Chirality-Economy Catalysis: Asymmetric Transfer Hydrogenation of Ketones by Ru-Catalysts of Minimal Stereogenicity
Chen, Fumin; He, Dongxu; Chen, Li; Chang, Xiaoyong; Wang, David Zhigang; Xu, Chen; Xing, Xiangyou; ACS Catalysis 9 (2019) 5562–; doi:10.1021/acscatal.9b01535

data_4514420
_publ_section_title
;
 Chirality-Economy Catalysis: Asymmetric Transfer Hydrogenation of Ketones
 by Ru-Catalysts of Minimal Stereogenicity
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5562
_journal_paper_doi               10.1021/acscatal.9b01535
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C45 H44 Cl2 N2 P2 Ru, 2(C7 H8)'
_chemical_formula_sum            'C59 H60 Cl2 N2 P2 Ru'
_chemical_formula_weight         1031.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9656(6)
_cell_length_b                   11.9509(6)
_cell_length_c                   38.4007(19)
_cell_measurement_reflns_used    9545
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.52
_cell_volume                     5032.4(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            62274
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.331
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1128 before and 0.0598 after correction. The Ratio of minimum to maximum transmission is 0.6955. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(7)
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         11579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+2.8050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0586
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                11359
_reflns_number_total             11579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01535_si_004.cif
_cod_data_source_block           cxy0621_0m
_cod_depositor_comments
'Adding full bibliography for 4514419--4514420.cif.'
_cod_database_code               4514420
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C38(H38), C39(H39)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C45(H45), C44(H44), C43(H43), C42(H42), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36), C2(H2), C3(H3), C4(H4), C5(H5),
 C6(H6), C12(H12), C11(H11), C10(H10), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C51(H51), C46(H46), C48(H48), C49(H49), C50(H50), C53(H53),
  C58(H58), C57(H57), C55(H55), C56(H56)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C52(H52A,H52B,H52C), C59(H59A,H59B,
 H59C)
;
_olex2_submission_special_instructions 'No special instructions were received'