Ethyl 3-(4-hydroxy-phen-oxy)-2-(4-methoxy-phen-yl)acrylate.

In the title compound, C(18)H(18)O(5), the dihedral angle between the two benzene rings is 55.2 (3)°. The ethyl acrylate linkage is planar and forms dihedral angles of 21.3 (3) and 41.0 (3)°, respectively, with the hydroxy-phenyl and methoxy-phenyl rings. In the crystal structure, mol-ecules are linked into zigzag chains along the b axis by O-H⋯O hydrogen bonds.

Related literature

For general background, see: Huang et al. (2008 ▶); Li et al. (2008 ▶); Liu et al. (2008 ▶); Shi et al. (2008 ▶); Xiao et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H18O5

M = 314.33

Orthorhombic,

a = 7.4773 (16) Å

b = 11.661 (2) Å

c = 18.417 (4) Å

V = 1605.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.981

5527 measured reflections

1822 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.134

S = 1.05

1822 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803571X/ci2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803571X/ci2693Isup2.hkl

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

C18H18O5	F000 = 664
Mr = 314.33	Dx = 1.304 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1213 reflections
a = 7.4773 (16) Å	θ = 3.2–26.1º
b = 11.661 (2) Å	µ = 0.10 mm−1
c = 18.417 (4) Å	T = 298 (2) K
V = 1605.8 (6) Å3	Prism, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	1822 independent reflections
Radiation source: fine-focus sealed tube	1486 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 298(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.963, Tmax = 0.981	k = −10→14
5527 measured reflections	l = −22→22

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.4887P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1822 reflections	Δρmax = 0.26 e Å−3
211 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.0040 (5)	0.4964 (3)	0.73124 (16)	0.0401 (8)
C2	0.0773 (6)	0.4306 (3)	0.78656 (17)	0.0485 (9)
H2	0.1463	0.3669	0.7750	0.058*
C3	0.0490 (6)	0.4589 (3)	0.85909 (18)	0.0489 (10)
H3	0.0990	0.4144	0.8957	0.059*
C4	−0.0543 (6)	0.5537 (3)	0.87635 (17)	0.0444 (9)
C5	−0.1311 (5)	0.6181 (3)	0.82193 (17)	0.0454 (9)
H5	−0.2019	0.6810	0.8335	0.054*
C6	−0.1024 (5)	0.5887 (3)	0.74921 (17)	0.0471 (9)
H6	−0.1556	0.6319	0.7126	0.057*
C7	0.0419 (5)	0.6087 (3)	0.47594 (16)	0.0370 (7)
C8	−0.0503 (5)	0.5959 (3)	0.41071 (17)	0.0407 (8)
H8	−0.0970	0.5246	0.3984	0.049*
C9	−0.0734 (5)	0.6872 (3)	0.36402 (17)	0.0462 (9)
H9	−0.1336	0.6762	0.3204	0.055*
C10	−0.0083 (5)	0.7946 (3)	0.38124 (18)	0.0441 (9)
C11	0.0842 (5)	0.8107 (3)	0.44550 (19)	0.0463 (9)
H11	0.1287	0.8826	0.4578	0.056*
C12	0.1095 (5)	0.7176 (3)	0.49137 (19)	0.0440 (9)
H12	0.1741	0.7282	0.5340	0.053*
C13	0.0301 (5)	0.5385 (3)	0.60130 (17)	0.0415 (8)
H13	0.0000	0.6138	0.6123	0.050*
C14	0.0590 (5)	0.5141 (3)	0.52943 (17)	0.0394 (8)
C15	0.1049 (5)	0.3973 (3)	0.50927 (17)	0.0397 (8)
C16	0.1644 (7)	0.2682 (3)	0.41167 (18)	0.0513 (10)
H16A	0.0775	0.2121	0.4281	0.062*
H16B	0.2814	0.2462	0.4297	0.062*
C17	0.1658 (6)	0.2743 (3)	0.33027 (17)	0.0549 (10)
H17A	0.0455	0.2826	0.3128	0.082*
H17B	0.2170	0.2053	0.3109	0.082*
H17C	0.2357	0.3390	0.3150	0.082*
C18	−0.0024 (7)	0.9941 (3)	0.3518 (3)	0.0668 (13)
H18A	−0.0656	1.0139	0.3954	0.100*
H18B	−0.0374	1.0450	0.3134	0.100*
H18C	0.1239	1.0008	0.3600	0.100*
O5	0.0407 (4)	0.4650 (3)	0.65807 (14)	0.0662 (8)
O1	0.1315 (4)	0.3188 (2)	0.55214 (12)	0.0541 (7)
O2	0.1174 (4)	0.3810 (2)	0.43764 (12)	0.0468 (7)
O3	−0.0441 (5)	0.8795 (2)	0.33197 (14)	0.0618 (8)
O4	−0.0756 (5)	0.5803 (2)	0.94804 (12)	0.0601 (8)
H4	−0.1019	0.6483	0.9520	0.090*

	U11	U22	U33	U12	U13	U23
C1	0.047 (2)	0.0446 (17)	0.0288 (16)	−0.0058 (17)	−0.0002 (15)	−0.0054 (14)
C2	0.062 (2)	0.0465 (19)	0.0373 (17)	−0.003 (2)	0.0026 (18)	−0.0020 (15)
C3	0.071 (3)	0.0439 (18)	0.0320 (16)	−0.008 (2)	−0.0065 (18)	0.0043 (15)
C4	0.060 (2)	0.0450 (19)	0.0281 (15)	−0.011 (2)	0.0040 (16)	−0.0038 (14)
C5	0.053 (2)	0.0458 (19)	0.0379 (18)	0.0008 (19)	0.0010 (17)	−0.0091 (16)
C6	0.054 (2)	0.056 (2)	0.0313 (16)	0.002 (2)	−0.0039 (16)	0.0043 (16)
C7	0.0403 (17)	0.0406 (17)	0.0302 (15)	−0.0005 (17)	0.0009 (15)	−0.0029 (14)
C8	0.046 (2)	0.0405 (18)	0.0352 (17)	−0.0062 (17)	−0.0021 (16)	−0.0060 (14)
C9	0.058 (2)	0.052 (2)	0.0282 (15)	−0.004 (2)	−0.0067 (16)	−0.0010 (15)
C10	0.048 (2)	0.0461 (19)	0.0376 (18)	−0.0014 (18)	0.0041 (17)	−0.0001 (15)
C11	0.053 (2)	0.0395 (17)	0.0464 (19)	−0.0077 (18)	0.0007 (18)	−0.0043 (16)
C12	0.045 (2)	0.049 (2)	0.0385 (18)	−0.0055 (18)	−0.0048 (17)	−0.0065 (16)
C13	0.048 (2)	0.0437 (18)	0.0329 (16)	0.0006 (18)	−0.0030 (15)	−0.0030 (15)
C14	0.0419 (19)	0.0441 (18)	0.0321 (16)	−0.0035 (17)	−0.0041 (16)	−0.0026 (14)
C15	0.048 (2)	0.0404 (17)	0.0303 (16)	−0.0023 (18)	0.0012 (16)	−0.0017 (14)
C16	0.081 (3)	0.0400 (19)	0.0332 (17)	0.001 (2)	0.002 (2)	−0.0028 (15)
C17	0.075 (3)	0.055 (2)	0.0348 (18)	−0.005 (2)	0.0052 (19)	−0.0094 (17)
C18	0.068 (3)	0.047 (2)	0.086 (3)	0.000 (2)	0.000 (3)	0.014 (2)
O5	0.080 (2)	0.0751 (18)	0.0436 (14)	0.0007 (19)	0.0009 (15)	−0.0010 (14)
O1	0.087 (2)	0.0428 (13)	0.0328 (12)	0.0010 (15)	0.0023 (14)	0.0029 (11)
O2	0.0716 (17)	0.0392 (12)	0.0296 (11)	0.0028 (13)	0.0012 (13)	−0.0037 (10)
O3	0.092 (2)	0.0451 (14)	0.0488 (14)	−0.0026 (16)	−0.0042 (16)	0.0095 (12)
O4	0.098 (2)	0.0527 (15)	0.0292 (12)	−0.0039 (18)	0.0073 (14)	−0.0048 (11)

C1—C6	1.379 (5)	C11—C12	1.388 (5)
C1—C2	1.388 (5)	C11—H11	0.93
C1—O5	1.423 (4)	C12—H12	0.93
C2—C3	1.392 (5)	C13—O5	1.354 (4)
C2—H2	0.93	C13—C14	1.371 (4)
C3—C4	1.386 (5)	C13—H13	0.93
C3—H3	0.93	C14—C15	1.454 (4)
C4—O4	1.366 (4)	C15—O1	1.225 (4)
C4—C5	1.377 (5)	C15—O2	1.336 (4)
C5—C6	1.399 (5)	C16—O2	1.444 (4)
C5—H5	0.93	C16—C17	1.501 (5)
C6—H6	0.93	C16—H16A	0.97
C7—C8	1.393 (5)	C16—H16B	0.97
C7—C12	1.396 (4)	C17—H17A	0.96
C7—C14	1.484 (4)	C17—H17B	0.96
C8—C9	1.379 (5)	C17—H17C	0.96
C8—H8	0.93	C18—O3	1.420 (5)
C9—C10	1.381 (5)	C18—H18A	0.96
C9—H9	0.93	C18—H18B	0.96
C10—O3	1.369 (4)	C18—H18C	0.96
C10—C11	1.384 (5)	O4—H4	0.82
C6—C1—C2	118.9 (3)	C11—C12—H12	118.7
C6—C1—O5	122.7 (3)	C7—C12—H12	118.7
C2—C1—O5	118.5 (3)	O5—C13—C14	127.3 (3)
C1—C2—C3	120.9 (4)	O5—C13—H13	116.4
C1—C2—H2	119.6	C14—C13—H13	116.4
C3—C2—H2	119.6	C13—C14—C15	118.5 (3)
C4—C3—C2	119.6 (3)	C13—C14—C7	118.3 (3)
C4—C3—H3	120.2	C15—C14—C7	123.2 (3)
C2—C3—H3	120.2	O1—C15—O2	121.3 (3)
O4—C4—C5	122.1 (3)	O1—C15—C14	125.0 (3)
O4—C4—C3	117.9 (3)	O2—C15—C14	113.7 (3)
C5—C4—C3	120.0 (3)	O2—C16—C17	106.8 (3)
C4—C5—C6	120.0 (3)	O2—C16—H16A	110.4
C4—C5—H5	120.0	C17—C16—H16A	110.4
C6—C5—H5	120.0	O2—C16—H16B	110.4
C1—C6—C5	120.6 (3)	C17—C16—H16B	110.4
C1—C6—H6	119.7	H16A—C16—H16B	108.6
C5—C6—H6	119.7	C16—C17—H17A	109.5
C8—C7—C12	116.9 (3)	C16—C17—H17B	109.5
C8—C7—C14	122.3 (3)	H17A—C17—H17B	109.5
C12—C7—C14	120.7 (3)	C16—C17—H17C	109.5
C9—C8—C7	121.1 (3)	H17A—C17—H17C	109.5
C9—C8—H8	119.4	H17B—C17—H17C	109.5
C7—C8—H8	119.4	O3—C18—H18A	109.5
C8—C9—C10	120.9 (3)	O3—C18—H18B	109.5
C8—C9—H9	119.6	H18A—C18—H18B	109.5
C10—C9—H9	119.6	O3—C18—H18C	109.5
O3—C10—C9	115.8 (3)	H18A—C18—H18C	109.5
O3—C10—C11	124.5 (3)	H18B—C18—H18C	109.5
C9—C10—C11	119.7 (3)	C13—O5—C1	123.8 (3)
C10—C11—C12	118.9 (3)	C15—O2—C16	118.3 (3)
C10—C11—H11	120.6	C10—O3—C18	117.8 (3)
C12—C11—H11	120.6	C4—O4—H4	109.5
C11—C12—C7	122.5 (3)
C6—C1—C2—C3	−1.9 (6)	C14—C7—C12—C11	−174.8 (3)
O5—C1—C2—C3	178.6 (3)	O5—C13—C14—C15	0.5 (6)
C1—C2—C3—C4	0.2 (6)	O5—C13—C14—C7	−179.4 (3)
C2—C3—C4—O4	−178.4 (4)	C8—C7—C14—C13	−134.7 (4)
C2—C3—C4—C5	1.2 (6)	C12—C7—C14—C13	41.3 (5)
O4—C4—C5—C6	178.7 (4)	C8—C7—C14—C15	45.3 (5)
C3—C4—C5—C6	−1.0 (6)	C12—C7—C14—C15	−138.6 (4)
C2—C1—C6—C5	2.2 (6)	C13—C14—C15—O1	−4.9 (6)
O5—C1—C6—C5	−178.4 (3)	C7—C14—C15—O1	175.0 (4)
C4—C5—C6—C1	−0.7 (6)	C13—C14—C15—O2	175.4 (3)
C12—C7—C8—C9	−0.2 (5)	C7—C14—C15—O2	−4.7 (5)
C14—C7—C8—C9	176.0 (3)	C14—C13—O5—C1	−178.3 (4)
C7—C8—C9—C10	−1.1 (6)	C6—C1—O5—C13	23.2 (6)
C8—C9—C10—O3	−178.0 (4)	C2—C1—O5—C13	−157.3 (4)
C8—C9—C10—C11	1.2 (6)	O1—C15—O2—C16	−0.4 (6)
O3—C10—C11—C12	179.1 (4)	C14—C15—O2—C16	179.3 (3)
C9—C10—C11—C12	0.0 (6)	C17—C16—O2—C15	179.1 (3)
C10—C11—C12—C7	−1.4 (6)	C9—C10—O3—C18	171.3 (4)
C8—C7—C12—C11	1.5 (6)	C11—C10—O3—C18	−7.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1i	0.82	2.00	2.812 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1i	0.82	2.00	2.812 (3)	169

Symmetry code: (i) .