(1R*,5R*,6S*,7R*)-6,7-Di­hydroxy-6-hydroxy­methyl-2-oxabi­cyclo­[3.2.0]heptan-3-one

The title compound C₇H₁₀O₅, crystallizes in the space group P3₁ as individual mol­ecules on a three old screw axis, and is stabilized by strong intermolecular hydrogen bonds between the methyl­ene alcohol [O—H...O 1.75 (5) Å] and the two secondary alcohol moieties [O—H...O 1.81 (3) and 1.91 (3) Å] .

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.035
• wR factor = 0.067
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) .       3.24 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang..          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ......          3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.27
           From the CIF: _reflns_number_total               1009
           Count of symmetry unique reflns         1008
           Completeness (_total/calc)            100.10%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia,1999).

(I)

Crystal data

C7H10O5	Dx = 1.414 Mg m^−3
Mr = 174.15	Mo Kα radiation, λ = 0.71069 Å
Trigonal, P31	Cell parameters from 293 reflections
Hall symbol: P 31	θ = 4–21°
a = 11.532 (5) Å	µ = 0.12 mm^−1
c = 5.328 (5) Å	T = 293 K
V = 613.6 (7) Å^3	Cuboid, colorless
Z = 3	0.26 × 0.12 × 0.1 mm
F(000) = 276

Data collection

Bruker SMART 1K CCD diffractometer	586 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 28.3°, θmin = 2.0°
ω scans	h = −15→15
4357 measured reflections	k = −15→13
1009 independent reflections	l = −5→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.027P)^2] where P = (Fo^2 + 2Fc^2)/3
1009 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.18 e Å^−3

Special details

Experimental. The intensity data were collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 10 s/frame. A total of 1315 frames were collected with a frame width of 0.3° covering up to θ = 28.27° with 99.9% completeness accomplished. The first 50 frames were recollected at the end of the data collection to check for decay; none was found.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0050 (2)	0.45504 (18)	0.1634 (3)	0.0387 (6)
O3	0.9692 (2)	0.1223 (2)	0.6143 (3)	0.0386 (5)
O4	1.0261 (2)	0.1584 (2)	0.1071 (4)	0.0426 (6)
O5	1.2491 (2)	0.5562 (3)	0.4200 (5)	0.0554 (7)
C4	0.9689 (3)	0.3293 (3)	0.5463 (5)	0.0335 (7)
H4	1.0294	0.356	0.6909	0.04*
C1	1.0420 (3)	0.3670 (3)	0.2913 (5)	0.0286 (7)
C2	0.9579 (3)	0.2202 (3)	0.2074 (5)	0.0309 (7)
H2	0.8855	0.2086	0.095	0.037*
C3	0.9058 (3)	0.1804 (3)	0.4784 (5)	0.0312 (7)
H3	0.8079	0.1305	0.4912	0.037*
O2	0.8645 (3)	0.5322 (3)	0.2175 (5)	0.0831 (9)
C6	0.9122 (3)	0.4682 (3)	0.2979 (6)	0.0458 (8)
C7	1.1914 (3)	0.4313 (3)	0.2899 (6)	0.0465 (9)
H7A	1.2178	0.3727	0.3706	0.056*
H7B	1.2237	0.446	0.1182	0.056*
C5	0.8821 (4)	0.3942 (4)	0.5409 (6)	0.0508 (9)
H5A	0.788	0.3267	0.5503	0.061*
H5B	0.9035	0.4553	0.6811	0.061*
H04	1.006 (3)	0.146 (3)	−0.047 (7)	0.060 (12)*
H03	0.925 (5)	0.032 (4)	0.567 (8)	0.103 (16)*
H05	1.255 (5)	0.621 (6)	0.306 (9)	0.120 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0576 (14)	0.0382 (12)	0.0311 (12)	0.0320 (11)	0.0000 (11)	0.0052 (9)
O3	0.0620 (14)	0.0333 (13)	0.0262 (11)	0.0281 (12)	−0.0045 (10)	0.0015 (10)
O4	0.0682 (16)	0.0570 (15)	0.0232 (13)	0.0468 (12)	−0.0048 (11)	−0.0068 (11)
O5	0.0433 (15)	0.0375 (14)	0.0691 (19)	0.0079 (11)	−0.0151 (12)	0.0012 (13)
C4	0.0487 (19)	0.0344 (17)	0.0236 (16)	0.0254 (16)	−0.0014 (14)	−0.0025 (14)
C1	0.0366 (18)	0.0300 (16)	0.0257 (17)	0.0214 (15)	−0.0012 (13)	0.0032 (13)
C2	0.0334 (17)	0.0370 (17)	0.0266 (16)	0.0207 (15)	−0.0064 (13)	−0.0034 (14)
C3	0.0339 (17)	0.0306 (16)	0.0306 (17)	0.0172 (14)	−0.0006 (13)	−0.0005 (14)
O2	0.125 (3)	0.107 (2)	0.075 (2)	0.102 (2)	−0.0075 (18)	0.0076 (17)
C6	0.063 (2)	0.046 (2)	0.046 (2)	0.040 (2)	−0.0069 (18)	−0.0020 (17)
C7	0.040 (2)	0.047 (2)	0.051 (2)	0.0202 (17)	0.0037 (16)	0.0027 (18)
C5	0.067 (2)	0.050 (2)	0.051 (2)	0.040 (2)	0.0137 (19)	0.0034 (17)

Geometric parameters (Å, º)

O1—C6	1.358 (4)	C1—C7	1.497 (4)
O1—C1	1.453 (3)	C1—C2	1.538 (4)
O3—C3	1.413 (3)	C2—C3	1.543 (4)
O3—H03	0.93 (4)	C2—H2	0.98
O4—C2	1.404 (3)	C3—H3	0.98
O4—H04	0.85 (4)	O2—C6	1.198 (4)
O5—C7	1.428 (4)	C6—C5	1.493 (5)
O5—H05	0.94 (6)	C7—H7A	0.97
C4—C5	1.521 (4)	C7—H7B	0.97
C4—C3	1.536 (4)	C5—H5A	0.97
C4—C1	1.542 (4)	C5—H5B	0.97
C4—H4	0.98
C6—O1—C1	110.7 (2)	O3—C3—C4	110.0 (2)
C3—O3—H03	105 (3)	O3—C3—C2	113.8 (2)
C2—O4—H04	106 (2)	C4—C3—C2	89.5 (2)
C7—O5—H05	107 (3)	O3—C3—H3	113.7
C5—C4—C3	119.0 (3)	C4—C3—H3	113.7
C5—C4—C1	104.3 (2)	C2—C3—H3	113.7
C3—C4—C1	89.6 (2)	O2—C6—O1	120.7 (3)
C5—C4—H4	113.6	O2—C6—C5	127.9 (3)
C3—C4—H4	113.6	O1—C6—C5	111.4 (3)
C1—C4—H4	113.6	O5—C7—C1	109.7 (2)
O1—C1—C7	108.6 (2)	O5—C7—H7A	109.7
O1—C1—C2	112.9 (2)	C1—C7—H7A	109.7
C7—C1—C2	118.7 (2)	O5—C7—H7B	109.7
O1—C1—C4	107.4 (2)	C1—C7—H7B	109.7
C7—C1—C4	118.4 (2)	H7A—C7—H7B	108.2
C2—C1—C4	89.5 (2)	C6—C5—C4	106.0 (3)
O4—C2—C1	117.7 (2)	C6—C5—H5A	110.5
O4—C2—C3	116.0 (2)	C4—C5—H5A	110.5
C1—C2—C3	89.6 (2)	C6—C5—H5B	110.5
O4—C2—H2	110.7	C4—C5—H5B	110.5
C1—C2—H2	110.7	H5A—C5—H5B	108.7
C3—C2—H2	110.7
C6—O1—C1—C7	−133.5 (3)	C1—C4—C3—O3	105.2 (2)
C6—O1—C1—C2	92.7 (3)	C5—C4—C3—C2	96.2 (3)
C6—O1—C1—C4	−4.4 (3)	C1—C4—C3—C2	−10.0 (2)
C5—C4—C1—O1	4.0 (3)	O4—C2—C3—O3	19.2 (3)
C3—C4—C1—O1	123.9 (2)	C1—C2—C3—O3	−101.7 (2)
C5—C4—C1—C7	127.3 (3)	O4—C2—C3—C4	130.9 (2)
C3—C4—C1—C7	−112.7 (3)	C1—C2—C3—C4	10.0 (2)
C5—C4—C1—C2	−109.9 (2)	C1—O1—C6—O2	−176.5 (3)
C3—C4—C1—C2	10.0 (2)	C1—O1—C6—C5	2.9 (3)
O1—C1—C2—O4	121.8 (2)	O1—C1—C7—O5	60.9 (3)
C7—C1—C2—O4	−6.9 (4)	C2—C1—C7—O5	−168.4 (2)
C4—C1—C2—O4	−129.4 (3)	C4—C1—C7—O5	−61.8 (3)
O1—C1—C2—C3	−118.7 (2)	O2—C6—C5—C4	179.2 (3)
C7—C1—C2—C3	112.5 (3)	O1—C6—C5—C4	−0.3 (4)
C4—C1—C2—C3	−10.0 (2)	C3—C4—C5—C6	−100.0 (3)
C5—C4—C3—O3	−148.6 (3)	C1—C4—C5—C6	−2.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H04···O3^i	0.85 (4)	1.84 (4)	2.688 (4)	178 (4)
O3—H03···O4^ii	0.93 (4)	1.78 (5)	2.706 (3)	173 (4)
O5—H05···O5^iii	0.94 (6)	1.75 (6)	2.673 (3)	165 (4)

Symmetry codes: (i) x, y, z−1; (ii) −y+1, x−y−1, z+1/3; (iii) −x+y+2, −x+2, z−1/3.