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#$Date: 2025-04-05 04:59:28 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298741 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/43/7134309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134309
loop_
_publ_author_name
'Nan, Jiang'
'Yang, Shuai'
'Huang, Guanjie'
'Fan, Liangxin'
_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         'C13 H11 N O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-19
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.049(3)
_cell_length_b                   6.8887(17)
_cell_length_c                   11.412(3)
_cell_measurement_reflns_used    2557
_cell_measurement_temperature    293.30
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.71
_cell_volume                     1183.1(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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.30
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10423
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.707
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1098 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8061.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0528
_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/[σ²(Fo²)+(0.0304P)²+0.5829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1025
_reflns_number_total             1463
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc00008d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7134308--7134310.cif.'
_cod_original_cell_volume        1183.0(5)
_cod_database_code               7134309
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.963
_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. Others
 Fixed Sof: H7C(0.5) H7A(0.5) H7B(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C7(H7C,H7A,H7B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27665(5) 0.750000 0.61425(8) 0.0660(3) Uani 1 2 d S T P . .
O1 O 0.22696(12) 0.5734(4) 0.62526(16) 0.1003(8) Uani 1 1 d . . . . .
O2 O 0.63146(15) 0.750000 0.5861(3) 0.0915(10) Uani 1 2 d S T P . .
N1 N 0.47739(16) 0.750000 0.5676(2) 0.0498(6) Uani 1 2 d S T P . .
C1 C 0.5659(2) 0.750000 0.5261(3) 0.0618(9) Uani 1 2 d S T P . .
C2 C 0.5586(2) 0.750000 0.3984(3) 0.0648(9) Uani 1 2 d S T P . .
H2 H 0.606853 0.750000 0.347549 0.078 Uiso 1 2 calc R U P . .
C3 C 0.4748(2) 0.750000 0.3644(3) 0.0575(8) Uani 1 2 d S T P . .
C4 C 0.4413(4) 0.750000 0.2411(3) 0.0823(13) Uani 1 2 d S T P . .
H4A H 0.4059(18) 0.637(4) 0.223(3) 0.109(11) Uiso 1 1 d . . . . .
H4B H 0.493(3) 0.750000 0.197(4) 0.085(13) Uiso 1 2 d S . P . .
C5 C 0.4185(2) 0.750000 0.4709(3) 0.0502(7) Uani 1 2 d S T P . .
C6 C 0.3298(2) 0.750000 0.4785(3) 0.0570(8) Uani 1 2 d S T P . .
C7 C 0.2642(2) 0.750000 0.3785(3) 0.0850(13) Uani 1 2 d S T P . .
H7C H 0.207752 0.796254 0.405885 0.128 Uiso 0.5 1 calc R U P A -1
H7A H 0.257750 0.620371 0.348861 0.128 Uiso 0.5 1 calc R U P A -1
H7B H 0.285488 0.833375 0.317226 0.128 Uiso 0.5 1 calc R U P A -1
C8 C 0.3623(2) 0.750000 0.7165(3) 0.0558(8) Uani 1 2 d S T P . .
C9 C 0.3355(2) 0.750000 0.8332(3) 0.0755(11) Uani 1 2 d S T P . .
H9 H 0.275210 0.750000 0.851273 0.091 Uiso 1 2 calc R U P . .
C10 C 0.3967(3) 0.750000 0.9213(3) 0.0915(14) Uani 1 2 d S T P . .
H10 H 0.378820 0.750000 0.999302 0.110 Uiso 1 2 calc R U P . .
C11 C 0.4854(3) 0.750000 0.8925(3) 0.0857(13) Uani 1 2 d S T P . .
H11 H 0.527584 0.750000 0.952043 0.103 Uiso 1 2 calc R U P . .
C12 C 0.5132(2) 0.750000 0.7776(3) 0.0667(10) Uani 1 2 d S T P . .
H12 H 0.573661 0.750000 0.760606 0.080 Uiso 1 2 calc R U P . .
C13 C 0.4517(2) 0.750000 0.6865(3) 0.0492(7) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O1 116.1(2) 7_575 . ?
O1 S1 C6 108.50(10) . . ?
O1 S1 C6 108.50(10) 7_575 . ?
O1 S1 C8 109.13(10) 7_575 . ?
O1 S1 C8 109.13(10) . . ?
C8 S1 C6 104.86(15) . . ?
C1 N1 C5 109.2(3) . . ?
C13 N1 C1 125.5(3) . . ?
C13 N1 C5 125.3(2) . . ?
O2 C1 N1 125.6(3) . . ?
O2 C1 C2 129.1(3) . . ?
N1 C1 C2 105.2(3) . . ?
C1 C2 H2 124.3 . . ?
C3 C2 C1 111.5(3) . . ?
C3 C2 H2 124.3 . . ?
C2 C3 C4 126.8(4) . . ?
C2 C3 C5 107.8(3) . . ?
C5 C3 C4 125.4(4) . . ?
C3 C4 H4A 112.8(19) . . ?
C3 C4 H4A 112.8(19) . 7_575 ?
C3 C4 H4B 103(3) . . ?
H4A C4 H4A 107(4) . 7_575 ?
H4A C4 H4B 110(2) . . ?
H4B C4 H4A 110(2) . 7_575 ?
N1 C5 C3 106.3(3) . . ?
C6 C5 N1 125.1(3) . . ?
C6 C5 C3 128.6(3) . . ?
C5 C6 S1 121.0(2) . . ?
C5 C6 C7 127.1(3) . . ?
C7 C6 S1 111.8(2) . . ?
C6 C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7C C7 H7A 109.5 . . ?
H7C C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C9 C8 S1 115.3(3) . . ?
C13 C8 S1 123.5(2) . . ?
C13 C8 C9 121.1(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(4) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 N1 120.2(3) . . ?
C8 C13 C12 117.4(3) . . ?
C12 C13 N1 122.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.434(2) 7_575 ?
S1 O1 1.434(2) . ?
S1 C6 1.743(3) . ?
S1 C8 1.739(3) . ?
O2 C1 1.201(4) . ?
N1 C1 1.414(4) . ?
N1 C5 1.416(4) . ?
N1 C13 1.411(4) . ?
C1 C2 1.461(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.319(5) . ?
C3 C4 1.495(5) . ?
C3 C5 1.482(4) . ?
C4 H4A 0.97(3) . ?
C4 H4A 0.97(3) 7_575 ?
C4 H4B 0.93(4) . ?
C5 C6 1.337(4) . ?
C6 C7 1.509(4) . ?
C7 H7C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C8 C9 1.391(4) . ?
C8 C13 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.364(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C8 C9 C10 180.000(1) . . . . ?
S1 C8 C13 N1 0.000(1) . . . . ?
S1 C8 C13 C12 180.000(1) . . . . ?
O1 S1 C6 C5 116.50(10) 7_575 . . . ?
O1 S1 C6 C5 -116.50(10) . . . . ?
O1 S1 C6 C7 63.50(10) . . . . ?
O1 S1 C6 C7 -63.50(10) 7_575 . . . ?
O1 S1 C8 C9 -63.93(11) . . . . ?
O1 S1 C8 C9 63.93(11) 7_575 . . . ?
O1 S1 C8 C13 116.07(11) . . . . ?
O1 S1 C8 C13 -116.07(11) 7_575 . . . ?
O2 C1 C2 C3 180.000(1) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N1 C5 C6 S1 0.000(0) . . . . ?
N1 C5 C6 C7 180.000(0) . . . . ?
C1 N1 C5 C3 0.000(0) . . . . ?
C1 N1 C5 C6 180.000(0) . . . . ?
C1 N1 C13 C8 180.000(1) . . . . ?
C1 N1 C13 C12 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C1 C2 C3 C5 0.000(0) . . . . ?
C2 C3 C5 N1 0.000(0) . . . . ?
C2 C3 C5 C6 180.000(0) . . . . ?
C3 C5 C6 S1 180.000(0) . . . . ?
C3 C5 C6 C7 0.000(1) . . . . ?
C4 C3 C5 N1 180.000(0) . . . . ?
C4 C3 C5 C6 0.000(1) . . . . ?
C5 N1 C1 O2 180.000(1) . . . . ?
C5 N1 C1 C2 0.000(0) . . . . ?
C5 N1 C13 C8 0.000(1) . . . . ?
C5 N1 C13 C12 180.000(1) . . . . ?
C6 S1 C8 C9 180.000(1) . . . . ?
C6 S1 C8 C13 0.000(0) . . . . ?
C8 S1 C6 C5 0.000(0) . . . . ?
C8 S1 C6 C7 180.000(0) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C8 C13 N1 180.000(1) . . . . ?
C9 C8 C13 C12 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C11 C12 C13 N1 180.000(1) . . . . ?
C11 C12 C13 C8 0.000(1) . . . . ?
C13 N1 C1 O2 0.000(1) . . . . ?
C13 N1 C1 C2 180.000(0) . . . . ?
C13 N1 C5 C3 180.000(0) . . . . ?
C13 N1 C5 C6 0.000(1) . . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
