Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

Jomon P. Jacob; M. Sithambaresan; Christy Kunjachan; M. R. Prathapachandra Kurup; W. T A Harrison

doi:10.1107/S2056989014026334

Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

Jomon P. Jacob, M. Sithambaresan^*, Christy Kunjachan, M. R. Prathapachandra Kurup, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

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Abstract

The title compound, C₄₀H₂₂Cl₂O₄, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroaceto-phenone in the presence of KOH in methanol. The dihedral angles between the central cyclopenta[a]acenaphthylene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chlorobenzoyl rings are 62.25(10) and 70.19(10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intramolecular aromatic π-π stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid-centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C - H⋯π interaction between one of the H atoms of the central moiety and the 4-chlorobenzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carboxylic acid inversion dimers generate R ₂²(8) loops. The dimers are linked by weak C - H⋯O and C - H⋯Cl hydrogen bonds and C - H⋯π interactions, generating a three-dimensional architecture.

Original language	English
Pages (from-to)	38-41
Number of pages	4
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	1
DOIs	https://doi.org/10.1107/S2056989014026334
Publication status	Published - 1 Jan 2015

Bibliographical note

JPJ and CK are obliged to Dr S. Prathapan for introducing them to the field of domino reactions. SAIF (STIC) CUSAT, Kochi, India, provided spectroscopic, analytical and single crystal X-ray diffraction data.

Keywords

4-chloroacetophenone
Acenaphthenequinone
Crystal structure
Domino reaction
Hydrogen bonding

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Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7Hcyclopenta[a]acenaphthylen-9-yl]naphthalene-1-
© 2015 Jacob et al. Licence: Creative Commons Attribution (CC-BY) http://creativecommons.org/licenses/by/4.0
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title = "Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid",

abstract = "The title compound, C40H22Cl2O4, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroaceto-phenone in the presence of KOH in methanol. The dihedral angles between the central cyclopenta[a]acenaphthylene fused-ring system (r.m.s. deviation = 0.066 {\AA}) and the 4-chlorobenzoyl rings are 62.25(10) and 70.19(10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intramolecular aromatic π-π stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid-centroid distances of 3.4533 (16) and 3.5311 (16) {\AA}, and a C - H⋯π interaction between one of the H atoms of the central moiety and the 4-chlorobenzoyl ring with an H⋯π distance of 2.57 {\AA}. In the crystal, carboxylic acid inversion dimers generate R 22(8) loops. The dimers are linked by weak C - H⋯O and C - H⋯Cl hydrogen bonds and C - H⋯π interactions, generating a three-dimensional architecture.",

keywords = "4-chloroacetophenone, Acenaphthenequinone, Crystal structure, Domino reaction, Hydrogen bonding",

author = "Jacob, {Jomon P.} and M. Sithambaresan and Christy Kunjachan and {Prathapachandra Kurup}, {M. R.} and Harrison, {W. T A}",

note = "JPJ and CK are obliged to Dr S. Prathapan for introducing them to the field of domino reactions. SAIF (STIC) CUSAT, Kochi, India, provided spectroscopic, analytical and single crystal X-ray diffraction data.",

year = "2015",

month = jan,

day = "1",

doi = "10.1107/S2056989014026334",

language = "English",

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journal = "Acta Crystallographica Section E: Structure Reports Online",

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T1 - Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

AU - Jacob, Jomon P.

AU - Sithambaresan, M.

AU - Kunjachan, Christy

AU - Prathapachandra Kurup, M. R.

A2 - Harrison, W. T A

N1 - JPJ and CK are obliged to Dr S. Prathapan for introducing them to the field of domino reactions. SAIF (STIC) CUSAT, Kochi, India, provided spectroscopic, analytical and single crystal X-ray diffraction data.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - The title compound, C40H22Cl2O4, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroaceto-phenone in the presence of KOH in methanol. The dihedral angles between the central cyclopenta[a]acenaphthylene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chlorobenzoyl rings are 62.25(10) and 70.19(10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intramolecular aromatic π-π stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid-centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C - H⋯π interaction between one of the H atoms of the central moiety and the 4-chlorobenzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carboxylic acid inversion dimers generate R 22(8) loops. The dimers are linked by weak C - H⋯O and C - H⋯Cl hydrogen bonds and C - H⋯π interactions, generating a three-dimensional architecture.

AB - The title compound, C40H22Cl2O4, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroaceto-phenone in the presence of KOH in methanol. The dihedral angles between the central cyclopenta[a]acenaphthylene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chlorobenzoyl rings are 62.25(10) and 70.19(10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intramolecular aromatic π-π stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid-centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C - H⋯π interaction between one of the H atoms of the central moiety and the 4-chlorobenzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carboxylic acid inversion dimers generate R 22(8) loops. The dimers are linked by weak C - H⋯O and C - H⋯Cl hydrogen bonds and C - H⋯π interactions, generating a three-dimensional architecture.

KW - 4-chloroacetophenone

KW - Acenaphthenequinone

KW - Crystal structure

KW - Domino reaction

KW - Hydrogen bonding

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U2 - 10.1107/S2056989014026334

DO - 10.1107/S2056989014026334

M3 - Article

AN - SCOPUS:84928128635

SN - 1600-5368

VL - 71

SP - 38

EP - 41

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 1

ER -

Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

Abstract

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Keywords

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