Chiral (η6-p-Cymene)ruthenium(II) Complexes Containing Monodentate Acylthiourea Ligands for Efficient Asymmetric Transfer Hydrogenation of Ketones
Sheeba, Mani Mary; Muthu Tamizh, Manoharan; Farrugia, Louis J.; Endo, Akira; Karvembu, Ramasamy; Organometallics 33 (2014) 540–; doi:10.1021/om4010548

data_4082302
_publ_section_title
;
 Chiral (\h6-p-Cymene)ruthenium(II) Complexes Containing Monodentate
 Acylthiourea Ligands for Efficient Asymmetric Transfer Hydrogenation of
 Ketones
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              540
_journal_paper_doi               10.1021/om4010548
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H14 N2 O S2'
_chemical_formula_sum            'C14 H14 N2 O S2'
_chemical_formula_weight         290.39
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-06-12T12:58:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1813(2)
_cell_length_b                   9.8395(2)
_cell_length_c                   19.6244(5)
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     1386.67(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.057277
_diffrn_orient_matrix_UB_12      -0.060367
_diffrn_orient_matrix_UB_13      0.03523
_diffrn_orient_matrix_UB_21      0.034992
_diffrn_orient_matrix_UB_22      -0.066591
_diffrn_orient_matrix_UB_23      -0.036303
_diffrn_orient_matrix_UB_31      0.122006
_diffrn_orient_matrix_UB_32      0.047439
_diffrn_orient_matrix_UB_33      -0.006128
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            94195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_reduction_process
;

        Scaled and merged with Sortav

        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58

        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397

;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.988
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;

        P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.

        (1965), 18, 1035-1038

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.497
_exptl_crystal_size_min          0.477
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;

 Flack x determined using 2567 quotients [(I+)-(I-)]/[(I+)+(I-)]

 (Parsons and Flack (2004), Acta Cryst. A60, s61).

;
_refine_ls_abs_structure_Flack   0.022(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         6086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.0851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.06
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                5955
_reflns_number_total             6086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om4010548_si_002.cif
_cod_data_source_block           comp-L1
_cod_database_code               4082302
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.841