Received 25 February 2013
In the title compound, C11H5I2N, the two iodine-atom substitutents with their large atomic sizes lead to short intramolecular IH distances (3.01 Å). In the crystal, the trisubstituted azulene system forms -stacks [centroid-centroid distance = 3.6343 (11) Å] along the a-axis direction, showing the characteristic azulene interaction mode between the electron-rich five-membered ring and the electron-deficient seven-membered ring. II [3.9129 (2) Å] non-covalent contacts are observed along with weak C-HN and C-H. bonds.
For the naphthalene isomer azulene, see: Plattner & Pfau (1937). For the use of azulene derivatives for medical purposes, see: Shi et al. (2011). The synthesis of the title compound was performed starting from the azulene derivative 2-cyanoazulene (Nozoe et al., 1962). For the synthesis of related compounds, see Schmitt et al. (1998); Suzuka & Yasunami (2008). For related structures, see: Förster et al. (2012); Hussain et al. (2005); Rahman et al. (2004). For halogen interactions in molecular crystal structures, see: Awwadi et al. (2006); Metrangolo et al. (2008). For weak C-HN hydrogen bonding, see: Desiraju & Steiner (1999). For C-H interactions, see: Nishio et al. (2009).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2002 ).
This work was performed within the Cluster of Excellence Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE), which is financially supported by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK).
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