#------------------------------------------------------------------------------
#$Date: 2025-11-29 23:14:50 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303962 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/08/7160819.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_7160819
loop_
_publ_author_name
'Solodyankina, Olga V.'
'Baykova, Svetlana O.'
'Baykov, Sergey V.'
'Togyzbayeva, Nurila'
'Zhussupova, Leilya'
'Novikov, Mikhail S.'
'Turmanov, Rakhymzhan'
'Boyarskiy, Vadim P.'
_publ_section_title
;
 Access to 4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4H)-ones
 via an amidoxime O-heteroarylation/cyclization reaction sequence.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10398
_journal_page_last               10407
_journal_paper_doi               10.1039/d5ob01387a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C13 H8 Cl N3 O2 S'
_chemical_formula_sum            'C13 H8 Cl N3 O2 S'
_chemical_formula_weight         305.73
_chemical_name_systematic
3-(3-chlorophenyl)-4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.245(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.1298(12)
_cell_length_b                   6.4573(2)
_cell_length_c                   8.0989(3)
_cell_measurement_reflns_used    6586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3360
_cell_measurement_theta_min      3.5690
_cell_volume                     1293.67(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(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 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  24.00   1.00    2.00    --  -47.14  52.00 142.00   47
  2  ω    -95.00 -44.00   1.00    2.00    --  -47.14 -52.00  -2.00   51
  3  ω     17.00  52.00   1.00    2.00    --   47.14 -52.00  -2.00   35
  4  ω     36.00 119.00   1.00    2.00    --   47.14  52.00 142.00   83
  5  ω   -176.00 -93.00   1.00    8.00    -- -106.00 -52.00  -2.00   83
  6  ω    -59.00 -34.00   1.00    8.00    -- -106.00  52.00 142.00   25
  7  ω    115.00 140.00   1.00    8.00    --  113.25  52.00 142.00   25
  8  ω    -40.00  26.00   1.00    2.00    --  -47.14  37.00 -60.00   66
  9  ω    -25.00  23.00   1.00    2.00    --  -47.14  19.00 -60.00   48
 10  ω     60.00  85.00   1.00    2.00    --   47.14  19.00   0.00   25
 11  ω    -26.00  13.00   1.00    2.00    --   47.14 -19.00   0.00   39
 12  ω    -70.00 -34.00   1.00    8.00    -- -106.00  61.00 -90.00   36
 13  ω    -92.00 -41.00   1.00    8.00    -- -106.00  77.00  60.00   51
 14  ω    -71.00 -35.00   1.00    8.00    -- -106.00  77.00-180.00   36
 15  ω   -149.00 -95.00   1.00    8.00    -- -106.00 -45.00 -90.00   54
 16  ω    -63.00 -36.00   1.00    8.00    -- -106.00  61.00 -30.00   27
 17  ω    -69.00 -36.00   1.00    8.00    -- -106.00  61.00-120.00   33
 18  ω    -69.00 -41.00   1.00    8.00    -- -106.00  61.00 120.00   28
 19  ω    -63.00 -37.00   1.00    8.00    -- -106.00  61.00 -60.00   26
 20  ω   -176.00 -92.00   1.00    8.00    -- -106.00 -61.00  90.00   84
 21  ω    -71.00 -46.00   1.00    8.00    -- -106.00  61.00-180.00   25
 22  ω    102.00 163.00   1.00    8.00    --  113.25  30.00-180.00   61
 23  ω     43.00  94.00   1.00    8.00    --  113.25 -77.00-120.00   51
 24  ω     42.00  67.00   1.00    8.00    --  113.25 -61.00  30.00   25
 25  ω     45.00  70.00   1.00    8.00    --  113.25 -61.00 -30.00   25
 26  ω     43.00  68.00   1.00    8.00    --  113.25 -61.00-120.00   25
 27  ω     44.00 107.00   1.00    8.00    --  113.25-125.00-180.00   63
 28  ω    104.00 165.00   1.00    8.00    --  113.25  30.00  90.00   61
 29  ω    111.00 136.00   1.00    8.00    --  113.25  45.00-120.00   25
 30  ω    102.00 162.00   1.00    8.00    --  113.25  77.00-180.00   60
 31  ω     42.00  67.00   1.00    8.00    --  113.25 -61.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0566526000
_diffrn_orient_matrix_UB_12      0.0530830000
_diffrn_orient_matrix_UB_13      -0.0113020000
_diffrn_orient_matrix_UB_21      -0.0098287000
_diffrn_orient_matrix_UB_22      0.1419185000
_diffrn_orient_matrix_UB_23      -0.1634463000
_diffrn_orient_matrix_UB_31      -0.0239157000
_diffrn_orient_matrix_UB_32      -0.1842933000
_diffrn_orient_matrix_UB_33      -0.1291718000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.402
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0513
_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)+(0.0692P)²+1.9717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2537
_reflns_number_total             2716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01387a3.cif
_cod_data_source_block           105-003_end-088
_cod_depositor_comments
'Adding full bibliography for 7160818--7160821.cif.'
_cod_database_code               7160819
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H10ClN3O
_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   0.634
_shelx_estimated_absorpt_t_min   0.489
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Restrained distances
 C8A-C7A = C6A-C7A
 1.384 with sigma of 0.02
 C6A-C7A
 1.384 with sigma of 0.002
 C7A-C8A
 1.384 with sigma of 0.02
 C5-C6A
 1.384 with sigma of 0.002
 C6-C5
 1.384 with sigma of 0.001
 C3-C8A
 1.384 with sigma of 0.001
 C8-C3
 1.384 with sigma of 0.001
 C6-C7 = C7-C8
 1.384 with sigma of 0.001
 C8A-C7A
 1.384 with sigma of 0.001
2. Others
 Sof(C6)=Sof(H6)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=1-FVAR(1)
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C4(H4), C6(H6), C8(H8), C7(H7), C8A(H8A), C7A(H7A),
 C6A(H6A)
;
_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 2.508
_oxdiff_exptl_absorpt_empirical_full_min 0.438
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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 0.41576(2) 0.65290(9) -0.04863(8) 0.02728(18) Uani 1 1 d . . . . .
Cl1 Cl 0.16987(3) 0.62615(16) 0.03819(13) 0.0607(3) Uani 1 1 d . . . . .
O2 O 0.48175(7) 0.3196(3) 0.0731(2) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.39787(7) 0.1132(3) 0.1100(2) 0.0254(4) Uani 1 1 d . . . . .
N3 N 0.43234(8) 0.3035(3) 0.3794(3) 0.0260(4) Uani 1 1 d . . . . .
N2 N 0.39231(8) 0.3067(3) 0.0309(3) 0.0251(4) Uani 1 1 d . . . . .
N1 N 0.35296(8) 0.6180(3) -0.0563(3) 0.0302(5) Uani 1 1 d . . . . .
C9 C 0.41832(9) 0.1233(4) 0.3001(3) 0.0231(5) Uani 1 1 d . . . . .
C10 C 0.42150(9) -0.0667(4) 0.3838(3) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.408700 -0.209262 0.307002 0.030 Uiso 1 1 calc R U . . .
C1 C 0.43808(9) 0.4012(4) 0.0290(3) 0.0232(5) Uani 1 1 d . . . . .
C11 C 0.44190(9) -0.0636(4) 0.5703(3) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.445582 -0.206355 0.645202 0.032 Uiso 1 1 calc R U . . .
C2 C 0.34764(9) 0.4320(4) -0.0092(3) 0.0279(5) Uani 1 1 d . . . . .
C13 C 0.45243(10) 0.3016(4) 0.5631(3) 0.0286(5) Uani 1 1 d . . . . .
C12 C 0.45768(10) 0.1230(4) 0.6615(3) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.29655(11) 0.3547(4) -0.0045(4) 0.0404(7) Uani 1 1 d D . . . .
C4 C 0.26164(10) 0.5040(5) 0.0116(4) 0.0383(6) Uani 1 1 d . . . . .
H4 H 0.272533 0.666697 0.023246 0.046 Uiso 1 1 calc R U . . .
C5 C 0.21279(11) 0.4419(5) 0.0126(5) 0.0499(8) Uani 1 1 d D . . . .
C6 C 0.1957(2) 0.2397(6) -0.0337(12) 0.070(3) Uani 0.673(13) 1 d D . P A 2
H6 H 0.156046 0.193872 -0.044015 0.084 Uiso 0.673(13) 1 calc R U P A 2
C8 C 0.27860(19) 0.1539(5) -0.0539(13) 0.0557(19) Uani 0.673(13) 1 d D . P A 2
H8 H 0.304167 0.042884 -0.082157 0.067 Uiso 0.673(13) 1 calc R U P A 2
C7 C 0.2281(2) 0.0947(8) -0.0672(15) 0.077(3) Uani 0.673(13) 1 d D . P A 2
H7 H 0.214017 -0.063108 -0.103301 0.092 Uiso 0.673(13) 1 calc R U P A 2
H13 H 0.4647(12) 0.436(5) 0.619(4) 0.032(8) Uiso 1 1 d . . . . .
H12 H 0.4715(14) 0.133(5) 0.788(5) 0.045(9) Uiso 1 1 d . . . . .
C8A C 0.2877(3) 0.1547(6) 0.0386(14) 0.028(2) Uani 0.327(13) 1 d D . P A 1
H8A H 0.318962 0.039339 0.062756 0.034 Uiso 0.327(13) 1 calc R U P A 1
C7A C 0.2403(3) 0.0965(12) 0.0520(14) 0.030(2) Uani 0.327(13) 1 d D . P A 1
H7A H 0.232060 -0.066666 0.060090 0.036 Uiso 0.327(13) 1 calc R U P A 1
C6A C 0.2034(4) 0.2424(6) 0.0553(16) 0.031(2) Uani 0.327(13) 1 d D . P A 1
H6A H 0.169681 0.203500 0.088853 0.037 Uiso 0.327(13) 1 calc R U P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 S1 C1 94.79(11) . . ?
N2 O1 C9 112.53(17) . . ?
C9 N3 C13 115.8(2) . . ?
O1 N2 C1 118.27(18) . . ?
C2 N2 O1 123.82(19) . . ?
C2 N2 C1 116.2(2) . . ?
C2 N1 S1 110.30(17) . . ?
N3 C9 O1 118.9(2) . . ?
N3 C9 C10 126.9(2) . . ?
C10 C9 O1 114.2(2) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 C9 116.0(2) . . ?
C11 C10 H10 122.0 . . ?
O2 C1 S1 131.32(19) . . ?
O2 C1 N2 125.3(2) . . ?
N2 C1 S1 103.41(16) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
N2 C2 C3 122.3(2) . . ?
N1 C2 N2 115.0(2) . . ?
N1 C2 C3 122.7(2) . . ?
N3 C13 C12 122.8(2) . . ?
N3 C13 H13 114.0(18) . . ?
C12 C13 H13 123.1(18) . . ?
C11 C12 H12 123(2) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 118(2) . . ?
C4 C3 C2 116.5(2) . . ?
C8 C3 C2 121.8(3) . . ?
C8 C3 C4 120.2(3) . . ?
C8A C3 C2 125.4(3) . . ?
C8A C3 C4 115.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.4(2) . . ?
C6 C5 Cl1 120.8(3) . . ?
C6 C5 C4 119.1(4) . . ?
C6A C5 Cl1 114.0(3) . . ?
C6A C5 C4 123.0(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C3 C8A H8A 118.8 . . ?
C7A C8A C3 122.4(6) . . ?
C7A C8A H8A 118.8 . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A C8A 121.3(7) . . ?
C6A C7A H7A 119.4 . . ?
C5 C6A C7A 114.8(6) . . ?
C5 C6A H6A 122.6 . . ?
C7A C6A H6A 122.6 . . ?
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 N1 1.695(2) . ?
S1 C1 1.758(2) . ?
Cl1 C5 1.736(3) . ?
O2 C1 1.209(3) . ?
O1 N2 1.384(2) . ?
O1 C9 1.408(3) . ?
N3 C9 1.308(3) . ?
N3 C13 1.358(3) . ?
N2 C1 1.389(3) . ?
N2 C2 1.380(3) . ?
N1 C2 1.286(3) . ?
C9 C10 1.387(3) . ?
C10 H10 1.0850 . ?
C10 C11 1.380(3) . ?
C11 H11 1.0850 . ?
C11 C12 1.386(4) . ?
C2 C3 1.488(3) . ?
C13 C12 1.376(4) . ?
C13 H13 0.97(3) . ?
C12 H12 0.94(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.3853(10) . ?
C3 C8A 1.3846(10) . ?
C4 H4 1.0850 . ?
C4 C5 1.388(4) . ?
C5 C6 1.3848(10) . ?
C5 C6A 1.384(2) . ?
C6 H6 1.0850 . ?
C6 C7 1.3845(10) . ?
C8 H8 1.0850 . ?
C8 C7 1.3845(10) . ?
C7 H7 1.0850 . ?
C8A H8A 1.0850 . ?
C8A C7A 1.3843(10) . ?
C7A H7A 1.0850 . ?
C7A C6A 1.384(2) . ?
C6A H6A 1.0850 . ?
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 N1 C2 N2 -1.5(3) . . . . ?
S1 N1 C2 C3 -179.4(2) . . . . ?
Cl1 C5 C6 C7 175.4(6) . . . . ?
Cl1 C5 C6A C7A -174.3(6) . . . . ?
O1 N2 C1 S1 -171.16(15) . . . . ?
O1 N2 C1 O2 8.6(3) . . . . ?
O1 N2 C2 N1 169.8(2) . . . . ?
O1 N2 C2 C3 -12.3(4) . . . . ?
O1 C9 C10 C11 179.32(19) . . . . ?
N3 C9 C10 C11 -0.3(4) . . . . ?
N3 C13 C12 C11 0.0(4) . . . . ?
N2 O1 C9 N3 -3.9(3) . . . . ?
N2 O1 C9 C10 176.42(19) . . . . ?
N2 C2 C3 C4 159.6(3) . . . . ?
N2 C2 C3 C8 -34.5(6) . . . . ?
N2 C2 C3 C8A -0.2(7) . . . . ?
N1 S1 C1 O2 -176.0(2) . . . . ?
N1 S1 C1 N2 3.73(16) . . . . ?
N1 C2 C3 C4 -22.6(4) . . . . ?
N1 C2 C3 C8 143.3(5) . . . . ?
N1 C2 C3 C8A 177.6(6) . . . . ?
C9 O1 N2 C1 79.9(2) . . . . ?
C9 O1 N2 C2 -84.8(3) . . . . ?
C9 N3 C13 C12 -0.3(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C1 S1 N1 C2 -1.4(2) . . . . ?
C1 N2 C2 N1 4.8(3) . . . . ?
C1 N2 C2 C3 -177.3(2) . . . . ?
C2 N2 C1 S1 -5.3(2) . . . . ?
C2 N2 C1 O2 174.5(2) . . . . ?
C2 C3 C4 C5 178.6(3) . . . . ?
C2 C3 C8 C7 -172.8(6) . . . . ?
C2 C3 C8A C7A 175.6(6) . . . . ?
C13 N3 C9 O1 -179.12(19) . . . . ?
C13 N3 C9 C10 0.5(4) . . . . ?
C3 C4 C5 Cl1 178.4(2) . . . . ?
C3 C4 C5 C6 -11.1(6) . . . . ?
C3 C4 C5 C6A 21.0(7) . . . . ?
C3 C8 C7 C6 1.2(12) . . . . ?
C3 C8A C7A C6A -11.8(14) . . . . ?
C4 C3 C8 C7 -7.4(9) . . . . ?
C4 C3 C8A C7A 15.6(10) . . . . ?
C4 C5 C6 C7 5.1(9) . . . . ?
C4 C5 C6A C7A -15.8(11) . . . . ?
C5 C6 C7 C8 0.0(11) . . . . ?
C8 C3 C4 C5 12.4(6) . . . . ?
C8A C3 C4 C5 -19.6(6) . . . . ?
C8A C7A C6A C5 10.9(13) . . . . ?
