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Volume 69 
Part 5 
Page o804  
May 2013  

Received 17 April 2013
Accepted 24 April 2013
Online 30 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.094
Data-to-parameter ratio = 17.2
Details
Open access

L-Histidinium p-toluenesulfonate

aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title salt, C6H10N3O2+·C7H7O3S-, the imidazole ring makes a dihedral angle of 70.93 (12)° with the plane of the toluene ring. In the crystal, the ions are linked via N-H...O and weak C-H...O hydrogen bonds forming two-dimensional networks lying parallel to (001). These networks are linked via C-H...[pi] interactions, forming a three-dimensional structure.

Related literature

For related structures of 4-toluenesulfonate salts, see: Koshima et al. (2004[Koshima, H., Miyamoto, H., Yagi, I. & Uosaki, K. (2004). Cryst. Growth Des. 4,807-811.]); Biradha & Mahata (2005[Biradha, K. & Mahata, G. (2005). Cryst. Growth Des. 5, 49-51.]); Sivakumar et al. (2012[Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.]). For the structure of L-histidine, see: Madden et al. (1972[Madden, J. J., McGandy, E. L. & Seeman, N. C. (1972). Acta Cryst. B28, 2377-2382.]); Andra et al. (2010[Andra, K. K., Bullinger, J. C., Bann, J. G. & Eichhorn, D. M. (2010). Acta Cryst. E66, o2713.]).

[Scheme 1]

Experimental

Crystal data
  • C6H10N3O2+·C7H7O3S-

  • Mr = 327.36

  • Orthorhombic, P 21 21 21

  • a = 5.2700 (2) Å

  • b = 7.3691 (3) Å

  • c = 38.2042 (14) Å

  • V = 1483.67 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.930, Tmax = 0.952

  • 8400 measured reflections

  • 3638 independent reflections

  • 3533 reflections with I > 2[sigma](I)

  • Rint = 0.022

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

  • wR(F2) = 0.094

  • S = 1.20

  • 3638 reflections

  • 212 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1479 Friedel pairs

  • Flack parameter: 0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids the C1-C6 and N1/N2/C8-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.86 2.00 2.828 (2) 160
N2-H2A...O3ii 0.86 1.89 2.746 (2) 175
N3-H3B...O4iii 0.96 (3) 1.80 (3) 2.755 (2) 176 (2)
N3-H3C...O4iv 0.83 (3) 2.10 (3) 2.896 (2) 161 (2)
N3-H3D...O3i 0.92 (2) 2.15 (2) 3.000 (2) 153.4 (19)
C8-H8...O1v 0.93 2.41 2.967 (3) 118
C9-H9...O5vi 0.93 2.47 3.062 (3) 122
C6-H6...Cg2 0.93 2.73 3.515 (2) 143
C8-H8...Cg1ii 0.93 2.71 3.394 (2) 131
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x-1, y, z; (v) x+1, y-1, z; (vi) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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.]); 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: SU2589 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for data collection. TS and DV thank the UGC (SAP-CAS) for the departmental facilities. TS also thanks the DST Inspire program for financial assistance.

References

Andra, K. K., Bullinger, J. C., Bann, J. G. & Eichhorn, D. M. (2010). Acta Cryst. E66, o2713.  [CrossRef] [details]
Biradha, K. & Mahata, G. (2005). Cryst. Growth Des. 5, 49-51.  [CSD] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Koshima, H., Miyamoto, H., Yagi, I. & Uosaki, K. (2004). Cryst. Growth Des. 4,807-811.  [CrossRef] [ChemPort]
Madden, J. J., McGandy, E. L. & Seeman, N. C. (1972). Acta Cryst. B28, 2377-2382.  [CrossRef] [ChemPort] [details] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o804  [ doi:10.1107/S1600536813011161 ]

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