Received 3 February 2012
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 - stacking interaction; no remarkable spatial contact is recognized within the stacking of molecule B.
For the preparation of the title compound, see: Cuniberti et al. (1996). For the related structure of a diacetylene compound having 9-carbazolyl groups at both ends, see: Mayerle & Flandera (1978). For the related structure of an ynamine compound that carrys an H atom at an acetylene terminal, see: Tabata & Okuno (2011). For related structures of ynamine compounds, see: Galli et al. (1988, 1989); Okuno et al. (2006); Tabata et al. (2012).
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare, et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2144 ).
This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency.
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