Synthetic Route to Chiral Indolines via Ring-Opening/C-N Cyclization of Activated 2-Haloarylaziridines
Manas K. Ghorai; Y. Nanaji; Journal of Organic Chemistry 78 (2013) 3867–3878; doi:10.1021/jo400287a

data_4028166
_publ_section_title
;
 Synthetic Route to Chiral Indolines via Ring-Opening/C-N Cyclization of
 Activated 2-Haloarylaziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3867
_journal_page_last               3878
_journal_paper_doi               10.1021/jo400287a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C22 H21 N O2 S2'
_chemical_formula_sum            'C22 H21 N O2 S2'
_chemical_formula_weight         395.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.125(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.161(5)
_cell_length_b                   9.101(5)
_cell_length_c                   25.376(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.30
_cell_volume                     1884.8(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9876
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.9507
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+1.6055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2868
_reflns_number_total             3492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400287a_si_003_3.cif
_cod_data_source_block           Compound12b
_cod_database_code               4028166