# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 2453268'
_audit_update_record             
;
2025-11-18 deposited with the CCDC.	2026-01-11 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            'C13 H16 Cl Cu N3 O S'
_chemical_formula_weight         361.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.999(4)
_cell_length_b                   21.072(13)
_cell_length_c                   12.373(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.18(3)
_cell_angle_gamma                90
_cell_volume                     1559.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    770
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.703
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.442
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'photon 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23745
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         25.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2736
_reflns_number_gt                2583
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0827P)²+1.1491P] 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         2736
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.21594(5) 0.69194(2) 0.54326(3) 0.0233(2) Uani 1 1 d . . . . .
S1 S 0.93132(12) 0.74185(4) 0.70730(6) 0.0326(2) Uani 1 1 d . . . . .
Cl1 Cl -0.31278(14) 0.40428(4) 0.72225(8) 0.0444(3) Uani 1 1 d . . . . .
O1 O 0.2870(3) 0.61444(10) 0.61852(19) 0.0345(5) Uani 1 1 d . . . . .
N1 N -0.0546(4) 0.65576(11) 0.47151(18) 0.0239(5) Uani 1 1 d . . . . .
N2 N 0.1458(4) 0.76856(12) 0.4425(2) 0.0281(5) Uani 1 1 d . . . . .
H2A H 0.214(7) 0.7591(19) 0.382(4) 0.042(10) Uiso 1 1 d . . . . .
N3 N 0.5030(4) 0.72645(12) 0.6038(2) 0.0323(6) Uani 1 1 d . . . . .
C1 C 0.1452(5) 0.56929(13) 0.6382(2) 0.0259(6) Uani 1 1 d . . . . .
C2 C 0.2152(5) 0.52065(14) 0.7132(3) 0.0312(6) Uani 1 1 d . . . . .
H2 H 0.362018 0.522401 0.747477 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0773(5) 0.47112(14) 0.7378(3) 0.0324(7) Uani 1 1 d . . . . .
H3 H 0.129608 0.439298 0.787822 0.039 Uiso 1 1 calc R U . . .
C4 C -0.1411(5) 0.46803(14) 0.6884(3) 0.0309(6) Uani 1 1 d . . . . .
C5 C -0.2169(5) 0.51304(14) 0.6150(3) 0.0294(6) Uani 1 1 d . . . . .
H5 H -0.364443 0.510169 0.581813 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0761(5) 0.56413(13) 0.5882(2) 0.0245(6) Uani 1 1 d . . . . .
C7 C -0.1605(5) 0.60704(13) 0.5036(2) 0.0262(6) Uani 1 1 d . . . . .
H7 H -0.304408 0.598624 0.469350 0.031 Uiso 1 1 calc R U . . .
C8 C -0.1508(6) 0.69423(13) 0.3806(3) 0.0319(7) Uani 1 1 d . . . . .
H8A H -0.315019 0.688515 0.372631 0.038 Uiso 1 1 calc R U . . .
H8B H -0.088468 0.680697 0.312385 0.038 Uiso 1 1 calc R U . . .
C9 C -0.0943(5) 0.76371(14) 0.4034(2) 0.0291(6) Uani 1 1 d . . . . .
H9A H -0.123226 0.789082 0.336537 0.035 Uiso 1 1 calc R U . . .
H9B H -0.189004 0.780497 0.459125 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2093(6) 0.83212(16) 0.4845(3) 0.0395(8) Uani 1 1 d . . . . .
H10A H 0.370817 0.831702 0.507541 0.047 Uiso 1 1 calc R U . . .
H10B H 0.127469 0.840308 0.549747 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1642(8) 0.88704(18) 0.4054(3) 0.0536(10) Uani 1 1 d . . . . .
H11A H 0.234885 0.877855 0.337301 0.064 Uiso 1 1 calc R U . . .
H11B H 0.001079 0.891017 0.387917 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2538(10) 0.9487(2) 0.4518(4) 0.0699(14) Uani 1 1 d . . . . .
H12A H 0.180075 0.958747 0.517860 0.105 Uiso 1 1 calc R U . . .
H12B H 0.224521 0.982726 0.398601 0.105 Uiso 1 1 calc R U . . .
H12C H 0.415289 0.944950 0.469241 0.105 Uiso 1 1 calc R U . . .
C13 C 0.6801(5) 0.73275(12) 0.6477(2) 0.0229(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.913(2) . ?
Cu1 N1 1.947(2) . ?
Cu1 N3 1.966(3) . ?
Cu1 N2 2.065(3) . ?
S1 C13 1.640(3) . ?
Cl1 C4 1.762(3) . ?
O1 C1 1.311(4) . ?
N1 C7 1.286(4) . ?
N1 C8 1.470(4) . ?
N2 C10 1.477(4) . ?
N2 C9 1.489(4) . ?
N2 H2A 0.91(4) . ?
N3 C13 1.165(4) . ?
C1 C2 1.425(4) . ?
C1 C6 1.427(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(4) . ?
C5 C6 1.423(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.446(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.527(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.505(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 92.09(10) . . ?
O1 Cu1 N3 88.42(10) . . ?
N1 Cu1 N3 174.75(10) . . ?
O1 Cu1 N2 171.97(11) . . ?
N1 Cu1 N2 84.53(10) . . ?
N3 Cu1 N2 94.30(11) . . ?
C1 O1 Cu1 125.82(18) . . ?
C7 N1 C8 120.1(2) . . ?
C7 N1 Cu1 125.9(2) . . ?
C8 N1 Cu1 113.62(19) . . ?
C10 N2 C9 113.3(2) . . ?
C10 N2 Cu1 117.4(2) . . ?
C9 N2 Cu1 106.96(17) . . ?
C10 N2 H2A 112(3) . . ?
C9 N2 H2A 102(3) . . ?
Cu1 N2 H2A 104(3) . . ?
C13 N3 Cu1 164.4(2) . . ?
O1 C1 C2 118.6(3) . . ?
O1 C1 C6 124.8(3) . . ?
C2 C1 C6 116.6(3) . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 Cl1 121.0(2) . . ?
C3 C4 Cl1 118.3(2) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C7 117.4(3) . . ?
C1 C6 C7 122.1(3) . . ?
N1 C7 C6 124.6(3) . . ?
N1 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
N1 C8 C9 108.6(2) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C8 108.8(2) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 115.6(3) . . ?
N2 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
N2 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 111.6(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 S1 178.9(3) . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.125

####################################################################### 
# 
# 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_f_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2453269'
_audit_update_record             
;
2025-11-18 deposited with the CCDC.	2026-01-11 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            'C13 H16 Br Cu N3 O S'
_chemical_formula_weight         405.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.0003(2)
_cell_length_b                   21.1415(8)
_cell_length_c                   12.3189(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.472(2)
_cell_angle_gamma                90
_cell_volume                     1557.96(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    888
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.098
_shelx_estimated_absorpt_T_min   0.526
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'photon 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57750
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3425
_reflns_number_gt                3069
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0330P)²+1.2088P] 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         3425
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.78171(4) 0.69302(2) 0.45605(2) 0.02637(8) Uani 1 1 d . . . . .
Br1 Br 1.30576(4) 0.40024(2) 0.27334(2) 0.04342(9) Uani 1 1 d . . . . .
S1 S 0.06794(9) 0.74113(3) 0.29051(5) 0.03540(14) Uani 1 1 d . . . . .
O1 O 0.7077(2) 0.61595(8) 0.38216(14) 0.0367(4) Uani 1 1 d . . . . .
N1 N 1.0541(3) 0.65772(8) 0.52615(14) 0.0271(4) Uani 1 1 d . . . . .
N2 N 0.8546(3) 0.76906(9) 0.55597(16) 0.0317(4) Uani 1 1 d . . . . .
H2A H 0.787(5) 0.7632(13) 0.610(2) 0.038(7) Uiso 1 1 d . . . . .
N3 N 0.4953(3) 0.72720(9) 0.39416(16) 0.0346(4) Uani 1 1 d . . . . .
C1 C 0.8460(3) 0.57080(10) 0.36247(18) 0.0289(4) Uani 1 1 d . . . . .
C2 C 0.7726(4) 0.52225(11) 0.28884(19) 0.0338(5) Uani 1 1 d . . . . .
H2 H 0.624555 0.523982 0.255487 0.041 Uiso 1 1 calc R U . . .
C3 C 0.9070(4) 0.47315(11) 0.26417(19) 0.0352(5) Uani 1 1 d . . . . .
H3 H 0.852016 0.441231 0.214834 0.042 Uiso 1 1 calc R U . . .
C4 C 1.1257(4) 0.46993(10) 0.31165(19) 0.0321(4) Uani 1 1 d . . . . .
C5 C 1.2054(4) 0.51462(10) 0.38432(18) 0.0309(4) Uani 1 1 d . . . . .
H5 H 1.353969 0.511497 0.416708 0.037 Uiso 1 1 calc R U . . .
C6 C 1.0685(3) 0.56550(10) 0.41170(17) 0.0273(4) Uani 1 1 d . . . . .
C7 C 1.1566(3) 0.60896(10) 0.49425(17) 0.0289(4) Uani 1 1 d . . . . .
H7 H 1.301983 0.600762 0.527491 0.035 Uiso 1 1 calc R U . . .
C8 C 1.1549(4) 0.69657(11) 0.61560(19) 0.0350(5) Uani 1 1 d . . . . .
H8A H 1.319350 0.691333 0.621363 0.042 Uiso 1 1 calc R U . . .
H8B H 1.098029 0.683148 0.685311 0.042 Uiso 1 1 calc R U . . .
C9 C 1.0950(4) 0.76506(10) 0.59293(18) 0.0317(4) Uani 1 1 d . . . . .
H9A H 1.126083 0.790541 0.659819 0.038 Uiso 1 1 calc R U . . .
H9B H 1.186207 0.781999 0.535973 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7880(5) 0.83211(12) 0.5136(2) 0.0430(6) Uani 1 1 d . . . . .
H10A H 0.626189 0.831292 0.490515 0.052 Uiso 1 1 calc R U . . .
H10B H 0.868833 0.840730 0.448110 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8325(6) 0.88619(14) 0.5938(3) 0.0592(8) Uani 1 1 d . . . . .
H11A H 0.763603 0.876348 0.662274 0.071 Uiso 1 1 calc R U . . .
H11B H 0.995710 0.890623 0.611070 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7395(8) 0.94739(16) 0.5483(3) 0.0814(12) Uani 1 1 d . . . . .
H12A H 0.818050 0.959325 0.484567 0.122 Uiso 1 1 calc R U . . .
H12B H 0.759972 0.980529 0.603839 0.122 Uiso 1 1 calc R U . . .
H12C H 0.579814 0.942290 0.526882 0.122 Uiso 1 1 calc R U . . .
C13 C 0.3189(3) 0.73267(10) 0.35102(17) 0.0268(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9018(15) . ?
Cu1 N1 1.9377(17) . ?
Cu1 N3 1.9626(18) . ?
Cu1 N2 2.0511(19) . ?
Br1 C4 1.908(2) . ?
S1 C13 1.637(2) . ?
O1 C1 1.300(3) . ?
N1 C7 1.278(3) . ?
N1 C8 1.467(3) . ?
N2 C10 1.475(3) . ?
N2 C9 1.481(3) . ?
N2 H2A 0.81(3) . ?
N3 C13 1.153(3) . ?
C1 C2 1.417(3) . ?
C1 C6 1.427(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(3) . ?
C5 C6 1.410(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.440(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.500(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 92.32(7) . . ?
O1 Cu1 N3 87.99(7) . . ?
N1 Cu1 N3 176.00(8) . . ?
O1 Cu1 N2 171.71(8) . . ?
N1 Cu1 N2 84.35(7) . . ?
N3 Cu1 N2 94.80(8) . . ?
C1 O1 Cu1 126.15(13) . . ?
C7 N1 C8 120.18(18) . . ?
C7 N1 Cu1 125.68(14) . . ?
C8 N1 Cu1 113.78(14) . . ?
C10 N2 C9 113.02(19) . . ?
C10 N2 Cu1 117.16(15) . . ?
C9 N2 Cu1 107.25(13) . . ?
C10 N2 H2A 107(2) . . ?
C9 N2 H2A 106(2) . . ?
Cu1 N2 H2A 106(2) . . ?
C13 N3 Cu1 163.91(19) . . ?
O1 C1 C2 118.71(19) . . ?
O1 C1 C6 124.60(19) . . ?
C2 C1 C6 116.68(19) . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 Br1 121.43(17) . . ?
C3 C4 Br1 117.77(17) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.09(19) . . ?
C5 C6 C7 117.82(19) . . ?
C1 C6 C7 122.00(19) . . ?
N1 C7 C6 124.93(19) . . ?
N1 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
N1 C8 C9 108.62(17) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 108.86(18) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 114.8(2) . . ?
N2 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 111.4(3) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 S1 179.4(2) . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.063

