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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 [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 17.5
Details
Open access

Triclinic polymorph of dibenzotetrathiafulvalene

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[Nakayama, J., Fujiwara, K. & Hoshino, M. (1976). Bull. Chem. Soc. Jpn, 49, 3567-3573.]). For the monoclinic polymorphs of DBTTF, see: Emge et al. (1982[Emge, T. J., Wiygul, F. M., Chappell, J. S., Bloch, A. N., Ferraris, J. P., Cowan, D. O. & Kistenmacher, T. J. (1982). Mol. Cryst. Liq. Cryst. 87, 137-161.]); Brillante et al. (2008[Brillante, A., Bilotti, I., Valle, R. G. D., Venuti, E., Milita, S., Dionigi, C., Borgatti, F., Lazar, A. N., Biscarini, F., Mas-Torrent, M., Oxtoby, N. S., Crivillers, N., Veciana, J., Rovira, C., Leufgen, M., Schmidt, G. & Molenkamp, L. W. (2008). CrystEngComm, 10, 1899-1909.]). For the electronic properties of DBTTF, see: Jigami et al. (1998[Jigami, T., Takimiya, K., Otsubo, T. & Aso, Y. (1998). J. Org. Chem. 63, 8865-8872.]). For the characteristics of field-effect transistors based on DBTTF, see, for example: Mas-Torrent et al. (2005[Mas-Torrent, M., Hadley, P., Bromley, S. T., Crivillers, N., Veciana, J. & Rovira, C. (2005). Appl. Phys. Lett. 86, 012110.]); Shibata et al. (2008[Shibata, K., Ishikawa, K., Takezoe, H., Wada, H. & Mori, T. (2008). Appl. Phys. Lett. 92, 023305.]). For related structures, see: Mas-Torrent et al. (2004[Mas-Torrent, M., Durkut, M., Hadley, P., Ribas, X. & Rovira, C. (2004). J. Am. Chem. Soc. 126, 984-985.]); Naraso et al. (2006[Naraso, Nishida, J., Kumaki, D., Tokito, S. & Yamashita, Y. (2006). J. Am. Chem. Soc. 128, 9598-9599.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8S4

  • Mr = 304.46

  • Triclinic, [P \overline 1]

  • a = 8.6562 (4) Å

  • b = 9.4144 (5) Å

  • c = 9.5144 (4) Å

  • [alpha] = 74.0424 (15)°

  • [beta] = 63.6158 (13)°

  • [gamma] = 65.5653 (14)°

  • V = 628.43 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.663, Tmax = 0.896

  • 6216 measured reflections

  • 2871 independent reflections

  • 2193 reflections with F2 > 2[sigma](F2)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.110

  • S = 1.12

  • 2871 reflections

  • 164 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007[Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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

Brillante, A., Bilotti, I., Valle, R. G. D., Venuti, E., Milita, S., Dionigi, C., Borgatti, F., Lazar, A. N., Biscarini, F., Mas-Torrent, M., Oxtoby, N. S., Crivillers, N., Veciana, J., Rovira, C., Leufgen, M., Schmidt, G. & Molenkamp, L. W. (2008). CrystEngComm, 10, 1899-1909.  [ISI] [CSD] [CrossRef] [ChemPort]
Emge, T. J., Wiygul, F. M., Chappell, J. S., Bloch, A. N., Ferraris, J. P., Cowan, D. O. & Kistenmacher, T. J. (1982). Mol. Cryst. Liq. Cryst. 87, 137-161.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Jigami, T., Takimiya, K., Otsubo, T. & Aso, Y. (1998). J. Org. Chem. 63, 8865-8872.  [CrossRef] [ChemPort]
Mas-Torrent, M., Durkut, M., Hadley, P., Ribas, X. & Rovira, C. (2004). J. Am. Chem. Soc. 126, 984-985.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mas-Torrent, M., Hadley, P., Bromley, S. T., Crivillers, N., Veciana, J. & Rovira, C. (2005). Appl. Phys. Lett. 86, 012110.  [ISI] [CrossRef]
Nakayama, J., Fujiwara, K. & Hoshino, M. (1976). Bull. Chem. Soc. Jpn, 49, 3567-3573.  [CrossRef] [ChemPort] [ISI]
Naraso, Nishida, J., Kumaki, D., Tokito, S. & Yamashita, Y. (2006). J. Am. Chem. Soc. 128, 9598-9599.  [CSD] [CrossRef] [PubMed] [ChemPort]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shibata, K., Ishikawa, K., Takezoe, H., Wada, H. & Mori, T. (2008). Appl. Phys. Lett. 92, 023305.  [ISI] [CrossRef]


Acta Cryst (2009). E65, o2083  [ doi:10.1107/S1600536809030013 ]

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