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1-Phenyl-6,7,8,9-hexa-hydro-1H,5H-cyclo-hepta-[1',2':2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue.

ABSTRACT: The title compound, C(17)H(18)N(4), contains a pyrazolopyridine system fused with a seven-membered carbocyclic ring. The pyrazole ring is coplanar with the pyridine ring, while the phenyl ring is twisted by a dihedral angle of 14.38?(14)° with respect to the pyridine ring. The seven-membered ring displays a chair conformation. The packing is stabilized by N-H?N hydrogen bonds and N-H??(arene) inter-actions.

SUBMITTER: Zhang L

PROVIDER: S-EPMC2961386 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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1-Phenyl-6,7,8,9-hexa-hydro-1H,5H-cyclo-hepta-[1',2':2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue.

Zhang Lijun L Shi Daxin D Li Jiarong J Zhang Ling L Fan Yanqiu Y

Acta crystallographica. Section E, Structure reports online 20080510 Pt 6

The title compound, C(17)H(18)N(4), contains a pyrazolopyridine system fused with a seven-membered carbocyclic ring. The pyrazole ring is coplanar with the pyridine ring, while the phenyl ring is twisted by a dihedral angle of 14.38 (14)° with respect to the pyridine ring. The seven-membered ring displays a chair conformation. The packing is stabilized by N-H⋯N hydrogen bonds and N-H⋯π(arene) inter-actions. ...[more]

PMID: 21202575

Similar Datasets

Crystal structures of 2-benzyl-amino-4-(4-bromo-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile and 2-benzyl-amino-4-(4-chloro-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta[b]pyridine-3-carbo-nitrile.

Project description:In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-amino-pyridine ring is fused with a cyclo-heptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N-H⋯Nnitrile hydrogen bonds link the mol-ecules, forming inversion dimers with R 2 (2)(12) ring motifs. In (I), the resulting dimers are connected through C-H⋯Br hydrogen bonds, forming sheets parallel to (10-1), and π-π inter-actions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π-π inter-actions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001).

| S-EPMC4331894 | biostudies-literature

2-(4-Bromo-phen-yl)-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine.

Project description:In the title compound, C23H22BrNO, the cyclo-heptane ring adopts a chair conformation. The pyridine ring makes dihedral angles of 58.63 (15) and 8.27 (16)° with the benzene rings. The dihedral angle between the benzene rings is 56.68 (17)°. The crystal packing features C-Br⋯π inter-actions [Br⋯centroid distances= 3.813 (2) and 3.839 (2) Å; C-Br⋯centroid = 126.25 (10) and 138.31 (10)°, respectively, forming a three dimensional supramolecular architecture.

| S-EPMC3685096 | biostudies-literature

Crystal structure of 2-benzyl-amino-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile.

Project description:The title compound, C25H25N3O, comprises a 2-amino-pyridine ring fused with a cyclo-heptane ring, which adopts a chair conformation. The central pyridine ring (r.m.s. deviation = 0.013?Å) carries three substituents, viz. a benzyl-amino group, a meth-oxy-phenyl ring and a carbo-nitrile group. The N atom of the carbo-nitrile group is significantly displaced [by 0.2247?(1)?Å] from the plane of the pyridine ring, probably due to steric crowding involving the adjacent substituents. The phenyl and benzene rings are inclined to one another by 58.91?(7)° and to the pyridine ring by 76.68?(7) and 49.80?(6)°, respectively. In the crystal, inversion dimers linked by pairs of N-H?Nnitrile hydrogen bonds generate R 2 (2)(14) loops. The dimers are linked by C-H?? and slipped parallel ?-? inter-actions [centroid-centroid distance = 3.6532?(3)?Å] into a three-dimensional structure.

| S-EPMC4257429 | biostudies-literature

7,8,9,10-Tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(13)H(13)NO, the dihedral angle between the benzene and pyrrole rings is 1.05?(5)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular N-H?O hydrogen bonds form centrosymmetric dimers. A C-H?? inter-action, involving the benzene ring, is also found in the structure.

| S-EPMC2960645 | biostudies-literature

2,5-Dimethyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(15)H(17)NO, the dihedral angle between the benzene and pyrrole rings is 1.45?(13)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular C-H?O hydrogen bonds are found.

| S-EPMC3009033 | biostudies-literature

2-Chloro-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(13)H(12)ClNO, the dihedral angle between the benzene and pyrrole rings is 1.38?(9)°. The cyclo-heptene ring adopts a distorted twist chair and sofa conformation. Inter-molecular N-H?O hydrogen bonds form an R(2) (2)(10) loop in the crystal packing. Further, weak C-H?O and C-H?? (involving the benzene ring) inter-actions are found in the crystal structure.

| S-EPMC3379447 | biostudies-literature

4-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title compound, C(14)H(15)NO, the seven-membered ring exhibits a slightly distorted twist-boat conformation. The pyrrole ring forms a dihedral angle of 1.44 (10)° with the fused benzene ring. N-H⋯O hydrogen bonds form a centrosymmetric dimer and weak C-H⋯π inter-actions are also found in the crystal structure.

| S-EPMC2968932 | biostudies-literature

7,8,9,10-Tetra-hydro-2-methyl-cyclo-hepta-[b]indol-6(5H)-one.

Project description:The title compound, C(14)H(15)NO, was synthesized from 2-hydroxy-methyl-enecyclo-hepta-none via a Japp-Klingemann acid-catalyzed cyclization. The seven-membered ring exhibits a slightly distorted envelope conformation. N-H⋯O hydrogen bonds form a centrosymmetric dimer; C-H⋯O hydrogen bonds and π-π stacking inter-actions (the centers of the atoms involved in the stacking interaction are separated by 3.504 Å) give rise to another type of centrosymmetric dimer. In combination, these inter-actions create a stair-like chain of mol-ecules that inter-acts only loosely with neighboring chains via van der Waals inter-actions and weak C-H⋯π contacts.

| S-EPMC2961774 | biostudies-literature

5-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Project description:In the title mol-ecule, C(14)H(15)NO, the dihedral angle between the benzene and pyrrole rings is 1.99?(12)°. The cyclo-heptene ring adopts a slightly distorted boat conformation.

| S-EPMC3120537 | biostudies-other

syn,syn-15,17-Di-2-naphthyl-hexa-cyclo-[10.2.1.1.1.0.0]hepta-decane deuterochloro-form monosolvate.

Project description:The main molecule of the title compound, C(37)H(36)·CDCl(3), is a hydro-carbon with two naphthalene segments attached to opposite ends of a rigid norbornylogous spacer with an overall structure that is approximately C-shaped. The dihedral angle between the naphthalene ring planes is 9.27?(7)°. The cleft that exists between the naphthalene rings is large enough that the compound crystallizes with a solvent mol-ecule (CDCl(3)) in the cleft. The CDCl(3) solvent mol-ecule is present in two disordered orientations in a 3:2 ratio, each involving C-D?? to C(6) ring centers.

| S-EPMC2970454 | biostudies-literature

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