35 6-Methoxy-5-(phenyldiazenyl)salicylaldehyde

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35 6-Methoxy-5-(phenyldiazenyl)salicylaldehyde
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 6-Methoxy-5-(phenyldiazenyl)salicylaldehyde Cem C¨uneyt Ersanlı, Mustafa Odabas¸o ˇglu, C¸i ˇgdem Albayrak and Ahmet Erd ¨onmez Copyright © International Union of CrystallographyAuthor(s) of this paper may load this reprint on their own web site provided that this cover page is retained. Republication of this article or itsstorage in electronic databases or the like is not permitted without prior permission in writing from the IUCr. Acta Cryst. (2004). E 60 , o230–o231 Cem C¨uneyt Ersanlı et al. ¯ C 14 H 12 N 2 O 3  organic papers o230 Cem CuÈ neyt Ersanlõ et al.  C 14 H 12 N 2 O 3 DOI: 10.1107/S1600536804000819 Acta Cryst. (2004). E 60 , o230±o231 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 6-Methoxy-5-(phenyldiazenyl)salicylaldehyde Cem CuÈneyt Ersanlõ, a * MustafaOdabasËogÏlu, b CËigÏdem Albayrak b and Ahmet ErdoÈnmez a a Department of Physics, Faculty of Arts andSciences, Ondokuz Mayõs University, 55139Kurupelit Samsun, Turkey, and b Department of Chemistry, Faculty of Arts and Sciences,Ondokuz Mayõs University, 55139 KurupelitSamsun, TurkeyCorrespondence e-mail: ccersan@omu.edu.tr Key indicators Single-crystal X-ray study T  = 293 KMean '  (C±C) = 0.002 AÊ R factor = 0.042 wR factor = 0.100Data-to-parameter ratio = 14.2For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e. # 2004 International Union of CrystallographyPrinted in Great Britain ± all rights reserved The structure of the title compound, C 14 H 12 N 2 O 3 , determinedat room temperature, shows that the molecule is approx-imately planar in the solid state, as found for other diazene(azobenzene) derivatives. The compound exhibits trans geometry with respect to the azo double bond. Comment Diazenes have been the most widely used class of dyes, owingto their versatile applications in various ®elds, such as dyeingtextile ®bres, colouring different materials and plastics,biological±medical studies, and lasers, liquid-crystallinedisplays, electro-optical devices and ink-jet printers in high-technology areas (Catino & Farris, 1985; Gregory, 1991). Thecrystal and molecular structures of the title compound, (I),have been investigated in order to determine the conform-ation and also to con®rm the stereochemistry.Aview of the molecule of (I) is shown in Fig. 1, and selectedbond distances and angles are given in Table 1. The structureof (I) is very similar to those of azo compounds studiedpreviously (Maginn, 1993; IsËik et al. , 1997, 1998; Zhang et al. ,1998; OdabasËog Ælu et al. , 2003). The two aromatic rings are in a trans con®guration with respect to the azo double-bond.The CÐO(hydroxyl) [1.342 (2) AÊ], ÐN NÐ [1.255 (2) AÊ,indicative of a double bond] and CÐN [1.432 (2) AÊ, indicativeof a single bond] bond lengths are consistent with valuesobserved in related compounds (IsËik et al. , 1997, 1998;OdabasËog Ælu et al. , 2003). The C14ÐO3 bond [1.417 (2) AÊ] isapproximately equal to that usually associated with a methylCÐO bond in a methoxy group attached to an aromatic ring(1.424 AÊ; Allen et al. , 1987). Received 5 January 2004Accepted 12 January 2004Online 17 January 2004 Figure 1 A view of the molecule of (I), showing the atom-labelling scheme andwith displacement ellipsoids drawn at the 50% probability level. electronic reprint  In (I), the dihedral angle   1 , between the mean planes of thephenyl ring (C1±C6) and the C1ÐN1 N2ÐC7 azo bridge, is8.9 (1)  . The angle   2 between the C1ÐN1 N2ÐC7 azogroup and the substituted phenyl ring (C7±C12) is 1.0 (1)  .The angle   3 between the planes of the rings is 8.02 (8)  ; thusthe molecule is approximately planar.The molecule of (I) contains a strong intramolecular O ÁÁÁ Ohydrogen bond [2.627 (2) AÊ; see Table 2 for details]. Experimental The title compound, (I), was prepared using the literature method of OdabasËog Ælu et al. (2003), with o -vanilline and aniline as startingmaterials (yield 95%; m.p. 422±424 K). Crystal data C 14 H 12 N 2 O 3 M  r  = 256.26Orthorhombic, Pbcna = 10.6039 (11) AÊ b = 12.9904 (14) AÊ c = 18.1168 (14) AÊ V  = 2495.6 (4) AÊ 3 Z  = 8 D  x = 1.364 Mg m À 3 Mo K   radiationCell parameters from 7873re¯ections   = 1.9±26.5  " = 0.10 mm À 1 T  = 293 (2) KPrism, brown0.40 Â 0.37 Â 0.31 mm Data collection Stoe IPDS2 diffractometer 3 scansAbsorption correction: byintegration (  X-RED 32;Stoe & Cie, 2002) T  min = 0.962, T  max = 0.97716 964 measured re¯ections2457 independent re¯ections1503 re¯ections with I  > 2 '  (  I  ) R int = 0.137   max = 26.0  h = À 13 3 12 k = À 16 3 16 l  = À 22 3 21 Re®nement  Re®nement on F  2 R [ F  2 > 2 '  ( F  2 )] = 0.042 wR ( F  2 ) = 0.100 S = 0.842457 re¯ections173 parametersH-atom parameters constrained w = 1/[ '  2 ( F  o 2 ) + (0.0654 P ) 2 ]where P = ( F  o 2 + 2 F  c 2 )/3( Á / '  ) max < 0.001 Á & max = 0.25 e AÊ À 3 Á & min = À 0.17 e AÊ À 3 Table 1 Selected geometric parameters (AÊ,  ). C1ÐN1 1.4315 (18)C7ÐN2 1.4176 (18)C10ÐO2 1.3425 (17)C11ÐO3 1.3578 (16)C13ÐO1 1.224 (2)C14ÐO3 1.4166 (19)N1ÐN2 1.2553 (17)C6ÐC1ÐN1 123.64 (14)C2ÐC1ÐN1 116.68 (13)C8ÐC7ÐN2 115.15 (12)C12ÐC7ÐN2 124.64 (13)O2ÐC10ÐC9 122.46 (14)O2ÐC10ÐC11 117.62 (12)O3ÐC11ÐC12 126.27 (14)O3ÐC11ÐC10 114.21 (12)O1ÐC13ÐC9 124.87 (16)N2ÐN1ÐC1 112.99 (12)N1ÐN2ÐC7 115.72 (12)C11ÐO3ÐC14 116.83 (11) Table 2 Hydrogen-bonding geometry (AÊ,  ). D ÐH ÁÁÁ  A D ÐH H ÁÁÁ  A D ÁÁÁ  A D ÐH ÁÁÁ  A O2ÐH2  A ÁÁÁ O1 0.82 1.91 2.627 (2) 146 H atoms were added at calculated positions and re®ned using ariding model, with isotropic displacement parameters equal to 1.2 (or1.5 for methyl and hydroxyl H atoms) times the equivalent isotropicdisplacement parameter of the atom to which they are attached.Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:  X-AREA ; data reduction: X-RED 32 (Stoe & Cie, 2002); program(s)used to solve structure: SHELXS 97 (Sheldrick, 1990); program(s)used to re®ne structure: SHELXL 97 (Sheldrick, 1997); moleculargraphics: ORTEP -3 for Windows (Farrugia, 1997); software used toprepare material for publication: WinGX  (Farrugia, 1999). The authors wish to acknowledge the Faculty of Arts andSciences, Ondokuz Mayõs University, Turkey, for the use of theStoe IPDS2 diffractometer (purchased under grant No. F279of the University Research Fund). References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1±19.Catino, S. C. & Farris, R. E. (1985). Azo Dyes , in Kirk±Othmer ConciseEncyclopaedia of Chemical Technology , edited by M. Grayson. New York:John Wiley and Sons.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837±838.Gregory, P. (1991). Colorants for High Technology , in Colour Chemistry: TheDesign and Synthesis of Organic Dyes and Pigments , edited by A. T. Peters& H. S. Freeman. London, New York: Elsevier.IsËik, SË., Aygu È n, M., Kocaokutgen, H. & Tahir, N. (1998).  Acta Cryst. C 54 , 1145±1146.IsËik, SË., Aygu È n, M., SÎasÎmaz, S., Kendi, E., Bu È yu È kgu È ngo È r, O. & Erdo È nmez, A.(1997). Acta Cryst. C 53 , 593±594.Maginn, S. J. (1993). Dyes Pigm. 23 , 159±178.OdabasËog Ælu, M., Albayrak, CË. Bu È yu È kgu È ngo È r, O. & Goesmann, H. (2003). ActaCryst. C 59 , o234±o236.Sheldrick, G. M. (1990). Acta Cryst. A 46 , 467±473.Sheldrick, G. M. (1997). SHELXL 97. University of Go È ttingen, Germany.Stoe & Cie (2002).  X-AREA (Version 1.18) and  X-RED 32 (Version 1.04). Stoe& Cie, Darmstadt, Germany.Zhang, D.-C., Ge, L.-Q., Fei, Z.-H., Zhang, Y.-Q. & Yu, K. -B. (1998). ActaCryst. C 54 , 1909±1911. Acta Cryst. (2004). E 60 , o230±o231 Cem CuÈ neyt Ersanlõ et al.  C 14 H 12 N 2 O 3 o231 organic papers electronic reprint
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