Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P' Complex.
Seo, Chris S. G.; Tannoux, Thibault; Smith, Samantha A. M.; Lough, Alan J.; Morris, Robert H.; The Journal of organic chemistry 84 (2019) 12040–12049; doi:10.1021/acs.joc.9b01964

data_4034499
_publ_section_title
;
 Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an
 Iron(II) P-NH-P' Complex.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12040
_journal_page_last               12049
_journal_paper_doi               10.1021/acs.joc.9b01964
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 N O P S'
_chemical_formula_sum            'C18 H18 N O P S'
_chemical_formula_weight         327.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   mixed
_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                   11.4607(2)
_cell_length_b                   11.4607(2)
_cell_length_c                   12.8304(3)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.74
_cell_measurement_theta_min      3.86
_cell_volume                     1685.24(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32151
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.965
_diffrn_reflns_theta_max         66.965
_diffrn_reflns_theta_min         3.857
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.016(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0370P)^2^+0.3394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2787
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01964_si_002.cif
_cod_data_source_block           3j_d18147_a
_cod_original_cell_volume        1685.24(7)
_cod_database_code               4034499
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.490
_shelx_estimated_absorpt_t_max   0.781
_shelx_res_checksum              73980
_shelx_hkl_checksum              29569