organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

2,3,6,3′,4′-Penta-O-acetyl-4,1′,6′-tri­chloro-4,1′,6′-tride­­oxy­sucrose

aEast China University of Science and Technology, 200237 Shanghai, People's Republic of China
*Correspondence e-mail: fzwu@ecust.edu.cn

(Received 19 July 2011; accepted 8 August 2011; online 11 August 2011)

In the title compound, C22H29Cl3O13, the glucopyran ring exists in the chair conformation while the glucofuran ring adopts an envelope conformation. Intra­molecular C—H⋯O hydrogen bonds occur. In the crystal, adjacent mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For general background to sucralose (4,1′,6′-trichloro-4,1′,6′-tride­oxy-galacto-sucrose), see: John et al. (2000[John, B. A., Wood, S. G. & Hawkins, D. R. (2000). Food Chem. Toxicol. 38, 99-111.]); Khan (1972[Khan, R. (1972). Carbohydr. Res. 25, 504-510.]); Mclean (2000[Mclean, B. I. (2000). Food Chem. Toxicol. 38, 123-129.]). For details of the synthesis, see: Kille et al. (2000[Kille, J. W., Tesh, J. M. & Mcanulty, P. A. (2000). Food Chem. Toxicol. 38, 43-45.]); Wu et al. (2010[Wu, F.-Z., Long, Z.-Z. & Zhang, P. (2010). J. Chem. Ind. Eng. 61, 2731-2737.]).

[Scheme 1]

Experimental

Crystal data
  • C22H29Cl3O13

  • Mr = 607.80

  • Orthorhombic, P 21 21 21

  • a = 8.9813 (6) Å

  • b = 15.5062 (10) Å

  • c = 19.9737 (13) Å

  • V = 2781.7 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.39 mm−1

  • T = 293 K

  • 0.37 × 0.31 × 0.21 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.]) Tmin = 0.777, Tmax = 1.000

  • 15159 measured reflections

  • 5463 independent reflections

  • 5081 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.06

  • 5463 reflections

  • 348 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.19 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2367 Friedel pairs

  • Flack parameter: 0.00 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12B⋯O13 0.96 2.51 3.304 (3) 139
C16—H16B⋯O11i 0.96 2.57 3.300 (4) 133
C19—H19B⋯O3ii 0.96 2.40 3.351 (4) 172
C21—H21C⋯O3iii 0.96 2.44 3.396 (4) 174
C22—H22A⋯O1 0.97 2.49 3.321 (3) 143
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The well known sucralose (4,1',6'-Trichloro-4,1',6'–trideoxy-galacto-sucrose) is a low calorie sweetener made from suger and tastes similar to sugar. It is about 600 times sweeter than suger. Sucralose can be safely consumed and used wherein there is a need to avoid use of sugar. More particularly it is very useful for preparing food, beverages and nutritional product wherein the use of sugar needs to be avoided. The sucralose is used in foods sweetening beverage and nutritional products ingredient world wide. Sucralose is a high-sensitivity artificial sweetener (John et al., 2000; Khan, 1972; Mclean et al., 2000), and many convertional methods of producing sucralose have already been reported (Kille et al., 2000). The title compound (4,1',6'-Trichloro-4,1',6'-trideoxy-2,3,6,3',4'-sucrose pentaacetate), as the key intermediate of sucralose, was obtained by ourselves (Wu et al., 2010). Herein, we report the synthesis, characterization and crystal structure of the title compound.

The compound crystallizes in the orthorhombic space group P212121, with one molecule in the asymmetric unit. The molecule structure consists of a glucopyran ring and a glucofuran ring (Fig. 1). The glucopyran ring exists in the form of chair, while the glucofuran ring adopts envelope conformation. The two rings attach to one oxygen atom by equation bonds. Even though non-classical hydrogen bonds observed in the crystal structure, two kind of weak intermolecular C—H···O and C—H···Cl hydrogen bonds play an important role in the formation of a three-dimensional suparmolecular architecture (Fig. 2).

Related literature top

For general background to sucralose (4,1',6'-trichloro-4,1',6'-trideoxy-galacto-sucrose), see: John et al. (2000); Khan (1972); Mclean (2000). For details of the synthesis, see: Kille et al. (2000); Wu et al. (2010).

Experimental top

2,3,6,3',4'-Penta-O-acetylsucrose (4.5 mmol) and thionyl chloride (5.0 mmol) in toluene (10 ml) were refluxed for 4 h. Then solvent was removed on a vacuum rotary evaporator. Crude product (2.84 g, 90% yield) was recrystallized from EtOH to give crystals suitable for single-crystal X-ray diffraction (yield 85%).

Refinement top

All H atoms were placed in geometrically idealized positions with C—H = 0.98–0.96 Å and refined in riding mode with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 molecular structure showing ellipsoids at the 30% probability level. Hydrogen atoms have been omitted for clarity.
[Figure 2] Fig. 2. Packing diagram view along the a axis.
2,3,6,3',4'-Penta-O-acetyl-4,1',6'-trichloro-4,1',6'-trideoxysucrose top
Crystal data top
C22H29Cl3O13F(000) = 1264
Mr = 607.80Dx = 1.451 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6865 reflections
a = 8.9813 (6) Åθ = 2.4–25.6°
b = 15.5062 (10) ŵ = 0.39 mm1
c = 19.9737 (13) ÅT = 293 K
V = 2781.7 (3) Å3Prism, colourless
Z = 40.37 × 0.31 × 0.21 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5463 independent reflections
Radiation source: fine-focus sealed tube5081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1011
Tmin = 0.777, Tmax = 1.000k = 1912
15159 measured reflectionsl = 2424
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.3705P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.007
5463 reflectionsΔρmax = 0.32 e Å3
348 parametersΔρmin = 0.19 e Å3
0 restraintsAbsolute structure: Flack (1983), 2367 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (5)
Crystal data top
C22H29Cl3O13V = 2781.7 (3) Å3
Mr = 607.80Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.9813 (6) ŵ = 0.39 mm1
b = 15.5062 (10) ÅT = 293 K
c = 19.9737 (13) Å0.37 × 0.31 × 0.21 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5463 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
5081 reflections with I > 2σ(I)
Tmin = 0.777, Tmax = 1.000Rint = 0.021
15159 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.32 e Å3
S = 1.06Δρmin = 0.19 e Å3
5463 reflectionsAbsolute structure: Flack (1983), 2367 Friedel pairs
348 parametersAbsolute structure parameter: 0.00 (5)
0 restraints
Special details top

Experimental. 1H NMR (400 MHz, DMSO-d6): σ 2.03 (3H, s, COCH3), 2.05 (3H, s, COCH3), 2.06 (6H, s, COCH3), 2.07 (3H, s, COCH3), 3.82–3.96 (4H, m, 2ClCH2), 4.16 (2H, d, J = 5.6 Hz, CH2OAc), 4.26–4.31 (1H, m), 4.55 (1H, t, J = 5.8 Hz), 4.85 (1H, dd, J = 1.0, 3.4 Hz), 5.15 (1H, dd, J = 3.6, 8.1 Hz), 5.34–5.40 (2H, m), 5.64 (1H, d, J = 7.2 Hz), 5.68 (1H, d, J = 3.6 Hz).

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 > σ(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
Cl10.18975 (7)0.24388 (4)0.12651 (3)0.05417 (15)
Cl20.09410 (10)0.70991 (4)0.09992 (4)0.0764 (2)
Cl30.38581 (8)0.40249 (5)0.17639 (5)0.0757 (2)
O10.16446 (17)0.35433 (9)0.00841 (7)0.0428 (3)
O20.0328 (2)0.21775 (11)0.08279 (9)0.0582 (5)
O30.1521 (3)0.09365 (15)0.09253 (11)0.0966 (9)
O40.0716 (2)0.39925 (11)0.18950 (8)0.0562 (4)
O50.1314 (2)0.32350 (16)0.21651 (11)0.0778 (6)
O60.14003 (19)0.53711 (9)0.10439 (8)0.0482 (4)
O70.3616 (3)0.54004 (15)0.15533 (15)0.0985 (8)
O80.02654 (16)0.48044 (9)0.01512 (7)0.0415 (3)
O90.15910 (17)0.51900 (10)0.11205 (7)0.0447 (3)
O100.23093 (18)0.51482 (10)0.07552 (8)0.0484 (4)
O110.2683 (3)0.65461 (13)0.05707 (14)0.0862 (7)
O120.1484 (2)0.47132 (10)0.21759 (8)0.0522 (4)
O130.1041 (3)0.33524 (11)0.24732 (9)0.0669 (5)
C10.0421 (2)0.30399 (14)0.01580 (11)0.0421 (5)
H10.05090.32860.00130.050*
C20.0366 (2)0.30306 (14)0.09186 (11)0.0403 (4)
H20.05620.27500.10580.048*
C30.0374 (2)0.39501 (13)0.11934 (10)0.0417 (5)
H30.05950.42200.11110.050*
C40.1589 (2)0.44793 (13)0.08635 (11)0.0403 (5)
H40.25590.42800.10260.048*
C50.1564 (2)0.44207 (13)0.01042 (11)0.0398 (5)
H50.24330.47250.00750.048*
C60.0430 (3)0.54111 (14)0.06840 (10)0.0410 (5)
C70.0980 (2)0.53377 (14)0.11150 (10)0.0424 (5)
H70.11140.58670.13760.051*
C80.0613 (3)0.46004 (15)0.15774 (11)0.0445 (5)
H80.08380.40460.13650.053*
C90.1065 (3)0.47010 (14)0.16894 (10)0.0449 (5)
H90.12400.50300.21010.054*
C100.0605 (3)0.21462 (15)0.01212 (13)0.0539 (6)
H10A0.00910.17550.00920.065*
H10B0.16070.19390.00370.065*
C110.0786 (3)0.14943 (14)0.11772 (13)0.0513 (6)
C120.0301 (3)0.15198 (16)0.18838 (13)0.0567 (6)
H12A0.07370.13750.19110.085*
H12B0.04550.20890.20610.085*
H12C0.08700.11120.21390.085*
C130.0184 (4)0.35766 (17)0.23298 (13)0.0618 (7)
C140.0489 (6)0.3574 (3)0.30054 (15)0.1107 (16)
H14A0.12690.31510.30230.166*
H14B0.08950.41330.31010.166*
H14C0.02590.34350.33310.166*
C150.2519 (3)0.57680 (15)0.13722 (12)0.0542 (6)
C160.2162 (4)0.66902 (16)0.14929 (15)0.0766 (9)
H16A0.30240.69780.16680.115*
H16B0.18700.69570.10790.115*
H16C0.13600.67320.18090.115*
C170.0780 (3)0.62800 (15)0.03785 (12)0.0502 (5)
H17A0.00030.64350.00660.060*
H17B0.17060.62420.01300.060*
C180.3104 (3)0.58228 (18)0.05202 (13)0.0558 (6)
C190.4519 (3)0.5537 (2)0.02097 (17)0.0764 (9)
H19A0.51340.52670.05430.115*
H19B0.43100.51310.01410.115*
H19C0.50310.60260.00260.115*
C200.1637 (3)0.40117 (15)0.25818 (12)0.0497 (5)
C210.2646 (4)0.42122 (19)0.31566 (15)0.0718 (8)
H21A0.27090.37200.34460.108*
H21B0.36200.43510.29910.108*
H21C0.22570.46940.34020.108*
C220.1891 (3)0.38625 (16)0.17245 (13)0.0522 (6)
H22A0.16530.35190.13330.063*
H22B0.15690.35450.21170.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0536 (3)0.0469 (3)0.0621 (3)0.0062 (3)0.0132 (3)0.0079 (3)
Cl20.0967 (6)0.0442 (3)0.0881 (5)0.0107 (4)0.0013 (4)0.0182 (3)
Cl30.0544 (4)0.0727 (5)0.1000 (6)0.0109 (3)0.0020 (4)0.0109 (4)
O10.0459 (8)0.0387 (7)0.0437 (8)0.0032 (6)0.0028 (6)0.0014 (6)
O20.0691 (11)0.0485 (9)0.0569 (10)0.0143 (9)0.0188 (9)0.0138 (8)
O30.156 (2)0.0704 (13)0.0633 (12)0.0511 (16)0.0096 (14)0.0051 (10)
O40.0768 (12)0.0511 (9)0.0408 (8)0.0128 (9)0.0033 (8)0.0013 (7)
O50.0640 (12)0.0976 (16)0.0719 (13)0.0123 (12)0.0156 (10)0.0165 (11)
O60.0612 (9)0.0342 (7)0.0492 (8)0.0014 (7)0.0071 (7)0.0001 (6)
O70.0832 (16)0.0680 (14)0.144 (2)0.0071 (12)0.0512 (16)0.0181 (14)
O80.0402 (7)0.0437 (8)0.0405 (7)0.0026 (7)0.0018 (6)0.0080 (6)
O90.0444 (8)0.0460 (8)0.0436 (8)0.0028 (7)0.0055 (6)0.0007 (6)
O100.0451 (9)0.0479 (9)0.0524 (8)0.0026 (7)0.0029 (7)0.0070 (7)
O110.0912 (16)0.0523 (11)0.1152 (18)0.0098 (11)0.0340 (14)0.0051 (12)
O120.0643 (10)0.0472 (9)0.0452 (8)0.0014 (8)0.0120 (7)0.0034 (7)
O130.0935 (14)0.0459 (10)0.0611 (11)0.0005 (10)0.0128 (10)0.0030 (8)
C10.0393 (11)0.0385 (11)0.0485 (11)0.0020 (9)0.0056 (9)0.0016 (9)
C20.0357 (10)0.0373 (11)0.0480 (11)0.0008 (9)0.0042 (9)0.0054 (9)
C30.0472 (11)0.0386 (11)0.0392 (11)0.0020 (9)0.0001 (9)0.0019 (9)
C40.0444 (12)0.0336 (10)0.0430 (11)0.0009 (9)0.0037 (9)0.0019 (8)
C50.0358 (11)0.0398 (10)0.0439 (11)0.0010 (8)0.0004 (8)0.0029 (8)
C60.0457 (11)0.0369 (10)0.0405 (10)0.0012 (9)0.0032 (9)0.0063 (9)
C70.0458 (11)0.0409 (11)0.0406 (11)0.0009 (9)0.0020 (9)0.0077 (9)
C80.0501 (12)0.0417 (11)0.0418 (11)0.0013 (10)0.0045 (9)0.0069 (9)
C90.0556 (13)0.0433 (11)0.0357 (10)0.0005 (10)0.0020 (9)0.0058 (9)
C100.0616 (15)0.0431 (12)0.0571 (14)0.0010 (11)0.0108 (12)0.0034 (10)
C110.0585 (14)0.0362 (11)0.0591 (13)0.0015 (10)0.0091 (11)0.0018 (10)
C120.0630 (15)0.0497 (14)0.0573 (14)0.0026 (12)0.0040 (12)0.0086 (11)
C130.084 (2)0.0514 (14)0.0502 (13)0.0030 (14)0.0166 (13)0.0065 (11)
C140.188 (5)0.098 (3)0.0462 (15)0.057 (3)0.001 (2)0.0106 (16)
C150.0730 (17)0.0422 (12)0.0473 (13)0.0118 (12)0.0048 (12)0.0021 (10)
C160.123 (3)0.0427 (13)0.0645 (17)0.0157 (17)0.0068 (18)0.0037 (12)
C170.0589 (14)0.0414 (12)0.0503 (12)0.0015 (11)0.0000 (10)0.0030 (10)
C180.0555 (13)0.0609 (16)0.0511 (13)0.0152 (12)0.0035 (11)0.0094 (12)
C190.0586 (16)0.093 (2)0.0774 (19)0.0142 (16)0.0169 (15)0.0131 (17)
C200.0597 (14)0.0471 (13)0.0422 (12)0.0086 (11)0.0023 (10)0.0077 (10)
C210.088 (2)0.0648 (17)0.0623 (16)0.0054 (16)0.0263 (15)0.0004 (14)
C220.0555 (13)0.0489 (13)0.0523 (13)0.0033 (11)0.0045 (11)0.0011 (10)
Geometric parameters (Å, º) top
Cl1—C21.793 (2)C6—C171.512 (3)
Cl2—C171.781 (2)C6—C71.536 (3)
Cl3—C221.786 (3)C7—C81.506 (3)
O1—C51.414 (3)C7—H70.9800
O1—C11.432 (3)C8—C91.532 (3)
O2—C111.333 (3)C8—H80.9800
O2—C101.434 (3)C9—C221.498 (3)
O3—C111.199 (3)C9—H90.9800
O4—C131.351 (3)C10—H10A0.9700
O4—C31.436 (3)C10—H10B0.9700
O5—C131.191 (4)C11—C121.478 (4)
O6—C151.348 (3)C12—H12A0.9600
O6—C41.439 (2)C12—H12B0.9600
O7—C151.195 (3)C12—H12C0.9600
O8—C51.405 (3)C13—C141.479 (5)
O8—C61.428 (2)C14—H14A0.9600
O9—C61.402 (3)C14—H14B0.9600
O9—C91.445 (3)C14—H14C0.9600
O10—C181.350 (3)C15—C161.485 (4)
O10—C71.424 (3)C16—H16A0.9600
O11—C181.188 (3)C16—H16B0.9600
O12—C201.364 (3)C16—H16C0.9600
O12—C81.439 (3)C17—H17A0.9700
O13—C201.174 (3)C17—H17B0.9700
C1—C101.503 (3)C18—C191.483 (4)
C1—C21.520 (3)C19—H19A0.9600
C1—H10.9800C19—H19B0.9600
C2—C31.528 (3)C19—H19C0.9600
C2—H20.9800C20—C211.495 (4)
C3—C41.516 (3)C21—H21A0.9600
C3—H30.9800C21—H21B0.9600
C4—C51.519 (3)C21—H21C0.9600
C4—H40.9800C22—H22A0.9700
C5—H50.9800C22—H22B0.9700
C5—O1—C1113.30 (16)O2—C10—H10A110.0
C11—O2—C10115.76 (19)C1—C10—H10A110.0
C13—O4—C3118.6 (2)O2—C10—H10B110.0
C15—O6—C4118.21 (19)C1—C10—H10B110.0
C5—O8—C6117.60 (16)H10A—C10—H10B108.4
C6—O9—C9111.99 (16)O3—C11—O2121.6 (2)
C18—O10—C7117.29 (19)O3—C11—C12125.6 (2)
C20—O12—C8116.86 (18)O2—C11—C12112.8 (2)
O1—C1—C10107.04 (18)C11—C12—H12A109.5
O1—C1—C2111.57 (17)C11—C12—H12B109.5
C10—C1—C2111.45 (18)H12A—C12—H12B109.5
O1—C1—H1108.9C11—C12—H12C109.5
C10—C1—H1108.9H12A—C12—H12C109.5
C2—C1—H1108.9H12B—C12—H12C109.5
C1—C2—C3110.49 (17)O5—C13—O4123.0 (3)
C1—C2—Cl1111.46 (16)O5—C13—C14126.8 (3)
C3—C2—Cl1109.58 (15)O4—C13—C14110.1 (3)
C1—C2—H2108.4C13—C14—H14A109.5
C3—C2—H2108.4C13—C14—H14B109.5
Cl1—C2—H2108.4H14A—C14—H14B109.5
O4—C3—C4104.23 (18)C13—C14—H14C109.5
O4—C3—C2113.23 (17)H14A—C14—H14C109.5
C4—C3—C2110.64 (18)H14B—C14—H14C109.5
O4—C3—H3109.5O7—C15—O6123.0 (2)
C4—C3—H3109.5O7—C15—C16126.0 (3)
C2—C3—H3109.5O6—C15—C16111.0 (3)
O6—C4—C3109.05 (18)C15—C16—H16A109.5
O6—C4—C5107.80 (16)C15—C16—H16B109.5
C3—C4—C5113.00 (18)H16A—C16—H16B109.5
O6—C4—H4109.0C15—C16—H16C109.5
C3—C4—H4109.0H16A—C16—H16C109.5
C5—C4—H4109.0H16B—C16—H16C109.5
O8—C5—O1110.70 (17)C6—C17—Cl2111.80 (16)
O8—C5—C4110.45 (17)C6—C17—H17A109.3
O1—C5—C4108.81 (17)Cl2—C17—H17A109.3
O8—C5—H5108.9C6—C17—H17B109.3
O1—C5—H5108.9Cl2—C17—H17B109.3
C4—C5—H5108.9H17A—C17—H17B107.9
O9—C6—O8112.31 (17)O11—C18—O10122.3 (3)
O9—C6—C17108.34 (18)O11—C18—C19126.2 (3)
O8—C6—C17107.93 (18)O10—C18—C19111.5 (2)
O9—C6—C7104.27 (16)C18—C19—H19A109.5
O8—C6—C7106.46 (17)C18—C19—H19B109.5
C17—C6—C7117.62 (19)H19A—C19—H19B109.5
O10—C7—C8109.63 (18)C18—C19—H19C109.5
O10—C7—C6115.08 (17)H19A—C19—H19C109.5
C8—C7—C6102.71 (17)H19B—C19—H19C109.5
O10—C7—H7109.7O13—C20—O12122.6 (2)
C8—C7—H7109.7O13—C20—C21126.8 (2)
C6—C7—H7109.7O12—C20—C21110.6 (2)
O12—C8—C7107.36 (17)C20—C21—H21A109.5
O12—C8—C9113.64 (18)C20—C21—H21B109.5
C7—C8—C9103.13 (18)H21A—C21—H21B109.5
O12—C8—H8110.8C20—C21—H21C109.5
C7—C8—H8110.8H21A—C21—H21C109.5
C9—C8—H8110.8H21B—C21—H21C109.5
O9—C9—C22109.29 (18)C9—C22—Cl3111.67 (17)
O9—C9—C8105.08 (17)C9—C22—H22A109.3
C22—C9—C8113.9 (2)Cl3—C22—H22A109.3
O9—C9—H9109.5C9—C22—H22B109.3
C22—C9—H9109.5Cl3—C22—H22B109.3
C8—C9—H9109.5H22A—C22—H22B107.9
O2—C10—C1108.36 (18)
C5—O1—C1—C10176.05 (17)O8—C6—C7—O1034.1 (2)
C5—O1—C1—C261.8 (2)C17—C6—C7—O1087.0 (2)
O1—C1—C2—C353.4 (2)O9—C6—C7—C834.0 (2)
C10—C1—C2—C3172.96 (19)O8—C6—C7—C884.92 (19)
O1—C1—C2—Cl168.7 (2)C17—C6—C7—C8153.96 (19)
C10—C1—C2—Cl150.9 (2)C20—O12—C8—C7162.76 (19)
C13—O4—C3—C4179.9 (2)C20—O12—C8—C983.9 (2)
C13—O4—C3—C259.8 (3)O10—C7—C8—O1282.9 (2)
C1—C2—C3—O4164.59 (19)C6—C7—C8—O12154.33 (17)
Cl1—C2—C3—O441.4 (2)O10—C7—C8—C9156.84 (16)
C1—C2—C3—C448.0 (2)C6—C7—C8—C934.0 (2)
Cl1—C2—C3—C475.18 (19)C6—O9—C9—C22123.71 (19)
C15—O6—C4—C3120.1 (2)C6—O9—C9—C81.1 (2)
C15—O6—C4—C5116.9 (2)O12—C8—C9—O9138.49 (17)
O4—C3—C4—O668.0 (2)C7—C8—C9—O922.6 (2)
C2—C3—C4—O6169.99 (16)O12—C8—C9—C22101.9 (2)
O4—C3—C4—C5172.15 (17)C7—C8—C9—C22142.19 (19)
C2—C3—C4—C550.1 (2)C11—O2—C10—C1164.5 (2)
C6—O8—C5—O1108.77 (19)O1—C1—C10—O270.0 (2)
C6—O8—C5—C4130.65 (18)C2—C1—C10—O2167.7 (2)
C1—O1—C5—O860.5 (2)C10—O2—C11—O37.7 (4)
C1—O1—C5—C461.1 (2)C10—O2—C11—C12172.8 (2)
O6—C4—C5—O854.3 (2)C3—O4—C13—O56.3 (4)
C3—C4—C5—O866.3 (2)C3—O4—C13—C14170.4 (3)
O6—C4—C5—O1176.01 (16)C4—O6—C15—O74.5 (4)
C3—C4—C5—O155.4 (2)C4—O6—C15—C16177.7 (2)
C9—O9—C6—O894.3 (2)O9—C6—C17—Cl260.4 (2)
C9—O9—C6—C17146.60 (17)O8—C6—C17—Cl2177.80 (15)
C9—O9—C6—C720.6 (2)C7—C6—C17—Cl257.4 (2)
C5—O8—C6—O935.1 (2)C7—O10—C18—O114.5 (4)
C5—O8—C6—C1784.3 (2)C7—O10—C18—C19175.0 (2)
C5—O8—C6—C7148.60 (17)C8—O12—C20—O133.4 (4)
C18—O10—C7—C8155.65 (19)C8—O12—C20—C21176.3 (2)
C18—O10—C7—C689.2 (2)O9—C9—C22—Cl356.5 (2)
O9—C6—C7—O10153.05 (17)C8—C9—C22—Cl3173.66 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O130.962.513.304 (3)139
C16—H16B···O11i0.962.573.300 (4)133
C19—H19B···O3ii0.962.403.351 (4)172
C21—H21C···O3iii0.962.443.396 (4)174
C22—H22A···O10.972.493.321 (3)143
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1/2, y+1/2, z; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H29Cl3O13
Mr607.80
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.9813 (6), 15.5062 (10), 19.9737 (13)
V3)2781.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.37 × 0.31 × 0.21
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.777, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
15159, 5463, 5081
Rint0.021
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.06
No. of reflections5463
No. of parameters348
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.19
Absolute structureFlack (1983), 2367 Friedel pairs
Absolute structure parameter0.00 (5)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O130.962.513.304 (3)139
C16—H16B···O11i0.962.573.300 (4)133
C19—H19B···O3ii0.962.403.351 (4)172
C21—H21C···O3iii0.962.443.396 (4)174
C22—H22A···O10.972.493.321 (3)143
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1/2, y+1/2, z; (iii) x, y+1/2, z+1/2.
 

Acknowledgements

The authors thank the East China University of Science and Technology (No. 2006–02) and Shanghai Dongyue Biochemical Ltd. (No. 2010–10) for financial support of this work.

References

First citationBruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJohn, B. A., Wood, S. G. & Hawkins, D. R. (2000). Food Chem. Toxicol. 38, 99–111.  Google Scholar
First citationKhan, R. (1972). Carbohydr. Res. 25, 504–510.  CrossRef CAS Google Scholar
First citationKille, J. W., Tesh, J. M. & Mcanulty, P. A. (2000). Food Chem. Toxicol. 38, 43–45.  Google Scholar
First citationMclean, B. I. (2000). Food Chem. Toxicol. 38, 123–129.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, F.-Z., Long, Z.-Z. & Zhang, P. (2010). J. Chem. Ind. Eng. 61, 2731–2737.  CAS Google Scholar

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