Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine-Nickel Complex.
Sato, Ryo; Tosaka, Takuya; Masu, Hyuma; Arai, Takayoshi; The Journal of organic chemistry 84 (2019) 14248–14257; doi:10.1021/acs.joc.9b02006

data_4034531
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a
 Ts-PyBidine-Nickel Complex.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14248
_journal_page_last               14257
_journal_paper_doi               10.1021/acs.joc.9b02006
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H41 Br N2 O9'
_chemical_formula_weight         713.61
_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_update_record
;
2019-07-26 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.8420(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9644(2)
_cell_length_b                   30.3343(5)
_cell_length_c                   11.0367(2)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.1780
_cell_measurement_theta_min      4.0537
_cell_volume                     3627.15(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            47691
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.305
_diffrn_reflns_theta_min         4.054
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.258
_refine_ls_abs_structure_details
;
Flack x determined using 5849 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     867
_refine_ls_number_reflns         12885
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.5142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                12586
_reflns_number_total             12885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02006_si_003.cif
_cod_data_source_block           u190521mas1
_cod_database_code               4034531
_shelx_res_checksum              45967
_shelx_hkl_checksum              85669