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_4028164
_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 O4 S'
_chemical_formula_sum            'C22 H21 N O4 S'
_chemical_formula_weight         395.46
_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                90.00
_cell_angle_beta                 95.322(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.493(5)
_cell_length_b                   13.546(5)
_cell_length_c                   30.223(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.6
_cell_volume                     3870(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega 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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21508
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       Block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0809P)^2^+2.5584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1735
_reflns_number_gt                5622
_reflns_number_total             7617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400287a_si_003_1.cif
_cod_data_source_block           compound7b
_cod_database_code               4028164