2-(4-Acetamido-phen-oxy)-2-methyl-propanoic acid.

In the title compound, C12H15NO4, the dihedral angle between the acetamide group and the ring is 29.6 (2)(su?)°. In the crystal mol-ecules are linked through N-H⋯O and O-H⋯O hydrogen bonds, thereby forming corrugated sheets propagating in the ac plane. These sheets are composed of R4(4)(28) graph-set motifs.

Related literature

For related literature on analogous structures with analgesic and anti­dyslipidemic activities, see: Kis et al. (2005 ▶); Navarrete-Vázquez et al. (2008 ▶, 2011 ▶); Thorp & Waring (1962 ▶); Miller & Spence (1998 ▶); Forcheron et al. (2002 ▶). For information on hydrogen bonding, see: Bernstein et al. (1995 ▶); Jeffrey (1997 ▶); Desiraju (1996 ▶).

Experimental

Crystal data

C12H15NO4

M = 237.25

Monoclinic,

a = 8.3184 (4) Å

b = 13.1554 (6) Å

c = 12.0452 (5) Å

β = 109.959 (5)°

V = 1238.96 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.19 × 0.14 × 0.13 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.982, T max = 0.988

34747 measured reflections

2179 independent reflections

1738 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

2179 reflections

161 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and DIAMOND (Crystal Impact, 2006 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004856/gw2131sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004856/gw2131Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004856/gw2131Isup3.cml

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

C12H15NO4	Dx = 1.272 Mg m−3
Mr = 237.25	Melting point: 438 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.3184 (4) Å	Cell parameters from 9500 reflections
b = 13.1554 (6) Å	θ = 3.0–29.3°
c = 12.0452 (5) Å	µ = 0.10 mm−1
β = 109.959 (5)°	T = 293 K
V = 1238.96 (10) Å3	Prism, colourless
Z = 4	0.19 × 0.14 × 0.13 mm
F(000) = 504

Agilent Xcalibur Atlas Gemini diffractometer	2179 independent reflections
Radiation source: (Mo) X-ray Source	1738 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.3659 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −15→15
Tmin = 0.982, Tmax = 0.988	l = −14→14
34747 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.3201P] where P = (Fo2 + 2Fc2)/3
2179 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.18 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
C1	0.57142 (18)	0.98467 (12)	0.81385 (13)	0.0332 (3)
C2	0.67842 (19)	0.96019 (12)	0.92728 (13)	0.0350 (4)
H2A	0.6433	0.9739	0.9912	0.042*
C3	0.83553 (19)	0.91600 (12)	0.94636 (13)	0.0355 (4)
H3	0.9059	0.9006	1.0229	0.043*
C4	0.88934 (18)	0.89431 (11)	0.85144 (13)	0.0320 (3)
C5	0.7820 (2)	0.91711 (13)	0.73829 (13)	0.0397 (4)
H5	0.8165	0.9023	0.6744	0.048*
C6	0.6234 (2)	0.96183 (13)	0.71873 (13)	0.0419 (4)
H6	0.5523	0.9764	0.6422	0.050*
C7	0.29399 (19)	1.06405 (12)	0.69952 (13)	0.0347 (4)
C8	0.3597 (3)	1.15075 (14)	0.64257 (18)	0.0578 (5)
H8A	0.4046	1.2038	0.6995	0.087*
H8B	0.2675	1.1771	0.5768	0.087*
H8C	0.4484	1.1259	0.6155	0.087*
C9	0.1450 (2)	1.10112 (13)	0.73554 (14)	0.0421 (4)
H9A	0.1112	1.0482	0.7779	0.063*
H9B	0.0504	1.1185	0.6662	0.063*
H9C	0.1798	1.1599	0.7852	0.063*
C10	0.23247 (19)	0.97382 (12)	0.61524 (12)	0.0349 (4)
C11	1.1489 (2)	0.79383 (12)	0.95558 (14)	0.0400 (4)
C12	1.3223 (2)	0.76481 (17)	0.95380 (19)	0.0633 (6)
H12A	1.4078	0.7842	1.0271	0.095*
H12B	1.3434	0.7990	0.8897	0.095*
H12C	1.3267	0.6926	0.9434	0.095*
H1	1.099 (3)	0.8691 (17)	0.8137 (17)	0.076*
N1	1.05465 (16)	0.85358 (10)	0.86741 (11)	0.0362 (3)
O1	0.41935 (13)	1.03044 (9)	0.80935 (8)	0.0390 (3)
O2	0.20332 (16)	0.89154 (9)	0.66919 (9)	0.0454 (3)
H2	0.1674	0.8458	0.6208	0.068*
O3	0.20982 (17)	0.97740 (11)	0.51131 (9)	0.0566 (4)
O4	1.09585 (17)	0.76373 (10)	1.03443 (11)	0.0555 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0302 (8)	0.0358 (8)	0.0335 (8)	−0.0015 (6)	0.0109 (6)	−0.0033 (6)
C2	0.0367 (8)	0.0422 (9)	0.0286 (7)	0.0008 (7)	0.0145 (6)	−0.0035 (7)
C3	0.0374 (8)	0.0405 (9)	0.0279 (7)	0.0021 (7)	0.0101 (6)	−0.0001 (7)
C4	0.0341 (8)	0.0301 (8)	0.0351 (8)	−0.0017 (6)	0.0161 (6)	0.0002 (6)
C5	0.0417 (9)	0.0518 (10)	0.0307 (8)	0.0021 (8)	0.0190 (7)	0.0000 (7)
C6	0.0401 (9)	0.0567 (11)	0.0282 (8)	0.0039 (8)	0.0106 (7)	0.0009 (7)
C7	0.0328 (8)	0.0373 (9)	0.0325 (8)	0.0009 (7)	0.0092 (6)	0.0047 (7)
C8	0.0660 (13)	0.0443 (11)	0.0709 (13)	−0.0051 (9)	0.0333 (10)	0.0093 (9)
C9	0.0390 (9)	0.0435 (9)	0.0423 (9)	0.0073 (7)	0.0121 (7)	0.0020 (7)
C10	0.0314 (8)	0.0453 (9)	0.0281 (8)	0.0011 (7)	0.0105 (6)	0.0036 (7)
C11	0.0423 (9)	0.0361 (9)	0.0462 (9)	0.0052 (7)	0.0210 (8)	0.0040 (7)
C12	0.0519 (11)	0.0667 (13)	0.0807 (14)	0.0208 (10)	0.0346 (11)	0.0217 (11)
N1	0.0377 (7)	0.0386 (7)	0.0385 (7)	0.0047 (6)	0.0211 (6)	0.0056 (6)
O1	0.0312 (6)	0.0541 (7)	0.0295 (5)	0.0068 (5)	0.0073 (4)	−0.0041 (5)
O2	0.0633 (8)	0.0415 (7)	0.0362 (6)	−0.0136 (6)	0.0231 (6)	−0.0078 (5)
O3	0.0713 (9)	0.0697 (9)	0.0273 (6)	−0.0061 (7)	0.0149 (6)	0.0010 (6)
O4	0.0630 (8)	0.0584 (8)	0.0571 (7)	0.0249 (6)	0.0362 (7)	0.0247 (6)

C1—O1	1.3852 (18)	C8—H8A	0.9600
C1—C6	1.389 (2)	C8—H8B	0.9600
C1—C2	1.390 (2)	C8—H8C	0.9600
C2—C3	1.376 (2)	C9—H9A	0.9600
C2—H2A	0.9300	C9—H9B	0.9600
C3—C4	1.392 (2)	C9—H9C	0.9600
C3—H3	0.9300	C10—O3	1.2015 (17)
C4—C5	1.383 (2)	C10—O2	1.3268 (19)
C4—N1	1.4264 (19)	C11—O4	1.2410 (18)
C5—C6	1.389 (2)	C11—N1	1.339 (2)
C5—H5	0.9300	C11—C12	1.499 (2)
C6—H6	0.9300	C12—H12A	0.9600
C7—O1	1.4461 (18)	C12—H12B	0.9600
C7—C8	1.525 (2)	C12—H12C	0.9600
C7—C9	1.526 (2)	N1—H1	0.86 (2)
C7—C10	1.532 (2)	O2—H2	0.8200
O1—C1—C6	126.82 (13)	C7—C8—H8C	109.5
O1—C1—C2	114.14 (12)	H8A—C8—H8C	109.5
C6—C1—C2	119.04 (14)	H8B—C8—H8C	109.5
C3—C2—C1	120.99 (13)	C7—C9—H9A	109.5
C3—C2—H2A	119.5	C7—C9—H9B	109.5
C1—C2—H2A	119.5	H9A—C9—H9B	109.5
C2—C3—C4	120.18 (14)	C7—C9—H9C	109.5
C2—C3—H3	119.9	H9A—C9—H9C	109.5
C4—C3—H3	119.9	H9B—C9—H9C	109.5
C5—C4—C3	118.96 (14)	O3—C10—O2	123.53 (15)
C5—C4—N1	118.86 (13)	O3—C10—C7	123.93 (14)
C3—C4—N1	122.12 (13)	O2—C10—C7	112.52 (12)
C4—C5—C6	121.01 (14)	O4—C11—N1	121.96 (14)
C4—C5—H5	119.5	O4—C11—C12	121.67 (15)
C6—C5—H5	119.5	N1—C11—C12	116.36 (14)
C1—C6—C5	119.80 (14)	C11—C12—H12A	109.5
C1—C6—H6	120.1	C11—C12—H12B	109.5
C5—C6—H6	120.1	H12A—C12—H12B	109.5
O1—C7—C8	112.51 (14)	C11—C12—H12C	109.5
O1—C7—C9	103.87 (11)	H12A—C12—H12C	109.5
C8—C7—C9	109.84 (14)	H12B—C12—H12C	109.5
O1—C7—C10	110.04 (12)	C11—N1—C4	127.18 (12)
C8—C7—C10	111.79 (13)	C11—N1—H1	116.3 (15)
C9—C7—C10	108.42 (12)	C4—N1—H1	116.5 (15)
C7—C8—H8A	109.5	C1—O1—C7	122.17 (11)
C7—C8—H8B	109.5	C10—O2—H2	109.5
H8A—C8—H8B	109.5
O1—C1—C2—C3	−178.80 (14)	O1—C7—C10—O2	43.10 (16)
C6—C1—C2—C3	1.4 (2)	C8—C7—C10—O2	168.89 (14)
C1—C2—C3—C4	−0.5 (2)	C9—C7—C10—O2	−69.88 (16)
C2—C3—C4—C5	−0.5 (2)	O4—C11—N1—C4	2.6 (3)
C2—C3—C4—N1	176.59 (14)	C12—C11—N1—C4	−177.66 (16)
C3—C4—C5—C6	0.6 (2)	C5—C4—N1—C11	−153.32 (16)
N1—C4—C5—C6	−176.60 (15)	C3—C4—N1—C11	29.6 (2)
O1—C1—C6—C5	178.93 (15)	C6—C1—O1—C7	−2.1 (2)
C2—C1—C6—C5	−1.3 (2)	C2—C1—O1—C7	178.16 (13)
C4—C5—C6—C1	0.3 (3)	C8—C7—O1—C1	−65.53 (19)
O1—C7—C10—O3	−138.24 (15)	C9—C7—O1—C1	175.74 (13)
C8—C7—C10—O3	−12.4 (2)	C10—C7—O1—C1	59.85 (17)
C9—C7—C10—O3	108.79 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.87 (2)	2.21 (2)	3.081 (2)	174 (2)
O2—H2···O4ii	0.82	1.76	2.572 (2)	172
C3—H3···O4	0.93	2.37	2.874 (2)	114
C2—H2A···O1iii	0.93	2.63	3.536	166
C5—H5···O3iv	0.93	2.69	3.333	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.87 (2)	2.21 (2)	3.081 (2)	174 (2)
O2—H2⋯O4ii	0.82	1.76	2.572 (2)	172
C2—H2A⋯O1iii	0.93	2.63	3.536	166
C5—H5⋯O3iv	0.93	2.69	3.333	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .