# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 2225545'
loop_
_audit_author_name
_audit_author_address
'Walid rekik'
;Sfax University, Sfax faculty of sciences
Tunisia
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Cl8 N4 Sb2'
_chemical_formula_weight         745.40

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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 '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                   7.9767(7)
_cell_length_b                   9.0843(8)
_cell_length_c                   9.3456(8)
_cell_angle_alpha                86.352(6)
_cell_angle_beta                 69.069(5)
_cell_angle_gamma                74.829(5)
_cell_volume                     610.14(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1339
_cell_measurement_theta_min      2.324
_cell_measurement_theta_max      27.497

_exptl_crystal_description       platelet
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    3.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21842
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2796
_reflns_number_gt                2417
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0105P)²+0.3054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0451
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Sb1 Sb 0.67070(2) 0.08227(2) 0.08659(2) 0.03288(7) Uani 1 1 d . . . . .
Cl1 Cl 0.34576(10) -0.02653(8) 0.22265(8) 0.04535(19) Uani 1 1 d . . . . .
Cl2 Cl 0.45775(11) 0.31852(8) 0.08407(9) 0.0491(2) Uani 1 1 d . . . . .
Cl3 Cl 0.66378(11) 0.13599(9) 0.33813(8) 0.0507(2) Uani 1 1 d . . . . .
Cl4 Cl 0.93033(11) 0.20392(10) -0.04416(9) 0.0540(2) Uani 1 1 d . . . . .
N1 N 0.0296(3) 0.2906(3) 0.3461(3) 0.0413(6) Uani 1 1 d . . . . .
H1 H 0.1273 0.2243 0.2916 0.050 Uiso 1 1 calc R U . . .
N2 N 0.0601(3) 0.1628(3) 0.5595(3) 0.0530(7) Uani 1 1 d . . . . .
H2A H 0.1572 0.0984 0.5014 0.064 Uiso 1 1 calc R U . . .
H2B H 0.0223 0.1531 0.6573 0.064 Uiso 1 1 calc R U . . .
C1 C -0.3051(5) 0.6338(4) 0.2716(4) 0.0706(11) Uani 1 1 d . . . . .
H1A H -0.2358 0.6247 0.1635 0.106 Uiso 1 1 calc R U . . .
H1B H -0.3138 0.7321 0.3100 0.106 Uiso 1 1 calc R U . . .
H1C H -0.4275 0.6229 0.2901 0.106 Uiso 1 1 calc R U . . .
C2 C -0.2084(4) 0.5113(3) 0.3519(3) 0.0410(7) Uani 1 1 d . . . . .
C3 C -0.2725(4) 0.5014(3) 0.5113(3) 0.0439(7) Uani 1 1 d . . . . .
H3 H -0.3764 0.5750 0.5696 0.053 Uiso 1 1 calc R U . . .
C4 C -0.1891(4) 0.3885(3) 0.5842(3) 0.0411(7) Uani 1 1 d . . . . .
H4 H -0.2361 0.3848 0.6905 0.049 Uiso 1 1 calc R U . . .
C5 C -0.0316(4) 0.2776(3) 0.4983(3) 0.0367(6) Uani 1 1 d . . . . .
C6 C -0.0548(4) 0.4029(4) 0.2734(3) 0.0450(7) Uani 1 1 d . . . . .
H6 H -0.0059 0.4055 0.1671 0.054 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
Sb1 Cl2 2.3677(8) . ?
Sb1 Cl3 2.4097(8) . ?
Sb1 Cl4 2.4942(8) . ?
Sb1 Cl1 2.8527(8) . ?
N1 C5 1.337(3) . ?
N1 C6 1.354(4) . ?
N1 H1 0.8600 . ?
N2 C5 1.332(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C2 1.501(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C6 1.352(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?

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
Cl2 Sb1 Cl3 92.69(3) . . ?
Cl2 Sb1 Cl4 88.93(3) . . ?
Cl3 Sb1 Cl4 92.94(3) . . ?
Cl2 Sb1 Cl1 84.39(3) . . ?
Cl3 Sb1 Cl1 89.81(3) . . ?
Cl4 Sb1 Cl1 172.89(3) . . ?
C5 N1 C6 123.3(2) . . ?
C5 N1 H1 118.4 . . ?
C6 N1 H1 118.4 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C2 C3 116.1(3) . . ?
C6 C2 C1 121.7(3) . . ?
C3 C2 C1 122.2(3) . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 N1 119.0(3) . . ?
N2 C5 C4 123.8(3) . . ?
N1 C5 C4 117.1(3) . . ?
C2 C6 N1 121.5(3) . . ?
C2 C6 H6 119.2 . . ?
N1 C6 H6 119.2 . . ?

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
N1 H1 Cl1 0.86 2.44 3.246(2) 156.3 .
N2 H2A Cl1 0.86 2.65 3.402(3) 146.9 .
N2 H2B Cl4 0.86 2.66 3.487(3) 162.6 1_456

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.086



