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

El Ashry, E.S.H.; Amer, M.R.; Shah, M.R.; Ng, S.W.

doi:10.1107/S1600536809014743

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1106

doi:10.1107/S1600536809014743

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

El Sayed H. El Ashry,^a Mohammed R. Amer,^a M. Raza Shah ^a and Seik Weng Ng ^b ^*

^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 , 2008 ), Haikel et al. (2003 ). For the deconvolution of non-merohedrally twinned diffraction data, see: Spek (2009 ).

Experimental

Crystal data

C₂₉H₃₃Cl₂NO₁₀S₂
M_r = 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 ) T_min = 0.852, T_max = 0.992
15059 measured reflections
7402 independent reflections
5732 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.99 e Å⁻³
Absolute structure: Flack (1983 ), 3420 Friedel pairs
Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014743/tk2430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014743/tk2430Isup2.hkl

checkCIF report

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).

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

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

C₂₉H₃₃Cl₂NO₁₀S₂	F(000) = 720
M_r = 690.58	D_x = 1.402 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2620 reflections
a = 13.8257 (4) Å	θ = 2.8–21.7°
b = 8.7697 (3) Å	µ = 0.38 mm⁻¹
c = 14.0690 (4) Å	T = 100 K
β = 106.486 (2)°	Plate, orange
V = 1635.70 (9) Å³	0.35 × 0.15 × 0.02 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	7402 independent reflections
Radiation source: fine-focus sealed tube	5732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.852, T_max = 0.992	k = −11→11
15059 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.092	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.263	w = 1/[σ²(F_o²) + (0.1355P)² + 3.0358P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
7402 reflections	Δρ_max = 1.06 e Å⁻³
408 parameters	Δρ_min = −0.99 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 3420 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (2)

Crystal data top

C₂₉H₃₃Cl₂NO₁₀S₂	V = 1635.70 (9) Å³
M_r = 690.58	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 13.8257 (4) Å	µ = 0.38 mm⁻¹
b = 8.7697 (3) Å	T = 100 K
c = 14.0690 (4) Å	0.35 × 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)
T_min = 0.852, T_max = 0.992	R_int = 0.065
15059 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.092	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.263	Δρ_max = 1.06 e Å⁻³
S = 1.09	Δρ_min = −0.99 e Å⁻³
7402 reflections	Absolute structure: Flack (1983), 3420 Friedel pairs
408 parameters	Absolute structure parameter: 0.1 (2)
2 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.78612 (13)	0.4998 (2)	0.07646 (13)	0.0206 (4)
S2	0.70294 (13)	0.2505 (2)	−0.06603 (14)	0.0213 (4)
Cl1	0.7299 (2)	0.4115 (3)	−0.39454 (16)	0.0473 (6)
Cl2	0.8139 (2)	−0.0943 (3)	−0.57216 (16)	0.0449 (6)
O1	0.9601 (5)	0.5765 (7)	0.0630 (4)	0.0350 (14)
O2	0.5862 (4)	0.4620 (5)	0.0353 (4)	0.0192 (10)
O3	0.4399 (4)	0.3463 (6)	−0.1291 (4)	0.0214 (11)
O4	0.3754 (5)	0.5700 (6)	−0.1994 (4)	0.0327 (13)
O5	0.4186 (4)	0.2941 (6)	0.1614 (4)	0.0238 (11)
O6	0.3331 (5)	0.4616 (7)	0.2260 (5)	0.0368 (15)
O7	0.5631 (4)	0.5043 (6)	0.3097 (3)	0.0216 (10)
O8	0.5287 (5)	0.2970 (7)	0.3894 (4)	0.0328 (14)
O9	0.7568 (4)	0.4371 (6)	0.2862 (4)	0.0245 (11)
O10	0.8313 (5)	0.6649 (7)	0.2879 (4)	0.0380 (15)
N1	0.8206 (4)	0.2397 (8)	−0.2053 (4)	0.0204 (12)
H1	0.774 (5)	0.218 (11)	−0.176 (6)	0.03 (3)*
C1	0.8882 (5)	0.3347 (8)	−0.1512 (5)	0.0167 (13)
C2	0.9760 (5)	0.3714 (8)	−0.1929 (5)	0.0211 (15)
H2A	1.0162	0.2773	−0.1904	0.025*
H2B	0.9479	0.3992	−0.2636	0.025*
C3	1.0468 (5)	0.4979 (9)	−0.1419 (6)	0.0231 (14)
C4	1.0629 (5)	0.4783 (9)	−0.0316 (5)	0.0209 (15)
H4A	1.0920	0.3764	−0.0108	0.025*
H4B	1.1113	0.5560	0.0048	0.025*
C5	0.9649 (5)	0.4947 (9)	−0.0061 (5)	0.0224 (15)
C6	0.8785 (5)	0.4039 (9)	−0.0634 (5)	0.0199 (14)
C7	1.0011 (7)	0.6559 (9)	−0.1783 (7)	0.0316 (18)
H7A	0.9774	0.6565	−0.2509	0.047*
H7B	1.0527	0.7348	−0.1556	0.047*
H7C	0.9443	0.6764	−0.1514	0.047*
C8	1.1460 (6)	0.4828 (11)	−0.1689 (7)	0.0336 (19)
H8A	1.1726	0.3792	−0.1537	0.050*
H8B	1.1949	0.5565	−0.1304	0.050*
H8C	1.1341	0.5029	−0.2398	0.050*
C9	0.7936 (5)	0.3796 (8)	−0.0239 (5)	0.0189 (14)
C11	0.6779 (5)	0.4207 (8)	0.1073 (5)	0.0181 (13)
H11	0.6838	0.3071	0.1115	0.022*
C12	0.6713 (5)	0.4842 (9)	0.2059 (5)	0.0208 (14)
H12	0.6652	0.5979	0.2031	0.025*
C13	0.5805 (5)	0.4115 (8)	0.2314 (5)	0.0171 (13)
H13	0.5976	0.3051	0.2559	0.021*
C14	0.4841 (5)	0.4106 (9)	0.1444 (5)	0.0207 (14)
H14	0.4501	0.5123	0.1375	0.025*
C15	0.5079 (5)	0.3665 (8)	0.0481 (5)	0.0185 (14)
H15	0.5297	0.2574	0.0513	0.022*
C16	0.4140 (6)	0.3897 (9)	−0.0387 (5)	0.0252 (16)
H16A	0.3581	0.3254	−0.0304	0.030*
H16B	0.3924	0.4977	−0.0425	0.030*
C17	0.4192 (6)	0.4505 (9)	−0.2029 (6)	0.0245 (16)
C18	0.4605 (7)	0.3996 (10)	−0.2836 (6)	0.0339 (18)
H18A	0.5175	0.4648	−0.2855	0.051*
H18B	0.4079	0.4066	−0.3471	0.051*
H18C	0.4834	0.2937	−0.2719	0.051*
C19	0.3470 (6)	0.3317 (10)	0.2036 (6)	0.0281 (17)
C20	0.2888 (8)	0.1967 (12)	0.2189 (9)	0.052 (3)
H20A	0.2653	0.2126	0.2777	0.077*
H20B	0.3319	0.1061	0.2285	0.077*
H20C	0.2306	0.1823	0.1607	0.077*
C21	0.5345 (6)	0.4330 (9)	0.3822 (6)	0.0252 (16)
C22	0.5020 (7)	0.5445 (11)	0.4462 (7)	0.037 (2)
H22A	0.5078	0.4982	0.5110	0.056*
H22B	0.4318	0.5738	0.4150	0.056*
H22C	0.5451	0.6352	0.4550	0.056*
C23	0.8296 (6)	0.5446 (11)	0.3232 (7)	0.035 (2)
C24	0.8238 (5)	0.1667 (9)	−0.2938 (5)	0.0215 (15)
C25	0.9019 (7)	0.4892 (15)	0.4157 (7)	0.050 (3)
H25A	0.9698	0.5260	0.4192	0.075*
H25B	0.9018	0.3774	0.4164	0.075*
H25C	0.8821	0.5275	0.4729	0.075*
C26	0.7794 (6)	0.2291 (9)	−0.3864 (6)	0.0257 (16)
C27	0.7763 (7)	0.1509 (11)	−0.4737 (6)	0.0301 (17)
H27	0.7479	0.1967	−0.5367	0.036*
C28	0.8154 (7)	0.0059 (11)	−0.4659 (6)	0.0321 (18)
C29	0.8613 (7)	−0.0591 (9)	−0.3748 (6)	0.0320 (19)
H29	0.8900	−0.1581	−0.3712	0.038*
C30	0.8655 (6)	0.0206 (9)	−0.2893 (6)	0.0253 (16)
H30	0.8970	−0.0242	−0.2266	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0217 (8)	0.0199 (8)	0.0235 (8)	−0.0054 (7)	0.0115 (7)	−0.0049 (7)
S2	0.0182 (8)	0.0227 (8)	0.0256 (9)	−0.0056 (7)	0.0107 (7)	−0.0072 (7)
Cl1	0.0630 (15)	0.0380 (12)	0.0311 (11)	0.0245 (12)	−0.0025 (10)	−0.0023 (9)
Cl2	0.0575 (14)	0.0491 (14)	0.0272 (10)	0.0067 (12)	0.0103 (10)	−0.0145 (10)
O1	0.037 (3)	0.045 (3)	0.028 (3)	−0.023 (3)	0.017 (3)	−0.019 (3)
O2	0.018 (2)	0.019 (2)	0.019 (2)	0.0023 (19)	0.004 (2)	0.0006 (18)
O3	0.027 (3)	0.022 (3)	0.016 (2)	0.001 (2)	0.007 (2)	−0.0001 (19)
O4	0.044 (4)	0.021 (3)	0.038 (3)	0.003 (3)	0.019 (3)	0.002 (2)
O5	0.017 (2)	0.026 (3)	0.032 (3)	−0.001 (2)	0.014 (2)	0.000 (2)
O6	0.034 (3)	0.029 (3)	0.056 (4)	0.009 (2)	0.028 (3)	0.011 (3)
O7	0.027 (3)	0.023 (2)	0.017 (2)	0.005 (2)	0.011 (2)	−0.001 (2)
O8	0.048 (4)	0.031 (3)	0.024 (3)	−0.005 (3)	0.016 (3)	0.002 (2)
O9	0.019 (3)	0.027 (3)	0.026 (3)	−0.004 (2)	0.004 (2)	−0.002 (2)
O10	0.051 (4)	0.035 (3)	0.030 (3)	−0.022 (3)	0.014 (3)	−0.014 (3)
N1	0.016 (3)	0.028 (3)	0.020 (3)	−0.005 (3)	0.010 (2)	−0.003 (2)
C1	0.014 (3)	0.016 (3)	0.019 (3)	−0.002 (3)	0.003 (3)	−0.001 (3)
C2	0.020 (3)	0.023 (4)	0.022 (3)	0.003 (3)	0.008 (3)	−0.001 (3)
C3	0.016 (3)	0.026 (4)	0.027 (4)	−0.006 (3)	0.005 (3)	0.000 (3)
C4	0.013 (3)	0.028 (4)	0.021 (3)	−0.007 (3)	0.005 (3)	−0.003 (3)
C5	0.025 (4)	0.025 (3)	0.023 (3)	−0.006 (3)	0.016 (3)	−0.007 (3)
C6	0.018 (3)	0.024 (4)	0.019 (3)	−0.008 (3)	0.008 (3)	−0.002 (3)
C7	0.038 (5)	0.022 (4)	0.038 (5)	0.000 (4)	0.016 (4)	−0.001 (3)
C8	0.029 (4)	0.040 (5)	0.039 (5)	−0.010 (4)	0.022 (4)	−0.013 (4)
C9	0.018 (3)	0.017 (3)	0.020 (3)	0.003 (3)	0.004 (3)	0.004 (3)
C11	0.016 (3)	0.021 (3)	0.016 (3)	0.005 (3)	0.002 (3)	0.002 (3)
C12	0.022 (3)	0.022 (4)	0.021 (3)	0.000 (3)	0.011 (3)	0.003 (3)
C13	0.018 (3)	0.019 (3)	0.015 (3)	−0.002 (3)	0.005 (3)	−0.004 (3)
C14	0.023 (4)	0.019 (3)	0.025 (4)	0.002 (3)	0.015 (3)	0.001 (3)
C15	0.010 (3)	0.025 (4)	0.020 (3)	0.002 (3)	0.003 (3)	−0.005 (3)
C16	0.025 (4)	0.029 (4)	0.019 (3)	0.006 (3)	0.003 (3)	0.000 (3)
C17	0.025 (4)	0.024 (4)	0.024 (4)	−0.004 (3)	0.007 (3)	−0.003 (3)
C18	0.040 (5)	0.032 (4)	0.033 (4)	0.003 (4)	0.015 (4)	0.008 (4)
C19	0.020 (4)	0.038 (5)	0.028 (4)	0.004 (3)	0.011 (3)	0.007 (3)
C20	0.030 (5)	0.048 (6)	0.085 (8)	−0.013 (4)	0.030 (5)	−0.003 (6)
C21	0.024 (4)	0.031 (4)	0.023 (4)	0.002 (3)	0.011 (3)	0.005 (3)
C22	0.045 (5)	0.041 (5)	0.037 (5)	0.010 (4)	0.030 (4)	0.000 (4)
C23	0.029 (4)	0.046 (6)	0.033 (5)	−0.006 (4)	0.014 (4)	−0.022 (4)
C24	0.018 (3)	0.028 (4)	0.018 (3)	−0.003 (3)	0.006 (3)	−0.005 (3)
C25	0.037 (5)	0.074 (7)	0.034 (5)	−0.025 (5)	0.002 (4)	0.000 (5)
C26	0.022 (4)	0.030 (4)	0.025 (4)	0.005 (3)	0.006 (3)	−0.004 (3)
C27	0.032 (4)	0.039 (4)	0.017 (4)	0.002 (4)	0.004 (3)	−0.008 (3)
C28	0.036 (4)	0.038 (5)	0.024 (4)	0.001 (4)	0.011 (3)	−0.006 (4)
C29	0.046 (5)	0.023 (4)	0.029 (4)	0.017 (4)	0.015 (4)	0.003 (3)
C30	0.035 (4)	0.022 (4)	0.023 (4)	0.005 (3)	0.013 (3)	0.004 (3)

Geometric parameters (Å, º) top

S1—C9	1.788 (7)	C8—H8B	0.9800
S1—C11	1.811 (7)	C8—H8C	0.9800
S2—C9	1.668 (7)	C11—C12	1.521 (9)
Cl1—C26	1.730 (8)	C11—H11	1.0000
Cl2—C28	1.729 (8)	C12—C13	1.539 (9)
O1—C5	1.226 (9)	C12—H12	1.0000
O2—C15	1.420 (8)	C13—C14	1.532 (10)
O2—C11	1.426 (8)	C13—H13	1.0000
O3—C17	1.351 (9)	C14—C15	1.532 (9)
O3—C16	1.466 (9)	C14—H14	1.0000
O4—C17	1.219 (10)	C15—C16	1.523 (9)
O5—C19	1.332 (9)	C15—H15	1.0000
O5—C14	1.429 (9)	C16—H16A	0.9900
O6—C19	1.212 (10)	C16—H16B	0.9900
O7—C21	1.348 (9)	C17—C18	1.477 (11)
O7—C13	1.444 (8)	C18—H18A	0.9800
O8—C21	1.201 (10)	C18—H18B	0.9800
O9—C23	1.369 (10)	C18—H18C	0.9800
O9—C12	1.445 (9)	C19—C20	1.481 (12)
O10—C23	1.169 (12)	C20—H20A	0.9800
N1—C1	1.321 (9)	C20—H20B	0.9800
N1—C24	1.411 (9)	C20—H20C	0.9800
N1—H1	0.881 (10)	C21—C22	1.483 (11)
C1—C6	1.415 (10)	C22—H22A	0.9800
C1—C2	1.525 (10)	C22—H22B	0.9800
C2—C3	1.519 (10)	C22—H22C	0.9800
C2—H2A	0.9900	C23—C25	1.481 (14)
C2—H2B	0.9900	C24—C26	1.385 (11)
C3—C4	1.514 (10)	C24—C30	1.400 (11)
C3—C8	1.529 (10)	C25—H25A	0.9800
C3—C7	1.548 (11)	C25—H25B	0.9800
C4—C5	1.504 (9)	C25—H25C	0.9800
C4—H4A	0.9900	C26—C27	1.398 (11)
C4—H4B	0.9900	C27—C28	1.374 (13)
C5—C6	1.471 (10)	C27—H27	0.9500
C6—C9	1.451 (9)	C28—C29	1.381 (12)
C7—H7A	0.9800	C29—C30	1.379 (11)
C7—H7B	0.9800	C29—H29	0.9500
C7—H7C	0.9800	C30—H30	0.9500
C8—H8A	0.9800

C9—S1—C11	101.5 (3)	C15—C14—C13	110.5 (5)
C15—O2—C11	108.4 (5)	O5—C14—H14	110.6
C17—O3—C16	116.2 (6)	C15—C14—H14	110.6
C19—O5—C14	118.9 (6)	C13—C14—H14	110.6
C21—O7—C13	117.6 (6)	O2—C15—C16	109.1 (6)
C23—O9—C12	116.7 (7)	O2—C15—C14	109.0 (5)
C1—N1—C24	127.0 (6)	C16—C15—C14	109.1 (5)
C1—N1—H1	111 (6)	O2—C15—H15	109.9
C24—N1—H1	122 (6)	C16—C15—H15	109.9
N1—C1—C6	123.1 (6)	C14—C15—H15	109.9
N1—C1—C2	114.9 (6)	O3—C16—C15	107.4 (6)
C6—C1—C2	121.9 (6)	O3—C16—H16A	110.2
C3—C2—C1	116.7 (6)	C15—C16—H16A	110.2
C3—C2—H2A	108.1	O3—C16—H16B	110.2
C1—C2—H2A	108.1	C15—C16—H16B	110.2
C3—C2—H2B	108.1	H16A—C16—H16B	108.5
C1—C2—H2B	108.1	O4—C17—O3	123.4 (7)
H2A—C2—H2B	107.3	O4—C17—C18	126.5 (8)
C4—C3—C2	106.8 (6)	O3—C17—C18	110.1 (7)
C4—C3—C8	111.3 (6)	C17—C18—H18A	109.5
C2—C3—C8	108.8 (6)	C17—C18—H18B	109.5
C4—C3—C7	111.6 (7)	H18A—C18—H18B	109.5
C2—C3—C7	110.5 (6)	C17—C18—H18C	109.5
C8—C3—C7	107.8 (7)	H18A—C18—H18C	109.5
C5—C4—C3	110.7 (6)	H18B—C18—H18C	109.5
C5—C4—H4A	109.5	O6—C19—O5	122.8 (7)
C3—C4—H4A	109.5	O6—C19—C20	125.5 (8)
C5—C4—H4B	109.5	O5—C19—C20	111.8 (8)
C3—C4—H4B	109.5	C19—C20—H20A	109.5
H4A—C4—H4B	108.1	C19—C20—H20B	109.5
O1—C5—C6	122.3 (6)	H20A—C20—H20B	109.5
O1—C5—C4	120.0 (7)	C19—C20—H20C	109.5
C6—C5—C4	117.6 (6)	H20A—C20—H20C	109.5
C1—C6—C9	124.0 (6)	H20B—C20—H20C	109.5
C1—C6—C5	116.6 (6)	O8—C21—O7	124.4 (7)
C9—C6—C5	119.3 (6)	O8—C21—C22	124.4 (7)
C3—C7—H7A	109.5	O7—C21—C22	111.0 (7)
C3—C7—H7B	109.5	C21—C22—H22A	109.5
H7A—C7—H7B	109.5	C21—C22—H22B	109.5
C3—C7—H7C	109.5	H22A—C22—H22B	109.5
H7A—C7—H7C	109.5	C21—C22—H22C	109.5
H7B—C7—H7C	109.5	H22A—C22—H22C	109.5
C3—C8—H8A	109.5	H22B—C22—H22C	109.5
C3—C8—H8B	109.5	O10—C23—O9	124.2 (9)
H8A—C8—H8B	109.5	O10—C23—C25	125.4 (9)
C3—C8—H8C	109.5	O9—C23—C25	110.3 (8)
H8A—C8—H8C	109.5	C26—C24—C30	118.1 (7)
H8B—C8—H8C	109.5	C26—C24—N1	122.3 (7)
C6—C9—S2	124.9 (5)	C30—C24—N1	119.4 (7)
C6—C9—S1	116.8 (5)	C23—C25—H25A	109.5
S2—C9—S1	118.4 (4)	C23—C25—H25B	109.5
O2—C11—C12	106.4 (5)	H25A—C25—H25B	109.5
O2—C11—S1	111.1 (5)	C23—C25—H25C	109.5
C12—C11—S1	110.2 (5)	H25A—C25—H25C	109.5
O2—C11—H11	109.7	H25B—C25—H25C	109.5
C12—C11—H11	109.7	C24—C26—C27	121.9 (7)
S1—C11—H11	109.7	C24—C26—Cl1	119.3 (6)
O9—C12—C11	111.2 (6)	C27—C26—Cl1	118.8 (6)
O9—C12—C13	103.8 (5)	C28—C27—C26	118.1 (8)
C11—C12—C13	109.0 (6)	C28—C27—H27	121.0
O9—C12—H12	110.9	C26—C27—H27	121.0
C11—C12—H12	110.9	C27—C28—C29	121.5 (7)
C13—C12—H12	110.9	C27—C28—Cl2	119.5 (7)
O7—C13—C14	108.5 (5)	C29—C28—Cl2	118.8 (7)
O7—C13—C12	105.6 (5)	C30—C29—C28	119.7 (7)
C14—C13—C12	113.5 (5)	C30—C29—H29	120.2
O7—C13—H13	109.7	C28—C29—H29	120.2
C14—C13—H13	109.7	C29—C30—C24	120.6 (7)
C12—C13—H13	109.7	C29—C30—H30	119.7
O5—C14—C15	105.8 (6)	C24—C30—H30	119.7
O5—C14—C13	108.6 (6)

C24—N1—C1—C6	179.5 (7)	O9—C12—C13—C14	−165.2 (6)
C24—N1—C1—C2	2.5 (11)	C11—C12—C13—C14	−46.6 (8)
N1—C1—C2—C3	170.9 (6)	C19—O5—C14—C15	−146.1 (6)
C6—C1—C2—C3	−6.1 (10)	C19—O5—C14—C13	95.3 (7)
C1—C2—C3—C4	40.8 (8)	O7—C13—C14—O5	−85.2 (6)
C1—C2—C3—C8	161.1 (7)	C12—C13—C14—O5	157.9 (6)
C1—C2—C3—C7	−80.7 (8)	O7—C13—C14—C15	159.2 (6)
C2—C3—C4—C5	−61.7 (8)	C12—C13—C14—C15	42.2 (8)
C8—C3—C4—C5	179.6 (7)	C11—O2—C15—C16	−170.2 (5)
C7—C3—C4—C5	59.1 (8)	C11—O2—C15—C14	70.8 (7)
C3—C4—C5—O1	−132.3 (8)	O5—C14—C15—O2	−170.0 (5)
C3—C4—C5—C6	50.7 (9)	C13—C14—C15—O2	−52.6 (8)
N1—C1—C6—C9	−0.5 (12)	O5—C14—C15—C16	71.0 (7)
C2—C1—C6—C9	176.3 (7)	C13—C14—C15—C16	−171.6 (6)
N1—C1—C6—C5	174.0 (7)	C17—O3—C16—C15	−127.5 (7)
C2—C1—C6—C5	−9.1 (10)	O2—C15—C16—O3	61.0 (7)
O1—C5—C6—C1	169.7 (8)	C14—C15—C16—O3	−180.0 (6)
C4—C5—C6—C1	−13.3 (10)	C16—O3—C17—O4	−4.9 (11)
O1—C5—C6—C9	−15.4 (12)	C16—O3—C17—C18	173.0 (6)
C4—C5—C6—C9	161.5 (7)	C14—O5—C19—O6	2.1 (12)
C1—C6—C9—S2	8.6 (11)	C14—O5—C19—C20	−177.9 (7)
C5—C6—C9—S2	−165.8 (6)	C13—O7—C21—O8	4.9 (11)
C1—C6—C9—S1	−170.6 (6)	C13—O7—C21—C22	−169.7 (7)
C5—C6—C9—S1	15.0 (9)	C12—O9—C23—O10	−7.7 (11)
C11—S1—C9—C6	−175.6 (5)	C12—O9—C23—C25	169.7 (7)
C11—S1—C9—S2	5.2 (5)	C1—N1—C24—C26	−92.1 (10)
C15—O2—C11—C12	−75.1 (6)	C1—N1—C24—C30	93.4 (10)
C15—O2—C11—S1	164.9 (4)	C30—C24—C26—C27	−0.5 (12)
C9—S1—C11—O2	−74.5 (5)	N1—C24—C26—C27	−175.1 (7)
C9—S1—C11—C12	167.7 (5)	C30—C24—C26—Cl1	−178.4 (6)
C23—O9—C12—C11	104.5 (7)	N1—C24—C26—Cl1	7.0 (10)
C23—O9—C12—C13	−138.5 (6)	C24—C26—C27—C28	2.4 (13)
O2—C11—C12—O9	174.8 (5)	Cl1—C26—C27—C28	−179.6 (7)
S1—C11—C12—O9	−64.6 (6)	C26—C27—C28—C29	−3.3 (13)
O2—C11—C12—C13	61.0 (7)	C26—C27—C28—Cl2	−179.5 (7)
S1—C11—C12—C13	−178.4 (5)	C27—C28—C29—C30	2.2 (14)
C21—O7—C13—C14	95.4 (7)	Cl2—C28—C29—C30	178.4 (7)
C21—O7—C13—C12	−142.7 (6)	C28—C29—C30—C24	−0.1 (13)
O9—C12—C13—O7	76.2 (6)	C26—C24—C30—C29	−0.7 (11)
C11—C12—C13—O7	−165.3 (5)	N1—C24—C30—C29	174.1 (7)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₉H₃₃Cl₂NO₁₀S₂
M_r	690.58
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	13.8257 (4), 8.7697 (3), 14.0690 (4)
β (°)	106.486 (2)
V (Å³)	1635.70 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.35 × 0.15 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.852, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	15059, 7402, 5732
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.092, 0.263, 1.09
No. of reflections	7402
No. of parameters	408
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.99
Absolute structure	Flack (1983), 3420 Friedel pairs
Absolute structure parameter	0.1 (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···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.88 (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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El Ashry, E. S. H., Awad, L. F. & Atta, A. I. (2006). Tetrahedron, 62, 2943–2998. Web of Science CrossRef CAS Google Scholar
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. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Haikel, A. Z., El Ashry, E. S. H. & Banoub, J. (2003). Carbohydr. Res. 338, 2291–2299. Web of Science PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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