Highly enantioselective Ir/f-amphox-catalyzed hydrogenation of ketoamides: efficient access to chiral hydroxy amides
Hu, Yang; Yin, Xuguang; Chen, Ziyi; Dong, Xiu-Qin; Zhang, Xumu; Organic Chemistry Frontiers 5 (2018) 2000–; doi:10.1039/C8QO00307F

data_1554304
_publ_section_title
;
 Highly enantioselective Ir/f-amphox-catalyzed hydrogenation of
 ketoamides: efficient access to chiral hydroxy amides
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2000
_journal_paper_doi               10.1039/C8QO00307F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C17 H18 Cl N O2'
_chemical_formula_weight         303.77
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.352(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9758(3)
_cell_length_b                   8.5937(4)
_cell_length_c                   15.7695(7)
_cell_measurement_reflns_used    5164
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.47
_cell_measurement_theta_min      2.81
_cell_volume                     808.45(7)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7618
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        64.999
_diffrn_reflns_theta_max         64.999
_diffrn_reflns_theta_min         2.807
_exptl_absorpt_coefficient_mu    2.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.052(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2388
_reflns_number_total             2587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00307f2.cif
_cod_data_source_block           cu_180312E_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554304
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.816
_shelx_res_checksum              6777
_shelx_hkl_checksum              80874