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_4034326
_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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.054(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6916(8)
_cell_length_b                   14.1510(8)
_cell_length_c                   11.5590(3)
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7960
_cell_measurement_theta_min      4.9470
_cell_volume                     2060.27(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -63.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -90.0000 27

  2 omega  -59.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   30.0000 58

  3 omega -103.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -90.0000 37

  4 omega  -32.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   30.0000 87

  5 omega    8.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 49

  6 omega   62.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 27

  7 omega   41.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 35

  8 omega  -36.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  150.0000 42

  9 omega   -2.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 32

 10 omega   33.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  150.0000 39

 11 omega   40.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 34

 12 omega   97.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 37

 13 omega  149.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 27

 14 omega   41.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 80

 15 omega   41.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 26

 16 omega   44.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 60

 17 omega   76.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 38

 18 omega   89.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 46

 19 omega   41.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 51

 20 omega   82.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 26

 21 omega   91.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1171376000
_diffrn_orient_matrix_UB_12      0.0062890000
_diffrn_orient_matrix_UB_13      -0.0217692000
_diffrn_orient_matrix_UB_21      0.0055521000
_diffrn_orient_matrix_UB_22      -0.1086141000
_diffrn_orient_matrix_UB_23      -0.0060105000
_diffrn_orient_matrix_UB_31      -0.0347654000
_diffrn_orient_matrix_UB_32      0.0038408000
_diffrn_orient_matrix_UB_33      -0.1323686000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.099
_diffrn_reflns_theta_max         67.099
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99446
_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    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0717P)^2^+0.2172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2827
_reflns_number_total             3666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00186_si_003.cif
_cod_data_source_block           201804208
_cod_database_code               4034326
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.746
_reflns_odcompleteness_completeness 99.69
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'