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

Hamzah, N.; Ngah, N.; Abd Hamid, S.; Abdul Rahim, A.S.

doi:10.1107/S160053681105389X

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.086
Data-to-parameter ratio = 13.4
Details

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

Nurasyikin Hamzah,^a Nurziana Ngah,^a Shafida Abd Hamid ^a ^* and Aisyah Saad Abdul Rahim ^b

^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-HN hydrogen bonds, which link two molecules into a centrosymmetric dimer. Weak C-HO 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 SS contacts of 3.495 (1) Å.

Related literature

For details of the synthesis and related structures, see: Wright (1951); Preston (1974); Hamzah et al. (2010); Arumugam et al. 2011); Ruiz et al. (2010); Chou et al. (2011). For the therapeutic properties of benzimidazole derivatives, see: Li et al. (2006); Hwu et al. (2008); Cui et al. (2010); Sasmal et al. (2011); Demirayak et al. (2011). For bond lengths in organic compounds, see: Allen et al. (1987). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₅H₂₀N₂O₃S
M_r = 308.39
Triclinic, $[P \overline 1]$
a = 8.3909 (1) Å
b = 8.8277 (2) Å
c = 11.5025 (2) Å
= 110.218 (1)°
= 102.529 (1)°
= 99.101 (1)°
V = 754.78 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.941, T_max = 0.985
6027 measured reflections
2627 independent reflections
2243 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(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
_max = 0.24 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3N1ⁱ	0.84 (2)	2.01 (2)	2.808 (2)	159 (2)
C11-H11AO1ⁱⁱ	0.99	2.39	3.224 (2)	142
C11-H11BO3ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

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