X-ray structure and activity analysis of 3-bromomethyl -2-chloro-quinoline
##plugins.themes.bootstrap3.article.main##
Abstract
The structure of 3-bromomethyl-2-chloro-quinoline crystallizes in the triclinic crystal space group P‘1 with unit cell parameters a=6.587(2), b=7.278(3), c=10.442(3) Å, a= 83.59(3)°, b= 75.42(2)°, g= 77.39(3)°, Z= 2, V= 471.9(3)Å3. The structure has converged to a final R-value of 0.0734. The phenyl Ring-B has normal geometry while the pyridine Ring-A has slightly distorted conformation. The asymmetry parameter calculations, i.e., DC2 and DCs for the pyridine ring indicates that the structure is planar. There exists one intramolecular hydrogen bonded interaction of the type C-H…Cl and one C-H…N intermolecular interaction. The structure is stabilized by Van der Waals forces.
##plugins.themes.bootstrap3.article.details##
##plugins.themes.bootstrap3.article.details##
Keywords
Crystal structure, Activity, Quinoline, Hetereocyclic compounds, X-ray structure
References
Chand, B. (2008). A study of molecular and crystal structures of some steroidal molecules’, Ph.D. Thesis University of Jammu, Jammu Tawi, India.
CrysAlisPro and CrysAlisRED (2007). Softwares for crystal data collection and reduction, Oxford Diffraction Limited, Abingdon, Oxfordshire, England.
Duax, W.L. and Norton, D.A. (1975). Atlas of Steroid Structure, New York, Plenum Press, 1, 18.
Farrugia, L. J. (1997), Molecular Graphics-ORTEP-3 for Windows. Journal of Applied Crystallography, 30, 565.
Garcia, M. S., Martinez, J. A. H., Palma, A.R. and Kpuznetsov, V. (2000). Crystal structure of Spiro[cyclohexane-1,2’-6’- methoxy-1’-(a-chloroacetyl)-1’,2’,3’,4’-tetrahydro-4’- methyl quinoline. Analytical Sciences, 16: 889.
Gilchrist, T.L. (1997). Heterocyclic Chemistry’, 3rd ed., Addison Wesley Longman, England, 231.
Kouznetsov, V., Palma, A., Ewert, C. and Varlamov, A. (1998). Some aspects of reduced quinoline chemistry, Journal of Heterocyclic Chemistry, 35: 761.
Lekhok, K.C., Prajapati, D. and Boruah, R.C. (2008). Indium(III) Trifluoromethanesulfonate: An efficient reusable catalyst for the alkynylation- Cyclization of 2- Aminoaryl ketones and synthesis of 2, 4- disubstituted quinolines. Synlet, 5: 0655-0658.
Nardelli, M. (1995). A system of computer routines for calculating molecular structure parameters from the results of crystal structure analysis, Journal of Applied Crystallography, 28 : 59.
Palani, K., Ponnuswamy, A., Ponnuswamy, M.N.G., Yathirajan, H.S., Prabhuswamy, B., Raju, C.R., Nagaraja, P. and Shashikanth, S. (2004). Crystal structure of 2-chloro-3- (ß-nitrovinyl)quinoline, Analytical Sciences, 20: 403.
Rajnikant, Gupta, V. K., Deshmukh, M. B., Varghese, B. and Dinesh (2002). Crystal structure analysis of 4- phenylquinolin-2-(1H)-one. Crystallographic Reports, 47: 449.
Robert, A. and Meunier, B. (1998). Is alkylation the main mechanism of action of the antimalarial drug artemisinin, Chemical Society Review, 27: 273.
Saito, I., Sando, S., and Nakatani, K. (2001). Improved selectivity for the binding of napthyridine dimmer to quininequanine mismatch, Bioorganic and Medicinal Chemistry Letters, 9:2381.
Schneider, G., Baringhaus, K-H and Hugo (2008). In: Molecular design: Concepts and Applications, Wiley-VCH, 262.
Sheldrick, G.M. (1986). SHELXS86: Program for crystal structure determination, University of Gottingen, Germany.
Sheldrick, G.M. (1997). SHELXL97: Program for the refinement of crystal structures, University of Gottingen, Germany.
Sudha, L., Subramanian, K., Sivaraman, J., Ramakrishnan, V.T.R., Steiner, Th. and Koellner, G. (1995a). 5-(Isopropylamino)- 8-methyl-2-quinoline. Acta Crystallography, C51: 1026.
Sudha, L., Subramanian, K., Sivaraman, J., Sriraghavana, K. and Steiner,Th. (1995b). 5- Amino- 8-methyl-2-quinoline. Acta Crystallography, C51: 1689.
Sudha, L., Subramanian, K., Steiner, Th., Koellner, G., Ramakrishnan, V.T.R. and Sriraghavana, K. (1997). 5-Dimethylamino-8-methyl-2-quinoline. Acta Crystallography, C53: 606
CrysAlisPro and CrysAlisRED (2007). Softwares for crystal data collection and reduction, Oxford Diffraction Limited, Abingdon, Oxfordshire, England.
Duax, W.L. and Norton, D.A. (1975). Atlas of Steroid Structure, New York, Plenum Press, 1, 18.
Farrugia, L. J. (1997), Molecular Graphics-ORTEP-3 for Windows. Journal of Applied Crystallography, 30, 565.
Garcia, M. S., Martinez, J. A. H., Palma, A.R. and Kpuznetsov, V. (2000). Crystal structure of Spiro[cyclohexane-1,2’-6’- methoxy-1’-(a-chloroacetyl)-1’,2’,3’,4’-tetrahydro-4’- methyl quinoline. Analytical Sciences, 16: 889.
Gilchrist, T.L. (1997). Heterocyclic Chemistry’, 3rd ed., Addison Wesley Longman, England, 231.
Kouznetsov, V., Palma, A., Ewert, C. and Varlamov, A. (1998). Some aspects of reduced quinoline chemistry, Journal of Heterocyclic Chemistry, 35: 761.
Lekhok, K.C., Prajapati, D. and Boruah, R.C. (2008). Indium(III) Trifluoromethanesulfonate: An efficient reusable catalyst for the alkynylation- Cyclization of 2- Aminoaryl ketones and synthesis of 2, 4- disubstituted quinolines. Synlet, 5: 0655-0658.
Nardelli, M. (1995). A system of computer routines for calculating molecular structure parameters from the results of crystal structure analysis, Journal of Applied Crystallography, 28 : 59.
Palani, K., Ponnuswamy, A., Ponnuswamy, M.N.G., Yathirajan, H.S., Prabhuswamy, B., Raju, C.R., Nagaraja, P. and Shashikanth, S. (2004). Crystal structure of 2-chloro-3- (ß-nitrovinyl)quinoline, Analytical Sciences, 20: 403.
Rajnikant, Gupta, V. K., Deshmukh, M. B., Varghese, B. and Dinesh (2002). Crystal structure analysis of 4- phenylquinolin-2-(1H)-one. Crystallographic Reports, 47: 449.
Robert, A. and Meunier, B. (1998). Is alkylation the main mechanism of action of the antimalarial drug artemisinin, Chemical Society Review, 27: 273.
Saito, I., Sando, S., and Nakatani, K. (2001). Improved selectivity for the binding of napthyridine dimmer to quininequanine mismatch, Bioorganic and Medicinal Chemistry Letters, 9:2381.
Schneider, G., Baringhaus, K-H and Hugo (2008). In: Molecular design: Concepts and Applications, Wiley-VCH, 262.
Sheldrick, G.M. (1986). SHELXS86: Program for crystal structure determination, University of Gottingen, Germany.
Sheldrick, G.M. (1997). SHELXL97: Program for the refinement of crystal structures, University of Gottingen, Germany.
Sudha, L., Subramanian, K., Sivaraman, J., Ramakrishnan, V.T.R., Steiner, Th. and Koellner, G. (1995a). 5-(Isopropylamino)- 8-methyl-2-quinoline. Acta Crystallography, C51: 1026.
Sudha, L., Subramanian, K., Sivaraman, J., Sriraghavana, K. and Steiner,Th. (1995b). 5- Amino- 8-methyl-2-quinoline. Acta Crystallography, C51: 1689.
Sudha, L., Subramanian, K., Steiner, Th., Koellner, G., Ramakrishnan, V.T.R. and Sriraghavana, K. (1997). 5-Dimethylamino-8-methyl-2-quinoline. Acta Crystallography, C53: 606
Issue
Section
Research Articles
This work is licensed under Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) © Author (s)
How to Cite
X-ray structure and activity analysis of 3-bromomethyl -2-chloro-quinoline. (2010). Journal of Applied and Natural Science, 2(1), 106-110. https://doi.org/10.31018/jans.v2i1.107
