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_7250559
_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         'C15 H15 Cl O S'
_chemical_formula_sum            'C15 H15 Cl O S'
_chemical_formula_weight         278.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                76.4892(19)
_cell_angle_beta                 82.2856(18)
_cell_angle_gamma                71.4025(19)
_cell_formula_units_Z            4
_cell_length_a                   9.2974(2)
_cell_length_b                   10.0625(2)
_cell_length_c                   15.8641(4)
_cell_measurement_reflns_used    12123
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2610
_cell_measurement_theta_min      2.8380
_cell_volume                     1364.86(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.961
_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    -69.00 -27.00   0.50    0.05    -- -100.00  61.00 120.00   84
  2  \w    -67.00 -29.00   0.50    0.05    -- -100.00  61.00  90.00   76
  3  \w    -62.00 -33.00   0.50    0.05    -- -100.00  61.00  60.00   58
  4  \w    -68.00 -28.00   0.50    0.05    -- -100.00  61.00  30.00   80
  5  \w    -28.00  25.00   0.50    0.05    --  -45.64  19.00  60.00  106
  6  \w    -28.00  32.00   0.50    0.05    --  -45.64  19.00-120.00  120
  7  \w     55.00  80.00   0.50    0.05    --   45.64-162.00-142.00   50
  8  \w    102.00 137.00   0.50    0.05    --  105.05-162.00-142.00   70
  9  \w     82.00 112.00   0.50    0.05    --  105.05-125.00 -90.00   60
 10  \w     43.00  73.00   0.50    0.05    --  105.05-125.00 -90.00   60
 11  \w     60.00 112.00   0.50    0.05    --  105.05-125.00 -30.00  104
 12  \w     70.00 109.00   0.50    0.05    --  105.05-117.00   7.00   78
 13  \w     68.00 108.00   0.50    0.05    --  105.05-106.00  34.70   80
 14  \w     32.00  76.00   0.50    0.05    --  105.05 -94.00 -90.00   88
 15  \w     46.00  80.00   0.50    0.05    --  105.05 -94.00-150.00   68
 16  \w     13.00  58.00   0.50    0.05    --   45.64-117.00   7.00   90
 17  \w     39.00  65.00   0.50    0.05    --  105.05 -77.00 120.00   52
 18  \w     32.00  70.00   0.50    0.05    --  105.05 -61.00 120.00   76
 19  \w     36.00  61.00   0.50    0.05    --  105.05 -61.00 150.00   50
 20  \w     68.00  93.00   0.50    0.05    --  105.05 -77.00 120.00   50
 21  \w     32.00  72.00   0.50    0.05    --  105.05 -61.00 -30.00   80
 22  \w     48.00  81.00   0.50    0.05    --  105.05 -77.00-150.00   66
 23  \w    107.00 141.00   0.50    0.05    --  105.05 117.00  94.00   68
 24  \w     89.00 174.00   0.50    0.05    --  105.05  45.00  90.00  170
 25  \w     55.00 118.00   0.50    0.05    --   45.64 162.00-115.00  126
 26  \w     81.00 106.00   0.50    0.05    --  105.05 162.00-115.00   50
 27  \w     96.00 169.00   0.50    0.05    --  105.05  30.00-180.00  146
 28  \w     58.00 119.00   0.50    0.05    --   45.64  57.00-120.00  122
 29  \w   -117.00 -23.00   0.50    0.05    --  -45.64 -77.00 -60.00  188
 30  \w   -112.00 -80.00   0.50    0.05    -- -100.00 -15.00-180.00   64
 31  \w   -175.00-128.00   0.50    0.05    -- -100.00 -15.00-180.00   94
 32  \w   -148.00 -84.00   0.50    0.05    -- -100.00 -45.00 -90.00  128
 33  \w   -135.00-109.00   0.50    0.05    -- -100.00 -30.00  60.00   52
 34  \w   -175.00-138.00   0.50    0.05    -- -100.00 -30.00  60.00   74
 35  \w   -152.00-108.00   0.50    0.05    -- -100.00-117.00   7.00   88
 36  \w   -105.00 -75.00   0.50    0.05    --  -45.64-162.00-142.00   60
 37  \w   -127.00-102.00   0.50    0.05    -- -100.00-162.00-142.00   50
 38  \w   -114.00 -76.00   0.50    0.05    -- -100.00-125.00  60.00   76
 39  \w   -169.00-126.00   0.50    0.05    -- -100.00-125.00  60.00   86
 40  \w    -81.00 -15.00   0.50    0.05    --  -45.64 117.00  94.00  132
 41  \w    -86.00 -61.00   0.50    0.05    -- -100.00 117.00  94.00   50
 42  \w   -111.00 -70.00   0.50    0.05    -- -100.00 125.00  30.00   82
 43  \w   -102.00 -74.00   0.50    0.05    --  -45.64 162.00-115.00   56
 44  \w   -104.00 -50.00   0.50    0.05    -- -100.00 162.00-115.00  108
;
_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      0.0848716000
_diffrn_orient_matrix_UB_12      0.0411935000
_diffrn_orient_matrix_UB_13      0.0621051000
_diffrn_orient_matrix_UB_21      -0.0563942000
_diffrn_orient_matrix_UB_22      -0.0999577000
_diffrn_orient_matrix_UB_23      0.0771464000
_diffrn_orient_matrix_UB_31      0.1425142000
_diffrn_orient_matrix_UB_32      -0.1246130000
_diffrn_orient_matrix_UB_33      -0.0144319000
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.481
_diffrn_reflns_theta_min         2.871
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75955
_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    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0806P)^2^+0.2139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4993
_reflns_number_total             5444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc02604k2.cif
_cod_data_source_block           gujy_a_241224_auto
_cod_depositor_comments
'Adding full bibliography for 7250559--7250560.cif.'
_cod_original_cell_volume        1364.85(5)
_cod_database_code               7250559
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOSCl
_shelx_estimated_absorpt_t_max   0.660
_shelx_estimated_absorpt_t_min   0.519
_reflns_odcompleteness_completeness 99.90
_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
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C8(H8A,H8B), C9(H9A,H9B),
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C30(H30), C5(H5), C15(H15), C19(H19), C26(H26), C17(H17),
 C4(H4), C27(H27), C29(H29), C14(H14), C1(H1), C3(H3), C18(H18), C2(H2),
 C11(H11), C12(H12)
;
_shelx_res_checksum              1078
_shelx_hkl_checksum              15189
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.523