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Volume 66 
Part 6 
Pages o1450-o1451  
June 2010  

Received 14 April 2010
Accepted 19 May 2010
Online 26 May 2010

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.004 Å
R = 0.065
wR = 0.220
Data-to-parameter ratio = 14.7
Details
Open access

4-[(Dimethylamino)methylidene]-2-(4-nitrophenyl)-1,3-oxazol-5(4H)-one

Gilberto A. Romeiro,a Carlos M. R. Ribeiro,a Solange M. S. V. Wardell,b James L. Wardell,c+ Seik Weng Ngd and Edward R. T. Tiekinkd*

aUniversidade Federal Fluminense, Departamento de Química Orgãnica, Instituto de Química, Outeiro de São João Baptista, 24020-141 Niterói, RJ, Brazil,bCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland,cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The title molecule, C12H11N3O4, is essentially planar, the r.m.s. deviation for all non-H atoms being 0.068 Å. An intramolecular C-H...N hydrogen bond occurs. The crystal packing is dominated by [pi]-[pi] interactions [shortest centroid-centroid distance = 3.6312 (16) Å], which lead to supramolecular chains that are linked into a three-dimensional network via C-H...O contacts. The crystal was found to be a non-merohedral twin (twin law -1 0 0/0 -1 0/ 0.784 0 1), the fractional contribution of the minor component being approximately 22%.

Related literature

For the synthesis, synthetic uses and properties of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives, see: Singh & Singh (1994[Singh, K. K. & Singh, R. M. (1994). Indian J. Chem. Sect. B, 33, 232-235.], 2008[Singh, V. K. & Singh, D. (2008). Asian J. Chem. 20, 3349-3352.]); Takahashi & Izawa (2005[Takahashi, D. & Izawa, K. (2005). Eur. Patent 2004-256811 20041104.]); Singh et al. (1994[Singh, K. K., Singh, M. K. & Singh, R. M. (1994). Indian J. Chem. Sect. B, 33, 1119-1122.]); Kmetic & Stanovnik (1995[Kmetic, M. & Stanovnik, B. (1995). J. Heterocycl. Chem. 32, 1563-1565.]). For the Vilsmeier-Haack reaction, see: Meth-Cohn & Stanforth (1991[Meth-Cohn, O. & Stanforth, S. P. (1991). Comp. Org. Synth. 2, 777-794.]). For related structures, see Vasuki et al. (2002[Vasuki, G., Thamotharan, S., Ramamurthi, K., Ambika, S. & Singh, R. M. (2002). Acta Cryst. E58, o740-o741.]); Vijayalakshmi et al. (1998[Vijayalakshmi, L., Parthasarathi, V., Perumal, P. T. & Majo, V. J. (1998). Acta Cryst. C54, 1683-1685.]). For the treatment of twinned diffraction data, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data

  • C12H11N3O4

  • Mr = 261.24

  • Monoclinic, P 21 /c

  • a = 9.5313 (2) Å

  • b = 9.5204 (3) Å

  • c = 13.0349 (4) Å

  • [beta] = 106.661 (2)°

  • V = 1133.15 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 120 K

  • 0.42 × 0.38 × 0.22 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.661, Tmax = 1.000

  • 14210 measured reflections

  • 2581 independent reflections

  • 2030 reflections with I > 2[sigma](I)

  • Rint = 0.071
Refinement

  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.220

  • S = 1.19

  • 2581 reflections

  • 176 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5c...N1 0.98 2.28 3.074 (5) 137
C5-H5a...O2i 0.98 2.53 3.504 (4) 177
C5-H5c...O4ii 0.98 2.57 3.259 (5) 127
C9-H9...O1iii 0.95 2.56 3.304 (4) 135
C11-H11...O2iv 0.95 2.45 3.144 (4) 130
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2209 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Kmetic, M. & Stanovnik, B. (1995). J. Heterocycl. Chem. 32, 1563-1565.  [CrossRef] [ChemPort]
Meth-Cohn, O. & Stanforth, S. P. (1991). Comp. Org. Synth. 2, 777-794.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, K. K. & Singh, R. M. (1994). Indian J. Chem. Sect. B, 33, 232-235.
Singh, V. K. & Singh, D. (2008). Asian J. Chem. 20, 3349-3352.  [ChemPort]
Singh, K. K., Singh, M. K. & Singh, R. M. (1994). Indian J. Chem. Sect. B, 33, 1119-1122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takahashi, D. & Izawa, K. (2005). Eur. Patent 2004-256811 20041104.
Vasuki, G., Thamotharan, S., Ramamurthi, K., Ambika, S. & Singh, R. M. (2002). Acta Cryst. E58, o740-o741.  [CSD] [CrossRef] [details]
Vijayalakshmi, L., Parthasarathi, V., Perumal, P. T. & Majo, V. J. (1998). Acta Cryst. C54, 1683-1685.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.

Acta Cryst (2010). E66, o1450-o1451   [ doi:10.1107/S1600536810018635 ]

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