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Volume 68 
Part 1 
Pages o197-o198  
January 2012  

Received 12 December 2011
Accepted 14 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.086
Data-to-parameter ratio = 13.4
Details
Open access

Ethyl 1-(2-hydroxyethyl)-2-[2-(methylsulfanyl)ethyl]-1H-benzimidazole-5-carboxylate

aKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia, and bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia
Correspondence e-mail: shafida@iium.edu.my

In the crystal structure of the title compound, C15H20N2O3S, the hydroxy group is involved in the formation of O-H...N hydrogen bonds, which link two molecules into a centrosymmetric dimer. Weak C-H...O hydrogen bonds further link these dimers into chains propagating along the a axis. The crystal packing exhibits [pi]-[pi] interactions between the five- and six-membered rings of neighbouring molecules [centroid-centroid distance = 3.819 (2) Å] and short intermolecular S...S contacts of 3.495 (1) Å.

Related literature

For details of the synthesis and related structures, see: Wright (1951[Wright, J. B. (1951). Chem. Rev. 48, 387-541.]); Preston (1974[Preston, P. N. (1974). Chem. Rev. 74, 279-314.]); Hamzah et al. (2010[Hamzah, N., Abd. Hamid, S., Abdul Rahim, A. S., Rosli, M. M. & Fun, H.-K. (2010). Acta Cryst. E66, o1824-o1825.]); Arumugam et al. 2011[Arumugam, N., Ngah, N., Abd Hamid, S. & Abdul Rahim, A. S. (2011). Acta Cryst. E67, o2938.]); Ruiz et al. (2010[Ruiz, V. R., Corma, A. & Sabater, M. J. (2010). Tetrahedron, 66, 730-735.]); Chou et al. (2011[Chou, C.-T., Yellol, G. S., Chang, W.-J., Sun, M.-L. & Sun, C.-M. (2011). Tetrahedron, 67, 2110-2117.]). For the therapeutic properties of benzimidazole derivatives, see: Li et al. (2006[Li, Y.-F., Wang, G.-F., He, P.-L., Huang, W.-G., Zhu, F. H., Gao, H.-Y., Luo, Y., Feng, C.-L., Shi, L.-P., Ren, Y.-D., Lu, W. & Zuo, J.-P. (2006). J. Med. Chem. 49, 4790-4794.]); Hwu et al. (2008[Hwu, J. R., Singha, R., Hong, S. C., Chang, Y. H., Das, A. R., Vliegen, I., De Clercq, E. & Neyts, J. (2008). Antivir. Res. 77, 157-162.]); Cui et al. (2010[Cui, M., Ono, M., Kimura, H., Kawashima, H., Liu, B. L. & Saji, H. (2010). Nucl. Med. Biol. 38, 313-320.]); Sasmal et al. (2011[Sasmal, P., Sasmal, S., Abbineni, C., Venkatesham, B., Rao, P. T., Roshaiah, M., Khanna, I., Sebastian, V. J., Suresh, J., Singh, M. P., Talwar, R., Shashikumar, D., Reddy, K. H., Frimurer, T. M., Rist, O., Elster, L. & Hogberg, T. (2011). Med. Chem. Commun. 2, 385-389.]); Demirayak et al. (2011[Demirayak, S., Kajagil, I. & Yurttas, L. (2011). Eur. J. Med. Chem. 46, 411-416.]). For bond lengths in organic compounds, 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 low-temperature device used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C15H20N2O3S

  • Mr = 308.39

  • Triclinic, [P \overline 1]

  • a = 8.3909 (1) Å

  • b = 8.8277 (2) Å

  • c = 11.5025 (2) Å

  • [alpha] = 110.218 (1)°

  • [beta] = 102.529 (1)°

  • [gamma] = 99.101 (1)°

  • V = 754.78 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 100 K

  • 0.27 × 0.24 × 0.07 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.985

  • 6027 measured reflections

  • 2627 independent reflections

  • 2243 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.086

  • S = 1.04

  • 2627 reflections

  • 196 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...N1i 0.84 (2) 2.01 (2) 2.808 (2) 159 (2)
C11-H11A...O1ii 0.99 2.39 3.224 (2) 142
C11-H11B...O3iii 0.99 2.42 3.222 (2) 138
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+3, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: CV5217 ).


Acknowledgements

NH, SAH and ASAR gratefully acknowledge the International Islamic University Malaysia (IIUM) for the FRGS Grant (No. FRGS0510-119), the USM Research Grant (No. 304/PFARMASI/650544/I121) and MOSTI (grant no. 09-05-lfn-med-004) for funding the synthetic chemistry work.

References

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.
Arumugam, N., Ngah, N., Abd Hamid, S. & Abdul Rahim, A. S. (2011). Acta Cryst. E67, o2938.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Chou, C.-T., Yellol, G. S., Chang, W.-J., Sun, M.-L. & Sun, C.-M. (2011). Tetrahedron, 67, 2110-2117.  [CrossRef] [ChemPort]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cui, M., Ono, M., Kimura, H., Kawashima, H., Liu, B. L. & Saji, H. (2010). Nucl. Med. Biol. 38, 313-320.  [CrossRef] [PubMed]
Demirayak, S., Kajagil, I. & Yurttas, L. (2011). Eur. J. Med. Chem. 46, 411-416.  [CrossRef] [ChemPort] [PubMed]
Hamzah, N., Abd. Hamid, S., Abdul Rahim, A. S., Rosli, M. M. & Fun, H.-K. (2010). Acta Cryst. E66, o1824-o1825.  [CSD] [CrossRef] [details]
Hwu, J. R., Singha, R., Hong, S. C., Chang, Y. H., Das, A. R., Vliegen, I., De Clercq, E. & Neyts, J. (2008). Antivir. Res. 77, 157-162.  [CrossRef] [PubMed] [ChemPort]
Li, Y.-F., Wang, G.-F., He, P.-L., Huang, W.-G., Zhu, F. H., Gao, H.-Y., Luo, Y., Feng, C.-L., Shi, L.-P., Ren, Y.-D., Lu, W. & Zuo, J.-P. (2006). J. Med. Chem. 49, 4790-4794.  [CrossRef] [PubMed] [ChemPort]
Preston, P. N. (1974). Chem. Rev. 74, 279-314.  [CrossRef] [ChemPort] [ISI]
Ruiz, V. R., Corma, A. & Sabater, M. J. (2010). Tetrahedron, 66, 730-735.  [CrossRef] [ChemPort]
Sasmal, P., Sasmal, S., Abbineni, C., Venkatesham, B., Rao, P. T., Roshaiah, M., Khanna, I., Sebastian, V. J., Suresh, J., Singh, M. P., Talwar, R., Shashikumar, D., Reddy, K. H., Frimurer, T. M., Rist, O., Elster, L. & Hogberg, T. (2011). Med. Chem. Commun. 2, 385-389.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wright, J. B. (1951). Chem. Rev. 48, 387-541.  [CrossRef]


Acta Cryst (2012). E68, o197-o198   [ doi:10.1107/S160053681105389X ]

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