(E)-2,3-Bis(4-methoxy-phen-yl)acrylic acid.

In the title mol-ecule, C(17)H(16)O(4), the angle between the aromatic ring planes is 69.1 (6)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds; mol-ecules related by a centre of symmetry are linked to form inversion dimers.

Related literature

For the biological properties and synthesis of resveratrol (trans-3,4′,5-trihydroxy­stilbene) and its derivatives, see: Huang, Ruan et al. (2007 ▶); Huang et al. (2008 ▶); Jang et al. (1997 ▶); Ruan et al. (2006 ▶); Schulze et al. (2005 ▶); Shi et al. (2005 ▶). For related crystal structures, see: Huang, Li et al. (2007 ▶); Stomberg et al. (2001 ▶).

Experimental

Crystal data

C17H16O4

M = 284.30

Triclinic,

a = 5.8690 (12) Å

b = 9.1480 (18) Å

c = 13.992 (3) Å

α = 83.65 (3)°

β = 85.43 (3)°

γ = 80.92 (3)°

V = 735.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

3196 measured reflections

2895 independent reflections

1779 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.151

S = 1.08

2895 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011751/wn2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011751/wn2320Isup2.hkl

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

C17H16O4	Z = 2
Mr = 284.30	F(000) = 300
Triclinic, P1	Dx = 1.283 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8690 (12) Å	Cell parameters from 1625 reflections
b = 9.1480 (18) Å	θ = 2.2–24.8°
c = 13.992 (3) Å	µ = 0.09 mm−1
α = 83.65 (3)°	T = 298 K
β = 85.43 (3)°	Block, colorless
γ = 80.92 (3)°	0.30 × 0.20 × 0.10 mm
V = 735.8 (3) Å3

Enraf–Nonius CAD-4 diffractometer	2895 independent reflections
Radiation source: fine-focus sealed tube	1779 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω/2θ scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→7
Tmin = 0.973, Tmax = 0.991	k = −11→11
3196 measured reflections	l = −17→17

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.024P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2895 reflections	Δρmax = 0.18 e Å−3
194 parameters	Δρmin = −0.17 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: 0.044 (7)

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	0.7983 (6)	1.3447 (4)	−0.0150 (2)	0.0938 (11)
H1A	0.6774	1.2848	−0.0132	0.141*
H1B	0.8108	1.3993	−0.0774	0.141*
H1C	0.7629	1.4130	0.0333	0.141*
C2	1.0269 (4)	1.1661 (3)	0.08912 (15)	0.0505 (6)
C3	0.8532 (4)	1.1641 (3)	0.16030 (17)	0.0565 (6)
H3A	0.7103	1.2225	0.1513	0.068*
C4	0.8905 (4)	1.0754 (3)	0.24524 (17)	0.0548 (6)
H4	0.7705	1.0752	0.2929	0.066*
C5	1.0983 (4)	0.9870 (2)	0.26254 (15)	0.0423 (5)
C6	1.2741 (4)	0.9919 (3)	0.19039 (16)	0.0553 (6)
H6	1.4182	0.9357	0.2001	0.066*
C7	1.2382 (4)	1.0786 (3)	0.10484 (17)	0.0621 (7)
H7	1.3573	1.0786	0.0568	0.074*
C8	1.1324 (4)	0.8926 (2)	0.35563 (15)	0.0462 (6)
C9	1.2916 (4)	0.9385 (3)	0.41980 (16)	0.0495 (6)
C10	1.0275 (4)	0.7750 (2)	0.38730 (16)	0.0500 (6)
H10	1.0582	0.7349	0.4498	0.060*
C11	0.8736 (4)	0.6996 (2)	0.34031 (15)	0.0466 (6)
C12	0.7562 (4)	0.5977 (3)	0.39652 (17)	0.0563 (7)
H12	0.7770	0.5821	0.4623	0.068*
C13	0.6106 (4)	0.5188 (3)	0.35884 (17)	0.0577 (7)
H13	0.5354	0.4505	0.3985	0.069*
C14	0.5767 (4)	0.5414 (2)	0.26176 (17)	0.0495 (6)
C15	0.6987 (4)	0.6386 (3)	0.20313 (16)	0.0550 (6)
H15	0.6826	0.6504	0.1370	0.066*
C16	0.8418 (4)	0.7169 (2)	0.24152 (16)	0.0521 (6)
H16	0.9198	0.7831	0.2013	0.063*
C17	0.2995 (5)	0.3745 (3)	0.2726 (2)	0.0746 (8)
H17A	0.3998	0.2948	0.3053	0.112*
H17B	0.2067	0.3345	0.2315	0.112*
H17C	0.2009	0.4283	0.3192	0.112*
O1	1.0108 (3)	1.2517 (2)	0.00292 (12)	0.0753 (6)
O2	1.3849 (3)	1.04878 (19)	0.39719 (11)	0.0674 (6)
O3	1.3251 (3)	0.85636 (19)	0.50110 (11)	0.0691 (6)
H3	1.4025	0.8958	0.5341	0.104*
O4	0.4348 (3)	0.47241 (18)	0.21611 (12)	0.0641 (5)

	U11	U22	U33	U12	U13	U23
C1	0.091 (2)	0.104 (2)	0.074 (2)	0.007 (2)	−0.0214 (18)	0.0273 (18)
C2	0.0525 (15)	0.0561 (14)	0.0426 (12)	−0.0126 (12)	−0.0038 (11)	0.0029 (10)
C3	0.0391 (13)	0.0660 (16)	0.0582 (14)	0.0010 (12)	−0.0025 (11)	0.0085 (12)
C4	0.0350 (12)	0.0696 (16)	0.0543 (14)	−0.0040 (11)	0.0048 (10)	0.0067 (12)
C5	0.0397 (12)	0.0455 (12)	0.0429 (12)	−0.0120 (10)	−0.0034 (9)	−0.0004 (9)
C6	0.0366 (13)	0.0690 (16)	0.0543 (14)	0.0024 (11)	0.0015 (11)	0.0018 (12)
C7	0.0468 (15)	0.0817 (18)	0.0506 (14)	−0.0023 (13)	0.0095 (12)	0.0054 (13)
C8	0.0419 (13)	0.0483 (13)	0.0475 (12)	−0.0076 (10)	−0.0032 (10)	0.0010 (10)
C9	0.0472 (13)	0.0552 (14)	0.0451 (13)	−0.0108 (11)	−0.0061 (11)	0.0061 (11)
C10	0.0515 (14)	0.0544 (14)	0.0432 (12)	−0.0101 (11)	−0.0037 (11)	0.0034 (10)
C11	0.0437 (13)	0.0481 (13)	0.0465 (13)	−0.0074 (10)	−0.0032 (10)	0.0030 (10)
C12	0.0595 (16)	0.0638 (16)	0.0461 (13)	−0.0183 (13)	−0.0028 (11)	0.0053 (11)
C13	0.0527 (15)	0.0620 (15)	0.0595 (15)	−0.0223 (12)	0.0017 (12)	0.0050 (12)
C14	0.0434 (13)	0.0456 (13)	0.0588 (14)	−0.0050 (11)	−0.0071 (11)	−0.0009 (11)
C15	0.0662 (16)	0.0519 (14)	0.0475 (13)	−0.0145 (12)	−0.0108 (12)	0.0059 (11)
C16	0.0544 (14)	0.0522 (14)	0.0502 (14)	−0.0178 (12)	−0.0027 (11)	0.0064 (11)
C17	0.0668 (18)	0.0648 (17)	0.097 (2)	−0.0284 (15)	−0.0050 (16)	−0.0028 (15)
O1	0.0737 (13)	0.0920 (14)	0.0513 (10)	−0.0045 (11)	−0.0040 (9)	0.0201 (9)
O2	0.0759 (12)	0.0728 (12)	0.0594 (11)	−0.0376 (10)	−0.0217 (9)	0.0176 (9)
O3	0.0865 (14)	0.0735 (12)	0.0535 (10)	−0.0355 (10)	−0.0255 (9)	0.0150 (9)
O4	0.0639 (11)	0.0610 (11)	0.0720 (11)	−0.0240 (9)	−0.0171 (9)	0.0030 (9)

C1—O1	1.418 (3)	C9—O3	1.303 (2)
C1—H1A	0.9600	C10—C11	1.455 (3)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.384 (3)
C2—O1	1.364 (3)	C11—C16	1.398 (3)
C2—C3	1.368 (3)	C12—C13	1.371 (3)
C2—C7	1.385 (3)	C12—H12	0.9300
C3—C4	1.375 (3)	C13—C14	1.377 (3)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.376 (3)	C14—O4	1.356 (3)
C4—H4	0.9300	C14—C15	1.386 (3)
C5—C6	1.387 (3)	C15—C16	1.362 (3)
C5—C8	1.490 (3)	C15—H15	0.9300
C6—C7	1.372 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—O4	1.423 (3)
C7—H7	0.9300	C17—H17A	0.9600
C8—C10	1.339 (3)	C17—H17B	0.9600
C8—C9	1.482 (3)	C17—H17C	0.9600
C9—O2	1.222 (3)	O3—H3	0.8200
O1—C1—H1A	109.5	C8—C10—C11	130.8 (2)
O1—C1—H1B	109.5	C8—C10—H10	114.6
H1A—C1—H1B	109.5	C11—C10—H10	114.6
O1—C1—H1C	109.5	C12—C11—C16	116.9 (2)
H1A—C1—H1C	109.5	C12—C11—C10	117.9 (2)
H1B—C1—H1C	109.5	C16—C11—C10	125.1 (2)
O1—C2—C3	124.8 (2)	C13—C12—C11	122.4 (2)
O1—C2—C7	116.4 (2)	C13—C12—H12	118.8
C3—C2—C7	118.8 (2)	C11—C12—H12	118.8
C2—C3—C4	119.8 (2)	C12—C13—C14	119.5 (2)
C2—C3—H3A	120.1	C12—C13—H13	120.3
C4—C3—H3A	120.1	C14—C13—H13	120.3
C3—C4—C5	122.6 (2)	O4—C14—C13	125.2 (2)
C3—C4—H4	118.7	O4—C14—C15	115.5 (2)
C5—C4—H4	118.7	C13—C14—C15	119.3 (2)
C4—C5—C6	117.04 (19)	C16—C15—C14	120.6 (2)
C4—C5—C8	121.03 (19)	C16—C15—H15	119.7
C6—C5—C8	121.9 (2)	C14—C15—H15	119.7
C7—C6—C5	121.0 (2)	C15—C16—C11	121.2 (2)
C7—C6—H6	119.5	C15—C16—H16	119.4
C5—C6—H6	119.5	C11—C16—H16	119.4
C6—C7—C2	120.8 (2)	O4—C17—H17A	109.5
C6—C7—H7	119.6	O4—C17—H17B	109.5
C2—C7—H7	119.6	H17A—C17—H17B	109.5
C10—C8—C9	117.8 (2)	O4—C17—H17C	109.5
C10—C8—C5	126.2 (2)	H17A—C17—H17C	109.5
C9—C8—C5	115.95 (18)	H17B—C17—H17C	109.5
O2—C9—O3	122.1 (2)	C2—O1—C1	118.0 (2)
O2—C9—C8	121.2 (2)	C9—O3—H3	109.5
O3—C9—C8	116.7 (2)	C14—O4—C17	118.3 (2)
O1—C2—C3—C4	−178.7 (2)	C9—C8—C10—C11	−176.6 (2)
C7—C2—C3—C4	−0.3 (4)	C5—C8—C10—C11	5.9 (4)
C2—C3—C4—C5	0.1 (4)	C8—C10—C11—C12	−168.2 (2)
C3—C4—C5—C6	0.9 (4)	C8—C10—C11—C16	14.8 (4)
C3—C4—C5—C8	179.8 (2)	C16—C11—C12—C13	−1.5 (4)
C4—C5—C6—C7	−1.7 (4)	C10—C11—C12—C13	−178.8 (2)
C8—C5—C6—C7	179.4 (2)	C11—C12—C13—C14	−0.5 (4)
C5—C6—C7—C2	1.5 (4)	C12—C13—C14—O4	−178.9 (2)
O1—C2—C7—C6	178.1 (2)	C12—C13—C14—C15	2.9 (4)
C3—C2—C7—C6	−0.4 (4)	O4—C14—C15—C16	178.3 (2)
C4—C5—C8—C10	66.9 (3)	C13—C14—C15—C16	−3.3 (4)
C6—C5—C8—C10	−114.2 (3)	C14—C15—C16—C11	1.3 (4)
C4—C5—C8—C9	−110.7 (2)	C12—C11—C16—C15	1.1 (3)
C6—C5—C8—C9	68.2 (3)	C10—C11—C16—C15	178.2 (2)
C10—C8—C9—O2	−176.7 (2)	C3—C2—O1—C1	−0.5 (4)
C5—C8—C9—O2	1.1 (3)	C7—C2—O1—C1	−178.9 (2)
C10—C8—C9—O3	2.9 (3)	C13—C14—O4—C17	3.6 (3)
C5—C8—C9—O3	−179.4 (2)	C15—C14—O4—C17	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	1.80	2.608 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.80	2.608 (2)	169

Symmetry code: (i) .