Asymmetric hydrogenation of ketones using a ruthenium(II) catalyst containing BINOL-derived monodonor phosphorus-donor ligands.
Xu, Yingjian; Alcock, Nat W.; Clarkson, Guy J.; Docherty, Gordon; Woodward, Gary; Wills, Martin; Organic letters 6 (2004) 4105–4107; doi:10.1021/ol0481840

data_1556109
_publ_section_title
;
 Asymmetric hydrogenation of ketones using a ruthenium(II) catalyst
 containing BINOL-derived monodonor phosphorus-donor ligands.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4105
_journal_page_last               4107
_journal_paper_doi               10.1021/ol0481840
_journal_volume                  6
_journal_year                    2004
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C67.5 H54.5 Br2 Cl2 N2 O6 P2 Ru'
_chemical_formula_weight         1383.36
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb (-1/2*x+z,1/2*x,y)'
_space_group_name_H-M_alt        'P 1 21 1 (c,2*a+c,b)'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 (c,2*a+c,b)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                89.58
_cell_formula_units_Z            4
_cell_length_a                   16.649(2)
_cell_length_b                   19.163(2)
_cell_length_c                   27.224(3)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     8685.4(17)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Siemens SMART diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_av_sigmaI/netI    0.3813
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            27051
_diffrn_reflns_theta_full        29.07
_diffrn_reflns_theta_max         29.07
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2798
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.00128(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         18346
_refine_ls_number_restraints     583
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.2120
_refine_ls_R_factor_gt           0.0962
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2447
_reflns_number_gt                6829
_reflns_number_total             18346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0481840si20040920_053344.cif
_cod_data_source_block           yj4ort
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        8685.0(19)
_cod_original_sg_symbol_Hall     c_2c
_cod_original_sg_symbol_H-M      C112(1)
_cod_original_formula_sum        'C67.50 H54.50 Br2 Cl2 N2 O6 P2 Ru'
_cod_database_code               1556109