A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N Cyclization.
Sayyad, Masthanvali; Mal, Abhijit; Wani, Imtiyaz Ahmad; Ghorai, Manas K.; The Journal of organic chemistry 81 (2016) 6424–6432; doi:10.1021/acs.joc.6b01049

data_4036947
_publ_section_title
;
 A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of
 Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N
 Cyclization.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6424
_journal_page_last               6432
_journal_paper_doi               10.1021/acs.joc.6b01049
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C24 H20 Br Cl N2 O2 S'
_chemical_formula_weight         515.84
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 113.089(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   14.537(5)
_cell_length_b                   10.994(5)
_cell_length_c                   15.122(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2223.2(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21986
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.088
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0575P)^2^+2.1069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                3918
_reflns_number_total             5498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01049_si_002.cif
_cod_data_source_block           4j
_cod_database_code               4036947