Synthesis of 2-arylethenesulfonyl fluorides and isoindolinones: Ru-catalyzed C-H activation of nitrones with ethenesulfonyl fluoride.
Wang, Tong-Tong; Zhao, Li-Ming; Chemical communications (Cambridge, England) 58 (2022) 11099–11102; doi:10.1039/d2cc03418b

data_7130707
_publ_section_title
;
 Synthesis of 2-arylethenesulfonyl fluorides and isoindolinones:
 Ru-catalyzed C-H activation of nitrones with ethenesulfonyl fluoride.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11099
_journal_page_last               11102
_journal_paper_doi               10.1039/d2cc03418b
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C13 H16 F N O3 S'
_chemical_formula_sum            'C13 H16 F N O3 S'
_chemical_formula_weight         285.33
_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             2021-12-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-29 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.592(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7846(12)
_cell_length_b                   16.6680(18)
_cell_length_c                   16.942(2)
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4700
_cell_measurement_theta_min      2.4270
_cell_volume                     3011.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -38.00  34.00   1.00    7.50    --  -16.59  19.00 -30.00   72
  2  \w    -25.00  20.00   1.00    7.50    --  -16.59 -99.00 -60.00   45
  3  \w    -44.00  10.00   1.00    7.50    --   15.65 -57.00 150.00   54
  4  \w     42.00  85.00   1.00    7.50    --   15.65 178.00 -60.00   43
  5  \w     43.00  75.00   1.00    7.50    --   15.65 178.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0619424000
_diffrn_orient_matrix_UB_12      -0.0039300000
_diffrn_orient_matrix_UB_13      0.0087076000
_diffrn_orient_matrix_UB_21      -0.0045218000
_diffrn_orient_matrix_UB_22      -0.0385136000
_diffrn_orient_matrix_UB_23      -0.0182216000
_diffrn_orient_matrix_UB_31      0.0234861000
_diffrn_orient_matrix_UB_32      -0.0178414000
_diffrn_orient_matrix_UB_33      0.0372091000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13084
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.500
_diffrn_reflns_theta_max         24.500
_diffrn_reflns_theta_min         1.910
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+1.6501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03418b2.cif
_cod_data_source_block           exp_10487
_cod_depositor_comments          'Adding full bibliography for 7130707.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130707
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C8, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C19(H19), C17(H17), C3(H3), C20(H20), C15(H15), C6(H6),
 C5(H5), C7(H7), C4(H4), C00V(H00V), C16(H16), C8(H8)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C13(H13A,H13B,H13C), C24(H24A,H24B,H24C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C), C25(H25A,H25B,H25C)
;
_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.608