Asymmetric Transfer Hydrogenation of (Hetero)arylketones with Tethered Rh(III)-N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine Complexes: Scope and Limitations.
Zheng, Long-Sheng; Llopis, Quentin; Echeverria, Pierre-Georges; Férard, Charlène; Guillamot, Gérard; Phansavath, Phannarath; Ratovelomanana-Vidal, Virginie; The Journal of organic chemistry 82 (2017) 5607–5615; doi:10.1021/acs.joc.7b00436

data_4032556
_publ_section_title
;
 Asymmetric Transfer Hydrogenation of (Hetero)arylketones with Tethered
 Rh(III)-N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine Complexes:
 Scope and Limitations.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5607
_journal_page_last               5615
_journal_paper_doi               10.1021/acs.joc.7b00436
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C40 H40 Cl10 F N2 O2 Rh S'
_chemical_formula_sum            'C40 H40 Cl10 F N2 O2 Rh S'
_chemical_formula_weight         1089.21
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2252(8)
_cell_length_b                   17.5063(11)
_cell_length_c                   19.1686(11)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.33
_cell_volume                     4773.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61040
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.831
_diffrn_reflns_theta_min         2.129
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 4287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         12361
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+3.6691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                10718
_reflns_number_total             12361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00436_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4032556
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              83199
_shelx_hkl_checksum              41064