Copper-catalyzed synthesis of N-fused heterocycles through regioselective 1,2-aminothiolation of 1,1-dibromoalkenes.
Xu, Hui; Zhang, Yin; Huang, Jianqiang; Chen, Wanzhi; Organic letters 12 (2010) 3704–3707; doi:10.1021/ol101563f

data_1503153
_publ_section_title
;
 Copper-catalyzed synthesis of N-fused heterocycles through regioselective
 1,2-aminothiolation of 1,1-dibromoalkenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3704
_journal_page_last               3707
_journal_paper_doi               10.1021/ol101563f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C17 H23 Br N2 O0 S'
_chemical_formula_weight         367.34
_chemical_name_systematic
; 
 ? 
;
_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                 112.788(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7689(3)
_cell_length_b                   24.7018(6)
_cell_length_c                   9.0693(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1811.14(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10798
_diffrn_reflns_theta_full        66.92
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    4.121
_exptl_absorpt_correction_T_max  0.6376
_exptl_absorpt_correction_T_min  0.2764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0630P)^2^+0.8968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2504
_reflns_number_total             3218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101563f_si_002.cif
_cod_data_source_block           100328_xuhuir443
_cod_original_cell_volume        1811.14(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503153