One-Pot Synthesis of Iodo-Dibenzothiazines from 2-Biaryl Sulfides.
Ma, Yan-Na; Bian, Yajing; Liu, Xin; Zhang, Jie; Chen, Xuenian; The Journal of organic chemistry 84 (2019) 450–457; doi:10.1021/acs.joc.8b02729

data_4035893
_publ_section_title
;
 One-Pot Synthesis of Iodo-Dibenzothiazines from 2-Biaryl Sulfides.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              450
_journal_page_last               457
_journal_paper_doi               10.1021/acs.joc.8b02729
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H11 I2 N O S'
_chemical_formula_sum            'C14 H11 I2 N O S'
_chemical_formula_weight         495.10
_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             2018-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.157(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4188(3)
_cell_length_b                   5.00910(10)
_cell_length_c                   20.2178(3)
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8300
_cell_measurement_theta_min      4.4080
_cell_volume                     1541.61(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.977
_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   -105.00 -17.00   1.00    1.00    --  -35.50 -38.00 -60.00   88
  2  \w   -105.00 -17.00   1.00    1.00    --  -35.50 -38.00-150.00   88
  3  \w     19.00 103.00   1.00    1.00    --   35.50  57.00-180.00   84
  4  \w     23.00  89.00   1.00    1.00    --   35.50-125.00   0.00   66
  5  \w     23.00  89.00   1.00    1.00    --   35.50-125.00 -60.00   66
  6  \w    -36.00  65.00   1.00    1.00    --   35.50 -19.00-150.00  101
  7  \w    -32.00  52.00   1.00    1.00    --   35.50 -57.00-150.00   84
  8  \w      9.00 103.00   1.00    1.00    --   35.50  77.00 -60.00   94
  9  \w     39.00 109.00   1.00    2.40    --  108.69 -95.00-120.00   70
 10  \w     39.00 130.00   1.00    2.40    --  108.69 -30.00 150.00   91
 11  \w     39.00 114.00   1.00    2.40    --  108.69-115.00  52.00   75
 12  \w     70.00 178.00   1.00    2.40    --  108.69  15.00-120.00  108
 13  \w     39.00 130.00   1.00    2.40    --  108.69 -30.00-120.00   91
 14  \w     91.00 176.00   1.00    2.40    --  108.69  61.00 -60.00   85
 15  \w     39.00 109.00   1.00    2.40    --  108.69 -95.00  90.00   70
 16  \w   -103.00  -9.00   1.00    1.00    --  -35.50 -77.00  60.00   94
 17  \w   -106.00 -43.00   1.00    1.00    --  -35.50-168.00 -91.00   63
 18  \w    -32.00  62.00   1.00    1.00    --   35.50 -77.00 120.00   94
 19  \w      1.00  74.00   1.00    1.00    --   35.50 -99.00 120.00   73
;
_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      0.0947593000
_diffrn_orient_matrix_UB_12      0.1081744000
_diffrn_orient_matrix_UB_13      0.0098434000
_diffrn_orient_matrix_UB_21      -0.0097766000
_diffrn_orient_matrix_UB_22      0.0603338000
_diffrn_orient_matrix_UB_23      -0.0755570000
_diffrn_orient_matrix_UB_31      -0.0343461000
_diffrn_orient_matrix_UB_32      0.2812581000
_diffrn_orient_matrix_UB_33      0.0123865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8835
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.085
_diffrn_reflns_theta_min         4.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    33.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.142
_refine_diff_density_min         -1.738
_refine_diff_density_rms         0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0598
_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^)+(0.1021P)^2^+0.5992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02729_si_002.cif
_cod_data_source_block           myn-20180731
_cod_database_code               4035893
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 H1 O1 S1 I1'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 6.702
_oxdiff_exptl_absorpt_empirical_full_min 0.453