trans-4-(Phenoxy-meth-yl)cyclo-hexane-carboxylic acid.

The title compound, C(14)H(18)O(3), is an important model compound in the synthesis of phenolic ethers. The cyclo-hexane ring adopts a chair conformation. In the crystal structure, adjacent mol-ecules are linked by O-H⋯O hydrogen bonds.

Related literature

For related literature, see: Dunitz & Strickler (1966 ▶); Sekera & Marvel (1933 ▶); Luger et al. (1972 ▶).

Experimental

Crystal data

C14H18O3

M = 234.28

Monoclinic,

a = 6.178 (3) Å

b = 35.042 (8) Å

c = 6.526 (3) Å

β = 113.93 (4)°

V = 1291.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 (2) K

0.45 × 0.25 × 0.24 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2657 measured reflections

2330 independent reflections

1301 reflections with I > 2σ(I)

R int = 0.001

3 standard reflections every 250 reflections intensity decay: 1.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.149

S = 0.97

2330 reflections

156 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007381/bv2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007381/bv2092Isup2.hkl

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

C14H18O3	F(000) = 504
Mr = 234.28	Dx = 1.205 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.178 (3) Å	Cell parameters from 30 reflections
b = 35.042 (8) Å	θ = 4.5–9.5°
c = 6.526 (3) Å	µ = 0.08 mm−1
β = 113.93 (4)°	T = 292 K
V = 1291.4 (9) Å3	Block, colourless
Z = 4	0.45 × 0.25 × 0.24 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.001
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 3.5°
graphite	h = −7→6
ω/2–θ scans	k = 0→42
2657 measured reflections	l = −1→7
2330 independent reflections	3 standard reflections every 250 reflections
1301 reflections with I > 2σ(I)	intensity decay: 1.8%

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0395P)2] where P = (Fo2 + 2Fc2)/3
2330 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.17 e Å−3
9 restraints	Δρmin = −0.17 e Å−3

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	0.5351 (13)	0.8410 (2)	−0.0641 (11)	0.084 (2)
O2	1.0653 (15)	0.9709 (3)	0.8119 (13)	0.110 (3)
H2	1.1166	0.9870	0.9115	0.132*
O3	0.7287 (14)	0.9889 (2)	0.8198 (11)	0.104 (3)
C1	0.584 (2)	0.8016 (3)	−0.328 (2)	0.087 (4)
H1	0.7444	0.8012	−0.2354	0.105*
C2	0.494 (4)	0.7816 (4)	−0.531 (3)	0.112 (6)
H2A	0.5971	0.7680	−0.5758	0.134*
C3	0.260 (4)	0.7818 (4)	−0.662 (3)	0.117 (6)
H3	0.2030	0.7679	−0.7951	0.141*
C4	0.103 (3)	0.8026 (4)	−0.6030 (19)	0.102 (5)
H4	−0.0571	0.8032	−0.6962	0.123*
C5	0.192 (3)	0.8225 (3)	−0.3991 (19)	0.085 (4)
H5	0.0893	0.8360	−0.3543	0.102*
C6	0.425 (3)	0.8221 (3)	−0.268 (2)	0.074 (4)
C7	0.3845 (19)	0.8640 (3)	0.0058 (16)	0.080 (4)
H7A	0.2653	0.8483	0.0257	0.096*
H7B	0.3052	0.8834	−0.1060	0.096*
C8	0.5426 (19)	0.8826 (3)	0.2262 (15)	0.062 (3)
H8	0.6310	0.8625	0.3314	0.074*
C9	0.3865 (17)	0.9033 (3)	0.3227 (15)	0.076 (4)
H9A	0.2912	0.9223	0.2163	0.092*
H9B	0.2802	0.8852	0.3460	0.092*
C10	0.5351 (19)	0.9225 (3)	0.5425 (15)	0.076 (4)
H10A	0.4323	0.9360	0.5975	0.092*
H10B	0.6210	0.9033	0.6524	0.092*
C11	0.7078 (19)	0.9501 (3)	0.5158 (16)	0.066 (3)
H11	0.6143	0.9689	0.4037	0.079*
C12	0.8661 (18)	0.9296 (3)	0.4193 (15)	0.075 (3)
H12A	0.9704	0.9480	0.3942	0.091*
H12B	0.9635	0.9108	0.5261	0.091*
C13	0.7164 (19)	0.9100 (3)	0.2005 (16)	0.077 (3)
H13A	0.6310	0.9292	0.0898	0.092*
H13B	0.8191	0.8964	0.1460	0.092*
C14	0.842 (2)	0.9717 (4)	0.7277 (17)	0.073 (4)

	U11	U22	U33	U12	U13	U23
O1	0.102 (6)	0.090 (6)	0.065 (5)	−0.001 (5)	0.040 (5)	−0.021 (5)
O2	0.103 (7)	0.143 (9)	0.085 (6)	0.002 (7)	0.040 (6)	−0.046 (5)
O3	0.109 (7)	0.127 (8)	0.083 (6)	0.020 (6)	0.046 (5)	−0.031 (5)
C1	0.120 (12)	0.073 (9)	0.093 (9)	0.000 (8)	0.068 (9)	−0.004 (8)
C2	0.179 (18)	0.097 (12)	0.102 (12)	−0.012 (13)	0.100 (13)	−0.017 (10)
C3	0.20 (2)	0.099 (12)	0.078 (11)	−0.008 (14)	0.078 (13)	−0.007 (9)
C4	0.152 (14)	0.093 (11)	0.070 (9)	−0.011 (10)	0.052 (10)	−0.013 (8)
C5	0.114 (12)	0.088 (10)	0.058 (8)	0.000 (9)	0.038 (8)	−0.009 (8)
C6	0.108 (12)	0.063 (9)	0.063 (8)	0.000 (9)	0.045 (9)	0.002 (7)
C7	0.098 (9)	0.090 (9)	0.066 (7)	−0.006 (8)	0.049 (7)	−0.010 (7)
C8	0.080 (8)	0.056 (8)	0.051 (6)	0.001 (7)	0.029 (6)	−0.004 (6)
C9	0.088 (9)	0.095 (10)	0.061 (7)	−0.013 (7)	0.045 (7)	−0.013 (7)
C10	0.096 (9)	0.090 (9)	0.062 (7)	−0.025 (8)	0.052 (7)	−0.021 (7)
C11	0.084 (9)	0.065 (8)	0.050 (6)	0.005 (7)	0.030 (6)	−0.010 (6)
C12	0.088 (9)	0.079 (9)	0.067 (7)	−0.012 (7)	0.039 (7)	−0.011 (7)
C13	0.089 (9)	0.098 (10)	0.059 (7)	−0.013 (8)	0.044 (7)	−0.017 (7)
C14	0.068 (9)	0.102 (10)	0.055 (7)	0.013 (9)	0.030 (7)	0.004 (7)

O1—C6	1.394 (12)	C7—H7B	0.9700
O1—C7	1.438 (10)	C8—C13	1.501 (12)
O2—C14	1.261 (11)	C8—C9	1.532 (11)
O2—H2	0.8200	C8—H8	0.9800
O3—C14	1.248 (11)	C9—C10	1.512 (12)
C1—C6	1.392 (14)	C9—H9A	0.9700
C1—C2	1.401 (16)	C9—H9B	0.9700
C1—H1	0.9300	C10—C11	1.501 (12)
C2—C3	1.350 (18)	C10—H10A	0.9700
C2—H2A	0.9300	C10—H10B	0.9700
C3—C4	1.386 (17)	C11—C14	1.497 (13)
C3—H3	0.9300	C11—C12	1.540 (12)
C4—C5	1.402 (13)	C11—H11	0.9800
C4—H4	0.9300	C12—C13	1.514 (12)
C5—C6	1.341 (14)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C7—C8	1.519 (12)	C13—H13A	0.9700
C7—H7A	0.9700	C13—H13B	0.9700
C6—O1—C7	116.2 (9)	C10—C9—H9A	109.4
C14—O2—H2	109.5	C8—C9—H9A	109.4
C6—C1—C2	118.1 (14)	C10—C9—H9B	109.4
C6—C1—H1	120.9	C8—C9—H9B	109.4
C2—C1—H1	120.9	H9A—C9—H9B	108.0
C3—C2—C1	120.5 (16)	C11—C10—C9	111.3 (8)
C3—C2—H2A	119.8	C11—C10—H10A	109.4
C1—C2—H2A	119.8	C9—C10—H10A	109.4
C2—C3—C4	121.1 (16)	C11—C10—H10B	109.4
C2—C3—H3	119.5	C9—C10—H10B	109.4
C4—C3—H3	119.5	H10A—C10—H10B	108.0
C3—C4—C5	118.5 (14)	C14—C11—C10	111.9 (8)
C3—C4—H4	120.7	C14—C11—C12	114.1 (10)
C5—C4—H4	120.7	C10—C11—C12	110.2 (8)
C6—C5—C4	120.3 (12)	C14—C11—H11	106.7
C6—C5—H5	119.8	C10—C11—H11	106.7
C4—C5—H5	119.8	C12—C11—H11	106.7
C5—C6—C1	121.5 (12)	C13—C12—C11	110.5 (9)
C5—C6—O1	125.9 (11)	C13—C12—H12A	109.5
C1—C6—O1	112.7 (13)	C11—C12—H12A	109.5
O1—C7—C8	106.9 (9)	C13—C12—H12B	109.5
O1—C7—H7A	110.3	C11—C12—H12B	109.5
C8—C7—H7A	110.3	H12A—C12—H12B	108.1
O1—C7—H7B	110.3	C8—C13—C12	112.1 (7)
C8—C7—H7B	110.3	C8—C13—H13A	109.2
H7A—C7—H7B	108.6	C12—C13—H13A	109.2
C13—C8—C7	112.5 (8)	C8—C13—H13B	109.2
C13—C8—C9	109.9 (8)	C12—C13—H13B	109.2
C7—C8—C9	108.8 (9)	H13A—C13—H13B	107.9
C13—C8—H8	108.5	O3—C14—O2	122.0 (11)
C7—C8—H8	108.5	O3—C14—C11	118.6 (11)
C9—C8—H8	108.5	O2—C14—C11	119.4 (11)
C10—C9—C8	111.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.83	2.626 (10)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	1.83	2.626 (10)	164

Symmetry code: (i) .