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Volume 68 
Part 1 
Page o183  
January 2012  

Received 20 November 2011
Accepted 1 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.170
Data-to-parameter ratio = 14.1
Details
Open access

4-Isopropylamino-3-nitrobenzonitrile

aDepartment of Biological and Chemical Engineering, Chien-shiung Institute of Technology, Taicang 215411, Suzhou, People's Republic of China
Correspondence e-mail: ntfenger@163.com

In the title compound, C10H11N3O2, the nitro group is essentially coplanar with the aromatic ring [dihedral angle = 3.4 (3)°] and forms an intramolecular N-H...O hydrogen bond with the amine group. In the crystal, weak aromatic C-H...O and C-H...N hydrogen bonds link the molecules. Weak aromatic ring [pi]-[pi] interactions [minimum ring centroid-centroid separation = 3.9841 (16) Å] are also present.

Related literature

For the synthesis of the title compound, see: Ates-Alagoz & Buyukbingol (2001[Ates-Alagoz, Z. & Buyukbingol, E. (2001). Heterocycl. Commun. 7, 455-460.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11N3O2

  • Mr = 205.22

  • Monoclinic, P 21 /n

  • a = 6.6640 (13) Å

  • b = 20.678 (4) Å

  • c = 7.8900 (16) Å

  • [beta] = 105.74 (3)°

  • V = 1046.5 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 four-circle diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.982, Tmax = 0.991

  • 2821 measured reflections

  • 1926 independent reflections

  • 1228 reflections with I > 2[sigma](I)

  • Rint = 0.020

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.170

  • S = 1.00

  • 1926 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O2 0.86 1.99 2.643 (2) 132
C1-H1A...N1i 0.93 2.61 3.469 (3) 153
C4-H4A...O1ii 0.93 2.40 3.298 (3) 163
C5-H5A...N1iii 0.93 2.60 3.529 (4) 175
Symmetry codes: (i) -x, -y, -z; (ii) x, y, z+1; (iii) -x, -y, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1994)[Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]; cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2168 ).


Acknowledgements

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ates-Alagoz, Z. & Buyukbingol, E. (2001). Heterocycl. Commun. 7, 455-460.  [ChemPort]
Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o183  [ doi:10.1107/S1600536811051737 ]

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