organic compounds
Ethyl 1-sec-butyl-2-(2-hydroxyphenyl)-1H-benzimidazole-5-carboxylate 0.25-hydrate
aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the title compound, C20H22N2O3·0.25H2O, the water molecule (occupancy 0.25) is disordered across a crystallographic inversion center. The dihedral angle between the hydroxyphenyl ring and the benzimidazole ring system is 59.31 (9)°. In the molecules are connected by intermolecular O—H⋯N and C—H⋯O hydrogen bonds. The is further stabilized by a weak C—H⋯π interaction involving the imidazole ring.
Related literature
For background to benzimidazoles and their biological importance, see: Garuti et al. (2004); Bonfanti et al. (2008); Ozden et al. (2008); Shao et al. (2005); Blythin et al. (1986); Snow (2007). For the synthesis of benzimidazoles, see: Arumugam et al. (2010a,b,c). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S1600536810015448/sj2770sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015448/sj2770Isup2.hkl
The title compound was synthesised according to the previous procedure described by us (Arumugam et al., 2010a,b,c). The product was recrystallized from EtOAc to yield the title compound as colourless crystals.
All hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.97Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. In the final
cycles the occupancy of the water molecule, O1W, which is disordered over a crystallographic inversion centre, was fixed at 25%.Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activity such as antitumour (Garuti et al., 2004), antiviral (Bonfanti et al., 2008), antibacterial (Ozden et al., 2008) and analgesic properties (Shao et al., 2005). These derivatives are anti-inflammatory (Blythin et al., 1986) and can be carcinogenic (Snow et al., 2007). As the benzimidazole derivative is of much importance, we have undertaken the X-ray
determination of the title compound.The
(Fig. 1) contains an ethyl-1-sec-butyl-2- (2-hydroxyphenyl)-1H-benzimidazole-5-carboxylate molecule and a water molecule(O1W), occupancy 0.25, which is disordered across a crystallographic inversion center (symmetry code = -x, -y+2, -z+1). The dihedral angle between the benzimidazole ring system (N1–N2/C1–C7) and the phenyl ring (C15–C20) is 59.31 (9)° .In the π interactions (Table 1), involving the imidazole ring, N1–N2/C1–C2/C7 (centroid Cg1).
(Fig. 2), molecules are connected by intermolecular O1—H1O1···N1 and C14—H14C···O1 (Table 1) hydrogen bonds. The is further stabilized by C—H···For background to and the biological importance of benimidazoles, see: Garuti et al. (2004); Bonfanti et al. (2008); Ozden et al. (2008); Shao et al. (2005); Blythin et al. (1986); Snow (2007). For the synthesis of benzimidazoles, see: Arumugam et al. (2010a,b,c). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell
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).C20H22N2O3·0.25H2O | F(000) = 730 |
Mr = 342.90 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3454 reflections |
a = 7.0484 (11) Å | θ = 2.6–28.6° |
b = 27.262 (4) Å | µ = 0.09 mm−1 |
c = 9.4673 (14) Å | T = 100 K |
β = 97.495 (3)° | Plate, colourless |
V = 1803.6 (5) Å3 | 0.34 × 0.21 × 0.05 mm |
Z = 4 |
Bruker APEX DUO CCD area-detector diffractometer | 4738 independent reflections |
Radiation source: fine-focus sealed tube | 3152 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 29.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.971, Tmax = 0.996 | k = −37→36 |
18277 measured reflections | l = −12→12 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.232 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1283P)2 + 0.731P] where P = (Fo2 + 2Fc2)/3 |
4738 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C20H22N2O3·0.25H2O | V = 1803.6 (5) Å3 |
Mr = 342.90 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.0484 (11) Å | µ = 0.09 mm−1 |
b = 27.262 (4) Å | T = 100 K |
c = 9.4673 (14) Å | 0.34 × 0.21 × 0.05 mm |
β = 97.495 (3)° |
Bruker APEX DUO CCD area-detector diffractometer | 4738 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3152 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.996 | Rint = 0.064 |
18277 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.232 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.35 e Å−3 |
4738 reflections | Δρmin = −0.46 e Å−3 |
243 parameters |
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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.3724 (2) | 0.72773 (6) | 0.28243 (18) | 0.0229 (4) | |
O2 | −0.2905 (3) | 0.97944 (7) | −0.0919 (2) | 0.0330 (5) | |
O3 | −0.1402 (3) | 0.95244 (8) | −0.2726 (2) | 0.0416 (5) | |
N1 | 0.3512 (3) | 0.83123 (7) | 0.0078 (2) | 0.0194 (4) | |
N2 | 0.3227 (3) | 0.83949 (7) | 0.2392 (2) | 0.0198 (4) | |
C1 | 0.4138 (3) | 0.81661 (8) | 0.1391 (2) | 0.0185 (4) | |
C2 | 0.1912 (3) | 0.87134 (8) | 0.1673 (2) | 0.0200 (5) | |
C3 | 0.0594 (3) | 0.90402 (10) | 0.2134 (3) | 0.0257 (5) | |
H3A | 0.0478 | 0.9080 | 0.3095 | 0.031* | |
C4 | −0.0530 (3) | 0.93018 (9) | 0.1083 (3) | 0.0258 (5) | |
H4A | −0.1424 | 0.9523 | 0.1349 | 0.031* | |
C5 | −0.0366 (3) | 0.92453 (9) | −0.0362 (3) | 0.0243 (5) | |
C6 | 0.0965 (3) | 0.89227 (9) | −0.0812 (3) | 0.0220 (5) | |
H6A | 0.1090 | 0.8886 | −0.1772 | 0.026* | |
C7 | 0.2102 (3) | 0.86571 (8) | 0.0232 (2) | 0.0191 (5) | |
C8 | −0.1585 (4) | 0.95277 (10) | −0.1479 (3) | 0.0284 (5) | |
C9 | −0.4223 (4) | 1.00752 (11) | −0.1914 (3) | 0.0356 (6) | |
H9A | −0.3573 | 1.0187 | −0.2697 | 0.043* | |
H9B | −0.4652 | 1.0362 | −0.1437 | 0.043* | |
C10 | −0.5894 (4) | 0.97724 (12) | −0.2473 (4) | 0.0468 (8) | |
H10A | −0.6797 | 0.9970 | −0.3072 | 0.070* | |
H10B | −0.6490 | 0.9646 | −0.1694 | 0.070* | |
H10C | −0.5481 | 0.9505 | −0.3018 | 0.070* | |
C11 | 0.3656 (3) | 0.83308 (9) | 0.3956 (2) | 0.0231 (5) | |
H11A | 0.4583 | 0.8063 | 0.4127 | 0.028* | |
C12 | 0.4596 (4) | 0.87887 (10) | 0.4644 (3) | 0.0286 (5) | |
H12A | 0.3742 | 0.9066 | 0.4430 | 0.034* | |
H12B | 0.4790 | 0.8745 | 0.5669 | 0.034* | |
C13 | 0.6503 (4) | 0.89027 (11) | 0.4137 (3) | 0.0350 (6) | |
H13A | 0.7075 | 0.9181 | 0.4648 | 0.053* | |
H13B | 0.6305 | 0.8975 | 0.3136 | 0.053* | |
H13C | 0.7336 | 0.8624 | 0.4305 | 0.053* | |
C14 | 0.1872 (3) | 0.81788 (11) | 0.4596 (3) | 0.0314 (6) | |
H14A | 0.1249 | 0.7914 | 0.4050 | 0.047* | |
H14B | 0.1013 | 0.8453 | 0.4580 | 0.047* | |
H14C | 0.2228 | 0.8074 | 0.5562 | 0.047* | |
C15 | 0.5701 (3) | 0.78084 (8) | 0.1704 (2) | 0.0187 (5) | |
C16 | 0.7463 (3) | 0.79107 (9) | 0.1229 (3) | 0.0217 (5) | |
H16A | 0.7627 | 0.8203 | 0.0753 | 0.026* | |
C17 | 0.8956 (3) | 0.75806 (10) | 0.1464 (3) | 0.0262 (5) | |
H17A | 1.0132 | 0.7653 | 0.1167 | 0.031* | |
C18 | 0.8696 (3) | 0.71439 (10) | 0.2137 (3) | 0.0259 (5) | |
H18A | 0.9697 | 0.6920 | 0.2282 | 0.031* | |
C19 | 0.6961 (3) | 0.70333 (9) | 0.2606 (3) | 0.0228 (5) | |
H19A | 0.6800 | 0.6736 | 0.3056 | 0.027* | |
C20 | 0.5463 (3) | 0.73679 (9) | 0.2401 (2) | 0.0195 (5) | |
H1O1 | 0.382 (5) | 0.7052 (13) | 0.361 (4) | 0.048 (10)* | |
O1W | 0.0628 (16) | 0.9740 (3) | 0.4867 (10) | 0.055 (3) | 0.25 |
H1W1 | −0.0325 | 0.9804 | 0.4320 | 0.083* | 0.25 |
H2W1 | 0.1385 | 0.9962 | 0.4785 | 0.083* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0148 (7) | 0.0317 (9) | 0.0230 (9) | −0.0007 (6) | 0.0046 (6) | 0.0064 (7) |
O2 | 0.0285 (9) | 0.0373 (11) | 0.0324 (10) | 0.0122 (8) | 0.0006 (8) | 0.0084 (8) |
O3 | 0.0423 (12) | 0.0533 (13) | 0.0275 (11) | 0.0139 (10) | −0.0021 (9) | 0.0073 (9) |
N1 | 0.0160 (8) | 0.0256 (10) | 0.0167 (9) | −0.0001 (7) | 0.0026 (7) | −0.0001 (7) |
N2 | 0.0157 (8) | 0.0273 (10) | 0.0164 (9) | 0.0032 (7) | 0.0013 (7) | 0.0018 (7) |
C1 | 0.0149 (9) | 0.0238 (11) | 0.0169 (11) | −0.0005 (8) | 0.0024 (7) | 0.0014 (8) |
C2 | 0.0156 (10) | 0.0261 (12) | 0.0180 (11) | 0.0011 (8) | 0.0010 (8) | 0.0021 (8) |
C3 | 0.0202 (11) | 0.0323 (13) | 0.0247 (12) | 0.0062 (9) | 0.0039 (9) | 0.0006 (10) |
C4 | 0.0194 (11) | 0.0302 (13) | 0.0281 (13) | 0.0060 (9) | 0.0034 (9) | 0.0020 (10) |
C5 | 0.0211 (11) | 0.0251 (12) | 0.0255 (12) | 0.0014 (9) | −0.0016 (9) | 0.0034 (9) |
C6 | 0.0222 (11) | 0.0259 (12) | 0.0175 (11) | −0.0005 (9) | 0.0012 (8) | 0.0013 (9) |
C7 | 0.0152 (9) | 0.0223 (11) | 0.0197 (11) | −0.0006 (8) | 0.0013 (8) | 0.0006 (8) |
C8 | 0.0259 (12) | 0.0295 (13) | 0.0285 (13) | 0.0034 (10) | −0.0012 (10) | 0.0046 (10) |
C9 | 0.0289 (13) | 0.0371 (15) | 0.0392 (16) | 0.0106 (11) | −0.0018 (11) | 0.0118 (12) |
C10 | 0.0392 (16) | 0.0443 (18) | 0.054 (2) | 0.0057 (13) | −0.0043 (14) | −0.0063 (15) |
C11 | 0.0211 (10) | 0.0331 (13) | 0.0153 (11) | 0.0045 (9) | 0.0034 (8) | 0.0030 (9) |
C12 | 0.0278 (12) | 0.0352 (14) | 0.0226 (12) | 0.0057 (10) | 0.0020 (9) | −0.0015 (10) |
C13 | 0.0280 (13) | 0.0375 (15) | 0.0375 (16) | −0.0050 (11) | −0.0034 (11) | −0.0039 (12) |
C14 | 0.0234 (12) | 0.0494 (16) | 0.0225 (13) | 0.0021 (11) | 0.0066 (9) | 0.0076 (11) |
C15 | 0.0164 (10) | 0.0239 (11) | 0.0157 (10) | −0.0001 (8) | 0.0019 (8) | −0.0010 (8) |
C16 | 0.0177 (10) | 0.0280 (12) | 0.0200 (11) | −0.0010 (9) | 0.0050 (8) | 0.0018 (9) |
C17 | 0.0162 (10) | 0.0388 (14) | 0.0245 (12) | 0.0029 (9) | 0.0060 (9) | −0.0011 (10) |
C18 | 0.0201 (11) | 0.0334 (13) | 0.0245 (12) | 0.0069 (9) | 0.0042 (9) | 0.0005 (10) |
C19 | 0.0228 (11) | 0.0267 (12) | 0.0189 (11) | 0.0025 (9) | 0.0026 (8) | 0.0011 (9) |
C20 | 0.0151 (10) | 0.0279 (12) | 0.0157 (10) | −0.0006 (8) | 0.0030 (7) | −0.0011 (8) |
O1W | 0.099 (8) | 0.032 (4) | 0.046 (5) | −0.004 (5) | 0.052 (6) | 0.000 (4) |
O1—C20 | 1.361 (3) | C10—H10C | 0.9600 |
O1—H1O1 | 0.96 (4) | C11—C12 | 1.519 (4) |
O2—C8 | 1.343 (3) | C11—C14 | 1.523 (3) |
O2—C9 | 1.452 (3) | C11—H11A | 0.9800 |
O3—C8 | 1.204 (3) | C12—C13 | 1.518 (4) |
N1—C1 | 1.325 (3) | C12—H12A | 0.9700 |
N1—C7 | 1.389 (3) | C12—H12B | 0.9700 |
N2—C1 | 1.363 (3) | C13—H13A | 0.9600 |
N2—C2 | 1.383 (3) | C13—H13B | 0.9600 |
N2—C11 | 1.483 (3) | C13—H13C | 0.9600 |
C1—C15 | 1.472 (3) | C14—H14A | 0.9600 |
C2—C7 | 1.396 (3) | C14—H14B | 0.9600 |
C2—C3 | 1.397 (3) | C14—H14C | 0.9600 |
C3—C4 | 1.386 (3) | C15—C20 | 1.391 (3) |
C3—H3A | 0.9300 | C15—C16 | 1.403 (3) |
C4—C5 | 1.396 (4) | C16—C17 | 1.380 (3) |
C4—H4A | 0.9300 | C16—H16A | 0.9300 |
C5—C6 | 1.393 (3) | C17—C18 | 1.374 (4) |
C5—C8 | 1.487 (3) | C17—H17A | 0.9300 |
C6—C7 | 1.392 (3) | C18—C19 | 1.388 (3) |
C6—H6A | 0.9300 | C18—H18A | 0.9300 |
C9—C10 | 1.479 (4) | C19—C20 | 1.389 (3) |
C9—H9A | 0.9700 | C19—H19A | 0.9300 |
C9—H9B | 0.9700 | O1W—O1Wi | 1.708 (18) |
C10—H10A | 0.9600 | O1W—H1W1 | 0.8114 |
C10—H10B | 0.9600 | O1W—H2W1 | 0.8187 |
C20—O1—H1O1 | 112 (2) | C12—C11—C14 | 112.9 (2) |
C8—O2—C9 | 116.6 (2) | N2—C11—H11A | 107.4 |
C1—N1—C7 | 105.09 (19) | C12—C11—H11A | 107.4 |
C1—N2—C2 | 106.95 (19) | C14—C11—H11A | 107.4 |
C1—N2—C11 | 125.96 (18) | C13—C12—C11 | 112.8 (2) |
C2—N2—C11 | 127.02 (19) | C13—C12—H12A | 109.0 |
N1—C1—N2 | 112.65 (19) | C11—C12—H12A | 109.0 |
N1—C1—C15 | 122.5 (2) | C13—C12—H12B | 109.0 |
N2—C1—C15 | 124.82 (19) | C11—C12—H12B | 109.0 |
N2—C2—C7 | 105.54 (19) | H12A—C12—H12B | 107.8 |
N2—C2—C3 | 132.6 (2) | C12—C13—H13A | 109.5 |
C7—C2—C3 | 121.9 (2) | C12—C13—H13B | 109.5 |
C4—C3—C2 | 116.4 (2) | H13A—C13—H13B | 109.5 |
C4—C3—H3A | 121.8 | C12—C13—H13C | 109.5 |
C2—C3—H3A | 121.8 | H13A—C13—H13C | 109.5 |
C3—C4—C5 | 122.3 (2) | H13B—C13—H13C | 109.5 |
C3—C4—H4A | 118.8 | C11—C14—H14A | 109.5 |
C5—C4—H4A | 118.8 | C11—C14—H14B | 109.5 |
C6—C5—C4 | 120.9 (2) | H14A—C14—H14B | 109.5 |
C6—C5—C8 | 117.4 (2) | C11—C14—H14C | 109.5 |
C4—C5—C8 | 121.7 (2) | H14A—C14—H14C | 109.5 |
C7—C6—C5 | 117.4 (2) | H14B—C14—H14C | 109.5 |
C7—C6—H6A | 121.3 | C20—C15—C16 | 119.4 (2) |
C5—C6—H6A | 121.3 | C20—C15—C1 | 122.27 (19) |
N1—C7—C6 | 129.1 (2) | C16—C15—C1 | 118.3 (2) |
N1—C7—C2 | 109.77 (19) | C17—C16—C15 | 120.5 (2) |
C6—C7—C2 | 121.1 (2) | C17—C16—H16A | 119.8 |
O3—C8—O2 | 124.0 (2) | C15—C16—H16A | 119.8 |
O3—C8—C5 | 124.6 (2) | C18—C17—C16 | 119.6 (2) |
O2—C8—C5 | 111.4 (2) | C18—C17—H17A | 120.2 |
O2—C9—C10 | 110.5 (2) | C16—C17—H17A | 120.2 |
O2—C9—H9A | 109.5 | C17—C18—C19 | 120.9 (2) |
C10—C9—H9A | 109.5 | C17—C18—H18A | 119.6 |
O2—C9—H9B | 109.5 | C19—C18—H18A | 119.6 |
C10—C9—H9B | 109.5 | C18—C19—C20 | 119.9 (2) |
H9A—C9—H9B | 108.1 | C18—C19—H19A | 120.1 |
C9—C10—H10A | 109.5 | C20—C19—H19A | 120.1 |
C9—C10—H10B | 109.5 | O1—C20—C19 | 122.5 (2) |
H10A—C10—H10B | 109.5 | O1—C20—C15 | 117.73 (19) |
C9—C10—H10C | 109.5 | C19—C20—C15 | 119.8 (2) |
H10A—C10—H10C | 109.5 | O1Wi—O1W—H1W1 | 60.9 |
H10B—C10—H10C | 109.5 | O1Wi—O1W—H2W1 | 75.8 |
N2—C11—C12 | 110.6 (2) | H1W1—O1W—H2W1 | 106.0 |
N2—C11—C14 | 110.99 (19) | ||
C7—N1—C1—N2 | −0.1 (2) | C6—C5—C8—O3 | −5.9 (4) |
C7—N1—C1—C15 | −178.0 (2) | C4—C5—C8—O3 | 173.6 (3) |
C2—N2—C1—N1 | 0.0 (3) | C6—C5—C8—O2 | 175.0 (2) |
C11—N2—C1—N1 | −176.9 (2) | C4—C5—C8—O2 | −5.5 (3) |
C2—N2—C1—C15 | 177.8 (2) | C8—O2—C9—C10 | 87.3 (3) |
C11—N2—C1—C15 | 0.8 (4) | C1—N2—C11—C12 | 109.2 (2) |
C1—N2—C2—C7 | 0.1 (2) | C2—N2—C11—C12 | −67.2 (3) |
C11—N2—C2—C7 | 177.0 (2) | C1—N2—C11—C14 | −124.7 (2) |
C1—N2—C2—C3 | −179.9 (3) | C2—N2—C11—C14 | 59.0 (3) |
C11—N2—C2—C3 | −2.9 (4) | N2—C11—C12—C13 | −62.2 (3) |
N2—C2—C3—C4 | −179.3 (2) | C14—C11—C12—C13 | 172.8 (2) |
C7—C2—C3—C4 | 0.7 (4) | N1—C1—C15—C20 | −121.4 (2) |
C2—C3—C4—C5 | −0.1 (4) | N2—C1—C15—C20 | 61.0 (3) |
C3—C4—C5—C6 | −0.6 (4) | N1—C1—C15—C16 | 56.0 (3) |
C3—C4—C5—C8 | 179.9 (2) | N2—C1—C15—C16 | −121.5 (2) |
C4—C5—C6—C7 | 0.7 (3) | C20—C15—C16—C17 | −0.7 (3) |
C8—C5—C6—C7 | −179.8 (2) | C1—C15—C16—C17 | −178.3 (2) |
C1—N1—C7—C6 | −179.3 (2) | C15—C16—C17—C18 | 1.5 (4) |
C1—N1—C7—C2 | 0.2 (2) | C16—C17—C18—C19 | −1.0 (4) |
C5—C6—C7—N1 | 179.4 (2) | C17—C18—C19—C20 | −0.4 (4) |
C5—C6—C7—C2 | −0.1 (3) | C18—C19—C20—O1 | 179.3 (2) |
N2—C2—C7—N1 | −0.2 (2) | C18—C19—C20—C15 | 1.2 (4) |
C3—C2—C7—N1 | 179.8 (2) | C16—C15—C20—O1 | −178.9 (2) |
N2—C2—C7—C6 | 179.3 (2) | C1—C15—C20—O1 | −1.4 (3) |
C3—C2—C7—C6 | −0.7 (4) | C16—C15—C20—C19 | −0.6 (3) |
C9—O2—C8—O3 | 2.8 (4) | C1—C15—C20—C19 | 176.8 (2) |
C9—O2—C8—C5 | −178.2 (2) |
Symmetry code: (i) −x, −y+2, −z+1. |
Cg1 is the centroid of the N1,N2,C1,C2,N7 imidazole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1ii | 0.96 (4) | 1.75 (4) | 2.691 (3) | 168 (3) |
C14—H14C···O1ii | 0.96 | 2.45 | 3.398 (3) | 168 |
C17—H17A···Cg1iii | 0.93 | 2.96 | 3.734 (3) | 142 |
Symmetry codes: (ii) x, −y+3/2, z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H22N2O3·0.25H2O |
Mr | 342.90 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.0484 (11), 27.262 (4), 9.4673 (14) |
β (°) | 97.495 (3) |
V (Å3) | 1803.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.34 × 0.21 × 0.05 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.971, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18277, 4738, 3152 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.232, 1.08 |
No. of reflections | 4738 |
No. of parameters | 243 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.46 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the N1,N2,C1,C2,N7 imidazole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1i | 0.96 (4) | 1.75 (4) | 2.691 (3) | 168 (3) |
C14—H14C···O1i | 0.9600 | 2.4500 | 3.398 (3) | 167.60 |
C17—H17A···Cg1ii | 0.9300 | 2.9600 | 3.734 (3) | 142.00 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, y, z. |
Acknowledgements
NA, ASAR and HO acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under Research University Grant (1001/PFARMASI/815026). NA also thanks USM for the award of postdoctoral fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012 and MH also thanks USM for a post-doctoral research fellowship.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activity such as antitumour (Garuti et al., 2004), antiviral (Bonfanti et al., 2008), antibacterial (Ozden et al., 2008) and analgesic properties (Shao et al., 2005). These derivatives are anti-inflammatory (Blythin et al., 1986) and can be carcinogenic (Snow et al., 2007). As the benzimidazole derivative is of much importance, we have undertaken the X-ray crystal structure determination of the title compound.
The asymmetric unit (Fig. 1) contains an ethyl-1-sec-butyl-2- (2-hydroxyphenyl)-1H-benzimidazole-5-carboxylate molecule and a water molecule(O1W), occupancy 0.25, which is disordered across a crystallographic inversion center (symmetry code = -x, -y+2, -z+1). The dihedral angle between the benzimidazole ring system (N1–N2/C1–C7) and the phenyl ring (C15–C20) is 59.31 (9)° .
In the crystal structure (Fig. 2), molecules are connected by intermolecular O1—H1O1···N1 and C14—H14C···O1 (Table 1) hydrogen bonds. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the imidazole ring, N1–N2/C1–C2/C7 (centroid Cg1).