Extending lead-free hybrid photovoltaic materials to new structures: thiazolium, aminothiazolium and imidazolium iodobismuthates.
Li, Tianyue; Wang, Qifei; Nichol, Gary S.; Morrison, Carole A.; Han, Hongwei; Hu, Yue; Robertson, Neil; Dalton transactions (Cambridge, England : 2003) 47 (2018) 7050–7058; doi:10.1039/c8dt00864g

data_7046287
_publ_section_title
;
 Extending lead-free hybrid photovoltaic materials to new structures:
 thiazolium, aminothiazolium and imidazolium iodobismuthates.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7050
_journal_page_last               7058
_journal_paper_doi               10.1039/c8dt00864g
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'Bi2 I9, 3(C3 H4 N S)'
_chemical_formula_sum            'C9 H12 Bi2 I9 N3 S3'
_chemical_formula_weight         1818.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-04-11 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8257(2)
_cell_length_b                   14.6666(3)
_cell_length_c                   23.2957(4)
_cell_measurement_reflns_used    28557
_cell_measurement_temperature    250.0
_cell_measurement_theta_max      28.8850
_cell_measurement_theta_min      3.4310
_cell_volume                     3357.13(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43h (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43h (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43h (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00  31.00   0.50   20.00    --   -9.27 -99.00  90.00  102
  2  \w    -26.00  89.00   0.50   20.00    --   10.68  19.00-180.00  230
  3  \w    -59.00  37.00   0.50   20.00    --   10.68 -57.00   0.00  192
  4  \w    -20.00  51.00   0.50   20.00    --   10.68 -99.00 -30.00  142
  5  \w    -20.00  51.00   0.50   20.00    --   10.68 -99.00-120.00  142
  6  \w    -59.00  37.00   0.50   20.00    --   10.68 -57.00-180.00  192
  7  \w    -59.00  37.00   0.50   20.00    --   10.68 -57.00  60.00  192
  8  \w    -20.00  31.00   0.50   20.00    --   -9.27 -99.00 150.00  102
  9  \w    -79.00  17.00   0.50   20.00    --   -9.27 -57.00 -90.00  192
 10  \w    -20.00  31.00   0.50   20.00    --   -9.27 -99.00 -30.00  102
 11  \w    -20.00  31.00   0.50   20.00    --   -9.27 -99.00-180.00  102
 12  \w    -49.00  -1.00   0.50   20.00    --   -9.27  99.00  55.00   96
 13  \w    -20.00  51.00   0.50   20.00    --   10.68 -99.00-180.00  142
 14  \w    -41.00  65.00   0.50   20.00    --   -9.27  77.00-150.00  212
 15  \w    -82.00  13.00   0.50   20.00    --   -9.27 -38.00 120.00  190
 16  \w    -20.00  51.00   0.50   20.00    --   10.68 -99.00 -90.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford DIffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0237657000
_diffrn_orient_matrix_UB_12      0.0007186000
_diffrn_orient_matrix_UB_13      -0.0287407000
_diffrn_orient_matrix_UB_21      0.0057614000
_diffrn_orient_matrix_UB_22      -0.0481609000
_diffrn_orient_matrix_UB_23      -0.0013296000
_diffrn_orient_matrix_UB_31      -0.0679328000
_diffrn_orient_matrix_UB_32      -0.0043238000
_diffrn_orient_matrix_UB_33      0.0099508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            96745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.347
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    18.937
_exptl_absorpt_correction_T_max  0.7908
_exptl_absorpt_correction_T_min  0.1888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1102 before and 0.0979 after correction. The Ratio of minimum to maximum transmission is 0.2387. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    3.598
_exptl_crystal_description       plate
_exptl_crystal_F_000             3112
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of ethanol and water by solvent layering'
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.562
_refine_diff_density_min         -2.199
_refine_diff_density_rms         0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.332
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.339
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+117.9315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3086
_reflns_number_total             3158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt00864g2.cif
_cod_data_source_block           nr16005x2
_cod_depositor_comments
'Adding full bibliography for 7046287--7046288.cif.'
_cod_database_code               7046287
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C3 H4 N1 S1 Bi1 I4'
_chemical_oxdiff_usercomment     '@ 250 K THB'
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.189
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Shared sites
{C3, S2A}
3. Restrained distances
 C2-C2_$1 = C5A-C4A = C5-C4
 1.35 with sigma of 0.02
 N1-C2 = N2A-C4A = N2-C4
 1.37 with sigma of 0.02
 N1-C1 = N2-C3 = N2A-C3A
 1.3 with sigma of 0.02
 S1-C1 = S2-C3 = S2A-C3A
 1.69 with sigma of 0.02
 S1-C2 = S2-C5 = S2A-C5A
 1.68 with sigma of 0.02
 C1-C2 = C4-C3 = C4A-C3A
 2.18 with sigma of 0.04
4. Restrained planarity
 S2, N2, C3, C4, C5
 with sigma of 0.1
 S2A, N2A, C3A, C4A, C5A
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(N1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C3) = Uanis(S2A)
Uanis(S2A) = Uanis(C3)
6. Rigid body (RIGU) restrains
 S1, N1, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S2, N2, C3, C4, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S2A, N2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, N1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(S2A)=Sof(C3A)=Sof(H3A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(N2A)=
 Sof(H2AA)=1-FVAR(1)
 Sof(S2)=Sof(N2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=FVAR(1)
 Fixed Sof: S1(0.5) N1(0.5) H1(0.5) H1A(0.25) H1B(0.25) H2A(0.5) H2B(0.5)
8.a Everything fixed:
 C3A, C5A, C4A, N2A
8.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C1(H1B), C2(H2A), C2(H2B), N2(H2), C3(H3), C3A(H3A), C4(H4),
 C5(H5), C5A(H5A), C4A(H4A), N2A(H2AA)
;
_shelx_res_checksum              86905
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id THB
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 2.287
_oxdiff_exptl_absorpt_empirical_full_min 0.609