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_7132167
_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 unk
_chemical_formula_moiety         'C21 H17 N O2 S'
_chemical_formula_sum            'C21 H17 N O2 S'
_chemical_formula_weight         347.41
_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     dual
_audit_creation_date             2023-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-06-13 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.140(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7591(3)
_cell_length_b                   7.23760(10)
_cell_length_c                   17.3492(3)
_cell_measurement_reflns_used    9495
_cell_measurement_temperature    295.50(11)
_cell_measurement_theta_max      76.0670
_cell_measurement_theta_min      2.8050
_cell_volume                     1776.42(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.50(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.946
_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     21.00 114.00   0.50    0.05    --   44.32   8.00 -36.00  186
  2  \w    132.00 173.00   0.50    0.05    --  109.62 125.00-150.00   82
  3  \w     79.00 110.00   0.50    0.05    --  109.62 125.00-150.00   62
  4  \w     98.00 156.00   0.50    0.05    --  109.62   8.00 -36.00  116
  5  \w     60.00  88.00   0.50    0.05    --  109.62   8.00 -36.00   56
  6  \w     41.00 111.00   0.50    0.05    --  109.62-125.00 150.00  140
  7  \w     36.00 107.00   0.50    0.05    --  109.62-125.00 120.00  142
  8  \w     37.00  62.00   0.50    0.05    --  109.62 -61.00 120.00   50
  9  \w     39.00  68.00   0.50    0.05    --  109.62 -61.00  30.00   58
 10  \w     39.00  65.00   0.50    0.05    --  109.62 -61.00   0.00   52
 11  \w     36.00  61.00   0.50    0.05    --  109.62 -61.00 -30.00   50
 12  \w     41.00  67.00   0.50    0.05    --  109.62 -61.00-180.00   52
 13  \w    -27.00  34.00   0.50    0.05    --   44.32 -37.00   0.00  122
 14  \w    -22.00   3.00   0.50    0.05    --  -44.32   8.00 -36.00   50
 15  \w    -29.00  -4.00   0.50    0.05    --   44.32  -8.00 148.00   50
 16  \w     43.00  68.00   0.50    0.05    --  109.62 -61.00 150.00   50
 17  \w   -147.00 -60.00   0.50    0.05    -- -100.00  -8.00 148.00  174
 18  \w   -120.00 -16.00   0.50    0.05    --  -44.32  -8.00 148.00  208
 19  \w    -53.00 -28.00   0.50    0.05    -- -100.00  61.00 150.00   50
 20  \w   -103.00 -69.00   0.50    0.05    -- -100.00  77.00  90.00   68
 21  \w    -73.00 -44.00   0.50    0.05    -- -100.00  61.00  30.00   58
 22  \w    -52.00 -26.00   0.50    0.05    -- -100.00  45.00   0.00   52
 23  \w    -52.00 -25.00   0.50    0.05    -- -100.00  45.00 -90.00   54
 24  \w   -121.00 -82.00   0.50    0.05    --  -44.32 179.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237521000
_diffrn_orient_matrix_UB_12      0.0124153000
_diffrn_orient_matrix_UB_13      0.0960327000
_diffrn_orient_matrix_UB_21      0.1057142000
_diffrn_orient_matrix_UB_22      0.0187989000
_diffrn_orient_matrix_UB_23      0.0225180000
_diffrn_orient_matrix_UB_31      -0.0107603000
_diffrn_orient_matrix_UB_32      0.2116197000
_diffrn_orient_matrix_UB_33      -0.0076569000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10993
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.691
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.265
_diffrn_reflns_theta_min         3.124
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5123
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0787P)^2^+0.2709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.459
_reflns_Friedel_fraction_full    0.487
_reflns_Friedel_fraction_max     0.435
_reflns_number_gt                4779
_reflns_number_total             5123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03745b2.cif
_cod_data_source_block           wangyilin-lych_0302_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            'C42 H34 N2 O4 S2'
_cod_original_formula_weight         694.83
_cod_original_formula_moiety         '2(C21 H17 N O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7132167
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.04
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C16(H16), C18(H18), C25(H25), C27(H27), C28(H28), C30(H30),
 C31(H31), C32(H32), C35(H35), C36(H36), C40(H40), C42(H42), C5(H5), C9(H9),
 C10(H10), C11(H11), C14(H14), C17(H17), C21(H21), C22(H22), C24(H24), C29(H29),
  C34(H34), C37(H37), C38(H38), C41(H41)
;
_shelx_res_checksum              92885
_shelx_hkl_checksum              90536
_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.414