Extending lead-free organic–inorganic semiconducting materials to new polymeric structures: 2,2′-bipyridinium iodoantimonate and quinoxalinium iodobismuthate
Hrizi, Chakib; Hamdouni, Monia; Essid, Marwa; Nouiri, Mourad; Khatyr, Abderrahim; Knorr, Michael; Viau, Lydie; Schmidt, Annika; Strohmann, Carsten; Chaabouni, Slaheddine; RSC Advances 15 (2025) 43523–43541; doi:10.1039/D5RA06189J

data_7251246
_publ_section_title
;
 Extending lead-free organic--inorganic semiconducting materials to new
 polymeric structures: 2,2&#x2032;-bipyridinium iodoantimonate and
 quinoxalinium iodobismuthate
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              43523
_journal_page_last               43541
_journal_paper_doi               10.1039/D5RA06189J
_journal_volume                  15
_journal_year                    2025
_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
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
;
2025-10-27 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                76.552(2)
_cell_angle_beta                 86.660(2)
_cell_angle_gamma                84.3830(10)
_cell_formula_units_Z            1
_cell_length_a                   7.5699(3)
_cell_length_b                   9.6520(3)
_cell_length_c                   11.5436(6)
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.38
_cell_measurement_theta_min      2.71
_cell_volume                     815.82(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_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)'
_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       '\w and \f scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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_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
_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 \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.516
_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
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0205
_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/[\s^2^(Fo^2^)+(0.0170P)^2^+3.7828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5735
_reflns_number_total             5972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra06189j2.cif
_cod_data_source_block           b2638
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7251246
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.340
_shelx_estimated_absorpt_t_min   0.150
_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)
;
_shelx_res_checksum              68836
_olex2_submission_special_instructions 'No special instructions were received'