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Volume 70 
Part 1 
Page o15  
January 2014  

Received 21 November 2013
Accepted 28 November 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 299 K
Mean [sigma](C-C) = 0.004 Å
R = 0.063
wR = 0.150
Data-to-parameter ratio = 13.4
Details
Open access

4-Nitro­phenyl­hydrazinium picrate monohydrate

aSchool of Chemistry and Material Science, Ludong University, Yantai 264025, People's Republic of China
Correspondence e-mail: honglan_cai@126.com

In the crystal structure of the title compound, C6H8N3O2+·C6H2N3O7-·H2O, N-H...O and O-H...O hydrogen bonds link the components into a two-dimensional network parallel to (010). In addition, there are pairs of weak inversion-related C-H...O hydrogen bonds within the two-dimensional network. The three nitro groups are twisted by 1.6 (3), 7.8 (3) and 12.1 (3)° from the ring plane in the anion, while in the cation, the nitro group makes a dihedral angle of 4.6 (2)° with the ring.

Related literature

For the use of picric acid acid as a co-crystallization agent, see: Herbstein & Kaftory (1976[Herbstein, F. H. & Kaftory, M. (1976). Acta Cryst. B32, 387-396.]); Dubost et al. (1981[Dubost, J.-P., Léger, J.-M., Hickel, D. & Colleter, J.-C. (1981). Acta Cryst. B37, 751-754.]); Harrison et al. (2007[Harrison, W. T. A., Swamy, M. T., Nagaraja, P., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3892.]); Peng et al. (2011[Peng, Y., Zhang, A.-J., Dong, M. & Wang, Y.-W. (2011). Chem. Commun. 47, 4505-4507.]); Zeng et al. (2011[Zeng, B., Li, J. & Wang, G. (2011). Acta Cryst. E67, o1464.]); Dey et al. (2011[Dey, S. K., Pramanik, A. & Das, G. (2011). CrystEngComm, 13, 1664-1675.]).

[Scheme 1]

Experimental

Crystal data
  • C6H8N3O2+·C6H2N3O7-·H2O

  • Mr = 400.28

  • Monoclinic, P 21 /c

  • a = 4.8483 (3) Å

  • b = 28.798 (2) Å

  • c = 11.6352 (8) Å

  • [beta] = 101.360 (1)°

  • V = 1592.70 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 299 K

  • 0.20 × 0.08 × 0.04 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.994

  • 16632 measured reflections

  • 3643 independent reflections

  • 2487 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.150

  • S = 1.05

  • 3643 reflections

  • 271 parameters

  • 10 restraints

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O10i 0.87 (1) 2.05 (1) 2.916 (3) 177 (2)
N1-H1B...O10 0.87 (1) 1.94 (1) 2.809 (3) 172 (2)
N1-H1B...O9ii 0.87 (1) 2.56 (3) 2.908 (3) 105 (2)
N1-H1C...O6iii 0.87 (1) 2.08 (1) 2.947 (3) 170 (2)
N2-H2A...O4 0.86 (1) 2.13 (2) 2.868 (3) 144 (3)
O10-H10A...O3 0.82 (1) 2.09 (2) 2.832 (3) 150 (3)
O10-H10A...O4 0.82 (1) 2.24 (2) 2.743 (3) 120 (2)
O10-H10B...O3ii 0.83 (1) 2.05 (1) 2.869 (3) 171 (3)
O10-H10B...O9ii 0.83 (1) 2.43 (3) 2.898 (3) 117 (3)
C11-H11...O8iv 0.93 2.51 3.433 (3) 172
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z-1; (iv) -x+3, -y+1, -z+2.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: 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: LH5673 ).


Acknowledgements

This work received financial support mainly from the National Key Fundamental Project (No. 20603030).

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Dey, S. K., Pramanik, A. & Das, G. (2011). CrystEngComm, 13, 1664-1675.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Dubost, J.-P., Léger, J.-M., Hickel, D. & Colleter, J.-C. (1981). Acta Cryst. B37, 751-754.  [CSD] [CrossRef] [IUCr Journals]
Harrison, W. T. A., Swamy, M. T., Nagaraja, P., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3892.  [CSD] [CrossRef] [IUCr Journals]
Herbstein, F. H. & Kaftory, M. (1976). Acta Cryst. B32, 387-396.  [CSD] [CrossRef] [IUCr Journals]
Peng, Y., Zhang, A.-J., Dong, M. & Wang, Y.-W. (2011). Chem. Commun. 47, 4505-4507.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zeng, B., Li, J. & Wang, G. (2011). Acta Cryst. E67, o1464.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2014). E70, o15  [ doi:10.1107/S1600536813032479 ]

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