Transition metal-free α-C<sub>sp<sup>3</sup></sub>-H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides.
Qiao, Mengjun; Zhang, Jinli; Chen, Ling; Zhou, Fengyi; Zhang, Yali; Zhou, Lingfei; Wu, Yangjie; Organic & biomolecular chemistry 17 (2019) 3790–3796; doi:10.1039/c9ob00336c

data_7156734
_publ_section_title
;
 Transition metal-free \a-C<sub>sp<sup>3</sup></sub>-H oxidative
 sulfuration of benzyl thiosulfates with anilines to form N-aryl
 thioamides.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3790
_journal_page_last               3796
_journal_paper_doi               10.1039/c9ob00336c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 F3 N S'
_chemical_formula_sum            'C14 H10 F3 N S'
_chemical_formula_weight         281.29
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-03-15
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2018-04-23 deposited with the CCDC.    2019-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.101(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5721(6)
_cell_length_b                   12.8938(8)
_cell_length_c                   7.9189(4)
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6110
_cell_measurement_theta_min      4.8200
_cell_volume                     1331.42(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -87.00  -46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 41

  2 omega  -49.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 84

  3 omega   11.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 64

  4 omega  -28.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  120.0000 59

  5 omega   75.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 35

  6 omega    7.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  -60.0000 66

  7 omega   18.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 54

  8 omega   39.00  133.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 94

  9 omega  111.00  153.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 42

 10 omega   42.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 72

 11 omega   45.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 46

 12 omega   99.00  176.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 77

 13 omega   41.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  136.0000 28

 14 omega   80.00  160.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 80

 15 omega   37.00   88.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0372534000
_diffrn_orient_matrix_UB_12      0.1083222000
_diffrn_orient_matrix_UB_13      -0.0372337000
_diffrn_orient_matrix_UB_21      -0.1058652000
_diffrn_orient_matrix_UB_22      0.0222737000
_diffrn_orient_matrix_UB_23      -0.1283360000
_diffrn_orient_matrix_UB_31      -0.0367870000
_diffrn_orient_matrix_UB_32      0.0455757000
_diffrn_orient_matrix_UB_33      0.1518792000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0610
_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^)+(0.1080P)^2^+0.2845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1834
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00336c2.cif
_cod_data_source_block           201803177
_cod_depositor_comments          'Adding full bibliography for 7156734.cif.'
_cod_database_code               7156734
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H20N2O8S1
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.661
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C8-F1
 1.4 with sigma of 0.02
 C8-F3A
 1.4 with sigma of 0.02
 C8-F2
 1.4 with sigma of 0.02
 C8-F1A
 1.4 with sigma of 0.02
 C8-F3
 1.4 with sigma of 0.02
 C8-F2A
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'