Advertisement

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
ORIGINAL PAPER

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 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.

Keywords

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

Notes

Acknowledgments

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.

References

  1. 1.
    Satoshi H, Tominari C (2001) Nat Prod Rep 18:66–87CrossRefGoogle Scholar
  2. 2.
    Gribble GW (2000) J Chem Soc Perkins Trans 1:1045–1075Google Scholar
  3. 3.
    Knolker HJ, Reddy KR (2002) Chem Rev 102:4303–4427CrossRefGoogle Scholar
  4. 4.
    Kawasaki T, Higuchi K (2005) Nat Prod Rep 22:761–793CrossRefGoogle Scholar
  5. 5.
    Bennasar ML, Vidal B, Bosch J (1993) J Am Chem Soc 115:5340–5341CrossRefGoogle Scholar
  6. 6.
    Bennasar ML, Vidal B, Bosch J (1997) J Org Chem 62:3597–3609CrossRefGoogle Scholar
  7. 7.
    Bennasar ML, Zulaica E, Juan C, Llauger L, Bosch J (1999) Tetrahedron Lett 40:3961CrossRefGoogle Scholar
  8. 8.
    Bennasar ML, Zulaica E, Sole D, Alonso A (2008) Synlett 667–670Google Scholar
  9. 9.
    Benoit J, Routier S, Merour JY, Colson P, Hoursier C, Bailly C (2000) Anticancer Res 20:3307Google Scholar
  10. 10.
    Clivio P, Richard B, Nuzillard JM, Zeches-Hanrot M (1995) Phytochemistry 40:987–990CrossRefGoogle Scholar
  11. 11.
    Bennasar ML, Vidal B, Kumar R, Lasaro A, Bosch J (2000) Eur J Org Chem 3919Google Scholar
  12. 12.
    Bennasar ML, Vidal B, Lazaro A, Kumar R, Bosch J (1996) Tetrahedron Lett 37:3541–3544CrossRefGoogle Scholar
  13. 13.
    Sridharan M, Rajendra Prasad KJ, Gunaseelan A, Thiruvalluvar A, Butcher RJ (2009) Acta Cryst E65:o698Google Scholar
  14. 14.
    Hegde V, Hung C-Y, Madhukar P, Cunningham R, Hopfner T, Thummel RP (1993) J Am Chem Soc 115:872CrossRefGoogle Scholar
  15. 15.
    Kavitha V, Rajendra Prasad KJ (1999) J Heterocycl Comm 5:481–487Google Scholar
  16. 16.
    Apex2 v2.1-4 (2000) Bruker advanced X-ray solutions. Bruker AXS Inc, MadisonGoogle Scholar
  17. 17.
    SHELXTL (Version 6.14) (2000–2003) Bruker advanced X-ray solutions, Bruker AXS Inc., Madison, Wisconsin, USAGoogle Scholar
  18. 18.
    Gavezzotti A (2008) CrystEngComm 10(4):389–398Google Scholar
  19. 19.
    Dabros M, Emery PR, Thalladi VR (2007) Angew Chem Int Ed 46(22):4132–4135CrossRefGoogle Scholar
  20. 20.
    Lynch DE, Smith G, Byriel KA, Kennard CHL (1992) J Chem Soc Chem Commun 300–301Google Scholar
  21. 21.
    Smolka T, Boese R, Sustmann R (1999) Struct Chem 10:429–431CrossRefGoogle Scholar
  22. 22.
    Aakeröy CB, Beatty AM, Helfrich BA (2001) Angew Chem Int Ed 40:3240–3242CrossRefGoogle Scholar
  23. 23.
    Cheung EY, Kitchin SJ, Harris KDM, Imai Y, Tajima N, Kuroda RJ (2003) Am Chem Soc 125:14658–14659CrossRefGoogle Scholar
  24. 24.
    Aakeröy CB, Desper J, Urbina JF (2005) Chem Commun 2820–2822Google Scholar
  25. 25.
    Bhogala BR, Basavoju S, Nangia A (2005) Cryst Growth Des 5:1683–1686CrossRefGoogle Scholar
  26. 26.
    Friščić T, Trask AV, Jones W, Motherwell WDS (2006) Angew Chem Int Ed 45:7546–7550CrossRefGoogle Scholar
  27. 27.
    Sridharan M, Rajendra Prasad KJ, Kotheimer AE, Wagner TR, Zeller M (2009) J Chem Cryst 39(11):804–811CrossRefGoogle Scholar

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

Personalised recommendations