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Volume 69 
Part 5 
Page o661  
May 2013  

Received 26 March 2013
Accepted 28 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.122
Data-to-parameter ratio = 17.1
Details
Open access

Bis(pyridin-2-ylmethyl)ammonium nitrate

aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: abubakr.abrahams@nmmu.ac.za

In the title compound, C12H14N3+·NO3-, the mononitrate of protonated bis(pyridin-2-ylmethyl)amine, the least-squares planes defined by the non-H atoms of the two aromatic moieties intersect at an angle of 7.91 (6)°. In the crystal, N-H...N, N-H...O and C-H...N hydrogen bonds, as well as C-H...O contacts, connect the entities into a three-dimensional network. The shortest centroid-centroid distance between two aromatic systems is 3.7255 (8) Å and is apparent between the two different aromatic moieties.

Related literature

For the crystal structure of the trinitrate of bis(pyridin-2-ylmethyl)amine, see: Junk et al. (2006[Junk, P. C., Kim, Y., Skelton, B. W. & White, A. H. (2006). Z. Anorg. Allg. Chem. 632, 1340-1350.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N3+·NO3-

  • Mr = 262.27

  • Orthorhombic, P b c a

  • a = 11.2236 (2) Å

  • b = 13.4714 (4) Å

  • c = 16.5303 (4) Å

  • V = 2499.34 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.50 × 0.35 × 0.24 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.923, Tmax = 1.000

  • 12816 measured reflections

  • 3082 independent reflections

  • 2568 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.122

  • S = 1.04

  • 3082 reflections

  • 180 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...N2 0.95 2.61 3.5339 (18) 164
N1-H71...O3i 0.893 (18) 2.349 (18) 3.0721 (15) 138.2 (14)
N1-H72...O2ii 0.902 (19) 1.982 (19) 2.8831 (15) 176.1 (15)
N1-H72...O1ii 0.902 (19) 2.584 (18) 3.2201 (16) 128.1 (14)
N1-H72...N2ii 0.902 (19) 2.651 (18) 3.4905 (15) 155.1 (14)
C15-H15...O2iii 0.95 2.39 3.1858 (19) 141
C1-H1A...O1iv 0.99 2.54 3.5132 (18) 167
C25-H25...O1v 0.95 2.53 3.3959 (16) 151
C24-H24...O2vi 0.95 2.55 3.4620 (16) 161
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (v) -x+1, -y, -z+1; (vi) x, y, z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin,USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin,USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VN2068 ).


Acknowledgements

The authors thank NMMU for the allocation of research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SADABS Bruker Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin,USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Junk, P. C., Kim, Y., Skelton, B. W. & White, A. H. (2006). Z. Anorg. Allg. Chem. 632, 1340-1350.  [CSD] [CrossRef] [ChemPort]
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]
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]


Acta Cryst (2013). E69, o661  [ doi:10.1107/S1600536813008593 ]

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