Journal of Chemical Crystallography

, Volume 40, Issue 5, pp 402–411 | Cite as

Structural Investigations on 4-Chloro-6-Phenyl-7,8,9,14-Tetrahydroquinolino [2′,3′:7,6]cyclohept[b]indoles

  • Ezhumalai Yamuna
  • Makuteswaran Sridharan
  • Karnam Jayarampillai Rajendra Prasad
  • Matthias Zeller


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 Abstract

Four 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.


Crystal structure Disorder Solid solution Z′ = 2 Quinolinocyclohept[b]indoles 



We acknowledge UGC, New Delhi, India, for the award of Major Research Project Grant No.F.No.31-122/2005. M.S thanks UGC, New Delhi for the award of research fellowship. Our sincere thanks to the Director, ISO Quality Assurance Cell, IICT, Hyderabad and, The Chairman, NMR Research Center, IISc, Bangalore for providing NMR spectra. The X-ray diffractometer was funded by NSF Grant 0087210, Ohio Board of Regents Grant CAP-491, and by Youngstown State University.


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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Ezhumalai Yamuna
    • 1
  • Makuteswaran Sridharan
    • 1
  • Karnam Jayarampillai Rajendra Prasad
    • 1
  • Matthias Zeller
    • 2
  1. 1.Department of ChemistryBharathiar UniversityCoimbatoreIndia
  2. 2.Department of ChemistryYoungstown State UniversityYoungstownUSA

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