Received 26 October 2012
The asymmetric unit of the title compound, C12H10N2, which may serve as a model for mitosenes, contains two independent molecules. The conformation of the five-membered rings in both molecules is envelope, with the central CH2-CH2-CH2 C atom at the flap in each case. In the crystal, they interact by a combination of weak C-HN and - interactions [centroid-centroid distances = 3.616 (1) and 3.499 (1) Å] and C-H contacts.
For the synthesis of the title compound by intramolecular Heck reaction of [1-(2-bromophenyl)pyrrolidin-2-ylidene]-acetonitrile, see: Michael et al. (1993). For an alternative synthesis by cyclization of [2-(2-oxopyrrolidin-1-yl)phenyl]acetonitrile with sodium hydride, see: Verboom et al. (1986). For background to mitosenes, see: Franck (1978); Kasai & Kono (1992).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2462 ).
This work was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work. Ms C. Wilson is thanked for carrying out the preliminary synthesis.
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