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Crystal structure and Hirshfeld surface analysis of 6-amino-8-phenyl-1,3,4,8-tetra-hydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbo-nitrile.

ABSTRACT: In the title compound, C₁₆H₁₅N₅, the 1,4-di-hydro-pyridine ring has a shallow boat conformation, while the 1,3-diazinane ring adopts an envelope conformation. In the crystal, pairwise N-H⋯N hydrogen bonds generate centrosymmetric dimers featuring R ² ₂(12) motifs and C-H⋯N contacts connect these dimers to form double layers lying parallel to (001). Weak C-H⋯π and N-H⋯π inter-actions help to consolidate the double layers and van der Waals inter-actions occur between layers. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (38.5%), N⋯H/H⋯N (33.3%) and C⋯H/H⋯C (27.3%) contacts.

SUBMITTER: Naghiyev FN

PROVIDER: S-EPMC8100277 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of 6-imino-8-(4-methyl-phen-yl)-1,3,4,6-tetra-hydro-2<i>H</i>-pyrido[1,2-<i>a</i>]pyrimidine-7,9-dicarbo-nitrile.

Project description:In the ten-membered 1,3,4,6-tetra-hydro-2H-pyrido[1,2-a]pyrimidine ring system of the title compound, C17H15N5, the 1,2-di-hydro-pyridine ring is essentially planar (r.m.s. deviation = 0.001 Å), while the 1,3-diazinane ring has a distorted twist-boat conformation. In the crystal, mol-ecules are linked by N-H⋯N and C-H⋯N hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions form layers parallel to the (100) plane. Thus, crystal-structure cohesion is ensured. According to a Hirshfeld surface study, H⋯H (40.4%), N⋯H/H⋯N (28.6%) and C⋯H/H⋯C (24.1%) inter-actions are the most important contributors to the crystal packing.

| S-EPMC10993597 | biostudies-literature

6-Amino-2-methyl-8-phenyl-1,2,3,4-tetra-hydro-iso-quinoline-5,7-dicarbo-nitrile.

Project description:In the title compound, C18H16N4, the dihedral angle between the benzene and phenyl rings is 61.40?(4)°. In the crystal, mol-ecules are linked by N-H?N(nitrile) hydrogen bonds, forming inversion dimers. The dimers are further linked by N-H?N(amine) hydrogen bonds, and both units are arranged almost perpendicular to each other [angle between dimer mean planes = 84.43?(12)°]. This arrangement is extended to form a ladder-like structure parallel to the c axis.

| S-EPMC3685078 | biostudies-literature

Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemi-hydrate and 1,6-di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile.

Project description:In 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemihydrate, C18H14BrN3O·0.5H2O, (I), pairs of mol-ecules 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 inter-actions, forming layers parallel to the (010) plane. 1,6-Di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile, C13H9N5O, (II), crystallizes in the triclinic space group P with two independent mol-ecules (IIA and IIB) in the asymmetric unit. In the crystal of (II), mol-ecules IIA and IIB are linked by inter-molecular 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 inter-actions connect adjacent mol-ecules, forming chains along the a-axis direction. In (I) and (II), the stability of the packing is ensured by van der Waals inter-actions 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%) inter-actions, while in (II), H⋯H inter-actions are the most significant contributors to the crystal packing (27.6% for mol-ecule IIA and 23.1% for mol-ecule IIB).

| S-EPMC9361375 | biostudies-literature

3,12-Dimeth-oxy-5,6,9,10-tetra-hydro-[5]helicene-7,8-dicarbo-nitrile.

Project description:The complete molecule of the title compound, C26H20N2O2, is generated by a crystallographic twofold axis. The torsion angle between the terminal and central benzene rings is -32.5?(2)°. The torsion angle along the inner helical rim of the molecule is -18.8?(2)° with each other. The C?C distance between the terminal rings is 3.016?(2)?Å. In the crystal, weak C-H?N hydrogen bonds are observed.

| S-EPMC4158476 | biostudies-literature

1,3,3-Trimethyl-1,2,3,4-tetra-hydro-pyrido[1,2-a]benzimidazol-1-ol.

Project description:In the title compound, C(14)H(18)N(2)O, the benzimidazole grouping is close to planar, with a maximum deviation of 0.042 Å; the six-membered non-aromatic ring adopts an envelope conformation. In the crystal structure, mol-ecules are linked into infinite sheets lying parallel to the bc plane by O-H⋯N and C-H⋯O hydrogen bonds.

| S-EPMC3006987 | biostudies-literature

4,5-Diphen-oxy-benzene-1,2-dicarbo-nitrile.

Project description:In the title compound, C(20)H(12)N(2)O(2), the phenyl and benzene rings are mutually perpendicular, with the dihedral angle between the phenyl rings being 87.92?(16)° and those formed between the phenyl rings and the benzene rings being 73.68?(15) and 84.65?(15)°. Helical supra-molecular chains along [010], mediated by C-H?N inter-actions, are found in the crystal structure.

| S-EPMC3297324 | biostudies-literature

trans-1-Phenyl-pyrrolidine-2,5-dicarbo-nitrile.

Project description:In the title compound, C(12)H(11)N(3), the plane of the phenyl ring and the least-squares plane of the pyrrolidine ring enclose an angle of 14.30 (6)°. The intra-cyclic N atom features a nearly trigonal-planar coordination geometry due to π-inter-actions with the aromatic system. The pyrrolidine ring is present in a twist conformation for which the closest pucker descriptor is (C9)T(C8). Weak inter-molecular C-H⋯N and C-H⋯π contacts occur.

| S-EPMC2979938 | biostudies-literature

4-Phenyl-1,2,3,4-tetra-hydro-pyrimido[1,2-a]benzimidazol-2-one.

Project description:In the title compound, C(16)H(13)N(3)O, the tetrahydropyrimidin-one ring adopts a sofa conformation. In the crystal structure, mol-ecules are linked by N-H?N hydrogen bonds and C-H?? inter-actions.

| S-EPMC2959681 | biostudies-literature

6-Benzyl 4-ethyl 2-chloro-5,6,7,8-tetra-hydro-pyrido[4,3-d]pyrimidine-4,6-di-carboxyl-ate.

Project description:In the title compound, C(18)H(18)ClN(3)O(4), the dihedral angle between the pyrimidine ring and the N-bonded ester grouping is 56.27?(7)° and the dihedral angle between the aromatic rings is 11.23?(7)°.

| S-EPMC3200750 | biostudies-literature

5-Methyl-3,6,7,8a-tetra-hydro-2H-diimidazo[1,2-c:1',2'-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide.

Project description:The structure of the title compound, C(12)H(16)N(5) (+)·I(-), shows that the methyl-ation reaction with CH(3)I occurred at the imine N atom at position 5 of the 3,6,7,8a-tetra-hydro-2H-diimidazo[1,2-c:1',2'-e]pyrido[1,2-a][1,3,5]triazine system. In the cation, the sp(3)-hybridized C atom belonging to the fused dihydro-pyrine and dihydro-1,3,5-triazine rings deviates by 0.514?(3)?Å from the best plane defined by the remaining cationic non-H atoms. The fused dihydro-pyridine and dihydro-1,3,5-triazine rings are each in a half-chair conformation with the sp(3)-hybridized C atom as a flap. The iodide anion is 3.573?(2)?Å from the methyl-ated N atom and exhibits five short C-H?I(-) contacts with distances less than 3.16?Å. The structure has been determined from a non-merohedral twin with twin law [-1 0 0 0 - 1 0 0.115 0 1], minor domain = 0.1559?(12).

| S-EPMC2979596 | biostudies-literature

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