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Volume 70 
Part 1 
Pages o45-o46  
January 2014  

Received 20 November 2013
Accepted 8 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.056
wR = 0.155
Data-to-parameter ratio = 20.7
Details
Open access

2-(3-Cyano-4-{3-[1-(2-hy­droxy­eth­yl)-3,3-dimethyl-1,3-di­hydro­indol-2-yl­idene]prop-2-en­yl}-5,5-dimethyl-5H-furan-2-yl­idene)malono­nitrile

The title compound, C25H24N4O2, adopts a cisoid configuration and has twofold orientational disorder of the 2-hy­droxy­ethyl group. The mol­ecule is twisted from planarity so that the dihedral angle between the terminating indol-2-yl­idene and the furan-2-yl­idene moiety mean planes is 12.75 (7)°. Conformational disorder occurs at the indol-2-yl­idene N atom, which results in two orientations for the hy­droxy­ethyl group [occupancy ratio = 0.896 (2):0.104 (2)], and the hy­droxy O atom of the 2-hy­droxy­ethyl group is located over three sites [occupancy ratio = 0.548 (2):0.348 (2):0.104 (2)]. An intra­molecular C-H...O hydrogen bond involving the lowest occupancy hy­droxy O atom is observed. In the crystal, the mol­ecules pack in parallel dimeric sheets about centres of symmetry, utilizing O-H...N(cyano), C-H...N(cyano) and O-H...O hydrogen bonds, in two sets parallel to (02-1) and (021) planes.

Related literature

For general background to organic non-linear optical (NLO) materials and details of similar structures, see: Kay et al. (2004[Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.]); Dalton et al. (1999[Dalton, L. R., Steier, W. H., Robinson, B. H., Zhang, C., Ren, A. & Garner, S. (1999). J. Mater. Chem. 9, 1905-1920.]); Harper et al. (1999[Harper, A. W., Mao, S. S. H., Ra, Y., Zhang, C., Zhu, J. & Dalton, L. R. (1999). Chem. Mater. 11, 2886-2891.]); Kay et al. (2001a[Kay, A. J., Woolhouse, A. D., Gainsford, G. J., Haskell, T. G., Barnes, T. H., McKinnie, I. T. & Wyss, C. P. (2001a). J. Mater. Chem. 11, 996-1002.],b[Kay, A. J., Woolhouse, A. D., Gainsford, G. J., Haskell, T. G., Wyss, C. P. & Griffin, S. M. (2001b). J. Mater. Chem. 11, 2271-2281.]); Bhuiyan et al. (2011[Bhuiyan, M. D. H., Gainsford, G. J., Kutuvantavida, Y., Quilty, J. W., Kay, A. J., Williams, G. V. M. & Waterland, M. R. (2011). Mol. Cryst. Liq. Cryst. 548, 272-283.]); Gainsford et al. (2011[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3026.]); Ma et al. (2002[Ma, H., Jen, A. K.-Y. & Dalton, L. R. (2002). Adv. Mater. 14, 1339-1365.]); Mao et al. (1998[Mao, S. S. H., Ra, Y., Guo, L., Zhang, C. & Dalton, L. R. (1998). Chem. Mater. 10, 146-155.]); Smith et al. (2010[Smith, G. J., Middleton, A. P., Clarke, D. J., Teshome, A., Kay, A. J. & Bhuiyan, M. D. H. (2010). Opt. Mater. 32, 1237-1243.]); Teshome et al. (2009[Teshome, A., Kay, A. J., Woolhouse, A. D., Clays, K., Asselberghs, I. & Smith, G. J. (2009). Opt. Mater. 31, 575-582.]). For the synthesis of the title compound, see: Bhuiyan et al. (2011[Bhuiyan, M. D. H., Gainsford, G. J., Kutuvantavida, Y., Quilty, J. W., Kay, A. J., Williams, G. V. M. & Waterland, M. R. (2011). Mol. Cryst. Liq. Cryst. 548, 272-283.]). For the definition of bond-length alternation (BLA), see: Marder et al. (1993[Marder, S. R., Perry, J. W., Tiemann, B. G., Gorman, C. B., Gilmour, S., Biddle, S. L. & Bourhill, G. (1993). J. Am. Chem. Soc. 115, 2524-2526.]). For hydrogen-bond 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 details of the Cambridge Structural Database (CSD), see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C25H24N4O2

  • Mr = 412.48

  • Monoclinic, P 21 /n

  • a = 9.4276 (4) Å

  • b = 21.5486 (9) Å

  • c = 11.1178 (5) Å

  • [beta] = 103.916 (2)°

  • V = 2192.31 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.65 × 0.31 × 0.13 mm

Data collection
  • Bruker-Nonius APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.629, Tmax = 0.746

  • 50145 measured reflections

  • 6431 independent reflections

  • 4754 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.155

  • S = 1.03

  • 6431 reflections

  • 311 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2A1-H211...N3i 0.85 (3) 2.17 (4) 2.925 (3) 148 (6)
O2A2-H212...O2A1ii 0.84 2.27 2.939 (4) 137
C8-H8B...N1iii 0.98 2.62 3.501 (2) 150
C9-H9C...N3iv 0.98 2.60 3.539 (2) 160
C13-H13...O2B 0.95 2.57 3.299 (11) 134
C20-H20...N2v 0.95 2.65 3.442 (2) 141
C24A-H24A...N2v 0.99 2.59 3.555 (2) 166
C25A-H25B...N1i 0.99 2.55 3.348 (3) 137
C25B-H25E...N2v 0.99 2.45 3.420 (17) 167
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1; (v) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: 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., 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: SHELXL2012, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2507 ).


Acknowledgements

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

References

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]
Bhuiyan, M. D. H., Gainsford, G. J., Kutuvantavida, Y., Quilty, J. W., Kay, A. J., Williams, G. V. M. & Waterland, M. R. (2011). Mol. Cryst. Liq. Cryst. 548, 272-283.  [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dalton, L. R., Steier, W. H., Robinson, B. H., Zhang, C., Ren, A. & Garner, S. (1999). J. Mater. Chem. 9, 1905-1920.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3026.  [CSD] [CrossRef] [IUCr Journals]
Harper, A. W., Mao, S. S. H., Ra, Y., Zhang, C., Zhu, J. & Dalton, L. R. (1999). Chem. Mater. 11, 2886-2891.  [Web of Science] [CrossRef] [ChemPort]
Kay, A. J., Woolhouse, A. D., Gainsford, G. J., Haskell, T. G., Barnes, T. H., McKinnie, I. T. & Wyss, C. P. (2001a). J. Mater. Chem. 11, 996-1002.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Kay, A. J., Woolhouse, A. D., Gainsford, G. J., Haskell, T. G., Wyss, C. P. & Griffin, S. M. (2001b). J. Mater. Chem. 11, 2271-2281.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.  [Web of Science] [CrossRef] [ChemPort]
Ma, H., Jen, A. K.-Y. & Dalton, L. R. (2002). Adv. Mater. 14, 1339-1365.  [Web of Science] [CrossRef] [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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mao, S. S. H., Ra, Y., Guo, L., Zhang, C. & Dalton, L. R. (1998). Chem. Mater. 10, 146-155.  [Web of Science] [CrossRef] [ChemPort]
Marder, S. R., Perry, J. W., Tiemann, B. G., Gorman, C. B., Gilmour, S., Biddle, S. L. & Bourhill, G. (1993). J. Am. Chem. Soc. 115, 2524-2526.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, G. J., Middleton, A. P., Clarke, D. J., Teshome, A., Kay, A. J. & Bhuiyan, M. D. H. (2010). Opt. Mater. 32, 1237-1243.  [Web of Science] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Teshome, A., Kay, A. J., Woolhouse, A. D., Clays, K., Asselberghs, I. & Smith, G. J. (2009). Opt. Mater. 31, 575-582.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o45-o46   [ doi:10.1107/S1600536813033242 ]

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