A rearrangement of saccharin-derived cyclic ketimines with 3-chlorooxindoles leading to spiro-1,3-benzothiazine oxindoles.
Li, Rui-Li; Fang, Qing-Yun; Li, Mei-Yuan; Wang, Xiang-Shan; Zhao, Li-Ming; Chemical communications (Cambridge, England) 57 (2021) 11322–11325; doi:10.1039/d1cc04179g

data_7129102
_publ_section_title
;
 A rearrangement of saccharin-derived cyclic ketimines with
 3-chlorooxindoles leading to spiro-1,3-benzothiazine oxindoles.
;
_journal_issue                   86
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11322
_journal_page_last               11325
_journal_paper_doi               10.1039/d1cc04179g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H14 N2 O3 S, C3 H6 O'
_chemical_formula_sum            'C24 H20 N2 O4 S'
_chemical_formula_weight         432.48
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-24 deposited with the CCDC.	2021-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.107(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7954(13)
_cell_length_b                   19.899(3)
_cell_length_c                   13.0118(18)
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.2920
_cell_measurement_theta_min      2.6280
_cell_volume                     2164.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -30.00  31.00   1.00    2.50    --  -16.43  19.00 -30.00   61
  2  \w    -52.00  20.00   1.00    2.50    --   15.65 -57.00-150.00   72
  3  \w     -9.00  20.00   1.00    2.50    --  -16.43 -99.00-120.00   29
  4  \w    -24.00  23.00   1.00    2.50    --  -16.43 -99.00  90.00   47
  5  \w     45.00  70.00   1.00    2.50    --   15.65 178.00 -90.00   25
  6  \w     53.00  88.00   1.00    2.50    --   15.65 178.00 120.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0044272000
_diffrn_orient_matrix_UB_12      0.0311363000
_diffrn_orient_matrix_UB_13      -0.0254168000
_diffrn_orient_matrix_UB_21      0.0022305000
_diffrn_orient_matrix_UB_22      0.0171717000
_diffrn_orient_matrix_UB_23      0.0482025000
_diffrn_orient_matrix_UB_31      0.0847458000
_diffrn_orient_matrix_UB_32      -0.0021074000
_diffrn_orient_matrix_UB_33      0.0178724000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10380
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.494
_diffrn_reflns_theta_max         24.494
_diffrn_reflns_theta_min         1.939
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0459P)^2^+0.7424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2098
_reflns_number_total             3596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04179g2.cif
_cod_data_source_block           exp_9468
_cod_depositor_comments          'Adding full bibliography for 7129102.cif.'
_cod_database_code               7129102
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C21(H21), C10(H10), C20(H20), C17(H17), C11(H11), C12(H12),
 C18(H18), C19(H19), C3(H3), C6(H6), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.787