54
Ç. Albayrak et al. / Journal of Molecular Structure 932 (2009) 43–54
The (E)-2-acetyl-4-(4-fluorophenyldiazenyl)phenol molecules
no. CCDC 712626. Copies of the data can be obtained, free of
charge, on application to CCDC, 12 Union Road, Cambridge CB2
1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.
ac.uk). Supplementary data associated with this article can
are linked into [S(6)R44(34)] motifs [18] (Fig. 12). A significant intra-
molecular interaction is noted, involving phenolic atom H and car-
bonyl atom O1, such that a six-membered ring is formed S(6) and
the weak intermolecular C–Hꢀ ꢀ ꢀO and C–Hꢀ ꢀ ꢀN hydrogen bonds re-
sult in the formation R44(34) ring motif (Fig. 12 and 13, Table 10).
The C13–O1 double bond distance in 4c is also consistent with
the value of the C@O double bond in carbonyl compounds [19].
The C10–O1, –N1@N2–, C1–N1 and C7–N2 bond lengths are con-
sistent with values observed in related compounds [14–17,20–24].
References
[1] S.C. Catino, E. Farris, Concise Encyclopedia of Chemical Technology, John Wiley
& Sons, New York, 1985.
[2] K. Venkataraman, The Chemistry of Synthetic Dyes, Academic Press, New York
and London, 1970 (Chapter VI).
4. Conclusion
[3] R. Egli, in: A.P. Peter, H.S. Freeman (Eds.), Colour Chemistry the Design and
Synthesis of Organic Dyes and Pigments, Elsevier, London, 1991 (Chapter
VII).
[4] D.M. Marmion, Handbook of U.S. Colorants, third ed., Wiley, New York, 1991.
[5] H.G. Garg, R.A. Sharma, J. Med. Chem. 12 (1969) 1122.
[6] G.E. Foley, E.J. Modest, H.N. Schlein, J. Pharm. Pharmacol. 9 (1957) 68.
[7] L.K. Ravindranath, S.R. Ramadas, S.B. Rao, Electrochim. Acta 28 (1983) 601.
[8] R.H. Boyd, in: J.F. Coetzee, C.D. Ritchie (Eds.), Solute–Solvent Interactions,
Dekker, New York, 1969, pp. 94–202.
In the present work, we report the synthesis and characteriza-
tion of some substituted azo compounds using microanalyses
(C,H,N), IR, UV–Vis, 1H and 13C NMR spectroscopic techniques.
The structures of some of these compounds were determined by
X-ray diffraction studies. In the IR spectra of substituted azo com-
pounds, the
m(C@O) and m(N@N) bands are observed at 1630–
1650 cmꢂ1 and 1409–1433 cmꢂ1, respectively.
[9] N.M. Rageh, Chem. Pap. 59 (2005) 244.
In the 13C NMR spectra of these azo compounds the carbonyl
carbon (C14) resonates at 174–204 ppm. Furter data are presented
in Table 5. In the 1H NMR spectra, the resonance of hydroxyl proton
at 11–12 ppm is due to the presence of intramolecular hydrogen
[10] M. Odabasßog˘lu, Ç. Albayrak, R. Özkanca, F.Z. Akyan, P. Lonecke, J. Mol. Struct.
840 (2007) 71.
[11] R.M. Silverstein, F.X. Webster, D.J. Kiemle, Spectrometric Identification of
Organic Compounds, seventh ed., John Wiley & Sons, New York, 2005.
[12] L.J. Farrugia, J. Appl. Crystallogr. 30 (1997) 565.
bonding
m
(O–Hꢀ ꢀ ꢀO) frequencies in the structure.
[13] L.J. Farrugia, WinGX. University of Glasgow, Scotland, 1998.
_
[14] N.O. Iskeleli, Ç. Albayrak, E. Ag˘ar, Acta Crystallogr. E62 (2006) o4802.
X-ray investigations show that the (E)-2-acetyl-4-(phenyldiaze-
nyl)phenols the aromatic rings, which adopt a trans configuration
about the N@N double bond are nearly coplanar. The (E)-2-acet-
yl-4-(4-fluorophenyldiazenyl)phenol molecules are linked into
[S(6)R44(34)] motifs. A significant intramolecular interaction is
noted, involving phenolic atom H and carbonyl atom O, such that
a six-membered ring is formed.
[15] Ö. Deveci, Sß. Isßık, Ç. Albayrak, E. Ag˘ar, Acta Crystallogr. E61 (2005) o2878.
[16] G. Özdemir, Sß. Isßık, Ç. Albayrak, E. Ag˘ar, Acta Crystallogr. E61 (2005) o342.
[17] Ö. Deveci, Sß. Ißsık, Ç. Albayrak, E. Ag˘ar, Acta Crystallogr. E61 (2005)
o3226.
[18] M.C. Eter, Acc. Chem. Res. 23 (1990) 120.
[19] M.G. Loudon, Organic Chemistry, fourth ed., Oxford University press, 2002.
[20] Ç. Albayrak, M. Odabasßog˘lu, O. Büyükgüngör, P. Lonecke, Acta Crystallogr. C60
(2004) o318.
[21] M. Odabasßog˘lu, Ç. Albayrak, O. Büyükgüngör, H. Goesmann, Acta Crystallogr.
C59 (2003) o234.
Appendix Supplementary. material
[22] C.C. Ersanlı, Ç. Albayrak, M. Odabasßog˘lu, C. Thöne, A. Erdönmez, Acta
Crystallogr. C60 (2004) o133.
[23] C.C. Ersanlı, M. Odabasßog˘lu, Ç. Albayrak, A. Erdönmez, Acta Crystallogr. E60
Crystallographic data (excluding structure factors) for the struc-
tures in this paper have been deposited with the Cambridge
Crystallographic Data Centre as the supplementary publication
(2004) o230.
[24] C.C. Ersanlı, Ç. Albayrak, M. Odabasßog˘lu, C. Kazak, A. Erdönmez, Acta
Crystallogr. C60 (2004) o455.