2-Isopropyl-4-meth-oxy-5-methyl-phenyl acetate.

In the title compound, C13H18O3, the benzene ring is almost perpendicular to the acet-oxy plane, making a dihedral angle of 89.33 (11)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a zigzag chain along the c-axis direction.

Related literature

For background to natural monoterpenic phenols and their derivatives, see: Yuan-Lang & Erdtman (1962 ▶); Ündeğer et al. (2009 ▶); Osorio et al. (2006 ▶). For a related structure, see: Rajouani et al. (2008 ▶).

Experimental

Crystal data

C13H18O3

M = 222.27

Monoclinic,

a = 10.829 (2) Å

b = 9.600 (2) Å

c = 12.530 (3) Å

β = 100.34 (2)°

V = 1281.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 300 K

0.3 × 0.15 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.521, T max = 0.992

3366 measured reflections

2780 independent reflections

1594 reflections with I > 2σ(I)

R int = 0.018

2 standard reflections every 60 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.02

2780 reflections

151 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, hasacetf. DOI: 10.1107/S160053681302922X/is5314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302922X/is5314Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302922X/is5314Isup3.cml

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

C13H18O3	F(000) = 480
Mr = 222.27	Dx = 1.152 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.829 (2) Å	θ = 10–15°
b = 9.600 (2) Å	µ = 0.08 mm−1
c = 12.530 (3) Å	T = 300 K
β = 100.34 (2)°	Prism, colourless
V = 1281.4 (5) Å3	0.3 × 0.15 × 0.1 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1594 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 27.0°, θmin = 2.7°
ω/2θ scans	h = −13→1
Absorption correction: ψ scan (North et al., 1968)	k = −1→12
Tmin = 0.521, Tmax = 0.992	l = −15→15
3366 measured reflections	2 standard reflections every 60 min
2780 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2201P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2780 reflections	Δρmax = 0.16 e Å−3
151 parameters	Δρmin = −0.13 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: 0.016 (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	0.76460 (12)	0.08305 (13)	0.33870 (9)	0.0587 (4)
O2	0.76646 (18)	−0.07552 (19)	0.46746 (13)	0.1062 (7)
O3	0.43208 (12)	−0.20942 (15)	0.03401 (10)	0.0673 (4)
C1	0.68418 (16)	−0.00154 (18)	0.26312 (13)	0.0496 (4)
C2	0.73387 (16)	−0.09160 (17)	0.19660 (13)	0.0476 (4)
C3	0.64806 (16)	−0.16266 (18)	0.11839 (14)	0.0522 (4)
H1	0.6777	−0.2242	0.0715	0.063*
C4	0.52031 (16)	−0.14316 (18)	0.10945 (13)	0.0514 (4)
C5	0.47183 (17)	−0.0533 (2)	0.17877 (14)	0.0562 (5)
C6	0.55666 (17)	0.0175 (2)	0.25510 (14)	0.0570 (5)
H2	0.5272	0.0792	0.3020	0.068*
C7	0.79534 (17)	0.0364 (2)	0.44091 (15)	0.0612 (5)
C8	0.8695 (2)	0.1412 (3)	0.51249 (17)	0.0803 (7)
H3	0.8841	0.1081	0.5860	0.096*
H4	0.8239	0.2274	0.5082	0.096*
H5	0.9485	0.1559	0.4896	0.096*
C9	0.4748 (2)	−0.2910 (2)	−0.04666 (16)	0.0742 (6)
H6	0.5283	−0.2355	−0.0830	0.089*
H7	0.4041	−0.3229	−0.0983	0.089*
H8	0.5210	−0.3697	−0.0132	0.089*
C10	0.33271 (18)	−0.0334 (3)	0.16960 (19)	0.0812 (7)
H9	0.3168	0.0323	0.2233	0.097*
H10	0.2943	−0.1210	0.1810	0.097*
H11	0.2982	0.0011	0.0986	0.097*
C11	0.87402 (16)	−0.11360 (19)	0.20594 (15)	0.0546 (5)
H12	0.9162	−0.0529	0.2641	0.066*
C12	0.9114 (2)	−0.2629 (2)	0.23722 (18)	0.0747 (6)
H13	0.8718	−0.3250	0.1813	0.090*
H14	0.8850	−0.2857	0.3043	0.090*
H15	1.0009	−0.2723	0.2458	0.090*
C13	0.9195 (2)	−0.0725 (3)	0.10231 (18)	0.0785 (6)
H16	1.0093	−0.0797	0.1133	0.094*
H17	0.8949	0.0218	0.0837	0.094*
H19	0.8830	−0.1335	0.0445	0.094*

	U11	U22	U33	U12	U13	U23
O1	0.0685 (8)	0.0536 (7)	0.0512 (7)	−0.0086 (6)	0.0036 (6)	−0.0056 (6)
O2	0.1266 (15)	0.1007 (13)	0.0758 (10)	−0.0443 (11)	−0.0236 (10)	0.0304 (10)
O3	0.0564 (7)	0.0792 (9)	0.0621 (8)	−0.0073 (7)	−0.0007 (6)	−0.0123 (7)
C1	0.0553 (10)	0.0460 (10)	0.0448 (9)	−0.0017 (8)	0.0022 (8)	0.0014 (8)
C2	0.0509 (9)	0.0444 (9)	0.0464 (9)	−0.0011 (8)	0.0054 (7)	0.0033 (8)
C3	0.0574 (11)	0.0510 (10)	0.0475 (9)	−0.0004 (8)	0.0079 (8)	−0.0034 (8)
C4	0.0508 (10)	0.0521 (10)	0.0481 (9)	−0.0037 (8)	0.0006 (8)	0.0019 (8)
C5	0.0516 (10)	0.0583 (11)	0.0562 (10)	0.0076 (9)	0.0030 (8)	0.0052 (9)
C6	0.0624 (11)	0.0543 (11)	0.0543 (11)	0.0077 (9)	0.0108 (9)	−0.0040 (9)
C7	0.0533 (11)	0.0727 (13)	0.0545 (11)	−0.0043 (10)	0.0013 (9)	0.0009 (10)
C8	0.0706 (13)	0.0957 (17)	0.0675 (13)	−0.0095 (12)	−0.0071 (11)	−0.0155 (12)
C9	0.0796 (14)	0.0819 (15)	0.0586 (11)	−0.0200 (12)	0.0054 (10)	−0.0148 (11)
C10	0.0567 (12)	0.0940 (17)	0.0900 (16)	0.0120 (12)	0.0052 (11)	−0.0100 (13)
C11	0.0504 (10)	0.0560 (11)	0.0559 (10)	−0.0048 (9)	0.0053 (8)	−0.0048 (9)
C12	0.0615 (12)	0.0719 (14)	0.0860 (15)	0.0071 (11)	0.0006 (11)	0.0076 (12)
C13	0.0652 (13)	0.0903 (16)	0.0839 (15)	−0.0030 (12)	0.0236 (11)	0.0106 (13)

O1—C7	1.341 (2)	C11—C12	1.522 (3)
O1—C1	1.421 (2)	C8—H3	0.9600
O2—C7	1.183 (2)	C8—H4	0.9600
O3—C4	1.374 (2)	C8—H5	0.9600
O3—C9	1.420 (2)	C9—H6	0.9600
C1—C2	1.376 (2)	C9—H7	0.9600
C1—C6	1.379 (2)	C9—H8	0.9600
C2—C3	1.401 (2)	C10—H9	0.9600
C2—C11	1.516 (2)	C10—H10	0.9600
C3—C4	1.380 (2)	C10—H11	0.9600
C3—H1	0.9300	C11—H12	0.9800
C4—C5	1.392 (3)	C12—H13	0.9600
C5—C6	1.380 (2)	C12—H14	0.9600
C5—C10	1.502 (3)	C12—H15	0.9600
C6—H2	0.9300	C13—H16	0.9600
C7—C8	1.484 (3)	C13—H17	0.9600
C11—C13	1.521 (3)	C13—H19	0.9600
C7—O1—C1	117.57 (14)	O3—C9—H7	109.5
C4—O3—C9	118.02 (15)	H6—C9—H7	109.5
C2—C1—C6	122.33 (16)	O3—C9—H8	109.5
C2—C1—O1	120.23 (15)	H6—C9—H8	109.5
C6—C1—O1	117.31 (16)	H7—C9—H8	109.5
C1—C2—C3	116.58 (16)	C5—C10—H9	109.5
C1—C2—C11	122.40 (15)	C5—C10—H10	109.5
C3—C2—C11	121.02 (16)	H9—C10—H10	109.5
C4—C3—C2	121.33 (17)	C5—C10—H11	109.5
C4—C3—H1	119.3	H9—C10—H11	109.5
C2—C3—H1	119.3	H10—C10—H11	109.5
O3—C4—C3	123.79 (16)	C2—C11—C13	111.77 (15)
O3—C4—C5	115.01 (16)	C2—C11—C12	111.54 (15)
C3—C4—C5	121.20 (16)	C13—C11—C12	110.65 (17)
C6—C5—C4	117.32 (16)	C2—C11—H12	107.5
C6—C5—C10	121.61 (18)	C13—C11—H12	107.5
C4—C5—C10	121.07 (17)	C12—C11—H12	107.5
C1—C6—C5	121.23 (17)	C11—C12—H13	109.5
C1—C6—H2	119.4	C11—C12—H14	109.5
C5—C6—H2	119.4	H13—C12—H14	109.5
O2—C7—O1	122.63 (18)	C11—C12—H15	109.5
O2—C7—C8	125.96 (19)	H13—C12—H15	109.5
O1—C7—C8	111.41 (18)	H14—C12—H15	109.5
C7—C8—H3	109.5	C11—C13—H16	109.5
C7—C8—H4	109.5	C11—C13—H17	109.5
H3—C8—H4	109.5	H16—C13—H17	109.5
C7—C8—H5	109.5	C11—C13—H19	109.5
H3—C8—H5	109.5	H16—C13—H19	109.5
H4—C8—H5	109.5	H17—C13—H19	109.5
O3—C9—H6	109.5
C7—O1—C1—C2	−95.9 (2)	C3—C4—C5—C6	1.3 (3)
C7—O1—C1—C6	88.2 (2)	O3—C4—C5—C10	0.3 (3)
C6—C1—C2—C3	0.8 (3)	C3—C4—C5—C10	−179.34 (18)
O1—C1—C2—C3	−174.89 (14)	C2—C1—C6—C5	−0.3 (3)
C6—C1—C2—C11	−179.47 (17)	O1—C1—C6—C5	175.57 (16)
O1—C1—C2—C11	4.8 (2)	C4—C5—C6—C1	−0.8 (3)
C1—C2—C3—C4	−0.3 (2)	C10—C5—C6—C1	179.85 (19)
C11—C2—C3—C4	179.98 (16)	C1—O1—C7—O2	6.1 (3)
C9—O3—C4—C3	−7.0 (3)	C1—O1—C7—C8	−174.65 (16)
C9—O3—C4—C5	173.38 (16)	C1—C2—C11—C13	−118.73 (19)
C2—C3—C4—O3	179.64 (15)	C3—C2—C11—C13	61.0 (2)
C2—C3—C4—C5	−0.8 (3)	C1—C2—C11—C12	116.80 (19)
O3—C4—C5—C6	−179.06 (15)	C3—C2—C11—C12	−63.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H1···O2i	0.93	2.60	3.523 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H1⋯O2i	0.93	2.60	3.523 (3)	171

Symmetry code: (i) .