[Journal logo]

Volume 69 
Part 4 
Page o555  
April 2013  

Received 8 March 2013
Accepted 14 March 2013
Online 20 March 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 17.3
Details
Open access

(Z)-9-(1,2-Dichlorovinyl)-9H-carbazole

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

There are two independent molecules in the asymmetric unit of the title compound, C14H9Cl2N, in which the dihedral angles between the dichlorovinyl unit (r.m.s. deviations = 0.0003 and 0.0009 Å), and the carbazole ring are 87.77 (3) and 72.90 (3)°.

Related literature

For the preparation of the title compound, see: Okamoto & Kundu (1970[Okamoto, Y. & Kundu, S. K. (1970). J. Org. Chem. 35, 4250-4252.]); Cuniberti et al. (1996[Cuniberti, C., Dellepiane, G., Piaggio, P., Franco, R., Musso, G. F. C., Dell'Erba, C. & Garbarino, G. (1996). Chem. Mater. 8, 708-713.]). For the structure of 9-vinylcarbazole, see: Tsutsui et al. (1976[Tsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049-3053.]); Tian et al. (2006[Tian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994-1006.]). For the optoelectric properties of vinylcarbazoles, see: Ye et al. (2010[Ye, T., Chen, J. & Ma, D. (2010). Phys. Chem. Chem. Phys. 12, 15410-15413.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Cl2N

  • Mr = 262.14

  • Monoclinic, P 21 /c

  • a = 6.6552 (7) Å

  • b = 24.872 (3) Å

  • c = 14.8636 (15) Å

  • [beta] = 93.7529 (16)°

  • V = 2455.1 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 93 K

  • 0.14 × 0.11 × 0.07 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.939, Tmax = 0.965

  • 19841 measured reflections

  • 5595 independent reflections

  • 5154 reflections with F2 > 2[sigma](F2)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.04

  • 5594 reflections

  • 323 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 forWindows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2093 ).


Acknowledgements

This work was supported by the Adaptable and Seamless Technology Transfer Program through Target-driven R&D from the Japan Science and Technology Agency (JST).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Cuniberti, C., Dellepiane, G., Piaggio, P., Franco, R., Musso, G. F. C., Dell'Erba, C. & Garbarino, G. (1996). Chem. Mater. 8, 708-713.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Okamoto, Y. & Kundu, S. K. (1970). J. Org. Chem. 35, 4250-4252.  [CrossRef] [ChemPort]
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994-1006.  [CSD] [CrossRef] [ChemPort]
Tsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049-3053.  [CrossRef] [details] [ISI]
Ye, T., Chen, J. & Ma, D. (2010). Phys. Chem. Chem. Phys. 12, 15410-15413.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o555  [ doi:10.1107/S1600536813007137 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.