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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3250–o3251.
Published online 2010 November 20. doi:  10.1107/S1600536810047069
PMCID: PMC3011472

Ethyl 3,6-di-O-benzyl-2-de­oxy-N-phthalimido-1-thio-β-d-glucopyran­oside

Abstract

In the title compound, C30H31NO6S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thio­ethyl group has the exo-anomeric conformation. The hy­droxy group forms an inter­molecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close π–π contacts with centroid–centroid distances less than 4.0 Å, all with dihedral angles between the inter­acting π systems of only [similar, equals] 8°, supporting energetically favourable stacking inter­actions.

Related literature

The title thio­glycoside is a valuable inter­mediate in synthesis of oligosaccharides containing N-acetyl-d-glucosa­mine residues, see: Söderman et al. (2002 [triangle]). For the exo-anomeric effect, see: Thøgersen et al. (1982 [triangle]). For total puckering amplitudes for previously described pyran­osides, see: Färnbäck et al. (2007 [triangle]). For the synthesis, see: Macindoe et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3250-scheme1.jpg

Experimental

Crystal data

  • C30H31NO6S
  • M r = 533.62
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3250-efi1.jpg
  • a = 8.5313 (1) Å
  • b = 14.7728 (2) Å
  • c = 21.1940 (4) Å
  • V = 2671.11 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 100 K
  • 0.25 × 0.10 × 0.05 mm

Data collection

  • Oxford Diffraction Xcalibur II with Sapphire-3 CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.96, T max = 0.98
  • 17362 measured reflections
  • 5059 independent reflections
  • 4023 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.067
  • S = 0.95
  • 5059 reflections
  • 346 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.27 e Å−3
  • Absolute structure: Flack (1983) [triangle], 2173 Friedel pairs
  • Flack parameter: 0.01 (7)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047069/nk2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047069/nk2066Isup2.hkl

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

Acknowledgments

This work was supported by a grant from the Swedish Research Council and by the Faculty of Natural Sciences at Stockholm University

supplementary crystallographic information

Comment

The title thioglycoside is a valuable intermediate in synthesis of oligosaccharides containing N-acetyl-D-glucosamine residues (Söderman et al. 2002). In the structure the least square plane of the N-phthaloyl group makes a dihedral angle of 72.8 (1)° to the sugar ring plane defined by the four atoms (C2,C3,C5,O5). The conformation of the glycosidic torsion angle [var phi] (H1—C1—S1—C7) is govered by the exo-anomeric effect (Thøgersen et al., 1982) and also for this thioglucoside the torsion angles of 47.4° is typical of what is observed for glucosides with an oxygen atom at the glycosidic linkage. The Cremer-Pople parameters for the sugar ring (O5 → C5) are: Q=0.582 (2) Å, θ=12.5 (2)° and [var phi]=310 (1)°. The Q-value is similar to total puckering amplitudes for previously described pyranosides (Färnbäck et al., 2007).

The hydroxy group present in the title compound forms an intermolecular hydrogen bond with O5 in a neighbouring molecule, making up chains along the [100] direction. Besides this conventional hydrogen bond the intermolecular packing is stabilized by interactions between substituents of the sugar rings. There are four close π–π contacts with d(CgCg) < 4.0 Å, all with dihedral angles between the interacting π systems of only ≈ 8° supporting energetically favourable stacking interactions.

Experimental

The title compound (Macindoe et al., 1995) was obtained from ethyl 4,6-O-benzylidene-2-deoxy-N-phtalimido-1-thio-β-D– glucopyranoside by bensylation of O3 and subsequent reductive opening of the 4,6-O-benzylidene group using NaCNBH3 and HCl(g) in tetrahydrofuran to give the 3,6-di-O-benzyl derivative. The title compound was crystallized from diethyl ether/pentane at ambient temperature to give colorless crystals.

Refinement

The hydrogen atoms were positioned in calculated positions and refined in riding mode with C–H = 0.95–1.00 Å, O–H = 0.84 Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C,O) for methyl and hydroxy H atoms. The hydroxy H atom initial position was determined with a tetrahedral C—O—H angle and location such that it forms a favourable hydrogen bond to another oxygen atom. Finally the hydroxy H atoms were allowed to rotate about the C—O bond. The Flack parameter was determined to be 0.01 (7) from 2173 Friedel pairs.

Figures

Fig. 1.
Molecular structure showing 50% probability displacement ellipsoids.

Crystal data

C30H31NO6SF(000) = 1128
Mr = 533.62Dx = 1.327 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6086 reflections
a = 8.5313 (1) Åθ = 3.7–32.3°
b = 14.7728 (2) ŵ = 0.17 mm1
c = 21.1940 (4) ÅT = 100 K
V = 2671.11 (7) Å3Prism, colourless
Z = 40.25 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur II with Sapphire-3 CCD diffractometer5059 independent reflections
Radiation source: Enhance (Mo) X-ray Source4023 reflections with I > 2σ(I)
graphiteRint = 0.054
Detector resolution: 16.5467 pixels mm-1θmax = 25.7°, θmin = 3.7°
ω scans at differnt [var phi]h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −13→18
Tmin = 0.96, Tmax = 0.98l = −25→25
17362 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044w = 1/[σ2(Fo2) + (0.0261P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.067(Δ/σ)max = 0.001
S = 0.95Δρmax = 0.49 e Å3
5059 reflectionsΔρmin = −0.27 e Å3
346 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0028 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2173 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.01 (7)

Special details

Experimental. CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.29.2. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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)

xyzUiso*/Ueq
S10.32681 (7)0.66068 (4)0.88067 (3)0.01942 (15)
C70.3666 (3)0.73807 (17)0.81586 (11)0.0255 (6)
H7A0.32520.71270.77600.031*
H7B0.31420.79680.82370.031*
C80.5419 (3)0.75202 (18)0.81042 (12)0.0301 (6)
H8A0.58220.77710.85000.045*
H8B0.56390.79410.77580.045*
H8C0.59290.69390.80190.045*
C10.1170 (2)0.66968 (15)0.88275 (11)0.0156 (5)
H10.07410.66380.83900.019*
C20.0500 (3)0.59407 (14)0.92453 (10)0.0149 (5)
H20.10980.59460.96510.018*
C3−0.1227 (3)0.60855 (14)0.94058 (11)0.0147 (5)
H3−0.18890.59300.90320.018*
C4−0.1537 (3)0.70604 (14)0.96039 (11)0.0150 (5)
H4−0.10020.71841.00150.018*
C5−0.0901 (3)0.76978 (15)0.91011 (11)0.0153 (5)
H5−0.13690.75400.86830.018*
O50.07730 (18)0.75651 (10)0.90779 (7)0.0171 (4)
C6−0.1223 (3)0.86722 (14)0.92464 (11)0.0195 (6)
H6A−0.23660.87670.92930.023*
H6B−0.07110.88410.96490.023*
N20.0742 (2)0.50558 (12)0.89529 (8)0.0144 (4)
C210.1697 (3)0.43819 (15)0.92183 (11)0.0206 (6)
O220.2428 (2)0.44655 (11)0.97041 (8)0.0297 (4)
C230.1603 (3)0.36067 (14)0.87817 (12)0.0203 (5)
C240.2295 (3)0.27621 (16)0.88227 (12)0.0295 (6)
H240.29660.26080.91640.035*
C250.1966 (3)0.21488 (16)0.83440 (12)0.0315 (7)
H250.24010.15580.83640.038*
C260.1023 (3)0.23773 (16)0.78409 (12)0.0265 (6)
H260.08310.19440.75190.032*
C270.0348 (3)0.32341 (15)0.77964 (11)0.0211 (6)
H27−0.02900.33990.74470.025*
C280.0649 (3)0.38319 (15)0.82828 (11)0.0165 (5)
C290.0087 (3)0.47748 (15)0.83788 (11)0.0152 (5)
O30−0.07326 (19)0.52424 (10)0.80436 (7)0.0210 (4)
O3−0.15948 (18)0.54906 (10)0.99189 (7)0.0198 (4)
C31−0.3063 (3)0.50213 (15)0.98636 (11)0.0223 (6)
H31A−0.38210.54110.96370.027*
H31B−0.34870.49031.02910.027*
C32−0.2895 (3)0.41349 (15)0.95149 (11)0.0223 (6)
C33−0.1825 (3)0.34987 (17)0.97248 (13)0.0380 (7)
H33−0.11690.36281.00760.046*
C34−0.1718 (4)0.26677 (19)0.94180 (16)0.0544 (10)
H34−0.10100.22210.95690.065*
C35−0.2628 (4)0.2490 (2)0.88986 (18)0.0575 (10)
H35−0.25410.19250.86870.069*
C36−0.3653 (4)0.3123 (2)0.86889 (16)0.0570 (10)
H36−0.42770.30030.83270.068*
C37−0.3799 (3)0.3945 (2)0.89988 (13)0.0406 (8)
H37−0.45320.43810.88510.049*
O4−0.31735 (17)0.71949 (11)0.96734 (7)0.0214 (4)
H4A−0.34030.72051.00590.032*
O6−0.06402 (19)0.92258 (10)0.87509 (8)0.0278 (4)
C61−0.1367 (3)1.01026 (15)0.87450 (13)0.0273 (6)
H61A−0.07011.05270.85030.033*
H61B−0.14431.03320.91830.033*
C62−0.2970 (3)1.00801 (15)0.84587 (11)0.0215 (6)
C63−0.4318 (3)0.99598 (14)0.88219 (12)0.0211 (5)
H63−0.42340.99380.92690.025*
C64−0.5772 (3)0.98725 (15)0.85426 (12)0.0274 (6)
H64−0.66700.97670.87970.033*
C65−0.5930 (3)0.99374 (16)0.78969 (12)0.0301 (7)
H65−0.69320.98800.77050.036*
C66−0.4620 (4)1.00867 (17)0.75332 (13)0.0368 (7)
H66−0.47231.01430.70890.044*
C67−0.3158 (3)1.01558 (15)0.78078 (12)0.0305 (7)
H67−0.22661.02570.75490.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0140 (3)0.0220 (3)0.0222 (3)0.0024 (3)0.0021 (3)0.0003 (3)
C70.0210 (16)0.0300 (15)0.0256 (15)−0.0020 (12)0.0010 (11)0.0062 (12)
C80.0232 (16)0.0318 (15)0.0353 (17)−0.0039 (13)0.0063 (12)0.0013 (13)
C10.0131 (12)0.0157 (12)0.0180 (13)0.0045 (10)−0.0022 (10)−0.0044 (11)
C20.0171 (13)0.0156 (13)0.0118 (13)0.0027 (11)−0.0043 (10)−0.0024 (10)
C30.0166 (14)0.0183 (13)0.0091 (13)−0.0013 (10)−0.0003 (10)−0.0001 (10)
C40.0081 (13)0.0219 (13)0.0148 (13)0.0027 (11)−0.0007 (10)−0.0028 (10)
C50.0132 (14)0.0177 (13)0.0151 (13)0.0018 (10)−0.0007 (10)−0.0032 (10)
O50.0155 (9)0.0154 (9)0.0203 (9)0.0016 (7)0.0001 (7)−0.0039 (7)
C60.0176 (14)0.0193 (14)0.0217 (14)0.0040 (11)0.0015 (11)0.0014 (11)
N20.0189 (11)0.0129 (10)0.0114 (10)0.0031 (9)−0.0011 (8)−0.0028 (8)
C210.0265 (15)0.0184 (13)0.0168 (14)0.0034 (13)0.0000 (12)0.0002 (11)
O220.0424 (12)0.0276 (10)0.0190 (10)0.0120 (9)−0.0102 (9)−0.0042 (8)
C230.0293 (14)0.0155 (13)0.0162 (13)0.0038 (11)0.0019 (12)−0.0029 (11)
C240.0447 (17)0.0248 (14)0.0190 (14)0.0126 (13)−0.0043 (14)−0.0001 (13)
C250.0480 (19)0.0146 (13)0.0319 (16)0.0104 (13)0.0022 (14)−0.0001 (12)
C260.0360 (17)0.0201 (15)0.0236 (15)−0.0035 (13)0.0041 (13)−0.0070 (12)
C270.0261 (15)0.0193 (14)0.0180 (14)−0.0025 (12)0.0007 (11)−0.0021 (11)
C280.0211 (14)0.0149 (13)0.0135 (13)0.0005 (11)0.0049 (11)0.0012 (10)
C290.0139 (13)0.0159 (13)0.0159 (13)−0.0005 (10)0.0036 (11)0.0008 (11)
O300.0234 (10)0.0190 (9)0.0205 (10)0.0025 (8)−0.0060 (8)−0.0023 (7)
O30.0218 (9)0.0205 (9)0.0172 (9)−0.0045 (8)0.0014 (7)0.0037 (7)
C310.0197 (14)0.0204 (13)0.0269 (14)−0.0048 (12)0.0062 (11)0.0018 (11)
C320.0269 (16)0.0179 (13)0.0221 (14)−0.0060 (12)0.0077 (12)0.0028 (11)
C330.056 (2)0.0241 (16)0.0342 (17)−0.0014 (15)0.0080 (15)0.0051 (13)
C340.083 (3)0.0226 (17)0.057 (2)0.0080 (18)0.032 (2)0.0126 (16)
C350.075 (3)0.0244 (17)0.073 (3)−0.0148 (17)0.031 (2)−0.0201 (19)
C360.057 (2)0.064 (2)0.051 (2)−0.0161 (19)−0.0022 (18)−0.0312 (19)
C370.0401 (19)0.0418 (18)0.0397 (19)−0.0019 (14)−0.0013 (15)−0.0122 (14)
O40.0150 (9)0.0266 (9)0.0225 (9)0.0008 (8)0.0042 (8)−0.0009 (8)
O60.0289 (10)0.0167 (9)0.0377 (11)0.0066 (8)0.0098 (9)0.0046 (8)
C610.0272 (16)0.0168 (14)0.0378 (17)0.0014 (11)0.0061 (13)0.0024 (12)
C620.0341 (16)0.0085 (12)0.0221 (14)0.0057 (12)0.0075 (12)−0.0010 (10)
C630.0266 (15)0.0178 (13)0.0189 (13)0.0078 (12)0.0016 (13)0.0005 (12)
C640.0289 (16)0.0210 (15)0.0325 (16)0.0097 (13)0.0042 (13)0.0024 (12)
C650.0388 (18)0.0205 (14)0.0311 (16)0.0077 (14)−0.0114 (14)−0.0002 (13)
C660.066 (2)0.0267 (16)0.0182 (15)0.0091 (16)−0.0061 (15)−0.0012 (12)
C670.0456 (19)0.0170 (14)0.0289 (16)0.0037 (14)0.0160 (14)0.0012 (12)

Geometric parameters (Å, °)

S1—C11.796 (2)C26—H260.9500
S1—C71.819 (2)C27—C281.381 (3)
C7—C81.513 (3)C27—H270.9500
C7—H7A0.9900C28—C291.487 (3)
C7—H7B0.9900C29—O301.213 (3)
C8—H8A0.9800O3—C311.436 (3)
C8—H8B0.9800C31—C321.510 (3)
C8—H8C0.9800C31—H31A0.9900
C1—O51.429 (2)C31—H31B0.9900
C1—C21.536 (3)C32—C371.367 (4)
C1—H11.0000C32—C331.383 (3)
C2—N21.462 (3)C33—C341.392 (4)
C2—C31.526 (3)C33—H330.9500
C2—H21.0000C34—C351.373 (5)
C3—O31.433 (3)C34—H340.9500
C3—C41.523 (3)C35—C361.356 (4)
C3—H31.0000C35—H350.9500
C4—O41.417 (2)C36—C371.386 (4)
C4—C51.522 (3)C36—H360.9500
C4—H41.0000C37—H370.9500
C5—O51.442 (3)O4—H4A0.8400
C5—C61.498 (3)O6—C611.436 (3)
C5—H51.0000C61—C621.496 (3)
C6—O61.421 (3)C61—H61A0.9900
C6—H6A0.9900C61—H61B0.9900
C6—H6B0.9900C62—C671.393 (3)
N2—C291.402 (3)C62—C631.395 (3)
N2—C211.404 (3)C63—C641.381 (3)
C21—O221.210 (3)C63—H630.9500
C21—C231.474 (3)C64—C651.378 (3)
C23—C281.376 (3)C64—H640.9500
C23—C241.383 (3)C65—C661.376 (4)
C24—C251.389 (3)C65—H650.9500
C24—H240.9500C66—C671.380 (4)
C25—C261.377 (3)C66—H660.9500
C25—H250.9500C67—H670.9500
C26—C271.394 (3)
C1—S1—C799.10 (11)C24—C25—H25119.2
C8—C7—S1109.13 (17)C25—C26—C27121.1 (2)
C8—C7—H7A109.9C25—C26—H26119.5
S1—C7—H7A109.9C27—C26—H26119.5
C8—C7—H7B109.9C28—C27—C26117.0 (2)
S1—C7—H7B109.9C28—C27—H27121.5
H7A—C7—H7B108.3C26—C27—H27121.5
C7—C8—H8A109.5C23—C28—C27121.9 (2)
C7—C8—H8B109.5C23—C28—C29108.2 (2)
H8A—C8—H8B109.5C27—C28—C29129.9 (2)
C7—C8—H8C109.5O30—C29—N2124.7 (2)
H8A—C8—H8C109.5O30—C29—C28129.7 (2)
H8B—C8—H8C109.5N2—C29—C28105.5 (2)
O5—C1—C2110.52 (17)C3—O3—C31115.16 (17)
O5—C1—S1108.16 (14)O3—C31—C32112.04 (18)
C2—C1—S1109.35 (15)O3—C31—H31A109.2
O5—C1—H1109.6C32—C31—H31A109.2
C2—C1—H1109.6O3—C31—H31B109.2
S1—C1—H1109.6C32—C31—H31B109.2
N2—C2—C3110.89 (18)H31A—C31—H31B107.9
N2—C2—C1110.68 (18)C37—C32—C33119.4 (2)
C3—C2—C1112.68 (17)C37—C32—C31121.0 (2)
N2—C2—H2107.4C33—C32—C31119.6 (2)
C3—C2—H2107.4C32—C33—C34119.5 (3)
C1—C2—H2107.4C32—C33—H33120.3
O3—C3—C4109.41 (17)C34—C33—H33120.3
O3—C3—C2107.13 (17)C35—C34—C33120.4 (3)
C4—C3—C2111.22 (18)C35—C34—H34119.8
O3—C3—H3109.7C33—C34—H34119.8
C4—C3—H3109.7C36—C35—C34119.7 (3)
C2—C3—H3109.7C36—C35—H35120.1
O4—C4—C5109.72 (18)C34—C35—H35120.1
O4—C4—C3109.43 (18)C35—C36—C37120.5 (3)
C5—C4—C3109.25 (17)C35—C36—H36119.8
O4—C4—H4109.5C37—C36—H36119.8
C5—C4—H4109.5C32—C37—C36120.5 (3)
C3—C4—H4109.5C32—C37—H37119.7
O5—C5—C6108.63 (19)C36—C37—H37119.7
O5—C5—C4107.04 (18)C4—O4—H4A109.5
C6—C5—C4112.65 (18)C6—O6—C61111.98 (18)
O5—C5—H5109.5O6—C61—C62112.21 (19)
C6—C5—H5109.5O6—C61—H61A109.2
C4—C5—H5109.5C62—C61—H61A109.2
C1—O5—C5111.66 (16)O6—C61—H61B109.2
O6—C6—C5109.69 (18)C62—C61—H61B109.2
O6—C6—H6A109.7H61A—C61—H61B107.9
C5—C6—H6A109.7C67—C62—C63117.5 (2)
O6—C6—H6B109.7C67—C62—C61120.4 (2)
C5—C6—H6B109.7C63—C62—C61122.2 (2)
H6A—C6—H6B108.2C64—C63—C62121.1 (2)
C29—N2—C21111.67 (18)C64—C63—H63119.5
C29—N2—C2125.19 (18)C62—C63—H63119.5
C21—N2—C2123.14 (18)C65—C64—C63120.5 (3)
O22—C21—N2124.6 (2)C65—C64—H64119.8
O22—C21—C23129.9 (2)C63—C64—H64119.8
N2—C21—C23105.5 (2)C66—C65—C64119.2 (3)
C28—C23—C24121.3 (2)C66—C65—H65120.4
C28—C23—C21109.05 (19)C64—C65—H65120.4
C24—C23—C21129.7 (2)C65—C66—C67120.7 (2)
C23—C24—C25117.2 (2)C65—C66—H66119.7
C23—C24—H24121.4C67—C66—H66119.7
C25—C24—H24121.4C66—C67—C62121.1 (2)
C26—C25—C24121.6 (2)C66—C67—H67119.5
C26—C25—H25119.2C62—C67—H67119.5
C7—S1—C1—H147.4C24—C25—C26—C27−0.6 (4)
C1—S1—C7—C8172.39 (18)C25—C26—C27—C28−1.0 (4)
C7—S1—C1—O5−72.06 (17)C24—C23—C28—C27−0.8 (4)
C7—S1—C1—C2167.52 (16)C21—C23—C28—C27179.8 (2)
O5—C1—C2—N2173.35 (17)C24—C23—C28—C29179.6 (2)
S1—C1—C2—N2−67.7 (2)C21—C23—C28—C290.2 (3)
O5—C1—C2—C348.5 (2)C26—C27—C28—C231.7 (4)
S1—C1—C2—C3167.49 (15)C26—C27—C28—C29−178.8 (2)
N2—C2—C3—O370.3 (2)C21—N2—C29—O30−177.1 (2)
C1—C2—C3—O3−164.98 (17)C2—N2—C29—O302.2 (3)
N2—C2—C3—C4−170.16 (17)C21—N2—C29—C281.4 (2)
C1—C2—C3—C4−45.5 (2)C2—N2—C29—C28−179.31 (19)
O3—C3—C4—O4−69.0 (2)C23—C28—C29—O30177.4 (2)
C2—C3—C4—O4172.88 (17)C27—C28—C29—O30−2.1 (4)
O3—C3—C4—C5170.90 (17)C23—C28—C29—N2−1.0 (2)
C2—C3—C4—C552.7 (2)C27—C28—C29—N2179.5 (2)
O4—C4—C5—O5176.83 (17)C4—C3—O3—C31102.6 (2)
C3—C4—C5—O5−63.2 (2)C2—C3—O3—C31−136.77 (18)
O4—C4—C5—C657.5 (2)C3—O3—C31—C3288.6 (2)
C3—C4—C5—C6177.45 (19)O3—C31—C32—C37−125.6 (3)
C2—C1—O5—C5−61.2 (2)O3—C31—C32—C3355.3 (3)
S1—C1—O5—C5179.08 (15)C37—C32—C33—C34−1.8 (4)
C6—C5—O5—C1−169.14 (17)C31—C32—C33—C34177.4 (2)
C4—C5—O5—C169.0 (2)C32—C33—C34—C352.1 (4)
O5—C5—C6—O663.3 (2)C33—C34—C35—C36−0.9 (5)
C4—C5—C6—O6−178.31 (19)C34—C35—C36—C37−0.6 (5)
C3—C2—N2—C2962.2 (3)C33—C32—C37—C360.3 (4)
C1—C2—N2—C29−63.6 (3)C31—C32—C37—C36−178.9 (3)
C3—C2—N2—C21−118.6 (2)C35—C36—C37—C320.9 (5)
C1—C2—N2—C21115.6 (2)C5—C6—O6—C61159.61 (19)
C29—N2—C21—O22178.0 (2)C6—O6—C61—C62−78.3 (3)
C2—N2—C21—O22−1.3 (4)O6—C61—C62—C67−85.7 (3)
C29—N2—C21—C23−1.3 (3)O6—C61—C62—C6392.6 (3)
C2—N2—C21—C23179.4 (2)C67—C62—C63—C643.3 (3)
O22—C21—C23—C28−178.6 (3)C61—C62—C63—C64−175.0 (2)
N2—C21—C23—C280.7 (3)C62—C63—C64—C65−2.5 (3)
O22—C21—C23—C242.1 (5)C63—C64—C65—C660.3 (4)
N2—C21—C23—C24−178.7 (2)C64—C65—C66—C671.1 (4)
C28—C23—C24—C25−0.9 (4)C65—C66—C67—C62−0.3 (4)
C21—C23—C24—C25178.4 (3)C63—C62—C67—C66−1.9 (3)
C23—C24—C25—C261.6 (4)C61—C62—C67—C66176.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···O5i0.841.992.817 (2)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2066).

References

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