Nickel(ii)-catalyzed C(sp<sup>2</sup>)-H sulfuration/annulation with elemental sulfur: selective access to benzoisothiazolones.
Guo, Jun-Ru; Gong, Jun-Fang; Song, Mao-Ping; Organic & biomolecular chemistry 17 (2019) 5029–5037; doi:10.1039/c9ob00449a

data_7156812
_publ_section_title
;
 Nickel(ii)-catalyzed C(sp<sup>2</sup>)-H sulfuration/annulation with
 elemental sulfur: selective access to benzoisothiazolones.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5029
_journal_page_last               5037
_journal_paper_doi               10.1039/c9ob00449a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C18 H17 N3 O S'
_chemical_formula_sum            'C18 H17 N3 O S'
_chemical_formula_weight         323.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-24 deposited with the CCDC.    2019-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                79.216(5)
_cell_angle_beta                 89.365(4)
_cell_angle_gamma                75.485(4)
_cell_formula_units_Z            8
_cell_length_a                   12.3938(4)
_cell_length_b                   14.5761(8)
_cell_length_c                   18.8153(11)
_cell_measurement_reflns_used    6668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7630
_cell_measurement_theta_min      4.2180
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_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
;
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)'
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_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -40.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -30.0000 29

  2 omega    0.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega -102.00  -48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -30.0000 54

  4 omega  -59.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 55

  5 omega   60.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 27

  6 omega    2.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 33

  7 omega   61.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  8 omega   -2.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 75

  9 omega   59.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 47

 10 omega   64.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 46

 11 omega   58.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 50

 12 omega   59.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   90.0000 26

 13 omega   26.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 30

 14 omega   38.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 26

 15 omega   45.00   72.00   1.0000    1.5000
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    -       36.4734  -99.0000  -90.0000 27

 16 omega   15.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 87

 17 omega  -35.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  120.0000 48

 18 omega   15.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 27

 19 omega   67.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 26

 20 omega   69.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 39

 21 omega   14.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 27

 22 omega   15.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734    0.0000  120.0000 26

 23 omega   76.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 26

 24 omega   47.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 61

 25 omega   41.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 44

 26 omega   41.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 25

 27 omega   39.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 48

 28 omega   40.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 56

 29 omega   48.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 62

 30 omega   37.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 34

 31 omega   40.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 73

 32 omega   39.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 69

 33 omega   91.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 86

 34 omega   46.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 46

 35 omega  129.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 39

 36 omega  137.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 33

 37 omega   41.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 38 omega   88.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 26

 39 omega   55.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 32

 40 omega   45.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 26

 41 omega   44.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000    0.0000 134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0164601000
_diffrn_orient_matrix_UB_12      0.1007787000
_diffrn_orient_matrix_UB_13      -0.0480336000
_diffrn_orient_matrix_UB_21      -0.0223006000
_diffrn_orient_matrix_UB_22      -0.0410734000
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_diffrn_orient_matrix_UB_31      -0.1254654000
_diffrn_orient_matrix_UB_32      0.0228997000
_diffrn_orient_matrix_UB_33      0.0149112000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24480
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81397
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.480
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_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     841
_refine_ls_number_reflns         11514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0787
_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^)+(0.0802P)^2^+6.5800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8902
_reflns_number_total             11514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00449a2.cif
_cod_data_source_block           201809358
_cod_depositor_comments          'Adding full bibliography for 7156812.cif.'
_cod_original_cell_volume        3230.2(3)
_cod_database_code               7156812
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.796
_shelx_estimated_absorpt_t_min   0.721
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C14B(H14B), C15B(H15B),
 C16B(H16B), C17B(H17B), C1C(H1C), C2C(H2C), C3C(H3C), C4C(H4C), C14C(H14C),
 C15C(H15C), C16C(H16C), C17C(H17C)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C9A(H9AA,H9AB,
 H9AC), C10A(H10D,H10E,H10F), C18A(H18D,H18E,H18F), C9B(H9BA,H9BB,H9BC),
 C10B(H10G,H10H,H10I), C18B(H18G,H18H,H18I), C9C(H9CA,H9CB,H9CC), C10C(H10J,
 H10K,H10L), C18C(H18J,H18K,H18L)
;
_olex2_submission_special_instructions 'No special instructions were received'