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_1564738
_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         'C10 H19 N O3 S'
_chemical_formula_sum            'C10 H19 N O3 S'
_chemical_formula_weight         233.32
_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             2018-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-06-24 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.019(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7797(3)
_cell_length_b                   10.1425(2)
_cell_length_c                   9.6720(2)
_cell_measurement_reflns_used    8601
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.2940
_cell_measurement_theta_min      2.5850
_cell_volume                     1149.20(4)
_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 1.000
_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    -85.00  30.00   1.00   20.00    --    4.20 -44.00  70.00  115
  2  \w    -35.00  80.00   1.00   20.00    --   -9.90  44.00-139.00  115
  3  \w    -34.00  80.00   1.00   20.00    --   -9.90  38.00  60.00  114
  4  \w    -34.00  80.00   1.00   20.00    --   -9.90  38.00 -30.00  114
  5  \w    -99.00 -40.00   1.00   20.00    --   -9.90 -72.00 120.00   59
  6  \w    -99.00  22.00   1.00   20.00    --   -9.90 -72.00 -60.00  121
;
_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      -0.0063620000
_diffrn_orient_matrix_UB_12      -0.0317138000
_diffrn_orient_matrix_UB_13      -0.0657241000
_diffrn_orient_matrix_UB_21      0.0550001000
_diffrn_orient_matrix_UB_22      0.0222633000
_diffrn_orient_matrix_UB_23      -0.0128507000
_diffrn_orient_matrix_UB_31      0.0244766000
_diffrn_orient_matrix_UB_32      -0.0582258000
_diffrn_orient_matrix_UB_33      0.0308853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86883
_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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0390P)^2^+0.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2630
_reflns_number_total             2642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04245a2.cif
_cod_data_source_block           cd1667
_cod_database_code               1564738
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C12H12S1O3N1
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.877
_reflns_odcompleteness_completeness 99.89
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C1(H1A,
 H1B), C8(H8A,H8B), C7(H7A,H7B), C4(H4A,H4B)
;
_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 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.865