Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.
Miao, Lei; Haque, Imranul; Manzoni, Maria R.; Tham, Weng Siong; Chemler, Sherry R.; Organic letters 12 (2010) 4739–4741; doi:10.1021/ol102233g

data_1503286
_publ_section_title
;
 Diastereo- and enantioselective copper-catalyzed intramolecular
 carboamination of alkenes for the synthesis of
 hexahydro-1H-benz[f]indoles.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4739
_journal_page_last               4741
_journal_paper_doi               10.1021/ol102233g
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C14 H19 N O3 S'
_chemical_formula_sum            'C14 H19 N O3 S'
_chemical_formula_weight         281.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.3710(10)
_cell_angle_beta                 91.0270(10)
_cell_angle_gamma                91.3550(10)
_cell_formula_units_Z            2
_cell_length_a                   5.34120(10)
_cell_length_b                   10.8365(3)
_cell_length_c                   11.3636(3)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.694
_cell_measurement_theta_min      4.993
_cell_volume                     655.50(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26669
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0386P)^2^+0.3767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                2940
_reflns_number_total             3269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102233g_si_007.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      P_-1
_cod_database_code               1503286