . ?
C35 N4 Cu2 115.92(14) . . ?
C40 N5 C36 121.35(17) . . ?
C40 N5 Cu2 119.22(14) . . ?
C36 N5 Cu2 119.40(14) . . ?
N1 C1 C2 122.3(2) . . ?
N1 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
N1 C5 C4 121.77(19) . . ?
N1 C5 C6 113.68(18) . . ?
C4 C5 C6 124.54(19) . . ?
N2 C6 C7 120.73(18) . . ?
N2 C6 C5 112.39(18) . . ?
C7 C6 C5 126.87(19) . . ?
C6 C7 C8 119.45(19) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C9 C8 C7 117.97(19) . . ?
C9 C8 C16 121.00(19) . . ?
C7 C8 C16 121.03(19) . . ?
C10 C9 C8 119.75(19) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 120.94(19) . . ?
N2 C10 C11 112.32(18) . . ?
C9 C10 C11 126.74(19) . . ?
N3 C11 C12 121.7(2) . . ?
N3 C11 C10 114.14(18) . . ?
C12 C11 C10 124.1(2) . . ?
C11 C12 C13 118.2(2) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C15 C14 C13 118.1(2) . . ?
C15 C14 H14A 120.9 . . ?
C13 C14 H14A 120.9 . . ?
N3 C15 C14 122.6(2) . . ?
N3 C15 H15A 118.7 . . ?
C14 C15 H15A 118.7 . . ?
C21 C16 C17 118.2(2) . . ?
C21 C16 C8 121.0(2) . . ?
C17 C16 C8 120.8(2) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H18A 120.8 . . ?
C17 C18 H18A 120.8 . . ?
F1 C19 C18 118.7(3) . . ?
F1 C19 C20 118.4(3) . . ?
C18 C19 C20 122.9(3) . . ?
C19 C20 C21 118.0(3) . . ?
C19 C20 H20A 121.0 . . ?
C21 C20 H20A 121.0 . . ?
C20 C21 C16 121.4(2) . . ?
C20 C21 H21A 119.3 . . ?
C16 C21 H21A 119.3 . . ?
N4 C31 C32 123.2(2) . . ?
N4 C31 H31A 118.4 . . ?
C32 C31 H31A 118.4 . . ?
C33 C32 C31 118.2(2) . . ?
C33 C32 H32A 120.9 . . ?
C31 C32 H32A 120.9 . . ?
C32 C33 C34 119.7(2) . . ?
C32 C33 H33A 120.2 . . ?
C34 C33 H33A 120.2 . . ?
C35 C34 C33 118.7(2) . . ?
C35 C34 H34A 120.6 . . ?
C33 C34 H34A 120.6 . . ?
N4 C35 C34 121.69(19) . . ?
N4 C35 C36 113.19(18) . . ?
C34 C35 C36 125.12(19) . . ?
N5 C36 C37 120.70(19) . . ?
N5 C36 C35 112.69(17) . . ?
C37 C36 C35 126.58(19) . . ?
C36 C37 C38 119.32(19) . . ?
C36 C37 H37A 120.3 . . ?
C38 C37 H37A 120.3 . . ?
C37 C38 C39 118.59(18) . . ?
C37 C38 C46 120.53(18) . . ?
C39 C38 C46 120.83(19) . . ?
C40 C39 C38 119.27(19) . . ?
C40 C39 H39A 120.4 . . ?
C38 C39 H39A 120.4 . . ?
N5 C40 C39 120.76(19) . . ?
N5 C40 C41 112.65(17) . . ?
C39 C40 C41 126.58(19) . . ?
N6 C41 C42 121.6(2) . . ?
N6 C41 C40 113.87(18) . . ?
C42 C41 C40 124.5(2) . . ?
C41 C42 C43 118.8(2) . . ?
C41 C42 H42A 120.6 . . ?
C43 C42 H42A 120.6 . . ?
C44 C43 C42 119.6(2) . . ?
C44 C43 H43A 120.2 . . ?
C42 C43 H43A 120.2 . . ?
C43 C44 C45 119.3(2) . . ?
C43 C44 H44A 120.4 . . ?
C45 C44 H44A 120.3 . . ?
N6 C45 C44 121.9(2) . . ?
N6 C45 H45A 119.1 . . ?
C44 C45 H45A 119.1 . . ?
C47 C46 C51 118.2(2) . . ?
C47 C46 C38 121.0(2) . . ?
C51 C46 C38 120.8(2) . . ?
C48 C47 C46 121.5(2) . . ?
C48 C47 H47A 119.3 . . ?
C46 C47 H47A 119.3 . . ?
C49 C48 C47 118.5(3) . . ?
C49 C48 H48A 120.8 . . ?
C47 C48 H48A 120.8 . . ?
C48 C49 F2 118.8(3) . . ?
C48 C49 C50 122.5(2) . . ?
F2 C49 C50 118.6(3) . . ?
C49 C50 C51 119.0(3) . . ?
C49 C50 H50A 120.5 . . ?
C51 C50 H50A 120.5 . . ?
C46 C51 C50 120.3(3) . . ?
C46 C51 H51A 119.9 . . ?
C50 C51 H51A 119.9 . . ?
H01E O1 H01F 103(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
C5 N1 C1 C2 -1.4(3) . . . . ?
Cu1 N1 C1 C2 179.56(17) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C1 N1 C5 C4 1.4(3) . . . . ?
Cu1 N1 C5 C4 -179.51(15) . . . . ?
C1 N1 C5 C6 -179.37(17) . . . . ?
Cu1 N1 C5 C6 -0.2(2) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C6 -179.39(19) . . . . ?
C10 N2 C6 C7 2.9(3) . . . . ?
Cu1 N2 C6 C7 -173.70(14) . . . . ?
C10 N2 C6 C5 -176.51(16) . . . . ?
Cu1 N2 C6 C5 6.9(2) . . . . ?
N1 C5 C6 N2 -4.0(2) . . . . ?
C4 C5 C6 N2 175.19(18) . . . . ?
N1 C5 C6 C7 176.64(18) . . . . ?
C4 C5 C6 C7 -4.1(3) . . . . ?
N2 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 179.68(18) . . . . ?
C6 C7 C8 C9 -2.6(3) . . . . ?
C6 C7 C8 C16 177.04(17) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
C16 C8 C9 C10 -177.98(17) . . . . ?
C6 N2 C10 C9 -3.8(3) . . . . ?
Cu1 N2 C10 C9 172.73(14) . . . . ?
C6 N2 C10 C11 175.77(16) . . . . ?
Cu1 N2 C10 C11 -7.7(2) . . . . ?
C8 C9 C10 N2 1.5(3) . . . . ?
C8 C9 C10 C11 -178.03(17) . . . . ?
C15 N3 C11 C12 0.1(3) . . . . ?
Cu1 N3 C11 C12 -179.43(15) . . . . ?
C15 N3 C11 C10 -177.48(17) . . . . ?
Cu1 N3 C11 C10 3.0(2) . . . . ?
N2 C10 C11 N3 2.7(2) . . . . ?
C9 C10 C11 N3 -177.70(18) . . . . ?
N2 C10 C11 C12 -174.82(18) . . . . ?
C9 C10 C11 C12 4.8(3) . . . . ?
N3 C11 C12 C13 -1.4(3) . . . . ?
C10 C11 C12 C13 176.01(19) . . . . ?
C11 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 C15 -1.4(4) . . . . ?
C11 N3 C15 C14 0.5(3) . . . . ?
Cu1 N3 C15 C14 -179.98(17) . . . . ?
C13 C14 C15 N3 0.1(4) . . . . ?
C9 C8 C16 C21 163.9(2) . . . . ?
C7 C8 C16 C21 -15.7(3) . . . . ?
C9 C8 C16 C17 -15.0(3) . . . . ?
C7 C8 C16 C17 165.41(19) . . . . ?
C21 C16 C17 C18 2.0(3) . . . . ?
C8 C16 C17 C18 -179.0(2) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 F1 -179.7(2) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
F1 C19 C20 C21 -179.1(3) . . . . ?
C18 C19 C20 C21 2.9(5) . . . . ?
C19 C20 C21 C16 -1.6(4) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C8 C16 C21 C20 -179.7(2) . . . . ?
C35 N4 C31 C32 0.4(4) . . . . ?
Cu2 N4 C31 C32 176.60(18) . . . . ?
N4 C31 C32 C33 0.2(4) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C31 N4 C35 C34 -0.9(3) . . . . ?
Cu2 N4 C35 C34 -177.44(16) . . . . ?
C31 N4 C35 C36 179.47(19) . . . . ?
Cu2 N4 C35 C36 2.9(2) . . . . ?
C33 C34 C35 N4 0.7(3) . . . . ?
C33 C34 C35 C36 -179.70(19) . . . . ?
C40 N5 C36 C37 -0.3(3) . . . . ?
Cu2 N5 C36 C37 177.77(14) . . . . ?
C40 N5 C36 C35 177.77(17) . . . . ?
Cu2 N5 C36 C35 -4.1(2) . . . . ?
N4 C35 C36 N5 0.6(2) . . . . ?
C34 C35 C36 N5 -179.02(19) . . . . ?
N4 C35 C36 C37 178.58(19) . . . . ?
C34 C35 C36 C37 -1.1(3) . . . . ?
N5 C36 C37 C38 0.2(3) . . . . ?
C35 C36 C37 C38 -177.59(18) . . . . ?
C36 C37 C38 C39 -0.7(3) . . . . ?
C36 C37 C38 C46 176.88(17) . . . . ?
C37 C38 C39 C40 1.3(3) . . . . ?
C46 C38 C39 C40 -176.29(18) . . . . ?
C36 N5 C40 C39 0.9(3) . . . . ?
Cu2 N5 C40 C39 -177.16(14) . . . . ?
C36 N5 C40 C41 -177.69(17) . . . . ?
Cu2 N5 C40 C41 4.2(2) . . . . ?
C38 C39 C40 N5 -1.4(3) . . . . ?
C38 C39 C40 C41 176.99(18) . . . . ?
C45 N6 C41 C42 1.5(3) . . . . ?
Cu2 N6 C41 C42 178.21(16) . . . . ?
C45 N6 C41 C40 -178.88(18) . . . . ?
Cu2 N6 C41 C40 -2.1(2) . . . . ?
N5 C40 C41 N6 -1.2(2) . . . . ?
C39 C40 C41 N6 -179.71(19) . . . . ?
N5 C40 C41 C42 178.5(2) . . . . ?
C39 C40 C41 C42 -0.1(3) . . . . ?
N6 C41 C42 C43 -0.7(3) . . . . ?
C40 C41 C42 C43 179.7(2) . . . . ?
C41 C42 C43 C44 -0.9(4) . . . . ?
C42 C43 C44 C45 1.7(4) . . . . ?
C41 N6 C45 C44 -0.6(3) . . . . ?
Cu2 N6 C45 C44 -176.97(18) . . . . ?
C43 C44 C45 N6 -1.0(4) . . . . ?
C37 C38 C46 C47 -154.8(2) . . . . ?
C39 C38 C46 C47 22.7(3) . . . . ?
C37 C38 C46 C51 23.5(3) . . . . ?
C39 C38 C46 C51 -158.9(2) . . . . ?
C51 C46 C47 C48 -1.5(3) . . . . ?
C38 C46 C47 C48 176.9(2) . . . . ?
C46 C47 C48 C49 -0.2(4) . . . . ?
C47 C48 C49 F2 -178.5(2) . . . . ?
C47 C48 C49 C50 1.8(4) . . . . ?
C48 C49 C50 C51 -1.7(4) . . . . ?
F2 C49 C50 C51 178.7(2) . . . . ?
C47 C46 C51 C50 1.6(4) . . . . ?
C38 C46 C51 C50 -176.8(2) . . . . ?
C49 C50 C51 C46 -0.1(4) . . . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.085



####################################################################### 
# 
# 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_E
_database_code_depnum_ccdc_archive 'CCDC 2044629'
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2021-02-08 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         'C25 H21 Cl2 Cu N5 O'
_chemical_formula_sum            'C25 H21 Cl2 Cu N5 O'
_chemical_formula_weight         541.92

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      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                   7.3829(8)
_cell_length_b                   26.310(2)
_cell_length_c                   12.513(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.947(11)
_cell_angle_gamma                90
_cell_volume                     2348.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6272
_cell_measurement_theta_min      3.3930
_cell_measurement_theta_max      29.2660

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.187
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            15003
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         29.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5575
_reflns_number_gt                4390
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0484P)²+0.7799P] 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_number_reflns         5575
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.27499(4) -0.09858(2) 0.71503(2) 0.03868(11) Uani 1 1 d . . . . .
Cl1 Cl 0.27641(12) -0.18006(3) 0.76456(6) 0.0588(2) Uani 1 1 d . . . . .
Cl2 Cl 0.00017(9) -0.05832(2) 0.76422(5) 0.04463(16) Uani 1 1 d . . . . .
O1 O 0.8085(4) 0.38918(9) 0.3725(2) 0.0766(7) Uani 1 1 d . . . . .
N1 N 0.1456(3) -0.10619(7) 0.55064(17) 0.0367(4) Uani 1 1 d . . . . .
N2 N 0.3508(3) -0.03566(7) 0.65555(16) 0.0351(4) Uani 1 1 d . . . . .
N3 N 0.4727(3) -0.07252(8) 0.84758(17) 0.0402(5) Uani 1 1 d . . . . .
N4 N 0.4515(6) 0.30132(12) 0.3891(3) 0.0941(11) Uani 1 1 d . . . . .
N5 N 0.9745(4) 0.32727(10) 0.4773(2) 0.0596(6) Uani 1 1 d . . . . .
C1 C 0.0557(4) -0.14719(10) 0.5015(2) 0.0437(6) Uani 1 1 d . . . . .
H1A H 0.047793 -0.175674 0.544092 0.052 Uiso 1 1 calc R U . . .
C2 C -0.0261(4) -0.14861(11) 0.3894(2) 0.0494(7) Uani 1 1 d . . . . .
H2A H -0.087431 -0.177745 0.356585 0.059 Uiso 1 1 calc R U . . .
C3 C -0.0158(4) -0.10651(10) 0.3269(2) 0.0480(6) Uani 1 1 d . . . . .
H3A H -0.069547 -0.106959 0.250982 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0746(3) -0.06343(10) 0.3767(2) 0.0403(5) Uani 1 1 d . . . . .
H4A H 0.080713 -0.034333 0.335532 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1555(3) -0.06461(9) 0.48878(19) 0.0336(5) Uani 1 1 d . . . . .
C6 C 0.2666(3) -0.02257(9) 0.55178(19) 0.0336(5) Uani 1 1 d . . . . .
C7 C 0.2897(3) 0.02554(9) 0.5126(2) 0.0346(5) Uani 1 1 d . . . . .
H7A H 0.227808 0.034667 0.440680 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4066(3) 0.06022(9) 0.5820(2) 0.0353(5) Uani 1 1 d . . . . .
C9 C 0.4984(3) 0.04474(9) 0.6892(2) 0.0374(5) Uani 1 1 d . . . . .
H9A H 0.579849 0.066699 0.736743 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4665(3) -0.00380(9) 0.7236(2) 0.0361(5) Uani 1 1 d . . . . .
C11 C 0.5456(3) -0.02654(9) 0.8342(2) 0.0378(5) Uani 1 1 d . . . . .
C12 C 0.6811(4) -0.00376(10) 0.9176(2) 0.0457(6) Uani 1 1 d . . . . .
H12A H 0.731922 0.027558 0.906678 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7392(4) -0.02889(12) 1.0180(2) 0.0552(7) Uani 1 1 d . . . . .
H13A H 0.829856 -0.014498 1.075812 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6624(4) -0.07496(12) 1.0313(2) 0.0569(7) Uani 1 1 d . . . . .
H14A H 0.700020 -0.092056 1.098488 0.068 Uiso 1 1 calc R U . . .
C15 C 0.5297(4) -0.09581(10) 0.9452(2) 0.0498(6) Uani 1 1 d . . . . .
H15A H 0.477889 -0.127123 0.955087 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4309(3) 0.11266(9) 0.5428(2) 0.0374(5) Uani 1 1 d . . . . .
C17 C 0.5080(4) 0.15180(10) 0.6157(2) 0.0492(6) Uani 1 1 d . . . . .
H17A H 0.552999 0.144852 0.690771 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5182(4) 0.20041(11) 0.5780(3) 0.0544(7) Uani 1 1 d . . . . .
H18A H 0.568346 0.226201 0.627625 0.065 Uiso 1 1 calc R U . . .
C19 C 0.4542(4) 0.21126(10) 0.4663(3) 0.0484(6) Uani 1 1 d . . . . .
C20 C 0.3803(4) 0.17294(10) 0.3933(2) 0.0498(6) Uani 1 1 d . . . . .
H20A H 0.338254 0.179998 0.318145 0.060 Uiso 1 1 calc R U . . .
C21 C 0.3681(4) 0.12427(10) 0.4308(2) 0.0461(6) Uani 1 1 d . . . . .
H21A H 0.317292 0.098744 0.380581 0.055 Uiso 1 1 calc R U . . .
C22 C 0.4572(5) 0.26280(12) 0.4231(3) 0.0619(8) Uani 1 1 d . . . . .
C31 C 0.8992(5) 0.37318(12) 0.4608(3) 0.0574(7) Uani 1 1 d . . . . .
H31A H 0.917208 0.394729 0.521539 0.069 Uiso 1 1 calc R U . . .
C32 C 0.9439(6) 0.29167(14) 0.3877(4) 0.0910(13) Uani 1 1 d . . . . .
H32A H 1.007713 0.260446 0.413356 0.136 Uiso 1 1 calc R U . . .
H32B H 0.812055 0.285256 0.360469 0.136 Uiso 1 1 calc R U . . .
H32C H 0.991593 0.305464 0.329346 0.136 Uiso 1 1 calc R U . . .
C33 C 1.0830(7) 0.31228(19) 0.5854(4) 0.1081(17) Uani 1 1 d . . . . .
H33A H 1.126775 0.278077 0.582601 0.162 Uiso 1 1 calc R U . . .
H33B H 1.188351 0.334685 0.609207 0.162 Uiso 1 1 calc R U . . .
H33C H 1.006248 0.314086 0.636667 0.162 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
Cu1 N2 1.9552(19) . ?
Cu1 N3 2.025(2) . ?
Cu1 N1 2.042(2) . ?
Cu1 Cl1 2.2308(7) . ?
Cu1 Cl2 2.5023(7) . ?
O1 C31 1.210(4) . ?
N1 C1 1.331(3) . ?
N1 C5 1.353(3) . ?
N2 C6 1.332(3) . ?
N2 C10 1.335(3) . ?
N3 C15 1.334(3) . ?
N3 C11 1.352(3) . ?
N4 C22 1.096(4) . ?
N5 C31 1.324(4) . ?
N5 C32 1.433(5) . ?
N5 C33 1.439(5) . ?
C1 C2 1.378(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.478(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.395(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.398(3) . ?
C8 C16 1.490(3) . ?
C9 C10 1.388(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.482(3) . ?
C11 C12 1.382(4) . ?
C12 C13 1.386(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.393(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.372(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.385(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.375(4) . ?
C19 C22 1.462(4) . ?
C20 C21 1.374(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 78.96(8) . . ?
N2 Cu1 N1 78.76(8) . . ?
N3 Cu1 N1 155.39(8) . . ?
N2 Cu1 Cl1 159.73(6) . . ?
N3 Cu1 Cl1 98.46(6) . . ?
N1 Cu1 Cl1 98.80(6) . . ?
N2 Cu1 Cl2 93.74(6) . . ?
N3 Cu1 Cl2 96.54(6) . . ?
N1 Cu1 Cl2 95.22(6) . . ?
Cl1 Cu1 Cl2 106.53(3) . . ?
C1 N1 C5 119.0(2) . . ?
C1 N1 Cu1 126.35(18) . . ?
C5 N1 Cu1 114.62(15) . . ?
C6 N2 C10 121.4(2) . . ?
C6 N2 Cu1 118.83(16) . . ?
C10 N2 Cu1 119.17(16) . . ?
C15 N3 C11 118.8(2) . . ?
C15 N3 Cu1 125.80(19) . . ?
C11 N3 Cu1 115.32(16) . . ?
C31 N5 C32 120.0(3) . . ?
C31 N5 C33 120.4(3) . . ?
C32 N5 C33 119.6(3) . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C6 113.9(2) . . ?
C4 C5 C6 124.2(2) . . ?
N2 C6 C7 120.8(2) . . ?
N2 C6 C5 112.5(2) . . ?
C7 C6 C5 126.7(2) . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 C16 120.6(2) . . ?
C9 C8 C16 121.0(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
N2 C10 C9 120.8(2) . . ?
N2 C10 C11 112.1(2) . . ?
C9 C10 C11 127.1(2) . . ?
N3 C11 C12 121.9(2) . . ?
N3 C11 C10 113.7(2) . . ?
C12 C11 C10 124.4(2) . . ?
C11 C12 C13 118.2(3) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
N3 C15 C14 122.0(3) . . ?
N3 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C21 C16 C17 118.0(2) . . ?
C21 C16 C8 119.8(2) . . ?
C17 C16 C8 122.1(2) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 C22 118.4(3) . . ?
C18 C19 C22 122.0(3) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C20 C21 C16 120.9(3) . . ?
C20 C21 H21A 119.5 . . ?
C16 C21 H21A 119.5 . . ?
N4 C22 C19 177.0(4) . . ?
O1 C31 N5 124.8(3) . . ?
O1 C31 H31A 117.6 . . ?
N5 C31 H31A 117.6 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N5 C33 H33A 109.5 . . ?
N5 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N5 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C5 N1 C1 C2 0.6(4) . . . . ?
Cu1 N1 C1 C2 -179.49(19) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C1 N1 C5 C4 0.3(3) . . . . ?
Cu1 N1 C5 C4 -179.65(17) . . . . ?
C1 N1 C5 C6 -177.2(2) . . . . ?
Cu1 N1 C5 C6 2.9(2) . . . . ?
C3 C4 C5 N1 -1.2(4) . . . . ?
C3 C4 C5 C6 176.0(2) . . . . ?
C10 N2 C6 C7 -3.0(3) . . . . ?
Cu1 N2 C6 C7 167.98(16) . . . . ?
C10 N2 C6 C5 176.0(2) . . . . ?
Cu1 N2 C6 C5 -13.0(2) . . . . ?
N1 C5 C6 N2 6.1(3) . . . . ?
C4 C5 C6 N2 -171.3(2) . . . . ?
N1 C5 C6 C7 -175.0(2) . . . . ?
C4 C5 C6 C7 7.6(4) . . . . ?
N2 C6 C7 C8 1.7(3) . . . . ?
C5 C6 C7 C8 -177.2(2) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C8 C16 -178.7(2) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C16 C8 C9 C10 177.6(2) . . . . ?
C6 N2 C10 C9 1.9(3) . . . . ?
Cu1 N2 C10 C9 -169.05(17) . . . . ?
C6 N2 C10 C11 -179.3(2) . . . . ?
Cu1 N2 C10 C11 9.7(3) . . . . ?
C8 C9 C10 N2 0.5(3) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C15 N3 C11 C12 1.9(4) . . . . ?
Cu1 N3 C11 C12 179.69(19) . . . . ?
C15 N3 C11 C10 -178.0(2) . . . . ?
Cu1 N3 C11 C10 -0.2(3) . . . . ?
N2 C10 C11 N3 -5.9(3) . . . . ?
C9 C10 C11 N3 172.8(2) . . . . ?
N2 C10 C11 C12 174.3(2) . . . . ?
C9 C10 C11 C12 -7.0(4) . . . . ?
N3 C11 C12 C13 -1.4(4) . . . . ?
C10 C11 C12 C13 178.5(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C11 N3 C15 C14 -1.3(4) . . . . ?
Cu1 N3 C15 C14 -178.8(2) . . . . ?
C13 C14 C15 N3 0.2(5) . . . . ?
C7 C8 C16 C21 -12.9(3) . . . . ?
C9 C8 C16 C21 167.7(2) . . . . ?
C7 C8 C16 C17 164.2(2) . . . . ?
C9 C8 C16 C17 -15.1(3) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
C8 C16 C17 C18 -176.0(2) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C17 C18 C19 C22 178.1(3) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C22 C19 C20 C21 -177.5(3) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?
C17 C16 C21 C20 -0.6(4) . . . . ?
C8 C16 C21 C20 176.7(2) . . . . ?
C32 N5 C31 O1 -2.9(5) . . . . ?
C33 N5 C31 O1 178.8(4) . . . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_Z
_database_code_depnum_ccdc_archive 'CCDC 2044628'
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2021-02-08 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         'C22 H18 Cl2 Cu N3 O1.50'
_chemical_formula_sum            'C22 H18 Cl2 Cu N3 O1.50'
_chemical_formula_weight         482.83

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'
Cl Cl 0.1484 0.1585 '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                   12.9439(13)
_cell_length_b                   13.6561(8)
_cell_length_c                   13.1523(16)
_cell_angle_alpha                90
_cell_angle_beta                 118.661(14)
_cell_angle_gamma                90
_cell_volume                     2040.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      3.4850
_cell_measurement_theta_max      28.1700

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.354
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            11109
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         29.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4794
_reflns_number_gt                2621
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0833P)²+1.8285P] 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_number_reflns         4794
_refine_ls_number_parameters     280
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
Cu1 Cu 0.52478(4) 0.07254(4) 0.15809(5) 0.0441(2) Uani 1 1 d . . . . .
Cl1 Cl 0.52226(10) 0.09304(8) 0.34934(11) 0.0502(3) Uani 1 1 d . . . . .
Cl2 Cl 0.71831(9) 0.07083(9) 0.22332(11) 0.0542(3) Uani 1 1 d . . . . .
O1 O -0.2535(3) -0.1147(3) -0.2673(4) 0.0898(15) Uani 1 1 d . . . . .
H1A H -0.324856 -0.107269 -0.306061 0.135 Uiso 1 1 calc R U . . .
N1 N 0.4960(3) -0.0752(3) 0.1411(3) 0.0464(9) Uani 1 1 d . . . . .
N2 N 0.3557(3) 0.0696(2) 0.0584(3) 0.0403(8) Uani 1 1 d . . . . .
N3 N 0.4912(3) 0.2166(3) 0.1149(3) 0.0436(9) Uani 1 1 d . . . . .
C1 C 0.5762(4) -0.1464(4) 0.1852(5) 0.0587(14) Uani 1 1 d . . . . .
H1B H 0.655676 -0.130020 0.224846 0.070 Uiso 1 1 calc R U . . .
C2 C 0.5445(4) -0.2420(4) 0.1735(5) 0.0592(14) Uani 1 1 d . . . . .
H2A H 0.602622 -0.289866 0.204911 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4306(5) -0.2691(4) 0.1174(5) 0.0636(15) Uani 1 1 d . . . . .
H3A H 0.409654 -0.334896 0.110844 0.076 Uiso 1 1 calc R U . . .
C4 C 0.3455(4) -0.1971(3) 0.0697(5) 0.0554(13) Uani 1 1 d . . . . .
H4A H 0.266023 -0.213342 0.029294 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3810(4) -0.1005(3) 0.0834(4) 0.0427(10) Uani 1 1 d . . . . .
C6 C 0.2993(4) -0.0160(3) 0.0349(4) 0.0403(10) Uani 1 1 d . . . . .
C7 C 0.1778(4) -0.0195(3) -0.0290(4) 0.0420(10) Uani 1 1 d . . . . .
H7A H 0.139312 -0.079515 -0.043595 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1133(3) 0.0657(3) -0.0716(4) 0.0358(9) Uani 1 1 d . . . . .
C9 C 0.1756(3) 0.1534(3) -0.0479(4) 0.0392(10) Uani 1 1 d . . . . .
H9A H 0.135547 0.212173 -0.075809 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2972(4) 0.1529(3) 0.0173(4) 0.0378(10) Uani 1 1 d . . . . .
C11 C 0.3759(3) 0.2393(3) 0.0506(4) 0.0389(10) Uani 1 1 d . . . . .
C12 C 0.3378(4) 0.3338(3) 0.0189(4) 0.0469(11) Uani 1 1 d . . . . .
H12A H 0.258124 0.347412 -0.026561 0.056 Uiso 1 1 calc R U . . .
C13 C 0.4211(4) 0.4094(3) 0.0562(4) 0.0534(12) Uani 1 1 d . . . . .
H13A H 0.397705 0.474105 0.036032 0.064 Uiso 1 1 calc R U . . .
C14 C 0.5363(4) 0.3866(4) 0.1224(5) 0.0571(13) Uani 1 1 d . . . . .
H14A H 0.592855 0.435827 0.149018 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5696(4) 0.2905(4) 0.1500(4) 0.0521(12) Uani 1 1 d . . . . .
H15A H 0.649228 0.276023 0.194608 0.063 Uiso 1 1 calc R U . . .
C16 C -0.0174(3) 0.0634(3) -0.1417(3) 0.0356(9) Uani 1 1 d . . . . .
C17 C -0.0773(4) -0.0244(3) -0.1754(4) 0.0450(11) Uani 1 1 d . . . . .
H17A H -0.035836 -0.083045 -0.154061 0.054 Uiso 1 1 calc R U . . .
C18 C -0.1997(4) -0.0256(3) -0.2411(4) 0.0503(12) Uani 1 1 d . . . . .
C19 C -0.2623(4) 0.0593(3) -0.2764(4) 0.0506(12) Uani 1 1 d . . . . .
H19A H -0.343678 0.057867 -0.322598 0.061 Uiso 1 1 calc R U . . .
C20 C -0.2037(4) 0.1468(4) -0.2427(5) 0.0561(13) Uani 1 1 d . . . . .
H20A H -0.246063 0.205024 -0.265504 0.067 Uiso 1 1 calc R U . . .
C21 C -0.0818(4) 0.1501(3) -0.1749(4) 0.0491(12) Uani 1 1 d . . . . .
H21A H -0.043424 0.210062 -0.151776 0.059 Uiso 1 1 calc R U . . .
O2 O 0.6913(7) -0.0962(5) 0.4522(7) 0.076(2) Uani 0.5 1 d D . P . .
H2B H 0.700741 -0.041078 0.480103 0.114 Uiso 0.5 1 calc R U P . .
C23 C 0.5933(9) -0.1429(7) 0.4565(10) 0.103(6) Uani 0.5 1 d D . P . .
H23A H 0.617504 -0.138067 0.538484 0.123 Uiso 0.5 1 calc R U P . .
H23B H 0.532739 -0.093302 0.420499 0.123 Uiso 0.5 1 calc R U P . .
C22 C 0.5265(11) -0.2268(9) 0.4272(13) 0.121(6) Uani 0.5 1 d D . P . .
H22A H 0.467241 -0.220947 0.450878 0.181 Uiso 0.5 1 calc R U P . .
H22B H 0.489541 -0.236080 0.344830 0.181 Uiso 0.5 1 calc R U P . .
H22C H 0.576182 -0.281836 0.465426 0.181 Uiso 0.5 1 calc R U P . .


_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 N2 1.938(3) . ?
Cu1 N3 2.036(4) . ?
Cu1 N1 2.044(4) . ?
Cu1 Cl2 2.2250(12) . ?
Cu1 Cl1 2.5465(14) . ?
O1 C18 1.362(5) . ?
O1 H1A 0.8200 . ?
N1 C1 1.335(6) . ?
N1 C5 1.351(6) . ?
N2 C10 1.329(5) . ?
N2 C6 1.334(5) . ?
N3 C15 1.347(6) . ?
N3 C11 1.352(5) . ?
C1 C2 1.355(7) . ?
C1 H1B 0.9300 . ?
C2 C3 1.346(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.487(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.384(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.393(5) . ?
C8 C16 1.489(5) . ?
C9 C10 1.385(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.481(6) . ?
C11 C12 1.374(6) . ?
C12 C13 1.400(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.354(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(7) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(6) . ?
C16 C21 1.392(6) . ?
C17 C18 1.393(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.362(6) . ?
C19 C20 1.371(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.392(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
O2 C23 1.4442(10) . ?
O2 H2B 0.8200 . ?
C23 C22 1.3743(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 79.06(13) . . ?
N2 Cu1 N1 79.54(14) . . ?
N3 Cu1 N1 156.88(15) . . ?
N2 Cu1 Cl2 163.25(12) . . ?
N3 Cu1 Cl2 99.67(10) . . ?
N1 Cu1 Cl2 98.29(11) . . ?
N2 Cu1 Cl1 97.21(12) . . ?
N3 Cu1 Cl1 93.86(11) . . ?
N1 Cu1 Cl1 97.40(12) . . ?
Cl2 Cu1 Cl1 99.54(5) . . ?
C18 O1 H1A 109.5 . . ?
C1 N1 C5 118.4(4) . . ?
C1 N1 Cu1 127.5(3) . . ?
C5 N1 Cu1 114.1(3) . . ?
C10 N2 C6 120.9(3) . . ?
C10 N2 Cu1 119.7(3) . . ?
C6 N2 Cu1 119.3(3) . . ?
C15 N3 C11 117.9(4) . . ?
C15 N3 Cu1 127.1(3) . . ?
C11 N3 Cu1 114.8(3) . . ?
N1 C1 C2 121.5(5) . . ?
N1 C1 H1B 119.3 . . ?
C2 C1 H1B 119.3 . . ?
C3 C2 C1 121.3(5) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 118.6(5) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 C6 114.0(4) . . ?
C4 C5 C6 124.2(4) . . ?
N2 C6 C7 120.5(4) . . ?
N2 C6 C5 112.5(4) . . ?
C7 C6 C5 127.0(4) . . ?
C6 C7 C8 120.4(4) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C9 117.4(4) . . ?
C7 C8 C16 121.3(4) . . ?
C9 C8 C16 121.3(3) . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
N2 C10 C9 120.9(4) . . ?
N2 C10 C11 112.6(3) . . ?
C9 C10 C11 126.6(4) . . ?
N3 C11 C12 122.2(4) . . ?
N3 C11 C10 113.5(4) . . ?
C12 C11 C10 124.3(4) . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C14 C13 C12 118.7(4) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
N3 C15 C14 122.4(4) . . ?
N3 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C17 C16 C21 118.6(4) . . ?
C17 C16 C8 120.9(4) . . ?
C21 C16 C8 120.6(4) . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
O1 C18 C19 121.7(4) . . ?
O1 C18 C17 117.3(4) . . ?
C19 C18 C17 121.0(4) . . ?
C18 C19 C20 119.0(4) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20A 119.4 . . ?
C21 C20 H20A 119.4 . . ?
C16 C21 C20 119.9(4) . . ?
C16 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C23 O2 H2B 109.5 . . ?
C22 C23 O2 143.4(2) . . ?
C22 C23 H23A 101.1 . . ?
O2 C23 H23A 101.1 . . ?
C22 C23 H23B 101.1 . . ?
O2 C23 H23B 101.1 . . ?
H23A C23 H23B 104.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 N1 C1 C2 -0.2(8) . . . . ?
Cu1 N1 C1 C2 175.7(4) . . . . ?
N1 C1 C2 C3 -0.4(9) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C1 N1 C5 C4 0.1(7) . . . . ?
Cu1 N1 C5 C4 -176.3(4) . . . . ?
C1 N1 C5 C6 -178.3(4) . . . . ?
Cu1 N1 C5 C6 5.2(5) . . . . ?
C3 C4 C5 N1 0.5(8) . . . . ?
C3 C4 C5 C6 178.8(5) . . . . ?
C10 N2 C6 C7 -2.6(7) . . . . ?
Cu1 N2 C6 C7 175.3(3) . . . . ?
C10 N2 C6 C5 176.9(4) . . . . ?
Cu1 N2 C6 C5 -5.2(5) . . . . ?
N1 C5 C6 N2 -0.3(6) . . . . ?
C4 C5 C6 N2 -178.7(5) . . . . ?
N1 C5 C6 C7 179.1(4) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?
N2 C6 C7 C8 1.3(7) . . . . ?
C5 C6 C7 C8 -178.1(4) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C6 C7 C8 C16 179.3(4) . . . . ?
C7 C8 C9 C10 -0.9(6) . . . . ?
C16 C8 C9 C10 -179.8(4) . . . . ?
C6 N2 C10 C9 2.1(7) . . . . ?
Cu1 N2 C10 C9 -175.8(3) . . . . ?
C6 N2 C10 C11 -178.5(4) . . . . ?
Cu1 N2 C10 C11 3.6(5) . . . . ?
C8 C9 C10 N2 -0.3(7) . . . . ?
C8 C9 C10 C11 -179.6(4) . . . . ?
C15 N3 C11 C12 1.3(7) . . . . ?
Cu1 N3 C11 C12 176.8(4) . . . . ?
C15 N3 C11 C10 -179.5(4) . . . . ?
Cu1 N3 C11 C10 -4.1(5) . . . . ?
N2 C10 C11 N3 0.6(5) . . . . ?
C9 C10 C11 N3 179.9(4) . . . . ?
N2 C10 C11 C12 179.7(4) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
N3 C11 C12 C13 -1.2(7) . . . . ?
C10 C11 C12 C13 179.8(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C13 C14 C15 1.0(8) . . . . ?
C11 N3 C15 C14 -0.3(7) . . . . ?
Cu1 N3 C15 C14 -175.1(4) . . . . ?
C13 C14 C15 N3 -0.9(8) . . . . ?
C7 C8 C16 C17 -5.9(6) . . . . ?
C9 C8 C16 C17 172.9(4) . . . . ?
C7 C8 C16 C21 174.1(4) . . . . ?
C9 C8 C16 C21 -7.1(6) . . . . ?
C21 C16 C17 C18 0.0(7) . . . . ?
C8 C16 C17 C18 -180.0(4) . . . . ?
C16 C17 C18 O1 -177.4(4) . . . . ?
C16 C17 C18 C19 1.9(8) . . . . ?
O1 C18 C19 C20 177.0(5) . . . . ?
C17 C18 C19 C20 -2.4(8) . . . . ?
C18 C19 C20 C21 0.9(8) . . . . ?
C17 C16 C21 C20 -1.4(7) . . . . ?
C8 C16 C21 C20 178.6(4) . . . . ?
C19 C20 C21 C16 1.0(8) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.083



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_D_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2044624'
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-02-08 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         'C21 H18 Cl2 Cu I N3 O2.50'
_chemical_formula_sum            'C21 H18 Cl2 Cu I N3 O2.50'
_chemical_formula_weight         613.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   7.8431(5)
_cell_length_b                   11.2987(13)
_cell_length_c                   13.8696(12)
_cell_angle_alpha                71.792(9)
_cell_angle_beta                 87.316(6)
_cell_angle_gamma                73.962(8)
_cell_volume                     1121.04(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2942
_cell_measurement_theta_min      3.0240
_cell_measurement_theta_max      27.5630

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_F_000             602
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    2.615
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            9821
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         29.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5212
_reflns_number_gt                3113
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0676P)²+1.3509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5212
_refine_ls_number_parameters     277
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      5.230
_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 2.11675(8) -0.13642(7) 0.92585(5) 0.0375(2) Uani 1 1 d . . . . .
Cl1 Cl 2.3004(2) -0.18932(19) 1.05971(12) 0.0559(5) Uani 1 1 d . . . . .
Cl2 Cl 2.30725(17) -0.26829(14) 0.81554(11) 0.0397(3) Uani 1 1 d . . . . .
I1 I 0.98050(5) 0.24850(5) 0.36775(3) 0.05261(18) Uani 1 1 d . . . . .
N1 N 1.9708(6) -0.2638(5) 0.9843(3) 0.0363(11) Uani 1 1 d . . . . .
N2 N 1.9114(5) -0.0600(4) 0.8315(3) 0.0317(10) Uani 1 1 d . . . . .
N3 N 2.1586(6) 0.0383(5) 0.8471(3) 0.0386(11) Uani 1 1 d . . . . .
C1 C 2.0078(7) -0.3675(6) 1.0685(4) 0.0435(15) Uani 1 1 d . . . . .
H1A H 2.109935 -0.384242 1.107588 0.052 Uiso 1 1 calc R U . . .
C2 C 1.9012(9) -0.4503(7) 1.0996(5) 0.0519(17) Uani 1 1 d . . . . .
H2A H 1.929519 -0.520385 1.158828 0.062 Uiso 1 1 calc R U . . .
C3 C 1.7524(8) -0.4264(6) 1.0405(5) 0.0476(16) Uani 1 1 d . . . . .
H3A H 1.678944 -0.481166 1.058859 0.057 Uiso 1 1 calc R U . . .
C4 C 1.7122(7) -0.3211(6) 0.9540(4) 0.0425(15) Uani 1 1 d . . . . .
H4A H 1.611353 -0.304056 0.913737 0.051 Uiso 1 1 calc R U . . .
C5 C 1.8224(6) -0.2410(5) 0.9274(4) 0.0336(13) Uani 1 1 d . . . . .
C6 C 1.7898(6) -0.1242(5) 0.8376(4) 0.0309(12) Uani 1 1 d . . . . .
C7 C 1.6518(6) -0.0801(5) 0.7672(4) 0.0336(12) Uani 1 1 d . . . . .
H7A H 1.568385 -0.126213 0.772452 0.040 Uiso 1 1 calc R U . . .
C8 C 1.6368(6) 0.0351(5) 0.6870(4) 0.0322(12) Uani 1 1 d . . . . .
C9 C 1.7642(7) 0.1006(5) 0.6850(4) 0.0348(13) Uani 1 1 d . . . . .
H9A H 1.757559 0.178155 0.633807 0.042 Uiso 1 1 calc R U . . .
C10 C 1.8998(7) 0.0515(6) 0.7582(4) 0.0339(13) Uani 1 1 d . . . . .
C11 C 2.0402(7) 0.1111(6) 0.7691(4) 0.0383(13) Uani 1 1 d . . . . .
C12 C 2.0510(8) 0.2310(6) 0.7086(5) 0.0457(15) Uani 1 1 d . . . . .
H12A H 1.966598 0.280413 0.656238 0.055 Uiso 1 1 calc R U . . .
C13 C 2.1870(8) 0.2772(7) 0.7262(5) 0.0519(17) Uani 1 1 d . . . . .
H13A H 2.196808 0.357650 0.685454 0.062 Uiso 1 1 calc R U . . .
C14 C 2.3082(8) 0.2029(7) 0.8047(6) 0.0555(18) Uani 1 1 d . . . . .
H14A H 2.401293 0.232551 0.817901 0.067 Uiso 1 1 calc R U . . .
C15 C 2.2910(7) 0.0848(7) 0.8635(5) 0.0454(16) Uani 1 1 d . . . . .
H15A H 2.373799 0.035067 0.916685 0.054 Uiso 1 1 calc R U . . .
C16 C 1.4882(7) 0.0851(5) 0.6099(4) 0.0339(12) Uani 1 1 d . . . . .
C17 C 1.4668(8) 0.1995(6) 0.5311(5) 0.0507(17) Uani 1 1 d . . . . .
H17A H 1.550907 0.245342 0.524450 0.061 Uiso 1 1 calc R U . . .
C18 C 1.3250(8) 0.2476(6) 0.4621(5) 0.0527(18) Uani 1 1 d . . . . .
H18A H 1.313449 0.325030 0.409852 0.063 Uiso 1 1 calc R U . . .
C19 C 1.2001(7) 0.1803(6) 0.4709(4) 0.0363(13) Uani 1 1 d . . . . .
C20 C 1.2211(7) 0.0645(6) 0.5444(4) 0.0390(14) Uani 1 1 d . . . . .
H20A H 1.139173 0.017463 0.548455 0.047 Uiso 1 1 calc R U . . .
C21 C 1.3651(7) 0.0164(6) 0.6135(4) 0.0390(14) Uani 1 1 d . . . . .
H21A H 1.379326 -0.063483 0.663238 0.047 Uiso 1 1 calc R U . . .
O3 O 1.6544(10) 0.4365(6) 0.5717(5) 0.111(2) Uani 1 1 d D . . . .
H3E H 1.647747 0.503947 0.521197 0.133 Uiso 1 1 d DR U . . .
H3F H 1.574417 0.464457 0.608967 0.133 Uiso 1 1 d DR U . . .
O2 O 2.5673(10) -0.5202(7) 0.7601(5) 0.122(3) Uani 1 1 d . . . . .
H2E H 2.502367 -0.448626 0.765087 0.147 Uiso 1 1 d R U . . .
H2F H 2.631714 -0.503276 0.709447 0.147 Uiso 1 1 d R U . . .
O1 O 2.000000 0.500000 0.500000 0.182(6) Uani 1 2 d DS . P . .
H01E H 2.028790 0.565750 0.503620 0.218 Uiso 0.5 1 d DR U P . .
H01A H 1.951440 0.536400 0.440680 0.218 Uiso 0.5 1 d DR U P . .


_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 N2 1.943(4) . ?
Cu1 N1 2.033(5) . ?
Cu1 N3 2.043(5) . ?
Cu1 Cl1 2.2270(15) . ?
Cu1 Cl2 2.6025(16) . ?
I1 C19 2.101(5) . ?
N1 C1 1.345(7) . ?
N1 C5 1.356(7) . ?
N2 C10 1.332(7) . ?
N2 C6 1.334(7) . ?
N3 C15 1.344(7) . ?
N3 C11 1.351(7) . ?
C1 C2 1.381(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.475(7) . ?
C6 C7 1.368(7) . ?
C7 C8 1.403(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.393(7) . ?
C8 C16 1.482(7) . ?
C9 C10 1.375(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.476(8) . ?
C11 C12 1.376(9) . ?
C12 C13 1.371(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.371(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(10) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.382(8) . ?
C16 C21 1.387(8) . ?
C17 C18 1.374(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.376(8) . ?
C18 H18A 0.9300 . ?
C19 C20 1.357(8) . ?
C20 C21 1.388(7) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
O3 H3E 0.8500 . ?
O3 H3F 0.8500 . ?
O2 H2E 0.8500 . ?
O2 H2F 0.8500 . ?
O1 H01E 0.8500 . ?
O1 H01A 0.8500 . ?
O1 H01E 0.8500 2_966 ?
O1 H01A 0.8500 2_966 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 79.45(18) . . ?
N2 Cu1 N3 78.88(18) . . ?
N1 Cu1 N3 156.01(17) . . ?
N2 Cu1 Cl1 163.05(14) . . ?
N1 Cu1 Cl1 98.86(13) . . ?
N3 Cu1 Cl1 98.84(14) . . ?
N2 Cu1 Cl2 95.11(14) . . ?
N1 Cu1 Cl2 95.21(14) . . ?
N3 Cu1 Cl2 96.86(13) . . ?
Cl1 Cu1 Cl2 101.84(6) . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Cu1 128.0(4) . . ?
C5 N1 Cu1 114.0(3) . . ?
C10 N2 C6 121.2(4) . . ?
C10 N2 Cu1 119.5(3) . . ?
C6 N2 Cu1 119.2(3) . . ?
C15 N3 C11 118.2(6) . . ?
C15 N3 Cu1 127.1(4) . . ?
C11 N3 Cu1 114.7(4) . . ?
N1 C1 C2 123.1(5) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C3 C2 C1 118.1(6) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 119.5(6) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
N1 C5 C4 121.6(5) . . ?
N1 C5 C6 114.5(5) . . ?
C4 C5 C6 124.0(5) . . ?
N2 C6 C7 121.3(5) . . ?
N2 C6 C5 112.3(4) . . ?
C7 C6 C5 126.5(5) . . ?
C6 C7 C8 119.6(5) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 117.1(5) . . ?
C9 C8 C16 122.2(5) . . ?
C7 C8 C16 120.6(5) . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
N2 C10 C9 120.2(5) . . ?
N2 C10 C11 112.5(5) . . ?
C9 C10 C11 127.2(5) . . ?
N3 C11 C12 121.6(5) . . ?
N3 C11 C10 113.8(5) . . ?
C12 C11 C10 124.5(5) . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C12 118.9(7) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C15 C14 C13 119.5(6) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
N3 C15 C14 122.2(6) . . ?
N3 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C17 C16 C21 117.0(5) . . ?
C17 C16 C8 122.4(5) . . ?
C21 C16 C8 120.6(5) . . ?
C18 C17 C16 122.0(6) . . ?
C18 C17 H17A 119.0 . . ?
C16 C17 H17A 119.0 . . ?
C17 C18 C19 119.5(5) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 I1 118.4(4) . . ?
C18 C19 I1 121.3(4) . . ?
C19 C20 C21 119.8(5) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C16 C21 C20 121.3(5) . . ?
C16 C21 H21A 119.4 . . ?
C20 C21 H21A 119.4 . . ?
H3E O3 H3F 102.1 . . ?
H2E O2 H2F 107.7 . . ?
H01E O1 H01A 95.4 . . ?
H01E O1 H01E 180.0 . 2_966 ?
H01A O1 H01E 84.6 . 2_966 ?
H01E O1 H01A 84.6 . 2_966 ?
H01A O1 H01A 180.0 . 2_966 ?
H01E O1 H01A 95.4 2_966 2_966 ?

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
C5 N1 C1 C2 -0.6(9) . . . . ?
Cu1 N1 C1 C2 -177.8(5) . . . . ?
N1 C1 C2 C3 1.1(10) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C2 C3 C4 C5 0.2(10) . . . . ?
C1 N1 C5 C4 -0.2(8) . . . . ?
Cu1 N1 C5 C4 177.5(4) . . . . ?
C1 N1 C5 C6 178.9(5) . . . . ?
Cu1 N1 C5 C6 -3.5(6) . . . . ?
C3 C4 C5 N1 0.3(9) . . . . ?
C3 C4 C5 C6 -178.6(6) . . . . ?
C10 N2 C6 C7 2.0(8) . . . . ?
Cu1 N2 C6 C7 -173.9(4) . . . . ?
C10 N2 C6 C5 -176.8(5) . . . . ?
Cu1 N2 C6 C5 7.2(6) . . . . ?
N1 C5 C6 N2 -2.1(7) . . . . ?
C4 C5 C6 N2 176.9(5) . . . . ?
N1 C5 C6 C7 179.1(5) . . . . ?
C4 C5 C6 C7 -1.8(9) . . . . ?
N2 C6 C7 C8 -0.3(8) . . . . ?
C5 C6 C7 C8 178.4(5) . . . . ?
C6 C7 C8 C9 -1.3(8) . . . . ?
C6 C7 C8 C16 -179.8(5) . . . . ?
C7 C8 C9 C10 1.2(8) . . . . ?
C16 C8 C9 C10 179.7(5) . . . . ?
C6 N2 C10 C9 -2.1(8) . . . . ?
Cu1 N2 C10 C9 173.8(4) . . . . ?
C6 N2 C10 C11 176.0(5) . . . . ?
Cu1 N2 C10 C11 -8.0(6) . . . . ?
C8 C9 C10 N2 0.5(8) . . . . ?
C8 C9 C10 C11 -177.4(5) . . . . ?
C15 N3 C11 C12 -1.2(8) . . . . ?
Cu1 N3 C11 C12 -179.8(4) . . . . ?
C15 N3 C11 C10 -179.7(5) . . . . ?
Cu1 N3 C11 C10 1.8(6) . . . . ?
N2 C10 C11 N3 3.7(7) . . . . ?
C9 C10 C11 N3 -178.3(5) . . . . ?
N2 C10 C11 C12 -174.7(5) . . . . ?
C9 C10 C11 C12 3.3(10) . . . . ?
N3 C11 C12 C13 1.4(9) . . . . ?
C10 C11 C12 C13 179.6(6) . . . . ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C12 C13 C14 C15 0.1(10) . . . . ?
C11 N3 C15 C14 0.5(9) . . . . ?
Cu1 N3 C15 C14 178.9(5) . . . . ?
C13 C14 C15 N3 0.0(10) . . . . ?
C9 C8 C16 C17 0.2(9) . . . . ?
C7 C8 C16 C17 178.7(6) . . . . ?
C9 C8 C16 C21 179.1(5) . . . . ?
C7 C8 C16 C21 -2.4(8) . . . . ?
C21 C16 C17 C18 3.5(10) . . . . ?
C8 C16 C17 C18 -177.5(6) . . . . ?
C16 C17 C18 C19 -0.3(11) . . . . ?
C17 C18 C19 C20 -2.9(10) . . . . ?
C17 C18 C19 I1 -179.9(5) . . . . ?
C18 C19 C20 C21 2.7(10) . . . . ?
I1 C19 C20 C21 179.8(4) . . . . ?
C17 C16 C21 C20 -3.7(9) . . . . ?
C8 C16 C21 C20 177.3(5) . . . . ?
C19 C20 C21 C16 0.7(9) . . . . ?

_refine_diff_density_max         1.408
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.126



####################################################################### 
# 
# 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_D_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2044626'
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2021-02-08 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         'C21 H15 Cl2 Cu N3 O'
_chemical_formula_sum            'C21 H15 Cl2 Cu N3 O'
_chemical_formula_weight         459.80

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'
Cl Cl 0.1484 0.1585 '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                   13.922(3)
_cell_length_b                   12.541(2)
_cell_length_c                   10.8692(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.105(17)
_cell_angle_gamma                90
_cell_volume                     1823.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4683
_cell_measurement_theta_min      3.8000
_cell_measurement_theta_max      29.0410

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.509
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3818
_diffrn_reflns_number            10154
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.046
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4303
_reflns_number_gt                3450
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_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)+(0.0468P)²+0.7067P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4303
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.85286(2) 0.01572(2) 0.48255(2) 0.03578(12) Uani 1 1 d . . . . .
Cl1 Cl 0.69368(5) 0.03659(5) 0.55647(6) 0.04249(17) Uani 1 1 d . . . . .
Cl2 Cl 0.96948(5) -0.01498(6) 0.66513(6) 0.04799(19) Uani 1 1 d . . . . .
O1 O 0.42242(14) 0.16103(16) -0.43695(15) 0.0529(5) Uani 1 1 d . . . . .
H1A H 0.404910 0.105817 -0.477354 0.079 Uiso 1 1 calc R U . . .
N1 N 0.82023(15) -0.13611(16) 0.42065(17) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.78020(14) 0.03977(16) 0.30566(17) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.87172(14) 0.17553(17) 0.47066(16) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.8445(2) -0.2244(2) 0.4895(2) 0.0427(6) Uani 1 1 d . . . . .
H1B H 0.882089 -0.218485 0.574501 0.051 Uiso 1 1 calc R U . . .
C2 C 0.8166(2) -0.3237(2) 0.4406(3) 0.0482(7) Uani 1 1 d . . . . .
H2A H 0.834771 -0.383797 0.491827 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7616(2) -0.3336(2) 0.3155(3) 0.0503(7) Uani 1 1 d . . . . .
H3A H 0.742973 -0.400556 0.279985 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7345(2) -0.2427(2) 0.2432(2) 0.0432(6) Uani 1 1 d . . . . .
H4A H 0.696939 -0.247346 0.158011 0.052 Uiso 1 1 calc R U . . .
C5 C 0.76345(18) -0.14504(19) 0.2984(2) 0.0340(5) Uani 1 1 d . . . . .
C6 C 0.73892(17) -0.04160(19) 0.2330(2) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.67911(18) -0.0250(2) 0.1102(2) 0.0349(5) Uani 1 1 d . . . . .
H7A H 0.649634 -0.082711 0.060128 0.042 Uiso 1 1 calc R U . . .
C8 C 0.66276(17) 0.07776(19) 0.0612(2) 0.0329(5) Uani 1 1 d . . . . .
C9 C 0.70926(17) 0.1613(2) 0.1404(2) 0.0347(5) Uani 1 1 d . . . . .
H9A H 0.700865 0.231281 0.111036 0.042 Uiso 1 1 calc R U . . .
C10 C 0.76759(17) 0.13939(19) 0.2623(2) 0.0321(5) Uani 1 1 d . . . . .
C11 C 0.82308(17) 0.21790(19) 0.35667(19) 0.0324(5) Uani 1 1 d . . . . .
C12 C 0.8292(2) 0.3242(2) 0.3314(2) 0.0413(6) Uani 1 1 d . . . . .
H12A H 0.795768 0.352111 0.251734 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8858(2) 0.3890(2) 0.4263(2) 0.0470(6) Uani 1 1 d . . . . .
H13A H 0.891925 0.461318 0.410931 0.056 Uiso 1 1 calc R U . . .
C14 C 0.9327(2) 0.3466(2) 0.5429(2) 0.0447(6) Uani 1 1 d . . . . .
H14A H 0.970082 0.389650 0.608516 0.054 Uiso 1 1 calc R U . . .
C15 C 0.92411(18) 0.2396(2) 0.5619(2) 0.0397(6) Uani 1 1 d . . . . .
H15A H 0.956068 0.210794 0.641602 0.048 Uiso 1 1 calc R U . . .
C16 C 0.59904(17) 0.0989(2) -0.0696(2) 0.0343(5) Uani 1 1 d . . . . .
C17 C 0.5752(2) 0.2013(2) -0.1140(2) 0.0515(7) Uani 1 1 d . . . . .
H17A H 0.598863 0.258671 -0.059990 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5173(2) 0.2199(2) -0.2365(3) 0.0557(8) Uani 1 1 d . . . . .
H18A H 0.502642 0.289680 -0.264324 0.067 Uiso 1 1 calc R U . . .
C19 C 0.48063(18) 0.1371(2) -0.3184(2) 0.0396(6) Uani 1 1 d . . . . .
C20 C 0.5036(2) 0.0346(2) -0.2769(2) 0.0432(6) Uani 1 1 d . . . . .
H20A H 0.479923 -0.022416 -0.331556 0.052 Uiso 1 1 calc R U . . .
C21 C 0.5620(2) 0.0165(2) -0.1539(2) 0.0405(6) Uani 1 1 d . . . . .
H21A H 0.576870 -0.053382 -0.126599 0.049 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
Cu1 N2 1.9318(18) . ?
Cu1 N1 2.029(2) . ?
Cu1 N3 2.030(2) . ?
Cu1 Cl2 2.2214(8) . ?
Cu1 Cl1 2.5716(8) . ?
O1 C19 1.352(3) . ?
N1 C1 1.326(3) . ?
N1 C5 1.350(3) . ?
N2 C6 1.321(3) . ?
N2 C10 1.330(3) . ?
N3 C15 1.327(3) . ?
N3 C11 1.346(3) . ?
C1 C2 1.367(4) . ?
C2 C3 1.369(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.374(3) . ?
C5 C6 1.473(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.396(3) . ?
C8 C16 1.476(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.476(3) . ?
C11 C12 1.369(3) . ?
C12 C13 1.376(3) . ?
C13 C14 1.363(4) . ?
C14 C15 1.367(4) . ?
C16 C17 1.379(4) . ?
C16 C21 1.382(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.371(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.377(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 79.00(8) . . ?
N2 Cu1 N3 79.85(8) . . ?
N1 Cu1 N3 157.90(7) . . ?
N2 Cu1 Cl2 165.32(6) . . ?
N1 Cu1 Cl2 100.05(6) . . ?
N3 Cu1 Cl2 98.78(5) . . ?
N2 Cu1 Cl1 92.08(6) . . ?
N1 Cu1 Cl1 93.79(6) . . ?
N3 Cu1 Cl1 93.28(6) . . ?
Cl2 Cu1 Cl1 102.60(3) . . ?
C1 N1 C5 118.3(2) . . ?
C1 N1 Cu1 126.71(16) . . ?
C5 N1 Cu1 114.87(16) . . ?
C6 N2 C10 121.40(19) . . ?
C6 N2 Cu1 119.72(16) . . ?
C10 N2 Cu1 118.74(15) . . ?
C15 N3 C11 118.8(2) . . ?
C15 N3 Cu1 127.19(16) . . ?
C11 N3 Cu1 114.05(15) . . ?
N1 C1 C2 122.7(2) . . ?
C1 C2 C3 119.3(3) . . ?
C2 C3 C4 118.7(3) . . ?
C5 C4 C3 119.2(2) . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 113.3(2) . . ?
C4 C5 C6 125.0(2) . . ?
N2 C6 C7 120.5(2) . . ?
N2 C6 C5 112.81(19) . . ?
C7 C6 C5 126.7(2) . . ?
C6 C7 C8 120.1(2) . . ?
C7 C8 C9 117.5(2) . . ?
C7 C8 C16 121.8(2) . . ?
C9 C8 C16 120.8(2) . . ?
C10 C9 C8 119.5(2) . . ?
N2 C10 C9 120.9(2) . . ?
N2 C10 C11 112.83(19) . . ?
C9 C10 C11 126.2(2) . . ?
N3 C11 C12 121.7(2) . . ?
N3 C11 C10 114.2(2) . . ?
C12 C11 C10 124.0(2) . . ?
C11 C12 C13 118.6(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 119.0(2) . . ?
N3 C15 C14 122.3(2) . . ?
C17 C16 C21 117.0(2) . . ?
C17 C16 C8 121.7(2) . . ?
C21 C16 C8 121.2(2) . . ?
C18 C17 C16 121.2(2) . . ?
C19 C18 C17 120.9(3) . . ?
O1 C19 C20 123.1(2) . . ?
O1 C19 C18 117.8(2) . . ?
C20 C19 C18 119.1(2) . . ?
C19 C20 C21 119.7(2) . . ?
C20 C21 C16 122.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.7(4) . . . . ?
Cu1 N1 C1 C2 177.9(2) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C1 N1 C5 C4 -2.8(4) . . . . ?
Cu1 N1 C5 C4 -179.42(19) . . . . ?
C1 N1 C5 C6 178.3(2) . . . . ?
Cu1 N1 C5 C6 1.7(3) . . . . ?
C3 C4 C5 N1 1.9(4) . . . . ?
C3 C4 C5 C6 -179.4(2) . . . . ?
C10 N2 C6 C7 -1.6(4) . . . . ?
Cu1 N2 C6 C7 173.98(17) . . . . ?
C10 N2 C6 C5 179.0(2) . . . . ?
Cu1 N2 C6 C5 -5.3(3) . . . . ?
N1 C5 C6 N2 2.1(3) . . . . ?
C4 C5 C6 N2 -176.7(2) . . . . ?
N1 C5 C6 C7 -177.1(2) . . . . ?
C4 C5 C6 C7 4.0(4) . . . . ?
N2 C6 C7 C8 0.8(4) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C16 -179.8(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C16 C8 C9 C10 179.5(2) . . . . ?
C6 N2 C10 C9 1.3(4) . . . . ?
Cu1 N2 C10 C9 -174.41(17) . . . . ?
C6 N2 C10 C11 -177.7(2) . . . . ?
Cu1 N2 C10 C11 6.6(3) . . . . ?
C8 C9 C10 N2 -0.1(4) . . . . ?
C8 C9 C10 C11 178.8(2) . . . . ?
C15 N3 C11 C12 2.3(4) . . . . ?
Cu1 N3 C11 C12 -178.75(19) . . . . ?
C15 N3 C11 C10 179.8(2) . . . . ?
Cu1 N3 C11 C10 -1.3(3) . . . . ?
N2 C10 C11 N3 -3.2(3) . . . . ?
C9 C10 C11 N3 177.8(2) . . . . ?
N2 C10 C11 C12 174.2(2) . . . . ?
C9 C10 C11 C12 -4.7(4) . . . . ?
N3 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C11 N3 C15 C14 -2.0(4) . . . . ?
Cu1 N3 C15 C14 179.24(19) . . . . ?
C13 C14 C15 N3 0.1(4) . . . . ?
C7 C8 C16 C17 173.8(2) . . . . ?
C9 C8 C16 C17 -6.3(4) . . . . ?
C7 C8 C16 C21 -7.3(4) . . . . ?
C9 C8 C16 C21 172.5(2) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
C8 C16 C17 C18 178.9(3) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 O1 178.8(3) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
O1 C19 C20 C21 -178.8(2) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C8 C16 C21 C20 -179.0(2) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.066



