Copper-Catalyzed Double Thiolation To Access Sulfur-Bridged Imidazopyridines with Isothiocyanate.
Tian, Lu-Lu; Lu, Shuai; Zhang, Zhe-Hua; Huang, En-Ling; Yan, Hua-Ting; Zhu, Xinju; Hao, Xin-Qi; Song, Mao-Ping; The Journal of organic chemistry 84 (2019) 5213–5221; doi:10.1021/acs.joc.9b00186

data_4034325
_publ_section_title
;
 Copper-Catalyzed Double Thiolation To Access Sulfur-Bridged
 Imidazopyridines with Isothiocyanate.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5213
_journal_page_last               5221
_journal_paper_doi               10.1021/acs.joc.9b00186
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C26 H18 N4 S'
_chemical_formula_sum            'C26 H18 N4 S'
_chemical_formula_weight         418.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1414(4)
_cell_length_b                   13.8740(6)
_cell_length_c                   12.6453(5)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6700
_cell_measurement_theta_min      3.5730
_cell_volume                     2083.21(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -58.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   30.0000 35

  2 omega  -94.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -90.0000 36

  3 omega    4.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   30.0000 29

  4 omega   29.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 63

  5 omega   18.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 52

  6 omega   62.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 48

  7 omega   71.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 32

  8 omega   66.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 38

  9 omega   57.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 50

 10 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 25

 11 omega   49.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 46

 12 omega   39.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 110

 13 omega   54.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

 14 omega   42.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 66

 15 omega  100.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 64

 16 omega   42.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 40

 17 omega   88.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 89

 18 omega   58.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

 19 omega   54.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0770411000
_diffrn_orient_matrix_UB_12      0.0892629000
_diffrn_orient_matrix_UB_13      -0.0202698000
_diffrn_orient_matrix_UB_21      -0.0714483000
_diffrn_orient_matrix_UB_22      -0.0409960000
_diffrn_orient_matrix_UB_23      0.0768861000
_diffrn_orient_matrix_UB_31      0.0760926000
_diffrn_orient_matrix_UB_32      0.0517963000
_diffrn_orient_matrix_UB_33      0.0958778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8069
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.593
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0719P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2897
_reflns_number_total             3703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00186_si_002.cif
_cod_data_source_block           201805251
_cod_original_cell_volume        2083.20(15)
_cod_database_code               4034325
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N4S1
_shelx_estimated_absorpt_t_max   0.802
_shelx_estimated_absorpt_t_min   0.700
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'