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Volume 69 
Part 7 
Page o1158  
July 2013  

Received 7 June 2013
Accepted 19 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 13.2
Details
Open access

4-Methyl-5-(4-nitrobenzylidene)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

aCallaghan Innovation Research Limited, PO Box 31-310, Lower Hutt, New Zealand
Correspondence e-mail: g.gainsford@irl.cri.nz

Molecules of the potential non-linear optical title compound, C13H9N3O3, form dimeric stacks of molecules along the a axis cross-linked around inversion centers by N-H...O hydrogen bonds and weak (phenyl)C-H...O intermolecular interactions, forming a `collaboration' of R22(8) and R22(16) ring motifs. The molecules are then further linked by weak C-H...O and C-H...N interactions into sheets parallel to (121).

Related literature

For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For chemical synthesis literature, see: Shrestha-Dawadi & Lugtenburg (2007[Shrestha-Dawadi, P. B. & Lugtenburg, J. (2007). Eur. J. Org. Chem. pp. 1294-1300.]). For background literature, see: Bert et al. (2006[Bert, M., Maarten, K., Gitte, V. B., Mario, S. & Wim, D. (2006). Tetrahedron, 62, 6018-6028.]); Colin et al. (2002[Colin, J. H. M., Ryan, G., David, M. S., Philip, L., Alexandra, M. Z. S. & Elizabeth, J. M. (2002). Tetrahedron, 58, 5547-5565.]); Hasan et al. (2012[Hasan, Z.-B., Mehdi, M., Khadijeh, H. & Maryam, G. (2012). J. Org. Chem. 77, 5808-5812.]); Stephen et al. (2011[Stephen, L., Carson, J. B., Hiroyuki, M., Rocio, P. O., Antonio, F., Samuel, I. S. & Tobin, J. M. (2011). J. Am. Chem. Soc. 133, 8142-8145.]); Tarek et al. (2013[Tarek, A., Stanislav, L. Jr, Antonín, L., Jan, V., Zdenek, E., Ales, R., Zdenka, P. & Radim, H. (2013). Dyes Pigments, 98, 530-539.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9N3O3

  • Mr = 255.23

  • Monoclinic, P 21 /c

  • a = 3.7456 (2) Å

  • b = 14.9193 (9) Å

  • c = 21.6077 (17) Å

  • [beta] = 92.273 (7)°

  • V = 1206.52 (14) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.86 mm-1

  • T = 120 K

  • 0.44 × 0.05 × 0.03 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.633, Tmax = 1.000

  • 7096 measured reflections

  • 2283 independent reflections

  • 1941 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.139

  • S = 1.05

  • 2283 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.88 1.98 2.8256 (18) 159
C9-H9...O1ii 0.95 2.43 3.336 (2) 159
C12-H12...N2iii 0.95 2.59 3.374 (3) 141
C13-H13...O2iv 0.95 2.58 3.372 (2) 141
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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.]); software used to prepare material for publication: SHELXL97 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: JJ2169 ).


Acknowledgements

The authors thank Dr J. Wikaira of the University of Canterbury for the data collection.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bert, M., Maarten, K., Gitte, V. B., Mario, S. & Wim, D. (2006). Tetrahedron, 62, 6018-6028.
Colin, J. H. M., Ryan, G., David, M. S., Philip, L., Alexandra, M. Z. S. & Elizabeth, J. M. (2002). Tetrahedron, 58, 5547-5565.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hasan, Z.-B., Mehdi, M., Khadijeh, H. & Maryam, G. (2012). J. Org. Chem. 77, 5808-5812.  [PubMed]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shrestha-Dawadi, P. B. & Lugtenburg, J. (2007). Eur. J. Org. Chem. pp. 1294-1300.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stephen, L., Carson, J. B., Hiroyuki, M., Rocio, P. O., Antonio, F., Samuel, I. S. & Tobin, J. M. (2011). J. Am. Chem. Soc. 133, 8142-8145.  [Web of Science] [PubMed]
Tarek, A., Stanislav, L. Jr, Antonín, L., Jan, V., Zdenek, E., Ales, R., Zdenka, P. & Radim, H. (2013). Dyes Pigments, 98, 530-539.


Acta Cryst (2013). E69, o1158  [ doi:10.1107/S1600536813017066 ]

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