# 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. 
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data_b2638
_database_code_depnum_ccdc_archive 'CCDC 2422176'
loop_
_audit_author_name
_audit_author_address
'HRIZI chakib'
;Gabes university, Tunisia
Tunisia
;
_audit_update_record             
;
2025-10-27 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I8, C H4 O, 2(C8 H7 N2)'
_chemical_formula_sum            'C17 H18 Bi2 I8 N4 O'
_chemical_formula_weight         1727.51
_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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 '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                   7.5699(3)
_cell_length_b                   9.6520(3)
_cell_length_c                   11.5436(6)
_cell_angle_alpha                76.552(2)
_cell_angle_beta                 86.660(2)
_cell_angle_gamma                84.3830(10)
_cell_volume                     815.82(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.38
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.340
_shelx_estimated_absorpt_T_min   0.150
_exptl_absorpt_coefficient_mu    18.357
_exptl_absorpt_correction_T_max  0.5656
_exptl_absorpt_correction_T_min  0.3065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1482 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.5419.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             746
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            86682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.601
_diffrn_reflns_theta_min         2.497
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker D8 VENTURE area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'CPAD PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5735
_reflns_number_total             5972
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.590
_refine_diff_density_min         -1.887
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       0.00092(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5972
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+3.7828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0476
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-C9
 1.45 with sigma of 0.02
 C1-C2 \\sim C1-C6 \\sim C2-C3 \\sim C3-C4 \\sim C4-C5 \\sim C5-C6 \\sim C7-C8
 with sigma of 0.05
 C1A-C2A \\sim C1A-C6A \\sim C2A-C3A \\sim C3A-C4A \\sim C4A-C5A \\sim C5A-C6A
\\sim C7A-C8A
 with sigma of 0.05
3. Rigid body (RIGU) restrains
 N1, N2, C1, C2, C3, C4, C5, C6, C7, C8, N1A, N2A, C1A, C2A, C3A, C4A, C5A,
 C6A, C7A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(N1A)=Sof(H1A)=Sof(N2A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=
 Sof(H8A)=1-FVAR(1)
 Sof(N1)=Sof(H1)=Sof(N2)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=FVAR(1)
 Fixed Sof: O1(0.5) H1B(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A),
 C8A(H8A)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
5.c Idealised tetrahedral OH refined with riding coordinates:
 O1(H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Bi1 Bi 0.26737(2) 0.93044(2) 0.41328(2) 0.01569(3) Uani 1 1 d . . . . .
I1 I 0.60706(3) 0.77300(2) 0.53964(2) 0.01995(5) Uani 1 1 d . . . . .
I2 I -0.08133(3) 1.09648(3) 0.31882(2) 0.02111(5) Uani 1 1 d . . . . .
I3 I 0.43083(3) 0.98408(3) 0.17214(2) 0.02266(5) Uani 1 1 d . . . . .
I4 I 0.15201(3) 0.65275(2) 0.40747(2) 0.02353(5) Uani 1 1 d . . . . .
O1 O 0.9825(17) 0.8947(10) 0.0833(10) 0.080(4) Uani 0.5 1 d D . P A -1
H1B H 0.942436 0.915354 0.147149 0.120 Uiso 0.5 1 calc R U P A -1
C9 C 1.002(5) 1.0219(19) -0.005(3) 0.038(4) Uani 0.5 1 d D . P A -1
H9A H 0.949542 1.014465 -0.078624 0.058 Uiso 0.5 1 calc R U P A -1
H9B H 1.128251 1.036076 -0.019896 0.058 Uiso 0.5 1 calc R U P A -1
H9C H 0.941033 1.103239 0.022957 0.058 Uiso 0.5 1 calc R U P A -1
N1 N 0.7885(16) 0.6826(15) 0.1238(11) 0.0270(17) Uani 0.74(4) 1 d . . P B 1
H1 H 0.836093 0.763185 0.092455 0.032 Uiso 0.74(4) 1 calc R U P B 1
N2 N 0.6427(13) 0.4336(17) 0.2234(11) 0.037(2) Uani 0.74(4) 1 d . . P B 1
C1 C 0.771(3) 0.5893(14) 0.0557(11) 0.0189(17) Uani 0.74(4) 1 d D . P B 1
C2 C 0.824(3) 0.6281(19) -0.0677(13) 0.022(2) Uani 0.74(4) 1 d D . P B 1
H2 H 0.873(10) 0.712(8) -0.101(7) 0.030(18) Uiso 0.74(4) 1 d . . P B 1
C3 C 0.804(3) 0.5298(18) -0.1333(13) 0.028(2) Uani 0.74(4) 1 d D . P B 1
H3 H 0.838426 0.551128 -0.215605 0.034 Uiso 0.74(4) 1 calc R U P B 1
C4 C 0.735(3) 0.3971(18) -0.0825(14) 0.035(2) Uani 0.74(4) 1 d D . P B 1
H4 H 0.727(8) 0.334(7) -0.136(6) 0.017(15) Uiso 0.74(4) 1 d . . P B 1
C5 C 0.6823(16) 0.3589(12) 0.0369(15) 0.033(2) Uani 0.74(4) 1 d D . P B 1
H5 H 0.626(11) 0.275(9) 0.077(7) 0.04(2) Uiso 0.74(4) 1 d . . P B 1
C6 C 0.6976(16) 0.4582(13) 0.1080(10) 0.0232(16) Uani 0.74(4) 1 d D . P B 1
C7 C 0.6585(16) 0.528(2) 0.2863(8) 0.038(3) Uani 0.74(4) 1 d D . P B 1
H7 H 0.616(11) 0.514(9) 0.368(7) 0.04(2) Uiso 0.74(4) 1 d . . P B 1
C8 C 0.7348(15) 0.6545(19) 0.2374(10) 0.034(2) Uani 0.74(4) 1 d D . P B 1
H8 H 0.761(9) 0.729(7) 0.284(6) 0.023(16) Uiso 0.74(4) 1 d . . P B 1
N1A N 0.810(5) 0.717(3) 0.107(2) 0.019(4) Uani 0.26(4) 1 d . . P B 2
H1A H 0.859592 0.794419 0.069432 0.023 Uiso 0.26(4) 1 calc R U P B 2
N2A N 0.670(4) 0.471(3) 0.2395(19) 0.023(4) Uani 0.26(4) 1 d . . P B 2
C1A C 0.778(8) 0.615(5) 0.046(3) 0.020(4) Uani 0.26(4) 1 d D . P B 2
C2A C 0.811(10) 0.608(6) -0.072(4) 0.025(6) Uani 0.26(4) 1 d D . P B 2
H2A H 0.860848 0.687948 -0.122526 0.029 Uiso 0.26(4) 1 calc R U P B 2
C3A C 0.781(8) 0.503(5) -0.124(4) 0.030(6) Uani 0.26(4) 1 d D . P B 2
H3A H 0.806114 0.511664 -0.207206 0.036 Uiso 0.26(4) 1 calc R U P B 2
C4A C 0.714(8) 0.381(5) -0.056(4) 0.034(6) Uani 0.26(4) 1 d D . P B 2
H4A H 0.693913 0.301874 -0.087517 0.040 Uiso 0.26(4) 1 calc R U P B 2
C5A C 0.679(5) 0.383(4) 0.060(3) 0.031(5) Uani 0.26(4) 1 d D . P B 2
H5A H 0.629583 0.301827 0.109931 0.037 Uiso 0.26(4) 1 calc R U P B 2
C6A C 0.710(5) 0.493(4) 0.111(2) 0.022(4) Uani 0.26(4) 1 d D . P B 2
C7A C 0.701(4) 0.574(3) 0.2862(18) 0.021(5) Uani 0.26(4) 1 d D . P B 2
H7A H 0.676834 0.565651 0.369141 0.025 Uiso 0.26(4) 1 calc R U P B 2
C8A C 0.769(4) 0.699(3) 0.219(2) 0.023(4) Uani 0.26(4) 1 d D . P B 2
H8A H 0.786044 0.773148 0.257798 0.027 Uiso 0.26(4) 1 calc R U P B 2


_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
Bi1 I1 3.1129(3) . ?
Bi1 I1 3.2724(3) 2_676 ?
Bi1 I2 3.0691(3) . ?
Bi1 I2 3.2870(3) 2_576 ?
Bi1 I3 2.9328(3) . ?
Bi1 I4 2.9154(3) . ?
O1 H1B 0.8400 . ?
O1 C9 1.414(14) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1 H1 0.8800 . ?
N1 C1 1.346(13) . ?
N1 C8 1.324(10) . ?
N2 C6 1.346(12) . ?
N2 C7 1.305(13) . ?
C1 C2 1.430(13) . ?
C1 C6 1.421(9) . ?
C2 H2 0.91(7) . ?
C2 C3 1.369(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.417(12) . ?
C4 H4 0.97(6) . ?
C4 C5 1.386(13) . ?
C5 H5 0.96(8) . ?
C5 C6 1.415(10) . ?
C7 H7 0.96(8) . ?
C7 C8 1.390(12) . ?
C8 H8 1.03(7) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.39(4) . ?
N1A C8A 1.29(3) . ?
N2A C6A 1.47(3) . ?
N2A C7A 1.29(2) . ?
C1A C2A 1.39(3) . ?
C1A C6A 1.37(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.33(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.38(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.35(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.37(2) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.40(2) . ?
C8A H8A 0.9500 . ?

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
I1 Bi1 I1 87.708(7) . 2_676 ?
I1 Bi1 I2 82.887(7) 2_676 2_576 ?
I1 Bi1 I2 86.690(7) . 2_576 ?
I2 Bi1 I1 172.687(7) . . ?
I2 Bi1 I1 88.698(7) . 2_676 ?
I2 Bi1 I2 86.547(7) . 2_576 ?
I3 Bi1 I1 92.163(8) . 2_676 ?
I3 Bi1 I1 95.477(8) . . ?
I3 Bi1 I2 91.020(7) . . ?
I3 Bi1 I2 174.525(8) . 2_576 ?
I4 Bi1 I1 88.643(7) . . ?
I4 Bi1 I1 171.994(8) . 2_676 ?
I4 Bi1 I2 89.792(8) . 2_576 ?
I4 Bi1 I2 94.110(8) . . ?
I4 Bi1 I3 95.278(8) . . ?
Bi1 I1 Bi1 92.292(7) . 2_676 ?
Bi1 I2 Bi1 93.453(7) . 2_576 ?
C9 O1 H1B 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 H1 119.6 . . ?
C8 N1 H1 119.6 . . ?
C8 N1 C1 120.7(7) . . ?
C7 N2 C6 120.6(7) . . ?
N1 C1 C2 118.2(10) . . ?
N1 C1 C6 119.1(8) . . ?
C6 C1 C2 122.6(12) . . ?
C1 C2 H2 122(5) . . ?
C3 C2 C1 116.2(13) . . ?
C3 C2 H2 121(5) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(12) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 116(4) . . ?
C5 C4 C3 122.0(12) . . ?
C5 C4 H4 122(4) . . ?
C4 C5 H5 127(5) . . ?
C4 C5 C6 117.9(10) . . ?
C6 C5 H5 114(5) . . ?
N2 C6 C1 118.6(8) . . ?
N2 C6 C5 122.3(7) . . ?
C5 C6 C1 119.1(9) . . ?
N2 C7 H7 122(5) . . ?
N2 C7 C8 121.4(7) . . ?
C8 C7 H7 117(5) . . ?
N1 C8 C7 119.4(8) . . ?
N1 C8 H8 115(4) . . ?
C7 C8 H8 125(4) . . ?
C1A N1A H1A 119.7 . . ?
C8A N1A H1A 119.7 . . ?
C8A N1A C1A 121(2) . . ?
C7A N2A C6A 115(2) . . ?
N1A C1A C2A 132(4) . . ?
C6A C1A N1A 117(3) . . ?
C6A C1A C2A 111(4) . . ?
C1A C2A H2A 115.8 . . ?
C3A C2A C1A 128(5) . . ?
C3A C2A H2A 115.8 . . ?
C2A C3A H3A 120.6 . . ?
C2A C3A C4A 119(4) . . ?
C4A C3A H3A 120.6 . . ?
C3A C4A H4A 122.4 . . ?
C5A C4A C3A 115(4) . . ?
C5A C4A H4A 122.4 . . ?
C4A C5A H5A 117.7 . . ?
C4A C5A C6A 125(3) . . ?
C6A C5A H5A 117.7 . . ?
C1A C6A N2A 122(2) . . ?
C1A C6A C5A 122(3) . . ?
C5A C6A N2A 116(2) . . ?
N2A C7A H7A 118.9 . . ?
N2A C7A C8A 122.3(18) . . ?
C8A C7A H7A 118.9 . . ?
N1A C8A C7A 123(2) . . ?
N1A C8A H8A 118.7 . . ?
C7A C8A H8A 118.7 . . ?

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
N1 C1 C2 C3 179.9(17) . . . . ?
N1 C1 C6 N2 2.1(19) . . . . ?
N1 C1 C6 C5 -178.8(14) . . . . ?
N2 C7 C8 N1 1.8(13) . . . . ?
C1 N1 C8 C7 -0.5(17) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C1 C6 N2 -176.6(19) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 1.0(18) . . . . ?
C4 C5 C6 N2 176.9(13) . . . . ?
C4 C5 C6 C1 -2.1(16) . . . . ?
C6 N2 C7 C8 -1.1(13) . . . . ?
C6 C1 C2 C3 -1(3) . . . . ?
C7 N2 C6 C1 -0.8(15) . . . . ?
C7 N2 C6 C5 -179.8(9) . . . . ?
C8 N1 C1 C2 177.3(17) . . . . ?
C8 N1 C1 C6 -1(2) . . . . ?
N1A C1A C2A C3A 177(6) . . . . ?
N1A C1A C6A N2A 1(6) . . . . ?
N1A C1A C6A C5A -177(4) . . . . ?
N2A C7A C8A N1A -2(4) . . . . ?
C1A N1A C8A C7A 4(5) . . . . ?
C1A C2A C3A C4A -2(10) . . . . ?
C2A C1A C6A N2A 178(5) . . . . ?
C2A C1A C6A C5A -1(6) . . . . ?
C2A C3A C4A C5A 2(7) . . . . ?
C3A C4A C5A C6A -2(6) . . . . ?
C4A C5A C6A N2A -177(4) . . . . ?
C4A C5A C6A C1A 1(6) . . . . ?
C6A N2A C7A C8A 0(3) . . . . ?
C6A C1A C2A C3A 2(9) . . . . ?
C7A N2A C6A C1A 0(4) . . . . ?
C7A N2A C6A C5A 179(3) . . . . ?
C8A N1A C1A C2A -179(6) . . . . ?
C8A N1A C1A C6A -4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_b1250neu_0m
_database_code_depnum_ccdc_archive 'CCDC 2494203'
loop_
_audit_author_name
_audit_author_address
'HRIZI chakib'
;Gabes university, Tunisia
Tunisia
;
_audit_update_record             
;
2025-10-09 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I4 Sb, C10 H9 N2'
_chemical_formula_sum            'C10 H9 I4 N2 Sb'
_chemical_formula_weight         786.54
_chemical_absolute_configuration ?
_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'
I I -0.4742 1.8119 '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'

_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.2685(4)
_cell_length_b                   18.2626(6)
_cell_length_c                   7.5924(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8640(10)
_cell_angle_gamma                90
_cell_volume                     1700.21(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.316
_shelx_estimated_absorpt_T_min   0.245
_exptl_absorpt_coefficient_mu    8.869
_exptl_absorpt_correction_T_max  0.5645
_exptl_absorpt_correction_T_min  0.3883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0873 before and 0.0379 after correction.
The Ratio of minimum to maximum transmission is 0.6879.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    3.073
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.169
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36006
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.518
_diffrn_reflns_theta_min         2.230
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker D8 VENTURE area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'CPAD PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                4896
_reflns_number_total             5090
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         5090
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0146
_refine_ls_R_factor_gt           0.0134
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0086P)²+1.8006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0281
_refine_ls_wR_factor_ref         0.0284
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.55(4)
 0.45(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.14196(4) 0.43484(3) 0.17986(7) 0.01883(13) Uani 1 1 d . . . . .
I2 I 0.14556(4) 0.32549(3) 0.64945(7) 0.02014(13) Uani 1 1 d . . . . .
I3 I -0.14483(4) 0.32526(3) 0.34703(7) 0.01944(12) Uani 1 1 d . . . . .
I4 I -0.14096(4) 0.43526(3) 0.81623(7) 0.01794(12) Uani 1 1 d . . . . .
Sb1 Sb 0.00102(7) 0.43020(2) 0.49762(12) 0.01352(4) Uani 1 1 d . . . . .
N1 N 0.5790(4) 0.3693(3) 0.5527(7) 0.0274(10) Uani 1 1 d . . . . .
H1 H 0.642086 0.385217 0.595730 0.033 Uiso 1 1 calc R U . . .
N2 N 0.4098(6) 0.5312(4) 0.4298(10) 0.0270(19) Uani 1 1 d . . . . .
C1 C 0.5589(5) 0.2925(3) 0.5300(8) 0.0291(11) Uani 1 1 d . . . . .
H1A H 0.612638 0.258225 0.569252 0.035 Uiso 1 1 calc R U . . .
C2 C 0.4621(5) 0.2675(3) 0.4513(8) 0.0302(11) Uani 1 1 d . . . . .
H2 H 0.448949 0.216393 0.440481 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3856(4) 0.3166(2) 0.3894(6) 0.0298(9) Uani 1 1 d . . . . .
H3 H 0.320174 0.299224 0.333652 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4025(5) 0.3905(3) 0.4071(9) 0.0247(11) Uani 1 1 d . . . . .
H4 H 0.352434 0.424745 0.356079 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5006(11) 0.41533(18) 0.5077(19) 0.0209(9) Uani 1 1 d . . . . .
C6 C 0.5055(9) 0.49624(17) 0.5070(16) 0.0146(9) Uani 1 1 d . . . . .
C7 C 0.5898(7) 0.5313(4) 0.5641(9) 0.0170(17) Uani 1 1 d . . . . .
H7 H 0.652559 0.504979 0.604477 0.020 Uiso 1 1 calc R U . . .
C8 C 0.5905(7) 0.6077(4) 0.5676(10) 0.0165(15) Uani 1 1 d . . . . .
H8 H 0.653028 0.634429 0.607199 0.020 Uiso 1 1 calc R U . . .
C9 C 0.4919(8) 0.64410(19) 0.5085(14) 0.0183(10) Uani 1 1 d . . . . .
H9 H 0.484020 0.695632 0.519306 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4113(8) 0.6025(6) 0.4372(13) 0.034(2) Uani 1 1 d . . . . .
H10 H 0.349645 0.627434 0.387638 0.040 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
I1 Sb1 3.0148(10) . ?
I2 Sb1 2.8280(9) . ?
I3 Sb1 2.8371(9) . ?
I4 Sb1 3.0280(10) . ?
N1 H1 0.8800 . ?
N1 C1 1.433(7) . ?
N1 C5 1.313(13) . ?
N2 C6 1.444(13) . ?
N2 C10 1.302(13) . ?
C1 H1A 0.9500 . ?
C1 C2 1.389(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.370(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.476(15) . ?
C5 C6 1.479(4) . ?
C6 C7 1.279(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.438(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.347(14) . ?
C10 H10 0.9500 . ?

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
I1 Sb1 I4 176.640(8) . . ?
I2 Sb1 I1 88.67(3) . . ?
I2 Sb1 I3 94.957(7) . . ?
I2 Sb1 I4 93.69(3) . . ?
I3 Sb1 I1 93.85(3) . . ?
I3 Sb1 I4 88.33(3) . . ?
C1 N1 H1 120.9 . . ?
C5 N1 H1 120.9 . . ?
C5 N1 C1 118.3(6) . . ?
C10 N2 C6 114.5(7) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 N1 121.0(5) . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.1(5) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 121.1(5) . . ?
N1 C5 C6 127.6(11) . . ?
C4 C5 C6 109.7(9) . . ?
N2 C6 C5 114.3(10) . . ?
C7 C6 N2 123.6(3) . . ?
C7 C6 C5 122.1(10) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(7) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 121.6 . . ?
C7 C8 C9 116.8(7) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.6(4) . . ?
C10 C9 H9 121.2 . . ?
N2 C10 C9 126.1(8) . . ?
N2 C10 H10 116.9 . . ?
C9 C10 H10 116.9 . . ?

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
N1 C1 C2 C3 2.0(7) . . . . ?
N1 C5 C6 N2 172.7(10) . . . . ?
N1 C5 C6 C7 -5(2) . . . . ?
N2 C6 C7 C8 5.2(17) . . . . ?
C1 N1 C5 C4 -10.9(14) . . . . ?
C1 N1 C5 C6 -175.1(11) . . . . ?
C1 C2 C3 C4 -1.3(8) . . . . ?
C2 C3 C4 C5 -5.1(10) . . . . ?
C3 C4 C5 N1 11.7(14) . . . . ?
C3 C4 C5 C6 178.3(8) . . . . ?
C4 C5 C6 N2 7.1(14) . . . . ?
C4 C5 C6 C7 -170.3(9) . . . . ?
C5 N1 C1 C2 4.3(9) . . . . ?
C5 C6 C7 C8 -177.6(10) . . . . ?
C6 N2 C10 C9 0.0(15) . . . . ?
C6 C7 C8 C9 1.4(13) . . . . ?
C7 C8 C9 C10 -6.9(15) . . . . ?
C8 C9 C10 N2 6.3(17) . . . . ?
C10 N2 C6 C5 176.6(10) . . . . ?
C10 N2 C6 C7 -6.1(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.55(4)
2 0.45(4)

