Radical-mediated chemo-divergent recyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides: alkyl migration and dearomatization.
Nan, Jiang; Yang, Shuai; Huang, Guanjie; Fan, Liangxin; Chemical communications (Cambridge, England) 61 (2025) 5503–5506; doi:10.1039/d5cc00008d

data_7134310
_publ_section_title
;
 Radical-mediated chemo-divergent recyclization of
 1,2,3,4-benzothiatriazine-1,1-dioxides: alkyl migration and
 dearomatization.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5503
_journal_page_last               5506
_journal_paper_doi               10.1039/d5cc00008d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C30 H32 N2 O2 S2), C6 H14'
_chemical_formula_sum            'C66 H78 N4 O4 S4'
_chemical_formula_weight         1119.56
_chemical_name_systematic        ????1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                107.715(7)
_cell_angle_beta                 102.575(7)
_cell_angle_gamma                96.844(6)
_cell_formula_units_Z            1
_cell_length_a                   9.3937(16)
_cell_length_b                   12.665(2)
_cell_length_c                   14.285(3)
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    296.20
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.68
_cell_volume                     1548.3(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      296.20
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5408
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.267
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1613 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.7885.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1646
_refine_ls_R_factor_gt           0.1051
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2784
_refine_ls_wR_factor_ref         0.3333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3068
_reflns_number_total             5408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00008d2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7134308--7134310.cif.'
_cod_database_code               7134310
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.696(6)
 0.304(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C32-C31 = C33-C32 = C33-C33_$1
 1.54 with sigma of 0.001
 C24-C23 = C29-C28 = C9-C8 = C14-C13
 1.5 with sigma of 0.01
 C31-C33 = C33_$1-C32
 2.515 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C33 \\sim C32 \\sim C31: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C27(H27), C25(H25), C2(H2A), C3(H3), C4(H4), C5(H5), C20(H20),
  C19(H19), C18(H18), C17(H17), C12(H12), C10(H10)
5.c Fitted hexagon refined as free rotating group:
 C28(C27,C26,C25,C23,C22), C6(C1,C2,C3,C4,C5), C16(C21,C20,C19,C18,C17),
 C13(C12,C11,C10,C8,C7)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C15(H15A,H15B,H15C), C30(H30A,H30B,
 H30C), C9(H9A,H9B,H9C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              71945
_shelx_hkl_checksum              66322
_olex2_submission_special_instructions 'No special instructions were received'