Cu(II)-Mediated C-S/N-S Bond Formation via C-H Activation: Access to Benzoisothiazolones Using Elemental Sulfur.
Chen, Fa-Jie; Liao, Gang; Li, Xin; Wu, Jun; Shi, Bing-Feng; Organic letters 16 (2014) 5644–5647; doi:10.1021/ol5027156

data_1518048
_publ_section_title
;
 Cu(II)-Mediated C-S/N-S Bond Formation via C-H Activation: Access to
 Benzoisothiazolones Using Elemental Sulfur.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5644
_journal_page_last               5647
_journal_paper_doi               10.1021/ol5027156
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H14 N2 O S'
_chemical_formula_sum            'C15 H14 N2 O S'
_chemical_formula_weight         270.34
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.062(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0001(11)
_cell_length_b                   11.6331(9)
_cell_length_c                   10.9008(12)
_cell_measurement_reflns_used    1271
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      29.5274
_cell_measurement_theta_min      3.2806
_cell_volume                     1301.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0608538000
_diffrn_orient_matrix_UB_12      0.0073167000
_diffrn_orient_matrix_UB_13      0.0519477000
_diffrn_orient_matrix_UB_21      -0.0159103000
_diffrn_orient_matrix_UB_22      -0.0448975000
_diffrn_orient_matrix_UB_23      0.0355940000
_diffrn_orient_matrix_UB_31      0.0285960000
_diffrn_orient_matrix_UB_32      -0.0406006000
_diffrn_orient_matrix_UB_33      -0.0300093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5028
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                1779
_reflns_number_total             2371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5027156_si_003.cif
_cod_data_source_block           140507_lx1_176_10a
_cod_depositor_comments          'Adding full bibliography for 1518048.cif.'
_cod_database_code               1518048
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;