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Volume 69 
Part 6 
Page o860  
June 2013  

Received 24 April 2013
Accepted 3 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.114
Data-to-parameter ratio = 13.9
Details
Open access

Ammonium 2-(3,4-dimethylbenzoyl)benzoate dihydrate

aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, People's Republic of China
Correspondence e-mail: kjf416@163.com

In the anion of the title compound, NH4+·C16H13O3-·2H2O, the benzene rings are twisted with respect to each other by 73.56 (10)°. In the crystal, extensive N-H...O and O-H...O hydrogen bonds link the cations, anions and lattice water molecules into a three dimensional supramolecular structure.

Related literature

For the synthesis of the title compound, see: Elofson et al. (1965[Elofson, R. M., Schulz, K. F., Galbraith, B. E. & Newton, R. (1965). Can. J. Chem. 43, 1553-1559.]). For related compounds, see: Boon et al. (1986[Boon, J. A., Levisky, J. A., Pflug, J. L. & Wilkes, J. S. (1986). J. Org. Chem. 51, 480-483.]); Yeung et al. (2002[Yeung, K. S., Farkas, M. E., Qiu, Z. & Yang, Z. (2002). Tetrahedron Lett. 43, 5793-5795.]); Gopalakrishnan et al. (2005[Gopalakrishnan, M., Sureshkumar, P., Kanagarajan, V. & Thanusu, J. (2005). Catal. Commun. 6, 753-756.]); Qiao et al. (2008[Qiao, W.-Z., Zheng, J., Wang, Y.-J., Song, N.-H., Wan, X.-H. & Wang, Z.-Y. (2008). Org. Lett. 10, 241-244.]); Gouda et al. (2010[Gouda, M. A., Berghot, M. A., Shoeib, A. M. & Khalil, A. M. (2010). Eur. J. Med. Chem. 45, 1843-1848.]).

[Scheme 1]

Experimental

Crystal data
  • NH4+·C16H13O3-·2H2O

  • Mr = 307.34

  • Triclinic, [P \overline 1]

  • a = 7.5039 (15) Å

  • b = 7.7458 (15) Å

  • c = 14.439 (3) Å

  • [alpha] = 81.63 (3)°

  • [beta] = 79.15 (3)°

  • [gamma] = 78.67 (3)°

  • V = 803.0 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Rigaku MM007-HF CCD (Saturn 724+) diffractometer

  • 6289 measured reflections

  • 2791 independent reflections

  • 1674 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.01

  • 2791 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O4W 0.93 1.98 2.836 (2) 152
N1-H1B...O3 0.93 1.90 2.820 (2) 170
N1-H1C...O3i 0.96 1.88 2.823 (3) 167
N1-H1D...O5Wii 0.96 2.03 2.871 (3) 144
N1-H1D...O4Wiii 0.96 2.45 3.067 (3) 121
O4W-H4WA...O2iv 0.90 1.93 2.809 (2) 164
O4W-H4WB...O2ii 0.90 1.91 2.808 (2) 172
O5W-H5WA...O1v 0.87 2.04 2.899 (2) 171
O5W-H5WB...O2 0.85 2.31 3.032 (2) 142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) -x+2, -y+1, -z+1; (v) x-1, y, z.

Data collection: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC. (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalStructure; data reduction: CrystalStructure; 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5697 ).


Acknowledgements

The work was supported by the Youth Fund of Yunnan Normal University and the Scientific Research Foundation of Yunnan Provincial Department of Education (grant No. 22012Z019).

References

Boon, J. A., Levisky, J. A., Pflug, J. L. & Wilkes, J. S. (1986). J. Org. Chem. 51, 480-483.  [CrossRef] [ChemPort]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Elofson, R. M., Schulz, K. F., Galbraith, B. E. & Newton, R. (1965). Can. J. Chem. 43, 1553-1559.  [CrossRef] [ChemPort] [ISI]
Gopalakrishnan, M., Sureshkumar, P., Kanagarajan, V. & Thanusu, J. (2005). Catal. Commun. 6, 753-756.  [ISI] [CrossRef] [ChemPort]
Gouda, M. A., Berghot, M. A., Shoeib, A. M. & Khalil, A. M. (2010). Eur. J. Med. Chem. 45, 1843-1848.  [ISI] [CrossRef] [ChemPort] [PubMed]
Qiao, W.-Z., Zheng, J., Wang, Y.-J., Song, N.-H., Wan, X.-H. & Wang, Z.-Y. (2008). Org. Lett. 10, 241-244.  [ISI] [CrossRef] [PubMed]
Rigaku/MSC. (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yeung, K. S., Farkas, M. E., Qiu, Z. & Yang, Z. (2002). Tetrahedron Lett. 43, 5793-5795.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o860  [ doi:10.1107/S1600536813012087 ]

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