Limits...
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.

Nagalakshmi RA, Suresh J, Maharani S, Kumar RR, Lakshman PL - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: 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⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Physics, The Madura College, Madurai 625 011, India.

ABSTRACT
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⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.

No MeSH data available.


Related in: MedlinePlus

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4257429&req=5

fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The mol­ecular structure of the title compound is shown in Fig. 1 ▶. The pyridine ring is connected to a benzene ring by a –CH2—NH2– chain. The cyclo­heptane ring adopts a chair conformation with puckering parameters Q2 = 0.4634 (15) Å, ϕ2 = 304.24 (18)° and Q3 = 0.6481 (16) Å and ϕ3 = 284.37 (12)°. The phenyl (C22–C27) and benzene (C31–C36) rings are inclined to one another by 58.91 (7)° and to the pyridine (N3/C2–C6) ring by 76.68 (7) and 49.80 (6)°, respectively. The N atom of the carbo­nitrile group, N1, is significantly displaced by 0.2247 (1) Å from the plane of the pyridine ring, perhaps due to steric crowding. The shortening of the C—N distance [C5—N3 = 1.3390 (14) Å] and the opening of the N3—C5—C4 angle to 124.47 (10)° may be attributed to the size of the substituent at C1, and correlates well with the values observed in a similar structure (Çelik et al., 2013 ▶). There is conjugation between the donor (NH) and the acceptor (CN) groups via the C2—C6 bond. Thus the C6—N2 distance of 1.3502 (14) Å is shorter than the average conjugated C—N single bond, 1.370 (1) Å, found in the Cambridge Structural Database (Version 5.35; Groom & Allen, 2014 ▶). Steric hindrances rotate the benzene ring out of the plane of the central pyridine ring by 49.80 (6)°. This twist may be due to the non-bonded inter­actions between one of the ortho H atoms of the benzene ring and atom H7B of the cyclo­heptane ring. As a result of the π–π conjugation of atom O1, the O1—C34 bond length of 1.3618 (15) Å is significantly shorter than the O1—C37 distance of 1.410 (2) Å. An enlarge­ment of bond angle [C33—C34—O1 = 124.34 (13)°] on one side and a narrowing of bond angle [C35—C34—O1 = 116.29 (12)°] on the other side of the benzene ring may be due to the steric repulsion between the aromatic rings and the methyl group, as found in a similar structure (Tokuno et al., 1986 ▶).


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.

Nagalakshmi RA, Suresh J, Maharani S, Kumar RR, Lakshman PL - Acta Crystallogr Sect E Struct Rep Online (2014)

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257429&req=5

fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The mol­ecular structure of the title compound is shown in Fig. 1 ▶. The pyridine ring is connected to a benzene ring by a –CH2—NH2– chain. The cyclo­heptane ring adopts a chair conformation with puckering parameters Q2 = 0.4634 (15) Å, ϕ2 = 304.24 (18)° and Q3 = 0.6481 (16) Å and ϕ3 = 284.37 (12)°. The phenyl (C22–C27) and benzene (C31–C36) rings are inclined to one another by 58.91 (7)° and to the pyridine (N3/C2–C6) ring by 76.68 (7) and 49.80 (6)°, respectively. The N atom of the carbo­nitrile group, N1, is significantly displaced by 0.2247 (1) Å from the plane of the pyridine ring, perhaps due to steric crowding. The shortening of the C—N distance [C5—N3 = 1.3390 (14) Å] and the opening of the N3—C5—C4 angle to 124.47 (10)° may be attributed to the size of the substituent at C1, and correlates well with the values observed in a similar structure (Çelik et al., 2013 ▶). There is conjugation between the donor (NH) and the acceptor (CN) groups via the C2—C6 bond. Thus the C6—N2 distance of 1.3502 (14) Å is shorter than the average conjugated C—N single bond, 1.370 (1) Å, found in the Cambridge Structural Database (Version 5.35; Groom & Allen, 2014 ▶). Steric hindrances rotate the benzene ring out of the plane of the central pyridine ring by 49.80 (6)°. This twist may be due to the non-bonded inter­actions between one of the ortho H atoms of the benzene ring and atom H7B of the cyclo­heptane ring. As a result of the π–π conjugation of atom O1, the O1—C34 bond length of 1.3618 (15) Å is significantly shorter than the O1—C37 distance of 1.410 (2) Å. An enlarge­ment of bond angle [C33—C34—O1 = 124.34 (13)°] on one side and a narrowing of bond angle [C35—C34—O1 = 116.29 (12)°] on the other side of the benzene ring may be due to the steric repulsion between the aromatic rings and the methyl group, as found in a similar structure (Tokuno et al., 1986 ▶).

Bottom Line: 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⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Physics, The Madura College, Madurai 625 011, India.

ABSTRACT
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⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.

No MeSH data available.


Related in: MedlinePlus