Solvent-controlled highly regio-selective thieno[2,3-b]indole formation under metal-free conditions
Deng, Guo-Jun; Ni, Penghui; Li, Bin; Huang, Huawen; Xiao, Fuhong; Green Chem.  (2017) –; doi:10.1039/C7GC02818K

data_7229391
_publ_section_title
;
 Solvent-controlled highly regio-selective thieno[2,3-b]indole formation
 under metal-free conditions
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02818K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 N S'
_chemical_formula_sum            'C17 H13 N S'
_chemical_formula_weight         263.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-30 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4797(4)
_cell_length_b                   9.5670(7)
_cell_length_c                   24.6309(17)
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4691
_cell_measurement_theta_min      2.2838
_cell_volume                     1291.26(16)
_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., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.1096
              2theta: -19.8653
;
_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       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1679
_diffrn_orient_matrix_UB_12      0.0401
_diffrn_orient_matrix_UB_13      0.0593
_diffrn_orient_matrix_UB_21      -0.0265
_diffrn_orient_matrix_UB_22      -0.1009
_diffrn_orient_matrix_UB_23      -0.0067
_diffrn_orient_matrix_UB_31      0.0122
_diffrn_orient_matrix_UB_32      -0.0057
_diffrn_orient_matrix_UB_33      0.0383
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5038
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.270
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0326P)^2^+0.3727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                2653
_reflns_number_total             2767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc02818k2.cif
_cod_data_source_block           sa4848a
_cod_database_code               7229391
_diffrn_number_total             1739
_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), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              50435
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'