# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 2092549'
loop_
_audit_author_name
_audit_author_address
'Houcine Naili'
;University of sfax
Tunisia
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2022-11-15 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            'C18 H21 Br8 Cd N3'
_chemical_formula_weight         1031.06

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'
Cd Cd -0.8075 1.2024 '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'

_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                   15.4709(14)
_cell_length_b                   8.1826(10)
_cell_length_c                   23.466(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.590(10)
_cell_angle_gamma                90
_cell_volume                     2929.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6444
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.44

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_F_000             1912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    11.670
_shelx_estimated_absorpt_T_min   0.179
_shelx_estimated_absorpt_T_max   0.388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.170
_exptl_absorpt_correction_T_max  0.353
_exptl_absorpt_process_details   ?
_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  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64272
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6738
_reflns_number_gt                4209
_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-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)+(0.0316P)²+4.0639P] 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         6738
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Cd1 Cd 0.53082(3) 0.99926(5) 0.16647(2) 0.04166(11) Uani 1 1 d . . . . .
Br1 Br 0.47532(4) 1.25458(7) 0.24347(2) 0.04299(14) Uani 1 1 d . . . . .
Br3 Br 0.56368(4) 0.74510(7) 0.09403(2) 0.05140(16) Uani 1 1 d . . . . .
Br2 Br 0.69401(4) 1.05978(7) 0.22714(2) 0.04396(15) Uani 1 1 d . . . . .
Br4 Br 0.35105(4) 0.95498(8) 0.13964(3) 0.05421(17) Uani 1 1 d . . . . .
Br8 Br 0.07671(5) 0.37259(10) 0.95467(3) 0.0689(2) Uani 1 1 d . . . . .
Br6 Br 0.03970(5) 0.08532(11) 0.11504(4) 0.0834(2) Uani 1 1 d . . . . .
Br5 Br 0.54055(4) 1.24227(7) 0.08567(2) 0.05266(17) Uani 1 1 d . . . . .
Br7 Br 0.95519(5) 0.13544(10) 0.29352(4) 0.0806(2) Uani 1 1 d . . . . .
N1 N -0.3480(3) 0.0125(6) 0.0041(2) 0.0547(13) Uani 1 1 d . . . . .
HN1A H -0.366298 -0.086143 0.012726 0.082 Uiso 1 1 calc R U . . .
HN1B H -0.353769 0.022740 -0.034148 0.082 Uiso 1 1 calc R U . . .
HN1C H -0.380023 0.088573 0.017902 0.082 Uiso 1 1 calc R U . . .
N2 N 1.3428(3) -0.0353(6) 0.2938(2) 0.0539(13) Uani 1 1 d . . . . .
HN2A H 1.372381 -0.032417 0.329730 0.081 Uiso 1 1 calc R U . . .
HN2B H 1.365892 0.036309 0.272062 0.081 Uiso 1 1 calc R U . . .
HN2C H 1.345925 -0.135227 0.279338 0.081 Uiso 1 1 calc R U . . .
N3 N 0.3943(3) 0.5379(6) 1.1406(2) 0.0506(12) Uani 1 1 d . . . . .
HN3A H 0.379330 0.614897 1.163875 0.076 Uiso 1 1 calc R U . . .
HN3B H 0.438714 0.573278 1.124191 0.076 Uiso 1 1 calc R U . . .
HN3C H 0.410410 0.447987 1.160940 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3180(4) 0.5002(7) 1.0949(2) 0.0412(13) Uani 1 1 d . . . . .
C8 C 0.3294(4) 0.4806(8) 1.0382(3) 0.0540(16) Uani 1 1 d . . . . .
H8 H 0.384775 0.491865 1.028135 0.065 Uiso 1 1 calc R U . . .
C10 C 0.1757(4) 0.4264(7) 1.0122(2) 0.0493(14) Uani 1 1 d . . . . .
C1 C -0.2546(4) 0.0330(7) 0.0302(2) 0.0485(15) Uani 1 1 d . . . . .
C11 C 0.1643(4) 0.4497(9) 1.0688(3) 0.0607(17) Uani 1 1 d . . . . .
H11 H 0.108755 0.441309 1.078737 0.073 Uiso 1 1 calc R U . . .
C13 C 1.2499(4) 0.0072(7) 0.2943(2) 0.0415(13) Uani 1 1 d . . . . .
C5 C -0.1413(5) 0.0084(8) 0.1132(3) 0.0621(18) Uani 1 1 d . . . . .
H5 H -0.123344 -0.019192 0.151754 0.074 Uiso 1 1 calc R U . . .
C6 C -0.2284(4) -0.0111(8) 0.0877(3) 0.0578(17) Uani 1 1 d . . . . .
H6 H -0.268914 -0.053416 0.108954 0.069 Uiso 1 1 calc R U . . .
C14 C 1.2142(4) 0.1415(7) 0.2640(3) 0.0572(16) Uani 1 1 d . . . . .
H14 H 1.248341 0.205229 0.243531 0.069 Uiso 1 1 calc R U . . .
C2 C -0.1956(4) 0.0983(9) -0.0015(3) 0.0649(19) Uani 1 1 d . . . . .
H2 H -0.214086 0.130689 -0.039581 0.078 Uiso 1 1 calc R U . . .
C17 C 1.1128(4) -0.0514(8) 0.3245(3) 0.0547(16) Uani 1 1 d . . . . .
H17 H 1.078817 -0.116799 0.344513 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2362(4) 0.4858(8) 1.1110(3) 0.0583(17) Uani 1 1 d . . . . .
H12 H 0.229391 0.499949 1.149318 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2571(4) 0.4436(8) 0.9960(3) 0.0575(17) Uani 1 1 d . . . . .
H9 H 0.263670 0.430877 0.957526 0.069 Uiso 1 1 calc R U . . .
C4 C -0.0816(4) 0.0688(8) 0.0811(3) 0.0550(16) Uani 1 1 d . . . . .
C16 C 1.0759(4) 0.0836(7) 0.2941(3) 0.0495(15) Uani 1 1 d . . . . .
C18 C 1.2006(4) -0.0892(7) 0.3251(3) 0.0537(16) Uani 1 1 d . . . . .
H18 H 1.225871 -0.178423 0.346103 0.064 Uiso 1 1 calc R U . . .
C3 C -0.1070(5) 0.1157(9) 0.0242(3) 0.068(2) Uani 1 1 d . . . . .
H3 H -0.066270 0.158119 0.003168 0.082 Uiso 1 1 calc R U . . .
C15 C 1.1263(4) 0.1821(8) 0.2640(3) 0.0585(17) Uani 1 1 d . . . . .
H15 H 1.101762 0.273707 0.244070 0.070 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
Cd1 Br2 2.7292(8) . ?
Cd1 Br5 2.7690(7) . ?
Cd1 Br4 2.7712(8) . ?
Cd1 Br3 2.7859(7) . ?
Cd1 Br1 2.9242(7) 2_645 ?
Cd1 Br1 2.9806(7) . ?
Br8 C10 1.917(6) . ?
Br6 C4 1.917(6) . ?
Br7 C16 1.913(6) . ?
N1 C1 1.482(8) . ?
N1 HN1A 0.8900 . ?
N1 HN1B 0.8900 . ?
N1 HN1C 0.8900 . ?
N2 C13 1.481(7) . ?
N2 HN2A 0.8900 . ?
N2 HN2B 0.8900 . ?
N2 HN2C 0.8900 . ?
N3 C7 1.489(7) . ?
N3 HN3A 0.8900 . ?
N3 HN3B 0.8900 . ?
N3 HN3C 0.8900 . ?
C7 C8 1.381(8) . ?
C7 C12 1.385(8) . ?
C8 C9 1.398(8) . ?
C8 H8 0.9300 . ?
C10 C9 1.382(8) . ?
C10 C11 1.383(8) . ?
C1 C2 1.378(8) . ?
C1 C6 1.390(8) . ?
C11 C12 1.390(9) . ?
C11 H11 0.9300 . ?
C13 C14 1.374(8) . ?
C13 C18 1.382(8) . ?
C5 C4 1.376(9) . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C14 C15 1.401(9) . ?
C14 H14 0.9300 . ?
C2 C3 1.410(9) . ?
C2 H2 0.9300 . ?
C17 C16 1.386(8) . ?
C17 C18 1.390(8) . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C4 C3 1.383(9) . ?
C16 C15 1.392(9) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
C15 H15 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
Br2 Cd1 Br5 94.35(2) . . ?
Br2 Cd1 Br4 161.52(2) . . ?
Br5 Cd1 Br4 96.04(2) . . ?
Br2 Cd1 Br3 101.93(2) . . ?
Br5 Cd1 Br3 94.70(2) . . ?
Br4 Cd1 Br3 92.41(2) . . ?
Br2 Cd1 Br1 83.44(2) . 2_645 ?
Br5 Cd1 Br1 176.99(2) . 2_645 ?
Br4 Cd1 Br1 85.55(2) . 2_645 ?
Br3 Cd1 Br1 87.77(2) . 2_645 ?
Br2 Cd1 Br1 83.77(2) . . ?
Br5 Cd1 Br1 88.04(2) . . ?
Br4 Cd1 Br1 81.36(2) . . ?
Br3 Cd1 Br1 173.44(2) . . ?
Br1 Cd1 Br1 89.682(16) 2_645 . ?
Cd1 Br1 Cd1 164.88(2) 2_655 . ?
C1 N1 HN1A 109.5 . . ?
C1 N1 HN1B 109.5 . . ?
HN1A N1 HN1B 109.5 . . ?
C1 N1 HN1C 109.5 . . ?
HN1A N1 HN1C 109.5 . . ?
HN1B N1 HN1C 109.5 . . ?
C13 N2 HN2A 109.5 . . ?
C13 N2 HN2B 109.5 . . ?
HN2A N2 HN2B 109.5 . . ?
C13 N2 HN2C 109.5 . . ?
HN2A N2 HN2C 109.5 . . ?
HN2B N2 HN2C 109.5 . . ?
C7 N3 HN3A 109.5 . . ?
C7 N3 HN3B 109.5 . . ?
HN3A N3 HN3B 109.5 . . ?
C7 N3 HN3C 109.5 . . ?
HN3A N3 HN3C 109.5 . . ?
HN3B N3 HN3C 109.5 . . ?
C8 C7 C12 121.5(5) . . ?
C8 C7 N3 120.3(5) . . ?
C12 C7 N3 118.2(5) . . ?
C7 C8 C9 119.5(6) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C9 C10 C11 121.2(6) . . ?
C9 C10 Br8 119.2(4) . . ?
C11 C10 Br8 119.6(5) . . ?
C2 C1 C6 120.8(6) . . ?
C2 C1 N1 120.6(5) . . ?
C6 C1 N1 118.6(5) . . ?
C10 C11 C12 119.9(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C14 C13 C18 121.2(6) . . ?
C14 C13 N2 119.3(5) . . ?
C18 C13 N2 119.4(5) . . ?
C4 C5 C6 119.9(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.5(6) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C16 C17 C18 120.0(6) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C7 C12 C11 118.8(6) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C10 C9 C8 119.0(6) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 Br6 119.9(5) . . ?
C3 C4 Br6 118.9(5) . . ?
C17 C16 C15 120.4(6) . . ?
C17 C16 Br7 119.8(5) . . ?
C15 C16 Br7 119.8(5) . . ?
C13 C18 C17 119.4(6) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C16 C15 C14 119.2(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?

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
C12 C7 C8 C9 -0.7(9) . . . . ?
N3 C7 C8 C9 179.4(5) . . . . ?
C9 C10 C11 C12 -2.2(10) . . . . ?
Br8 C10 C11 C12 178.8(5) . . . . ?
C4 C5 C6 C1 -1.0(10) . . . . ?
C2 C1 C6 C5 -1.1(10) . . . . ?
N1 C1 C6 C5 -179.5(6) . . . . ?
C18 C13 C14 C15 -0.2(9) . . . . ?
N2 C13 C14 C15 179.7(5) . . . . ?
C6 C1 C2 C3 2.0(10) . . . . ?
N1 C1 C2 C3 -179.6(6) . . . . ?
C8 C7 C12 C11 0.4(10) . . . . ?
N3 C7 C12 C11 -179.7(6) . . . . ?
C10 C11 C12 C7 1.0(10) . . . . ?
C11 C10 C9 C8 1.9(10) . . . . ?
Br8 C10 C9 C8 -179.1(5) . . . . ?
C7 C8 C9 C10 -0.5(10) . . . . ?
C6 C5 C4 C3 2.1(10) . . . . ?
C6 C5 C4 Br6 -176.8(5) . . . . ?
C18 C17 C16 C15 0.1(10) . . . . ?
C18 C17 C16 Br7 -179.8(5) . . . . ?
C14 C13 C18 C17 1.3(9) . . . . ?
N2 C13 C18 C17 -178.5(5) . . . . ?
C16 C17 C18 C13 -1.3(9) . . . . ?
C5 C4 C3 C2 -1.1(11) . . . . ?
Br6 C4 C3 C2 177.8(5) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
C17 C16 C15 C14 1.1(9) . . . . ?
Br7 C16 C15 C14 -179.0(5) . . . . ?
C13 C14 C15 C16 -1.0(9) . . . . ?

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
N1 HN1A Br3 0.89 2.72 3.475(5) 143.0 1_445 yes
N1 HN1B Br4 0.89 2.49 3.375(5) 173.3 3_565 yes
N1 HN1C Br5 0.89 2.50 3.358(5) 160.9 1_445 yes
N2 HN2A Br5 0.89 2.87 3.587(5) 138.2 2_735 yes
N2 HN2B Br1 0.89 2.62 3.469(5) 158.8 1_645 yes
N2 HN2C Br2 0.89 2.57 3.384(5) 152.5 2_735 yes
N3 HN3A Br4 0.89 2.86 3.477(5) 127.9 1_556 yes
N3 HN3B Br3 0.89 2.58 3.448(5) 164.3 1_556 yes
N3 HN3C Br1 0.89 2.57 3.430(5) 162.2 1_546 yes

_refine_diff_density_max         0.679
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.155

