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_4034532
_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_formula_sum            'C24 H24 N2 O5'
_chemical_formula_weight         420.45
_chemical_name_common            tosaka20161121
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                82.581(4)
_cell_angle_beta                 78.044(4)
_cell_angle_gamma                79.541(3)
_cell_formula_units_Z            2
_cell_length_a                   9.413(3)
_cell_length_b                   10.263(3)
_cell_length_c                   11.789(3)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.1032
_cell_measurement_theta_min      2.2403
_cell_volume                     1090.7(5)
_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      293
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6098
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.323
_diffrn_reflns_theta_min         2.240
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0931
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0193P)^2^+2.0623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                3160
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02006_si_002.cif
_cod_data_source_block           arai20161121tosaka_a
_cod_database_code               4034532
_shelx_res_checksum              70712
_shelx_hkl_checksum              52009