# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2169042'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl2 Cu2 N4 O2'
_chemical_formula_weight         496.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   12.892(17)
_cell_length_b                   9.895(13)
_cell_length_c                   17.43(2)
_cell_angle_alpha                90.00(4)
_cell_angle_beta                 105.86(3)
_cell_angle_gamma                90.00(4)
_cell_volume                     2139(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3727
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17150
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4819
_reflns_number_gt                3110
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.4385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu2 Cu 0.13481(5) 0.35959(6) 0.30387(3) 0.0649(2) Uani 1 1 d . . .
Cu1 Cu -0.03672(4) 0.19911(5) 0.32848(3) 0.05805(18) Uani 1 1 d . . .
Cl2 Cl 0.20386(9) 0.16167(12) 0.26436(8) 0.0717(3) Uani 1 1 d . . .
Cl1 Cl 0.03491(10) 0.39685(11) 0.39043(7) 0.0747(4) Uani 1 1 d . . .
C15 C 1.0506(3) 0.9015(4) 0.1347(3) 0.0679(12) Uani 1 1 d . . .
H43 H 1.1163 0.9080 0.1734 0.082 Uiso 1 1 calc R . .
C14 C 1.0207(3) 0.7760(4) 0.0957(3) 0.0702(13) Uani 1 1 d . . .
H33 H 1.0670 0.7024 0.1087 0.084 Uiso 1 1 calc R . .
C13 C 0.9211(3) 0.7621(4) 0.0373(2) 0.0504(9) Uani 1 1 d . . .
H24 H 0.9010 0.6803 0.0113 0.061 Uiso 1 1 calc R . .
C12 C 0.8525(3) 0.8770(3) 0.01942(19) 0.0388(7) Uani 1 1 d . . .
C16 C 0.8887(3) 1.0009(3) 0.0604(2) 0.0472(8) Uani 1 1 d . . .
H26 H 0.8440 1.0761 0.0478 0.057 Uiso 1 1 calc R . .
C11 C 0.6845(3) 0.7655(3) -0.07139(19) 0.0386(7) Uani 1 1 d . . .
C10 C 0.5766(3) 0.7965(4) -0.1342(2) 0.0483(9) Uani 1 1 d . . .
H21A H 0.5820 0.7708 -0.1867 0.058 Uiso 1 1 calc R . .
H21B H 0.5623 0.8927 -0.1348 0.058 Uiso 1 1 calc R . .
C9 C 0.4810(3) 0.7173(4) -0.1151(2) 0.0462(8) Uani 1 1 d . . .
H3A H 0.4159 0.7300 -0.1583 0.055 Uiso 1 1 calc R . .
H3B H 0.4975 0.6215 -0.1111 0.055 Uiso 1 1 calc R . .
C8 C 0.4609(3) 0.7668(4) -0.0356(2) 0.0541(9) Uani 1 1 d . . .
H4A H 0.5275 0.7598 0.0067 0.065 Uiso 1 1 calc R . .
H4B H 0.4402 0.8613 -0.0410 0.065 Uiso 1 1 calc R . .
C7 C 0.3720(3) 0.6849(4) -0.0121(2) 0.0504(9) Uani 1 1 d . . .
H29A H 0.3917 0.5900 -0.0081 0.061 Uiso 1 1 calc R . .
H29B H 0.3048 0.6940 -0.0537 0.061 Uiso 1 1 calc R . .
C6 C 0.3545(3) 0.7322(3) 0.0684(2) 0.0445(8) Uani 1 1 d . . .
C5 C 0.3085(3) 0.6415(3) 0.1908(2) 0.0417(8) Uani 1 1 d . . .
C1 C 0.2540(3) 0.5306(4) 0.2143(2) 0.0475(8) Uani 1 1 d . . .
H22 H 0.2384 0.4559 0.1808 0.057 Uiso 1 1 calc R . .
C2 C 0.2469(4) 0.6394(4) 0.3324(2) 0.0638(11) Uani 1 1 d . . .
H35 H 0.2265 0.6392 0.3797 0.077 Uiso 1 1 calc R . .
C4 C 0.3330(4) 0.7577(4) 0.2426(2) 0.0590(10) Uani 1 1 d . . .
H34 H 0.3686 0.8324 0.2296 0.071 Uiso 1 1 calc R . .
C3 C 0.3006(4) 0.7537(5) 0.3139(2) 0.0702(12) Uani 1 1 d . . .
H41 H 0.3149 0.8268 0.3487 0.084 Uiso 1 1 calc R . .
N4 N 0.9850(3) 1.0153(3) 0.11704(19) 0.0545(8) Uani 1 1 d . . .
N3 N 0.7476(2) 0.8777(3) -0.03924(18) 0.0432(7) Uani 1 1 d . . .
H3 H 0.719(3) 0.951(4) -0.0514(19) 0.036(9) Uiso 1 1 d . . .
N2 N 0.3348(3) 0.6287(3) 0.11622(19) 0.0480(8) Uani 1 1 d . . .
H2 H 0.329(3) 0.557(4) 0.099(2) 0.050(12) Uiso 1 1 d . . .
N1 N 0.2233(3) 0.5278(3) 0.28332(19) 0.0556(8) Uani 1 1 d . . .
O2 O 0.7136(2) 0.6449(2) -0.05001(16) 0.0526(6) Uani 1 1 d . . .
O1 O 0.3592(3) 0.8553(2) 0.08858(16) 0.0628(8) Uani 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
Cu2 N1 2.103(4) . ?
Cu2 Cl1 2.266(2) . ?
Cu2 Cl2 2.332(3) . ?
Cu2 Cu1 2.801(3) 2 ?
Cu2 Cu1 2.849(3) . ?
Cu1 N4 2.076(4) 2_645 ?
Cu1 Cl1 2.303(3) . ?
Cu1 Cl2 2.344(3) 2 ?
Cu1 Cu2 2.801(3) 2 ?
Cl2 Cu1 2.344(3) 2 ?
C15 N4 1.391(5) . ?
C15 C14 1.417(6) . ?
C15 H43 0.9300 . ?
C14 C13 1.409(6) . ?
C14 H33 0.9300 . ?
C13 C12 1.422(5) . ?
C13 H24 0.9300 . ?
C12 C16 1.432(5) . ?
C12 N3 1.455(5) . ?
C16 N4 1.366(5) . ?
C16 H26 0.9300 . ?
C11 O2 1.276(4) . ?
C11 N3 1.400(5) . ?
C11 C10 1.547(5) . ?
C10 C9 1.572(5) . ?
C10 H21A 0.9700 . ?
C10 H21B 0.9700 . ?
C9 C8 1.555(5) . ?
C9 H3A 0.9700 . ?
C9 H3B 0.9700 . ?
C8 C7 1.548(5) . ?
C8 H4A 0.9700 . ?
C8 H4B 0.9700 . ?
C7 C6 1.552(5) . ?
C7 H29A 0.9700 . ?
C7 H29B 0.9700 . ?
C6 O1 1.265(4) . ?
C6 N2 1.387(5) . ?
C5 C1 1.422(5) . ?
C5 N2 1.437(5) . ?
C5 C4 1.441(5) . ?
C1 N1 1.365(5) . ?
C1 H22 0.9300 . ?
C2 N1 1.379(5) . ?
C2 C3 1.409(6) . ?
C2 H35 0.9300 . ?
C4 C3 1.416(6) . ?
C4 H34 0.9300 . ?
C3 H41 0.9300 . ?
N4 Cu1 2.076(4) 2_665 ?
N3 H3 0.82(4) . ?
N2 H2 0.76(4) . ?

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
N1 Cu2 Cl1 114.71(11) . . ?
N1 Cu2 Cl2 110.23(13) . . ?
Cl1 Cu2 Cl2 131.74(6) . . ?
N1 Cu2 Cu1 116.89(11) . 2 ?
Cl1 Cu2 Cu1 115.45(9) . 2 ?
Cl2 Cu2 Cu1 53.39(7) . 2 ?
N1 Cu2 Cu1 161.14(10) . . ?
Cl1 Cu2 Cu1 52.01(7) . . ?
Cl2 Cu2 Cu1 87.19(10) . . ?
Cu1 Cu2 Cu1 67.28(7) 2 . ?
N4 Cu1 Cl1 119.51(13) 2_645 . ?
N4 Cu1 Cl2 107.28(11) 2_645 2 ?
Cl1 Cu1 Cl2 129.30(7) . 2 ?
N4 Cu1 Cu2 152.83(10) 2_645 2 ?
Cl1 Cu1 Cu2 86.41(9) . 2 ?
Cl2 Cu1 Cu2 52.99(6) 2 2 ?
N4 Cu1 Cu2 113.08(12) 2_645 . ?
Cl1 Cu1 Cu2 50.84(6) . . ?
Cl2 Cu1 Cu2 126.10(8) 2 . ?
Cu2 Cu1 Cu2 75.78(8) 2 . ?
Cu2 Cl2 Cu1 73.62(7) . 2 ?
Cu2 Cl1 Cu1 77.15(7) . . ?
N4 C15 C14 122.3(4) . . ?
N4 C15 H43 118.9 . . ?
C14 C15 H43 118.9 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H33 119.8 . . ?
C15 C14 H33 119.8 . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 H24 121.0 . . ?
C12 C13 H24 121.0 . . ?
C13 C12 C16 118.4(3) . . ?
C13 C12 N3 124.2(3) . . ?
C16 C12 N3 117.4(3) . . ?
N4 C16 C12 123.9(3) . . ?
N4 C16 H26 118.0 . . ?
C12 C16 H26 118.0 . . ?
O2 C11 N3 122.2(3) . . ?
O2 C11 C10 121.8(3) . . ?
N3 C11 C10 116.0(3) . . ?
C11 C10 C9 110.9(3) . . ?
C11 C10 H21A 109.5 . . ?
C9 C10 H21A 109.5 . . ?
C11 C10 H21B 109.5 . . ?
C9 C10 H21B 109.5 . . ?
H21A C10 H21B 108.0 . . ?
C8 C9 C10 111.3(3) . . ?
C8 C9 H3A 109.4 . . ?
C10 C9 H3A 109.4 . . ?
C8 C9 H3B 109.4 . . ?
C10 C9 H3B 109.4 . . ?
H3A C9 H3B 108.0 . . ?
C7 C8 C9 112.7(3) . . ?
C7 C8 H4A 109.0 . . ?
C9 C8 H4A 109.0 . . ?
C7 C8 H4B 109.0 . . ?
C9 C8 H4B 109.0 . . ?
H4A C8 H4B 107.8 . . ?
C8 C7 C6 112.5(3) . . ?
C8 C7 H29A 109.1 . . ?
C6 C7 H29A 109.1 . . ?
C8 C7 H29B 109.1 . . ?
C6 C7 H29B 109.1 . . ?
H29A C7 H29B 107.8 . . ?
O1 C6 N2 123.1(3) . . ?
O1 C6 C7 122.3(3) . . ?
N2 C6 C7 114.6(3) . . ?
C1 C5 N2 116.7(3) . . ?
C1 C5 C4 118.4(3) . . ?
N2 C5 C4 124.8(3) . . ?
N1 C1 C5 123.7(3) . . ?
N1 C1 H22 118.2 . . ?
C5 C1 H22 118.2 . . ?
N1 C2 C3 122.6(4) . . ?
N1 C2 H35 118.7 . . ?
C3 C2 H35 118.7 . . ?
C3 C4 C5 117.4(4) . . ?
C3 C4 H34 121.3 . . ?
C5 C4 H34 121.3 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H41 119.8 . . ?
C4 C3 H41 119.8 . . ?
C16 N4 C15 116.9(3) . . ?
C16 N4 Cu1 122.4(2) . 2_665 ?
C15 N4 Cu1 120.6(3) . 2_665 ?
C11 N3 C12 127.2(3) . . ?
C11 N3 H3 115(2) . . ?
C12 N3 H3 117(2) . . ?
C6 N2 C5 127.3(3) . . ?
C6 N2 H2 118(3) . . ?
C5 N2 H2 114(3) . . ?
C1 N1 C2 117.5(3) . . ?
C1 N1 Cu2 117.9(2) . . ?
C2 N1 Cu2 124.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.155
####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2169052'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl2 Cu2 N4 O2'
_chemical_formula_weight         496.32

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   12.3785(14)
_cell_length_b                   9.4933(10)
_cell_length_c                   16.918(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.036(3)
_cell_angle_gamma                90.00
_cell_volume                     1910.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7699
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16473
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.27
_reflns_number_total             4727
_reflns_number_gt                3784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+1.1527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4727
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.04053(3) 0.20205(4) 0.17387(2) 0.02485(11) Uani 1 1 d . . .
Cu2 Cu -0.13419(3) 0.35515(4) 0.19296(2) 0.02681(11) Uani 1 1 d . . .
N2 N -0.3360(2) 0.6263(2) 0.38153(14) 0.0205(5) Uani 1 1 d . . .
N1 N -0.2244(2) 0.5236(2) 0.21311(14) 0.0240(5) Uani 1 1 d . . .
N3 N -0.7503(2) 0.8793(2) 0.53995(14) 0.0197(5) Uani 1 1 d . . .
N4 N -0.9890(2) 1.0171(2) 0.38230(15) 0.0254(5) Uani 1 1 d . . .
O2 O -0.71686(17) 0.64475(18) 0.55047(12) 0.0237(4) Uani 1 1 d . . .
O1 O -0.35876(19) 0.85589(19) 0.41009(13) 0.0277(5) Uani 1 1 d . . .
C9 C -0.4818(2) 0.7156(3) 0.61553(17) 0.0220(5) Uani 1 1 d . . .
H9A H -0.4122 0.7282 0.6609 0.026 Uiso 1 1 calc R . .
H9B H -0.4998 0.6137 0.6109 0.026 Uiso 1 1 calc R . .
C10 C -0.5780(2) 0.7955(3) 0.63591(16) 0.0216(5) Uani 1 1 d . . .
H10A H -0.5838 0.7662 0.6908 0.026 Uiso 1 1 calc R . .
H10B H -0.5622 0.8978 0.6377 0.026 Uiso 1 1 calc R . .
C11 C -0.6879(2) 0.7659(3) 0.57192(16) 0.0181(5) Uani 1 1 d . . .
C5 C -0.3096(2) 0.6398(3) 0.30622(16) 0.0195(5) Uani 1 1 d . . .
C12 C -0.8554(2) 0.8787(3) 0.48046(16) 0.0184(5) Uani 1 1 d . . .
C1 C -0.2555(2) 0.5260(3) 0.28228(16) 0.0215(5) Uani 1 1 d . . .
H1 H -0.2399 0.4458 0.3171 0.026 Uiso 1 1 calc R . .
C6 C -0.3547(2) 0.7313(3) 0.43004(17) 0.0199(5) Uani 1 1 d . . .
C16 C -0.8915(2) 1.0044(3) 0.43972(17) 0.0219(5) Uani 1 1 d . . .
H16 H -0.8444 1.0848 0.4535 0.026 Uiso 1 1 calc R . .
C8 C -0.4618(3) 0.7667(3) 0.53543(17) 0.0249(6) Uani 1 1 d . . .
H8A H -0.5328 0.7589 0.4909 0.030 Uiso 1 1 calc R . .
H8B H -0.4403 0.8675 0.5412 0.030 Uiso 1 1 calc R . .
C7 C -0.3709(2) 0.6845(3) 0.51135(17) 0.0229(6) Uani 1 1 d . . .
H7A H -0.2991 0.6958 0.5547 0.028 Uiso 1 1 calc R . .
H7B H -0.3907 0.5832 0.5080 0.028 Uiso 1 1 calc R . .
C4 C -0.3338(3) 0.7573(3) 0.25458(17) 0.0258(6) Uani 1 1 d . . .
H4 H -0.3714 0.8370 0.2683 0.031 Uiso 1 1 calc R . .
C2 C -0.2475(3) 0.6365(3) 0.16356(17) 0.0280(6) Uani 1 1 d . . .
H2A H -0.2262 0.6358 0.1137 0.034 Uiso 1 1 calc R . .
C13 C -0.9252(2) 0.7616(3) 0.46115(18) 0.0242(6) Uani 1 1 d . . .
H13 H -0.9040 0.6742 0.4884 0.029 Uiso 1 1 calc R . .
C15 C -1.0554(3) 0.9035(3) 0.3629(2) 0.0304(7) Uani 1 1 d . . .
H15 H -1.1247 0.9112 0.3213 0.036 Uiso 1 1 calc R . .
C3 C -0.3010(3) 0.7534(3) 0.18292(18) 0.0304(7) Uani 1 1 d . . .
H3 H -0.3155 0.8319 0.1467 0.036 Uiso 1 1 calc R . .
C14 C -1.0258(3) 0.7758(3) 0.4015(2) 0.0313(7) Uani 1 1 d . . .
H14 H -1.0749 0.6974 0.3869 0.038 Uiso 1 1 calc R . .
Cl2 Cl -0.20676(6) 0.15728(8) 0.23157(5) 0.03182(18) Uani 1 1 d . . .
Cl1 Cl -0.02905(7) 0.40081(8) 0.10923(5) 0.03347(18) Uani 1 1 d . . .
H5 H -0.720(3) 0.948(4) 0.553(2) 0.022(8) Uiso 1 1 d . . .
H2 H -0.328(3) 0.547(4) 0.401(2) 0.023(8) 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 N4 2.015(2) 2_445 ?
Cu1 Cl1 2.2311(8) . ?
Cu1 Cl2 2.2707(8) 2 ?
Cu1 Cu2 2.6627(5) 2 ?
Cu1 Cu2 2.6983(5) . ?
Cu1 Cu1 3.0118(8) 2 ?
Cu2 N1 2.033(2) . ?
Cu2 Cl1 2.2153(8) . ?
Cu2 Cl2 2.2553(8) . ?
Cu2 Cu1 2.6627(5) 2 ?
N2 C6 1.352(3) . ?
N2 C5 1.406(3) . ?
N1 C1 1.329(3) . ?
N1 C2 1.342(4) . ?
N3 C11 1.348(3) . ?
N3 C12 1.409(3) . ?
N4 C16 1.329(3) . ?
N4 C15 1.340(4) . ?
N4 Cu1 2.015(2) 2_465 ?
O2 C11 1.229(3) . ?
O1 C6 1.227(3) . ?
C9 C8 1.523(4) . ?
C9 C10 1.529(4) . ?
C10 C11 1.512(4) . ?
C5 C1 1.389(4) . ?
C5 C4 1.397(4) . ?
C12 C13 1.390(4) . ?
C12 C16 1.389(4) . ?
C6 C7 1.511(4) . ?
C8 C7 1.515(4) . ?
C4 C3 1.381(4) . ?
C2 C3 1.378(4) . ?
C13 C14 1.376(4) . ?
C15 C14 1.378(4) . ?
Cl2 Cu1 2.2707(8) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 Cl1 118.49(7) 2_445 . ?
N4 Cu1 Cl2 106.04(7) 2_445 2 ?
Cl1 Cu1 Cl2 130.97(3) . 2 ?
N4 Cu1 Cu2 151.89(7) 2_445 2 ?
Cl1 Cu1 Cu2 88.39(3) . 2 ?
Cl2 Cu1 Cu2 53.70(2) 2 2 ?
N4 Cu1 Cu2 111.48(7) 2_445 . ?
Cl1 Cu1 Cu2 52.37(2) . . ?
Cl2 Cu1 Cu2 128.08(3) 2 . ?
Cu2 Cu1 Cu2 77.334(18) 2 . ?
N4 Cu1 Cu1 105.46(8) 2_445 2 ?
Cl1 Cu1 Cu1 104.15(2) . 2 ?
Cl2 Cu1 Cu1 81.29(3) 2 2 ?
Cu2 Cu1 Cu1 56.381(14) 2 2 ?
Cu2 Cu1 Cu1 55.260(13) . 2 ?
N1 Cu2 Cl1 113.61(7) . . ?
N1 Cu2 Cl2 108.99(7) . . ?
Cl1 Cu2 Cl2 134.39(3) . . ?
N1 Cu2 Cu1 114.74(7) . 2 ?
Cl1 Cu2 Cu1 116.90(3) . 2 ?
Cl2 Cu2 Cu1 54.23(2) . 2 ?
N1 Cu2 Cu1 160.00(7) . . ?
Cl1 Cu2 Cu1 52.90(2) . . ?
Cl2 Cu2 Cu1 89.00(3) . . ?
Cu1 Cu2 Cu1 68.359(18) 2 . ?
C6 N2 C5 127.2(2) . . ?
C1 N1 C2 118.2(2) . . ?
C1 N1 Cu2 117.88(18) . . ?
C2 N1 Cu2 123.7(2) . . ?
C11 N3 C12 126.7(2) . . ?
C16 N4 C15 118.5(2) . . ?
C16 N4 Cu1 121.93(19) . 2_465 ?
C15 N4 Cu1 119.52(19) . 2_465 ?
C8 C9 C10 111.7(2) . . ?
C11 C10 C9 110.4(2) . . ?
O2 C11 N3 122.7(2) . . ?
O2 C11 C10 121.1(2) . . ?
N3 C11 C10 116.2(2) . . ?
C1 C5 C4 118.4(3) . . ?
C1 C5 N2 116.4(2) . . ?
C4 C5 N2 125.2(2) . . ?
C13 C12 C16 118.5(2) . . ?
C13 C12 N3 124.2(2) . . ?
C16 C12 N3 117.3(2) . . ?
N1 C1 C5 123.4(2) . . ?
O1 C6 N2 123.0(3) . . ?
O1 C6 C7 121.9(2) . . ?
N2 C6 C7 115.1(2) . . ?
N4 C16 C12 122.9(2) . . ?
C7 C8 C9 113.0(2) . . ?
C6 C7 C8 112.9(2) . . ?
C3 C4 C5 117.6(3) . . ?
N1 C2 C3 121.9(3) . . ?
C14 C13 C12 118.1(2) . . ?
N4 C15 C14 121.8(3) . . ?
C2 C3 C4 120.5(3) . . ?
C13 C14 C15 120.2(3) . . ?
Cu2 Cl2 Cu1 72.07(3) . 2 ?
Cu2 Cl1 Cu1 74.72(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.177
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2169043'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl2 Cu2 N4 O2'
_chemical_formula_weight         496.32

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   12.3916(9)
_cell_length_b                   9.4953(7)
_cell_length_c                   16.9063(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.072(2)
_cell_angle_gamma                90.00
_cell_volume                     1911.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7850
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      36.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    2.523
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12510
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3367
_reflns_number_gt                2826
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.8278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3367
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -1.04008(3) -0.79807(4) 0.32651(3) 0.02574(15) Uani 1 1 d . . .
Cu2 Cu -0.86613(4) -0.64427(5) 0.30688(3) 0.02859(16) Uani 1 1 d . . .
Cl1 Cl -0.97063(8) -0.59958(10) 0.39106(6) 0.0357(3) Uani 1 1 d . . .
Cl2 Cl -0.79381(7) -0.84212(10) 0.26783(6) 0.0331(2) Uani 1 1 d . . .
C5 C -0.6910(3) -0.3597(3) 0.1932(2) 0.0198(7) Uani 1 1 d . . .
C9 C -0.5184(3) -0.2838(4) -0.1153(2) 0.0223(7) Uani 1 1 d . . .
H9A H -0.5878 -0.2704 -0.1608 0.027 Uiso 1 1 calc R . .
H9B H -0.5011 -0.3858 -0.1110 0.027 Uiso 1 1 calc R . .
C12 C -0.1448(3) -0.1208(3) 0.0193(2) 0.0190(7) Uani 1 1 d . . .
C13 C -0.0753(3) -0.2376(4) 0.0386(2) 0.0240(8) Uani 1 1 d . . .
H13 H -0.0967 -0.3249 0.0114 0.029 Uiso 1 1 calc R . .
C11 C -0.3127(3) -0.2341(3) -0.0720(2) 0.0192(7) Uani 1 1 d . . .
C6 C -0.6451(3) -0.2686(3) 0.0696(2) 0.0208(7) Uani 1 1 d . . .
C1 C -0.7449(3) -0.4731(3) 0.2175(2) 0.0221(7) Uani 1 1 d . . .
H1 H -0.7607 -0.5533 0.1826 0.026 Uiso 1 1 calc R . .
C10 C -0.4214(3) -0.2044(4) -0.1353(2) 0.0229(8) Uani 1 1 d . . .
H10A H -0.4156 -0.2334 -0.1903 0.027 Uiso 1 1 calc R . .
H10B H -0.4367 -0.1019 -0.1370 0.027 Uiso 1 1 calc R . .
C7 C -0.6288(3) -0.3159(4) -0.0112(2) 0.0242(8) Uani 1 1 d . . .
H7A H -0.7006 -0.3055 -0.0547 0.029 Uiso 1 1 calc R . .
H7B H -0.6085 -0.4170 -0.0074 0.029 Uiso 1 1 calc R . .
C4 C -0.6671(3) -0.2428(4) 0.2453(2) 0.0264(8) Uani 1 1 d . . .
H4 H -0.6294 -0.1630 0.2318 0.032 Uiso 1 1 calc R . .
C3 C -0.6996(3) -0.2464(4) 0.3164(2) 0.0330(9) Uani 1 1 d . . .
H3 H -0.6849 -0.1679 0.3526 0.040 Uiso 1 1 calc R . .
C14 C 0.0252(3) -0.2242(4) 0.0981(3) 0.0320(9) Uani 1 1 d . . .
H14 H 0.0742 -0.3027 0.1126 0.038 Uiso 1 1 calc R . .
C16 C -0.1091(3) 0.0039(4) 0.0600(2) 0.0224(7) Uani 1 1 d . . .
H16 H -0.1564 0.0842 0.0463 0.027 Uiso 1 1 calc R . .
C8 C -0.5386(3) -0.2334(4) -0.0357(2) 0.0266(8) Uani 1 1 d . . .
H8A H -0.5605 -0.1329 -0.0416 0.032 Uiso 1 1 calc R . .
H8B H -0.4676 -0.2407 0.0089 0.032 Uiso 1 1 calc R . .
C15 C 0.0545(3) -0.0970(4) 0.1366(3) 0.0300(9) Uani 1 1 d . . .
H15 H 0.1238 -0.0897 0.1782 0.036 Uiso 1 1 calc R . .
C2 C -0.7534(3) -0.3629(4) 0.3358(2) 0.0298(9) Uani 1 1 d . . .
H2 H -0.7752 -0.3631 0.3854 0.036 Uiso 1 1 calc R . .
N3 N -0.2500(2) -0.1208(3) -0.04006(18) 0.0201(6) Uani 1 1 d . . .
H5 H -0.281(3) -0.045(4) -0.055(2) 0.010(8) Uiso 1 1 d . . .
N2 N -0.6645(2) -0.3732(3) 0.11804(19) 0.0216(6) Uani 1 1 d . . .
H6 H -0.672(3) -0.448(4) 0.098(2) 0.008(9) Uiso 1 1 d . . .
N4 N -0.0111(2) 0.0172(3) 0.11771(19) 0.0252(7) Uani 1 1 d . . .
N1 N -0.7758(3) -0.4758(3) 0.28670(19) 0.0266(7) Uani 1 1 d . . .
O2 O -0.2832(2) -0.3556(2) -0.05049(15) 0.0238(5) Uani 1 1 d . . .
O1 O -0.6413(2) -0.1441(2) 0.08996(16) 0.0291(6) Uani 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 N4 2.009(3) 2_445 ?
Cu1 Cl1 2.2279(10) . ?
Cu1 Cl2 2.2668(10) 2_355 ?
Cu1 Cu2 2.6680(6) 2_355 ?
Cu1 Cu2 2.6991(6) . ?
Cu1 Cu1 3.0171(9) 2_355 ?
Cu2 N1 2.034(3) . ?
Cu2 Cl1 2.2143(10) . ?
Cu2 Cl2 2.2573(10) . ?
Cu2 Cu1 2.6680(6) 2_355 ?
Cl2 Cu1 2.2668(10) 2_355 ?
C5 C1 1.388(5) . ?
C5 C4 1.397(5) . ?
C5 N2 1.402(5) . ?
C9 C8 1.513(5) . ?
C9 C10 1.535(5) . ?
C12 C16 1.380(5) . ?
C12 C13 1.387(5) . ?
C12 N3 1.408(4) . ?
C13 C14 1.373(5) . ?
C11 O2 1.234(4) . ?
C11 N3 1.350(4) . ?
C11 C10 1.497(5) . ?
C6 O1 1.229(4) . ?
C6 N2 1.351(5) . ?
C6 C7 1.504(5) . ?
C1 N1 1.329(4) . ?
C7 C8 1.513(5) . ?
C4 C3 1.370(5) . ?
C3 C2 1.378(5) . ?
C14 C15 1.372(5) . ?
C16 N4 1.337(4) . ?
C15 N4 1.340(5) . ?
C2 N1 1.337(5) . ?
N4 Cu1 2.009(3) 2_465 ?

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
N4 Cu1 Cl1 118.67(9) 2_445 . ?
N4 Cu1 Cl2 106.04(9) 2_445 2_355 ?
Cl1 Cu1 Cl2 130.78(4) . 2_355 ?
N4 Cu1 Cu2 151.83(9) 2_445 2_355 ?
Cl1 Cu1 Cu2 88.27(3) . 2_355 ?
Cl2 Cu1 Cu2 53.70(3) 2_355 2_355 ?
N4 Cu1 Cu2 111.78(8) 2_445 . ?
Cl1 Cu1 Cu2 52.36(3) . . ?
Cl2 Cu1 Cu2 127.87(3) 2_355 . ?
Cu2 Cu1 Cu2 77.04(2) 2_355 . ?
N4 Cu1 Cu1 105.45(9) 2_445 2_355 ?
Cl1 Cu1 Cu1 104.23(3) . 2_355 ?
Cl2 Cu1 Cu1 81.20(3) 2_355 2_355 ?
Cu2 Cu1 Cu1 56.286(16) 2_355 2_355 ?
Cu2 Cu1 Cu1 55.308(15) . 2_355 ?
N1 Cu2 Cl1 113.81(9) . . ?
N1 Cu2 Cl2 108.91(9) . . ?
Cl1 Cu2 Cl2 134.24(4) . . ?
N1 Cu2 Cu1 114.82(9) . 2_355 ?
Cl1 Cu2 Cu1 116.92(3) . 2_355 ?
Cl2 Cu2 Cu1 54.03(3) . 2_355 ?
N1 Cu2 Cu1 160.24(9) . . ?
Cl1 Cu2 Cu1 52.81(3) . . ?
Cl2 Cu2 Cu1 88.91(3) . . ?
Cu1 Cu2 Cu1 68.41(2) 2_355 . ?
Cu2 Cl1 Cu1 74.83(3) . . ?
Cu2 Cl2 Cu1 72.27(3) . 2_355 ?
C1 C5 C4 117.7(3) . . ?
C1 C5 N2 116.7(3) . . ?
C4 C5 N2 125.6(3) . . ?
C8 C9 C10 111.9(3) . . ?
C16 C12 C13 118.5(3) . . ?
C16 C12 N3 117.4(3) . . ?
C13 C12 N3 124.1(3) . . ?
C14 C13 C12 118.5(3) . . ?
O2 C11 N3 122.5(3) . . ?
O2 C11 C10 121.4(3) . . ?
N3 C11 C10 116.1(3) . . ?
O1 C6 N2 122.5(3) . . ?
O1 C6 C7 122.5(3) . . ?
N2 C6 C7 115.0(3) . . ?
N1 C1 C5 123.8(3) . . ?
C11 C10 C9 110.8(3) . . ?
C6 C7 C8 112.9(3) . . ?
C3 C4 C5 118.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C15 C14 C13 119.7(3) . . ?
N4 C16 C12 123.1(3) . . ?
C9 C8 C7 113.3(3) . . ?
N4 C15 C14 122.4(3) . . ?
N1 C2 C3 121.8(3) . . ?
C11 N3 C12 127.0(3) . . ?
C6 N2 C5 127.4(3) . . ?
C16 N4 C15 117.8(3) . . ?
C16 N4 Cu1 122.0(2) . 2_465 ?
C15 N4 Cu1 120.2(2) . 2_465 ?
C1 N1 C2 118.0(3) . . ?
C1 N1 Cu2 118.0(2) . . ?
C2 N1 Cu2 123.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.172
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2169053'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Br2 Cu2 N4 O2'
_chemical_formula_weight         585.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   13.097(2)
_cell_length_b                   9.6809(15)
_cell_length_c                   16.800(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.535(5)
_cell_angle_gamma                90.00
_cell_volume                     2031.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4026
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.78

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    6.046
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13774
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.27
_reflns_number_total             3675
_reflns_number_gt                2425
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+2.3417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3675
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 1.29636(5) -0.34145(6) 0.23836(4) 0.0703(2) Uani 1 1 d . . .
Br1 Br 1.45921(5) -0.09307(6) 0.10551(4) 0.0690(2) Uani 1 1 d . . .
Cu1 Cu 1.52455(5) -0.30534(7) 0.17060(5) 0.0660(2) Uani 1 1 d . . .
Cu2 Cu 1.37742(6) -0.13125(7) 0.21026(5) 0.0716(2) Uani 1 1 d . . .
O2 O 0.7927(3) 0.1495(3) 0.5489(2) 0.0547(9) Uani 1 1 d . . .
N3 N 0.7639(3) 0.3801(4) 0.5398(2) 0.0449(10) Uani 1 1 d . . .
C12 C 0.6596(4) 0.3800(4) 0.4840(3) 0.0426(11) Uani 1 1 d . . .
N2 N 1.1705(3) 0.1275(4) 0.3884(3) 0.0514(11) Uani 1 1 d . . .
N4 N 0.5259(3) 0.5146(4) 0.3867(3) 0.0587(12) Uani 1 1 d . . .
O1 O 1.1417(3) 0.3506(3) 0.4142(3) 0.0676(11) Uani 1 1 d . . .
N1 N 1.2897(3) 0.0321(4) 0.2281(3) 0.0588(12) Uani 1 1 d . . .
C11 C 0.8234(4) 0.2672(5) 0.5709(3) 0.0433(11) Uani 1 1 d . . .
C7 C 1.1263(4) 0.1811(5) 0.5138(3) 0.0532(13) Uani 1 1 d . . .
H9A H 1.1922 0.1897 0.5595 0.064 Uiso 1 1 calc R . .
H9B H 1.1067 0.0842 0.5083 0.064 Uiso 1 1 calc R . .
C10 C 0.9303(4) 0.2943(5) 0.6338(3) 0.0519(13) Uani 1 1 d . . .
H10A H 0.9273 0.2688 0.6889 0.062 Uiso 1 1 calc R . .
H10B H 0.9461 0.3923 0.6344 0.062 Uiso 1 1 calc R . .
C9 C 1.0190(4) 0.2142(5) 0.6144(3) 0.0517(13) Uani 1 1 d . . .
H11A H 1.0004 0.1169 0.6095 0.062 Uiso 1 1 calc R . .
H11B H 1.0843 0.2244 0.6604 0.062 Uiso 1 1 calc R . .
C13 C 0.5895(4) 0.2699(5) 0.4704(4) 0.0562(14) Uani 1 1 d . . .
H12 H 0.6099 0.1871 0.4987 0.067 Uiso 1 1 calc R . .
C16 C 0.6231(4) 0.5006(5) 0.4415(3) 0.0550(14) Uani 1 1 d . . .
H13 H 0.6688 0.5765 0.4515 0.066 Uiso 1 1 calc R . .
C1 C 1.2557(4) 0.0342(5) 0.2947(4) 0.0532(13) Uani 1 1 d . . .
H14 H 1.2700 -0.0424 0.3297 0.064 Uiso 1 1 calc R . .
C15 C 0.4605(4) 0.4070(5) 0.3738(4) 0.0696(17) Uani 1 1 d . . .
H15 H 0.3925 0.4150 0.3357 0.084 Uiso 1 1 calc R . .
C5 C 1.2004(4) 0.1426(5) 0.3156(3) 0.0476(12) Uani 1 1 d . . .
C8 C 1.0394(4) 0.2617(5) 0.5346(3) 0.0573(14) Uani 1 1 d . . .
H17A H 0.9736 0.2530 0.4889 0.069 Uiso 1 1 calc R . .
H17B H 1.0590 0.3586 0.5400 0.069 Uiso 1 1 calc R . .
C6 C 1.1460(4) 0.2290(5) 0.4346(3) 0.0473(12) Uani 1 1 d . . .
C14 C 0.4900(4) 0.2843(5) 0.4149(4) 0.0695(18) Uani 1 1 d . . .
H19 H 0.4421 0.2108 0.4050 0.083 Uiso 1 1 calc R . .
C4 C 1.1791(5) 0.2568(5) 0.2619(4) 0.0649(16) Uani 1 1 d . . .
H20 H 1.1420 0.3328 0.2729 0.078 Uiso 1 1 calc R . .
C2 C 1.2689(5) 0.1425(6) 0.1775(4) 0.0682(16) Uani 1 1 d . . .
H1 H 1.2923 0.1434 0.1305 0.082 Uiso 1 1 calc R . .
C3 C 1.2135(5) 0.2545(6) 0.1936(4) 0.0747(18) Uani 1 1 d . . .
H2 H 1.1996 0.3293 0.1572 0.090 Uiso 1 1 calc R . .
H4 H 0.7975 0.4711 0.5514 0.037(12) Uiso 1 1 d R . .
H3 H 1.1774 0.0328 0.4042 0.079(18) Uiso 1 1 d R . .


_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
Br2 Cu2 2.4068(10) . ?
Br2 Cu1 2.4086(10) 2_855 ?
Br1 Cu2 2.3489(10) . ?
Br1 Cu1 2.3636(9) . ?
Cu1 N4 2.004(4) 2_745 ?
Cu1 Br2 2.4086(10) 2_855 ?
Cu1 Cu2 2.6356(10) 2_855 ?
Cu1 Cu2 2.7878(10) . ?
Cu1 Cu1 2.9266(17) 2_855 ?
Cu2 N1 2.029(4) . ?
Cu2 Cu1 2.6356(10) 2_855 ?
O2 C11 1.227(5) . ?
N3 C11 1.353(6) . ?
N3 C12 1.405(6) . ?
C12 C16 1.377(6) . ?
C12 C13 1.380(7) . ?
N2 C6 1.349(6) . ?
N2 C5 1.400(7) . ?
N4 C15 1.325(6) . ?
N4 C16 1.334(6) . ?
N4 Cu1 2.004(4) 2_765 ?
O1 C6 1.222(5) . ?
N1 C1 1.324(6) . ?
N1 C2 1.342(7) . ?
C11 C10 1.501(7) . ?
C7 C6 1.503(7) . ?
C7 C8 1.506(7) . ?
C10 C9 1.512(7) . ?
C9 C8 1.514(7) . ?
C13 C14 1.361(7) . ?
C1 C5 1.379(7) . ?
C15 C14 1.370(7) . ?
C5 C4 1.401(7) . ?
C4 C3 1.352(8) . ?
C2 C3 1.376(8) . ?

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
Cu2 Br2 Cu1 66.37(3) . 2_855 ?
Cu2 Br1 Cu1 72.53(3) . . ?
N4 Cu1 Br1 120.86(13) 2_745 . ?
N4 Cu1 Br2 107.21(12) 2_745 2_855 ?
Br1 Cu1 Br2 124.58(4) . 2_855 ?
N4 Cu1 Cu2 159.28(13) 2_745 2_855 ?
Br1 Cu1 Cu2 79.69(3) . 2_855 ?
Br2 Cu1 Cu2 56.78(3) 2_855 2_855 ?
N4 Cu1 Cu2 119.24(13) 2_745 . ?
Br1 Cu1 Cu2 53.49(3) . . ?
Br2 Cu1 Cu2 123.16(4) 2_855 . ?
Cu2 Cu1 Cu2 69.24(4) 2_855 . ?
N4 Cu1 Cu1 107.83(14) 2_745 2_855 ?
Br1 Cu1 Cu1 105.87(3) . 2_855 ?
Br2 Cu1 Cu1 81.98(4) 2_855 2_855 ?
Cu2 Cu1 Cu1 59.89(3) 2_855 2_855 ?
Cu2 Cu1 Cu1 54.87(3) . 2_855 ?
N1 Cu2 Br1 113.21(13) . . ?
N1 Cu2 Br2 109.11(13) . . ?
Br1 Cu2 Br2 127.42(4) . . ?
N1 Cu2 Cu1 123.66(14) . 2_855 ?
Br1 Cu2 Cu1 116.22(4) . 2_855 ?
Br2 Cu2 Cu1 56.85(3) . 2_855 ?
N1 Cu2 Cu1 165.75(13) . . ?
Br1 Cu2 Cu1 53.98(3) . . ?
Br2 Cu2 Cu1 85.02(3) . . ?
Cu1 Cu2 Cu1 65.25(4) 2_855 . ?
C11 N3 C12 126.1(4) . . ?
C16 C12 C13 117.4(4) . . ?
C16 C12 N3 117.5(4) . . ?
C13 C12 N3 125.1(4) . . ?
C6 N2 C5 127.2(4) . . ?
C15 N4 C16 117.9(4) . . ?
C15 N4 Cu1 120.1(3) . 2_765 ?
C16 N4 Cu1 121.9(3) . 2_765 ?
C1 N1 C2 117.8(5) . . ?
C1 N1 Cu2 119.1(3) . . ?
C2 N1 Cu2 123.0(4) . . ?
O2 C11 N3 122.4(4) . . ?
O2 C11 C10 121.7(4) . . ?
N3 C11 C10 115.9(4) . . ?
C6 C7 C8 112.9(4) . . ?
C11 C10 C9 111.9(4) . . ?
C10 C9 C8 112.7(4) . . ?
C14 C13 C12 119.1(5) . . ?
N4 C16 C12 123.6(4) . . ?
N1 C1 C5 124.3(5) . . ?
N4 C15 C14 121.9(5) . . ?
C1 C5 N2 116.7(4) . . ?
C1 C5 C4 117.0(5) . . ?
N2 C5 C4 126.3(5) . . ?
C7 C8 C9 113.3(4) . . ?
O1 C6 N2 122.7(5) . . ?
O1 C6 C7 122.6(5) . . ?
N2 C6 C7 114.7(4) . . ?
C13 C14 C15 120.0(5) . . ?
C3 C4 C5 118.7(5) . . ?
N1 C2 C3 121.4(6) . . ?
C4 C3 C2 120.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2169055'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl2 Cu2 N4 O2'
_chemical_formula_weight         496.32

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   12.5432(15)
_cell_length_b                   9.5412(11)
_cell_length_c                   16.985(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.366(4)
_cell_angle_gamma                90.00
_cell_volume                     1950.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4961
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.26

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17092
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.30
_reflns_number_total             4827
_reflns_number_gt                2963
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0771P)²+0.7871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4827
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -1.03661(4) -0.30089(5) 0.82852(3) 0.0575(2) Uani 1 1 d . . .
Cu2 Cu -0.86529(5) -0.14050(6) 0.80383(3) 0.0636(2) Uani 1 1 d . . .
Cl2 Cl -0.79620(10) -0.33821(13) 0.76429(9) 0.0701(4) Uani 1 1 d . . .
Cl1 Cl -0.96519(12) -0.10311(13) 0.89038(8) 0.0738(4) Uani 1 1 d . . .
N2 N -0.6654(3) 0.1284(4) 0.6163(2) 0.0460(8) Uani 1 1 d . . .
H6 H -0.667(4) 0.054(5) 0.600(3) 0.055(14) Uiso 1 1 d . . .
N3 N -0.2523(3) 0.3777(3) 0.4608(2) 0.0427(8) Uani 1 1 d . . .
H5 H -0.282(3) 0.438(4) 0.448(2) 0.030(11) Uiso 1 1 d . . .
N1 N -0.7768(3) 0.0277(4) 0.7830(2) 0.0542(9) Uani 1 1 d . . .
N4 N -0.0155(3) 0.5145(3) 0.6168(2) 0.0533(9) Uani 1 1 d . . .
O1 O -0.6409(3) 0.3552(3) 0.58831(18) 0.0612(8) Uani 1 1 d . . .
O2 O -0.2864(2) 0.1451(2) 0.45016(18) 0.0519(7) Uani 1 1 d . . .
C11 C -0.3154(3) 0.2654(4) 0.4285(2) 0.0390(8) Uani 1 1 d . . .
C5 C -0.6911(3) 0.1415(4) 0.6908(2) 0.0415(8) Uani 1 1 d . . .
C9 C -0.5194(3) 0.2171(4) 0.3849(2) 0.0462(9) Uani 1 1 d . . .
H9A H -0.5866 0.2299 0.3403 0.055 Uiso 1 1 calc R . .
H9B H -0.5021 0.1178 0.3891 0.055 Uiso 1 1 calc R . .
C12 C -0.1476(3) 0.3774(4) 0.5194(2) 0.0384(8) Uani 1 1 d . . .
C10 C -0.4242(3) 0.2964(4) 0.3654(2) 0.0471(9) Uani 1 1 d . . .
H10A H -0.4194 0.2693 0.3115 0.057 Uiso 1 1 calc R . .
H10B H -0.4389 0.3963 0.3646 0.057 Uiso 1 1 calc R . .
C16 C -0.1121(3) 0.5011(4) 0.5602(2) 0.0466(9) Uani 1 1 d . . .
H16 H -0.1583 0.5790 0.5473 0.056 Uiso 1 1 calc R . .
C1 C -0.7464(3) 0.0309(4) 0.7142(2) 0.0467(9) Uani 1 1 d . . .
H1 H -0.7633 -0.0463 0.6795 0.056 Uiso 1 1 calc R . .
C6 C -0.6456(3) 0.2319(4) 0.5683(2) 0.0437(9) Uani 1 1 d . . .
C7 C -0.6281(4) 0.1851(4) 0.4878(2) 0.0509(10) Uani 1 1 d . . .
H7A H -0.6082 0.0866 0.4918 0.061 Uiso 1 1 calc R . .
H7B H -0.6976 0.1949 0.4449 0.061 Uiso 1 1 calc R . .
C8 C -0.5396(4) 0.2663(5) 0.4639(3) 0.0545(10) Uani 1 1 d . . .
H8A H -0.4708 0.2590 0.5076 0.065 Uiso 1 1 calc R . .
H8B H -0.5607 0.3644 0.4583 0.065 Uiso 1 1 calc R . .
C2 C -0.7533(4) 0.1388(5) 0.8322(3) 0.0612(12) Uani 1 1 d . . .
H2 H -0.7741 0.1385 0.8806 0.073 Uiso 1 1 calc R . .
C13 C -0.0791(3) 0.2622(4) 0.5375(3) 0.0493(10) Uani 1 1 d . . .
H13 H -0.1001 0.1771 0.5110 0.059 Uiso 1 1 calc R . .
C14 C 0.0211(4) 0.2766(4) 0.5959(3) 0.0675(14) Uani 1 1 d . . .
H14 H 0.0693 0.2007 0.6093 0.081 Uiso 1 1 calc R . .
C3 C -0.6993(5) 0.2534(5) 0.8138(3) 0.0712(14) Uani 1 1 d . . .
H3 H -0.6840 0.3292 0.8496 0.085 Uiso 1 1 calc R . .
C4 C -0.6674(4) 0.2576(4) 0.7429(3) 0.0579(11) Uani 1 1 d . . .
H4 H -0.6312 0.3355 0.7298 0.069 Uiso 1 1 calc R . .
C15 C 0.0502(4) 0.4015(4) 0.6343(3) 0.0639(13) Uani 1 1 d . . .
H15 H 0.1182 0.4088 0.6741 0.077 Uiso 1 1 calc R . .


_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 N4 2.013(3) 2_446 ?
Cu1 Cl1 2.2220(13) . ?
Cu1 Cl2 2.2687(13) 2_356 ?
Cu1 Cu2 2.7112(8) 2_356 ?
Cu1 Cu2 2.7647(8) . ?
Cu1 Cu1 3.0560(13) 2_356 ?
Cu2 N1 2.039(4) . ?
Cu2 Cl1 2.2130(14) . ?
Cu2 Cl2 2.2557(14) . ?
Cu2 Cu1 2.7112(8) 2_356 ?
Cl2 Cu1 2.2686(13) 2_356 ?
N2 C6 1.347(5) . ?
N2 C5 1.397(5) . ?
N3 C11 1.353(5) . ?
N3 C12 1.407(5) . ?
N1 C1 1.327(5) . ?
N1 C2 1.331(5) . ?
N4 C16 1.324(5) . ?
N4 C15 1.338(5) . ?
N4 Cu1 2.013(3) 2_466 ?
O1 C6 1.222(4) . ?
O2 C11 1.229(4) . ?
C11 C10 1.508(5) . ?
C5 C1 1.380(5) . ?
C5 C4 1.396(5) . ?
C9 C8 1.508(6) . ?
C9 C10 1.526(6) . ?
C12 C13 1.375(5) . ?
C12 C16 1.378(5) . ?
C6 C7 1.511(5) . ?
C7 C8 1.501(6) . ?
C2 C3 1.369(7) . ?
C13 C14 1.372(6) . ?
C14 C15 1.357(6) . ?
C3 C4 1.372(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 Cl1 119.34(11) 2_446 . ?
N4 Cu1 Cl2 107.43(10) 2_446 2_356 ?
Cl1 Cu1 Cl2 129.23(6) . 2_356 ?
N4 Cu1 Cu2 152.77(10) 2_446 2_356 ?
Cl1 Cu1 Cu2 86.62(4) . 2_356 ?
Cl2 Cu1 Cu2 52.97(4) 2_356 2_356 ?
N4 Cu1 Cu2 112.92(10) 2_446 . ?
Cl1 Cu1 Cu2 51.29(4) . . ?
Cl2 Cu1 Cu2 125.96(4) 2_356 . ?
Cu2 Cu1 Cu2 75.66(3) 2_356 . ?
N4 Cu1 Cu1 105.34(11) 2_446 2_356 ?
Cl1 Cu1 Cu1 103.44(4) . 2_356 ?
Cl2 Cu1 Cu1 80.78(4) 2_356 2_356 ?
Cu2 Cu1 Cu1 56.91(2) 2_356 2_356 ?
Cu2 Cu1 Cu1 55.248(19) . 2_356 ?
N1 Cu2 Cl1 115.25(10) . . ?
N1 Cu2 Cl2 109.45(11) . . ?
Cl1 Cu2 Cl2 132.03(6) . . ?
N1 Cu2 Cu1 116.26(10) . 2_356 ?
Cl1 Cu2 Cu1 115.61(4) . 2_356 ?
Cl2 Cu2 Cu1 53.40(3) . 2_356 ?
N1 Cu2 Cu1 161.22(11) . . ?
Cl1 Cu2 Cu1 51.58(4) . . ?
Cl2 Cu2 Cu1 87.85(4) . . ?
Cu1 Cu2 Cu1 67.84(3) 2_356 . ?
Cu2 Cl2 Cu1 73.63(4) . 2_356 ?
Cu2 Cl1 Cu1 77.13(4) . . ?
C6 N2 C5 127.8(3) . . ?
C11 N3 C12 127.4(3) . . ?
C1 N1 C2 117.9(4) . . ?
C1 N1 Cu2 118.5(3) . . ?
C2 N1 Cu2 123.5(3) . . ?
C16 N4 C15 117.6(3) . . ?
C16 N4 Cu1 122.1(3) . 2_466 ?
C15 N4 Cu1 120.2(3) . 2_466 ?
O2 C11 N3 121.9(3) . . ?
O2 C11 C10 121.8(3) . . ?
N3 C11 C10 116.2(3) . . ?
C1 C5 C4 117.3(4) . . ?
C1 C5 N2 117.1(3) . . ?
C4 C5 N2 125.6(4) . . ?
C8 C9 C10 112.1(3) . . ?
C13 C12 C16 118.6(3) . . ?
C13 C12 N3 124.0(3) . . ?
C16 C12 N3 117.3(3) . . ?
C11 C10 C9 110.8(3) . . ?
N4 C16 C12 123.2(3) . . ?
N1 C1 C5 124.3(4) . . ?
O1 C6 N2 122.7(4) . . ?
O1 C6 C7 121.9(4) . . ?
N2 C6 C7 115.4(3) . . ?
C8 C7 C6 113.6(3) . . ?
C7 C8 C9 113.8(3) . . ?
N1 C2 C3 121.9(4) . . ?
C14 C13 C12 118.0(4) . . ?
C15 C14 C13 120.2(4) . . ?
C2 C3 C4 120.7(4) . . ?
C3 C4 C5 118.0(4) . . ?
N4 C15 C14 122.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.553
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.171
####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2169054'
loop_
_audit_author_name
_audit_author_address
'Zhenlan Fang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Br2 Cu2 N4 O2'
_chemical_formula_weight         585.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   13.0123(13)
_cell_length_b                   9.6529(9)
_cell_length_c                   16.7087(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.453(3)
_cell_angle_gamma                90.00
_cell_volume                     2002.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6190
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.77

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    6.133
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17717
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         28.87
_reflns_number_total             5251
_reflns_number_gt                3606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0511P)²+4.3786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5251
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 2.02698(5) -0.80168(6) 0.17196(4) 0.02716(17) Uani 1 1 d . . .
Cu2 Cu 1.87780(5) -0.63409(6) 0.20689(5) 0.02972(17) Uani 1 1 d . . .
Br2 Br 1.79383(4) -0.84231(5) 0.23553(4) 0.03098(15) Uani 1 1 d . . .
Br1 Br 1.96239(4) -0.59028(5) 0.10337(4) 0.03061(15) Uani 1 1 d . . .
N3 N 1.2618(3) -0.1198(4) 0.5396(3) 0.0204(9) Uani 1 1 d . . .
H3 H 1.291(3) -0.050(5) 0.553(3) 0.002(11) Uiso 1 1 d . . .
N4 N 1.0227(3) 0.0177(4) 0.3861(3) 0.0283(10) Uani 1 1 d . . .
N1 N 1.7905(3) -0.4692(4) 0.2250(3) 0.0258(9) Uani 1 1 d . . .
N2 N 1.6703(3) -0.3732(4) 0.3866(3) 0.0222(9) Uani 1 1 d . . .
C12 C 1.1562(4) -0.1186(4) 0.4833(3) 0.0182(9) Uani 1 1 d . . .
C11 C 1.3210(4) -0.2331(5) 0.5705(3) 0.0188(9) Uani 1 1 d . . .
C7 C 1.6264(4) -0.3203(5) 0.5135(3) 0.0228(10) Uani 1 1 d . . .
H7A H 1.6940 -0.3119 0.5605 0.027 Uiso 1 1 calc R . .
H7B H 1.6060 -0.4194 0.5076 0.027 Uiso 1 1 calc R . .
C3 C 1.7005(4) -0.3576(5) 0.3134(3) 0.0202(10) Uani 1 1 d . . .
C16 C 1.1203(4) 0.0040(5) 0.4408(3) 0.0229(11) Uani 1 1 d . . .
H16 H 1.1675 0.0814 0.4512 0.027 Uiso 1 1 calc R . .
C9 C 1.5176(4) -0.2884(5) 0.6148(3) 0.0238(10) Uani 1 1 d . . .
H9A H 1.5847 -0.2799 0.6621 0.029 Uiso 1 1 calc R . .
H9B H 1.4971 -0.3875 0.6088 0.029 Uiso 1 1 calc R . .
C10 C 1.4286(4) -0.2057(5) 0.6348(3) 0.0224(10) Uani 1 1 d . . .
H10A H 1.4249 -0.2315 0.6912 0.027 Uiso 1 1 calc R . .
H10B H 1.4454 -0.1056 0.6354 0.027 Uiso 1 1 calc R . .
C15 C 0.9561(4) -0.0914(5) 0.3721(4) 0.0328(13) Uani 1 1 d . . .
H15 H 0.8865 -0.0825 0.3329 0.039 Uiso 1 1 calc R . .
C13 C 1.0865(4) -0.2312(5) 0.4691(4) 0.0246(11) Uani 1 1 d . . .
H13 H 1.1081 -0.3165 0.4975 0.030 Uiso 1 1 calc R . .
C2 C 1.7561(4) -0.4693(5) 0.2924(3) 0.0239(11) Uani 1 1 d . . .
H2 H 1.7698 -0.5485 0.3278 0.029 Uiso 1 1 calc R . .
C14 C 0.9850(4) -0.2162(5) 0.4126(4) 0.0296(13) Uani 1 1 d . . .
H14 H 0.9355 -0.2912 0.4018 0.036 Uiso 1 1 calc R . .
C8 C 1.5388(4) -0.2391(5) 0.5346(3) 0.0252(11) Uani 1 1 d . . .
H8A H 1.4714 -0.2469 0.4875 0.030 Uiso 1 1 calc R . .
H8B H 1.5595 -0.1400 0.5408 0.030 Uiso 1 1 calc R . .
C4 C 1.6802(4) -0.2421(5) 0.2604(3) 0.0278(12) Uani 1 1 d . . .
H4 H 1.6424 -0.1642 0.2721 0.033 Uiso 1 1 calc R . .
C6 C 1.6466(4) -0.2717(5) 0.4339(3) 0.0201(10) Uani 1 1 d . . .
C1 C 1.7707(4) -0.3584(5) 0.1749(4) 0.0288(11) Uani 1 1 d . . .
H1 H 1.7947 -0.3580 0.1265 0.035 Uiso 1 1 calc R . .
C5 C 1.7159(5) -0.2439(5) 0.1915(4) 0.0327(13) Uani 1 1 d . . .
H5 H 1.7032 -0.1665 0.1548 0.039 Uiso 1 1 calc R . .
O2 O 1.2901(3) -0.3516(3) 0.5491(2) 0.0248(8) Uani 1 1 d . . .
O1 O 1.6419(3) -0.1489(3) 0.4137(2) 0.0287(8) Uani 1 1 d . . .
H10 H 1.677(5) -0.448(7) 0.406(4) 0.036(18) 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 N4 2.006(4) 2_845 ?
Cu1 Br1 2.3677(8) . ?
Cu1 Br2 2.4121(8) 2_955 ?
Cu1 Cu2 2.5971(9) 2_955 ?
Cu1 Cu2 2.7213(9) . ?
Cu1 Cu1 2.8969(15) 2_955 ?
Cu2 N1 2.031(4) . ?
Cu2 Br1 2.3504(9) . ?
Cu2 Br2 2.4034(8) . ?
Cu2 Cu1 2.5971(9) 2_955 ?
Br2 Cu1 2.4121(8) 2_955 ?
N3 C11 1.348(6) . ?
N3 C12 1.413(6) . ?
N4 C16 1.331(6) . ?
N4 C15 1.339(6) . ?
N4 Cu1 2.006(4) 2_865 ?
N1 C2 1.331(7) . ?
N1 C1 1.335(6) . ?
N2 C6 1.352(6) . ?
N2 C3 1.399(7) . ?
C12 C16 1.387(6) . ?
C12 C13 1.390(6) . ?
C11 O2 1.229(5) . ?
C11 C10 1.510(7) . ?
C7 C6 1.506(7) . ?
C7 C8 1.510(7) . ?
C3 C4 1.399(7) . ?
C3 C2 1.400(7) . ?
C9 C8 1.523(7) . ?
C9 C10 1.524(7) . ?
C15 C14 1.377(7) . ?
C13 C14 1.381(7) . ?
C4 C5 1.365(8) . ?
C6 O1 1.229(6) . ?
C1 C5 1.388(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 Br1 119.94(13) 2_845 . ?
N4 Cu1 Br2 106.13(12) 2_845 2_955 ?
Br1 Cu1 Br2 125.80(3) . 2_955 ?
N4 Cu1 Cu2 158.06(13) 2_845 2_955 ?
Br1 Cu1 Cu2 81.81(3) . 2_955 ?
Br2 Cu1 Cu2 57.20(2) 2_955 2_955 ?
N4 Cu1 Cu2 118.26(13) 2_845 . ?
Br1 Cu1 Cu2 54.48(2) . . ?
Br2 Cu1 Cu2 125.02(3) 2_955 . ?
Cu2 Cu1 Cu2 70.54(3) 2_955 . ?
N4 Cu1 Cu1 107.78(14) 2_845 2_955 ?
Br1 Cu1 Cu1 106.80(3) . 2_955 ?
Br2 Cu1 Cu1 82.63(3) 2_955 2_955 ?
Cu2 Cu1 Cu1 59.08(2) 2_955 2_955 ?
Cu2 Cu1 Cu1 54.96(2) . 2_955 ?
N1 Cu2 Br1 112.05(12) . . ?
N1 Cu2 Br2 108.52(12) . . ?
Br1 Cu2 Br2 129.66(4) . . ?
N1 Cu2 Cu1 121.97(13) . 2_955 ?
Br1 Cu2 Cu1 117.80(3) . 2_955 ?
Br2 Cu2 Cu1 57.52(2) . 2_955 ?
N1 Cu2 Cu1 164.83(12) . . ?
Br1 Cu2 Cu1 55.07(2) . . ?
Br2 Cu2 Cu1 86.66(3) . . ?
Cu1 Cu2 Cu1 65.96(3) 2_955 . ?
Cu2 Br2 Cu1 65.28(3) . 2_955 ?
Cu2 Br1 Cu1 70.45(3) . . ?
C11 N3 C12 126.3(4) . . ?
C16 N4 C15 118.4(4) . . ?
C16 N4 Cu1 121.4(3) . 2_865 ?
C15 N4 Cu1 120.1(3) . 2_865 ?
C2 N1 C1 118.8(4) . . ?
C2 N1 Cu2 118.1(3) . . ?
C1 N1 Cu2 123.0(4) . . ?
C6 N2 C3 127.3(4) . . ?
C16 C12 C13 118.5(4) . . ?
C16 C12 N3 117.3(4) . . ?
C13 C12 N3 124.2(4) . . ?
O2 C11 N3 122.9(4) . . ?
O2 C11 C10 121.5(4) . . ?
N3 C11 C10 115.6(4) . . ?
C6 C7 C8 112.9(4) . . ?
C4 C3 N2 126.1(4) . . ?
C4 C3 C2 118.0(5) . . ?
N2 C3 C2 115.9(4) . . ?
N4 C16 C12 122.8(4) . . ?
C8 C9 C10 112.2(4) . . ?
C11 C10 C9 110.9(4) . . ?
N4 C15 C14 122.4(5) . . ?
C14 C13 C12 118.4(4) . . ?
N1 C2 C3 122.8(5) . . ?
C15 C14 C13 119.4(4) . . ?
C7 C8 C9 113.0(4) . . ?
C5 C4 C3 118.4(5) . . ?
O1 C6 N2 122.6(5) . . ?
O1 C6 C7 122.4(4) . . ?
N2 C6 C7 115.0(4) . . ?
N1 C1 C5 121.7(5) . . ?
C4 C5 C1 120.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.87
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.346
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.152
