Synthesis of dibenzothiazines from sulfides by one-pot N,O-transfer and intramolecular C–H amination
Ma, Yan-Na; Guo, Chen-Yang; Zhao, Qianyi; Zhang, Jie; Chen, Xuenian; Green Chemistry 20 (2018) 2953–; doi:10.1039/C8GC01057A

data_7230705
_publ_section_title
;
 Synthesis of dibenzothiazines from sulfides by one-pot N,O-transfer and
 intramolecular C--H amination
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              2953
_journal_paper_doi               10.1039/C8GC01057A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C13 H10 Cl N O S'
_chemical_formula_sum            'C13 H10 Cl N O S'
_chemical_formula_weight         263.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-02 deposited with the CCDC.
2018-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.484(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4863(2)
_cell_length_b                   9.6208(2)
_cell_length_c                   12.3830(2)
_cell_measurement_reflns_used    4127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2030
_cell_measurement_theta_min      4.7380
_cell_volume                     1162.48(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -89.00  -2.00   1.00    1.77    --  -36.07 125.00 120.00   87
  2  \w     17.00 105.00   1.00    1.77    --   36.07  38.00 120.00   88
  3  \w     19.00 103.00   1.00    1.77    --   36.07  57.00-120.00   84
  4  \w     19.00 103.00   1.00    1.77    --   36.07  57.00   0.00   84
  5  \w      9.00 104.00   1.00    1.77    --   36.07  77.00 120.00   95
  6  \w     23.00  89.00   1.00    1.77    --   36.07-125.00 -90.00   66
  7  \w     23.00  89.00   1.00    1.77    --   36.07-125.00 150.00   66
  8  \w     39.00 116.00   1.00    7.06    --  109.31-111.00 -90.00   77
  9  \w     41.00 127.00   1.00    7.06    --  109.31 -45.00  30.00   86
 10  \w     40.00 109.00   1.00    7.06    --  109.31 -95.00  60.00   69
 11  \w     83.00 177.00   1.00    7.06    --  109.31  77.00  30.00   94
 12  \w     40.00 109.00   1.00    7.06    --  109.31 -95.00 -60.00   69
 13  \w     42.00 127.00   1.00    7.06    --  109.31 -61.00  90.00   85
 14  \w     42.00 136.00   1.00    7.06    --  109.31 -77.00 -90.00   94
 15  \w     40.00 178.00   1.00    7.06    --  109.31   0.00   0.00  138
 16  \w    -31.00  41.00   1.00    1.77    --   36.07 -57.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0128688000
_diffrn_orient_matrix_UB_12      0.1429406000
_diffrn_orient_matrix_UB_13      -0.0511977000
_diffrn_orient_matrix_UB_21      0.0776157000
_diffrn_orient_matrix_UB_22      -0.0677974000
_diffrn_orient_matrix_UB_23      -0.0706303000
_diffrn_orient_matrix_UB_31      -0.1368372000
_diffrn_orient_matrix_UB_32      -0.0249137000
_diffrn_orient_matrix_UB_33      -0.1013140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.391
_diffrn_reflns_theta_min         4.746
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.426
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0454
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2023
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01057a2.cif
_cod_data_source_block           myn20180124
_cod_depositor_comments          'Adding full bibliography for 7230705.cif.'
_cod_database_code               7230705
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'Cl1 C1 N1 O1 H1 '
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.472