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_1576498
_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         '2(C18 H20 O2 S)'
_chemical_formula_sum            'C36 H40 O4 S2'
_chemical_formula_weight         600.80
_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             2024-07-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-13 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.632(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   5.9180(3)
_cell_length_b                   8.0256(4)
_cell_length_c                   16.8884(9)
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.881
_cell_measurement_theta_min      4.609
_cell_volume                     793.04(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      170.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7231
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.856
_diffrn_reflns_theta_min         4.608
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.2690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.1027 after correction.
The Ratio of minimum to maximum transmission is 0.3583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2598
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08731g2.cif
_cod_data_source_block           240715gl_1
_cod_database_code               1576498
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.823
_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)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              70253
_shelx_hkl_checksum              59471
_olex2_submission_special_instructions 'No special instructions were received'