(E)-1-(2-Fur-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

The title mol-ecule, C(16)H(16)O(5), is twisted; the dihedral angle between the furan and 3,4,5-trimeth-oxy-phenyl rings is 12.14 (13)°. The two meth-oxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C-O-C-C = -0.6 (3) and 1.4 (3)°], whereas the third meth-oxy group, at the para position, is (+)-anti-clinal with respect to the benzene ring [C-O-C-C = 104.9 (2)°]. In the crystal, mol-ecules are linked by weak C-H⋯O bonds to stack along the b axis and further C-H⋯O inter-actions consolidate the structure.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Batovska et al. (2007 ▶); Gu et al. (2009 ▶); Jung et al. (2008 ▶); Prasad et al. (2008 ▶); Saxena et al. (2007 ▶); Tewtrakul et al. (2003 ▶).

Experimental

Crystal data

C16H16O5

M = 288.29

Orthorhombic,

a = 24.2677 (4) Å

b = 3.9916 (1) Å

c = 14.0816 (2) Å

V = 1364.04 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.978

17261 measured reflections

2063 independent reflections

1907 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.06

2063 reflections

254 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.36 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004451X/hb5713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004451X/hb5713Isup2.hkl

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

C16H16O5	Dx = 1.404 Mg m−3
Mr = 288.29	Melting point = 420–421 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2063 reflections
a = 24.2677 (4) Å	θ = 2.2–30.0°
b = 3.9916 (1) Å	µ = 0.11 mm−1
c = 14.0816 (2) Å	T = 100 K
V = 1364.04 (5) Å3	Block, pale yellow
Z = 4	0.35 × 0.24 × 0.21 mm
F(000) = 608

Bruker APEXII CCD diffractometer	2063 independent reflections
Radiation source: sealed tube	1907 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −29→34
Tmin = 0.965, Tmax = 0.978	k = −5→5
17261 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.4265P] where P = (Fo2 + 2Fc2)/3
2063 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.25005 (6)	0.6063 (4)	0.72174 (11)	0.0251 (3)
O2	0.34121 (7)	0.1635 (4)	0.87377 (12)	0.0271 (4)
O3	0.41052 (6)	0.5004 (4)	0.26993 (10)	0.0181 (3)
O4	0.50168 (6)	0.1761 (4)	0.32189 (11)	0.0181 (3)
O5	0.51882 (6)	−0.0146 (4)	0.50322 (11)	0.0190 (3)
C1	0.33965 (11)	0.1379 (8)	0.96954 (19)	0.0333 (6)
H1A	0.3722 (14)	0.001 (7)	0.995 (2)	0.036 (8)*
C2	0.29645 (12)	0.3011 (8)	1.00503 (17)	0.0342 (6)
H2A	0.2846 (17)	0.331 (11)	1.057 (3)	0.064 (13)*
C3	0.26677 (10)	0.4471 (7)	0.92549 (17)	0.0247 (5)
H3A	0.2426 (12)	0.568 (8)	0.922 (2)	0.026 (8)*
C4	0.29621 (8)	0.3538 (5)	0.84793 (14)	0.0171 (4)
C5	0.28952 (8)	0.4380 (5)	0.74728 (14)	0.0168 (4)
C6	0.33353 (8)	0.3224 (5)	0.68267 (15)	0.0171 (4)
H6A	0.3628 (11)	0.190 (7)	0.709 (2)	0.020 (6)*
C7	0.33640 (8)	0.4294 (5)	0.59260 (14)	0.0167 (4)
H7A	0.3082 (12)	0.566 (7)	0.570 (2)	0.023 (7)*
C8	0.37985 (8)	0.3565 (5)	0.52384 (13)	0.0155 (4)
C9	0.37237 (8)	0.4630 (5)	0.43008 (15)	0.0154 (3)
H9A	0.3401 (11)	0.568 (7)	0.410 (2)	0.019 (6)*
C10	0.41374 (8)	0.4064 (5)	0.36290 (13)	0.0143 (3)
C11	0.46246 (8)	0.2434 (5)	0.38936 (13)	0.0145 (3)
C12	0.46971 (8)	0.1383 (5)	0.48394 (14)	0.0151 (4)
C13	0.42857 (8)	0.1923 (5)	0.55057 (14)	0.0155 (4)
H13A	0.4332 (10)	0.125 (6)	0.615 (2)	0.014 (6)*
C14	0.36071 (8)	0.6651 (6)	0.24098 (15)	0.0189 (4)
H14C	0.3554 (11)	0.873 (7)	0.274 (2)	0.020 (7)*
H14B	0.3290 (12)	0.513 (7)	0.248 (2)	0.019 (7)*
H14A	0.3628 (12)	0.717 (7)	0.177 (2)	0.023 (7)*
C15	0.54913 (9)	0.3915 (6)	0.32550 (18)	0.0224 (4)
H15A	0.5639 (17)	0.395 (12)	0.393 (3)	0.069 (13)*
H15B	0.5367 (14)	0.627 (8)	0.309 (2)	0.040 (9)*
H15C	0.5741 (12)	0.315 (8)	0.277 (2)	0.032 (8)*
C16	0.52677 (9)	−0.1308 (6)	0.59880 (14)	0.0198 (4)
H16A	0.4975 (11)	−0.287 (7)	0.617 (2)	0.022 (7)*
H16B	0.5618 (12)	−0.249 (7)	0.598 (2)	0.023 (7)*
H16C	0.5293 (11)	0.058 (8)	0.645 (2)	0.021 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0218 (7)	0.0366 (8)	0.0169 (7)	0.0091 (7)	0.0035 (6)	0.0052 (7)
O2	0.0229 (7)	0.0313 (9)	0.0272 (9)	−0.0017 (7)	−0.0050 (6)	0.0068 (7)
O3	0.0184 (7)	0.0243 (7)	0.0114 (6)	0.0016 (6)	0.0005 (5)	0.0028 (5)
O4	0.0166 (6)	0.0244 (7)	0.0133 (6)	−0.0004 (6)	0.0038 (5)	−0.0033 (6)
O5	0.0166 (6)	0.0255 (7)	0.0149 (7)	0.0045 (6)	0.0004 (5)	0.0027 (6)
C1	0.0318 (12)	0.0426 (15)	0.0256 (12)	−0.0123 (11)	−0.0095 (9)	0.0101 (10)
C2	0.0455 (15)	0.0456 (15)	0.0113 (9)	−0.0270 (12)	0.0002 (10)	−0.0011 (10)
C3	0.0218 (9)	0.0340 (12)	0.0182 (10)	−0.0103 (10)	0.0068 (8)	−0.0077 (9)
C4	0.0156 (8)	0.0214 (9)	0.0142 (9)	−0.0018 (7)	0.0018 (7)	0.0023 (7)
C5	0.0161 (8)	0.0217 (9)	0.0126 (8)	−0.0029 (7)	0.0028 (7)	0.0009 (7)
C6	0.0154 (8)	0.0185 (9)	0.0175 (9)	0.0017 (7)	0.0017 (7)	−0.0001 (8)
C7	0.0126 (8)	0.0226 (10)	0.0149 (8)	0.0008 (7)	0.0017 (7)	−0.0017 (7)
C8	0.0142 (8)	0.0190 (9)	0.0134 (8)	−0.0022 (7)	0.0008 (6)	−0.0009 (7)
C9	0.0145 (7)	0.0187 (9)	0.0130 (8)	−0.0004 (7)	0.0001 (7)	−0.0006 (7)
C10	0.0162 (8)	0.0154 (8)	0.0112 (8)	−0.0023 (7)	−0.0006 (7)	−0.0001 (7)
C11	0.0141 (7)	0.0167 (8)	0.0127 (8)	−0.0017 (7)	0.0035 (6)	−0.0018 (7)
C12	0.0139 (8)	0.0160 (9)	0.0153 (9)	0.0003 (7)	−0.0017 (6)	−0.0016 (7)
C13	0.0164 (8)	0.0195 (9)	0.0107 (8)	−0.0022 (7)	0.0008 (7)	0.0002 (7)
C14	0.0185 (9)	0.0226 (10)	0.0157 (9)	0.0005 (8)	−0.0033 (7)	0.0026 (8)
C15	0.0196 (9)	0.0214 (10)	0.0262 (10)	−0.0027 (8)	0.0090 (8)	−0.0005 (9)
C16	0.0193 (9)	0.0240 (10)	0.0161 (9)	0.0014 (8)	−0.0025 (8)	0.0046 (8)

O1—C5	1.224 (3)	C7—C8	1.461 (3)
O2—C1	1.353 (3)	C7—H7A	0.93 (3)
O2—C4	1.379 (3)	C8—C9	1.399 (3)
O3—C10	1.364 (2)	C8—C13	1.403 (3)
O3—C14	1.435 (2)	C9—C10	1.398 (3)
O4—C11	1.372 (2)	C9—H9A	0.93 (3)
O4—C15	1.438 (3)	C10—C11	1.400 (3)
O5—C12	1.366 (2)	C11—C12	1.407 (3)
O5—C16	1.437 (2)	C12—C13	1.387 (3)
C1—C2	1.332 (5)	C13—H13A	0.96 (3)
C1—H1A	1.03 (3)	C14—H14C	0.96 (3)
C2—C3	1.454 (4)	C14—H14B	0.99 (3)
C2—H2A	0.80 (5)	C14—H14A	0.93 (3)
C3—C4	1.357 (3)	C15—H15A	1.02 (5)
C3—H3A	0.76 (3)	C15—H15B	1.01 (3)
C4—C5	1.466 (3)	C15—H15C	0.96 (3)
C5—C6	1.477 (3)	C16—H16A	0.98 (3)
C6—C7	1.340 (3)	C16—H16B	0.97 (3)
C6—H6A	0.96 (3)	C16—H16C	1.00 (3)
C1—O2—C4	106.4 (2)	O3—C10—C9	124.33 (18)
C10—O3—C14	116.54 (16)	O3—C10—C11	115.57 (17)
C11—O4—C15	114.47 (16)	C9—C10—C11	120.10 (17)
C12—O5—C16	116.60 (16)	O4—C11—C10	119.52 (17)
C2—C1—O2	111.0 (2)	O4—C11—C12	120.68 (17)
C2—C1—H1A	137.1 (19)	C10—C11—C12	119.74 (17)
O2—C1—H1A	111.8 (19)	O5—C12—C13	124.26 (18)
C1—C2—C3	107.3 (2)	O5—C12—C11	115.50 (17)
C1—C2—H2A	135 (3)	C13—C12—C11	120.25 (17)
C3—C2—H2A	118 (3)	C12—C13—C8	119.85 (18)
C4—C3—C2	104.4 (2)	C12—C13—H13A	121.0 (15)
C4—C3—H3A	122 (3)	C8—C13—H13A	119.1 (15)
C2—C3—H3A	133 (3)	O3—C14—H14C	111.7 (17)
C3—C4—O2	110.8 (2)	O3—C14—H14B	110.3 (16)
C3—C4—C5	131.1 (2)	H14C—C14—H14B	112 (2)
O2—C4—C5	117.99 (17)	O3—C14—H14A	109.5 (18)
O1—C5—C4	119.79 (18)	H14C—C14—H14A	107 (3)
O1—C5—C6	123.80 (19)	H14B—C14—H14A	106 (2)
C4—C5—C6	116.36 (18)	O4—C15—H15A	109 (3)
C7—C6—C5	121.40 (19)	O4—C15—H15B	107.9 (19)
C7—C6—H6A	120.0 (17)	H15A—C15—H15B	108 (3)
C5—C6—H6A	118.1 (17)	O4—C15—H15C	106.8 (19)
C6—C7—C8	126.96 (19)	H15A—C15—H15C	116 (3)
C6—C7—H7A	118.4 (18)	H15B—C15—H15C	109 (3)
C8—C7—H7A	114.6 (18)	O5—C16—H16A	110.7 (17)
C9—C8—C13	120.28 (17)	O5—C16—H16B	105.3 (17)
C9—C8—C7	118.13 (18)	H16A—C16—H16B	109 (2)
C13—C8—C7	121.57 (17)	O5—C16—H16C	111.9 (18)
C10—C9—C8	119.77 (17)	H16A—C16—H16C	111 (2)
C10—C9—H9A	118.2 (18)	H16B—C16—H16C	109 (2)
C8—C9—H9A	122.0 (18)
C4—O2—C1—C2	−0.1 (3)	C14—O3—C10—C11	179.43 (17)
O2—C1—C2—C3	0.1 (3)	C8—C9—C10—O3	−179.95 (18)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—O2	0.0 (2)	C15—O4—C11—C10	104.9 (2)
C2—C3—C4—C5	−175.9 (2)	C15—O4—C11—C12	−77.7 (2)
C1—O2—C4—C3	0.1 (3)	O3—C10—C11—O4	−2.9 (3)
C1—O2—C4—C5	176.5 (2)	C9—C10—C11—O4	177.11 (18)
C3—C4—C5—O1	−4.4 (4)	O3—C10—C11—C12	179.71 (18)
O2—C4—C5—O1	179.97 (19)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	172.9 (2)	C16—O5—C12—C13	1.4 (3)
O2—C4—C5—C6	−2.7 (3)	C16—O5—C12—C11	−178.70 (17)
O1—C5—C6—C7	8.0 (3)	O4—C11—C12—O5	3.4 (3)
C4—C5—C6—C7	−169.2 (2)	C10—C11—C12—O5	−179.21 (17)
C5—C6—C7—C8	174.83 (19)	O4—C11—C12—C13	−176.68 (18)
C6—C7—C8—C9	173.3 (2)	C10—C11—C12—C13	0.7 (3)
C6—C7—C8—C13	−8.3 (3)	O5—C12—C13—C8	179.05 (18)
C13—C8—C9—C10	−0.2 (3)	C11—C12—C13—C8	−0.8 (3)
C7—C8—C9—C10	178.14 (18)	C9—C8—C13—C12	0.6 (3)
C14—O3—C10—C9	−0.6 (3)	C7—C8—C13—C12	−177.69 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1i	0.99 (3)	2.54 (3)	3.503 (3)	166 (2)
C15—H15B···O4ii	1.01 (3)	2.36 (3)	3.337 (3)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1i	0.99 (3)	2.54 (3)	3.503 (3)	166 (2)
C15—H15B⋯O4ii	1.01 (3)	2.36 (3)	3.337 (3)	162 (2)

Symmetry codes: (i) ; (ii) .