Enantioselective Synthesis of Dihydro-1H-benzindoles
Gustavo P. Silveira; Joseph P. Marino; Journal of Organic Chemistry 78 (2013) 3379–3383; doi:10.1021/jo302798j

data_4028077
_publ_contact_author_address     '268 SHCB'
_publ_contact_author_email       gpsilveira@hotmail.com
_publ_contact_author_name        'Gustavo Silveira'
_publ_contact_author_phone       1-0967
_publ_section_title
;
 Enantioselective Synthesis of Dihydro-1H-benzindoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3379
_journal_page_last               3383
_journal_paper_doi               10.1021/jo302798j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H21 Cl4 N O4 S2'
_chemical_formula_sum            'C24 H21 Cl4 N O4 S2'
_chemical_formula_weight         593.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.636(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1467(10)
_cell_length_b                   23.558(4)
_cell_length_c                   9.1819(15)
_cell_measurement_reflns_used    9651
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      2.33
_cell_volume                     1267.1(4)
_computing_cell_refinement       'Bruker SAINT v7.60A'
_computing_data_collection       'Bruker APEX-II v2009-5'
_computing_data_reduction        'Bruker SAINT v7.60A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23154
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.9029
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Sheldrick, 2008'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       rod
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+0.1580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0619
_reflns_number_gt                6339
_reflns_number_total             6849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302798j_si_001.cif
_cod_data_source_block           gspd296
_cod_database_code               4028077