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Volume 70 
Part 1 
Pages o29-o30  
January 2014  

Received 28 November 2013
Accepted 3 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.054
wR = 0.153
Data-to-parameter ratio = 28.2
Details
Open access

2-{2-[5-(4-Cyano-5-di­cyano­methyl­idene-2,2-dimethyl-2,5-di­hydro­furan-3-yl)penta-2,4-dienyl­idene]-3,3-dimethyl-2,3-di­hydro-1H-indol-1-yl}ethyl 3,5-bis­(benz­yloxy)benzoate

In the title mol­ecule, C48H42N4O5, a potential non-linear optical compound, the furan ring [r.m.s. deviation = 0.010 (1) Å] and the indolyl­idene ring system [r.m.s. deviation = 0.013 (2) Å] are inclined to one another by 18.52 (6)°. This is similar to the arrangement [16.51 (18)°] found for the N-hy­droxy­ethyl adduct of the title compound [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, 1-12.]). Mol. Cryst. Liq. Cryst. 548, 1-12]. Replacing the hy­droxy­ethyl group with 3,5-di­benzyl­oxybenzoate has not resulted in a non-centrosymmetric lattice arrangement or significant changes to the basic mol­ecular structure. In the crystal, mol­ecules are linked via pairs of C-H...N hydrogen bonds, forming inversion dimers with an R22(20) ring motif. The dimers are linked via C-H...O hydrogen bonds, forming C(17) chains along [010]. The chains are linked by further C-H...N hydrogen bonds, forming layers parallel to (001) and enclosing R22(44) ring motifs. There are also C-H...[pi] inter­actions present, stabilizing the inter­layer orientation of the pendant bis­(benz­yloxy)benzo­yloxy group.

Related literature

For general background to organic non-linear optical (NLO) materials and details of similar structures, see: Kim et al. (2007[Kim, T. D., Kang, J. W., Luo, J. & Jang, S. H. (2007). J. Am. Chem. Soc. 2007, 129, 488-489.]); Gainsford et al. (2007[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2007). Acta Cryst. C63, o633-o637.], 2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.]); Smith et al. (2006[Smith, G. J., Dunford, C. L., Kay, A. J. & Woolhouse, A. D. (2006). J. Photochem. Photobiol. A Chem. 179, 237-242.]); 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, 1-12.]); 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.]); Ojala et al. (2012[Ojala, A., Burckstummer, H., Hwang, J., Graf, K., Von Vacano, B., Meerholz, K., Erk, P. & Wurthner, F. (2012). J. Mater. Chem. 22, 4473-4482.]). For the synthesis of the title compound, see: Clarke et al. (2009[Clarke, D. J., Middleton, A., Teshome, A., Bhuiyan, M. D. H., Ashraf, M., Gainsford, G. J., Asselberghs, I., Clays, K., Smith, G. J. & Kay, A. J. (2009). AIP Conf. Proc. V, 1151, 90-93.]). For details of the N-hy­droxy­ethyl adduct 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, 1-12.]). 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
  • C48H42N4O5

  • Mr = 754.86

  • Monoclinic, P 21 /c

  • a = 16.1925 (5) Å

  • b = 15.6802 (5) Å

  • c = 17.6529 (6) Å

  • [beta] = 115.038 (2)°

  • V = 4060.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.31 × 0.26 × 0.25 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.682, Tmax = 0.746

  • 106328 measured reflections

  • 14582 independent reflections

  • 9621 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.153

  • S = 1.02

  • 14582 reflections

  • 518 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C29-C34 ring.

D-H...A D-H H...A D...A D-H...A
C15-H15...N3i 0.95 2.48 3.404 (2) 165
C30-H30...O1ii 0.95 2.50 3.4136 (17) 162
C32-H32...N2iii 0.95 2.54 3.475 (2) 167
C9-H9A...Cg1iii 0.98 2.89 3.8454 (16) 166
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. 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., 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: SU2670 ).


Acknowledgements

We thank Drs J. Wikaira and C. Fitchett of the University of Canterbury, New Zealand, for their assistance with 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, 1-12.  [CrossRef]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [IUCr Journals]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clarke, D. J., Middleton, A., Teshome, A., Bhuiyan, M. D. H., Ashraf, M., Gainsford, G. J., Asselberghs, I., Clays, K., Smith, G. J. & Kay, A. J. (2009). AIP Conf. Proc. V, 1151, 90-93.  [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. (2007). Acta Cryst. C63, o633-o637.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kim, T. D., Kang, J. W., Luo, J. & Jang, S. H. (2007). J. Am. Chem. Soc. 2007, 129, 488-489.
Li, S.-Y., Song, Y.-Y., You, Z.-L., Wen, Y.-W. & Qin, J.-G. (2005). Acta Cryst. E61, o2093-o2095.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Ojala, A., Burckstummer, H., Hwang, J., Graf, K., Von Vacano, B., Meerholz, K., Erk, P. & Wurthner, F. (2012). J. Mater. Chem. 22, 4473-4482.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, G. J., Dunford, C. L., Kay, A. J. & Woolhouse, A. D. (2006). J. Photochem. Photobiol. A Chem. 179, 237-242.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o29-o30   [ doi:10.1107/S1600536813032868 ]

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