[Journal logo]

Volume 69 
Part 8 
Page o1281  
August 2013  

Received 11 July 2013
Accepted 12 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.008 Å
R = 0.036
wR = 0.091
Data-to-parameter ratio = 574.1
Details
Open access

2-Cyano-1-methylpyridinium iodide

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 cation in the title compound, C7H7N2+·I-, is planar (r.m.s. deviation for the nine fitted non-H atoms = 0.040 Å). The crystal packing is best described as undulating layers of cations and anions associated via C-H...I interactions.

Related literature

For the structure of 2-cyano-N-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.]). For structures of 3-cyano-N-methylpyridinium salts, see: Koplitz et al. (2003[Koplitz, L. V., Bay, K. D., DiGiovanni, N. & Mague, J. T. (2003). J. Chem. Crystallogr. 33, 391-402.]); 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 structures of 4-cyano-N-methylpyridinium salts, see: Kammer, Koplitz & Mague (2012[Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012). Acta Cryst. E68, o2514.]); Kammer, Mague & Koplitz (2012[Kammer, M. N., Mague, J. T. & Koplitz, L. V. (2012). Acta Cryst. E68, o2409.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7N2+·I-

  • Mr = 246.05

  • Orthorhombic, P b c a

  • a = 9.5785 (6) Å

  • b = 8.5687 (5) Å

  • c = 20.2229 (13) Å

  • V = 1659.80 (18) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.79 mm-1

  • T = 100 K

  • 0.16 × 0.14 × 0.07 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 = 0.58, Tmax = 0.77

  • 58292 measured reflections

  • 53390 independent reflections

  • 40858 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.091

  • S = 1.03

  • 53390 reflections

  • 93 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.14 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-H1B...I1i 0.98 3.20 4.014 (5) 141
C1-H1C...I1ii 0.98 3.11 4.021 (5) 156
C5-H5...I1iii 0.95 3.12 3.810 (5) 131
C6-H6...I1iv 0.95 3.03 3.677 (5) 126
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, y+1, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iv) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Göttingen, Germany.]); 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 and CELL_NOW (Sheldrick, 2008b[Sheldrick, G. M. (2008a). CELL_NOW. University of Göttingen, Germany.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5240 ).


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 APEX diffractometer. Michael Kammer was supported by Louisiana Board of Regents grant LEQSF(2007-12)-ENH-PKSFI-PES-03 during the summer of 2011.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012). Acta Cryst. E68, o2514.  [CSD] [CrossRef] [IUCr Journals]
Kammer, M. N., Mague, J. T. & Koplitz, L. V. (2012). Acta Cryst. E68, o2409.  [CSD] [CrossRef] [IUCr Journals]
Koplitz, L. V., Bay, K. D., DiGiovanni, N. & Mague, J. T. (2003). J. Chem. Crystallogr. 33, 391-402.  [Web of Science] [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] [IUCr Journals]
Mague, J. T., Ivie, R. M., Hartsock, R. W., Koplitz, L. V. & Spulak, M. (2005). Acta Cryst. E61, o851-o853.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008a). CELL_NOW. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany.
Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Göttingen, Germany.


Acta Cryst (2013). E69, o1281  [ doi:10.1107/S1600536813019302 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.