77 ( Z)-4- ( E)-(4-Butylphenyl)diazenyl -6- 1,3-dihydroxy-2

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77 ( Z)-4- ( E)-(4-Butylphenyl)diazenyl -6- 1,3-dihydroxy-2
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson ( Z  )-4-[( E  )-(4-Butylphenyl)diazenyl]-6-   [1,3-dihydroxy-2-(hydroxymeth-yl)propan-2-ylamino]methylene   -2-methoxycyclohexa-2,4-dienone Cem C¨uneyt Ersanlı, C¸i ˇgdem Albayrak, Mustafa Odabas¸o ˇglu and OrhanB¨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. (2005). E 61 , o4139–o4141 Ersanlı et al. ¯ C 22 H 29 N 3 O 5  organic papers Acta Cryst. (2005). E 61 , o4139–o4141 doi:10.1107/S1600536805037177 Ersanlı et al.  C 22 H 29 N 3 O 5 o4139 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 (  Z  )-4-[( E  )-(4-Butylphenyl)diazenyl]-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone Cem Cu¨neyt Ersanlı, a * C¸igˇdemAlbayrak, b Mustafa Odabas¸ogˇlu b and Orhan Bu¨yu¨kgu¨ngo¨r a a Department of Physics, Faculty of Arts andSciences, Ondokuz Mayıs University, 55139Kurupelit Samsun, Turkey, and b Departmentof Chemistry, Faculty of Arts and Sciences,Ondokuz Mayıs University, 55139 KurupelitSamsun, TurkeyCorrespondence e-mail: ccersan@omu.edu.tr Key indicators Single-crystal X-ray study T  = 296 KMean   (C–C) = 0.007 A˚Disorder in main residue R factor = 0.083 wR factor = 0.250Data-to-parameter ratio = 16.6For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e. # 2005 International Union of CrystallographyPrinted in Great Britain – all rights reserved The title compound, C 22 H 29 N 3 O 5 , is approximately planarwith the aromatic rings in a trans configuration with respect tothe azo double bond. The eneamine portion of the moleculeexists as the keto–amine tautomer, stabilized by a strongintramolecular N—H ÁÁÁ O hydrogen bond. IntramolecularN—H ÁÁÁ O and O—H ÁÁÁ O and intermolecular O—H ÁÁÁ Oand C—H ÁÁÁ O interactions influence the conformation of themolecules and the crystal packing. Comment Azo compounds are the most widely used class of dyes, owingto their versatile application in various fields, such as dyeingand colouring, and high-technology areas, such as electro-optical devices and ink-jet printers (Peters & Freeman, 1991).There is interest in Schiff base ligands and their complexeswith regard to their impressive antitumour activities (Zhou et al. , 2000). Schiff base compounds can be classified by theirphotochromic and thermochromic characteristics (Cohen et al. , 1964; Moustakali etal. , 1978; Hadjoudis etal. , 1987). On thebasis of studies of some thermochromic and photochromicSchiff base compounds, it has been proposed that moleculesexhibiting thermochromism are planar, while those exhibitingphotochromism are non-planar (Moustakali et al. , 1978).We report here the structure of the Schiff base compound,(I) (Fig. 1 and Table 1). There are two possible tautomers thatthis molecule could adopt, viz . the keto–amine and enol–iminetautomeric forms. The structural data clearly show that (I)adopts the keto–amine form, stabilized by the formation of anN—H ÁÁÁ O hydrogen bond. Similar o -hydroxy Schiff baseshave been found to adopt the keto (Ersanlı et al. , 2003;Ersanlı, Albayrak, Odabas¸og ˇ lu, Tho ¨ ne & Erdo ¨ nmez, 2004;Ersanlı et al. , 2005), enol (Ersanlı, Albayrak, Odabas¸og ˇ lu &Erdo ¨ nmez, 2004; Ersanlı, Odabas¸og ˇ lu et al. , 2004) or enol/keto Received 1 November 2005Accepted 11 November 2005Online 16 November 2005 electronic reprint  forms (Nazır et al. , 2000). The C14—O2 and C18—N3 bonddistances (Table 1) are reasonably similar, a characteristic of systems in the keto–amine form, and comparable to thosefound in 4-[(2-chlorophenyl)diazenyl]-6-methoxy-2-{[tris-(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2 H  )-one [1.287 (2) and 1.294 (2) A˚; Ersanlı, Albayrak,Odabas¸og ˇ lu, Tho ¨ ne & Erdo ¨ nmez, 2004]. In contrast, thecorresponding distances are significantly different in systemsknown to adopt the enol-imine tautomeric form, with a muchlonger C—O bond, for example, 1.354 (2) and 1.275 (2) A˚in2-[2-(hydroxymethyl)phenyliminomethyl]phenol (Ersanlı,Odabas¸og ˇ lu et al. , 2004), and 1.355 (2) and 1.278 (2) A˚in 4-(2-hydroxyphenyliminomethylene)phenol (Ersanlı, Albayrak,Odabas¸og ˇ lu & Erdo ¨ nmez, 2004).Intramolecular N3—H1 ÁÁÁ O2 and C22—O5—H5 ÁÁÁ O4hydrogen bonds influence the conformation of the molecule(Table 2). The packing is also stabilized by a number of intermolecular O—H ÁÁÁ O and C—H ÁÁÁ O interactions (Fig. 2). Experimental The title compound, (I), was prepared as previously described(Ersanlı, Albayrak, Odabas¸og ˇ lu, Tho ¨ ne & Erdo ¨ nmez, 2004) Theproduct was recrystallized from ethanol and well shaped crystals wereobtained by slow evaporation of an acetonitrile solution (m.p. 461–463 K). Crystal data C 22 H 29 N 3 O 5 M  r  = 415.48Monoclinic, P 2 1 = ca = 18.3934 (13) A˚ b = 10.6960 (7) A˚ c = 10.8516 (8) A˚  = 95.488 (6)  V  = 2125.1 (3) A˚ 3 Z  = 4 D  x = 1.299 Mg m À 3 Mo K   radiationCell parameters from 17039reflections   = 1.9–27.9   = 0.09 mm À 1 T  = 296 (2) KPlate, orange0.30 Â 0.20 Â 0.05 mm Data collection Stoe IPDS-II diffractometer ! scansAbsorption correction: integration(  X-RED32 ; Stoe & Cie, 2002) T  min = 0.975, T  max = 0.99623762 measured reflections4173 independent reflections2194 reflections with I  > 2   (  I  ) R int = 0.097   max = 26.0  h = À 22 ! 22 k = À 13 ! 13 l  = À 13 ! 13 Refinement  Refinement on F  2 R [ F  2 > 2   ( F  2 )] = 0.083 wR ( F  2 ) = 0.250 S = 1.024173 reflections252 parametersH atoms treated by a mixture of independent and constrainedrefinement w = 1/[   2 ( F  o2 ) + (0.1495 P ) 2 ]where P = ( F  o2 + 2 F  c2 )/3( Á /   ) max = 0.001 Á  max = 0.52 e A˚ À 3 Á  min = À 0.52 e A˚ À 3 Table 1 Selected geometric parameters (A˚,  ). C1—N1 1.427 (7)C4—C7 1.525 (8)C11—N2 1.406 (6)C13—O1 1.363 (5)C14—O2 1.276 (5)C17—O1 1.423 (6)C18—N3 1.289 (5)C20—O3 1.422 (5)C21—O4 1.416 (5)C22—O5 1.416 (5)N1—N2 1.238 (5)C16—C11—N2 116.6 (4)N2—C11—C12 123.9 (4)C12—C13—O1 125.9 (4)O2—C14—C15 123.2 (3)O2—C14—C13 120.3 (3)N3—C18—C15 122.7 (4)N1—N2—C11 115.5 (4)C18—N3—C19 129.2 (3)C1—N1—N2—C11 À 175.6 (5) Table 2 Hydrogen-bond geometry (A˚,  ). D —H ÁÁÁ  A D —H H ÁÁÁ  A D ÁÁÁ  A D —H ÁÁÁ  A O4—H4 ÁÁÁ O3 i 0.82 2.03 2.769 (4) 150O3—H3 ÁÁÁ O4 i 0.82 2.00 2.769 (4) 155O5—H5 ÁÁÁ O3 ii 0.82 2.37 2.771 (3) 111C20—H20 B ÁÁÁ O4 iii 0.97 2.55 3.310 (5) 135C22—H22 B ÁÁÁ O2 ii 0.97 2.42 3.375 (5) 169N3—H1 ÁÁÁ O2 0.88 (5) 1.88 (5) 2.603 (4) 138 (4)O5—H5 ÁÁÁ O4 0.82 2.56 3.088 (4) 124 Symmetry codes: (i) À  x þ 2 ; À  y ; À z þ 2; (ii) À  x þ 2 ;  y À 12 ; À z þ 32 ; (iii) À  x þ 2 ;  y þ 12 ; À z þ 32 . organic papers o4140 Ersanlı et al.  C 22 H 29 N 3 O 5 Acta Cryst. (2005). E 61 , o4139–o4141 Figure 2 Packing diagram for (I), with hydrogen bonds drawn as dashed lines. Forthe sake of clarity, all H atoms, except for H3, H4, H5, H20 B and H22 B ,have been omitted. Figure 1 A view of (I), with the atom-numbering scheme and 50% probabilitydisplacement ellipsoids. There is orientational disorder in the C1–C6benzene ring; occupancy factors for atoms C2a/C3a/C5a/C6a and C2b/C3b/C5b/C6b are 0.617 (6) and 0.383 (6), respectively. Hydrogen bondsare shown as dashed lines. electronic reprint  The crystals were weakly diffracting but attempts to find one of better quality were not successful. Furthermore, high displacementparameters for atoms in the benzene ring suggested possible disorder.This was resolved by refining alternative positions for the unsub-stituted atoms C2, C3, C5 and C6 of the benzene ring. Their occu-pancies refined to 0.617 (6) and 0.383 (6), respectively. All H atomsbound to C atoms were refined using a riding model [C—H = 0.93 A˚and U  iso (H) = 1.2 U  eq (C) for aromatic C atoms, C—H = 0.97 A˚and U  iso (H) = 1.2 U  eq (C) for methylene C atoms, and C—H = 0.96 A˚and U  iso (H) = 1.5 U  eq (C) for methyl C atoms]. The H atoms of the hydroxyO atoms were refined with O—H constrained to 0.82 A˚and with U  iso (H) = 1.5 U  eq (O). The H atom bonded to N was refined freely,with U  iso (H) = 1.2 U  eq (N).Data collection: X-AREA (Stoe & Cie, 2002); cell refinement:  X-AREA ; data reduction: X-RED32 (Stoe & Cie, 2002); program(s)used to solve structure: SHELXS97  (Sheldrick, 1997); program(s)used to refine structure: SHELXL97  (Sheldrick, 1997); moleculargraphics: ORTEP-3 for Windows (Farrugia, 1997); software used toprepare material for publication: WinGX  (Farrugia, 1999). The authors acknowledge the Faculty of Arts and Sciences,Ondokuz Mayıs University, Turkey, for the use of the StoeIPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund). References Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2068–2073.Ersanlı, C. C., Albayrak, C¸., Odabas¸og ˇ lu, M. & Erdo ¨ nmez, A. (2003). ActaCryst. C 59 , o601–o602.Ersanlı, C. C., Albayrak, C¸., Odabas¸og ˇ lu, M. & Erdo ¨ nmez, A. (2004). ActaCryst. E 60 , o389–o391.Ersanlı, C. C., Albayrak, C¸., Odabas¸og ˇ lu, M. & Kazak, C. (2005). Acta Cryst. E 61 , o4051–o4053.Ersanlı, C. C., Albayrak, C¸., Odabas¸og ˇ lu, M., Tho ¨ ne, C. & Erdo ¨ nmez, A.(2004). Acta Cryst. C 60 , o133–o135.Ersanlı, C. C., Odabas¸og ˇ lu, M., Albayrak, C¸. & Erdo ¨ nmez, A. (2004). ActaCryst. E 60 , o264–o266.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837–838.Hadjoudis, E., Vitterakis, M., Moustakali, I. & Mavridis, I. (1987). Tetrahedron , 43 , 1345–1360.Moustakali, I., Mavridis, I., Hadjoudis, E. & Mavridis, A. (1978). Acta Cryst. B 34 , 3709–3715.Nazır, H., Yıldız, M., Yılmaz, H., Tahir, M. N. & U ¨ lku ¨ , D. (2000). J. Mol.Struct. 524 , 241–250.Peters, A. T. & Freeman, H. S. (1991). Colour Chemistry , pp. 193–223. London:Elsevier Science Publishers Ltd.Sheldrick, G. M. (1997). SHELXL97  and SHELXS97. University of Go ¨ ttingen, Germany.Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe& Cie, Darmstadt, Germany.Zhou, Y.-S., Zhang, L.-J., Zeng, X.-R., Vittal, J. J. & You, X.-Z. (2000). J. Mol.Struct. 533 , 25–30. organic papers Acta Cryst. (2005). E 61 , o4139–o4141 Ersanlı et al.  C 22 H 29 N 3 O 5 o4141 electronic reprint
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