Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by the TolBINAP/DMAPEN-Ruthenium(II) Complex: A Significant Effect of N-Substituents of Chiral 1,2-Diamine Ligands on Enantioselectivity
Hirohito Ooka; Noriyoshi Arai; Keita Azuma; Nobuhito Kurono; Takeshi Ohkuma; Journal of Organic Chemistry 73 (2008) 9084–9093; doi:10.1021/jo801863q

data_4023868
_publ_section_title
;
 Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by the
 TolBINAP/DMAPEN-Ruthenium(II) Complex: A Significant Effect of
 N-Substituents of Chiral 1,2-Diamine Ligands on Enantioselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9084
_journal_page_last               9093
_journal_paper_doi               10.1021/jo801863q
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C66 H76 Cl2 N2 O2 P2 Ru '
_chemical_formula_sum            'C66 H76 Cl2 N2 O2 P2 Ru'
_chemical_formula_weight         1163.26
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2008-04-28
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   21.1651(15)
_cell_length_b                   21.4566(18)
_cell_length_c                   12.9527(11)
_cell_measurement_reflns_used    81239
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.0
_cell_volume                     5882.2(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44778
_diffrn_reflns_theta_full        27.35
_diffrn_reflns_theta_max         27.35
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2440.00
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_refine_diff_density_max         1.11
_refine_diff_density_min         -1.34
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  5901 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     753
_refine_ls_number_reflns         13142
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.0013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1723
_reflns_number_gt                11230
_reflns_number_total             13142
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo801863q_si_002.cif
_cod_data_source_block           '_arai080229_______________'
_cod_original_formula_sum        'C66 H76 Cl2 N2 O2 P2 Ru '
_cod_database_code               4023868