(E)-2-Meth-oxy-4-(3-oxobut-1-en-yl)phenyl acetate.

The title compound, C(13)H(14)O(4), belongs to the class of α,β-unsaturated ketones, which have potential bactericidal, fungicidal, anti-tumor and anti-inflammatory properties. The C atoms and attached H atoms of the ethenyl part of the title mol-ecule are disordered over two orientations with refined occupancies of 0.583 (7) and 0.417 (3). Mol-ecules are connected by two inter-molecular C-H⋯O inter-actions, forming a dimer with symmetry.

Related literature

For related literature, see: Steiner et al. (1998 ▶); Kuo et al. (2005 ▶); Buszek et al. (2007 ▶); Yarishkin et al. (2008 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C13H14O4

M = 234.24

Triclinic,

a = 6.2534 (5) Å

b = 7.5797 (5) Å

c = 13.9718 (8) Å

α = 96.611 (2)°

β = 91.487 (2)°

γ = 110.599 (2)°

V = 614.21 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 299 (2) K

0.30 × 0.23 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.981, T max = 0.989

3984 measured reflections

2381 independent reflections

1423 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.220

S = 1.10

2381 reflections

173 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 I, global. DOI: 10.1107/S1600536808021417/fb2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021417/fb2101Isup2.hkl

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

C13H14O4	Z = 2
Mr = 234.24	F000 = 248
Triclinic, P1	Dx = 1.267 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.2534 (5) Å	Cell parameters from 1174 reflections
b = 7.5797 (5) Å	θ = 3.8–27.7º
c = 13.9718 (8) Å	µ = 0.09 mm−1
α = 96.611 (2)º	T = 299 (2) K
β = 91.487 (2)º	Block, colourless
γ = 110.599 (2)º	0.30 × 0.23 × 0.20 mm
V = 614.21 (7) Å3

Bruker SMART 4K CCD area-detector diffractometer	2381 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 299(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −7→7
Tmin = 0.981, Tmax = 0.989	k = −8→9
3984 measured reflections	l = −10→17

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: difference Fourier map
wR(F2) = 0.220	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1082P)2 + 0.0333P] where P = (Fo2 + 2Fc2)/3
2381 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.23 e Å−3
14 restraints	Δρmin = −0.47 e Å−3
61 constraints	Extinction correction: none

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)
C1	0.7293 (5)	0.3948 (4)	0.2545 (3)	0.0882 (10)
C2	0.9194 (5)	0.5292 (4)	0.3052 (2)	0.0738 (8)
H2	0.9074	0.5763	0.3685	0.089*
C3	1.1270 (4)	0.5962 (3)	0.26515 (19)	0.0624 (7)
C4	1.1411 (4)	0.5259 (3)	0.16982 (19)	0.0609 (7)
C5	0.9549 (5)	0.3919 (4)	0.1173 (2)	0.0768 (8)
H5	0.9673	0.3460	0.0538	0.092*
C6	0.7504 (5)	0.3261 (4)	0.1588 (3)	0.0937 (11)
H6	0.6241	0.2349	0.1232	0.112*
C7	0.4817 (6)	0.2784 (6)	0.2726 (3)	0.0590 (12)	0.568 (5)
H7	0.3809	0.1860	0.2267	0.071*	0.568 (5)
C8	0.4287 (6)	0.3213 (5)	0.3572 (2)	0.0590 (12)	0.568 (5)
H8	0.5350	0.4157	0.4006	0.071*	0.568 (5)
C7'	0.5396 (6)	0.3583 (5)	0.3256 (2)	0.0695 (19)	0.432 (5)
H7'	0.5659	0.4348	0.3849	0.083*	0.432 (5)
C8'	0.3469 (9)	0.2245 (8)	0.3042 (3)	0.0690 (17)	0.432 (5)
H8'	0.3087	0.1433	0.2462	0.083*	0.432 (5)
C9	0.1831 (5)	0.2135 (5)	0.3871 (3)	0.0823 (9)
C10	−0.0103 (8)	0.0611 (5)	0.3285 (3)	0.1215 (14)
H10A	−0.1400	0.0213	0.3668	0.182*
H10B	0.0349	−0.0452	0.3082	0.182*
H10C	−0.0506	0.1090	0.2728	0.182*
C11	1.3290 (6)	0.7714 (5)	0.4125 (2)	0.0957 (10)
H11A	1.2309	0.8425	0.4272	0.144*
H11B	1.4830	0.8466	0.4371	0.144*
H11C	1.2771	0.6568	0.4420	0.144*
C12	1.4400 (5)	0.7588 (4)	0.10439 (18)	0.0678 (7)
C13	1.6743 (5)	0.7974 (5)	0.0730 (2)	0.0937 (10)
H13A	1.6724	0.6999	0.0222	0.141*
H13B	1.7741	0.7986	0.1266	0.141*
H13C	1.7286	0.9187	0.0497	0.141*
O1	0.1650 (4)	0.2704 (4)	0.46647 (19)	0.1071 (8)
O2	1.3230 (3)	0.7243 (3)	0.31006 (13)	0.0802 (6)
O3	1.3305 (3)	0.8606 (3)	0.10693 (14)	0.0814 (6)
O4	1.3533 (3)	0.5806 (2)	0.13013 (12)	0.0693 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0607 (15)	0.0758 (16)	0.144 (2)	0.0288 (13)	0.0191 (15)	0.0587 (17)
C2	0.0849 (16)	0.0753 (14)	0.0869 (16)	0.0450 (13)	0.0302 (12)	0.0313 (12)
C3	0.0681 (13)	0.0545 (11)	0.0715 (14)	0.0262 (10)	0.0083 (11)	0.0124 (10)
C4	0.0657 (13)	0.0539 (11)	0.0710 (14)	0.0260 (10)	0.0114 (10)	0.0120 (10)
C5	0.0794 (16)	0.0613 (13)	0.0850 (16)	0.0210 (12)	−0.0046 (12)	0.0102 (11)
C6	0.0754 (17)	0.0681 (15)	0.127 (2)	0.0162 (13)	−0.0100 (16)	0.0285 (15)
C7	0.071 (3)	0.047 (2)	0.056 (2)	0.022 (2)	−0.007 (2)	−0.0067 (18)
C8	0.069 (4)	0.060 (3)	0.051 (3)	0.024 (3)	0.001 (2)	0.003 (2)
C8'	0.075 (4)	0.072 (4)	0.059 (4)	0.029 (3)	0.015 (3)	0.009 (3)
C7'	0.061 (4)	0.046 (3)	0.067 (5)	0.019 (3)	0.001 (3)	0.006 (3)
C9	0.0968 (19)	0.0915 (17)	0.0871 (18)	0.0544 (16)	0.0341 (15)	0.0406 (15)
C10	0.170 (3)	0.105 (2)	0.111 (2)	0.077 (2)	−0.014 (2)	0.0052 (17)
C11	0.118 (2)	0.1023 (18)	0.0702 (16)	0.0465 (16)	−0.0048 (13)	−0.0076 (13)
C12	0.0737 (14)	0.0587 (13)	0.0602 (13)	0.0164 (11)	0.0068 (10)	−0.0040 (9)
C13	0.0821 (17)	0.0900 (17)	0.1022 (19)	0.0205 (14)	0.0215 (13)	0.0031 (13)
O1	0.1010 (13)	0.1159 (14)	0.0938 (13)	0.0276 (11)	0.0235 (10)	0.0089 (11)
O2	0.0838 (11)	0.0797 (10)	0.0694 (10)	0.0189 (9)	0.0060 (7)	−0.0027 (7)
O3	0.0893 (11)	0.0624 (9)	0.0981 (12)	0.0285 (9)	0.0171 (8)	0.0156 (8)
O4	0.0753 (10)	0.0609 (9)	0.0759 (10)	0.0279 (7)	0.0172 (7)	0.0076 (7)

C1—C2	1.375 (4)	C7'—H7'	0.9300
C1—C6	1.405 (5)	C8'—C9	1.556 (4)
C1—C7	1.533 (4)	C8'—H8'	0.9300
C1—C7'	1.538 (4)	C9—O1	1.166 (3)
C2—C3	1.377 (4)	C9—C10	1.488 (5)
C2—H2	0.9300	C10—H10A	0.9600
C3—O2	1.349 (3)	C10—H10B	0.9600
C3—C4	1.393 (3)	C10—H10C	0.9600
C4—C5	1.370 (4)	C11—O2	1.431 (3)
C4—O4	1.395 (3)	C11—H11A	0.9600
C5—C6	1.370 (4)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	C12—O3	1.197 (3)
C7—C8	1.273 (3)	C12—O4	1.362 (3)
C7—H7	0.9300	C12—C13	1.479 (4)
C8—C9	1.559 (4)	C13—H13A	0.9600
C8—H8	0.9300	C13—H13B	0.9600
C7'—C8'	1.274 (4)	C13—H13C	0.9600
C2—C1—C6	118.2 (3)	C7'—C8'—H8'	124.2
C2—C1—C7	138.3 (3)	C9—C8'—H8'	124.2
C6—C1—C7	103.5 (3)	O1—C9—C10	121.7 (3)
C2—C1—C7'	105.1 (3)	O1—C9—C8'	145.9 (3)
C6—C1—C7'	136.7 (3)	C10—C9—C8'	92.4 (3)
C1—C2—C3	122.0 (3)	O1—C9—C8	109.7 (3)
C1—C2—H2	119.0	C10—C9—C8	128.6 (3)
C3—C2—H2	119.0	C9—C10—H10A	109.5
O2—C3—C2	126.0 (3)	C9—C10—H10B	109.5
O2—C3—C4	115.8 (2)	H10A—C10—H10B	109.5
C2—C3—C4	118.2 (3)	C9—C10—H10C	109.5
C5—C4—C3	121.3 (2)	H10A—C10—H10C	109.5
C5—C4—O4	119.3 (2)	H10B—C10—H10C	109.5
C3—C4—O4	119.2 (2)	O2—C11—H11A	109.5
C4—C5—C6	119.6 (3)	O2—C11—H11B	109.5
C4—C5—H5	120.2	H11A—C11—H11B	109.5
C6—C5—H5	120.2	O2—C11—H11C	109.5
C5—C6—C1	120.8 (3)	H11A—C11—H11C	109.5
C5—C6—H6	119.6	H11B—C11—H11C	109.5
C1—C6—H6	119.6	O3—C12—O4	121.7 (2)
C8—C7—C1	112.9 (2)	O3—C12—C13	128.1 (3)
C8—C7—H7	123.6	O4—C12—C13	110.2 (3)
C1—C7—H7	123.6	C12—C13—H13A	109.5
C7—C8—C9	119.1 (3)	C12—C13—H13B	109.5
C7—C8—H8	120.5	H13A—C13—H13B	109.5
C9—C8—H8	120.5	C12—C13—H13C	109.5
C8'—C7'—C1	120.7 (3)	H13A—C13—H13C	109.5
C8'—C7'—H7'	119.6	H13B—C13—H13C	109.5
C1—C7'—H7'	119.6	C3—O2—C11	117.5 (2)
C7'—C8'—C9	111.7 (2)	C12—O4—C4	118.03 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.58	3.507 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.58	3.507 (4)	172

Symmetry code: (i) .