3-(2-Acetamido­phen­yl)sydnone

Grossie, D.A.; Turnbull, K.; Felix-Balderrama, S.; Raghavapuram, S.

doi:10.1107/S1600536809005066

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 (C-C) = 0.001 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 20.4
Details

3-(2-Acetamidophenyl)sydnone

David A. Grossie,^a ^* Kenneth Turnbull,^a Sandra Felix-Balderrama ^a and Shravanthi Raghavapuram ^a

^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-HO and C-HO 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). For the synthesis and structural information, see: Grossie et al. (1992, 2001, 2007); Riddle et al. 2004a,b,c; Hope & Thiessen (1968); Hodson & Turnbull (1985); Baker & Ollis (1957). For a description of the Cambridge Structural Database, see: Allen (2002). For related literature, see: Kier & Roche (1966); Matsunaga (1957); Ollis & Ramsden (1976).

Experimental

Crystal data

C₁₀H₉N₃O₃
M_r = 219.20
Monoclinic, P 2₁ /c
a = 7.7348 (4) Å
b = 13.7212 (7) Å
c = 9.6698 (5) Å
= 106.083 (1)°
V = 986.10 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.895, T_max = 0.970
8741 measured reflections
3053 independent reflections
2711 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(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
_max = 0.44 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N12-H12O17Aⁱ	0.876 (15)	2.056 (15)	2.9272 (10)	173.2 (14)
C4-H4O5ⁱⁱ	0.96	2.28	3.1860 (12)	156
C13-H13O17A	0.96	2.29	2.8587 (14)	117
C15-H15O5ⁱⁱⁱ	0.96	2.41	3.3612 (14)	173
C16-H16O5^iv	0.96	2.57	3.4700 (13)	157
C18-H18BO17Aⁱ	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); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and OSCAIL X, (McArdle, 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004), publCIF (Westrip, 2009) and PLATON (Spek, 2009).

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.
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.
Baker, W. & Ollis, W. D. (1957). Q. Rev. Chem. Soc. 11, 15-29.
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.
Grossie, D. A. & Turnbull, K. (1992). Acta Cryst. C48, 377-379.
Grossie, D. A., Turnbull, K. & Krein, D. M. (2001). Acta Cryst. E57, o985-o987.
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.
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.
Matsunaga, Y. (1957). Bull. Chem. Soc. Jpn, 30, 227-230.
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.
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004a). Acta Cryst. E60, o977-o978.
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004b). Acta Cryst. E60, o1568-o1570.
Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004c). Acta Cryst. E60, o258-o259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds