4,5-Diamino­benzene-1,2-dicarbonitrile

Zhang, X.; Wang, W.; Jiang, J.; Ni, Z.

doi:10.1107/S1600536809008733

Volume 65
Part 4
Page o837
April 2009

Received 3 March 2009
Accepted 10 March 2009
Online 25 March 2009

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.146
Data-to-parameter ratio = 13.8
Details

4,5-Diaminobenzene-1,2-dicarbonitrile

Xiuwen Zhang,^a Wei Wang,^a Jianzhuang Jiang ^a ^* and Zhonghai Ni ^a

^aSchool of Chemistry & Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
Correspondence e-mail: nizhh@sdu.edu.cn

The molecular skeleton of the title molecule, C₈H₆N₄, is essentially planar [maximum deviation from the mean plane of 0.037 (2) Å]. All N atoms are involved in the formation of intermolecular N-HN hydrogen bonds. The crystal packing exhibits also dipole-dipole interactions between the cyano groups of neighbouring molecules [CC 3.473 (2) Å].

Related literature

For details of the synthesis, see: Cheeseman (1962); Mitzel et al. (2003). For applications of diamido compounds, see: Rusanova et al. (2002); Youngblood (2006). For a related crystal structure, see: Zhang & Lu (2007).

Experimental

Crystal data

C₈H₆N₄
M_r = 158.17
Monoclinic, P 2₁ /c
a = 8.2966 (11) Å
b = 17.100 (2) Å
c = 5.5295 (7) Å
= 102.256 (2)°
V = 766.60 (17) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 273 K
0.20 × 0.18 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.980, T_max = 0.988
4031 measured reflections
1502 independent reflections
1201 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.146
S = 0.95
1502 reflections
109 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AN3ⁱ	0.86	2.47	3.283 (2)	158
N2-H2BN4ⁱⁱ	0.86	2.37	3.225 (2)	171
N1-H1AN1ⁱⁱⁱ	0.86	2.52	3.3729 (16)	169
N1-H1BN4ⁱⁱ	0.86	2.34	3.188 (2)	171
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z-1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2527 ).

Acknowledgements

This work was supported by the Postdoctoral Scientific Special Foundation of China (grant No. 200801414) and the Postdoctoral Scientific Foundation of Shandong Province (grant No. 200701010).

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheeseman, G. W. H. (1962). J. Chem. Soc. pp. 1170-1176.
Mitzel, F., FitzGerald, S., Beeby, A. & Faust, R. (2003). Chem. Eur. J. 9, 1233-1241.
Rusanova, J., Pilkington, M. & Decurtins, S. (2002). Chem. Commun. pp. 2236-2237.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Youngblood, W. J. (2006). J. Org. Chem. 71, 3345-3356.
Zhang, X.-M. & Lu, J.-T. (2007). Acta Cryst. E63, o3861.

organic compounds