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Volume 69 
Part 7 
Page o1164  
July 2013  

Received 27 May 2013
Accepted 20 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.106
Data-to-parameter ratio = 14.7
Details
Open access

4-(4-Nitrobenzyl)pyridine

aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
Correspondence e-mail: kailani@ju.edu.jo

The title compound, C12H10N2O2, has a twisted conformation, with a dihedral angle between the planes of the pyridine and benzene rings of 78.4 (2)°. The nitro group is coplanar with the attached benzene ring within experimental error. The molecules form centrosymmetric dimers via Car-H...O interactions (H...O = 2.49 Å) and the dimers are [pi]-stacked along the b axis [the separation between ring centroids is 3.788 (2) Å].

Related literature

For adducts of the title compound with different organic acids, see: Smith et al. (1997[Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.]); Smith & Wermuth (2010[Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.], 2013[Smith, G. & Wermuth, U. D. (2013). Acta Cryst. E69, o206.]). For a zinc complex of the title compound, see: Smith et al. (2011[Smith, G., Wermuth, U. D. & Williams, M. L. (2011). Acta Cryst. E67, m359.]). For the analysis of [pi]-stacking interactions, see: Dolomanov et al. (2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N2O2

  • Mr = 214.22

  • Monoclinic, P 21 /c

  • a = 11.4138 (9) Å

  • b = 6.1241 (5) Å

  • c = 15.5812 (13) Å

  • [beta] = 104.561 (9)°

  • V = 1054.13 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.4 × 0.2 × 0.15 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.770, Tmax = 1.000

  • 4351 measured reflections

  • 2136 independent reflections

  • 1514 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.106

  • S = 1.03

  • 2136 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9A...O2i 0.93 2.49 3.302 (2) 146
Symmetry code: (i) -x, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2106 ).


Acknowledgements

The authors thank the University of Jordan and Hamdi Mango Center for Scientific Research for providing support and time to collect the single-crystal X-ray diffraction data set.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.  [CrossRef] [ChemPort] [Web of Science]
Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.  [CSD] [CrossRef] [IUCr Journals]
Smith, G. & Wermuth, U. D. (2013). Acta Cryst. E69, o206.  [CrossRef] [IUCr Journals]
Smith, G., Wermuth, U. D. & Williams, M. L. (2011). Acta Cryst. E67, m359.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1164  [ doi:10.1107/S1600536813017145 ]

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