(Z)-3-Hy-droxy-4-(4-meth-oxy-phen-yl)but-3-en-2-one.

The title compound, C11H12O3, is potentially a butane-2,3-dione derivative but exists in the enol form in the solid state. In the mol-ecule, the 3-hy-droxy-but-3-en-2-one, benzene and methoxyl fragments are almost co-planar. The 3-hy-droxy-but-3-en-2-one fragment is almost planar with an r.m.s. deviation of 0.040 Å. The dihedral angle between this plane and that of the benzene ring is 5.88 (4)°. The 4-meth-oxy group also lies close to the benzene ring plane, with deviations of 0.0206 (11) Å for the O and 0.087 (2) Å for methyl C atoms. Hence, the whole mol-ecule is almost planar with an r.m.s. deviation of 0.0617 Å from a plane through all 14 non-H atoms. In the crystal, the molecules are linked by O-H⋯O hydrogen bonds, generating [010] chains.

Related literature

The synthesis of the compound is described by Wang & Huang (2010 ▶). For applications of aromatic ketones as fragrances, see: Tong et al. (2009 ▶). For the relationship between structure and fragrance, see: Griesbeck et al. (2012 ▶). For related structures and details of their synthesis, see: Yamane et al. (2005 ▶); Si et al. (1990 ▶); Salimbeni et al. (1987 ▶); Mosrin et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12O3

M = 192.21

Monoclinic,

a = 18.8076 (13) Å

b = 5.3007 (4) Å

c = 10.1439 (8) Å

β = 103.425 (7)°

V = 983.65 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 223 K

0.50 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur (Atlas CCD, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.915, T max = 1.000

6213 measured reflections

1829 independent reflections

1505 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.01

1829 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2004 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813002262/sj5292sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002262/sj5292Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002262/sj5292Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002262/sj5292Isup4.cml

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

C11H12O3	F(000) = 408
Mr = 192.21	Dx = 1.298 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1975 reflections
a = 18.8076 (13) Å	θ = 3.3–29.4°
b = 5.3007 (4) Å	µ = 0.09 mm−1
c = 10.1439 (8) Å	T = 223 K
β = 103.425 (7)°	Block, yellow
V = 983.65 (13) Å3	0.50 × 0.40 × 0.35 mm
Z = 4

Agilent Xcalibur (Atlas CCD, Gemini) diffractometer	1829 independent reflections
Radiation source: fine-focus sealed tube	1505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −22→22
Tmin = 0.915, Tmax = 1.000	k = −6→6
6213 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2906P] where P = (Fo2 + 2Fc2)/3
1829 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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
O1	0.48064 (6)	0.4343 (3)	0.31418 (12)	0.0567 (4)
O2	0.38385 (6)	0.2608 (2)	0.10575 (12)	0.0548 (4)
H2	0.4252	0.2145	0.1431	0.082*
O3	0.06871 (6)	0.4633 (2)	−0.32947 (11)	0.0527 (4)
C1	0.40895 (10)	0.7551 (4)	0.38093 (17)	0.0556 (5)
H1A	0.3996	0.9078	0.3289	0.083*
H1B	0.4513	0.7774	0.4538	0.083*
H1C	0.3675	0.7155	0.4173	0.083*
C2	0.42216 (9)	0.5450 (3)	0.29207 (16)	0.0421 (4)
C3	0.36530 (8)	0.4639 (3)	0.17241 (15)	0.0396 (4)
C4	0.30191 (8)	0.5866 (3)	0.12778 (15)	0.0396 (4)
H4	0.2938	0.7202	0.1818	0.048*
C5	0.24383 (8)	0.5416 (3)	0.00700 (15)	0.0372 (4)
C6	0.18417 (9)	0.7074 (3)	−0.02124 (16)	0.0425 (4)
H6	0.1830	0.8411	0.0375	0.051*
C7	0.12736 (9)	0.6784 (3)	−0.13315 (16)	0.0446 (4)
H7	0.0886	0.7918	−0.1494	0.053*
C8	0.12795 (8)	0.4798 (3)	−0.22176 (15)	0.0394 (4)
C9	0.18628 (9)	0.3141 (3)	−0.19755 (16)	0.0443 (4)
H9	0.1872	0.1815	−0.2572	0.053*
C10	0.24337 (9)	0.3452 (3)	−0.08458 (16)	0.0439 (4)
H10	0.2823	0.2323	−0.0695	0.053*
C11	0.06626 (10)	0.2552 (4)	−0.41902 (18)	0.0573 (5)
H11A	0.0221	0.2630	−0.4891	0.086*
H11B	0.0672	0.1005	−0.3694	0.086*
H11C	0.1077	0.2616	−0.4590	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0445 (7)	0.0652 (8)	0.0530 (7)	0.0081 (6)	−0.0037 (5)	−0.0056 (6)
O2	0.0446 (7)	0.0531 (8)	0.0577 (7)	0.0111 (6)	−0.0064 (5)	−0.0111 (6)
O3	0.0452 (7)	0.0585 (8)	0.0466 (7)	0.0075 (6)	−0.0052 (5)	−0.0051 (6)
C1	0.0533 (10)	0.0689 (13)	0.0415 (9)	0.0015 (9)	0.0045 (8)	−0.0094 (9)
C2	0.0400 (9)	0.0485 (10)	0.0366 (8)	−0.0028 (8)	0.0067 (6)	0.0051 (7)
C3	0.0402 (8)	0.0408 (9)	0.0372 (8)	−0.0031 (7)	0.0076 (7)	0.0013 (7)
C4	0.0398 (8)	0.0415 (9)	0.0373 (8)	−0.0018 (7)	0.0084 (6)	−0.0014 (7)
C5	0.0352 (8)	0.0368 (8)	0.0395 (8)	−0.0010 (7)	0.0085 (6)	0.0029 (6)
C6	0.0460 (9)	0.0385 (9)	0.0425 (9)	0.0051 (7)	0.0092 (7)	−0.0028 (7)
C7	0.0420 (9)	0.0435 (9)	0.0461 (9)	0.0110 (7)	0.0060 (7)	0.0033 (7)
C8	0.0365 (8)	0.0436 (9)	0.0361 (8)	−0.0006 (7)	0.0044 (6)	0.0044 (7)
C9	0.0427 (9)	0.0432 (9)	0.0447 (9)	0.0035 (7)	0.0056 (7)	−0.0063 (7)
C10	0.0372 (8)	0.0428 (9)	0.0485 (9)	0.0075 (7)	0.0032 (7)	−0.0037 (7)
C11	0.0547 (11)	0.0566 (12)	0.0512 (10)	−0.0028 (9)	−0.0067 (8)	−0.0082 (9)

O1—C2	1.2206 (19)	C5—C10	1.394 (2)
O2—C3	1.3592 (19)	C5—C6	1.401 (2)
O2—H2	0.8200	C6—C7	1.375 (2)
O3—C8	1.3703 (18)	C6—H6	0.9300
O3—C11	1.423 (2)	C7—C8	1.386 (2)
C1—C2	1.490 (2)	C7—H7	0.9300
C1—H1A	0.9600	C8—C9	1.382 (2)
C1—H1B	0.9600	C9—C10	1.386 (2)
C1—H1C	0.9600	C9—H9	0.9300
C2—C3	1.483 (2)	C10—H10	0.9300
C3—C4	1.341 (2)	C11—H11A	0.9600
C4—C5	1.459 (2)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C3—O2—H2	109.5	C7—C6—H6	119.0
C8—O3—C11	117.29 (13)	C5—C6—H6	119.0
C2—C1—H1A	109.5	C6—C7—C8	119.92 (15)
C2—C1—H1B	109.5	C6—C7—H7	120.0
H1A—C1—H1B	109.5	C8—C7—H7	120.0
C2—C1—H1C	109.5	O3—C8—C9	124.47 (15)
H1A—C1—H1C	109.5	O3—C8—C7	116.00 (14)
H1B—C1—H1C	109.5	C9—C8—C7	119.54 (14)
O1—C2—C3	117.32 (15)	C8—C9—C10	120.12 (15)
O1—C2—C1	121.21 (15)	C8—C9—H9	119.9
C3—C2—C1	121.47 (15)	C10—C9—H9	119.9
C4—C3—O2	121.79 (14)	C9—C10—C5	121.55 (15)
C4—C3—C2	123.48 (15)	C9—C10—H10	119.2
O2—C3—C2	114.64 (14)	C5—C10—H10	119.2
C3—C4—C5	129.63 (15)	O3—C11—H11A	109.5
C3—C4—H4	115.2	O3—C11—H11B	109.5
C5—C4—H4	115.2	H11A—C11—H11B	109.5
C10—C5—C6	116.83 (14)	O3—C11—H11C	109.5
C10—C5—C4	124.68 (14)	H11A—C11—H11C	109.5
C6—C5—C4	118.49 (14)	H11B—C11—H11C	109.5
C7—C6—C5	122.04 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.27	3.0315 (17)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.27	3.0315 (17)	154

Symmetry code: (i) .