Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidine-7,9-dicarbonitrile

Naghiyev, Farid N.; Tereshina, Tatiana A.; Khrustalev, Victor N.; Akkurt, Mehmet; Rzayev, R. M.; Akobirshoeva, Anzurat A.; Мамедов, И. Г.

doi:10.1107/s2056989021003583

Cited by 16 publications

(15 citation statements)

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“…Thus, in the framework of our ongoing structural studies (Naghiyev et al, 2020(Naghiyev et al, , 2021(Naghiyev et al, , 2022Khalilov et al, 2022), we report the crystal structure and Hirshfeld surface analysis of the title compound, 2,2 0 -(phenylazanediyl)bis(1-phenylethan-1-one).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one)

et al. 2022

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The whole molecule of the title compound, C22H19NO2, is generated by twofold rotational symmetry. The N atom exhibits a trigonal-planar geometry and is located on the twofold rotation axis. In the crystal, molecules are linked by C—H...O contacts with R 2 2(12) ring motifs, and C—H...π interactions, resulting in ribbons along the c-axis direction. van der Waals interactions between these ribbons consolidate the molecular packing. Hirshfeld surface analysis indicates that the greatest contributions to the crystal packing are from H...H (45.5%), C...H/H...C (38.2%) and O...H/H...O (16.0%) interactions.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one)

et al. 2022

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“…Thus, in the framework of our ongoing structural studies (Naghiyev et al, 2020(Naghiyev et al, , 2021(Naghiyev et al, , 2022Khalilov et al, 2022), we report the crystal structure and Hirshfeld surface analysis of the racemic title compound, 4-bromo-2-[3-methyl-5-(2,4,6trimethylbenzyl)oxazolidin-2-yl]phenol.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol

et al. 2022

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The title compound, C20H24BrNO2, is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes dihedral angles of 77.74 (10) and 45.50 (11)°, respectively, with the 4-bromophenol and 1,3,5-trimethylbenzene rings. In the crystal, adjacent molecules are connected via C—H...O hydrogen bonds and C—H...π interactions into layers parallel to the (200) plane. The packing is strengthened by van der Waals interactions between parallel molecular layers. A Hirshfeld surface analysis shows that H...H (58.2%), C...H/H...C (18.9%), and Br...H/H...Br (11.5%) interactions are the most abundant in the crystal packing.

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“…A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al, 2016) gave eleven compounds closely related to the title compounds, viz. CSD refcodes YAXQAT (I) (Mamedov et al, 2022), OZAKOS (II) (Naghiyev et al, 2021), JEBREQ (III) (Mohana et al, 2017), JEBRAM (IV) (Mohana et al, 2017), SETWUK (V) (Suresh et al, 2007), SETWOE (VI) (Suresh et al, 2007), IQEFOC (VII) (Naghiyev et al, 2021a), MOKBUL (VIII) (Mohamed et al, 2014), PAVQIO (IX) (Al-Said et al, 2012), YIZGOE01 (X) (Jia & Tu, 2008) and YIBZAL (XI) (Eyduran et al, 2007).…”

Section: Database Surveymentioning

confidence: 99%

“…In view of the growing biological value of pyridine derivatives, we have considered the study of this class of compounds (Naghiyev et al, 2020b) to be of great interest. Thus, in the framework of our ongoing structural studies (Naghiyev et al, 2020a(Naghiyev et al, ,b, 2021(Naghiyev et al, , 2021a(Naghiyev et al, ,b, 2022, we report here the crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromophenyl)-6-oxo-1phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate (I) and 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5dicarbonitrile (II).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate and 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile

Naghiyev¹,

Хрусталев²,

Venskovsky³

et al. 2022

Acta Cryst E

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In 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate, C18H14BrN3O·0.5H2O, (I), pairs of molecules are linked by pairs of N—H...N hydrogen bonds, forming dimers with an R 2 2(12) ring motif. The dimers are connected by N—H...Br and O—H...O hydrogen bonds, and C—Br...π interactions, forming layers parallel to the (010) plane. 1,6-Diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile, C13H9N5O, (II), crystallizes in the triclinic space group P\overline{1} with two independent molecules (IIA and IIB) in the asymmetric unit. In the crystal of (II), molecules IIA and IIB are linked by intermolecular N—H...N and N—H...O hydrogen bonds into layers parallel to (001). These layers are connected along the c-axis direction by weak C—H...N contacts. C—H...π and C—N...π interactions connect adjacent molecules, forming chains along the a-axis direction. In (I) and (II), the stability of the packing is ensured by van der Waals interactions between the layers. In (I), Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H...H (37.9%), C...H/H...C (18.4%), Br...H/H...Br (13.3%), N...H/H...N (11.5%) and O...H/H...O (10.0%) interactions, while in (II), H...H interactions are the most significant contributors to the crystal packing (27.6% for molecule IIA and 23.1% for molecule IIB).

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Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile

Cited by 16 publications

References 40 publications

Crystal structure and Hirshfeld surface analysis of 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one)

Crystal structure and Hirshfeld surface analysis of 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one)

Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol

Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate and 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile

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