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

Graeme J Gainsford,Mohamed Ashraf,Andrew J Kay

doi:10.1107/s1600536812050842

Abstract

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 ▶). 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 [R 2 2(8) and R 2 2(9)]. Adjacent dimeric sets then form a herringbone configuration.

Highlights

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 title compound, C36H39ClN4OS (3, Figure 1) was synthesized as part of our ongoing research involving the development of organic nonlinear optical (NLO) chromophores. As part of this we have previously reported the crystallographic parameters for chromophores containing an indoline donor coupled to a 2-(3-cyano-4,5,5-trimethyl-5Hfuran-2-ylidene)-malononitrile electron acceptor group (Bhuiyan et al, 2011)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z−1/2

Summary

Data collection

Key indicators: single-crystal X-ray study; T = 116 K; mean (C–C) = 0.006 Å; disorder in main residue; R factor = 0.059; wR factor = 0.177; data-to-parameter ratio = 13.2. 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). 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. 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)].

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