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

Mulla, K.; Zhao, Y.; Dawe, L.N.

doi:10.1107/S1600536812045254

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.058
wR = 0.160
Data-to-parameter ratio = 14.9
Details

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

Karimulla Mulla,^a Yuming Zhao ^a and Louise N. Dawe ^b ^*

^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-HS and C-HN 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) and Jia et al. (2005), respectively. For information on the photophysical properties of tetrathiafulvalene vinylogues, see: Mulla et al. (2012). For synthesis via Cu-catalysed alkyne-azide coupling reactions employed for the title compound, see: Meldal & Tornøe (2008); Hein et al. (2010); Zhao et al. (2012). For a discussion of hydrogen bonding, including non-traditional interactions, see: Desiraju (2011); Arunan et al. (2011). For standard bond lengths, see: Allen et al. (1987) and for a description of the Cambridge Structural Database, see Allen (2002).

Experimental

Crystal data

C₅₈H₄₄N₆S₈
M_r = 1081.47
Monoclinic, C 2/c
a = 15.906 (4) Å
b = 14.737 (3) Å
c = 21.570 (5) Å
= 98.846 (7)°
V = 4996 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.765, T_max = 0.952
24431 measured reflections
5169 independent reflections
4127 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.160
S = 1.06
5169 reflections
347 parameters
3 restraints
H-atom parameters constrained
_max = 0.70 e Å^-3
_min = -0.62 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C28-H28CN2ⁱ	0.98	2.55	3.495 (5)	161
C25-H25S2ⁱⁱ	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); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

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

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organic compounds