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Volume 69 
Part 1 
Page o102  
January 2013  

Received 5 December 2012
Accepted 8 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.090
Data-to-parameter ratio = 11.6
Details
Open access

N,N'-(Pyridine-2,6-diyl)dibenzamide

aSama Technical and Vocational Training College, Islamic Azad University, Mamaghan Branch, Mamaghan, Iran,bDepartment of Chemistry, University of Zanjan, 45195-313 Zanjan, Iran, and cChemistry Department, The University of Warsaw, Pasteura 1, 02093 Warszawa, Poland
Correspondence e-mail: nadernoshiranzadeh@yahoo.com

The molecule of the title compound, C19H15N3O2, is completed by the application of crystallographic twofold symmetry, with the pyridine N atom lying on the rotation axis. The molecular structure is approximately planar, the dihedral angle between the mean planes of the pyridine and benzene rings being 7.53 (11)°. In the crystal, N-H...O hydrogen bonds link the molecules into a two-dimensional array perpendicular to the c axis.

Related literature

For metal complexes of carboxamide ligands, see: Adolph et al. (2012[Adolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92-98.]); Amiri et al. (2009[Amiri, A., Amirnasr, M., Meghdadi, S., Mereiter, K., Ghodsi, V. & Gholami, A. (2009). Inorg. Chim. Acta, 362, 3934-3940.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O2

  • Mr = 317.34

  • Tetragonal, P 41 21 2

  • a = 5.0314 (1) Å

  • c = 58.701 (3) Å

  • V = 1486.02 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.21 × 0.09 × 0.02 mm

Data collection
  • Oxford Diffraction Xcalibur Opal diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.986, Tmax = 1.000

  • 1298 measured reflections

  • 16463 independent reflections

  • 1168 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.090

  • S = 1.23

  • 1298 reflections

  • 112 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.86 2.25 3.030 (2) 151
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2006[Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5180 ).


Acknowledgements

The authors are grateful to the University of Zanjan, Islamic Azad University (Mamagghan Branch) and the University of Warsaw for financial support.

References

Adolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92-98.  [CSD] [CrossRef] [ChemPort]
Amiri, A., Amirnasr, M., Meghdadi, S., Mereiter, K., Ghodsi, V. & Gholami, A. (2009). Inorg. Chim. Acta, 362, 3934-3940.  [ISI] [CSD] [CrossRef] [ChemPort]
Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o102  [ doi:10.1107/S1600536812050167 ]

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