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_1503152
_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            'C16 H12 N2 O0 S'
_chemical_formula_weight         264.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 112.754(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.0234(10)
_cell_length_b                   10.3429(4)
_cell_length_c                   14.4289(8)
_cell_measurement_temperature    293(2)
_cell_volume                     2618.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5733
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.8964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                1479
_reflns_number_total             2329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101563f_si_002.cif
_cod_data_source_block           100317_r541
_cod_original_cell_volume        2618.0(2)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1503152