2,3-O-Isopropyl-idene-3-C-phenyl-erythrofuran-ose.

The title compound, C(13)H(16)O, comprises two fused five-membered rings. Each ring has an envelope conformation, with the ether O atom in the furan-ose ring, and the CMe(2) atom in the acetonide ring as the flap atoms. In the crystal, centrosymmetrically related mol-ecules associate via hydr-oxy-ether O-H⋯O hydrogen bonds and the resulting dimers are linked into a supra-molecular chain with a flattened topology via C-H⋯O(hydr-oxy) contacts, and aligned in the a-axis direction.

Related literature

For the relevance and chemistry of systems related to the title compound, see: Pedersen et al. (2009 ▶); Robinson et al. (2006 ▶, 2009 ▶); Valente et al. (2009 ▶). For the reactions of Co(II) complexes with endoperoxides, see: Boyd et al. (1980 ▶); Sutbeyaz et al. (1988 ▶); Greatrex et al. (2003 ▶); Greatrex & Taylor (2005 ▶).

Experimental

Crystal data

C13H16O4

M = 236.26

Triclinic,

a = 5.716 (2) Å

b = 9.201 (4) Å

c = 11.871 (6) Å

α = 89.76 (3)°

β = 78.72 (2)°

γ = 73.70 (2)°

V = 586.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.35 × 0.35 × 0.10 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.773, T max = 1.000

14572 measured reflections

2408 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.157

S = 1.16

2408 reflections

157 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904848X/sj2687sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904848X/sj2687Isup2.hkl

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

C13H16O4	Z = 2
Mr = 236.26	F(000) = 252
Triclinic, P1	Dx = 1.337 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 5.716 (2) Å	Cell parameters from 2428 reflections
b = 9.201 (4) Å	θ = 3.5–27.5°
c = 11.871 (6) Å	µ = 0.10 mm−1
α = 89.76 (3)°	T = 173 K
β = 78.72 (2)°	Prism, pale-yellow
γ = 73.70 (2)°	0.35 × 0.35 × 0.10 mm
V = 586.9 (4) Å3

Rigaku AFC12κ/SATURN724 diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	2361 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
Tmin = 0.773, Tmax = 1.000	k = −10→11
14572 measured reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0929P)2 + 0.1356P] where P = (Fo2 + 2Fc2)/3
2408 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.25 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
O1	−0.11375 (18)	0.89747 (11)	0.40885 (9)	0.0294 (3)
O2	0.29860 (19)	0.86868 (13)	0.42473 (9)	0.0335 (3)
H2O	0.2683	0.9394	0.4747	0.050*
O3	0.1029 (2)	0.87393 (12)	0.15795 (9)	0.0321 (3)
O4	−0.09610 (17)	0.69527 (11)	0.20274 (8)	0.0270 (3)
C2	0.1242 (3)	0.91139 (17)	0.35425 (12)	0.0281 (3)
H2	0.1102	1.0170	0.3296	0.034*
C3	0.2058 (3)	0.79968 (16)	0.25019 (12)	0.0264 (3)
H3	0.3905	0.7548	0.2291	0.032*
C4	0.0642 (2)	0.67820 (16)	0.28391 (11)	0.0248 (3)
C5	−0.0944 (3)	0.73843 (16)	0.40319 (12)	0.0273 (3)
H5A	−0.2612	0.7226	0.4120	0.033*
H5B	−0.0130	0.6864	0.4645	0.033*
C6	−0.0013 (3)	0.77251 (17)	0.10732 (12)	0.0300 (4)
C41	0.2235 (2)	0.51612 (16)	0.28472 (12)	0.0263 (3)
C42	0.4230 (3)	0.48304 (18)	0.34152 (13)	0.0322 (4)
H42	0.4620	0.5630	0.3772	0.039*
C43	0.5645 (3)	0.33463 (19)	0.34623 (15)	0.0380 (4)
H43	0.7000	0.3135	0.3849	0.046*
C44	0.5092 (3)	0.21693 (18)	0.29478 (14)	0.0378 (4)
H44	0.6059	0.1151	0.2982	0.045*
C45	0.3115 (3)	0.24891 (18)	0.23827 (13)	0.0362 (4)
H45	0.2735	0.1686	0.2025	0.043*
C46	0.1683 (3)	0.39770 (17)	0.23361 (12)	0.0307 (4)
H46	0.0323	0.4184	0.1953	0.037*
C61	0.1984 (3)	0.6632 (2)	0.02004 (14)	0.0398 (4)
H61A	0.1252	0.5942	−0.0141	0.060*
H61B	0.3294	0.6045	0.0582	0.060*
H61C	0.2701	0.7202	−0.0405	0.060*
C62	−0.2175 (3)	0.8637 (2)	0.05769 (14)	0.0397 (4)
H62A	−0.2898	0.7948	0.0229	0.060*
H62B	−0.1591	0.9276	−0.0011	0.060*
H62C	−0.3439	0.9279	0.1191	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0253 (5)	0.0272 (6)	0.0334 (6)	−0.0055 (4)	−0.0032 (4)	−0.0028 (4)
O2	0.0280 (6)	0.0361 (6)	0.0352 (6)	−0.0045 (4)	−0.0103 (4)	−0.0069 (4)
O3	0.0409 (6)	0.0306 (6)	0.0301 (6)	−0.0151 (5)	−0.0124 (4)	0.0082 (4)
O4	0.0261 (5)	0.0309 (6)	0.0258 (5)	−0.0093 (4)	−0.0082 (4)	0.0054 (4)
C2	0.0248 (7)	0.0279 (7)	0.0316 (7)	−0.0071 (5)	−0.0062 (5)	0.0009 (6)
C3	0.0258 (7)	0.0266 (7)	0.0272 (7)	−0.0083 (5)	−0.0051 (5)	0.0028 (5)
C4	0.0236 (7)	0.0282 (8)	0.0237 (7)	−0.0080 (5)	−0.0066 (5)	0.0025 (5)
C5	0.0258 (7)	0.0279 (8)	0.0274 (7)	−0.0071 (5)	−0.0042 (5)	0.0014 (5)
C6	0.0343 (8)	0.0326 (8)	0.0258 (7)	−0.0128 (6)	−0.0079 (6)	0.0056 (6)
C41	0.0265 (7)	0.0271 (8)	0.0243 (6)	−0.0075 (6)	−0.0030 (5)	0.0025 (5)
C42	0.0308 (8)	0.0308 (8)	0.0358 (8)	−0.0077 (6)	−0.0105 (6)	0.0022 (6)
C43	0.0332 (8)	0.0367 (9)	0.0420 (9)	−0.0038 (6)	−0.0114 (7)	0.0070 (7)
C44	0.0419 (9)	0.0275 (8)	0.0365 (8)	−0.0006 (6)	−0.0037 (7)	0.0053 (6)
C45	0.0479 (9)	0.0276 (8)	0.0325 (8)	−0.0108 (7)	−0.0065 (7)	0.0011 (6)
C46	0.0347 (8)	0.0304 (8)	0.0283 (7)	−0.0102 (6)	−0.0080 (6)	0.0031 (6)
C61	0.0430 (9)	0.0468 (10)	0.0281 (8)	−0.0141 (7)	−0.0015 (6)	−0.0018 (7)
C62	0.0437 (9)	0.0442 (10)	0.0355 (8)	−0.0130 (7)	−0.0176 (7)	0.0125 (7)

O1—C2	1.4278 (18)	C41—C46	1.388 (2)
O1—C5	1.4370 (19)	C41—C42	1.397 (2)
O2—C2	1.3972 (17)	C42—C43	1.385 (2)
O2—H2O	0.8400	C42—H42	0.9500
O3—C6	1.4295 (18)	C43—C44	1.385 (3)
O3—C3	1.4254 (17)	C43—H43	0.9500
O4—C6	1.4323 (18)	C44—C45	1.386 (2)
O4—C4	1.4339 (16)	C44—H44	0.9500
C2—C3	1.522 (2)	C45—C46	1.391 (2)
C2—H2	1.0000	C45—H45	0.9500
C3—C4	1.563 (2)	C46—H46	0.9500
C3—H3	1.0000	C61—H61A	0.9800
C4—C41	1.515 (2)	C61—H61B	0.9800
C4—C5	1.535 (2)	C61—H61C	0.9800
C5—H5A	0.9900	C62—H62A	0.9800
C5—H5B	0.9900	C62—H62B	0.9800
C6—C62	1.509 (2)	C62—H62C	0.9800
C6—C61	1.513 (2)
C2—O1—C5	106.30 (11)	O4—C6—C61	111.43 (13)
C2—O2—H2O	107.7	C62—C6—C61	113.45 (14)
C6—O3—C3	107.42 (11)	C46—C41—C42	118.91 (14)
C6—O4—C4	108.29 (10)	C46—C41—C4	120.93 (13)
O2—C2—O1	111.99 (12)	C42—C41—C4	120.10 (13)
O2—C2—C3	108.35 (12)	C43—C42—C41	120.58 (15)
O1—C2—C3	104.47 (11)	C43—C42—H42	119.7
O2—C2—H2	110.6	C41—C42—H42	119.7
O1—C2—H2	110.6	C44—C43—C42	120.26 (15)
C3—C2—H2	110.6	C44—C43—H43	119.9
O3—C3—C2	108.22 (12)	C42—C43—H43	119.9
O3—C3—C4	104.64 (11)	C43—C44—C45	119.46 (15)
C2—C3—C4	104.60 (11)	C43—C44—H44	120.3
O3—C3—H3	112.9	C45—C44—H44	120.3
C2—C3—H3	112.9	C46—C45—C44	120.51 (15)
C4—C3—H3	112.9	C46—C45—H45	119.7
O4—C4—C41	112.22 (11)	C44—C45—H45	119.7
O4—C4—C5	108.90 (11)	C45—C46—C41	120.27 (14)
C41—C4—C5	112.12 (12)	C45—C46—H46	119.9
O4—C4—C3	103.36 (10)	C41—C46—H46	119.9
C41—C4—C3	116.44 (11)	C6—C61—H61A	109.5
C5—C4—C3	102.99 (11)	C6—C61—H61B	109.5
O1—C5—C4	105.33 (11)	H61A—C61—H61B	109.5
O1—C5—H5A	110.7	C6—C61—H61C	109.5
C4—C5—H5A	110.7	H61A—C61—H61C	109.5
O1—C5—H5B	110.7	H61B—C61—H61C	109.5
C4—C5—H5B	110.7	C6—C62—H62A	109.5
H5A—C5—H5B	108.8	C6—C62—H62B	109.5
O3—C6—O4	104.00 (11)	H62A—C62—H62B	109.5
O3—C6—C62	109.07 (13)	C6—C62—H62C	109.5
O4—C6—C62	108.34 (12)	H62A—C62—H62C	109.5
O3—C6—C61	110.10 (13)	H62B—C62—H62C	109.5
C5—O1—C2—O2	−76.45 (14)	C3—O3—C6—O4	34.96 (14)
C5—O1—C2—C3	40.60 (13)	C3—O3—C6—C62	150.39 (12)
C6—O3—C3—C2	−133.84 (12)	C3—O3—C6—C61	−84.52 (14)
C6—O3—C3—C4	−22.73 (13)	C4—O4—C6—O3	−33.70 (14)
O2—C2—C3—O3	−154.79 (11)	C4—O4—C6—C62	−149.65 (13)
O1—C2—C3—O3	85.67 (13)	C4—O4—C6—C61	84.87 (14)
O2—C2—C3—C4	94.07 (13)	O4—C4—C41—C46	−14.92 (18)
O1—C2—C3—C4	−25.47 (13)	C5—C4—C41—C46	108.02 (15)
C6—O4—C4—C41	−107.03 (13)	C3—C4—C41—C46	−133.74 (14)
C6—O4—C4—C5	128.23 (12)	O4—C4—C41—C42	167.76 (12)
C6—O4—C4—C3	19.23 (13)	C5—C4—C41—C42	−69.29 (16)
O3—C3—C4—O4	2.14 (13)	C3—C4—C41—C42	48.95 (18)
C2—C3—C4—O4	115.84 (12)	C46—C41—C42—C43	0.4 (2)
O3—C3—C4—C41	125.66 (12)	C4—C41—C42—C43	177.73 (13)
C2—C3—C4—C41	−120.64 (13)	C41—C42—C43—C44	−0.2 (2)
O3—C3—C4—C5	−111.22 (12)	C42—C43—C44—C45	0.2 (2)
C2—C3—C4—C5	2.48 (13)	C43—C44—C45—C46	−0.4 (2)
C2—O1—C5—C4	−39.18 (13)	C44—C45—C46—C41	0.6 (2)
O4—C4—C5—O1	−88.03 (13)	C42—C41—C46—C45	−0.6 (2)
C41—C4—C5—O1	147.17 (11)	C4—C41—C46—C45	−177.92 (13)
C3—C4—C5—O1	21.22 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1i	0.84	1.93	2.755 (2)	166
C5—H5a···O2ii	0.99	2.47	3.296 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1i	0.84	1.93	2.755 (2)	166
C5—H5a⋯O2ii	0.99	2.47	3.296 (3)	140

Symmetry codes: (i) ; (ii) .