#------------------------------------------------------------------------------
#$Date: 2023-06-06 08:31:25 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022749.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022749
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Khrustalev, Victor N.'
'Akkurt, Mehmet'
'Khalilov, Ali N.'
'Bhattarai, Ajaya'
'Kerimli, Fuad Sh.'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1,6-diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_journal_coeditor_code           TX2066
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              494
_journal_page_last               498
_journal_paper_doi               10.1107/S2056989023003237
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C11 H7 N5 O S'
_chemical_formula_moiety         'C11 H7 N5 O S'
_chemical_formula_sum            'C11 H7 N5 O S'
_chemical_formula_weight         257.28
_chemical_name_systematic
;
1,6-Diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90.9441(9)
_cell_angle_beta                 104.1197(10)
_cell_angle_gamma                111.7451(10)
_cell_formula_units_Z            4
_cell_length_a                   8.94782(10)
_cell_length_b                   9.03908(9)
_cell_length_c                   14.87299(18)
_cell_measurement_reflns_used    26181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.78
_cell_measurement_theta_min      3.06
_cell_volume                     1075.92(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32558
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.279
_diffrn_reflns_theta_min         3.086
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.457
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.046P)²+1.11P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                4467
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2066sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022749.cif.'
_cod_database_code               2022749
_cod_database_fobs_code          2022749
_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_min   0.557
_shelx_estimated_absorpt_t_max   0.619
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.42276(5) 0.52922(6) 0.09865(3) 0.02122(13) Uani d 1 . .
O O1 0.79462(15) 0.40083(16) 0.42272(9) 0.0213(3) Uani d 1 . .
N N1 0.96105(17) 0.46444(18) 0.32428(10) 0.0155(3) Uani d 1 . .
N N2 1.07380(19) 0.4068(2) 0.38163(11) 0.0204(3) Uani d 1 . .
H H2A 1.022(3) 0.306(3) 0.3791(16) 0.024 Uiso d 1 . .
H H2B 1.100(3) 0.458(3) 0.4416(17) 0.024 Uiso d 1 . .
N N3 0.44940(19) 0.4937(2) 0.33818(11) 0.0234(3) Uani d 1 . .
N N4 0.9777(2) 0.6738(2) 0.03594(12) 0.0287(4) Uani d 1 . .
N N5 1.14206(19) 0.5269(2) 0.23148(11) 0.0209(3) Uani d 1 . .
H H5A 1.166(3) 0.560(3) 0.1804(18) 0.025 Uiso d 1 . .
H H5B 1.208(3) 0.495(3) 0.2738(17) 0.025 Uiso d 1 . .
C C2 0.8182(2) 0.4562(2) 0.34957(12) 0.0167(3) Uani d 1 . .
C C3 0.7099(2) 0.5149(2) 0.28660(12) 0.0180(3) Uani d 1 . .
C C4 0.7451(2) 0.5773(2) 0.20585(12) 0.0178(3) Uani d 1 . .
C C5 0.8932(2) 0.5840(2) 0.18606(12) 0.0170(3) Uani d 1 . .
C C6 1.0017(2) 0.5258(2) 0.24648(12) 0.0168(3) Uani d 1 . .
C C7 0.5643(2) 0.5051(2) 0.31343(12) 0.0181(3) Uani d 1 . .
C C8 0.6340(2) 0.6391(2) 0.14265(12) 0.0175(3) Uani d 1 . .
C C9 0.6819(2) 0.7868(2) 0.10847(12) 0.0175(3) Uani d 1 . .
H H9 0.7933 0.8642 0.1235 0.021 Uiso calc 1 . .
C C10 0.5435(3) 0.8072(2) 0.04835(14) 0.0249(4) Uani d 1 . .
H H10 0.5523 0.9018 0.0193 0.030 Uiso calc 1 . .
C C11 0.3974(2) 0.6796(2) 0.03603(13) 0.0239(4) Uani d 1 . .
H H11 0.2935 0.6741 -0.0026 0.029 Uiso calc 1 . .
C C12 0.9363(2) 0.6369(2) 0.10243(13) 0.0202(4) Uani d 1 . .
S S2 0.80863(7) -0.08316(7) 0.72047(4) 0.02529(14) Uani d 0.9 A 1
S S2' 0.6895(15) -0.0343(17) 0.8718(3) 0.0314(5) Uani d 0.1 A 2
O O2 0.11544(15) -0.02340(16) 0.64254(9) 0.0214(3) Uani d 1 . .
N N6 0.31497(17) 0.12527(18) 0.57464(10) 0.0160(3) Uani d 1 . .
N N7 0.19787(19) 0.1759(2) 0.51471(11) 0.0193(3) Uani d 1 . .
H H7A 0.129(3) 0.094(3) 0.4695(17) 0.023 Uiso d 1 . .
H H7B 0.140(3) 0.197(3) 0.5497(16) 0.023 Uiso d 1 . .
N N8 0.2765(2) -0.1813(2) 0.82807(11) 0.0230(3) Uani d 1 . .
N N9 0.86800(19) 0.19394(19) 0.57542(11) 0.0213(3) Uani d 1 . .
N N10 0.4975(2) 0.25717(19) 0.48991(11) 0.0190(3) Uani d 1 . .
H H10A 0.424(3) 0.292(3) 0.4638(16) 0.023 Uiso d 1 . .
H H10B 0.591(3) 0.293(3) 0.4796(16) 0.023 Uiso d 1 . .
C C13 0.2627(2) 0.0251(2) 0.64097(12) 0.0174(3) Uani d 1 . .
C C14 0.3908(2) -0.0122(2) 0.70405(12) 0.0198(4) Uani d 1 . .
C C15 0.5502(2) 0.0312(2) 0.69219(12) 0.0194(4) Uani d 1 . .
C C16 0.5878(2) 0.1196(2) 0.61720(12) 0.0161(3) Uani d 1 . .
C C17 0.4699(2) 0.1710(2) 0.55950(12) 0.0164(3) Uani d 1 . .
C C18 0.3323(2) -0.1073(2) 0.77379(12) 0.0181(3) Uani d 1 . .
C C19 0.6737(2) -0.0168(2) 0.75586(11) 0.0189(3) Uani d 1 . .
C C20 0.6928(6) -0.0243(7) 0.84874(15) 0.0314(5) Uani d 0.9 A 1
H H20 0.6287 0.0068 0.8819 0.038 Uiso calc 0.9 A 1
C C21 0.8164(3) -0.0824(3) 0.89227(16) 0.0287(5) Uani d 0.9 A 1
H H21 0.8463 -0.0917 0.9571 0.034 Uiso calc 0.9 A 1
C C22 0.8866(3) -0.1231(3) 0.82943(14) 0.0211(4) Uani d 0.9 A 1
H H22 0.9689 -0.1681 0.8445 0.025 Uiso calc 0.9 A 1
C C20' 0.7887(14) -0.0522(15) 0.7247(13) 0.02529(14) Uani d 0.1 A 2
H H20A 0.7989 -0.0491 0.6626 0.030 Uiso calc 0.1 A 2
C C21' 0.891(2) -0.0945(14) 0.8000(13) 0.0211(4) Uani d 0.1 A 2
H H21A 0.9796 -0.1234 0.7924 0.025 Uiso calc 0.1 A 2
C C22' 0.8558(11) -0.0913(9) 0.8836(15) 0.0287(5) Uani d 0.1 A 2
H H22A 0.9139 -0.1166 0.9398 0.034 Uiso calc 0.1 A 2
C C23 0.7447(2) 0.1620(2) 0.59624(12) 0.0170(3) Uani d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C8 . . 91.74(9) ?
C6 N1 C2 . . 124.17(14) ?
C6 N1 N2 . . 116.35(13) ?
C2 N1 N2 . . 119.48(14) ?
N1 N2 H2A . . 106.5(16) ?
N1 N2 H2B . . 105.8(14) ?
H2A N2 H2B . . 111(2) ?
C6 N5 H5A . . 118.2(16) ?
C6 N5 H5B . . 119.1(15) ?
H5A N5 H5B . . 123(2) ?
O1 C2 N1 . . 118.98(15) ?
O1 C2 C3 . . 125.41(15) ?
N1 C2 C3 . . 115.61(14) ?
C4 C3 C7 . . 122.82(15) ?
C4 C3 C2 . . 122.37(15) ?
C7 C3 C2 . . 114.82(15) ?
C3 C4 C5 . . 118.57(15) ?
C3 C4 C8 . . 121.73(15) ?
C5 C4 C8 . . 119.68(15) ?
C4 C5 C6 . . 120.31(15) ?
C4 C5 C12 . . 123.03(15) ?
C6 C5 C12 . . 116.49(15) ?
N5 C6 N1 . . 117.64(15) ?
N5 C6 C5 . . 123.40(16) ?
N1 C6 C5 . . 118.96(15) ?
N3 C7 C3 . . 176.99(18) ?
C9 C8 C4 . . 126.08(16) ?
C9 C8 S1 . . 111.33(13) ?
C4 C8 S1 . . 122.57(13) ?
C8 C9 C10 . . 111.33(16) ?
C8 C9 H9 . . 124.3 ?
C10 C9 H9 . . 124.3 ?
C11 C10 C9 . . 113.81(17) ?
C11 C10 H10 . . 123.1 ?
C9 C10 H10 . . 123.1 ?
C10 C11 S1 . . 111.78(14) ?
C10 C11 H11 . . 124.1 ?
S1 C11 H11 . . 124.1 ?
N4 C12 C5 . . 175.40(18) ?
C22 S2 C19 . . 92.90(9) ?
C19 S2' C22' . . 91.8(9) ?
C17 N6 C13 . . 124.25(14) ?
C17 N6 N7 . . 117.12(14) ?
C13 N6 N7 . . 118.50(13) ?
N6 N7 H7A . . 108.6(15) ?
N6 N7 H7B . . 106.1(15) ?
H7A N7 H7B . . 110(2) ?
C17 N10 H10A . . 117.1(16) ?
C17 N10 H10B . . 121.3(16) ?
H10A N10 H10B . . 120(2) ?
O2 C13 N6 . . 119.40(15) ?
O2 C13 C14 . . 124.96(16) ?
N6 C13 C14 . . 115.63(15) ?
C15 C14 C18 . . 124.60(16) ?
C15 C14 C13 . . 122.10(16) ?
C18 C14 C13 . . 113.12(15) ?
C14 C15 C16 . . 118.19(15) ?
C14 C15 C19 . . 119.86(15) ?
C16 C15 C19 . . 121.94(15) ?
C17 C16 C15 . . 121.00(15) ?
C17 C16 C23 . . 116.69(15) ?
C15 C16 C23 . . 122.31(15) ?
N10 C17 N6 . . 117.38(15) ?
N10 C17 C16 . . 124.41(16) ?
N6 C17 C16 . . 118.18(15) ?
N8 C18 C14 . . 175.66(18) ?
C20 C19 C15 . . 126.3(2) ?
C20' C19 C15 . . 120.7(8) ?
C20' C19 S2' . . 113.7(9) ?
C15 C19 S2' . . 125.6(3) ?
C20 C19 S2 . . 109.75(18) ?
C15 C19 S2 . . 123.87(12) ?
C19 C20 C21 . . 114.3(3) ?
C19 C20 H20 . . 122.8 ?
C21 C20 H20 . . 122.8 ?
C22 C21 C20 . . 111.4(2) ?
C22 C21 H21 . . 124.3 ?
C20 C21 H21 . . 124.3 ?
C21 C22 S2 . . 111.52(17) ?
C21 C22 H22 . . 124.2 ?
S2 C22 H22 . . 124.2 ?
C19 C20' C21' . . 109.0(15) ?
C19 C20' H20A . . 125.5 ?
C21' C20' H20A . . 125.5 ?
C22' C21' C20' . . 116(2) ?
C22' C21' H21A . . 121.9 ?
C20' C21' H21A . . 121.9 ?
C21' C22' S2' . . 109.3(16) ?
C21' C22' H22A . . 125.3 ?
S2' C22' H22A . . 125.3 ?
N9 C23 C16 . . 177.12(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . 1.713(2) ?
S1 C8 . 1.7239(18) ?
O1 C2 . 1.237(2) ?
N1 C6 . 1.362(2) ?
N1 C2 . 1.395(2) ?
N1 N2 . 1.4148(19) ?
N2 H2A . 0.85(3) ?
N2 H2B . 0.93(2) ?
N3 C7 . 1.145(2) ?
N4 C12 . 1.151(2) ?
N5 C6 . 1.325(2) ?
N5 H5A . 0.87(3) ?
N5 H5B . 0.88(3) ?
C2 C3 . 1.433(2) ?
C3 C4 . 1.391(2) ?
C3 C7 . 1.426(2) ?
C4 C5 . 1.406(2) ?
C4 C8 . 1.468(2) ?
C5 C6 . 1.412(2) ?
C5 C12 . 1.429(2) ?
C8 C9 . 1.388(3) ?
C9 C10 . 1.415(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.353(3) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
S2 C22 . 1.702(2) ?
S2 C19 . 1.7120(17) ?
S2' C19 . 1.711(3) ?
S2' C22' . 1.719(3) ?
O2 C13 . 1.232(2) ?
N6 C17 . 1.369(2) ?
N6 C13 . 1.397(2) ?
N6 N7 . 1.4192(19) ?
N7 H7A . 0.91(3) ?
N7 H7B . 0.88(2) ?
N8 C18 . 1.147(2) ?
N9 C23 . 1.153(2) ?
N10 C17 . 1.322(2) ?
N10 H10A . 0.85(2) ?
N10 H10B . 0.84(3) ?
C13 C14 . 1.442(2) ?
C14 C15 . 1.389(2) ?
C14 C18 . 1.432(2) ?
C15 C16 . 1.417(2) ?
C15 C19 . 1.471(2) ?
C16 C17 . 1.414(2) ?
C16 C23 . 1.427(2) ?
C19 C20 . 1.356(2) ?
C19 C20' . 1.360(3) ?
C20 C21 . 1.418(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.360(2) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C20' C21' . 1.420(3) ?
C20' H20A . 0.9500 ?
C21' C22' . 1.359(3) ?
C21' H21A . 0.9500 ?
C22' H22A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A O2 2_656 0.85(3) 2.37(3) 3.212(2) 174(2)
N2 H2B O1 2_766 0.93(2) 2.16(3) 3.086(2) 169(2)
N5 H5B N3 1_655 0.88(3) 2.14(3) 2.944(2) 151(2)
N7 H7A O2 2_556 0.91(3) 2.26(2) 3.010(2) 139(2)
N7 H7B N9 1_455 0.88(2) 2.55(2) 3.348(2) 152(2)
N10 H10A N3 . 0.85(2) 2.62(2) 3.196(2) 126(2)
N10 H10B O1 . 0.84(3) 2.11(3) 2.921(2) 165(2)
N5 H5B N2 . 0.88(3) 2.22(3) 2.606(2) 106(2)
N10 H10A N7 . 0.85(3) 2.23(3) 2.626(3) 109(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 O1 . . . . -178.66(16) ?
N2 N1 C2 O1 . . . . 1.2(2) ?
C6 N1 C2 C3 . . . . 1.1(3) ?
N2 N1 C2 C3 . . . . -179.01(15) ?
O1 C2 C3 C4 . . . . 179.29(18) ?
N1 C2 C3 C4 . . . . -0.5(3) ?
O1 C2 C3 C7 . . . . -0.4(3) ?
N1 C2 C3 C7 . . . . 179.81(16) ?
C7 C3 C4 C5 . . . . 179.12(17) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C7 C3 C4 C8 . . . . 0.6(3) ?
C2 C3 C4 C8 . . . . -179.13(17) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C8 C4 C5 C6 . . . . 179.65(16) ?
C3 C4 C5 C12 . . . . 176.19(17) ?
C8 C4 C5 C12 . . . . -5.2(3) ?
C2 N1 C6 N5 . . . . 179.57(16) ?
N2 N1 C6 N5 . . . . -0.3(2) ?
C2 N1 C6 C5 . . . . -0.7(3) ?
N2 N1 C6 C5 . . . . 179.46(16) ?
C4 C5 C6 N5 . . . . 179.26(18) ?
C12 C5 C6 N5 . . . . 3.8(3) ?
C4 C5 C6 N1 . . . . -0.5(3) ?
C12 C5 C6 N1 . . . . -175.92(16) ?
C3 C4 C8 C9 . . . . 129.8(2) ?
C5 C4 C8 C9 . . . . -48.7(3) ?
C3 C4 C8 S1 . . . . -52.1(2) ?
C5 C4 C8 S1 . . . . 129.31(16) ?
C11 S1 C8 C9 . . . . -0.62(14) ?
C11 S1 C8 C4 . . . . -178.91(15) ?
C4 C8 C9 C10 . . . . 179.27(16) ?
S1 C8 C9 C10 . . . . 1.05(19) ?
C8 C9 C10 C11 . . . . -1.1(2) ?
C9 C10 C11 S1 . . . . 0.6(2) ?
C8 S1 C11 C10 . . . . 0.01(15) ?
C17 N6 C13 O2 . . . . -172.12(17) ?
N7 N6 C13 O2 . . . . 3.8(2) ?
C17 N6 C13 C14 . . . . 8.5(2) ?
N7 N6 C13 C14 . . . . -175.61(15) ?
O2 C13 C14 C15 . . . . 172.61(18) ?
N6 C13 C14 C15 . . . . -8.0(3) ?
O2 C13 C14 C18 . . . . -2.9(3) ?
N6 C13 C14 C18 . . . . 176.52(15) ?
C18 C14 C15 C16 . . . . 177.10(17) ?
C13 C14 C15 C16 . . . . 2.2(3) ?
C18 C14 C15 C19 . . . . -2.0(3) ?
C13 C14 C15 C19 . . . . -176.95(17) ?
C14 C15 C16 C17 . . . . 3.9(3) ?
C19 C15 C16 C17 . . . . -177.03(16) ?
C14 C15 C16 C23 . . . . -176.47(17) ?
C19 C15 C16 C23 . . . . 2.6(3) ?
C13 N6 C17 N10 . . . . 175.40(16) ?
N7 N6 C17 N10 . . . . -0.6(2) ?
C13 N6 C17 C16 . . . . -2.9(3) ?
N7 N6 C17 C16 . . . . -178.87(15) ?
C15 C16 C17 N10 . . . . 178.19(17) ?
C23 C16 C17 N10 . . . . -1.5(3) ?
C15 C16 C17 N6 . . . . -3.6(3) ?
C23 C16 C17 N6 . . . . 176.68(15) ?
C14 C15 C19 C20 . . . . -36.9(4) ?
C16 C15 C19 C20 . . . . 144.0(4) ?
C14 C15 C19 C20' . . . . 146.3(6) ?
C16 C15 C19 C20' . . . . -32.8(6) ?
C14 C15 C19 S2' . . . . -33.7(6) ?
C16 C15 C19 S2' . . . . 147.2(6) ?
C14 C15 C19 S2 . . . . 139.30(16) ?
C16 C15 C19 S2 . . . . -39.8(2) ?
C22' S2' C19 C20 . . . . -73(10) ?
C22' S2' C19 C20' . . . . 0.00(9) ?
C22' S2' C19 C15 . . . . 179.99(5) ?
C22' S2' C19 S2 . . . . 6.2(6) ?
C22 S2 C19 C20 . . . . 0.9(3) ?
C22 S2 C19 C20' . . . . 120(7) ?
C22 S2 C19 C15 . . . . -175.83(17) ?
C22 S2 C19 S2' . . . . -1.9(5) ?
C20' C19 C20 C21 . . . . -6.0(10) ?
C15 C19 C20 C21 . . . . 177.0(2) ?
S2' C19 C20 C21 . . . . 102(10) ?
S2 C19 C20 C21 . . . . 0.3(5) ?
C19 C20 C21 C22 . . . . -1.8(5) ?
C20 C21 C22 S2 . . . . 2.4(3) ?
C19 S2 C22 C21 . . . . -1.95(19) ?
C20 C19 C20' C21' . . . . 2.8(8) ?
C15 C19 C20' C21' . . . . -179.99(8) ?
S2' C19 C20' C21' . . . . 0.01(13) ?
S2 C19 C20' C21' . . . . -60(7) ?
C19 C20' C21' C22' . . . . -0.01(19) ?
C20' C21' C22' S2' . . . . 0.01(18) ?
C19 S2' C22' C21' . . . . -0.01(11) ?
