# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2143545'
loop_
_audit_author_name
_audit_author_address
'Mukesh Choudhary'
;NIT Patna
India
;
_audit_update_record             
;
2022-01-21 deposited with the CCDC.	2022-03-17 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         ?
_chemical_formula_sum            'C28 H20 Cl4 Cu N2 O4'
_chemical_formula_weight         653.80

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'
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'

_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                   12.4630(12)
_cell_length_b                   9.2765(10)
_cell_length_c                   12.6425(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.863(3)
_cell_angle_gamma                90
_cell_volume                     1356.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9686
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      33.08

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.238
_shelx_estimated_absorpt_T_min   0.723
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52736
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  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       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3943
_reflns_number_gt                3300
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0703P)²+0.4715P] 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         3943
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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 0.500000 0.500000 0.500000 0.02631(11) Uani 1 2 d S . P . .
Cl1 Cl 1.06218(4) 0.18781(7) 0.82472(5) 0.04838(16) Uani 1 1 d . . . . .
Cl2 Cl 0.87991(5) 0.63281(8) 0.54220(7) 0.0659(2) Uani 1 1 d . . . . .
C1 C 0.62510(16) 0.2721(2) 0.65815(17) 0.0334(4) Uani 1 1 d . . . . .
H1 H 0.625486 0.189400 0.702572 0.040 Uiso 1 1 calc R U . . .
C2 C 0.73662(15) 0.3262(2) 0.66696(16) 0.0303(4) Uani 1 1 d . . . . .
C3 C 0.74734(14) 0.44991(19) 0.60616(15) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.86250(17) 0.4858(2) 0.61729(18) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.95764(16) 0.4085(2) 0.68397(16) 0.0337(4) Uani 1 1 d . . . . .
H5 H 1.032928 0.436631 0.689817 0.040 Uiso 1 1 calc R U . . .
C6 C 0.94246(16) 0.2887(2) 0.74268(17) 0.0338(4) Uani 1 1 d . . . . .
C7 C 0.83417(17) 0.2471(2) 0.73506(18) 0.0369(4) Uani 1 1 d . . . . .
H7 H 0.825099 0.164938 0.775772 0.044 Uiso 1 1 calc R U . . .
C8 C 0.42994(15) 0.23548(19) 0.59922(16) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.38125(18) 0.2586(2) 0.68000(18) 0.0369(4) Uani 1 1 d . . . . .
H9 H 0.407562 0.335781 0.732805 0.044 Uiso 1 1 calc R U . . .
C10 C 0.29374(18) 0.1683(2) 0.68324(18) 0.0386(4) Uani 1 1 d . . . . .
H10 H 0.261083 0.182864 0.739364 0.046 Uiso 1 1 calc R U . . .
C11 C 0.25375(17) 0.0573(2) 0.60545(17) 0.0344(4) Uani 1 1 d . . . . .
C12 C 0.3008(2) 0.0356(2) 0.52302(19) 0.0393(4) Uani 1 1 d . . . . .
H12 H 0.272971 -0.039636 0.468679 0.047 Uiso 1 1 calc R U . . .
C13 C 0.38952(18) 0.1258(2) 0.52102(18) 0.0368(4) Uani 1 1 d . . . . .
H13 H 0.422437 0.111477 0.465067 0.044 Uiso 1 1 calc R U . . .
C14 C 0.1182(3) -0.1324(3) 0.5305(3) 0.0600(7) Uani 1 1 d . . . . .
H14A H 0.081718 -0.086067 0.455910 0.090 Uiso 1 1 calc R U . . .
H14B H 0.060103 -0.187427 0.548478 0.090 Uiso 1 1 calc R U . . .
H14C H 0.179392 -0.197482 0.528568 0.090 Uiso 1 1 calc R U . . .
N1 N 0.52538(13) 0.32301(16) 0.59716(13) 0.0287(3) Uani 1 1 d . . . . .
O1 O 0.66176(11) 0.52963(15) 0.54432(13) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.16684(17) -0.0249(2) 0.61539(16) 0.0493(4) 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 O1 1.9007(13) . ?
Cu1 O1 1.9007(13) 3_666 ?
Cu1 N1 2.0037(15) . ?
Cu1 N1 2.0038(15) 3_666 ?
Cl1 C6 1.7395(19) . ?
Cl2 C4 1.7207(19) . ?
C1 N1 1.284(2) . ?
C1 C2 1.442(2) . ?
C1 H1 0.9500 . ?
C2 C7 1.406(3) . ?
C2 C3 1.415(2) . ?
C3 O1 1.294(2) . ?
C3 C4 1.428(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.376(3) . ?
C8 C9 1.385(3) . ?
C8 N1 1.449(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 O2 1.368(2) . ?
C11 C12 1.388(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O2 1.424(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 N1 91.71(6) . . ?
O1 Cu1 N1 88.29(6) 3_666 . ?
O1 Cu1 N1 88.29(6) . 3_666 ?
O1 Cu1 N1 91.71(6) 3_666 3_666 ?
N1 Cu1 N1 180.00(8) . 3_666 ?
N1 C1 C2 127.45(17) . . ?
N1 C1 H1 116.3 . . ?
C2 C1 H1 116.3 . . ?
C7 C2 C3 121.37(16) . . ?
C7 C2 C1 117.03(17) . . ?
C3 C2 C1 121.55(16) . . ?
O1 C3 C2 124.64(16) . . ?
O1 C3 C4 119.88(16) . . ?
C2 C3 C4 115.49(16) . . ?
C5 C4 C3 123.00(17) . . ?
C5 C4 Cl2 119.68(15) . . ?
C3 C4 Cl2 117.32(14) . . ?
C4 C5 C6 119.21(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.94(17) . . ?
C7 C6 Cl1 119.56(15) . . ?
C5 C6 Cl1 119.49(15) . . ?
C6 C7 C2 119.99(18) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 120.03(17) . . ?
C13 C8 N1 118.98(16) . . ?
C9 C8 N1 120.97(17) . . ?
C8 C9 C10 119.53(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.52(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O2 C11 C10 115.98(18) . . ?
O2 C11 C12 123.96(19) . . ?
C10 C11 C12 120.06(17) . . ?
C11 C12 C13 119.11(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 120.73(18) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C8 113.63(15) . . ?
C1 N1 Cu1 124.47(13) . . ?
C8 N1 Cu1 121.81(11) . . ?
C3 O1 Cu1 129.83(12) . . ?
C11 O2 C14 116.74(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 -176.6(2) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
C7 C2 C3 O1 -178.20(19) . . . . ?
C1 C2 C3 O1 4.4(3) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C4 -176.18(18) . . . . ?
O1 C3 C4 C5 178.13(19) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
O1 C3 C4 Cl2 -2.1(3) . . . . ?
C2 C3 C4 Cl2 178.44(15) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
Cl2 C4 C5 C6 -178.95(16) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 Cl1 178.54(16) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
Cl1 C6 C7 C2 -178.62(17) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C1 C2 C7 C6 176.9(2) . . . . ?
C13 C8 C9 C10 1.7(3) . . . . ?
N1 C8 C9 C10 -176.81(19) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 O2 -179.6(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
O2 C11 C12 C13 -179.8(2) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
N1 C8 C13 C12 177.50(19) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C2 C1 N1 C8 174.49(19) . . . . ?
C2 C1 N1 Cu1 -2.2(3) . . . . ?
C13 C8 N1 C1 -88.5(2) . . . . ?
C9 C8 N1 C1 90.0(2) . . . . ?
C13 C8 N1 Cu1 88.28(19) . . . . ?
C9 C8 N1 Cu1 -93.2(2) . . . . ?
C2 C3 O1 Cu1 -8.1(3) . . . . ?
C4 C3 O1 Cu1 172.56(14) . . . . ?
C10 C11 O2 C14 175.1(2) . . . . ?
C12 C11 O2 C14 -4.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O1 0.95 2.55 3.428(2) 153.8 2_646 yes
C14 H14B Cl2 0.98 2.77 3.731(2) 165.3 1_445 yes

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2143550'
loop_
_audit_author_name
_audit_author_address
'Mukesh Choudhary'
;NIT Patna
India
;
_audit_update_record             
;
2022-01-21 deposited with the CCDC.	2022-03-17 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         ?
_chemical_formula_sum            'C26 H14 Br6 Cu N2 O2'
_chemical_formula_weight         929.39

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'
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'
Br Br -0.2901 2.4595 '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                   10.1185(13)
_cell_length_b                   10.9809(12)
_cell_length_c                   12.5803(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.795(4)
_cell_angle_gamma                90
_cell_volume                     1357.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9508
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      31.02

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             878
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    9.664
_shelx_estimated_absorpt_T_min   0.248
_shelx_estimated_absorpt_T_max   0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60792
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3949
_reflns_number_gt                2851
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0361P)²+3.1132P] 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         3949
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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
Cu2 Cu 0.500000 0.500000 0.500000 0.03356(18) Uani 1 2 d S . P . .
C1 C 0.4594(4) 0.2862(4) 0.3587(4) 0.0346(9) Uani 1 1 d . . . . .
H1 H 0.471637 0.202134 0.346044 0.042 Uiso 1 1 calc R U . . .
C2 C 0.3714(4) 0.3537(4) 0.2719(3) 0.0312(8) Uani 1 1 d . . . . .
C3 C 0.3655(5) 0.4831(4) 0.2740(3) 0.0337(9) Uani 1 1 d . . . . .
C4 C 0.2806(5) 0.5411(4) 0.1824(4) 0.0382(10) Uani 1 1 d . . . . .
H4 H 0.274308 0.627422 0.181352 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2064(5) 0.4756(4) 0.0945(4) 0.0383(10) Uani 1 1 d . . . . .
H5 H 0.148172 0.516526 0.034835 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2174(5) 0.3491(4) 0.0938(4) 0.0367(9) Uani 1 1 d . . . . .
C7 C 0.2985(4) 0.2885(4) 0.1807(4) 0.0357(9) Uani 1 1 d . . . . .
H7 H 0.305266 0.202224 0.179175 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6160(4) 0.2515(3) 0.5248(3) 0.0308(8) Uani 1 1 d . . . . .
C9 C 0.7517(5) 0.2862(4) 0.5584(3) 0.0350(9) Uani 1 1 d . . . . .
C10 C 0.8462(5) 0.2165(4) 0.6299(4) 0.0373(9) Uani 1 1 d . . . . .
H10 H 0.938722 0.241099 0.651622 0.045 Uiso 1 1 calc R U . . .
C11 C 0.8031(4) 0.1106(4) 0.6690(3) 0.0361(9) Uani 1 1 d . . . . .
C12 C 0.6688(5) 0.0747(4) 0.6394(4) 0.0404(10) Uani 1 1 d . . . . .
H12 H 0.640787 0.002051 0.668707 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5750(5) 0.1447(4) 0.5666(4) 0.0354(9) Uani 1 1 d . . . . .
H13 H 0.482513 0.119749 0.545251 0.042 Uiso 1 1 calc R U . . .
N1 N 0.5227(4) 0.3293(3) 0.4516(3) 0.0310(7) Uani 1 1 d . . . . .
O1 O 0.4370(4) 0.5504(3) 0.3522(3) 0.0421(8) Uani 1 1 d . . . . .
Br1 Br 0.93489(6) 0.01334(5) 0.76448(4) 0.05180(16) Uani 1 1 d . . . . .
Br2 Br 0.80824(5) 0.43291(5) 0.50459(5) 0.05803(18) Uani 1 1 d . . . . .
Br3 Br 0.12232(6) 0.26071(5) -0.03068(4) 0.05581(17) 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 O1 1.899(3) . ?
Cu2 O1 1.899(3) 3_666 ?
Cu2 N1 2.001(3) . ?
Cu2 N1 2.001(3) 3_666 ?
C1 N1 1.282(5) . ?
C1 C2 1.439(6) . ?
C1 H1 0.9500 . ?
C2 C7 1.404(6) . ?
C2 C3 1.423(6) . ?
C3 O1 1.303(5) . ?
C3 C4 1.414(6) . ?
C4 C5 1.381(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(6) . ?
C6 Br3 1.898(4) . ?
C7 H7 0.9500 . ?
C8 C13 1.388(6) . ?
C8 C9 1.390(6) . ?
C8 N1 1.433(5) . ?
C9 C10 1.378(6) . ?
C9 Br2 1.889(4) . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(7) . ?
C11 Br1 1.897(4) . ?
C12 C13 1.385(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu2 O1 180.0(2) . 3_666 ?
O1 Cu2 N1 90.64(13) . . ?
O1 Cu2 N1 89.36(13) 3_666 . ?
O1 Cu2 N1 89.36(13) . 3_666 ?
O1 Cu2 N1 90.63(13) 3_666 3_666 ?
N1 Cu2 N1 180.0 . 3_666 ?
N1 C1 C2 125.9(4) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C7 C2 C3 120.6(4) . . ?
C7 C2 C1 117.8(4) . . ?
C3 C2 C1 121.4(4) . . ?
O1 C3 C4 118.7(4) . . ?
O1 C3 C2 124.2(4) . . ?
C4 C3 C2 117.1(4) . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 Br3 119.9(3) . . ?
C5 C6 Br3 119.3(3) . . ?
C6 C7 C2 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C13 C8 C9 118.6(4) . . ?
C13 C8 N1 122.4(4) . . ?
C9 C8 N1 118.9(4) . . ?
C10 C9 C8 121.8(4) . . ?
C10 C9 Br2 119.0(3) . . ?
C8 C9 Br2 119.1(3) . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 121.5(4) . . ?
C10 C11 Br1 117.9(3) . . ?
C12 C11 Br1 120.6(3) . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C1 N1 C8 118.3(3) . . ?
C1 N1 Cu2 123.7(3) . . ?
C8 N1 Cu2 118.0(2) . . ?
C3 O1 Cu2 124.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 -172.9(4) . . . . ?
N1 C1 C2 C3 11.7(7) . . . . ?
C7 C2 C3 O1 -175.3(4) . . . . ?
C1 C2 C3 O1 0.0(7) . . . . ?
C7 C2 C3 C4 1.9(7) . . . . ?
C1 C2 C3 C4 177.2(4) . . . . ?
O1 C3 C4 C5 177.3(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
C4 C5 C6 C7 1.6(7) . . . . ?
C4 C5 C6 Br3 -176.8(3) . . . . ?
C5 C6 C7 C2 0.2(7) . . . . ?
Br3 C6 C7 C2 178.5(3) . . . . ?
C3 C2 C7 C6 -2.0(7) . . . . ?
C1 C2 C7 C6 -177.4(4) . . . . ?
C13 C8 C9 C10 1.3(7) . . . . ?
N1 C8 C9 C10 179.0(4) . . . . ?
C13 C8 C9 Br2 -178.7(3) . . . . ?
N1 C8 C9 Br2 -1.0(5) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
Br2 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C9 C10 C11 Br1 178.4(3) . . . . ?
C10 C11 C12 C13 1.5(7) . . . . ?
Br1 C11 C12 C13 -177.7(4) . . . . ?
C11 C12 C13 C8 -0.7(7) . . . . ?
C9 C8 C13 C12 -0.6(7) . . . . ?
N1 C8 C13 C12 -178.2(4) . . . . ?
C2 C1 N1 C8 -174.4(4) . . . . ?
C2 C1 N1 Cu2 5.0(6) . . . . ?
C13 C8 N1 C1 -61.8(6) . . . . ?
C9 C8 N1 C1 120.6(5) . . . . ?
C13 C8 N1 Cu2 118.7(4) . . . . ?
C9 C8 N1 Cu2 -58.9(5) . . . . ?
C4 C3 O1 Cu2 154.8(3) . . . . ?
C2 C3 O1 Cu2 -28.0(6) . . . . ?
N1 Cu2 O1 C3 33.6(4) . . . . ?
N1 Cu2 O1 C3 -146.4(4) 3_666 . . . ?

_refine_diff_density_max         1.165
_refine_diff_density_min         -1.407
_refine_diff_density_rms         0.148

