Isolation of unique heterocycles formed from pyridine-thiocarboxamides as diiodine, iodide, or polyiodide salts
Peloquin, Andrew J.; McMillen, Colin; Pennington, William; CrystEngComm  (2022) –; doi:10.1039/D2CE00904H

data_7245362
_publ_section_title
;
 Isolation of unique heterocycles formed from pyridine-thiocarboxamides as
 diiodine, iodide, or polyiodide salts
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00904H
_journal_year                    2022
_chemical_formula_moiety         'Bi2 I9, C12 H10 N4 S, 3(H2 O), C12 H9 N4 S'
_chemical_formula_sum            'C24 H25 Bi2 I9 N8 O3 S2'
_chemical_formula_weight         2097.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3663(5)
_cell_length_b                   24.1622(12)
_cell_length_c                   12.9374(8)
_cell_measurement_reflns_used    9605
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.68
_cell_volume                     2506.2(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015<i>b</i>)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0509
_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       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            77273
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.635
_diffrn_reflns_theta_min         1.846
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.671
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.148
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         3.772
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.215
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         13925
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0094P)^2^+10.7712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0718
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                13212
_reflns_number_total             13925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_5846_27mar22_ajp1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245362
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.256
_shelx_estimated_absorpt_t_min   0.149
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.99005
 0.00995
2. Restrained distances
 N4-H4
 0.86 with sigma of 0.02
 H7-N7
 0.86 with sigma of 0.02
 H1O3-O3 = H2O3-O3
 0.87 with sigma of 0.02
 H2O3-H1O3
 1.38 with sigma of 0.04
 C1-N2A \\sim C7-N2B
 with sigma of 0.02
 C7-S1A \\sim C1-S1B
 with sigma of 0.02
 C17-H7 \\sim C16-H7
 with sigma of 0.02
 H1O3-O3 \\sim H2O3-O3
 with sigma of 0.001
3. Restrained planarity
 N7, H7, C16, C17
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S1B \\sim N2B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
S1A \\sim N2A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
S2 \\sim N6: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5. Others
 Sof(S1B)=Sof(N2B)=1-FVAR(1)
 Sof(S1A)=Sof(N2A)=FVAR(1)
 Fixed X: H1A(0.25933) H1B(0.191991) H2C(1.31604) H2D(1.313) H1O3(0.828701)
 H2O3(0.788)
 Fixed Y: H1A(0.21096) H1B(0.24797) H2C(0.73082) H2D(0.780509) H1O3(0.30181)
 H2O3(0.35797)
 Fixed Z: H1A(-0.246739) H1B(-0.18998) H2C(1.132721) H2D(1.080189)
 H1O3(0.73037) H2O3(0.706539)
6.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
 C24(H24), C3(H3), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              91284
_olex2_submission_special_instructions 'No special instructions were received'