3-Methyl­anilinium hydrogen phthalate

Liu, M.-L.

doi:10.1107/S1600536811054353

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 (C-C) = 0.005 Å
R = 0.066
wR = 0.165
Data-to-parameter ratio = 13.3
Details

3-Methylanilinium hydrogen phthalate

Ming-Liang Liu ^a ^*

^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-HO 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-HO 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); Ye et al. (2010). For a related structure, see: Kadirvelraj et al. (1996).

Experimental

Crystal data

C₇H₁₀N⁺·C₈H₅O₄^-
M_r = 273.28
Monoclinic, P 2₁ /n
a = 7.9325 (16) Å
b = 17.931 (4) Å
c = 19.575 (4) Å
= 93.37 (3)°
V = 2779.5 (10) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.963, T_max = 0.971
22962 measured reflections
4906 independent reflections
2489 reflections with I > 2(I)
R_int = 0.090

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.165
S = 1.03
4906 reflections
368 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO5ⁱ	0.89	1.87	2.739 (3)	166
N2-H2BO2ⁱⁱ	0.89	1.93	2.815 (3)	178
N2-H2CO8	0.89	1.90	2.789 (3)	178
N1-H1AO6ⁱ	0.89	1.94	2.826 (3)	177
N1-H1BO1ⁱ	0.89	1.91	2.784 (3)	166
N1-H1CO4ⁱⁱⁱ	0.89	1.90	2.788 (3)	172
O3-H3O2	0.82	1.58	2.392 (3)	173
O7-H7O6	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); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Kadirvelraj, R., Umarji, A. M., Robinson, W. T., Bhattacharya, S. & Row, T. N. G. (1996). Chem. Mater. 8, 2313-2323.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (2010). J. Appl. Cryst. 43, 1031-1035.

organic compounds