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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 66| Part 9| September 2010| Page o2341
https://doi.org/10.1107/S1600536810032368

2,3;5,6-Di-O-iso­propyl­­idene-1-O-(2-phenyl­acet­yl)-α-D-manno­furan­ose

Iulia A. Sacui,a Peter Norrisa and Matthias Zellera*

aDepartment of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555-3663, USA
*Correspondence e-mail: mzeller@ysu.edu

(Received 22 July 2010; accepted 11 August 2010; online 18 August 2010)

The title compound, C20H26O7, was prepared by esterification of 2,3;5,6-di-O-isopropyl­idene-α-D-mannofuran­ose with phenyl­acetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) con­ditions. The solid-state structure confirms the retention of the α-configuration at the anomeric C atom. The compound is characterized by a relatively rigid framework with only a few degrees of freedom. Comparison with other di-O-isopropyl­idenemannofuran­ose derivatives shows the main differences to be associated with the flexible dimethyl­dioxolane ring, and that there are only small differences for the 2,3-O-isopropyl­idene-α-D-manno­furan­ose backbone. The packing is marked by a large number of weak C—H⋯O inter­actions.

Related literature

For general background, see: Sacui et al. (2008[Sacui, I. A., Zeller, M. & Norris, P. (2008). Carbohydr. Res. 343, 1819-1823.]). For related structures, see: Aebischer et al. (1982[Aebischer, B. M., Hanssen, H. W., Vasella, A. T. & Schweizer, W. B. (1982). J. Chem. Soc. Perkin Trans. 1, 2139-2147.]); Dang et al. (2001[Dang, H.-S., Roberts, B. P. & Tocher, D. A. (2001). J. Chem. Soc. Perkin Trans. 1, pp. 2452-2461.]); Miner et al. (2004[Miner, P. L., Norris, P. & Zeller, M. (2004). Private communication (refcode CUFYIL01). CCDC, Union Road, Cambridge, England.]); Sheldrick et al. (1985[Sheldrick, B., Mackie, W. & Akrigg, D. (1985). Acta Cryst. C41, 431-433.]); Zhao et al. (2006[Zhao, S.-S., Zhao, J.-Q., Li, J.-X., Wang, Q. & Zhao, D.-M. (2006). Acta Cryst. E62, o3372-o3373.]). For details of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C20H26O7

  • Mr = 378.41

  • Orthorhombic, P 21 21 21

  • a = 5.6174 (3) Å

  • b = 13.0946 (8) Å

  • c = 25.2021 (15) Å

  • V = 1853.81 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.60 × 0.33 × 0.12 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA.]) Tmin = 0.812, Tmax = 0.988

  • 18953 measured reflections

  • 2668 independent reflections

  • 2652 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.117

  • S = 1.33

  • 2668 reflections

  • 248 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯O6i 1.00 2.46 3.382 (3) 153
C17—H17⋯O5ii 0.95 2.54 3.483 (3) 172
C2—H2⋯O7iii 1.00 2.65 3.591 (3) 156
C3—H3⋯O1iii 1.00 2.67 3.559 (3) 148
C8—H8C⋯O1iii 0.98 2.62 3.570 (3) 164
C12—H12A⋯O7iv 0.98 2.70 3.323 (4) 122
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]; (iii) x-1, y, z; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART for WNT/2000 (Bruker, 2002[Bruker (2002). SMART for WNT/2000. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032368/bv2157sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032368/bv2157Isup2.hkl

checkCIF report


Comment top

The title compound, 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose, was prepared as part of our ongoing work on the synthesis and metal-catalyzed decomposition of carbohydrate-derived diazo compounds (Sacui et al., 2008). It was prepared by esterification of commercially available 2,3;5,6-di-O-isopropylidene-α-D-mannofuranose with phenylacetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) conditions. From 1H NMR data, the precursor lactol (before esterification) exists in solution only as the α-anomer, which is in agreement with the reported solid state structure (Sheldrick et al., 1985; Miner et al., 2004). 1H NMR data point in the same direction for the title compound. To obtain proof of the configuration of the title compound in the solid state we investigated its structure by single-crystal diffraction.

Slow evaporation of a solution of the compound in 95% ethyl alcohol led to formation of crystals of the title compound that could be analyzed by single-crystal diffraction. The compound crystallizes in an orthorhombic setting in P212121 with one crystallographically independent molecule. The solid state structure confirms retention of the α-configuration at C-1 of the furanose ring under the conditions of the DCC-promoted esterification.

No strong directional intermolecular interactions are present in the structure of the title compound. For the carbohydrate part of the molecules the packing is instead marked by a large number of weaker C—H···O interactions as depicted in Fig. 2 (for numerical values, see Table 1). The phenyl rings are not involved in any π–π stacking interactions but instead they do group with the isopropylidene moieties to form layers perpendicular to the (110) plane characterized by the absence of any directional forces. Thus a semi-layered structure is created with alternating sections dominated by C—H···O interactions (the carbohydrate layers) and layers with only van der Waals / dispersion forces (the phenyl-isopropylidene layers).

All bond lengths and angles in the title compound are within the expected ranges for an organic compound. For the dihedral angles, most are fixed by the rigid backbone of the isopropylidene-mannofuranose skeleton, and the molecule exhibits only a few selected degrees of freedom. This becomes clearly apparent when, for example, comparing the title compound with other related compounds with a 2,3;5,6-di-O-isopropylidene-mannofuranose skeleton. A search in the Cambridge Crystallographic Database (version 5.31, 2010; Allen, 2002) revealed four related compounds, one of which has an L-mannofuranose sugar (BIRFUD, Aebischer et al., 1982), and one a β connection at carbon C1 (QEMKID, Zhao et al., 2006). The other two compounds are the lactol itself (CUFYIL, Sheldrick et al., 1985; Miner et al., 2004), and the 1-O-methyl derivative of the title compound (BOXQAG, Dang et al., 2001). Least square overlays of the latter two with the title compound are shown in Figs. 3a and 3b (title compound in red). The 2,3-O-isopropylidene-mannofuranose skeleton in all three compounds shows only small deviations and virtually all conformational differences are limited to the more flexible second isopropylidene moiety, which is rotated differently when compared to the title compound and which also exhibits different types of envelope conformations: In the title compound the isopropylidene unit is out of plane with the other four atoms constituting the five membered ring. In the methyl derivative it is the C—H group, and in the lactol, the methylene group, thus confirming that the energies of the different conformers of the dimethyldioxolane rings are indeed very close. For compound QEMKID (Zhao et al., 2006), which features a β connection at carbon C1, a different conformation is also found for the actual sugar with C1 and O1 changing their roles in the five membered ring (Figure 3c). Overall, the crystal structure of the title compound provides evidence that appending an ester group at C-1 does little to alter the conformation of the mannofuranose ring.

Related literature top

For general background, see: Sacui et al. (2008). For related structures, see: Aebischer et al. (1982); Dang et al. (2001); Miner et al. (2004); Sheldrick et al. (1985); Zhao et al. (2006). For details of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound was prepared from 1,2;5,6-di-O-isopropylidene-α-D-mannofuranose by esterification with phenylacetic acid using standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) conditions in a similar fashion to that described earlier (Sacui et al., 2008). A colorless solid was obtained after column chromatography (silica gel, 4:1 hexanes–EtOAc). Crystallization from 95% ethyl alcohol yielded colourless crystals suitable for single-crystal X-ray diffraction.

Refinement top

Treatment of hydrogen atoms: Hydrogen atoms have been added in calculated positions with C—H bond lengths between 0.95 and 1.00 Å and have been refined with an isotropic displacement parameter of 1.5 times (CH3) or 1.2 times (C—H and CH2) that of the equivalent isotropic displacement parameter of the adjacent carbon atom. Methyl H atoms were allowed to rotate to best fit the experimental electron density.

Assignment of absolute structure: Friedel pairs have been merged before refinement. The absolute structure assignment is based on the known configuration of carbon atoms retaining their configuration during the synthesis.

Structure description top

The title compound, 1-O-(2-phenylacetyl)-2,3;5,6-di-O-isopropylidene-α-D-mannofuranose, was prepared as part of our ongoing work on the synthesis and metal-catalyzed decomposition of carbohydrate-derived diazo compounds (Sacui et al., 2008). It was prepared by esterification of commercially available 2,3;5,6-di-O-isopropylidene-α-D-mannofuranose with phenylacetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) conditions. From 1H NMR data, the precursor lactol (before esterification) exists in solution only as the α-anomer, which is in agreement with the reported solid state structure (Sheldrick et al., 1985; Miner et al., 2004). 1H NMR data point in the same direction for the title compound. To obtain proof of the configuration of the title compound in the solid state we investigated its structure by single-crystal diffraction.

Slow evaporation of a solution of the compound in 95% ethyl alcohol led to formation of crystals of the title compound that could be analyzed by single-crystal diffraction. The compound crystallizes in an orthorhombic setting in P212121 with one crystallographically independent molecule. The solid state structure confirms retention of the α-configuration at C-1 of the furanose ring under the conditions of the DCC-promoted esterification.

No strong directional intermolecular interactions are present in the structure of the title compound. For the carbohydrate part of the molecules the packing is instead marked by a large number of weaker C—H···O interactions as depicted in Fig. 2 (for numerical values, see Table 1). The phenyl rings are not involved in any π–π stacking interactions but instead they do group with the isopropylidene moieties to form layers perpendicular to the (110) plane characterized by the absence of any directional forces. Thus a semi-layered structure is created with alternating sections dominated by C—H···O interactions (the carbohydrate layers) and layers with only van der Waals / dispersion forces (the phenyl-isopropylidene layers).

All bond lengths and angles in the title compound are within the expected ranges for an organic compound. For the dihedral angles, most are fixed by the rigid backbone of the isopropylidene-mannofuranose skeleton, and the molecule exhibits only a few selected degrees of freedom. This becomes clearly apparent when, for example, comparing the title compound with other related compounds with a 2,3;5,6-di-O-isopropylidene-mannofuranose skeleton. A search in the Cambridge Crystallographic Database (version 5.31, 2010; Allen, 2002) revealed four related compounds, one of which has an L-mannofuranose sugar (BIRFUD, Aebischer et al., 1982), and one a β connection at carbon C1 (QEMKID, Zhao et al., 2006). The other two compounds are the lactol itself (CUFYIL, Sheldrick et al., 1985; Miner et al., 2004), and the 1-O-methyl derivative of the title compound (BOXQAG, Dang et al., 2001). Least square overlays of the latter two with the title compound are shown in Figs. 3a and 3b (title compound in red). The 2,3-O-isopropylidene-mannofuranose skeleton in all three compounds shows only small deviations and virtually all conformational differences are limited to the more flexible second isopropylidene moiety, which is rotated differently when compared to the title compound and which also exhibits different types of envelope conformations: In the title compound the isopropylidene unit is out of plane with the other four atoms constituting the five membered ring. In the methyl derivative it is the C—H group, and in the lactol, the methylene group, thus confirming that the energies of the different conformers of the dimethyldioxolane rings are indeed very close. For compound QEMKID (Zhao et al., 2006), which features a β connection at carbon C1, a different conformation is also found for the actual sugar with C1 and O1 changing their roles in the five membered ring (Figure 3c). Overall, the crystal structure of the title compound provides evidence that appending an ester group at C-1 does little to alter the conformation of the mannofuranose ring.

For general background, see: Sacui et al. (2008). For related structures, see: Aebischer et al. (1982); Dang et al. (2001); Miner et al. (2004); Sheldrick et al. (1985); Zhao et al. (2006). For details of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Molecular packing and intermolecular interactions. C—H···O interactions are symbolized by blue dashed lines. View down the a axis.
[Figure 3] Fig. 3. Least square overlays of the title compound with (a) 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (CUFYIL, Sheldrick et al., 1985; Miner et al., 2004), (b) methyl 2,3:5,6-di-O-isopropylidene-β-L-gulofuranoside (BOXQAG, Dang et al., 2001), (c) 5-tert-butyl-3-((6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro(3,4-d)(1,3)dioxol-4-yloxy)methyl)-2-hydroxybenzaldehyde (QEMKID, Zhao et al., 2006).
2,3;5,6-Di-O-isopropylidene-1-O-(2-phenylacetyl)- α-D-mannofuranose top
Crystal data top
C20H26O7F(000) = 808
Mr = 378.41Dx = 1.356 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9604 reflections
a = 5.6174 (3) Åθ = 2.9–30.4°
b = 13.0946 (8) ŵ = 0.10 mm−1
c = 25.2021 (15) ÅT = 100 K
V = 1853.81 (19) Å3Block, colourless
Z = 40.60 × 0.33 × 0.12 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		2668 independent reflections
Radiation source: fine-focus sealed tube2652 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)		h = −7→7
Tmin = 0.812, Tmax = 0.988k = −17→17
18953 measured reflectionsl = −32→33
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.33 w = 1/[σ2(Fo2) + (0.0345P)2 + 1.2578P]
where P = (Fo2 + 2Fc2)/3
2668 reflections(Δ/σ)max < 0.001
248 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C20H26O7V = 1853.81 (19) Å3
Mr = 378.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.6174 (3) ŵ = 0.10 mm−1
b = 13.0946 (8) ÅT = 100 K
c = 25.2021 (15) Å0.60 × 0.33 × 0.12 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		2668 independent reflections
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)		2652 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.988Rint = 0.040
18953 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.33Δρmax = 0.37 e Å−3
2668 reflectionsΔρmin = −0.26 e Å−3
248 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
O10.9107 (3)0.56927 (14)0.25276 (7)0.0161 (4)
O60.9344 (4)0.81639 (14)0.35444 (8)0.0199 (4)
O71.1329 (3)0.56059 (15)0.14428 (7)0.0193 (4)
O20.7450 (3)0.56285 (14)0.16757 (7)0.0167 (4)
O40.5450 (4)0.47655 (14)0.33085 (7)0.0200 (4)
O30.5940 (4)0.37204 (14)0.26113 (8)0.0230 (4)
O50.6671 (3)0.69122 (14)0.36960 (7)0.0184 (4)
C50.8432 (5)0.6452 (2)0.33622 (10)0.0166 (5)
H50.90900.58240.35340.020*
C130.9301 (5)0.57991 (19)0.13408 (10)0.0155 (5)
C30.5230 (5)0.54195 (19)0.28614 (9)0.0140 (5)
H30.36390.57610.28460.017*
C181.2659 (6)0.5338 (2)−0.04967 (10)0.0250 (6)
H181.36160.5120−0.07860.030*
C171.0503 (6)0.4865 (2)−0.03966 (11)0.0257 (6)
H170.99640.4330−0.06210.031*
C40.7276 (5)0.61858 (19)0.28397 (9)0.0147 (5)
H40.67380.68240.26570.018*
C160.9133 (5)0.5172 (2)0.00314 (11)0.0208 (6)
H160.76680.48360.01020.025*
C100.7721 (5)0.77973 (19)0.39329 (10)0.0167 (5)
C20.5653 (5)0.47073 (19)0.23826 (10)0.0158 (5)
H20.43230.47330.21190.019*
C150.9879 (5)0.59677 (19)0.03595 (9)0.0162 (5)
C120.5801 (6)0.8580 (2)0.40282 (12)0.0248 (6)
H12A0.65120.92010.41760.037*
H12B0.46290.83050.42780.037*
H12C0.50130.87430.36920.037*
C201.2031 (5)0.6441 (2)0.02492 (10)0.0192 (5)
H201.25610.69860.04680.023*
C80.2243 (5)0.3600 (2)0.31076 (11)0.0183 (5)
H8A0.15810.36570.34660.028*
H8B0.19020.29200.29640.028*
H8C0.15200.41200.28790.028*
C10.8021 (4)0.50643 (19)0.21488 (9)0.0145 (5)
H10.90610.44670.20630.017*
C61.0386 (5)0.72767 (19)0.33117 (10)0.0178 (5)
H6A1.18430.70720.35050.021*
H6B1.07950.73990.29350.021*
C90.6133 (5)0.3004 (3)0.34852 (14)0.0324 (8)
H9A0.78550.31250.34820.049*
H9B0.58040.23100.33590.049*
H9C0.55280.30810.38480.049*
C191.3418 (5)0.6130 (2)−0.01758 (11)0.0225 (6)
H191.48900.6461−0.02470.027*
C70.4927 (5)0.3763 (2)0.31284 (10)0.0176 (5)
C110.9020 (6)0.7498 (2)0.44388 (11)0.0244 (6)
H11A1.02450.69890.43560.037*
H11B0.78820.72080.46920.037*
H11C0.97700.81040.45940.037*
C140.8400 (5)0.6279 (2)0.08310 (10)0.0215 (6)
H14A0.67270.60710.07720.026*
H14B0.84360.70320.08660.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0129 (8)0.0187 (9)0.0166 (8)−0.0001 (8)0.0006 (7)−0.0021 (7)
O60.0192 (9)0.0144 (8)0.0259 (9)−0.0018 (8)0.0071 (8)−0.0006 (7)
O70.0156 (9)0.0206 (9)0.0216 (9)−0.0011 (8)0.0021 (8)0.0027 (8)
O20.0154 (9)0.0201 (8)0.0145 (8)0.0026 (8)0.0005 (7)0.0000 (7)
O40.0233 (10)0.0199 (9)0.0169 (8)−0.0102 (8)−0.0028 (8)0.0029 (7)
O30.0250 (10)0.0139 (9)0.0300 (10)0.0024 (8)0.0110 (9)0.0008 (8)
O50.0172 (9)0.0199 (9)0.0180 (8)−0.0060 (8)0.0029 (8)−0.0050 (7)
C50.0160 (12)0.0179 (11)0.0160 (11)−0.0028 (11)0.0003 (10)0.0013 (9)
C130.0192 (12)0.0127 (11)0.0146 (11)0.0018 (10)0.0006 (10)−0.0026 (9)
C30.0128 (11)0.0145 (11)0.0148 (10)−0.0010 (9)−0.0007 (9)−0.0001 (9)
C180.0350 (16)0.0256 (13)0.0143 (11)0.0100 (13)0.0066 (12)0.0025 (10)
C170.0376 (17)0.0194 (12)0.0200 (12)0.0000 (13)−0.0058 (12)−0.0029 (10)
C40.0152 (11)0.0136 (10)0.0152 (10)0.0009 (10)0.0001 (10)−0.0002 (9)
C160.0208 (13)0.0176 (12)0.0240 (13)−0.0025 (11)−0.0035 (11)0.0054 (10)
C100.0165 (12)0.0148 (11)0.0187 (11)−0.0045 (10)0.0022 (10)−0.0016 (9)
C20.0137 (11)0.0157 (11)0.0181 (11)−0.0010 (10)0.0008 (10)−0.0020 (9)
C150.0179 (12)0.0166 (11)0.0141 (11)0.0042 (10)−0.0010 (10)0.0049 (9)
C120.0226 (14)0.0208 (12)0.0309 (14)0.0019 (12)0.0099 (12)0.0019 (11)
C200.0222 (13)0.0156 (11)0.0196 (11)0.0017 (11)−0.0039 (11)−0.0009 (10)
C80.0127 (11)0.0183 (12)0.0239 (12)−0.0008 (10)0.0009 (10)−0.0026 (10)
C10.0121 (11)0.0157 (11)0.0157 (10)0.0018 (10)0.0027 (9)−0.0005 (9)
C60.0168 (12)0.0165 (11)0.0202 (11)−0.0016 (10)0.0022 (10)−0.0027 (10)
C90.0131 (13)0.0340 (16)0.0501 (19)−0.0029 (13)−0.0004 (13)0.0234 (15)
C190.0187 (13)0.0227 (13)0.0262 (13)0.0025 (12)0.0027 (11)0.0076 (11)
C70.0130 (11)0.0175 (12)0.0223 (12)0.0000 (10)−0.0003 (10)0.0023 (10)
C110.0241 (14)0.0281 (14)0.0209 (12)−0.0015 (13)−0.0035 (12)−0.0045 (11)
C140.0211 (13)0.0251 (13)0.0183 (12)0.0079 (12)0.0028 (11)0.0039 (10)
Geometric parameters (Å, º) top
O1—C11.400 (3)C10—C121.507 (4)
O1—C41.447 (3)C10—C111.520 (4)
O6—C101.421 (3)C2—C11.528 (3)
O6—C61.427 (3)C2—H21.0000
O7—C131.195 (3)C15—C201.386 (4)
O2—C131.358 (3)C15—C141.506 (4)
O2—C11.439 (3)C12—H12A0.9800
O4—C71.420 (3)C12—H12B0.9800
O4—C31.421 (3)C12—H12C0.9800
O3—C71.423 (3)C20—C191.386 (4)
O3—C21.424 (3)C20—H200.9500
O5—C101.431 (3)C8—C71.523 (4)
O5—C51.432 (3)C8—H8A0.9800
C5—C41.509 (3)C8—H8B0.9800
C5—C61.545 (4)C8—H8C0.9800
C5—H51.0000C1—H11.0000
C13—C141.517 (3)C6—H6A0.9900
C3—C41.527 (4)C6—H6B0.9900
C3—C21.543 (3)C9—C71.502 (4)
C3—H31.0000C9—H9A0.9800
C18—C191.382 (4)C9—H9B0.9800
C18—C171.384 (5)C9—H9C0.9800
C18—H180.9500C19—H190.9500
C17—C161.385 (4)C11—H11A0.9800
C17—H170.9500C11—H11B0.9800
C4—H41.0000C11—H11C0.9800
C16—C151.395 (4)C14—H14A0.9900
C16—H160.9500C14—H14B0.9900
C1—O1—C4108.84 (19)H12A—C12—H12B109.5
C10—O6—C6105.74 (19)C10—C12—H12C109.5
C13—O2—C1115.40 (19)H12A—C12—H12C109.5
C7—O4—C3106.61 (18)H12B—C12—H12C109.5
C7—O3—C2106.85 (19)C19—C20—C15121.0 (3)
C10—O5—C5107.5 (2)C19—C20—H20119.5
O5—C5—C4108.2 (2)C15—C20—H20119.5
O5—C5—C6104.2 (2)C7—C8—H8A109.5
C4—C5—C6113.3 (2)C7—C8—H8B109.5
O5—C5—H5110.3H8A—C8—H8B109.5
C4—C5—H5110.3C7—C8—H8C109.5
C6—C5—H5110.3H8A—C8—H8C109.5
O7—C13—O2124.2 (2)H8B—C8—H8C109.5
O7—C13—C14126.0 (2)O1—C1—O2111.1 (2)
O2—C13—C14109.8 (2)O1—C1—C2107.23 (19)
O4—C3—C4111.0 (2)O2—C1—C2106.4 (2)
O4—C3—C2104.02 (19)O1—C1—H1110.6
C4—C3—C2104.7 (2)O2—C1—H1110.6
O4—C3—H3112.2C2—C1—H1110.6
C4—C3—H3112.2O6—C6—C5104.1 (2)
C2—C3—H3112.2O6—C6—H6A110.9
C19—C18—C17120.0 (3)C5—C6—H6A110.9
C19—C18—H18120.0O6—C6—H6B110.9
C17—C18—H18120.0C5—C6—H6B110.9
C18—C17—C16119.9 (3)H6A—C6—H6B109.0
C18—C17—H17120.1C7—C9—H9A109.5
C16—C17—H17120.1C7—C9—H9B109.5
O1—C4—C5105.8 (2)H9A—C9—H9B109.5
O1—C4—C3105.15 (19)C7—C9—H9C109.5
C5—C4—C3116.4 (2)H9A—C9—H9C109.5
O1—C4—H4109.8H9B—C9—H9C109.5
C5—C4—H4109.8C18—C19—C20119.9 (3)
C3—C4—H4109.8C18—C19—H19120.0
C17—C16—C15120.8 (3)C20—C19—H19120.0
C17—C16—H16119.6O4—C7—O3104.2 (2)
C15—C16—H16119.6O4—C7—C9109.1 (2)
O6—C10—O5104.52 (19)O3—C7—C9110.0 (2)
O6—C10—C12109.8 (2)O4—C7—C8110.2 (2)
O5—C10—C12108.8 (2)O3—C7—C8111.0 (2)
O6—C10—C11110.9 (2)C9—C7—C8112.0 (2)
O5—C10—C11109.8 (2)C10—C11—H11A109.5
C12—C10—C11112.7 (2)C10—C11—H11B109.5
O3—C2—C1109.6 (2)H11A—C11—H11B109.5
O3—C2—C3104.44 (19)C10—C11—H11C109.5
C1—C2—C3104.5 (2)H11A—C11—H11C109.5
O3—C2—H2112.6H11B—C11—H11C109.5
C1—C2—H2112.6C15—C14—C13111.8 (2)
C3—C2—H2112.6C15—C14—H14A109.3
C20—C15—C16118.5 (2)C13—C14—H14A109.3
C20—C15—C14121.2 (2)C15—C14—H14B109.3
C16—C15—C14120.3 (3)C13—C14—H14B109.3
C10—C12—H12A109.5H14A—C14—H14B107.9
C10—C12—H12B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O6i1.002.463.382 (3)153
C17—H17···O5ii0.952.543.483 (3)172
C2—H2···O7iii1.002.653.591 (3)156
C3—H3···O1iii1.002.673.559 (3)148
C8—H8C···O1iii0.982.623.570 (3)164
C12—H12A···O7iv0.982.703.323 (4)122
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2; (iii) x−1, y, z; (iv) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC20H26O7
Mr378.41
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)5.6174 (3), 13.0946 (8), 25.2021 (15)
V (Å3)1853.81 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.60 × 0.33 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS in SAINT-Plus; Bruker, 2003)
Tmin, Tmax0.812, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		18953, 2668, 2652
Rint0.040
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.117, 1.33
No. of reflections2668
No. of parameters248
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.26

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O6i1.002.463.382 (3)152.8
C17—H17···O5ii0.952.543.483 (3)172.3
C2—H2···O7iii1.002.653.591 (3)156.1
C3—H3···O1iii1.002.673.559 (3)148.0
C8—H8C···O1iii0.982.623.570 (3)163.5
C12—H12A···O7iv0.982.703.323 (4)121.9
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2; (iii) x−1, y, z; (iv) −x+2, y+1/2, −z+1/2.
 

Acknowledgements

IAS and PN thank the American Chemical Society Petroleum Research Fund for financial support (grant No. 43948-B1). The diffractometer was funded by NSF grant No. 0087210, by Ohio Board of Regents grant No. CAP-491 and by YSU.

References

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2341
https://doi.org/10.1107/S1600536810032368
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