(2S)-2-(3-Oxo-1,4-dioxaspiro-[4.5]decan-2-yl)ethanoic acid.

The title compound, C(10)H(14)O(5), is an inter-mediate in our study of the asymmetric synthesis of α-hydroxy-alkanoic acids. The structure consists of 1,4-dioxaspiro[4,5]decane skeleton formed when the cyclohexylidene group binds to both of the hydroxyl groups of carboxylic groups of the starting malic acid. The six-membered ring adopts a chair conformation.

Related literature

For related literature, see: Coppola & Schuster (1997 ▶); Díez et al. (2001 ▶); Dixon et al. (2005 ▶); Hanessian et al. (1993 ▶); Heimgartner & Obrecht (1990 ▶); Horgen et al. (2000 ▶); Liang et al. (2000 ▶); Sitachitta et al. (2000 ▶); Sugiyama et al. (1990 ▶).

Experimental

Crystal data

C10H14O5

M = 214.21

Orthorhombic,

a = 6.7098 (6) Å

b = 10.3463 (8) Å

c = 15.3175 (13) Å

V = 1063.37 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 (2) K

0.50 × 0.45 × 0.35 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scanSADABS; Bruker, 2004 ▶) T min = 0.948, T max = 0.963

7861 measured reflections

2206 independent reflections

1814 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.05

2206 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801146X/wk2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801146X/wk2081Isup2.hkl

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

C10H14O5	F000 = 456
Mr = 214.21	Dx = 1.338 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3702 reflections
a = 6.7098 (6) Å	θ = 2.4–31.6º
b = 10.3463 (8) Å	µ = 0.11 mm−1
c = 15.3175 (13) Å	T = 295 (2) K
V = 1063.37 (15) Å3	Tabular, colourless
Z = 4	0.50 × 0.45 × 0.35 mm

Bruker Kappa APEXII CCD diffractometer	2206 independent reflections
Radiation source: fine-focus sealed tube	1814 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 295(2) K	θmax = 33.3º
ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 2004	h = −10→8
Tmin = 0.948, Tmax = 0.963	k = −15→9
7861 measured reflections	l = −13→22

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0907P)2 + 0.0732P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.31 e Å−3
2206 reflections	Δρmin = −0.17 e Å−3
138 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (9)
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	0.7046 (2)	0.66387 (12)	0.06930 (8)	0.0516 (3)
O2	0.4717 (2)	0.51238 (14)	0.10628 (8)	0.0584 (4)
O3	0.2465 (2)	0.28916 (12)	0.00641 (11)	0.0613 (4)
O4	−0.0034 (2)	0.40271 (14)	−0.04693 (12)	0.0647 (4)
H4A	−0.0620	0.3336	−0.0414	0.097*
O5	0.6684 (3)	0.66532 (14)	−0.07558 (9)	0.0614 (4)
C1	0.6310 (2)	0.61950 (15)	−0.00602 (11)	0.0438 (3)
C2	0.4985 (3)	0.50524 (14)	0.01414 (10)	0.0406 (3)
H2A	0.5662	0.4245	−0.0015	0.049*
C3	0.2983 (3)	0.51228 (15)	−0.03022 (12)	0.0454 (3)
H3A	0.2220	0.5827	−0.0051	0.055*
H3B	0.3176	0.5309	−0.0917	0.055*
C4	0.1827 (2)	0.38946 (15)	−0.02119 (10)	0.0393 (3)
C5	0.6327 (3)	0.58484 (16)	0.14185 (11)	0.0461 (4)
C6	0.5544 (4)	0.6724 (2)	0.21270 (13)	0.0615 (5)
H6A	0.4875	0.6209	0.2568	0.074*
H6B	0.4577	0.7317	0.1880	0.074*
C7	0.7215 (5)	0.7482 (2)	0.25453 (14)	0.0702 (7)
H7A	0.7760	0.8083	0.2122	0.084*
H7B	0.6687	0.7981	0.3029	0.084*
C8	0.8859 (4)	0.6613 (2)	0.28737 (14)	0.0686 (6)
H8A	0.8347	0.6064	0.3336	0.082*
H8B	0.9925	0.7136	0.3114	0.082*
C9	0.9671 (3)	0.5778 (2)	0.21429 (14)	0.0643 (5)
H9A	1.0289	0.6322	0.1704	0.077*
H9B	1.0681	0.5200	0.2372	0.077*
C10	0.8011 (3)	0.49950 (18)	0.17303 (13)	0.0547 (4)
H10A	0.8540	0.4511	0.1240	0.066*
H10B	0.7502	0.4381	0.2154	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0599 (8)	0.0417 (6)	0.0531 (6)	−0.0192 (6)	−0.0063 (6)	0.0093 (5)
O2	0.0631 (8)	0.0668 (8)	0.0454 (6)	−0.0280 (7)	−0.0004 (6)	0.0098 (6)
O3	0.0445 (6)	0.0356 (5)	0.1039 (11)	−0.0022 (5)	−0.0091 (7)	0.0121 (7)
O4	0.0425 (6)	0.0513 (7)	0.1003 (11)	−0.0049 (6)	−0.0158 (7)	0.0192 (7)
O5	0.0622 (8)	0.0654 (9)	0.0565 (7)	−0.0148 (7)	0.0016 (6)	0.0219 (7)
C1	0.0436 (7)	0.0370 (6)	0.0509 (8)	−0.0079 (6)	0.0021 (7)	0.0086 (6)
C2	0.0434 (7)	0.0330 (6)	0.0455 (7)	−0.0058 (6)	−0.0007 (6)	0.0048 (6)
C3	0.0436 (7)	0.0360 (7)	0.0568 (8)	−0.0043 (6)	−0.0036 (7)	0.0096 (6)
C4	0.0376 (6)	0.0365 (6)	0.0440 (7)	−0.0006 (6)	−0.0002 (6)	0.0009 (5)
C5	0.0516 (9)	0.0420 (7)	0.0448 (7)	−0.0098 (7)	−0.0003 (7)	0.0040 (6)
C6	0.0602 (11)	0.0677 (12)	0.0564 (10)	0.0122 (10)	−0.0036 (9)	−0.0061 (9)
C7	0.0984 (19)	0.0535 (11)	0.0588 (11)	0.0035 (11)	−0.0118 (12)	−0.0117 (9)
C8	0.0772 (15)	0.0712 (13)	0.0575 (10)	−0.0108 (12)	−0.0193 (10)	−0.0002 (10)
C9	0.0513 (10)	0.0734 (13)	0.0683 (11)	0.0032 (10)	−0.0065 (9)	0.0130 (11)
C10	0.0663 (11)	0.0425 (8)	0.0552 (8)	0.0047 (9)	0.0025 (9)	0.0053 (7)

O1—C1	1.336 (2)	C5—C10	1.511 (3)
O1—C5	1.4617 (19)	C6—C7	1.511 (3)
O2—C5	1.423 (2)	C6—H6A	0.9700
O2—C2	1.425 (2)	C6—H6B	0.9700
O3—C4	1.199 (2)	C7—C8	1.510 (4)
O4—C4	1.317 (2)	C7—H7A	0.9700
O4—H4A	0.8200	C7—H7B	0.9700
O5—C1	1.193 (2)	C8—C9	1.515 (3)
C1—C2	1.511 (2)	C8—H8A	0.9700
C2—C3	1.507 (2)	C8—H8B	0.9700
C2—H2A	0.9800	C9—C10	1.515 (3)
C3—C4	1.495 (2)	C9—H9A	0.9700
C3—H3A	0.9700	C9—H9B	0.9700
C3—H3B	0.9700	C10—H10A	0.9700
C5—C6	1.508 (3)	C10—H10B	0.9700
C1—O1—C5	110.00 (12)	C7—C6—H6A	109.4
C5—O2—C2	108.11 (13)	C5—C6—H6B	109.4
C4—O4—H4A	109.5	C7—C6—H6B	109.4
O5—C1—O1	123.82 (15)	H6A—C6—H6B	108.0
O5—C1—C2	128.12 (16)	C8—C7—C6	111.94 (17)
O1—C1—C2	108.05 (13)	C8—C7—H7A	109.2
O2—C2—C3	109.37 (15)	C6—C7—H7A	109.2
O2—C2—C1	103.66 (13)	C8—C7—H7B	109.2
C3—C2—C1	113.23 (12)	C6—C7—H7B	109.2
O2—C2—H2A	110.1	H7A—C7—H7B	107.9
C3—C2—H2A	110.1	C7—C8—C9	110.88 (17)
C1—C2—H2A	110.1	C7—C8—H8A	109.5
C4—C3—C2	112.30 (13)	C9—C8—H8A	109.5
C4—C3—H3A	109.1	C7—C8—H8B	109.5
C2—C3—H3A	109.1	C9—C8—H8B	109.5
C4—C3—H3B	109.1	H8A—C8—H8B	108.1
C2—C3—H3B	109.1	C10—C9—C8	110.37 (19)
H3A—C3—H3B	107.9	C10—C9—H9A	109.6
O3—C4—O4	122.26 (15)	C8—C9—H9A	109.6
O3—C4—C3	125.67 (15)	C10—C9—H9B	109.6
O4—C4—C3	112.07 (14)	C8—C9—H9B	109.6
O2—C5—O1	104.72 (12)	H9A—C9—H9B	108.1
O2—C5—C6	109.10 (17)	C5—C10—C9	111.66 (15)
O1—C5—C6	109.04 (14)	C5—C10—H10A	109.3
O2—C5—C10	112.38 (15)	C9—C10—H10A	109.3
O1—C5—C10	108.68 (15)	C5—C10—H10B	109.3
C6—C5—C10	112.58 (15)	C9—C10—H10B	109.3
C5—C6—C7	111.0 (2)	H10A—C10—H10B	107.9
C5—C6—H6A	109.4