46 1- (4-Acetylphenylamino)methylene naphthalen-2(1H)-one

Please download to get full document.

View again

of 3
6 views
PDF
All materials on our website are shared by users. If you have any questions about copyright issues, please report us to resolve them. We are always happy to assist you.
Document Description
46 1- (4-Acetylphenylamino)methylene naphthalen-2(1H)-one
Document Share
Document Tags
Document Transcript
  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 1-[(4-Acetylphenylamino)methylene]naphthalen-2(1 H  )-one S¨uheyla Y¨uce, Arzu¨Ozek, 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 , o1217–o1218 S¨uheyla Y¨uce et al. ¯ C 19 H 15 NO 2  Acta Cryst. (2004). E 60 , o1217±o1218 DOI: 10.1107/S1600536804010633 SuÈ heyla YuÈ ce et al.  C 19 H 15 NO 2 o1217 organic papers Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 1-[(4-Acetylphenylamino)methylene]-naphthalen-2(1 H )-one SuÈheyla YuÈce, a * Arzu OÈzek, 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: syuce@omu.edu.tr Key indicators Single-crystal X-ray study T  = 293 KMean '  (C±C) = 0.002 AÊ R factor = 0.036 wR factor = 0.089Data-to-parameter ratio = 11.1For 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 19 H 15 NO 2 , is nearlyplanar and adopts the keto±amine tautomeric form, with astrong intramolecular NÐH ÁÁÁ O [2.5383 (17) AÊ] hydrogenbond. Comment Schiff bases have been widely used as ligands in the ®eld of coordination chemistry (Calligaris & Randaccio, 1987). Schiff base compounds show photochromism and thermochromismin the solid state by proton transfer from the hydroxyl O atomto the imine N atom (Cohen et al. , 1964), i.e. phenol±imineketo±amine tautomerism. In solution, this tautomerism, whichdepends on the formation of intramolecular hydrogen bonds,is possible (Filarowski & Koll, 1998; Yõldõz et al. , 1998; Nazõr et al. , 2000; Deziembowska et al. , 2001; U È nver et al. , 2001). In thesolid state, the keto±amine tautomer is dominant innaphthaldimine (Ho È kelek et al. , 2002; U È nver et al. , 2002;OdabasËog Ælu et al. , 2004), while the phenol±imine tautomer isfound in salicylaldimine Schiff bases (Kaitner & Pavlovic,1996; Yõldõz et al. , 1998; Elmalõ et al. , 1998; Karadayõ et al. ,2003; OdabasËog Ælu et al. , 2004; Yu È ce et al. , 2004).The title compound, (I), adopts the keto±imine tautomericform, with a strong intramolecular N1ÐH1 ÁÁÁ O1 hydrogenbond (Fig. 1). The rather short C1ÐO1, C18ÐO2 and C2ÐC3, C5ÐC6, C7ÐC8 bonds can be considered as C O andC C double bonds, respectively. This suggests the presenceof a signi®cant quinoidal effect. A similar effect was observedin 1-[ N  -(  p -hydroxyphenyl)aminomethylidene]naphthalen-2(1 H  )-one propan-1-ol hemisolvate [C O = 1.292 (2) and1.295 AÊ; OdabasËog Ælu et al. , 2004] and N  - n -propyl-2-oxo-1-naphthylidenemethylamine [C O = 1.277 (2) AÊ; Kaitner &Pavlovic, 1996].The study of Schiff bases has led to the proposal thatmolecules exhibiting thermochromism are planar, while thoseexhibiting photochromism are non-planar. Molecule (I) isnearly planar; the dihedral angle between the rings A (atomsC12±C17) and B (atoms C1±C10) is 10.98 (4)  . Experimental The title compound, (I), was prepared as described in the literature(OdabasËog Ælu et al. , 2004), using 4-acetylaniline and 2-hydroxy-1- Received 20 April 2004Accepted 30 April 2004Online 19 June 2004 electronic reprint  organic papers o1218 SuÈ heyla YuÈ ce et al.  C 19 H 15 NO 2 Acta Cryst. (2004). E 60 , o1217±o1218 naphthol as starting materials. Crystals of (I) were obtained by slowevaporation of an acetone solution (yield 92%, m.p. 479±481 K). Crystal data C 19 H 15 NO 2 M  r  = 289.32Monoclinic, P 2 1 a ca = 6.7815 (4) AÊ b = 14.0948 (12) AÊ c = 15.0855 (10) AÊ  = 90.050 (5)  V  = 1441.93 (18) AÊ 3 Z  = 4 D  x = 1.333 Mg m À 3 Mo K  radiationCell parameters from 11906re¯ections   = 2.0±28.4  " = 0.09 mm À 1 T  = 293 (2) KPrism, orange0.38 Â 0.31 Â 0.28 mm Data collection Stoe IPDS-2 diffractometer 3 scansAbsorption correction: none20326 measured re¯ections2839 independent re¯ections1731 re¯ections with I  > 2 '  (  I  ) R int = 0.044   max = 26.0  h = À 8 3 8 k = À 17 3 17 l  = À 18 3 18 Re®nement  Re®nement on F  2 R [ F  2 > 2 '  ( F  2 )] = 0.036 wR ( F  2 ) = 0.089 S = 0.852839 re¯ections255 parametersH atoms treated by a mixture of independent and constrainedre®nement w = 1/[ '  2 ( F  o 2 ) + (0.0571 P ) 2 ]where P = ( F  o 2 + 2 F  c 2 )/3( Á / '  ) max < 0.001 Á & max = 0.10 e AÊ À 3 Á & min = À 0.15 e AÊ À 3 Table 1 Selected geometric parameters (AÊ,  ). C1ÐO1 1.2822 (17)C1ÐC10 1.4305 (19)C1ÐC2 1.436 (2)C2ÐC3 1.336 (2)C3ÐC4 1.425 (2)C4ÐC5 1.401 (2)C5ÐC6 1.357 (2)C6ÐC7 1.390 (2)C7ÐC8 1.369 (2)C8ÐC9 1.402 (2)C9ÐC10 1.4508 (19)C10ÐC11 1.3988 (19)C11ÐN1 1.3161 (17)C12ÐN1 1.4056 (17)C18ÐO2 1.2141 (18)C18ÐC19 1.499 (2)N1ÐH1 0.86O1ÐC1ÐC10 122.07 (13)O1ÐC1ÐC2 119.74 (14)C11ÐC10ÐC1 119.14 (13)C11ÐC10ÐC9 120.95 (12)N1ÐC11ÐC10 123.08 (14)N1ÐC11ÐH8 118.2 (8)C13ÐC12ÐN1 122.46 (12)C17ÐC12ÐN1 118.01 (13)C11ÐN1ÐC12 126.33 (12)O1ÐC1ÐC2ÐC3 À 179.34 (15)C1ÐC10ÐC11ÐN1 0.9 (2)C9ÐC10ÐC11ÐN1 178.75 (13)N1ÐC12ÐC13ÐC14 À 178.88 (13)N1ÐC12ÐC17ÐC16 178.46 (13)C10ÐC11ÐN1ÐC12 178.81 (13)C13ÐC12ÐN1ÐC11 À 11.0 (2)C17ÐC12ÐN1ÐC11 170.54 (13) Table 2 Hydrogen-bonding geometry (AÊ,  ). D ÐH ÁÁÁ  A D ÐH H ÁÁÁ  A D ÁÁÁ  A D ÐH ÁÁÁ  A N1ÐH1 ÁÁÁ O1 0.86 1.84 2.5383 (16) 137 All H atoms were found in difference density maps. H1 attached toN1 was re®ned as riding, with NÐH = 0.86 AÊand U  iso (H) =1.2 U  eq (N). H atoms attached to carbon were re®ned freely [CÐH =0.92 (2)±0.99 (2) AÊ].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 Calligaris, M & Randaccio, L. (1987). Comprehensive Coordination Chemistry ,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.Deziembowska, T., Rozvadowski, Z., Filarowski, A. & Hansen, P. E. (2001). Magn. Reson. Chem. 39 , 67±80.Elmalõ, A., Elerman, Y. & Zeyrek, C. T. (1998). J. Mol. Struct. 443 , 123±130.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837±838.Filarowski, A. & Koll, A. (1998). Vib . Spectrosc. 17 , 123±131.Ho È kelek, T., KilicË, Z. & IsËõklan, M. (2002). J. Mol. Struct. 523 , 61±69.Kaitner, B. & Pavlovic, G. (1996). Acta Cryst. C 52 , 2573±2575.Karadayõ, N., Go È zu È yesËil, S., Gu È zel, B. & Bu È yu È kgu È ngo È r, O. (2003). Acta Cryst. E 59 , o161±o163.Nazõr, H., Yõldõz, M., Yõlmaz, H., M. N. & U È lku È , D. (2000). J. Mol. Struct. 524 ,241±250.OdabasËog Ælu, M., Albayrak, CË. & Bu È yu È kgu È ngo È r, O. (2004). Acta Cryst. E 60 ,o142±o144.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.Yõldõ z , M., KõlõcË. Z. & Ho È kelek, T. (1998). J. Mol. Struct. 441 , 1±10.Yu È ce, S., O È zek, A., Albayrak, CË., OdabasËog Ælu, M. & Bu È yu È kgu È ngo È r, O. (2004).  Acta Cryst. E 60 , o718±o719. Figure 2 A view of the packing in (I). Figure 1 Aview of the title compound, with the atom-numbering scheme and 50%probability displacement ellipsoids. The dashed line indicates theintramolecular hydrogen bond. electronic reprint
Search Related
We Need Your Support
Thank you for visiting our website and your interest in our free products and services. We are nonprofit website to share and download documents. To the running of this website, we need your help to support us.

Thanks to everyone for your continued support.

No, Thanks