Metal-Free Dehydrogenative Double C-H Sulfuration To Access Thieno[2,3-<i>b</i>]indoles Using Elemental Sulfur.
Liu, Jianming; Zhang, Yanyan; Yue, Yuanyuan; Wang, Zhixian; Shao, Huibin; Zhuo, Kelei; Lv, Qingzhang; Zhang, Zhiguo; The Journal of organic chemistry 84 (2019) 12946–12959; doi:10.1021/acs.joc.9b01586

data_4034084
_publ_section_title
;
 Metal-Free Dehydrogenative Double C-H Sulfuration To Access
 Thieno[2,3-<i>b</i>]indoles Using Elemental Sulfur.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12946
_journal_page_last               12959
_journal_paper_doi               10.1021/acs.joc.9b01586
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C23 H15 N O S'
_chemical_formula_sum            'C23 H15 N O S'
_chemical_formula_weight         353.42
_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             2018-03-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5470)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.165(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1945(11)
_cell_length_b                   14.5760(14)
_cell_length_c                   10.7976(11)
_cell_measurement_reflns_used    4587
_cell_measurement_temperature    289.1(4)
_cell_measurement_theta_max      27.9340
_cell_measurement_theta_min      3.7050
_cell_volume                     1860.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_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  55.00   1.00    5.59    --   16.13 -99.00 -90.00   75
  2  \w    -51.00  33.00   1.00    5.59    --   16.13 -57.00 -60.00   84
  3  \w    -53.00  35.00   1.00    5.59    --   16.13 -38.00  30.00   88
  4  \w    -34.00  50.00   1.00    5.59    --  -17.23  57.00-150.00   84
  5  \w    -11.00  27.00   1.00    5.59    --   16.13  77.00  60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531424000
_diffrn_orient_matrix_UB_12      -0.0221481000
_diffrn_orient_matrix_UB_13      -0.0091628000
_diffrn_orient_matrix_UB_21      0.0233292000
_diffrn_orient_matrix_UB_22      -0.0403357000
_diffrn_orient_matrix_UB_23      -0.0199663000
_diffrn_orient_matrix_UB_31      0.0152566000
_diffrn_orient_matrix_UB_32      -0.0158268000
_diffrn_orient_matrix_UB_33      0.0640850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12208
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.406
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.3654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2624
_reflns_number_total             3285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01586_si_002.cif
_cod_data_source_block           zyy-20180305
_cod_database_code               4034084
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 O1 S1 N1'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C6(H6), C26(H26), C3(H3), C18(H18), C4(H4), C5(H5),
 C22(H22), C15(H15), C25(H25), C17(H17), C24(H24), C16(H16), C23(H23)
;
_shelx_res_checksum              34360
_shelx_hkl_checksum              83379
_olex2_date_sample_data_collection 2018-03-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.469