[Journal logo]

Volume 68 
Part 3 
Page o828  
March 2012  

Received 3 February 2012
Accepted 17 February 2012
Online 24 February 2012

[nk2144sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.134
Data-to-parameter ratio = 9.0
Details
Open access

9-Ethynyl-9H-carbazole

Hideyuki Tabataa and Tsunehisa Okunoa*

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

The title compound, C14H9N, is the second crystallographically characterized example of an ynamine with an H atom in the C-terminal position. There are two independent molecules (A and B) in the asymmetric unit. The structures of both molecules are essentially planar (r.m.s. deviation = 0.0312 and 0.0152 Å). The N-Csp bond lengths are 1.353 (4) and 1.350 (4) Å, and those of the acetylene bonds are 1.189 (4) and 1.190 (4) Å. The Csp-H bond lengths are 0.95 (5) and 0.97 (4) Å. These geometries are consistent with those of the previously reported ynamine characterized by crystallography. In the crystal, the molecules stack along the c axis, forming two kinds of columnar structures. The acetylene C atoms of molecule A have a short contact [3.341 (4) Å and 3.396 (4) Å] with an adjacent molecule A at the C-C bond of the fused part, which originates in [pi]-[pi] stacking interaction; no remarkable spatial contact is recognized within the stacking of molecule B.

Related literature

For the preparation of the title compound, see: 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 related structure of a diacetylene compound having 9-carbazolyl groups at both ends, see: Mayerle & Flandera (1978[Mayerle, J. J. & Flandera, M. A. (1978). Acta Cryst. B34, 1374-1376.]). For the related structure of an ynamine compound that carrys an H atom at an acetylene terminal, see: Tabata & Okuno (2011[Tabata, H. & Okuno, T. (2011). Acta Cryst. E67, o3169.]). For related structures of ynamine compounds, see: Galli et al. (1988[Galli, R., Neuenschwander, M. & Engel, P. (1988). Helv. Chim. Acta, 71, 1914-1923.], 1989[Galli, R., Neuenschwander, M. & Engel, P. (1989). Helv. Chim. Acta, 72, 1324-1336.]); Okuno et al. (2006[Okuno, T., Ikeda, S., Kubo, N. & Sandman, D. J. (2006). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 456, 35-44.]); Tabata et al. (2012[Tabata, H., Tokoyama, H., Yamakado, H. & Okuno, T. (2012). J. Mater. Chem. 22, 115-122.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9N

  • Mr = 191.23

  • Orthorhombic, P n a 21

  • a = 23.642 (5) Å

  • b = 16.171 (4) Å

  • c = 5.1523 (11) Å

  • V = 1969.8 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 93 K

  • 0.15 × 0.07 × 0.04 mm
Data collection

  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.994, Tmax = 0.997

  • 16048 measured reflections

  • 2515 independent reflections

  • 2257 reflections with F2 > 2[sigma](F2)

  • Rint = 0.068
Refinement

  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.134

  • S = 1.10

  • 2513 reflections

  • 279 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.23 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: NK2144 ).

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency.

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. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Galli, R., Neuenschwander, M. & Engel, P. (1988). Helv. Chim. Acta, 71, 1914-1923.  [CrossRef] [ChemPort]
Galli, R., Neuenschwander, M. & Engel, P. (1989). Helv. Chim. Acta, 72, 1324-1336.  [CrossRef] [ChemPort]
Mayerle, J. J. & Flandera, M. A. (1978). Acta Cryst. B34, 1374-1376.  [CrossRef] [details] [ISI]
Okuno, T., Ikeda, S., Kubo, N. & Sandman, D. J. (2006). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 456, 35-44.  [CSD] [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]
Tabata, H. & Okuno, T. (2011). Acta Cryst. E67, o3169.  [CSD] [CrossRef] [details]
Tabata, H., Tokoyama, H., Yamakado, H. & Okuno, T. (2012). J. Mater. Chem. 22, 115-122.  [ISI] [CSD] [CrossRef] [ChemPort]

Acta Cryst (2012). E68, o828  [ doi:10.1107/S1600536812007143 ]

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.