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Volume 69 
Part 5 
Pages o755-o756  
May 2013  

Received 20 February 2013
Accepted 8 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.054
wR = 0.141
Data-to-parameter ratio = 19.8
Details
Open access

Benzylammonium heptanoate

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

The title 1:1 stoichiometric salt, C7H10N+·C7H13O2-, is formed by proton transfer between heptanoic acid and benzylamine. This combination contrasts to the recently published 2:1 acid-amine adduct of cation, anion and neutral acid molecule from the same components [Wood & Clarke (2013[Wood, M. H. & Clarke, S. M. (2013). Acta Cryst. E69, o346-o347.]). Acta Cryst. E69, o346-o347]. There are N-H...O hydrogen bonds of moderate strength in the structure [the most important graph-set motifs are R24(8) and R44(12)], as well as weak C-H...O interactions.

Related literature

For spectroscopic studies of acid-amine complexes, see: 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.]); 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.]); 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.]). 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 (2012a[Wood, M. H. & Clarke, S. M. (2012a). Acta Cryst. E68, o3004.],b[Wood, M. H. & Clarke, S. M. (2012b). Acta Cryst. E68, o3335.], 2013[Wood, M. H. & Clarke, S. M. (2013). Acta Cryst. E69, o346-o347.]). For the categorization of hydrogen bonds, see Gilli & Gilli (2009[Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory. International Union of Crystallography. Oxford Science Publications. p. 61. New York, Oxford: Oxford University Press, Inc.]). For graph-set motifs, see Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N+·C7H13O2-

  • Mr = 237.33

  • Triclinic, [P \overline 1]

  • a = 5.7379 (2) Å

  • b = 7.7338 (3) Å

  • c = 17.1670 (7) Å

  • [alpha] = 97.887 (2)°

  • [beta] = 92.864 (2)°

  • [gamma] = 107.340 (2)°

  • V = 716.96 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 180 K

  • 0.46 × 0.07 × 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 = 0.874, Tmax = 0.999

  • 8415 measured reflections

  • 3253 independent reflections

  • 2308 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.141

  • S = 1.03

  • 3253 reflections

  • 164 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2 0.99 (2) 1.80 (2) 2.7802 (17) 168.7 (19)
N1-H1B...O1i 0.98 (2) 1.73 (2) 2.6993 (17) 169 (2)
N1-H1C...O2ii 1.00 (2) 1.87 (2) 2.8590 (18) 167 (2)
C1-H1E...O1iii 0.99 2.40 3.280 (2) 148
C7-H7...O2 0.95 2.52 3.3528 (19) 146
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z.

Data collection: COLLECT (Nonius, 1998[Nonius (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. , 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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: FB2281 ).


Acknowledgements

We thank the Department of Chemistry, the BP Institute and the Oppenheimer Trust for financial and technical assistance, and Dr J. E. Davies and Dr A. D. Bond for assistance in collecting and analysing the X-ray data.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Gilli, G. & Gilli, P. (2009). The Nature of the Hydrogen Bond. Outline of a Comprehensive Hydrogen Bond Theory. International Union of Crystallography. Oxford Science Publications. p. 61. New York, Oxford: Oxford University Press, Inc.
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]
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 (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] [ChemPort] [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. (2012a). Acta Cryst. E68, o3004.  [CSD] [CrossRef] [details]
Wood, M. H. & Clarke, S. M. (2012b). Acta Cryst. E68, o3335.  [CSD] [CrossRef] [details]
Wood, M. H. & Clarke, S. M. (2013). Acta Cryst. E69, o346-o347.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o755-o756   [ doi:10.1107/S1600536813009574 ]

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