E. Yamuna, M. Sridharan, K. Rajendra Prasad
May 1, 2010
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Influential Citations
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Journal
Journal of Chemical Crystallography
Abstract
Several 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indole derivatives were obtained in one pot synthesis reactions via acid catalyzed condensation and cyclization of 1-oxo-1,2,3,4,5,10-hexahydrocyclohept[b]indoles with 2-amino-5-chlorobenzophenone in glacial acetic acid. Parent 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indole and the 10, 11, 12 and 13-methyl derivatives all crystallize in the triclinic space group P$$ \overline{1} $$. The 11-methyl derivative crystallizes with Z′ = 2, the 10 and 12-methyl isomers cocrystallize as a solid solution of the two molecules, and the 13-methyl derivative and the parent compound each with Z′ = 1. The unit cell parameters for the four structures are a = 10.1826(8), b = 12.3918(7), c = 16.3825(8)Å, α = 91.626(1), β = 95.718(1), γ = 94.966(1)° and V = 2,047.7(2) Å3 for the 11 methyl derivative; a = 10.168(2), b = 10.304(2), c = 10.610(2)Å, α = 89.169(3), β = 87.774(3), γ = 63.726(2)° and V = 996.0(3) Å3 for the solid solution of the 10 and 12-methyl derivative, a = 9.0412(5), b = 10.4926(6), c = 10.9093(6)Å, α = 94.482(1), β = 102.181(1), γ = 95.812(1)° and V = 1,001.13(10) Å3 for the 13-methyl compound, and a = 9.6463(6), b = 10.2395(6), c = 10.6062(6)Å, α = 91.7263(8), β = 94.7200(8), γ = 114.0812(7)° and 950.85(10) Å3 for the unsubstituted parent compound. The molecular shape of the molecules is not affected by the substitution pattern and all molecules exhibit the same conformation with very similar geometries. Intermolecular interactions are limited to weak C–H···Cl hydrogen bonds, a small number of π···π stacking interactions and several C–H···π interactions, which, in combination with shape recognition, dominate the packing of the quinolinocyclohept[b]indoles.Graphical AbstractFour crystals structures of several 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indole derivatives were investigated. The molecular conformations are unaffected by the position of differently located methyl substituents. One of the structures crystallizes with Z′ = 2, another as a solid solution of two substitutional isomers.