Crystal structure of 2-benzylamino-4-(4-bromo-phenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

R. A. Nagalakshmi; J. Suresh; S. Maharani; R. Ranjith Kumar; P. L. Nilantha Lakshman; W. T A Harrison

doi:10.1107/S2056989015002820

Crystal structure of 2-benzylamino-4-(4-bromo-phenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

R. A. Nagalakshmi, J. Suresh, S. Maharani, R. Ranjith Kumar, P. L. Nilantha Lakshman^*, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

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Abstract

In the title compound C₂₂H₁₈BrN₃, the cyclopentane ring adopts an envelope conformation with the central methylene C atom as the flap. The dihedral angles between the central pyridine ring and the pendant benzyl and and bromo-benzene rings are 82.65 (1) and 47.23 (1)°, respectively. In the crystal, inversion dimers linked by pairs of N - H⋯N_n (n = nitrile) hydrogen bonds generate R²₂(12) loops. These dimers are linked by weak π-π interactions [centroid-centroid distance = 3.7713 (14) Å] into a layered structure.

Original language	English
Pages (from-to)	296-298
Number of pages	3
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	3
Early online date	21 Feb 2015
DOIs	https://doi.org/10.1107/S2056989015002820
Publication status	Published - 1 Mar 2015

Bibliographical note

JS and RAN thank the management of The Madura College (Autonomous), Madurai, for their encouragement and support. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42–242/2013 (SR).

Keywords

Crystal structure
Cyclopentane ring
Envelope conformation
N - H⋯N hydrogen bonding
π-π interactions

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Crystal structure 2-benzylamino-4-(4-bromophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile
© 2015 Nagalakshmiet al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0/
Final published version, 452 KBLicence: CC BY

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title = "Crystal structure of 2-benzylamino-4-(4-bromo-phenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile",

abstract = "In the title compound C22H18BrN3, the cyclopentane ring adopts an envelope conformation with the central methylene C atom as the flap. The dihedral angles between the central pyridine ring and the pendant benzyl and and bromo-benzene rings are 82.65 (1) and 47.23 (1)°, respectively. In the crystal, inversion dimers linked by pairs of N - H⋯Nn (n = nitrile) hydrogen bonds generate R22(12) loops. These dimers are linked by weak π-π interactions [centroid-centroid distance = 3.7713 (14) {\AA}] into a layered structure.",

keywords = "Crystal structure, Cyclopentane ring, Envelope conformation, N - H⋯N hydrogen bonding, π-π interactions",

author = "Nagalakshmi, {R. A.} and J. Suresh and S. Maharani and {Ranjith Kumar}, R. and {Nilantha Lakshman}, {P. L.} and Harrison, {W. T A}",

note = "JS and RAN thank the management of The Madura College (Autonomous), Madurai, for their encouragement and support. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42–242/2013 (SR).",

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AU - Nagalakshmi, R. A.

AU - Suresh, J.

AU - Maharani, S.

AU - Ranjith Kumar, R.

AU - Nilantha Lakshman, P. L.

A2 - Harrison, W. T A

N1 - JS and RAN thank the management of The Madura College (Autonomous), Madurai, for their encouragement and support. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42–242/2013 (SR).

PY - 2015/3/1

Y1 - 2015/3/1

N2 - In the title compound C22H18BrN3, the cyclopentane ring adopts an envelope conformation with the central methylene C atom as the flap. The dihedral angles between the central pyridine ring and the pendant benzyl and and bromo-benzene rings are 82.65 (1) and 47.23 (1)°, respectively. In the crystal, inversion dimers linked by pairs of N - H⋯Nn (n = nitrile) hydrogen bonds generate R22(12) loops. These dimers are linked by weak π-π interactions [centroid-centroid distance = 3.7713 (14) Å] into a layered structure.

AB - In the title compound C22H18BrN3, the cyclopentane ring adopts an envelope conformation with the central methylene C atom as the flap. The dihedral angles between the central pyridine ring and the pendant benzyl and and bromo-benzene rings are 82.65 (1) and 47.23 (1)°, respectively. In the crystal, inversion dimers linked by pairs of N - H⋯Nn (n = nitrile) hydrogen bonds generate R22(12) loops. These dimers are linked by weak π-π interactions [centroid-centroid distance = 3.7713 (14) Å] into a layered structure.

KW - Crystal structure

KW - Cyclopentane ring

KW - Envelope conformation

KW - N - H⋯N hydrogen bonding

KW - π-π interactions

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JO - Acta Crystallographica Section E: Structure Reports Online

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Crystal structure of 2-benzylamino-4-(4-bromo-phenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

Abstract

Bibliographical note

Keywords

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