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Acta Cryst. (2009). E65, o2437    [ doi:10.1107/S1600536809032565 ]

3,4-O-Isopropylidene-2,7-di-O-p-tolylsulfonyl-[alpha]-L-xylo-3-heptulo-3,6-furanosononitrile

L. Ma, Y.-F. Li, X.-B. Meng and Z.-J. Li

Abstract top

In the title compound, C24H27NO10S2, derived from L-sorbofuranose, the fused five-membered rings display envelope conformations. The two tosylate branches are in equatorial positions with respect to the furanose ring, while the hydroxy group is in the axial position. In the crystal structure, the hydroxy group is involved in intermolecular O-H...O hydrogen bonds, linking molecules in chains along [100].

Comment top

The skeleton of the title compound is a derivative of L-sorbofuranose and consists of two tosyl, a cyano and a bridged ring. Both five-membered rings display an envelope conformation. The hydroxy group lies in axial bond of the furanose ring. The two tosylate branches lie in equatorial bonds of the five-membered furanose ring. The synthesis has been adapted from published procedures (Bianchi et al., 2001; Georges & Fraser-Reid, 1984; Sharma et al., 2003; Szarek et al., 1997).

Related literature top

For details of the synthesis, see: Bianchi et al. (2001); Georges & Fraser-Reid (1984); Sharma et al. (2003); Szarek et al. (1997).

Experimental top

The title compound was synthesized from the original compound 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose and the procedures are as follows: 2,3:4,6-di-O-isopropylidene-α-L-xylo-hexos-2-ulofuranose (obtained from the oxidization of 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose) was dissolved in HOAc (80%), followed by addition of NaCN, and after stirred at room temperature for 24 h., 3,4:5,7-di-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile was formed. The reaction mixture was then directly heated at 323 K for 12 h. to remove 4,6-isopropylidene, yielding 3,4-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile as a white solid after concentration in vacuo and subsequent column chromatography (petroleum-ethyl acetate 1:1). Finally 3,4-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile was dissolved in pyridine followed by addition of tosyl chloride, and the reaction mixture was stirred at room temperature for 12 h., to obtain the title compound (55% yield over four steps), which was crystallized from petroleum-ethyl acetate (4:1). After a week at room temperature colourless block-like crystals were obtained.

Refinement top

The completeness of diffraction data was limited to 0.945, because the crystal was lost before data collection was completed. The hydroxy H atom H5 was found in a difference map and refined with O—H bond length constrained to 0.82 Å, using a riding approximation, with Uiso(H5) = 1.5Ueq(O5). C-bound H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding, with Uiso(H)=1.2–1.5Ueq(C). The expected absolute configuration was confirmed by the refinement of a Flack parameter based on 1570 measured Friedel pairs.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title molecule, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.
3,4-O-Isopropylidene-2,7-di-O-p-tolylsulfonyl- α-L-xylo-3-heptulo-3,6-furanosononitrile top
Crystal data top
C24H27NO10S2F(000) = 580
Mr = 553.59Dx = 1.399 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3787 reflections
a = 5.6342 (11) Åθ = 1.5–27.5°
b = 28.771 (6) ŵ = 0.26 mm−1
c = 8.3226 (17) ÅT = 113 K
β = 103.00 (3)°Block, colourless
V = 1314.5 (5) Å30.16 × 0.12 × 0.08 mm
Z = 2
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4781 independent reflections
Radiation source: rotating anode4228 reflections with I > 2σ(I)
confocalRint = 0.039
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.5°
ω and φ scansh = −7→7
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −37→36
Tmin = 0.960, Tmax = 0.980l = −8→10
8980 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)] = 0.049H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0656P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4781 reflectionsΔρmax = 0.31 e Å−3
339 parametersΔρmin = −0.51 e Å−3
1 restraintAbsolute structure: Flack (1983), 1570 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.07 (7)
Crystal data top
C24H27NO10S2V = 1314.5 (5) Å3
Mr = 553.59Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.6342 (11) ŵ = 0.26 mm−1
b = 28.771 (6) ÅT = 113 K
c = 8.3226 (17) Å0.16 × 0.12 × 0.08 mm
β = 103.00 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4781 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		4228 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.980Rint = 0.039
8980 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.31 e Å−3
S = 1.05Δρmin = −0.51 e Å−3
4781 reflectionsAbsolute structure: Flack (1983), 1570 Friedel pairs
339 parametersFlack parameter: 0.07 (7)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1−0.32882 (13)0.19945 (2)0.07345 (11)0.01793 (18)
S2−0.17570 (13)0.48019 (2)0.32977 (11)0.01893 (18)
N10.2652 (6)0.26412 (11)0.3805 (5)0.0315 (7)
O1−0.4314 (4)0.48295 (9)0.3207 (3)0.0262 (6)
O2−0.0775 (4)0.49967 (8)0.2009 (3)0.0252 (6)
O3−0.1224 (4)0.42629 (8)0.3418 (3)0.0210 (5)
O4−0.0948 (4)0.34836 (7)0.1318 (3)0.0196 (5)
O50.4380 (4)0.35399 (8)0.2068 (3)0.0244 (5)
H50.56680.34870.18010.037*
O60.0421 (4)0.35979 (9)−0.2024 (3)0.0267 (6)
O7−0.2485 (4)0.31572 (8)−0.1269 (3)0.0206 (5)
O8−0.2598 (4)0.25334 (7)0.1007 (3)0.0196 (5)
O9−0.2258 (4)0.18218 (8)−0.0567 (3)0.0232 (5)
O10−0.5865 (4)0.19956 (9)0.0566 (3)0.0232 (5)
C1−0.0181 (6)0.50230 (11)0.5188 (5)0.0199 (7)
C2−0.1140 (7)0.49476 (12)0.6580 (5)0.0283 (9)
H2−0.25770.47810.64890.034*
C30.0070 (7)0.51242 (13)0.8098 (5)0.0313 (9)
H3−0.05700.50760.90210.038*
C40.2236 (7)0.53735 (12)0.8252 (6)0.0300 (9)
C50.3154 (6)0.54421 (13)0.6857 (6)0.0309 (9)
H5A0.45910.56090.69440.037*
C60.1973 (6)0.52669 (12)0.5336 (5)0.0245 (8)
H60.26270.53130.44170.029*
C70.3506 (8)0.55689 (15)0.9890 (6)0.0409 (11)
H7A0.52300.55760.99600.061*
H7B0.31710.53771.07570.061*
H7C0.29320.58791.00000.061*
C80.1045 (5)0.40951 (11)0.3035 (5)0.0219 (8)
H8A0.17610.38550.38140.026*
H8B0.22010.43490.31190.026*
C90.0493 (5)0.39035 (10)0.1331 (5)0.0188 (7)
H9−0.04210.41320.05600.023*
C100.2720 (5)0.37409 (11)0.0732 (5)0.0201 (7)
H100.34640.39960.02370.024*
C110.1613 (5)0.33768 (11)−0.0543 (4)0.0203 (7)
H110.27930.3142−0.07110.024*
C12−0.1785 (6)0.33503 (13)−0.2688 (5)0.0234 (7)
C13−0.0521 (5)0.31694 (10)0.0094 (5)0.0176 (7)
C14−0.3723 (7)0.36825 (15)−0.3504 (5)0.0363 (10)
H14A−0.39060.3922−0.27370.054*
H14B−0.52360.3519−0.38560.054*
H14C−0.32710.3820−0.44430.054*
C15−0.1348 (8)0.29602 (17)−0.3803 (6)0.0454 (12)
H15A−0.08840.3088−0.47530.068*
H15B−0.28130.2782−0.41490.068*
H15C−0.00680.2763−0.32160.068*
C16−0.0202 (5)0.26825 (11)0.0850 (4)0.0177 (7)
H160.04020.24710.01090.021*
C170.1446 (6)0.26673 (11)0.2511 (5)0.0227 (7)
C18−0.1844 (5)0.17379 (10)0.2592 (4)0.0159 (6)
C190.0301 (6)0.14921 (11)0.2676 (5)0.0222 (7)
H190.09250.14460.17450.027*
C200.1489 (6)0.13163 (11)0.4215 (5)0.0252 (8)
H200.29180.11470.42970.030*
C210.0598 (6)0.13870 (11)0.5629 (5)0.0240 (8)
C22−0.1557 (6)0.16375 (12)0.5487 (5)0.0258 (8)
H22−0.21790.16870.64180.031*
C23−0.2790 (6)0.18142 (11)0.3976 (5)0.0212 (7)
H23−0.42260.19810.38910.025*
C240.1933 (8)0.12001 (14)0.7275 (5)0.0345 (10)
H24A0.34180.10540.71590.052*
H24B0.09280.09760.76620.052*
H24C0.23040.14510.80520.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0172 (3)0.0193 (3)0.0174 (5)−0.0009 (3)0.0043 (3)−0.0008 (3)
S20.0184 (4)0.0219 (4)0.0171 (5)−0.0002 (3)0.0051 (3)−0.0031 (3)
N10.0297 (15)0.0327 (16)0.030 (2)0.0054 (13)0.0026 (15)0.0022 (15)
O10.0184 (10)0.0325 (13)0.0280 (16)0.0019 (10)0.0060 (11)−0.0039 (12)
O20.0333 (13)0.0257 (11)0.0195 (15)0.0003 (10)0.0122 (12)0.0025 (11)
O30.0190 (10)0.0209 (11)0.0250 (15)−0.0015 (9)0.0092 (10)−0.0048 (10)
O40.0154 (10)0.0175 (10)0.0292 (15)−0.0021 (8)0.0120 (10)−0.0044 (10)
O50.0133 (10)0.0336 (13)0.0263 (15)0.0013 (9)0.0044 (10)−0.0012 (11)
O60.0279 (12)0.0332 (12)0.0208 (15)−0.0061 (10)0.0095 (12)0.0024 (11)
O70.0162 (10)0.0277 (12)0.0160 (14)−0.0020 (9)−0.0004 (10)0.0049 (10)
O80.0144 (9)0.0201 (10)0.0253 (15)0.0019 (9)0.0063 (10)0.0009 (10)
O90.0295 (12)0.0239 (11)0.0186 (14)−0.0007 (10)0.0107 (11)−0.0050 (10)
O100.0142 (9)0.0299 (11)0.0238 (15)−0.0014 (9)0.0009 (10)0.0019 (12)
C10.0204 (14)0.0194 (14)0.021 (2)0.0003 (12)0.0069 (15)−0.0031 (14)
C20.0321 (18)0.0293 (17)0.025 (2)−0.0092 (14)0.0108 (18)0.0008 (16)
C30.041 (2)0.0345 (19)0.020 (2)−0.0061 (16)0.0082 (18)0.0003 (16)
C40.036 (2)0.0228 (16)0.031 (3)0.0041 (14)0.0057 (18)−0.0008 (16)
C50.0225 (17)0.0346 (19)0.035 (3)−0.0055 (15)0.0051 (17)−0.0051 (18)
C60.0235 (16)0.0269 (16)0.026 (2)−0.0009 (13)0.0120 (16)−0.0033 (15)
C70.050 (2)0.036 (2)0.032 (3)0.0001 (18)−0.001 (2)−0.005 (2)
C80.0146 (13)0.0243 (16)0.028 (2)0.0017 (12)0.0065 (14)−0.0043 (15)
C90.0149 (13)0.0161 (13)0.026 (2)−0.0016 (11)0.0054 (14)−0.0006 (13)
C100.0150 (13)0.0256 (15)0.020 (2)−0.0014 (12)0.0055 (14)−0.0026 (14)
C110.0156 (14)0.0270 (15)0.020 (2)−0.0012 (12)0.0070 (14)−0.0046 (14)
C120.0213 (15)0.0362 (18)0.0130 (19)−0.0070 (14)0.0048 (14)−0.0006 (15)
C130.0138 (13)0.0168 (14)0.022 (2)0.0024 (11)0.0030 (13)−0.0015 (14)
C140.0342 (19)0.043 (2)0.029 (3)−0.0029 (17)0.0004 (19)0.0153 (19)
C150.039 (2)0.062 (3)0.040 (3)−0.011 (2)0.018 (2)−0.026 (2)
C160.0134 (13)0.0208 (14)0.0194 (19)−0.0005 (11)0.0047 (13)−0.0009 (13)
C170.0215 (15)0.0241 (15)0.024 (2)0.0028 (13)0.0083 (16)0.0011 (14)
C180.0181 (14)0.0180 (14)0.0123 (18)−0.0009 (11)0.0049 (14)−0.0020 (12)
C190.0217 (15)0.0247 (15)0.021 (2)0.0018 (13)0.0055 (15)0.0009 (14)
C200.0202 (15)0.0239 (16)0.030 (2)0.0010 (13)0.0032 (16)0.0024 (15)
C210.0273 (17)0.0215 (15)0.018 (2)−0.0019 (13)−0.0061 (16)0.0020 (14)
C220.0336 (19)0.0255 (16)0.020 (2)0.0025 (14)0.0090 (17)0.0019 (15)
C230.0256 (16)0.0247 (15)0.0153 (19)0.0011 (13)0.0087 (15)0.0014 (14)
C240.041 (2)0.0337 (19)0.021 (2)−0.0005 (16)−0.0092 (19)0.0051 (18)
Geometric parameters (Å, °) top
S1—O101.427 (2)C8—H8A0.9700
S1—O91.428 (2)C8—H8B0.9700
S1—O81.602 (2)C9—C101.524 (4)
S1—C181.741 (4)C9—H90.9800
S2—O21.427 (3)C10—C111.521 (4)
S2—O11.428 (2)C10—H100.9800
S2—O31.578 (2)C11—C131.539 (4)
S2—C11.743 (4)C11—H110.9800
N1—C171.139 (5)C12—C141.494 (5)
O3—C81.467 (3)C12—C151.512 (5)
O4—C131.423 (4)C13—C161.530 (4)
O4—C91.454 (3)C14—H14A0.9600
O5—C101.406 (4)C14—H14B0.9600
O5—H50.8200C14—H14C0.9600
O6—C111.415 (4)C15—H15A0.9600
O6—C121.431 (4)C15—H15B0.9600
O7—C131.396 (4)C15—H15C0.9600
O7—C121.438 (4)C16—C171.483 (5)
O8—C161.450 (3)C16—H160.9800
C1—C61.383 (4)C18—C191.388 (4)
C1—C21.401 (5)C18—C231.391 (5)
C2—C31.390 (6)C19—C201.399 (5)
C2—H20.9300C19—H190.9300
C3—C41.396 (5)C20—C211.394 (5)
C3—H30.9300C20—H200.9300
C4—C51.388 (6)C21—C221.394 (5)
C4—C71.499 (6)C21—C241.506 (5)
C5—C61.386 (6)C22—C231.389 (5)
C5—H5A0.9300C22—H220.9300
C6—H60.9300C23—H230.9300
C7—H7A0.9600C24—H24A0.9600
C7—H7B0.9600C24—H24B0.9600
C7—H7C0.9600C24—H24C0.9600
C8—C91.488 (5)
O10—S1—O9120.29 (15)O6—C11—C13102.7 (2)
O10—S1—O8102.76 (13)C10—C11—C13104.9 (3)
O9—S1—O8108.47 (13)O6—C11—H11112.9
O10—S1—C18110.50 (14)C10—C11—H11112.9
O9—S1—C18109.72 (15)C13—C11—H11112.9
O8—S1—C18103.57 (14)O6—C12—O7104.5 (3)
O2—S2—O1119.71 (16)O6—C12—C14109.8 (3)
O2—S2—O3109.48 (13)O7—C12—C14108.2 (3)
O1—S2—O3103.49 (13)O6—C12—C15111.1 (3)
O2—S2—C1109.25 (16)O7—C12—C15109.3 (3)
O1—S2—C1109.28 (16)C14—C12—C15113.5 (4)
O3—S2—C1104.48 (15)O7—C13—O4111.5 (2)
C8—O3—S2118.17 (19)O7—C13—C16108.0 (2)
C13—O4—C9110.4 (2)O4—C13—C16108.1 (3)
C10—O5—H5109.5O7—C13—C11105.6 (3)
C11—O6—C12108.3 (3)O4—C13—C11105.7 (2)
C13—O7—C12110.1 (2)C16—C13—C11117.9 (2)
C16—O8—S1118.35 (17)C12—C14—H14A109.5
C6—C1—C2119.9 (4)C12—C14—H14B109.5
C6—C1—S2121.6 (3)H14A—C14—H14B109.5
C2—C1—S2118.5 (3)C12—C14—H14C109.5
C3—C2—C1119.6 (3)H14A—C14—H14C109.5
C3—C2—H2120.2H14B—C14—H14C109.5
C1—C2—H2120.2C12—C15—H15A109.5
C2—C3—C4120.8 (4)C12—C15—H15B109.5
C2—C3—H3119.6H15A—C15—H15B109.5
C4—C3—H3119.6C12—C15—H15C109.5
C5—C4—C3118.6 (4)H15A—C15—H15C109.5
C5—C4—C7121.1 (4)H15B—C15—H15C109.5
C3—C4—C7120.4 (4)O8—C16—C17107.9 (3)
C6—C5—C4121.3 (3)O8—C16—C13106.4 (2)
C6—C5—H5A119.3C17—C16—C13113.7 (3)
C4—C5—H5A119.3O8—C16—H16109.6
C1—C6—C5119.8 (3)C17—C16—H16109.6
C1—C6—H6120.1C13—C16—H16109.6
C5—C6—H6120.1N1—C17—C16177.1 (4)
C4—C7—H7A109.5C19—C18—C23122.0 (3)
C4—C7—H7B109.5C19—C18—S1119.2 (3)
H7A—C7—H7B109.5C23—C18—S1118.6 (2)
C4—C7—H7C109.5C18—C19—C20117.5 (3)
H7A—C7—H7C109.5C18—C19—H19121.2
H7B—C7—H7C109.5C20—C19—H19121.2
O3—C8—C9108.9 (3)C21—C20—C19122.1 (3)
O3—C8—H8A109.9C21—C20—H20119.0
C9—C8—H8A109.9C19—C20—H20119.0
O3—C8—H8B109.9C22—C21—C20118.4 (3)
C9—C8—H8B109.9C22—C21—C24120.6 (4)
H8A—C8—H8B108.3C20—C21—C24121.0 (3)
O4—C9—C8108.1 (3)C23—C22—C21120.9 (4)
O4—C9—C10104.0 (2)C23—C22—H22119.5
C8—C9—C10114.5 (3)C21—C22—H22119.5
O4—C9—H9110.0C22—C23—C18119.0 (3)
C8—C9—H9110.0C22—C23—H23120.5
C10—C9—H9110.0C18—C23—H23120.5
O5—C10—C11111.3 (3)C21—C24—H24A109.5
O5—C10—C9108.5 (3)C21—C24—H24B109.5
C11—C10—C9101.6 (2)H24A—C24—H24B109.5
O5—C10—H10111.6C21—C24—H24C109.5
C11—C10—H10111.6H24A—C24—H24C109.5
C9—C10—H10111.6H24B—C24—H24C109.5
O6—C11—C10109.7 (3)
O2—S2—O3—C833.2 (3)C13—O7—C12—O6−16.2 (3)
O1—S2—O3—C8161.9 (3)C13—O7—C12—C14−133.2 (3)
C1—S2—O3—C8−83.7 (3)C13—O7—C12—C15102.7 (3)
O10—S1—O8—C16−166.0 (2)C12—O7—C13—O4112.8 (3)
O9—S1—O8—C16−37.6 (3)C12—O7—C13—C16−128.6 (3)
C18—S1—O8—C1678.9 (3)C12—O7—C13—C11−1.6 (3)
O2—S2—C1—C6−12.2 (3)C9—O4—C13—O7−105.8 (3)
O1—S2—C1—C6−144.9 (3)C9—O4—C13—C16135.5 (3)
O3—S2—C1—C6104.8 (3)C9—O4—C13—C118.4 (3)
O2—S2—C1—C2168.0 (3)O6—C11—C13—O718.8 (3)
O1—S2—C1—C235.3 (3)C10—C11—C13—O7133.5 (3)
O3—S2—C1—C2−75.0 (3)O6—C11—C13—O4−99.5 (3)
C6—C1—C2—C30.8 (5)C10—C11—C13—O415.2 (3)
S2—C1—C2—C3−179.4 (3)O6—C11—C13—C16139.6 (3)
C1—C2—C3—C4−0.3 (6)C10—C11—C13—C16−105.7 (3)
C2—C3—C4—C50.1 (6)S1—O8—C16—C17−92.6 (3)
C2—C3—C4—C7179.0 (4)S1—O8—C16—C13145.0 (2)
C3—C4—C5—C6−0.3 (6)O7—C13—C16—O8−48.4 (3)
C7—C4—C5—C6−179.2 (4)O4—C13—C16—O872.5 (3)
C2—C1—C6—C5−1.0 (5)C11—C13—C16—O8−167.8 (3)
S2—C1—C6—C5179.2 (3)O7—C13—C16—C17−167.0 (3)
C4—C5—C6—C10.8 (6)O4—C13—C16—C17−46.2 (3)
S2—O3—C8—C9−100.7 (3)C11—C13—C16—C1773.5 (4)
C13—O4—C9—C8−150.7 (2)O10—S1—C18—C19147.6 (3)
C13—O4—C9—C10−28.7 (3)O9—S1—C18—C1912.7 (3)
O3—C8—C9—O4−67.9 (3)O8—S1—C18—C19−103.0 (3)
O3—C8—C9—C10176.7 (3)O10—S1—C18—C23−36.9 (3)
O4—C9—C10—O5−81.1 (3)O9—S1—C18—C23−171.8 (2)
C8—C9—C10—O536.6 (4)O8—S1—C18—C2372.5 (3)
O4—C9—C10—C1136.3 (3)C23—C18—C19—C200.7 (5)
C8—C9—C10—C11154.0 (3)S1—C18—C19—C20176.0 (2)
C12—O6—C11—C10−140.6 (3)C18—C19—C20—C21−0.9 (5)
C12—O6—C11—C13−29.4 (3)C19—C20—C21—C220.6 (5)
O5—C10—C11—O6−166.2 (2)C19—C20—C21—C24−179.1 (3)
C9—C10—C11—O678.4 (3)C20—C21—C22—C23−0.2 (5)
O5—C10—C11—C1384.1 (3)C24—C21—C22—C23179.5 (3)
C9—C10—C11—C13−31.3 (3)C21—C22—C23—C180.0 (5)
C11—O6—C12—O729.1 (3)C19—C18—C23—C22−0.3 (5)
C11—O6—C12—C14145.0 (3)S1—C18—C23—C22−175.7 (3)
C11—O6—C12—C15−88.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O4i0.822.032.844 (3)169
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O4i0.822.032.844 (3)169
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

We acknowledge financial support from the National Natural Science Foundation of China.

references
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