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 | |
| Publication status | Published - 1 Jan 2015 |
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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 journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=84928128635&partnerID=8YFLogxK
U2 - 10.1107/S2056989014026334
DO - 10.1107/S2056989014026334
M3 - Article
AN - SCOPUS:84928128635
VL - 71
SP - 38
EP - 41
JO - Acta Crystallographica Section E: Structure Reports Online
JF - Acta Crystallographica Section E: Structure Reports Online
SN - 1600-5368
IS - 1
ER -