N,N′-(Pyridine-2,6-di­yl)dibenzamide

Mahboubi Anarjan, P.; Noshiranzadeh, N.; Bikas, R.; Woińska, M.; Wozniak, K.

doi:10.1107/S1600536812050167

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.090
Data-to-parameter ratio = 11.6
Details

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

Parisa Mahboubi Anarjan,^a ⁺ Nader Noshiranzadeh,^b ^* Rahman Bikas,^b Magdalena Woinska ^c and Krzysztof Wozniak ^c

^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-HO 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); Amiri et al. (2009).

Experimental

Crystal data

C₁₉H₁₅N₃O₂
M_r = 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 radiation
= 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 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.986, T_max = 1.000
1298 measured reflections
16463 independent reflections
1168 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.090
S = 1.23
1298 reflections
112 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Amiri, A., Amirnasr, M., Meghdadi, S., Mereiter, K., Ghodsi, V. & Gholami, A. (2009). Inorg. Chim. Acta, 362, 3934-3940.
Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds