Direct Asymmetric Ruthenium-Catalyzed Reductive Amination of Alkyl-Aryl Ketones with Ammonia and Hydrogen.
Gallardo-Donaire, Joan; Hermsen, Marko; Wysocki, Jedrzej; Ernst, Martin; Rominger, Frank; Trapp, Oliver; Hashmi, A Stephen K; Schaefer, Ansgar; Comba, Peter; Schaub, Thomas; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b10496

data_4126908
_publ_section_title
;
 Direct Asymmetric Ruthenium-Catalyzed Reductive Amination of Alkyl-Aryl
 Ketones with Ammonia and Hydrogen.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b10496
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C73 H56 Fe I O P3 Ru'
_chemical_formula_weight         1325.90
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2603(3)
_cell_length_b                   19.3424(5)
_cell_length_c                   33.2993(11)
_cell_measurement_reflns_used    6219
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      2.25
_cell_volume                     6608.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            54554
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         1.217
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.8454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             2680
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
; 
 Flack x determined using 3229 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.024(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         11677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0344P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                9146
_reflns_number_total             11677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10496_si_001.cif
_cod_data_source_block           jgd4_sq
_cod_database_code               4126908
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              29056
_shelx_hkl_checksum              87870
_shelx_fab_checksum              71284