Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid
The title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroacetophenone 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)...
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doaj-904f57656af244bcb2ad6eb5996e77222020-11-24T22:25:49ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-01-01711384110.1107/S2056989014026334hb7324Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acidJomon P. Jacob0M. Sithambaresan1Christy Kunjachan2M. R. Prathapachandra Kurup3Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, IndiaDepartment of Chemistry, Faculty of Science, Eastern University, Chenkalady, Sri LankaDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, IndiaDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, IndiaThe title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroacetophenone 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 R22(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.http://scripts.iucr.org/cgi-bin/paper?S2056989014026334crystal structuredomino reactionacenaphthenequinone4-chloroacetophenonehydrogen bonding |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Jomon P. Jacob M. Sithambaresan Christy Kunjachan M. R. Prathapachandra Kurup |
spellingShingle |
Jomon P. Jacob M. Sithambaresan Christy Kunjachan M. R. Prathapachandra Kurup Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid Acta Crystallographica Section E: Crystallographic Communications crystal structure domino reaction acenaphthenequinone 4-chloroacetophenone hydrogen bonding |
author_facet |
Jomon P. Jacob M. Sithambaresan Christy Kunjachan M. R. Prathapachandra Kurup |
author_sort |
Jomon P. Jacob |
title |
Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
title_short |
Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
title_full |
Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
title_fullStr |
Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
title_full_unstemmed |
Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
title_sort |
crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7h-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2015-01-01 |
description |
The title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroacetophenone 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 R22(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. |
topic |
crystal structure domino reaction acenaphthenequinone 4-chloroacetophenone hydrogen bonding |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989014026334 |
work_keys_str_mv |
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