Diethyl­ammonium 4-hy­droxy­benzoate

Lu, Y.-H.

doi:10.1107/S1600536810040523

Volume 66
Part 11
Page o2920
November 2010

Received 21 June 2010
Accepted 9 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.130
Data-to-parameter ratio = 14.6
Details

Diethylammonium 4-hydroxybenzoate

Yong-Hong Lu ^a ^*

^aOrdered Matter Science Reserch Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: chmsunbw@seu.edu.cn

In the crystal structure of the title compound, C₄H₁₂N⁺·C₇H₅O₃^-, the cations and anions are linked by N-HO and O-HO hydrogen bonds, leading to the formation of a three-dimensional network.

Related literature

Hydrogen bonds in co-crystals have been widely used to design and synthesize one-, two- and three-dimensional supramolecular compounds, see: Aakeroÿ et al. (2002). 4-Hydroxybenzoic acid is a good hydrogen bond donor and can form co-crystals with other organic molecules, see: Vishweshwar et al. (2003).

Experimental

Crystal data

C₄H₁₂N⁺·C₇H₅O₃^-
M_r = 211.26
Orthorhombic, P b c a
a = 12.1270 (13) Å
b = 10.6829 (11) Å
c = 17.6066 (15) Å
V = 2281.0 (4) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.43 × 0.41 × 0.20 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.963, T_max = 0.982
8818 measured reflections
2016 independent reflections
1155 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.130
S = 1.06
2016 reflections
138 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.90	2.15	2.873 (3)	137
N1-H1AO1ⁱ	0.90	2.16	3.022 (3)	162
N1-H1BO2ⁱⁱ	0.90	1.83	2.724 (3)	174
O3-H3O1ⁱⁱⁱ	0.82	1.82	2.635 (3)	170
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

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: FL2305 ).

References

Aakeroÿ, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425-14432.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm, 5, 164-168.

organic compounds