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_4519163
_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         'C H Cl3, C32 H36 N O4 P S'
_chemical_formula_sum            'C33 H37 Cl3 N O4 P S'
_chemical_formula_weight         681.01
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8935(12)
_cell_length_b                   13.9039(16)
_cell_length_c                   21.127(3)
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.809
_cell_measurement_theta_min      2.421
_cell_volume                     3493.7(7)
_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      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.1019
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27119
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         1.965
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1128 before and 0.0798 after correction.
The Ratio of minimum to maximum transmission is 0.7218.
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    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1631 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7978
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0739
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+2.4668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.2019
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5270
_reflns_number_total             7978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03966_si_002.cif
_cod_data_source_block           mo_wtl_fsq_g1_150k_2_0m_a
_cod_original_cell_volume        3493.6(7)
_cod_database_code               4519163
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.845
_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
 N3-H3
 0.91 with sigma of 0.01
3. Rigid bond restraints
 C26, C27
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C26, C28
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C26, C29
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C26 \\sim C27: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C26 \\sim C28: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
C26 \\sim C29: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C31(H31)
5.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C4(H4), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
5.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              44812
_shelx_hkl_checksum              13118
_olex2_submission_special_instructions 'No special instructions were received'