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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1949.
Published online 2008 September 17. doi:  10.1107/S1600536808028626
PMCID: PMC2959391

2-(2-Hydroxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium acetate monohydrate

Abstract

In the title compound, C11H13N2O+·C2H3O2 ·H2O, the dihedral angle between the benzene ring and the imidazole ring is 7.83 (6)°. In the crystal structure, N—H(...)O and O—H(...)O hydrogen bonds form a two-dimensional network. All the methyl H atoms are disorderd over two sites with equal occupancies.

Related literature

For related literature, see: Maeda et al. (1984 [triangle]); Puratchikody & Doble (2007 [triangle]); Quattara et al. (1987 [triangle]); Ucucu et al. (2001 [triangle]); Scott et al. (2004 [triangle]); Seko et al. (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1949-scheme1.jpg

Experimental

Crystal data

  • C11H13N2O+·C2H3O2 ·H2O
  • M r = 266.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1949-efi1.jpg
  • a = 8.1655 (12) Å
  • b = 9.6542 (14) Å
  • c = 17.141 (3) Å
  • β = 96.374 (2)°
  • V = 1342.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 (2) K
  • 0.46 × 0.38 × 0.24 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.956, T max = 0.977
  • 8442 measured reflections
  • 2488 independent reflections
  • 1751 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.109
  • S = 1.05
  • 2488 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028626/lh2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028626/lh2684Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work is supported by the National Natural Science Foundation of China (20662007) and the Key Laboratory Open Foundation of Food Science of the Ministry of Education, Nanchang University (NCU200407).

supplementary crystallographic information

Comment

Imidazole derivatives can have a wide range of biological activities such as analgesic (Ucucu et al., 2001), antiinflammmatory (Maeda et al., 1984), antiparasitic (Quattara et al., 1987), antiepileptic and platelet aggregation inhibitors (Seko et al., 1991). The neutral imidizole component of the title compound could potentially exhibit biological activities (Puratchikody & Doble, 2007). In this paper, we report the crystal structure of the title compound (I).

In the title compound (Fig. 1), the benzene ring and the imidazole ring are approximately co-planar with a dihedral angle of 7.83 (6)° between them. The components of the salt are linked via N-H···O hydrogen bonds. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds link the components of the title compound into a two-dimensional network.

Experimental

The title compound was prepared according to a literature method (Scott et al., 2004). 1.72 g (20 mmol) butane-2,3-dione, 2.44 g (20 mmol), 4-hydroxybenzaldehyde and 5 g (>50 mmol) NH4Ac were placed in a sealed container with 100 ml CH3Cl:HAc (4:1) as the solvent and heated in a micro-wave at 350 W for 24 min. After the reaction, the solvent was evaporated. The pure product as a dark red crystalline solid was obtained by re-crystallization from hot EtOH/H2O in a yield of 81.6% and suitable for X-ray diffraction analysis.

Refinement

The water H atoms were located in a difference Fourier map and refined with idealized calculated O—H distances of 0.84Å and Uiso(H) = 1.5 Ueq(O). All other H atoms were placed at geometrically idealized positions with C—H (methyl) = 0.96 Å and C—H = 0.93Å for phenyl, N—H = 0.86 Å, and Uiso(H) = 1.2 Ueq(C,N). All methyl H atoms were refined as disorded over two sites with 0.5 occupancy.

Figures

Fig. 1.
: The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as spheres of arbitrary radii. Hydrogen bonds are shown as a dashed lines. Only ...
Fig. 2.
: Part of the crystal structure with hydrogen bonds shown as dashed lines.

Crystal data

C11H13N2O+·C2H3O2·H2OF(000) = 568
Mr = 266.29Dx = 1.317 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1719 reflections
a = 8.1655 (12) Åθ = 2.4–21.9°
b = 9.6542 (14) ŵ = 0.10 mm1
c = 17.141 (3) ÅT = 295 K
β = 96.374 (2)°Block, yellow
V = 1342.9 (3) Å30.46 × 0.38 × 0.24 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2488 independent reflections
Radiation source: fine-focus sealed tube1751 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.956, Tmax = 0.977k = −11→11
8442 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.109w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2995P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2488 reflectionsΔρmax = 0.20 e Å3
174 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0109 (16)

Special details

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)

xyzUiso*/UeqOcc. (<1)
O10.43862 (18)0.76646 (13)−0.03904 (8)0.0587 (4)
H10.50300.7086−0.05290.088*
O30.24781 (18)0.61838 (14)0.08451 (11)0.0777 (5)
O20.33771 (17)0.41072 (13)0.06150 (9)0.0600 (4)
O40.08440 (17)1.35614 (13)−0.05919 (8)0.0593 (4)
H1W0.13781.4036−0.02430.089*
H2W−0.01621.3770−0.06100.089*
N10.25223 (18)0.90693 (15)0.05447 (9)0.0435 (4)
H1D0.29380.82510.05450.052*
N20.17344 (18)1.11013 (14)0.01783 (9)0.0411 (4)
H2D0.15451.1834−0.01030.049*
C10.4058 (2)0.86127 (18)−0.09630 (11)0.0425 (4)
C20.3119 (2)0.97773 (17)−0.08056 (10)0.0385 (4)
C30.2787 (2)1.07700 (19)−0.13939 (11)0.0467 (5)
H30.21851.1555−0.12930.056*
C40.3333 (3)1.0612 (2)−0.21208 (12)0.0546 (5)
H40.30991.1282−0.25070.066*
C50.4233 (3)0.9446 (2)−0.22712 (12)0.0562 (6)
H50.45890.9326−0.27640.067*
C60.4602 (2)0.8466 (2)−0.17006 (12)0.0521 (5)
H60.52230.7695−0.18070.063*
C70.2492 (2)0.99653 (17)−0.00505 (10)0.0388 (4)
C80.1793 (2)0.96438 (19)0.11599 (11)0.0444 (5)
C90.1301 (2)1.09338 (18)0.09268 (11)0.0429 (5)
C100.1708 (3)0.8898 (2)0.19128 (12)0.0630 (6)
H10A0.21750.79910.18800.095*0.50
H10B0.05780.88180.20130.095*0.50
H10C0.23140.94050.23320.095*0.50
H10D0.12030.94850.22700.095*0.50
H10E0.28000.86580.21370.095*0.50
H10F0.10640.80710.18180.095*0.50
C110.0489 (3)1.2060 (2)0.13390 (12)0.0574 (6)
H11A0.03081.28460.09970.086*0.50
H11B0.11861.23250.18030.086*0.50
H11C−0.05471.17350.14820.086*0.50
H11D0.03231.17580.18580.086*0.50
H11E−0.05551.22790.10520.086*0.50
H11F0.11781.28690.13730.086*0.50
C120.3592 (2)0.53088 (18)0.08843 (11)0.0448 (5)
C130.5261 (3)0.5695 (2)0.12663 (14)0.0641 (6)
H13F0.60520.55990.08950.096*0.50
H13E0.55590.50970.17070.096*0.50
H13D0.52480.66380.14430.096*0.50
H13C0.51870.59570.18020.096*0.50
H13B0.56800.64590.09900.096*0.50
H13A0.59910.49180.12530.096*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0687 (10)0.0470 (8)0.0630 (9)0.0195 (7)0.0194 (8)0.0032 (7)
O30.0517 (9)0.0506 (9)0.1328 (15)0.0125 (7)0.0196 (10)0.0043 (9)
O20.0515 (9)0.0434 (8)0.0842 (11)0.0017 (6)0.0039 (7)−0.0110 (7)
O40.0526 (8)0.0550 (8)0.0698 (10)0.0083 (7)0.0045 (7)−0.0070 (7)
N10.0426 (9)0.0386 (8)0.0498 (10)0.0050 (7)0.0073 (7)0.0003 (7)
N20.0427 (9)0.0363 (8)0.0449 (9)0.0021 (7)0.0073 (7)−0.0021 (7)
C10.0399 (10)0.0394 (10)0.0482 (11)−0.0008 (8)0.0054 (9)−0.0036 (8)
C20.0358 (10)0.0358 (9)0.0443 (11)−0.0021 (7)0.0061 (8)−0.0057 (8)
C30.0444 (11)0.0444 (11)0.0513 (12)0.0015 (8)0.0054 (9)−0.0031 (9)
C40.0615 (13)0.0566 (12)0.0460 (12)−0.0016 (10)0.0074 (10)0.0015 (9)
C50.0599 (13)0.0641 (13)0.0463 (12)−0.0030 (11)0.0128 (10)−0.0110 (10)
C60.0529 (12)0.0492 (11)0.0558 (13)0.0038 (9)0.0130 (10)−0.0116 (10)
C70.0350 (10)0.0362 (9)0.0451 (11)0.0007 (7)0.0044 (8)−0.0042 (8)
C80.0411 (11)0.0474 (11)0.0455 (11)−0.0026 (8)0.0078 (9)−0.0026 (9)
C90.0387 (10)0.0456 (11)0.0452 (11)−0.0028 (8)0.0080 (8)−0.0074 (8)
C100.0687 (15)0.0692 (14)0.0525 (13)0.0011 (11)0.0132 (11)0.0092 (10)
C110.0586 (13)0.0541 (12)0.0624 (13)−0.0034 (10)0.0197 (11)−0.0159 (10)
C120.0430 (11)0.0398 (11)0.0532 (12)0.0012 (9)0.0117 (9)0.0049 (9)
C130.0551 (14)0.0678 (14)0.0682 (15)−0.0103 (11)0.0010 (11)−0.0017 (12)

Geometric parameters (Å, °)

O1—C11.347 (2)C8—C91.355 (2)
O1—H10.8200C8—C101.486 (3)
O3—C121.238 (2)C9—C111.492 (2)
O2—C121.254 (2)C10—H10A0.9600
O4—H1W0.8364C10—H10B0.9600
O4—H2W0.8428C10—H10C0.9600
N1—C71.336 (2)C10—H10D0.9600
N1—C81.383 (2)C10—H10E0.9600
N1—H1D0.8600C10—H10F0.9600
N2—C71.339 (2)C11—H11A0.9600
N2—C91.378 (2)C11—H11B0.9600
N2—H2D0.8600C11—H11C0.9600
C1—C61.393 (3)C11—H11D0.9600
C1—C21.404 (2)C11—H11E0.9600
C2—C31.396 (2)C11—H11F0.9600
C2—C71.455 (2)C12—C131.493 (3)
C3—C41.377 (3)C13—H13F0.9600
C3—H30.9300C13—H13E0.9600
C4—C51.384 (3)C13—H13D0.9600
C4—H40.9300C13—H13C0.9600
C5—C61.370 (3)C13—H13B0.9600
C5—H50.9300C13—H13A0.9600
C6—H60.9300
C1—O1—H1109.5H10A—C10—H10F56.3
H1W—O4—H2W108.9H10B—C10—H10F56.3
C7—N1—C8110.46 (14)H10C—C10—H10F141.1
C7—N1—H1D124.7H10D—C10—H10F109.5
C8—N1—H1D124.8H10E—C10—H10F109.5
C7—N2—C9110.57 (14)C9—C11—H11A109.5
C7—N2—H2D124.7C9—C11—H11B109.5
C9—N2—H2D124.7H11A—C11—H11B109.5
O1—C1—C6122.33 (16)C9—C11—H11C109.5
O1—C1—C2118.22 (16)H11A—C11—H11C109.5
C6—C1—C2119.44 (17)H11B—C11—H11C109.5
C3—C2—C1118.52 (16)C9—C11—H11D109.5
C3—C2—C7119.85 (15)H11A—C11—H11D141.1
C1—C2—C7121.63 (16)H11B—C11—H11D56.3
C4—C3—C2121.41 (18)H11C—C11—H11D56.3
C4—C3—H3119.3C9—C11—H11E109.5
C2—C3—H3119.3H11A—C11—H11E56.3
C3—C4—C5119.36 (19)H11B—C11—H11E141.1
C3—C4—H4120.3H11C—C11—H11E56.3
C5—C4—H4120.3H11D—C11—H11E109.5
C6—C5—C4120.52 (18)C9—C11—H11F109.5
C6—C5—H5119.7H11A—C11—H11F56.3
C4—C5—H5119.7H11B—C11—H11F56.3
C5—C6—C1120.73 (18)H11C—C11—H11F141.1
C5—C6—H6119.6H11D—C11—H11F109.5
C1—C6—H6119.6H11E—C11—H11F109.5
N1—C7—N2106.06 (15)O3—C12—O2122.65 (19)
N1—C7—C2128.32 (15)O3—C12—C13118.89 (18)
N2—C7—C2125.61 (16)O2—C12—C13118.46 (17)
C9—C8—N1106.41 (15)C12—C13—H13F109.5
C9—C8—C10131.30 (17)C12—C13—H13E109.5
N1—C8—C10122.25 (16)H13F—C13—H13E109.5
C8—C9—N2106.49 (15)C12—C13—H13D109.5
C8—C9—C11131.55 (17)H13F—C13—H13D109.5
N2—C9—C11121.95 (17)H13E—C13—H13D109.5
C8—C10—H10A109.5C12—C13—H13C109.5
C8—C10—H10B109.5H13F—C13—H13C141.1
H10A—C10—H10B109.5H13E—C13—H13C56.3
C8—C10—H10C109.5H13D—C13—H13C56.3
H10A—C10—H10C109.5C12—C13—H13B109.5
H10B—C10—H10C109.5H13F—C13—H13B56.3
C8—C10—H10D109.5H13E—C13—H13B141.1
H10A—C10—H10D141.1H13D—C13—H13B56.3
H10B—C10—H10D56.3H13C—C13—H13B109.5
H10C—C10—H10D56.3C12—C13—H13A109.5
C8—C10—H10E109.5H13F—C13—H13A56.3
H10A—C10—H10E56.3H13E—C13—H13A56.3
H10B—C10—H10E141.1H13D—C13—H13A141.1
H10C—C10—H10E56.3H13C—C13—H13A109.5
H10D—C10—H10E109.5H13B—C13—H13A109.5
C8—C10—H10F109.5
O1—C1—C2—C3179.44 (16)C9—N2—C7—C2−179.93 (16)
C6—C1—C2—C3−1.2 (3)C3—C2—C7—N1171.82 (17)
O1—C1—C2—C7−0.6 (3)C1—C2—C7—N1−8.1 (3)
C6—C1—C2—C7178.69 (16)C3—C2—C7—N2−7.3 (3)
C1—C2—C3—C41.3 (3)C1—C2—C7—N2172.81 (16)
C7—C2—C3—C4−178.65 (17)C7—N1—C8—C90.1 (2)
C2—C3—C4—C5−0.2 (3)C7—N1—C8—C10−177.72 (17)
C3—C4—C5—C6−1.0 (3)N1—C8—C9—N20.34 (19)
C4—C5—C6—C11.1 (3)C10—C8—C9—N2177.9 (2)
O1—C1—C6—C5179.40 (18)N1—C8—C9—C11−178.04 (19)
C2—C1—C6—C50.1 (3)C10—C8—C9—C11−0.4 (4)
C8—N1—C7—N2−0.59 (19)C7—N2—C9—C8−0.7 (2)
C8—N1—C7—C2−179.82 (17)C7—N2—C9—C11177.84 (17)
C9—N2—C7—N10.82 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2D···O40.861.932.7747 (19)169.
N1—H1D···O10.862.172.6956 (19)119.
N1—H1D···O30.862.102.834 (2)142.
O4—H2W···O3i0.841.892.710 (2)164.
O4—H1W···O2ii0.842.072.808 (2)146.
O1—H1···O2iii0.821.762.5624 (18)167.

Symmetry codes: (i) −x, −y+2, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2684).

References

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  • Scott, E. W., David, D. W., William, H. L., Yi, W., Zhijian, Z. & Craig, W. L. (2004). Org. Lett.6, 1453–1456. [PubMed]
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