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_7132172
_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_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 N O2 S'
_chemical_formula_sum            'C22 H19 N O2 S'
_chemical_formula_weight         361.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-30 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.376(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2972(15)
_cell_length_b                   7.4805(5)
_cell_length_c                   17.3374(16)
_cell_measurement_reflns_used    5083
_cell_measurement_temperature    302.9(2)
_cell_measurement_theta_max      30.9160
_cell_measurement_theta_min      2.4540
_cell_volume                     1893.4(3)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.9(2)
_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 0.804
_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    -28.00  65.00   0.50    8.21    --   -6.19   6.00 -49.00  186
  2  \w    -54.00 -27.00   0.50    8.21    --   -6.19  -6.00 133.00   54
  3  \w    -14.00  36.00   0.50    8.21    --    4.00 -99.00 150.00  100
  4  \w     28.00  59.00   0.50    8.21    --    4.00  37.00  90.00   62
  5  \w    -74.00   7.00   0.50    8.21    --   -6.19 -57.00 -60.00  162
;
_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      -0.0388981000
_diffrn_orient_matrix_UB_12      0.0063120000
_diffrn_orient_matrix_UB_13      0.0141467000
_diffrn_orient_matrix_UB_21      0.0291788000
_diffrn_orient_matrix_UB_22      0.0063556000
_diffrn_orient_matrix_UB_23      0.0402923000
_diffrn_orient_matrix_UB_31      0.0005974000
_diffrn_orient_matrix_UB_32      0.0943458000
_diffrn_orient_matrix_UB_33      -0.0036612000
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17540
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.778
_diffrn_reflns_theta_min         2.440
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29238
_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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7899
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0949
_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^)+(0.1746P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2786
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                4330
_reflns_number_total             7899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03745b2.cif
_cod_data_source_block           wangyil_0627_auto
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H38 N2 O4 S2'
_cod_original_formula_weight         722.88
_cod_original_formula_moiety         '2(C22 H19 N O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7132172
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.83
_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:
 C14(H14), C32(H32), C38(H38), C42(H42)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C16(H16), C24(H24), C25(H25), C28(H28), C29(H29), C31(H31),
 C33(H33), C35(H35), C36(H36), C37(H37), C39(H39), C41(H41), C2(H2), C5(H5),
 C7(H7), C11(H11), C15(H15), C17(H17), C19(H19), C21(H21), C22(H22), C26(H26),
 C27(H27), C30(H30), C40(H40), C43(H43)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              36549
_shelx_hkl_checksum              22587
_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 2.285
_oxdiff_exptl_absorpt_empirical_full_min 0.620