Access to S-Stereogenic Free Sulfoximines via Bifunctional Phosphonium Salt-Catalyzed Desymmetrization of Bisphenols
Fang, Siqiang; Liu, Zanjiao; Zhang, Hongkui; Pan, Jianke; Chen, Yuan; Ren, Xiaoyu; Wang, Tianli; ACS Catalysis 11 (2021) 13902–13912; doi:10.1021/acscatal.1c03966

data_4519164
_publ_section_title
;
 Access to S-Stereogenic Free Sulfoximines via Bifunctional Phosphonium
 Salt-Catalyzed Desymmetrization of Bisphenols
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13902
_journal_page_last               13912
_journal_paper_doi               10.1021/acscatal.1c03966
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O5 S2'
_chemical_formula_sum            'C19 H17 N O5 S2'
_chemical_formula_weight         403.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0907(3)
_cell_length_b                   19.9189(8)
_cell_length_c                   10.3884(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    304.0
_cell_measurement_theta_max      25.151
_cell_measurement_theta_min      2.216
_cell_volume                     1875.54(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      304.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36402
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.966
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1154 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9205.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2526 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8598
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0484P)^2^+0.4997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6568
_reflns_number_total             8598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03966_si_003.cif
_cod_data_source_block           mo_wtl_fsq_6a_0m_a
_cod_database_code               4519164
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N00C-H00C
 0.85 with sigma of 0.01
3. Rigid bond restraints
 S004, O00B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
S004 \\sim O00B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.01 within 2A
5.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C01B(H01B), C01C(H01E),
 C01D(H01F), C01E(H01G), C01F(H01H), C01G(H01I), C011(H011), C012(H012),
 C013(H013), C015(H015), C016(H016), C017(H017), C018(H018), C019(H019)
5.b Idealised Me refined as rotating group:
 C01H(H01J,H01K,H01L), C01I(H01A,H01C,H01D)
5.c Idealised tetrahedral OH refined as rotating group:
 O00D(H00D), O00E(H00E)
;
_shelx_res_checksum              23387
_shelx_hkl_checksum              75963
_olex2_submission_special_instructions 'No special instructions were received'