4,4′-(1,2,4,5-Tetra­zine-3,6-di­yl)dibenzo­nitrile

Dutkiewicz, G.; Borowiak, T.; Spychała, J.

doi:10.1107/S1600536809008599

Volume 65
Part 4
Page o824
April 2009

Received 16 February 2009
Accepted 9 March 2009
Online 25 March 2009

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.135
Data-to-parameter ratio = 15.2
Details

4,4'-(1,2,4,5-Tetrazine-3,6-diyl)dibenzonitrile

Grzegorz Dutkiewicz,^a Teresa Borowiak ^a ^* and Jaroslaw Spychala ^a

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Correspondence e-mail: borowiak@amu.edu.pl

Molecules of the title compound, C₁₆H₈N₆, lie on crystallographic inversion centres. A dihedral angle of 16.1 (1)° is formed between the central tetrazine ring and the plane of each cyanophenyl group. The molecules form stacks along [100] with a perpendicular interplanar separation of 3.25 (1) Å. C-HN interactions are formed between molecules in neighbouring stacks.

Related literature

For synthesis details, see: Spychala et al. (1994, 2000). For related structures and discussion, see: Higashi & Osaki (1981); Infantes et al. (2003).

Experimental

Crystal data

C₁₆H₈N₆
M_r = 284.28
Monoclinic, P 2₁ /c
a = 4.8447 (5) Å
b = 12.1054 (12) Å
c = 11.6927 (11) Å
= 94.363 (8)°
V = 683.75 (12) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 291 K
0.45 × 0.2 × 0.1 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Poland, Wroclaw, Poland.]$ ) T_min = 0.925, T_max = 0.991
5912 measured reflections
1768 independent reflections
1094 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.135
S = 1.06
1768 reflections
116 parameters
All H-atom parameters refined
_max = 0.16 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6N10ⁱ	0.989 (17)	2.539 (17)	3.370 (2)	141.6 (13)
C8-H8N2ⁱⁱ	0.956 (17)	2.850 (17)	3.6106 (19)	137.2 (12)
C9-H9N10ⁱⁱⁱ	0.993 (17)	2.754 (17)	3.431 (2)	125.8 (12)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Poland, Wroclaw, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Poland, Wroclaw, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2354 ).

Acknowledgements

This work was supported by funds from Adam Mickiewicz University, Faculty of Chemistry.

References

Higashi, T. & Osaki, K. (1981). Acta Cryst. B37, 777-779.
Infantes, L., Mahon, M. F., Male, L., Raithby, P. R., Teat, S. J., Sauer, J., Jagerovic, N., Elguero, J. & Motherwell, S. (2003). Helv. Chim. Acta, 86, 1205-1221.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Poland, Wroclaw, Poland.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1989). Stereochemical Workstation Operation Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spychala, J. (2000). Synth. Commun. 30, 1083-1094.
Spychala, J., Boykin, D. W., Wilson, W. D., Zhao, M., Tidwell, R. R., Dykstra, C. C., Hall, J. E., Jones, S. K. & Schinazi, R. F. (1994). Eur. J. Med. Chem. 29, 363-367.

organic compounds