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

In the title chalcone derivative, C(16)H(16)O(5), the dihedral angle between the furan and benzene rings is 2.06 (17)°. The two meth-oxy groups at the ortho and para positions are essentially coplanar with the benzene ring [C-O-C-C angles = -1.0 (5) and 178.5 (3)°], whereas the third one at the meta position is slightly twisted [C-O-C-C = 9.6 (5)°]. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into a sheet parallel to ([Formula: see text]02). An inter-molecular π-π inter-action between the furan and benzene rings is present [centroid-centroid distance = 3.772 (2) Å]. A short C⋯C contact [3.173 (5) Å] is also observed between neighbouring furan rings.

Related literature

For background to and applications of chalcones, see: Cheng et al. (2008 ▶); Jung et al. (2008 ▶); Lee et al. (2006 ▶); Liu et al. (2011 ▶); Nerya et al. (2004 ▶); Suwunwong et al. (2011 ▶); Tewtrakul et al. (2003 ▶). For related structures, see: Fun et al. (2010a ▶,b ▶, 2011 ▶). For the stability of the temperature controller, see: Cosier & Glazer, (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16O5

M = 288.29

Monoclinic,

a = 8.338 (2) Å

b = 8.610 (2) Å

c = 18.923 (5) Å

β = 94.467 (4)°

V = 1354.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.28 × 0.21 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.991

8001 measured reflections

2647 independent reflections

1663 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.175

S = 1.08

2647 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812000037/is5037sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000037/is5037Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000037/is5037Isup3.cml

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

C16H16O5	F(000) = 608
Mr = 288.29	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Melting point = 356–357 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.338 (2) Å	Cell parameters from 2647 reflections
b = 8.610 (2) Å	θ = 2.2–26.0°
c = 18.923 (5) Å	µ = 0.11 mm−1
β = 94.467 (4)°	T = 100 K
V = 1354.4 (6) Å3	Plate, yellow
Z = 4	0.28 × 0.21 × 0.09 mm

Bruker APEX DUO CCD area-detector diffractometer	2647 independent reflections
Radiation source: sealed tube	1663 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
Tmin = 0.971, Tmax = 0.991	k = −10→7
8001 measured reflections	l = −23→23

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0653P)2 + 1.5283P] where P = (Fo2 + 2Fc2)/3
2647 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.40 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 100.0 (1) K.

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
O1	0.8947 (3)	1.0580 (3)	0.56583 (11)	0.0221 (6)
O2	0.8198 (3)	0.6581 (3)	0.53014 (11)	0.0219 (6)
O3	0.5846 (3)	1.3849 (3)	0.41496 (11)	0.0234 (6)
O4	0.1930 (3)	1.2112 (3)	0.22782 (11)	0.0203 (6)
O5	0.2463 (3)	0.9265 (3)	0.26329 (11)	0.0211 (6)
C1	0.8927 (5)	0.5329 (4)	0.56403 (17)	0.0249 (9)
H1A	0.8673	0.4297	0.5539	0.030*
C2	1.0063 (4)	0.5797 (4)	0.61407 (17)	0.0244 (9)
H2A	1.0717	0.5167	0.6440	0.029*
C3	1.0061 (4)	0.7441 (4)	0.61196 (17)	0.0218 (8)
H3A	1.0719	0.8098	0.6404	0.026*
C4	0.8920 (4)	0.7884 (4)	0.56070 (15)	0.0177 (7)
C5	0.8371 (4)	0.9414 (4)	0.53558 (15)	0.0181 (8)
C6	0.7141 (4)	0.9497 (4)	0.47546 (15)	0.0177 (8)
H6A	0.6743	0.8590	0.4539	0.021*
C7	0.6597 (4)	1.0876 (4)	0.45188 (16)	0.0174 (8)
H7A	0.7039	1.1740	0.4756	0.021*
C8	0.5399 (4)	1.1191 (4)	0.39374 (15)	0.0157 (7)
C9	0.5031 (4)	1.2735 (4)	0.37474 (16)	0.0172 (8)
C10	0.3898 (4)	1.3086 (4)	0.31901 (15)	0.0162 (7)
H10A	0.3691	1.4115	0.3065	0.019*
C11	0.3084 (4)	1.1903 (4)	0.28248 (15)	0.0145 (7)
C12	0.3391 (4)	1.0334 (4)	0.30161 (15)	0.0152 (7)
C13	0.4544 (4)	1.0014 (4)	0.35535 (15)	0.0155 (7)
H13A	0.4769	0.8982	0.3668	0.019*
C14	0.5532 (5)	1.5429 (4)	0.39800 (19)	0.0317 (10)
H14B	0.6202	1.6080	0.4291	0.048*
H14C	0.4421	1.5656	0.4036	0.048*
H14D	0.5759	1.5621	0.3498	0.048*
C15	0.1539 (4)	1.3692 (4)	0.20725 (16)	0.0190 (8)
H15C	0.0763	1.3687	0.1670	0.029*
H15D	0.2495	1.4216	0.1951	0.029*
H15A	0.1098	1.4221	0.2460	0.029*
C16	0.2548 (5)	0.7704 (4)	0.28869 (17)	0.0234 (8)
H16D	0.1717	0.7097	0.2640	0.035*
H16A	0.2406	0.7694	0.3385	0.035*
H16B	0.3580	0.7272	0.2806	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0219 (15)	0.0236 (14)	0.0194 (11)	−0.0015 (11)	−0.0062 (10)	−0.0033 (10)
O2	0.0214 (15)	0.0215 (14)	0.0214 (11)	0.0010 (11)	−0.0076 (10)	0.0023 (10)
O3	0.0271 (16)	0.0136 (13)	0.0269 (12)	−0.0014 (11)	−0.0148 (11)	0.0006 (10)
O4	0.0225 (15)	0.0167 (13)	0.0198 (11)	0.0022 (11)	−0.0106 (10)	0.0018 (9)
O5	0.0236 (15)	0.0138 (13)	0.0239 (11)	−0.0038 (11)	−0.0105 (10)	−0.0012 (9)
C1	0.029 (2)	0.0191 (19)	0.0261 (17)	0.0075 (18)	0.0009 (16)	0.0063 (15)
C2	0.020 (2)	0.033 (2)	0.0205 (16)	0.0054 (17)	0.0015 (15)	0.0070 (15)
C3	0.016 (2)	0.030 (2)	0.0187 (15)	−0.0001 (16)	−0.0019 (14)	0.0027 (14)
C4	0.0135 (19)	0.0238 (19)	0.0153 (14)	−0.0026 (16)	−0.0016 (13)	−0.0002 (14)
C5	0.015 (2)	0.024 (2)	0.0155 (15)	0.0011 (16)	−0.0012 (13)	0.0006 (14)
C6	0.014 (2)	0.0200 (19)	0.0183 (15)	−0.0021 (15)	−0.0049 (13)	−0.0002 (13)
C7	0.0129 (19)	0.0218 (19)	0.0174 (15)	−0.0026 (14)	0.0011 (13)	−0.0004 (13)
C8	0.0157 (19)	0.0169 (18)	0.0140 (14)	−0.0004 (15)	−0.0018 (13)	0.0002 (13)
C9	0.0143 (19)	0.0176 (18)	0.0189 (15)	−0.0029 (15)	−0.0032 (14)	−0.0008 (13)
C10	0.0144 (19)	0.0155 (18)	0.0184 (15)	0.0016 (15)	0.0000 (13)	0.0022 (13)
C11	0.0096 (18)	0.0189 (18)	0.0146 (14)	0.0037 (14)	−0.0017 (13)	0.0016 (13)
C12	0.0115 (18)	0.0181 (18)	0.0155 (14)	−0.0002 (15)	−0.0023 (13)	−0.0017 (13)
C13	0.0132 (19)	0.0161 (18)	0.0166 (15)	0.0008 (14)	−0.0035 (13)	0.0006 (12)
C14	0.044 (3)	0.0117 (19)	0.036 (2)	−0.0027 (19)	−0.0158 (18)	0.0021 (16)
C15	0.019 (2)	0.0172 (18)	0.0196 (15)	0.0027 (15)	−0.0046 (14)	0.0063 (13)
C16	0.029 (2)	0.0140 (19)	0.0259 (17)	−0.0021 (16)	−0.0058 (15)	−0.0004 (14)

O1—C5	1.234 (4)	C7—C8	1.453 (5)
O2—C1	1.372 (4)	C7—H7A	0.9300
O2—C4	1.379 (4)	C8—C9	1.405 (5)
O3—C9	1.371 (4)	C8—C13	1.408 (4)
O3—C14	1.418 (4)	C9—C10	1.393 (5)
O4—C11	1.369 (4)	C10—C11	1.379 (5)
O4—C15	1.445 (4)	C10—H10A	0.9300
O5—C12	1.373 (4)	C11—C12	1.416 (5)
O5—C16	1.427 (4)	C12—C13	1.372 (4)
C1—C2	1.347 (5)	C13—H13A	0.9300
C1—H1A	0.9300	C14—H14B	0.9600
C2—C3	1.416 (5)	C14—H14C	0.9600
C2—H2A	0.9300	C14—H14D	0.9600
C3—C4	1.359 (5)	C15—H15C	0.9600
C3—H3A	0.9300	C15—H15D	0.9600
C4—C5	1.462 (5)	C15—H15A	0.9600
C5—C6	1.473 (4)	C16—H16D	0.9600
C6—C7	1.335 (5)	C16—H16A	0.9600
C6—H6A	0.9300	C16—H16B	0.9600
C1—O2—C4	106.3 (3)	C11—C10—C9	119.9 (3)
C9—O3—C14	118.1 (3)	C11—C10—H10A	120.1
C11—O4—C15	117.3 (3)	C9—C10—H10A	120.1
C12—O5—C16	116.2 (3)	O4—C11—C10	124.8 (3)
C2—C1—O2	110.8 (3)	O4—C11—C12	114.9 (3)
C2—C1—H1A	124.6	C10—C11—C12	120.2 (3)
O2—C1—H1A	124.6	C13—C12—O5	126.2 (3)
C1—C2—C3	106.3 (3)	C13—C12—C11	118.9 (3)
C1—C2—H2A	126.9	O5—C12—C11	114.9 (3)
C3—C2—H2A	126.9	C12—C13—C8	122.3 (3)
C4—C3—C2	107.4 (3)	C12—C13—H13A	118.8
C4—C3—H3A	126.3	C8—C13—H13A	118.8
C2—C3—H3A	126.3	O3—C14—H14B	109.5
C3—C4—O2	109.2 (3)	O3—C14—H14C	109.5
C3—C4—C5	132.0 (3)	H14B—C14—H14C	109.5
O2—C4—C5	118.8 (3)	O3—C14—H14D	109.5
O1—C5—C4	118.8 (3)	H14B—C14—H14D	109.5
O1—C5—C6	122.7 (3)	H14C—C14—H14D	109.5
C4—C5—C6	118.5 (3)	O4—C15—H15C	109.5
C7—C6—C5	120.0 (3)	O4—C15—H15D	109.5
C7—C6—H6A	120.0	H15C—C15—H15D	109.5
C5—C6—H6A	120.0	O4—C15—H15A	109.5
C6—C7—C8	128.0 (3)	H15C—C15—H15A	109.5
C6—C7—H7A	116.0	H15D—C15—H15A	109.5
C8—C7—H7A	116.0	O5—C16—H16D	109.5
C9—C8—C13	117.2 (3)	O5—C16—H16A	109.5
C9—C8—C7	119.6 (3)	H16D—C16—H16A	109.5
C13—C8—C7	123.1 (3)	O5—C16—H16B	109.5
O3—C9—C10	123.1 (3)	H16D—C16—H16B	109.5
O3—C9—C8	115.5 (3)	H16A—C16—H16B	109.5
C10—C9—C8	121.4 (3)
C4—O2—C1—C2	0.1 (4)	C7—C8—C9—O3	−1.1 (4)
O2—C1—C2—C3	−0.1 (4)	C13—C8—C9—C10	−1.6 (5)
C1—C2—C3—C4	0.1 (4)	C7—C8—C9—C10	179.5 (3)
C2—C3—C4—O2	0.0 (4)	O3—C9—C10—C11	−177.7 (3)
C2—C3—C4—C5	179.1 (3)	C8—C9—C10—C11	1.6 (5)
C1—O2—C4—C3	0.0 (3)	C15—O4—C11—C10	−0.1 (4)
C1—O2—C4—C5	−179.3 (3)	C15—O4—C11—C12	178.5 (3)
C3—C4—C5—O1	−3.5 (5)	C9—C10—C11—O4	178.8 (3)
O2—C4—C5—O1	175.6 (3)	C9—C10—C11—C12	0.3 (4)
C3—C4—C5—C6	177.0 (3)	C16—O5—C12—C13	9.6 (5)
O2—C4—C5—C6	−3.9 (4)	C16—O5—C12—C11	−170.0 (3)
O1—C5—C6—C7	−0.4 (5)	O4—C11—C12—C13	179.2 (3)
C4—C5—C6—C7	179.1 (3)	C10—C11—C12—C13	−2.1 (4)
C5—C6—C7—C8	179.9 (3)	O4—C11—C12—O5	−1.1 (4)
C6—C7—C8—C9	−177.3 (3)	C10—C11—C12—O5	177.6 (3)
C6—C7—C8—C13	4.0 (5)	O5—C12—C13—C8	−177.5 (3)
C14—O3—C9—C10	−1.0 (5)	C11—C12—C13—C8	2.1 (5)
C14—O3—C9—C8	179.6 (3)	C9—C8—C13—C12	−0.2 (5)
C13—C8—C9—O3	177.7 (3)	C7—C8—C13—C12	178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2i	0.96	2.47	3.363 (5)	154
C15—H15C···O1ii	0.96	2.43	3.365 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2i	0.96	2.47	3.363 (5)	154
C15—H15C⋯O1ii	0.96	2.43	3.365 (4)	165

Symmetry codes: (i) ; (ii) .