(S)-(−)-1-Phenyl­ethanaminium hexa­noate

Wood, M.H.; Clarke, S.M.

doi:10.1107/S1600536812045746

Volume 68
Part 12
Page o3335
December 2012

Received 26 October 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.004 Å
R = 0.040
wR = 0.087
Data-to-parameter ratio = 9.3
Details

(S)-(-)-1-Phenylethanaminium hexanoate

Mary H. Wood ^a ^* and Stuart M. Clarke ^a

^aBP Institute and Department of Chemistry, University of Cambridge, Cambridge CB3 0EZ, England
Correspondence e-mail: stuart@bpi.cam.ac.uk

A binary mixture of (S)-(-)-1-phenylethanamine and hexanoic acid was allowed to react to form the title salt, C₈H₁₂N⁺·C₆H₁₁O₂^-. This crystal contains a 1:1 stoichiometric mixture of the acid- and amine-derived species and displays a chiral structure with N-HO hydrogen-bonded chains propagating along the c-axis direction.

Related literature

For spectroscopic studies of acid-amine complexes, see: Karlsson et al. (2000); Paivarinta et al. (2000); Kohler et al. (1981); Smith et al. (2001, 2002); Klokkenburg et al. (2007). For recent diffraction studies of acid-amine complexes, see: Jefferson et al. (2011); Sun et al. (2011); Wood & Clarke (2012).

Experimental

Crystal data

C₈H₁₂N⁺·C₆H₁₁O₂^-
M_r = 237.33
Hexagonal, P 6₃
a = 19.5845 (5) Å
c = 6.6307 (2) Å
V = 2202.49 (10) Å³
Z = 6
Mo K radiation
= 0.07 mm^-1
T = 180 K
0.46 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.740, T_max = 0.999
11638 measured reflections
1461 independent reflections
1270 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.087
S = 1.06
1461 reflections
157 parameters
1 restraint
H-atom parameters constrained
_max = 0.11 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.91	1.84	2.753 (3)	176
N1-H1BO1	0.91	1.87	2.768 (3)	167
N1-H1CO1ⁱⁱ	0.91	1.82	2.714 (2)	168
Symmetry codes: (i) x, y, z-1; (ii) $[-x+1, -y+2, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2095 ).

Acknowledgements

The authors thank the Department of Chemistry, the BP Institute and the Oppenheimer Trust for financial and technical assistance and Dr J. E. Davies for collecting and analysing the X-ray data.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Jefferson, A. E., Sun, C., Bond, A. D. & Clarke, S. M. (2011). Acta Cryst. E67, o655.
Karlsson, S., Backlund, S. & Friman, R. (2000). Colloid Polym. Sci. 278, 8-14.
Klokkenburg, M., Hilhorst, J. & Erne, B. H. (2007). Vib. Spectrosc. 43, 243-248.
Kohler, F., Atrops, H., Kalali, H., Liebermann, E., Wilhelm, E., Ratkovics, F. & Salamon, T. (1981). J. Phys. Chem. 85, 2520-2524.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Nonius, B. V. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Paivarinta, J., Karlsson, S., Hotokka, M. & Poso, A. (2000). Chem. Phys. Lett. 327, 420-424.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Wermuth, U. D., Bott, R. C., Healy, P. C. & White, J. M. (2002). Aust. J. Chem. 55, 349-356.
Smith, G., Wermuth, U. D., Bott, R. C., White, J. M. & Willis, A. C. (2001). Aust. J. Chem. 54, 165-170.
Sun, S., Bojdys, M. J., Clarke, S. M., Harper, L. D., Castro, M. A. & Medina, S. (2011). Langmuir, 27, 3626-3637.
Wood, M. H. & Clarke, S. M. (2012). Acta Cryst. E68, o3004.

organic compounds