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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1106

2,3,4,6-Tetra-O-acetyl-β-D-galacto­pyranosyl 2-(2,4-di­chloro­anilino)-4,4-di­methyl-6-oxo­cyclo­hex-1-enecarbo­di­thio­ate

aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 April 2009; accepted 21 April 2009; online 25 April 2009)

The cyclo­hexene ring in the title compound, C29H33Cl2NO10S2, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.63 (1) Å from the plane through the other five ring atoms (r.m.s. deviation = 0.11 Å). The mol­ecular conformation is stabilized by an intra­molecular N—H⋯S hydrogen bond. The crystal studied was a non-merohedral twin, with a minor twin component of 29%.

Related literature

For background to thio­glycosides, see: El Ashry et al. (2006[El Ashry, E. S. H., Awad, L. F. & Atta, A. I. (2006). Tetrahedron, 62, 2943-2998.], 2008[El Ashry, E. S. H., Rashed, N., Awad, L. F., Ramadan, E. S., Abdel-Maggeed, S. M. & Rezki, N. (2008). J. Carbohydr. Chem. 27, 70-85.]), Haikel et al. (2003[Haikel, A. Z., El Ashry, E. S. H. & Banoub, J. (2003). Carbohydr. Res. 338, 2291-2299.]). For the deconvolution of non-merohedrally twinned diffraction data, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C29H33Cl2NO10S2

  • Mr = 690.58

  • Monoclinic, P 21

  • a = 13.8257 (4) Å

  • b = 8.7697 (3) Å

  • c = 14.0690 (4) Å

  • β = 106.486 (2)°

  • V = 1635.70 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 100 K

  • 0.35 × 0.15 × 0.02 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.852, Tmax = 0.992

  • 15059 measured reflections

  • 7402 independent reflections

  • 5732 reflections with I > 2σ(I)

  • Rint = 0.065

Refinement
  • R[F2 > 2σ(F2)] = 0.092

  • wR(F2) = 0.263

  • S = 1.09

  • 7402 reflections

  • 408 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.06 e Å−3

  • Δρmin = −0.99 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3420 Friedel pairs

  • Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S2 0.88 (1) 2.07 (5) 2.882 (6) 152 (9)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For background to thioglycosides, see: El Ashry et al. (2006, 2008), Haikel et al. (2003). For the deconvolution of non-merohedrally twinned diffraction data, see: Spek (2009).

Experimental top

A cooled (283 K) solution of (2,4-dichloroanilino)-5,5-dimethyl-cyclohex-2-en-1-one (0.1 mol) and sodium hydroxide (0.4 g) in DMSO (20 ml) and water (1 ml) was treated with carbon disulfide (0.3 mol). After 20 min, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (0.12 mol) was added and the reaction mixture was left for 24 h. Water (200 ml) was added and the mixture acidified with 10% hydrochloric acid. The product was purified on by silica-gel column-chromatography to give yellow crystals that were further crystallized from methanol (m.p. 480 K).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The amino H-atom was located in a difference Fourier map and was refined with a distance restraint of N–H 0.88±0.01 Å; its displacement factor was freely refined.

The structure initally refined to R = 0.118 but the displacement factors and bond dimensions for all atoms were normal. Subsequent analysis showed the structure to be a non-merohedral twin. PLATON (Spek, 2009) split the reflection data by the matrix (-1 0 0, 0 - 1 0, 0.578 0 1). The minor twin component refined to 0.287.

The final difference Fourier map had a large peak at 1.5 Å from H4a.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C29H33Cl2NOS2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate top
Crystal data top
C29H33Cl2NO10S2F(000) = 720
Mr = 690.58Dx = 1.402 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2620 reflections
a = 13.8257 (4) Åθ = 2.8–21.7°
b = 8.7697 (3) ŵ = 0.38 mm1
c = 14.0690 (4) ÅT = 100 K
β = 106.486 (2)°Plate, orange
V = 1635.70 (9) Å30.35 × 0.15 × 0.02 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer
7402 independent reflections
Radiation source: fine-focus sealed tube5732 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.852, Tmax = 0.992k = 1111
15059 measured reflectionsl = 1818
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)] = 0.092H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.263 w = 1/[σ2(Fo2) + (0.1355P)2 + 3.0358P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
7402 reflectionsΔρmax = 1.06 e Å3
408 parametersΔρmin = 0.99 e Å3
2 restraintsAbsolute structure: Flack (1983), 3420 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (2)
Crystal data top
C29H33Cl2NO10S2V = 1635.70 (9) Å3
Mr = 690.58Z = 2
Monoclinic, P21Mo Kα radiation
a = 13.8257 (4) ŵ = 0.38 mm1
b = 8.7697 (3) ÅT = 100 K
c = 14.0690 (4) Å0.35 × 0.15 × 0.02 mm
β = 106.486 (2)°
Data collection top
Bruker SMART APEX
diffractometer
7402 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5732 reflections with I > 2σ(I)
Tmin = 0.852, Tmax = 0.992Rint = 0.065
15059 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.092H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.263Δρmax = 1.06 e Å3
S = 1.09Δρmin = 0.99 e Å3
7402 reflectionsAbsolute structure: Flack (1983), 3420 Friedel pairs
408 parametersAbsolute structure parameter: 0.1 (2)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.78612 (13)0.4998 (2)0.07646 (13)0.0206 (4)
S20.70294 (13)0.2505 (2)0.06603 (14)0.0213 (4)
Cl10.7299 (2)0.4115 (3)0.39454 (16)0.0473 (6)
Cl20.8139 (2)0.0943 (3)0.57216 (16)0.0449 (6)
O10.9601 (5)0.5765 (7)0.0630 (4)0.0350 (14)
O20.5862 (4)0.4620 (5)0.0353 (4)0.0192 (10)
O30.4399 (4)0.3463 (6)0.1291 (4)0.0214 (11)
O40.3754 (5)0.5700 (6)0.1994 (4)0.0327 (13)
O50.4186 (4)0.2941 (6)0.1614 (4)0.0238 (11)
O60.3331 (5)0.4616 (7)0.2260 (5)0.0368 (15)
O70.5631 (4)0.5043 (6)0.3097 (3)0.0216 (10)
O80.5287 (5)0.2970 (7)0.3894 (4)0.0328 (14)
O90.7568 (4)0.4371 (6)0.2862 (4)0.0245 (11)
O100.8313 (5)0.6649 (7)0.2879 (4)0.0380 (15)
N10.8206 (4)0.2397 (8)0.2053 (4)0.0204 (12)
H10.774 (5)0.218 (11)0.176 (6)0.03 (3)*
C10.8882 (5)0.3347 (8)0.1512 (5)0.0167 (13)
C20.9760 (5)0.3714 (8)0.1929 (5)0.0211 (15)
H2A1.01620.27730.19040.025*
H2B0.94790.39920.26360.025*
C31.0468 (5)0.4979 (9)0.1419 (6)0.0231 (14)
C41.0629 (5)0.4783 (9)0.0316 (5)0.0209 (15)
H4A1.09200.37640.01080.025*
H4B1.11130.55600.00480.025*
C50.9649 (5)0.4947 (9)0.0061 (5)0.0224 (15)
C60.8785 (5)0.4039 (9)0.0634 (5)0.0199 (14)
C71.0011 (7)0.6559 (9)0.1783 (7)0.0316 (18)
H7A0.97740.65650.25090.047*
H7B1.05270.73480.15560.047*
H7C0.94430.67640.15140.047*
C81.1460 (6)0.4828 (11)0.1689 (7)0.0336 (19)
H8A1.17260.37920.15370.050*
H8B1.19490.55650.13040.050*
H8C1.13410.50290.23980.050*
C90.7936 (5)0.3796 (8)0.0239 (5)0.0189 (14)
C110.6779 (5)0.4207 (8)0.1073 (5)0.0181 (13)
H110.68380.30710.11150.022*
C120.6713 (5)0.4842 (9)0.2059 (5)0.0208 (14)
H120.66520.59790.20310.025*
C130.5805 (5)0.4115 (8)0.2314 (5)0.0171 (13)
H130.59760.30510.25590.021*
C140.4841 (5)0.4106 (9)0.1444 (5)0.0207 (14)
H140.45010.51230.13750.025*
C150.5079 (5)0.3665 (8)0.0481 (5)0.0185 (14)
H150.52970.25740.05130.022*
C160.4140 (6)0.3897 (9)0.0387 (5)0.0252 (16)
H16A0.35810.32540.03040.030*
H16B0.39240.49770.04250.030*
C170.4192 (6)0.4505 (9)0.2029 (6)0.0245 (16)
C180.4605 (7)0.3996 (10)0.2836 (6)0.0339 (18)
H18A0.51750.46480.28550.051*
H18B0.40790.40660.34710.051*
H18C0.48340.29370.27190.051*
C190.3470 (6)0.3317 (10)0.2036 (6)0.0281 (17)
C200.2888 (8)0.1967 (12)0.2189 (9)0.052 (3)
H20A0.26530.21260.27770.077*
H20B0.33190.10610.22850.077*
H20C0.23060.18230.16070.077*
C210.5345 (6)0.4330 (9)0.3822 (6)0.0252 (16)
C220.5020 (7)0.5445 (11)0.4462 (7)0.037 (2)
H22A0.50780.49820.51100.056*
H22B0.43180.57380.41500.056*
H22C0.54510.63520.45500.056*
C230.8296 (6)0.5446 (11)0.3232 (7)0.035 (2)
C240.8238 (5)0.1667 (9)0.2938 (5)0.0215 (15)
C250.9019 (7)0.4892 (15)0.4157 (7)0.050 (3)
H25A0.96980.52600.41920.075*
H25B0.90180.37740.41640.075*
H25C0.88210.52750.47290.075*
C260.7794 (6)0.2291 (9)0.3864 (6)0.0257 (16)
C270.7763 (7)0.1509 (11)0.4737 (6)0.0301 (17)
H270.74790.19670.53670.036*
C280.8154 (7)0.0059 (11)0.4659 (6)0.0321 (18)
C290.8613 (7)0.0591 (9)0.3748 (6)0.0320 (19)
H290.89000.15810.37120.038*
C300.8655 (6)0.0206 (9)0.2893 (6)0.0253 (16)
H300.89700.02420.22660.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0217 (8)0.0199 (8)0.0235 (8)0.0054 (7)0.0115 (7)0.0049 (7)
S20.0182 (8)0.0227 (8)0.0256 (9)0.0056 (7)0.0107 (7)0.0072 (7)
Cl10.0630 (15)0.0380 (12)0.0311 (11)0.0245 (12)0.0025 (10)0.0023 (9)
Cl20.0575 (14)0.0491 (14)0.0272 (10)0.0067 (12)0.0103 (10)0.0145 (10)
O10.037 (3)0.045 (3)0.028 (3)0.023 (3)0.017 (3)0.019 (3)
O20.018 (2)0.019 (2)0.019 (2)0.0023 (19)0.004 (2)0.0006 (18)
O30.027 (3)0.022 (3)0.016 (2)0.001 (2)0.007 (2)0.0001 (19)
O40.044 (4)0.021 (3)0.038 (3)0.003 (3)0.019 (3)0.002 (2)
O50.017 (2)0.026 (3)0.032 (3)0.001 (2)0.014 (2)0.000 (2)
O60.034 (3)0.029 (3)0.056 (4)0.009 (2)0.028 (3)0.011 (3)
O70.027 (3)0.023 (2)0.017 (2)0.005 (2)0.011 (2)0.001 (2)
O80.048 (4)0.031 (3)0.024 (3)0.005 (3)0.016 (3)0.002 (2)
O90.019 (3)0.027 (3)0.026 (3)0.004 (2)0.004 (2)0.002 (2)
O100.051 (4)0.035 (3)0.030 (3)0.022 (3)0.014 (3)0.014 (3)
N10.016 (3)0.028 (3)0.020 (3)0.005 (3)0.010 (2)0.003 (2)
C10.014 (3)0.016 (3)0.019 (3)0.002 (3)0.003 (3)0.001 (3)
C20.020 (3)0.023 (4)0.022 (3)0.003 (3)0.008 (3)0.001 (3)
C30.016 (3)0.026 (4)0.027 (4)0.006 (3)0.005 (3)0.000 (3)
C40.013 (3)0.028 (4)0.021 (3)0.007 (3)0.005 (3)0.003 (3)
C50.025 (4)0.025 (3)0.023 (3)0.006 (3)0.016 (3)0.007 (3)
C60.018 (3)0.024 (4)0.019 (3)0.008 (3)0.008 (3)0.002 (3)
C70.038 (5)0.022 (4)0.038 (5)0.000 (4)0.016 (4)0.001 (3)
C80.029 (4)0.040 (5)0.039 (5)0.010 (4)0.022 (4)0.013 (4)
C90.018 (3)0.017 (3)0.020 (3)0.003 (3)0.004 (3)0.004 (3)
C110.016 (3)0.021 (3)0.016 (3)0.005 (3)0.002 (3)0.002 (3)
C120.022 (3)0.022 (4)0.021 (3)0.000 (3)0.011 (3)0.003 (3)
C130.018 (3)0.019 (3)0.015 (3)0.002 (3)0.005 (3)0.004 (3)
C140.023 (4)0.019 (3)0.025 (4)0.002 (3)0.015 (3)0.001 (3)
C150.010 (3)0.025 (4)0.020 (3)0.002 (3)0.003 (3)0.005 (3)
C160.025 (4)0.029 (4)0.019 (3)0.006 (3)0.003 (3)0.000 (3)
C170.025 (4)0.024 (4)0.024 (4)0.004 (3)0.007 (3)0.003 (3)
C180.040 (5)0.032 (4)0.033 (4)0.003 (4)0.015 (4)0.008 (4)
C190.020 (4)0.038 (5)0.028 (4)0.004 (3)0.011 (3)0.007 (3)
C200.030 (5)0.048 (6)0.085 (8)0.013 (4)0.030 (5)0.003 (6)
C210.024 (4)0.031 (4)0.023 (4)0.002 (3)0.011 (3)0.005 (3)
C220.045 (5)0.041 (5)0.037 (5)0.010 (4)0.030 (4)0.000 (4)
C230.029 (4)0.046 (6)0.033 (5)0.006 (4)0.014 (4)0.022 (4)
C240.018 (3)0.028 (4)0.018 (3)0.003 (3)0.006 (3)0.005 (3)
C250.037 (5)0.074 (7)0.034 (5)0.025 (5)0.002 (4)0.000 (5)
C260.022 (4)0.030 (4)0.025 (4)0.005 (3)0.006 (3)0.004 (3)
C270.032 (4)0.039 (4)0.017 (4)0.002 (4)0.004 (3)0.008 (3)
C280.036 (4)0.038 (5)0.024 (4)0.001 (4)0.011 (3)0.006 (4)
C290.046 (5)0.023 (4)0.029 (4)0.017 (4)0.015 (4)0.003 (3)
C300.035 (4)0.022 (4)0.023 (4)0.005 (3)0.013 (3)0.004 (3)
Geometric parameters (Å, º) top
S1—C91.788 (7)C8—H8B0.9800
S1—C111.811 (7)C8—H8C0.9800
S2—C91.668 (7)C11—C121.521 (9)
Cl1—C261.730 (8)C11—H111.0000
Cl2—C281.729 (8)C12—C131.539 (9)
O1—C51.226 (9)C12—H121.0000
O2—C151.420 (8)C13—C141.532 (10)
O2—C111.426 (8)C13—H131.0000
O3—C171.351 (9)C14—C151.532 (9)
O3—C161.466 (9)C14—H141.0000
O4—C171.219 (10)C15—C161.523 (9)
O5—C191.332 (9)C15—H151.0000
O5—C141.429 (9)C16—H16A0.9900
O6—C191.212 (10)C16—H16B0.9900
O7—C211.348 (9)C17—C181.477 (11)
O7—C131.444 (8)C18—H18A0.9800
O8—C211.201 (10)C18—H18B0.9800
O9—C231.369 (10)C18—H18C0.9800
O9—C121.445 (9)C19—C201.481 (12)
O10—C231.169 (12)C20—H20A0.9800
N1—C11.321 (9)C20—H20B0.9800
N1—C241.411 (9)C20—H20C0.9800
N1—H10.881 (10)C21—C221.483 (11)
C1—C61.415 (10)C22—H22A0.9800
C1—C21.525 (10)C22—H22B0.9800
C2—C31.519 (10)C22—H22C0.9800
C2—H2A0.9900C23—C251.481 (14)
C2—H2B0.9900C24—C261.385 (11)
C3—C41.514 (10)C24—C301.400 (11)
C3—C81.529 (10)C25—H25A0.9800
C3—C71.548 (11)C25—H25B0.9800
C4—C51.504 (9)C25—H25C0.9800
C4—H4A0.9900C26—C271.398 (11)
C4—H4B0.9900C27—C281.374 (13)
C5—C61.471 (10)C27—H270.9500
C6—C91.451 (9)C28—C291.381 (12)
C7—H7A0.9800C29—C301.379 (11)
C7—H7B0.9800C29—H290.9500
C7—H7C0.9800C30—H300.9500
C8—H8A0.9800
C9—S1—C11101.5 (3)C15—C14—C13110.5 (5)
C15—O2—C11108.4 (5)O5—C14—H14110.6
C17—O3—C16116.2 (6)C15—C14—H14110.6
C19—O5—C14118.9 (6)C13—C14—H14110.6
C21—O7—C13117.6 (6)O2—C15—C16109.1 (6)
C23—O9—C12116.7 (7)O2—C15—C14109.0 (5)
C1—N1—C24127.0 (6)C16—C15—C14109.1 (5)
C1—N1—H1111 (6)O2—C15—H15109.9
C24—N1—H1122 (6)C16—C15—H15109.9
N1—C1—C6123.1 (6)C14—C15—H15109.9
N1—C1—C2114.9 (6)O3—C16—C15107.4 (6)
C6—C1—C2121.9 (6)O3—C16—H16A110.2
C3—C2—C1116.7 (6)C15—C16—H16A110.2
C3—C2—H2A108.1O3—C16—H16B110.2
C1—C2—H2A108.1C15—C16—H16B110.2
C3—C2—H2B108.1H16A—C16—H16B108.5
C1—C2—H2B108.1O4—C17—O3123.4 (7)
H2A—C2—H2B107.3O4—C17—C18126.5 (8)
C4—C3—C2106.8 (6)O3—C17—C18110.1 (7)
C4—C3—C8111.3 (6)C17—C18—H18A109.5
C2—C3—C8108.8 (6)C17—C18—H18B109.5
C4—C3—C7111.6 (7)H18A—C18—H18B109.5
C2—C3—C7110.5 (6)C17—C18—H18C109.5
C8—C3—C7107.8 (7)H18A—C18—H18C109.5
C5—C4—C3110.7 (6)H18B—C18—H18C109.5
C5—C4—H4A109.5O6—C19—O5122.8 (7)
C3—C4—H4A109.5O6—C19—C20125.5 (8)
C5—C4—H4B109.5O5—C19—C20111.8 (8)
C3—C4—H4B109.5C19—C20—H20A109.5
H4A—C4—H4B108.1C19—C20—H20B109.5
O1—C5—C6122.3 (6)H20A—C20—H20B109.5
O1—C5—C4120.0 (7)C19—C20—H20C109.5
C6—C5—C4117.6 (6)H20A—C20—H20C109.5
C1—C6—C9124.0 (6)H20B—C20—H20C109.5
C1—C6—C5116.6 (6)O8—C21—O7124.4 (7)
C9—C6—C5119.3 (6)O8—C21—C22124.4 (7)
C3—C7—H7A109.5O7—C21—C22111.0 (7)
C3—C7—H7B109.5C21—C22—H22A109.5
H7A—C7—H7B109.5C21—C22—H22B109.5
C3—C7—H7C109.5H22A—C22—H22B109.5
H7A—C7—H7C109.5C21—C22—H22C109.5
H7B—C7—H7C109.5H22A—C22—H22C109.5
C3—C8—H8A109.5H22B—C22—H22C109.5
C3—C8—H8B109.5O10—C23—O9124.2 (9)
H8A—C8—H8B109.5O10—C23—C25125.4 (9)
C3—C8—H8C109.5O9—C23—C25110.3 (8)
H8A—C8—H8C109.5C26—C24—C30118.1 (7)
H8B—C8—H8C109.5C26—C24—N1122.3 (7)
C6—C9—S2124.9 (5)C30—C24—N1119.4 (7)
C6—C9—S1116.8 (5)C23—C25—H25A109.5
S2—C9—S1118.4 (4)C23—C25—H25B109.5
O2—C11—C12106.4 (5)H25A—C25—H25B109.5
O2—C11—S1111.1 (5)C23—C25—H25C109.5
C12—C11—S1110.2 (5)H25A—C25—H25C109.5
O2—C11—H11109.7H25B—C25—H25C109.5
C12—C11—H11109.7C24—C26—C27121.9 (7)
S1—C11—H11109.7C24—C26—Cl1119.3 (6)
O9—C12—C11111.2 (6)C27—C26—Cl1118.8 (6)
O9—C12—C13103.8 (5)C28—C27—C26118.1 (8)
C11—C12—C13109.0 (6)C28—C27—H27121.0
O9—C12—H12110.9C26—C27—H27121.0
C11—C12—H12110.9C27—C28—C29121.5 (7)
C13—C12—H12110.9C27—C28—Cl2119.5 (7)
O7—C13—C14108.5 (5)C29—C28—Cl2118.8 (7)
O7—C13—C12105.6 (5)C30—C29—C28119.7 (7)
C14—C13—C12113.5 (5)C30—C29—H29120.2
O7—C13—H13109.7C28—C29—H29120.2
C14—C13—H13109.7C29—C30—C24120.6 (7)
C12—C13—H13109.7C29—C30—H30119.7
O5—C14—C15105.8 (6)C24—C30—H30119.7
O5—C14—C13108.6 (6)
C24—N1—C1—C6179.5 (7)O9—C12—C13—C14165.2 (6)
C24—N1—C1—C22.5 (11)C11—C12—C13—C1446.6 (8)
N1—C1—C2—C3170.9 (6)C19—O5—C14—C15146.1 (6)
C6—C1—C2—C36.1 (10)C19—O5—C14—C1395.3 (7)
C1—C2—C3—C440.8 (8)O7—C13—C14—O585.2 (6)
C1—C2—C3—C8161.1 (7)C12—C13—C14—O5157.9 (6)
C1—C2—C3—C780.7 (8)O7—C13—C14—C15159.2 (6)
C2—C3—C4—C561.7 (8)C12—C13—C14—C1542.2 (8)
C8—C3—C4—C5179.6 (7)C11—O2—C15—C16170.2 (5)
C7—C3—C4—C559.1 (8)C11—O2—C15—C1470.8 (7)
C3—C4—C5—O1132.3 (8)O5—C14—C15—O2170.0 (5)
C3—C4—C5—C650.7 (9)C13—C14—C15—O252.6 (8)
N1—C1—C6—C90.5 (12)O5—C14—C15—C1671.0 (7)
C2—C1—C6—C9176.3 (7)C13—C14—C15—C16171.6 (6)
N1—C1—C6—C5174.0 (7)C17—O3—C16—C15127.5 (7)
C2—C1—C6—C59.1 (10)O2—C15—C16—O361.0 (7)
O1—C5—C6—C1169.7 (8)C14—C15—C16—O3180.0 (6)
C4—C5—C6—C113.3 (10)C16—O3—C17—O44.9 (11)
O1—C5—C6—C915.4 (12)C16—O3—C17—C18173.0 (6)
C4—C5—C6—C9161.5 (7)C14—O5—C19—O62.1 (12)
C1—C6—C9—S28.6 (11)C14—O5—C19—C20177.9 (7)
C5—C6—C9—S2165.8 (6)C13—O7—C21—O84.9 (11)
C1—C6—C9—S1170.6 (6)C13—O7—C21—C22169.7 (7)
C5—C6—C9—S115.0 (9)C12—O9—C23—O107.7 (11)
C11—S1—C9—C6175.6 (5)C12—O9—C23—C25169.7 (7)
C11—S1—C9—S25.2 (5)C1—N1—C24—C2692.1 (10)
C15—O2—C11—C1275.1 (6)C1—N1—C24—C3093.4 (10)
C15—O2—C11—S1164.9 (4)C30—C24—C26—C270.5 (12)
C9—S1—C11—O274.5 (5)N1—C24—C26—C27175.1 (7)
C9—S1—C11—C12167.7 (5)C30—C24—C26—Cl1178.4 (6)
C23—O9—C12—C11104.5 (7)N1—C24—C26—Cl17.0 (10)
C23—O9—C12—C13138.5 (6)C24—C26—C27—C282.4 (13)
O2—C11—C12—O9174.8 (5)Cl1—C26—C27—C28179.6 (7)
S1—C11—C12—O964.6 (6)C26—C27—C28—C293.3 (13)
O2—C11—C12—C1361.0 (7)C26—C27—C28—Cl2179.5 (7)
S1—C11—C12—C13178.4 (5)C27—C28—C29—C302.2 (14)
C21—O7—C13—C1495.4 (7)Cl2—C28—C29—C30178.4 (7)
C21—O7—C13—C12142.7 (6)C28—C29—C30—C240.1 (13)
O9—C12—C13—O776.2 (6)C26—C24—C30—C290.7 (11)
C11—C12—C13—O7165.3 (5)N1—C24—C30—C29174.1 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S20.88 (1)2.07 (5)2.882 (6)152 (9)

Experimental details

Crystal data
Chemical formulaC29H33Cl2NO10S2
Mr690.58
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)13.8257 (4), 8.7697 (3), 14.0690 (4)
β (°) 106.486 (2)
V3)1635.70 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.35 × 0.15 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.852, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
15059, 7402, 5732
Rint0.065
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.092, 0.263, 1.09
No. of reflections7402
No. of parameters408
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.06, 0.99
Absolute structureFlack (1983), 3420 Friedel pairs
Absolute structure parameter0.1 (2)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S20.88 (1)2.07 (5)2.882 (6)152 (9)
 

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEl Ashry, E. S. H., Awad, L. F. & Atta, A. I. (2006). Tetrahedron, 62, 2943–2998.  Web of Science CrossRef CAS Google Scholar
First citationEl Ashry, E. S. H., Rashed, N., Awad, L. F., Ramadan, E. S., Abdel-Maggeed, S. M. & Rezki, N. (2008). J. Carbohydr. Chem. 27, 70–85.  Web of Science CrossRef CAS Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHaikel, A. Z., El Ashry, E. S. H. & Banoub, J. (2003). Carbohydr. Res. 338, 2291–2299.  Web of Science PubMed Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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Volume 65| Part 5| May 2009| Page o1106
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