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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o961-o962
https://doi.org/10.1107/S2056989015021854

Crystal structure of 1,2,3,4-di-O-methyl­ene-α-D-galacto­pyran­ose

Ioannis Tiritiris,a Stefan Tussetschlägera and Willi Kantlehnera*

aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@hs-aalen.de

Edited by M. Zeller, Youngstown State University, USA (Received 9 November 2015; accepted 16 November 2015; online 21 November 2015)

The title compound, C8H12O6, was synthesized by de­acetyl­ation of 6-acetyl-1,2,3,4-di-O-methyl­ene-α-D-galactose with sodium methoxide. The central part of the mol­ecule consists of a six-membered C5O pyran­ose ring with a twist-boat conformation. Both fused dioxolane rings adopt an envelope conformation with C and O atoms as the flap. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds are present between adjacent mol­ecules, generating a three-dimensional network.

CCDC reference: 1437272

Similar articles

1. Related literature

For the synthesis of 6-acetyl-1,2,3,4-di-O-methyl­ene-α-D-galactose, see: Bok et al. (1952[Bok, L. D. C., Petters, L. B., Hough, L., Jones, J. K. N., Magson, M. S., Bell, F., Braude, E. A., Fawcett, J. S., Smith, G. H., Smith, F. E. & Boon, W. R. (1952). J. Chem. Soc. pp. 1524-1532.]). For the crystal structures of the α- and β-anomers of D-galactose, see: Sheldrick (1976[Sheldrick, B. (1976). Acta Cryst. B32, 1016-1020.]). For the crystal structure of 6-O-cyano­methyl-1,2:3,4-di-O-iso­propyl­idene-α-D-galactose, see: Langer et al. (2005[Langer, V., Steiner, B., Mičová, J. & Koóš, M. (2005). Acta Cryst. E61, o779-o781.]). For the crystal structure of 6-[bis­(eth­oxy­carbon­yl)meth­yl]-6-de­oxy-1,2;3,4-di-O-iso­propyl­idene-D-galacto­pyran­ose, see: Doboszewski et al. (2010[Doboszewski, B., Silva, P. R. da, Nazarenko, A. Y. & Nemykin, V. N. (2010). Acta Cryst. E66, o3217-o3218.]). For the crystal structure of 1,2,3,5-di-O-methyl­ene-α-D-xylo­furan­ose see: Tiritiris et al. (2015a[Tiritiris, I., Saur, S. & Kantlehner, W. (2015a). Acta Cryst. E71, o916.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C8H12O6

  • Mr = 204.18

  • Orthorhombic, P 21 21 21

  • a = 6.4876 (6) Å

  • b = 6.6364 (5) Å

  • c = 20.1224 (16) Å

  • V = 866.36 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 100 K

  • 0.43 × 0.32 × 0.04 mm

2.2. Data collection

  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.705, Tmax = 0.746

  • 10453 measured reflections

  • 2680 independent reflections

  • 2464 reflections with I > 2σ(I)

  • Rint = 0.023

  • Standard reflections: 0

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.075

  • S = 1.06

  • 2680 reflections

  • 131 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H12⋯O5i 0.87 (3) 2.01 (3) 2.846 (2) 161
C3—H3⋯O4ii 1.00 2.49 3.447 (2) 160
C4—H4⋯O3iii 1.00 2.46 3.296 (2) 141
C5—H5⋯O2iv 1.00 2.45 3.405 (2) 160
C7—H7A⋯O1v 0.99 2.48 3.455 (2) 169
C7—H7B⋯O1ii 0.99 2.56 3.509 (2) 162
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) x-1, y, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x, y+1, z; (v) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1437272

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015021854/zl2651sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021854/zl2651Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021854/zl2651Isup3.cml

checkCIF report


Comment top

The synthesis of the protected sugar 1,2,3,4-di-O-methylene-α-D-galactopyranose has been well known for many years (Bok et al., 1952). Its crystal structure, however, remained undetermined. According to the structure analysis of the title compound, which we would like to report now, the central part of the molecule consists of a six-membered C5O ring, which is made up from the carbon atoms C1–C5 and O1 (Fig. 1). The chiral carbon atoms C1/C2/C4/C5 of the pyranose part show R-configuration and C3 shows S-configuration, in agreement with the expected configurations for an α-D-galactose ring. Both fused dioxolane rings adopt an envelope conformation with the carbon atom C7 (ring I) and oxygen atom O3 (ring II) as the flap, respectively. The pyranose ring shows a twist-boat conformation. A similar conformation of the pyranose ring has been observed in 6-[bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropylidene-D-galactopyranose (Doboszewski et al., 2010). The C–O and C–C and bond lengths in the molecule are comparable with the data from the crystal structure analysis of 1,2,3,5-di-O-methylene-α-D-xylofuranose (Tiritiris et al., 2015a) and other related compounds [see, for example: 6-O-cyanomethyl-1,2:3,4-di-O-isopropylidene-α-D-galactose (Langer et al., 2005), and the α- and β-anomers of D-galactose (Sheldrick, 1976)]. In the crystal structure, O—H···O hydrogen bonds between adjacent molecules are present [d(H···O) = 2.01 (3) Å] (Tab. 1), generating infinite one-dimensional chains with base vector [100] (Fig. 2). Taking additional C—H···O hydrogen bonds between adjacent molecules [d(H···O) = 2.45–2.56 Å] (Tab. 1) into account, a three-dimensional network is generated (Fig. 3).

Related literature top

For the synthesis of 6-acetyl-1,2,3,4-di-O-methylene-α-D-galactose, see: Bok et al. (1952). For the crystal structures of the α- and β-anomers of D-galactose, see: Sheldrick (1976). For the crystal structure of 6-O-cyanomethyl-1,2:3,4-di-O-isopropylidene-α-D-galactose, see: Langer et al. (2005). For the crystal structure of 6-[bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropylidene-D-galactopyranose, see: Doboszewski et al. (2010). For the crystal structure of 1,2,3,5-di-O-methylene-α-D-xylofuranose see: Tiritiris et al. (2015a).

Experimental top

According to the literature (Bok et al., 1952) a solution of 25 g (139 mmol) D-galactose in 20 ml water was mixed with 100 ml glacial acetic acid. 27.5 g (916 mmol) paraformaldehyde was then added at room temperature. Followed by dropwise addition of 12.5 ml concentrated sulfuric acid, the reaction mixture was heated to 373 K for one hour. After subsequent cooling to room temperature, 100 ml water was added to the mixture. The solution was extracted three times with chloroform and the combined extracts were washed with water and dried over sodium sulfate. After evaporation of the solvent, the crude product was destilled under reduced presure using a 20 cm Vigreux column. The fraction at 407 K (0.1 mbar) contained 4.28 g (13%) of 6-acetyl-1,2,3,4-di-O-methylene-α-D-galactose as the product. To a heated solution of 2.96 g (12 mmol) 6-acetyl-1,2,3,4-di-O-methylene-α-D-galactose (Bok et al., 1952) in 25 ml me thanol, 50 mg of sodium methoxide was added. After subsequent cooling to room temperature, 50 ml water was added to the mixture. The solution was extracted two times with diethyl ether and the combined extracts were dried over sodium sulfate. After evaporation of the solvent, the crude product was distilled under reduced presure using a 20 cm Vigreux column. The fraction at 395 K (0.1 mbar) contained 1.6 g (66%) of the title compound, which crystallized spontaneously after several days at room temperature, forming colorless single crystals suitable for X-ray analysis.

Refinement top

The O-bound H atom was located in a difference Fourier map and was refined freely [O2—H12 = 0.87 (3) Å]. The title compound crystallizes in the non-centrosymmetric space group P212121; however, in the absence of significant anomalous scattering effects, the Flack parameter is essentially meaningless and the absolute configuration was chosen based on known stereocenters unchanged during synthesis. The H atoms in CH2 and CH groups were placed in calculated positions with d(C—H) = 0.99 Å and d(C—H) = 1.00 Å and refined using a riding model, with Ueq(H) set to 1.2 Ueq(C).

Structure description top

The synthesis of the protected sugar 1,2,3,4-di-O-methylene-α-D-galactopyranose has been well known for many years (Bok et al., 1952). Its crystal structure, however, remained undetermined. According to the structure analysis of the title compound, which we would like to report now, the central part of the molecule consists of a six-membered C5O ring, which is made up from the carbon atoms C1–C5 and O1 (Fig. 1). The chiral carbon atoms C1/C2/C4/C5 of the pyranose part show R-configuration and C3 shows S-configuration, in agreement with the expected configurations for an α-D-galactose ring. Both fused dioxolane rings adopt an envelope conformation with the carbon atom C7 (ring I) and oxygen atom O3 (ring II) as the flap, respectively. The pyranose ring shows a twist-boat conformation. A similar conformation of the pyranose ring has been observed in 6-[bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropylidene-D-galactopyranose (Doboszewski et al., 2010). The C–O and C–C and bond lengths in the molecule are comparable with the data from the crystal structure analysis of 1,2,3,5-di-O-methylene-α-D-xylofuranose (Tiritiris et al., 2015a) and other related compounds [see, for example: 6-O-cyanomethyl-1,2:3,4-di-O-isopropylidene-α-D-galactose (Langer et al., 2005), and the α- and β-anomers of D-galactose (Sheldrick, 1976)]. In the crystal structure, O—H···O hydrogen bonds between adjacent molecules are present [d(H···O) = 2.01 (3) Å] (Tab. 1), generating infinite one-dimensional chains with base vector [100] (Fig. 2). Taking additional C—H···O hydrogen bonds between adjacent molecules [d(H···O) = 2.45–2.56 Å] (Tab. 1) into account, a three-dimensional network is generated (Fig. 3).

For the synthesis of 6-acetyl-1,2,3,4-di-O-methylene-α-D-galactose, see: Bok et al. (1952). For the crystal structures of the α- and β-anomers of D-galactose, see: Sheldrick (1976). For the crystal structure of 6-O-cyanomethyl-1,2:3,4-di-O-isopropylidene-α-D-galactose, see: Langer et al. (2005). For the crystal structure of 6-[bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropylidene-D-galactopyranose, see: Doboszewski et al. (2010). For the crystal structure of 1,2,3,5-di-O-methylene-α-D-xylofuranose see: Tiritiris et al. (2015a).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. O—H···O hydrogen bonds (black dashed lines) between adjacent molecules in the crystal structure of the title compound (ac view).
[Figure 3] Fig. 3. C—H···O and O—H···O hydrogen bonds (black dashed lines) between adjacent molecules in the crystal structure of the title compound (ac view).
1,2,3,4-di-O-Methylene-α-D-galactopyranose top
Crystal data top
C8H12O6Dx = 1.565 Mg m−3
Mr = 204.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2468 reflections
a = 6.4876 (6) Åθ = 2.0–30.7°
b = 6.6364 (5) ŵ = 0.14 mm−1
c = 20.1224 (16) ÅT = 100 K
V = 866.36 (12) Å3Plate, colorless
Z = 40.43 × 0.32 × 0.04 mm
F(000) = 432
Data collection top
Bruker Kappa APEXII DUO
diffractometer		2680 independent reflections
Radiation source: fine-focus sealed tube2464 reflections with I > 2σ(I)
Triumph monochromatorRint = 0.023
φ scans, and ω scansθmax = 30.7°, θmin = 2.0°
Absorption correction: multi-scan
(Blessing, 1995)		h = −9→6
Tmin = 0.705, Tmax = 0.746k = −9→8
10453 measured reflectionsl = −28→25
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.044P)2 + 0.0725P]
where P = (Fo2 + 2Fc2)/3
2680 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C8H12O6V = 866.36 (12) Å3
Mr = 204.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.4876 (6) ŵ = 0.14 mm−1
b = 6.6364 (5) ÅT = 100 K
c = 20.1224 (16) Å0.43 × 0.32 × 0.04 mm
Data collection top
Bruker Kappa APEXII DUO
diffractometer		2680 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		2464 reflections with I > 2σ(I)
Tmin = 0.705, Tmax = 0.746Rint = 0.023
10453 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.31 e Å−3
2680 reflectionsΔρmin = −0.18 e Å−3
131 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.34564 (16)0.56520 (14)0.10994 (5)0.0131 (2)
C10.2020 (2)0.4035 (2)0.11836 (7)0.0131 (3)
H10.21780.34520.16390.016*
O20.44408 (19)0.15283 (16)0.08328 (5)0.0213 (2)
H120.479 (4)0.093 (4)0.0465 (13)0.046 (7)*
C2−0.0156 (2)0.4835 (2)0.11004 (6)0.0144 (3)
H2−0.11860.37780.12240.017*
O30.12624 (15)0.64670 (16)0.25197 (5)0.0161 (2)
C3−0.0551 (2)0.6797 (2)0.15012 (6)0.0151 (3)
H3−0.17680.66080.18000.018*
O40.45725 (16)0.63594 (16)0.21656 (5)0.0173 (2)
C40.1274 (2)0.7537 (2)0.19020 (6)0.0134 (3)
H40.11350.90150.19870.016*
O5−0.04486 (17)0.54598 (15)0.04200 (5)0.0173 (2)
C50.3420 (2)0.70826 (19)0.16104 (7)0.0129 (2)
H50.40510.83650.14470.016*
O6−0.10172 (18)0.82816 (16)0.10055 (5)0.0209 (2)
C60.3323 (2)0.6556 (2)0.27434 (7)0.0162 (3)
H6A0.36080.54480.30600.019*
H6B0.35960.78570.29680.019*
C7−0.1757 (2)0.7162 (2)0.04575 (7)0.0193 (3)
H7A−0.16780.79670.00440.023*
H7B−0.32060.67460.05300.023*
C80.2518 (3)0.2439 (2)0.06717 (7)0.0179 (3)
H8A0.14190.14050.06660.021*
H8B0.25940.30570.02250.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0137 (5)0.0135 (4)0.0122 (4)−0.0019 (4)0.0031 (4)−0.0021 (3)
C10.0159 (6)0.0117 (5)0.0117 (6)−0.0017 (5)0.0011 (5)0.0002 (4)
O20.0284 (6)0.0197 (5)0.0156 (5)0.0096 (5)−0.0014 (5)−0.0029 (4)
C20.0142 (6)0.0171 (6)0.0118 (6)−0.0039 (5)0.0002 (5)0.0014 (5)
O30.0139 (5)0.0230 (5)0.0115 (4)−0.0016 (4)0.0002 (4)0.0030 (4)
C30.0129 (6)0.0206 (6)0.0119 (6)0.0025 (5)0.0008 (5)0.0006 (5)
O40.0127 (5)0.0262 (5)0.0131 (4)0.0037 (4)−0.0017 (4)−0.0034 (4)
C40.0137 (6)0.0151 (5)0.0113 (6)0.0026 (5)0.0015 (5)0.0003 (5)
O50.0174 (5)0.0238 (5)0.0105 (4)0.0015 (4)−0.0018 (4)0.0003 (4)
C50.0134 (6)0.0125 (5)0.0129 (6)−0.0007 (5)0.0000 (5)−0.0014 (4)
O60.0249 (6)0.0220 (5)0.0158 (5)0.0072 (4)−0.0051 (4)0.0008 (4)
C60.0155 (6)0.0203 (6)0.0128 (6)−0.0005 (5)−0.0005 (5)−0.0008 (5)
C70.0141 (7)0.0295 (7)0.0144 (6)0.0036 (6)−0.0020 (5)0.0015 (5)
C80.0237 (8)0.0145 (6)0.0155 (7)0.0020 (6)−0.0025 (5)−0.0022 (5)
Geometric parameters (Å, º) top
O1—C51.3997 (16)C3—H31.0000
O1—C11.4313 (16)O4—C61.4233 (17)
C1—C81.5123 (19)O4—C51.4275 (17)
C1—C21.518 (2)C4—C51.5404 (19)
C1—H11.0000C4—H41.0000
O2—C81.4237 (19)O5—C71.4152 (18)
O2—H120.87 (3)C5—H51.0000
C2—O51.4430 (16)O6—C71.4136 (18)
C2—C31.553 (2)C6—H6A0.9900
C2—H21.0000C6—H6B0.9900
O3—C61.4120 (17)C7—H7A0.9900
O3—C41.4313 (16)C7—H7B0.9900
C3—O61.4342 (17)C8—H8A0.9900
C3—C41.5146 (19)C8—H8B0.9900
C5—O1—C1114.24 (10)C5—C4—H4109.8
O1—C1—C8107.79 (11)C7—O5—C2104.94 (10)
O1—C1—C2109.29 (10)O1—C5—O4109.75 (10)
C8—C1—C2111.62 (11)O1—C5—C4115.33 (11)
O1—C1—H1109.4O4—C5—C4103.95 (11)
C8—C1—H1109.4O1—C5—H5109.2
C2—C1—H1109.4O4—C5—H5109.2
C8—O2—H12103.1 (18)C4—C5—H5109.2
O5—C2—C1109.12 (11)C7—O6—C3104.66 (11)
O5—C2—C3103.29 (11)O3—C6—O4105.95 (10)
C1—C2—C3112.93 (11)O3—C6—H6A110.5
O5—C2—H2110.4O4—C6—H6A110.5
C1—C2—H2110.4O3—C6—H6B110.5
C3—C2—H2110.4O4—C6—H6B110.5
C6—O3—C4104.54 (10)H6A—C6—H6B108.7
O6—C3—C4108.21 (12)O6—C7—O5104.91 (11)
O6—C3—C2104.46 (10)O6—C7—H7A110.8
C4—C3—C2114.78 (12)O5—C7—H7A110.8
O6—C3—H3109.7O6—C7—H7B110.8
C4—C3—H3109.7O5—C7—H7B110.8
C2—C3—H3109.7H7A—C7—H7B108.8
C6—O4—C5108.07 (11)O2—C8—C1109.23 (11)
O3—C4—C3107.31 (11)O2—C8—H8A109.8
O3—C4—C5103.80 (11)C1—C8—H8A109.8
C3—C4—C5116.12 (11)O2—C8—H8B109.8
O3—C4—H4109.8C1—C8—H8B109.8
C3—C4—H4109.8H8A—C8—H8B108.3
C5—O1—C1—C8−169.46 (11)C3—C2—O5—C7−24.54 (13)
C5—O1—C1—C269.05 (13)C1—O1—C5—O480.45 (13)
O1—C1—C2—O566.87 (13)C1—O1—C5—C4−36.51 (15)
C8—C1—C2—O5−52.27 (14)C6—O4—C5—O1−129.34 (12)
O1—C1—C2—C3−47.39 (14)C6—O4—C5—C4−5.45 (13)
C8—C1—C2—C3−166.53 (11)O3—C4—C5—O1103.14 (12)
O5—C2—C3—O60.05 (14)C3—C4—C5—O1−14.36 (17)
C1—C2—C3—O6117.79 (12)O3—C4—C5—O4−17.05 (13)
O5—C2—C3—C4−118.27 (12)C3—C4—C5—O4−134.55 (12)
C1—C2—C3—C4−0.54 (16)C4—C3—O6—C7147.17 (12)
C6—O3—C4—C3156.74 (11)C2—C3—O6—C724.45 (14)
C6—O3—C4—C533.27 (13)C4—O3—C6—O4−37.75 (14)
O6—C3—C4—O3159.69 (11)C5—O4—C6—O326.67 (14)
C2—C3—C4—O3−84.12 (13)C3—O6—C7—O5−41.25 (14)
O6—C3—C4—C5−84.77 (14)C2—O5—C7—O641.43 (14)
C2—C3—C4—C531.42 (16)O1—C1—C8—O268.75 (14)
C1—C2—O5—C7−144.91 (11)C2—C1—C8—O2−171.22 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H12···O5i0.87 (3)2.01 (3)2.846 (2)161
C3—H3···O4ii1.002.493.447 (2)160
C4—H4···O3iii1.002.463.296 (2)141
C5—H5···O2iv1.002.453.405 (2)160
C7—H7A···O1v0.992.483.455 (2)169
C7—H7B···O1ii0.992.563.509 (2)162
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x, y+1, z; (v) x−1/2, −y+3/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H12···O5i0.87 (3)2.01 (3)2.846 (2)161
C3—H3···O4ii1.002.493.447 (2)160
C4—H4···O3iii1.002.463.296 (2)141
C5—H5···O2iv1.002.453.405 (2)160
C7—H7A···O1v0.992.483.455 (2)169
C7—H7B···O1ii0.992.563.509 (2)162
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x, y+1, z; (v) x−1/2, −y+3/2, −z.
 

Acknowledgements

The authors thank Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for measuring the diffraction data.

References

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o961-o962
https://doi.org/10.1107/S2056989015021854
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