Received 21 January 2013
The reaction of 1-aminoanthraquinone with 7,7',8,8'-tetracyanoquinodimethane yielded the title charge-transfer complex, C14H9NO2·C12H4N4. The molecules have maximum deviations from the mean planes through the non-H atoms of 0.0769 (14) Å for an oxo O atom and 0.1175 (17) Å for a cyano N atom, respectively. The dihedral angle between the two planes is 3.55 (3)°. In the crystal, molecules are stacked into columns along the a-axis direction. Pairs of N-HN and N-HO interactions connect the molecules perpendicular to the stacking direction. Additionally, an intramolecular N-HO hydrogen-bond interaction is observed for 1-aminoanthraquinone.
For a revised structure of 1-aminoanthraquinone, see: Milic et al. (2012). For charge-transfer complexes of aromatic derivatives with 7,7',8,8'-tetracyanoquinodimethane, see: Press et al. (2012). For the conductivity of organic salts, see: Jérome (2004). For the coordination chemistry of 7,7',8,8'-tetracyanoquinodimethane, see: Kaim & Moscherosch (1994).
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6884 ).
We gratefully acknowledge financial support by the German Research Foundation (DFG) through the Collaborative Research Center SFB 813, Chemistry at Spin Centers, and by FAPITEC/SE/FUNTEC/CNPq through the PPP Program 04/2011. JNS also acknowledges CAPES for the award of a scholarship.
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