Enantioselective Imine Reduction Catalyzed by Phosphenium Ions.
Lundrigan, Travis; Welsh, Erin N.; Hynes, Toren; Tien, Chieh-Hung; Adams, Matt R.; Roy, Kayelani R.; Robertson, Katherine N.; Speed, Alexander W. H.; Journal of the American Chemical Society 141 (2019) 14083–14088; doi:10.1021/jacs.9b07293

data_4128780
_publ_section_title
;
 Enantioselective Imine Reduction Catalyzed by Phosphenium Ions.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14083
_journal_page_last               14088
_journal_paper_doi               10.1021/jacs.9b07293
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 N2 P S2, C F3 O3 S'
_chemical_formula_sum            'C23 H20 F3 N2 O3 P S3'
_chemical_formula_weight         556.56
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8209(12)
_cell_length_b                   14.103(2)
_cell_length_c                   22.253(3)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.61
_cell_measurement_theta_min      2.33
_cell_volume                     2454.5(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.953
_diffrn_reflns_theta_min         1.710
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0456P)^2^+0.0933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                5631
_reflns_number_total             6158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07293_si_002.cif
_cod_data_source_block           AS008
_cod_original_cell_volume        2454.4(7)
_cod_database_code               4128780
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.912
_shelx_res_checksum              78775
_shelx_hkl_checksum              91647