# Electronic Supplementary Material (ESI) for Materials 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 2281265'
loop_
_audit_author_name
_audit_author_address
'Lahcen El Ammari'
;Mohammed V University in Rabat
Morocco
;

#Added by publCIF



_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2024-02-14 downloaded from the CCDC.
;
_publcif_datablock.id            {6b85440a-533d-4dd6-a4f7-e054107b36d8}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cl4 Fe N2, C2 H8 N'
_chemical_formula_sum            'C14 H16 Cl4 Fe N3'
_chemical_formula_weight         423.95

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'
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      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                   8.4271(7)
_cell_length_b                   8.5571(7)
_cell_length_c                   12.7653(10)
_cell_angle_alpha                97.119(3)
_cell_angle_beta                 91.008(2)
_cell_angle_gamma                104.883(2)
_cell_volume                     881.61(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.485
_cell_measurement_theta_max      38.565

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             430

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    1.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_process_details   '(SADABS; Krause et al., 2015)'

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'INCOATEC I\mS micro-focus source'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Super DUO'
_diffrn_detector                 'PHOTON100 CMOS area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            74034
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         38.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9941
_reflns_number_gt                8216
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3(Farrugia,2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCIF (Westrip, 2010)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.1138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9942
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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
Fe1 Fe 0.82531(2) 0.72071(2) 0.22208(2) 0.02566(3) Uani 1 1 d . . . . .
Cl1 Cl 0.99611(3) 0.53092(3) 0.18386(2) 0.03480(5) Uani 1 1 d . . . . .
Cl2 Cl 0.64811(3) 0.87646(3) 0.27829(2) 0.03860(5) Uani 1 1 d . . . . .
Cl3 Cl 0.74486(3) 0.67652(3) 0.04407(2) 0.03785(5) Uani 1 1 d . . . . .
Cl4 Cl 1.05095(3) 0.93969(3) 0.21612(2) 0.03611(5) Uani 1 1 d . . . . .
N1 N 0.88309(9) 0.70229(8) 0.38678(5) 0.02688(11) Uani 1 1 d . . . . .
N2 N 0.64103(9) 0.50527(9) 0.25757(6) 0.02849(12) Uani 1 1 d . . . . .
N3 N 0.81548(11) 0.25627(11) -0.00688(7) 0.03952(17) Uani 1 1 d . . . . .
H3A H 0.894024 0.260865 -0.052985 0.047 Uiso 1 1 calc R U . . .
H3B H 0.837059 0.352684 0.033355 0.047 Uiso 1 1 calc R U . . .
C1 C 1.00104(12) 0.80442(11) 0.45056(7) 0.03342(16) Uani 1 1 d . . . . .
H1 H 1.070607 0.891670 0.423658 0.040 Uiso 1 1 calc R U . . .
C2 C 1.02486(14) 0.78598(14) 0.55671(8) 0.0401(2) Uani 1 1 d . . . . .
H2 H 1.107727 0.860807 0.599389 0.048 Uiso 1 1 calc R U . . .
C3 C 0.92516(15) 0.65698(14) 0.59702(7) 0.0412(2) Uani 1 1 d . . . . .
H3 H 0.938827 0.644122 0.667613 0.049 Uiso 1 1 calc R U . . .
C4 C 0.80137(12) 0.54343(12) 0.53080(7) 0.03354(16) Uani 1 1 d . . . . .
C5 C 0.78482(10) 0.57302(10) 0.42596(6) 0.02653(12) Uani 1 1 d . . . . .
C6 C 0.65783(10) 0.46541(10) 0.35573(6) 0.02716(13) Uani 1 1 d . . . . .
C7 C 0.55440(12) 0.32719(11) 0.39120(8) 0.03495(17) Uani 1 1 d . . . . .
C8 C 0.57631(15) 0.29858(14) 0.49804(9) 0.0445(2) Uani 1 1 d . . . . .
H8 H 0.508793 0.207030 0.521748 0.053 Uiso 1 1 calc R U . . .
C9 C 0.69337(16) 0.40234(15) 0.56490(8) 0.0442(2) Uani 1 1 d . . . . .
H9 H 0.704131 0.381952 0.634202 0.053 Uiso 1 1 calc R U . . .
C10 C 0.42946(13) 0.22825(13) 0.31934(10) 0.0447(2) Uani 1 1 d . . . . .
H10 H 0.360584 0.133464 0.338281 0.054 Uiso 1 1 calc R U . . .
C11 C 0.40998(14) 0.27246(14) 0.22135(10) 0.0455(2) Uani 1 1 d . . . . .
H11 H 0.325583 0.209938 0.174129 0.055 Uiso 1 1 calc R U . . .
C12 C 0.51831(12) 0.41267(12) 0.19294(8) 0.03680(18) Uani 1 1 d . . . . .
H12 H 0.503823 0.442034 0.126384 0.044 Uiso 1 1 calc R U . . .
C13 C 0.65778(17) 0.2303(2) -0.06565(15) 0.0626(4) Uani 1 1 d . . . . .
H13A H 0.635587 0.129368 -0.112351 0.094 Uiso 1 1 calc R U . . .
H13B H 0.662741 0.318585 -0.106172 0.094 Uiso 1 1 calc R U . . .
H13C H 0.571768 0.225892 -0.016910 0.094 Uiso 1 1 calc R U . . .
C14 C 0.8238(3) 0.1325(2) 0.06019(15) 0.0750(5) Uani 1 1 d . . . . .
H14A H 0.746267 0.132703 0.114372 0.112 Uiso 1 1 calc R U . . .
H14B H 0.932717 0.155903 0.092202 0.112 Uiso 1 1 calc R U . . .
H14C H 0.797910 0.027206 0.018194 0.112 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
Fe1 N1 2.1835(7) . ?
Fe1 N2 2.1856(7) . ?
Fe1 Cl4 2.3114(3) . ?
Fe1 Cl2 2.3117(3) . ?
Fe1 Cl3 2.3167(3) . ?
Fe1 Cl1 2.4447(3) . ?
N1 C1 1.3280(11) . ?
N1 C5 1.3568(10) . ?
N2 C12 1.3286(11) . ?
N2 C6 1.3531(10) . ?
N3 C14 1.4564(18) . ?
N3 C13 1.4664(17) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
C1 C2 1.4003(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.3670(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.4113(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.4035(11) . ?
C4 C9 1.4336(15) . ?
C5 C6 1.4326(12) . ?
C6 C7 1.4074(11) . ?
C7 C10 1.4080(16) . ?
C7 C8 1.4322(15) . ?
C8 C9 1.3500(19) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.3699(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.4005(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N1 Fe1 N2 75.47(3) . . ?
N1 Fe1 Cl4 92.79(2) . . ?
N2 Fe1 Cl4 167.59(2) . . ?
N1 Fe1 Cl2 89.32(2) . . ?
N2 Fe1 Cl2 88.50(2) . . ?
Cl4 Fe1 Cl2 95.466(12) . . ?
N1 Fe1 Cl3 167.02(2) . . ?
N2 Fe1 Cl3 93.47(2) . . ?
Cl4 Fe1 Cl3 97.671(10) . . ?
Cl2 Fe1 Cl3 97.267(11) . . ?
N1 Fe1 Cl1 84.01(2) . . ?
N2 Fe1 Cl1 84.34(2) . . ?
Cl4 Fe1 Cl1 90.533(11) . . ?
Cl2 Fe1 Cl1 171.238(10) . . ?
Cl3 Fe1 Cl1 88.227(10) . . ?
C1 N1 C5 118.28(7) . . ?
C1 N1 Fe1 126.72(6) . . ?
C5 N1 Fe1 115.00(5) . . ?
C12 N2 C6 118.53(7) . . ?
C12 N2 Fe1 126.54(6) . . ?
C6 N2 Fe1 114.92(5) . . ?
C14 N3 C13 115.27(13) . . ?
C14 N3 H3A 108.5 . . ?
C13 N3 H3A 108.5 . . ?
C14 N3 H3B 108.5 . . ?
C13 N3 H3B 108.5 . . ?
H3A N3 H3B 107.5 . . ?
N1 C1 C2 122.63(9) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.38(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.56(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 117.11(9) . . ?
C5 C4 C9 119.13(9) . . ?
C3 C4 C9 123.76(9) . . ?
N1 C5 C4 123.00(8) . . ?
N1 C5 C6 117.15(7) . . ?
C4 C5 C6 119.84(8) . . ?
N2 C6 C7 122.92(8) . . ?
N2 C6 C5 117.33(7) . . ?
C7 C6 C5 119.73(8) . . ?
C6 C7 C10 117.07(9) . . ?
C6 C7 C8 119.11(10) . . ?
C10 C7 C8 123.77(9) . . ?
C9 C8 C7 121.08(9) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C4 121.07(9) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C11 C10 C7 119.59(9) . . ?
C11 C10 H10 120.2 . . ?
C7 C10 H10 120.2 . . ?
C10 C11 C12 119.39(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N2 C12 C11 122.42(10) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C2 -1.64(13) . . . . ?
Fe1 N1 C1 C2 177.45(7) . . . . ?
N1 C1 C2 C3 0.96(15) . . . . ?
C1 C2 C3 C4 0.80(15) . . . . ?
C2 C3 C4 C5 -1.75(14) . . . . ?
C2 C3 C4 C9 178.48(9) . . . . ?
C1 N1 C5 C4 0.58(12) . . . . ?
Fe1 N1 C5 C4 -178.62(6) . . . . ?
C1 N1 C5 C6 179.57(8) . . . . ?
Fe1 N1 C5 C6 0.37(9) . . . . ?
C3 C4 C5 N1 1.10(13) . . . . ?
C9 C4 C5 N1 -179.12(8) . . . . ?
C3 C4 C5 C6 -177.87(8) . . . . ?
C9 C4 C5 C6 1.91(12) . . . . ?
C12 N2 C6 C7 2.15(13) . . . . ?
Fe1 N2 C6 C7 -177.56(7) . . . . ?
C12 N2 C6 C5 -176.21(8) . . . . ?
Fe1 N2 C6 C5 4.07(10) . . . . ?
N1 C5 C6 N2 -3.00(11) . . . . ?
C4 C5 C6 N2 176.02(8) . . . . ?
N1 C5 C6 C7 178.58(8) . . . . ?
C4 C5 C6 C7 -2.40(12) . . . . ?
N2 C6 C7 C10 0.21(14) . . . . ?
C5 C6 C7 C10 178.53(9) . . . . ?
N2 C6 C7 C8 -177.10(9) . . . . ?
C5 C6 C7 C8 1.22(13) . . . . ?
C6 C7 C8 C9 0.44(16) . . . . ?
C10 C7 C8 C9 -176.68(11) . . . . ?
C7 C8 C9 C4 -0.93(17) . . . . ?
C5 C4 C9 C8 -0.26(15) . . . . ?
C3 C4 C9 C8 179.51(10) . . . . ?
C6 C7 C10 C11 -2.33(16) . . . . ?
C8 C7 C10 C11 174.84(11) . . . . ?
C7 C10 C11 C12 2.12(18) . . . . ?
C6 N2 C12 C11 -2.43(16) . . . . ?
Fe1 N2 C12 C11 177.26(8) . . . . ?
C10 C11 C12 N2 0.31(19) . . . . ?

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
N3 H3A Cl1 0.89 2.60 3.2561(9) 131.1 2_765 yes
N3 H3A Cl4 0.89 2.66 3.3434(10) 134.8 2_765 yes
N3 H3B Cl1 0.89 2.44 3.2222(10) 147.1 . yes

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.063



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
