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

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o197-o198

doi:10.1107/S160053681105389X

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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

(Received 12 December 2011; accepted 14 December 2011; online 21 December 2011)

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 π–π 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 ); 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
α = 110.218 (1)°
β = 102.529 (1)°
γ = 99.101 (1)°
V = 754.78 (2) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(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
Δρ_max = 0.24 e Å⁻³
Δρ_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); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105389X/cv5217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105389X/cv5217Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105389X/cv5217Isup3.cml

checkCIF report

Comment top

Heteroaromatic compounds of benzimidazoles exhibit important values particularly in biological and pharmaceutical fields. The previledge sub-structures of benzimidazoles have been reported as potential inhibitors (Sasmal et al., 2011), probes for β-amyloid (Aβ) plaques in Alzheimer's disease (Cui et al., 2010), showed anti- cancer activities (Demirayak et al., 2011), anti hepatitis B (Li et al., 2006) and C virus (Hwu et al., 2008). Various methods have been employed to synthesize benzimidazole derivatives (Wright, 1951; Preston, 1974). However, two common methods widely used are either by reacting diamine with carboxylic acid or diamine with aldehyde using solid catalyst (Ruiz et al., 2010) or polymer bounds (Chou et al., 2011). In continuation of our work (Hamzah et al., 2010; Arumugam et al. 2011), we report herein the crystal structure of the title compound, (I).

The title molecule (Fig. 1), is similar with those reported earlier - ethyl 1-(2- hydroxyethyl)-2-phenyl-1H-benzimidazole-5-carboxylate (Hamzah et al., 2010) and ethyl 1-(2-hydroxyethyl)-2-propyl-1H-benzimidazole -5-carboxylate (Hamzah et al., 2011), in that only the 2-methylthioethyl substituent at the imidazole ring is different. The benzimidazole ring [N1/N2/C1—C7] is essentially planar and the C4 atom deviates by 0.012 (2)Å from that plane. The bond lengths and angles are in normal ranges (Allen et al., 1987) and are in agreement with those reported by Hamzah et al. (2010, 2011).

In the crystal structure, the hydroxy group is involved in formation intermolecular hydrogen bond O—H···N (Table 1), which link two molecules into centrosymmetric dimer (Fig. 2). Weak intermolecular C—H···O hydrogen bonds (Table 1) link further these dimers into chains propagated along a axis. The crystal packing exhibits π–π interactions between the benzimidazole fragments with Cg1···Cg2 distance of 3.819 (2)Å (Cg1 and Cg2 are centroids of N1/N2/C1/C6/C7 and C1-C6, respectively) and short intermolecular S···S contacts of 3.495 (1) Å.

Related literature top

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 top

A mixture of 3-amino-4-(2-hydroxylethanolamine)benzoic acid ethyl ester (0.1.0 g, 0.45 mmol), K10-montmorillonite (2.0 g), 3-(methylthio) propionaldehyde (0.098 g, 0.91 mmol) and 1 ml MeCN were irradiated in CEM^TM microwave at 80°C, 150 W, 5 bar and hold for 5 minutes. Then, another aliquot of aldehyde was added and the reation mixture was irradiated again at the same condition as before. The reaction was monitored by TLC (Hex:EtOAc,1:4). Upon completion, K10-montmorillonite was removed by filtration, washed with DCM and later evaporated in vacuo to afford brown precipitate. The compound was purified with PLC (Hex:EtOAc, 1:4) before it was recrystallized with hot MeOH to afford colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsods.
	Fig. 2. A portion of the crystal packing viewed down the b axis and showing the hydrogen-bonded (dashed lines) dimers.

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

Crystal data top

C₁₅H₂₀N₂O₃S	Z = 2
M_r = 308.39	F(000) = 328
Triclinic, P1	D_x = 1.357 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3909 (1) Å	Cell parameters from 2401 reflections
b = 8.8277 (2) Å	θ = 1.9–25.0°
c = 11.5025 (2) Å	µ = 0.23 mm⁻¹
α = 110.218 (1)°	T = 100 K
β = 102.529 (1)°	Plate, colourless
γ = 99.101 (1)°	0.27 × 0.24 × 0.07 mm
V = 754.78 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2627 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
T_min = 0.941, T_max = 0.985	l = −13→13
6027 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0307P)² + 0.5234P] where P = (F_o² + 2F_c²)/3
2627 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₂₀N₂O₃S	γ = 99.101 (1)°
M_r = 308.39	V = 754.78 (2) Å³
Triclinic, P1	Z = 2
a = 8.3909 (1) Å	Mo Kα radiation
b = 8.8277 (2) Å	µ = 0.23 mm⁻¹
c = 11.5025 (2) Å	T = 100 K
α = 110.218 (1)°	0.27 × 0.24 × 0.07 mm
β = 102.529 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2627 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2243 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.985	R_int = 0.026
6027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
2627 reflections	Δρ_min = −0.26 e Å⁻³
196 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open=flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.33465 (6)	0.81922 (6)	0.91756 (5)	0.02048 (15)
O1	0.36330 (17)	−0.07772 (17)	0.28863 (14)	0.0244 (3)
O2	0.46252 (16)	−0.29862 (16)	0.19992 (13)	0.0195 (3)
O3	1.32576 (17)	0.48466 (17)	0.39325 (14)	0.0213 (3)
H3	1.2305 (18)	0.505 (3)	0.391 (2)	0.035 (7)*
N1	0.94054 (19)	0.36073 (19)	0.58614 (15)	0.0151 (3)
N2	1.14023 (19)	0.26662 (19)	0.50164 (15)	0.0140 (3)
C1	0.8668 (2)	0.2070 (2)	0.48209 (18)	0.0140 (4)
C2	0.6994 (2)	0.1144 (2)	0.43009 (18)	0.0158 (4)
H2	0.6138	0.1549	0.4640	0.019*
C3	0.6610 (2)	−0.0396 (2)	0.32689 (18)	0.0153 (4)
C4	0.7890 (2)	−0.0998 (2)	0.27731 (18)	0.0166 (4)
H4	0.7597	−0.2063	0.2081	0.020*
C5	0.9553 (2)	−0.0084 (2)	0.32637 (18)	0.0164 (4)
H5	1.0408	−0.0485	0.2921	0.020*
C6	0.9912 (2)	0.1465 (2)	0.42935 (18)	0.0141 (4)
C7	1.1022 (2)	0.3904 (2)	0.59415 (18)	0.0145 (4)
C8	0.4814 (2)	−0.1364 (2)	0.27111 (18)	0.0169 (4)
C9	0.2882 (3)	−0.3974 (2)	0.1397 (2)	0.0231 (5)
H9A	0.2271	−0.3537	0.0798	0.028*
H9B	0.2301	−0.3927	0.2067	0.028*
C10	0.2919 (3)	−0.5719 (3)	0.0675 (2)	0.0391 (6)
H10A	0.3534	−0.5743	0.0038	0.059*
H10B	0.1762	−0.6412	0.0227	0.059*
H10C	0.3486	−0.6153	0.1282	0.059*
C11	1.3032 (2)	0.2629 (2)	0.47536 (19)	0.0165 (4)
H11A	1.3195	0.1490	0.4552	0.020*
H11B	1.3949	0.3403	0.5538	0.020*
C12	1.3139 (2)	0.3126 (2)	0.36286 (19)	0.0181 (4)
H12A	1.4139	0.2852	0.3363	0.022*
H12B	1.2125	0.2463	0.2884	0.022*
C13	1.2355 (2)	0.5380 (2)	0.69567 (18)	0.0171 (4)
H13A	1.2923	0.6013	0.6533	0.021*
H13B	1.3214	0.4989	0.7436	0.021*
C14	1.1634 (2)	0.6532 (2)	0.79092 (18)	0.0179 (4)
H14A	1.0995	0.5893	0.8293	0.022*
H14B	1.0850	0.7012	0.7452	0.022*
C15	1.2132 (3)	0.9482 (3)	0.9979 (2)	0.0253 (5)
H15A	1.1466	0.9862	0.9373	0.038*
H15B	1.2896	1.0452	1.0725	0.038*
H15C	1.1373	0.8836	1.0275	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0191 (3)	0.0174 (3)	0.0193 (3)	0.0018 (2)	0.0047 (2)	0.0024 (2)
O1	0.0171 (8)	0.0243 (8)	0.0270 (8)	0.0040 (6)	0.0062 (6)	0.0053 (7)
O2	0.0192 (7)	0.0149 (7)	0.0191 (7)	0.0003 (6)	0.0016 (6)	0.0046 (6)
O3	0.0165 (8)	0.0198 (7)	0.0332 (9)	0.0064 (6)	0.0106 (7)	0.0144 (7)
N1	0.0152 (8)	0.0137 (8)	0.0161 (8)	0.0033 (6)	0.0047 (7)	0.0054 (7)
N2	0.0126 (8)	0.0142 (8)	0.0167 (8)	0.0043 (6)	0.0057 (7)	0.0065 (7)
C1	0.0168 (10)	0.0131 (9)	0.0135 (10)	0.0056 (8)	0.0046 (8)	0.0062 (8)
C2	0.0161 (10)	0.0172 (10)	0.0160 (10)	0.0059 (8)	0.0058 (8)	0.0075 (8)
C3	0.0174 (10)	0.0162 (10)	0.0144 (10)	0.0040 (8)	0.0038 (8)	0.0090 (8)
C4	0.0224 (11)	0.0129 (9)	0.0141 (10)	0.0039 (8)	0.0054 (8)	0.0049 (8)
C5	0.0189 (10)	0.0167 (10)	0.0175 (10)	0.0070 (8)	0.0095 (8)	0.0077 (8)
C6	0.0143 (10)	0.0146 (9)	0.0153 (10)	0.0037 (8)	0.0043 (8)	0.0083 (8)
C7	0.0176 (10)	0.0132 (9)	0.0153 (10)	0.0057 (8)	0.0059 (8)	0.0074 (8)
C8	0.0208 (11)	0.0174 (10)	0.0136 (10)	0.0040 (8)	0.0049 (8)	0.0079 (8)
C9	0.0184 (11)	0.0230 (11)	0.0224 (11)	−0.0025 (8)	0.0015 (9)	0.0085 (9)
C10	0.0296 (13)	0.0301 (13)	0.0410 (15)	−0.0038 (10)	0.0105 (12)	−0.0004 (11)
C11	0.0140 (10)	0.0162 (10)	0.0213 (11)	0.0070 (8)	0.0075 (8)	0.0070 (8)
C12	0.0170 (10)	0.0185 (10)	0.0219 (11)	0.0072 (8)	0.0094 (9)	0.0082 (9)
C13	0.0161 (10)	0.0169 (10)	0.0183 (11)	0.0038 (8)	0.0056 (8)	0.0065 (8)
C14	0.0161 (10)	0.0187 (10)	0.0161 (10)	0.0032 (8)	0.0034 (8)	0.0047 (8)
C15	0.0294 (12)	0.0214 (11)	0.0222 (11)	0.0087 (9)	0.0075 (10)	0.0043 (9)

Geometric parameters (Å, º) top

S1—C15	1.799 (2)	C5—H5	0.9500
S1—C14	1.812 (2)	C7—C13	1.495 (3)
O1—C8	1.212 (2)	C9—C10	1.485 (3)
O2—C8	1.345 (2)	C9—H9A	0.9900
O2—C9	1.456 (2)	C9—H9B	0.9900
O3—C12	1.417 (2)	C10—H10A	0.9800
O3—H3	0.843 (10)	C10—H10B	0.9800
N1—C7	1.317 (2)	C10—H10C	0.9800
N1—C1	1.395 (2)	C11—C12	1.518 (3)
N2—C7	1.372 (2)	C11—H11A	0.9900
N2—C6	1.379 (2)	C11—H11B	0.9900
N2—C11	1.466 (2)	C12—H12A	0.9900
C1—C2	1.391 (3)	C12—H12B	0.9900
C1—C6	1.403 (2)	C13—C14	1.521 (3)
C2—C3	1.393 (3)	C13—H13A	0.9900
C2—H2	0.9500	C13—H13B	0.9900
C3—C4	1.414 (3)	C14—H14A	0.9900
C3—C8	1.485 (3)	C14—H14B	0.9900
C4—C5	1.379 (3)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.400 (3)	C15—H15C	0.9800

C15—S1—C14	99.19 (10)	C9—C10—H10A	109.5
C8—O2—C9	114.83 (15)	C9—C10—H10B	109.5
C12—O3—H3	110.8 (17)	H10A—C10—H10B	109.5
C7—N1—C1	104.86 (15)	C9—C10—H10C	109.5
C7—N2—C6	106.81 (14)	H10A—C10—H10C	109.5
C7—N2—C11	128.13 (16)	H10B—C10—H10C	109.5
C6—N2—C11	124.94 (15)	N2—C11—C12	111.81 (15)
C2—C1—N1	130.07 (17)	N2—C11—H11A	109.3
C2—C1—C6	120.17 (17)	C12—C11—H11A	109.3
N1—C1—C6	109.76 (16)	N2—C11—H11B	109.3
C1—C2—C3	118.05 (17)	C12—C11—H11B	109.3
C1—C2—H2	121.0	H11A—C11—H11B	107.9
C3—C2—H2	121.0	O3—C12—C11	113.02 (16)
C2—C3—C4	120.76 (17)	O3—C12—H12A	109.0
C2—C3—C8	117.54 (17)	C11—C12—H12A	109.0
C4—C3—C8	121.69 (17)	O3—C12—H12B	109.0
C5—C4—C3	121.96 (18)	C11—C12—H12B	109.0
C5—C4—H4	119.0	H12A—C12—H12B	107.8
C3—C4—H4	119.0	C7—C13—C14	112.12 (15)
C4—C5—C6	116.42 (17)	C7—C13—H13A	109.2
C4—C5—H5	121.8	C14—C13—H13A	109.2
C6—C5—H5	121.8	C7—C13—H13B	109.2
N2—C6—C5	131.88 (17)	C14—C13—H13B	109.2
N2—C6—C1	105.50 (16)	H13A—C13—H13B	107.9
C5—C6—C1	122.61 (17)	C13—C14—S1	109.23 (13)
N1—C7—N2	113.06 (17)	C13—C14—H14A	109.8
N1—C7—C13	124.93 (16)	S1—C14—H14A	109.8
N2—C7—C13	121.95 (16)	C13—C14—H14B	109.8
O1—C8—O2	122.83 (18)	S1—C14—H14B	109.8
O1—C8—C3	124.28 (18)	H14A—C14—H14B	108.3
O2—C8—C3	112.88 (16)	S1—C15—H15A	109.5
O2—C9—C10	107.31 (17)	S1—C15—H15B	109.5
O2—C9—H9A	110.3	H15A—C15—H15B	109.5
C10—C9—H9A	110.3	S1—C15—H15C	109.5
O2—C9—H9B	110.3	H15A—C15—H15C	109.5
C10—C9—H9B	110.3	H15B—C15—H15C	109.5
H9A—C9—H9B	108.5

C7—N1—C1—C2	179.65 (19)	C1—N1—C7—C13	−177.00 (17)
C7—N1—C1—C6	0.33 (19)	C6—N2—C7—N1	−0.9 (2)
N1—C1—C2—C3	−178.17 (17)	C11—N2—C7—N1	175.16 (16)
C6—C1—C2—C3	1.1 (3)	C6—N2—C7—C13	176.55 (16)
C1—C2—C3—C4	0.4 (3)	C11—N2—C7—C13	−7.4 (3)
C1—C2—C3—C8	−179.23 (16)	C9—O2—C8—O1	3.0 (3)
C2—C3—C4—C5	−1.4 (3)	C9—O2—C8—C3	−178.05 (15)
C8—C3—C4—C5	178.19 (17)	C2—C3—C8—O1	16.9 (3)
C3—C4—C5—C6	0.8 (3)	C4—C3—C8—O1	−162.71 (18)
C7—N2—C6—C5	−177.37 (19)	C2—C3—C8—O2	−162.02 (16)
C11—N2—C6—C5	6.4 (3)	C4—C3—C8—O2	18.4 (2)
C7—N2—C6—C1	1.00 (19)	C8—O2—C9—C10	−179.17 (17)
C11—N2—C6—C1	−175.20 (16)	C7—N2—C11—C12	−98.5 (2)
C4—C5—C6—N2	178.81 (18)	C6—N2—C11—C12	76.8 (2)
C4—C5—C6—C1	0.7 (3)	N2—C11—C12—O3	70.8 (2)
C2—C1—C6—N2	179.76 (16)	N1—C7—C13—C14	0.0 (3)
N1—C1—C6—N2	−0.84 (19)	N2—C7—C13—C14	−177.14 (16)
C2—C1—C6—C5	−1.7 (3)	C7—C13—C14—S1	175.48 (13)
N1—C1—C6—C5	177.72 (16)	C15—S1—C14—C13	171.67 (14)
C1—N1—C7—N2	0.3 (2)

Hydrogen-bond geometry (Å, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀N₂O₃S
M_r	308.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.3909 (1), 8.8277 (2), 11.5025 (2)
α, β, γ (°)	110.218 (1), 102.529 (1), 99.101 (1)
V (Å³)	754.78 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.27 × 0.24 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.941, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	6027, 2627, 2243
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 1.04
No. of reflections	2627
No. of parameters	196
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.844 (17)	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.

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. CrossRef Web of Science Google Scholar
Arumugam, N., Ngah, N., Abd Hamid, S. & Abdul Rahim, A. S. (2011). Acta Cryst. E67, o2938. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chou, C.-T., Yellol, G. S., Chang, W.-J., Sun, M.-L. & Sun, C.-M. (2011). Tetrahedron, 67, 2110–2117. Web of Science CrossRef CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cui, M., Ono, M., Kimura, H., Kawashima, H., Liu, B. L. & Saji, H. (2010). Nucl. Med. Biol. 38, 313–320. Web of Science CrossRef PubMed Google Scholar
Demirayak, S., Kajagil, I. & Yurttas, L. (2011). Eur. J. Med. Chem. 46, 411–416. Web of Science CrossRef CAS PubMed Google Scholar
Hamzah, N., Abd. Hamid, S., Abdul Rahim, A. S., Rosli, M. M. & Fun, H.-K. (2010). Acta Cryst. E66, o1824–o1825. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Preston, P. N. (1974). Chem. Rev. 74, 279–314. CrossRef CAS Web of Science Google Scholar
Ruiz, V. R., Corma, A. & Sabater, M. J. (2010). Tetrahedron, 66, 730–735. Web of Science CrossRef CAS Google Scholar
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. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wright, J. B. (1951). Chem. Rev. 48, 387–541. CrossRef Web of Science Google Scholar

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Volume 68| Part 1| January 2012| Pages o197-o198

doi:10.1107/S160053681105389X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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