Received 13 February 2012
The title compound [systematic name: (E)-2-hydroxy-5-(phenyldiazenyl)cyclohepta-2,4,6-trien-1-one], C13H10N2O2, is essentially planar with an r.m.s. deviation of 0.036 (2) Å and a dihedral angle of 1.57 (8)° between the phenyl and tropolone rings. In the crystal, molecules are linked by pairs of O-HO hydrogen bonds into inversion dimers. The dimers are further connected by C-HO hydrogen bonds and - stacking interactions, with centroid-centroid distances of 3.6934 (9) and 3.6282 (9) Å.
For synthetic background, see: Gao & Zheng (2001). For applications of azo-substituted tropolones, see: Mori et al. (2002). For related systems, see: Shimanouchi & Sasada (1973); Steyl & Roodt (2006). For a description of the Cambridge Structural Database, see: Allen (2002).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5073 ).
Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.
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