# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2171406'
loop_
_audit_author_name
_audit_author_address
'MUNIYANDI SANKARALINGAM'
;National Institute of Technology Calicut
India
;
_audit_update_record             
;
2022-05-08 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 Br Cu N3 O S'
_chemical_formula_weight         452.83

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/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                   9.534(8)
_cell_length_b                   13.267(10)
_cell_length_c                   14.527(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.96(3)
_cell_angle_gamma                90
_cell_volume                     1798(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    28371
_cell_measurement_theta_min      2.100
_cell_measurement_theta_max      28.312

_exptl_crystal_description       needls
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    3.562
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28371
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4449
_reflns_number_gt                3379
_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-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)+(0.0444P)²+1.2014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4449
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.06942(4) 0.20397(3) 0.96694(2) 0.04163(12) Uani 1 1 d . . . . .
Br1 Br -0.36723(4) 0.67058(3) 0.91396(3) 0.06411(14) Uani 1 1 d . . . . .
N3 N 0.0912(3) 0.10103(19) 1.06476(17) 0.0483(6) Uani 1 1 d . . . . .
O1 O -0.0610(2) 0.27723(17) 1.02549(15) 0.0542(6) Uani 1 1 d . . . . .
N1 N 0.0599(3) 0.30215(18) 0.86648(17) 0.0430(6) Uani 1 1 d . . . . .
N2 N 0.2060(3) 0.1299(2) 0.89458(17) 0.0455(6) Uani 1 1 d . . . . .
C6 C -0.1023(3) 0.4187(2) 0.91886(19) 0.0394(6) Uani 1 1 d . . . . .
C15 C 0.3155(6) -0.1752(3) 0.7946(4) 0.0833(14) Uani 1 1 d . . . . .
C5 C -0.1743(3) 0.5114(2) 0.8968(2) 0.0445(7) Uani 1 1 d . . . . .
C1 C -0.1262(3) 0.3622(2) 0.9975(2) 0.0430(6) Uani 1 1 d . . . . .
C3 C -0.2949(4) 0.4910(3) 1.0236(2) 0.0559(8) Uani 1 1 d . . . . .
C7 C -0.0098(3) 0.3856(2) 0.8587(2) 0.0427(7) Uani 1 1 d . . . . .
C2 C -0.2256(4) 0.4018(3) 1.0480(2) 0.0559(8) Uani 1 1 d . . . . .
C4 C -0.2692(3) 0.5466(2) 0.9473(2) 0.0462(7) Uani 1 1 d . . . . .
C11 C 0.3616(3) -0.0164(3) 0.8766(2) 0.0535(8) Uani 1 1 d . . . . .
C12 C 0.4707(4) -0.0003(3) 0.8278(3) 0.0582(9) Uani 1 1 d . . . . .
C9 C 0.2607(4) 0.2067(3) 0.8369(3) 0.0553(8) Uani 1 1 d . . . . .
C8 C 0.1397(4) 0.2734(3) 0.7931(3) 0.0588(9) Uani 1 1 d . . . . .
C10 C 0.3239(4) 0.0611(4) 0.9430(3) 0.0667(11) Uani 1 1 d . . . . .
C13 C 0.4988(5) -0.0710(4) 0.7640(3) 0.0745(12) Uani 1 1 d . . . . .
C16 C 0.2837(4) -0.1065(3) 0.8603(3) 0.0696(11) Uani 1 1 d . . . . .
C14 C 0.4211(6) -0.1577(4) 0.7468(4) 0.0852(14) Uani 1 1 d . . . . .
S1 S 0.13763(10) -0.06603(7) 1.18295(6) 0.0598(2) Uani 1 1 d . . . . .
C17 C 0.1101(3) 0.0313(2) 1.11308(19) 0.0397(6) Uani 1 1 d . . . . .
H7 H 0.304(4) 0.174(3) 0.790(2) 0.055(9) Uiso 1 1 d . . . . .
H2 H -0.357(4) 0.516(3) 1.056(2) 0.056(10) Uiso 1 1 d . . . . .
H5 H 0.177(4) 0.331(3) 0.771(3) 0.066(11) Uiso 1 1 d . . . . .
H4 H 0.000(3) 0.430(2) 0.813(2) 0.044(8) Uiso 1 1 d . . . . .
H3 H -0.158(4) 0.546(3) 0.851(3) 0.061(11) Uiso 1 1 d . . . . .
H15 H 0.213(4) -0.119(3) 0.895(3) 0.076(12) Uiso 1 1 d . . . . .
H9 H 0.405(4) 0.109(3) 0.966(2) 0.057(10) Uiso 1 1 d . . . . .
H8 H 0.330(4) 0.249(3) 0.878(3) 0.077(12) Uiso 1 1 d . . . . .
H11 H 0.527(4) 0.058(3) 0.839(3) 0.068(12) Uiso 1 1 d . . . . .
H6 H 0.071(5) 0.228(3) 0.740(3) 0.089(14) Uiso 1 1 d . . . . .
H1 H -0.245(4) 0.362(3) 1.103(3) 0.066(11) Uiso 1 1 d . . . . .
H14 H 0.264(4) -0.228(3) 0.787(3) 0.074(13) Uiso 1 1 d . . . . .
H12 H 0.568(6) -0.061(4) 0.733(4) 0.13(2) Uiso 1 1 d . . . . .
H10 H 0.290(5) 0.029(3) 0.993(3) 0.088(14) Uiso 1 1 d . . . . .
H13 H 0.439(5) -0.215(4) 0.703(3) 0.110(17) 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 1.911(2) . ?
Cu1 N1 1.944(3) . ?
Cu1 N3 1.951(3) . ?
Cu1 N2 2.082(3) . ?
Br1 C4 1.905(3) . ?
N3 C17 1.152(4) . ?
O1 C1 1.311(4) . ?
N1 C7 1.284(4) . ?
N1 C8 1.482(4) . ?
N2 C9 1.481(4) . ?
N2 C10 1.505(4) . ?
C6 C5 1.412(4) . ?
C6 C1 1.424(4) . ?
C6 C7 1.433(4) . ?
C15 C14 1.357(7) . ?
C15 C16 1.398(7) . ?
C15 H14 0.85(4) . ?
C5 C4 1.361(4) . ?
C5 H3 0.84(4) . ?
C1 C2 1.414(4) . ?
C3 C2 1.365(5) . ?
C3 C4 1.395(5) . ?
C3 H2 0.90(4) . ?
C7 H4 0.90(3) . ?
C2 H1 1.01(4) . ?
C11 C12 1.392(5) . ?
C11 C16 1.401(6) . ?
C11 C10 1.504(5) . ?
C12 C13 1.384(6) . ?
C12 H11 0.94(4) . ?
C9 C8 1.488(5) . ?
C9 H7 0.97(4) . ?
C9 H8 0.97(4) . ?
C8 H5 0.92(4) . ?
C8 H6 1.09(4) . ?
C10 H9 1.00(4) . ?
C10 H10 0.96(5) . ?
C13 C14 1.363(7) . ?
C13 H12 0.88(6) . ?
C16 H15 0.94(4) . ?
C14 H13 1.03(5) . ?
S1 C17 1.630(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 N1 93.43(11) . . ?
O1 Cu1 N3 90.74(11) . . ?
N1 Cu1 N3 175.74(11) . . ?
O1 Cu1 N2 175.98(9) . . ?
N1 Cu1 N2 82.76(11) . . ?
N3 Cu1 N2 93.09(11) . . ?
C17 N3 Cu1 170.1(2) . . ?
C1 O1 Cu1 127.57(18) . . ?
C7 N1 C8 119.4(3) . . ?
C7 N1 Cu1 125.9(2) . . ?
C8 N1 Cu1 114.6(2) . . ?
C9 N2 C10 111.4(3) . . ?
C9 N2 Cu1 107.0(2) . . ?
C10 N2 Cu1 122.4(2) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 117.4(3) . . ?
C1 C6 C7 123.3(3) . . ?
C14 C15 C16 121.8(5) . . ?
C14 C15 H14 123(3) . . ?
C16 C15 H14 116(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H3 120(3) . . ?
C6 C5 H3 119(3) . . ?
O1 C1 C2 118.9(3) . . ?
O1 C1 C6 123.9(3) . . ?
C2 C1 C6 117.2(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H2 121(2) . . ?
C4 C3 H2 118(2) . . ?
N1 C7 C6 125.6(3) . . ?
N1 C7 H4 120(2) . . ?
C6 C7 H4 115(2) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H1 120(2) . . ?
C1 C2 H1 118(2) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 Br1 120.3(2) . . ?
C3 C4 Br1 120.1(2) . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C10 121.6(4) . . ?
C16 C11 C10 120.2(4) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H11 119(2) . . ?
C11 C12 H11 120(2) . . ?
N2 C9 C8 108.6(3) . . ?
N2 C9 H7 110(2) . . ?
C8 C9 H7 112(2) . . ?
N2 C9 H8 109(2) . . ?
C8 C9 H8 107(2) . . ?
H7 C9 H8 110(3) . . ?
N1 C8 C9 108.3(3) . . ?
N1 C8 H5 109(2) . . ?
C9 C8 H5 108(2) . . ?
N1 C8 H6 109(2) . . ?
C9 C8 H6 106(2) . . ?
H5 C8 H6 116(3) . . ?
C11 C10 N2 111.7(3) . . ?
C11 C10 H9 112(2) . . ?
N2 C10 H9 103(2) . . ?
C11 C10 H10 111(3) . . ?
N2 C10 H10 107(3) . . ?
H9 C10 H10 113(3) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H12 118(4) . . ?
C12 C13 H12 121(4) . . ?
C15 C16 C11 119.3(4) . . ?
C15 C16 H15 122(3) . . ?
C11 C16 H15 119(3) . . ?
C15 C14 C13 119.0(5) . . ?
C15 C14 H13 116(3) . . ?
C13 C14 H13 125(3) . . ?
N3 C17 S1 179.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C6 C5 C4 -1.9(4) . . . . ?
C7 C6 C5 C4 177.0(3) . . . . ?
Cu1 O1 C1 C2 176.4(2) . . . . ?
Cu1 O1 C1 C6 -4.1(4) . . . . ?
C5 C6 C1 O1 -177.7(3) . . . . ?
C7 C6 C1 O1 3.5(5) . . . . ?
C5 C6 C1 C2 1.8(4) . . . . ?
C7 C6 C1 C2 -177.0(3) . . . . ?
C8 N1 C7 C6 173.8(3) . . . . ?
Cu1 N1 C7 C6 -4.9(5) . . . . ?
C5 C6 C7 N1 -177.5(3) . . . . ?
C1 C6 C7 N1 1.3(5) . . . . ?
C4 C3 C2 C1 -0.1(6) . . . . ?
O1 C1 C2 C3 178.6(3) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C6 C5 C4 C3 0.9(5) . . . . ?
C6 C5 C4 Br1 -178.7(2) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 Br1 179.7(3) . . . . ?
C16 C11 C12 C13 1.1(5) . . . . ?
C10 C11 C12 C13 -177.1(3) . . . . ?
C10 N2 C9 C8 -178.6(3) . . . . ?
Cu1 N2 C9 C8 -42.5(3) . . . . ?
C7 N1 C8 C9 153.1(3) . . . . ?
Cu1 N1 C8 C9 -28.1(4) . . . . ?
N2 C9 C8 N1 46.1(4) . . . . ?
C12 C11 C10 N2 92.8(4) . . . . ?
C16 C11 C10 N2 -85.3(4) . . . . ?
C9 N2 C10 C11 -77.5(4) . . . . ?
Cu1 N2 C10 C11 154.2(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C14 C15 C16 C11 0.9(6) . . . . ?
C12 C11 C16 C15 -1.6(5) . . . . ?
C10 C11 C16 C15 176.6(3) . . . . ?
C16 C15 C14 C13 0.4(7) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.074

