Methyl (4-acetyl­phenoxy)­acetate

The molecule of the title compound, C₁₁H₁₂O₄, is essentially planar. The OCH₂COOCH₃ group is extended away from the aromatic ring, with an O-C-C-O torsion angle of 173.9 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.144
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

As shown in Fig. 1, the title compound (I), in which the OCH₂COOCH₃ group is extended away from the aromatic ring with an O—C—C—O torsion angle of 173.9 (1)°, is essentially planar ignoring all hydrogen atoms.

The C10—O3 and C10—O4 bond lengths are 1.193 (2) and 1.327 (2) Å, respectively, and the O3—C10—O4 angle is 125.2 (1)°. The C10—O3 distance is shorter than that found in other similar coordinated ester molecules (Gonzàlez-Duarte et al., 1996; Ríos-Moreno et al., 2003), while the C10—O4 distance is shorter than that found in another similar ester (Ping et al., 2007).

Related literature

For related literature, see: Gonzàlez-Duarte et al. (1996); Ping et al. (2007); Ríos-Moreno et al. (2003).

S2. Experimental

A mixture of ethyl p-hydroxybenzoate (8.3 g, 50 mmol) and NaOH (2.0 g, 50 mmol) in DMSO (10 ml) was stirred at 333 K for 1 h, and then the methyl chloroacetate (5.4 g, 50 mmol) was added. The mixture was cooled to room temperature after stirring at 333 K for 2 h, then poured into 200 ml of water and a white solid formed immediately. The obtained precipitate (0.20 g) was dissolved in 15 ml me thanol, and colorless single crystals of (I) were obtained after several days at room temperature.

S3. Refinement

All H atoms on C atoms were positioned geometrically and refined as riding atoms, with d(C—H) = 0.93 Å, U_iso = 1.2U_eq(C) for aromatic, 0.97 Å, U_iso = 1.5U_eq(C) for CH₂ atoms and 0.96 Å, U_iso = 1.5U_eq(C) for CH₃ atoms.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker,1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. View of the structure of (I). Displacement ellipsoids are drawn at the 30% probability level.

Methyl 4-acetylphenoxyacetate

Crystal data

C11H12O4	F(000) = 880
Mr = 208.21	Dx = 1.333 Mg m^−3
Monoclinic, C2/c	Melting point: not measured K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71069 Å
a = 24.690 (1) Å	Cell parameters from 2421 reflections
b = 7.5580 (6) Å	θ = 3.3–28.2°
c = 11.1280 (9) Å	µ = 0.10 mm^−1
β = 92.230 (1)°	T = 273 K
V = 2075.0 (2) Å^3	Block, colorless
Z = 8	0.40 × 0.30 × 0.25 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2421 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 28.2°, θmin = 3.3°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −32→20
Tmin = 0.970, Tmax = 0.980	k = −9→9
6117 measured reflections	l = −14→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.081P)^2 + 0.3709P] where P = (Fo^2 + 2Fc^2)/3
2421 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.23473 (6)	0.5091 (3)	0.57792 (15)	0.0612 (4)
H1A	0.2014	0.5370	0.6155	0.092*
H1B	0.2285	0.4154	0.5208	0.092*
H1C	0.2477	0.6119	0.5373	0.092*
C2	0.27612 (5)	0.45135 (19)	0.67172 (12)	0.0462 (3)
C3	0.33143 (5)	0.40001 (17)	0.63545 (11)	0.0402 (3)
C4	0.36934 (5)	0.34295 (19)	0.72408 (12)	0.0446 (3)
H4	0.3596	0.3384	0.8039	0.054*
C5	0.42082 (5)	0.29360 (19)	0.69471 (12)	0.0465 (3)
H5	0.4456	0.2557	0.7544	0.056*
C6	0.43570 (5)	0.30052 (18)	0.57537 (12)	0.0428 (3)
C7	0.39911 (5)	0.3578 (2)	0.48646 (12)	0.0482 (3)
H7	0.4091	0.3632	0.4068	0.058*
C8	0.34732 (5)	0.40702 (19)	0.51710 (12)	0.0458 (3)
H8	0.3227	0.4455	0.4573	0.055*
C9	0.50411 (5)	0.2400 (2)	0.43547 (12)	0.0478 (3)
H9A	0.5012	0.3564	0.3991	0.057*
H9B	0.4814	0.1589	0.3886	0.057*
C10	0.56212 (5)	0.17801 (18)	0.43853 (12)	0.0448 (3)
C11	0.63673 (7)	0.1337 (3)	0.31544 (18)	0.0683 (5)
H11A	0.6459	0.1441	0.2327	0.102*
H11B	0.6412	0.0131	0.3410	0.102*
H11C	0.6601	0.2085	0.3640	0.102*
O1	0.26456 (5)	0.4471 (2)	0.77717 (10)	0.0760 (4)
O2	0.48748 (4)	0.24604 (15)	0.55592 (9)	0.0551 (3)
O3	0.58735 (4)	0.12804 (18)	0.52558 (10)	0.0651 (3)
O4	0.58085 (4)	0.18728 (16)	0.32852 (10)	0.0598 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0409 (7)	0.0861 (12)	0.0568 (9)	0.0101 (7)	0.0047 (6)	0.0061 (8)
C2	0.0401 (7)	0.0560 (8)	0.0428 (7)	−0.0026 (6)	0.0065 (5)	−0.0018 (6)
C3	0.0369 (6)	0.0444 (7)	0.0394 (7)	−0.0024 (5)	0.0032 (5)	−0.0017 (5)
C4	0.0442 (7)	0.0570 (8)	0.0328 (6)	−0.0010 (6)	0.0033 (5)	−0.0023 (5)
C5	0.0417 (7)	0.0619 (8)	0.0356 (7)	0.0034 (6)	−0.0034 (5)	−0.0007 (6)
C6	0.0348 (6)	0.0548 (8)	0.0389 (7)	0.0008 (5)	0.0016 (5)	−0.0031 (5)
C7	0.0426 (7)	0.0674 (9)	0.0346 (7)	0.0035 (6)	0.0039 (5)	0.0027 (6)
C8	0.0389 (7)	0.0598 (8)	0.0384 (7)	0.0036 (6)	−0.0001 (5)	0.0046 (6)
C9	0.0378 (7)	0.0668 (9)	0.0389 (7)	0.0043 (6)	0.0027 (5)	−0.0006 (6)
C10	0.0397 (7)	0.0509 (7)	0.0440 (7)	−0.0004 (5)	0.0023 (5)	−0.0050 (6)
C11	0.0483 (8)	0.0781 (11)	0.0800 (12)	0.0131 (7)	0.0222 (8)	0.0037 (9)
O1	0.0512 (7)	0.1315 (12)	0.0459 (6)	0.0128 (7)	0.0118 (5)	0.0011 (6)
O2	0.0374 (5)	0.0899 (8)	0.0381 (5)	0.0112 (5)	0.0021 (4)	−0.0023 (5)
O3	0.0523 (6)	0.0943 (9)	0.0485 (6)	0.0169 (6)	−0.0022 (5)	−0.0011 (5)
O4	0.0454 (6)	0.0848 (8)	0.0501 (6)	0.0140 (5)	0.0117 (4)	0.0036 (5)

Geometric parameters (Å, º)

C1—C2	1.497 (2)	C7—C8	1.3871 (18)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—O2	1.418 (2)
C2—O1	1.219 (2)	C9—C10	1.5062 (19)
C2—C3	1.4903 (18)	C9—H9A	0.9700
C3—C8	1.3898 (18)	C9—H9B	0.9700
C3—C4	1.4010 (18)	C10—O3	1.193 (2)
C4—C5	1.3761 (18)	C10—O4	1.327 (2)
C4—H4	0.9300	C11—O4	1.4505 (17)
C5—C6	1.3926 (18)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—O2	1.368 (2)	C11—H11C	0.9600
C6—C7	1.3830 (18)
C2—C1—H1A	109.5	C6—C7—H7	120.3
C2—C1—H1B	109.5	C8—C7—H7	120.3
H1A—C1—H1B	109.5	C7—C8—C3	121.31 (12)
C2—C1—H1C	109.5	C7—C8—H8	119.3
H1A—C1—H1C	109.5	C3—C8—H8	119.3
H1B—C1—H1C	109.5	O2—C9—C10	107.38 (11)
O1—C2—C3	120.35 (13)	O2—C9—H9A	110.2
O1—C2—C1	119.99 (13)	C10—C9—H9A	110.2
C3—C2—C1	119.66 (12)	O2—C9—H9B	110.2
C8—C3—C4	118.25 (12)	C10—C9—H9B	110.2
C8—C3—C2	122.82 (12)	H9A—C9—H9B	108.5
C4—C3—C2	118.92 (12)	O3—C10—O4	125.2 (1)
C5—C4—C3	120.95 (12)	O3—C10—C9	125.67 (13)
C5—C4—H4	119.5	O4—C10—C9	109.14 (11)
C3—C4—H4	119.5	O4—C11—H11A	109.5
C4—C5—C6	119.78 (12)	O4—C11—H11B	109.5
C4—C5—H5	120.1	H11A—C11—H11B	109.5
C6—C5—H5	120.1	O4—C11—H11C	109.5
O2—C6—C7	124.70 (12)	H11A—C11—H11C	109.5
O2—C6—C5	114.98 (11)	H11B—C11—H11C	109.5
C7—C6—C5	120.31 (12)	C6—O2—C9	117.77 (10)
C6—C7—C8	119.40 (12)	C10—O4—C11	116.4 (1)
O1—C2—C3—C8	−178.17 (14)	C6—C7—C8—C3	0.0 (2)
C1—C2—C3—C8	1.6 (2)	C4—C3—C8—C7	0.5 (2)
O1—C2—C3—C4	1.5 (2)	C2—C3—C8—C7	−179.83 (13)
C1—C2—C3—C4	−178.75 (13)	O2—C9—C10—O3	6.3 (2)
C8—C3—C4—C5	−0.6 (2)	O2—C9—C10—O4	−173.91 (12)
C2—C3—C4—C5	179.75 (13)	C7—C6—O2—C9	−3.0 (2)
C3—C4—C5—C6	0.1 (2)	C5—C6—O2—C9	176.37 (13)
C4—C5—C6—O2	−179.04 (12)	C10—C9—O2—C6	179.56 (11)
C4—C5—C6—C7	0.4 (2)	O3—C10—O4—C11	−0.8 (2)
O2—C6—C7—C8	178.92 (13)	C9—C10—O4—C11	179.40 (13)
C5—C6—C7—C8	−0.5 (2)