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Volume 64 
Part 4 
Pages o679-o680  
April 2008  

Received 1 March 2008
Accepted 1 March 2008
Online 7 March 2008


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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.146
Data-to-parameter ratio = 22.2
Details

2-Hydroxy-5-nitrobenzaldehyde 2,4-dinitrophenylhydrazone

Abdassalam A. Tameem,a Bahruddin Saad,a Abdussalam M. Salhin,a Samuel Robinson Jebasb+ and Hoong-Kun Funb*

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C13H9N5O7, one of the nitro groups is twisted away from the attached benzene ring by 16.21 (8)°. The dihedral angle between the two benzene rings is 4.63 (1)°. The molecular structure is stabilized by intramolecular N-H...O and O-H...N hydrogen bonds which generate an S(6) ring motif. The molecules pack as layers parallel to the ab plane; molecules of adjacent layers are linked into chains along the [101] direction through N-H...O hydrogen bonds.

Related literature

For related literature, see: Cordis et al. (1998[Cordis, G. A., Das, D. K. & Riedel, W. (1998). J. Chromatogr. A, 798, 117-123.]); Fun et al. (1996[Fun, H.-K., Sivakumar, K., Lu, Z.-L., Duan, C.-Y., Tian, Y.-P. & You, X.-Z. (1996). Acta Cryst. C52, 986-988.]); Guillaumont & Nakamura (2000[Guillaumont, D. & Nakamura, S. (2000). Dyes Pigm. 46, 85-92.]); Hanoune et al. (2006[Hanoune, B., Bris, T. L., Allou, L., Marchand, C. & Calve, S. L. (2006). Atmos. Environ. 40, 5768-5775.]); Lamberton et al. (1974[Lamberton, J. A., Nelson, E. R. & Triffett, C. K. (1974). Aust. J. Chem. 27, 1521-1529.]); Niknam et al. (2005[Niknam, K., Kiasat, A. R. & Karimi, S. (2005). Synth. Commun. 35, 2231-2236.]); Raj & Kurup (2007[Raj, B. N. B. & Kurup, M. R. P. (2007). Spectrochim. Acta Part A, 66, 898-903.]); Salhin et al. (2007[Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.]); Shan, Xu et al. (2003[Shan, S., Xu, D.-J. & Hu, W.-X. (2003). Acta Cryst. E59, o1173-o1174.]); Shan, Yu et al. (2003[Shan, S., Yu, H.-G., Hu, W.-X. & Xu, D.-J. (2003). Acta Cryst. E59, o1886-o1887.]); Tameem et al. (2007[Tameem, A. A., Salhin, A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2502.]); Uchiyama et al. (2003[Uchiyama, S., Ando, M. & Aoyagi, S. (2003). J. Chromatogr. A996, 95-102.]); Vogel et al. (2000[Vogel, M., Potter, W. & Karst, U. (2000). J. Chromatogr. A886, 303-307.]); Zegota (1999[Zegota, H. (1999). J. Chromatogr. A863, 227-233.]); Zlotorzynska & Lai (1999[Zlotorzynska, E. D. & Lai, E. P. C. (1999). J. Chromatogr. A853, 487-796.]). For ring motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9N5O7

  • Mr = 347.25

  • Monoclinic, P 21 /n

  • a = 12.7543 (5) Å

  • b = 8.1898 (3) Å

  • c = 13.8618 (5) Å

  • [beta] = 112.683 (2)°

  • V = 1335.94 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 100.0 (1) K

  • 0.29 × 0.27 × 0.11 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.985

  • 24539 measured reflections

  • 5195 independent reflections

  • 3513 reflections with I > 2[sigma](I)

  • Rint = 0.056
Refinement

  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.145

  • S = 1.09

  • 5195 reflections

  • 234 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O4i 0.89 (2) 2.54 (2) 3.0666 (15) 118 (2)
N1-H1N1...O1 0.89 (2) 2.07 (2) 2.6477 (15) 121 (2)
O5-H1O5...N2 0.92 (3) 1.82 (3) 2.6656 (14) 150 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2567 ).

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cordis, G. A., Das, D. K. & Riedel, W. (1998). J. Chromatogr. A, 798, 117-123.
Fun, H.-K., Sivakumar, K., Lu, Z.-L., Duan, C.-Y., Tian, Y.-P. & You, X.-Z. (1996). Acta Cryst. C52, 986-988.
Guillaumont, D. & Nakamura, S. (2000). Dyes Pigm. 46, 85-92.
Hanoune, B., Bris, T. L., Allou, L., Marchand, C. & Calve, S. L. (2006). Atmos. Environ. 40, 5768-5775.
Lamberton, J. A., Nelson, E. R. & Triffett, C. K. (1974). Aust. J. Chem. 27, 1521-1529.
Niknam, K., Kiasat, A. R. & Karimi, S. (2005). Synth. Commun. 35, 2231-2236.
Raj, B. N. B. & Kurup, M. R. P. (2007). Spectrochim. Acta Part A, 66, 898-903.
Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.
Shan, S., Xu, D.-J. & Hu, W.-X. (2003). Acta Cryst. E59, o1173-o1174.
Shan, S., Yu, H.-G., Hu, W.-X. & Xu, D.-J. (2003). Acta Cryst. E59, o1886-o1887.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Tameem, A. A., Salhin, A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2502.
Uchiyama, S., Ando, M. & Aoyagi, S. (2003). J. Chromatogr. A996, 95-102.
Vogel, M., Potter, W. & Karst, U. (2000). J. Chromatogr. A886, 303-307.
Zegota, H. (1999). J. Chromatogr. A863, 227-233.
Zlotorzynska, E. D. & Lai, E. P. C. (1999). J. Chromatogr. A853, 487-796.

Acta Cryst (2008). E64, o679-o680   [ doi:10.1107/S1600536808005825 ]

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