Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling.
Wang, Kuai; Ding, Zhengtian; Zhou, Zhijun; Kong, Wangqing; Journal of the American Chemical Society 140 (2018) 12364–12368; doi:10.1021/jacs.8b08190

data_4133053
_publ_section_title
;
 Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes
 by Domino Cyclization/Cross-Coupling.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12364
_journal_page_last               12368
_journal_paper_doi               10.1021/jacs.8b08190
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C76 H84 N4 O4'
_chemical_formula_weight         1117.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.119(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   9.0808(3)
_cell_length_b                   14.9109(4)
_cell_length_c                   12.3558(4)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5398
_cell_measurement_theta_min      2.2709
_cell_volume                     1607.24(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11885
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        62.785
_diffrn_reflns_theta_max         62.785
_diffrn_reflns_theta_min         3.724
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.0042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                4309
_reflns_number_total             4846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08190_si_001.cif
_cod_data_source_block           cu_WK_116_4_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4133053
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
 ?
;
_shelx_res_checksum              74322
_shelx_hkl_checksum              98651