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Volume 69 
Part 1 
Pages o120-o121  
January 2013  

Received 21 November 2012
Accepted 13 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 116 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.059
wR = 0.177
Data-to-parameter ratio = 13.2
Details
Open access

2-[4-(2-{5-tert-Butyl-2-chloro-3-[2-(3-pentyl-1,3-benzothiazol-2-ylidene)ethylidene]cyclohex-1-enyl}ethenyl)-3-cyano-5,5-dimethylfuran-2-ylidene]malononitrile

aIndustrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
Correspondence e-mail: g.gainsford@irl.cri.nz

In the title molecule, C36H39ClN4OS, the non-aromatic part of the cyclohex-1-enyl ring and the attached tert-butyl group are disordered over two conformations with occupancy ratios of 0.52 (3):0.48 (3) and 0.53 (3):0.47 (3), respectively. The polyene chain single- and double-bond dimensions contrast with a closely related compound [Bouit et al. (2007[Bouit, P.-A., Wetzel, G., Berginc, G., Loiseaux, B., Toupet, L., Feneyrou, P., Bretonniere, Y., Kamada, K., Maury, O. & Andraud, C. (2007). Chem. Mater. 19, 5325-5335.]). Chem. Mater. 19, 5325-5335] with an approximate 19° twist between donor and acceptor ends of the molecule, related to the additional intramolecular C-H...S interaction. In the title compound, the molecules pack into dimeric units about centres of symmetry utilizing weak C-H...N(cyano) and C-H...O attractive interactions, building both chain and ring motifs about the centres [R22(8) and R22(9)]. Adjacent dimeric sets then form a herringbone configuration.

Related literature

For general background to our ongoing research involving the development of organic non-linear optical (NLO) chromophores, see: Kay et al. (2004[Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 45, 1321-1330.]); 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.]). For related structures, see: Bouit et al. (2007[Bouit, P.-A., Wetzel, G., Berginc, G., Loiseaux, B., Toupet, L., Feneyrou, P., Bretonniere, Y., Kamada, K., Maury, O. & Andraud, C. (2007). Chem. Mater. 19, 5325-5335.], 2008[Bouit, P.-A., Di Piazza, E., Rigaut, S., Le Guennic, B., Aronica, B., Toupet, L., Andraud, C. & Maury, O. (2008). Org. Lett. 10, 4159-4162.]); Gainsford et al. (2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the BLA parameter, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C36H39ClN4OS

  • Mr = 611.22

  • Monoclinic, P 21 /n

  • a = 8.6293 (5) Å

  • b = 20.1267 (11) Å

  • c = 19.5299 (11) Å

  • [beta] = 102.236 (4)°

  • V = 3314.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 116 K

  • 0.71 × 0.30 × 0.10 mm

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

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) and SADABS (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.614, Tmax = 0.746

  • 32003 measured reflections

  • 5943 independent reflections

  • 3121 reflections with I > 2[sigma](I)

  • Rint = 0.106

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.177

  • S = 1.01

  • 5943 reflections

  • 451 parameters

  • 75 restraints

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9A...O1i 0.98 2.59 3.494 (6) 154
C32-H32A...N2ii 0.98 2.73 3.702 (5) 166
C33-H33B...N1ii 0.98 2.65 3.539 (6) 150
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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 (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: BX2431 ).


Acknowledgements

We thank Drs J. Wikaira & C. Fitchett of the University of Canterbury, New Zealand, for the data collection.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
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]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bouit, P.-A., Di Piazza, E., Rigaut, S., Le Guennic, B., Aronica, B., Toupet, L., Andraud, C. & Maury, O. (2008). Org. Lett. 10, 4159-4162.  [CrossRef] [PubMed] [ChemPort]
Bouit, P.-A., Wetzel, G., Berginc, G., Loiseaux, B., Toupet, L., Feneyrou, P., Bretonniere, Y., Kamada, K., Maury, O. & Andraud, C. (2007). Chem. Mater. 19, 5325-5335.  [CrossRef] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.  [CSD] [CrossRef] [details]
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 45, 1321-1330.  [CrossRef]
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. & Bourhill, G. (1993). J. Am. Chem. Soc. 115, 2524-2526.  [CrossRef] [ChemPort] [ISI]
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, o120-o121   [ doi:10.1107/S1600536812050842 ]

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