# Supplementary Information (SI) 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2305235'
loop_
_audit_author_name
_audit_author_address
'Partha Roy'
;Jadavpur University
India
;
_audit_update_record             
;
2023-11-02 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cu N2 O2'
_chemical_formula_sum            'C36 H40 Cu N2 O2'
_chemical_formula_weight         596.24

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6160(16)
_cell_length_b                   11.962(3)
_cell_length_c                   12.004(4)
_cell_angle_alpha                113.799(9)
_cell_angle_beta                 91.846(10)
_cell_angle_gamma                100.923(9)
_cell_volume                     719.2(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    144(2)
_cell_measurement_reflns_used    2693
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.65

_exptl_crystal_description       'Needle shaped'
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             315
_exptl_transmission_factor_min   0.826
_exptl_transmission_factor_max   0.923
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.796
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      144(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7758
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.180
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3266
_reflns_number_gt                2550
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.0110P)²+0.6881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.02345(15) Uani 1 2 d S . P . .
O1 O 0.8970(3) 0.55736(18) 0.65831(17) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.7842(4) 0.5898(2) 0.44916(19) 0.0217(5) Uani 1 1 d . . . . .
C11 C 0.6471(5) 0.6566(2) 0.5194(2) 0.0219(6) Uani 1 1 d . . . . .
C1 C 0.7603(5) 0.6363(3) 0.7095(2) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.6304(4) 0.6873(2) 0.6468(2) 0.0210(6) Uani 1 1 d . . . . .
C14 C 0.9838(5) 0.6302(3) 0.1634(2) 0.0261(6) Uani 1 1 d . . . . .
H14A H 0.987974 0.540622 0.119900 0.031 Uiso 1 1 calc R U . . .
H14B H 0.831965 0.642885 0.130740 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4579(5) 0.8000(2) 0.8379(2) 0.0235(6) Uani 1 1 d . . . . .
C9 C 0.5980(5) 0.7482(3) 0.8981(2) 0.0253(6) Uani 1 1 d . . . . .
H9 H 0.590464 0.768925 0.982871 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4740(5) 0.7705(2) 0.7115(2) 0.0224(6) Uani 1 1 d . . . . .
C6 C 0.1695(5) 0.9288(3) 0.8449(3) 0.0293(6) Uani 1 1 d . . . . .
H6 H 0.066400 0.981426 0.889167 0.035 Uiso 1 1 calc R U . . .
C15 C 1.2042(5) 0.7102(3) 0.1394(3) 0.0311(7) Uani 1 1 d . . . . .
H15A H 1.355664 0.690357 0.163566 0.037 Uiso 1 1 calc R U . . .
H15B H 1.194826 0.689800 0.050642 0.037 Uiso 1 1 calc R U . . .
C10 C 0.7415(5) 0.6701(3) 0.8369(2) 0.0253(6) Uani 1 1 d . . . . .
H10 H 0.831919 0.636931 0.879657 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3031(5) 0.8783(3) 0.9012(2) 0.0284(6) Uani 1 1 d . . . . .
H7 H 0.291760 0.896255 0.985248 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3344(5) 0.8257(3) 0.6566(3) 0.0282(6) Uani 1 1 d . . . . .
H4 H 0.343214 0.809526 0.572778 0.034 Uiso 1 1 calc R U . . .
C16 C 1.2150(6) 0.8494(3) 0.2107(3) 0.0350(7) Uani 1 1 d . . . . .
H16A H 1.074335 0.871427 0.178922 0.042 Uiso 1 1 calc R U . . .
H16B H 1.366533 0.898351 0.198177 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1859(5) 0.9023(3) 0.7214(3) 0.0311(7) Uani 1 1 d . . . . .
H5 H 0.093714 0.937476 0.681626 0.037 Uiso 1 1 calc R U . . .
C17 C 1.2099(6) 0.8841(3) 0.3477(3) 0.0322(7) Uani 1 1 d . . . . .
H17A H 1.205688 0.973738 0.390641 0.039 Uiso 1 1 calc R U . . .
H17B H 1.360244 0.871340 0.381736 0.039 Uiso 1 1 calc R U . . .
C18 C 0.9862(5) 0.8039(3) 0.3697(2) 0.0277(6) Uani 1 1 d . . . . .
H18A H 0.835886 0.821765 0.341607 0.033 Uiso 1 1 calc R U . . .
H18B H 0.989050 0.825829 0.458649 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7659(5) 0.5788(3) 0.3220(2) 0.0231(6) Uani 1 1 d . . . . .
H12A H 0.612491 0.600817 0.303700 0.028 Uiso 1 1 calc R U . . .
H12B H 0.758774 0.490838 0.264815 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9822(5) 0.6642(2) 0.3009(2) 0.0214(6) Uani 1 1 d . . . . .
H13 H 1.138(5) 0.648(2) 0.330(2) 0.026(7) Uiso 1 1 d . . . . .
H11 H 0.537(4) 0.689(2) 0.480(2) 0.017(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8935(18) . ?
Cu1 O1 1.8935(18) 2_766 ?
Cu1 N1 1.993(2) . ?
Cu1 N1 1.993(2) 2_766 ?
O1 C1 1.302(3) . ?
N1 C11 1.293(3) . ?
N1 C12 1.476(3) . ?
C11 C2 1.433(3) . ?
C11 H11 0.99(2) . ?
C1 C2 1.405(4) . ?
C1 C10 1.428(4) . ?
C2 C3 1.455(4) . ?
C14 C15 1.526(4) . ?
C14 C13 1.533(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 C7 1.410(4) . ?
C8 C3 1.423(4) . ?
C8 C9 1.426(4) . ?
C9 C10 1.353(4) . ?
C9 H9 0.9500 . ?
C3 C4 1.414(4) . ?
C6 C7 1.361(4) . ?
C6 C5 1.396(4) . ?
C6 H6 0.9500 . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C16 C17 1.528(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C5 H5 0.9500 . ?
C17 C18 1.529(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C13 1.532(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C12 C13 1.530(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.01(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_766 ?
O1 Cu1 N1 90.58(8) . . ?
O1 Cu1 N1 89.42(8) 2_766 . ?
O1 Cu1 N1 89.42(8) . 2_766 ?
O1 Cu1 N1 90.58(8) 2_766 2_766 ?
N1 Cu1 N1 180.0 . 2_766 ?
C1 O1 Cu1 131.30(17) . . ?
C11 N1 C12 115.3(2) . . ?
C11 N1 Cu1 124.66(18) . . ?
C12 N1 Cu1 120.03(16) . . ?
N1 C11 C2 128.2(2) . . ?
N1 C11 H11 115.9(14) . . ?
C2 C11 H11 115.9(14) . . ?
O1 C1 C2 124.0(2) . . ?
O1 C1 C10 116.8(2) . . ?
C2 C1 C10 119.2(2) . . ?
C1 C2 C11 120.7(2) . . ?
C1 C2 C3 119.6(2) . . ?
C11 C2 C3 119.6(2) . . ?
C15 C14 C13 111.2(2) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C7 C8 C3 119.9(2) . . ?
C7 C8 C9 121.1(2) . . ?
C3 C8 C9 119.0(2) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C4 C3 C8 116.8(2) . . ?
C4 C3 C2 124.0(2) . . ?
C8 C3 C2 119.2(2) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C16 C15 C14 111.5(2) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C9 C10 C1 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C1 C10 H10 119.2 . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C15 C16 C17 111.5(2) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.6 . . ?
C16 C17 C18 110.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C13 110.9(2) . . ?
C17 C18 H18A 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
N1 C12 C13 112.2(2) . . ?
N1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C18 113.5(2) . . ?
C12 C13 C14 110.2(2) . . ?
C18 C13 C14 109.7(2) . . ?
C12 C13 H13 108.1(15) . . ?
C18 C13 H13 108.2(15) . . ?
C14 C13 H13 106.9(15) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.078



####################################################################### 
# 
# 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 2305236'
loop_
_audit_author_name
_audit_author_address
'Partha Roy'
;Jadavpur University
India
;
_audit_update_record             
;
2023-11-02 deposited with the CCDC.	2024-07-30 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 H34 Br2 Cu N6 O10'
_chemical_formula_weight         813.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1767(6)
_cell_length_b                   8.1955(6)
_cell_length_c                   12.1083(8)
_cell_angle_alpha                92.454(2)
_cell_angle_beta                 109.282(2)
_cell_angle_gamma                95.012(2)
_cell_volume                     760.74(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.502
_cell_measurement_theta_max      27.565

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             411
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.410
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST AREA DETECTOR'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25925
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3505
_reflns_number_gt                3176
_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0747P)²+0.4814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3505
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Br1 Br 0.22634(4) 0.88906(4) 0.52906(2) 0.04000(12) Uani 1 1 d . . . . .
Cu1 Cu 1.000000 0.500000 0.500000 0.02659(13) Uani 1 2 d S . P . .
O2 O 0.9059(3) 0.6064(3) 0.60352(16) 0.0385(4) Uani 1 1 d . . . . .
O1 O 0.8758(3) 1.0386(3) 0.0879(2) 0.0506(6) Uani 1 1 d . . . . .
N1 N 0.8086(3) 0.7058(2) 0.14121(17) 0.0248(4) Uani 1 1 d . . . . .
N2 N 0.7848(3) 0.5235(2) 0.35912(17) 0.0250(4) Uani 1 1 d . . . . .
C7 C 0.6475(3) 0.5796(3) 0.3683(2) 0.0264(5) Uani 1 1 d . . . . .
O3 O 0.4390(3) 0.6406(4) 0.0586(3) 0.0662(8) Uani 1 1 d . . . . .
C8 C 0.6277(3) 0.6582(3) 0.4707(2) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.9033(4) 0.8408(3) 0.2339(2) 0.0388(6) Uani 1 1 d . . . . .
H4A H 1.027828 0.842200 0.250157 0.047 Uiso 1 1 calc R U . . .
H4B H 0.879537 0.820276 0.305685 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5675(4) 0.8130(4) 0.6613(2) 0.0364(6) Uani 1 1 d . . . . .
H11 H 0.547168 0.865201 0.724481 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7203(4) 0.7466(4) 0.6773(2) 0.0368(6) Uani 1 1 d . . . . .
H10 H 0.802534 0.753328 0.752257 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7764(4) 0.9167(4) -0.0021(3) 0.0460(7) Uani 1 1 d . . . . .
H2A H 0.792007 0.942753 -0.075595 0.055 Uiso 1 1 calc R U . . .
H2B H 0.653757 0.916920 -0.011971 0.055 Uiso 1 1 calc R U . . .
C3 C 0.8469(5) 1.0054(4) 0.1944(3) 0.0488(8) Uani 1 1 d . . . . .
H3A H 0.724030 1.006396 0.183514 0.059 Uiso 1 1 calc R U . . .
H3B H 0.911466 1.090903 0.254786 0.059 Uiso 1 1 calc R U . . .
C5 C 0.8693(3) 0.5411(3) 0.1764(2) 0.0284(5) Uani 1 1 d . . . . .
H5A H 0.990896 0.557627 0.225847 0.034 Uiso 1 1 calc R U . . .
H5B H 0.861613 0.474268 0.106482 0.034 Uiso 1 1 calc R U . . .
N3 N 0.3727(3) 0.7147(3) 0.1222(2) 0.0399(5) Uani 1 1 d . . . . .
C12 C 0.4416(3) 0.8021(3) 0.5495(2) 0.0289(5) Uani 1 1 d . . . . .
C13 C 0.4699(3) 0.7257(3) 0.4553(2) 0.0280(5) Uani 1 1 d . . . . .
H13 H 0.384800 0.718445 0.381438 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7654(3) 0.4484(3) 0.2418(2) 0.0276(5) Uani 1 1 d . . . . .
H6A H 0.643007 0.438619 0.194160 0.033 Uiso 1 1 calc R U . . .
H6B H 0.800203 0.338223 0.250334 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7575(3) 0.6674(3) 0.5826(2) 0.0284(5) Uani 1 1 d . . . . .
O4 O 0.4561(5) 0.8376(3) 0.1827(3) 0.0774(9) Uani 1 1 d . . . . .
O5 O 0.2324(4) 0.6587(5) 0.1264(3) 0.0850(10) Uani 1 1 d . . . . .
C1 C 0.8311(4) 0.7481(3) 0.0273(2) 0.0337(5) Uani 1 1 d . . . . .
H1A H 0.760932 0.667249 -0.034980 0.040 Uiso 1 1 calc R U . . .
H1B H 0.952149 0.745831 0.033311 0.040 Uiso 1 1 calc R U . . .
H7 H 0.541(4) 0.571(3) 0.299(2) 0.022(6) Uiso 1 1 d . . . . .
H1N H 0.691(5) 0.704(5) 0.131(3) 0.054(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.901(3) . ?
Cu1 O2 1.8935(19) 2_766 ?
Cu1 O2 1.8935(19) . ?
Cu1 N2 2.037(2) 2_766 ?
Cu1 N2 2.037(2) . ?
O2 C9 1.304(3) . ?
O1 C3 1.419(4) . ?
O1 C2 1.423(4) . ?
N1 C1 1.502(3) . ?
N1 C4 1.501(3) . ?
N1 C5 1.508(3) . ?
N1 H1N 0.92(4) . ?
N2 C7 1.285(3) . ?
N2 C6 1.477(3) . ?
C7 C8 1.436(3) . ?
C7 H7 0.98(3) . ?
O3 N3 1.244(4) . ?
C8 C13 1.408(3) . ?
C8 C9 1.413(3) . ?
C4 C3 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C11 C10 1.365(4) . ?
C11 C12 1.398(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.425(4) . ?
C10 H10 0.9300 . ?
C2 C1 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N3 O5 1.216(4) . ?
N3 O4 1.226(4) . ?
C12 C13 1.373(4) . ?
C13 H13 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 Cu1 O2 180.0 2_766 . ?
O2 Cu1 N2 91.79(8) 2_766 2_766 ?
O2 Cu1 N2 88.21(8) . 2_766 ?
O2 Cu1 N2 88.21(8) 2_766 . ?
O2 Cu1 N2 91.79(8) . . ?
N2 Cu1 N2 180.0 2_766 . ?
C9 O2 Cu1 130.35(17) . . ?
C3 O1 C2 109.6(2) . . ?
C1 N1 C4 108.89(19) . . ?
C1 N1 C5 111.88(19) . . ?
C4 N1 C5 111.6(2) . . ?
C1 N1 H1N 107(2) . . ?
C4 N1 H1N 107(2) . . ?
C5 N1 H1N 110(2) . . ?
C7 N2 C6 115.1(2) . . ?
C7 N2 Cu1 123.10(17) . . ?
C6 N2 Cu1 120.89(15) . . ?
N2 C7 C8 127.5(2) . . ?
N2 C7 H7 119.4(16) . . ?
C8 C7 H7 113.1(17) . . ?
C13 C8 C9 120.6(2) . . ?
C13 C8 C7 116.7(2) . . ?
C9 C8 C7 122.7(2) . . ?
N1 C4 C3 110.8(2) . . ?
N1 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
O1 C2 C1 111.2(2) . . ?
O1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 111.3(3) . . ?
O1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C5 C6 113.7(2) . . ?
N1 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O5 N3 O4 122.5(3) . . ?
O5 N3 O3 119.1(3) . . ?
O4 N3 O3 118.3(3) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 Br1 119.8(2) . . ?
C11 C12 Br1 119.4(2) . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
N2 C6 C5 115.3(2) . . ?
N2 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
N2 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
O2 C9 C8 123.9(2) . . ?
O2 C9 C10 119.0(2) . . ?
C8 C9 C10 117.0(2) . . ?
N1 C1 C2 110.2(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -1.131
_refine_diff_density_rms         0.110



