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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 62| Part 9| September 2006| Pages o3890-o3892
https://doi.org/10.1107/S1600536806031618

2,3:6,7-Di-O-di­ethyl­­idene-D-glycero-L-talo-heptono-1,4-lactone

CROSSMARK_Color_square_no_text.svg
Anders E. Håkansson,a* Jeroen van Ameijde,a Graeme Horne,b Luisa Guglielmini,a Robert J. Nash,c George W.J. Fleeta and David J. Watkind

aDepartment of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, bMNLpharma Limited, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, cMNLpharma Limited, Plas Gogerddan, Aberystwyth, Ceredigion SY23 3EB, Wales, and dDepartment of Chemical Crystallography, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England
*Correspondence e-mail: anders.hakansson@chem.ox.ac.uk

(Received 8 August 2006; accepted 10 August 2006; online 16 August 2006)

The title compound, C17H28O7, was prepared from protected D-glycero-D-gulo-heptono-1,4-lactone by tandem SN2 displacements. The relative configuration of the crystal structure establishes that two stereocentres have been inverted; the absolute configuration was determined by the use of D-glucose as the starting material. There are three independent mol­ecules in the asymmetric unit (Z′=3).

Comment

Although carbohydrates are the most widely used chiral scaffolds (Lichtenthaler & Peters, 2004[Hotchkiss, D., Soengas, R., Simone, M. I., Van Ameijde, J., Hunter, S., Cowley, A. R. & Fleet, G. W. J. (2004). Tetrahedron Lett. 45, 9461-9464.]; Bols, 1996[Bols, M. (1996). Carbohydrate Building Blocks, ISBN 0-471-13339-6. New York: John Wiley & Son.]), D-glycero-D-gulo-heptono-1,4-lactone – prepared industrially from D-glucose – is the only seven-carbon sugar that is cheaply available. The value of this carbohydrate lactone as a starting material has been illustrated by the syntheses of the anti­biotic gonifurfuran­one (Shing et al., 1992[Shing, T. K. M. & Tsui, H. C. (1992). Chem. Commun. 432-434.]; Shing & Tsui, 1992[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.]) and a number of imino sugars (Watson et al., 2001[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, UK.]; Asano et al., 2000[Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymm. 11, 1645-1680.]; Fairbanks et al., 1991[Fairbanks, A. J., Fleet, G. W. J., Jones, A. H., Bruce, I., Al Daher, S., Cenci di Bello, I. & Winchester, B. (1991). Tetrahedron, 47, 131-138.]; Myerscough et al., 1992[Lichtenthaler, F. W. & Peters, S. (2004). C. R. Chim. 7, 65-90.]). Otherwise the use of protected seven-carbon sugars is rare (Choi et al., 1991[Burke, S. D., Jung, K. W., Philips, J. R. & Perri, R. E. (1994). Tetrahedron Lett. 35, 703-706.]; Beacham et al., 1991[Beacham, A. R., Bruce, I., Choi, S., Doherty, O., Fairbanks, A. J., Fleet, G. W. J., Skead, B. M., Peach, J. M., Saunders, J. & Watkin, D. J. (1991). Tetrahedron Asymm. 2, 883-900.]).

[Scheme 1]

This paper reports the structure of the protected D-glycero-L-talo-heptono-1,4-lactone (3) which is likely to be another easily available and valuable seven-carbon sugar chiron for the enanti­ospecific synthesis of complex bioactive compounds. D-glycero-D-gulo-Heptono-1,4-lactone was treated with 3-penta­none to give the diketal (1) in which only the hydroxyl atom C5 is unprotected (Burke et al., 1994[Burke, S. D., Jung, K. W., Philips, J. R. & Perri, R. E. (1994). Tetrahedron Lett. 35, 703-706.]; Burke et al., 2000[Burke, S. D., Jung, K. W., Lambert, W. T., Philips, J. R. & Klovning, J. J. (2000). J. Org. Chem. 65, 4070-4087.]). Esterification of the alcohol group in (1) with triflic anhydride in the presence of pyridine gave the trifluoro­methane­sulfonate ester (2), which on treatment with hydroxide gives an open chain epoxide, which upon neutralization gives the title lactone (3). The X-ray crystal analysis of (3) shows that there has been an overall inversion of configuration at atoms C4 and C5 from the starting lactone (1); the absolute configuration of (3) arises from the use of D-glucose as the starting material for the synthesis of the protected lactone (1). The technique of double inversion of the stereochemistry at atoms C4 and C5 of sugar lactones used in this paper appears to be general (Hotchkiss et al., 2004[Hotchkiss, D., Soengas, R., Simone, M. I., Van Ameijde, J., Hunter, S., Cowley, A. R. & Fleet, G. W. J. (2004). Tetrahedron Lett. 45, 9461-9464.]; van Ameijde et al., 2004[Ameijde, J., Cowley, A. R., Fleet, G. W. J., Nash, R. J., Simone, M. I. & Soengas, R. (2004). Acta Cryst. E60, o2140-o2141.]) and may allow a considerable increase in the number of carbohydrate lactones available as synthetic inter­mediates.

There are three independent mol­ecules in the asymmetric unit. The mol­ecules C1–O24 (mol­ecule A) and C201–O224 (mol­ecule B) are related by an approximately pseudo twofold axis, with a pseudo-symmetry operator of form: 0.17 + x, 0.36 − y, 1.76 − z. On mol­ecular superposition, the r.m.s. positional deviation is 0.90 Å, the r.m.s. bond-length deviation is 0.019 Å, and the r.m.s. torsion-angle deviation is 48.06°. Mol­ecule C101–O124 (mol­ecule C) has no rational relationship with the other mol­ecules. The crystal structure consists of layers perpendic­ular to the b axis, with each layer composed solely of one type of mol­ecule (Fig. 2[link]). The layers form a type of sandwich, with the filling (mol­ecule C) hydrogen-bonded to mol­ecules A and B below and above it (Fig. 3[link]). There is no hydrogen bonding between the layers A and B.

[Figure 1]
Figure 1
Mol­ecule A of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 2]
Figure 2
Layers of mol­ecules perpendicular to the b-axis direction. The layers are linked by hydrogen bonds in the order mol­ecule B (green C atoms) to mol­ecule C (blue C atoms) to mol­ecule A (orange C atoms). Layers of mol­ecules A are not hydrogen-bonded to layers of mol­ecules B. Hydrogen bonds are shown as dotted lines.
[Figure 3]
Figure 3
The asymmetric hydrogen-bonding network. Layers of mol­ecules B and C are bonded by one donor and one acceptor hydrogen bond; layers of mol­ecules C and A are only linked by one type of bond. H atoms not involved in hydrogen bonding have been omitted. Blue, green and yellow C atoms are as in Fig. 2[link] and hydrogen bonds are shown as dotted lines.

Experimental

Diketal (1)(Burke et al., 2000[Burke, S. D., Jung, K. W., Lambert, W. T., Philips, J. R. & Klovning, J. J. (2000). J. Org. Chem. 65, 4070-4087.]) was converted into (2) by treatment with trifluoro­methane­sulfonic anhydride (1.3 eq) in the presence of pyridine (2.5 eq). Crude (2) was stirred under basic conditions (KOH, 3 eq) followed by a careful acidic work-up (Amberlyst 15) to produce (3) (Håkansson et al., 2006[Håkansson, A. E., van Ameijde, J., Horne, G., Guglielmini, L., Nash, R. J. & Fleet, G. W. J. (2006). In preparation.]). The title material was crystallized from heptane to yield fine colourless lath-like crystals with m.p. 366–367 K and [α]D21 = −28.4 (c=1.93, CHCl3).

Crystal data

  • C17H28O7

  • Mr = 344.41

  • Monoclinic, P 21

  • a = 6.7757 (2) Å

  • b = 27.7655 (6) Å

  • c = 14.8433 (3) Å

  • β = 101.4341 (8)°

  • V = 2737.06 (11) Å3

  • Z = 6

  • Dx = 1.254 Mg m−3

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 150 K

  • Lath, colourless

  • 0.40 × 0.20 × 0.06 mm
Data collection

  • Nonius KappaCCD diffractometer

  • ω scans

  • Absorption correction: multi-scan DENZO/SCALEPACK; Otwinowski & Minor, 1997[Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.]) Tmin = 0.37, Tmax = 0.99

  • 16244 measured reflections

  • 4828 independent reflections

  • 4828 reflections with I > −3σ(I)

  • Rint = 0.039

  • θmax = 25.0°
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.113

  • S = 0.97

  • 4828 reflections

  • 649 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(F2) + ( 0.05P)2 + 1.81P] , where P = (max(Fo2,0) + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O223—H2225⋯O115i 0.82 1.92 2.696 (2) 157
O123—H123⋯O224 0.83 1.90 2.719 (2) 166
O23—H23⋯O105i 0.80 1.96 2.738 (2) 162
Symmetry code: (i) x+1, y, z.

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

The H atoms were all located in a difference map, but those attached to C 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.

Data collection: COLLECT (Nonius, 1997-2001[Myerscough, P. M., Fairbanks, A. J., Jones, A. H., Choi, S.-S., Fleet, G. W. J., Al-Daher, S. S., Cenci di Bello, I. & Winchester, B. (1992). Tetrahedron, 48, 10177-10190.]).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Shing, T. K. M., Tsui, H. C. & Zhou, Z. H. (1992). Chem. Commun. 810-811.]); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks CRYSTALS_cif, 3. DOI: https://doi.org/10.1107/S1600536806031618/lh2158sup1.cif

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S1600536806031618/lh21583sup2.hkl


Computing details top

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

(3) top
Crystal data top
C17H28O7F(000) = 1116
Mr = 344.41Dx = 1.254 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4289 reflections
a = 6.7757 (2) Åθ = 5–25°
b = 27.7655 (6) ŵ = 0.10 mm−1
c = 14.8433 (3) ÅT = 150 K
β = 101.4341 (8)°Lath, colourless
V = 2737.06 (11) Å30.40 × 0.20 × 0.06 mm
Z = 6
Data collection top
Nonius KappaCCD
diffractometer		4828 reflections with I > −3.0σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 25.0°, θmin = 5.1°
Absorption correction: multi-scan
DENZO/SCALEPACK; Otwinowski & Minor, 1997)		h = −8→8
Tmin = 0.37, Tmax = 0.99k = −33→30
16244 measured reflectionsl = −17→17
4828 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.113 Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.05P)2 + 1.81P] ,
where P = (max(Fo2,0) + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4828 reflectionsΔρmax = 0.47 e Å−3
649 parametersΔρmin = −0.29 e Å−3
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C2010.8313 (5)0.33181 (14)0.8217 (2)0.0294
C2020.6660 (5)0.29794 (14)0.8383 (2)0.0302
O2030.6188 (4)0.31060 (10)0.92324 (17)0.0350
C2040.7446 (6)0.35047 (15)0.9604 (3)0.0335
O2050.8167 (4)0.37046 (10)0.88458 (17)0.0323
C2060.6132 (7)0.38806 (17)0.9944 (3)0.0450
C2070.4344 (8)0.4034 (2)0.9231 (4)0.0602
C2080.9150 (6)0.33053 (17)1.0332 (3)0.0426
C2091.0627 (8)0.3679 (2)1.0820 (4)0.0602
C2100.4894 (6)0.31130 (15)0.7613 (3)0.0340
O2110.5422 (4)0.34438 (10)0.70516 (17)0.0310
C2120.7613 (5)0.34914 (14)0.7236 (2)0.0284
C2130.8409 (6)0.31737 (14)0.6556 (3)0.0308
C2140.7491 (6)0.32936 (14)0.5568 (2)0.0318
O2150.8654 (4)0.30547 (10)0.49849 (17)0.0358
C2160.8417 (6)0.33184 (15)0.4152 (3)0.0375
O2170.7673 (4)0.37868 (10)0.43336 (17)0.0374
C2180.7664 (6)0.38150 (15)0.5293 (3)0.0372
C2210.6860 (7)0.30765 (17)0.3417 (3)0.0463
C2220.6278 (9)0.3360 (2)0.2527 (3)0.0620
C2191.0474 (7)0.33632 (19)0.3901 (3)0.0519
C2201.2024 (7)0.3604 (2)0.4641 (4)0.0703
O2230.7884 (4)0.26900 (10)0.67432 (19)0.0383
O2240.3175 (4)0.29725 (13)0.7512 (2)0.0507
H20110.96210.31690.83230.0349*
H20210.70160.26430.83760.0348*
H20610.69500.41591.01700.0541*
H20620.56500.37431.04580.0538*
H20710.36740.43010.94470.0896*
H20720.47480.41180.86630.0897*
H20730.34120.37710.91150.0900*
H20810.85080.31431.07930.0496*
H20820.98970.30771.00330.0504*
H20911.17170.35261.12350.0858*
H20920.99680.39051.11440.0860*
H20931.11730.38511.03700.0858*
H21210.79690.38240.71750.0336*
H21310.98690.32010.66610.0358*
H21410.60710.31890.54210.0379*
H21810.88970.39580.56260.0429*
H21820.65210.40030.54080.0430*
H22110.56430.30260.36580.0537*
H22120.74300.27660.32960.0541*
H22210.52100.31960.21280.0891*
H22220.58590.36820.26550.0890*
H22230.74140.33790.22310.0893*
H21911.03210.35580.33410.0640*
H21921.09200.30410.37940.0643*
H22011.32920.36390.44380.1036*
H22021.15560.39160.47830.1038*
H22031.22390.34130.51980.1038*
H22250.89300.25320.68150.0562*
C10.9236 (6)0.03387 (14)0.9400 (2)0.0315
C20.7418 (5)0.06629 (14)0.9237 (2)0.0306
O30.6392 (4)0.05689 (10)0.83259 (17)0.0352
C40.6881 (6)0.00855 (15)0.8104 (3)0.0346
O50.8709 (4)−0.00365 (11)0.87419 (18)0.0410
C60.5276 (6)−0.02698 (17)0.8276 (3)0.0436
C70.3217 (7)−0.0191 (2)0.7693 (4)0.0616
C80.7241 (7)0.00972 (18)0.7138 (3)0.0466
C90.7602 (9)−0.0394 (2)0.6740 (4)0.0635
C100.6215 (5)0.04923 (14)0.9944 (3)0.0314
O110.7324 (3)0.01923 (10)1.05519 (17)0.0306
C120.9365 (5)0.01475 (14)1.0386 (2)0.0274
C131.0763 (5)0.04417 (14)1.1096 (2)0.0280
C141.0668 (5)0.02896 (13)1.2060 (2)0.0275
O151.2350 (4)0.04941 (10)1.26846 (17)0.0358
C161.2767 (7)0.02018 (16)1.3488 (3)0.0428
O171.1777 (4)−0.02533 (10)1.32302 (18)0.0371
C181.0959 (6)−0.02409 (14)1.2270 (3)0.0338
C191.4973 (7)0.0134 (2)1.3797 (4)0.0563
C201.5924 (8)−0.0135 (2)1.3131 (4)0.0672
C211.1724 (8)0.04427 (18)1.4238 (3)0.0504
C221.1742 (9)0.0151 (2)1.5077 (4)0.0714
O231.0175 (4)0.09288 (10)1.09325 (19)0.0363
O240.4486 (4)0.05844 (11)0.9968 (2)0.0419
C1010.2944 (6)0.19339 (15)1.0398 (3)0.0338
C1020.4841 (5)0.22309 (14)1.0624 (3)0.0333
O1030.5567 (4)0.21757 (10)1.15862 (18)0.0372
C1040.4728 (7)0.17508 (17)1.1889 (3)0.0447
O1050.3271 (4)0.15780 (10)1.11168 (19)0.0384
C1060.6363 (7)0.13477 (19)1.2105 (3)0.0506
C1070.8008 (9)0.1459 (2)1.2925 (4)0.0720
C1080.3736 (8)0.1864 (2)1.2668 (4)0.0634
C1090.2113 (10)0.2236 (2)1.2437 (5)0.0802
C1100.6212 (6)0.20074 (15)1.0046 (3)0.0337
O1110.5123 (4)0.17239 (11)0.93880 (19)0.0399
C1120.3011 (5)0.16896 (14)0.9488 (3)0.0341
C1130.1680 (6)0.19372 (14)0.8680 (3)0.0368
C1140.2094 (6)0.17741 (16)0.7771 (3)0.0414
O1150.0596 (5)0.19682 (11)0.7036 (2)0.0491
C116−0.0007 (7)0.16029 (18)0.6343 (3)0.0516
O1170.1341 (6)0.12115 (13)0.6613 (2)0.0625
C1180.1961 (8)0.12378 (18)0.7596 (3)0.0592
C1210.0305 (8)0.1797 (2)0.5418 (3)0.0569
C1220.2377 (10)0.2034 (3)0.5465 (5)0.0895
C119−0.2182 (8)0.14645 (19)0.6341 (4)0.0584
C120−0.3106 (10)0.1115 (2)0.5590 (4)0.0741
O1230.1852 (4)0.24423 (10)0.88144 (19)0.0404
O1240.7996 (4)0.20554 (12)1.0113 (2)0.0458
H22241.05050.04970.93370.0371*
H210.77430.10050.93210.0359*
H610.5151−0.02500.89170.0511*
H620.5692−0.05910.81390.0509*
H710.2286−0.04160.78670.0911*
H720.27840.01370.77770.0910*
H730.3294−0.02370.70480.0909*
H810.60470.02370.67450.0552*
H820.84250.03080.71250.0549*
H910.8147−0.03440.61950.0951*
H920.6361−0.05740.66030.0950*
H930.8573−0.05670.71970.0950*
H1210.9757−0.01921.04200.0315*
H1311.21460.04031.09970.0313*
H1410.94040.03981.22140.0315*
H1811.1920−0.03741.19270.0384*
H1820.9708−0.04151.21490.0397*
H1911.56210.04571.39050.0665*
H1921.5172−0.00501.43890.0665*
H2011.7343−0.01611.33750.1020*
H2021.56880.00311.25440.1018*
H2031.5382−0.04591.30540.1019*
H2111.25080.07351.44220.0582*
H2121.03160.05161.39330.0578*
H10110.17010.21241.03770.0390*
H10210.45860.25711.04560.0390*
H10610.69960.13161.15680.0577*
H10620.57060.10501.22150.0581*
H10710.91230.12311.29600.1063*
H10720.84990.17931.28920.1062*
H10730.74300.14291.34780.1061*
H10810.47830.19841.31690.0790*
H10820.31740.15571.28500.0792*
H11210.26460.13440.94820.0401*
H11310.02860.18460.87070.0422*
H11410.34210.18990.77190.0465*
H11810.08910.10940.78860.0643*
H11820.32400.10700.78140.0642*
H1211−0.07240.20340.52190.0650*
H12120.00880.15290.49820.0647*
H12210.26740.20970.48450.1369*
H12220.24870.23320.58190.1372*
H12230.33690.18040.57950.1371*
H1191−0.29800.17610.62780.0659*
H1192−0.22290.13170.69520.0665*
H1201−0.43860.09730.56850.1061*
H1202−0.33480.12910.50050.1063*
H1203−0.21310.08570.55590.1065*
H2211.10570.03321.54920.1090*
H2221.31620.00881.53680.1093*
H2231.1045−0.01591.48940.1089*
H10910.15550.23041.29750.1249*
H10920.26360.25321.22210.1249*
H10930.10370.21021.19650.1249*
H1230.22750.25610.83720.0610*
H231.10280.11271.10960.0520*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2010.0293 (18)0.030 (2)0.0286 (18)0.0002 (15)0.0043 (14)−0.0047 (16)
C2020.0317 (19)0.0247 (19)0.033 (2)0.0011 (15)0.0030 (15)0.0036 (15)
O2030.0356 (14)0.0363 (15)0.0333 (14)−0.0021 (12)0.0071 (11)0.0028 (12)
C2040.036 (2)0.033 (2)0.033 (2)−0.0014 (17)0.0100 (16)0.0029 (16)
O2050.0391 (14)0.0312 (14)0.0282 (13)−0.0038 (12)0.0102 (11)−0.0029 (11)
C2060.054 (3)0.041 (3)0.044 (2)0.008 (2)0.020 (2)0.002 (2)
C2070.068 (3)0.058 (3)0.058 (3)0.028 (3)0.023 (2)0.008 (3)
C2080.042 (2)0.048 (3)0.036 (2)−0.001 (2)0.0034 (17)0.0014 (19)
C2090.059 (3)0.065 (3)0.053 (3)−0.015 (3)0.000 (2)0.004 (3)
C2100.032 (2)0.034 (2)0.034 (2)0.0013 (17)0.0032 (16)0.0034 (17)
O2110.0279 (13)0.0328 (14)0.0322 (13)0.0048 (11)0.0054 (10)0.0069 (12)
C2120.0282 (18)0.0278 (19)0.0289 (19)−0.0024 (15)0.0044 (14)0.0002 (15)
C2130.0292 (18)0.030 (2)0.0320 (19)0.0053 (16)0.0038 (15)−0.0004 (16)
C2140.0317 (19)0.029 (2)0.033 (2)0.0042 (16)0.0039 (15)−0.0053 (16)
O2150.0460 (16)0.0326 (15)0.0292 (14)0.0095 (12)0.0087 (12)−0.0001 (11)
C2160.046 (2)0.031 (2)0.036 (2)0.0066 (18)0.0121 (17)0.0013 (18)
O2170.0514 (16)0.0310 (15)0.0295 (14)0.0048 (12)0.0072 (12)−0.0002 (11)
C2180.043 (2)0.034 (2)0.034 (2)0.0019 (17)0.0056 (17)−0.0041 (17)
C2210.063 (3)0.039 (2)0.034 (2)−0.001 (2)0.0047 (19)−0.0027 (19)
C2220.090 (4)0.051 (3)0.037 (2)−0.003 (3)−0.007 (2)−0.001 (2)
C2190.057 (3)0.053 (3)0.050 (3)0.009 (2)0.022 (2)0.006 (2)
C2200.041 (3)0.095 (5)0.073 (4)0.000 (3)0.006 (2)0.027 (3)
O2230.0421 (15)0.0266 (14)0.0451 (16)0.0086 (12)0.0057 (12)−0.0004 (12)
O2240.0279 (15)0.071 (2)0.0491 (18)−0.0086 (14)−0.0014 (12)0.0145 (16)
C10.0299 (19)0.037 (2)0.0280 (19)−0.0014 (16)0.0065 (14)−0.0017 (16)
C20.0303 (19)0.030 (2)0.0296 (19)−0.0003 (16)0.0014 (15)0.0040 (16)
O30.0353 (14)0.0342 (15)0.0329 (14)0.0037 (12)−0.0010 (11)0.0020 (12)
C40.0313 (19)0.036 (2)0.034 (2)0.0029 (17)0.0015 (15)−0.0002 (17)
O50.0395 (15)0.0459 (18)0.0346 (15)0.0144 (13)−0.0002 (12)−0.0088 (13)
C60.044 (2)0.041 (3)0.046 (2)−0.0026 (19)0.0118 (19)−0.005 (2)
C70.043 (3)0.058 (3)0.082 (4)−0.010 (2)0.008 (2)−0.006 (3)
C80.046 (2)0.060 (3)0.033 (2)−0.002 (2)0.0059 (18)0.000 (2)
C90.072 (3)0.077 (4)0.044 (3)−0.005 (3)0.017 (2)−0.014 (3)
C100.029 (2)0.031 (2)0.034 (2)−0.0007 (16)0.0053 (15)−0.0002 (16)
O110.0270 (13)0.0341 (15)0.0316 (13)−0.0063 (11)0.0076 (10)0.0004 (11)
C120.0246 (17)0.030 (2)0.0289 (18)−0.0001 (15)0.0078 (14)0.0023 (16)
C130.0249 (17)0.030 (2)0.0287 (18)−0.0017 (15)0.0038 (14)0.0045 (15)
C140.0288 (18)0.027 (2)0.0261 (18)−0.0018 (15)0.0032 (14)0.0003 (15)
O150.0382 (14)0.0335 (15)0.0321 (14)−0.0073 (12)−0.0020 (11)0.0023 (11)
C160.055 (3)0.032 (2)0.034 (2)−0.009 (2)−0.0071 (18)0.0038 (18)
O170.0467 (16)0.0307 (15)0.0303 (14)−0.0035 (12)−0.0015 (12)0.0058 (12)
C180.040 (2)0.031 (2)0.0293 (19)−0.0039 (17)0.0046 (16)0.0021 (16)
C190.051 (3)0.055 (3)0.058 (3)−0.002 (2)−0.001 (2)0.001 (2)
C200.049 (3)0.094 (4)0.061 (3)−0.018 (3)0.016 (2)−0.014 (3)
C210.057 (3)0.046 (3)0.044 (2)0.003 (2)0.000 (2)−0.006 (2)
C220.083 (4)0.082 (4)0.052 (3)0.020 (3)0.021 (3)−0.006 (3)
O230.0392 (15)0.0247 (14)0.0413 (15)−0.0084 (11)−0.0011 (11)0.0051 (12)
O240.0273 (15)0.0465 (18)0.0538 (17)0.0033 (12)0.0128 (12)−0.0025 (14)
C1010.0287 (19)0.031 (2)0.040 (2)−0.0030 (16)0.0022 (15)0.0059 (17)
C1020.0310 (19)0.027 (2)0.040 (2)−0.0020 (16)0.0033 (16)0.0025 (17)
O1030.0363 (14)0.0357 (15)0.0384 (15)−0.0095 (12)0.0046 (11)0.0010 (12)
C1040.051 (2)0.042 (2)0.039 (2)−0.023 (2)0.0038 (18)0.000 (2)
O1050.0344 (15)0.0326 (15)0.0455 (16)−0.0093 (12)0.0010 (12)0.0094 (13)
C1060.047 (3)0.053 (3)0.049 (3)−0.006 (2)0.004 (2)0.000 (2)
C1070.073 (4)0.075 (4)0.058 (3)0.000 (3)−0.014 (3)0.007 (3)
C1080.066 (3)0.066 (4)0.063 (3)−0.016 (3)0.026 (3)−0.014 (3)
C1090.092 (4)0.072 (4)0.087 (4)−0.005 (3)0.045 (4)−0.020 (3)
C1100.031 (2)0.034 (2)0.035 (2)−0.0019 (17)0.0029 (16)0.0065 (17)
O1110.0297 (14)0.0423 (17)0.0453 (16)0.0046 (12)0.0019 (12)−0.0014 (13)
C1120.0286 (19)0.025 (2)0.048 (2)0.0015 (16)0.0058 (16)0.0034 (17)
C1130.0298 (19)0.028 (2)0.049 (2)−0.0003 (16)−0.0017 (16)−0.0012 (18)
C1140.038 (2)0.038 (2)0.043 (2)0.0120 (19)−0.0044 (17)0.0038 (19)
O1150.0556 (18)0.0358 (17)0.0445 (17)0.0155 (14)−0.0175 (13)−0.0094 (13)
C1160.057 (3)0.043 (3)0.048 (3)0.017 (2)−0.007 (2)−0.011 (2)
O1170.075 (2)0.052 (2)0.0487 (19)0.0295 (18)−0.0171 (16)−0.0162 (16)
C1180.065 (3)0.044 (3)0.056 (3)0.019 (2)−0.017 (2)−0.014 (2)
C1210.058 (3)0.057 (3)0.050 (3)0.014 (2)−0.003 (2)−0.011 (2)
C1220.074 (4)0.118 (6)0.078 (4)0.017 (4)0.020 (3)0.006 (4)
C1190.055 (3)0.048 (3)0.063 (3)0.003 (2)−0.011 (2)−0.004 (2)
C1200.087 (4)0.062 (4)0.061 (3)−0.013 (3)−0.017 (3)−0.001 (3)
O1230.0478 (16)0.0291 (15)0.0450 (16)0.0030 (13)0.0109 (13)0.0023 (12)
O1240.0264 (15)0.0537 (19)0.0572 (19)−0.0043 (13)0.0080 (12)0.0059 (15)
Geometric parameters (Å, º) top
C201—C2021.519 (5)C12—H1210.978
C201—O2051.439 (4)C13—C141.506 (5)
C201—C2121.517 (5)C13—O231.417 (5)
C201—H20110.963C13—H1310.982
C202—O2031.406 (5)C14—O151.436 (4)
C202—C2101.527 (5)C14—C181.510 (5)
C202—H20210.965C14—H1410.977
O203—C2041.439 (5)O15—C161.424 (5)
C204—O2051.425 (5)C16—O171.446 (5)
C204—C2061.521 (6)C16—C191.485 (6)
C204—C2081.521 (6)C16—C211.581 (7)
C206—C2071.503 (7)O17—C181.424 (4)
C206—H20610.971C18—H1810.975
C206—H20620.966C18—H1820.961
C207—H20710.957C19—C201.484 (8)
C207—H20720.966C19—H1910.997
C207—H20730.957C19—H1921.003
C208—C2091.522 (6)C20—H2010.960
C208—H20810.990C20—H2020.970
C208—H20820.971C20—H2030.971
C209—H20910.962C21—C221.483 (8)
C209—H20920.952C21—H2110.979
C209—H20930.954C21—H2120.992
C210—O2111.336 (5)C22—H2210.980
C210—O2241.209 (5)C22—H2220.989
O211—C2121.461 (4)C22—H2230.993
C212—C2131.518 (5)O23—H230.801
C212—H21210.964C101—C1021.508 (5)
C213—C2141.513 (5)C101—O1051.439 (5)
C213—O2231.431 (5)C101—C1121.520 (6)
C213—H21310.974C101—H10110.989
C214—O2151.443 (4)C102—O1031.424 (5)
C214—C2181.515 (6)C102—C1101.517 (6)
C214—H21410.988C102—H10210.984
O215—C2161.419 (5)O103—C1041.420 (5)
C216—O2171.440 (5)C104—O1051.439 (5)
C216—C2211.515 (6)C104—C1061.563 (7)
C216—C2191.518 (6)C104—C1081.482 (7)
O217—C2181.427 (5)C106—C1071.510 (7)
C218—H21810.968C106—H10610.981
C218—H21820.977C106—H10620.968
C221—C2221.521 (6)C107—H10710.979
C221—H22110.972C107—H10720.991
C221—H22120.976C107—H10730.981
C222—H22210.955C108—C1091.498 (9)
C222—H22220.969C108—H10810.978
C222—H22230.961C108—H10820.992
C219—C2201.517 (8)C109—H10910.967
C219—H21910.980C109—H10920.974
C219—H21920.967C109—H10930.979
C220—H22010.970C110—O1111.353 (5)
C220—H22020.960C110—O1241.200 (5)
C220—H22030.970O111—C1121.471 (5)
O223—H22250.823C112—C1131.515 (5)
C1—C21.506 (5)C112—H11210.990
C1—O51.425 (5)C113—C1141.500 (6)
C1—C121.542 (5)C113—O1231.418 (5)
C1—H22240.986C113—H11310.987
C2—O31.417 (4)C114—O1151.440 (5)
C2—C101.526 (5)C114—C1181.511 (7)
C2—H210.978C114—H11410.982
O3—C41.436 (5)O115—C1161.445 (5)
C4—O51.442 (4)C116—O1171.425 (5)
C4—C61.527 (6)C116—C1211.528 (7)
C4—C81.502 (6)C116—C1191.522 (7)
C6—C71.505 (7)O117—C1181.438 (6)
C6—H610.973C118—H11810.997
C6—H620.969C118—H11820.980
C7—H710.958C121—C1221.540 (9)
C7—H720.973C121—H12110.963
C7—H730.976C121—H12120.977
C8—C91.525 (7)C122—H12210.995
C8—H810.980C122—H12220.976
C8—H820.996C122—H12230.985
C9—H910.964C119—C1201.516 (7)
C9—H920.964C119—H11910.980
C9—H930.974C119—H11921.002
C10—O111.343 (5)C120—H12010.989
C10—O241.206 (4)C120—H12020.981
O11—C121.457 (4)C120—H12030.983
C12—C131.510 (5)O123—H1230.835
C202—C201—O205102.0 (3)C13—C12—H121111.0
C202—C201—C212104.6 (3)C12—C13—C14111.9 (3)
O205—C201—C212109.7 (3)C12—C13—O23106.3 (3)
C202—C201—H2011113.0C14—C13—O23111.5 (3)
O205—C201—H2011113.3C12—C13—H131108.8
C212—C201—H2011113.4C14—C13—H131109.4
C201—C202—O203107.3 (3)O23—C13—H131108.9
C201—C202—C210102.8 (3)C13—C14—O15108.9 (3)
O203—C202—C210109.0 (3)C13—C14—C18116.2 (3)
C201—C202—H2021113.8O15—C14—C18101.4 (3)
O203—C202—H2021110.7C13—C14—H141109.9
C210—C202—H2021112.8O15—C14—H141110.3
C202—O203—C204108.3 (3)C18—C14—H141109.7
O203—C204—O205105.5 (3)C14—O15—C16108.4 (3)
O203—C204—C206108.3 (3)O15—C16—O17105.8 (3)
O205—C204—C206108.0 (3)O15—C16—C19110.5 (4)
O203—C204—C208107.5 (3)O17—C16—C19110.9 (4)
O205—C204—C208111.8 (3)O15—C16—C21107.8 (3)
C206—C204—C208115.2 (3)O17—C16—C21107.9 (4)
C201—O205—C204107.5 (3)C19—C16—C21113.5 (4)
C204—C206—C207113.8 (4)C16—O17—C18108.2 (3)
C204—C206—H2061109.2C14—C18—O17103.8 (3)
C207—C206—H2061110.1C14—C18—H181109.6
C204—C206—H2062107.7O17—C18—H181110.2
C207—C206—H2062108.3C14—C18—H182112.3
H2061—C206—H2062107.4O17—C18—H182109.2
C206—C207—H2071110.7H181—C18—H182111.5
C206—C207—H2072110.7C16—C19—C20113.7 (4)
H2071—C207—H2072109.8C16—C19—H191108.7
C206—C207—H2073108.9C20—C19—H191108.9
H2071—C207—H2073108.1C16—C19—H192106.7
H2072—C207—H2073108.5C20—C19—H192109.1
C204—C208—C209115.1 (4)H191—C19—H192109.7
C204—C208—H2081106.4C19—C20—H201108.7
C209—C208—H2081108.6C19—C20—H202110.0
C204—C208—H2082107.7H201—C20—H202110.4
C209—C208—H2082108.1C19—C20—H203110.0
H2081—C208—H2082111.0H201—C20—H203107.5
C208—C209—H2091110.6H202—C20—H203110.1
C208—C209—H2092111.1C16—C21—C22115.4 (4)
H2091—C209—H2092110.2C16—C21—H211104.7
C208—C209—H2093108.5C22—C21—H211107.7
H2091—C209—H2093108.3C16—C21—H212106.8
H2092—C209—H2093108.2C22—C21—H212110.0
C202—C210—O211111.5 (3)H211—C21—H212112.2
C202—C210—O224127.4 (4)C21—C22—H221108.8
O211—C210—O224121.0 (3)C21—C22—H222108.0
C210—O211—C212109.5 (3)H221—C22—H222111.0
C201—C212—O211105.3 (3)C21—C22—H223108.6
C201—C212—C213111.6 (3)H221—C22—H223110.9
O211—C212—C213107.7 (3)H222—C22—H223109.5
C201—C212—H2121111.0C13—O23—H23116.3
O211—C212—H2121109.5C102—C101—O105102.2 (3)
C213—C212—H2121111.4C102—C101—C112105.5 (3)
C212—C213—C214112.6 (3)O105—C101—C112109.0 (3)
C212—C213—O223106.4 (3)C102—C101—H1011113.5
C214—C213—O223108.9 (3)O105—C101—H1011113.2
C212—C213—H2131109.4C112—C101—H1011112.7
C214—C213—H2131110.3C101—C102—O103105.9 (3)
O223—C213—H2131109.0C101—C102—C110104.0 (3)
C213—C214—O215108.2 (3)O103—C102—C110113.2 (3)
C213—C214—C218115.7 (3)C101—C102—H1021111.7
O215—C214—C218101.3 (3)O103—C102—H1021111.4
C213—C214—H2141110.2C110—C102—H1021110.3
O215—C214—H2141110.8C102—O103—C104109.0 (3)
C218—C214—H2141110.3O103—C104—O105106.2 (3)
C214—O215—C216107.7 (3)O103—C104—C106110.4 (4)
O215—C216—O217106.6 (3)O105—C104—C106105.7 (4)
O215—C216—C221109.9 (3)O103—C104—C108110.0 (4)
O217—C216—C221108.4 (3)O105—C104—C108110.3 (4)
O215—C216—C219107.8 (3)C106—C104—C108113.9 (4)
O217—C216—C219110.2 (4)C101—O105—C104110.0 (3)
C221—C216—C219113.7 (4)C104—C106—C107113.5 (4)
C216—O217—C218107.9 (3)C104—C106—H1061107.7
C214—C218—O217103.5 (3)C107—C106—H1061107.6
C214—C218—H2181111.1C104—C106—H1062108.4
O217—C218—H2181111.0C107—C106—H1062109.2
C214—C218—H2182110.9H1061—C106—H1062110.5
O217—C218—H2182111.4C106—C107—H1071110.4
H2181—C218—H2182108.9C106—C107—H1072110.7
C216—C221—C222114.8 (4)H1071—C107—H1072110.2
C216—C221—H2211108.6C106—C107—H1073107.7
C222—C221—H2211107.5H1071—C107—H1073109.5
C216—C221—H2212106.3H1072—C107—H1073108.2
C222—C221—H2212109.9C104—C108—C109113.1 (5)
H2211—C221—H2212109.8C104—C108—H1081107.0
C221—C222—H2221109.1C109—C108—H1081109.2
C221—C222—H2222110.1C104—C108—H1082106.8
H2221—C222—H2222110.2C109—C108—H1082110.5
C221—C222—H2223109.5H1081—C108—H1082110.1
H2221—C222—H2223108.7C108—C109—H1091109.6
H2222—C222—H2223109.2C108—C109—H1092111.0
C216—C219—C220113.3 (4)H1091—C109—H1092109.4
C216—C219—H2191107.8C108—C109—H1093108.1
C220—C219—H2191108.2H1091—C109—H1093107.9
C216—C219—H2192107.2H1092—C109—H1093110.7
C220—C219—H2192109.5C102—C110—O111109.8 (3)
H2191—C219—H2192110.9C102—C110—O124128.8 (4)
C219—C220—H2201110.3O111—C110—O124121.4 (4)
C219—C220—H2202110.2C110—O111—C112111.5 (3)
H2201—C220—H2202109.4C101—C112—O111105.2 (3)
C219—C220—H2203110.0C101—C112—C113112.5 (3)
H2201—C220—H2203109.0O111—C112—C113109.2 (3)
H2202—C220—H2203107.9C101—C112—H1121112.8
C213—O223—H2225106.5O111—C112—H1121108.0
C2—C1—O5103.9 (3)C113—C112—H1121108.9
C2—C1—C12104.4 (3)C112—C113—C114112.7 (3)
O5—C1—C12111.0 (3)C112—C113—O123108.5 (3)
C2—C1—H2224114.8C114—C113—O123113.6 (4)
O5—C1—H2224111.4C112—C113—H1131106.0
C12—C1—H2224110.9C114—C113—H1131108.1
C1—C2—O3105.9 (3)O123—C113—H1131107.5
C1—C2—C10103.6 (3)C113—C114—O115109.8 (3)
O3—C2—C10111.8 (3)C113—C114—C118115.9 (4)
C1—C2—H21113.8O115—C114—C118103.3 (3)
O3—C2—H21110.9C113—C114—H1141107.6
C10—C2—H21110.6O115—C114—H1141109.1
C2—O3—C4107.4 (3)C118—C114—H1141111.0
O3—C4—O5106.0 (3)C114—O115—C116109.5 (3)
O3—C4—C6111.2 (3)O115—C116—O117105.1 (3)
O5—C4—C6106.6 (3)O115—C116—C121108.8 (4)
O3—C4—C8106.7 (3)O117—C116—C121109.0 (4)
O5—C4—C8110.5 (3)O115—C116—C119108.4 (4)
C6—C4—C8115.4 (4)O117—C116—C119112.0 (4)
C4—O5—C1110.2 (3)C121—C116—C119113.2 (4)
C4—C6—C7114.8 (4)C116—O117—C118106.8 (3)
C4—C6—H61109.3C114—C118—O117102.7 (4)
C7—C6—H61107.7C114—C118—H1181110.2
C4—C6—H62108.2O117—C118—H1181109.1
C7—C6—H62106.7C114—C118—H1182113.2
H61—C6—H62110.0O117—C118—H1182111.8
C6—C7—H71109.5H1181—C118—H1182109.7
C6—C7—H72109.3C116—C121—C122113.4 (4)
H71—C7—H72110.1C116—C121—H1211107.3
C6—C7—H73108.7C122—C121—H1211108.6
H71—C7—H73110.2C116—C121—H1212107.3
H72—C7—H73108.9C122—C121—H1212111.8
C4—C8—C9114.8 (4)H1211—C121—H1212108.2
C4—C8—H81107.9C121—C122—H1221112.6
C9—C8—H81107.5C121—C122—H1222111.0
C4—C8—H82108.4H1221—C122—H1222109.9
C9—C8—H82109.0C121—C122—H1223105.7
H81—C8—H82109.1H1221—C122—H1223109.4
C8—C9—H91108.4H1222—C122—H1223108.1
C8—C9—H92110.2C116—C119—C120114.9 (5)
H91—C9—H92111.1C116—C119—H1191107.7
C8—C9—H93108.1C120—C119—H1191109.2
H91—C9—H93109.7C116—C119—H1192107.8
H92—C9—H93109.4C120—C119—H1192108.8
C2—C10—O11110.5 (3)H1191—C119—H1192108.3
C2—C10—O24127.5 (3)C119—C120—H1201113.4
O11—C10—O24121.9 (3)C119—C120—H1202107.7
C10—O11—C12111.2 (3)H1201—C120—H1202109.2
C1—C12—O11104.7 (3)C119—C120—H1203108.6
C1—C12—C13112.7 (3)H1201—C120—H1203109.3
O11—C12—C13108.7 (3)H1202—C120—H1203108.5
C1—C12—H121110.2C113—O123—H123108.1
O11—C12—H121109.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O223—H2225···O115i0.821.922.696 (2)157
O123—H123···O2240.831.902.719 (2)166
O23—H23···O105i0.801.962.738 (2)162
Symmetry code: (i) x+1, y, z.
 

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ISSN: 2056-9890
Volume 62| Part 9| September 2006| Pages o3890-o3892
https://doi.org/10.1107/S1600536806031618
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