Highly enantioselective hydrogenation of steric hindrance enones catalyzed by ru complexes with chiral diamine and achiral phosphane.
Chen, Xiangning; Zhou, Han; Zhang, Kunyu; Li, Jiawen; Huang, Hanmin; Organic letters 16 (2014) 3912–3915; doi:10.1021/ol501648a

data_1517203
_publ_section_title
;
 Highly enantioselective hydrogenation of steric hindrance enones
 catalyzed by ru complexes with chiral diamine and achiral phosphane.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3912
_journal_page_last               3915
_journal_paper_doi               10.1021/ol501648a
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C52 H44 Cl2 N2 O P2 Ru, C H2 Cl2'
_chemical_formula_sum            'C53 H46 Cl4 N2 O P2 Ru'
_chemical_formula_weight         1031.73
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.9933(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.20234(15)
_cell_length_b                   14.9864(3)
_cell_length_c                   14.7402(3)
_cell_measurement_reflns_used    9042
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6750
_cell_measurement_theta_min      4.1440
_cell_volume                     2353.60(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9704
_diffrn_measured_fraction_theta_max 0.8284
_diffrn_measurement_details
;
  1 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 25

  2 omega   27.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 43

  3 omega  -24.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 36

  4 omega  -80.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -60.0000 40

  5 omega  -23.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 30

  6 omega  -73.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000  120.0000 39

  7 omega -128.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000   90.0000 44

  8 omega  -55.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000   90.0000 30

  9 omega -124.00  -83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000  120.0000 41

 10 omega    4.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000  -99.0000  -30.0000 99

 11 omega -107.00  -46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 61

 12 omega   46.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 69

 13 omega   59.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -30.0000 40

 14 omega  105.00  155.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  150.0000 50

 15 omega   47.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   90.0000 37

 16 omega   46.00   90.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  150.0000 44

 17 omega   52.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 34

 18 omega   43.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -180.0000 42

 19 omega   97.00  123.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  150.0000 26

 20 omega   53.00   79.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  150.0000 26

 21 omega  115.00  149.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000 -150.0000 34

 22 omega  126.00  163.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -150.0000 37

 23 omega  145.00  171.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -30.0000 26

 24 omega   42.00   93.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000    0.0000 51

 25 omega   74.00  133.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000    0.0000 59

 26 omega   43.00   72.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 29

 27 omega   42.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  120.0000 46

 28 omega   44.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  150.0000 29

 29 omega  100.00  125.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -142.0000   -6.0000 25

 30 omega  100.00  161.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 61

 31 omega   65.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 34

 32 omega   47.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -142.0000   -6.0000 26

 33 omega   43.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -60.0000 25

 34 omega  124.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000   60.0000 52

 35 omega  104.00  131.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -30.0000 27

 36 omega  115.00  141.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -90.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0007052000
_diffrn_orient_matrix_UB_12      -0.0953905000
_diffrn_orient_matrix_UB_13      -0.0391888000
_diffrn_orient_matrix_UB_21      0.0210026000
_diffrn_orient_matrix_UB_22      -0.0380570000
_diffrn_orient_matrix_UB_23      0.1008215000
_diffrn_orient_matrix_UB_31      -0.1430174000
_diffrn_orient_matrix_UB_32      -0.0051017000
_diffrn_orient_matrix_UB_33      -0.0192925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12953
_diffrn_reflns_theta_full        71.00
_diffrn_reflns_theta_max         72.12
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.021(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         7716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.2965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                7575
_reflns_number_total             7716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501648a_si_001.cif
_cod_data_source_block           zhouhan0401
_cod_depositor_comments          'Adding full bibliography for 1517203.cif.'
_cod_original_cell_volume        2353.60(7)
_cod_database_code               1517203
_reflns_odcompleteness_completeness 97.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H11 of C11, H12 of C12, H13 of C13, H14 of C14, {H16A,H16B} of C16, H17 of
  C17, H18 of C18, H19 of C19, H20 of C20, H21 of C21, H9 of C9, H8 of C8, H6
  of C6, H5 of C5, H4 of C4, H3 of C3, {H1A,H1B} of C1, H1D of N1D, {H53A,H53B}
  of C53, H52 of C52, H51 of C51, H50 of C50, H49 of C49, H48 of C48, H46 of
  C46, H45 of C45, H1 of N1, H39 of C39, H42 of C42, H43 of C43, H44 of C44,
  H23 of C23, H24 of C24, H25 of C25, H26 of C26, H27 of C27, H30 of C30, H31
  of C31, H32 of C32, H33 of C33, H36 of C36, H37 of C37, H38 of C38
2.a Ternary CH refined with riding coordinates:
 N1(H1), N1D(H1D), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C16(H16A,H16B), C53(H53A,H53B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33), C36(H36),
 C37(H37), C38(H38), C39(H39), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46),
  C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
;