# 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 2023

####################################################################### 
# 
# 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_22ibw_hl2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2257235'
loop_
_audit_author_name
_audit_author_address
'Tunde Yusuf'
;University of Johannesburg
South Africa
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         '2(C13 H8 Br Cl2 N O)'
_chemical_formula_sum            'C26 H16 Br2 Cl4 N2 O2'
_chemical_formula_weight         690.046
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.367(3)
_cell_length_b                   3.9097(8)
_cell_length_c                   23.118(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.068(7)
_cell_angle_gamma                90
_cell_volume                     1298.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    885
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      21.94
_cell_measurement_theta_min      2.28
_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1485 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.4859.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       block
_exptl_crystal_F_000             680.691
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.062
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.9915
_diffrn_reflns_Laue_measured_fraction_max 0.9836
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19851
_diffrn_reflns_point_group_measured_fraction_full 0.9915
_diffrn_reflns_point_group_measured_fraction_max 0.9836
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.76
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.9915
_diffrn_measured_fraction_theta_max 0.9836
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                2010
_reflns_number_total             3056
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.0006
_refine_diff_density_min         -0.8172
_refine_diff_density_rms         0.1462
_refine_ls_d_res_high            0.7595
_refine_ls_d_res_low             11.5589
_refine_ls_goodness_of_fit_ref   1.1092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.1092
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+3.0720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1483
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1a), C7(H7), C4(H4), C9(H9), C5(H5), C10(H10), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br2 Br 0.83679(4) 0.3893(2) 0.49735(2) 0.0885(3) Uani 1.000000 .
Cl1 Cl 0.31422(9) 0.3458(4) 0.28704(6) 0.0691(4) Uani 1.000000 .
Cl2 Cl 1.10483(9) -0.0560(5) 0.34572(7) 0.0823(5) Uani 1.000000 .
O1 O 0.5992(2) 0.7563(11) 0.45471(14) 0.0596(9) Uani 1.000000 .
H1 H 0.6517(3) 0.732(17) 0.4415(11) 0.0894(14) Uiso 1.000000 GR
N1 N 0.7230(2) 0.4627(10) 0.38711(16) 0.0441(9) Uani 1.000000 .
C1 C 0.6555(3) 0.3733(12) 0.3541(2) 0.0446(10) Uani 1.000000 .
H1a H 0.6679(3) 0.2358(12) 0.3222(2) 0.0535(13) Uiso 1.000000 R
C2 C 0.5606(3) 0.4801(12) 0.36504(19) 0.0405(10) Uani 1.000000 .
C3 C 0.5360(3) 0.6583(13) 0.41505(19) 0.0454(11) Uani 1.000000 .
C4 C 0.4424(3) 0.7391(14) 0.4249(2) 0.0545(13) Uani 1.000000 .
H4 H 0.4256(3) 0.8556(14) 0.4584(2) 0.0654(15) Uiso 1.000000 R
C5 C 0.3757(3) 0.6477(14) 0.3857(2) 0.0562(13) Uani 1.000000 .
H5 H 0.3137(3) 0.7036(14) 0.3923(2) 0.0674(16) Uiso 1.000000 R
C6 C 0.4003(3) 0.4723(13) 0.3360(2) 0.0473(11) Uani 1.000000 .
C7 C 0.4914(3) 0.3867(13) 0.3255(2) 0.0474(11) Uani 1.000000 .
H7 H 0.5070(3) 0.2668(13) 0.2922(2) 0.0569(13) Uiso 1.000000 R
C8 C 0.8135(3) 0.3363(12) 0.37566(19) 0.0441(10) Uani 1.000000 .
C9 C 0.8459(3) 0.2696(14) 0.3204(2) 0.0511(12) Uani 1.000000 .
H9 H 0.8069(3) 0.3072(14) 0.2889(2) 0.0614(15) Uiso 1.000000 R
C10 C 0.9349(3) 0.1486(14) 0.3111(2) 0.0536(12) Uani 1.000000 .
H10 H 0.9554(3) 0.1024(14) 0.2737(2) 0.0643(15) Uiso 1.000000 R
C11 C 0.9927(3) 0.0973(14) 0.3572(2) 0.0537(13) Uani 1.000000 .
C12 C 0.9641(3) 0.1629(16) 0.4125(2) 0.0611(14) Uani 1.000000 .
H12 H 1.0037(3) 0.1244(16) 0.4437(2) 0.0733(17) Uiso 1.000000 R
C13 C 0.8746(3) 0.2887(14) 0.4211(2) 0.0510(12) Uani 1.000000 .


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 C13 1.887(5) . ?
Cl1 C6 1.748(5) . ?
Cl2 C11 1.740(5) . ?
O1 H1 0.8200 . ?
O1 C3 1.345(6) . ?
N1 C1 1.282(6) . ?
N1 C8 1.417(5) . ?
C1 H1a 0.9300 . ?
C1 C2 1.449(6) . ?
C2 C3 1.395(6) . ?
C2 C7 1.398(6) . ?
C3 C4 1.400(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(7) . ?
C6 C7 1.372(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(6) . ?
C8 C13 1.380(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(7) . ?
C11 C12 1.368(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(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
C3 O1 H1 109.5 . . ?
C8 N1 C1 119.2(4) . . ?
H1a C1 N1 119.0(3) . . ?
C2 C1 N1 121.9(4) . . ?
C2 C1 H1a 119.0(3) . . ?
C3 C2 C1 121.8(4) . . ?
C7 C2 C1 118.7(4) . . ?
C7 C2 C3 119.4(4) . . ?
C2 C3 O1 122.4(4) . . ?
C4 C3 O1 118.2(4) . . ?
C4 C3 C2 119.4(4) . . ?
H4 C4 C3 119.8(3) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8(3) . . ?
H5 C5 C4 120.0(3) . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0(3) . . ?
C5 C6 Cl1 119.8(4) . . ?
C7 C6 Cl1 119.4(4) . . ?
C7 C6 C5 120.8(4) . . ?
C6 C7 C2 119.9(4) . . ?
H7 C7 C2 120.0(3) . . ?
H7 C7 C6 120.0(3) . . ?
C9 C8 N1 123.2(4) . . ?
C13 C8 N1 119.2(4) . . ?
C13 C8 C9 117.6(4) . . ?
H9 C9 C8 119.3(3) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3(3) . . ?
H10 C10 C9 120.3(3) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3(3) . . ?
C10 C11 Cl2 119.6(4) . . ?
C12 C11 Cl2 119.1(4) . . ?
C12 C11 C10 121.3(4) . . ?
H12 C12 C11 120.7(3) . . ?
C13 C12 C11 118.5(5) . . ?
C13 C12 H12 120.7(3) . . ?
C8 C13 Br2 120.0(3) . . ?
C12 C13 Br2 118.3(4) . . ?
C12 C13 C8 121.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C13 C8 N1 0.3(5) . . . . ?
Br2 C13 C8 C9 177.8(4) . . . . ?
Br2 C13 C12 C11 -178.5(4) . . . . ?
Cl1 C6 C5 C4 178.2(4) . . . . ?
Cl1 C6 C7 C2 -178.6(4) . . . . ?
Cl2 C11 C10 C9 179.9(4) . . . . ?
Cl2 C11 C12 C13 179.4(5) . . . . ?
O1 C3 C2 C1 3.3(6) . . . . ?
O1 C3 C2 C7 -179.9(5) . . . . ?
O1 C3 C4 C5 179.4(5) . . . . ?
N1 C1 C2 C3 -6.3(6) . . . . ?
N1 C1 C2 C7 176.9(5) . . . . ?
N1 C8 C9 C10 179.6(5) . . . . ?
N1 C8 C13 C12 179.5(5) . . . . ?
C1 C2 C3 C4 -176.6(5) . . . . ?
C1 C2 C7 C6 177.3(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C2 C7 C6 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C8 C13 C12 C11 2.3(6) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_22ibw_nil2_173k_0m_a(3)
_database_code_depnum_ccdc_archive 'CCDC 2257237'
loop_
_audit_author_name
_audit_author_address
'Tunde Yusuf'
;University of Johannesburg
South Africa
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Br Cl2 N Ni0.5 O'
_chemical_formula_sum            'C13 H7 Br Cl2 N Ni0.50 O'
_chemical_formula_weight         373.36
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.974(2)
_cell_length_b                   10.356(2)
_cell_length_c                   12.438(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.626(6)
_cell_angle_gamma                90
_cell_volume                     1237.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    172.98
_cell_measurement_theta_max      21.94
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.663
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    4.477
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1652
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49272
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.845
_diffrn_reflns_theta_min         2.600
_diffrn_ambient_temperature      172.98
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1777
_reflns_number_total             3200
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.535
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+2.1237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C9(H9), C6(H6), C12(H12), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Ni1 Ni 0.500000 0.500000 0.500000 0.0362(2) Uani 1 2 d S . P . .
Br1 Br 0.17777(6) 0.42819(6) 0.51015(6) 0.0602(2) Uani 1 1 d . U . . .
Cl1 Cl 0.05770(15) 0.01245(15) 0.23865(11) 0.0560(4) Uani 1 1 d . . . . .
Cl2 Cl 0.86125(18) 0.26752(14) 1.03192(12) 0.0630(5) Uani 1 1 d . . . . .
O2 O 0.5773(4) 0.5562(3) 0.6412(3) 0.0425(9) Uani 1 1 d . . . . .
N1 N 0.4715(4) 0.3334(4) 0.5481(3) 0.0351(9) Uani 1 1 d . . . . .
C2 C 0.3722(5) 0.2523(5) 0.4745(4) 0.0339(11) Uani 1 1 d . . . . .
C7 C 0.5324(5) 0.2868(5) 0.6436(4) 0.0347(11) Uani 1 1 d . . . . .
H7 H 0.512722 0.199429 0.656923 0.042 Uiso 1 1 calc R U . . .
C8 C 0.6251(5) 0.3522(5) 0.7304(4) 0.0347(11) Uani 1 1 d . . . . .
C13 C 0.6422(5) 0.4861(5) 0.7238(4) 0.0343(11) Uani 1 1 d . . . . .
C11 C 0.7999(5) 0.4798(5) 0.9060(4) 0.0373(12) Uani 1 1 d . . . . .
H11 H 0.861761 0.523194 0.966745 0.045 Uiso 1 1 calc R U . . .
C1 C 0.2356(5) 0.2844(5) 0.4470(4) 0.0364(11) Uani 1 1 d . . . . .
C4 C 0.1811(6) 0.1059(5) 0.3288(4) 0.0405(13) Uani 1 1 d . . . . .
C9 C 0.6927(5) 0.2857(5) 0.8264(4) 0.0403(12) Uani 1 1 d . . . . .
H9 H 0.677596 0.195610 0.831917 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4145(6) 0.1451(5) 0.4290(4) 0.0405(12) Uani 1 1 d . . . . .
H6 H 0.510109 0.121725 0.448041 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7793(5) 0.3483(5) 0.9114(4) 0.0403(12) Uani 1 1 d . . . . .
C12 C 0.7329(5) 0.5460(5) 0.8151(4) 0.0397(12) Uani 1 1 d . . . . .
H12 H 0.747642 0.636420 0.812722 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1369(6) 0.2107(5) 0.3731(4) 0.0426(13) Uani 1 1 d . . . . .
H3 H 0.041093 0.233272 0.354274 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3167(6) 0.0709(5) 0.3550(4) 0.0441(13) Uani 1 1 d . . . . .
H5 H 0.344492 -0.004240 0.322715 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O2 1.813(3) . ?
Ni1 O2 1.813(3) 3_666 ?
Ni1 N1 1.873(4) 3_666 ?
Ni1 N1 1.873(4) . ?
Br1 C1 1.848(5) . ?
Cl1 C4 1.722(5) . ?
Cl2 C10 1.719(5) . ?
O2 C13 1.282(5) . ?
N1 C2 1.427(6) . ?
N1 C7 1.274(6) . ?
C2 C1 1.353(7) . ?
C2 C6 1.364(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(6) . ?
C8 C13 1.403(7) . ?
C8 C9 1.386(7) . ?
C13 C12 1.392(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.382(7) . ?
C11 C12 1.336(7) . ?
C1 C3 1.382(7) . ?
C4 C3 1.345(7) . ?
C4 C5 1.353(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.339(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.380(7) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5 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
O2 Ni1 O2 180.0 . 3_666 ?
O2 Ni1 N1 87.28(15) 3_666 . ?
O2 Ni1 N1 92.72(15) . . ?
O2 Ni1 N1 87.28(15) . 3_666 ?
O2 Ni1 N1 92.72(15) 3_666 3_666 ?
N1 Ni1 N1 180.0 3_666 . ?
C13 O2 Ni1 125.9(3) . . ?
C2 N1 Ni1 118.4(3) . . ?
C7 N1 Ni1 124.8(3) . . ?
C7 N1 C2 116.7(4) . . ?
C1 C2 N1 119.7(4) . . ?
C1 C2 C6 119.9(5) . . ?
C6 C2 N1 120.4(5) . . ?
N1 C7 H7 117.0 . . ?
N1 C7 C8 126.1(5) . . ?
C8 C7 H7 117.0 . . ?
C7 C8 C13 120.1(4) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 C13 120.2(4) . . ?
O2 C13 C8 124.3(4) . . ?
O2 C13 C12 118.6(4) . . ?
C12 C13 C8 117.1(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C2 C1 Br1 119.9(4) . . ?
C2 C1 C3 121.4(5) . . ?
C3 C1 Br1 118.7(4) . . ?
C3 C4 Cl1 117.7(4) . . ?
C3 C4 C5 122.3(5) . . ?
C5 C4 Cl1 120.0(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(5) . . ?
C10 C9 H9 120.0 . . ?
C2 C6 H6 120.4 . . ?
C2 C6 C5 119.2(5) . . ?
C5 C6 H6 120.4 . . ?
C11 C10 Cl2 118.7(4) . . ?
C9 C10 Cl2 120.4(4) . . ?
C9 C10 C11 120.8(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 121.9(5) . . ?
C11 C12 H12 119.0 . . ?
C1 C3 H3 121.1 . . ?
C4 C3 C1 117.7(5) . . ?
C4 C3 H3 121.1 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O2 C13 C8 -22.7(7) . . . . ?
Ni1 O2 C13 C12 159.3(4) . . . . ?
Ni1 N1 C2 C1 -65.8(6) . . . . ?
Ni1 N1 C2 C6 112.1(4) . . . . ?
Ni1 N1 C7 C8 3.1(8) . . . . ?
Br1 C1 C3 C4 -179.5(4) . . . . ?
Cl1 C4 C3 C1 178.9(4) . . . . ?
Cl1 C4 C5 C6 -178.7(4) . . . . ?
O2 Ni1 N1 C2 -19.5(4) 3_666 . . . ?
O2 Ni1 N1 C2 160.5(4) . . . . ?
O2 Ni1 N1 C7 162.1(4) 3_666 . . . ?
O2 Ni1 N1 C7 -17.9(4) . . . . ?
O2 C13 C12 C11 177.3(5) . . . . ?
N1 Ni1 O2 C13 27.5(4) . . . . ?
N1 Ni1 O2 C13 -152.5(4) 3_666 . . . ?
N1 C2 C1 Br1 -3.0(6) . . . . ?
N1 C2 C1 C3 177.8(4) . . . . ?
N1 C2 C6 C5 -177.7(4) . . . . ?
N1 C7 C8 C13 10.2(8) . . . . ?
N1 C7 C8 C9 -174.5(5) . . . . ?
C2 N1 C7 C8 -175.4(5) . . . . ?
C2 C1 C3 C4 -0.3(8) . . . . ?
C2 C6 C5 C4 0.2(8) . . . . ?
C7 N1 C2 C1 112.8(5) . . . . ?
C7 N1 C2 C6 -69.3(6) . . . . ?
C7 C8 C13 O2 -0.2(8) . . . . ?
C7 C8 C13 C12 177.8(5) . . . . ?
C7 C8 C9 C10 -178.2(5) . . . . ?
C8 C13 C12 C11 -0.8(8) . . . . ?
C8 C9 C10 Cl2 178.8(4) . . . . ?
C8 C9 C10 C11 1.6(8) . . . . ?
C13 C8 C9 C10 -2.9(8) . . . . ?
C1 C2 C6 C5 0.1(8) . . . . ?
C9 C8 C13 O2 -175.6(5) . . . . ?
C9 C8 C13 C12 2.5(7) . . . . ?
C6 C2 C1 Br1 179.1(4) . . . . ?
C6 C2 C1 C3 -0.1(8) . . . . ?
C10 C11 C12 C13 -0.5(8) . . . . ?
C12 C11 C10 Cl2 -177.2(4) . . . . ?
C12 C11 C10 C9 0.1(8) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C5 C4 C3 C1 0.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_22cu_L2_173K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2257236'
loop_
_audit_author_name
_audit_author_address
'Tunde Yusuf'
;University of Johannesburg
South Africa
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-09-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C26 H14 Br2 Cl4 Cu N2 O2'
_chemical_formula_sum            'C26 H14 Br2 Cl4 Cu N2 O2'
_chemical_formula_weight         751.576
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.966(4)
_cell_length_b                   10.774(4)
_cell_length_c                   11.925(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.479(8)
_cell_angle_gamma                90
_cell_volume                     1245.1(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    885
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.94
_cell_measurement_theta_min      2.28
_exptl_absorpt_coefficient_mu    4.546
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.6417.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_description       block
_exptl_crystal_F_000             735.430
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_Laue_measured_fraction_full 0.9978
_diffrn_reflns_Laue_measured_fraction_max 0.9899
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15573
_diffrn_reflns_point_group_measured_fraction_full 0.9978
_diffrn_reflns_point_group_measured_fraction_max 0.9899
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         2.58
_diffrn_ambient_temperature      173.01
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9899
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1742
_reflns_number_total             3140
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.1437
_refine_diff_density_min         -1.2181
_refine_diff_density_rms         0.2956
_refine_ls_d_res_high            0.7438
_refine_ls_d_res_low             7.8929
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      0.9991
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.1096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1138
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.18922(6) 0.56434(5) 0.49366(5) 0.0466(2) Uani 1.000000 1 . . .
Cu1 Cu 0.5 0.5 0.5 0.0306(2) Uani 1.000000 2 S T P
Cl1 Cl 0.06976(14) 0.98454(13) 0.23935(12) 0.0471(4) Uani 1.000000 1 . . .
Cl2 Cl 0.88304(15) 0.74320(13) 1.03171(12) 0.0499(4) Uani 1.000000 1 . . .
O1 O 0.4355(4) 0.5486(3) 0.3453(3) 0.0350(8) Uani 1.000000 1 . . .
N1 N 0.4755(4) 0.6712(3) 0.5491(3) 0.0278(9) Uani 1.000000 1 . . .
C1 C 0.2447(5) 0.7137(4) 0.4389(4) 0.0293(11) Uani 1.000000 1 . . .
C2 C 0.3805(5) 0.7497(4) 0.4727(4) 0.0275(11) Uani 1.000000 1 . . .
C3 C 0.4217(5) 0.8564(4) 0.4293(4) 0.0309(11) Uani 1.000000 1 . . .
H3 H 0.5159(5) 0.8806(4) 0.4500(4) 0.0371(14) Uiso 1.000000 1 R . .
C4 C 0.3272(5) 0.9286(4) 0.3557(4) 0.0346(12) Uani 1.000000 1 . . .
H4 H 0.3550(5) 1.0034(4) 0.3255(4) 0.0415(14) Uiso 1.000000 1 R . .
C5 C 0.1920(5) 0.8914(5) 0.3262(4) 0.0327(12) Uani 1.000000 1 . . .
C6 C 0.1480(5) 0.7843(4) 0.3647(4) 0.0313(12) Uani 1.000000 1 . . .
H6 H 0.0543(5) 0.7588(4) 0.3414(4) 0.0375(14) Uiso 1.000000 1 R . .
C7 C 0.5396(4) 0.7169(4) 0.6448(4) 0.0285(11) Uani 1.000000 1 . . .
H7 H 0.5253(4) 0.8024(4) 0.6579(4) 0.0342(13) Uiso 1.000000 1 R . .
C8 C 0.6312(5) 0.6506(4) 0.7341(4) 0.0303(11) Uani 1.000000 1 . . .
C9 C 0.7065(5) 0.7185(4) 0.8264(4) 0.0327(12) Uani 1.000000 1 . . .
H9 H 0.6979(5) 0.8063(4) 0.8273(4) 0.0392(14) Uiso 1.000000 1 R . .
C10 C 0.7920(5) 0.6594(5) 0.9151(4) 0.0325(12) Uani 1.000000 1 . . .
C11 C 0.8070(5) 0.5325(4) 0.9158(4) 0.0311(12) Uani 1.000000 1 . . .
H11 H 0.8694(5) 0.4923(4) 0.9774(4) 0.0373(14) Uiso 1.000000 1 R . .
C12 C 0.7305(5) 0.4654(4) 0.8263(4) 0.0311(12) Uani 1.000000 1 . . .
H12 H 0.7396(5) 0.3776(4) 0.8275(4) 0.0374(14) Uiso 1.000000 1 R . .
C13 C 0.6392(5) 0.5212(4) 0.7328(4) 0.0290(11) Uani 1.000000 1 . . .


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
Br1 C1 1.868(5) . ?
Cu1 O1 1.880(3) . ?
Cu1 O1 1.880(3) 3_666 ?
Cu1 N1 1.968(4) . ?
Cu1 N1 1.968(4) 3_666 ?
Cl1 C5 1.725(5) . ?
Cl2 C10 1.727(5) . ?
O1 C13 1.290(5) 3_666 ?
N1 C2 1.428(5) . ?
N1 C7 1.271(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.376(6) . ?
C2 C3 1.363(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(7) . ?
C5 C6 1.352(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.423(6) . ?
C8 C9 1.387(6) . ?
C8 C13 1.396(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.353(6) . ?
C10 C11 1.375(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(6) . ?

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 . ?
N1 Cu1 O1 90.39(14) 3_666 . ?
N1 Cu1 O1 89.61(14) 3_666 3_666 ?
N1 Cu1 O1 90.39(14) . 3_666 ?
N1 Cu1 O1 89.61(14) . . ?
N1 Cu1 N1 180.0 3_666 . ?
C13 O1 Cu1 123.6(3) 3_666 . ?
C2 N1 Cu1 118.4(3) . . ?
C7 N1 Cu1 124.0(3) . . ?
C7 N1 C2 117.6(4) . . ?
C2 C1 Br1 119.4(4) . . ?
C6 C1 Br1 118.7(4) . . ?
C6 C1 C2 121.8(4) . . ?
C1 C2 N1 118.8(4) . . ?
C3 C2 N1 121.9(4) . . ?
C3 C2 C1 119.3(4) . . ?
H3 C3 C2 120.0(3) . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0(3) . . ?
H4 C4 C3 120.5(3) . . ?
C5 C4 C3 119.1(5) . . ?
C5 C4 H4 120.5(3) . . ?
C4 C5 Cl1 119.9(4) . . ?
C6 C5 Cl1 117.4(4) . . ?
C6 C5 C4 122.6(5) . . ?
C5 C6 C1 117.1(4) . . ?
H6 C6 C1 121.4(3) . . ?
H6 C6 C5 121.4(3) . . ?
H7 C7 N1 117.3(3) . . ?
C8 C7 N1 125.3(4) . . ?
C8 C7 H7 117.3(3) . . ?
C9 C8 C7 117.6(4) . . ?
C13 C8 C7 121.4(4) . . ?
C13 C8 C9 120.9(4) . . ?
H9 C9 C8 120.1(3) . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9 120.1(3) . . ?
C9 C10 Cl2 120.1(4) . . ?
C11 C10 Cl2 118.6(4) . . ?
C11 C10 C9 121.3(4) . . ?
H11 C11 C10 120.6(3) . . ?
C12 C11 C10 118.8(4) . . ?
C12 C11 H11 120.6(3) . . ?
H12 C12 C11 118.8(3) . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 H12 118.8(3) . . ?
C8 C13 O1 124.4(4) . 3_666 ?
C12 C13 O1 118.9(4) . 3_666 ?
C12 C13 C8 116.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 N1 -0.0(4) . . . . ?
Br1 C1 C2 C3 177.6(4) . . . . ?
Br1 C1 C6 C5 -179.6(4) . . . . ?
Cu1 O1 C13 C8 31.3(4) . 3_666 . . ?
Cu1 O1 C13 C8 -31.3(4) . . 3_666 3_666 ?
Cu1 O1 C13 C12 151.9(4) . . 3_666 3_666 ?
Cu1 O1 C13 C12 -151.9(4) . 3_666 . . ?
Cu1 N1 C2 C1 58.9(4) 3_666 . . . ?
Cu1 N1 C2 C1 58.9(4) . . . . ?
Cu1 N1 C2 C3 -118.6(3) . . . . ?
Cu1 N1 C2 C3 -118.6(3) 3_666 . . . ?
Cu1 N1 C7 C8 -4.4(4) . . . . ?
Cu1 N1 C7 C8 -4.4(4) 3_666 . . . ?
Cl1 C5 C4 C3 176.9(4) . . . . ?
Cl1 C5 C6 C1 -176.6(4) . . . . ?
Cl2 C10 C9 C8 -178.6(4) . . . . ?
Cl2 C10 C11 C12 177.1(4) . . . . ?
O1 C13 C8 C7 -1.7(6) 3_666 . . . ?
O1 C13 C8 C9 174.3(5) 3_666 . . . ?
O1 C13 C12 C11 -176.0(4) 3_666 . . . ?
N1 C2 C1 C6 -179.4(4) . . . . ?
N1 C2 C3 C4 179.6(4) . . . . ?
N1 C7 C8 C9 171.6(5) . . . . ?
N1 C7 C8 C13 -12.2(6) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
C1 C6 C5 C4 2.0(6) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C7 C8 C9 C10 178.1(4) . . . . ?
C7 C8 C13 C12 -178.6(5) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C8 C13 C12 C11 1.0(5) . . . . ?
C9 C10 C11 C12 -1.9(6) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
