Methyl eucomate.

THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: methyl 3-carboxy-3-hydr-oxy-3-(4-hydroxy-benz-yl)propanoate], C(12)H(14)O(6), is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds. The mol-ecules are arranged in layers, parallel to (001), which are inter-connected by the O-H⋯O hydrogen bonds.

Related literature

For related literature, see: Heller & Tamm (1974 ▶); Jiang et al. (2002 ▶, 2006 ▶).

Experimental

Crystal data

C12H14O6

M = 254.23

Orthorhombic,

a = 5.9109 (6) Å

b = 7.0348 (7) Å

c = 29.109 (3) Å

V = 1210.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.40 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

6709 measured reflections

1279 independent reflections

1047 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.066

S = 1.05

1278 reflections

168 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT and XPREP in SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018734/fb2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018734/fb2096Isup2.hkl

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

C12H14O6	F000 = 536
Mr = 254.23	Dx = 1.395 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6709 reflections
a = 5.9109 (6) Å	θ = 1.4–25.0º
b = 7.0348 (7) Å	µ = 0.11 mm−1
c = 29.109 (3) Å	T = 293 (2) K
V = 1210.4 (2) Å3	Rectangular, colourless
Z = 4	0.40 × 0.32 × 0.25 mm

Bruker SMART/CCD diffractometer	1047 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Monochromator: graphite	θmax = 25.0º
T = 293(2) K	θmin = 1.4º
ω scans	h = −6→7
Absorption correction: none	k = −8→7
6709 measured reflections	l = −27→34
1279 independent reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0328P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.14 e Å−3
1278 reflections	Δρmin = −0.12 e Å−3
168 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
42 constraints	Extinction coefficient: 0.0070 (19)
Primary atom site location: structure-invariant direct methods	Absolute structure:
Secondary atom site location: difference Fourier map

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	0.2505 (3)	0.2830 (2)	0.32392 (5)	0.0466 (5)
H1	0.1313	0.2346	0.3323	0.070*
O2	0.5510 (2)	0.5081 (2)	0.11441 (5)	0.0400 (4)
H2	0.5099	0.5865	0.1335	0.060*
O3	0.1405 (3)	0.6278 (2)	0.13901 (5)	0.0425 (4)
O4	−0.0301 (3)	0.3948 (3)	0.09911 (6)	0.0499 (5)
H4	−0.1460	0.4500	0.1070	0.075*
O5	0.2745 (4)	0.6569 (3)	0.03265 (6)	0.0640 (6)
O6	0.3709 (3)	0.4543 (2)	−0.02286 (5)	0.0543 (5)
C1	0.2722 (4)	0.2631 (3)	0.27718 (8)	0.0344 (6)
C2	0.4773 (4)	0.3133 (3)	0.25799 (8)	0.0367 (6)
H2B	0.5932	0.3598	0.2764	0.044*
C3	0.5089 (4)	0.2940 (3)	0.21133 (8)	0.0370 (6)
H3A	0.6475	0.3286	0.1987	0.044*
C4	0.3420 (4)	0.2253 (3)	0.18265 (8)	0.0346 (6)
C5	0.1367 (4)	0.1752 (3)	0.20275 (8)	0.0389 (6)
H5A	0.0209	0.1285	0.1843	0.047*
C6	0.1010 (4)	0.1933 (3)	0.24947 (9)	0.0387 (6)
H6A	−0.0373	0.1588	0.2622	0.046*
C7	0.3804 (4)	0.2011 (3)	0.13179 (8)	0.0400 (6)
H7A	0.2693	0.1119	0.1201	0.048*
H7B	0.5286	0.1451	0.1272	0.048*
C8	0.3660 (4)	0.3855 (3)	0.10324 (7)	0.0336 (5)
C9	0.3831 (4)	0.3384 (3)	0.05217 (8)	0.0403 (6)
H9A	0.5339	0.2904	0.0459	0.048*
H9B	0.2767	0.2375	0.0452	0.048*
C10	0.3374 (4)	0.5023 (4)	0.02090 (8)	0.0424 (6)
C11	0.1476 (4)	0.4865 (4)	0.11534 (7)	0.0347 (5)
C12	0.3196 (5)	0.5985 (4)	−0.05667 (9)	0.0681 (9)
H12A	0.3552	0.5515	−0.0868	0.102*
H12B	0.4079	0.7102	−0.0505	0.102*
H12C	0.1617	0.6297	−0.0552	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.0418 (10)	0.0604 (11)	0.0377 (10)	−0.0079 (10)	0.0050 (8)	0.0063 (9)
O2	0.0255 (9)	0.0527 (11)	0.0418 (11)	−0.0021 (8)	0.0013 (7)	−0.0105 (9)
O3	0.0368 (9)	0.0474 (10)	0.0432 (10)	0.0061 (9)	0.0051 (8)	−0.0103 (8)
O4	0.0229 (9)	0.0617 (12)	0.0651 (12)	0.0047 (9)	−0.0011 (9)	−0.0157 (11)
O5	0.0819 (15)	0.0646 (12)	0.0454 (11)	0.0208 (12)	0.0057 (11)	−0.0017 (10)
O6	0.0678 (12)	0.0652 (11)	0.0298 (9)	−0.0045 (11)	0.0042 (10)	−0.0054 (9)
C1	0.0334 (13)	0.0335 (13)	0.0363 (14)	0.0024 (11)	0.0021 (11)	0.0060 (11)
C2	0.0315 (12)	0.0395 (14)	0.0391 (15)	−0.0086 (12)	−0.0029 (11)	0.0020 (12)
C3	0.0277 (12)	0.0404 (13)	0.0429 (15)	−0.0040 (12)	0.0035 (11)	0.0041 (12)
C4	0.0294 (12)	0.0326 (12)	0.0417 (14)	0.0046 (11)	−0.0010 (11)	0.0021 (11)
C5	0.0293 (12)	0.0412 (13)	0.0463 (15)	−0.0009 (12)	−0.0045 (12)	0.0000 (12)
C6	0.0263 (12)	0.0430 (13)	0.0470 (15)	−0.0029 (11)	0.0030 (11)	0.0068 (13)
C7	0.0336 (12)	0.0431 (13)	0.0431 (14)	0.0062 (12)	−0.0021 (12)	−0.0074 (12)
C8	0.0223 (11)	0.0441 (14)	0.0344 (13)	0.0009 (12)	−0.0012 (11)	−0.0054 (12)
C9	0.0334 (13)	0.0521 (14)	0.0356 (14)	0.0060 (12)	0.0028 (11)	−0.0071 (12)
C10	0.0315 (13)	0.0572 (16)	0.0385 (14)	−0.0011 (15)	0.0029 (12)	−0.0075 (14)
C11	0.0277 (12)	0.0460 (14)	0.0303 (12)	0.0012 (13)	−0.0001 (11)	0.0007 (12)
C12	0.085 (2)	0.080 (2)	0.0393 (15)	−0.023 (2)	−0.0078 (16)	0.0111 (16)

O1—C1	1.374 (3)	C4—C5	1.392 (3)
O1—H1	0.8200	C4—C7	1.507 (3)
O2—C8	1.430 (3)	C5—C6	1.382 (3)
O2—H2	0.8200	C5—H5A	0.9300
O3—C11	1.210 (3)	C6—H6A	0.9300
O4—C11	1.320 (3)	C7—C8	1.543 (3)
O4—H4	0.8200	C7—H7A	0.9700
O5—C10	1.200 (3)	C7—H7B	0.9700
O6—C10	1.333 (3)	C8—C11	1.515 (3)
O6—C12	1.446 (3)	C8—C9	1.526 (3)
C1—C2	1.380 (3)	C9—C10	1.494 (3)
C1—C6	1.384 (3)	C9—H9A	0.9700
C2—C3	1.378 (3)	C9—H9B	0.9700
C2—H2B	0.9300	C12—H12A	0.9600
C3—C4	1.380 (3)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C1—O1—H1	109.5	C8—C7—H7B	108.5
C8—O2—H2	109.5	H7A—C7—H7B	107.5
C11—O4—H4	109.5	O2—C8—C11	108.40 (17)
C10—O6—C12	116.2 (2)	O2—C8—C9	107.55 (19)
O1—C1—C2	117.2 (2)	C11—C8—C9	112.63 (19)
O1—C1—C6	123.0 (2)	O2—C8—C7	110.03 (18)
C2—C1—C6	119.8 (2)	C11—C8—C7	108.44 (18)
C3—C2—C1	119.5 (2)	C9—C8—C7	109.77 (19)
C3—C2—H2B	120.2	C10—C9—C8	114.4 (2)
C1—C2—H2B	120.2	C10—C9—H9A	108.6
C2—C3—C4	122.3 (2)	C8—C9—H9A	108.6
C2—C3—H3A	118.9	C10—C9—H9B	108.6
C4—C3—H3A	118.9	C8—C9—H9B	108.6
C3—C4—C5	117.2 (2)	H9A—C9—H9B	107.6
C3—C4—C7	121.8 (2)	O5—C10—O6	123.3 (2)
C5—C4—C7	121.0 (2)	O5—C10—C9	125.6 (2)
C6—C5—C4	121.5 (2)	O6—C10—C9	111.1 (2)
C6—C5—H5A	119.2	O3—C11—O4	125.3 (2)
C4—C5—H5A	119.2	O3—C11—C8	123.2 (2)
C5—C6—C1	119.6 (2)	O4—C11—C8	111.43 (19)
C5—C6—H6A	120.2	O6—C12—H12A	109.5
C1—C6—H6A	120.2	O6—C12—H12B	109.5
C4—C7—C8	115.19 (19)	H12A—C12—H12B	109.5
C4—C7—H7A	108.5	O6—C12—H12C	109.5
C8—C7—H7A	108.5	H12A—C12—H12C	109.5
C4—C7—H7B	108.5	H12B—C12—H12C	109.5
O1—C1—C2—C3	179.3 (2)	C4—C7—C8—C9	−174.1 (2)
C6—C1—C2—C3	0.3 (4)	O2—C8—C9—C10	−68.8 (2)
C1—C2—C3—C4	−0.2 (4)	C11—C8—C9—C10	50.5 (3)
C2—C3—C4—C5	0.1 (3)	C7—C8—C9—C10	171.5 (2)
C2—C3—C4—C7	−178.7 (2)	C12—O6—C10—O5	−2.1 (4)
C3—C4—C5—C6	0.0 (3)	C12—O6—C10—C9	176.6 (2)
C7—C4—C5—C6	178.7 (2)	C8—C9—C10—O5	−5.7 (4)
C4—C5—C6—C1	0.1 (4)	C8—C9—C10—O6	175.6 (2)
O1—C1—C6—C5	−179.2 (2)	O2—C8—C11—O3	−13.9 (3)
C2—C1—C6—C5	−0.2 (4)	C9—C8—C11—O3	−132.8 (2)
C3—C4—C7—C8	−78.5 (3)	C7—C8—C11—O3	105.5 (2)
C5—C4—C7—C8	102.8 (3)	O2—C8—C11—O4	169.74 (19)
C4—C7—C8—O2	67.7 (3)	C9—C8—C11—O4	50.9 (3)
C4—C7—C8—C11	−50.7 (3)	C7—C8—C11—O4	−70.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	1.96	2.775 (2)	172
O2—H2···O1ii	0.82	2.34	2.888 (2)	125
O4—H4···O2iii	0.82	1.85	2.639 (2)	161
C12—H12B···O5iv	0.96	2.42	3.268 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.96	2.775 (2)	172
O2—H2⋯O1ii	0.82	2.33	2.888 (2)	125
O4—H4⋯O2iii	0.82	1.85	2.639 (2)	161
C12—H12B⋯O5iv	0.96	2.42	3.268 (4)	148

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