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Volume 69 
Part 1 
Page o75  
January 2013  

Received 22 November 2012
Accepted 28 November 2012
Online 12 December 2012

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Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 13.4
Details
Open access

2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile

Syed Muhammad Saad,a Syed Moazzam Haider,a Shahnaz Perveen,b Khalid M. Khana and Sammer Yousufa*

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bPCSIR Labortories Complex, Karachi, Shahrah-e-Dr. Salmuzzaman Siddiqui, Karachi 75280, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

The title molecule, C10H10N4O2, is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me2), the dihedral angle between the two mean planes being 18.42 (11)°. The cyano group lies in the plane of the benzene ring [the C and N atoms deviating by 0.030 (3) and 0.040 (3) Å, respectively], while the nitro group makes a dihedral angle 5.8 (3)° with the benzene ring. There are two distinct intermolecular hydrogen bonds, C-H...O and C-H...N, that stabilize the crystal structure; the former interactions result in centrosymmetric dimers about inversion centers resulting in ten-membered rings, while the later give rise to chains of molecules running parallel to the b axis.

Related literature

For the biological activity of amidine derivatives, see: Sienkiewich et al. (2005[Sienkiewich, P., Bielawaski, K., Bielawaska, A. & Palka, J. (2005). Environ. Toxicol. Pharm. 20, 118-124.]); Sasaki et al. (1997[Sasaki, S., Fukushima, J., Arai, H., Kusakabe, K., Hamajima, K., Ishii, N., Hirahara, F., Okuda, K., Kawamoto, S., Ruysschaert, J. M., Vandenbranden, M. & Wahren, B. (1997). Eur. J. Immunol. 27 , 3121-9.]). For a related structure, see: Cizak et al. (1989[Ciszak, E., Gdaniec, M., Jaskólski, M., Kosturkiewicz, Z., Owsianski, J. & Tykarska, E. (1989). Acta Cryst. C45, 433-438.]).

[Scheme 1]

Experimental

Crystal data

  • C10H10N4O2

  • Mr = 218.22

  • Monoclinic, P 21 /n

  • a = 7.6496 (11) Å

  • b = 13.0693 (19) Å

  • c = 11.1617 (17) Å

  • [beta] = 106.475 (3)°

  • V = 1070.1 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 273 K

  • 0.25 × 0.24 × 0.09 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.991

  • 6194 measured reflections

  • 1976 independent reflections

  • 1427 reflections with I > 2[sigma](I)

  • Rint = 0.025
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.04

  • 1976 reflections

  • 147 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
C1-H1A...O1i 0.93 2.48 3.354 (3) 156
C8-H8A...N1ii 0.93 2.61 3.525 (2) 166
Symmetry codes: (i) -x+2, -y, -z+2; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2610 ).

Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan (Project No. 20-2073) and the Pakistan Academy of Sciences (PAS) for their financial support.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ciszak, E., Gdaniec, M., Jaskólski, M., Kosturkiewicz, Z., Owsianski, J. & Tykarska, E. (1989). Acta Cryst. C45, 433-438.  [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sasaki, S., Fukushima, J., Arai, H., Kusakabe, K., Hamajima, K., Ishii, N., Hirahara, F., Okuda, K., Kawamoto, S., Ruysschaert, J. M., Vandenbranden, M. & Wahren, B. (1997). Eur. J. Immunol. 27 , 3121-9.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sienkiewich, P., Bielawaski, K., Bielawaska, A. & Palka, J. (2005). Environ. Toxicol. Pharm. 20, 118-124.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2013). E69, o75  [ doi:10.1107/S1600536812048866 ]

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