Iodide-promoted transformations of imidazopyridines into sulfur-bridged imidazopyridines or 1,2,4-thiadiazoles.
Ma, Shi-Tang; Zhu, Xiao-Xiao; Xu, Jing-Yu; Li, Ying; Zhang, Xiao-Mei; Feng, Cheng-Tao; Yan, Yizhe; Chemical communications (Cambridge, England) 57 (2021) 5338–5341; doi:10.1039/d1cc01044a

data_7128236
_publ_section_title
;
 Iodide-promoted transformations of imidazopyridines into sulfur-bridged
 imidazopyridines or 1,2,4-thiadiazoles.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5338
_journal_page_last               5341
_journal_paper_doi               10.1039/d1cc01044a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C13 H9 N3 S'
_chemical_formula_sum            'C13 H9 N3 S'
_chemical_formula_weight         239.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.043(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8409(15)
_cell_length_b                   15.0587(15)
_cell_length_c                   12.4189(14)
_cell_measurement_reflns_used    6942
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.18
_cell_volume                     2307.9(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.134
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0783 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.9376.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0528P)^2^+0.4895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3171
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01044a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7128236.cif.'
_cod_database_code               7128236
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S1, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C3, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S2, N16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C12(H12), C5(H5), C14(H14), C7(H7), C8(H8),
 C6(H6), C19(H19), C23(H23), C28(H28), C25(H25), C20(H20), C27(H27), C26(H26),
 C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'