#------------------------------------------------------------------------------
#$Date: 2023-07-06 21:19:59 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285057 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022774.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_2022774
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Khrustalev, Victor N.'
'Mamedov, Huseyn M.'
'Akkurt, Mehmet'
'Khalilov, Ali N.'
'Bhattarai, Ajaya'
'Mamedov, İbrahim G'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 5-oxo-7-phenyl-2-(phenyl-amino)-1H-[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbo-nitrile
 dimethyl sulfoxide monosolvate.
;
_journal_coeditor_code           TX2068
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              567
_journal_page_last               570
_journal_paper_doi               10.1107/S2056989023004383
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C20 H12 N6 O, C2 H6 O S'
_chemical_formula_moiety         'C20 H12 N6 O, C2 H6 O S'
_chemical_formula_sum            'C22 H18 N6 O2 S'
_chemical_formula_weight         430.48
_chemical_name_systematic
'5-Oxo-7-phenyl-2-(phenylamino)-1H-[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbonitrile dimethyl sulfoxide monosolvate'
_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                100.9305(10)
_cell_angle_beta                 105.3054(11)
_cell_angle_gamma                112.6790(12)
_cell_formula_units_Z            2
_cell_length_a                   9.87885(12)
_cell_length_b                   10.46018(13)
_cell_length_c                   11.48307(12)
_cell_measurement_reflns_used    15870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3
_cell_measurement_theta_min      4.8
_cell_volume                     997.81(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22299
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.446
_diffrn_reflns_theta_min         4.225
_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    1.725
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.508
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0382
_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)+(0.0554P)²+0.554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                4124
_reflns_number_total             4314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2068sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022774.cif.'
_cod_original_cell_volume        997.81(2)
_cod_database_code               2022774
_cod_database_fobs_code          2022774
_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   0.703
_shelx_estimated_absorpt_t_max   0.820
_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
O O1 -0.06967(12) 0.20611(11) 0.42668(10) 0.0214(2) Uani d 1 . .
N N1 0.37412(14) 0.55891(13) 0.44627(11) 0.0171(2) Uani d 1 . .
H H1 0.465(2) 0.635(2) 0.4612(18) 0.021 Uiso d 1 . .
C C2 0.29261(16) 0.44403(15) 0.33251(13) 0.0163(3) Uani d 1 . .
N N2 0.35694(14) 0.44663(14) 0.24222(12) 0.0189(3) Uani d 1 . .
H H2 0.453(2) 0.523(2) 0.2678(18) 0.023 Uiso d 1 . .
N N3 0.15858(14) 0.34368(13) 0.32865(11) 0.0178(2) Uani d 1 . .
N N4 0.15615(14) 0.40235(12) 0.44782(11) 0.0159(2) Uani d 1 . .
C C5 0.03861(16) 0.32893(15) 0.49174(14) 0.0177(3) Uani d 1 . .
C C6 0.06152(16) 0.41513(15) 0.61676(13) 0.0176(3) Uani d 1 . .
C C7 0.19229(16) 0.55162(15) 0.69078(13) 0.0174(3) Uani d 1 . .
C C8 0.30798(16) 0.61215(15) 0.63984(13) 0.0172(3) Uani d 1 . .
C C8A 0.28510(16) 0.53211(15) 0.51784(13) 0.0167(3) Uani d 1 . .
C C9 0.29501(17) 0.34391(15) 0.11906(13) 0.0179(3) Uani d 1 . .
C C10 0.13802(18) 0.23723(17) 0.06025(15) 0.0227(3) Uani d 1 . .
H H10 0.0659 0.2308 0.1023 0.027 Uiso calc 1 . .
C C11 0.08828(19) 0.13987(18) -0.06143(15) 0.0262(3) Uani d 1 . .
H H11 -0.0189 0.0670 -0.1026 0.031 Uiso calc 1 . .
C C12 0.19282(19) 0.14769(18) -0.12345(15) 0.0265(3) Uani d 1 . .
H H12 0.1581 0.0794 -0.2056 0.032 Uiso calc 1 . .
C C13 0.34888(19) 0.25654(18) -0.06421(15) 0.0242(3) Uani d 1 . .
H H13 0.4208 0.2634 -0.1065 0.029 Uiso calc 1 . .
C C14 0.39982(17) 0.35488(17) 0.05611(14) 0.0211(3) Uani d 1 . .
H H14 0.5062 0.4298 0.0958 0.025 Uiso calc 1 . .
C C15 -0.06863(17) 0.35194(15) 0.65539(13) 0.0186(3) Uani d 1 . .
N N15 -0.18041(15) 0.29648(14) 0.67726(13) 0.0235(3) Uani d 1 . .
C C16 0.21011(16) 0.63048(16) 0.82000(13) 0.0178(3) Uani d 1 . .
C C17 0.25352(17) 0.78044(16) 0.85674(14) 0.0202(3) Uani d 1 . .
H H17 0.2689 0.8319 0.7977 0.024 Uiso calc 1 . .
C C18 0.27428(18) 0.85436(16) 0.97909(14) 0.0223(3) Uani d 1 . .
H H18 0.3041 0.9563 1.0037 0.027 Uiso calc 1 . .
C C19 0.25145(17) 0.77930(17) 1.06577(14) 0.0218(3) Uani d 1 . .
H H19 0.2658 0.8301 1.1495 0.026 Uiso calc 1 . .
C C20 0.20758(17) 0.62989(17) 1.03002(14) 0.0215(3) Uani d 1 . .
H H20 0.1913 0.5788 1.0892 0.026 Uiso calc 1 . .
C C21 0.18757(17) 0.55538(16) 0.90782(14) 0.0195(3) Uani d 1 . .
H H21 0.1587 0.4537 0.8839 0.023 Uiso calc 1 . .
C C22 0.44758(17) 0.74971(16) 0.70142(14) 0.0191(3) Uani d 1 . .
N N22 0.56198(16) 0.85887(14) 0.74045(13) 0.0251(3) Uani d 1 . .
S S1 0.73840(4) 0.86862(4) 0.42677(3) 0.01894(11) Uani d 1 . .
O O2 0.63433(12) 0.71002(11) 0.41226(10) 0.0215(2) Uani d 1 . .
C C23 0.6060(2) 0.94489(18) 0.39068(19) 0.0328(4) Uani d 1 . .
H H23A 0.5447 0.9058 0.2985 0.049 Uiso calc 1 . .
H H23B 0.6662 1.0518 0.4170 0.049 Uiso calc 1 . .
H H23C 0.5340 0.9190 0.4366 0.049 Uiso calc 1 . .
C C24 0.83449(19) 0.96161(17) 0.59410(15) 0.0249(3) Uani d 1 . .
H H24A 0.9001 0.9187 0.6319 0.037 Uiso calc 1 . .
H H24B 0.7551 0.9518 0.6326 0.037 Uiso calc 1 . .
H H24C 0.9013 1.0657 0.6101 0.037 Uiso calc 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
C8A N1 C2 . . 106.74(12) ?
C8A N1 H1 . . 130.6(12) ?
C2 N1 H1 . . 122.6(12) ?
N3 C2 N2 . . 128.74(13) ?
N3 C2 N1 . . 112.99(12) ?
N2 C2 N1 . . 118.26(13) ?
C2 N2 C9 . . 128.42(13) ?
C2 N2 H2 . . 113.3(12) ?
C9 N2 H2 . . 118.3(12) ?
C2 N3 N4 . . 102.08(11) ?
C8A N4 N3 . . 112.16(11) ?
C8A N4 C5 . . 124.35(12) ?
N3 N4 C5 . . 123.34(11) ?
O1 C5 N4 . . 121.08(13) ?
O1 C5 C6 . . 126.58(13) ?
N4 C5 C6 . . 112.33(12) ?
C7 C6 C15 . . 122.14(13) ?
C7 C6 C5 . . 124.47(13) ?
C15 C6 C5 . . 113.26(12) ?
C6 C7 C8 . . 118.34(13) ?
C6 C7 C16 . . 121.23(13) ?
C8 C7 C16 . . 120.43(13) ?
C8A C8 C7 . . 117.77(13) ?
C8A C8 C22 . . 116.44(12) ?
C7 C8 C22 . . 125.79(13) ?
N1 C8A N4 . . 106.01(12) ?
N1 C8A C8 . . 131.52(13) ?
N4 C8A C8 . . 122.47(13) ?
C10 C9 C14 . . 120.41(13) ?
C10 C9 N2 . . 123.15(13) ?
C14 C9 N2 . . 116.43(13) ?
C9 C10 C11 . . 118.88(14) ?
C9 C10 H10 . . 120.6 ?
C11 C10 H10 . . 120.6 ?
C12 C11 C10 . . 121.06(14) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C13 . . 119.36(14) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C14 C13 C12 . . 120.29(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C9 . . 119.96(14) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
N15 C15 C6 . . 175.03(16) ?
C17 C16 C21 . . 119.42(13) ?
C17 C16 C7 . . 120.65(13) ?
C21 C16 C7 . . 119.90(13) ?
C18 C17 C16 . . 120.31(13) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 120.05(14) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C20 . . 120.12(14) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C21 C20 C19 . . 120.12(14) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C20 C21 C16 . . 119.98(13) ?
C20 C21 H21 . . 120.0 ?
C16 C21 H21 . . 120.0 ?
N22 C22 C8 . . 173.67(15) ?
O2 S1 C24 . . 105.38(7) ?
O2 S1 C23 . . 105.07(7) ?
C24 S1 C23 . . 99.29(8) ?
S1 C23 H23A . . 109.5 ?
S1 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
S1 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
S1 C24 H24A . . 109.5 ?
S1 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
S1 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
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
O1 C5 . 1.2277(18) ?
N1 C8A . 1.3439(18) ?
N1 C2 . 1.3792(18) ?
N1 H1 . 0.88(2) ?
C2 N3 . 1.3178(18) ?
C2 N2 . 1.3508(18) ?
N2 C9 . 1.4102(18) ?
N2 H2 . 0.90(2) ?
N3 N4 . 1.4000(16) ?
N4 C8A . 1.3504(18) ?
N4 C5 . 1.4003(18) ?
C5 C6 . 1.4510(19) ?
C6 C7 . 1.403(2) ?
C6 C15 . 1.4297(19) ?
C7 C8 . 1.4088(19) ?
C7 C16 . 1.4829(19) ?
C8 C8A . 1.3988(19) ?
C8 C22 . 1.429(2) ?
C9 C10 . 1.390(2) ?
C9 C14 . 1.394(2) ?
C10 C11 . 1.394(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.388(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.391(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 N15 . 1.152(2) ?
C16 C17 . 1.399(2) ?
C16 C21 . 1.403(2) ?
C17 C18 . 1.388(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.392(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.393(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.391(2) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 N22 . 1.151(2) ?
S1 O2 . 1.5253(10) ?
S1 C24 . 1.7764(16) ?
S1 C23 . 1.7788(16) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
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
N1 H1 O2 . 0.88(2) 1.84(2) 2.6249(16) 146.9(17)
N2 H2 O2 . 0.90(2) 2.07(2) 2.8680(16) 147.7(17)
C10 H10 N3 . 0.95 2.39 2.9956(19) 120.9
C23 H23B O1 1_665 0.98 2.44 3.166(2) 130.6
C24 H24B N22 . 0.98 2.53 3.474(2) 162.3
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
C8A N1 C2 N3 . . . . -1.59(16) ?
C8A N1 C2 N2 . . . . 178.85(12) ?
N3 C2 N2 C9 . . . . 1.7(2) ?
N1 C2 N2 C9 . . . . -178.83(13) ?
N2 C2 N3 N4 . . . . -179.43(14) ?
N1 C2 N3 N4 . . . . 1.07(15) ?
C2 N3 N4 C8A . . . . -0.17(14) ?
C2 N3 N4 C5 . . . . -175.92(12) ?
C8A N4 C5 O1 . . . . -174.55(13) ?
N3 N4 C5 O1 . . . . 0.7(2) ?
C8A N4 C5 C6 . . . . 6.19(19) ?
N3 N4 C5 C6 . . . . -178.59(11) ?
O1 C5 C6 C7 . . . . 176.10(14) ?
N4 C5 C6 C7 . . . . -4.69(19) ?
O1 C5 C6 C15 . . . . -7.8(2) ?
N4 C5 C6 C15 . . . . 171.43(11) ?
C15 C6 C7 C8 . . . . -173.97(12) ?
C5 C6 C7 C8 . . . . 1.8(2) ?
C15 C6 C7 C16 . . . . 6.6(2) ?
C5 C6 C7 C16 . . . . -177.65(12) ?
C6 C7 C8 C8A . . . . 0.09(19) ?
C16 C7 C8 C8A . . . . 179.57(12) ?
C6 C7 C8 C22 . . . . 179.62(13) ?
C16 C7 C8 C22 . . . . -0.9(2) ?
C2 N1 C8A N4 . . . . 1.35(14) ?
C2 N1 C8A C8 . . . . -178.81(14) ?
N3 N4 C8A N1 . . . . -0.77(15) ?
C5 N4 C8A N1 . . . . 174.93(12) ?
N3 N4 C8A C8 . . . . 179.38(12) ?
C5 N4 C8A C8 . . . . -4.9(2) ?
C7 C8 C8A N1 . . . . -178.46(13) ?
C22 C8 C8A N1 . . . . 2.0(2) ?
C7 C8 C8A N4 . . . . 1.4(2) ?
C22 C8 C8A N4 . . . . -178.22(13) ?
C2 N2 C9 C10 . . . . 14.8(2) ?
C2 N2 C9 C14 . . . . -166.01(14) ?
C14 C9 C10 C11 . . . . 1.3(2) ?
N2 C9 C10 C11 . . . . -179.53(14) ?
C9 C10 C11 C12 . . . . 0.4(2) ?
C10 C11 C12 C13 . . . . -1.4(3) ?
C11 C12 C13 C14 . . . . 0.8(2) ?
C12 C13 C14 C9 . . . . 0.8(2) ?
C10 C9 C14 C13 . . . . -1.9(2) ?
N2 C9 C14 C13 . . . . 178.89(13) ?
C6 C7 C16 C17 . . . . -134.34(14) ?
C8 C7 C16 C17 . . . . 46.20(19) ?
C6 C7 C16 C21 . . . . 47.42(19) ?
C8 C7 C16 C21 . . . . -132.04(14) ?
C21 C16 C17 C18 . . . . 0.1(2) ?
C7 C16 C17 C18 . . . . -178.18(13) ?
C16 C17 C18 C19 . . . . -0.2(2) ?
C17 C18 C19 C20 . . . . -0.1(2) ?
C18 C19 C20 C21 . . . . 0.5(2) ?
C19 C20 C21 C16 . . . . -0.6(2) ?
C17 C16 C21 C20 . . . . 0.3(2) ?
C7 C16 C21 C20 . . . . 178.61(13) ?
