(E)-1-(2-Fur-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title heteroaryl chalcone derivative, C(16)H(16)O(5), the dihedral angle between the furan and benzene rings is 14.45 (6)°. The three meth-oxy groups are almost coplanar with their attached benzene ring [C-C-O-C torsion angles = 2.07 (17), -5.04 (17) and 2.85 (16)°]. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, adjacent mol-ecules are linked into X-shaped chains along the c axis by weak C-H⋯O(enone) inter-actions. These chains are stacked along the b axis. C⋯O [3.3308 (13)-3.4123 (14) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Suwunwong et al. (2009 ▶. For background to and applications of chalcones and heteroaryl chalcones, see: Gaber et al. (2008 ▶); Go et al. (2005 ▶); Jung et al. (2008 ▶); Ng et al. (2009 ▶); Ni et al. (2004 ▶); Nowakowska (2007 ▶); Patil & Dharmaprakash (2008 ▶) and Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C16H16O5

M = 288.29

Monoclinic,

a = 38.5688 (5) Å

b = 3.93493 (5) Å

c = 18.2638 (3) Å

β = 103.901 (1)°

V = 2690.68 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.41 × 0.15 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.990

20657 measured reflections

3941 independent reflections

3077 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.06

3941 reflections

254 parameters

All H-atom parameters refined

Δρmax = 0.35 e Å−3

Δρmin = −0.24 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/S1600536810035762/hb5630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035762/hb5630Isup2.hkl

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

C16H16O5	F(000) = 1216
Mr = 288.29	Dx = 1.423 Mg m−3
Monoclinic, C2/c	Melting point = 390–391 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.5688 (5) Å	Cell parameters from 3941 reflections
b = 3.93493 (5) Å	θ = 1.1–30.0°
c = 18.2638 (3) Å	µ = 0.11 mm−1
β = 103.901 (1)°	T = 100 K
V = 2690.68 (6) Å3	Block, colorless
Z = 8	0.41 × 0.15 × 0.09 mm

Bruker APEXII CCD diffractometer	3941 independent reflections
Radiation source: sealed tube	3077 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 30.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −54→54
Tmin = 0.957, Tmax = 0.990	k = −5→5
20657 measured reflections	l = −25→25

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0556P)2 + 1.4768P] where P = (Fo2 + 2Fc2)/3
3941 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.24 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 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	0.15077 (2)	0.0988 (3)	0.84899 (5)	0.0215 (2)
O2	0.21727 (2)	0.3478 (2)	0.90839 (4)	0.01663 (19)
O3	0.05690 (2)	−0.2197 (2)	0.65467 (5)	0.01694 (19)
O4	0.04708 (2)	−0.1724 (2)	0.39117 (5)	0.01735 (19)
O5	0.15024 (2)	0.2851 (2)	0.56781 (5)	0.01639 (19)
C1	0.25039 (3)	0.4913 (3)	0.92049 (7)	0.0174 (2)
H1	0.2651 (4)	0.474 (4)	0.9706 (8)	0.018 (4)*
C2	0.25591 (3)	0.6274 (3)	0.85645 (7)	0.0188 (3)
H2	0.2775 (4)	0.741 (4)	0.8513 (9)	0.027 (4)*
C3	0.22403 (3)	0.5659 (3)	0.79963 (7)	0.0174 (2)
H3	0.2194 (4)	0.630 (4)	0.7461 (9)	0.021 (4)*
C4	0.20144 (3)	0.3929 (3)	0.83315 (6)	0.0141 (2)
C5	0.16581 (3)	0.2391 (3)	0.80482 (6)	0.0150 (2)
C6	0.15171 (3)	0.2521 (3)	0.72275 (7)	0.0153 (2)
H6	0.1649 (4)	0.381 (4)	0.6935 (8)	0.019 (4)*
C7	0.12181 (3)	0.0762 (3)	0.69077 (6)	0.0145 (2)
H7	0.1101 (4)	−0.049 (4)	0.7240 (8)	0.020 (4)*
C8	0.10376 (3)	0.0332 (3)	0.61194 (6)	0.0133 (2)
C9	0.06997 (3)	−0.1318 (3)	0.59416 (6)	0.0132 (2)
C10	0.05156 (3)	−0.1931 (3)	0.52043 (7)	0.0150 (2)
H10	0.0282 (4)	−0.310 (4)	0.5082 (9)	0.027 (4)*
C11	0.06682 (3)	−0.0939 (3)	0.46185 (6)	0.0140 (2)
C12	0.09968 (3)	0.0689 (3)	0.47557 (6)	0.0139 (2)
H12	0.1100 (4)	0.127 (4)	0.4359 (8)	0.018 (4)*
C13	0.11766 (3)	0.1321 (3)	0.55034 (6)	0.0131 (2)
C14	0.02326 (3)	−0.3920 (3)	0.63942 (7)	0.0177 (2)
H14A	0.0040 (4)	−0.255 (4)	0.6091 (8)	0.018 (4)*
H14B	0.0253 (4)	−0.612 (4)	0.6129 (8)	0.021 (4)*
H14C	0.0183 (4)	−0.431 (4)	0.6887 (9)	0.023 (4)*
C15	0.06015 (4)	−0.0546 (4)	0.32866 (7)	0.0206 (3)
H15A	0.0833 (4)	−0.158 (4)	0.3269 (9)	0.024 (4)*
H15B	0.0411 (5)	−0.122 (4)	0.2834 (9)	0.032 (4)*
H15C	0.0620 (4)	0.196 (4)	0.3296 (9)	0.024 (4)*
C16	0.16511 (3)	0.3953 (3)	0.50694 (7)	0.0158 (2)
H16A	0.1703 (4)	0.200 (4)	0.4778 (9)	0.021 (4)*
H16B	0.1490 (4)	0.555 (4)	0.4762 (8)	0.015 (3)*
H16C	0.1875 (4)	0.511 (4)	0.5307 (8)	0.020 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0194 (4)	0.0314 (5)	0.0145 (4)	−0.0052 (4)	0.0057 (3)	0.0020 (4)
O2	0.0151 (4)	0.0227 (5)	0.0111 (4)	−0.0018 (3)	0.0012 (3)	0.0000 (3)
O3	0.0143 (4)	0.0231 (5)	0.0142 (4)	−0.0047 (3)	0.0049 (3)	0.0000 (3)
O4	0.0162 (4)	0.0239 (5)	0.0111 (4)	−0.0038 (3)	0.0015 (3)	−0.0018 (3)
O5	0.0130 (4)	0.0242 (5)	0.0119 (4)	−0.0051 (3)	0.0029 (3)	0.0009 (3)
C1	0.0152 (5)	0.0204 (6)	0.0157 (6)	−0.0013 (4)	0.0017 (4)	−0.0018 (5)
C2	0.0174 (6)	0.0211 (6)	0.0182 (6)	−0.0039 (5)	0.0049 (5)	−0.0022 (5)
C3	0.0193 (6)	0.0193 (6)	0.0133 (5)	−0.0018 (4)	0.0037 (4)	−0.0014 (5)
C4	0.0152 (5)	0.0171 (6)	0.0094 (5)	0.0016 (4)	0.0016 (4)	−0.0009 (4)
C5	0.0149 (5)	0.0171 (6)	0.0131 (5)	0.0011 (4)	0.0038 (4)	−0.0007 (4)
C6	0.0155 (5)	0.0172 (6)	0.0131 (5)	−0.0002 (4)	0.0033 (4)	0.0004 (4)
C7	0.0146 (5)	0.0169 (6)	0.0122 (5)	0.0018 (4)	0.0038 (4)	−0.0003 (4)
C8	0.0129 (5)	0.0147 (5)	0.0124 (5)	0.0009 (4)	0.0032 (4)	−0.0001 (4)
C9	0.0135 (5)	0.0139 (5)	0.0129 (5)	0.0006 (4)	0.0048 (4)	0.0008 (4)
C10	0.0125 (5)	0.0170 (6)	0.0150 (5)	−0.0007 (4)	0.0027 (4)	−0.0006 (4)
C11	0.0132 (5)	0.0153 (6)	0.0121 (5)	0.0011 (4)	0.0003 (4)	−0.0012 (4)
C12	0.0133 (5)	0.0163 (6)	0.0121 (5)	0.0014 (4)	0.0031 (4)	0.0006 (4)
C13	0.0106 (5)	0.0133 (5)	0.0152 (5)	−0.0001 (4)	0.0028 (4)	0.0002 (4)
C14	0.0142 (5)	0.0197 (6)	0.0199 (6)	−0.0029 (4)	0.0058 (5)	0.0018 (5)
C15	0.0232 (6)	0.0265 (7)	0.0117 (5)	−0.0043 (5)	0.0036 (5)	0.0000 (5)
C16	0.0143 (5)	0.0205 (6)	0.0133 (5)	−0.0023 (4)	0.0043 (4)	0.0024 (5)

O1—C5	1.2315 (14)	C7—C8	1.4507 (16)
O2—C1	1.3652 (14)	C7—H7	0.974 (15)
O2—C4	1.3745 (13)	C8—C13	1.4123 (15)
O3—C9	1.3648 (13)	C8—C9	1.4220 (15)
O3—C14	1.4307 (14)	C9—C10	1.3844 (16)
O4—C11	1.3673 (14)	C10—C11	1.3949 (16)
O4—C15	1.4317 (15)	C10—H10	0.988 (16)
O5—C13	1.3602 (13)	C11—C12	1.3883 (16)
O5—C16	1.4352 (14)	C12—C13	1.3974 (16)
C1—C2	1.3492 (17)	C12—H12	0.936 (15)
C1—H1	0.956 (15)	C14—H14A	0.976 (15)
C2—C3	1.4264 (17)	C14—H14B	1.003 (16)
C2—H2	0.970 (16)	C14—H14C	0.977 (16)
C3—C4	1.3617 (17)	C15—H15A	0.989 (16)
C3—H3	0.984 (15)	C15—H15B	1.001 (17)
C4—C5	1.4766 (16)	C15—H15C	0.990 (17)
C5—C6	1.4675 (16)	C16—H16A	0.982 (16)
C6—C7	1.3512 (16)	C16—H16B	0.963 (15)
C6—H6	0.967 (15)	C16—H16C	0.982 (16)
C1—O2—C4	106.39 (9)	C9—C10—C11	119.01 (10)
C9—O3—C14	117.18 (9)	C9—C10—H10	121.8 (9)
C11—O4—C15	117.18 (9)	C11—C10—H10	119.2 (9)
C13—O5—C16	118.08 (9)	O4—C11—C12	123.50 (10)
C2—C1—O2	111.12 (10)	O4—C11—C10	114.76 (10)
C2—C1—H1	132.6 (9)	C12—C11—C10	121.74 (10)
O2—C1—H1	116.2 (9)	C11—C12—C13	118.39 (10)
C1—C2—C3	105.98 (11)	C11—C12—H12	120.9 (9)
C1—C2—H2	125.8 (10)	C13—C12—H12	120.7 (9)
C3—C2—H2	128.2 (10)	O5—C13—C12	121.43 (10)
C4—C3—C2	106.90 (11)	O5—C13—C8	116.18 (10)
C4—C3—H3	126.4 (9)	C12—C13—C8	122.37 (10)
C2—C3—H3	126.7 (9)	O3—C14—H14A	112.3 (9)
C3—C4—O2	109.60 (10)	O3—C14—H14B	109.3 (8)
C3—C4—C5	133.59 (11)	H14A—C14—H14B	109.8 (12)
O2—C4—C5	116.74 (10)	O3—C14—H14C	105.3 (9)
O1—C5—C6	124.57 (11)	H14A—C14—H14C	108.5 (12)
O1—C5—C4	119.95 (10)	H14B—C14—H14C	111.5 (13)
C6—C5—C4	115.40 (10)	O4—C15—H15A	112.7 (9)
C7—C6—C5	119.48 (11)	O4—C15—H15B	104.0 (10)
C7—C6—H6	122.6 (9)	H15A—C15—H15B	110.8 (13)
C5—C6—H6	117.9 (9)	O4—C15—H15C	110.3 (9)
C6—C7—C8	130.17 (11)	H15A—C15—H15C	110.6 (13)
C6—C7—H7	117.8 (9)	H15B—C15—H15C	108.2 (14)
C8—C7—H7	112.0 (9)	O5—C16—H16A	110.8 (9)
C13—C8—C9	116.51 (10)	O5—C16—H16B	109.1 (8)
C13—C8—C7	125.09 (10)	H16A—C16—H16B	112.5 (12)
C9—C8—C7	118.36 (10)	O5—C16—H16C	105.8 (8)
O3—C9—C10	122.72 (10)	H16A—C16—H16C	109.3 (12)
O3—C9—C8	115.31 (10)	H16B—C16—H16C	109.2 (13)
C10—C9—C8	121.96 (10)
C4—O2—C1—C2	0.63 (14)	C7—C8—C9—O3	3.17 (16)
O2—C1—C2—C3	−0.01 (15)	C13—C8—C9—C10	0.06 (17)
C1—C2—C3—C4	−0.63 (14)	C7—C8—C9—C10	−177.77 (11)
C2—C3—C4—O2	1.03 (14)	O3—C9—C10—C11	179.79 (11)
C2—C3—C4—C5	−175.73 (13)	C8—C9—C10—C11	0.80 (18)
C1—O2—C4—C3	−1.03 (13)	C15—O4—C11—C12	−5.04 (17)
C1—O2—C4—C5	176.35 (10)	C15—O4—C11—C10	175.53 (11)
C3—C4—C5—O1	−178.75 (13)	C9—C10—C11—O4	178.49 (10)
O2—C4—C5—O1	4.67 (17)	C9—C10—C11—C12	−0.95 (18)
C3—C4—C5—C6	4.4 (2)	O4—C11—C12—C13	−179.17 (11)
O2—C4—C5—C6	−172.18 (10)	C10—C11—C12—C13	0.22 (18)
O1—C5—C6—C7	−6.08 (19)	C16—O5—C13—C12	2.85 (16)
C4—C5—C6—C7	170.60 (11)	C16—O5—C13—C8	−178.91 (10)
C5—C6—C7—C8	−176.44 (12)	C11—C12—C13—O5	178.81 (10)
C6—C7—C8—C13	10.2 (2)	C11—C12—C13—C8	0.69 (18)
C6—C7—C8—C9	−172.18 (12)	C9—C8—C13—O5	−179.03 (10)
C14—O3—C9—C10	2.07 (17)	C7—C8—C13—O5	−1.37 (17)
C14—O3—C9—C8	−178.87 (10)	C9—C8—C13—C12	−0.82 (17)
C13—C8—C9—O3	−179.00 (10)	C7—C8—C13—C12	176.84 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6···O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A···O4ii	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A···O1iii	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A···O1iii	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6⋯O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A⋯O4ii	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A⋯O1iii	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A⋯O1iii	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)

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