# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_22gtu259_brbnzylsh_ligand
_database_code_depnum_ccdc_archive 'CCDC 2221531'
loop_
_audit_author_name
_audit_author_address
'Hasan Piskin'
;Bogazici University
T?rkiye
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Br N2 S'
_chemical_formula_sum            'C15 H9 Br N2 S'
_chemical_formula_weight         329.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.827(3)
_cell_length_b                   7.757(4)
_cell_length_c                   13.338(6)
_cell_angle_alpha                81.106(7)
_cell_angle_beta                 83.918(8)
_cell_angle_gamma                86.476(8)
_cell_volume                     693.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.376
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_min  0.4842
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.553
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2095
_reflns_number_total             3151
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.4262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1320
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26709(8) 0.36695(6) 0.48312(3) 0.0878(2) Uani 1 1 d . . . . .
S1 S 0.21581(16) -0.20540(10) 0.13155(6) 0.0569(3) Uani 1 1 d . . . . .
C2 C 0.2505(4) -0.3933(4) -0.0237(2) 0.0388(7) Uani 1 1 d . . . . .
C3 C 0.2643(5) -0.5461(4) -0.0684(3) 0.0471(8) Uani 1 1 d . . . . .
N1 N 0.2616(5) -0.0914(4) -0.1363(2) 0.0619(8) Uani 1 1 d . . . . .
C1 C 0.2314(4) -0.4027(4) 0.0823(2) 0.0403(7) Uani 1 1 d . . . . .
C6 C 0.2249(5) -0.5677(4) 0.1417(3) 0.0496(8) Uani 1 1 d . . . . .
C13 C 0.2402(6) 0.1792(5) 0.4100(2) 0.0557(9) Uani 1 1 d . . . . .
C4 C 0.2589(5) -0.7087(5) -0.0071(3) 0.0558(9) Uani 1 1 d . . . . .
C9 C 0.1842(8) -0.2700(5) 0.2684(3) 0.0641(11) Uani 1 1 d . . . . .
C11 C 0.0387(7) -0.0032(6) 0.3418(3) 0.0621(10) Uani 1 1 d . . . . .
C5 C 0.2401(6) -0.7162(5) 0.0964(3) 0.0575(10) Uani 1 1 d . . . . .
C8 C 0.2823(5) -0.5331(5) -0.1773(3) 0.0594(10) Uani 1 1 d . . . . .
C10 C 0.2006(6) -0.1095(5) 0.3170(2) 0.0537(9) Uani 1 1 d . . . . .
N2 N 0.2951(6) -0.5203(6) -0.2641(3) 0.0873(12) Uani 1 1 d . . . . .
C12 C 0.0583(7) 0.1410(6) 0.3886(3) 0.0653(10) Uani 1 1 d . . . . .
C15 C 0.3829(7) -0.0636(6) 0.3368(3) 0.0672(11) Uani 1 1 d . . . . .
C14 C 0.4003(8) 0.0797(6) 0.3836(3) 0.0693(12) Uani 1 1 d . . . . .
C7 C 0.2560(5) -0.2251(4) -0.0877(2) 0.0435(7) Uani 1 1 d . . . . .
H6 H 0.223(5) -0.582(5) 0.212(3) 0.058(11) Uiso 1 1 d . . . . .
H9A H 0.048(6) -0.316(6) 0.287(3) 0.076(13) Uiso 1 1 d . . . . .
H9B H 0.279(8) -0.362(7) 0.288(4) 0.105(18) Uiso 1 1 d . . . . .
H14 H 0.511(6) 0.093(5) 0.390(3) 0.062(13) Uiso 1 1 d . . . . .
H15 H 0.477(6) -0.120(5) 0.320(3) 0.062(13) Uiso 1 1 d . . . . .
H11 H -0.078(6) -0.026(5) 0.327(3) 0.068(12) Uiso 1 1 d . . . . .
H4 H 0.273(6) -0.801(6) -0.042(3) 0.069(11) Uiso 1 1 d . . . . .
H12 H -0.047(6) 0.206(6) 0.406(3) 0.071(13) Uiso 1 1 d . . . . .
H5 H 0.240(6) -0.814(6) 0.138(3) 0.079(13) 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 C13 1.902(4) . ?
S1 C1 1.749(3) . ?
S1 C9 1.810(4) . ?
C2 C3 1.401(4) . ?
C2 C1 1.397(4) . ?
C2 C7 1.445(4) . ?
C3 C4 1.393(5) . ?
C3 C8 1.433(5) . ?
N1 C7 1.135(4) . ?
C1 C6 1.398(4) . ?
C6 C5 1.375(5) . ?
C13 C12 1.363(6) . ?
C13 C14 1.346(6) . ?
C4 C5 1.364(6) . ?
C9 C10 1.505(5) . ?
C11 C10 1.381(6) . ?
C11 C12 1.382(6) . ?
C8 N2 1.141(5) . ?
C10 C15 1.378(6) . ?
C15 C14 1.373(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C9 104.31(17) . . ?
C3 C2 C7 119.7(3) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 C7 119.9(3) . . ?
C2 C3 C8 119.3(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 C8 120.7(3) . . ?
C2 C1 S1 117.3(2) . . ?
C2 C1 C6 118.2(3) . . ?
C6 C1 S1 124.5(3) . . ?
C5 C6 C1 120.5(3) . . ?
C12 C13 Br1 120.0(3) . . ?
C14 C13 Br1 119.7(3) . . ?
C14 C13 C12 120.3(4) . . ?
C5 C4 C3 119.1(3) . . ?
C10 C9 S1 107.6(3) . . ?
C10 C11 C12 120.9(4) . . ?
C4 C5 C6 121.8(3) . . ?
N2 C8 C3 179.0(4) . . ?
C11 C10 C9 122.4(4) . . ?
C15 C10 C9 119.7(4) . . ?
C15 C10 C11 117.9(4) . . ?
C13 C12 C11 119.5(4) . . ?
C14 C15 C10 120.6(4) . . ?
C13 C14 C15 120.8(4) . . ?
N1 C7 C2 178.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9B Br1 0.96(5) 3.08(5) 3.756(4) 129(4) 1_545 yes

_olex2_submission_special_instructions 'No special instructions were received'
