Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor-Acceptor Cyclopropanes
Hu Xiong; Hao Xu; Saihu Liao; Zuowei Xie; Yong Tang; Journal of the American Chemical Society 135 (2013) 7851–7854; doi:10.1021/ja4042127

data_4119822
_publ_section_title
;
 Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles
 with Donor-Acceptor Cyclopropanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7851
_journal_page_last               7854
_journal_paper_doi               10.1021/ja4042127
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C51 H62 Br2 Cu N2 O2'
_chemical_formula_weight         958.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   22.604(3)
_cell_length_b                   22.604(3)
_cell_length_c                   17.635(3)
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.228
_cell_measurement_theta_min      4.760
_cell_volume                     7803(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1084
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9663
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06249
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            puple
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2982
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.089
_platon_squeeze_details
;
;
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     188
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0875P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                4878
_reflns_number_total             9663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4042127_L5c-CuBr2.cif
_cod_data_source_block           cd212587
_cod_original_cell_volume        7803.1(19)
_cod_database_code               4119822