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

In the title compound, C(11)H(13)N(2)O(+)·C(2)H(3)O(2) (-)·H(2)O, 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 ▶); Puratchikody & Doble (2007 ▶); Quattara et al. (1987 ▶); Ucucu et al. (2001 ▶); Scott et al. (2004 ▶); Seko et al. (1991 ▶).

Experimental

Crystal data

C11H13N2O+·C2H3O2 −·H2O

M = 266.29

Monoclinic,

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

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

C11H13N2O+·C2H3O2−·H2O	F(000) = 568
Mr = 266.29	Dx = 1.317 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1719 reflections
a = 8.1655 (12) Å	θ = 2.4–21.9°
b = 9.6542 (14) Å	µ = 0.10 mm−1
c = 17.141 (3) Å	T = 295 K
β = 96.374 (2)°	Block, yellow
V = 1342.9 (3) Å3	0.46 × 0.38 × 0.24 mm
Z = 4

Bruker SMART CCD diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1751 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.956, Tmax = 0.977	k = −11→11
8442 measured reflections	l = −20→20

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

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.43862 (18)	0.76646 (13)	−0.03904 (8)	0.0587 (4)
H1	0.5030	0.7086	−0.0529	0.088*
O3	0.24781 (18)	0.61838 (14)	0.08451 (11)	0.0777 (5)
O2	0.33771 (17)	0.41072 (13)	0.06150 (9)	0.0600 (4)
O4	0.08440 (17)	1.35614 (13)	−0.05919 (8)	0.0593 (4)
H1W	0.1378	1.4036	−0.0243	0.089*
H2W	−0.0162	1.3770	−0.0610	0.089*
N1	0.25223 (18)	0.90693 (15)	0.05447 (9)	0.0435 (4)
H1D	0.2938	0.8251	0.0545	0.052*
N2	0.17344 (18)	1.11013 (14)	0.01783 (9)	0.0411 (4)
H2D	0.1545	1.1834	−0.0103	0.049*
C1	0.4058 (2)	0.86127 (18)	−0.09630 (11)	0.0425 (4)
C2	0.3119 (2)	0.97773 (17)	−0.08056 (10)	0.0385 (4)
C3	0.2787 (2)	1.07700 (19)	−0.13939 (11)	0.0467 (5)
H3	0.2185	1.1555	−0.1293	0.056*
C4	0.3333 (3)	1.0612 (2)	−0.21208 (12)	0.0546 (5)
H4	0.3099	1.1282	−0.2507	0.066*
C5	0.4233 (3)	0.9446 (2)	−0.22712 (12)	0.0562 (6)
H5	0.4589	0.9326	−0.2764	0.067*
C6	0.4602 (2)	0.8466 (2)	−0.17006 (12)	0.0521 (5)
H6	0.5223	0.7695	−0.1807	0.063*
C7	0.2492 (2)	0.99653 (17)	−0.00505 (10)	0.0388 (4)
C8	0.1793 (2)	0.96438 (19)	0.11599 (11)	0.0444 (5)
C9	0.1301 (2)	1.09338 (18)	0.09268 (11)	0.0429 (5)
C10	0.1708 (3)	0.8898 (2)	0.19128 (12)	0.0630 (6)
H10A	0.2175	0.7991	0.1880	0.095*	0.50
H10B	0.0578	0.8818	0.2013	0.095*	0.50
H10C	0.2314	0.9405	0.2332	0.095*	0.50
H10D	0.1203	0.9485	0.2270	0.095*	0.50
H10E	0.2800	0.8658	0.2137	0.095*	0.50
H10F	0.1064	0.8071	0.1818	0.095*	0.50
C11	0.0489 (3)	1.2060 (2)	0.13390 (12)	0.0574 (6)
H11A	0.0308	1.2846	0.0997	0.086*	0.50
H11B	0.1186	1.2325	0.1803	0.086*	0.50
H11C	−0.0547	1.1735	0.1482	0.086*	0.50
H11D	0.0323	1.1758	0.1858	0.086*	0.50
H11E	−0.0555	1.2279	0.1052	0.086*	0.50
H11F	0.1178	1.2869	0.1373	0.086*	0.50
C12	0.3592 (2)	0.53088 (18)	0.08843 (11)	0.0448 (5)
C13	0.5261 (3)	0.5695 (2)	0.12663 (14)	0.0641 (6)
H13F	0.6052	0.5599	0.0895	0.096*	0.50
H13E	0.5559	0.5097	0.1707	0.096*	0.50
H13D	0.5248	0.6638	0.1443	0.096*	0.50
H13C	0.5187	0.5957	0.1802	0.096*	0.50
H13B	0.5680	0.6459	0.0990	0.096*	0.50
H13A	0.5991	0.4918	0.1253	0.096*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0687 (10)	0.0470 (8)	0.0630 (9)	0.0195 (7)	0.0194 (8)	0.0032 (7)
O3	0.0517 (9)	0.0506 (9)	0.1328 (15)	0.0125 (7)	0.0196 (10)	0.0043 (9)
O2	0.0515 (9)	0.0434 (8)	0.0842 (11)	0.0017 (6)	0.0039 (7)	−0.0110 (7)
O4	0.0526 (8)	0.0550 (8)	0.0698 (10)	0.0083 (7)	0.0045 (7)	−0.0070 (7)
N1	0.0426 (9)	0.0386 (8)	0.0498 (10)	0.0050 (7)	0.0073 (7)	0.0003 (7)
N2	0.0427 (9)	0.0363 (8)	0.0449 (9)	0.0021 (7)	0.0073 (7)	−0.0021 (7)
C1	0.0399 (10)	0.0394 (10)	0.0482 (11)	−0.0008 (8)	0.0054 (9)	−0.0036 (8)
C2	0.0358 (10)	0.0358 (9)	0.0443 (11)	−0.0021 (7)	0.0061 (8)	−0.0057 (8)
C3	0.0444 (11)	0.0444 (11)	0.0513 (12)	0.0015 (8)	0.0054 (9)	−0.0031 (9)
C4	0.0615 (13)	0.0566 (12)	0.0460 (12)	−0.0016 (10)	0.0074 (10)	0.0015 (9)
C5	0.0599 (13)	0.0641 (13)	0.0463 (12)	−0.0030 (11)	0.0128 (10)	−0.0110 (10)
C6	0.0529 (12)	0.0492 (11)	0.0558 (13)	0.0038 (9)	0.0130 (10)	−0.0116 (10)
C7	0.0350 (10)	0.0362 (9)	0.0451 (11)	0.0007 (7)	0.0044 (8)	−0.0042 (8)
C8	0.0411 (11)	0.0474 (11)	0.0455 (11)	−0.0026 (8)	0.0078 (9)	−0.0026 (9)
C9	0.0387 (10)	0.0456 (11)	0.0452 (11)	−0.0028 (8)	0.0080 (8)	−0.0074 (8)
C10	0.0687 (15)	0.0692 (14)	0.0525 (13)	0.0011 (11)	0.0132 (11)	0.0092 (10)
C11	0.0586 (13)	0.0541 (12)	0.0624 (13)	−0.0034 (10)	0.0197 (11)	−0.0159 (10)
C12	0.0430 (11)	0.0398 (11)	0.0532 (12)	0.0012 (9)	0.0117 (9)	0.0049 (9)
C13	0.0551 (14)	0.0678 (14)	0.0682 (15)	−0.0103 (11)	0.0010 (11)	−0.0017 (12)

O1—C1	1.347 (2)	C8—C9	1.355 (2)
O1—H1	0.8200	C8—C10	1.486 (3)
O3—C12	1.238 (2)	C9—C11	1.492 (2)
O2—C12	1.254 (2)	C10—H10A	0.9600
O4—H1W	0.8364	C10—H10B	0.9600
O4—H2W	0.8428	C10—H10C	0.9600
N1—C7	1.336 (2)	C10—H10D	0.9600
N1—C8	1.383 (2)	C10—H10E	0.9600
N1—H1D	0.8600	C10—H10F	0.9600
N2—C7	1.339 (2)	C11—H11A	0.9600
N2—C9	1.378 (2)	C11—H11B	0.9600
N2—H2D	0.8600	C11—H11C	0.9600
C1—C6	1.393 (3)	C11—H11D	0.9600
C1—C2	1.404 (2)	C11—H11E	0.9600
C2—C3	1.396 (2)	C11—H11F	0.9600
C2—C7	1.455 (2)	C12—C13	1.493 (3)
C3—C4	1.377 (3)	C13—H13F	0.9600
C3—H3	0.9300	C13—H13E	0.9600
C4—C5	1.384 (3)	C13—H13D	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.370 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300
C1—O1—H1	109.5	H10A—C10—H10F	56.3
H1W—O4—H2W	108.9	H10B—C10—H10F	56.3
C7—N1—C8	110.46 (14)	H10C—C10—H10F	141.1
C7—N1—H1D	124.7	H10D—C10—H10F	109.5
C8—N1—H1D	124.8	H10E—C10—H10F	109.5
C7—N2—C9	110.57 (14)	C9—C11—H11A	109.5
C7—N2—H2D	124.7	C9—C11—H11B	109.5
C9—N2—H2D	124.7	H11A—C11—H11B	109.5
O1—C1—C6	122.33 (16)	C9—C11—H11C	109.5
O1—C1—C2	118.22 (16)	H11A—C11—H11C	109.5
C6—C1—C2	119.44 (17)	H11B—C11—H11C	109.5
C3—C2—C1	118.52 (16)	C9—C11—H11D	109.5
C3—C2—C7	119.85 (15)	H11A—C11—H11D	141.1
C1—C2—C7	121.63 (16)	H11B—C11—H11D	56.3
C4—C3—C2	121.41 (18)	H11C—C11—H11D	56.3
C4—C3—H3	119.3	C9—C11—H11E	109.5
C2—C3—H3	119.3	H11A—C11—H11E	56.3
C3—C4—C5	119.36 (19)	H11B—C11—H11E	141.1
C3—C4—H4	120.3	H11C—C11—H11E	56.3
C5—C4—H4	120.3	H11D—C11—H11E	109.5
C6—C5—C4	120.52 (18)	C9—C11—H11F	109.5
C6—C5—H5	119.7	H11A—C11—H11F	56.3
C4—C5—H5	119.7	H11B—C11—H11F	56.3
C5—C6—C1	120.73 (18)	H11C—C11—H11F	141.1
C5—C6—H6	119.6	H11D—C11—H11F	109.5
C1—C6—H6	119.6	H11E—C11—H11F	109.5
N1—C7—N2	106.06 (15)	O3—C12—O2	122.65 (19)
N1—C7—C2	128.32 (15)	O3—C12—C13	118.89 (18)
N2—C7—C2	125.61 (16)	O2—C12—C13	118.46 (17)
C9—C8—N1	106.41 (15)	C12—C13—H13F	109.5
C9—C8—C10	131.30 (17)	C12—C13—H13E	109.5
N1—C8—C10	122.25 (16)	H13F—C13—H13E	109.5
C8—C9—N2	106.49 (15)	C12—C13—H13D	109.5
C8—C9—C11	131.55 (17)	H13F—C13—H13D	109.5
N2—C9—C11	121.95 (17)	H13E—C13—H13D	109.5
C8—C10—H10A	109.5	C12—C13—H13C	109.5
C8—C10—H10B	109.5	H13F—C13—H13C	141.1
H10A—C10—H10B	109.5	H13E—C13—H13C	56.3
C8—C10—H10C	109.5	H13D—C13—H13C	56.3
H10A—C10—H10C	109.5	C12—C13—H13B	109.5
H10B—C10—H10C	109.5	H13F—C13—H13B	56.3
C8—C10—H10D	109.5	H13E—C13—H13B	141.1
H10A—C10—H10D	141.1	H13D—C13—H13B	56.3
H10B—C10—H10D	56.3	H13C—C13—H13B	109.5
H10C—C10—H10D	56.3	C12—C13—H13A	109.5
C8—C10—H10E	109.5	H13F—C13—H13A	56.3
H10A—C10—H10E	56.3	H13E—C13—H13A	56.3
H10B—C10—H10E	141.1	H13D—C13—H13A	141.1
H10C—C10—H10E	56.3	H13C—C13—H13A	109.5
H10D—C10—H10E	109.5	H13B—C13—H13A	109.5
C8—C10—H10F	109.5
O1—C1—C2—C3	179.44 (16)	C9—N2—C7—C2	−179.93 (16)
C6—C1—C2—C3	−1.2 (3)	C3—C2—C7—N1	171.82 (17)
O1—C1—C2—C7	−0.6 (3)	C1—C2—C7—N1	−8.1 (3)
C6—C1—C2—C7	178.69 (16)	C3—C2—C7—N2	−7.3 (3)
C1—C2—C3—C4	1.3 (3)	C1—C2—C7—N2	172.81 (16)
C7—C2—C3—C4	−178.65 (17)	C7—N1—C8—C9	0.1 (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—N2	0.34 (19)
C4—C5—C6—C1	1.1 (3)	C10—C8—C9—N2	177.9 (2)
O1—C1—C6—C5	179.40 (18)	N1—C8—C9—C11	−178.04 (19)
C2—C1—C6—C5	0.1 (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—C11	177.84 (17)
C9—N2—C7—N1	0.82 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2D···O4	0.86	1.93	2.7747 (19)	169.
N1—H1D···O1	0.86	2.17	2.6956 (19)	119.
N1—H1D···O3	0.86	2.10	2.834 (2)	142.
O4—H2W···O3i	0.84	1.89	2.710 (2)	164.
O4—H1W···O2ii	0.84	2.07	2.808 (2)	146.
O1—H1···O2iii	0.82	1.76	2.5624 (18)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2D⋯O4	0.86	1.93	2.7747 (19)	169
N1—H1D⋯O1	0.86	2.17	2.6956 (19)	119
N1—H1D⋯O3	0.86	2.10	2.834 (2)	142
O4—H2W⋯O3i	0.84	1.89	2.710 (2)	164
O4—H1W⋯O2ii	0.84	2.07	2.808 (2)	146
O1—H1⋯O2iii	0.82	1.76	2.5624 (18)	167

Symmetry codes: (i) ; (ii) ; (iii) .