Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.
Wangweerawong, Apiwat; Hummel, Joshua R.; Bergman, Robert G.; Ellman, Jonathan A.; The Journal of organic chemistry 81 (2016) 1547–1557; doi:10.1021/acs.joc.5b02700

data_4031893
_publ_section_title
;
 Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its
 Application to the Asymmetric Synthesis of \a-Amino Acids.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1547
_journal_page_last               1557
_journal_paper_doi               10.1021/acs.joc.5b02700
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 Cl N2 O4'
_chemical_formula_sum            'C22 H23 Cl N2 O4'
_chemical_formula_weight         414.87
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                103.623(9)
_cell_angle_beta                 99.874(8)
_cell_angle_gamma                90.545(9)
_cell_formula_units_Z            2
_cell_length_a                   8.5086(6)
_cell_length_b                   10.4268(8)
_cell_length_c                   13.8730(10)
_cell_measurement_reflns_used    -182
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.3
_cell_volume                     1176.83(16)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
; 
PROBLEM: The value of Rint is greater than 0.18 
RESPONSE: See response to PLAT020. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2300
_diffrn_reflns_av_unetI/netI     0.1973
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23371
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        58.931
_diffrn_reflns_theta_max         58.931
_diffrn_reflns_theta_min         3.331
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         6208
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1015P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2282
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                4293
_reflns_number_total             6208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02700_si_002.cif
_cod_data_source_block           007-15175
_cod_database_code               4031893
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.635
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              74201
_shelx_hkl_checksum              93841
_shelx_fab_checksum              74692