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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1012.
Published online 2008 May 7. doi:  10.1107/S1600536808012567
PMCID: PMC2961596

2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone

Abstract

X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzyl­idene-d-xylono-1,4-lactone with diphenyl­diazo­methane proceeded smoothly to give the title compound, C25H22O5, with no accompanying epimerization. Unlike the analogously protected lyxono lactone, the isomeric xylono lactone has two mol­ecules present in the asymmetric unit (Z′ = 2). The 5-ring lactones adopt envelope conformations and the 6-ring ketals adopt chair conformations.

Related literature

For related literature, see: Collins & Ferrier (1995 [triangle]); Draths et al. (1992 [triangle]); Jackson et al. (1982 [triangle]); Petursson & Webber (1982 [triangle]); Petursson et al. (2007 [triangle]); Petursson (2001 [triangle], 2003 [triangle]); Best et al. (2008 [triangle]); Jenkinson et al. (2008 [triangle]); Görbitz (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1012-scheme1.jpg

Experimental

Crystal data

  • C25H22O5
  • M r = 402.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1012-efi1.jpg
  • a = 14.8159 (3) Å
  • b = 9.1959 (2) Å
  • c = 15.0797 (2) Å
  • β = 93.7245 (12)°
  • V = 2050.20 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 150 K
  • 0.80 × 0.30 × 0.10 mm

Data collection

  • Nonius KappaCCD area-detector diffractometer
  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.55, T max = 0.99
  • 25081 measured reflections
  • 4938 independent reflections
  • 3950 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.101
  • S = 0.89
  • 4938 reflections
  • 542 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 2001 [triangle]).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 [triangle]); molecular graphics: CAMERON (Watkin et al., 1996 [triangle]); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012567/lh2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012567/lh2623Isup2.hkl

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

supplementary crystallographic information

Comment

Carbohydrates provide excellent starting materials for the synthesis of small chiral molecules (Collins & Ferrier, 1995). They are relatively inexpensive and provide an almost boundless pool of chiral building blocks (Draths et al., 1992). Much of their synthetic utility is however dependent on developing successful protecting group strategies.

Diazodiphenylmethane has been found to be a useful protecting group in the synthesis of methyl 2,3,6-tri-O-methyl-α-D-glucopyranoside and kojibiose octa-acetate (Jackson et al., 1982); monoalkylations of vicinal diols have been achieved with this reagent and other diaryldiazoalkanes with high regioselectivities (Petursson & Webber, 1982; Petursson et al., 2007; Petursson, 2003; Petursson, 2001). This is of particular interest for the protection of base sensitive sugar lactones as the reaction is carried out under neutral conditions (Best et al. 2008; Jenkinson et al. 2008).

The utility of the benzhydryl group as a protecting group in carbohydrate chemistry has here been demonstrated with the reaction of 3,5-O-benzylidene-D-xylono-1,4-lactone 1 with diphenyldiazomethane (Fig. 1). No epimerization at C2 was observed (Fig. 2).

Unlike the analogously protected lyxono lactone (Jenkinson et al., 2008), the asymmetric unit of the isomeric xylono lactone contains two crystallographically distinct molecules which are related by a pseudo 2-fold axis of symmetry. These are similar in geometry with the exception of two of the phenyl rings which sit at approximately 90° to each other (Fig. 3). When the core 20 atoms, of the carbohydrate backbone and 1 phenyl group, are mapped there is good overlap- r.m.s. deviations: posn 0.1139 Å, bond 0.0104 Å, torsion 2.5205°.

The crystal packing shows alternating layers of molecules in the ac plane (Fig. 4). The 5-ring lactones adopt envelope conformations with C2 or C102 out of the plane. The 6-ring ketals adopt chair conformations. There is no classic hydrogen-bonding.

Experimental

The title lactone was recrystallized from a 1:1 mixture of ethyl acetate and cyclohexane: m.p. 395–397 K; [α]D23 +129.1 (c, 1.02 in CHCl3).

Refinement

In the absence of significant anomalous scattering, Friedel pairs were merged and the absolute configuration was assigned from the starting material.

The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:1.80) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Figures

Fig. 1.
Synthetic Scheme.
Fig. 2.
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. There are two molecules in the asymmetric repeating unit.
Fig. 3.
Overlay of the two molecules in the asymmetric unit.
Fig. 4.
Packing diagram for the molecule projected along the b-axis.

Crystal data

C25H22O5F000 = 848
Mr = 402.45Dx = 1.304 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4834 reflections
a = 14.8159 (3) Åθ = 5–27º
b = 9.1959 (2) ŵ = 0.09 mm1
c = 15.0797 (2) ÅT = 150 K
β = 93.7245 (12)ºPlate, colourless
V = 2050.20 (7) Å30.80 × 0.30 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer3950 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 150 Kθmax = 27.5º
ω scansθmin = 5.2º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)h = −19→19
Tmin = 0.55, Tmax = 0.99k = −11→11
25081 measured reflectionsl = −19→19
4938 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034  Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 16.9 24.9 12.6 3.46
wR(F2) = 0.101(Δ/σ)max = 0.0003
S = 0.89Δρmax = 0.25 e Å3
4938 reflectionsΔρmin = −0.27 e Å3
542 parametersExtinction correction: Larson (1970), Equation 22
1 restraintExtinction coefficient: 600 (50)
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.44166 (10)0.5327 (2)0.31715 (10)0.0244
C20.40499 (15)0.5336 (3)0.22694 (15)0.0242
C30.30725 (16)0.4866 (3)0.23203 (15)0.0254
O40.25857 (10)0.5219 (2)0.15093 (10)0.0265
C50.16129 (15)0.5192 (3)0.15751 (16)0.0257
C60.13142 (16)0.6490 (3)0.21052 (15)0.0252
C70.17991 (18)0.7781 (3)0.21395 (18)0.0330
C80.1517 (2)0.8947 (3)0.26476 (19)0.0403
C90.0760 (2)0.8806 (3)0.31222 (18)0.0432
C100.0264 (2)0.7539 (4)0.30826 (19)0.0437
C110.05367 (19)0.6375 (3)0.25762 (17)0.0335
C120.12135 (15)0.5140 (3)0.06274 (15)0.0255
C130.15139 (19)0.6107 (3)0.00038 (17)0.0339
C140.1185 (2)0.6028 (4)−0.08784 (18)0.0429
C150.0551 (2)0.4987 (4)−0.11333 (19)0.0486
C160.02472 (19)0.4030 (4)−0.0519 (2)0.0479
C170.05739 (17)0.4106 (4)0.03651 (19)0.0368
C180.31556 (18)0.3212 (3)0.23435 (18)0.0323
O190.26098 (14)0.2338 (2)0.25627 (16)0.0478
O200.39494 (13)0.2813 (2)0.20131 (13)0.0344
C210.44429 (17)0.4094 (3)0.17435 (16)0.0296
C220.54422 (17)0.3886 (3)0.19447 (16)0.0335
O230.56825 (11)0.3965 (2)0.28758 (11)0.0301
C240.53776 (15)0.5268 (3)0.32352 (15)0.0255
C250.56837 (16)0.5320 (3)0.42104 (16)0.0277
C260.53029 (17)0.6335 (3)0.47592 (17)0.0318
C270.5559 (2)0.6362 (4)0.56635 (19)0.0417
C280.6204 (2)0.5396 (4)0.6014 (2)0.0479
C290.6607 (2)0.4425 (4)0.5464 (2)0.0479
C300.63432 (19)0.4375 (3)0.45597 (19)0.0359
O1010.17514 (11)0.3628 (2)0.56763 (10)0.0280
C1020.26545 (16)0.3497 (3)0.60615 (15)0.0265
C1030.26225 (16)0.3956 (3)0.70212 (16)0.0266
O1040.34196 (11)0.3412 (2)0.74916 (10)0.0274
C1050.33862 (16)0.3463 (3)0.84483 (15)0.0254
C1060.27885 (16)0.2264 (3)0.87746 (17)0.0275
C1070.25628 (19)0.1047 (3)0.82618 (19)0.0368
C1080.2043 (2)−0.0056 (4)0.8592 (2)0.0473
C1090.17436 (19)0.0054 (4)0.9435 (3)0.0506
C1100.1966 (2)0.1261 (4)0.9956 (2)0.0512
C1110.2483 (2)0.2372 (4)0.9627 (2)0.0394
C1120.43660 (16)0.3392 (3)0.88150 (15)0.0254
C1130.49799 (18)0.4396 (3)0.85136 (18)0.0320
C1140.58750 (19)0.4422 (3)0.8863 (2)0.0383
C1150.61626 (18)0.3427 (3)0.95059 (18)0.0348
C1160.55682 (18)0.2406 (3)0.97998 (16)0.0318
C1170.46694 (17)0.2387 (3)0.94582 (15)0.0276
C1180.27224 (17)0.5609 (3)0.69587 (17)0.0307
O1190.25584 (16)0.6510 (3)0.75019 (14)0.0446
O1200.30885 (13)0.5960 (2)0.61933 (12)0.0333
C1210.32735 (16)0.4648 (3)0.56966 (16)0.0299
C1220.30971 (17)0.4926 (4)0.47132 (17)0.0357
O1230.21497 (11)0.4979 (2)0.44632 (11)0.0315
C1240.17243 (16)0.3695 (3)0.47308 (15)0.0280
C1250.07503 (16)0.3717 (3)0.43830 (16)0.0286
C1260.01418 (18)0.4674 (3)0.47230 (17)0.0354
C127−0.07582 (19)0.4661 (4)0.44074 (19)0.0426
C128−0.10512 (19)0.3684 (4)0.3750 (2)0.0417
C129−0.0444 (2)0.2749 (4)0.3393 (2)0.0412
C1300.0462 (2)0.2761 (3)0.37099 (18)0.0344
H210.41020.63080.19800.0310*
H310.28150.52920.28380.0300*
H510.14610.42850.19120.0293*
H710.23320.78970.17930.0378*
H810.18540.98280.26570.0498*
H910.05740.95860.34620.0522*
H101−0.02700.74560.34170.0499*
H1110.01930.55070.25590.0398*
H1310.19440.68310.01550.0428*
H1410.14170.6660−0.13050.0511*
H1510.02930.4918−0.17220.0598*
H161−0.01950.3290−0.06680.0570*
H1710.03840.34460.07680.0465*
H2110.43120.42570.10740.0355*
H2210.57800.46290.15870.0427*
H2220.56170.28960.17660.0439*
H2410.56270.61050.29090.0328*
H2610.48460.70130.45430.0393*
H2710.52980.70650.60430.0510*
H2810.63720.54190.66400.0566*
H2910.70870.37650.57040.0512*
H3010.66220.36860.41990.0430*
H10210.29090.25130.59390.0322*
H10310.20660.36710.73080.0308*
H10510.31310.44490.85890.0297*
H10710.27550.09770.76830.0447*
H10810.1886−0.09040.82410.0582*
H10910.1414−0.06920.96760.0609*
H11010.17770.13341.05310.0637*
H11110.26190.32110.99670.0452*
H11310.47900.50640.80200.0373*
H11410.62880.51140.86310.0459*
H11510.67690.34370.97450.0399*
H11610.57880.16941.02260.0391*
H11710.42230.16780.96520.0343*
H12110.39140.43810.58510.0389*
H12210.33780.58730.45630.0426*
H12220.33940.41380.43830.0433*
H12410.20310.28340.45060.0363*
H12610.03400.53260.51870.0406*
H1271−0.11840.53050.46600.0513*
H1281−0.16770.36700.35520.0470*
H1291−0.06490.21010.29290.0471*
H13010.08950.21050.34570.0399*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0232 (7)0.0288 (9)0.0210 (7)−0.0002 (7)0.0005 (6)−0.0019 (7)
C20.0265 (11)0.0255 (12)0.0202 (10)0.0009 (9)−0.0007 (8)0.0009 (9)
C30.0275 (11)0.0277 (13)0.0209 (10)−0.0006 (10)−0.0001 (8)0.0048 (10)
O40.0243 (8)0.0340 (10)0.0209 (7)0.0030 (7)−0.0011 (6)0.0044 (7)
C50.0245 (11)0.0251 (12)0.0276 (11)−0.0001 (10)0.0017 (8)0.0027 (10)
C60.0300 (11)0.0240 (11)0.0211 (10)0.0031 (10)−0.0022 (8)0.0024 (9)
C70.0352 (13)0.0288 (13)0.0346 (13)−0.0016 (11)−0.0004 (10)−0.0027 (11)
C80.0518 (16)0.0289 (14)0.0387 (14)−0.0017 (13)−0.0081 (12)−0.0037 (12)
C90.0659 (19)0.0334 (16)0.0298 (13)0.0140 (15)0.0001 (12)−0.0040 (12)
C100.0570 (18)0.0398 (17)0.0361 (15)0.0146 (14)0.0169 (13)0.0055 (13)
C110.0390 (13)0.0283 (13)0.0341 (13)0.0044 (11)0.0094 (10)0.0046 (11)
C120.0239 (10)0.0255 (12)0.0269 (11)0.0055 (9)−0.0005 (8)−0.0051 (10)
C130.0413 (14)0.0298 (14)0.0296 (12)−0.0048 (11)−0.0048 (10)−0.0012 (11)
C140.0528 (17)0.0505 (18)0.0244 (13)0.0027 (15)−0.0041 (11)0.0001 (13)
C150.0420 (15)0.072 (2)0.0303 (13)0.0034 (16)−0.0085 (11)−0.0144 (16)
C160.0305 (13)0.066 (2)0.0468 (16)−0.0103 (15)−0.0029 (11)−0.0195 (17)
C170.0269 (12)0.0416 (16)0.0422 (14)−0.0072 (12)0.0034 (10)−0.0072 (13)
C180.0321 (13)0.0315 (14)0.0318 (13)−0.0024 (11)−0.0098 (10)0.0067 (11)
O190.0394 (11)0.0384 (12)0.0638 (14)−0.0101 (10)−0.0106 (10)0.0201 (11)
O200.0399 (10)0.0248 (9)0.0376 (10)0.0003 (8)−0.0035 (8)−0.0012 (8)
C210.0357 (12)0.0308 (13)0.0223 (10)0.0026 (11)0.0027 (9)−0.0005 (10)
C220.0373 (13)0.0370 (14)0.0267 (12)0.0071 (12)0.0052 (10)−0.0038 (11)
O230.0300 (8)0.0340 (10)0.0264 (8)0.0074 (8)0.0021 (6)−0.0025 (8)
C240.0224 (10)0.0262 (12)0.0282 (11)0.0001 (10)0.0032 (8)−0.0014 (10)
C250.0245 (11)0.0280 (12)0.0303 (12)−0.0073 (10)−0.0004 (9)−0.0015 (10)
C260.0289 (12)0.0327 (14)0.0336 (13)−0.0030 (11)0.0009 (9)−0.0074 (11)
C270.0428 (15)0.0469 (18)0.0350 (14)−0.0127 (14)−0.0017 (11)−0.0100 (14)
C280.0585 (19)0.0486 (18)0.0344 (14)−0.0137 (16)−0.0135 (13)−0.0068 (14)
C290.0542 (18)0.0407 (18)0.0456 (17)0.0004 (15)−0.0219 (14)−0.0023 (14)
C300.0372 (13)0.0318 (14)0.0373 (14)0.0023 (11)−0.0080 (11)−0.0043 (12)
O1010.0258 (8)0.0354 (10)0.0223 (8)−0.0028 (7)−0.0020 (6)0.0045 (7)
C1020.0243 (11)0.0282 (12)0.0268 (11)0.0022 (10)−0.0011 (8)0.0006 (10)
C1030.0230 (10)0.0315 (13)0.0249 (11)0.0045 (10)0.0002 (8)0.0039 (10)
O1040.0251 (8)0.0349 (10)0.0219 (8)0.0045 (7)−0.0009 (6)0.0021 (7)
C1050.0276 (11)0.0253 (12)0.0234 (10)0.0012 (10)0.0017 (8)0.0004 (10)
C1060.0224 (11)0.0293 (13)0.0309 (12)0.0040 (10)0.0017 (9)0.0040 (10)
C1070.0379 (14)0.0348 (15)0.0367 (14)−0.0038 (12)−0.0050 (11)0.0054 (12)
C1080.0436 (16)0.0373 (17)0.0591 (19)−0.0105 (14)−0.0108 (13)0.0091 (15)
C1090.0315 (14)0.0453 (19)0.075 (2)0.0004 (13)0.0064 (14)0.0245 (18)
C1100.0442 (17)0.052 (2)0.060 (2)0.0125 (16)0.0272 (15)0.0164 (17)
C1110.0377 (14)0.0385 (16)0.0435 (15)0.0096 (13)0.0152 (12)0.0036 (13)
C1120.0268 (11)0.0262 (12)0.0230 (10)0.0003 (10)0.0003 (8)−0.0033 (9)
C1130.0333 (12)0.0267 (13)0.0356 (13)−0.0018 (10)−0.0012 (10)0.0016 (11)
C1140.0342 (14)0.0329 (15)0.0473 (15)−0.0060 (12)−0.0002 (11)−0.0029 (13)
C1150.0284 (12)0.0387 (15)0.0363 (13)0.0009 (11)−0.0051 (10)−0.0111 (12)
C1160.0329 (13)0.0377 (15)0.0239 (11)0.0081 (11)−0.0051 (9)−0.0038 (11)
C1170.0307 (12)0.0303 (13)0.0215 (10)0.0026 (10)0.0008 (9)−0.0010 (10)
C1180.0294 (12)0.0332 (14)0.0291 (12)0.0039 (10)−0.0005 (9)0.0015 (11)
O1190.0597 (13)0.0362 (11)0.0382 (10)0.0110 (10)0.0052 (9)−0.0041 (10)
O1200.0381 (10)0.0317 (10)0.0304 (9)−0.0055 (8)0.0030 (7)0.0035 (8)
C1210.0255 (11)0.0375 (14)0.0268 (11)−0.0026 (11)0.0028 (9)−0.0006 (11)
C1220.0268 (12)0.0527 (18)0.0278 (12)−0.0056 (12)0.0041 (9)0.0032 (13)
O1230.0274 (8)0.0407 (11)0.0264 (8)−0.0048 (8)0.0019 (6)0.0068 (8)
C1240.0308 (11)0.0300 (13)0.0231 (11)−0.0002 (10)0.0019 (9)0.0024 (10)
C1250.0297 (12)0.0313 (13)0.0247 (11)−0.0025 (10)0.0010 (9)0.0040 (10)
C1260.0334 (13)0.0430 (16)0.0294 (12)0.0014 (12)−0.0004 (10)−0.0060 (12)
C1270.0342 (13)0.0577 (19)0.0359 (14)0.0035 (14)0.0024 (11)0.0010 (14)
C1280.0325 (13)0.0510 (19)0.0407 (14)−0.0064 (13)−0.0058 (11)0.0092 (14)
C1290.0456 (16)0.0385 (16)0.0380 (14)−0.0092 (13)−0.0091 (12)−0.0012 (13)
C1300.0420 (14)0.0284 (13)0.0319 (13)−0.0018 (12)−0.0050 (11)−0.0005 (11)

Geometric parameters (Å, °)

O1—C21.432 (3)O101—C1021.429 (3)
O1—C241.422 (3)O101—C1241.425 (3)
C2—C31.518 (3)C102—C1031.511 (3)
C2—C211.527 (4)C102—C1211.526 (4)
C2—H211.000C102—H10211.002
C3—O41.416 (3)C103—O1041.428 (3)
C3—C181.526 (4)C103—C1181.531 (4)
C3—H310.973C103—H10310.991
O4—C51.451 (3)O104—C1051.448 (3)
C5—C61.518 (3)C105—C1061.516 (3)
C5—C121.512 (3)C105—C1121.521 (3)
C5—H511.009C105—H10511.011
C6—C71.387 (4)C106—C1071.388 (4)
C6—C111.396 (3)C106—C1111.393 (4)
C7—C81.398 (4)C107—C1081.385 (4)
C7—H710.980C107—H10710.938
C8—C91.374 (4)C108—C1091.377 (5)
C8—H810.952C108—H10810.963
C9—C101.377 (5)C109—C1101.387 (5)
C9—H910.933C109—H10910.930
C10—C111.390 (4)C110—C1111.388 (5)
C10—H1010.969C110—H11010.932
C11—H1110.947C111—H11110.941
C12—C131.388 (4)C112—C1131.393 (4)
C12—C171.382 (4)C112—C1171.393 (3)
C13—C141.389 (4)C113—C1141.395 (4)
C13—H1310.939C113—H11310.991
C14—C151.378 (5)C114—C1151.381 (4)
C14—H1410.948C114—H11410.964
C15—C161.374 (5)C115—C1161.380 (4)
C15—H1510.946C115—H11510.946
C16—C171.390 (4)C116—C1171.396 (3)
C16—H1610.961C116—H11610.960
C17—H1710.916C117—H11710.986
C18—O191.202 (3)C118—O1191.201 (3)
C18—O201.357 (3)C118—O1201.346 (3)
O20—C211.458 (3)O120—C1211.456 (3)
C21—C221.504 (4)C121—C1221.511 (3)
C21—H2111.026C121—H12110.994
C22—O231.428 (3)C122—O1231.430 (3)
C22—H2211.021C122—H12210.998
C22—H2220.989C122—H12220.998
O23—C241.402 (3)O123—C1241.409 (3)
C24—C251.511 (3)C124—C1251.503 (3)
C24—H2410.997C124—H12410.984
C25—C261.392 (4)C125—C1261.382 (4)
C25—C301.385 (4)C125—C1301.389 (4)
C26—C271.392 (4)C126—C1271.387 (4)
C26—H2610.961C126—H12610.953
C27—C281.385 (5)C127—C1281.386 (5)
C27—H2710.961C127—H12710.962
C28—C291.380 (5)C128—C1291.379 (5)
C28—H2810.962C128—H12810.955
C29—C301.394 (4)C129—C1301.394 (4)
C29—H2910.986C129—H12910.954
C30—H3010.948C130—H13010.977
C2—O1—C24112.39 (17)C102—O101—C124112.03 (17)
O1—C2—C3104.75 (18)O101—C102—C103106.20 (18)
O1—C2—C21110.80 (19)O101—C102—C121111.3 (2)
C3—C2—C21102.2 (2)C103—C102—C121102.0 (2)
O1—C2—H21112.6O101—C102—H1021110.8
C3—C2—H21112.2C103—C102—H1021117.7
C21—C2—H21113.5C121—C102—H1021108.5
C2—C3—O4108.98 (18)C102—C103—O104107.53 (19)
C2—C3—C18102.1 (2)C102—C103—C118102.1 (2)
O4—C3—C18106.5 (2)O104—C103—C118107.4 (2)
C2—C3—H31110.6C102—C103—H1031115.0
O4—C3—H31113.3O104—C103—H1031112.1
C18—C3—H31114.7C118—C103—H1031112.1
C3—O4—C5112.91 (17)C103—O104—C105113.76 (17)
O4—C5—C6110.32 (19)O104—C105—C106111.0 (2)
O4—C5—C12105.39 (18)O104—C105—C112105.51 (17)
C6—C5—C12114.4 (2)C106—C105—C112114.5 (2)
O4—C5—H51107.6O104—C105—H1051106.0
C6—C5—H51107.6C106—C105—H1051110.5
C12—C5—H51111.3C112—C105—H1051108.9
C5—C6—C7121.7 (2)C105—C106—C107122.0 (2)
C5—C6—C11119.1 (2)C105—C106—C111118.6 (2)
C7—C6—C11119.2 (2)C107—C106—C111119.4 (3)
C6—C7—C8120.3 (3)C106—C107—C108120.6 (3)
C6—C7—H71120.5C106—C107—H1071119.8
C8—C7—H71119.2C108—C107—H1071119.6
C7—C8—C9119.7 (3)C107—C108—C109119.9 (3)
C7—C8—H81119.1C107—C108—H1081121.1
C9—C8—H81121.2C109—C108—H1081119.0
C8—C9—C10120.6 (3)C108—C109—C110120.1 (3)
C8—C9—H91119.5C108—C109—H1091121.1
C10—C9—H91119.9C110—C109—H1091118.7
C9—C10—C11120.1 (3)C109—C110—C111120.2 (3)
C9—C10—H101119.7C109—C110—H1101120.7
C11—C10—H101120.1C111—C110—H1101119.1
C6—C11—C10120.0 (3)C106—C111—C110119.8 (3)
C6—C11—H111120.7C106—C111—H1111119.4
C10—C11—H111119.3C110—C111—H1111120.8
C5—C12—C13119.8 (2)C105—C112—C113118.8 (2)
C5—C12—C17120.8 (2)C105—C112—C117122.6 (2)
C13—C12—C17119.4 (2)C113—C112—C117118.6 (2)
C12—C13—C14120.5 (3)C112—C113—C114120.9 (3)
C12—C13—H131122.2C112—C113—H1131119.8
C14—C13—H131117.3C114—C113—H1131119.2
C13—C14—C15119.6 (3)C113—C114—C115119.7 (3)
C13—C14—H141119.9C113—C114—H1141119.0
C15—C14—H141120.5C115—C114—H1141121.2
C14—C15—C16120.3 (3)C114—C115—C116120.1 (2)
C14—C15—H151122.4C114—C115—H1151120.3
C16—C15—H151117.4C116—C115—H1151119.6
C15—C16—C17120.4 (3)C115—C116—C117120.2 (2)
C15—C16—H161122.9C115—C116—H1161118.9
C17—C16—H161116.7C117—C116—H1161120.8
C16—C17—C12119.9 (3)C116—C117—C112120.3 (2)
C16—C17—H171120.0C116—C117—H1171122.7
C12—C17—H171120.0C112—C117—H1171116.9
C3—C18—O19128.2 (3)C103—C118—O119128.2 (3)
C3—C18—O20109.4 (2)C103—C118—O120109.7 (2)
O19—C18—O20122.3 (3)O119—C118—O120122.0 (3)
C18—O20—C21110.2 (2)C118—O120—C121110.0 (2)
C2—C21—O20104.14 (18)C102—C121—O120104.57 (19)
C2—C21—C22113.2 (2)C102—C121—C122113.7 (2)
O20—C21—C22110.3 (2)O120—C121—C122109.8 (2)
C2—C21—H211110.3C102—C121—H1211109.4
O20—C21—H211109.0O120—C121—H1211107.1
C22—C21—H211109.7C122—C121—H1211111.9
C21—C22—O23111.80 (19)C121—C122—O123111.63 (19)
C21—C22—H221108.5C121—C122—H1221108.8
O23—C22—H221112.7O123—C122—H1221109.1
C21—C22—H222109.5C121—C122—H1222108.2
O23—C22—H222105.2O123—C122—H1222110.5
H221—C22—H222109.0H1221—C122—H1222108.5
C22—O23—C24110.9 (2)C122—O123—C124110.2 (2)
O1—C24—O23110.67 (19)O101—C124—O123109.8 (2)
O1—C24—C25107.49 (18)O101—C124—C125108.28 (18)
O23—C24—C25108.6 (2)O123—C124—C125109.0 (2)
O1—C24—H241109.8O101—C124—H1241109.1
O23—C24—H241109.3O123—C124—H1241110.5
C25—C24—H241111.0C125—C124—H1241110.2
C24—C25—C26119.5 (2)C124—C125—C126120.9 (2)
C24—C25—C30120.7 (2)C124—C125—C130119.3 (2)
C26—C25—C30119.9 (2)C126—C125—C130119.8 (2)
C25—C26—C27120.0 (3)C125—C126—C127120.2 (3)
C25—C26—H261122.5C125—C126—H1261119.7
C27—C26—H261117.5C127—C126—H1261120.0
C26—C27—C28120.0 (3)C126—C127—C128120.0 (3)
C26—C27—H271120.1C126—C127—H1271119.9
C28—C27—H271119.9C128—C127—H1271120.0
C27—C28—C29120.0 (3)C127—C128—C129120.1 (3)
C27—C28—H281119.3C127—C128—H1281119.0
C29—C28—H281120.7C129—C128—H1281121.0
C28—C29—C30120.3 (3)C128—C129—C130120.0 (3)
C28—C29—H291120.5C128—C129—H1291119.4
C30—C29—H291119.2C130—C129—H1291120.7
C29—C30—C25119.8 (3)C129—C130—C125119.9 (3)
C29—C30—H301118.6C129—C130—H1301120.3
C25—C30—H301121.6C125—C130—H1301119.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H81···O19i0.952.573.520 (4)173
C14—H141···O119ii0.952.553.309 (4)137
C28—H281···O19iii0.962.573.225 (4)126

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2623).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Best, D., Jenkinson, S. F., Rule, S. D., Higham, R., Mercer, T. B., Newell, R. J., Weymouth-Wilson, A. C., Fleet, G. W. J. & Petursson, S. (2008). Tetrahedron Lett.49, 2196–2199.
  • Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.
  • Collins, P. M. & Ferrier, R. J. (1995). In Monosaccharides: Their Chemistry and Their Roles in Natural Products. New York: John Wiley & Sons.
  • Draths, K. M., Pompliano, D. L., Conley, D. L., Frost, J. W., Berry, A., Disbrow, G. L., Staversky, R. J. & Lievenset, J. C. (1992). J. Am. Chem. Soc.114, 3956–3962.
  • Görbitz, C. H. (1999). Acta Cryst. B55, 1090–1098. [PubMed]
  • Jackson, G., Jones, H. F., Petursson, S. & Webber, J. M. (1982). Carbohydr. Res.102, 147–157.
  • Jenkinson, S. F., Rule, S. D., Booth, K. V., Fleet, G. W. J., Watkin, D. J. & Petursson, S. (2008). Acta Cryst. E64, o26. [PMC free article] [PubMed]
  • Nonius (2001). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Petursson, S. (2001). Carbohydr. Res.331, 239–245. [PubMed]
  • Petursson, S. (2003). Carbohydr. Res.338, 963–968. [PubMed]
  • Petursson, S., Jenkinson, S. F., Booth, K. V., Weymouth-Wilson, A. C., Watkin, D. J., Fleet, G. W. J. & Best, D. (2007). Acta Cryst. E63, o4121.
  • Petursson, S. & Webber, J. M. (1982). Carbohydr. Res.103, 41–52.
  • Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON Chemical Crystallography Laboratory, Oxford, UK.

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