24 Methyl 3-(2-oxobenzothiazolin-3-yl)propanoate

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24 Methyl 3-(2-oxobenzothiazolin-3-yl)propanoate
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Methyl 3-(2-oxobenzothiazolin-3-yl)propanoate Cem C¨uneyt Ersanlı, Yasemin D¨undar, U ˇgur Sarı, Ningur Noyanalpan, MustafaOdabas¸o ˇglu 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. (2003). E 59 , o1604–o1606 Cem C¨uneyt Ersanlı et al. ¯ C 11 H 11 NO 3 S  benzoyl)-2(3 H  )-benzothiazolone (Lamiot et al. , 1995), and1.743 (3) and 1.772 (3) AÊfor ethyl 4-(2-oxobenzothiazolin-3-yl)butanoate (Baysen et al. , 2002).There is a short intermolecular C9ÐH9B ÁÁÁ O1 i contactbetween the  atom of the methyl propionate substituent andthe carbonyl oxygen of the oxobenzothiazole group [C9 ÁÁÁ O1 i 3.241 (2) AÊ, H9 B ÁÁÁ O1 i 2.47 AÊ; symmetry code (i): À  x , 12 + y , 12 À z ]. These contacts link the molecules into in®nite chainsalong the b axis of the crystal. Experimental 10.0 mmol (1.51 g) of 2(3 H  )-benzothiazolone and 11.0 mmol (1.11 g,1.53 ml) of triethylamine were dissolved in 30 ml of methanol.11.0 mmol (0.95 g, 0.99 ml) of methyl acrylate was added to thesolution. The mixture was heated at 323±333 K for 6 h. It was thencooled to room temperature and 100 g ice-water was added andstirred for 1 h. The precipitate was collected by ®ltration, dried andwashed with 10% NaOH solution, followed by water until neutral,then dried again and crystallized from methanol; yield 1.66 g (70%). Crystal data C 11 H 11 NO 3 S M  r  = 237.27Monoclinic, P 2 1 a ca = 7.9109 (13) AÊ b = 8.386 (3) AÊ c = 16.4898 (16) AÊ  = 93.645 (12)  V  = 1091.8 (4) AÊ 3 Z  = 4 D  x = 1.443 Mg m À 3 Mo K   radiationCell parameters from 3603re¯ections   = 20.1±26.4  " = 0.29 mm À 1 T  = 293 (2) KPrism, yellow0.90  0.60  0.25 mm Data collection Rigaku AFC-7 S diffractometer 3 ±2   scansAbsorption correction: 2  scan(North et al. , 1968) T  min = 0.812, T  max = 0.9303383 measured re¯ections3176 independent re¯ections2039 re¯ections with I  > 2 '  (  I  ) R int = 0.040   max = 30.0  h = 0 3 11 k = 0 3 11 l  = À 23 3 233 standard re¯ectionsevery 150 re¯ectionsintensity decay: 0.6% Re®nement  Re®nement on F  2 R [ F  2 > 2 '  ( F  2 )] = 0.039 wR ( F  2 ) = 0.126 S = 1.033176 re¯ections146 parametersH-atom parameters constrained w = 1/[ '  2 ( F  o 2 ) + (0.0588 P ) 2 + 0.2099 P ]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 0.35 e AÊ À 3 Extinction correction: SHELXL Extinction coef®cient: 0.085 (5) Table 1 Selected geometric parameters (AÊ,  ). S1ÐC1 1.742 (2)S1ÐC7 1.768 (2)N1ÐC6 1.402 (2)N1ÐC7 1.371 (2)N1ÐC8 1.465 (2)O1ÐC7 1.217 (2)O2ÐC10 1.200 (2)O3ÐC10 1.330 (2)O3ÐC11 1.443 (2)C1ÐS1ÐC7 91.50 (8)C7ÐN1ÐC6 114.9 (2)C7ÐN1ÐC8 118.8 (2)C6ÐN1ÐC8 126.2 (2)C10ÐO3ÐC11 117.5 (2)C2ÐC1ÐC6 121.58 (16)C2ÐC1ÐS1 127.30 (14)C6ÐC1ÐS1 111.12 (13)C5ÐC6ÐN1 127.3 (2)C1ÐC6ÐN1 112.5 (2)O1ÐC7ÐN1 125.7 (2)O1ÐC7ÐS1 124.4 (2)N1ÐC7ÐS1 109.9 (2)N1ÐC8ÐC9 112.6 (2)O2ÐC10ÐO3 123.7 (2)O2ÐC10ÐC9 125.3 (2)O3ÐC10ÐC9 111.1 (2) Table 2 Hydrogen-bonding geometry (AÊ,  ). D ÐH ÁÁÁ  A D ÐH H ÁÁÁ  A D ÁÁÁ  A D ÐH ÁÁÁ  A C9ÐH9 B ÁÁÁ O1 i 0.97 2.47 3.241 (2) 136 Symmetry code: (i) À  x Y 12   y Y 12 À z . All H atoms were positioned geometrically (CÐH = 0.93±0.97 AÊand re®ned using a riding model, with U  iso (H) = 1.2 U  eq (C) [ U  iso (H) =1.5 U  eq (C) for methyl H atoms].Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell re®nement: MSC/AFC Diffractometer Control Software ; data reduction: TEXSAN for  Acta Cryst. (2003). E 59 , o1604±o1606 Cem CuÈ neyt Ersanlõ et al.  C 11 H 11 NO 3 S o1605 organic papers Figure 2 A packing diagram of the crystal structure of the title compound, showingthe CÐH ÁÁÁ O contacts as dashed lines. Figure 1 Aview of the molecule of the title compound, with the atomic numberingscheme. Displacement ellipsoids are drawn at the 50% probability level;H atoms are shown as small spheres of arbitrary radii. electronic reprint  organic papers o1606 Cem CuÈ neyt Ersanlõ et al.  C 11 H 11 NO 3 S Acta Cryst. (2003). E 59 , o1604±o1606 Windows (Molecular Structure Corporation, 1997); program(s) usedto solve structure: SHELXS 97 (Sheldrick, 1990); program(s) used tore®ne structure: SHELXL 97 (Sheldrick, 1997); molecular graphics: ORTEP III for Windows (Farrugia, 1997); software used to preparematerial for publication: WinGX  publication routines (Farrugia,1999). The authors thank the University of Kõrõkkale, Turkey forthe data collection. References Baysen, F., Yabasan, R., Ide, S., SËahin, E., CË akõr, B. & Du È ndar, Y. (2002). Z.Kristallogr. New Cryst. Struct. 217 , 529±530.Clayden, J., Greeves, N., Warren, S. & Wothers, P. (2001). Organic Chemistry ,pp. 164±165. Oxford University Press.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837±838.Khan, M. A., Taylor, R. W., Lehn, J. M. & Dietrich, B. (1988). Acta Cryst. C 44 ,1928±1931.Lamiot, J., Baert, F., Taverne, T., Houssin, R. & Lesieur, I. (1995). Acta Cryst. C 51 , 1912±1915.Molecular Structure Corporation (1994). MSC/AFC Diffractometer Control Software . MSC, 3200 Research Forest Drive, The Woodlands, TX 77381,USA.Molecular Structure Corporation (1997). TEXSAN for Windows (Version1.03) and Single Crystal Structure Analysis Software (Version 1.03). MSC,3200 Research Forest Drive, The Woodlands, TX 77381, USA.North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A 24 , 351±359.Rudd, S. & Barany, G. (1984). Acta Cryst. C 40 , 2118±2120.Sheldrick, G. M. (1990). Acta Cryst. A 46 , 467±473.Sheldrick, G. M. (1997). SHELXL 97. University of Go È ttingen, Germany.Varkonda, S., Hy blova , O., Sutoris, V., Konecny , V. & Mikula sek, S. (1985).Czechoslovakian Patent No. 239.411. electronic reprint
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