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Quinoline-2-carbonitrile.

ABSTRACT: In the title compound, C(10)H(6)N(2), the mol-ecule is almost planar, with an r.m.s. deviation of 0.014?Å. The dihedral angle between the aromatic rings is 1.28?(16)°. In the crystal, mol-ecules are stacked along the a axis by way of weak aromatic ?-? stacking inter-actions between the benzene and pyridine rings of adjacent mol-ecules [centroid-centroid separation = 3.7943?(19)?Å].

SUBMITTER: Loh WS

PROVIDER: S-EPMC3008022 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Quinoline-2-carbonitrile.

Loh Wan-Sin WS Quah Ching Kheng CK Hemamalini Madhukar M Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20100825 Pt 9

In the title compound, C(10)H(6)N(2), the mol-ecule is almost planar, with an r.m.s. deviation of 0.014 Å. The dihedral angle between the aromatic rings is 1.28 (16)°. In the crystal, mol-ecules are stacked along the a axis by way of weak aromatic π-π stacking inter-actions between the benzene and pyridine rings of adjacent mol-ecules [centroid-centroid separation = 3.7943 (19) Å]. ...[more]

PMID: 21588729

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Project description:The six-membered N-heterocyclic ring of the title compound, C(17)H(15)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The approximately planar nitro-gen-bearing ring (r.m.s. deviation 0.019?Å) is aromatic, and the N atom shows a trigonal-planar coordination; its benzene substituent is aligned at 77.1?(1) °. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, inversion-related mol-ecules are linked by pairs of N-H?O hydrogen bonds, generating dimers.

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4-(4-Bromo-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(20)H(13)BrN(2)O, the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 17.7?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 82.3?(1)° in order to avoid crowding the cyanide substituent. Two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer.

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8-Methyl-2-oxo-4-(thio-phen-2-yl)-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

Project description:In the title compound, C(15)H(14)N(2)OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011?Å) and the cyclo-hexene ring has a twisted half-boat conformation with the methyl-ene C atom adjacent to the methine C atom deviating by 0.592?(7)?Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108?Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649?(4):0.351?(4) ratio, and forms dihedral angles of 51.4?(3) (major component) and 54.2?(3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol-ecules associate via an eight-membered {?HNCO}(2) synthon and these are linked into a linear supra-molecular chain along the a axis by weak ?-? inter-actions that occur between centrosymmetrically related pyridinone rings [centroid-centroid distance = 3.889?(2)?Å].

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4-(4-Fluoro-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

Project description:In the mol-ecule of the title compound, C(20)H(13)FN(2)O, the fluoro-phenyl ring is oriented at a dihedral angle of 72.76 (3)° with respect to the fused benzene ring. In the crystal structure, inter-molecular N-H⋯O, C-H⋯O and C-H⋯F inter-actions link the mol-ecules into chains. π-π contacts between the quinoline and benzene rings [centroid-centroid distance = 3.918 (3) Å] may further stabilize the structure. A weak C-H⋯π inter-action is also present. The O atom and two of the CH(2) groups of the quinoline ring system are disordered over two positions. The O atom was refined with occupancies of 0.489 (17) and 0.511 (17), while C and H atoms were refined with occupancies of 0.435 (13) and 0.565 (13).

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4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa-hydro-quinoline-3-carbonitrile.

Project description:The six-membered N-heterocyclic ring of title compound, C(17)H(17)ClN(2)O, is fused with a methyl-substituted cyclo-hexene ring. The nitro-gen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432?(6)?Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011?Å); its benzene substituent is aligned at 84.7?(1)° to the latter plane. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, two mol-ecules are linked about a center of inversion by pairs of N-H?O hydrogen bonds, generating dimers. An ethyl-ene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3?(1)% minor component.

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