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Crystal structure and Hirshfeld surface analysis of (Z)-2-amino-4-(2,6-di-chloro-phen-yl)-5-(1-hy-droxy-ethyl-idene)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

ABSTRACT: The mol-ecular conformation of the title compound, C₂₀H₁₅Cl₂N₃O₂, is stabilized by an intra-molecular O-H⋯O hydrogen bond, forming an S(6) ring motif. The central pyridine ring is almost planar [maximum deviation = 0.074 (3) Å]. It subtends dihedral angles of 86.10 (15) and 87.17 (14)°, respectively, with the phenyl and di-chloro-phenyl rings, which are at an angle of 21.28 (15)° to each other. The =C(-OH)CH₃ group is coplanar. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N and C-H⋯N hydrogen bonds, and N-H⋯π and C-H⋯π inter-actions, forming a three-dimensional network. The most important contributions to the crystal packing are from H⋯H (33.1%), C⋯H/H⋯C (22.5%), Cl⋯H/H⋯Cl (14.1%), O⋯H/H⋯O (11.9%) and N⋯H/H⋯N (9.7%) inter-actions.

SUBMITTER: Naghiyev FN

PROVIDER: S-EPMC8423002 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of 2-amino-4-(4-meth-oxy-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Project description:The central tetra-hydro-pyridine ring of the title compound, C19H17N3O2, adopts a screw-boat conformation. In the crystal, strong C-H⋯O and N-H⋯N hydrogen bonds form dimers with R 2 2(14) and R 2 2(12) ring motifs, respectively, between consecutive mol-ecules along the c-axis direction. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds connect these dimers, forming a three-dimensional network. C-H⋯π inter-actions and π-π stacking inter-actions contribute to the stabilization of the mol-ecular packing. A Hirshfeld surface analysis indicates that the contributions from the most prevalent inter-actions are H⋯H (47.1%), C⋯H/H⋯C (20.9%), O⋯H/H⋯O (15.3%) and N⋯H/H⋯N (11.4%).

| S-EPMC8900505 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 5-acetyl-2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Project description:The crystal structure of the title compound, C20H16BrN3O2, was determined using an inversion twin. Its asymmetric unit comprises two crystallographically independent mol-ecules (A and B) being the stereoisomers. Both mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming a dimer with an R 2 2(16) ring motif. The dimers are connected by further N-H⋯O and N-H⋯N hydrogen bonds, forming chains along the c-axis direction·C-Br⋯π inter-actions between these chains contribute to the stabilization of the mol-ecular packing. Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, Br⋯H/H⋯Br and N⋯H/H⋯N inter-actions.

| S-EPMC8900508 | 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

Crystal structure and Hirshfeld surface analysis of 2-(4-bromo-phen-yl)-4-methyl-6-oxo-1-phenyl-1,6-di-hydro-pyridine-3-carbo-nitrile.

Project description:In the title compound, C19H13BrN2O, the pyridine ring is essentially planar [maximum deviation = 0.024 (4) Å for the N atom] and makes dihedral angles of 74.6 (2) and 65.8 (2)°, respectively, with the phenyl and bromo-phenyl rings, which subtend a dihedral angle of 63.1 (2)°. In the crystal, mol-ecules are connected along the c-axis direction via C-Br⋯π inter-actions, generating zigzag chains parallel to the (010) plane. C-H⋯N and C-H⋯O hydrogen-bonding inter-actions further connect the mol-ecules, forming a three-dimensional network and reinforcing the mol-ecular packing. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (36.2%), C⋯H/H⋯C (21.6%), N⋯H/H⋯N (12.2%), and Br⋯H/H⋯Br (10.8%) inter-actions.

| S-EPMC9361383 | biostudies-literature

Ethyl 1-benzoyl-4-hy-droxy-2,6-diphenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Project description:In the title compound, C(27)H(25)NO(4), the tetra-hydro-pyridine ring adopts a half-chair conformation. The three phenyl rings form dihedral angles of 66.33 (7), 87.36 (8) and 36.90 (7)° with the least-squares plane through the tetra-hydro-pyridine ring. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(6) motif.

| S-EPMC3052159 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetra-hydro-iso-quinoline-4-carbo-nitrile.

Project description:In the title compound, C28H21N3O, the 1,2-di-hydro-pyridine ring of the 1,2,7,8-tetra-hydro-iso-quinoline ring system is planar as expected, while the cyclo-hexa-1,3-diene ring has a twist-boat conformation, with Cremer-Pople parameters Q T = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the iso-quinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C-H⋯π bonds with a strong inter-action involving the phenyl H atoms. The role of the inter-molecular inter-actions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (46.0%), C⋯H/H⋯C (35.1%) and N⋯H/H⋯N (10.5%) contacts.

| S-EPMC7869549 | biostudies-literature

Crystal structure of 2-amino-7-hy-droxy-4-(4-hy-droxy-phen-yl)-4H-chromene-3-carbo-nitrile.

Project description:In the title compound, C16H12N2O3, the chromene ring system is nearly planar [maximum deviation from the mean plane = 0.057 (1) Å], and is almost perpendicular to the benzene ring, with a dihedral angle of 85.29 (5)°. In the crystal, mol-ecules are linked by classical N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, and weak C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular network. Furthermore, a weak π-π stacking inter-action is observed; the centroid-to-centroid distance is 3.7260 (7) Å.

| S-EPMC4571389 | biostudies-literature

Crystal structure of 1-amino-2-oxo-2,5,6,7,8,9-hexa-hydro-1H-cyclo-hepta-[b]pyridine-3-carbo-nitrile.

Project description:In the title compound, C11H13N3O, the seven-membered ring adopts a conformation such that the three atoms not involved in the aromatic plane lie on the same side of that plane. One hydrazinic H atom forms an intra-molecular hydrogen bond to the O atom; the other forms a classical inter-molecular hydrogen bond N-H?O, which combines with a 'weak' Har?O inter-action to build up double layers of mol-ecules parallel to the bc plane.

| S-EPMC5120696 | biostudies-other

Ethyl 4-hy-droxy-2,6-diphenyl-1-(2-thio-morpholino-acet-yl)-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Project description:In the title compound, C(26)H(30)N(2)O(4)S, the thio-morpholine ring adopts a chair conformation whereas the tetra-hydro-pyridine ring is in a half-chair conformation. The dihedral angle between the two phenyl rings is 33.3?(2)°. A strong intra-molecular O-H?O hydrogen bond generates an S(6) motif. In the crystal, mol-ecules are linked by inter-molecular C-H?O hydrogen bonds, generating a ribbon-like structure propagating along the a axis.

| S-EPMC3007352 | biostudies-literature

2,6-Bis(2-chloro-phen-yl)-4-oxo-3,5-diphenyl-heptane-1,1,7,7-tetra-carbo-nitrile.

Project description:In the title compound, C(35)H(24)Cl(2)N(4)O, the phenyl rings are oriented almost parallel to each other, making a dihedral angle of 0.6?(2)°, whereas the chloro-phenyl rings are oriented at a dihedral angle of 28.3?(1)°. The crystal structure is stabilized through an extensive series of C-H?N, C-H?O and C-H?Cl inter-actions. One of the C-H?N inter-actions generates an R(2) (2)(12) ring motif around a crystallographic inversion centre. C(5), C(10) and C(12) chain motifs are observed in the unit cell through C-H?N and C-H?Cl inter-actions. During the structure analysis, it was observed that the unit cell contains large accessible voids, which host disordered solvent mol-ecules. This affects the diffraction pattern, mostly at low scattering angles and was corrected with the SQUEEZE program [Spek, A. L. (2009 ?). Acta Cryst. D65, 148-155].

| S-EPMC3120456 | biostudies-literature

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