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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 [sigma](C-C) = 0.004 Å
R = 0.040
wR = 0.087
Data-to-parameter ratio = 9.3
Details
Open access

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

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-H...O hydrogen-bonded chains propagating along the c-axis direction.

Related literature

For spectroscopic studies of acid-amine complexes, see: Karlsson et al. (2000[Karlsson, S., Backlund, S. & Friman, R. (2000). Colloid Polym. Sci. 278, 8-14.]); Paivarinta et al. (2000[Paivarinta, J., Karlsson, S., Hotokka, M. & Poso, A. (2000). Chem. Phys. Lett. 327, 420-424.]); Kohler et al. (1981[Kohler, F., Atrops, H., Kalali, H., Liebermann, E., Wilhelm, E., Ratkovics, F. & Salamon, T. (1981). J. Phys. Chem. 85, 2520-2524.]); Smith et al. (2001[Smith, G., Wermuth, U. D., Bott, R. C., White, J. M. & Willis, A. C. (2001). Aust. J. Chem. 54, 165-170.], 2002[Smith, G., Wermuth, U. D., Bott, R. C., Healy, P. C. & White, J. M. (2002). Aust. J. Chem. 55, 349-356.]); Klokkenburg et al. (2007[Klokkenburg, M., Hilhorst, J. & Erne, B. H. (2007). Vib. Spectrosc. 43, 243-248.]). For recent diffraction studies of acid-amine complexes, see: Jefferson et al. (2011[Jefferson, A. E., Sun, C., Bond, A. D. & Clarke, S. M. (2011). Acta Cryst. E67, o655.]); Sun et al. (2011[Sun, S., Bojdys, M. J., Clarke, S. M., Harper, L. D., Castro, M. A. & Medina, S. (2011). Langmuir, 27, 3626-3637.]); Wood & Clarke (2012[Wood, M. H. & Clarke, S. M. (2012). Acta Cryst. E68, o3004.]).

[Scheme 1]

Experimental

Crystal data
  • C8H12N+·C6H11O2-

  • Mr = 237.33

  • Hexagonal, P 63

  • a = 19.5845 (5) Å

  • c = 6.6307 (2) Å

  • V = 2202.49 (10) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 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[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.740, Tmax = 0.999

  • 11638 measured reflections

  • 1461 independent reflections

  • 1270 reflections with I > 2[sigma](I)

  • Rint = 0.064

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

  • wR(F2) = 0.087

  • S = 1.06

  • 1461 reflections

  • 157 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.91 1.84 2.753 (3) 176
N1-H1B...O1 0.91 1.87 2.768 (3) 167
N1-H1C...O1ii 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[Nonius, B. V. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[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.]); 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.  [CrossRef] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Jefferson, A. E., Sun, C., Bond, A. D. & Clarke, S. M. (2011). Acta Cryst. E67, o655.  [CSD] [CrossRef] [details]
Karlsson, S., Backlund, S. & Friman, R. (2000). Colloid Polym. Sci. 278, 8-14.  [CrossRef] [ChemPort]
Klokkenburg, M., Hilhorst, J. & Erne, B. H. (2007). Vib. Spectrosc. 43, 243-248.  [ISI] [CrossRef] [ChemPort]
Kohler, F., Atrops, H., Kalali, H., Liebermann, E., Wilhelm, E., Ratkovics, F. & Salamon, T. (1981). J. Phys. Chem. 85, 2520-2524.  [CrossRef] [ChemPort] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Wermuth, U. D., Bott, R. C., Healy, P. C. & White, J. M. (2002). Aust. J. Chem. 55, 349-356.  [ISI] [CSD] [CrossRef] [ChemPort]
Smith, G., Wermuth, U. D., Bott, R. C., White, J. M. & Willis, A. C. (2001). Aust. J. Chem. 54, 165-170.  [ISI] [CSD] [CrossRef] [ChemPort]
Sun, S., Bojdys, M. J., Clarke, S. M., Harper, L. D., Castro, M. A. & Medina, S. (2011). Langmuir, 27, 3626-3637.  [ISI] [CrossRef] [ChemPort] [PubMed]
Wood, M. H. & Clarke, S. M. (2012). Acta Cryst. E68, o3004.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3335  [ doi:10.1107/S1600536812045746 ]

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