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Volume 68 
Part 12 
Pages o3298-o3299  
December 2012  

Received 23 September 2012
Accepted 1 November 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 168 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.058
wR = 0.160
Data-to-parameter ratio = 14.9
Details
Open access

1,2-Bis{4-[1-(anthracen-9-ylmethyl)-1H-1,2,3-triazol-4-yl]phenyl}-1,2-bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]ethane

aDepartment of Chemistry, Memorial University of Newfoundland, St Johns, NL, Canada A1B 3X7, and bDepartment of Chemistry and C-CART X-Ray Diffraction Lab, Memorial University of Newfoundland, St Johns, NL, Canada A1B 3X7
Correspondence e-mail: louise.dawe@mun.ca

The title molecule, C58H44N6S8, has point symmetry 2 (in the Schönfliess notation C2). The related crystallographic twofold axis bisects the central ethane bond while it is parallel to the monoclinic unique axis of the unit cell. The dithiole=C-C=dithiole torsion angle is 103.7 (4)° and the triazole-anthracene moieties adopt a pincer-like conformation. The crystal structure features C-H...S and C-H...N contacts. The distance between the stacked anthracene fragments [centroid-centroid separations of 3.6871 (19) Å, off-set by 1.516 (3) Å and mean anthracene plane-plane separations of 3.361 (2) Å], which are parallel to (101) and (-101), indicates intermolecular anthracene-anthracene [pi]-[pi] contacts. One of the terminal methylsulfanyl groups was modelled as being disordered with two refined orientations that converged to occupancies of 0.809 (5) and 0.191 (5).

Related literature

The simpler analogues, 4,4',5,5'-tetramethylthiolato-2,2'-ethanediylidene(1,3-dithiole) and bis(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)succinonitrile, were previously reported by Bryce et al. (1996[Bryce, M. R., Moore, A. J., Tanner, B. K., Whitehead, R., Clegg, W., Gerson, F., Lamprecht, A. & Pfenninger, S. (1996). Chem. Mater. 8, 1182-1188.]) and Jia et al. (2005[Jia, C., Liu, S.-X., Neels, A., Stoeckli-Evans, H. & Decurtins, S. (2005). Synthesis, 13, 2157-2160.]), respectively. For information on the photophysical properties of tetrathiafulvalene vinylogues, see: Mulla et al. (2012[Mulla, K., Dongare, P., Thompson, D. W. & Zhao, Y. (2012). Org. Biomol. Chem. 10, 2542-2544.]). For synthesis via Cu-catalysed alkyne-azide coupling reactions employed for the title compound, see: Meldal & Tornøe (2008[Meldal, M. & Tornøe, C. W. (2008). Chem. Rev. 108, 2952-3015.]); Hein et al. (2010[Hein, J. E. & Fokin, V. V. (2010). Chem. Soc. Rev. 39, 1302-1315.]); Zhao et al. (2012[Zhao, Y., Chen, G., Mulla, K., Mahmud, I., Liang, S., Dongare, P., Thompson, D. W., Dawe, L. N. & Bouzan, S. (2012). Pure Appl. Chem. 84, 1005-1025.]). For a discussion of hydrogen bonding, including non-traditional interactions, see: Desiraju (2011[Desiraju, G. R. (2011). Angew. Chem. Int. Ed. 50, 52-59.]); Arunan et al. (2011[Arunan, E., Desiraju, G. R., Klein, R. A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D. C., Crabtree, R. H., Dannenberg, J. J., Hobza, P., Kjaergaard, H. G., Legon, A. C., Mennucci, B. & Nesbitt, D. J. (2011). Pure Appl. Chem. 83, 1619-1636.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]) and for a description of the Cambridge Structural Database, see Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C58H44N6S8

  • Mr = 1081.47

  • Monoclinic, C 2/c

  • a = 15.906 (4) Å

  • b = 14.737 (3) Å

  • c = 21.570 (5) Å

  • [beta] = 98.846 (7)°

  • V = 4996 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 168 K

  • 0.27 × 0.23 × 0.12 mm

Data collection
  • Rigaku AFC8 diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.765, Tmax = 0.952

  • 24431 measured reflections

  • 5169 independent reflections

  • 4127 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.160

  • S = 1.06

  • 5169 reflections

  • 347 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C28-H28C...N2i 0.98 2.55 3.495 (5) 161
C25-H25...S2ii 0.95 3.00 3.784 (4) 141
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) 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: FB2271 ).


Acknowledgements

We acknowledge NSERC and the Memorial University of Newfoundland for funding support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arunan, E., Desiraju, G. R., Klein, R. A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D. C., Crabtree, R. H., Dannenberg, J. J., Hobza, P., Kjaergaard, H. G., Legon, A. C., Mennucci, B. & Nesbitt, D. J. (2011). Pure Appl. Chem. 83, 1619-1636.  [ISI] [CrossRef] [ChemPort]
Bryce, M. R., Moore, A. J., Tanner, B. K., Whitehead, R., Clegg, W., Gerson, F., Lamprecht, A. & Pfenninger, S. (1996). Chem. Mater. 8, 1182-1188.  [ChemPort]
Desiraju, G. R. (2011). Angew. Chem. Int. Ed. 50, 52-59.  [ISI] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Hein, J. E. & Fokin, V. V. (2010). Chem. Soc. Rev. 39, 1302-1315.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.
Jia, C., Liu, S.-X., Neels, A., Stoeckli-Evans, H. & Decurtins, S. (2005). Synthesis, 13, 2157-2160.
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.  [ISI] [CrossRef] [ChemPort] [details]
Meldal, M. & Tornøe, C. W. (2008). Chem. Rev. 108, 2952-3015.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mulla, K., Dongare, P., Thompson, D. W. & Zhao, Y. (2012). Org. Biomol. Chem. 10, 2542-2544.  [CrossRef] [ChemPort] [PubMed]
Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhao, Y., Chen, G., Mulla, K., Mahmud, I., Liang, S., Dongare, P., Thompson, D. W., Dawe, L. N. & Bouzan, S. (2012). Pure Appl. Chem. 84, 1005-1025.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3298-o3299   [ doi:10.1107/S1600536812045254 ]

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