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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 [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 12.3
Details
Open access

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

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-H...N hydrogen bonds. Further weak intramolecular N-H...N hydrogen bonding is responsible for the elongation of one of the Caromatic-N bonds.

Related literature

For general background to the title compound, see: Rivera et al. (2010[Rivera, A., Maldonado, M., Ríos-Motta, J., Navarro, M. A. & González-Salas, D. (2010). Tetrahedron Lett. 51, 102-104.]). For related structures, see: Rivera et al. (2010[Rivera, A., Maldonado, M., Ríos-Motta, J., Navarro, M. A. & González-Salas, D. (2010). Tetrahedron Lett. 51, 102-104.], 2011[Rivera, A., Maldonado, M., Casas, J. L., Dusek, M. & Fejfarová, K. (2011). Acta Cryst. E67, o990.]); Silversides et al. (2006[Silversides, J. D., Sparke, A. E. & Archibald, S. J. (2006). Acta Cryst. E62, o5944-o5946.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N4

  • Mr = 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[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.68, Tmax = 1

  • 9893 measured reflections

  • 1641 independent reflections

  • 1359 reflections with I > 3[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N4i 0.935 (18) 2.202 (19) 3.0946 (19) 159.2 (16)
N2-H2...N1 0.889 (18) 2.427 (18) 2.7524 (18) 102.0 (13)
N2-H2...N1ii 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CSD] [CrossRef] [details]
Rivera, A., Maldonado, M., Ríos-Motta, J., Navarro, M. A. & González-Salas, D. (2010). Tetrahedron Lett. 51, 102-104.  [ISI] [CSD] [CrossRef] [ChemPort]
Silversides, J. D., Sparke, A. E. & Archibald, S. J. (2006). Acta Cryst. E62, o5944-o5946.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3429  [ doi:10.1107/S1600536812047538 ]

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