Synthesis of benzo[<i>f</i>][1,2]thiazepine 1,1-dioxides based on the visible-light-mediated aza Paternò-Büchi reaction of benzo[<i>d</i>]isothiazole 1,1-dioxides with alkenes.
Wang, Yi-Lin; Liu, Peng-Xiang; Zhang, Huan-Huan; Xu, Peng-Fei; Luo, Yong-Chun; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc03745b

data_7132171
_publ_section_title
;
 Synthesis of benzo[<i>f</i>][1,2]thiazepine 1,1-dioxides based on the
 visible-light-mediated aza Patern&#xf2;-B&#xfc;chi reaction of
 benzo[<i>d</i>]isothiazole 1,1-dioxides with alkenes.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc03745b
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 N O2 S'
_chemical_formula_sum            'C22 H19 N O2 P S0.25'
_chemical_formula_weight         368.37
_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             2023-06-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-30 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.352(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6492(2)
_cell_length_b                   17.3276(5)
_cell_length_c                   12.0342(3)
_cell_measurement_reflns_used    11283
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.6100
_cell_measurement_theta_min      2.0660
_cell_volume                     1795.70(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.803
_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    -22.00  41.00   0.50    0.58    --    4.00  86.00  33.00  126
  2  \w    -20.00  63.00   0.50    0.58    --   -6.19  57.00-120.00  166
  3  \w     25.00  73.00   0.50    0.58    --    4.00  37.00-180.00   96
  4  \w    -33.00   5.00   0.50    0.58    --    4.00 -86.00 -84.00   76
  5  \w    -16.00  37.00   0.50    0.58    --    4.00 -99.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0230039000
_diffrn_orient_matrix_UB_12      -0.0330163000
_diffrn_orient_matrix_UB_13      -0.0291576000
_diffrn_orient_matrix_UB_21      -0.0352671000
_diffrn_orient_matrix_UB_22      0.0155836000
_diffrn_orient_matrix_UB_23      -0.0506680000
_diffrn_orient_matrix_UB_31      0.0707863000
_diffrn_orient_matrix_UB_32      0.0185146000
_diffrn_orient_matrix_UB_33      -0.0093399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.766
_diffrn_reflns_theta_min         2.066
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0404P)^2^+0.7240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3806
_reflns_number_total             4511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03745b2.cif
_cod_data_source_block           wangyil_0615_auto
_cod_original_cell_volume        1795.71(9)
_cod_database_code               7132171
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_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 Ternary CH refined with riding coordinates:
 C00A(H00A), C00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00J(H00L), C00K(H00M), C00L(H00N), C00M(H00O), C00N(H00P), C00O(H00Q),
 C00P(H00R), C00Q(H00S)
2.c Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K)
;
_shelx_res_checksum              68361
_shelx_hkl_checksum              70624
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.672