supplementary materials


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Acta Cryst. (2008). E64, o1868    [ doi:10.1107/S1600536808027189 ]

Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-[beta]-D-glucopyranoside

S. Manabe, K. Ishii, D. Hashizume and Y. Ito

Abstract top

In the crystal structure of the title compound, C27H27NO5S, the pyranose ring adopts a 4C1 chair conformation with puckering parameters Q = 0.639 (2) Å, [theta] = 174.11 (18) and [varphi] = 256 (2)°. The presence of the 2,3-trans-oxazolidinone fixes the conformation of the pyranose ring. The phenyl group attached to the S atom and the benzyl group bonding to the N atom are each disordered over two positions with site occupancies of 0.624 (3):0.376 (3) and 0.526 (3):0.474 (3), respectively. An intermolecular O-H...O hydrogen bond is observed.

Comment top

Recently, we and other groups reported 2,3-trans-oxazolidinone carrying novel glycosyl donors for α-selective glycosylation (Benakli et al., 2001; Boysen et al., 2005; Crich & Vinod, 2005; Manabe et al., 2006; Geng et al., 2008). Furthermore, we also found the 2,3-trans-oxazolidinone carrying pyranoses are easily anomerized via an endo-cleavage manner (Manabe et al., 2006; Satoh et al., 2008). In order to investigate the origin of the high stereosetectivity and its unique character, we are interested in the conformation of the pyranose ring with 2,3-trans-oxazolidinone group.

The pyranose ring of the title compound adapts a 4C1 chair conformation. The torsion angles (O1—C1—C2—C3, C1—C2—C3—C4, C2—C3—C4—C5, C3—C4—C5—O1, C4—C5—O1—C1 and C5—O1—C1—C2; see geometric parameters table in supplementary materials) and Cremer-Pople puckering parameters (Cremer & Pople, 1975), Q = 0.639 (2) Å, θ = 174.11 (18)° and φ = 256 (2)°, of the ring clearly indicate the 4C1 conformation.

Related literature top

For related literature, see: Benakli et al. (2001); Boysen et al. (2005); Cremer & Pople (1975); Crich & Vinod (2005); Geng et al. (2008); Manabe et al. (2006); Satoh et al. (2008).

Experimental top

The compound, (I), was prepared as described by Benakli et al. (2001). (I) was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single-crystal X-ray analysis.

Refinement top

The phenyl group bonding to the S atom and the benzyl group bonding to the N atom in (I) were disordered into two parts each other. Occupancy factors of each group were refined, where the atomic displacement parameters of the corresponding atoms in each group were constrained to be the same. Restraints were imposed on the C—C bond distances in the disordered phenyl groups to be 1.39 Å. The positions of H atoms on C atoms were calculated from geometries. The H atom of the hydroxyl group was located in a difference map. All H atoms were treated as riding atoms with C/O—H distances of 1.00, 0.99, 0.95 and 0.84 Å for methyne, methylene, phenyl and hydroxyl, respectively. The Uiso(H) values were fixed to be 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: CrystalClear SM (Rigaku/MSC, 2005); cell refinement: HKL2000 (Otwinowski & Minor, 1997); data reduction: HKL2000; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The minor parts of the disordered phenyl moieties are omitted for clarity.
Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside top
Crystal data top
C27H27NO5SF(000) = 504
Mr = 477.56Dx = 1.339 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7082 reflections
a = 13.8166 (7) Åθ = 1.4–27.5°
b = 5.7008 (3) ŵ = 0.18 mm−1
c = 15.0425 (9) ÅT = 90 K
β = 91.494 (4)°Needle, colourless
V = 1184.43 (11) Å30.30 × 0.08 × 0.07 mm
Z = 2
Data collection top
Rigaku AFC8
diffractometer with Saturn70 CCD		4965 independent reflections
Radiation source: fine-focus rotating anode3970 reflections with I > 2σ(I)
confocalRint = 0.040
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 1.4°
ω–scanh = −17→15
Absorption correction: multi-scan
(MULABS; Blessing, 1995)		k = −7→6
Tmin = 0.959, Tmax = 0.998l = −19→19
7074 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0942P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.011
4965 reflectionsΔρmax = 0.33 e Å−3
353 parametersΔρmin = −0.34 e Å−3
31 restraintsAbsolute structure: Flack (1983), 1983 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (11)
Crystal data top
C27H27NO5SV = 1184.43 (11) Å3
Mr = 477.56Z = 2
Monoclinic, P21Mo Kα radiation
a = 13.8166 (7) ŵ = 0.18 mm−1
b = 5.7008 (3) ÅT = 90 K
c = 15.0425 (9) Å0.30 × 0.08 × 0.07 mm
β = 91.494 (4)°
Data collection top
Rigaku AFC8
diffractometer with Saturn70 CCD		4965 independent reflections
Absorption correction: multi-scan
(MULABS; Blessing, 1995)		3970 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.998Rint = 0.040
7074 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.167Δρmax = 0.33 e Å−3
S = 1.03Δρmin = −0.34 e Å−3
4965 reflectionsAbsolute structure: Flack (1983), 1983 Friedel pairs
353 parametersFlack parameter: 0.05 (11)
31 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.34405 (4)0.61596 (13)0.35271 (4)0.03602 (14)
O10.16119 (10)0.6528 (3)0.30101 (9)0.0265 (3)
O20.07008 (11)0.0779 (3)0.44133 (9)0.0280 (4)
O3−0.06858 (11)0.3322 (3)0.31331 (10)0.0294 (4)
H3O−0.10540.30310.35550.035*
O40.05569 (11)0.9160 (3)0.17927 (9)0.0272 (4)
O50.16411 (12)−0.1618 (3)0.52679 (10)0.0333 (4)
N10.22987 (13)0.1425 (3)0.44686 (11)0.0266 (4)
C10.23048 (16)0.4742 (4)0.32615 (15)0.0268 (5)
H10.23830.36020.27630.032*
C20.18671 (15)0.3529 (4)0.40565 (13)0.0245 (5)
H20.17280.47140.45260.029*
C30.09332 (16)0.2431 (4)0.37230 (13)0.0254 (5)
H30.10760.15170.31740.030*
C40.01933 (15)0.4275 (4)0.34745 (13)0.0247 (5)
H40.00720.53290.39910.030*
C50.06745 (15)0.5641 (4)0.27204 (13)0.0240 (5)
H50.07600.45650.22030.029*
C60.00733 (16)0.7723 (4)0.24210 (14)0.0259 (5)
H61−0.05440.71550.21490.031*
H62−0.00840.86830.29460.031*
C70.15701 (17)0.0048 (4)0.47591 (14)0.0293 (5)
C8A0.39021 (14)0.6625 (6)0.24481 (13)0.0433 (7)0.624 (3)
C9A0.3372 (2)0.7700 (7)0.17667 (14)0.0450 (10)0.624 (3)
H9A0.27250.81850.18620.054*0.624 (3)
C10A0.37834 (16)0.8070 (8)0.09447 (18)0.0571 (11)0.624 (3)
H10A0.34280.87120.04530.068*0.624 (3)
C11A0.47501 (18)0.7437 (8)0.0892 (2)0.0800 (12)0.624 (3)
H11A0.50530.76690.03390.096*0.624 (3)
C12A0.5310 (2)0.6490 (10)0.15830 (17)0.094 (2)0.624 (3)
H12A0.59720.61150.15020.113*0.624 (3)
C13A0.48825 (16)0.6104 (10)0.2395 (2)0.0628 (13)0.624 (3)
H13A0.52430.55100.28920.075*0.624 (3)
C8B0.3898 (2)0.6505 (5)0.24391 (14)0.0433 (7)0.376 (3)
C9B0.3554 (3)0.8270 (7)0.18792 (19)0.0450 (10)0.376 (3)
H9B0.30310.92360.20520.054*0.376 (3)
C10B0.3982 (3)0.8608 (9)0.1063 (2)0.0571 (11)0.376 (3)
H10B0.37780.99610.07400.068*0.376 (3)
C11B0.4669 (4)0.7218 (6)0.0659 (3)0.0800 (12)0.376 (3)
H11B0.49790.76160.01240.096*0.376 (3)
C12B0.4845 (4)0.5173 (8)0.1138 (2)0.094 (2)0.376 (3)
H12B0.52310.39640.08960.113*0.376 (3)
C13B0.4453 (3)0.4903 (8)0.1974 (2)0.0628 (13)0.376 (3)
H13B0.45800.34490.22630.075*0.376 (3)
C140.323625 (11)0.13833 (2)0.49395 (2)0.0290 (5)
H1410.37480.17170.45090.035*
H1420.3350−0.02170.51750.035*
C15A0.333196 (11)0.31100 (2)0.56988 (2)0.0311 (5)0.526 (3)
C16A0.410308 (11)0.46761 (2)0.56994 (2)0.0464 (11)0.526 (3)
H16A0.45740.45740.52520.056*0.526 (3)
C17A0.4187 (2)0.6396 (6)0.63559 (18)0.0654 (15)0.526 (3)
H17A0.47420.73810.63680.078*0.526 (3)
C18A0.34885 (18)0.6723 (6)0.6995 (2)0.0455 (12)0.526 (3)
H18A0.35380.79550.74190.055*0.526 (3)
C19A0.2716 (2)0.5160 (5)0.6983 (2)0.0371 (7)0.526 (3)
H19A0.22370.52830.74220.045*0.526 (3)
C20A0.2633 (2)0.3421 (6)0.63375 (17)0.0306 (5)0.526 (3)
H20A0.20840.24170.63320.037*0.526 (3)
C15B0.33272 (2)0.30995 (3)0.57017 (3)0.0311 (5)0.474 (3)
C16B0.42307 (17)0.4031 (7)0.5928 (2)0.0464 (11)0.474 (3)
H16B0.47640.37100.55610.056*0.474 (3)
C17B0.4369 (2)0.5420 (9)0.6679 (2)0.0654 (15)0.474 (3)
H17B0.49780.61310.68120.078*0.474 (3)
C18B0.35861 (16)0.5736 (9)0.7230 (3)0.0455 (12)0.474 (3)
H18B0.36730.66130.77630.055*0.474 (3)
C19B0.2680 (2)0.4799 (6)0.7020 (2)0.0371 (7)0.474 (3)
H19B0.21470.51140.73880.045*0.474 (3)
C20B0.25570 (19)0.3397 (8)0.62686 (19)0.0306 (5)0.474 (3)
H20B0.19540.26520.61440.037*0.474 (3)
C210.0574 (2)0.8149 (4)0.09276 (14)0.0355 (6)
H211−0.00910.80920.06670.043*
H2120.08240.65250.09670.043*
C220.12116 (17)0.9594 (4)0.03426 (14)0.0297 (5)
C230.13491 (18)0.8889 (5)−0.05315 (14)0.0359 (6)
H230.10380.7511−0.07490.043*
C240.1933 (2)1.0167 (5)−0.10881 (16)0.0434 (7)
H240.20330.9649−0.16790.052*
C250.2369 (2)1.2195 (6)−0.07797 (18)0.0572 (9)
H250.27581.3094−0.11640.069*
C260.2243 (2)1.2937 (6)0.0092 (2)0.0610 (9)
H260.25431.43350.03040.073*
C270.1669 (2)1.1598 (5)0.06496 (15)0.0405 (7)
H270.15921.20740.12490.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0211 (2)0.0387 (3)0.0481 (3)−0.0025 (3)−0.0012 (2)0.0103 (3)
O10.0172 (6)0.0286 (7)0.0336 (7)−0.0016 (6)0.0000 (6)0.0039 (6)
O20.0292 (7)0.0257 (8)0.0292 (7)−0.0036 (6)0.0067 (6)0.0029 (6)
O30.0201 (7)0.0382 (8)0.0299 (7)−0.0081 (7)0.0018 (6)−0.0026 (7)
O40.0296 (8)0.0303 (7)0.0216 (6)−0.0015 (7)0.0019 (6)−0.0008 (6)
O50.0404 (9)0.0290 (8)0.0311 (7)0.0043 (7)0.0105 (7)0.0035 (6)
N10.0280 (9)0.0252 (8)0.0268 (8)0.0022 (8)0.0026 (7)0.0008 (7)
C10.0191 (10)0.0263 (10)0.0350 (11)0.0010 (9)0.0003 (9)0.0046 (9)
C20.0233 (10)0.0238 (10)0.0264 (9)−0.0009 (9)0.0026 (8)−0.0017 (8)
C30.0256 (10)0.0274 (10)0.0235 (9)−0.0059 (9)0.0064 (8)−0.0023 (8)
C40.0214 (10)0.0303 (10)0.0224 (9)−0.0066 (9)0.0024 (8)−0.0031 (8)
C50.0201 (9)0.0282 (11)0.0238 (9)−0.0028 (8)0.0004 (8)−0.0008 (8)
C60.0203 (10)0.0303 (11)0.0270 (10)−0.0034 (9)0.0003 (9)0.0005 (8)
C70.0348 (12)0.0273 (10)0.0263 (10)0.0019 (10)0.0079 (9)−0.0019 (8)
C8A0.0235 (11)0.0399 (13)0.0672 (15)0.0004 (11)0.0129 (11)0.0111 (12)
C9A0.0326 (17)0.060 (2)0.0426 (15)−0.0028 (18)0.0067 (14)−0.0048 (16)
C10A0.059 (2)0.069 (3)0.0444 (16)−0.024 (2)0.0153 (17)−0.0122 (18)
C11A0.085 (2)0.078 (2)0.080 (2)−0.016 (2)0.0654 (18)−0.004 (2)
C12A0.044 (2)0.116 (5)0.125 (4)0.012 (3)0.049 (2)0.001 (4)
C13A0.0211 (17)0.092 (3)0.076 (3)0.001 (2)0.0054 (17)0.002 (3)
C8B0.0235 (11)0.0399 (13)0.0672 (15)0.0004 (11)0.0129 (11)0.0111 (12)
C9B0.0326 (17)0.060 (2)0.0426 (15)−0.0028 (18)0.0067 (14)−0.0048 (16)
C10B0.059 (2)0.069 (3)0.0444 (16)−0.024 (2)0.0153 (17)−0.0122 (18)
C11B0.085 (2)0.078 (2)0.080 (2)−0.016 (2)0.0654 (18)−0.004 (2)
C12B0.044 (2)0.116 (5)0.125 (4)0.012 (3)0.049 (2)0.001 (4)
C13B0.0211 (17)0.092 (3)0.076 (3)0.001 (2)0.0054 (17)0.002 (3)
C140.0238 (9)0.0316 (11)0.0317 (10)0.0071 (10)0.0045 (8)0.0026 (10)
C15A0.0252 (11)0.0408 (12)0.0271 (10)0.0066 (10)−0.0008 (9)0.0045 (9)
C16A0.0222 (14)0.095 (3)0.0218 (16)−0.0046 (18)−0.0064 (13)−0.003 (2)
C17A0.0294 (17)0.134 (4)0.033 (2)−0.021 (2)−0.0030 (17)−0.025 (2)
C18A0.0459 (18)0.061 (3)0.0296 (17)−0.009 (2)0.0044 (15)−0.0054 (18)
C19A0.0285 (12)0.0524 (17)0.0306 (11)−0.0031 (12)0.0037 (10)−0.0021 (11)
C20A0.0249 (11)0.0373 (12)0.0296 (11)0.0044 (10)−0.0006 (10)0.0028 (10)
C15B0.0252 (11)0.0408 (12)0.0271 (10)0.0066 (10)−0.0008 (9)0.0045 (9)
C16B0.0222 (14)0.095 (3)0.0218 (16)−0.0046 (18)−0.0064 (13)−0.003 (2)
C17B0.0294 (17)0.134 (4)0.033 (2)−0.021 (2)−0.0030 (17)−0.025 (2)
C18B0.0459 (18)0.061 (3)0.0296 (17)−0.009 (2)0.0044 (15)−0.0054 (18)
C19B0.0285 (12)0.0524 (17)0.0306 (11)−0.0031 (12)0.0037 (10)−0.0021 (11)
C20B0.0249 (11)0.0373 (12)0.0296 (11)0.0044 (10)−0.0006 (10)0.0028 (10)
C210.0492 (14)0.0344 (11)0.0231 (10)−0.0067 (11)0.0037 (10)−0.0035 (9)
C220.0289 (11)0.0328 (11)0.0275 (10)0.0072 (10)0.0006 (9)0.0023 (9)
C230.0359 (12)0.0443 (13)0.0275 (10)0.0135 (11)0.0000 (10)0.0008 (10)
C240.0365 (13)0.0675 (16)0.0263 (11)0.0197 (13)0.0039 (10)0.0069 (11)
C250.0511 (17)0.087 (2)0.0340 (13)−0.0145 (17)0.0034 (13)0.0172 (14)
C260.068 (2)0.0681 (19)0.0474 (15)−0.0265 (17)0.0064 (15)0.0103 (14)
C270.0449 (14)0.0462 (14)0.0305 (11)−0.0062 (12)0.0009 (11)0.0041 (11)
Geometric parameters (Å, °) top
S1—C8A1.7791 (19)C11B—H11B0.9500
S1—C8B1.781 (2)C12B—C13B1.390 (3)
S1—C11.801 (2)C12B—H12B0.9500
O1—C11.441 (3)C13B—H13B0.9500
O1—C51.447 (2)C14—C15B1.5099 (4)
O2—C71.362 (3)C14—C15A1.5110 (4)
O2—C31.444 (2)C14—H1410.9900
O3—C41.415 (3)C14—H1420.9900
O3—H3O0.8400C15A—C16A1.3900 (2)
O4—C211.424 (3)C15A—C20A1.391 (2)
O4—C61.430 (3)C16A—C17A1.394 (2)
O5—C71.222 (3)C16A—H16A0.9500
N1—C71.358 (3)C17A—C18A1.393 (3)
N1—C141.4604 (18)C17A—H17A0.9500
N1—C21.470 (3)C18A—C19A1.390 (3)
C1—C21.520 (3)C18A—H18A0.9500
C1—H11.0000C19A—C20A1.390 (3)
C2—C31.508 (3)C19A—H19A0.9500
C2—H21.0000C20A—H20A0.9500
C3—C41.507 (3)C15B—C16B1.391 (2)
C3—H31.0000C15B—C20B1.391 (2)
C4—C51.541 (3)C16B—C17B1.389 (3)
C4—H41.0000C16B—H16B0.9500
C5—C61.511 (3)C17B—C18B1.391 (3)
C5—H51.0000C17B—H17B0.9500
C6—H610.9900C18B—C19B1.390 (3)
C6—H620.9900C18B—H18B0.9500
C8A—C9A1.387 (2)C19B—C20B1.390 (3)
C8A—C13A1.391 (2)C19B—H19B0.9500
C9A—C10A1.390 (2)C20B—H20B0.9500
C9A—H9A0.9500C21—C221.507 (3)
C10A—C11A1.388 (2)C21—H2110.9900
C10A—H10A0.9500C21—H2120.9900
C11A—C12A1.388 (3)C22—C271.379 (3)
C11A—H11A0.9500C22—C231.393 (3)
C12A—C13A1.388 (3)C23—C241.385 (4)
C12A—H12A0.9500C23—H230.9500
C13A—H13A0.9500C24—C251.379 (4)
C8B—C9B1.388 (3)C24—H240.9500
C8B—C13B1.393 (3)C25—C261.393 (4)
C9B—C10B1.390 (3)C25—H250.9500
C9B—H9B0.9500C26—C271.397 (4)
C10B—C11B1.389 (3)C26—H260.9500
C10B—H10B0.9500C27—H270.9500
C11B—C12B1.389 (3)
C8A—S1—C1101.28 (11)C9B—C10B—H10B115.9
C8B—S1—C1100.03 (13)C10B—C11B—C12B111.4 (4)
C1—O1—C5114.53 (15)C10B—C11B—H11B124.3
C7—O2—C3105.30 (16)C12B—C11B—H11B124.3
C4—O3—H3O109.5C11B—C12B—C13B119.7 (4)
C21—O4—C6113.05 (17)C11B—C12B—H12B120.2
C7—N1—C14119.35 (15)C13B—C12B—H12B120.2
C7—N1—C2108.16 (17)C12B—C13B—C8B127.9 (4)
C14—N1—C2124.26 (15)C12B—C13B—H13B116.1
O1—C1—C2104.63 (16)C8B—C13B—H13B116.1
O1—C1—S1108.08 (14)N1—C14—C15B114.39 (7)
C2—C1—S1113.07 (15)N1—C14—C15A114.53 (7)
O1—C1—H1110.3N1—C14—H141108.6
C2—C1—H1110.3N1—C14—H142108.6
S1—C1—H1110.3C16A—C15A—C20A117.64 (13)
N1—C2—C397.80 (16)C16A—C15A—C14118.1
N1—C2—C1122.53 (17)C20A—C15A—C14123.79 (12)
C3—C2—C1106.35 (17)C15A—C16A—C17A120.10 (12)
N1—C2—H2109.7C15A—C16A—H16A119.9
C3—C2—H2109.7C17A—C16A—H16A119.9
C1—C2—H2109.7C18A—C17A—C16A122.5 (3)
O2—C3—C4118.12 (17)C18A—C17A—H17A118.8
O2—C3—C2103.64 (16)C16A—C17A—H17A118.8
C4—C3—C2111.22 (17)C19A—C18A—C17A116.8 (3)
O2—C3—H3107.8C19A—C18A—H18A121.6
C4—C3—H3107.8C17A—C18A—H18A121.6
C2—C3—H3107.8C18A—C19A—C20A121.1 (3)
O3—C4—C3113.12 (17)C18A—C19A—H19A119.5
O3—C4—C5108.03 (16)C20A—C19A—H19A119.5
C3—C4—C5103.43 (16)C19A—C20A—C15A121.8 (3)
O3—C4—H4110.7C19A—C20A—H20A119.1
C3—C4—H4110.7C15A—C20A—H20A119.1
C5—C4—H4110.7C16B—C15B—C20B119.96 (18)
O1—C5—C6107.21 (16)C16B—C15B—C14119.31 (13)
O1—C5—C4110.79 (16)C20B—C15B—C14119.65 (14)
C6—C5—C4111.84 (17)C17B—C16B—C15B121.4 (2)
O1—C5—H5109.0C17B—C16B—H16B119.3
C6—C5—H5109.0C15B—C16B—H16B119.3
C4—C5—H5109.0C16B—C17B—C18B117.7 (3)
O4—C6—C5112.61 (17)C16B—C17B—H17B121.1
O4—C6—H61109.1C18B—C17B—H17B121.1
C5—C6—H61109.1C19B—C18B—C17B121.6 (3)
O4—C6—H62109.1C19B—C18B—H18B119.2
C5—C6—H62109.1C17B—C18B—H18B119.2
H61—C6—H62107.8C18B—C19B—C20B119.7 (3)
O5—C7—N1127.1 (2)C18B—C19B—H19B120.1
O5—C7—O2122.2 (2)C20B—C19B—H19B120.1
N1—C7—O2110.73 (18)C19B—C20B—C15B119.3 (3)
C9A—C8A—C13A123.2 (2)C19B—C20B—H20B120.4
C9A—C8A—S1123.05 (17)C15B—C20B—H20B120.4
C13A—C8A—S1113.15 (17)O4—C21—C22109.66 (19)
C8A—C9A—C10A120.3 (3)O4—C21—H211109.7
C8A—C9A—H9A119.9C22—C21—H211109.7
C10A—C9A—H9A119.9O4—C21—H212109.7
C11A—C10A—C9A115.3 (3)C22—C21—H212109.7
C11A—C10A—H10A122.4H211—C21—H212108.2
C9A—C10A—H10A122.4C27—C22—C23118.9 (2)
C12A—C11A—C10A125.3 (3)C27—C22—C21121.8 (2)
C12A—C11A—H11A117.4C23—C22—C21119.3 (2)
C10A—C11A—H11A117.4C24—C23—C22121.0 (2)
C11A—C12A—C13A118.6 (3)C24—C23—H23119.5
C11A—C12A—H12A120.7C22—C23—H23119.5
C13A—C12A—H12A120.7C25—C24—C23119.6 (2)
C12A—C13A—C8A117.0 (3)C25—C24—H24120.2
C12A—C13A—H13A121.5C23—C24—H24120.2
C8A—C13A—H13A121.5C24—C25—C26120.5 (3)
C9B—C8B—C13B110.8 (3)C24—C25—H25119.8
C9B—C8B—S1120.9 (2)C26—C25—H25119.8
C13B—C8B—S1127.1 (2)C25—C26—C27119.1 (3)
C8B—C9B—C10B119.3 (3)C25—C26—H26120.4
C8B—C9B—H9B120.3C27—C26—H26120.4
C10B—C9B—H9B120.3C22—C27—C26120.9 (2)
C11B—C10B—C9B128.2 (4)C22—C27—H27119.5
C11B—C10B—H10B115.9C26—C27—H27119.5
O1—C1—C2—C363.0 (2)C9A—C8A—C13A—C12A−6.4 (7)
C1—C2—C3—C4−68.1 (2)S1—C8A—C13A—C12A−178.0 (4)
C2—C3—C4—C561.6 (2)C1—S1—C8B—C9B77.6 (3)
C3—C4—C5—O1−55.9 (2)C1—S1—C8B—C13B−88.4 (4)
C4—C5—O1—C161.9 (2)C13B—C8B—C9B—C10B−17.1 (6)
C5—O1—C1—C2−63.1 (2)S1—C8B—C9B—C10B174.8 (3)
C5—O1—C1—S1176.16 (12)C8B—C9B—C10B—C11B8.0 (7)
C8A—S1—C1—O1−80.49 (16)C9B—C10B—C11B—C12B6.1 (8)
C8B—S1—C1—O1−82.40 (16)C10B—C11B—C12B—C13B−8.8 (7)
C8A—S1—C1—C2164.18 (16)C11B—C12B—C13B—C8B−2.0 (8)
C8B—S1—C1—C2162.27 (16)C9B—C8B—C13B—C12B15.3 (7)
C7—N1—C2—C3−30.61 (19)S1—C8B—C13B—C12B−177.6 (4)
C14—N1—C2—C3−178.55 (14)C7—N1—C14—C15B−88.23 (17)
C7—N1—C2—C1−145.7 (2)C2—N1—C14—C15B56.42 (17)
C14—N1—C2—C166.3 (2)C7—N1—C14—C15A−88.61 (17)
O1—C1—C2—N1173.76 (17)C2—N1—C14—C15A56.03 (17)
S1—C1—C2—N1−68.9 (2)N1—C14—C15A—C16A−125.37 (8)
S1—C1—C2—C3−179.65 (14)N1—C14—C15A—C20A46.43 (19)
C7—O2—C3—C4−154.83 (18)C20A—C15A—C16A—C17A3.7 (2)
C7—O2—C3—C2−31.33 (19)C14—C15A—C16A—C17A176.01 (17)
N1—C2—C3—O236.67 (17)C15A—C16A—C17A—C18A−4.1 (4)
C1—C2—C3—O2163.95 (15)C16A—C17A—C18A—C19A3.4 (5)
N1—C2—C3—C4164.59 (15)C17A—C18A—C19A—C20A−2.5 (5)
O2—C3—C4—O3−62.1 (2)C18A—C19A—C20A—C15A2.4 (5)
C2—C3—C4—O3178.25 (15)C16A—C15A—C20A—C19A−2.9 (4)
O2—C3—C4—C5−178.73 (16)C14—C15A—C20A—C19A−174.7 (2)
C1—O1—C5—C6−175.85 (16)N1—C14—C15B—C16B−150.3 (2)
O3—C4—C5—O1−176.08 (15)N1—C14—C15B—C20B41.6 (2)
O3—C4—C5—C664.4 (2)C20B—C15B—C16B—C17B−5.1 (5)
C3—C4—C5—C6−175.48 (17)C14—C15B—C16B—C17B−173.2 (3)
C21—O4—C6—C575.1 (2)C15B—C16B—C17B—C18B3.8 (6)
O1—C5—C6—O451.8 (2)C16B—C17B—C18B—C19B−3.1 (7)
C4—C5—C6—O4173.44 (16)C17B—C18B—C19B—C20B3.7 (7)
C14—N1—C7—O5−16.3 (3)C18B—C19B—C20B—C15B−4.8 (6)
C2—N1—C7—O5−166.1 (2)C16B—C15B—C20B—C19B5.5 (5)
C14—N1—C7—O2162.90 (14)C14—C15B—C20B—C19B173.5 (3)
C2—N1—C7—O213.1 (2)C6—O4—C21—C22−172.10 (18)
C3—O2—C7—O5−168.81 (19)O4—C21—C22—C27−1.1 (3)
C3—O2—C7—N112.0 (2)O4—C21—C22—C23178.6 (2)
C1—S1—C8A—C9A51.4 (3)C27—C22—C23—C240.0 (4)
C1—S1—C8A—C13A−136.9 (3)C21—C22—C23—C24−179.7 (2)
C13A—C8A—C9A—C10A7.4 (6)C22—C23—C24—C25−1.4 (4)
S1—C8A—C9A—C10A178.2 (3)C23—C24—C25—C261.4 (5)
C8A—C9A—C10A—C11A−4.0 (6)C24—C25—C26—C270.0 (5)
C9A—C10A—C11A—C12A0.1 (7)C23—C22—C27—C261.5 (4)
C10A—C11A—C12A—C13A0.8 (8)C21—C22—C27—C26−178.8 (3)
C11A—C12A—C13A—C8A2.2 (8)C25—C26—C27—C22−1.5 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O5i0.841.982.774 (2)158.
Symmetry codes: (i) −x, y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O5i0.841.982.774 (2)158.
Symmetry codes: (i) −x, y+1/2, −z+1.
Acknowledgements top

SM acknowledges Incentive Grant Research from RIKEN and Grants-in Aid for Scientific Research for Scientific Research (C) from the Japan Society for the Promotion of Science (grant No. 19590032).

references
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