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ISSN: 2056-9890

(E)-1-(4-Chloro­phen­yl)-3-[4-(2,3,4,6-tetra-O-acetyl-β-D-allo­pyranos­yl­oxy)phen­yl]prop-2-en-1-one

aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: chuandayouji217@163.com

(Received 1 December 2009; accepted 29 December 2009; online 9 January 2010)

The asymmetric unit of the title compound, C29H29ClO11, contains two independent mol­ecules of similar geometry, both adopting an E conformation about the C=C double bond. The dihedral angles formed by benzene rings are 10.73 (16) and 13.79 (18)°. The pyran­oside rings adopt a chair conformation. Intra­molecular C—H⋯O close contacts occur. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the biological properties of helicid [systematic name: 4-formyl­phenl-β-D-allopyran­oside], see: Chen et al. (1981[Chen, W. S., Lu, S. D. & Eberhard, B. (1981). Liebigs Ann. Chem. 10, 1893-1897.]); Sha & Mao (1987[Sha, J. Z. & Mao, H. K. (1987). Chin. Pharm. Bull. 22, 27-30.]). For the crystal structures of helicid derivatives, see: Fan et al. (2007[Fan, B., Li, J. L., Li, Y. & Yin, S. F. (2007). Chin. J. Org. Chem. 27, 1150-1154.]); Fu et al. (2009[Fu, L., Yin, X., Zheng, L., Li, Y. & Yin, S. (2009). Acta Cryst. E65, o679.]); Ye et al. (2009[Ye, D., Zhang, K., Chen, H., Yin, S. & Li, Y. (2009). Acta Cryst. E65, o1338.]): Yang et al. (2009[Yang, C., Luo, H., Yin, X., Li, Y. & Yin, S. (2009). Acta Cryst. E65, o634.]).

[Scheme 1]

Experimental

Crystal data
  • C29H29ClO11

  • Mr = 588.97

  • Monoclinic, P 21

  • a = 7.2387 (14) Å

  • b = 39.239 (8) Å

  • c = 10.297 (2) Å

  • β = 90.25 (3)°

  • V = 2924.7 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 113 K

  • 0.27 × 0.25 × 0.20 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear. Rigaku/MSC, The Woodlands ,Texas, USA.]) Tmin = 0.951, Tmax = 0.963

  • 17131 measured reflections

  • 11143 independent reflections

  • 8341 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.189

  • S = 1.04

  • 11143 reflections

  • 748 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.76 e Å−3

  • Δρmin = −0.37 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); 4380 Friedel pairs

  • Flack parameter: 0.03 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯O9i 1.00 2.38 3.185 (5) 137
C20—H20⋯O1 0.95 2.54 3.111 (5) 118
C20—H20⋯O9i 0.95 2.54 3.271 (5) 134
C30—H30⋯O20i 1.00 2.51 3.316 (5) 138
C32—H32⋯O20 1.00 2.53 3.031 (5) 111
C49—H49⋯O12 0.95 2.50 3.065 (5) 119
C49—H49⋯O20i 0.95 2.53 3.271 (6) 135
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear. Rigaku/MSC, The Woodlands ,Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The natural compound hecilid [systematic name: 4-formylphenl-β-D-allopyranoside], C13H16O7, extracted from the fruit of Helicia Nilagirica Beed (Chen et al., 1981), is a major active ingredient of Chinese herbal medicine. It has been reported to possess a variety of biological effects on the central nervous system including sedative, hypnotic and anticonvulsant activities (Sha & Mao, 1987). In order to improve its hypnotic-sedative activity, we have recently synthesized helicid derivatives and reported their structures (Fan et al., 2007; Fu et al., 2009); Ye et al., 2009, Yang et al., 2009).

The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1), adopting an E conformation about the C21C22 and C50C51 double bonds. The average of C–C bond length in the pyranoside rings is 1.520 (5) Å, the average C(sp3)–O and C(sp2)–O bond lengths are 1.436 (4) and 1.360 (5) Å, respectively. The pyranoside rings adopt the stable chair conformation. The substituents of the protected sugar at the C3 are in the axial position, while all other groups are in equatorial positions. The dihedral angles formed by the benzene rings in the two molecules are 10.73 (16) and 13.79 (18)°, respectively. The crystal packing is stabilized by intra- and intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the biological properties of helicid [systematic name: 4-formylphenl-β-D-allopyranoside], see: Chen et al. (1981); Sha & Mao (1987). For the crystal structures of helicid derivatives, see: Fan et al. (2007); Fu et al. (2009); Ye et al. (2009): Yang et al. (2009).

Experimental top

To a solution of E-4-β-D-allopyranoside-cinnamic-4-chlorophenyl ketone (2.06 g, 3.5 mmol) in DMF (2 ml) and triethanolamine (3 ml) was added dropwise acetyl anhydride (2.5 g, 25 mmol) under ice bath. The mixture was stirred vigorously at room temperature for5 h, then poured into 20 ml of ice water. The precipitate was filtered and washed with water. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2 Ueq (C) or 1.5 Ueq (C) for methyl H atoms.

Structure description top

The natural compound hecilid [systematic name: 4-formylphenl-β-D-allopyranoside], C13H16O7, extracted from the fruit of Helicia Nilagirica Beed (Chen et al., 1981), is a major active ingredient of Chinese herbal medicine. It has been reported to possess a variety of biological effects on the central nervous system including sedative, hypnotic and anticonvulsant activities (Sha & Mao, 1987). In order to improve its hypnotic-sedative activity, we have recently synthesized helicid derivatives and reported their structures (Fan et al., 2007; Fu et al., 2009); Ye et al., 2009, Yang et al., 2009).

The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1), adopting an E conformation about the C21C22 and C50C51 double bonds. The average of C–C bond length in the pyranoside rings is 1.520 (5) Å, the average C(sp3)–O and C(sp2)–O bond lengths are 1.436 (4) and 1.360 (5) Å, respectively. The pyranoside rings adopt the stable chair conformation. The substituents of the protected sugar at the C3 are in the axial position, while all other groups are in equatorial positions. The dihedral angles formed by the benzene rings in the two molecules are 10.73 (16) and 13.79 (18)°, respectively. The crystal packing is stabilized by intra- and intermolecular C—H···O hydrogen bonds (Table 1).

For the biological properties of helicid [systematic name: 4-formylphenl-β-D-allopyranoside], see: Chen et al. (1981); Sha & Mao (1987). For the crystal structures of helicid derivatives, see: Fan et al. (2007); Fu et al. (2009); Ye et al. (2009): Yang et al. (2009).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level.
(E)-1-(4-Chlorophenyl)-3-[4-(2,3,4,6-tetra-O-acetyl-β-D- allopyranosyloxy)phenyl]prop-2-en-1-one top
Crystal data top
C29H29ClO11F(000) = 1232
Mr = 588.97Dx = 1.338 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5501 reflections
a = 7.2387 (14) Åθ = 2.0–27.9°
b = 39.239 (8) ŵ = 0.19 mm1
c = 10.297 (2) ÅT = 113 K
β = 90.25 (3)°Block, colourless
V = 2924.7 (10) Å30.27 × 0.25 × 0.20 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
11143 independent reflections
Radiation source: rotating anode8341 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.041
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and φ scansh = 96
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 4951
Tmin = 0.951, Tmax = 0.963l = 1313
17131 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067 w = 1/[σ2(Fo2) + (0.0899P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.76 e Å3
11143 reflectionsΔρmin = 0.37 e Å3
748 parametersExtinction correction: SHELXL97 (Sheldrick, 2008)
1 restraintExtinction coefficient: 0.0394 (19)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983); 4380 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (8)
Crystal data top
C29H29ClO11V = 2924.7 (10) Å3
Mr = 588.97Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.2387 (14) ŵ = 0.19 mm1
b = 39.239 (8) ÅT = 113 K
c = 10.297 (2) Å0.27 × 0.25 × 0.20 mm
β = 90.25 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
11143 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
8341 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.963Rint = 0.041
17131 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.189Δρmax = 0.76 e Å3
S = 1.04Δρmin = 0.37 e Å3
11143 reflectionsAbsolute structure: Flack (1983); 4380 Friedel pairs
748 parametersAbsolute structure parameter: 0.03 (8)
1 restraint
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*/Ueq
Cl10.4045 (2)0.46856 (4)0.80542 (16)0.0871 (6)
O10.0935 (4)0.23162 (7)0.2486 (2)0.0331 (6)
O20.0223 (4)0.22091 (8)0.5168 (3)0.0409 (7)
O30.0068 (5)0.17591 (10)0.6492 (3)0.0583 (10)
O40.1770 (4)0.14634 (7)0.3739 (2)0.0325 (6)
O50.3944 (5)0.15196 (10)0.5296 (4)0.0676 (11)
O60.2152 (3)0.15628 (7)0.1075 (2)0.0307 (6)
O70.4675 (4)0.13160 (8)0.0196 (3)0.0467 (8)
O80.4323 (3)0.20767 (7)0.0084 (2)0.0327 (6)
O90.7123 (4)0.19670 (8)0.0942 (3)0.0454 (8)
O100.2147 (4)0.26256 (7)0.0803 (3)0.0361 (6)
O110.6370 (8)0.35722 (14)0.3468 (4)0.0944 (16)
C10.0449 (5)0.19838 (10)0.2976 (3)0.0327 (8)
H10.02760.18590.22970.039*
C20.2234 (5)0.17956 (10)0.3222 (3)0.0296 (8)
H20.30020.19240.38670.036*
C30.3300 (5)0.17529 (10)0.1964 (3)0.0301 (8)
H30.45020.16340.21200.036*
C40.3608 (5)0.21054 (10)0.1381 (3)0.0299 (8)
H40.44770.22400.19380.036*
C50.1765 (5)0.22917 (10)0.1247 (3)0.0303 (8)
H50.09310.21700.06250.036*
C60.0756 (6)0.20335 (12)0.4162 (4)0.0375 (9)
H6A0.18680.21660.39160.045*
H6B0.11660.18090.44870.045*
C70.0449 (6)0.20507 (14)0.6306 (4)0.0431 (10)
C80.1309 (8)0.22760 (18)0.7274 (4)0.0663 (16)
H8A0.03710.24280.76380.099*
H8B0.22760.24120.68580.099*
H8C0.18550.21380.79710.099*
C90.2725 (6)0.13525 (11)0.4806 (4)0.0394 (9)
C100.2024 (6)0.10208 (11)0.5231 (4)0.0405 (10)
H10A0.27900.09350.59470.061*
H10B0.20660.08600.45050.061*
H10C0.07450.10460.55260.061*
C110.3029 (6)0.13577 (10)0.0206 (4)0.0366 (9)
C120.1689 (7)0.12083 (13)0.0733 (4)0.0469 (11)
H12A0.11770.13890.12820.070*
H12B0.06870.10970.02580.070*
H12C0.23190.10400.12780.070*
C130.6163 (5)0.19973 (11)0.0015 (4)0.0380 (9)
C140.6735 (7)0.19570 (13)0.1389 (4)0.0514 (12)
H14A0.70640.21800.17480.077*
H14B0.57130.18590.18930.077*
H14C0.78070.18050.14340.077*
C150.0739 (6)0.27878 (10)0.0115 (4)0.0364 (9)
C160.1302 (7)0.30255 (11)0.0791 (4)0.0427 (10)
H160.25730.30800.08830.051*
C170.0025 (8)0.31829 (12)0.1565 (4)0.0526 (13)
H170.03520.33460.21940.063*
C180.1872 (8)0.31079 (12)0.1440 (4)0.0472 (11)
C190.2401 (7)0.28779 (12)0.0488 (4)0.0442 (10)
H190.36770.28300.03770.053*
C200.1119 (6)0.27163 (11)0.0308 (4)0.0396 (9)
H200.15010.25620.09630.047*
C210.3332 (8)0.32739 (14)0.2210 (5)0.0579 (14)
H210.45550.31960.20650.069*
C220.3144 (9)0.35191 (13)0.3078 (4)0.0595 (15)
H220.19490.36050.32730.071*
C230.4788 (10)0.36618 (16)0.3751 (5)0.0662 (16)
C240.4528 (9)0.39271 (13)0.4791 (4)0.0576 (15)
C250.6059 (10)0.40906 (17)0.5284 (5)0.080 (2)
H250.72380.40390.49330.096*
C260.5936 (10)0.43274 (15)0.6271 (5)0.0699 (18)
H260.70100.44370.65990.084*
C270.4251 (10)0.43989 (13)0.6758 (5)0.0652 (17)
C280.2635 (10)0.42421 (14)0.6317 (6)0.080 (2)
H280.14680.42900.66930.096*
C290.2821 (10)0.40076 (13)0.5282 (5)0.0651 (17)
H290.17500.39040.49210.078*
Cl20.4194 (3)0.24933 (4)1.58590 (17)0.0931 (7)
O120.1131 (4)0.48458 (7)0.5432 (2)0.0332 (6)
O130.0396 (4)0.49401 (8)0.2686 (2)0.0383 (7)
O140.0283 (5)0.54079 (9)0.1405 (3)0.0531 (9)
O150.2201 (4)0.56671 (7)0.3966 (2)0.0317 (6)
O160.4724 (4)0.55925 (9)0.2730 (3)0.0503 (8)
O170.2470 (4)0.56115 (7)0.6643 (2)0.0322 (6)
O180.4752 (6)0.59742 (12)0.6962 (5)0.1016 (19)
O190.4507 (4)0.51189 (7)0.7829 (2)0.0353 (6)
O200.7336 (4)0.52389 (9)0.7032 (3)0.0476 (8)
O210.2323 (4)0.45509 (7)0.7148 (3)0.0374 (6)
O220.6366 (6)0.36340 (14)1.1305 (4)0.0853 (14)
C300.0696 (5)0.51697 (10)0.4870 (3)0.0306 (8)
H300.00230.53100.55270.037*
C310.2533 (5)0.53414 (10)0.4569 (3)0.0320 (8)
H310.32660.51940.39710.038*
C320.3606 (5)0.53960 (10)0.5825 (3)0.0285 (7)
H320.48280.55050.56510.034*
C330.3851 (5)0.50576 (10)0.6528 (3)0.0333 (8)
H330.47380.49090.60480.040*
C340.1990 (6)0.48786 (10)0.6672 (3)0.0318 (8)
H340.11750.50080.72780.038*
C350.0543 (5)0.51158 (11)0.3716 (3)0.0342 (8)
H35A0.16360.49820.39830.041*
H35B0.09830.53390.33940.041*
C360.0665 (6)0.51104 (13)0.1566 (4)0.0413 (10)
C370.1418 (7)0.48837 (17)0.0542 (4)0.0635 (16)
H37A0.04070.47540.01420.095*
H37B0.23110.47260.09300.095*
H37C0.20320.50220.01210.095*
C380.3431 (5)0.57652 (11)0.3034 (4)0.0340 (8)
C390.2970 (6)0.61081 (12)0.2540 (4)0.0423 (10)
H39A0.34740.62810.31320.063*
H39B0.16250.61330.24860.063*
H39C0.35050.61380.16760.063*
C400.3226 (6)0.58947 (11)0.7148 (4)0.0420 (10)
C410.1861 (6)0.60711 (13)0.8003 (4)0.0465 (11)
H41A0.23850.62870.83080.070*
H41B0.15780.59260.87500.070*
H41C0.07250.61160.75100.070*
C420.6307 (6)0.52256 (11)0.7942 (4)0.0394 (9)
C430.6705 (7)0.53339 (16)0.9307 (5)0.0610 (14)
H43A0.78180.54760.93230.092*
H43B0.69020.51320.98500.092*
H43C0.56570.54650.96420.092*
C440.0878 (6)0.43935 (10)0.7811 (4)0.0356 (8)
C450.1393 (7)0.41400 (11)0.8695 (4)0.0434 (10)
H450.26500.40750.87890.052*
C460.0033 (7)0.39862 (11)0.9431 (4)0.0446 (11)
H460.03710.38121.00270.053*
C470.1812 (7)0.40791 (12)0.9324 (4)0.0449 (11)
C480.2288 (6)0.43279 (11)0.8400 (4)0.0419 (10)
H480.35460.43920.82990.050*
C490.0941 (6)0.44838 (11)0.7624 (4)0.0393 (9)
H490.12760.46470.69850.047*
C500.3288 (8)0.39263 (13)1.0094 (4)0.0514 (12)
H500.44920.40170.99620.062*
C510.3144 (8)0.36731 (13)1.0965 (4)0.0542 (13)
H510.19640.35811.11690.065*
C520.4804 (9)0.35371 (15)1.1606 (5)0.0604 (15)
C530.4584 (9)0.32656 (13)1.2633 (4)0.0571 (14)
C540.2858 (9)0.31860 (14)1.3170 (5)0.0609 (15)
H540.17780.32941.28490.073*
C550.2715 (10)0.29441 (16)1.4192 (6)0.078 (2)
H550.15590.28911.45840.094*
C560.4352 (10)0.27874 (13)1.4595 (5)0.0642 (17)
C570.6005 (10)0.28634 (16)1.4068 (5)0.0691 (17)
H570.70800.27501.43680.083*
C580.6159 (9)0.31037 (17)1.3100 (5)0.0726 (18)
H580.73390.31591.27500.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1132 (12)0.0597 (9)0.0879 (10)0.0278 (9)0.0615 (10)0.0396 (8)
O10.0384 (14)0.0309 (14)0.0301 (12)0.0033 (12)0.0032 (11)0.0014 (11)
O20.0488 (17)0.0437 (18)0.0304 (13)0.0014 (14)0.0054 (12)0.0050 (12)
O30.081 (3)0.059 (2)0.0346 (15)0.007 (2)0.0053 (16)0.0065 (16)
O40.0344 (13)0.0341 (15)0.0289 (12)0.0017 (12)0.0007 (11)0.0060 (11)
O50.073 (2)0.064 (2)0.066 (2)0.024 (2)0.0376 (19)0.0269 (19)
O60.0304 (13)0.0330 (15)0.0286 (12)0.0033 (11)0.0024 (10)0.0047 (10)
O70.0412 (17)0.056 (2)0.0426 (15)0.0091 (15)0.0042 (14)0.0118 (15)
O80.0322 (13)0.0378 (16)0.0280 (12)0.0002 (12)0.0001 (11)0.0035 (11)
O90.0278 (14)0.0521 (19)0.0562 (18)0.0024 (13)0.0023 (13)0.0171 (15)
O100.0437 (15)0.0267 (14)0.0379 (14)0.0021 (12)0.0011 (12)0.0022 (11)
O110.102 (4)0.105 (4)0.076 (3)0.048 (3)0.020 (3)0.044 (3)
C10.0361 (19)0.036 (2)0.0256 (16)0.0059 (17)0.0016 (15)0.0052 (15)
C20.0283 (17)0.035 (2)0.0257 (15)0.0012 (15)0.0005 (14)0.0038 (15)
C30.0343 (19)0.031 (2)0.0243 (15)0.0041 (16)0.0044 (14)0.0014 (14)
C40.0310 (18)0.032 (2)0.0264 (16)0.0044 (15)0.0002 (14)0.0020 (14)
C50.0366 (19)0.0256 (18)0.0289 (16)0.0001 (16)0.0015 (15)0.0035 (14)
C60.035 (2)0.043 (2)0.0335 (18)0.0012 (18)0.0018 (16)0.0008 (17)
C70.039 (2)0.059 (3)0.0311 (19)0.005 (2)0.0061 (17)0.0018 (19)
C80.065 (3)0.098 (5)0.037 (2)0.020 (3)0.009 (2)0.007 (3)
C90.041 (2)0.040 (2)0.0370 (19)0.0045 (18)0.0048 (18)0.0115 (18)
C100.046 (2)0.036 (2)0.040 (2)0.0033 (19)0.0032 (18)0.0129 (18)
C110.052 (2)0.028 (2)0.0293 (17)0.0035 (18)0.0013 (17)0.0008 (15)
C120.055 (3)0.051 (3)0.035 (2)0.011 (2)0.0038 (19)0.0076 (19)
C130.034 (2)0.035 (2)0.045 (2)0.0003 (17)0.0016 (18)0.0110 (18)
C140.058 (3)0.046 (3)0.050 (2)0.007 (2)0.022 (2)0.005 (2)
C150.050 (2)0.027 (2)0.0315 (18)0.0056 (18)0.0008 (17)0.0050 (15)
C160.056 (3)0.033 (2)0.038 (2)0.001 (2)0.0101 (19)0.0044 (17)
C170.083 (4)0.031 (2)0.044 (2)0.011 (2)0.014 (2)0.0134 (19)
C180.071 (3)0.034 (2)0.037 (2)0.019 (2)0.004 (2)0.0076 (18)
C190.056 (3)0.037 (2)0.039 (2)0.014 (2)0.001 (2)0.0048 (18)
C200.048 (2)0.037 (2)0.0338 (19)0.0006 (19)0.0047 (18)0.0053 (17)
C210.080 (4)0.053 (3)0.040 (2)0.031 (3)0.002 (2)0.006 (2)
C220.097 (4)0.047 (3)0.034 (2)0.034 (3)0.006 (2)0.0054 (19)
C230.100 (5)0.057 (4)0.042 (2)0.032 (3)0.003 (3)0.010 (2)
C240.104 (5)0.039 (3)0.030 (2)0.024 (3)0.008 (2)0.0048 (19)
C250.106 (5)0.090 (5)0.042 (3)0.058 (4)0.011 (3)0.017 (3)
C260.116 (5)0.056 (3)0.037 (2)0.040 (4)0.003 (3)0.007 (2)
C270.118 (5)0.035 (3)0.043 (2)0.001 (3)0.048 (3)0.000 (2)
C280.109 (5)0.043 (3)0.088 (4)0.025 (3)0.058 (4)0.027 (3)
C290.097 (4)0.034 (3)0.063 (3)0.003 (3)0.040 (3)0.013 (2)
Cl20.1117 (13)0.0730 (10)0.0952 (11)0.0367 (10)0.0665 (10)0.0504 (9)
O120.0432 (15)0.0285 (14)0.0280 (12)0.0027 (12)0.0013 (11)0.0005 (11)
O130.0479 (16)0.0391 (17)0.0278 (12)0.0071 (13)0.0025 (12)0.0065 (11)
O140.065 (2)0.056 (2)0.0382 (16)0.0074 (18)0.0110 (15)0.0066 (15)
O150.0353 (13)0.0315 (15)0.0284 (12)0.0013 (12)0.0056 (11)0.0032 (11)
O160.0458 (17)0.054 (2)0.0513 (18)0.0085 (16)0.0210 (15)0.0106 (16)
O170.0340 (13)0.0320 (15)0.0307 (12)0.0031 (12)0.0074 (11)0.0064 (11)
O180.071 (3)0.095 (4)0.140 (4)0.051 (3)0.065 (3)0.078 (3)
O190.0353 (13)0.0428 (17)0.0278 (12)0.0020 (12)0.0020 (11)0.0040 (12)
O200.0334 (15)0.055 (2)0.0546 (18)0.0000 (14)0.0025 (14)0.0123 (16)
O210.0443 (16)0.0315 (15)0.0363 (14)0.0001 (13)0.0021 (12)0.0041 (12)
O220.081 (3)0.105 (4)0.070 (3)0.039 (3)0.014 (2)0.035 (3)
C300.0300 (18)0.034 (2)0.0278 (16)0.0022 (16)0.0005 (14)0.0003 (15)
C310.039 (2)0.031 (2)0.0266 (16)0.0005 (16)0.0004 (15)0.0049 (15)
C320.0316 (17)0.0279 (19)0.0259 (15)0.0009 (15)0.0035 (14)0.0023 (14)
C330.039 (2)0.035 (2)0.0252 (16)0.0029 (17)0.0026 (15)0.0026 (15)
C340.040 (2)0.029 (2)0.0269 (16)0.0026 (16)0.0004 (15)0.0007 (14)
C350.0347 (19)0.040 (2)0.0278 (16)0.0048 (17)0.0029 (15)0.0062 (16)
C360.039 (2)0.055 (3)0.0303 (18)0.000 (2)0.0059 (17)0.0022 (19)
C370.055 (3)0.101 (5)0.034 (2)0.011 (3)0.001 (2)0.022 (3)
C380.0317 (19)0.039 (2)0.0315 (18)0.0054 (17)0.0034 (16)0.0036 (16)
C390.042 (2)0.044 (3)0.041 (2)0.000 (2)0.0055 (18)0.0118 (19)
C400.042 (2)0.038 (2)0.047 (2)0.0038 (19)0.0080 (19)0.0136 (19)
C410.039 (2)0.050 (3)0.051 (2)0.004 (2)0.001 (2)0.019 (2)
C420.037 (2)0.036 (2)0.045 (2)0.0028 (18)0.0136 (18)0.0097 (18)
C430.057 (3)0.080 (4)0.046 (2)0.013 (3)0.019 (2)0.010 (3)
C440.050 (2)0.0239 (19)0.0325 (17)0.0057 (18)0.0028 (17)0.0028 (15)
C450.055 (3)0.033 (2)0.041 (2)0.005 (2)0.012 (2)0.0057 (17)
C460.065 (3)0.033 (2)0.0353 (19)0.009 (2)0.009 (2)0.0085 (17)
C470.062 (3)0.038 (2)0.035 (2)0.019 (2)0.007 (2)0.0065 (17)
C480.048 (2)0.035 (2)0.042 (2)0.009 (2)0.0052 (19)0.0081 (18)
C490.055 (2)0.037 (2)0.0264 (17)0.0087 (19)0.0063 (17)0.0057 (16)
C500.067 (3)0.046 (3)0.040 (2)0.024 (2)0.006 (2)0.008 (2)
C510.087 (4)0.042 (3)0.033 (2)0.025 (3)0.002 (2)0.0037 (19)
C520.078 (4)0.064 (4)0.039 (2)0.030 (3)0.007 (2)0.010 (2)
C530.096 (4)0.046 (3)0.029 (2)0.026 (3)0.001 (2)0.0036 (19)
C540.080 (4)0.043 (3)0.059 (3)0.008 (3)0.029 (3)0.017 (2)
C550.099 (5)0.061 (4)0.075 (4)0.031 (3)0.049 (3)0.035 (3)
C560.107 (5)0.031 (3)0.055 (3)0.007 (3)0.044 (3)0.010 (2)
C570.096 (5)0.066 (4)0.045 (3)0.036 (4)0.002 (3)0.014 (3)
C580.094 (4)0.080 (4)0.044 (3)0.046 (4)0.005 (3)0.015 (3)
Geometric parameters (Å, º) top
Cl1—C271.753 (5)Cl2—C561.743 (5)
O1—C51.415 (4)O12—C341.423 (4)
O1—C11.443 (5)O12—C301.431 (5)
O2—C71.336 (5)O13—C361.348 (5)
O2—C61.430 (5)O13—C351.438 (5)
O3—C71.219 (6)O14—C361.211 (6)
O4—C91.367 (4)O15—C381.367 (4)
O4—C21.448 (5)O15—C311.441 (4)
O5—C91.208 (5)O16—C381.199 (5)
O6—C111.363 (5)O17—C401.342 (5)
O6—C31.441 (4)O17—C321.452 (4)
O7—C111.203 (5)O18—C401.164 (5)
O8—C131.373 (5)O19—C421.373 (5)
O8—C41.439 (4)O19—C331.440 (4)
O9—C131.208 (5)O20—C421.201 (5)
O10—C151.393 (5)O21—C441.396 (5)
O10—C51.416 (5)O21—C341.397 (4)
O11—C231.234 (8)O22—C521.232 (7)
C1—C21.509 (5)C30—C351.500 (5)
C1—C61.516 (5)C30—C311.524 (5)
C1—H11.0000C30—H301.0000
C2—C31.521 (5)C31—C321.521 (5)
C2—H21.0000C31—H311.0000
C3—C41.524 (5)C32—C331.523 (5)
C3—H31.0000C32—H321.0000
C4—C51.527 (5)C33—C341.527 (5)
C4—H41.0000C33—H331.0000
C5—H51.0000C34—H341.0000
C6—H6A0.9900C35—H35A0.9900
C6—H6B0.9900C35—H35B0.9900
C7—C81.468 (7)C36—C371.485 (6)
C8—H8A0.9800C37—H37A0.9800
C8—H8B0.9800C37—H37B0.9800
C8—H8C0.9800C37—H37C0.9800
C9—C101.465 (6)C38—C391.476 (6)
C10—H10A0.9800C39—H39A0.9800
C10—H10B0.9800C39—H39B0.9800
C10—H10C0.9800C39—H39C0.9800
C11—C121.487 (5)C40—C411.496 (6)
C12—H12A0.9800C41—H41A0.9800
C12—H12B0.9800C41—H41B0.9800
C12—H12C0.9800C41—H41C0.9800
C13—C141.485 (6)C42—C431.494 (6)
C14—H14A0.9800C43—H43A0.9800
C14—H14B0.9800C43—H43B0.9800
C14—H14C0.9800C43—H43C0.9800
C15—C161.382 (6)C44—C491.376 (6)
C15—C201.389 (6)C44—C451.398 (5)
C16—C171.390 (7)C45—C461.384 (6)
C16—H160.9500C45—H450.9500
C17—C181.376 (7)C46—C471.388 (7)
C17—H170.9500C46—H460.9500
C18—C191.388 (6)C47—C481.405 (6)
C18—C211.470 (6)C47—C501.462 (6)
C19—C201.388 (6)C48—C491.404 (6)
C19—H190.9500C48—H480.9500
C20—H200.9500C49—H490.9500
C21—C221.321 (7)C50—C511.342 (6)
C21—H210.9500C50—H500.9500
C22—C231.484 (8)C51—C521.474 (7)
C22—H220.9500C51—H510.9500
C23—C241.506 (7)C52—C531.509 (7)
C24—C291.374 (9)C53—C581.392 (7)
C24—C251.375 (7)C53—C541.399 (8)
C25—C261.380 (7)C54—C551.421 (7)
C25—H250.9500C54—H540.9500
C26—C271.351 (9)C55—C561.400 (9)
C26—H260.9500C55—H550.9500
C27—C281.396 (8)C56—C571.346 (9)
C28—C291.415 (7)C57—C581.377 (7)
C28—H280.9500C57—H570.9500
C29—H290.9500C58—H580.9500
C5—O1—C1111.0 (3)C34—O12—C30112.1 (3)
C7—O2—C6118.0 (4)C36—O13—C35117.6 (3)
C9—O4—C2117.7 (3)C38—O15—C31116.4 (3)
C11—O6—C3116.9 (3)C40—O17—C32118.4 (3)
C13—O8—C4116.1 (3)C42—O19—C33116.0 (3)
C15—O10—C5116.3 (3)C44—O21—C34116.8 (3)
O1—C1—C2106.9 (3)O12—C30—C35109.0 (3)
O1—C1—C6107.9 (3)O12—C30—C31106.5 (3)
C2—C1—C6115.0 (3)C35—C30—C31114.9 (3)
O1—C1—H1108.9O12—C30—H30108.8
C2—C1—H1108.9C35—C30—H30108.8
C6—C1—H1108.9C31—C30—H30108.8
O4—C2—C1107.6 (3)O15—C31—C32109.0 (3)
O4—C2—C3109.5 (3)O15—C31—C30109.6 (3)
C1—C2—C3110.4 (3)C32—C31—C30109.4 (3)
O4—C2—H2109.8O15—C31—H31109.6
C1—C2—H2109.8C32—C31—H31109.6
C3—C2—H2109.8C30—C31—H31109.6
O6—C3—C2107.7 (3)O17—C32—C31106.7 (3)
O6—C3—C4107.8 (3)O17—C32—C33107.3 (3)
C2—C3—C4108.1 (3)C31—C32—C33109.8 (3)
O6—C3—H3111.0O17—C32—H32111.0
C2—C3—H3111.0C31—C32—H32111.0
C4—C3—H3111.0C33—C32—H32111.0
O8—C4—C3110.4 (3)O19—C33—C32109.5 (3)
O8—C4—C5105.7 (3)O19—C33—C34105.9 (3)
C3—C4—C5109.9 (3)C32—C33—C34110.2 (3)
O8—C4—H4110.2O19—C33—H33110.4
C3—C4—H4110.2C32—C33—H33110.4
C5—C4—H4110.2C34—C33—H33110.4
O1—C5—O10108.2 (3)O21—C34—O12107.8 (3)
O1—C5—C4109.0 (3)O21—C34—C33107.8 (3)
O10—C5—C4107.5 (3)O12—C34—C33109.7 (3)
O1—C5—H5110.7O21—C34—H34110.5
O10—C5—H5110.7O12—C34—H34110.5
C4—C5—H5110.7C33—C34—H34110.5
O2—C6—C1111.1 (3)O13—C35—C30111.6 (3)
O2—C6—H6A109.4O13—C35—H35A109.3
C1—C6—H6A109.4C30—C35—H35A109.3
O2—C6—H6B109.4O13—C35—H35B109.3
C1—C6—H6B109.4C30—C35—H35B109.3
H6A—C6—H6B108.0H35A—C35—H35B108.0
O3—C7—O2122.5 (4)O14—C36—O13124.1 (4)
O3—C7—C8126.0 (4)O14—C36—C37124.4 (4)
O2—C7—C8111.4 (5)O13—C36—C37111.4 (4)
C7—C8—H8A109.5C36—C37—H37A109.5
C7—C8—H8B109.5C36—C37—H37B109.5
H8A—C8—H8B109.5H37A—C37—H37B109.5
C7—C8—H8C109.5C36—C37—H37C109.5
H8A—C8—H8C109.5H37A—C37—H37C109.5
H8B—C8—H8C109.5H37B—C37—H37C109.5
O5—C9—O4121.9 (4)O16—C38—O15122.4 (4)
O5—C9—C10127.7 (4)O16—C38—C39127.0 (4)
O4—C9—C10110.4 (3)O15—C38—C39110.6 (3)
C9—C10—H10A109.5C38—C39—H39A109.5
C9—C10—H10B109.5C38—C39—H39B109.5
H10A—C10—H10B109.5H39A—C39—H39B109.5
C9—C10—H10C109.5C38—C39—H39C109.5
H10A—C10—H10C109.5H39A—C39—H39C109.5
H10B—C10—H10C109.5H39B—C39—H39C109.5
O7—C11—O6123.4 (4)O18—C40—O17122.9 (4)
O7—C11—C12125.7 (4)O18—C40—C41127.1 (4)
O6—C11—C12110.8 (4)O17—C40—C41110.0 (4)
C11—C12—H12A109.5C40—C41—H41A109.5
C11—C12—H12B109.5C40—C41—H41B109.5
H12A—C12—H12B109.5H41A—C41—H41B109.5
C11—C12—H12C109.5C40—C41—H41C109.5
H12A—C12—H12C109.5H41A—C41—H41C109.5
H12B—C12—H12C109.5H41B—C41—H41C109.5
O9—C13—O8121.1 (4)O20—C42—O19122.6 (4)
O9—C13—C14127.2 (4)O20—C42—C43127.2 (4)
O8—C13—C14111.7 (3)O19—C42—C43110.2 (4)
C13—C14—H14A109.5C42—C43—H43A109.5
C13—C14—H14B109.5C42—C43—H43B109.5
H14A—C14—H14B109.5H43A—C43—H43B109.5
C13—C14—H14C109.5C42—C43—H43C109.5
H14A—C14—H14C109.5H43A—C43—H43C109.5
H14B—C14—H14C109.5H43B—C43—H43C109.5
C16—C15—C20121.4 (4)C49—C44—O21122.4 (4)
C16—C15—O10115.8 (4)C49—C44—C45121.8 (4)
C20—C15—O10122.8 (4)O21—C44—C45115.8 (4)
C15—C16—C17118.8 (5)C46—C45—C44118.6 (4)
C15—C16—H16120.6C46—C45—H45120.7
C17—C16—H16120.6C44—C45—H45120.7
C18—C17—C16121.4 (4)C45—C46—C47121.9 (4)
C18—C17—H17119.3C45—C46—H46119.1
C16—C17—H17119.3C47—C46—H46119.1
C17—C18—C19118.5 (4)C46—C47—C48118.0 (4)
C17—C18—C21123.5 (4)C46—C47—C50123.7 (4)
C19—C18—C21118.0 (5)C48—C47—C50118.3 (5)
C18—C19—C20121.9 (5)C49—C48—C47121.3 (4)
C18—C19—H19119.1C49—C48—H48119.4
C20—C19—H19119.1C47—C48—H48119.4
C19—C20—C15117.9 (4)C44—C49—C48118.3 (4)
C19—C20—H20121.0C44—C49—H49120.8
C15—C20—H20121.0C48—C49—H49120.8
C22—C21—C18127.7 (6)C51—C50—C47127.7 (5)
C22—C21—H21116.1C51—C50—H50116.2
C18—C21—H21116.1C47—C50—H50116.2
C21—C22—C23120.4 (6)C50—C51—C52120.4 (5)
C21—C22—H22119.8C50—C51—H51119.8
C23—C22—H22119.8C52—C51—H51119.8
O11—C23—C22121.7 (5)O22—C52—C51121.7 (5)
O11—C23—C24118.9 (5)O22—C52—C53119.2 (5)
C22—C23—C24119.4 (6)C51—C52—C53119.1 (5)
C29—C24—C25118.8 (5)C58—C53—C54119.5 (5)
C29—C24—C23122.4 (5)C58—C53—C52118.7 (6)
C25—C24—C23118.8 (6)C54—C53—C52121.7 (5)
C24—C25—C26122.1 (7)C53—C54—C55120.3 (5)
C24—C25—H25119.0C53—C54—H54119.9
C26—C25—H25119.0C55—C54—H54119.9
C27—C26—C25118.3 (6)C56—C55—C54117.0 (6)
C27—C26—H26120.8C56—C55—H55121.5
C25—C26—H26120.8C54—C55—H55121.5
C26—C27—C28123.0 (5)C57—C56—C55122.4 (5)
C26—C27—Cl1119.7 (4)C57—C56—Cl2120.2 (5)
C28—C27—Cl1117.2 (5)C55—C56—Cl2117.4 (5)
C27—C28—C29116.7 (7)C56—C57—C58120.9 (6)
C27—C28—H28121.7C56—C57—H57119.6
C29—C28—H28121.7C58—C57—H57119.6
C24—C29—C28121.0 (5)C57—C58—C53119.9 (6)
C24—C29—H29119.5C57—C58—H58120.1
C28—C29—H29119.5C53—C58—H58120.1
C5—O1—C1—C266.7 (3)C34—O12—C30—C35168.3 (3)
C5—O1—C1—C6169.0 (3)C34—O12—C30—C3167.3 (4)
C9—O4—C2—C1133.4 (3)C38—O15—C31—C3295.5 (4)
C9—O4—C2—C3106.6 (4)C38—O15—C31—C30144.8 (3)
O1—C1—C2—O4178.9 (3)O12—C30—C31—O15178.5 (3)
C6—C1—C2—O459.1 (4)C35—C30—C31—O1557.8 (4)
O1—C1—C2—C361.6 (4)O12—C30—C31—C3262.0 (4)
C6—C1—C2—C3178.5 (3)C35—C30—C31—C32177.2 (3)
C11—O6—C3—C2148.9 (3)C40—O17—C32—C31127.7 (4)
C11—O6—C3—C494.7 (4)C40—O17—C32—C33114.7 (4)
O4—C2—C3—O658.6 (4)O15—C31—C32—O1760.0 (4)
C1—C2—C3—O659.7 (4)C30—C31—C32—O1759.9 (4)
O4—C2—C3—C4174.8 (3)O15—C31—C32—C33175.9 (3)
C1—C2—C3—C456.5 (4)C30—C31—C32—C3356.1 (4)
C13—O8—C4—C377.2 (4)C42—O19—C33—C3271.9 (4)
C13—O8—C4—C5163.9 (3)C42—O19—C33—C34169.3 (3)
O6—C3—C4—O853.8 (4)O17—C32—C33—O1952.2 (4)
C2—C3—C4—O8170.0 (3)C31—C32—C33—O19167.8 (3)
O6—C3—C4—C562.4 (4)O17—C32—C33—C3464.0 (4)
C2—C3—C4—C553.7 (4)C31—C32—C33—C3451.6 (4)
C1—O1—C5—O10178.0 (3)C44—O21—C34—O1285.7 (4)
C1—O1—C5—C465.5 (4)C44—O21—C34—C33156.0 (3)
C15—O10—C5—O188.4 (4)C30—O12—C34—O21178.8 (3)
C15—O10—C5—C4154.1 (3)C30—O12—C34—C3364.1 (4)
O8—C4—C5—O1177.4 (3)O19—C33—C34—O2170.0 (4)
C3—C4—C5—O158.3 (4)C32—C33—C34—O21171.6 (3)
O8—C4—C5—O1065.5 (4)O19—C33—C34—O12172.8 (3)
C3—C4—C5—O10175.4 (3)C32—C33—C34—O1254.4 (4)
C7—O2—C6—C1119.7 (4)C36—O13—C35—C30115.0 (4)
O1—C1—C6—O262.2 (4)O12—C30—C35—O1366.4 (4)
C2—C1—C6—O257.0 (5)C31—C30—C35—O1352.9 (5)
C6—O2—C7—O33.6 (6)C35—O13—C36—O145.4 (6)
C6—O2—C7—C8174.2 (4)C35—O13—C36—C37172.4 (4)
C2—O4—C9—O51.5 (6)C31—O15—C38—O160.2 (5)
C2—O4—C9—C10177.4 (3)C31—O15—C38—C39177.7 (3)
C3—O6—C11—O74.0 (6)C32—O17—C40—O180.3 (7)
C3—O6—C11—C12173.8 (3)C32—O17—C40—C41177.5 (3)
C4—O8—C13—O92.7 (6)C33—O19—C42—O206.4 (6)
C4—O8—C13—C14177.2 (3)C33—O19—C42—C43170.7 (4)
C5—O10—C15—C16151.4 (4)C34—O21—C44—C4923.5 (5)
C5—O10—C15—C2028.1 (5)C34—O21—C44—C45155.7 (3)
C20—C15—C16—C173.2 (7)C49—C44—C45—C462.4 (6)
O10—C15—C16—C17176.3 (4)O21—C44—C45—C46176.8 (3)
C15—C16—C17—C180.4 (7)C44—C45—C46—C470.7 (7)
C16—C17—C18—C192.1 (7)C45—C46—C47—C482.5 (7)
C16—C17—C18—C21178.3 (5)C45—C46—C47—C50179.2 (4)
C17—C18—C19—C201.9 (7)C46—C47—C48—C491.2 (6)
C21—C18—C19—C20178.2 (4)C50—C47—C48—C49179.7 (4)
C18—C19—C20—C150.8 (7)O21—C44—C49—C48175.6 (4)
C16—C15—C20—C193.4 (6)C45—C44—C49—C483.5 (6)
O10—C15—C20—C19176.1 (4)C47—C48—C49—C441.7 (6)
C17—C18—C21—C222.4 (8)C46—C47—C50—C512.5 (8)
C19—C18—C21—C22173.8 (5)C48—C47—C50—C51175.9 (5)
C18—C21—C22—C23178.9 (5)C47—C50—C51—C52176.7 (4)
C21—C22—C23—O114.5 (9)C50—C51—C52—O224.8 (8)
C21—C22—C23—C24176.6 (5)C50—C51—C52—C53176.7 (4)
O11—C23—C24—C29171.2 (6)O22—C52—C53—C587.6 (8)
C22—C23—C24—C299.9 (8)C51—C52—C53—C58170.9 (5)
O11—C23—C24—C257.6 (8)O22—C52—C53—C54169.1 (6)
C22—C23—C24—C25171.3 (5)C51—C52—C53—C5412.4 (7)
C29—C24—C25—C261.3 (9)C58—C53—C54—C550.6 (8)
C23—C24—C25—C26177.6 (5)C52—C53—C54—C55176.1 (5)
C24—C25—C26—C270.1 (9)C53—C54—C55—C561.7 (9)
C25—C26—C27—C280.6 (9)C54—C55—C56—C571.2 (9)
C25—C26—C27—Cl1177.5 (4)C54—C55—C56—Cl2179.4 (4)
C26—C27—C28—C292.2 (8)C55—C56—C57—C580.4 (10)
Cl1—C27—C28—C29179.1 (4)Cl2—C56—C57—C58177.7 (5)
C25—C24—C29—C282.9 (8)C56—C57—C58—C531.5 (9)
C23—C24—C29—C28175.9 (5)C54—C53—C58—C571.0 (9)
C27—C28—C29—C243.3 (8)C52—C53—C58—C57177.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O9i1.002.383.185 (5)137
C20—H20···O10.952.543.111 (5)118
C20—H20···O9i0.952.543.271 (5)134
C30—H30···O20i1.002.513.316 (5)138
C32—H32···O201.002.533.031 (5)111
C49—H49···O120.952.503.065 (5)119
C49—H49···O20i0.952.533.271 (6)135
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC29H29ClO11
Mr588.97
Crystal system, space groupMonoclinic, P21
Temperature (K)113
a, b, c (Å)7.2387 (14), 39.239 (8), 10.297 (2)
β (°) 90.25 (3)
V3)2924.7 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.27 × 0.25 × 0.20
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.951, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
17131, 11143, 8341
Rint0.041
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.189, 1.04
No. of reflections11143
No. of parameters748
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.76, 0.37
Absolute structureFlack (1983); 4380 Friedel pairs
Absolute structure parameter0.03 (8)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O9i1.002.383.185 (5)137
C20—H20···O10.952.543.111 (5)118
C20—H20···O9i0.952.543.271 (5)134
C30—H30···O20i1.002.513.316 (5)138
C32—H32···O201.002.533.031 (5)111
C49—H49···O120.952.503.065 (5)119
C49—H49···O20i0.952.533.271 (6)135
Symmetry code: (i) x1, y, z.
 

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

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First citationRigaku/MSC. (2005). CrystalClear. Rigaku/MSC, The Woodlands ,Texas, USA.  Google Scholar
First citationSha, J. Z. & Mao, H. K. (1987). Chin. Pharm. Bull. 22, 27–30.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationYe, D., Zhang, K., Chen, H., Yin, S. & Li, Y. (2009). Acta Cryst. E65, o1338.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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