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_4034500
_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         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.35
_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   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 105.061(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0431(5)
_cell_length_b                   10.1175(6)
_cell_length_c                   8.8692(6)
_cell_measurement_reflns_used    6304
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.38
_cell_volume                     696.95(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.378
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       Shard
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0365P)^2^+0.0674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2966
_reflns_number_total             3221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01964_si_002.cif
_cod_data_source_block           4a_d18148_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034500
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              62596
_shelx_hkl_checksum              12910