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Volume 69 
Part 2 
Page o301  
February 2013  

Received 21 January 2013
Accepted 22 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.135
Data-to-parameter ratio = 11.3
Details
Open access

The charge-transfer complex 1-aminoanthraquinone-7,7',8,8'-tetracyanoquinodimethane (1/1)

aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and bInstitut für Anorganische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany
Correspondence e-mail: adriano@daad-alumni.de

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-H...N and N-H...O interactions connect the molecules perpendicular to the stacking direction. Additionally, an intramolecular N-H...O hydrogen-bond interaction is observed for 1-aminoanthraquinone.

Related literature

For a revised structure of 1-aminoanthraquinone, see: Milic et al. (2012[Milic, D., Dzolic, Z., Cametti, M., Prugovecki, B. & Zinic, M. (2012). J. Mol. Struct. 920, 178-182.]). For charge-transfer complexes of aromatic derivatives with 7,7',8,8'-tetracyanoquinodimethane, see: Press et al. (2012[Press, D. J., Back, T. G. & Sutherland, T. C. (2012). Tetrahedron Lett. 53, 1603-1605.]). For the conductivity of organic salts, see: Jérome (2004[Jérome, D. (2004). Chem. Rev. 104, 5565-5591.]). For the coordination chemistry of 7,7',8,8'-tetracyanoquinodimethane, see: Kaim & Moscherosch (1994[Kaim, W. & Moscherosch, M. (1994). Coord. Chem. Rev. 129, 157-193.]).

[Scheme 1]

Experimental

Crystal data
  • C12H4N4·C14H9NO2

  • Mr = 427.41

  • Monoclinic, P 21 /c

  • a = 7.4916 (2) Å

  • b = 9.4321 (3) Å

  • c = 28.8093 (8) Å

  • [beta] = 95.8785 (15)°

  • V = 2025.00 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.29 × 0.05 × 0.04 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: analytical (Alcock, 1970[Alcock, N. W. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, p. 271. Copenhagen: Munksgaard.]) Tmin = 0.974, Tmax = 0.996

  • 19055 measured reflections

  • 3972 independent reflections

  • 2324 reflections with I > 2[sigma](I)

  • Rint = 0.147

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.135

  • S = 1.01

  • 3972 reflections

  • 350 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O2 0.93 (3) 1.96 (3) 2.654 (3) 130 (2)
N1-HN1...O2i 0.93 (3) 2.25 (3) 3.019 (3) 139 (2)
N1-HN2...N3ii 1.02 (3) 2.22 (3) 3.229 (3) 171 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6884 ).


Acknowledgements

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.

References

Alcock, N. W. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, p. 271. Copenhagen: Munksgaard.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Jérome, D. (2004). Chem. Rev. 104, 5565-5591.  [ISI] [PubMed]
Kaim, W. & Moscherosch, M. (1994). Coord. Chem. Rev. 129, 157-193.  [CrossRef] [ChemPort] [ISI]
Milic, D., Dzolic, Z., Cametti, M., Prugovecki, B. & Zinic, M. (2012). J. Mol. Struct. 920, 178-182.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Press, D. J., Back, T. G. & Sutherland, T. C. (2012). Tetrahedron Lett. 53, 1603-1605.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o301  [ doi:10.1107/S1600536813002195 ]

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