Palladium-catalyzed benzothieno[2,3-b]indole formation via dehydrative-dehydrogenative double C-H sulfuration using sulfur powder, indoles and cyclohexanones
Yunfeng Liao; Yi Peng; Hongrui Qi; Guo-Jun Deng; Hang Gonga; Chao-Jun Li; Chem.Commun. 51 (2015) 1031–; doi:10.1039/C4cc08370A

data_7116338
_publ_section_title
;
 Palladium-catalyzed benzothieno[2,3-b]indole formation via
 dehydrative-dehydrogenative double C-H sulfuration using sulfur powder,
 indoles and cyclohexanones
;
_journal_name_full               Chem.Commun.
_journal_page_first              1031
_journal_paper_doi               10.1039/C4cc08370A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C16 H13 N S'
_chemical_formula_sum            'C16 H13 N S'
_chemical_formula_weight         251.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-10-21 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.7076(11)
_cell_length_b                   20.718(4)
_cell_length_c                   21.125(4)
_cell_measurement_reflns_used    7368
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4845
_cell_measurement_theta_min      2.1897
_cell_volume                     2498.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0931
_diffrn_orient_matrix_UB_12      -0.0980
_diffrn_orient_matrix_UB_13      0.1115
_diffrn_orient_matrix_UB_21      0.0387
_diffrn_orient_matrix_UB_22      -0.0044
_diffrn_orient_matrix_UB_23      0.0285
_diffrn_orient_matrix_UB_31      -0.0128
_diffrn_orient_matrix_UB_32      0.0390
_diffrn_orient_matrix_UB_33      0.0236
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15510
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.304
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.304
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0531P)^2^+2.4999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1774
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2624
_reflns_number_total             2862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08370a2.cif
_cod_data_source_block           sa3433b
_cod_original_cell_volume        2498.0(9)
_cod_database_code               7116338
_shelxl_version_number           2013-4
_diffrn_number_total             3331
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              10013