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

Research output: Contribution to journalArticle

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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 languageEnglish
Pages (from-to)38-41
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number1
DOIs
Publication statusPublished - 1 Jan 2015

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Dihedral angle
Naphthalene
Carboxylic Acids
Carboxylic acids
naphthalene
carboxylic acids
Dimers
Crystal structure
crystal structure
Acids
rings
Methanol
Hydrogen bonds
Atoms
centroids
Crystals
dihedral angle
dimers
acids
twisting

Keywords

  • 4-chloroacetophenone
  • Acenaphthenequinone
  • Crystal structure
  • Domino reaction
  • Hydrogen bonding

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

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 journalArticle

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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.",
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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.",
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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

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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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JO - Acta Crystallographica Section E: Structure Reports Online

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SN - 1600-5368

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