33 4-(4Methylphenylazo)-2-allylphenolmonohydrate

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33 4-(4Methylphenylazo)-2-allylphenolmonohydrate
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 4-(4-Methylphenylazo)-2-allylphenol monohydrate Nevzat Karadayı, G¨unseli Turgut, Mustafa Odabas¸o ˇglu and Orhan B¨uy¨ukg¨ung  ¨or 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 , o176–o178 Nevzat Karadayı et al. ¯ C 16 H 16 N 2 O ¡  H 2 O  organic papers o176 Nevzat Karadayõ et al.  C 16 H 16 N 2 O Á H 2 O DOI: 10.1107/S1600536803029751 Acta Cryst. (2004). E 60 , o176±o178 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 4-(4-Methylphenylazo)-2-allylphenolmonohydrate Nevzat Karadayõ, a * GuÈnseliTurgut, b Mustafa OdabasËogÆlu b and Orhan BuÈyuÈkguÈngoÈr a a Department of Physics, Faculty of Arts andSciences, Ondokuz Mayõs University,TR-55139, Samsun, Turkey, and b Departmentof Chemistry, Faculty of Arts and Sciences,Ondokuz Mayõs University, TR-55139, Samsun,TurkeyCorrespondence e-mail: nevzatk@omu.edu.tr Key indicators Single-crystal X-ray study T  = 293 KMean '  (C±C) = 0.008 AÊDisorder in main residue R factor = 0.068 wR factor = 0.180Data-to-parameter ratio = 13.0For 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 In the title compound, C 16 H 16 N 2 O Á H 2 O, the azobenzenemoiety has a trans con®guration, and the two phenyl rings areinclined with respect to each other by 14.23 (17)  . There areintermolecular OÐH ÁÁÁ O and OÐH ÁÁÁ N hydrogen bondsinvolving the water molecule. Comment Azo compounds are the most widely used class of dyes, due totheir versatile application in various ®elds, such as the dyeingof textiles, and ®bers, the coloring of different materials, andhigh-technology areas, such as electro-optical devices and ink- jet printers (Peters & Freeman, 1991).The molecular structure of (I) is shown in Fig. 1 with theatom numbering scheme. The compound contains twobenzene rings (C1±C6 and C7±C12), and an azo linkage (C4ÐN1ÐN2ÐC7). The benzene rings adopt a trans -con®gurationabout the azo functional group, as observed in the crystalstructure of other azo compounds. Atom C15 of the allylgroup shows a positional disorder over two sites, C15  A andC15 B . The allyl C14ÐC15  A ÐC16 moiety is twisted out of theplane of its attached benzene ring by 74.08 (2)  . All the CÐCbond distances in the benzene rings have typical C  sp 2 ÐC  sp 2 values. The average CÐC bond distances within these two Received 22 December 2003Accepted 24 December 2003Online 10 January 2004 Figure 1 The molecular structure of (I), showing the atom-numbering scheme.Displacement ellipsoids for non-H atoms are shown at the 50%probability level. The hydrogen bond is indicated by a dashed line. Thesite-occupancy factors of C15  A and C15 B are 0.677 (10) and 0.323 (10),respectively. electronic reprint  rings are 1.370 (7) and 1.410 (7) AÊ. The N1 N2 bond lengthof 1.272 (5) AÊis typical for a double bond and this isapproximately equal to a previously reported N N double-bond length (OdabasËog Ælu, et al. , 2003; Doman ski et al. , 2001;Yatsenko & Paseshnichenko, 2001). The CÐO bond length is1.378 (6) AÊand agrees with the literature value (Jottier et al. ,1991; Stomberg et al. , 1998). There are intermolecular OÐH ÁÁÁ O and OÐH ÁÁÁ N hydrogen bonds involving the watermolecule (Fig. 2 and Table 2). Experimental The title compound (I) was obtained as described previously(OdabasËog Ælu, et al. , 1999). Single crystals of (I) suitable for X-raydiffraction analysis were obtained by slow evaporation of an ethylalcohol solution over 2 d (yield 85%; m.p. 357±358 K). Crystal data C 16 H 16 N 2 O Á H 2 O M  r  = 270.32Orthorhombic, Pbcna = 27.2961 (9) AÊ b = 14.4293 (17) AÊ c = 7.568 (4) AÊ V  = 2980.8 (16) AÊ 3 Z  = 8 D  x = 1.205 Mg m À 3 Mo K   radiationCell parameters from 3655re¯ections   = 1.5±21.6  " = 0.08 mm À 1 T  = 293 KPrism, light brown0.30  0.17  0.10 mm Data collection Stoe IPDS 2 diffractometer 3 rotation scansAbsorption correction: none17874 measured re¯ections2629 independent re¯ections806 re¯ections with I  >2 '  (  I  ) R int = 0.175   max = 25.0  h = À 32 3 32 k = À 17 3 17 l  = À 8 3 8 Re®nement  Re®nement on F  2 R [ F  2 > 2 '  ( F  2 )] = 0.069 wR ( F  2 ) = 0.180 S = 0.882629 re¯ections202 parametersH atoms treated by a mixture of independent and constrainedre®nement w = 1/[ '  2 ( F  o 2 ) + (0.062 P ) 2 ]where P = ( F  o 2 + 2 F  c 2 )/3( Á / '  ) max = 0.030 Á & max = 0.22 e AÊ À 3 Á & min = À 0.19 e AÊ À 3 Extinction correction: SHELXL Extinction coef®cient: 0.0040 (6) Table 1 Selected geometric parameters (AÊ,  ). O1ÐC1 1.378 (6)N1ÐN2 1.272 (5)N1ÐC4 1.441 (6)N2ÐC7 1.450 (6)C1ÐC6 1.374 (7)C1ÐC2 1.392 (7)C2ÐC3 1.403 (7)C2ÐC14 1.520 (7)C3ÐC4 1.410 (7)C4ÐC5 1.348 (7)C5ÐC6 1.383 (7)N2ÐN1ÐC4 114.8 (5)N1ÐN2ÐC7 111.9 (5)C6ÐC1ÐO1 120.9 (6)O1ÐC1ÐC2 116.9 (5)C5ÐC4ÐC3 120.1 (5)C5ÐC4ÐN1 117.0 (5)C8ÐC7ÐN2 114.8 (6)C12ÐC7ÐN2 124.4 (6)C4ÐN1ÐN2ÐC7 À 178.1 (5) Table 2 Hydrogen-bonding geometry (AÊ,  ). D ÐH ÁÁÁ  A D ÐH H ÁÁÁ  A D ÁÁÁ  A D ÐH ÁÁÁ  A O1ÐH1 ÁÁÁ O2 0.82 1.91 2.674 (6) 154.8O2ÐH1  A ÁÁÁ N1 i 0.87 (2) 2.22 (12) 2.908 (7) 136 (14)O2ÐH1 B ÁÁÁ O1 ii 0.84 (2) 2.17 (9) 2.864 (6) 140 (12) Symmetry codes: (i) 12 À x Y  y À 12 Y z ; (ii) 12 À x Y 12 À y Y z À 12 . The R int was relatively poor (0.17). As a result of the long unit-celldimension, a = 27.2961 (9) AÊ, the diffraction spots were close to eachother and their integration might introduce some error in theintensity data. Atom C15 of the allyl group shows positional disorderover two sites, C15  A and C15 B , with occupation factors of 0.677 (10)and 0.323 (10), respectively. The positions of the H atoms bonded toC14 and C16 were calculated, neglecting the minor component(C15 B ). The atomic displacement parameters of C15  A and C15 B were restrained to be equal to those of C14. The H atoms of the watermolecule were found and re®ned. All other H atoms were placed incalculated positions and re®ned using a riding model, with ®xed CÐH distances of 0.93 AÊfor C  sp 2 ÐH bonds and 0.96 AÊfor methyl CÐHbonds and 0.93±0.97 for methylene CÐH, and an OÐH distance of 0.82 AÊ. Their U  iso parameters were ®xed at 1.2 U  eq (CÐH and OÐH)and 1.5 U  eq (methyl groups) of the parent atoms.Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:  X-AREA ; data reduction: X-RE  D32 (Stoe & Cie, 2002); program(s)used to solve structure: SHELXS 97 (Sheldrick, 1997); program(s)used to re®ne structure: SHELXL 97 (Sheldrick, 1997); moleculargraphics: ORTEP III (Burnett & Johnson, 1996); PLUTON  (Spek,1997); software used to prepare material for publication: WinGX  (Farrugia, 1999). References Burnett, M. N. & Johnson, C. K. (1996). ORTEP III. Report ORNL-6895. OakRidge National Laboratory, Tennessee, USA.Doman ski, A., Ejsmont, K., Kyziol, J. B. & Zaleski, J. (2001). Acta Cryst. C 57 ,467±470.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837±838.Jottier, W. I., De Winter, H. L., Blaton, N. M., Peeters, O. M. & De Ranter, C. J.(1991). Acta Cryst. C 57 , 1517±1520.OdabasËog Ælu, M., Turgut, G. & Kocaokutgen, H. (1999). Phosphorus SulfurandSilicon , 152 , 27±34.OdabasËog Ælu, M., Albayrak, CË., Bu È yu È kgu È ngo È r, O. & Goesmann, H. (2003).  ActaCryst. C 59 , o 234±236. Acta Cryst. (2004). E 60 , o176±o178 Nevzat Karadayõ et al.  C 16 H 16 N 2 O Á H 2 O o177 organic papers Figure 2 The crystal structure of (I). Hydrogen bonds are indicated by dashedlines. electronic reprint  organic papers o178 Nevzat Karadayõ et al.  C 16 H 16 N 2 O Á H 2 O Acta Cryst. (2004). E 60 , o176±o178 Peters, A. T. & Freeman, H. S. (1991). Colour Chemistry . London: ElsevierScience.Sheldrick, G. M. (1997). SHELXS 97 and SHELXL 97. University of GoÈttingen, Germany.Spek, A. L. (1997). PLUTON. Version of May 1997. University of Utrecht,The Netherlands.Stoe & Cie (2002).  X-AREA (Version 1.18) and  X-RED 32 (Version 1.04). Stoe& Cie, Darmstadt, Germany.Stomberg, R., Li, S., Lundquist, K. & Albinsson, B. (1998). Acta Cryst. C 54 ,1929±1934.Yatsenko, A. V. & Paseshnichenko, K. A. (2001). Acta Cryst. C 57 , 961±964. electronic reprint
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