The compounds, 5-methyl-5H-dibenzo[b,f]azepine (1) and 5-(4-methylbenzyl)-5H-dibenzo[b,f]azepine (2), were synthesized and characterized by spectral studies, and finally confirmed by single crystal X-ray diffraction method. The compound 1 crystallizes in the orthorhombic crystal system in Pca21 space group, having cell parameters (18) ？, (18) ？, (13) ？, and and (3) ？3. And the compound 2 crystallizes in the orthorhombic crystal system and space group Pbca, with cell parameters (5) ？, (2) ？, (7) ？, and and (16) ？3. The azepine ring of both molecules 1 and 2 adopts boat conformation with nitrogen atom showing maximum deviations of 0.483 (2) ？ and 0.5025 (10) ？, respectively. The C–H？π short contacts were observed. The dihedral angle between fused benzene rings to the azepine motif is 47.1 (2)° for compound 1 and 52.59 (6)° for compound 2, respectively. The short contacts were analyzed and Hirshfeld surfaces computational method for both molecules revealed that the major contribution is from C？H and H？H intercontacts. 1. Introduction Azepine derivatives have showed to be associated with different pharmacological activities such as antiviral, anticancer, anti-insecticidal, and vasopressin antagonist. Iminostilbene derivatives are found in montainine, coccinine, manthine, and pancracine alkaloids present in Haemanthus and Rhodophiala species [1]. They are the derivatives of drugs, such as carbamazepine [2], opipramol [3], and oxcarbazepine [4], which are used as anticonvulsants and antidepressants and in the treatment of epilepsy and trigeminal neuralgia [5]. Another compound, G32883, an iminostilbene derivative, shows effect on peripheral nerves [6]. Recently, it is reported that carbamazepine with magnesium oxide is used to treat anticonvulsant in albino rats [7]. Lateral dibenzazepine moieties are known to have potential to act as substituents for the binding site of the acetylcholine M2 receptor [8]. The 11-phenyl-[b,e]-dibenzazepine compounds are proved to be novel antitumor compounds [9]. Synthesis and crystal structures of other iminostilbene derivatives, 5-(prop-2-yn-1-yl)-5H-dibenzo[b,f]-azepine, orthorhombic polymorph, and 5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)methyl]-5H-dibenzo[b,f]azepine have been reported [10, 11]. As a part of our ongoing research on the synthesis and crystal structures and their importance of iminostilbene derivatives, we report here the synthesis and characterization by spectral studies and crystal structure using single crystal X-ray crystal diffraction of compounds 5-methyl-5H-dibenzo[b,f]azepine (1) and
References
[1]
P. Panneerselvam, K. Sandya, and K. Vijayalakshmi, “Dibenazoazepine, a pharmacologically active moiety,” ISOR Journal of Applied Chemistry, vol. 1, no. 6, pp. 41–44, 2012.
[2]
B. W. Rockliff and E. H. Davis, “Controlled sequential trials of carbamazepine in trigeminal neuralgia,” Archives of Neurology, vol. 15, no. 2, pp. 129–136, 1966.
[3]
H.-J. M？ller, H.-P. Volz, I. W. Reimann, and K.-D. Stoll, “Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group,” Journal of Clinical Psychopharmacology, vol. 21, no. 1, pp. 59–65, 2001.
[4]
P. C. Fuenfschilling, W. Zaugg, U. Beutler et al., “A new industrial process for oxcarbazepine,” Organic Process Research and Development, vol. 9, no. 3, pp. 272–277, 2005.
[5]
M. P. Sadashiva, B. H. Doreswamy, Basappa, K. S. Rangappa, M. A. Sridhar, and J. S. Prasad, “Synthesis and crystal structure of 5-allyl-5H-dibenzo[b,f]azepine,” Journal of Chemical Crystallography, vol. 35, no. 3, pp. 171–175, 2005.
[6]
H. Honda and M. B. Allen, “The effect of an iminostilbene derivative (G32883) on peripheral nerves,” Journal of the Medical Association of Georgia, vol. 62, no. 2, pp. 38–42, 1973.
[7]
N. A. Patil, H. S. Somashekar, S. Narendranath, P. Prashanth, S. K. Reddy, and A. Bhandarkar, “Evaluation of anticonvulsant activity of magnesium oxide alone and along with carbamazepine,” Asian Journal of Pharmaceutical and Clinical Research, vol. 5, no. 2, pp. 142–145, 2012.
[8]
R. Li, C. Trankle, K. Mohr, and U. Holzgrabe, “Hexamethonium-type allosteric modulators of the muscarinic receptors bearing lateral dibenzazepine moieties,” Archiv der Pharmazie, vol. 334, no. 4, pp. 121–124, 2001.
[9]
R. A. Al-Qawasmeh, Y. Lee, M.-Y. Cao et al., “11-phenyl-[b,e]-dibenzazepine compounds: novel antitumor agents,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 1, pp. 104–107, 2009.
[10]
M. M. M. Abdoh, S. Madan Kumar, K. S. Vinay kumar, B. C. Manjunath, M. P. Sadashiva, and N. K. Lokanath, “5-(prop-2-yn-1-yl)-5H-dibenzo[b,f]-azepine: orthorhombic polymorph,” Acta Crystallographica E, vol. 69, p. o17, 2013.
[11]
B. C. Manjunath, K. S. Vinay Kumar, S. Madan Kumar, M. P. Sadashiva, and N. K. Lokanath, “5-[(4-benzyl-1H -1,2,3-triazol-1-yl)methyl]-5H -dibenzo[b,f ]azepine,” Acta Crystallographica E, vol. 69, p. o1233, 2013.
[12]
S. Madan Kumar, B. C. Manjunath, G. S. Lingaraju, M. M. M. Abdoh, M. P. Sadashiva, and N. K. Lokanath, “A Hirshfeld surface analysis and crystal structure of 2′-[1-(2-fluoro-phenyl)-1H-tetrazol-5-yl]-4-methoxy-biphenyl-2-carbaldehyde,” Crystal Structure Theory and Applications, vol. 3, pp. 124–131, 2013.
[13]
Apex2 (Version 2013), Program for Bruker CCD X-Ray Diffractometer Control, Bruker AXS Inc., Madison, Wis, USA, 2013.
[14]
G. M. Sheldrick, “A short history of SHELX,” Acta Crystallographica A, vol. 64, no. 1, pp. 112–122, 2008.
[15]
C. F. Macrae, I. J. Bruno, J. A. Chisholm et al., “Mercury CSD 2.0—new features for the visualization and investigation of crystal structures,” Journal of Applied Crystallography, vol. 41, no. 2, pp. 466–470, 2008.
[16]
S. K. Wolff, D. J. Grimwood, J. J. McKinnon, D. Jayatilaka, and M. A. Spackman, CrystalExplorer 3.0, University of Western Australia, Perth, Australia, 2001.
[17]
M. A. Spackman and J. J. McKinnon, “Fingerprinting intermolecular interactions in molecular crystals,” CrystEngComm, vol. 4, no. 66, pp. 378–392, 2002.
[18]
M. A. Spackman, J. J. McKinnon, and D. Jayatilaka, “Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals,” CrystEngComm, vol. 10, no. 4, pp. 377–388, 2008.
[19]
D. Jayatilaka, D. J. Grimwood, A. Lee et al., TONTO—A System for Computational Chemistry, The University of Western Australia, Nedlands, Australia, 2005.
[20]
D. Cremer and J. A. Pople, “A general definition of ring puckering coordinates,” Journal of the American Chemical Society, vol. 97, no. 6, pp. 1354–1358, 1975.
