[Journal logo]

Volume 69 
Part 8 
Page o1288  
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) = 0.002 Å
R = 0.016
wR = 0.041
Data-to-parameter ratio = 23.0
Details
Open access

2-Cyanoanilinium iodide

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

The solid-state structure of the title salt, C7H7N2+.I-, consists of cation-anion sheets lying parallel to (110), with the components linked by N-H...I hydrogen bonds.

Related literature

For the structure of 2-cyano-1-methylpyridinium iodide, see: Kammer et al. (2013[Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2013). Acta Cryst. E69, o1281.]). For structures of other 2-cyanoanilinium salts, see: Cui & Chen (2010[Cui, L.-J. & Chen, X.-Y. (2010). Acta Cryst. E66, o467.]); Zhang (2009[Zhang, L. (2009). Acta Cryst. E65, o2407.]); Cui & Wen (2008[Cui, L.-J. & Wen, X.-C. (2008). Acta Cryst. E64, o1620.]); Oueslati et al. (2005[Oueslati, A., Kefi, R., Akriche, S. & Ben Nasr, C. (2005). Z. Kristallogr. 220, 365.]). For the structures of 4-cyanoanilinium halides, see: Mague et al. (2012[Mague, J. T., Vumbaco, D. J., Kammer, M. N. & Koplitz, L. V. (2012). Acta Cryst. E68, o2623.]); Vumbaco et al. (2012[Vumbaco, D. J., Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012). Acta Cryst. E68, o2884.]); Colapietro et al. (1981[Colapietro, M., Domenicano, A., Marciante, C. & Portalone, G. (1981). Acta Cryst. B37, 387-394.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7N2+·I-

  • Mr = 246.05

  • Orthorhombic, P b c a

  • a = 10.1474 (15) Å

  • b = 8.6979 (13) Å

  • c = 18.073 (3) Å

  • V = 1595.2 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.94 mm-1

  • T = 100 K

  • 0.20 × 0.19 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.43, Tmax = 0.58

  • 25911 measured reflections

  • 2112 independent reflections

  • 2030 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.016

  • wR(F2) = 0.041

  • S = 1.10

  • 2112 reflections

  • 92 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.58 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...I1 0.88 2.74 3.6069 (13) 169
N1-H1B...I1i 0.88 2.71 3.5501 (14) 160
N1-H1C...I1ii 0.88 2.84 3.6615 (13) 156
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXM (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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: HB7106 ).


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.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2010). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.
Colapietro, M., Domenicano, A., Marciante, C. & Portalone, G. (1981). Acta Cryst. B37, 387-394.  [CrossRef] [Web of Science] [IUCr Journals]
Cui, L.-J. & Chen, X.-Y. (2010). Acta Cryst. E66, o467.  [CSD] [CrossRef] [IUCr Journals]
Cui, L.-J. & Wen, X.-C. (2008). Acta Cryst. E64, o1620.  [CSD] [CrossRef] [IUCr Journals]
Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2013). Acta Cryst. E69, o1281.  [CrossRef] [IUCr Journals]
Mague, J. T., Vumbaco, D. J., Kammer, M. N. & Koplitz, L. V. (2012). Acta Cryst. E68, o2623.  [CSD] [CrossRef] [IUCr Journals]
Oueslati, A., Kefi, R., Akriche, S. & Ben Nasr, C. (2005). Z. Kristallogr. 220, 365.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vumbaco, D. J., Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2012). Acta Cryst. E68, o2884.  [CSD] [CrossRef] [IUCr Journals]
Zhang, L. (2009). Acta Cryst. E65, o2407.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1288  [ doi:10.1107/S1600536813019314 ]

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.