# Supplementary Information (SI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2371583'
loop_
_audit_author_name
_audit_author_address
'Walid rekik'
;Sfax University, Sfax faculty of sciences
Tunisia
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2025-08-26 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 Cl4 Fe0.20 N4 Zn0.80'
_chemical_formula_weight         423.57

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'
Zn Zn 0.2839 1.4301 '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'
Fe Fe 0.3463 0.8444 '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                   8.0559(7)
_cell_length_b                   14.7738(12)
_cell_length_c                   15.7854(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.783(5)
_cell_angle_gamma                90
_cell_volume                     1839.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    182899
_cell_measurement_theta_min      2.975
_cell_measurement_theta_max      27.500

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             861
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.811
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            182899
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.1176
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.975
_diffrn_reflns_theta_max         27.500
_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             4222
_reflns_number_gt                2528
_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)+(0.0367P)²+1.3885P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4222
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_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
Zn Zn 0.37351(5) 0.39873(3) 0.29667(3) 0.05723(18) Uani 0.796(11) 1 d . . P . .
Fe Fe 0.37351(5) 0.39873(3) 0.29667(3) 0.05723(18) Uani 0.204(11) 1 d . . P . .
Cl1 Cl 0.36714(12) 0.33062(6) 0.42653(6) 0.0707(3) Uani 1 1 d . . . . .
Cl2 Cl 0.48336(13) 0.30083(6) 0.21308(6) 0.0754(3) Uani 1 1 d . . . . .
Cl3 Cl 0.11473(12) 0.44829(7) 0.23605(6) 0.0741(3) Uani 1 1 d . . . . .
Cl4 Cl 0.56291(12) 0.51578(6) 0.32564(6) 0.0738(3) Uani 1 1 d . . . . .
N1 N 0.0727(4) 0.3527(2) 0.5352(2) 0.0729(9) Uani 1 1 d . . . . .
HN1 H 0.1602 0.3481 0.5121 0.088 Uiso 1 1 calc R U . . .
N2 N 0.6745(4) 0.4773(2) 0.12922(18) 0.0683(8) Uani 1 1 d . . . . .
HN2 H 0.6481 0.4637 0.1778 0.082 Uiso 1 1 calc R U . . .
N3 N -0.0712(5) 0.4162(2) 0.4075(2) 0.0894(10) Uani 1 1 d . . . . .
H3A H 0.0179 0.4106 0.3858 0.107 Uiso 1 1 calc R U . . .
H3B H -0.1619 0.4395 0.3771 0.107 Uiso 1 1 calc R U . . .
N4 N 0.6038(4) 0.6249(2) 0.1527(2) 0.0892(10) Uani 1 1 d . . . . .
H4A H 0.5779 0.6093 0.2008 0.107 Uiso 1 1 calc R U . . .
H4B H 0.5939 0.6805 0.1362 0.107 Uiso 1 1 calc R U . . .
C1 C -0.0686(4) 0.3888(2) 0.4883(2) 0.0624(9) Uani 1 1 d . . . . .
C2 C -0.1966(4) 0.3655(2) 0.6082(2) 0.0655(9) Uani 1 1 d . . . . .
H2 H -0.2911 0.3705 0.6333 0.079 Uiso 1 1 calc R U . . .
C3 C -0.0486(5) 0.3276(2) 0.6562(2) 0.0671(9) Uani 1 1 d . . . . .
C4 C 0.6594(4) 0.5630(3) 0.1036(2) 0.0642(9) Uani 1 1 d . . . . .
C5 C 0.0850(5) 0.3229(3) 0.6174(3) 0.0723(10) Uani 1 1 d . . . . .
H5 H 0.1870 0.2990 0.6473 0.087 Uiso 1 1 calc R U . . .
C6 C -0.2067(4) 0.3950(2) 0.5270(2) 0.0643(9) Uani 1 1 d . . . . .
H6 H -0.3076 0.4197 0.4966 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7709(4) 0.4267(3) 0.0072(2) 0.0685(10) Uani 1 1 d . . . . .
C8 C 0.7544(5) 0.5160(3) -0.0222(2) 0.0725(10) Uani 1 1 d . . . . .
H8 H 0.7807 0.5300 -0.0753 0.087 Uiso 1 1 calc R U . . .
C9 C 0.7016(5) 0.5822(3) 0.0244(2) 0.0734(10) Uani 1 1 d . . . . .
H9 H 0.6932 0.6412 0.0035 0.088 Uiso 1 1 calc R U . . .
C10 C 0.7285(5) 0.4109(3) 0.0840(3) 0.0733(10) Uani 1 1 d . . . . .
H10 H 0.7370 0.3524 0.1062 0.088 Uiso 1 1 calc R U . . .
C11 C -0.0367(7) 0.2969(3) 0.7483(3) 0.1028(15) Uani 1 1 d . . . . .
H11A H 0.0584 0.2568 0.7645 0.154 Uiso 1 1 calc R U . . .
H11B H -0.1389 0.2657 0.7530 0.154 Uiso 1 1 calc R U . . .
H11C H -0.0219 0.3485 0.7859 0.154 Uiso 1 1 calc R U . . .
C12 C 0.8276(6) 0.3528(3) -0.0453(3) 0.1052(15) Uani 1 1 d . . . . .
H12A H 0.7759 0.2967 -0.0340 0.158 Uiso 1 1 calc R U . . .
H12B H 0.9487 0.3470 -0.0299 0.158 Uiso 1 1 calc R U . . .
H12C H 0.7946 0.3672 -0.1057 0.158 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
Zn Cl3 2.2323(10) . ?
Zn Cl2 2.2568(10) . ?
Zn Cl4 2.2896(10) . ?
Zn Cl1 2.2934(10) . ?
N1 C1 1.336(4) . ?
N1 C5 1.354(5) . ?
N1 HN1 0.8600 . ?
N2 C4 1.326(4) . ?
N2 C10 1.337(4) . ?
N2 HN2 0.8600 . ?
N3 C1 1.335(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C4 1.334(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C1 C6 1.378(4) . ?
C2 C6 1.341(5) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.345(5) . ?
C3 C11 1.507(5) . ?
C4 C9 1.391(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.346(5) . ?
C7 C8 1.395(5) . ?
C7 C12 1.498(5) . ?
C8 C9 1.344(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
Cl3 Zn Cl2 113.76(4) . . ?
Cl3 Zn Cl4 111.34(4) . . ?
Cl2 Zn Cl4 106.02(4) . . ?
Cl3 Zn Cl1 109.74(4) . . ?
Cl2 Zn Cl1 108.93(4) . . ?
Cl4 Zn Cl1 106.77(4) . . ?
C1 N1 C5 123.2(3) . . ?
C1 N1 HN1 118.4 . . ?
C5 N1 HN1 118.4 . . ?
C4 N2 C10 123.9(3) . . ?
C4 N2 HN2 118.1 . . ?
C10 N2 HN2 118.1 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N3 C1 N1 119.8(3) . . ?
N3 C1 C6 123.2(4) . . ?
N1 C1 C6 117.0(3) . . ?
C6 C2 C3 121.9(3) . . ?
C6 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C5 C3 C2 116.7(3) . . ?
C5 C3 C11 121.7(4) . . ?
C2 C3 C11 121.6(4) . . ?
N2 C4 N4 119.9(3) . . ?
N2 C4 C9 116.4(3) . . ?
N4 C4 C9 123.7(4) . . ?
C3 C5 N1 120.8(3) . . ?
C3 C5 H5 119.6 . . ?
N1 C5 H5 119.6 . . ?
C2 C6 C1 120.4(3) . . ?
C2 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C10 C7 C8 116.0(4) . . ?
C10 C7 C12 122.3(4) . . ?
C8 C7 C12 121.6(4) . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 120.4(4) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
N2 C10 C7 121.6(4) . . ?
N2 C10 H10 119.2 . . ?
C7 C10 H10 119.2 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C5 N1 C1 N3 -179.6(3) . . . . ?
C5 N1 C1 C6 -0.2(5) . . . . ?
C6 C2 C3 C5 0.8(6) . . . . ?
C6 C2 C3 C11 178.3(4) . . . . ?
C10 N2 C4 N4 179.7(4) . . . . ?
C10 N2 C4 C9 0.7(5) . . . . ?
C2 C3 C5 N1 -1.1(5) . . . . ?
C11 C3 C5 N1 -178.5(4) . . . . ?
C1 N1 C5 C3 0.8(6) . . . . ?
C3 C2 C6 C1 -0.3(6) . . . . ?
N3 C1 C6 C2 179.4(4) . . . . ?
N1 C1 C6 C2 0.0(5) . . . . ?
C10 C7 C8 C9 0.9(6) . . . . ?
C12 C7 C8 C9 179.2(4) . . . . ?
C7 C8 C9 C4 -0.8(6) . . . . ?
N2 C4 C9 C8 0.0(6) . . . . ?
N4 C4 C9 C8 -179.0(4) . . . . ?
C4 N2 C10 C7 -0.6(6) . . . . ?
C8 C7 C10 N2 -0.2(6) . . . . ?
C12 C7 C10 N2 -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
N1 HN1 Cl1 0.86 2.36 3.215(3) 170.3 .
N2 HN2 Cl2 0.86 2.86 3.429(3) 125.5 .
N2 HN2 Cl4 0.86 2.68 3.447(3) 149.8 .
N3 H3A Cl3 0.86 2.69 3.383(3) 138.1 .
N3 H3B Cl4 0.86 2.47 3.311(4) 165.7 1_455
N4 H4A Cl4 0.86 2.43 3.245(4) 158.5 .
N4 H4B Cl1 0.86 2.48 3.313(4) 164.9 2_655
C5 H5 Cl2 0.93 2.82 3.734(4) 168.6 4_566
C6 H6 Cl1 0.93 2.94 3.603(4) 129.5 1_455

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.058

