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

Oliveira, A.B. de; Beck, J.; Daniels, J.; Santos, J.N.; Feitosa, B.R.S.

doi:10.1107/S1600536813002195

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 (C-C) = 0.003 Å
R = 0.052
wR = 0.135
Data-to-parameter ratio = 11.3
Details

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

Adriano Bof de Oliveira,^a ^* Johannes Beck,^b Jörg Daniels,^b Jaciara Nascimento Santos ^a and Bárbara Regina Santos Feitosa ^a

^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-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.

Related literature

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).

Experimental

Crystal data

C₁₂H₄N₄·C₁₄H₉NO₂
M_r = 427.41
Monoclinic, P 2₁ /c
a = 7.4916 (2) Å
b = 9.4321 (3) Å
c = 28.8093 (8) Å
= 95.8785 (15)°
V = 2025.00 (10) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.29 × 0.05 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: analytical (Alcock, 1970) T_min = 0.974, T_max = 0.996
19055 measured reflections
3972 independent reflections
2324 reflections with I > 2(I)
R_int = 0.147

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.135
S = 1.01
3972 reflections
350 parameters
All H-atom parameters refined
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-HN1O2	0.93 (3)	1.96 (3)	2.654 (3)	130 (2)
N1-HN1O2ⁱ	0.93 (3)	2.25 (3)	3.019 (3)	139 (2)
N1-HN2N3ⁱⁱ	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); 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 ).

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.
Kaim, W. & Moscherosch, M. (1994). Coord. Chem. Rev. 129, 157-193.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds