Direct α-C-H alkylation of alcohols <i>via</i> photoinduced hydrogen atom transfer.
Wu, Mingzhong; Wang, Yaru; Lv, Xin; Ma, Zhengxian; Sheng, Xiaojing; Wang, Mengjie; Zhang, Yalin; An, Zhenyu; Wang, Xuekun; Organic & biomolecular chemistry 23 (2025) 2365–2369; doi:10.1039/d4ob01874e

data_7160363
_publ_section_title
;
 Direct &#x3b1;-C-H alkylation of alcohols <i>via</i> photoinduced
 hydrogen atom transfer.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2365
_journal_page_last               2369
_journal_paper_doi               10.1039/d4ob01874e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C14 H20 O3 S'
_chemical_formula_sum            'C14 H20 O3 S'
_chemical_formula_weight         268.36
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7926(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.0552(3)
_cell_length_b                   5.67162(7)
_cell_length_c                   22.7509(3)
_cell_measurement_reflns_used    5146
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8850
_cell_measurement_theta_min      3.9350
_cell_volume                     2812.44(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_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     11.00 112.00   0.50    0.50    --   42.30 -13.00-101.00  202
  2  \w    -44.00 -18.00   0.50    0.50    --   42.30 -13.00-101.00   52
  3  \w     18.00  43.00   0.50    0.50    --   42.30  13.00  70.00   50
  4  \w      4.00  75.00   0.50    0.50    --   93.40 -13.00-101.00  142
  5  \w    -10.00  15.00   0.50    0.50    --   42.30 -82.00 -90.00   50
  6  \w    -47.00 -15.00   0.50    0.50    --   42.30 -82.00 -90.00   64
  7  \w    106.00 131.00   0.50    0.50    --   42.30  65.00-120.00   50
  8  \w    -46.00  -7.00   0.50    0.50    --   42.30 -82.00   0.00   78
  9  \w    -40.00   2.00   0.50    0.50    --   42.30 -43.00 120.00   84
 10  \w     25.00  65.00   0.50    0.50    --   42.30 -43.00 120.00   80
 11  \w     16.00  70.00   0.50    0.50    --   42.30 -82.00  90.00  108
 12  \w     64.00  89.00   0.50    0.50    --   42.30  65.00-120.00   50
 13  \w    -30.00  14.00   0.50    0.50    --   42.30 -65.00  90.00   88
 14  \w     44.00  69.00   0.50    0.50    --   42.30 -82.00   0.00   50
 15  \w     33.00  66.00   0.50    0.50    --   42.30 -65.00  90.00   66
 16  \w    -42.00  42.00   0.50    0.50    --   42.30 -82.00  30.00  168
 17  \w      4.00  85.00   0.50    0.50    --   93.40 -42.00-180.00  162
 18  \w     72.00 163.00   0.50    0.50    --   93.40  68.00 150.00  182
 19  \w     61.00  88.00   0.50    0.50    --   93.40 -82.00  60.00   54
 20  \w     18.00  96.00   0.50    0.50    --   93.40 -82.00 150.00  156
 21  \w     70.00  96.00   0.50    0.50    --   93.40 -77.00 -30.00   52
 22  \w      8.00  34.00   0.50    0.50    --   93.40 -77.00 -30.00   52
 23  \w     57.00  93.00   0.50    0.50    --   93.40 -82.00  90.00   72
 24  \w     10.00  36.00   0.50    0.50    --   93.40 -82.00  60.00   52
 25  \w      5.00  72.00   0.50    0.50    --   93.40 -50.00-120.00  134
 26  \w     99.00 124.00   0.50    0.50    --   93.40 -42.00-180.00   50
 27  \w      4.00 119.00   0.50    0.50    --   93.40 -77.00-180.00  230
 28  \w     78.00 178.00   0.50    0.50    --   93.40  13.00  70.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0628725000
_diffrn_orient_matrix_UB_12      0.0443594000
_diffrn_orient_matrix_UB_13      -0.0195594000
_diffrn_orient_matrix_UB_21      0.0310254000
_diffrn_orient_matrix_UB_22      -0.0128588000
_diffrn_orient_matrix_UB_23      0.0653487000
_diffrn_orient_matrix_UB_31      0.0089023000
_diffrn_orient_matrix_UB_32      -0.2677377000
_diffrn_orient_matrix_UB_33      -0.0063882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7352
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.964
_diffrn_reflns_theta_min         3.932
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0684P)^2^+0.6653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2297
_reflns_number_total             2539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01874e2.cif
_cod_data_source_block           mwj_auto
_cod_depositor_comments          'Adding full bibliography for 7160363.cif.'
_cod_database_code               7160363
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.888
_diffrn_oxdiff_digest_frames
;
0121644f552762a2d0a94f323ac4c433c00003009fd
;
_diffrn_oxdiff_digest_hkl
;
01562fdee9e77a28912c9a2442b46a769b1305
;
_reflns_odcompleteness_completeness 99.50
_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, All C(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C5(H5A,H5B), C1(H1A,H1B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C12(H12), C13(H13), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              13287
_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 2.560
_oxdiff_exptl_absorpt_empirical_full_min 0.627