# 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 2024

####################################################################### 
# 
# 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_xm_a
_database_code_depnum_ccdc_archive 'CCDC 2338587'
loop_
_audit_author_name
_audit_author_address
'SEGUN OLADIPO'
;OLABISI ONABANJO UNIVERSITY
Nigeria
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-07-03 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         'C34 H20 Cl4 Cu N2 O2'
_chemical_formula_sum            'C34 H20 Cl4 Cu N2 O2'
_chemical_formula_weight         693.86

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3287(6)
_cell_length_b                   15.8649(11)
_cell_length_c                   21.7887(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2879.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7540
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.29

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.167
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37728
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3311
_reflns_number_gt                2874
_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-Seed (Barbour, 2020; Atwood & Barbour, 2003)'
_computing_publication_material  ?
_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)+(0.0400P)²+7.3444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 1.000000 0.500000 0.500000 0.01412(13) Uani 1 2 d S . P . .
Cl1 Cl 0.70706(9) 0.28306(5) 0.58524(3) 0.02437(18) Uani 1 1 d . . . . .
Cl2 Cl 0.69114(9) 0.60922(4) 0.51269(3) 0.02274(17) Uani 1 1 d . . . . .
O1 O 1.0113(2) 0.48209(12) 0.41362(9) 0.0175(4) Uani 1 1 d . . . . .
N1 N 0.8001(3) 0.43394(15) 0.50380(10) 0.0150(5) Uani 1 1 d . . . . .
C12 C 0.6941(3) 0.44831(18) 0.55298(12) 0.0158(5) Uani 1 1 d . . . . .
C9 C 0.7791(3) 0.29432(17) 0.36688(12) 0.0144(5) Uani 1 1 d . . . . .
C4 C 0.8325(3) 0.28842(18) 0.30530(13) 0.0175(5) Uani 1 1 d . . . . .
C11 C 0.7562(3) 0.37940(17) 0.46219(12) 0.0158(5) Uani 1 1 d . . . . .
H11 H 0.662382 0.347402 0.470599 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8353(3) 0.36310(17) 0.40535(12) 0.0155(5) Uani 1 1 d . . . . .
C5 C 0.7766(3) 0.22180(19) 0.26774(13) 0.0202(6) Uani 1 1 d . . . . .
H5 H 0.810155 0.218943 0.226115 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6739(3) 0.23143(18) 0.38849(13) 0.0188(6) Uani 1 1 d . . . . .
H8 H 0.637150 0.233871 0.429726 0.023 Uiso 1 1 calc R U . . .
C1 C 0.9515(3) 0.42020(17) 0.38264(12) 0.0162(5) Uani 1 1 d . . . . .
C13 C 0.6417(3) 0.38640(18) 0.59389(13) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.9447(4) 0.34950(19) 0.28337(13) 0.0219(6) Uani 1 1 d . . . . .
H3 H 0.979343 0.346701 0.241880 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6754(4) 0.16153(19) 0.29028(14) 0.0228(6) Uani 1 1 d . . . . .
H6 H 0.640685 0.116569 0.264719 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6231(4) 0.16635(18) 0.35124(14) 0.0205(6) Uani 1 1 d . . . . .
H7 H 0.552274 0.124688 0.367009 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6385(3) 0.53042(18) 0.56403(13) 0.0178(6) Uani 1 1 d . . . . .
C2 C 1.0030(4) 0.41135(19) 0.32004(13) 0.0210(6) Uani 1 1 d . . . . .
H2 H 1.079836 0.449736 0.303973 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5407(4) 0.5501(2) 0.61356(14) 0.0228(6) Uani 1 1 d . . . . .
H16 H 0.509207 0.606743 0.620967 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5400(4) 0.4044(2) 0.64169(13) 0.0227(6) Uani 1 1 d . . . . .
H14 H 0.503795 0.360496 0.667877 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4901(4) 0.4863(2) 0.65185(14) 0.0246(7) Uani 1 1 d . . . . .
H15 H 0.420768 0.498676 0.685281 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9057(19) . ?
Cu1 O1 1.9057(19) 5_766 ?
Cu1 N1 1.969(2) . ?
Cu1 N1 1.969(2) 5_766 ?
Cl1 C13 1.738(3) . ?
Cl2 C17 1.734(3) . ?
O1 C1 1.292(3) . ?
N1 C11 1.305(3) . ?
N1 C12 1.407(3) . ?
C12 C13 1.396(4) . ?
C12 C17 1.403(4) . ?
C9 C8 1.409(4) . ?
C9 C4 1.417(4) . ?
C9 C10 1.453(4) . ?
C4 C5 1.415(4) . ?
C4 C3 1.428(4) . ?
C11 C10 1.426(4) . ?
C11 H11 0.9500 . ?
C10 C1 1.415(4) . ?
C5 C6 1.366(4) . ?
C5 H5 0.9500 . ?
C8 C7 1.380(4) . ?
C8 H8 0.9500 . ?
C1 C2 1.437(4) . ?
C13 C14 1.373(4) . ?
C3 C2 1.356(4) . ?
C3 H3 0.9500 . ?
C6 C7 1.400(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C17 C16 1.388(4) . ?
C2 H2 0.9500 . ?
C16 C15 1.377(5) . ?
C16 H16 0.9500 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 H15 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 Cu1 O1 180.00(11) . 5_766 ?
O1 Cu1 N1 90.23(9) . . ?
O1 Cu1 N1 89.77(9) 5_766 . ?
O1 Cu1 N1 89.77(9) . 5_766 ?
O1 Cu1 N1 90.23(9) 5_766 5_766 ?
N1 Cu1 N1 180.0 . 5_766 ?
C1 O1 Cu1 127.62(18) . . ?
C11 N1 C12 117.4(2) . . ?
C11 N1 Cu1 124.07(19) . . ?
C12 N1 Cu1 118.45(17) . . ?
C13 C12 C17 116.1(2) . . ?
C13 C12 N1 124.6(3) . . ?
C17 C12 N1 119.2(2) . . ?
C8 C9 C4 117.7(2) . . ?
C8 C9 C10 122.6(2) . . ?
C4 C9 C10 119.6(2) . . ?
C5 C4 C9 119.6(3) . . ?
C5 C4 C3 121.9(3) . . ?
C9 C4 C3 118.5(3) . . ?
N1 C11 C10 126.5(3) . . ?
N1 C11 H11 116.8 . . ?
C10 C11 H11 116.8 . . ?
C1 C10 C11 120.2(3) . . ?
C1 C10 C9 120.0(2) . . ?
C11 C10 C9 119.2(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
O1 C1 C10 124.6(3) . . ?
O1 C1 C2 117.1(3) . . ?
C10 C1 C2 118.3(3) . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 Cl1 118.2(2) . . ?
C12 C13 Cl1 119.8(2) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C16 C17 C12 122.4(3) . . ?
C16 C17 Cl2 119.2(2) . . ?
C12 C17 Cl2 118.4(2) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C12 C13 59.4(4) . . . . ?
Cu1 N1 C12 C13 -123.1(3) . . . . ?
C11 N1 C12 C17 -122.6(3) . . . . ?
Cu1 N1 C12 C17 55.0(3) . . . . ?
C8 C9 C4 C5 1.4(4) . . . . ?
C10 C9 C4 C5 -179.5(2) . . . . ?
C8 C9 C4 C3 -177.3(3) . . . . ?
C10 C9 C4 C3 1.8(4) . . . . ?
C12 N1 C11 C10 171.8(3) . . . . ?
Cu1 N1 C11 C10 -5.6(4) . . . . ?
N1 C11 C10 C1 -14.8(4) . . . . ?
N1 C11 C10 C9 174.1(3) . . . . ?
C8 C9 C10 C1 174.6(3) . . . . ?
C4 C9 C10 C1 -4.5(4) . . . . ?
C8 C9 C10 C11 -14.3(4) . . . . ?
C4 C9 C10 C11 166.6(2) . . . . ?
C9 C4 C5 C6 -1.9(4) . . . . ?
C3 C4 C5 C6 176.8(3) . . . . ?
C4 C9 C8 C7 -0.5(4) . . . . ?
C10 C9 C8 C7 -179.5(3) . . . . ?
Cu1 O1 C1 C10 14.8(4) . . . . ?
Cu1 O1 C1 C2 -167.67(19) . . . . ?
C11 C10 C1 O1 10.5(4) . . . . ?
C9 C10 C1 O1 -178.5(2) . . . . ?
C11 C10 C1 C2 -167.0(3) . . . . ?
C9 C10 C1 C2 4.0(4) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
N1 C12 C13 C14 178.9(3) . . . . ?
C17 C12 C13 Cl1 -178.6(2) . . . . ?
N1 C12 C13 Cl1 -0.5(4) . . . . ?
C5 C4 C3 C2 -177.3(3) . . . . ?
C9 C4 C3 C2 1.3(4) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C9 C8 C7 C6 -0.1(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C13 C12 C17 C16 1.7(4) . . . . ?
N1 C12 C17 C16 -176.5(3) . . . . ?
C13 C12 C17 Cl2 -176.9(2) . . . . ?
N1 C12 C17 Cl2 4.9(4) . . . . ?
C4 C3 C2 C1 -1.8(5) . . . . ?
O1 C1 C2 C3 -178.6(3) . . . . ?
C10 C1 C2 C3 -0.9(4) . . . . ?
C12 C17 C16 C15 -3.0(4) . . . . ?
Cl2 C17 C16 C15 175.6(2) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
Cl1 C13 C14 C15 177.4(2) . . . . ?
C17 C16 C15 C14 1.7(5) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.091


####################################################################### 
# 
# 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_CuL2_2_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2338588'
loop_
_audit_author_name
_audit_author_address
'SEGUN OLADIPO'
;OLABISI ONABANJO UNIVERSITY
Nigeria
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_vrf_PLAT026_CuL2_2_a_sq         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        44% Check 
RESPONSE: Crystal deteriorates over time at room temperature. 
When collection attempted at low temperature the crystal twins in the coldstream
;
_vrf_PLAT905_CuL2_2_a_sq         
;
PROBLEM: Negative K value in the Analysis of Variance ...    -17.749 Report
RESPONSE: Crystal deteriorates over time at room temperature. 
When collection attempted at low temperature the crystal twins in the coldstream
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H18 Br2 Cl4 Cu N2 O2'
_chemical_formula_sum            'C34 H18 Br2 Cl4 Cu N2 O2'
_chemical_formula_weight         851.66

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'
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                   18.9437(6)
_cell_length_b                   9.0738(3)
_cell_length_c                   22.7712(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.1150(10)
_cell_angle_gamma                90
_cell_volume                     3875.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      20.67

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.058
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_max          0.528
_exptl_absorpt_coefficient_mu    2.931
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50048
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8878
_reflns_number_gt                3899
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-Seed (Barbour, 2020; Atwood & Barbour, 2003)'
_computing_publication_material  ?
_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)+(0.0966P)²+1.5948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8878
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1970
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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 0.75148(4) 0.36702(7) 0.25137(3) 0.0549(2) Uani 1 1 d . . . . .
Br1 Br 0.78506(4) 1.02549(7) 0.43226(4) 0.0905(3) Uani 1 1 d . . . . .
Br1' Br 0.74839(7) -0.32021(9) 0.09818(5) 0.1483(5) Uani 1 1 d . . . . .
Cl1' Cl 0.71696(12) 0.27657(19) 0.06271(8) 0.1005(7) Uani 1 1 d . . . . .
Cl2' Cl 0.67639(13) 0.04442(19) 0.27278(8) 0.1047(7) Uani 1 1 d . . . . .
Cl2 Cl 0.87298(15) 0.6735(2) 0.25973(11) 0.1311(10) Uani 1 1 d . . . . .
Cl1 Cl 0.74386(15) 0.42678(19) 0.42821(10) 0.1318(10) Uani 1 1 d . . . . .
O1 O 0.8211(2) 0.2426(4) 0.22666(16) 0.0628(10) Uani 1 1 d . . . . .
N1 N 0.8190(2) 0.4247(4) 0.32090(19) 0.0504(11) Uani 1 1 d . . . . .
N1' N 0.6812(2) 0.2864(5) 0.18845(19) 0.0530(11) Uani 1 1 d . . . . .
O1' O 0.6864(2) 0.5115(5) 0.26941(18) 0.0757(12) Uani 1 1 d . . . . .
C12 C 0.8106(3) 0.5628(5) 0.3480(2) 0.0489(13) Uani 1 1 d . . . . .
C1' C 0.6271(3) 0.5521(6) 0.2390(3) 0.0605(15) Uani 1 1 d . . . . .
C11' C 0.6220(3) 0.3522(6) 0.1671(3) 0.0586(15) Uani 1 1 d . . . . .
H11' H 0.593752 0.304893 0.136000 0.070 Uiso 1 1 calc R U . . .
C10' C 0.5958(3) 0.4878(6) 0.1860(3) 0.0567(14) Uani 1 1 d . . . . .
C11 C 0.8750(3) 0.3481(5) 0.3424(2) 0.0522(14) Uani 1 1 d . . . . .
H11 H 0.900785 0.381546 0.377643 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9006(3) 0.2182(5) 0.3172(2) 0.0488(13) Uani 1 1 d . . . . .
C15 C 0.7934(3) 0.8387(6) 0.3971(3) 0.0621(16) Uani 1 1 d . . . . .
C9 C 0.9597(3) 0.1374(6) 0.3497(3) 0.0589(15) Uani 1 1 d . . . . .
C1 C 0.8749(3) 0.1792(6) 0.2586(3) 0.0533(14) Uani 1 1 d . . . . .
C4 C 0.9949(3) 0.0294(6) 0.3193(3) 0.0594(15) Uani 1 1 d . . . . .
C12' C 0.6944(3) 0.1457(6) 0.1655(2) 0.0550(14) Uani 1 1 d . . . . .
C13 C 0.7759(3) 0.5810(6) 0.3965(3) 0.0628(16) Uani 1 1 d . . . . .
C3 C 0.9688(4) -0.0016(6) 0.2593(3) 0.0749(19) Uani 1 1 d . . . . .
H3 H 0.992067 -0.072096 0.239395 0.090 Uiso 1 1 calc R U . . .
C9' C 0.5313(3) 0.5500(7) 0.1533(3) 0.0677(17) Uani 1 1 d . . . . .
C14 C 0.7673(3) 0.7159(6) 0.4212(3) 0.0670(17) Uani 1 1 d . . . . .
H14 H 0.743789 0.724101 0.454306 0.080 Uiso 1 1 calc R U . . .
C17 C 0.8339(3) 0.6904(6) 0.3235(3) 0.0647(16) Uani 1 1 d . . . . .
C2 C 0.9113(3) 0.0675(7) 0.2299(3) 0.0651(16) Uani 1 1 d . . . . .
H2 H 0.895085 0.042441 0.190718 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8273(3) 0.8279(6) 0.3477(3) 0.0698(18) Uani 1 1 d . . . . .
H16 H 0.845256 0.911103 0.331189 0.084 Uiso 1 1 calc R U . . .
C14' C 0.7282(4) -0.0122(7) 0.0885(3) 0.079(2) Uani 1 1 d . . . . .
H14' H 0.738989 -0.024387 0.050224 0.095 Uiso 1 1 calc R U . . .
C13' C 0.7124(3) 0.1249(6) 0.1090(3) 0.0652(16) Uani 1 1 d . . . . .
C8 C 0.9851(3) 0.1566(7) 0.4102(3) 0.0729(18) Uani 1 1 d . . . . .
H8 H 0.962810 0.225416 0.431669 0.088 Uiso 1 1 calc R U . . .
C2' C 0.5902(4) 0.6738(7) 0.2617(3) 0.0766(19) Uani 1 1 d . . . . .
H2' H 0.608880 0.715836 0.297805 0.092 Uiso 1 1 calc R U . . .
C4' C 0.4981(3) 0.6697(7) 0.1773(3) 0.0681(17) Uani 1 1 d . . . . .
C17' C 0.6947(3) 0.0218(6) 0.2013(3) 0.0670(17) Uani 1 1 d . . . . .
C3' C 0.5296(4) 0.7280(7) 0.2320(4) 0.083(2) Uani 1 1 d . . . . .
H3' H 0.507632 0.806841 0.248222 0.100 Uiso 1 1 calc R U . . .
C16' C 0.7115(4) -0.1162(6) 0.1822(3) 0.082(2) Uani 1 1 d . . . . .
H16' H 0.711853 -0.197246 0.207194 0.098 Uiso 1 1 calc R U . . .
C5 C 1.0530(4) -0.0486(7) 0.3504(4) 0.084(2) Uani 1 1 d . . . . .
H5 H 1.075900 -0.119555 0.330499 0.100 Uiso 1 1 calc R U . . .
C5' C 0.4353(4) 0.7302(9) 0.1459(4) 0.095(2) Uani 1 1 d . . . . .
H5' H 0.413153 0.808125 0.162595 0.114 Uiso 1 1 calc R U . . .
C15' C 0.7276(4) -0.1322(7) 0.1265(3) 0.083(2) Uani 1 1 d . . . . .
C7 C 1.0408(4) 0.0790(8) 0.4386(3) 0.091(2) Uani 1 1 d . . . . .
H7 H 1.055183 0.094599 0.478855 0.109 Uiso 1 1 calc R U . . .
C8' C 0.5009(4) 0.4990(9) 0.0979(4) 0.103(3) Uani 1 1 d . . . . .
H8' H 0.522615 0.421566 0.080556 0.123 Uiso 1 1 calc R U . . .
C6 C 1.0763(4) -0.0226(8) 0.4087(4) 0.087(2) Uani 1 1 d . . . . .
H6 H 1.115701 -0.072719 0.428155 0.105 Uiso 1 1 calc R U . . .
C6' C 0.4065(4) 0.6783(11) 0.0924(4) 0.115(3) Uani 1 1 d . . . . .
H6' H 0.365413 0.720952 0.072202 0.138 Uiso 1 1 calc R U . . .
C7' C 0.4388(5) 0.5604(11) 0.0675(4) 0.124(3) Uani 1 1 d . . . . .
H7' H 0.419062 0.522720 0.030904 0.149 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.882(4) . ?
Cu1 O1' 1.885(4) . ?
Cu1 N1 1.961(4) . ?
Cu1 N1' 1.955(4) . ?
Br1 C15 1.891(5) . ?
Br1' C15' 1.884(6) . ?
Cl1' C13' 1.743(6) . ?
Cl2' C17' 1.725(6) . ?
Cl2 C17 1.727(6) . ?
Cl1 C13 1.723(6) . ?
O1 C1 1.300(6) . ?
N1 C11 1.305(6) . ?
N1 C12 1.415(6) . ?
N1' C11' 1.304(7) . ?
N1' C12' 1.415(6) . ?
O1' C1' 1.287(7) . ?
C12 C13 1.374(7) . ?
C12 C17 1.384(7) . ?
C1' C10' 1.395(8) . ?
C1' C2' 1.441(8) . ?
C11' C10' 1.416(7) . ?
C10' C9' 1.453(8) . ?
C11 C10 1.426(7) . ?
C10 C1 1.400(7) . ?
C10 C9 1.451(7) . ?
C15 C14 1.365(8) . ?
C15 C16 1.374(8) . ?
C9 C4 1.418(7) . ?
C9 C8 1.406(8) . ?
C1 C2 1.434(7) . ?
C4 C3 1.415(9) . ?
C4 C5 1.413(9) . ?
C12' C13' 1.390(8) . ?
C12' C17' 1.387(8) . ?
C13 C14 1.367(7) . ?
C3 C2 1.350(8) . ?
C9' C8' 1.390(9) . ?
C9' C4' 1.404(8) . ?
C17 C16 1.377(7) . ?
C14' C13' 1.377(8) . ?
C14' C15' 1.391(9) . ?
C8 C7 1.353(8) . ?
C2' C3' 1.340(9) . ?
C4' C3' 1.408(9) . ?
C4' C5' 1.409(9) . ?
C17' C16' 1.378(8) . ?
C16' C15' 1.353(8) . ?
C5 C6 1.359(9) . ?
C5' C6' 1.349(11) . ?
C7 C6 1.377(9) . ?
C8' C7' 1.393(10) . ?
C6' C7' 1.392(11) . ?

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' 172.11(18) . . ?
O1 Cu1 N1 89.84(17) . . ?
O1' Cu1 N1 90.59(18) . . ?
O1 Cu1 N1' 89.40(17) . . ?
O1' Cu1 N1' 91.23(18) . . ?
N1 Cu1 N1' 172.20(17) . . ?
C1 O1 Cu1 128.7(3) . . ?
C11 N1 C12 116.3(4) . . ?
C11 N1 Cu1 124.3(3) . . ?
C12 N1 Cu1 119.2(4) . . ?
C11' N1' C12' 117.6(5) . . ?
C11' N1' Cu1 124.3(4) . . ?
C12' N1' Cu1 118.1(4) . . ?
C1' O1' Cu1 129.0(4) . . ?
C13 C12 C17 116.1(5) . . ?
C13 C12 N1 123.6(5) . . ?
C17 C12 N1 120.2(5) . . ?
O1' C1' C10' 125.3(5) . . ?
O1' C1' C2' 117.2(6) . . ?
C10' C1' C2' 117.6(6) . . ?
N1' C11' C10' 127.2(5) . . ?
C1' C10' C11' 120.2(6) . . ?
C1' C10' C9' 120.3(5) . . ?
C11' C10' C9' 119.1(5) . . ?
N1 C11 C10 126.5(5) . . ?
C1 C10 C11 120.0(5) . . ?
C1 C10 C9 119.8(5) . . ?
C11 C10 C9 119.6(5) . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 Br1 120.3(4) . . ?
C16 C15 Br1 119.1(4) . . ?
C4 C9 C8 116.4(5) . . ?
C4 C9 C10 118.8(5) . . ?
C8 C9 C10 124.8(5) . . ?
O1 C1 C10 124.1(5) . . ?
O1 C1 C2 116.5(5) . . ?
C10 C1 C2 119.2(5) . . ?
C3 C4 C5 121.7(6) . . ?
C3 C4 C9 119.0(6) . . ?
C5 C4 C9 119.2(6) . . ?
C13' C12' C17' 116.9(5) . . ?
C13' C12' N1' 122.9(5) . . ?
C17' C12' N1' 120.1(5) . . ?
C12 C13 C14 122.5(5) . . ?
C12 C13 Cl1 118.4(4) . . ?
C14 C13 Cl1 119.1(4) . . ?
C2 C3 C4 122.2(6) . . ?
C8' C9' C4' 117.3(6) . . ?
C8' C9' C10' 123.2(6) . . ?
C4' C9' C10' 119.5(6) . . ?
C13 C14 C15 119.6(5) . . ?
C12 C17 C16 123.0(5) . . ?
C12 C17 Cl2 117.6(4) . . ?
C16 C17 Cl2 119.4(4) . . ?
C3 C2 C1 120.6(6) . . ?
C15 C16 C17 118.2(5) . . ?
C13' C14' C15' 118.4(6) . . ?
C14' C13' C12' 122.0(6) . . ?
C14' C13' Cl1' 118.5(5) . . ?
C12' C13' Cl1' 119.5(4) . . ?
C7 C8 C9 122.6(6) . . ?
C3' C2' C1' 121.6(6) . . ?
C9' C4' C3' 118.5(6) . . ?
C9' C4' C5' 119.8(7) . . ?
C3' C4' C5' 121.7(7) . . ?
C12' C17' C16' 122.2(5) . . ?
C12' C17' Cl2' 118.2(4) . . ?
C16' C17' Cl2' 119.5(5) . . ?
C2' C3' C4' 122.4(6) . . ?
C15' C16' C17' 119.1(6) . . ?
C6 C5 C4 121.7(6) . . ?
C6' C5' C4' 121.8(7) . . ?
C16' C15' C14' 121.4(6) . . ?
C16' C15' Br1' 120.2(5) . . ?
C14' C15' Br1' 118.4(5) . . ?
C8 C7 C6 121.0(7) . . ?
C9' C8' C7' 122.0(7) . . ?
C5 C6 C7 118.9(7) . . ?
C5' C6' C7' 119.4(8) . . ?
C6' C7' C8' 119.7(8) . . ?

_refine_diff_density_max         0.778
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.068






