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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o236.
Published online 2007 December 12. doi:  10.1107/S1600536807064951
PMCID: PMC2915296

2,3,4,6-Tetra-O-benzoyl-4-nitro­phenyl-1-thio-α-d-mannopyran­oside–dichloro­methane–diethyl ether mixed solvate (1/0.53/0.38)

Abstract

The title compound, C40H31NO11S·0.53CH2Cl2·0.38C4H10O, was synthesized in two steps from mannose penta­acetate and single crystals were grown by slow evaporation. The structure was determined by single-crystal X-ray diffraction, confirming the α-configuration of the anomeric thioaryl substituent. The asymmetric unit contains two crystallographically distinct mol­ecules of the carbohydrate. The central pyran­ose rings of these are geometrically similar, but there are differences in the orientations of the benzoate substituents.

Related literature

For related literature, see: Cao et al. (1998 [triangle]); Shah & Bahl (1974 [triangle]); Cosier & Glazer (1986 [triangle]); France et al. (2004 [triangle]); Mootoo et al. (1988 [triangle]); Prince (1982 [triangle]); Roy et al. (1992 [triangle]); Watkin (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o236-scheme1.jpg

Experimental

Crystal data

  • C40H31NO11S·0.534CH2Cl2·0.382C4H10O
  • M r = 770.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o236-efi1.jpg
  • a = 11.7508 (2) Å
  • b = 20.5564 (3) Å
  • c = 16.4633 (2) Å
  • β = 105.8699 (16)°
  • V = 3825.20 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 150 K
  • 0.34 × 0.28 × 0.24 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.94, T max = 0.96
  • 35711 measured reflections
  • 15110 independent reflections
  • 13111 reflections with I > 3σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.056
  • S = 1.09
  • 13111 reflections
  • 990 parameters
  • 17 restraints
  • H-atom parameters not refined
  • Δρmax = 1.02 e Å−3
  • Δρmin = −0.92 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 6226 Friedel pairs
  • Flack parameter: 0.03 (5)

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO; 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: SHELXTL (Bruker, 2000 [triangle]); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064951/lw2055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064951/lw2055Isup2.hkl

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

Acknowledgments

The authors thank the EPSRC (project studentship GR/T24692/01 to LD) for financial support, and Dr Sarah Jenkinson for assistance with the preparation of the manuscript.

supplementary crystallographic information

Comment

Thioglycosides are extremely useful and versatile glycoside donors for the synthesis of oligosaccharides, which may be activated by a wide range of electrophiles and also by electrochemical methods (France et al., 2004). The nature of an aromatic substituent of an aryl thioglycoside has a strongly modulating effect on the reactivity of such a thioglycoside; strongly electron withdrawing substituents greatly reduce their reactivity towards electrophiles (Roy et al., 1992) and also increase their oxidation potentials. Such 'disarmed' (Mootoo et al., 1988) thioglycosides may themselves therefore be used as acceptors for the glycosylation of more reactive 'armed' thioglycoside donors. The title compound was obtained by a trans-esterification sequence from the corresponding peracetylated thioglycoside, itself synthesized from mannose penta-acetate by treatment with 4-nitrothiophenol and boron trifluoride etherate in dichloromethane, by Zemplen deacetylation followed by reaction with benzoyl chloride in pyridine in the presence of N,N-dimethylaminopyridine (DMAP).

Experimental

1,2,3,4,6-Penta-O-acetyl-D-mannopyranoside (2.17 g, 3.55 mmol) and 4-nitrothiophenol (1.75 g, 11.26 mmol) were suspended in anhydrous dichloromethane (15 ml), under an atmosphere of argon, the mixture was cooled to 0°C, and boron trifluoride diethyl etherate (3.3 ml, 26 mmol) was added dropwise. The reaction mixture was then stirred at room temperature until after 66 h, t.l.c. (petroleum ether/ethyl acetate, 1:1) indicated complete consumption of the starting material, and the formation of a single product (Rf 1/2). The reaction was quenched by the addition of triethylamine (10 ml), and the mixture was then partitioned between water (200 ml) and dichloromethane (200 ml). The aqueous layer was re-extracted with dichloromethane (3 x 200 ml), and the combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether/ethyl acetate, 7:3) to afford 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (1.98 g, 74%) which recrystallized from petroleum ether/ethyl acetate as a yellow crystalline solid; m.p 134–136°C (petroleum ether/ethyl acetate); lit., 135–136°C (methanol, Shah & Bahl, 1974); [α]D23 +158 (c, 0.9 CHCl3); lit., [α]D +142.6 (c, 0.93 CHCl3, Shah & Bahl,(1974): νmax (KBr) 1752 (νC=O ester), 1513, 1579, 1599 (νArC=C), 1233 (νCO ether), 1066 (νCO ether) cm-1; δH (400 MHz, CDCl3) 2.03 (3H, s, CH3CO), 2.04 (3, s, CH3CO), 2.07 (3H, s, CH3CO), 2.19 (3H, s, CH3CO), 4.10 (1H, dd, J5,6 2.5 Hz, J6,6' 12.0 Hz, H-6), 4.31 (1H, dd, J5,6' 6.0 Hz, J6,6' 12.0 Hz, H-6'), 4.41 (1H, ddd, J4,5 9.5 Hz, J5,6 2.5 Hz, J5,6' 6.0 Hz, H-5), 5.28 (1H, dd, J2,3 3.5 Hz, J3,4 10.0 Hz, H-3), 5.37 (1H, at, J3,4 10.0 Hz, J4,5 10.0 Hz, H-4), 5.48 (1H, dd, J1,2 2.0 Hz, J2,3 3.5 Hz, H-2), 5.70 (1H, d, J1,2 2.0 Hz, H-1), 7.60 (2 x 1H, 2 x dd, J 7.0 Hz, J 2.0 Hz, 2 x ArH), 8.17 (2 x 1H, dd, J 7.0 Hz, J 2.0 Hz, 2 x ArH); δC (100 MHz, CDCl3) 20.9 (2 x CH3CO), 21.0 (CH3CO), 21.1 (CH3CO), 62.4 (C-6), 66.2 (C-4), 69.4 (C-3), 70.4 (C-5), 70.8 (C-2), 84.3 (C-1), 124.3 (2 x ArCH), 129.8 (2 x ArCH), 142.9 (ArC), 146.9 (ArC), 169.9 (C=O), 170.1 (C=O), 170.1 (C=O), 170.6 (C=O); (HMRS (ESI) Calcd. For C20H27O11N2S (M+NH4)+ 503.1336. Found 503.1334). (Found: C, 49.49; H, 4.79; N, 2.88. C20H23O11SN requires: C, 49.48; H, 4.77; N, 2.88%).

4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside, as prepared above, (1.66 g, 3.43 mmol) was dissolved in methanol (26 ml) and sodium methoxide (0.20 g, 3.80 mmol) was added. The reaction mixture was then stirred at 22°C and, after 45 min, t.l.c. (petroleum ether/ethyl acetate, 1:1) indicated complete consumption of the starting material (Rf 0.6) and the formation of a single product (Rf 0.1). Cation exchange resin IR-120 was then added until neutral pH was attained, and then the mixture was filtered and the solvent was removed under reduced pressure. Azeotropic evaporation with toluene (15 ml) furnished the crude product, which was used in the next step without further purification. The residue was dissolved in pyridine (10 ml) and the mixture was cooled to 0°C. Benzoyl chloride (2.5 ml, 21.52 mmol), and N,N-dimethylaminopyridine (97 mg, 0.79 mmol) were added and the reaction mixture was stirred at room temperature for 24 h after which time, t.l.c.(petroleum ether/ethyl acetate, 7:3) indicated complete consumption of the starting material (Rf 0.0) and the formation of three major products (Rf 0.2 identified as 4-nitrothiophenyl 2,3,6-tri-O-benzoyl-α,D-mannopyranoside; Rf 0.3, Rf 0.4 identified as 1,2,3,4,6-penta-O-benzoyl-D-mannopyranoside; Rf 0.5 identified as the desired 4-nitrothiophenyl 2,3,4,6-tetra-O-benzoyl-α,D-mannopyranoside). The mixture was partitioned between water (40 ml) and dichloromethane (70 ml), and the aqueous layer was re-extracted with dichloromethane (3 x 70 ml). The combined organic extracts were washed with aqueous hydrochloric acid (1M, 3 x 70 ml), a saturated aqueous solution of sodium hydrogen carbonate (140 ml), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (petroleum ether/ethyl acetate) and then re-crystallized from petroleum ether/ethyl acetate to afford 4-nitrothiophenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside (934 mg, 37%) as yellow crystals; m.p 119–120°C (from petroleum ether/ethyl acetate); a sample suitable for X-ray analysis was then re-crystallized by slow evaporation of a solution in dichloromethane/diethyl ether; [α]D23 +77 (c, 1.0 in CHCl3); νmax (KBr) 1728 (νC=O ester), 1452, 1518, 1581, 1600 (νArC=C), 1265 (νCO ester), 1093 (νCO ester), 709 (νArCH) cm-1; δH (400 MHz, CDCl3) 4.61 (1H, dd, J5,6 6.0 Hz, J6,6' 12.5 Hz, H-6), 4.66 (1H, dd, J5,6' 3.0 Hz, J6,6' 12.5 Hz, H-6'), 4.93 (1H, dd, J4,5 10.0 Hz, J5,6 6.0 Hz, J5,6' 3.0 Hz, H-5), 5.88 (1H, dd, J2,3 3.0 Hz, J3,4 10.0 Hz, H-3), 5.96 (1H, dd, J1,2 1.5 Hz, J2,3 3.0 Hz, H-2), 6.04 (1H, d, J1,2 1.5 Hz, H-1), 6.14 (1H, at, J3,4 10.0 Hz, J4,5 10.0 Hz, H– 4), 7.20–8.20 (24 x 1H, m, 24 x ArH); δC (100 MHz, CDCl3) 60.6 (C-6), 63.0 (C-4), 67.0 (C-3), 70.4 (C-5), 71.6 (C-2), 84.0 (C-1), 124.3 (2 x ArCH), 128.6 (2 x ArCH), 128.8 (2 x ArCH), 128.9 (2 x ArCH), 129.1 (2 x ArC), 129.5 (2 x ArCH), 129.6 (2 x ArC), 129.8 (2 x ArCH), 130.0 (2 x ArCH), 130.1 (2 x ArCH), 130.1 (2 x ArCH), 130.2 (2 x ArCH), 133.6 (ArCH), 133.7 (ArCH), 133.9 (ArCH), 134.0 (ArCH), 142.6 (ArC), 146.7 (ArC), 165.5 (C=O), 165.7 (2 x C=O), 166.1 (C=O); m/z (ESI) 792.12 ([M+NH4+CH3CN]+, 100%). (Found: C, 65.40; H, 4.78; N, 1.98; S, 4.27. C40H31O11SN requires: C, 65.48; H, 4.26; N, 1.91; S, 4.37%).

Refinement

A single-crystal (approximately 0.24 x 0.28 x 0.34 mm) was mounted on a glass fibre using perfluoropolyether oil and cooled rapidly to 150 K in a stream of cold N2 using an Oxford Cryosystems CRYOSTREAM unit (Cosier and Glazer, 1986). Diffraction data were measured using an Enraf–Nonius KappaCCD diffractometer (graphite-monochromated Mo Kα radiation, λ = 0.71073 Å). Intensity data were processed using the DENZO-SMN package (Otwinowski and Minor, 1997).

The structure was solved in the space group P 21 using the direct-methods program SIR92 (Altomare et al., 1994), which located all ordered non-hydrogen atoms. Subsequent full-matrix least-squares refinement was carried out using the CRYSTALS program suite (Betteridge et al., 2003). Coordinates and anisotropic thermal parameters of all non-hydrogen atoms were refined.

A difference Fourier map showed the presence of several peaks of electron density located within a small cavity within the lattice. These were identified as the non-hydrogen atoms of a disordered mixture of CH2Cl2 and Et2O. The coordinates, isotropic thermal parameters and site occupancies of these were refined. The C—Cl distances were restrained to 1.77 (2) Å, the C—O distances to 1.44 (2) Å and the C—C distances to 1.50 (2) Å. Bond angles were restrained to 112 (2)° and similarity restraints applied to the thermal parameters of directly-bonded atoms.

All hydrogen atoms were positioned geometrically after each cycle of refinement. A 3-term Chebychev polynomial weighting scheme was applied w = [1-(||Fo|-Fc||/6σ(Fo))2]2 / [1.64T0(x)+0.395T1(x) + 1.16]*Tn-1(x)] (Watkin, 1994, Prince, 1982).

Figures

Fig. 1.
Synthesis of (I).
Fig. 2.
The molecular structure of 4-Nitrophenyl-2,3,4,6,-tetra-O-benzoyl-1-thio-α-D-mannopyranoside (I) drawn with probability ellipsoids drawn at 50%.
Fig. 3.
The crystal structure of (I) viewed down the c axis. The diethylether (the minor component of the disordered solvent) is omitted for clarity and intermolecular contacts are shown with a broken bond.

Crystal data

C40H31NO11S·0.534CH2Cl2·0.382C4H10OF000 = 1604.9
Mr = 770.56Dx = 1.338 Mg m3
Monoclinic, P21Melting point = 392–393 K
Hall symbol: P 2ybMo Kα radiation λ = 0.71073 Å
a = 11.7508 (2) ÅCell parameters from 35711 reflections
b = 20.5564 (3) Åθ = 5–28º
c = 16.4633 (2) ŵ = 0.19 mm1
β = 105.8699 (16)ºT = 150 K
V = 3825.20 (10) Å3Block, colourless
Z = 40.34 × 0.28 × 0.24 mm

Data collection

Nonius KappaCCD diffractometer13111 reflections with I > 3σ(I)
Monochromator: graphiteRint = 0.033
T = 150 Kθmax = 27.5º
ω scansθmin = 5.2º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)h = −15→15
Tmin = 0.94, Tmax = 0.96k = −22→26
35711 measured reflectionsl = −21→20
15110 independent reflections

Refinement

Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.047  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: 1.64 0.395 1.16
wR(F2) = 0.056(Δ/σ)max = 0.022
S = 1.09Δρmax = 1.02 e Å3
13111 reflectionsΔρmin = −0.92 e Å3
990 parametersExtinction correction: None
17 restraintsAbsolute structure: Flack (1983), 6226 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (5)

Special details

Refinement. Geometric restraints were applied to the disordered solvent. The C—Cl bond lengths of the dichloromethane were restrained to 1.77 (2) Å and the Cl—C—Cl angle t0 112 (2) °. The C—O bond lengths of the diethyl ether were restrained to 1.44 (2) Å, the C—C bond lengths to 1.50 (2) Å and athe C—O—C and C—C—O angles to 112 (2) °. Similarity restraints were applied to the displacement parameters of directly-bonded atoms.

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

xyzUiso*/UeqOcc. (<1)
C10.3485 (2)0.20275 (12)0.75601 (14)0.0334
C20.4009 (2)0.24747 (12)0.83156 (14)0.0327
C30.5206 (2)0.22266 (14)0.88413 (14)0.0351
C40.5142 (2)0.15140 (13)0.90501 (15)0.0347
C50.4704 (2)0.11426 (13)0.82197 (14)0.0333
C60.4623 (2)0.04204 (14)0.83407 (16)0.0419
O10.35374 (13)0.13699 (9)0.78018 (10)0.0333
S10.42285 (5)0.21933 (4)0.67336 (4)0.0367
C70.3479 (2)0.16471 (13)0.59285 (14)0.0350
C80.4099 (2)0.14367 (18)0.53705 (19)0.0517
C90.3541 (3)0.10490 (19)0.46936 (19)0.0558
C100.2387 (2)0.08738 (14)0.45869 (15)0.0387
C110.1773 (2)0.10510 (14)0.51562 (15)0.0377
C120.2327 (2)0.14418 (15)0.58333 (16)0.0412
N10.17696 (19)0.04720 (13)0.38677 (14)0.0445
O20.08023 (17)0.02439 (11)0.38503 (13)0.0502
O30.2256 (2)0.03731 (16)0.33113 (15)0.0737
O40.32209 (14)0.24493 (9)0.88592 (10)0.0341
C130.2288 (2)0.28532 (14)0.86521 (16)0.0401
O50.2118 (2)0.32160 (13)0.80651 (15)0.0661
C140.1482 (2)0.27773 (14)0.92039 (15)0.0397
C150.0434 (3)0.3124 (2)0.89847 (18)0.0582
C16−0.0371 (3)0.3063 (2)0.9459 (2)0.0672
C17−0.0103 (3)0.2666 (2)1.0161 (2)0.0643
C180.0939 (3)0.23243 (18)1.03802 (19)0.0543
C190.1729 (2)0.23770 (14)0.98923 (16)0.0430
O60.55718 (16)0.25928 (10)0.96153 (10)0.0401
C200.63117 (19)0.31012 (15)0.96216 (16)0.0405
O70.6610 (2)0.32637 (12)0.90037 (15)0.0612
C210.6683 (2)0.34271 (15)1.04521 (18)0.0455
C220.7575 (3)0.3887 (2)1.0578 (3)0.0674
C230.7963 (3)0.4197 (2)1.1352 (3)0.0811
C240.7428 (4)0.4052 (2)1.1990 (3)0.0810
C250.6532 (5)0.3621 (2)1.1864 (2)0.0847
C260.6147 (4)0.3292 (2)1.1087 (2)0.0655
O80.63060 (15)0.12817 (10)0.94727 (10)0.0376
C270.6491 (2)0.10785 (14)1.02859 (15)0.0397
O90.5775 (2)0.11496 (13)1.06783 (12)0.0579
C280.7662 (2)0.07626 (14)1.06209 (16)0.0404
C290.7884 (3)0.04481 (15)1.13976 (17)0.0458
C300.8962 (3)0.01456 (17)1.17299 (19)0.0538
C310.9806 (3)0.0155 (2)1.1289 (2)0.0646
C320.9594 (3)0.0466 (2)1.0523 (2)0.0704
C330.8506 (3)0.0774 (2)1.0176 (2)0.0569
O100.42552 (16)0.00992 (9)0.75326 (12)0.0423
C340.5109 (2)−0.00435 (14)0.71473 (18)0.0434
O110.61203 (18)0.01133 (13)0.74273 (16)0.0635
C350.4616 (2)−0.04244 (13)0.63676 (16)0.0381
C360.5396 (2)−0.07579 (16)0.6013 (2)0.0494
C370.4961 (3)−0.11516 (18)0.5318 (2)0.0562
C380.3762 (3)−0.12077 (18)0.49602 (18)0.0552
C390.2977 (3)−0.08711 (18)0.53029 (19)0.0544
C400.3405 (2)−0.04780 (16)0.60101 (18)0.0450
C410.26154 (19)0.41580 (12)0.67278 (14)0.0315
C420.18643 (19)0.37068 (12)0.60558 (15)0.0328
C430.17341 (18)0.39855 (12)0.51761 (14)0.0309
C440.12700 (18)0.46724 (12)0.51285 (14)0.0304
C450.21561 (19)0.50790 (12)0.57930 (14)0.0314
C460.1785 (2)0.57783 (13)0.58226 (16)0.0373
O120.22502 (14)0.48116 (9)0.66179 (9)0.0321
S20.41553 (5)0.40293 (4)0.67172 (4)0.0381
C470.49023 (19)0.45247 (12)0.75730 (14)0.0324
C480.5753 (2)0.49391 (15)0.74431 (16)0.0413
C490.6451 (2)0.52957 (16)0.81047 (19)0.0472
C500.6256 (2)0.52333 (15)0.88889 (17)0.0417
C510.5401 (3)0.48353 (18)0.90353 (17)0.0504
C520.4707 (3)0.44757 (16)0.83690 (17)0.0464
N20.6997 (2)0.56152 (14)0.95943 (17)0.0532
O130.6792 (2)0.55904 (17)1.02758 (15)0.0808
O140.7772 (2)0.59475 (16)0.94602 (18)0.0797
O150.07157 (13)0.36799 (9)0.62155 (10)0.0331
C530.0279 (2)0.30843 (14)0.62848 (16)0.0395
O160.0725 (2)0.25897 (11)0.6129 (2)0.0670
C54−0.0811 (2)0.31107 (15)0.65817 (15)0.0381
C55−0.1444 (3)0.25400 (17)0.6570 (3)0.0622
C56−0.2436 (3)0.25451 (19)0.6878 (3)0.0680
C57−0.2768 (2)0.3098 (2)0.72114 (19)0.0549
C58−0.2135 (2)0.36720 (18)0.72253 (18)0.0500
C59−0.1163 (2)0.36789 (14)0.68942 (16)0.0397
O170.09266 (14)0.35917 (9)0.45580 (10)0.0355
C600.1424 (2)0.30785 (15)0.42710 (16)0.0412
O180.24693 (18)0.29581 (12)0.44975 (15)0.0578
C610.0530 (3)0.26855 (15)0.36537 (18)0.0485
C620.0943 (4)0.21823 (19)0.3241 (2)0.0659
C630.0116 (6)0.1813 (2)0.2643 (3)0.0904
C64−0.1078 (6)0.1937 (2)0.2493 (3)0.1019
C65−0.1476 (4)0.2425 (2)0.2901 (3)0.0978
C66−0.0677 (3)0.28158 (19)0.3485 (3)0.0688
O190.12558 (13)0.49534 (9)0.43191 (9)0.0333
C670.0178 (2)0.50624 (13)0.37719 (15)0.0341
O20−0.07288 (14)0.48790 (12)0.38980 (12)0.0470
C680.0252 (2)0.54598 (12)0.30379 (14)0.0322
C69−0.0793 (2)0.57149 (14)0.25221 (15)0.0381
C70−0.0772 (2)0.61037 (15)0.18393 (16)0.0439
C710.0292 (3)0.62314 (16)0.16675 (17)0.0474
C720.1334 (3)0.59729 (16)0.21751 (18)0.0485
C730.1322 (2)0.55882 (14)0.28612 (15)0.0395
O210.27237 (16)0.61394 (9)0.63867 (11)0.0395
C740.3472 (2)0.64617 (15)0.60414 (17)0.0423
O220.3395 (2)0.64607 (15)0.52988 (14)0.0735
C750.4403 (2)0.68082 (14)0.66897 (17)0.0400
C760.5086 (3)0.72712 (18)0.64269 (18)0.0537
C770.5959 (3)0.76050 (19)0.7011 (2)0.0598
C780.6167 (3)0.74684 (17)0.7860 (2)0.0536
C790.5496 (3)0.70121 (16)0.81305 (18)0.0491
C800.4611 (2)0.66776 (14)0.75483 (17)0.0424
C810.1792 (8)0.4317 (5)0.1287 (6)0.0898 (14)*0.534 (4)
Cl10.1465 (2)0.37865 (12)0.20622 (15)0.0858 (8)*0.534 (4)
Cl20.2986 (3)0.40333 (15)0.09106 (18)0.0981 (9)*0.534 (4)
O230.2198 (6)0.3899 (4)0.1234 (5)0.079 (2)*0.382 (9)
C820.1264 (9)0.4009 (6)0.1491 (7)0.074 (2)*0.382 (9)
C830.0459 (9)0.4470 (5)0.1026 (7)0.072 (2)*0.382 (9)
C840.2408 (9)0.4219 (5)0.0637 (7)0.069 (2)*0.382 (9)
C850.3509 (8)0.4000 (5)0.0541 (7)0.068 (2)*0.382 (9)
H110.26230.21220.73230.0403*
H210.41020.29210.81010.0400*
H310.57910.22820.85050.0420*
H410.46030.14510.94200.0414*
H510.52860.12210.78870.0400*
H610.54150.02510.86630.0489*
H620.40320.03310.86640.0489*
H810.49450.15650.54580.0644*
H910.39770.08980.42850.0702*
H1110.09410.09000.50810.0455*
H1210.18960.15760.62530.0501*
H1510.02560.34190.84830.0703*
H161−0.11390.33040.92930.0822*
H171−0.06720.26271.05120.0805*
H1810.11280.20381.08900.0678*
H1910.24810.21211.00450.0521*
H2210.79390.39941.01120.0794*
H2310.86200.45221.14520.0910*
H2410.77140.42731.25500.0875*
H2510.61420.35351.23220.0994*
H2610.54940.29641.09940.0783*
H2910.72670.04411.17130.0533*
H3010.9129−0.00801.22890.0609*
H3111.0583−0.00671.15310.0724*
H3211.02160.04711.02120.0834*
H3310.83420.09990.96170.0668*
H3610.6269−0.07120.62630.0606*
H3710.5523−0.13980.50730.0701*
H3810.3454−0.14910.44530.0650*
H3910.2105−0.09110.50420.0628*
H4010.2842−0.02360.62590.0529*
H4110.25200.40510.72980.0381*
H4210.22360.32670.60800.0390*
H4310.25260.39870.50600.0373*
H4410.04610.46690.52160.0371*
H4510.29180.50650.56330.0380*
H4610.10600.57990.60290.0440*
H4620.16090.59710.52440.0440*
H4810.58680.49830.68660.0503*
H4910.70830.55920.80170.0576*
H5110.52780.48040.96120.0601*
H5210.40720.41840.84590.0556*
H551−0.11920.21300.63430.0784*
H561−0.29100.21380.68550.0850*
H571−0.34690.30910.74460.0680*
H581−0.23750.40770.74710.0605*
H591−0.07210.40930.68820.0480*
H6210.18080.20870.33680.0799*
H6310.03910.14600.23250.1099*
H641−0.16610.16630.20770.1106*
H651−0.23450.25050.27830.1058*
H661−0.09660.31820.37760.0773*
H691−0.15630.56170.26450.0443*
H701−0.15240.62910.14730.0502*
H7110.03110.65120.11750.0566*
H7210.21010.60650.20440.0593*
H7310.20760.54040.32270.0467*
H7610.49450.73640.58110.0656*
H7710.64380.79440.68200.0720*
H7810.68110.77030.82820.0629*
H7910.56450.69210.87480.0579*
H8010.41260.63440.77440.0507*
H8110.20020.47560.15470.1077*0.534
H8120.10710.43530.07980.1077*0.534
H8210.15360.41640.20890.0892*0.382
H8220.08320.35870.14700.0892*0.382
H8310.08090.46870.06070.0858*0.382
H8320.02890.48030.14200.0858*0.382
H833−0.02930.42460.07220.0858*0.382
H8410.24510.46940.07730.0833*0.382
H8420.17680.41410.01030.0833*0.382
H8510.37010.42440.00710.0812*0.382
H8520.41420.40770.10780.0812*0.382
H8530.34590.35250.04080.0812*0.382

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0348 (11)0.0378 (14)0.0282 (10)−0.0020 (9)0.0098 (8)0.0008 (9)
C20.0385 (11)0.0328 (13)0.0287 (10)−0.0015 (9)0.0124 (9)−0.0002 (9)
C30.0375 (11)0.0385 (13)0.0290 (10)−0.0065 (10)0.0083 (8)−0.0071 (10)
C40.0321 (11)0.0400 (14)0.0315 (11)−0.0002 (9)0.0078 (9)0.0015 (10)
C50.0341 (11)0.0338 (13)0.0322 (11)−0.0005 (9)0.0094 (9)−0.0026 (9)
C60.0522 (14)0.0359 (14)0.0343 (12)−0.0005 (11)0.0063 (10)−0.0055 (10)
O10.0317 (7)0.0353 (9)0.0312 (8)−0.0043 (6)0.0057 (6)0.0000 (7)
S10.0418 (3)0.0403 (3)0.0303 (3)−0.0084 (3)0.0137 (2)−0.0034 (2)
C70.0388 (12)0.0403 (15)0.0275 (11)0.0008 (10)0.0115 (9)0.0017 (9)
C80.0393 (13)0.071 (2)0.0507 (15)−0.0119 (13)0.0225 (12)−0.0155 (15)
C90.0456 (14)0.081 (2)0.0491 (15)−0.0076 (14)0.0265 (12)−0.0249 (15)
C100.0376 (12)0.0467 (16)0.0317 (11)0.0001 (10)0.0092 (9)−0.0071 (10)
C110.0333 (11)0.0467 (15)0.0338 (11)0.0008 (10)0.0105 (9)−0.0049 (11)
C120.0380 (12)0.0505 (17)0.0367 (12)−0.0010 (11)0.0132 (10)−0.0075 (11)
N10.0401 (11)0.0582 (16)0.0367 (11)0.0032 (10)0.0130 (9)−0.0124 (10)
O20.0414 (10)0.0613 (14)0.0462 (10)−0.0042 (9)0.0090 (8)−0.0164 (9)
O30.0587 (13)0.111 (2)0.0564 (13)−0.0140 (13)0.0236 (11)−0.0436 (14)
O40.0394 (8)0.036 (1)0.0287 (7)0.0014 (7)0.0128 (6)0.0003 (7)
C130.0420 (13)0.0426 (15)0.0370 (12)0.0054 (10)0.0132 (10)0.0061 (11)
O50.0702 (14)0.0738 (18)0.0638 (13)0.0298 (12)0.0342 (11)0.0348 (13)
C140.0408 (12)0.0464 (16)0.0315 (11)0.0013 (10)0.0090 (10)−0.0033 (10)
C150.0546 (15)0.077 (2)0.0441 (14)0.0182 (17)0.0154 (12)0.0118 (16)
C160.0498 (16)0.099 (3)0.0562 (17)0.0191 (18)0.0213 (13)0.008 (2)
C170.0559 (17)0.090 (3)0.0554 (18)0.0011 (17)0.0294 (15)0.0001 (17)
C180.0590 (17)0.067 (2)0.0435 (14)0.0053 (14)0.0248 (13)0.0080 (14)
C190.0428 (13)0.0506 (18)0.0370 (12)0.0042 (11)0.0133 (10)0.0052 (11)
O60.0450 (9)0.0457 (11)0.0298 (8)−0.0091 (8)0.0104 (7)−0.0112 (7)
C200.0289 (10)0.0447 (14)0.0472 (13)−0.0025 (10)0.0093 (9)−0.0125 (13)
O70.0669 (13)0.0626 (16)0.0641 (13)−0.0295 (11)0.0348 (11)−0.0241 (11)
C210.0392 (12)0.0455 (16)0.0470 (14)0.0074 (11)0.0033 (11)−0.0163 (12)
C220.0427 (15)0.073 (3)0.083 (2)−0.0063 (14)0.0111 (15)−0.042 (2)
C230.0489 (17)0.077 (3)0.102 (3)0.0016 (16)−0.0062 (18)−0.060 (2)
C240.079 (2)0.075 (3)0.065 (2)0.024 (2)−0.0213 (19)−0.043 (2)
C250.117 (3)0.081 (3)0.0506 (19)−0.002 (3)0.013 (2)−0.027 (2)
C260.080 (2)0.069 (3)0.0467 (16)−0.0095 (17)0.0162 (15)−0.0203 (15)
O80.0356 (8)0.0465 (11)0.0291 (8)0.0001 (7)0.0061 (6)0.0000 (7)
C270.0449 (13)0.0434 (15)0.0284 (11)−0.0005 (11)0.0062 (9)−0.0050 (10)
O90.0641 (13)0.0794 (17)0.0353 (9)0.0232 (11)0.0221 (9)0.0074 (10)
C280.0417 (12)0.0421 (15)0.0332 (11)−0.0026 (10)0.0030 (9)−0.0059 (10)
C290.0504 (14)0.0447 (16)0.0383 (13)−0.0001 (12)0.0050 (11)0.0005 (12)
C300.0545 (16)0.0551 (19)0.0427 (15)0.0018 (13)−0.0018 (12)0.0049 (13)
C310.0415 (15)0.076 (2)0.064 (2)0.0066 (14)−0.0073 (13)0.0021 (17)
C320.0377 (15)0.106 (3)0.065 (2)0.0067 (16)0.0099 (13)0.010 (2)
C330.0417 (14)0.079 (2)0.0461 (15)0.0024 (14)0.0059 (12)0.0082 (15)
O100.0431 (9)0.0378 (10)0.0442 (10)−0.0035 (7)0.0091 (8)−0.0095 (8)
C340.0360 (12)0.0407 (15)0.0532 (15)0.0025 (10)0.0119 (11)−0.0020 (12)
O110.0382 (10)0.0710 (16)0.0776 (15)−0.0068 (10)0.0096 (10)−0.0244 (12)
C350.0379 (12)0.0363 (14)0.0389 (12)0.0011 (10)0.0085 (10)0.0018 (10)
C360.0377 (13)0.0578 (19)0.0560 (16)0.0009 (11)0.0184 (12)−0.0018 (13)
C370.0618 (17)0.066 (2)0.0477 (15)0.0091 (15)0.0261 (14)−0.0027 (14)
C380.0607 (17)0.063 (2)0.0384 (13)0.0064 (14)0.0086 (12)−0.0089 (13)
C390.0449 (14)0.066 (2)0.0466 (15)0.0032 (13)0.0018 (12)−0.0070 (14)
C400.0390 (13)0.0512 (17)0.0421 (13)0.0089 (11)0.0068 (10)−0.0029 (12)
C410.0289 (10)0.0355 (13)0.0308 (10)0.0007 (8)0.0092 (8)0.0026 (9)
C420.0278 (10)0.0337 (13)0.0359 (11)−0.0021 (9)0.0072 (8)0.0020 (10)
C430.0269 (9)0.0357 (13)0.0307 (10)−0.0055 (9)0.0089 (8)−0.0033 (9)
C440.0274 (10)0.0372 (13)0.0282 (10)−0.0028 (8)0.0102 (8)0.0007 (9)
C450.0311 (10)0.0375 (14)0.0264 (10)−0.0049 (9)0.0095 (8)0.0031 (9)
C460.0391 (12)0.0337 (14)0.0373 (12)−0.0062 (10)0.0076 (9)0.0015 (10)
O120.0361 (8)0.0348 (9)0.0263 (7)−0.0016 (6)0.0099 (6)−0.0002 (6)
S20.0288 (2)0.0468 (4)0.0366 (3)−0.0002 (2)0.0056 (2)−0.0082 (3)
C470.0290 (10)0.0332 (13)0.0323 (11)0.0030 (9)0.0039 (8)−0.0038 (9)
C480.0359 (12)0.0532 (17)0.0367 (12)−0.0047 (11)0.0131 (10)−0.0059 (11)
C490.0375 (12)0.0537 (18)0.0528 (15)−0.0090 (11)0.0161 (11)−0.0118 (13)
C500.0340 (11)0.0481 (17)0.0408 (13)0.0033 (10)0.0063 (10)−0.0121 (11)
C510.0491 (15)0.066 (2)0.0356 (13)−0.0083 (14)0.0097 (11)−0.0070 (13)
C520.0507 (15)0.0531 (18)0.0352 (12)−0.0147 (12)0.0115 (11)−0.0008 (12)
N20.0364 (11)0.0617 (17)0.0580 (15)0.0009 (11)0.0070 (10)−0.0244 (13)
O130.0728 (15)0.123 (3)0.0431 (12)−0.0163 (16)0.0106 (11)−0.0338 (14)
O140.0610 (14)0.096 (2)0.0817 (17)−0.0294 (14)0.0179 (12)−0.0446 (16)
O150.0312 (7)0.0325 (9)0.0385 (8)−0.0003 (6)0.0144 (7)0.0050 (7)
C530.0371 (11)0.0329 (13)0.0507 (13)0.0009 (10)0.0156 (10)0.0012 (12)
O160.0563 (12)0.0360 (12)0.124 (2)−0.0050 (9)0.0505 (14)−0.0074 (13)
C540.0324 (10)0.0403 (13)0.0432 (12)−0.0030 (10)0.0134 (9)0.0073 (12)
C550.0524 (16)0.0423 (18)0.101 (3)−0.0005 (13)0.0370 (17)0.0115 (18)
C560.0467 (16)0.056 (2)0.110 (3)−0.0028 (14)0.0359 (18)0.027 (2)
C570.0376 (12)0.079 (2)0.0534 (15)0.0057 (15)0.0211 (11)0.0234 (17)
C580.0387 (13)0.071 (2)0.0421 (14)0.0058 (13)0.0131 (11)−0.0019 (13)
C590.0346 (11)0.0471 (16)0.0382 (12)0.0011 (10)0.0114 (10)0.0033 (11)
O170.0313 (7)0.0393 (10)0.0341 (8)−0.0049 (6)0.0059 (6)−0.0060 (7)
C600.0444 (12)0.0416 (15)0.0388 (12)−0.0091 (11)0.0135 (10)−0.0047 (12)
O180.0448 (10)0.0617 (15)0.0696 (13)0.0009 (9)0.0203 (10)−0.0206 (11)
C610.0607 (17)0.0391 (16)0.0437 (14)−0.0129 (12)0.0111 (12)−0.0047 (12)
C620.096 (3)0.0479 (19)0.0562 (18)−0.0132 (18)0.0243 (17)−0.0141 (16)
C630.158 (5)0.053 (2)0.064 (2)−0.030 (3)0.036 (3)−0.0232 (19)
C640.145 (5)0.062 (3)0.069 (3)−0.038 (3)−0.020 (3)−0.011 (2)
C650.090 (3)0.069 (3)0.106 (3)−0.033 (2)−0.022 (3)−0.010 (3)
C660.063 (2)0.055 (2)0.075 (2)−0.0173 (16)−0.0038 (17)−0.0102 (17)
O190.0279 (7)0.0441 (10)0.0269 (7)−0.0040 (6)0.0058 (6)0.0040 (7)
C670.0313 (11)0.0352 (13)0.0323 (11)0.0000 (9)0.0026 (8)−0.0042 (9)
O200.0285 (8)0.0665 (14)0.0439 (10)−0.0055 (8)0.0062 (7)0.0091 (9)
C680.0328 (11)0.0338 (13)0.0275 (10)0.0003 (9)0.0040 (8)−0.0011 (9)
C690.0381 (12)0.0389 (14)0.0339 (11)0.0029 (10)0.0040 (9)−0.0020 (10)
C700.0469 (14)0.0426 (16)0.0360 (12)0.0074 (11)0.0011 (10)0.0008 (11)
C710.0589 (16)0.0488 (18)0.0337 (12)0.0084 (13)0.0116 (11)0.0098 (11)
C720.0467 (14)0.0575 (19)0.0441 (14)0.0024 (12)0.0172 (11)0.0094 (13)
C730.0378 (12)0.0454 (16)0.0337 (11)0.0056 (10)0.0072 (9)0.0034 (10)
O210.0462 (9)0.0371 (10)0.0351 (8)−0.0083 (7)0.0108 (7)0.0003 (7)
C740.0482 (14)0.0419 (16)0.0384 (13)−0.0109 (11)0.0145 (11)−0.0019 (11)
O220.0796 (16)0.105 (2)0.0397 (11)−0.0443 (15)0.0233 (11)−0.0079 (12)
C750.0410 (13)0.0375 (15)0.0419 (13)−0.0053 (10)0.0118 (10)−0.0026 (11)
C760.0556 (16)0.063 (2)0.0456 (14)−0.0186 (14)0.0186 (12)0.0017 (14)
C770.0572 (17)0.063 (2)0.0600 (18)−0.0248 (15)0.0172 (14)−0.0008 (15)
C780.0449 (14)0.0547 (19)0.0578 (17)−0.0136 (13)0.0080 (12)−0.0062 (14)
C790.0478 (14)0.0525 (19)0.0446 (14)−0.0049 (12)0.0086 (11)0.0021 (12)
C800.0425 (13)0.0420 (15)0.0424 (13)−0.0035 (11)0.0108 (10)0.0044 (11)

Geometric parameters (Å, °)

C1—H111.000C43—C441.508 (4)
C1—S11.839 (2)C44—H4411.000
C1—O11.406 (3)C44—O191.448 (3)
C1—C21.534 (3)C44—C451.535 (3)
C2—H211.000C45—H4511.000
C2—O41.454 (3)C45—O121.441 (3)
C2—C31.524 (3)C45—C461.507 (4)
C3—H311.000C46—H4621.000
C3—O61.441 (3)C46—H4611.000
C3—C41.511 (4)C46—O211.439 (3)
C4—H411.000S2—C471.765 (2)
C4—O81.436 (3)C47—C521.395 (4)
C4—C51.527 (3)C47—C481.374 (4)
C5—H511.000C48—H4811.000
C5—O11.434 (3)C48—C491.381 (4)
C5—C61.504 (4)C49—H4911.000
C6—H621.000C49—C501.378 (4)
C6—H611.000C50—N21.473 (3)
C6—O101.442 (3)C50—C511.367 (4)
S1—C71.776 (3)C51—H5111.000
C7—C121.386 (4)C51—C521.388 (4)
C7—C81.389 (4)C52—H5211.000
C8—H811.000N2—O141.207 (4)
C8—C91.381 (4)N2—O131.211 (4)
C9—H911.000O15—C531.344 (3)
C9—C101.368 (4)C53—C541.492 (3)
C10—N11.463 (3)C53—O161.203 (4)
C10—C111.379 (3)C54—C591.384 (4)
C11—H1111.000C54—C551.387 (4)
C11—C121.384 (4)C55—H5511.000
C12—H1211.000C55—C561.392 (5)
N1—O31.222 (3)C56—H5611.000
N1—O21.223 (3)C56—C571.365 (6)
O4—C131.343 (3)C57—H5711.000
C13—C141.488 (4)C57—C581.392 (5)
C13—O51.193 (3)C58—H5811.000
C14—C191.366 (4)C58—C591.394 (4)
C14—C151.382 (4)C59—H5911.000
C15—H1511.000O17—C601.352 (4)
C15—C161.387 (4)C60—C611.485 (4)
C16—H1611.000C60—O181.208 (3)
C16—C171.379 (5)C61—C661.395 (5)
C17—H1711.000C61—C621.395 (5)
C17—C181.371 (5)C62—H6211.000
C18—H1811.000C62—C631.402 (6)
C18—C191.388 (4)C63—H6311.000
C19—H1911.000C63—C641.380 (8)
O6—C201.358 (3)C64—H6411.000
C20—C211.477 (4)C64—C651.359 (9)
C20—O71.210 (3)C65—H6511.000
C21—C261.389 (5)C65—C661.399 (5)
C21—C221.384 (5)C66—H6611.000
C22—H2211.000O19—C671.357 (3)
C22—C231.386 (5)C67—C681.481 (3)
C23—H2311.000C67—O201.201 (3)
C23—C241.396 (7)C68—C731.392 (3)
C24—H2411.000C68—C691.390 (3)
C24—C251.348 (7)C69—H6911.000
C25—H2511.000C69—C701.385 (4)
C25—C261.408 (5)C70—H7011.000
C26—H2611.000C70—C711.381 (4)
O8—C271.362 (3)C71—H7111.000
C27—C281.485 (4)C71—C721.386 (4)
C27—O91.201 (3)C72—H7211.000
C28—C331.385 (4)C72—C731.382 (4)
C28—C291.392 (4)C73—H7311.000
C29—H2911.000O21—C741.345 (3)
C29—C301.383 (4)C74—C751.485 (4)
C30—H3011.000C74—O221.201 (3)
C30—C311.380 (5)C75—C801.393 (4)
C31—H3111.000C75—C761.388 (4)
C31—C321.375 (5)C76—H7611.000
C32—H3211.000C76—C771.382 (4)
C32—C331.401 (5)C77—H7711.000
C33—H3311.000C77—C781.381 (5)
O10—C341.357 (3)C78—H7811.000
C34—C351.480 (4)C78—C791.376 (4)
C34—O111.195 (3)C79—H7911.000
C35—C401.388 (4)C79—C801.388 (4)
C35—C361.393 (4)C80—H8011.000
C36—H3611.000C81—H8121.000
C36—C371.381 (5)C81—H8111.000
C37—H3711.000C81—Cl21.780 (9)
C37—C381.376 (5)C81—Cl11.798 (10)
C38—H3811.000O23—C841.262 (11)
C38—C391.390 (5)O23—C821.298 (11)
C39—H3911.000C82—H8221.000
C39—C401.393 (4)C82—H8211.000
C40—H4011.000C82—C831.408 (12)
C41—H4111.000C83—H8331.000
C41—S21.833 (2)C83—H8321.000
C41—O121.407 (3)C83—H8311.000
C41—C421.526 (3)C84—H8421.000
C42—H4211.000C84—H8411.000
C42—O151.445 (3)C84—C851.418 (12)
C42—C431.526 (3)C85—H8531.000
C43—H4311.000C85—H8521.000
C43—O171.436 (3)C85—H8511.000
H11—C1—S1108.133O17—C43—C42109.64 (19)
H11—C1—O1105.002C44—C43—C42110.00 (19)
S1—C1—O1113.25 (16)H441—C44—O19111.263
H11—C1—C2109.784H441—C44—C45112.798
S1—C1—C2108.81 (16)O19—C44—C45105.87 (17)
O1—C1—C2111.72 (18)H441—C44—C43109.343
H21—C2—O4113.523O19—C44—C43109.53 (18)
H21—C2—C3109.556C45—C44—C43107.91 (18)
O4—C2—C3106.43 (18)H451—C45—O12113.187
H21—C2—C1108.826H451—C45—C46108.868
O4—C2—C1107.19 (18)O12—C45—C46106.36 (19)
C3—C2—C1111.3 (2)H451—C45—C44106.177
H31—C3—O6110.270O12—C45—C44109.04 (18)
H31—C3—C4108.728C46—C45—C44113.35 (19)
O6—C3—C4109.06 (19)H462—C46—H461109.467
H31—C3—C2108.323H462—C46—O21109.445
O6—C3—C2109.5 (2)H461—C46—O21109.445
C4—C3—C2110.98 (19)H462—C46—C45109.446
H41—C4—O8109.877H461—C46—C45109.446
H41—C4—C5111.404O21—C46—C45109.6 (2)
O8—C4—C5108.1 (2)C41—O12—C45115.32 (17)
H41—C4—C3110.112C47—S2—C41100.71 (11)
O8—C4—C3109.44 (19)C52—C47—C48120.3 (2)
C5—C4—C3107.86 (19)C52—C47—S2122.3 (2)
H51—C5—O1113.085C48—C47—S2117.24 (18)
H51—C5—C6108.034H481—C48—C49119.770
O1—C5—C6107.33 (19)H481—C48—C47119.770
H51—C5—C4107.263C49—C48—C47120.5 (2)
O1—C5—C4108.10 (19)H491—C49—C50120.842
C6—C5—C4113.1 (2)H491—C49—C48120.842
H62—C6—H61109.467C50—C49—C48118.3 (3)
H62—C6—O10109.313N2—C50—C51119.0 (3)
H61—C6—O10109.314N2—C50—C49118.4 (3)
H62—C6—C5109.313C51—C50—C49122.7 (2)
H61—C6—C5109.314H511—C51—C52120.629
O10—C6—C5110.1 (2)H511—C51—C50120.629
C1—O1—C5114.29 (17)C52—C51—C50118.7 (3)
C7—S1—C1101.30 (11)H521—C52—C51120.258
C12—C7—C8120.3 (2)H521—C52—C47120.258
C12—C7—S1123.15 (19)C51—C52—C47119.5 (3)
C8—C7—S1116.6 (2)O14—N2—O13123.0 (3)
H81—C8—C9120.193O14—N2—C50118.1 (3)
H81—C8—C7120.193O13—N2—C50118.9 (3)
C9—C8—C7119.6 (2)C53—O15—C42116.57 (19)
H91—C9—C10120.297C54—C53—O16124.3 (3)
H91—C9—C8120.298C54—C53—O15112.1 (2)
C10—C9—C8119.4 (2)O16—C53—O15123.6 (2)
N1—C10—C11117.6 (2)C59—C54—C55120.3 (2)
N1—C10—C9120.5 (2)C59—C54—C53121.5 (2)
C11—C10—C9121.9 (2)C55—C54—C53118.1 (3)
H111—C11—C12120.571H551—C55—C56120.389
H111—C11—C10120.571H551—C55—C54120.387
C12—C11—C10118.9 (2)C56—C55—C54119.2 (3)
H121—C12—C11120.076H561—C56—C57119.561
H121—C12—C7120.074H561—C56—C55119.561
C11—C12—C7119.8 (2)C57—C56—C55120.9 (3)
O3—N1—O2122.7 (2)H571—C57—C58119.952
O3—N1—C10118.1 (2)H571—C57—C56119.952
O2—N1—C10119.2 (2)C58—C57—C56120.1 (2)
C13—O4—C2115.77 (19)H581—C58—C59120.198
C14—C13—O5124.5 (2)H581—C58—C57120.198
C14—C13—O4113.0 (2)C59—C58—C57119.6 (3)
O5—C13—O4122.4 (2)H591—C59—C54120.102
C19—C14—C15119.9 (3)H591—C59—C58120.102
C19—C14—C13122.9 (2)C54—C59—C58119.8 (3)
C15—C14—C13117.2 (2)C60—O17—C43114.99 (18)
H151—C15—C16119.913C61—C60—O18124.7 (3)
H151—C15—C14119.914C61—C60—O17111.8 (2)
C16—C15—C14120.2 (3)O18—C60—O17123.5 (2)
H161—C16—C17120.318C66—C61—C62121.0 (3)
H161—C16—C15120.318C66—C61—C60121.5 (3)
C17—C16—C15119.4 (3)C62—C61—C60117.5 (3)
H171—C17—C18119.771H621—C62—C63120.781
H171—C17—C16119.769H621—C62—C61120.782
C18—C17—C16120.5 (3)C63—C62—C61118.4 (4)
H181—C18—C19120.080H631—C63—C64119.944
H181—C18—C17120.080H631—C63—C62119.949
C19—C18—C17119.8 (3)C64—C63—C62120.1 (4)
H191—C19—C14119.879H641—C64—C65119.396
H191—C19—C18119.879H641—C64—C63119.408
C14—C19—C18120.2 (3)C65—C64—C63121.2 (4)
C20—O6—C3116.38 (19)H651—C65—C66119.789
C21—C20—O7124.9 (3)H651—C65—C64119.793
C21—C20—O6112.5 (2)C66—C65—C64120.4 (5)
O7—C20—O6122.6 (2)H661—C66—C61120.608
C26—C21—C22120.3 (3)H661—C66—C65120.608
C26—C21—C20121.7 (3)C61—C66—C65118.8 (4)
C22—C21—C20117.9 (3)C67—O19—C44116.78 (17)
H221—C22—C23120.084C68—C67—O20124.5 (2)
H221—C22—C21120.083C68—C67—O19112.38 (19)
C23—C22—C21119.8 (4)O20—C67—O19123.0 (2)
H231—C23—C24120.295C73—C68—C69119.9 (2)
H231—C23—C22120.295C73—C68—C67122.2 (2)
C24—C23—C22119.4 (4)C69—C68—C67117.9 (2)
H241—C24—C25119.413H691—C69—C70119.845
H241—C24—C23119.413H691—C69—C68119.845
C25—C24—C23121.2 (3)C70—C69—C68120.3 (2)
H251—C25—C26119.999H701—C70—C71120.193
H251—C25—C24119.999H701—C70—C69120.194
C26—C25—C24120.0 (4)C71—C70—C69119.6 (2)
H261—C26—C21120.406H711—C71—C72119.868
H261—C26—C25120.407H711—C71—C70119.868
C21—C26—C25119.2 (4)C72—C71—C70120.3 (3)
C27—O8—C4116.93 (19)H721—C72—C73119.754
C28—C27—O9124.6 (2)H721—C72—C71119.754
C28—C27—O8112.4 (2)C73—C72—C71120.5 (3)
O9—C27—O8123.0 (2)H731—C73—C72120.291
C33—C28—C29120.8 (3)H731—C73—C68120.291
C33—C28—C27121.4 (2)C72—C73—C68119.4 (2)
C29—C28—C27117.8 (2)C74—O21—C46117.13 (19)
H291—C29—C30120.205C75—C74—O22124.6 (2)
H291—C29—C28120.206C75—C74—O21111.8 (2)
C30—C29—C28119.6 (3)O22—C74—O21123.6 (2)
H301—C30—C31120.055C80—C75—C76119.5 (2)
H301—C30—C29120.055C80—C75—C74121.8 (2)
C31—C30—C29119.9 (3)C76—C75—C74118.7 (2)
H311—C31—C32119.579H761—C76—C77119.801
H311—C31—C30119.580H761—C76—C75119.801
C32—C31—C30120.8 (3)C77—C76—C75120.4 (3)
H321—C32—C33119.989H771—C77—C78120.126
H321—C32—C31119.989H771—C77—C76120.127
C33—C32—C31120.0 (3)C78—C77—C76119.7 (3)
H331—C33—C28120.556H781—C78—C79119.742
H331—C33—C32120.556H781—C78—C77119.742
C28—C33—C32118.9 (3)C79—C78—C77120.5 (3)
C34—O10—C6117.2 (2)H791—C79—C80119.948
C35—C34—O11126.1 (3)H791—C79—C78119.948
C35—C34—O10110.9 (2)C80—C79—C78120.1 (3)
O11—C34—O10123.0 (3)H801—C80—C79120.136
C40—C35—C36119.9 (2)H801—C80—C75120.136
C40—C35—C34121.5 (2)C79—C80—C75119.7 (3)
C36—C35—C34118.5 (2)H812—C81—H811109.469
H361—C36—C37120.040H812—C81—Cl2108.589
H361—C36—C35120.040H811—C81—Cl2108.588
C37—C36—C35119.9 (3)H812—C81—Cl1108.585
H371—C37—C38119.747H811—C81—Cl1108.585
H371—C37—C36119.747Cl2—C81—Cl1113.0 (5)
C38—C37—C36120.5 (3)C84—O23—C82121.8 (8)
H381—C38—C39119.995H822—C82—H821109.462
H381—C38—C37119.995H822—C82—C83107.770
C39—C38—C37120.0 (3)H821—C82—C83107.769
H391—C39—C40120.001H822—C82—O23107.761
H391—C39—C38120.002H821—C82—O23107.762
C40—C39—C38120.0 (3)C83—C82—O23116.2 (9)
H401—C40—C35120.188H833—C83—H832109.477
H401—C40—C39120.188H833—C83—H831109.473
C35—C40—C39119.6 (3)H832—C83—H831109.479
H411—C41—S2109.987H833—C83—C82109.465
H411—C41—O12102.869H832—C83—C82109.468
S2—C41—O12113.81 (16)H831—C83—C82109.466
H411—C41—C42110.796H842—C84—H841109.457
S2—C41—C42106.38 (16)H842—C84—C85109.960
O12—C41—C42113.05 (18)H841—C84—C85110.000
H421—C42—O15112.140H842—C84—O23109.950
H421—C42—C43107.906H841—C84—O23109.980
O15—C42—C43109.32 (17)C85—C84—O23107.5 (9)
H421—C42—C41111.144H853—C85—H852109.475
O15—C42—C41105.98 (19)H853—C85—H851109.494
C43—C42—C41110.35 (19)H852—C85—H851109.469
H431—C43—O17109.614H853—C85—C84109.480
H431—C43—C44109.257H852—C85—C84109.443
O17—C43—C44109.35 (17)H851—C85—C84109.467
H431—C43—C42108.964

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LW2055).

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