47 1- (5-Chloro-2-hydroxyphenylamino)methylene

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47 1- (5-Chloro-2-hydroxyphenylamino)methylene
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 1-[(5-Chloro-2-hydroxyphenylamino)methylene]naphthalen-2(1 H  )-one Arzu¨Ozek, S¨uheyla Y¨uce, 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. (2004). E 60 , o1162–o1164 Arzu¨Ozek et al. ¯ C 17 H 12 ClNO 2  organic papers o1162 Arzu OÈ zek et al.  C 17 H 12 ClNO 2 DOI: 10.1107/S1600536804013728 Acta Cryst. (2004). E 60 , o1162±o1164 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 1-[(5-Chloro-2-hydroxyphenylamino)methylene]-naphthalen-2(1 H )-one Arzu OÈzek, a * SuÈheyla YuÈce, a CËigÆdem Albayrak, b Mustafa OdabasËogÆlu b andOrhan BuÈyuÈkguÈngoÈr a a Department of Physics, Ondokuz MayõsUniversity, TR-55139, Samsun, Turkey, and b Department of Chemistry, Ondokuz MayõsUniversity, TR-55139, Samsun, TurkeyCorrespondence e-mail: arzuozek@omu.edu.tr Key indicators Single-crystal X-ray study T  = 293 KMean '  (C±C) = 0.006 AÊ R factor = 0.063 wR factor = 0.112Data-to-parameter ratio = 13.3For 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 molecule of the title compound, C 17 H 12 ClNO 2 , is notexactly planar, and adopts the keto±amine tautomeric form.There is an intramolecular NÐH ÁÁÁ O hydrogen bond, andintermolecular OÐH ÁÁÁ O hydrogen bonds link the moleculesinto a three-dimensional network. Comment Although Schiff bases have been widely used as ligands in theformation of transition metal complexes and structurallycharacterized, a relatively small number of free Schiff baseshave been similarly characterized (Calligaris & Randaccio,1987). Schiff bases play an important role in many ®elds of chemistry and biochemistry (Lozier et al. , 1975; Garnovskii et al. , 1993). Two characteristic properties of Schiff bases arephotochromism and thermochromism (Cohen et al. , 1964;Moustakali-Mavridis et al. , 1978). These properties are causedby proton transfer from the hydroxyl O atom to the imine Natom (Hadjoudis et al. , 1987; Xu et al. , 1994). Schiff basesdisplay two possible tautomeric forms, viz . the phenol-imineand keto-amine forms. In the solid state, the keto-aminetautomer has been found in naphthaldimine Schiff bases(Ho È kelek et al. , 2000; U È nver et al. , 2001; OdabasËog Ælu et al. ,2003; O È zek et al. , 2004), whereas the phenol-imine tautomerexists in salicylaldimine Schiff bases (Kaitner & Pavlovic,1996; Yõldõz et al. , 1998).In the title compound, (I), the keto-amine tautomer isfavoured over the phenol-imine form (Fig. 1 and Table 1), andthere is a strong intramolecular hydrogen bond, N1ÐH1 a ÁÁÁ O1. The sum of the van der Waals radii of oxygen andnitrogen is 3.07 AÊ(Bondi, 1964), and the intramolecularhydrogen bond in (I) is much shorter than this, viz .2.590 (4) AÊ.The somewhat short C2ÐO1 and C1ÐC11 bonds can beconsidered as C O and C C double bonds, respectively.This fact, together with the very short C3ÐC4 bond, suggeststhe presence of a signi®cant quinoidal effect. A similar effectwas observed for 1-[(3-hydroxypyridin-2-ylamino)methylene]-1 H  -naphthalen-2-one [C O 1.276 (2) AÊ; O È zek et al. , 2004], 1-[ N  -(  p -hydroxyphenyl)aminomethylidene]naphthalen-2(1 H  )-one propan-1-ol hemisolvate] [C O 1.292 (2) AÊand Received 3 June 2004Accepted 7 June 2004Online 12 June 2004 electronic reprint  1.295 (2) AÊ; OdabasËog Ælu et al. , 2004] and N  - n -propyl-2-oxo-1-naphthylidenemethylamine [C O 1.277 (2) AÊ; Kaitner &Pavlovic, 1996]. The keto-amine form is also dominant in N  -(  -naphthyl)-2-oxo-1-naphthaldimine [C O 1.287 (5) AÊ;Gavranic et al. , 1996].The title molecule is not exactly planar, with a dihedralangle of 10.20 (15)  between ring A (atoms C12±C17) and ring B (atoms C1±C5/C10). The hydrogen-bonded ring (N1, H1 a ,O1, C2, C1, C11) is almost planar. The C11ÐN1 bond lengthand C11ÐN1ÐC12 bond angle are 1.313 (4) AÊand 130.6 (3)  ,respectively, compared with 1.3237 (19) AÊand 125.96 (16)  in1-[(3-hydroxypyridin-2-ylamino)methylene]-1 H  -naphthalen-2-one (O È zek et al. , 2004).The molecules are linked by strong intermolecular OÐH ÁÁÁ O hydrogen bonds (Table 2) into a three-dimensionalnetwork. Experimental The title compound, (I), was prepared as described in the literature(OdabasËog Ælu et al. , 2003), using 2-amino-4-chlorophenol and 2-hydroxy-1-naphthol as starting materials. Crystals of (I) wereobtained by slow evaporation of a THF solution (yield 87%, m.p.545±546 K). Crystal data C 17 H 12 ClNO 2 M  r  = 297.73Triclinic, P 1 a = 7.293 (5) AÊ b = 7.865 (5) AÊ c = 13.628 (5) AÊ  = 88.973 (5)   = 74.668 (5)    = 63.876 (5)  V  = 672.5 (7) AÊ 3 Z  = 2 D  x = 1.470 Mg m À 3 Mo K   radiationCell parameters from 4334re¯ections   = 2.9±28.8  " = 0.29 mm À 1 T  = 293 (2) KPlate, orange0.16 Â 0.12 Â 0.04 mm Data collection Stoe IPDS 2 diffractometer 3 scansAbsorption correction: byintegration (  X-RED 32;Stoe & Cie, 2002) T  min = 0.951, T  max = 0.9909652 measured re¯ections2638 independent re¯ections1319 re¯ections with I  > 2 '  (  I  ) R int = 0.123   max = 26.0  h = À 8 3 8 k = À 9 3 9 l  = À 16 3 16 Re®nement  Re®nement on F  2 R [ F  2 > 2 '  ( F  2 )] = 0.063 wR ( F  2 ) = 0.112 S = 0.942638 re¯ections198 parametersH atoms treated by a mixture of independent and constrainedre®nement w = 1/[ '  2 ( F  o 2 ) + (0.0318 P ) 2 ]where P = ( F  o 2 + 2 F  c 2 )/3( Á / '  ) max < 0.001 Á & max = 0.19 e AÊ À 3 Á & min = À 0.18 e AÊ À 3 Table 1 Selected geometric parameters (AÊ,  ). C1ÐC11 1.388 (5)C1ÐC2 1.426 (5)C1ÐC10 1.454 (4)C2ÐO1 1.291 (4)C2ÐC3 1.419 (5)C3ÐC4 1.349 (5)C4ÐC5 1.422 (5)C5ÐC10 1.412 (5)C11ÐN1 1.313 (4)C12ÐN1 1.401 (4)N1ÐH1a 0.88 (4)C11ÐC1ÐC2 120.1 (3)C11ÐC1ÐC10 120.1 (3)O1ÐC2ÐC3 120.7 (3)O1ÐC2ÐC1 121.4 (3)N1ÐC11ÐC1 124.9 (3)C17ÐC12ÐN1 116.7 (3)C13ÐC12ÐN1 124.0 (3)C11ÐN1ÐC12 130.6 (3)C11ÐC1ÐC2ÐO1 À 7.7 (6)C2ÐC1ÐC11ÐN1 2.1 (6)C10ÐC1ÐC11ÐN1 À 178.9 (4)C1ÐC11ÐN1ÐC12 À 178.6 (4) Table 2 Hydrogen-bonding geometry (AÊ,  ). D ÐH ÁÁÁ  A D ÐH H ÁÁÁ  A D ÁÁÁ  A D ÐH ÁÁÁ  A N1ÐH1 a ÁÁÁ O1 0.88 (4) 1.82 (4) 2.590 (4) 144 (3)O2ÐH2 a ÁÁÁ O1 i 0.96 (5) 1.61 (5) 2.557 (4) 166 (4) Symmetry code: (i) x Y 1   y Y z . The H atoms attached to N and O were re®ned freely. Other Hatoms were positioned geometrically (CÐH = 0.93 AÊ) and re®nedusing a riding model, with U  iso (H) = 1.2 U  eq (parent atom). organic papers Acta Cryst. (2004). E 60 , o1162±o1164 Arzu OÈ zek et al.  C 17 H 12 ClNO 2 o1163 Figure 2 An ORTEP packing diagram. Dashed lines indicate intra- andintermolecular hydrogen bonds. Figure 1 An ORTEP view of (I), with the atom-numbering scheme and 50%probability displacement ellipsoids. The intramolecular hydrogen bond isindicated by the dashed line. electronic reprint  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, 1997); 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). References Bondi, A. (1964). J. Phys. Chem. 68 , 441±451.Calligaris, M. & Randaccio, L. (1987). Comprehensive CoordinationChemistry , Vol. 2, edited by G. Wilkinson, pp. 715±738. London: Pergamon.Cohen, M. D., Schmidt, G. M. J. & Flavian, J. (1964). J. Chem. Soc. pp. 2041±2051.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837±838.Garnovskii, A. D. Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem.Rev. 126 , 1±69.Gavranic, M., Kaitner, B. & Mestrovic, E. (1996). J. Chem Crystallogr. 26 , 23±28.Hadjoudis, E., Vitterakis, M. & Mavridis, I. M. (1987). Tetrahedron , 43 , 1345±1360.Ho È kelek, T., KõlõcË. Z. , IsËõklan, M. & Toy, M. (2000). J. Mol. Struct. 523 , 61±69.Kaitner, B. & Pavlovic, G. (1996). Acta Cryst. C 52 , 2573±2575.Lozier, R. Bogomolni, R. A. & Stoekenius, W. (1975). J. Biophys. 15 , 955±962.Moustakali-Mavridis, I., Hadjous, E. & Mavridis, A. (1978). Acta Cryst. B 34 ,3709±3715.OdabasËog Ælu, M., Albayrak, CË. & Bu È yu È kgu È ngo È r, O. (2004). Acta Cryst. E 60 ,o142±o144.OdabasËog Ælu, M., Albayrak, CË. & Bu È yu È kgu È ngo È r, O. & Lo È nneche, P. (2003).  ActaCryst. C 59 , o616±o619.O È zek, A., Yu È ce, S., Albayrak, CË., OdabasËog Ælu, M. & Bu È yu È kgu È ngo È r, O. (2004).  Acta Cryst. E 60 , o356±o358.Sheldrick, G. M. (1997). SHELXL 97 and SHELXS 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.U È nver, H., Kabak, M., Zengin, D. M. & Durlu, T. N. (2001). J. Chem.Crystallogr. 31 , 203±209.Xu, X.-X., You, X.-Z., Sun, Z.-F., Wang, X. & Liu, H.-X. (1994). Acta Cryst. C 50 , 1169±1171.Yõldõz, M., KõlõcË, Z. & Ho È kelek, T. (1998). J. Mol. Struct. 441 , 1±10. organic papers o1164 Arzu OÈ zek et al.  C 17 H 12 ClNO 2 Acta Cryst. (2004). E 60 , o1162±o1164 electronic reprint
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