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Volume 69 
Part 8 
Page o1196  
August 2013  

Received 24 June 2013
Accepted 27 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.074
Data-to-parameter ratio = 23.4
Details
Open access

3-{5-Bromo-2-[(triphenylphosphanylidene)amino]phenyl}-4,5-dihydro-1,2,3-oxadiazol-3-ylium-5-olate

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

In general, sydnone compounds are synthesized with an aromatic substituent at the N-3 position and this feature adds to the stability of the mesoionic five-membered heterocyclic ring. In the title compound, C26H19BrN3O2P, the aromatic substitutent is triphenylphosphine 4-bromophenylimide. The dihedral angle between the planes of the sydnone and the attached phenyl ring is 45.98 (7)°. In the crystal, the molecules packed as pairs in which the sydnone rings lie in parallel planes separated by 0.849 Å and sandwiched between two parallel phenyl rings. The molecules interact through cyclic C-H...O=C hydrogen bonds.

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 their synthesis and structures, 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.]); Ollis & Ramsden (1976[Ollis, W. D. & Ramsden, C. A. (1976). Adv. Heterocycl. Chem. 19, 1-122.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H19BrN3O2P

  • Mr = 516.33

  • Monoclinic, P 21 /n

  • a = 7.5207 (8) Å

  • b = 13.8672 (15) Å

  • c = 21.816 (2) Å

  • [beta] = 95.449 (2)°

  • V = 2264.9 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.92 mm-1

  • T = 173 K

  • 0.43 × 0.30 × 0.28 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Siemens, 1996[Siemens (1996). SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.50, Tmax = 0.58

  • 46513 measured reflections

  • 6964 independent reflections

  • 5914 reflections with I > 2.0[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.074

  • S = 0.92

  • 6964 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.86 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H41...O5i 0.91 2.48 3.344 (2) 159
C72-H721...O5i 0.94 2.37 3.297 (2) 173
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: GG2120 ).


Acknowledgements

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

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 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [CrossRef] [IUCr Journals]
Grossie, D. A., Turnbull, K. & Krein, D. M. (2001). Acta Cryst. E57, o985-o987.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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.  [CrossRef] [ChemPort] [IUCr Journals]
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] [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]
Siemens (1996). SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2013). E69, o1196  [ doi:10.1107/S1600536813017765 ]

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