2,2′-[1,2-Phenyl­enebis(aza­nedi­yl)]di­aceto­nitrile

Rivera, A.; Jiménez-Cruz, L.; Maldonado, M.; Kučeráková, M.; Dušek, M.

doi:10.1107/S1600536812047538

Volume 68
Part 12
Page o3429
December 2012

Received 17 November 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 12.3
Details

2,2'-[1,2-Phenylenebis(azanediyl)]diacetonitrile

Augusto Rivera,^a ^* Leonardo Jiménez-Cruz,^a Mauricio Maldonado,^a Monika Kuceráková ^b and Michal Dusek ^b

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The title compound, C₁₀H₁₀N₄, shows chemical but not crystallographic C₂ symmetry. The two cyanomethyl groups are located in an anti position with respect to the aromatic ring. In the crystal, molecules form parallel ladder-like tapes linked through two N-HN hydrogen bonds. Further weak intramolecular N-HN hydrogen bonding is responsible for the elongation of one of the C_aromatic-N bonds.

Related literature

For general background to the title compound, see: Rivera et al. (2010). For related structures, see: Rivera et al. (2010, 2011); Silversides et al. (2006).

Experimental

Crystal data

C₁₀H₁₀N₄
M_r = 186.2
Orthorhombic, P b c a
a = 7.6404 (3) Å
b = 15.1703 (7) Å
c = 15.9168 (7) Å
V = 1844.87 (14) Å³
Z = 8
Cu K radiation
= 0.69 mm^-1
T = 120 K
0.17 × 0.15 × 0.10 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.68, T_max = 1
9893 measured reflections
1641 independent reflections
1359 reflections with I > 3(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.104
S = 1.55
1641 reflections
133 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N4ⁱ	0.935 (18)	2.202 (19)	3.0946 (19)	159.2 (16)
N2-H2N1	0.889 (18)	2.427 (18)	2.7524 (18)	102.0 (13)
N2-H2N1ⁱⁱ	0.889 (18)	2.494 (17)	3.2536 (16)	143.8 (15)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6866 ).

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well the Praemium Academiae project of the Academy of Sciences of the Czech Republic. LJ-C acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Maldonado, M., Casas, J. L., Dusek, M. & Fejfarová, K. (2011). Acta Cryst. E67, o990.
Rivera, A., Maldonado, M., Ríos-Motta, J., Navarro, M. A. & González-Salas, D. (2010). Tetrahedron Lett. 51, 102-104.
Silversides, J. D., Sparke, A. E. & Archibald, S. J. (2006). Acta Cryst. E62, o5944-o5946.

organic compounds