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

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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Crystal structure of 8-[7, 8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid. / Jacob, Jomon P.; Sithambaresan, M.; Kunjachan, Christy; Prathapachandra Kurup, M. R.; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 1, 01.01.2015, p. 38-41.

Research output: Contribution to journal › Article › peer-review

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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",

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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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DO - 10.1107/S2056989014026334

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AN - SCOPUS:84928128635

VL - 71

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EP - 41

JO - Acta Crystallographica Section E: Structure Reports Online

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SN - 1600-5368

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