4-Isopropyl­amino-3-nitro­benzonitrile

Jia, H.

doi:10.1107/S1600536811051737

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.170
Data-to-parameter ratio = 14.1
Details

4-Isopropylamino-3-nitrobenzonitrile

Hong-sheng Jia ^a ^*

^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-HO hydrogen bond with the amine group. In the crystal, weak aromatic C-HO and C-HN 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). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₁₁N₃O₂
M_r = 205.22
Monoclinic, P 2₁ /n
a = 6.6640 (13) Å
b = 20.678 (4) Å
c = 7.8900 (16) Å
= 105.74 (3)°
V = 1046.5 (4) Å³
Z = 4
Mo K radiation
= 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: scan (North et al., 1968) T_min = 0.982, T_max = 0.991
2821 measured reflections
1926 independent reflections
1228 reflections with I > 2(I)
R_int = 0.020
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.170
S = 1.00
1926 reflections
137 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO2	0.86	1.99	2.643 (2)	132
C1-H1AN1ⁱ	0.93	2.61	3.469 (3)	153
C4-H4AO1ⁱⁱ	0.93	2.40	3.298 (3)	163
C5-H5AN1ⁱⁱⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds