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Volume 69 
Part 6 
Pages o941-o942  
June 2013  

Received 7 May 2013
Accepted 15 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.026
wR = 0.056
Data-to-parameter ratio = 18.2
Details
Open access

4-Hydroxy-1,2,6-trimethylpyridinium bromide monohydrate

aDepartment of Physics, Government Arts College (Autonomous), Karur 639 005, India,bCarbon Nanomaterials Laboratory, Department of Physics, National Institute of Technology, Tiruchirappalli 620 015, India,cSchool of Physics, Bharathidasan University, Tiruchirappalli 620 024, India,dFaculty of Health and Life Sciences, Coventry University, Coventry CV1 5FB, England, and eDepartment of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
Correspondence e-mail: seetha_b2002@yahoo.com

The title salt, C8H12NO+·Br-·H2O, is isomorphous with the chloride analogue [Seethalakshmi et al. (2013). Acta Cryst. E69, o835-o836]. In the solid state, the cations, anions and water molecules are interlinked by a network of O-H...O, O-H...Br and C-H...Br interactions. The water molecule makes two O-H...Br hydrogen bonds, generating [010] zigzag chains of alternating water molecules and bromide anions. The cation is involved in two intermolecular C-H...Cl interactions in the chloride salt, whereas three intermolecular C-H...Br interactions are observed in the title bromide salt. This additional intermolecular C-H...Br interaction links the adjacent water and bromide zigzag chains via cationic molecules. In addition, weak [pi]-[pi] stacking interactions are observed between pyridinium rings [centroid-centroid distance = 3.5664 (13) Å].

Related literature

For related structures, see: Seethalakshmi et al. (2006a[Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.],b[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.],c[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.], 2007[Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.], 2013a[Seethalakshmi, T., Manivannan, S., Dhanuskodi, S., Lynch, D. E. & Thamotharan, S. (2013a). Acta Cryst. E69, o835-o836.],b[Seethalakshmi, T., Venkatesan, P., Nallu, M., Lynch, D. E. & Thamotharan, S. (2013b). Acta Cryst. E69, o884.]). For related compounds, see: Dhanuskodi et al. (2006[Dhanuskodi, S., Manivannan, S. & Kirschbaum, K. (2006). Spectrochim. Acta Part A, 64, 504-511.], 2008[Dhanuskodi, S., Manivannan, S. & Philip, J. (2008). Spectrochim. Acta Part A, 69, 1207-1212.]). For graph-set motifs, see: 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
  • C8H12NO+·Br-·H2O

  • Mr = 236.11

  • Monoclinic, P 21 /n

  • a = 8.4796 (4) Å

  • b = 8.5874 (6) Å

  • c = 13.8479 (9) Å

  • [beta] = 99.504 (4)°

  • V = 994.53 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.10 mm-1

  • T = 120 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker-Nonius 95mm CCD camera on [kappa]-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.373, Tmax = 0.427

  • 11830 measured reflections

  • 2277 independent reflections

  • 1888 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.056

  • S = 1.06

  • 2277 reflections

  • 125 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1Wi 0.83 (2) 1.78 (2) 2.607 (2) 174 (3)
O1W-H1W...Br1 0.81 (2) 2.44 (2) 3.2407 (18) 170 (3)
O1W-H2W...Br1ii 0.83 (2) 2.43 (2) 3.2527 (18) 168 (3)
C3-H3...Br1i 0.95 2.86 3.785 (2) 164
C5-H5...Br1iii 0.95 2.90 3.837 (2) 170
C9-H9A...Br1iv 0.98 2.91 3.822 (2) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; method used to solve structure: isomorphous; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5224 ).


Acknowledgements

The authors thank the EPSRC National Crystallography Service (University of Southampton, UK) for the X-ray data collection. ST thanks the management of SASTRA University for their encouragement.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Dhanuskodi, S., Manivannan, S. & Kirschbaum, K. (2006). Spectrochim. Acta Part A, 64, 504-511.  [CSD] [CrossRef] [ChemPort]
Dhanuskodi, S., Manivannan, S. & Philip, J. (2008). Spectrochim. Acta Part A, 69, 1207-1212.  [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Manivannan, S., Dhanuskodi, S., Lynch, D. E. & Thamotharan, S. (2013a). Acta Cryst. E69, o835-o836.  [CrossRef] [details]
Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.  [CSD] [CrossRef] [ChemPort] [details]
Seethalakshmi, T., Venkatesan, P., Nallu, M., Lynch, D. E. & Thamotharan, S. (2013b). Acta Cryst. E69, o884.  [CrossRef] [details]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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, o941-o942   [ doi:10.1107/S1600536813013330 ]

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