(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

Gainsford, G.J.; Clarke, D.J.; Kay, A.J.

doi:10.1107/S1600536812050532

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 (C-C) = 0.003 Å
R = 0.048
wR = 0.144
Data-to-parameter ratio = 14.1
Details

(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

Graeme J. Gainsford,^a ^* David J. Clarke ^b and Andrew J. Kay ^b

^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-HN(cyano), C-HO(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); Gainsford et al. (2008, 2013); Gainsford, Anderson et al. (2011); Gainsford, Ashraf & Kay (2011). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For calculation software, see: Marder et al. (1993).

Experimental

Crystal data

C₄₅H₄₀N₄O₅
M_r = 716.81
Monoclinic, C 2/c
a = 29.7208 (16) Å
b = 16.0089 (4) Å
c = 16.5105 (6) Å
= 106.705 (5)°
V = 7524.1 (5) Å³
Z = 8
Cu K radiation
= 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 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.638, T_max = 1.000
31832 measured reflections
6878 independent reflections
4748 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.144
S = 1.02
6878 reflections
488 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C8-H8AN3ⁱ	0.99	2.54	3.504 (3)	163
C19-H19N2ⁱⁱ	0.95	2.47	3.347 (3)	153
C22-H22BN2ⁱⁱ	0.98	2.59	3.454 (3)	147
C29-H29O5ⁱⁱⁱ	0.95	2.54	3.430 (3)	156
C12-H12ACg1ⁱⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP in WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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Bhuiyan, M. D. H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gainsford, G. J., Anderson, J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3046-o3047.
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Gainsford, G. J., Ashraf, M. & Kay, A. J. (2013). Acta Cryst. E69, o120-o121.
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Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.