(E)-4-(4-Meth-oxy-phen-yl)but-3-en-2-one.

In the title compound, C(11)H(12)O(2), the dihedral angle between the benzene ring and the but-3-en-2-one group is 4.04 (5)°. The crystal packing features chains, parallel to [-101], composed of dimers connected by weak C-H⋯O inter-actions..

Related literature

For related structures, see: Jasinski et al. (2010 ▶); Fun et al. (2011 ▶); Dutkiewicz et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12O2

M = 176.21

Monoclinic,

a = 10.1623 (19) Å

b = 13.292 (3) Å

c = 6.6488 (13) Å

β = 98.486 (3)°

V = 888.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.920, T max = 0.980

4492 measured reflections

1556 independent reflections

1332 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.150

S = 1.10

1556 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012214/gk2469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012214/gk2469Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012214/gk2469Isup3.cml

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

C11H12O2	F(000) = 376
Mr = 176.21	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2041 reflections
a = 10.1623 (19) Å	θ = 2.5–28.1°
b = 13.292 (3) Å	µ = 0.09 mm−1
c = 6.6488 (13) Å	T = 100 K
β = 98.486 (3)°	Hexagonal plate, colourless
V = 888.3 (3) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	1556 independent reflections
Radiation source: fine-focus sealed tube	1332 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.5°
phi and ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→14
Tmin = 0.920, Tmax = 0.980	l = −7→7
4492 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0943P)2 + 0.0951P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
1556 reflections	Δρmax = 0.36 e Å−3
121 parameters	Δρmin = −0.60 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.093 (13)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.32731 (14)	0.16937 (12)	0.2922 (2)	0.0270 (4)
H1A	0.4029	0.1751	0.2218	0.040*
H1B	0.3505	0.1293	0.4123	0.040*
H1C	0.3005	0.2352	0.3298	0.040*
O2	0.23069 (10)	0.09565 (8)	−0.01128 (16)	0.0272 (4)
C2	0.21533 (15)	0.12060 (11)	0.1565 (2)	0.0216 (4)
C3	0.08653 (15)	0.10549 (11)	0.2238 (2)	0.0205 (4)
H3	0.0184	0.0778	0.1318	0.025*
C4	0.06085 (14)	0.12829 (10)	0.4045 (2)	0.0197 (4)
H4	0.1314	0.1531	0.4961	0.024*
O5	−0.42876 (10)	0.09838 (8)	0.69111 (15)	0.0255 (4)
C6	−0.43869 (14)	0.12266 (12)	0.8912 (2)	0.0257 (4)
H6A	−0.3794	0.0808	0.9809	0.039*
H6B	−0.5284	0.1119	0.9157	0.039*
H6C	−0.4152	0.1920	0.9155	0.039*
C1'	−0.06661 (14)	0.11909 (10)	0.4784 (2)	0.0194 (4)
C2'	−0.07619 (13)	0.15059 (11)	0.6694 (2)	0.0209 (4)
H2'	−0.0009	0.1759	0.7502	0.025*
C3'	−0.19429 (14)	0.14616 (11)	0.7475 (2)	0.0220 (4)
H3'	−0.1984	0.1693	0.8784	0.026*
C4'	−0.30685 (14)	0.10736 (10)	0.6309 (2)	0.0199 (4)
C5'	−0.29933 (14)	0.07434 (11)	0.4401 (2)	0.0221 (4)
H5'	−0.3743	0.0479	0.3605	0.027*
C6'	−0.18091 (14)	0.07994 (11)	0.3644 (2)	0.0212 (4)
H6'	−0.1770	0.0569	0.2333	0.025*

	U11	U22	U33	U12	U13	U23
C1	0.0235 (8)	0.0307 (8)	0.0275 (9)	−0.0024 (6)	0.0064 (6)	−0.0031 (6)
O2	0.0258 (7)	0.0343 (7)	0.0224 (7)	−0.0017 (4)	0.0069 (5)	−0.0039 (4)
C2	0.0237 (8)	0.0181 (7)	0.0232 (9)	0.0031 (6)	0.0047 (6)	0.0033 (6)
C3	0.0185 (8)	0.0207 (8)	0.0217 (9)	−0.0005 (5)	0.0012 (6)	0.0005 (5)
C4	0.0193 (8)	0.0163 (7)	0.0229 (9)	0.0002 (5)	0.0010 (6)	0.0018 (6)
O5	0.0179 (6)	0.0374 (7)	0.0217 (7)	−0.0014 (4)	0.0039 (4)	−0.0016 (4)
C6	0.0222 (8)	0.0321 (9)	0.0241 (9)	0.0019 (6)	0.0077 (6)	−0.0007 (7)
C1'	0.0206 (8)	0.0153 (7)	0.0220 (8)	0.0018 (5)	0.0021 (6)	0.0027 (6)
C2'	0.0198 (8)	0.0189 (8)	0.0227 (9)	−0.0015 (6)	−0.0006 (6)	0.0003 (6)
C3'	0.0250 (8)	0.0205 (8)	0.0201 (8)	0.0009 (6)	0.0021 (6)	−0.0006 (6)
C4'	0.0181 (8)	0.0207 (8)	0.0210 (9)	0.0023 (6)	0.0035 (6)	0.0030 (6)
C5'	0.0209 (7)	0.0247 (8)	0.0194 (8)	−0.0007 (6)	−0.0012 (6)	0.0006 (6)
C6'	0.0229 (8)	0.0226 (8)	0.0177 (8)	0.0016 (6)	0.0015 (6)	0.0006 (6)

C1—C2	1.492 (2)	C6—H6B	0.9600
C1—H1A	0.9600	C6—H6C	0.9600
C1—H1B	0.9600	C1'—C2'	1.355 (2)
C1—H1C	0.9600	C1'—C6'	1.391 (2)
O2—C2	1.1959 (18)	C2'—C3'	1.377 (2)
C2—C3	1.458 (2)	C2'—H2'	0.9300
C3—C4	1.302 (2)	C3'—C4'	1.383 (2)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C1'	1.4568 (19)	C4'—C5'	1.355 (2)
C4—H4	0.9300	C5'—C6'	1.373 (2)
O5—C4'	1.3622 (16)	C5'—H5'	0.9300
O5—C6	1.3872 (18)	C6'—H6'	0.9300
C6—H6A	0.9600
C2—C1—H1A	109.5	H6A—C6—H6C	109.5
C2—C1—H1B	109.5	H6B—C6—H6C	109.5
H1A—C1—H1B	109.5	C2'—C1'—C6'	117.18 (13)
C2—C1—H1C	109.5	C2'—C1'—C4	118.74 (13)
H1A—C1—H1C	109.5	C6'—C1'—C4	124.08 (14)
H1B—C1—H1C	109.5	C1'—C2'—C3'	121.82 (13)
O2—C2—C3	119.65 (14)	C1'—C2'—H2'	119.1
O2—C2—C1	119.45 (13)	C3'—C2'—H2'	119.1
C3—C2—C1	120.87 (13)	C2'—C3'—C4'	119.97 (14)
C4—C3—C2	124.22 (14)	C2'—C3'—H3'	120.0
C4—C3—H3	117.9	C4'—C3'—H3'	120.0
C2—C3—H3	117.9	C5'—C4'—O5	115.21 (13)
C3—C4—C1'	126.94 (14)	C5'—C4'—C3'	119.27 (13)
C3—C4—H4	116.5	O5—C4'—C3'	125.52 (13)
C1'—C4—H4	116.5	C4'—C5'—C6'	119.95 (13)
C4'—O5—C6	117.34 (11)	C4'—C5'—H5'	120.0
O5—C6—H6A	109.5	C6'—C5'—H5'	120.0
O5—C6—H6B	109.5	C5'—C6'—C1'	121.81 (14)
H6A—C6—H6B	109.5	C5'—C6'—H6'	119.1
O5—C6—H6C	109.5	C1'—C6'—H6'	119.1
O2—C2—C3—C4	178.60 (14)	C6—O5—C4'—C3'	−5.4 (2)
C1—C2—C3—C4	−3.1 (2)	C2'—C3'—C4'—C5'	−0.2 (2)
C2—C3—C4—C1'	177.22 (12)	C2'—C3'—C4'—O5	179.55 (12)
C3—C4—C1'—C2'	−177.26 (15)	O5—C4'—C5'—C6'	−179.98 (12)
C3—C4—C1'—C6'	2.5 (2)	C3'—C4'—C5'—C6'	−0.2 (2)
C6'—C1'—C2'—C3'	−1.2 (2)	C4'—C5'—C6'—C1'	−0.1 (2)
C4—C1'—C2'—C3'	178.55 (12)	C2'—C1'—C6'—C5'	0.8 (2)
C1'—C2'—C3'—C4'	1.0 (2)	C4—C1'—C6'—C5'	−178.96 (12)
C6—O5—C4'—C5'	174.34 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6′—H6′···O2i	0.93	2.52	3.296 (2)	141
C6—H6B···O2ii	0.96	2.57	3.533 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6′—H6′⋯O2i	0.93	2.52	3.296 (2)	141
C6—H6B⋯O2ii	0.96	2.57	3.533 (2)	176

Symmetry codes: (i) ; (ii) .