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2-Amino-4-(2-fluoro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile.

ABSTRACT: In the title compound, C(20)H(14)FN(3), the F atom of the fluoro-substituted benzene ring in the 4-position of the 5,6-dihydro-benzo[h]quinoline system is disordered over two positions (0.80 and 0.20 occupancy). The dihedral angle between the pyridine and fluorobenzene rings is 73.2?(2)?Å. The crystal structure is established by inter-molecular N-H?N hydrogen bonds, forming a three-dimensional network.

SUBMITTER: Wang W

PROVIDER: S-EPMC3050399 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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2-Amino-4-(2-fluoro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile.

Wang Wei W Tang Shi-Gui SG Guo Cheng C Luan Chang-Jun CJ Du Ren-Jun RJ

Acta crystallographica. Section E, Structure reports online 20101211 Pt 1

In the title compound, C(20)H(14)FN(3), the F atom of the fluoro-substituted benzene ring in the 4-position of the 5,6-dihydro-benzo[h]quinoline system is disordered over two positions (0.80 and 0.20 occupancy). The dihedral angle between the pyridine and fluorobenzene rings is 73.2 (2) Å. The crystal structure is established by inter-molecular N-H⋯N hydrogen bonds, forming a three-dimensional network. ...[more]

PMID: 21522805

Similar Datasets

2-Amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile-3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (1/4).

Project description:The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.2C(20)H(14)ClN(3)·0.8C(22)H(14)ClN(3), has the atoms of the fused-ring system and those of the amino, cyano and chloro-phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring. There are two independent overlapped mol-ecules in the asymmetric unit. In one independent mol-ecule, the two flanking aromatic rings are twisted by 24.4?(1)° and the ring of the chloro-phenyl substituent is twisted by 87.3?(1)° relative to the amino- and cyano-bearing aromatic ring. In the second mol-ecule, the respective dihedral angles are 26.1?(1) and 57.8?(1)°. The two independent mol-ecules are linked by N-H?N hydrogen bonds into dimers.

| S-EPMC3247609 | biostudies-literature

2-Amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile-3-amino-1-phenyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (5/3).

Project description:The asymmetric unit of the 5:3 title co-crystal of 2-amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-phenyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.625C(20)H(15)N(3).0.375C(22)H(15)N(3), has the atoms of the fused-ring system and those of the amino, cyano and phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring, the two flanking aromatic rings being twisted by 20.1?(1)°. This ethyl-ene portion is disordered over two positions in a 1:1 ratio. The phenyl ring is twisted by 69.5?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, two mol-ecules are linked by an N-H?N hydrogen bond, generating a a helical chain along [010].

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

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2-Amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbo-nitrile-3-amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (1/19).

Project description:The asymmetric unit of the 1:19 title co-crystal of 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbo-nitrile and 3-amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.05C(22)H(19)N(3)O(2)·0.95C(24)H(19)N(3)O(2), has the atoms of the fused-ring system and those of the amino, cyano and dimeth-oxy-phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring with the two flanking aromatic rings being twisted by 31.9?(1)°. The ring of the dimeth-oxy-phenyl substituent is twisted by 72.4?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, mol-ecules are linked by duplex amine N-H?O(meth-oxy) hydrogen bonds in a cyclic association [graph-set R(2) (2)(7)], generating a helical chain structure extending along [201].

| S-EPMC3247608 | biostudies-literature

3-Amino-1-(4-fluoro-phen-yl)-7-meth-oxy-1H-benzo[f]chromene-2-carbonitrile.

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3-Amino-1-(4-fluoro-phen-yl)-8-meth-oxy-1H-benzo[f]chromene-2-carbonitrile.

Project description:The title compound, C21H15FN2O2, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052?Å), with the fluoro-benzene ring being almost perpendicular to this [dihedral angle = 85.30?(7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132?(2)?Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107?Å). In the crystal, inversion dimers are formed via pairs of amine-cyano N-H?N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C-H?N(cyano), C-H?? and ?-? [inter-centroid distance = 3.6671?(10)?Å] inter-actions.

| S-EPMC3629515 | biostudies-literature

6-(2-Fluoro-phen-yl)-5,6-dihydro-benzimidazolo[1,2-c]quinazoline.

Project description:In the title compound, C(20)H(14)FN(3), the pyrimidine ring adopts a half-chair conformation. The dihedral angle between the benzimidazole ring system and the fluoro-phenyl ring is 84.18 (10)°. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to the bc plane by N-H⋯N and C-H⋯F hydrogen bonds.

| S-EPMC2959727 | biostudies-literature

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

Project description:In the mol-ecule of the title compound, C(18)H(12)N(2)OS, 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 16.0?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 59.5?(2)° (for the major disordered thienyl component) in order to avoid crowding the cyanide substituent. In the crystal, two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer. The thienyl ring is disordered over two sites in a 72.7?(2):27.3 ratio.

| S-EPMC3200622 | biostudies-literature

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.

| S-EPMC3200630 | biostudies-literature

2-Amino-4-(4-fluoro-phen-yl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile.

Project description:The title compound, C(22)H(14)FN(3), was prepared by a one-pot condensation using malononitrile, an aromatic aldehyde, a methyl ketone and ammonium acetate as reacta-nts under microwave irradiation. The pyridine ring is twisted with respect to the benzene ring and the naphthalene ring system, making dihedral angles of 41.9?(1) and 45.2?(1)°, respectively. In the crystal, mol-ecules are connected via inter-molecular N-H?N and C-H?F hydrogen bonds, forming a three-dimensional network.

| S-EPMC3050308 | biostudies-literature

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