Chiral Lewis base/Lewis acid/Brønsted acid cooperative catalysis enabled regio- and enantioselective electrophilic sulfenylation/semipinacol rearrangement of allenols.
Wei, Zheng-Wei; Cai, Qing-Yun; Yang, Li-Miao; Huo, Yu-Xuan; Li, Ze-Long; Gong, Xue-Qing; Chen, Zhi-Min; Chemical science 17 (2026) 2802–2810; doi:10.1039/d5sc06981e

data_1576736
_publ_section_title
;
 Chiral Lewis base/Lewis acid/Br&#xf8;nsted acid cooperative catalysis
 enabled regio- and enantioselective electrophilic
 sulfenylation/semipinacol rearrangement of allenols.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              2802
_journal_page_last               2810
_journal_paper_doi               10.1039/d5sc06981e
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C20 H16 Br F3 N0 O S'
_chemical_formula_sum            'C20 H16 Br F3 N0 O S'
_chemical_formula_weight         441.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V137 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-07-17 deposited with the CCDC.	2025-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8548(6)
_cell_length_b                   8.0071(3)
_cell_length_c                   25.9391(10)
_cell_measurement_reflns_used    6901
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.294
_cell_measurement_theta_min      3.4075
_cell_volume                     3708.4(2)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS 8.5.0.27 Release/2023-03-20 and APEX5 2023.9-2'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1785
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.459
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.396
_exptl_absorpt_correction_T_max  0.753056
_exptl_absorpt_correction_T_min  0.605974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L., 
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0586
_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^)+(0.1501P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2640
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  0.14345
_twin_individual_twin_matrix_12  0.02187
_twin_individual_twin_matrix_13  0.94481
_twin_individual_twin_matrix_21  0.94427
_twin_individual_twin_matrix_22  0.03986
_twin_individual_twin_matrix_23  -0.72257
_twin_individual_twin_matrix_31  -0.11283
_twin_individual_twin_matrix_32  0.99581
_twin_individual_twin_matrix_33  -0.15671
_cod_data_source_file            d5sc06981e2.cif
_cod_data_source_block           t_a
_cod_database_code               1576736
_shelx_shelxl_version_number     2019/1
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              82981
_shelx_hkl_checksum              960