Anti-Markovnikov hydrosulfenylation of unactivated alkenes/alkynes via visible-light organic photocatalysis
Gu, Jiayi; Xin, Meixiu; Cheng, Zhuo; Zou, Zhiru; Du, Zhibo; Cheng, Xinyi; Wang, Yan; Zou, Yong; Green Chemistry 27 (2025) 7763–7770; doi:10.1039/D5GC02604K

data_7250560
_publ_section_title
;
 Anti-Markovnikov hydrosulfenylation of unactivated alkenes/alkynes via
 visible-light organic photocatalysis
;
_journal_issue                   26
_journal_name_full               'Green Chemistry'
_journal_page_first              7763
_journal_page_last               7770
_journal_paper_doi               10.1039/D5GC02604K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 F6 O2 S'
_chemical_formula_sum            'C18 H16 F6 O2 S'
_chemical_formula_weight         410.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.690(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0767(9)
_cell_length_b                   9.2205(4)
_cell_length_c                   9.3765(3)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8390
_cell_measurement_theta_min      2.1410
_cell_volume                     1813.23(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -79.00 -54.00   0.50    0.50    --  -45.39 127.00 150.00   50
  2  \w   -117.00 -62.00   0.50    0.50    --  -45.39-143.00 -94.00  110
  3  \w   -103.00 -61.00   0.50    0.50    --  -45.39 143.00 -39.00   84
  4  \w     69.00  96.00   0.50    0.50    --   45.39 143.00 -39.00   54
  5  \w     43.00  68.00   0.50    0.50    --   45.39-143.00 -94.00   50
  6  \w   -121.00 -32.00   0.50    3.00    -- -100.00 143.00 -39.00  178
  7  \w   -161.00 -94.00   0.50    3.00    -- -100.00-127.00  75.00  134
  8  \w     99.00 125.00   0.50    3.00    --  105.05-143.00 -94.00   52
  9  \w     34.00  66.00   0.50    3.00    --  105.05-127.00  75.00   64
 10  \w    135.00 161.00   0.50    3.00    --  105.05 143.00 -39.00   52
 11  \w    -24.00  23.00   0.50    0.50    --  -45.39  19.00-180.00   94
 12  \w    -15.00  31.00   0.50    0.50    --  -45.39  19.00-150.00   92
 13  \w     21.00 112.00   0.50    0.50    --   45.39  77.00 150.00  182
 14  \w   -106.00 -69.00   0.50    3.00    -- -100.00 103.00  82.99   74
 15  \w    -68.00 -31.00   0.50    3.00    -- -100.00  61.00 -60.00   74
 16  \w   -172.00 -84.00   0.50    3.00    -- -100.00 -94.00-180.00  176
 17  \w     32.00  68.00   0.50    3.00    --  105.05 -94.00  90.00   72
 18  \w     34.00  74.00   0.50    3.00    --  105.05 -77.00  90.00   80
 19  \w     32.00  58.00   0.50    3.00    --  105.05 -61.00 150.00   52
 20  \w    140.00 166.00   0.50    3.00    --  105.05  30.00  90.00   52
 21  \w     88.00 129.00   0.50    3.00    --  105.05  30.00  90.00   82
 22  \w     78.00 103.00   0.50    3.00    --  105.05 -77.00  90.00   50
 23  \w    123.00 178.00   0.50    3.00    --  105.05  30.00 150.00  110
 24  \w     74.00 104.00   0.50    3.00    --  105.05 -94.00  90.00   60
 25  \w     32.00  76.00   0.50    3.00    --  105.05 -94.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0676953000
_diffrn_orient_matrix_UB_12      0.0646468000
_diffrn_orient_matrix_UB_13      0.0109556000
_diffrn_orient_matrix_UB_21      0.0282445000
_diffrn_orient_matrix_UB_22      -0.1538093000
_diffrn_orient_matrix_UB_23      -0.0056943000
_diffrn_orient_matrix_UB_31      -0.0037777000
_diffrn_orient_matrix_UB_32      0.0095243000
_diffrn_orient_matrix_UB_33      -0.1646326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11553
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.063
_diffrn_reflns_theta_min         2.107
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.1030
_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^)+(0.1058P)^2^+9.7504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2660
_refine_ls_wR_factor_ref         0.2803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             3546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc02604k2.cif
_cod_data_source_block           gujy_b_241224_auto
_cod_depositor_comments
'Adding full bibliography for 7250559--7250560.cif.'
_cod_database_code               7250560
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNFS
_shelx_estimated_absorpt_t_max   0.774
_shelx_estimated_absorpt_t_min   0.662
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C1(H1), C11(H11), C15(H15), C12(H12), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              46299
_shelx_hkl_checksum              48300
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.585
_oxdiff_exptl_absorpt_empirical_full_min 0.319