Copper-Catalyzed Desymmetric Intramolecular Ullmann C-N Coupling: An Enantioselective Preparation of Indolines
Fengtao Zhou; Jiajia Guo; Jianguang Liu; Ke Ding; Shouyun Yu; Qian Cai; Journal of the American Chemical Society 134 (2012) 14326–14329; doi:10.1021/ja306631z

data_4118581
_publ_section_title
;
 Copper-Catalyzed Desymmetric Intramolecular Ullmann C-N Coupling: An
 Enantioselective Preparation of Indolines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14326
_journal_page_last               14329
_journal_paper_doi               10.1021/ja306631z
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C18 H16 Br2 I N O2'
_chemical_formula_weight         565.04
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.76968(13)
_cell_length_b                   12.3217(3)
_cell_length_c                   26.6953(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1897.83(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0788
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            44901
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    18.276
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             1080
_refine_diff_density_max         2.444
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.262
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0682
_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^)+(0.1232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                3223
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306631z_si_001.cif
_cod_data_source_block           d
_cod_original_cell_volume        1897.83(7)
_cod_database_code               4118581