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

ABSTRACT: 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.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3200630 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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

Asiri Abdullah M AM Faidallah Hassan M HM Al-Youbi Abdulrahman O AO Alamry Khalid A KA Ng Seik Weng SW

Acta crystallographica. Section E, Structure reports online 20110827 Pt 9

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. ...[more]

PMID: 22064644

Similar Datasets

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

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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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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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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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