Photoinduced C(sp3)‒H Sulfination Empowers a Direct and Chemoselective Introduction of the Sulfonyl Group
Jin, Shengfei; Haug, Graham C.; Trevino, Ramon; Nguyen, Viet D.; Arman, Hadi; Larionov, Oleg V.; Chemical Science  (2021) –; doi:10.1039/D1SC04245A

data_1564736
_publ_section_title
;
 Photoinduced C(sp3)--H Sulfination Empowers a Direct and Chemoselective
 Introduction of the Sulfonyl Group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04245A
_journal_year                    2021
_chemical_formula_moiety         'C13 H18 O3 S'
_chemical_formula_sum            'C13 H18 O3 S'
_chemical_formula_weight         254.33
_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             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.051(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8529(2)
_cell_length_b                   9.2662(3)
_cell_length_c                   19.1898(5)
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.2930
_cell_measurement_theta_min      3.0420
_cell_volume                     1218.56(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -42.00  80.00   1.00   35.00    --   -9.70  69.00 -26.00  122
  2  \w    -34.00  80.00   1.00   35.00    --   -9.70  38.00  90.00  114
  3  \w    -99.00 -74.00   1.00   35.00    --   -9.70 -72.00 120.00   25
  4  \w    -34.00  80.00   1.00   35.00    --   -9.70  38.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139358000
_diffrn_orient_matrix_UB_12      -0.0029448000
_diffrn_orient_matrix_UB_13      0.0365864000
_diffrn_orient_matrix_UB_21      -0.0645250000
_diffrn_orient_matrix_UB_22      -0.0597520000
_diffrn_orient_matrix_UB_23      0.0019933000
_diffrn_orient_matrix_UB_31      0.0797817000
_diffrn_orient_matrix_UB_32      -0.0477517000
_diffrn_orient_matrix_UB_33      -0.0047438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.441
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0300P)^2^+1.4500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2728
_reflns_number_total             2778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04245a2.cif
_cod_data_source_block           cd1683c
_cod_database_code               1564736
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         S1o4C20H20
_chemical_oxdiff_usercomment     'bicyclooctane with C=O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C2(H2A,H2B), C7(H7A,H7B), C10(H10A,H10B), C4(H4A,
 H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.928