1-(2-Hy-droxy-5-meth-oxy-phen-yl)-3-methyl-but-2-en-1-one.

The title compound, C(12)H(14)O(3), is a natural product derived from the medium-sized hawthorn Crataegus persimilis ('prunifolia'). The mean plane of the butene moiety is twisted by 13.27 (7)° with respect to the that of the dioxobenzaldehyde moiety. There is an intra-molecular hydrogen bond between the hydroxyl group and the carbonyl O atom.

Related literature

For isolation from plant material, see: Castro et al. (1989 ▶). For the synthesis, see: Camps et al. (1985 ▶). For photolysis to form 4-chromanones, see: Primo et al. (1982 ▶). For a related structure, see: Zeller et al. (2010 ▶).

Experimental

Crystal data

C12H14O3

M = 206.23

Monoclinic,

a = 14.027 (3) Å

b = 5.816 (1) Å

c = 12.829 (3) Å

β = 91.409 (8)°

V = 1046.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.37 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor 1997 ▶) T min = 0.959, T max = 0.979

6425 measured reflections

3784 independent reflections

3179 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.04

3784 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042158/im2405sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042158/im2405Isup2.hkl

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

C12H14O3	F(000) = 440
Mr = 206.23	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3442 reflections
a = 14.027 (3) Å	θ = 2.5–32.6°
b = 5.816 (1) Å	µ = 0.09 mm−1
c = 12.829 (3) Å	T = 100 K
β = 91.409 (8)°	Fragment, yellow
V = 1046.3 (4) Å3	0.45 × 0.37 × 0.23 mm
Z = 4

Nonius KappaCCD diffractometer	3784 independent reflections
Radiation source: sealed tube	3179 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.018
Detector resolution: 9 pixels mm-1	θmax = 32.6°, θmin = 3.2°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (HKLSCALEPACK; Otwinowski & Minor 1997)	k = −8→7
Tmin = 0.959, Tmax = 0.979	l = −19→19
6425 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0692P)2 + 0.2297P] where P = (Fo2 + 2Fc2)/3
3784 reflections	(Δ/σ)max = 0.001
143 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.22 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
C1	0.38220 (6)	1.03873 (14)	0.88580 (6)	0.01713 (16)
C2	0.31710 (6)	0.89827 (14)	0.93398 (6)	0.01652 (15)
H2	0.3003	0.9281	1.0040	0.020*
C3	0.27530 (6)	0.71019 (14)	0.87973 (6)	0.01641 (15)
C4	0.30238 (6)	0.66752 (15)	0.77617 (6)	0.01796 (16)
C5	0.36779 (6)	0.81313 (15)	0.72851 (6)	0.01992 (17)
H5	0.3853	0.7853	0.6586	0.024*
C6	0.40689 (6)	0.99610 (16)	0.78231 (6)	0.01999 (17)
H6	0.4509	1.0944	0.7491	0.024*
C7	0.20366 (6)	0.55840 (14)	0.92711 (7)	0.01901 (16)
C8	0.17084 (6)	0.60621 (15)	1.03279 (7)	0.01893 (16)
H8	0.1897	0.7485	1.0632	0.023*
C9	0.11620 (6)	0.46622 (15)	1.09083 (7)	0.01933 (16)
C10	0.08404 (7)	0.54666 (17)	1.19537 (7)	0.02467 (19)
H10A	0.1069	0.7037	1.2079	0.037*
H10B	0.1100	0.4446	1.2498	0.037*
H10C	0.0142	0.5442	1.1967	0.037*
C11	0.08255 (7)	0.23100 (16)	1.05970 (8)	0.02593 (19)
H11A	0.0197	0.2424	1.0251	0.039*
H11B	0.0781	0.1342	1.1219	0.039*
H11C	0.1279	0.1625	1.0117	0.039*
C12	0.40983 (6)	1.26466 (15)	1.03865 (7)	0.02072 (17)
H12A	0.3425	1.3041	1.0465	0.031*
H12B	0.4497	1.3925	1.0637	0.031*
H12C	0.4249	1.1263	1.0794	0.031*
O1	0.42786 (5)	1.22263 (11)	0.93148 (5)	0.02247 (15)
O2	0.26717 (5)	0.49087 (12)	0.71825 (5)	0.02388 (15)
H2A	0.2287 (12)	0.416 (3)	0.7580 (14)	0.052 (5)*
O3	0.17042 (5)	0.39337 (13)	0.87547 (6)	0.02755 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0188 (3)	0.0184 (3)	0.0143 (3)	−0.0008 (3)	0.0011 (3)	0.0000 (3)
C2	0.0168 (3)	0.0186 (3)	0.0142 (3)	0.0004 (3)	0.0009 (3)	0.0004 (3)
C3	0.0166 (3)	0.0175 (3)	0.0152 (3)	0.0007 (3)	0.0007 (3)	0.0006 (3)
C4	0.0195 (3)	0.0188 (3)	0.0156 (3)	0.0018 (3)	−0.0008 (3)	−0.0011 (3)
C5	0.0230 (4)	0.0234 (4)	0.0134 (3)	−0.0002 (3)	0.0018 (3)	−0.0006 (3)
C6	0.0226 (4)	0.0235 (4)	0.0140 (3)	−0.0026 (3)	0.0031 (3)	0.0010 (3)
C7	0.0181 (3)	0.0192 (4)	0.0198 (4)	−0.0002 (3)	0.0004 (3)	0.0002 (3)
C8	0.0179 (3)	0.0191 (3)	0.0199 (4)	−0.0006 (3)	0.0027 (3)	0.0002 (3)
C9	0.0157 (3)	0.0199 (4)	0.0224 (4)	0.0013 (3)	0.0007 (3)	0.0035 (3)
C10	0.0241 (4)	0.0267 (4)	0.0236 (4)	−0.0015 (3)	0.0071 (3)	0.0029 (3)
C11	0.0265 (4)	0.0208 (4)	0.0305 (5)	−0.0040 (3)	0.0023 (4)	0.0039 (3)
C12	0.0243 (4)	0.0223 (4)	0.0157 (3)	−0.0029 (3)	0.0026 (3)	−0.0027 (3)
O1	0.0286 (3)	0.0238 (3)	0.0153 (3)	−0.0094 (2)	0.0052 (2)	−0.0030 (2)
O2	0.0301 (3)	0.0225 (3)	0.0190 (3)	−0.0042 (3)	0.0017 (3)	−0.0051 (2)
O3	0.0317 (4)	0.0260 (3)	0.0251 (3)	−0.0101 (3)	0.0034 (3)	−0.0049 (3)

C1—O1	1.3708 (10)	C8—H8	0.95
C1—C2	1.3824 (11)	C9—C11	1.4982 (13)
C1—C6	1.4023 (12)	C9—C10	1.5003 (13)
C2—C3	1.4159 (11)	C10—H10A	0.98
C2—H2	0.95	C10—H10B	0.98
C3—C4	1.4127 (12)	C10—H10C	0.98
C3—C7	1.4795 (12)	C11—H11A	0.98
C4—O2	1.3540 (10)	C11—H11B	0.98
C4—C5	1.4002 (12)	C11—H11C	0.98
C5—C6	1.3751 (12)	C12—O1	1.4251 (11)
C5—H5	0.95	C12—H12A	0.98
C6—H6	0.95	C12—H12B	0.98
C7—O3	1.2499 (11)	C12—H12C	0.98
C7—C8	1.4690 (12)	O2—H2A	0.870 (18)
C8—C9	1.3538 (12)
O1—C1—C2	125.22 (7)	C8—C9—C11	125.55 (8)
O1—C1—C6	114.77 (7)	C8—C9—C10	119.40 (8)
C2—C1—C6	120.00 (8)	C11—C9—C10	115.05 (8)
C1—C2—C3	120.46 (7)	C9—C10—H10A	109.5
C1—C2—H2	119.8	C9—C10—H10B	109.5
C3—C2—H2	119.8	H10A—C10—H10B	109.5
C4—C3—C2	118.71 (7)	C9—C10—H10C	109.5
C4—C3—C7	118.86 (7)	H10A—C10—H10C	109.5
C2—C3—C7	122.43 (7)	H10B—C10—H10C	109.5
O2—C4—C5	116.96 (8)	C9—C11—H11A	109.5
O2—C4—C3	123.13 (8)	C9—C11—H11B	109.5
C5—C4—C3	119.91 (8)	H11A—C11—H11B	109.5
C6—C5—C4	120.43 (8)	C9—C11—H11C	109.5
C6—C5—H5	119.8	H11A—C11—H11C	109.5
C4—C5—H5	119.8	H11B—C11—H11C	109.5
C5—C6—C1	120.48 (8)	O1—C12—H12A	109.5
C5—C6—H6	119.8	O1—C12—H12B	109.5
C1—C6—H6	119.8	H12A—C12—H12B	109.5
O3—C7—C8	120.88 (8)	O1—C12—H12C	109.5
O3—C7—C3	119.26 (8)	H12A—C12—H12C	109.5
C8—C7—C3	119.85 (7)	H12B—C12—H12C	109.5
C9—C8—C7	126.04 (8)	C1—O1—C12	117.01 (7)
C9—C8—H8	117	C4—O2—H2A	106.4 (12)
C7—C8—H8	117
O1—C1—C2—C3	−178.95 (8)	C2—C1—C6—C5	−0.92 (13)
C6—C1—C2—C3	0.33 (13)	C4—C3—C7—O3	1.59 (12)
C1—C2—C3—C4	0.82 (12)	C2—C3—C7—O3	−179.06 (8)
C1—C2—C3—C7	−178.54 (8)	C4—C3—C7—C8	−176.96 (7)
C2—C3—C4—O2	179.35 (7)	C2—C3—C7—C8	2.39 (12)
C7—C3—C4—O2	−1.28 (12)	O3—C7—C8—C9	11.11 (14)
C2—C3—C4—C5	−1.39 (12)	C3—C7—C8—C9	−170.37 (8)
C7—C3—C4—C5	177.99 (8)	C7—C8—C9—C11	2.89 (14)
O2—C4—C5—C6	−179.87 (8)	C7—C8—C9—C10	−176.50 (8)
C3—C4—C5—C6	0.82 (13)	C2—C1—O1—C12	3.14 (12)
C4—C5—C6—C1	0.34 (13)	C6—C1—O1—C12	−176.18 (8)
O1—C1—C6—C5	178.43 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.87 (2)	1.74 (2)	2.523 (1)	149 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.87 (2)	1.74 (2)	2.523 (1)	149 (2)