Triclinic polymorph of dibenzotetra­thia­fulvalene

Mamada, M.; Yamashita, Y.

doi:10.1107/S1600536809030013

Volume 65
Part 9
Page o2083
September 2009

Received 24 July 2009
Accepted 29 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 17.5
Details

Triclinic polymorph of dibenzotetrathiafulvalene

Masashi Mamada ^a and Yoshiro Yamashita ^a ^*

^aDepartment of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan
Correspondence e-mail: yoshiro@echem.titech.ac.jp

Crystals of the title compound (DBTTF), C₁₄H₈S₄, feature a triclinic polymorph different from two known monoclinic polymorphs. In this form, there are two independent centrosymmetric half-molecules in the asymmetric unit. Although the molecular orientations are relatively similar to one of monoclinic polymorphs, the packing motif is different.

Related literature

For the synthesis, see: Nakayama et al. (1976). For the monoclinic polymorphs of DBTTF, see: Emge et al. (1982); Brillante et al. (2008). For the electronic properties of DBTTF, see: Jigami et al. (1998). For the characteristics of field-effect transistors based on DBTTF, see, for example: Mas-Torrent et al. (2005); Shibata et al. (2008). For related structures, see: Mas-Torrent et al. (2004); Naraso et al. (2006).

Experimental

Crystal data

C₁₄H₈S₄
M_r = 304.46
Triclinic, $[P \overline 1]$
a = 8.6562 (4) Å
b = 9.4144 (5) Å
c = 9.5144 (4) Å
= 74.0424 (15)°
= 63.6158 (13)°
= 65.5653 (14)°
V = 628.43 (5) Å³
Z = 2
Mo K radiation
= 0.73 mm^-1
T = 93 K
0.35 × 0.25 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.663, T_max = 0.896
6216 measured reflections
2871 independent reflections
2193 reflections with F² > 2(F²)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.110
S = 1.12
2871 reflections
164 parameters
All H-atom parameters refined
_max = 0.56 e Å^-3
_min = -0.46 e Å^-3

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5019 ).

Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (No. 19350092) from the Ministry of Education, Culture, Sports, Science and Technology, Japan, the Mizuho Foundation for the Promotion of Sciences, the Global COE program `Education and Research Center for Emergence of New Molecular Chemistry' and the Research Fellows of the Japan Society for the Promotion of Science.

References

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organic compounds