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Volume 69 
Part 9 
Pages o1365-o1366  
September 2013  

Received 20 July 2013
Accepted 26 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.119
Data-to-parameter ratio = 21.9
Details
Open access

2-(3-Cyano-4-methyl-5,5-diphenyl-5H-furan-2-ylidene)malononitrile

aCallaghan Innovation Research Limited, PO Box 31-310, Lower Hutt, New Zealand, and bIndustrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
Correspondence e-mail: graeme.gainsford@callaghaninnovation.govt.nz

The title compound, C21H13N3O, crystallizes with two independent molecules with similar conformations per asymmetric unit. The dihydrofuran rings are essentially planar with maximum deviations of 0.017 (1) and 0.006 (1) Å for the O atoms. The dihedral angles between the dihydrofuran ring and the attached phenyl rings are 79.90 (6) and 82.07 (6)° in one molecule and 79.36 (6) and 72.26 (6)° in the other. In the crystal, the molecules are linked by weak C-H...[pi] and C-H...N interactions similar to those in other closely related crystals. The replacement of appended methyl by phenyl groups has not significantly affected the dihydrofuran ring structure or the crystal packing interactions.

Related literature

For general background to NLO chromophores, see: Smith et al. (2006[Smith, G. J., Dunford, C. L., Kay, A. J. & Woolhouse, A. D. (2006). J. Photochem. Photobiol. A, 179, 237-242.], 2010[Smith, G. J., Middleton, A. P., Clarke, D. J., Teshome, A., Kay, A. J., Bhuiyan, M. D. H., Asselberghs, I. & Clay, K. (2010). Opt. Mater. 32, 1237-1243.]); Carey et al. (2002[Carey, J. J., Bailey, R. T., Pugh, D., Sherwood, J. N., Cruikshank, F. R. & Wynne, K. (2002). Appl. Phys. Lett. 81, 4335-4337.]); Kay et al. (2004[Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.]). For details of the synthesis, see: Anderson (2009[Anderson, J. (2009). BSc (Hons.) project report. Victoria University of Wellington, New Zealand.]). For related structures, see: Anderson (2009[Anderson, J. (2009). BSc (Hons.) project report. Victoria University of Wellington, New Zealand.]); Gainsford et al. (2011[Gainsford, G. J., Anderson, J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3046-o3047.]); Li et al. (2005[Li, S.-Y., Song, Y.-Y., You, Z.-L., Wen, Y.-W. & Qin, J.-G. (2005). Acta Cryst. E61, o2093-o2095.]); Liao et al. (2005[Liao, Y., Eichinger, B. E., Firestone, K. A., Haller, M., Luo, J., Kaminsky, W., Benedict, J. B., Reid, P. J., Jen, A. K.-Y., Dalton, L. R. & Robinson, B. H. (2005). J. Am. Chem. Soc. 127, 2758-2766.]). For geometric analysis of structures, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). 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
  • C21H13N3O

  • Mr = 323.34

  • Triclinic, [P \overline 1]

  • a = 9.2308 (3) Å

  • b = 12.5991 (4) Å

  • c = 14.3043 (4) Å

  • [alpha] = 89.954 (2)°

  • [beta] = 89.052 (2)°

  • [gamma] = 79.233 (2)°

  • V = 1634.07 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 123 K

  • 0.36 × 0.32 × 0.29 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.651, Tmax = 0.746

  • 45305 measured reflections

  • 9930 independent reflections

  • 7329 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.119

  • S = 1.04

  • 9930 reflections

  • 453 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 phenyl ring

D-H...A D-H H...A D...A D-H...A
C20'-H20'...Cg1i 0.95 2.69 3.4041 (14) 133
C9-H9B...N3' 0.98 2.70 3.4560 (14) 134
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: RZ5081 ).


Acknowledgements

This work was supported by a New Zealand Foundation for Research Science and Technology grant (contract No. C08X0704). We thank Dr C. Fitchett of the University of Canterbury, New Zealand, for his assistance.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Anderson, J. (2009). BSc (Hons.) project report. Victoria University of Wellington, New Zealand.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carey, J. J., Bailey, R. T., Pugh, D., Sherwood, J. N., Cruikshank, F. R. & Wynne, K. (2002). Appl. Phys. Lett. 81, 4335-4337.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gainsford, G. J., Anderson, J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3046-o3047.  [CSD] [CrossRef] [ChemPort] [details]
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.  [ISI] [CrossRef] [ChemPort]
Li, S.-Y., Song, Y.-Y., You, Z.-L., Wen, Y.-W. & Qin, J.-G. (2005). Acta Cryst. E61, o2093-o2095.  [CSD] [CrossRef] [ChemPort] [details]
Liao, Y., Eichinger, B. E., Firestone, K. A., Haller, M., Luo, J., Kaminsky, W., Benedict, J. B., Reid, P. J., Jen, A. K.-Y., Dalton, L. R. & Robinson, B. H. (2005). J. Am. Chem. Soc. 127, 2758-2766.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Smith, G. J., Dunford, C. L., Kay, A. J. & Woolhouse, A. D. (2006). J. Photochem. Photobiol. A, 179, 237-242.  [CrossRef] [ChemPort]
Smith, G. J., Middleton, A. P., Clarke, D. J., Teshome, A., Kay, A. J., Bhuiyan, M. D. H., Asselberghs, I. & Clay, K. (2010). Opt. Mater. 32, 1237-1243.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1365-o1366   [ doi:10.1107/S1600536813020849 ]

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