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Volume 69 
Part 11 
Page o1662  
November 2013  

Received 9 July 2013
Accepted 2 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.121
Data-to-parameter ratio = 20.5
Details
Open access

4-Acetyl-3-[2-(eth­oxy­carbon­yl)phen­yl]sydnone

aDepartment of Chemistry, Wright State University, Dayton, OH 45435, USA
Correspondence e-mail: david.grossie@wright.edu

Sydnones, which contain a mesoionic five-membered heterocyclic ring, are more stable if synthesized with an aromatic substutuent at the N3 position. In the title compound {sys­tematic name: 4-acetyl-3-[2-(eth­oxy­carbon­yl)phen­yl]-1,2,3-oxa­diazol-3-ylium-5-olate}, C13H12N2O5, the aromatic substitutent is 2-(eth­oxy­carbon­yl)phenyl. Intra- and inter­molecular hydrogen bonds are observed. The inter­planar angle between the sydnone and benzene rings is 71.94 (8)°. [pi]-ring...carbon­yl inter­actions of 3.2038 (16) Å arise between the sydnone ring and a symmetry-related C=O group.

Related literature

For more information on the sydnone family of compounds, see: Ohta & Kato (1969[Ohta, M. & Kato, H. (1969). Nonbenzenoid Aromatics, edited by J. P. Snyder, pp. 117-248. New York: Academic Press.]). For synthesis and structure information, see: Grossie & Turnbull (1992[Grossie, D. A. & Turnbull, K. (1992). Acta Cryst. C48, 377-379.]); Grossie et al. (2001[Grossie, D. A., Turnbull, K. & Krein, D. M. (2001). Acta Cryst. E57, o985-o987.], 2007[Grossie, D. A., Sun, L. & Turnbull, K. (2007). Acta Cryst. E63, o2042-o2043.]); Hope & Thiessen (1969[Hope, H. & Thiessen, W. E. (1969). Acta Cryst. B25, 1237-1247.]); Hodson & Turnbull (1985[Hodson, S. J. & Turnbull, K. (1985). J. Heterocycl. Chem. 22, 1223-1227.]); Riddle et al. (2004a[Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004a). Acta Cryst. E60, o977-o978.],b[Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004b). Acta Cryst. E60, o1568-o1570.],c[Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004c). Acta Cryst. E60, o258-o259.]); Hanley et al. (1976[Hanley, R. N., Ollis, W. D. & Ramsden, C. A. (1976). J. Chem. Soc. Chem. Commun. 9, 306-307.]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12N2O5

  • Mr = 276.25

  • Monoclinic, P 21 /n

  • a = 11.353 (3) Å

  • b = 8.093 (2) Å

  • c = 14.607 (4) Å

  • [beta] = 112.582 (4)°

  • V = 1239.1 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 173 K

  • 0.22 × 0.20 × 0.17 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.90, Tmax = 0.98

  • 13826 measured reflections

  • 3718 independent reflections

  • 2783 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.121

  • S = 0.96

  • 3718 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C36-H361...O5i 0.95 2.51 3.253 (2) 136
C40-H401...O41ii 0.97 2.46 3.116 (2) 124
C42-H423...O5 0.96 2.51 3.065 (2) 117
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2123 ).


Acknowledgements

The authors acknowledge the diffractometer time granted by A. Hunter, Youngstown State University, USA.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [Web of Science] [CrossRef] [IUCr Journals]
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Grossie, D. A., Sun, L. & Turnbull, K. (2007). Acta Cryst. E63, o2042-o2043.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Grossie, D. A. & Turnbull, K. (1992). Acta Cryst. C48, 377-379.  [CSD] [CrossRef] [IUCr Journals]
Grossie, D. A., Turnbull, K. & Krein, D. M. (2001). Acta Cryst. E57, o985-o987.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Hanley, R. N., Ollis, W. D. & Ramsden, C. A. (1976). J. Chem. Soc. Chem. Commun. 9, 306-307.  [CrossRef] [Web of Science]
Hodson, S. J. & Turnbull, K. (1985). J. Heterocycl. Chem. 22, 1223-1227.  [CrossRef] [ChemPort]
Hope, H. & Thiessen, W. E. (1969). Acta Cryst. B25, 1237-1247.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ohta, M. & Kato, H. (1969). Nonbenzenoid Aromatics, edited by J. P. Snyder, pp. 117-248. New York: Academic Press.
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004a). Acta Cryst. E60, o977-o978.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004b). Acta Cryst. E60, o1568-o1570.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004c). Acta Cryst. E60, o258-o259.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2013). E69, o1662  [ doi:10.1107/S1600536813027207 ]

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