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Volume 68 
Part 1 
Page o228  
January 2012  

Received 7 November 2011
Accepted 17 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.066
wR = 0.165
Data-to-parameter ratio = 13.3
Details
Open access

3-Methylanilinium hydrogen phthalate

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: jgsdxlml@163.com

The asymmetric unit of the title salt, C7H10N+·C8H5O4-, consists of two 3-methylphenylammonium cations and two hydrogen phthalate anions. There are strong intramolecular O-H...O hydrogen bonds in the virtually planar (r.m.s. deviations = 0.054 Å) phthalate anions. In the crystal, the cations and anions are connected via an extensive sytem of N-H...O hydrogen bonds into a corrugated layer extended parallel to (001).

Related literature

The title compound was investigated as part of work looking for new ferroelectric compounds. For background to ferroelectric compounds consisting of organic cations and inorganic anions, see: Fu et al. (2011[Fu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780-12786.]); Ye et al. (2010[Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Appl. Cryst. 43, 1031-1035.]). For a related structure, see: Kadirvelraj et al. (1996[Kadirvelraj, R., Umarji, A. M., Robinson, W. T., Bhattacharya, S. & Row, T. N. G. (1996). Chem. Mater. 8, 2313-2323.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N+·C8H5O4-

  • Mr = 273.28

  • Monoclinic, P 21 /n

  • a = 7.9325 (16) Å

  • b = 17.931 (4) Å

  • c = 19.575 (4) Å

  • [beta] = 93.37 (3)°

  • V = 2779.5 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.36 × 0.32 × 0.28 mm

Data collection
  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.963, Tmax = 0.971

  • 22962 measured reflections

  • 4906 independent reflections

  • 2489 reflections with I > 2[sigma](I)

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.165

  • S = 1.03

  • 4906 reflections

  • 368 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O5i 0.89 1.87 2.739 (3) 166
N2-H2B...O2ii 0.89 1.93 2.815 (3) 178
N2-H2C...O8 0.89 1.90 2.789 (3) 178
N1-H1A...O6i 0.89 1.94 2.826 (3) 177
N1-H1B...O1i 0.89 1.91 2.784 (3) 166
N1-H1C...O4iii 0.89 1.90 2.788 (3) 172
O3-H3...O2 0.82 1.58 2.392 (3) 173
O7-H7...O6 0.82 1.57 2.392 (3) 180
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y+1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2431 ).


Acknowledgements

The author thanks an anonymous advisor from the Ordered Matter Science Research Centre, Southeast University, for great help in the revision of this paper.

References

Fu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780-12786.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Kadirvelraj, R., Umarji, A. M., Robinson, W. T., Bhattacharya, S. & Row, T. N. G. (1996). Chem. Mater. 8, 2313-2323.  [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Appl. Cryst. 43, 1031-1035.  [ISI] [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o228  [ doi:10.1107/S1600536811054353 ]

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