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Volume 69 
Part 6 
Pages o981-o982  
June 2013  

Received 29 April 2013
Accepted 20 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.092
Data-to-parameter ratio = 15.7
Details
Open access

4-Cyano-1-methylpyridinium nitrate

aDepartment of Physics, Loyola University, New Orleans, LA 70118, USA,bDepartment of Chemistry, Loyola University, New Orleans, LA 70118, USA, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
Correspondence e-mail: joelt@tulane.edu

The title molecular salt, C7H7N2+·NO3-, displays an interpenetrating sheet structure parallel to a with each sheet containing nearly coplanar cations and anions, each ion being bisected by a crystallographic mirror plane. C-H...O hydrogen bonds involving both ring and methyl H atoms in addition to cation-cation C-H...N hydrogen bonds (ring H to cyano N) serve to link the sheets together. In each set of parallel layers, the cations and anions stack with short distances of 3.094 (2) (between aligned nitrate N and pyridine N atoms) and 3.057 (2) Å (between a nitrate O atom and the ring centroid). This motif is strikingly similar to the one that features in the isomeric salt 2-cyano-1-methylpyridinium nitrate.

Related literature

For structures of other 4-cyano-1-methylpyridinium salts, see: Bockman & Kochi (1989[Bockman, T. M. & Kochi, J. A. (1989). J. Am. Chem. Soc. 111, 4669-4683.]); Bockman & Kochi (1992[Bockman, T. M. & Kochi, J. K. (1992). New J. Chem. 16, 39-49.]); Hardacre et al. (2008[Hardacre, C., Holbrey, J. D., Mullan, C. L., Nieuwenhuyzen, M., Reichert, W. M., Seddon, K. R. & Teat, S. J. (2008). New J. Chem. 32, 1953-1967.], 2010[Hardacre, C., Holbrey, J. D., Mullan, C. L., Nieuwenhuyzen, M., Youngs, T. G. A., Bowron, D. T. & Teat, S. J. (2010). Phys. Chem. Chem. Phys. 12, 1842-1853.]); Kammer et al. (2012a[Kammer, M. N., Mague, J. T. & Koplitz, L. V. (2012a). Acta Cryst. E68, o2409.],b[Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012b). Acta Cryst. E68, o2514.]. For the structure of 2-cyano-1-methylpyridinium nitrate, see: Koplitz et al. (2012[Koplitz, L. V., Mague, J. T., Kammer, M. N., McCormick, C. A., Renfro, H. E. & Vumbaco, D. J. (2012). Acta Cryst. E68, o1653.]), of 3-cyano-1-methylpyridinium chloride, see: Koplitz et al. (2003[Koplitz, L. V., Bay, K. D., DiGiovanni, N. & Mague, J. T. (2003). J. Chem. Crystallogr. 33, 391-402.]) and of 3-cyano-N-methylpyridinium bromide, see: Mague et al. (2005[Mague, J. T., Ivie, R. M., Hartsock, R. W., Koplitz, L. V. & Spulak, M. (2005). Acta Cryst. E61, o851-o853.]). For a discussion of anion-[pi] interactions, see: Frontera et al. (2011[Frontera, A., Gamez, P., Mascal, M., Mooibroeck, T. J. & Reedijk, J. (2011). Angew. Chem. Int. Ed. 50, 9564-9583.]). For the structure of 2-cyanoanilinium nitrate, see: Cui & Wen (2008[Cui, L.-J. & Wen, X.-C. (2008). Acta Cryst. E64, o1620.]) and of 3-cyanoanilinium nitrate, see: Wang (2009[Wang, B. (2009). Acta Cryst. E65, o2395.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7N2+·NO3-

  • Mr = 181.16

  • Orthorhombic, P m n 21

  • a = 8.195 (3) Å

  • b = 7.289 (3) Å

  • c = 6.721 (3) Å

  • V = 401.5 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.33 × 0.23 × 0.13 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 2009[Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany.]) Tmin = 0.860, Tmax = 0.985

  • 6751 measured reflections

  • 1116 independent reflections

  • 1089 reflections with I > 2[sigma](I)

  • Rint = 0.091

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.092

  • S = 1.09

  • 1116 reflections

  • 71 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...O1i 0.96 2.71 3.3826 (19) 127
C1-H1A...O1ii 0.96 2.71 3.3826 (19) 127
C1-H1B...O1iii 0.90 2.60 3.4485 (15) 159
C2-H2...O1iv 0.95 2.65 3.3763 (17) 134
C2-H2...O2iv 0.95 2.29 3.2379 (15) 172
C3-H3...N2iv 0.95 2.51 3.2272 (15) 132
C3-H3...O1v 0.95 2.56 3.2568 (17) 131
Symmetry codes: (i) x, y-1, z; (ii) -x+1, y-1, z; (iii) [x-{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (iv) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]; (v) [-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: FLIPPER option in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7076 ).


Acknowledgements

We thank the Chemistry Department of Tulane University for support of the X-ray laboratory and the Louisiana Board of Regents through the Louisiana Educational Quality Support Fund [grant LEQSF (2003-2003)-ENH -TR-67] for the purchase of the diffractometer.

References

Bockman, T. M. & Kochi, J. A. (1989). J. Am. Chem. Soc. 111, 4669-4683.  [CrossRef] [ChemPort]
Bockman, T. M. & Kochi, J. K. (1992). New J. Chem. 16, 39-49.  [ChemPort]
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cui, L.-J. & Wen, X.-C. (2008). Acta Cryst. E64, o1620.  [CSD] [CrossRef] [details]
Frontera, A., Gamez, P., Mascal, M., Mooibroeck, T. J. & Reedijk, J. (2011). Angew. Chem. Int. Ed. 50, 9564-9583.  [ISI] [CrossRef] [ChemPort]
Hardacre, C., Holbrey, J. D., Mullan, C. L., Nieuwenhuyzen, M., Reichert, W. M., Seddon, K. R. & Teat, S. J. (2008). New J. Chem. 32, 1953-1967.  [CrossRef] [ChemPort]
Hardacre, C., Holbrey, J. D., Mullan, C. L., Nieuwenhuyzen, M., Youngs, T. G. A., Bowron, D. T. & Teat, S. J. (2010). Phys. Chem. Chem. Phys. 12, 1842-1853.  [CrossRef] [ChemPort] [PubMed]
Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012b). Acta Cryst. E68, o2514.  [CrossRef] [details]
Kammer, M. N., Mague, J. T. & Koplitz, L. V. (2012a). Acta Cryst. E68, o2409.  [CrossRef] [details]
Koplitz, L. V., Bay, K. D., DiGiovanni, N. & Mague, J. T. (2003). J. Chem. Crystallogr. 33, 391-402.  [ISI] [CSD] [CrossRef] [ChemPort]
Koplitz, L. V., Mague, J. T., Kammer, M. N., McCormick, C. A., Renfro, H. E. & Vumbaco, D. J. (2012). Acta Cryst. E68, o1653.  [CSD] [CrossRef] [details]
Mague, J. T., Ivie, R. M., Hartsock, R. W., Koplitz, L. V. & Spulak, M. (2005). Acta Cryst. E61, o851-o853.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, B. (2009). Acta Cryst. E65, o2395.  [CrossRef] [details]


Acta Cryst (2013). E69, o981-o982   [ doi:10.1107/S1600536813014025 ]

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