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Volume 69 
Part 1 
Pages o103-o104  
January 2013  

Received 27 November 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.144
Data-to-parameter ratio = 14.1
Details
Open access

(E)-5-[3-Cyano-2-(dicyanomethylene)-1-oxaspiro[4.5]dec-3-en-4-yl]-3-(1-methyl-1,4-dihydropyridin-4-ylidene)pent-4-en-1-yl 3,5-bis(benzyloxy)benzoate

aCarbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand, and bPhotonics Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand 5040
Correspondence e-mail: g.gainsford@irl.cri.nz

In the title compound, C45H40N4O5, the cyclohexane entity on the (3-cyano-2,5-dihydrofuran-2-ylidene)propanedinitrile group, which replaces the usual dimethyl substituents, has not perturbed the delocalization geometry significantly. Weak intermolecular interactions, viz. C-H...N(cyano), C-H...O(ether), C-H...[pi] and [pi]-[pi] [between the aromatic rings with the shortest centroid-centroid distance of 3.603 (3) Å], consolidate the crystal packing, which exhibits voids of 57 Å3.

Related literature

For related structures, see Bhuiyan et al. (2011[Bhuiyan, M. D. H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.]); Gainsford et al. (2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.], 2013[Gainsford, G. J., Ashraf, M. & Kay, A. J. (2013). Acta Cryst. E69, o120-o121.]); Gainsford, Anderson et al. (2011[Gainsford, G. J., Anderson, J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3046-o3047.]); Gainsford, Ashraf & Kay (2011[Gainsford, G. J., Ashraf, M. & Kay, A. J. (2011). Acta Cryst. E67, o893.]). 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 calculation software, see: Marder et al. (1993[Marder, S. R., Perry, J. W., Tiemann, B. G., Gorman, C. B., Gilmour, S. & Biddle, S. L. (1993). J. Am. Chem. Soc. 115, 2524-2526.]).

[Scheme 1]

Experimental

Crystal data
  • C45H40N4O5

  • Mr = 716.81

  • Monoclinic, C 2/c

  • a = 29.7208 (16) Å

  • b = 16.0089 (4) Å

  • c = 16.5105 (6) Å

  • [beta] = 106.705 (5)°

  • V = 7524.1 (5) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 120 K

  • 0.49 × 0.45 × 0.01 mm

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

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.638, Tmax = 1.000

  • 31832 measured reflections

  • 6878 independent reflections

  • 4748 reflections with I > 2[sigma](I)

  • Rint = 0.071

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

  • wR(F2) = 0.144

  • S = 1.02

  • 6878 reflections

  • 488 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C33-C38 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C8-H8A...N3i 0.99 2.54 3.504 (3) 163
C19-H19...N2ii 0.95 2.47 3.347 (3) 153
C22-H22B...N2ii 0.98 2.59 3.454 (3) 147
C29-H29...O5iii 0.95 2.54 3.430 (3) 156
C12-H12A...Cg1iii 0.99 2.55 3.542 (3) 177
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP in WinGX (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: CV5370 ).


Acknowledgements

We thank Dr J. Wikaira of the University of Canterbury, New Zealand, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bhuiyan, M. D. H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.  [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] [details]
Gainsford, G. J., Ashraf, M. & Kay, A. J. (2011). Acta Cryst. E67, o893.  [CSD] [CrossRef] [details]
Gainsford, G. J., Ashraf, M. & Kay, A. J. (2013). Acta Cryst. E69, o120-o121. [CrossRef] [details]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Marder, S. R., Perry, J. W., Tiemann, B. G., Gorman, C. B., Gilmour, S. & Biddle, S. L. (1993). J. Am. Chem. Soc. 115, 2524-2526.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o103-o104   [ doi:10.1107/S1600536812050532 ]

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