Ru-catalyzed highly diastereoselective hydrogenation of N-tert-butylsulfinyl ketimines for the synthesis of aryl glycine derivatives
Wei, qiaoling; Zhang, Feng; zhao, xiaofang; Wang, Chao; Xiao, Jianling; Tang, Weijun; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01329A

data_7155693
_publ_section_title
;
 Ru-catalyzed highly diastereoselective hydrogenation of
 N-tert-butylsulfinyl ketimines for the synthesis of aryl glycine
 derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01329A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 F N O3 S'
_chemical_formula_sum            'C15 H20 F N O3 S'
_chemical_formula_weight         313.38
_chemical_melting_point          339.1(7)
_chemical_name_systematic
'isopropyl (S,Z)-2-((tert-butylsulfinyl)imino)-2-(4-fluorophenyl)acetate'
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-05-18 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8617(7)
_cell_length_b                   13.1073(12)
_cell_length_c                   28.600(2)
_cell_measurement_reflns_used    3973
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.6860
_cell_measurement_theta_min      3.9490
_cell_volume                     3322.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -40.00  -2.00   1.00    3.50    --  -11.51  57.00  90.00   38
  2  \w     28.00  61.00   1.00    3.50    --  -11.51  57.00  90.00   33
  3  \w     35.00  93.00   1.00    3.50    --   11.74 178.00 -60.00   58
  4  \w     51.00  99.00   1.00    3.50    --   11.74 178.00  90.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0666887000
_diffrn_orient_matrix_UB_12      -0.0191402000
_diffrn_orient_matrix_UB_13      0.0105995000
_diffrn_orient_matrix_UB_21      -0.0422882000
_diffrn_orient_matrix_UB_22      0.0143416000
_diffrn_orient_matrix_UB_23      -0.0200016000
_diffrn_orient_matrix_UB_31      0.0136380000
_diffrn_orient_matrix_UB_32      -0.0484968000
_diffrn_orient_matrix_UB_33      -0.0101150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15296
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.615
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0434P)^2^+0.0664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                6358
_reflns_number_total             7637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01329a2.cif
_cod_data_source_block           exp_551
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '338.4-339.8' was changed to
'339.1(7)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155693
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C011(H011)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C5(H5), C00N(H00N), C00O(H00O), C00R(H00R), C6(H6), C00V(H00V)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C00X(H00A,H00B,H00C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C), C010(H01A,H01B,H01C), C10(H10A,H10B,H10C), C013(H01D,H01E,H01F),
 C014(H01G,H01H,H01I), C11(H11A,H11B,H11C), C016(H01J,H01K,H01L)
;
_olex2_date_sample_data_collection 2017-05-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.497
_oxdiff_exptl_absorpt_empirical_full_min 0.530