(Z)-2-(2-Hy-droxy-4-meth-oxy-benzyl-idene)-1-benzofuran-3(2H)-one.

In the title compound, C(16)H(12)O(4), the 1-benzofuran-one unit is in a planar conformation [C-C-C-C = 179.69 (12)°]. The conformation around the C=C double bond [1.3370 (17) Å] is Z. In the crystal, the mol-ecules are stabilized by O-H⋯O (running parallel to the bc plane) and C-H⋯O hydrogen bonds.

Related literature

For the synthesis and biological activity of substituted aurones, see: Varma & Varma (1992 ▶); Beney et al. (2001 ▶); Sim et al. (2008 ▶); Souard et al. (2010 ▶); Wang et al. (2007 ▶). For aurones as structural scaffolds in natural and synthetic compounds possessing diverse biological properties, see: Villemin et al. (1998 ▶). The title compound, which is an analogue of naturally occurring aurones, holds promise as an inhibitor against human melanocytes tyrosinase towards anti­hyper­pig­ment­ation, see: Okombi et al. (2006 ▶). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983 ▶, 1995 ▶); Klyne & Prelog (1960 ▶).

Experimental

Crystal data

C16H12O4

M = 268.26

Monoclinic,

a = 7.1083 (4) Å

b = 12.7072 (7) Å

c = 14.4024 (8) Å

β = 100.161 (2)°

V = 1280.52 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.906, T max = 0.975

19357 measured reflections

4765 independent reflections

2533 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.150

S = 1.02

4765 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016217/ds2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016217/ds2109Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016217/ds2109Isup3.cml

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

C16H12O4	F(000) = 560
Mr = 268.26	Dx = 1.391 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3249 reflections
a = 7.1083 (4) Å	θ = 2.9–25.3°
b = 12.7072 (7) Å	µ = 0.10 mm−1
c = 14.4024 (8) Å	T = 293 K
β = 100.161 (2)°	Block, yellow
V = 1280.52 (12) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4765 independent reflections
Radiation source: fine-focus sealed tube	2533 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω and φ scans	θmax = 32.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→5
Tmin = 0.906, Tmax = 0.975	k = −17→19
19357 measured reflections	l = −21→21

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.0121P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4765 reflections	Δρmax = 0.26 e Å−3
187 parameters	Δρmin = −0.19 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: 0.0043 (16)

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
C1	0.33155 (18)	0.81587 (10)	0.10935 (9)	0.0378 (3)
C2	0.3577 (2)	0.79394 (12)	0.20448 (10)	0.0498 (4)
H2	0.3493	0.8460	0.2490	0.060*
C3	0.3967 (2)	0.69092 (12)	0.22996 (11)	0.0544 (4)
H3	0.4168	0.6732	0.2936	0.065*
C4	0.4072 (2)	0.61232 (12)	0.16407 (11)	0.0529 (4)
H4	0.4321	0.5433	0.1840	0.064*
C5	0.3811 (2)	0.63594 (11)	0.06989 (11)	0.0487 (4)
H5	0.3888	0.5838	0.0254	0.058*
C6	0.34267 (17)	0.73990 (10)	0.04224 (9)	0.0383 (3)
C7	0.31090 (19)	0.79320 (10)	−0.04815 (9)	0.0409 (3)
C8	0.27856 (18)	0.90379 (10)	−0.02558 (9)	0.0380 (3)
C9	0.24089 (17)	0.98235 (10)	−0.08784 (9)	0.0388 (3)
H9	0.2352	0.9621	−0.1503	0.047*
C10	0.20767 (16)	1.09256 (10)	−0.07510 (9)	0.0362 (3)
C11	0.2172 (2)	1.14095 (10)	0.01304 (10)	0.0440 (3)
H11	0.2418	1.0999	0.0673	0.053*
C12	0.1913 (2)	1.24709 (11)	0.02151 (10)	0.0492 (4)
H12	0.1987	1.2772	0.0809	0.059*
C13	0.15384 (19)	1.30956 (10)	−0.05866 (10)	0.0412 (3)
C14	0.14158 (17)	1.26536 (10)	−0.14673 (9)	0.0389 (3)
H14	0.1155	1.3072	−0.2004	0.047*
C15	0.16833 (18)	1.15787 (10)	−0.15485 (9)	0.0383 (3)
C16	0.0907 (2)	1.48154 (11)	−0.12239 (11)	0.0557 (4)
H16A	0.1933	1.4791	−0.1577	0.083*
H16B	0.0756	1.5523	−0.1015	0.083*
H16C	−0.0256	1.4589	−0.1617	0.083*
O1	0.29265 (13)	0.91457 (7)	0.07146 (6)	0.0425 (2)
O2	0.30983 (16)	0.75813 (8)	−0.12769 (7)	0.0611 (3)
O3	0.15733 (16)	1.11203 (8)	−0.24045 (7)	0.0558 (3)
O4	0.13342 (16)	1.41402 (8)	−0.04288 (7)	0.0556 (3)
H3A	0.153 (3)	1.1617 (15)	−0.2855 (16)	0.092 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0425 (6)	0.0355 (7)	0.0351 (7)	−0.0041 (5)	0.0061 (5)	0.0037 (6)
C2	0.0625 (9)	0.0539 (9)	0.0334 (7)	−0.0009 (7)	0.0092 (6)	0.0034 (7)
C3	0.0590 (9)	0.0622 (10)	0.0417 (8)	0.0000 (7)	0.0081 (7)	0.0153 (8)
C4	0.0516 (8)	0.0457 (9)	0.0598 (10)	0.0006 (6)	0.0052 (7)	0.0184 (7)
C5	0.0538 (8)	0.0382 (8)	0.0518 (9)	0.0018 (6)	0.0032 (6)	0.0015 (7)
C6	0.0413 (6)	0.0349 (7)	0.0370 (7)	−0.0023 (5)	0.0021 (5)	0.0023 (5)
C7	0.0511 (7)	0.0367 (7)	0.0333 (7)	−0.0009 (6)	0.0029 (5)	−0.0028 (6)
C8	0.0476 (7)	0.0364 (7)	0.0299 (6)	−0.0026 (5)	0.0065 (5)	−0.0015 (5)
C9	0.0496 (7)	0.0357 (7)	0.0314 (6)	−0.0021 (5)	0.0079 (5)	−0.0001 (5)
C10	0.0419 (6)	0.0339 (7)	0.0339 (7)	−0.0024 (5)	0.0099 (5)	0.0007 (5)
C11	0.0608 (8)	0.0390 (7)	0.0347 (7)	0.0017 (6)	0.0154 (6)	0.0027 (6)
C12	0.0736 (9)	0.0420 (8)	0.0361 (8)	0.0030 (7)	0.0212 (7)	−0.0029 (6)
C13	0.0490 (7)	0.0324 (7)	0.0455 (8)	0.0011 (5)	0.0175 (6)	−0.0015 (6)
C14	0.0476 (7)	0.0336 (7)	0.0362 (7)	−0.0005 (5)	0.0096 (5)	0.0043 (5)
C15	0.0463 (7)	0.0354 (7)	0.0337 (7)	−0.0051 (5)	0.0086 (5)	−0.0018 (5)
C16	0.0749 (10)	0.0352 (8)	0.0597 (10)	0.0034 (7)	0.0194 (8)	0.0045 (7)
O1	0.0612 (6)	0.0353 (5)	0.0313 (5)	−0.0006 (4)	0.0092 (4)	0.0004 (4)
O2	0.1001 (9)	0.0452 (6)	0.0353 (6)	0.0094 (5)	0.0048 (5)	−0.0087 (5)
O3	0.1003 (8)	0.0346 (6)	0.0317 (5)	−0.0049 (5)	0.0092 (5)	−0.0017 (4)
O4	0.0859 (7)	0.0353 (6)	0.0495 (6)	0.0077 (5)	0.0222 (5)	−0.0011 (5)

C1—O1	1.3764 (15)	C9—H9	0.9300
C1—C6	1.3781 (19)	C10—C11	1.4014 (18)
C1—C2	1.3782 (19)	C10—C15	1.4046 (18)
C2—C3	1.374 (2)	C11—C12	1.3696 (18)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (2)	C12—C13	1.3876 (19)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.370 (2)	C13—O4	1.3588 (16)
C4—H4	0.9300	C13—C14	1.3758 (18)
C5—C6	1.3927 (18)	C14—C15	1.3868 (18)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.4495 (18)	C15—O3	1.3533 (16)
C7—O2	1.2280 (16)	C16—O4	1.4203 (17)
C7—C8	1.4697 (18)	C16—H16A	0.9600
C8—C9	1.3370 (17)	C16—H16B	0.9600
C8—O1	1.3902 (15)	C16—H16C	0.9600
C9—C10	1.4373 (17)	O3—H3A	0.90 (2)
O1—C1—C6	113.12 (11)	C11—C10—C15	116.89 (12)
O1—C1—C2	124.11 (12)	C11—C10—C9	124.08 (12)
C6—C1—C2	122.77 (12)	C15—C10—C9	119.01 (11)
C3—C2—C1	116.33 (14)	C12—C11—C10	121.80 (13)
C3—C2—H2	121.8	C12—C11—H11	119.1
C1—C2—H2	121.8	C10—C11—H11	119.1
C2—C3—C4	122.35 (14)	C11—C12—C13	119.89 (13)
C2—C3—H3	118.8	C11—C12—H12	120.1
C4—C3—H3	118.8	C13—C12—H12	120.1
C5—C4—C3	120.32 (14)	O4—C13—C14	124.18 (12)
C5—C4—H4	119.8	O4—C13—C12	115.47 (12)
C3—C4—H4	119.8	C14—C13—C12	120.34 (12)
C4—C5—C6	118.46 (14)	C13—C14—C15	119.51 (12)
C4—C5—H5	120.8	C13—C14—H14	120.2
C6—C5—H5	120.8	C15—C14—H14	120.2
C1—C6—C5	119.77 (13)	O3—C15—C14	120.93 (12)
C1—C6—C7	106.47 (11)	O3—C15—C10	117.50 (12)
C5—C6—C7	133.75 (13)	C14—C15—C10	121.57 (12)
O2—C7—C6	130.00 (13)	O4—C16—H16A	109.5
O2—C7—C8	125.30 (13)	O4—C16—H16B	109.5
C6—C7—C8	104.70 (11)	H16A—C16—H16B	109.5
C9—C8—O1	124.83 (12)	O4—C16—H16C	109.5
C9—C8—C7	125.89 (12)	H16A—C16—H16C	109.5
O1—C8—C7	109.29 (10)	H16B—C16—H16C	109.5
C8—C9—C10	131.29 (12)	C1—O1—C8	106.42 (10)
C8—C9—H9	114.4	C15—O3—H3A	110.1 (13)
C10—C9—H9	114.4	C13—O4—C16	117.98 (11)
O1—C1—C2—C3	−179.59 (12)	C8—C9—C10—C11	2.7 (2)
C6—C1—C2—C3	0.2 (2)	C8—C9—C10—C15	−179.18 (13)
C1—C2—C3—C4	−0.8 (2)	C15—C10—C11—C12	−0.59 (19)
C2—C3—C4—C5	0.9 (2)	C9—C10—C11—C12	177.54 (13)
C3—C4—C5—C6	−0.4 (2)	C10—C11—C12—C13	0.2 (2)
O1—C1—C6—C5	−179.94 (11)	C11—C12—C13—O4	−178.96 (13)
C2—C1—C6—C5	0.23 (19)	C11—C12—C13—C14	0.4 (2)
O1—C1—C6—C7	0.83 (14)	O4—C13—C14—C15	178.78 (12)
C2—C1—C6—C7	−178.99 (12)	C12—C13—C14—C15	−0.47 (19)
C4—C5—C6—C1	−0.12 (19)	C13—C14—C15—O3	−179.95 (11)
C4—C5—C6—C7	178.85 (14)	C13—C14—C15—C10	0.05 (18)
C1—C6—C7—O2	179.03 (14)	C11—C10—C15—O3	−179.53 (11)
C5—C6—C7—O2	0.0 (3)	C9—C10—C15—O3	2.24 (17)
C1—C6—C7—C8	−0.86 (14)	C11—C10—C15—C14	0.47 (18)
C5—C6—C7—C8	−179.93 (14)	C9—C10—C15—C14	−177.76 (11)
O2—C7—C8—C9	0.9 (2)	C6—C1—O1—C8	−0.43 (14)
C6—C7—C8—C9	−179.20 (12)	C2—C1—O1—C8	179.39 (12)
O2—C7—C8—O1	−179.27 (13)	C9—C8—O1—C1	179.68 (12)
C6—C7—C8—O1	0.63 (14)	C7—C8—O1—C1	−0.15 (13)
O1—C8—C9—C10	0.5 (2)	C14—C13—O4—C16	2.1 (2)
C7—C8—C9—C10	−179.69 (12)	C12—C13—O4—C16	−178.64 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2i	0.90 (2)	1.80 (2)	2.6952 (14)	170.0 (19)
C16—H16A···O3i	0.96	2.59	3.3328 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.90 (2)	1.80 (2)	2.6952 (14)	170.0 (19)
C16—H16A⋯O3i	0.96	2.59	3.3328 (14)	135

Symmetry code: (i) .