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Volume 69 
Part 9 
Pages o1483-o1484  
September 2013  

Received 26 July 2013
Accepted 23 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.066
wR = 0.141
Data-to-parameter ratio = 16.9
Details
Open access

6-Amino-2-(pivaloylamino)pyridinium benzoate

aStructural Chemistry and Crystallography Group, University of Lodz, Pomorska 163/165, PL-90-236 Lódz, Poland,bFaculty of Technology and Chemical Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland, and cDepartment of Chemistry, University of Jyväskylä, PO Box 35, FI-40014 Jyväskylä, Finland
Correspondence e-mail: lilach@uni.lodz.pl

In the crystal structure of the title salt, C10H16N3O+·C7H5O2-, the cations and anions are linked to each other via N-H...O hydrogen bonds, forming infinite chains running along [010]. The crystal structure also features C-H...O and [pi]-[pi] stacking interactions, which assemble the chains into supramolecular layers parallel to (100). The [pi]-[pi] stacking interactions are observed between the pyridine rings of inversion-related cations with a centroid-centroid distance of 3.867 (2) Å.

Related literature

For co-crystallization of pharmaceuticals, see: Vishweshwar et al. (2006[Vishweshwar, P., McMahon, J. A., Bis, J. A. & Zaworotko, M. J. (2006). J. Pharm. Sci. 95, 499-516.]); Lemmerer (2012[Lemmerer, A. (2012). CrystEngComm, 14, 2465-2478.]). For the crystal structures of related compounds, see: Osmialowski et al. (2010b[Osmialowski, B., Kolehmainen, E., Dobosz, R., Gawinecki, R., Kauppinen, R., Valkonen, A., Koivukorpi, J. & Rissanen, K. (2010b). J. Phys. Chem. A, 114, 10421-10426.]); Aakeröy et al. (2006[Aakeröy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474-480.], 2010[Aakeröy, C. B., Rajbanshi, A., Li, Z. J. & Desper, J. (2010). CrystEngComm, 12, 4231-4239.]). For the role of steric effects in hydrogen-bonded compounds, see Osmialowski et al. (2012a[Osmialowski, B., Kolehmainen, E., Ikonen, S., Valkonen, A., Kwiatkowski, A., Grela, I. & Haapaniemi, E. (2012a). J. Org. Chem. 77, 9609-9619.],b[Osmialowski, B., Kolehmainen, E. & Kowalska, M. (2012b). J. Org. Chem. 77, 1653-1662.], 2010a[Osmialowski, B., Kolehmainen, E., Gawinecki, R., Dobosz, R. & Kaupinen, R. (2010a). J. Phys. Chem. A, 114, 12881-12887.],b[Osmialowski, B., Kolehmainen, E., Dobosz, R., Gawinecki, R., Kauppinen, R., Valkonen, A., Koivukorpi, J. & Rissanen, K. (2010b). J. Phys. Chem. A, 114, 10421-10426.]). For the synthesis of 2-pivaloylamino-6-aminopyridine, see: Osmialowski et al. (2010a[Osmialowski, B., Kolehmainen, E., Gawinecki, R., Dobosz, R. & Kaupinen, R. (2010a). J. Phys. Chem. A, 114, 12881-12887.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16N3O+·C7H5O2-

  • Mr = 315.37

  • Monoclinic, P 21 /c

  • a = 15.1438 (4) Å

  • b = 5.7099 (2) Å

  • c = 18.7388 (6) Å

  • [beta] = 91.967 (2)°

  • V = 1619.38 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 123 K

  • 0.13 × 0.10 × 0.08 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer with APEXII detector

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.988, Tmax = 0.993

  • 10993 measured reflections

  • 3724 independent reflections

  • 2054 reflections with I > 2[sigma](I)

  • Rint = 0.094

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.141

  • S = 1.00

  • 3724 reflections

  • 220 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O13Ai 0.91 (2) 1.67 (2) 2.571 (2) 170 (2)
N6-H6A...O13Bi 0.90 (2) 2.05 (2) 2.934 (3) 167 (2)
N6-H6B...O13Bii 0.91 (2) 2.05 (2) 2.869 (3) 149 (2)
N7-H7...O13Ai 0.86 (2) 2.24 (2) 2.984 (3) 146 (2)
C4-H4...O8iii 0.95 2.49 3.433 (3) 172
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y, -z+1.

Data collection: COLLECT (Bruker, 2008[Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: DENZO-SMN (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-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2103 ).


Acknowledgements

Financial support from the National Science Centre in Kraków (grant No. NCN204 356840) is gratefully acknowledged. Academy Professor Kari Rissanen (Academy of Finland grant Nos. 122350, 140718, 265328 and 263256) and the University of Jyväskylä (postdoc grant to AV) are also gratefully acknowledged for financial support.

References

Aakeröy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474-480.
Aakeröy, C. B., Rajbanshi, A., Li, Z. J. & Desper, J. (2010). CrystEngComm, 12, 4231-4239.
Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Lemmerer, A. (2012). CrystEngComm, 14, 2465-2478.  [CrossRef] [ChemPort]
Osmialowski, B., Kolehmainen, E., Dobosz, R., Gawinecki, R., Kauppinen, R., Valkonen, A., Koivukorpi, J. & Rissanen, K. (2010b). J. Phys. Chem. A, 114, 10421-10426.  [PubMed]
Osmialowski, B., Kolehmainen, E., Gawinecki, R., Dobosz, R. & Kaupinen, R. (2010a). J. Phys. Chem. A, 114, 12881-12887.  [PubMed]
Osmialowski, B., Kolehmainen, E., Ikonen, S., Valkonen, A., Kwiatkowski, A., Grela, I. & Haapaniemi, E. (2012a). J. Org. Chem. 77, 9609-9619.  [PubMed]
Osmialowski, B., Kolehmainen, E. & Kowalska, M. (2012b). J. Org. Chem. 77, 1653-1662.  [PubMed]
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.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Vishweshwar, P., McMahon, J. A., Bis, J. A. & Zaworotko, M. J. (2006). J. Pharm. Sci. 95, 499-516.  [ISI] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1483-o1484   [ doi:10.1107/S1600536813023787 ]

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