Asymmetric hydrogenation of bicyclic ketones catalyzed by BINAP/IPHAN-Ru(II) complex.
Arai, Noriyoshi; Akashi, Masaya; Sugizaki, Satoshi; Ooka, Hirohito; Inoue, Tsutomu; Ohkuma, Takeshi; Organic letters 12 (2010) 3380–3383; doi:10.1021/ol101200z

data_1503070
_publ_section_title
;
 Asymmetric hydrogenation of bicyclic ketones catalyzed by
 BINAP/IPHAN-Ru(II) complex.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3380
_journal_page_last               3383
_journal_paper_doi               10.1021/ol101200z
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C53 H52 Cl2 N2 O2 P2 Ru '
_chemical_formula_sum            'C53 H52 Cl2 N2 O2 P2 Ru'
_chemical_formula_weight         982.93
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.8594(5)
_cell_length_b                   21.0813(8)
_cell_length_c                   23.1923(10)
_cell_measurement_reflns_used    63588
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     5309.4(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.040
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            81087
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         2.34
_refine_diff_density_min         -0.79
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  5437 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.00(3)
_refine_ls_extinction_coef       1358(94)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     613
_refine_ls_number_reflns         12109
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.0025
_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         0.1513
_reflns_number_gt                9761
_reflns_number_total             12109
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol101200z_si_002.cif
_cod_data_source_block           '_arai-100310'
_cod_original_formula_sum        'C53 H52 Cl2 N2 O2 P2 Ru '
_cod_database_code               1503070