Eucomic acid methanol monosolvate.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 2-hy-droxy-2-(4-hy-droxy-benz-yl)butane-dioic acid methanol monosolvate], C(11)H(12)O(6)·CH(3)OH, the dihedral angles between the planes of the carboxyl groups and the benzene ring are 51.23 (9) and 87.97 (9)°. Inter-molecular O-H⋯O hydrogen-bonding inter-actions involving the hy-droxy and carb-oxy-lic acid groups and the methanol solvent mol-ecule give a three-dimensional structure.

Related literature

For general background to natural existance and related structures, see: Jiang et al. (2006 ▶); Li et al. (2008 ▶). For the absolute configuration of eucomic acid, see: Heller & Tamm (1974 ▶).

Experimental

Crystal data

C11H12O6·CH4O

M = 272.25

Orthorhombic,

a = 5.8970 (2) Å

b = 7.2088 (3) Å

c = 31.3290 (4) Å

V = 1331.81 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.60 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

7417 measured reflections

1408 independent reflections

1184 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.05

1408 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART and SAINT (Bruker, 1998 ▶); data reduction: 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030017/zs2127sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030017/zs2127Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030017/zs2127Isup3.cml

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

C11H12O6·CH4O	Dx = 1.358 Mg m−3
Mr = 272.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2341 reflections
a = 5.8970 (2) Å	θ = 1.3–25.0°
b = 7.2088 (3) Å	µ = 0.11 mm−1
c = 31.3290 (4) Å	T = 293 K
V = 1331.81 (7) Å3	Prism, colourless
Z = 4	0.60 × 0.20 × 0.10 mm
F(000) = 576

Bruker SMART 1000 CCD diffractometer	1184 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.0°, θmin = 1.3°
ω scans	h = −7→6
7417 measured reflections	k = −8→6
1408 independent reflections	l = −36→37

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.0811P] where P = (Fo2 + 2Fc2)/3
1408 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 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
O4	0.5195 (3)	0.2588 (3)	0.38870 (6)	0.0496 (5)
H4	0.6358	0.3081	0.3799	0.074*
O2	−0.0623 (2)	0.3712 (2)	0.37354 (5)	0.0399 (4)
H2	−0.0175	0.4478	0.3561	0.060*
O1	0.2583 (3)	0.1398 (3)	0.18267 (5)	0.0503 (5)
H1	0.3811	0.0962	0.1756	0.075*
O3	0.3496 (3)	0.4842 (3)	0.35125 (5)	0.0465 (5)
C5	−0.0136 (4)	0.1541 (3)	0.28608 (7)	0.0390 (6)
H5	−0.1536	0.1885	0.2972	0.047*
C4	0.1514 (4)	0.0859 (3)	0.31338 (7)	0.0346 (5)
C1	0.2305 (4)	0.1201 (3)	0.22599 (7)	0.0373 (5)
C8	0.1204 (4)	0.2530 (3)	0.38545 (7)	0.0337 (5)
C3	0.3574 (4)	0.0333 (3)	0.29570 (7)	0.0401 (6)
H3	0.4705	−0.0139	0.3133	0.048*
O6	−0.0015 (5)	0.3883 (3)	0.49413 (6)	0.0750 (6)
H6	0.0124	0.4873	0.5068	0.112*
C6	0.0240 (4)	0.1722 (3)	0.24286 (7)	0.0380 (6)
H6A	−0.0889	0.2193	0.2252	0.046*
O5	0.2358 (4)	0.5185 (3)	0.44936 (6)	0.0769 (7)
C11	0.3419 (4)	0.3486 (4)	0.37382 (7)	0.0361 (5)
C2	0.3976 (4)	0.0497 (4)	0.25230 (7)	0.0420 (6)
H2A	0.5365	0.0136	0.2409	0.050*
C7	0.1074 (4)	0.0688 (3)	0.36073 (7)	0.0397 (6)
H7A	0.2170	−0.0167	0.3728	0.048*
H7B	−0.0421	0.0156	0.3649	0.048*
C10	0.1187 (4)	0.3916 (4)	0.45945 (7)	0.0449 (6)
C9	0.0974 (4)	0.2185 (4)	0.43323 (7)	0.0412 (6)
H9A	−0.0491	0.1622	0.4388	0.049*
H9B	0.2134	0.1311	0.4421	0.049*
O7	0.0058 (6)	0.6834 (4)	0.54040 (10)	0.1137 (10)
H7	−0.0761	0.7730	0.5357	0.171*
C12	0.1744 (7)	0.7337 (6)	0.56770 (13)	0.1048 (14)
H12A	0.3167	0.6874	0.5573	0.157*
H12B	0.1446	0.6828	0.5954	0.157*
H12C	0.1808	0.8666	0.5696	0.157*

	U11	U22	U33	U12	U13	U23
O4	0.0228 (8)	0.0617 (12)	0.0644 (12)	−0.0021 (9)	−0.0012 (8)	0.0092 (9)
O2	0.0262 (8)	0.0491 (10)	0.0446 (9)	−0.0002 (8)	0.0008 (7)	0.0065 (8)
O1	0.0462 (10)	0.0669 (13)	0.0378 (9)	0.0088 (10)	0.0061 (8)	−0.0085 (9)
O3	0.0389 (10)	0.0530 (11)	0.0474 (10)	−0.0084 (9)	0.0064 (8)	0.0099 (9)
C5	0.0297 (12)	0.0451 (14)	0.0421 (13)	0.0043 (12)	0.0037 (10)	−0.0067 (11)
C4	0.0293 (11)	0.0371 (12)	0.0374 (12)	−0.0031 (11)	−0.0008 (10)	−0.0057 (10)
C1	0.0362 (12)	0.0398 (13)	0.0360 (12)	−0.0020 (11)	0.0037 (10)	−0.0075 (11)
C8	0.0232 (11)	0.0434 (13)	0.0345 (12)	0.0004 (11)	−0.0002 (9)	0.0034 (10)
C3	0.0312 (13)	0.0442 (14)	0.0449 (13)	0.0002 (12)	−0.0058 (11)	−0.0028 (11)
O6	0.0911 (16)	0.0758 (14)	0.0580 (12)	−0.0167 (15)	0.0377 (12)	−0.0163 (10)
C6	0.0336 (13)	0.0430 (13)	0.0375 (13)	0.0072 (12)	−0.0018 (10)	−0.0022 (10)
O5	0.0892 (16)	0.0762 (15)	0.0653 (12)	−0.0429 (13)	0.0272 (12)	−0.0222 (11)
C11	0.0272 (12)	0.0485 (15)	0.0325 (12)	−0.0041 (12)	0.0018 (10)	−0.0049 (12)
C2	0.0287 (12)	0.0488 (14)	0.0485 (14)	0.0006 (12)	0.0033 (11)	−0.0114 (12)
C7	0.0344 (13)	0.0416 (13)	0.0430 (13)	−0.0068 (12)	0.0000 (10)	0.0015 (11)
C10	0.0399 (14)	0.0588 (16)	0.0361 (13)	−0.0049 (14)	0.0047 (11)	0.0011 (12)
C9	0.0361 (13)	0.0501 (14)	0.0373 (13)	−0.0072 (12)	0.0027 (10)	0.0033 (11)
O7	0.134 (2)	0.0946 (19)	0.112 (2)	0.0550 (19)	−0.042 (2)	−0.0518 (17)
C12	0.101 (3)	0.096 (3)	0.118 (3)	0.032 (3)	−0.028 (3)	−0.024 (3)

O4—H4	0.8200	C3—H3	0.9300
O4—C11	1.317 (3)	C3—C2	1.385 (3)
O2—H2	0.8200	O6—H6	0.8200
O2—C8	1.424 (3)	O6—C10	1.298 (3)
O1—H1	0.8200	C6—H6A	0.9300
O1—C1	1.374 (3)	O5—C10	1.189 (3)
O3—C11	1.207 (3)	C2—H2A	0.9300
C5—H5	0.9300	C7—H7A	0.9700
C5—C4	1.386 (3)	C7—H7B	0.9700
C5—C6	1.378 (3)	C10—C9	1.499 (4)
C4—C3	1.388 (3)	C9—H9A	0.9700
C4—C7	1.511 (3)	C9—H9B	0.9700
C1—C6	1.380 (3)	O7—H7	0.8200
C1—C2	1.381 (3)	O7—C12	1.361 (4)
C8—C11	1.521 (3)	C12—H12A	0.9600
C8—C7	1.539 (3)	C12—H12B	0.9600
C8—C9	1.523 (3)	C12—H12C	0.9600
C11—O4—H4	109.5	O3—C11—C8	122.6 (2)
C8—O2—H2	109.5	C1—C2—C3	119.7 (2)
C1—O1—H1	109.5	C1—C2—H2A	120.2
C4—C5—H5	119.1	C3—C2—H2A	120.2
C6—C5—H5	119.1	C4—C7—C8	114.53 (19)
C6—C5—C4	121.8 (2)	C4—C7—H7A	108.6
C5—C4—C3	117.7 (2)	C4—C7—H7B	108.6
C5—C4—C7	120.9 (2)	C8—C7—H7A	108.6
C3—C4—C7	121.3 (2)	C8—C7—H7B	108.6
O1—C1—C6	117.1 (2)	H7A—C7—H7B	107.6
O1—C1—C2	122.8 (2)	O6—C10—C9	113.4 (2)
C6—C1—C2	120.1 (2)	O5—C10—O6	123.6 (2)
O2—C8—C11	108.42 (17)	O5—C10—C9	122.9 (2)
O2—C8—C7	110.29 (18)	C8—C9—H9A	108.9
O2—C8—C9	106.74 (18)	C8—C9—H9B	108.9
C11—C8—C7	108.24 (18)	C10—C9—C8	113.2 (2)
C11—C8—C9	112.71 (18)	C10—C9—H9A	108.9
C9—C8—C7	110.41 (19)	C10—C9—H9B	108.9
C4—C3—H3	119.4	H9A—C9—H9B	107.7
C2—C3—C4	121.2 (2)	C12—O7—H7	109.5
C2—C3—H3	119.4	O7—C12—H12A	109.5
C10—O6—H6	109.5	O7—C12—H12B	109.5
C5—C6—C1	119.5 (2)	O7—C12—H12C	109.5
C5—C6—H6A	120.2	H12A—C12—H12B	109.5
C1—C6—H6A	120.2	H12A—C12—H12C	109.5
O4—C11—C8	112.08 (19)	H12B—C12—H12C	109.5
O3—C11—O4	125.1 (2)
O2—C8—C11—O4	171.94 (19)	C6—C5—C4—C7	179.4 (2)
O2—C8—C11—O3	−12.4 (3)	C6—C1—C2—C3	−0.5 (4)
O2—C8—C7—C4	68.0 (2)	O5—C10—C9—C8	−32.1 (4)
O2—C8—C9—C10	−62.6 (2)	C11—C8—C7—C4	−50.5 (3)
O1—C1—C6—C5	179.5 (2)	C11—C8—C9—C10	56.3 (3)
O1—C1—C2—C3	−179.8 (2)	C2—C1—C6—C5	0.2 (4)
C5—C4—C3—C2	0.6 (3)	C7—C4—C3—C2	−179.7 (2)
C5—C4—C7—C8	−77.1 (3)	C7—C8—C11—O4	−68.4 (2)
C4—C5—C6—C1	0.5 (4)	C7—C8—C11—O3	107.2 (2)
C4—C3—C2—C1	0.1 (4)	C7—C8—C9—C10	177.5 (2)
C3—C4—C7—C8	103.2 (3)	C9—C8—C11—O4	54.0 (3)
O6—C10—C9—C8	148.3 (2)	C9—C8—C11—O3	−130.3 (2)
C6—C5—C4—C3	−0.9 (3)	C9—C8—C7—C4	−174.29 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	1.97	2.781 (3)	170
O2—H2···O3	0.82	2.19	2.655 (2)	116
O2—H2···O1ii	0.82	2.33	2.861 (2)	123
O4—H4···O2iii	0.82	1.85	2.639 (2)	162
O6—H6···O7	0.82	1.76	2.575 (4)	170
O7—H7···O5iv	0.82	1.93	2.694 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.97	2.781 (3)	170
O2—H2⋯O1ii	0.82	2.33	2.861 (2)	123
O4—H4⋯O2iii	0.82	1.85	2.639 (2)	162
O6—H6⋯O7	0.82	1.76	2.575 (4)	170
O7—H7⋯O5iv	0.82	1.93	2.694 (4)	156

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