Diastereoselective synthesis of cyclopropyl sulfoxides <i>via</i> hydrosulfenation.
Yuwen, Liyan; Tang, Jiazhong; Qi, Yayu; Zou, Tianyi; Zhang, Shaotong; Zhang, Ya-Qian; Zhang, Qing-Wei; Chemical science 17 (2026) 3171–3177; doi:10.1039/d5sc08731g

data_1576495
_publ_section_title
;
 Diastereoselective synthesis of cyclopropyl sulfoxides <i>via</i>
 hydrosulfenation.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              3171
_journal_page_last               3177
_journal_paper_doi               10.1039/d5sc08731g
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H20 O S'
_chemical_formula_sum            'C19 H20 O S'
_chemical_formula_weight         296.41
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-16 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.273(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1143(5)
_cell_length_b                   7.2877(3)
_cell_length_c                   12.1106(6)
_cell_measurement_reflns_used    4098
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.389
_cell_measurement_theta_min      2.623
_cell_volume                     796.04(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8276
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.624
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1653 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.7933.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0530P)^2^+0.0040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.772
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                2632
_reflns_number_total             3156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08731g2.cif
_cod_data_source_block           241119wjw
_cod_database_code               1576495
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              65914
_shelx_hkl_checksum              83337
_olex2_submission_special_instructions 'No special instructions were received'