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Volume 69 
Part 9 
Pages o1485-o1486  
September 2013  

Received 15 August 2013
Accepted 20 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.124
Data-to-parameter ratio = 15.5
Details
Open access

2-(4-Hydroxyphenyl)-1H-benzimidazol-3-ium chloride monohydrate

aLaboratorio de Biofisica y Biocatálisis, Sección de Estudios de Posgrado e Investigación de la Escuela Superior de Medicina del Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón s/n Casco de Santo Tomás, México, DF 11340, Mexico,bLaboratorio de Investigación en Química, Departamento de Ciencias Básicas, Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional, Av. Acueducto s/n Barrio la laguna Ticoman, México, DF 07340, Mexico, and cCentro de Investigaciones Químicas, Universidad Autonoma del Estado de Hidalgo, km. 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo 42184, Mexico
Correspondence e-mail: ipadillamar@ipn.mx

The title molecular salt, C13H11N2O+·Cl-·H2O, crystallizes as a monohydrate. In the cation, the phenol and benzimidazole rings are almost coplanar, making a dihedral angle of 3.18 (4)°. The chloride anion and benzimidazole cation are linked by two N+-H...Cl- hydrogen bonds, forming chains propagating along [010]. These chains are linked through O-H...Cl hydrogen bonds involving the water molecule and the chloride anion, which form a diamond core, giving rise to the formation of two-dimensional networks lying parallel to (10-2). Two [pi]-[pi] interactions involving the imidazolium ring with the benzene and phenol rings [centroid-centroid distances = 3.859 (3) and 3.602 (3) Å, respectively], contribute to this second dimension. A strong O-H...O hydrogen bond involving the water molecule and the phenol substituent on the benzimidazole unit links the networks, forming a three-dimensional structure.

Related literature

For biological properties of benzimidazoles and their applications, see: Ansari & Lal (2009[Ansari, K. F. & Lal, C. (2009). J. Chem. Sci. 121 , 1017-1025.]); Laryea et al. (2010[Laryea, D., Gullbo, J., Isakssoon, A., Larsson, R. & Nygren, P. (2010). Anti-Cancer Drugs, 21, 33-42.]); Mohan et al. (2011[Mohan, V. G., Sreenivasulu, N., Rao, A. S. & Chigiri, S. (2011). Der Pharma Chem., 3, 446-452.]); Refaat (2010[Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.]); Zhou et al. (2013[Zhou, B., Li, B., Yi, W., Bu, X. & Ma, L. (2013). Bioorg. Med. Chem. Lett. 23, 3759-3763.]); Khan et al. (2012[Khan, K.-M., Khan, M., Ambreen, N., Rahim, F., Naureen, S., Perveen, S., Choudhary, M. I. & Voelter, W. (2012). Med. Chem. 8, 421-427.]). For their use in crystal-engineering, see: Cai et al. (2002[Cai, C.-X., Tian, Y.-Q., Li, Y.-Z. & You, X.-Z. (2002). Acta Cryst. C58, m459-m460.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the structures of benzimidazole halohydrates, see: Akkurt et al. (2010[Akkurt, M., Çelik, Í., Küçükbay, H., Sireci, N. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1770-o1771.]); Baktir et al. (2010[Baktir, Z., Akkurt, M., Sireci, N. & Küçükbay, H. (2010). Acta Cryst. E66, o2393-o2394.]). For the microwave synthesis of neutral 4-(1H-benzimidazol-2-yl)phenol, see: Navarrete-Vázquez et al. (2006[Navarrete-Vázquez, G., Moreno-Díaz, H., Aguirre-Crespo, F., León-Rivera, I., Villalobos-Molina, R., Muñoz-Muñiz, O. & Estrada-Soto, S. (2006). Bioorg. Med. Chem. Lett. 16, 4169-4173.]). For its crystal structure, see: Zhan et al. (2007[Zhan, Q.-G., Liu, M.-S., Zeng, R.-H., Yang, D.-Q. & Cai, Y.-P. (2007). Acta Cryst. E63, o3470.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N2O+·Cl-·H2O

  • Mr = 264.70

  • Monoclinic, C 2/c

  • a = 10.3225 (5) Å

  • b = 16.3159 (5) Å

  • c = 15.4618 (8) Å

  • [beta] = 101.071 (5)°

  • V = 2555.6 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 293 K

  • 0.38 × 0.33 × 0.28 × 0.15 (radius) mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: for a sphere [the interpolation procedure of (Dwiggins, 1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.]) was used with some modification] Tmin = 0.861, Tmax = 0.862

  • 12720 measured reflections

  • 2519 independent reflections

  • 2032 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.06

  • 2519 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...Cl1 0.86 2.29 3.1167 (16) 162
N3-H3...Cl1i 0.86 2.32 3.1625 (16) 168
O1-H1A...Cl1ii 0.89 2.39 3.266 (2) 167
O1-H1B...Cl1 0.92 2.33 3.243 (2) 171
O13-H13...O1iii 0.82 1.86 2.666 (3) 166
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2637 ).


Acknowledgements

The authors gratefully acknowledge financial support from Conacyt and SIP-IPN.

References

Akkurt, M., Çelik, Í., Küçükbay, H., Sireci, N. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1770-o1771.  [CrossRef] [ChemPort] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ansari, K. F. & Lal, C. (2009). J. Chem. Sci. 121 , 1017-1025.  [CrossRef] [ChemPort]
Baktir, Z., Akkurt, M., Sireci, N. & Küçükbay, H. (2010). Acta Cryst. E66, o2393-o2394.  [CSD] [CrossRef] [details]
Cai, C.-X., Tian, Y.-Q., Li, Y.-Z. & You, X.-Z. (2002). Acta Cryst. C58, m459-m460.  [CSD] [CrossRef] [details]
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khan, K.-M., Khan, M., Ambreen, N., Rahim, F., Naureen, S., Perveen, S., Choudhary, M. I. & Voelter, W. (2012). Med. Chem. 8, 421-427.  [ChemPort] [PubMed]
Laryea, D., Gullbo, J., Isakssoon, A., Larsson, R. & Nygren, P. (2010). Anti-Cancer Drugs, 21, 33-42.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mohan, V. G., Sreenivasulu, N., Rao, A. S. & Chigiri, S. (2011). Der Pharma Chem., 3, 446-452.
Navarrete-Vázquez, G., Moreno-Díaz, H., Aguirre-Crespo, F., León-Rivera, I., Villalobos-Molina, R., Muñoz-Muñiz, O. & Estrada-Soto, S. (2006). Bioorg. Med. Chem. Lett. 16, 4169-4173.  [PubMed]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhan, Q.-G., Liu, M.-S., Zeng, R.-H., Yang, D.-Q. & Cai, Y.-P. (2007). Acta Cryst. E63, o3470.  [CrossRef] [details]
Zhou, B., Li, B., Yi, W., Bu, X. & Ma, L. (2013). Bioorg. Med. Chem. Lett. 23, 3759-3763.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1485-o1486   [ doi:10.1107/S1600536813023441 ]

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