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Volume 70 
Part 1 
Page o77  
January 2014  

Received 6 December 2013
Accepted 12 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.112
Data-to-parameter ratio = 17.2
Details
Open access

5-Chloro-2-methyl­sulfanyl-6-(naphtha­len-1-yl­oxy)-1H-benzimidazole methanol monosolvate

aFacultad de Química, Departamento de Farmacia, UNAM, México DF, 04510, Mexico, and bFacultad de Química, Universidad Nacional Autónoma de México, México DF, 04510, Mexico
Correspondence e-mail: mfa@unam.mx

In the title compound, C18H13ClN2OS·CH3OH, the dihedral angle between the benzimidazole group and the naphth­yloxy moiety [82.89 (5)°] very near to orthogonality. The H atom in the five-membered ring is disordered with equal occupancies at the two N atoms and the H atom of the methano­lic hy­droxy group is disordered with equal occupancies over two sites at the O atom. The methanol mol­ecule acts as a hydrogen-bond acceptor for the amino H atom and donates a hydrogen bond to the nonprotonated ring N atom. As a result, chains are formed running along the a axis.

Related literature

For related literature on compound alpha, see: Rivera et al. (2004[Rivera, N., Ibarra, I., Zepeda, A., Fortoul, T., Hernández, A., Castillo, R. & Cantó, G. (2004). Parasitol. Res. 93, 283-286.]); Vera-Montenegro et al. (2003[Vera-Montenegro, Y., Ibarra-Velarde, F., Quiroz-Romero, H., Hernández-Campos, A. & Castillo, R. (2003). Parasitol. Res. 91, 1-4.]); Fairweather (2009[Fairweather, I. (2009). J. Helminthol. 83, 139-150.]); McConville et al. (2010[McConville, M., Hanna, R. E. B., Brennan, G. P., McCoy, M., Edgar, H. W. J., McConell, S., Castillo, R., Hernández-Campos, A. & Fairweather, I. (2010). Parasitol. Res. 106, 311-323.]). For the synthesis of compound alpha, see: Hernández et al. (2002[Hernández, C. A., Ibarra, V. F., Vera, M. Y. F., Rivera, N. & Castillo, B. R. (2002). Chem. Pharm. Bull. 50, 649-652.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13ClN2OS·CH4O

  • Mr = 372.85

  • Triclinic, [P \overline 1]

  • a = 7.4094 (6) Å

  • b = 9.1941 (8) Å

  • c = 14.4253 (11) Å

  • [alpha] = 73.978 (7)°

  • [beta] = 75.315 (7)°

  • [gamma] = 75.136 (7)°

  • V = 895.09 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 298 K

  • 0.6 × 0.56 × 0.17 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.785, Tmax = 0.945

  • 6945 measured reflections

  • 4118 independent reflections

  • 2706 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.112

  • S = 1.03

  • 4118 reflections

  • 239 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1O...N2 0.94 (12) 1.87 (11) 2.768 (2) 158 (7)
O2-H2O...N1i 0.76 (11) 2.04 (11) 2.781 (3) 162 (9)
N1-H1N...O2ii 0.84 (8) 2.03 (8) 2.781 (3) 148 (7)
N2-H2N...O2 0.80 (9) 1.99 (9) 2.768 (2) 164 (7)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6948 ).


Acknowledgements

This work was supported by the Dirección General de Asuntos del Personal Académico (DGAPA) with the project IT201113. MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Fairweather, I. (2009). J. Helminthol. 83, 139-150.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hernández, C. A., Ibarra, V. F., Vera, M. Y. F., Rivera, N. & Castillo, B. R. (2002). Chem. Pharm. Bull. 50, 649-652.  [PubMed]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
McConville, M., Hanna, R. E. B., Brennan, G. P., McCoy, M., Edgar, H. W. J., McConell, S., Castillo, R., Hernández-Campos, A. & Fairweather, I. (2010). Parasitol. Res. 106, 311-323.  [Web of Science] [CrossRef] [PubMed]
Rivera, N., Ibarra, I., Zepeda, A., Fortoul, T., Hernández, A., Castillo, R. & Cantó, G. (2004). Parasitol. Res. 93, 283-286.  [Web of Science] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vera-Montenegro, Y., Ibarra-Velarde, F., Quiroz-Romero, H., Hernández-Campos, A. & Castillo, R. (2003). Parasitol. Res. 91, 1-4.  [PubMed] [ChemPort]


Acta Cryst (2014). E70, o77  [ doi:10.1107/S1600536813033709 ]

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