4-(3-Methoxy-phen-oxy)butyric acid.

In the title compound, C(11)H(14)O(4), an inter-mediate for the synthesis of a new kind of estrogen receptor modulator, all non-H atoms lie on a common plane (r.m.s. deviation = 0.0472 Å). All C-C bonds in the side chain are in a trans conformation, and the hydroxyl group is also trans to the methyl-ene chain. In the crystal structure, mol-ecules form centrosymmetric dimers showing a head-to-head arrangement which is stabilized by O-H⋯O hydrogen bonds. A weak C-H⋯O contact is also present.

Related literature

For the synthesis of 4-(3-meth­oxy-phen­oxy)-butyric acid, see Tandon et al. (1990 ▶). For estrogen receptor modulators, see Lloyd et al. (2004 ▶). For a similar carboxylic acid, see: Smith et al. (1989 ▶).

Experimental

Crystal data

C11H14O4

M = 210.22

Monoclinic,

a = 9.6509 (6) Å

b = 5.3998 (4) Å

c = 20.2033 (13) Å

β = 90.822 (5)°

V = 1052.74 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.32 × 0.27 × 0.25 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: none

15489 measured reflections

2945 independent reflections

2458 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.07

2945 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008186/ng2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008186/ng2557Isup2.hkl

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

C11H14O4	F(000) = 448
Mr = 210.22	Dx = 1.326 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15224 reflections
a = 9.6509 (6) Å	θ = 3.7–29.5°
b = 5.3998 (4) Å	µ = 0.10 mm−1
c = 20.2033 (13) Å	T = 173 K
β = 90.822 (5)°	Block, colourless
V = 1052.74 (12) Å3	0.32 × 0.27 × 0.25 mm
Z = 4

Stoe IPDS-II two-circle diffractometer	2458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 29.6°, θmin = 3.7°
ω scans	h = −13→13
15489 measured reflections	k = −7→7
2945 independent reflections	l = −28→25

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.1161P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2945 reflections	Δρmax = 0.31 e Å−3
142 parameters	Δρmin = −0.20 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: 0.048 (5)

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
O1	0.32321 (7)	0.55314 (15)	0.64594 (4)	0.03035 (19)
C1	0.36009 (11)	0.72446 (18)	0.59488 (5)	0.0263 (2)
H1A	0.3840	0.6344	0.5539	0.032*
H1B	0.4411	0.8248	0.6091	0.032*
C2	0.23475 (10)	0.89015 (19)	0.58265 (5)	0.0265 (2)
H2A	0.2151	0.9860	0.6232	0.032*
H2B	0.1527	0.7866	0.5721	0.032*
C3	0.26116 (11)	1.0679 (2)	0.52546 (5)	0.0286 (2)
H3A	0.3491	1.1572	0.5343	0.034*
H3B	0.2727	0.9704	0.4844	0.034*
C4	0.14701 (11)	1.25525 (19)	0.51430 (5)	0.0269 (2)
O41	0.17803 (9)	1.41971 (15)	0.46803 (4)	0.0342 (2)
H41	0.1036 (18)	1.526 (3)	0.4617 (8)	0.056 (5)*
O42	0.03810 (8)	1.25686 (16)	0.54438 (5)	0.0382 (2)
C11	0.42179 (10)	0.38789 (18)	0.66811 (5)	0.0245 (2)
C12	0.55358 (10)	0.36401 (18)	0.64103 (5)	0.0253 (2)
H12	0.5814	0.4682	0.6058	0.030*
C13	0.64437 (10)	0.18317 (18)	0.66685 (5)	0.0243 (2)
C14	0.60524 (11)	0.02991 (19)	0.71884 (5)	0.0263 (2)
H14	0.6668	−0.0927	0.7358	0.032*
C15	0.47284 (10)	0.06066 (19)	0.74563 (5)	0.0278 (2)
H15	0.4454	−0.0420	0.7813	0.033*
C16	0.38130 (11)	0.23721 (19)	0.72120 (5)	0.0270 (2)
H16	0.2923	0.2562	0.7401	0.032*
O13	0.77149 (8)	0.17389 (15)	0.63728 (4)	0.0316 (2)
C17	0.86678 (11)	−0.0111 (2)	0.66159 (5)	0.0334 (3)
H17A	0.8863	0.0179	0.7087	0.050*
H17B	0.9532	−0.0014	0.6369	0.050*
H17C	0.8257	−0.1758	0.6558	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0250 (4)	0.0310 (4)	0.0350 (4)	0.0067 (3)	0.0021 (3)	0.0095 (3)
C1	0.0255 (5)	0.0255 (5)	0.0277 (5)	0.0032 (4)	−0.0012 (4)	0.0029 (4)
C2	0.0262 (5)	0.0251 (5)	0.0281 (5)	0.0052 (4)	−0.0032 (4)	0.0004 (4)
C3	0.0290 (5)	0.0275 (5)	0.0294 (5)	0.0056 (4)	−0.0011 (4)	0.0014 (4)
C4	0.0291 (5)	0.0247 (5)	0.0268 (5)	0.0022 (4)	−0.0036 (4)	0.0007 (4)
O41	0.0362 (4)	0.0313 (4)	0.0351 (4)	0.0080 (3)	0.0025 (3)	0.0096 (3)
O42	0.0318 (4)	0.0371 (5)	0.0458 (5)	0.0105 (3)	0.0055 (4)	0.0148 (4)
C11	0.0238 (4)	0.0231 (4)	0.0266 (5)	0.0024 (3)	−0.0027 (4)	0.0014 (4)
C12	0.0263 (5)	0.0255 (5)	0.0240 (4)	0.0018 (3)	−0.0002 (3)	0.0035 (3)
C13	0.0237 (4)	0.0257 (4)	0.0235 (4)	0.0021 (3)	−0.0008 (3)	−0.0002 (4)
C14	0.0273 (5)	0.0250 (5)	0.0265 (5)	0.0018 (4)	−0.0033 (4)	0.0035 (4)
C15	0.0280 (5)	0.0282 (5)	0.0273 (5)	−0.0025 (4)	−0.0011 (4)	0.0050 (4)
C16	0.0245 (5)	0.0286 (5)	0.0280 (5)	−0.0010 (4)	0.0002 (4)	0.0020 (4)
O13	0.0266 (4)	0.0380 (4)	0.0303 (4)	0.0100 (3)	0.0048 (3)	0.0095 (3)
C17	0.0301 (5)	0.0382 (6)	0.0319 (5)	0.0128 (4)	0.0026 (4)	0.0059 (4)

O1—C11	1.3747 (11)	C11—C16	1.4061 (14)
O1—C1	1.4343 (12)	C12—C13	1.4072 (13)
C1—C2	1.5219 (13)	C12—H12	0.9500
C1—H1A	0.9900	C13—O13	1.3732 (12)
C1—H1B	0.9900	C13—C14	1.3935 (14)
C2—C3	1.5263 (14)	C14—C15	1.4047 (14)
C2—H2A	0.9900	C14—H14	0.9500
C2—H2B	0.9900	C15—C16	1.3858 (14)
C3—C4	1.5103 (14)	C15—H15	0.9500
C3—H3A	0.9900	C16—H16	0.9500
C3—H3B	0.9900	O13—C17	1.4394 (12)
C4—O42	1.2217 (13)	C17—H17A	0.9800
C4—O41	1.3268 (13)	C17—H17B	0.9800
O41—H41	0.927 (18)	C17—H17C	0.9800
C11—C12	1.3977 (13)
C11—O1—C1	118.38 (8)	O1—C11—C16	115.18 (9)
O1—C1—C2	106.92 (8)	C12—C11—C16	120.64 (9)
O1—C1—H1A	110.3	C11—C12—C13	118.96 (9)
C2—C1—H1A	110.3	C11—C12—H12	120.5
O1—C1—H1B	110.3	C13—C12—H12	120.5
C2—C1—H1B	110.3	O13—C13—C14	124.03 (9)
H1A—C1—H1B	108.6	O13—C13—C12	114.80 (8)
C1—C2—C3	110.58 (8)	C14—C13—C12	121.16 (9)
C1—C2—H2A	109.5	C13—C14—C15	118.56 (9)
C3—C2—H2A	109.5	C13—C14—H14	120.7
C1—C2—H2B	109.5	C15—C14—H14	120.7
C3—C2—H2B	109.5	C16—C15—C14	121.53 (9)
H2A—C2—H2B	108.1	C16—C15—H15	119.2
C4—C3—C2	113.88 (9)	C14—C15—H15	119.2
C4—C3—H3A	108.8	C15—C16—C11	119.14 (9)
C2—C3—H3A	108.8	C15—C16—H16	120.4
C4—C3—H3B	108.8	C11—C16—H16	120.4
C2—C3—H3B	108.8	C13—O13—C17	116.57 (8)
H3A—C3—H3B	107.7	O13—C17—H17A	109.5
O42—C4—O41	123.38 (9)	O13—C17—H17B	109.5
O42—C4—C3	124.16 (9)	H17A—C17—H17B	109.5
O41—C4—C3	112.46 (9)	O13—C17—H17C	109.5
C4—O41—H41	109.2 (11)	H17A—C17—H17C	109.5
O1—C11—C12	124.18 (9)	H17B—C17—H17C	109.5
C11—O1—C1—C2	−177.45 (8)	C11—C12—C13—C14	−0.36 (15)
O1—C1—C2—C3	−176.12 (8)	O13—C13—C14—C15	178.91 (9)
C1—C2—C3—C4	−174.52 (9)	C12—C13—C14—C15	−0.52 (15)
C2—C3—C4—O42	−5.13 (16)	C13—C14—C15—C16	0.51 (16)
C2—C3—C4—O41	174.73 (9)	C14—C15—C16—C11	0.38 (16)
C1—O1—C11—C12	−4.53 (15)	O1—C11—C16—C15	178.32 (9)
C1—O1—C11—C16	175.88 (9)	C12—C11—C16—C15	−1.28 (15)
O1—C11—C12—C13	−178.30 (9)	C14—C13—O13—C17	1.43 (15)
C16—C11—C12—C13	1.27 (15)	C12—C13—O13—C17	−179.11 (9)
C11—C12—C13—O13	−179.83 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O41—H41···O42i	0.927 (18)	1.804 (19)	2.7292 (11)	175.5 (16)
C17—H17B···O42ii	0.98	2.48	3.2477 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O41—H41⋯O42i	0.927 (18)	1.804 (19)	2.7292 (11)	175.5 (16)
C17—H17B⋯O42ii	0.98	2.48	3.2477 (14)	135

Symmetry codes: (i) ; (ii) .