(E)-1-(2,4,6-Trimeth-oxy-phen-yl)pent-1-en-3-one.

The title compound, C(14)H(18)O(4), was obtained unintentionally as the major product of an attempted synthesis of (E,E)-2,5-bis-[2-(2,4,6-trimeth-oxy-phen-yl)ethen-yl]pyrazine. The crystal packing features layers based on two weak C-H⋯O hydrogen bonds involving the O atom of the carbonyl group and two O(meth-oxy)⋯C(meth-oxy) inter-actions [3.109 (2) Å]. The sheets are inter-connected via meth-oxy-meth-oxy dimers and C-H⋯π inter-actions.

Related literature

For related compounds containing the Ph—CH=CH—CO— fragment, see: Zhang et al. (2008 ▶); Degen & Bolte (1999 ▶); Zonouzi et al. (2009 ▶); Wang et al. (2005 ▶). For π-bridged donor–acceptor–donor systems as candidates for organic light-emitting diodes and their non-linear optical properties, see Liu et al. (2001 ▶); Grimsdale et al. (1997 ▶); Chemla (1987 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H18O4

M = 250.28

Triclinic,

a = 6.8626 (8) Å

b = 8.297 (1) Å

c = 12.068 (2) Å

α = 71.96 (1)°

β = 84.28 (1)°

γ = 84.90 (1)°

V = 648.88 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.24 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4732 measured reflections

2366 independent reflections

1589 reflections with > 2/s(I)

R int = 0.020

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.03

2366 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); 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: WinGX (Farrugia, 1999 ▶), Mercury (Macrae et al., 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034641/zl2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034641/zl2296Isup2.hkl

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

C14H18O4	Z = 2
Mr = 250.28	F(000) = 268
Triclinic, P1	Dx = 1.281 Mg m−3
Hall symbol: -P 1	Melting point: 401 K
a = 6.8626 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.297 (1) Å	Cell parameters from 25 reflections
c = 12.068 (2) Å	θ = 5.8–10.7°
α = 71.96 (1)°	µ = 0.09 mm−1
β = 84.28 (1)°	T = 293 K
γ = 84.90 (1)°	Prism, yellow
V = 648.88 (15) Å3	0.3 × 0.24 × 0.18 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 1.8°
graphite	h = −8→8
non–profiled ω/2θ scans	k = −9→9
4732 measured reflections	l = −14→14
2366 independent reflections	3 standard reflections every 60 min
1589 reflections with > 2/s(I)	intensity decay: none

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.1212P] where P = (Fo2 + 2Fc2)/3
2366 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.17 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
C12	1.6553 (3)	−0.2420 (2)	0.97422 (19)	0.0572 (5)
H12A	1.6978	−0.1867	1.0259	0.086*
H12B	1.7585	−0.2453	0.9149	0.086*
H12C	1.6235	−0.3558	1.0179	0.086*
O2	0.41445 (17)	0.31488 (16)	0.60482 (12)	0.0544 (4)
O1	0.90913 (18)	−0.12493 (15)	0.63577 (11)	0.0498 (3)
O3	0.95452 (17)	0.26141 (15)	0.84353 (11)	0.0508 (4)
C2	0.8301 (2)	0.0153 (2)	0.66303 (15)	0.0389 (4)
C1	0.9334 (2)	0.0684 (2)	0.73980 (14)	0.0373 (4)
O4	1.4852 (2)	−0.34752 (17)	0.81476 (13)	0.0675 (4)
C3	0.6593 (2)	0.1019 (2)	0.61907 (15)	0.0434 (4)
H3	0.5942	0.0657	0.5679	0.052*
C7	1.1125 (2)	−0.0161 (2)	0.79054 (14)	0.0383 (4)
H7	1.1607	0.0323	0.8414	0.046*
C6	0.8527 (2)	0.2139 (2)	0.76858 (14)	0.0375 (4)
C8	1.2193 (2)	−0.1515 (2)	0.77646 (16)	0.0440 (4)
H8	1.1771	−0.2042	0.7262	0.053*
C5	0.6805 (2)	0.3019 (2)	0.72569 (15)	0.0405 (4)
H5	0.6307	0.3975	0.7462	0.049*
C9	1.3985 (2)	−0.2232 (2)	0.83457 (15)	0.0414 (4)
C21	0.3216 (3)	0.4540 (3)	0.63919 (19)	0.0590 (5)
H21A	0.2956	0.4200	0.7226	0.088*
H21B	0.2003	0.4891	0.6027	0.088*
H21C	0.4061	0.5469	0.6155	0.088*
C10	1.4756 (3)	−0.1447 (2)	0.91735 (15)	0.0427 (4)
H10A	1.3731	−0.1395	0.9778	0.051*
H10B	1.5081	−0.0292	0.8748	0.051*
C4	0.5856 (2)	0.2428 (2)	0.65167 (15)	0.0408 (4)
C31	0.8968 (3)	0.4174 (2)	0.86731 (18)	0.0548 (5)
H31A	0.8984	0.5088	0.7953	0.082*
H31B	0.9863	0.4371	0.9174	0.082*
H31C	0.7667	0.4115	0.9053	0.082*
C11	0.8077 (3)	−0.1881 (2)	0.56160 (17)	0.0535 (5)
H11A	0.6802	−0.2198	0.5982	0.080*
H11B	0.8809	−0.2856	0.5486	0.080*
H11C	0.7938	−0.1015	0.4882	0.080*

	U11	U22	U33	U12	U13	U23
C12	0.0540 (12)	0.0567 (12)	0.0682 (13)	0.0125 (9)	−0.0247 (10)	−0.0277 (10)
O2	0.0432 (7)	0.0571 (8)	0.0729 (9)	0.0161 (6)	−0.0281 (6)	−0.0321 (7)
O1	0.0480 (7)	0.0507 (7)	0.0651 (8)	0.0121 (6)	−0.0228 (6)	−0.0368 (7)
O3	0.0475 (7)	0.0496 (7)	0.0707 (9)	0.0177 (6)	−0.0281 (6)	−0.0391 (7)
C2	0.0383 (9)	0.0378 (9)	0.0456 (10)	0.0026 (7)	−0.0072 (7)	−0.0201 (8)
C1	0.0339 (9)	0.0384 (9)	0.0434 (10)	0.0034 (7)	−0.0085 (7)	−0.0177 (8)
O4	0.0663 (9)	0.0600 (9)	0.0944 (11)	0.0310 (7)	−0.0347 (8)	−0.0504 (8)
C3	0.0412 (10)	0.0478 (10)	0.0495 (11)	0.0017 (8)	−0.0167 (8)	−0.0241 (9)
C7	0.0358 (9)	0.0394 (9)	0.0452 (10)	0.0036 (7)	−0.0106 (7)	−0.0199 (8)
C6	0.0355 (9)	0.0389 (9)	0.0431 (9)	0.0025 (7)	−0.0095 (7)	−0.0190 (8)
C8	0.0435 (10)	0.0436 (10)	0.0538 (11)	0.0070 (8)	−0.0168 (8)	−0.0261 (9)
C5	0.0385 (9)	0.0364 (9)	0.0498 (10)	0.0063 (7)	−0.0096 (8)	−0.0181 (8)
C9	0.0405 (9)	0.0371 (9)	0.0497 (11)	0.0073 (8)	−0.0087 (8)	−0.0190 (8)
C21	0.0445 (11)	0.0633 (13)	0.0740 (14)	0.0208 (9)	−0.0200 (10)	−0.0298 (11)
C10	0.0436 (10)	0.0390 (9)	0.0485 (10)	0.0055 (8)	−0.0107 (8)	−0.0175 (8)
C4	0.0330 (9)	0.0431 (10)	0.0463 (10)	0.0042 (7)	−0.0098 (8)	−0.0132 (8)
C31	0.0526 (11)	0.0507 (11)	0.0773 (14)	0.0156 (9)	−0.0255 (10)	−0.0415 (11)
C11	0.0562 (11)	0.0568 (12)	0.0629 (12)	0.0039 (9)	−0.0177 (9)	−0.0385 (10)

C12—C10	1.514 (2)	C7—H7	0.9300
C12—H12A	0.9600	C6—C5	1.390 (2)
C12—H12B	0.9600	C8—C9	1.463 (2)
C12—H12C	0.9600	C8—H8	0.9300
O2—C4	1.3620 (19)	C5—C4	1.381 (2)
O2—C21	1.423 (2)	C5—H5	0.9300
O1—C2	1.3584 (19)	C9—C10	1.508 (2)
O1—C11	1.4287 (19)	C21—H21A	0.9600
O3—C6	1.3629 (19)	C21—H21B	0.9600
O3—C31	1.4253 (19)	C21—H21C	0.9600
C2—C3	1.382 (2)	C10—H10A	0.9700
C2—C1	1.412 (2)	C10—H10B	0.9700
C1—C6	1.409 (2)	C31—H31A	0.9600
C1—C7	1.452 (2)	C31—H31B	0.9600
O4—C9	1.2206 (19)	C31—H31C	0.9600
C3—C4	1.385 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C7—C8	1.332 (2)	C11—H11C	0.9600
C10—C12—H12A	109.5	O4—C9—C8	118.99 (15)
C10—C12—H12B	109.5	O4—C9—C10	120.39 (15)
H12A—C12—H12B	109.5	C8—C9—C10	120.62 (14)
C10—C12—H12C	109.5	O2—C21—H21A	109.5
H12A—C12—H12C	109.5	O2—C21—H21B	109.5
H12B—C12—H12C	109.5	H21A—C21—H21B	109.5
C4—O2—C21	118.09 (13)	O2—C21—H21C	109.5
C2—O1—C11	118.44 (13)	H21A—C21—H21C	109.5
C6—O3—C31	119.00 (12)	H21B—C21—H21C	109.5
O1—C2—C3	122.66 (14)	C9—C10—C12	113.02 (14)
O1—C2—C1	115.88 (14)	C9—C10—H10A	109.0
C3—C2—C1	121.46 (14)	C12—C10—H10A	109.0
C6—C1—C2	116.34 (14)	C9—C10—H10B	109.0
C6—C1—C7	118.79 (15)	C12—C10—H10B	109.0
C2—C1—C7	124.87 (14)	H10A—C10—H10B	107.8
C2—C3—C4	119.62 (15)	O2—C4—C5	124.12 (15)
C2—C3—H3	120.2	O2—C4—C3	114.18 (14)
C4—C3—H3	120.2	C5—C4—C3	121.69 (15)
C8—C7—C1	130.83 (16)	O3—C31—H31A	109.5
C8—C7—H7	114.6	O3—C31—H31B	109.5
C1—C7—H7	114.6	H31A—C31—H31B	109.5
O3—C6—C5	121.97 (14)	O3—C31—H31C	109.5
O3—C6—C1	115.08 (13)	H31A—C31—H31C	109.5
C5—C6—C1	122.94 (14)	H31B—C31—H31C	109.5
C7—C8—C9	124.60 (15)	O1—C11—H11A	109.5
C7—C8—H8	117.7	O1—C11—H11B	109.5
C9—C8—H8	117.7	H11A—C11—H11B	109.5
C4—C5—C6	117.93 (15)	O1—C11—H11C	109.5
C4—C5—H5	121.0	H11A—C11—H11C	109.5
C6—C5—H5	121.0	H11B—C11—H11C	109.5
C11—O1—C2—C3	−2.0 (2)	C7—C1—C6—C5	−179.07 (16)
C11—O1—C2—C1	177.92 (16)	C1—C7—C8—C9	−179.80 (17)
O1—C2—C1—C6	179.96 (15)	O3—C6—C5—C4	−178.96 (16)
C3—C2—C1—C6	−0.1 (2)	C1—C6—C5—C4	0.0 (3)
O1—C2—C1—C7	−0.5 (3)	C7—C8—C9—O4	−179.72 (18)
C3—C2—C1—C7	179.42 (17)	C7—C8—C9—C10	0.1 (3)
O1—C2—C3—C4	179.20 (16)	O4—C9—C10—C12	−3.5 (3)
C1—C2—C3—C4	−0.8 (3)	C8—C9—C10—C12	176.69 (17)
C6—C1—C7—C8	−178.60 (19)	C21—O2—C4—C5	−3.7 (3)
C2—C1—C7—C8	1.9 (3)	C21—O2—C4—C3	176.19 (16)
C31—O3—C6—C5	−7.9 (3)	C6—C5—C4—O2	178.94 (16)
C31—O3—C6—C1	173.02 (16)	C6—C5—C4—C3	−0.9 (3)
C2—C1—C6—O3	179.50 (15)	C2—C3—C4—O2	−178.58 (16)
C7—C1—C6—O3	0.0 (2)	C2—C3—C4—C5	1.3 (3)
C2—C1—C6—C5	0.5 (3)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.93	2.59	3.517 (2)	177
C31—H31C···O4i	0.96	2.70	3.286 (2)	120
C21—H21C···O2ii	0.96	2.76	3.419 (2)	127
C11—H11A···O4iii	0.96	2.75	3.557 (2)	142
C12—H12C···O4iv	0.96	2.76	3.706 (2)	167
C10—H10B···Cgv	0.97	2.77	3.59	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.93	2.59	3.517 (2)	177
C31—H31C⋯O4i	0.96	2.70	3.286 (2)	120
C21—H21C⋯O2ii	0.96	2.76	3.419 (2)	127
C11—H11A⋯O4iii	0.96	2.75	3.557 (2)	142
C12—H12C⋯O4iv	0.96	2.76	3.706 (2)	167
C10—H10B⋯Cgv	0.97	2.77	3.59	142

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