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Volume 65 
Part 3 
Pages o554-o555  
March 2009  

Received 5 February 2009
Accepted 11 February 2009
Online 21 February 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.001 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 20.4
Details
Open access

3-(2-Acetamidophenyl)sydnone

aDepartment of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, Ohio 45435, USA
Correspondence e-mail: david.grossie@wright.edu

Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C10H9N3O3, the aromatic substitutent is 2-acetamidophenyl. The two planar ring fragments are twisted relative to one another, with a interplanar angle of 63.13 (5)°. The molecules are packed into the unit cell via [pi]-[pi] interactions between the phenyl rings [interplanar separation = 3.4182 (4) Å] and between the sydnone rings [interplanar separation = 3.2095 (4) Å]. N-H...O and C-H...O hydrogen bonding is also found internally and externally to the molecule.

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 the synthesis and structural information, see: Grossie et al. (1992[Grossie, D. A. & Turnbull, K. (1992). Acta Cryst. C48, 377-379.], 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.]); 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.]; Hope & Thiessen (1968[Hope, H. & Thiessen, W. E. (1968). In The Structures of 4,4'-Dichloro-3,3'-ethylenebissydnone and 3,3'-Ethylenebys-sydnone. Department of Chemistry, University of California, USA.]); Hodson & Turnbull (1985[Hodson, S. J. & Turnbull, K. (1985). In Bromination of 3-(2-Aminophenyl)sydnone and Related Compounds. Department of Chemistry, Wright State University, Dayton, Ohio, USA.]); Baker & Ollis (1957[Baker, W. & Ollis, W. D. (1957). Q. Rev. Chem. Soc. 11, 15-29.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For related literature, see: Kier & Roche (1966[Kier, L. B. & Roche, E. B. (1966). J. Pharm. Sci. 55, 807-12.]); Matsunaga (1957[Matsunaga, Y. (1957). Bull. Chem. Soc. Jpn, 30, 227-230.]); Ollis & Ramsden (1976[Ollis, W. D. & Ramsden, C. A. (1976). Adv. Heterocycl. Chem. 19, 1-122.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9N3O3

  • Mr = 219.20

  • Monoclinic, P 21 /c

  • a = 7.7348 (4) Å

  • b = 13.7212 (7) Å

  • c = 9.6698 (5) Å

  • [beta] = 106.083 (1)°

  • V = 986.10 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.45 × 0.40 × 0.26 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.895, Tmax = 0.970

  • 8741 measured reflections

  • 3053 independent reflections

  • 2711 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.05

  • 3053 reflections

  • 150 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N12-H12...O17Ai 0.876 (15) 2.056 (15) 2.9272 (10) 173.2 (14)
C4-H4...O5ii 0.96 2.28 3.1860 (12) 156
C13-H13...O17A 0.96 2.29 2.8587 (14) 117
C15-H15...O5iii 0.96 2.41 3.3612 (14) 173
C16-H16...O5iv 0.96 2.57 3.4700 (13) 157
C18-H18B...O17Ai 0.98 2.54 3.3201 (12) 136
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and OSCAIL X, (McArdle, 2008[McArdle, P. (2008). OSCAIL X. National University of Ireland, Ireland.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]), publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2130 ).


Acknowledgements

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

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [CrossRef] [details]
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Baker, W. & Ollis, W. D. (1957). Q. Rev. Chem. Soc. 11, 15-29.  [CrossRef] [ChemPort]
Bruker (2003). SADABS, SMART and SAINT-Plus, Bruker AXS Inc., Madison, Wisconsin, USA.
Grossie, D. A., Sun, L. & Turnbull, K. (2007). Acta Cryst. E63, o2042-o2043.  [CSD] [CrossRef] [details]
Grossie, D. A. & Turnbull, K. (1992). Acta Cryst. C48, 377-379.  [CrossRef] [details]
Grossie, D. A., Turnbull, K. & Krein, D. M. (2001). Acta Cryst. E57, o985-o987.  [CSD] [CrossRef] [details]
Hodson, S. J. & Turnbull, K. (1985). In Bromination of 3-(2-Aminophenyl)sydnone and Related Compounds. Department of Chemistry, Wright State University, Dayton, Ohio, USA.
Hope, H. & Thiessen, W. E. (1968). In The Structures of 4,4'-Dichloro-3,3'-ethylenebissydnone and 3,3'-Ethylenebys-sydnone. Department of Chemistry, University of California, USA.
Kier, L. B. & Roche, E. B. (1966). J. Pharm. Sci. 55, 807-12.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Matsunaga, Y. (1957). Bull. Chem. Soc. Jpn, 30, 227-230.  [CrossRef] [ChemPort] [ISI]
McArdle, P. (2008). OSCAIL X. National University of Ireland, Ireland.
Ohta, M. & Kato, H. (1969). Nonbenzenoid Aromatics, edited by J. P. Snyder, pp. 117-248. New York: Academic Press. .
Ollis, W. D. & Ramsden, C. A. (1976). Adv. Heterocycl. Chem. 19, 1-122.  [CrossRef] [ChemPort]
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004a). Acta Cryst. E60, o977-o978.  [CSD] [CrossRef] [details]
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004b). Acta Cryst. E60, o1568-o1570.  [CSD] [CrossRef] [details]
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004c). Acta Cryst. E60, o258-o259.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.


Acta Cryst (2009). E65, o554-o555   [ doi:10.1107/S1600536809005066 ]

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