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The structure of the title compound, C22H24N2O9S2, is described. This compound consists of a sugar ring and a heterocyclic base linked unusually by an S atom. The sugar is in a 4C1 chair conformation and forms dihedral angles of 49.54 (4) and 33.42 (5)° with the thia­diazole and phen­yl rings, respectively. The S atom occupies an equatorial position of the sugar ring and lies 1.807 (2) Å out of the corresponding mean plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105003951/ty1004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105003951/ty1004Isup2.hkl
Contains datablock I

CCDC reference: 282184

Comment top

1,3,4-Thiadiazole derivatives display a broad spectrum of biological activities, such as fungicidal (Zou et al., 2002), antibacterial (Deibel et al., 2004), antidepressant (Clerici et al., 2001) and antiepileptic (Masereel et al., 2002) properties. However, the application of 1,3,4-thiadiazoles is limited because of their poor solubility, both in organic solvents and in water. In the course of identifying new chemical structures that may serve as leads in the design of novel antiviral agents, we were particularly interested in the linking of thio-1,3,4-thiadiazoles to hydrophilic moieties such as D-glucose. The present structure determination is part of an investigation into the nucleophilic substitution of a bromosugar to a thioheterocyclic compound. Here, we report the X-ray crystal structure determination of the title compound (I) (Fig. 1).

The 2,3,4,6-tetra-O-acetyglucopyranosyl ring of (I) assumes a 4C1 chair conformation, with atoms C2 and C5 displaced from the C1—C3—C4—O1 mean plane. The mean C—C and CO(hydroxyl) bond lengths of 1.519 (2) and 1.422 (2) Å, respectively, in the sugar moiety compare well with similar averages observed in pyranose sugars (Berman et al., 1967). The two endocyclic C—O bonds, C1—O1 and C5—O1, are nearly equal [1.432 (2) and 1.422 (2) Å, respectively]. The conformation about the exocyclic C1—C6 bond is gauchetrans, with torsion angles O2—C6—C1—O1 = −59.7 (2)° and O2—C6—C1—C2 = 60.9 (2)°.

The heterocyclic phenyl-1,3,4-thiadiazole ring is planar to within experimental error and the lengths of the endocyclic bonds, C15—N1 = 1.299 (2) Å and C16—N2 = 1.306 (2) Å, clearly indicate that they are double bonds. The N1—N2 bond length of 1.375 (2) Å is slightly shorter than the single-bond value of 1.393 (4) Å in the hydrochloride of 5-(4-methoxyphenyl)-4-phenyl-1,3,4-thiadiazolium-2-phenylaminide (Cheung et al., 1992). The large deviation of the bond angle (Value?) in the ring from the value of 120° usually found in trigonal planar arrangements is common in five-membered rings (Downie et al., 1972). The phenyl ring linked to atom C16 forms a dihedral angle of 16.95 (6)° with the heterocyclic plane.

The S atom of the thioglucosidic linkage bridges the sugar and heterocyclic rings. The dihedral angles between the mean plane of the sugar ring and the thiadiazole and phenyl planes are 49.54 (4) and 33.42 (5)°, respectively. The orientation of the thiadiazole moiety relative to the glucose ring may be described by the torsion angles N1—C15—S1—C5 = −106.9 (2)°, S2—C15—S1—C5 = 78.2 (1)°, C15—S1—C5—O1 = −67.1 (1)° and C15—S1—C5—C4 = 176.3 (1)°.

Experimental top

2-Phenyl-5-thiol-1,3,4-thiadiazole (0.582 g, 3 mmol), α-acetobromoglucose (1.230 g, 3 mol) and KOH (0.168 g, 3 mmol) were reacted at room temperature for 12 h. The product was obtained via column-chromatograpic purification and the crystals were recrystallized by slow evaporation from petroleum ether–ethyl acetate (4:1) (m.p. 424–426 K). Spectroscopic analysis: 1H NMR (400 MHz, CDCl3, δ, p.p.m): 2.018 (s, 3 H), 2.040 (s, 3 H), 2.060 (s, 3 H), 2.088 (s, 3 H), 3.845–3.886 (m, 1 H), 4.166 (dd, J = 2.0 and 12.8 Hz, 1 H), 4.302 (dd, J = 4.8 and 12.8 Hz, 1 H), 5.137–5.205 (m, 2 H), 5.309 (t, J = 9.2 Hz, 1 H), 5.444 (d, J = 10.4 Hz, 1 H), 7.459–7.511 (m, 3 H), 7.899–7.922 (m, 2 H).

Refinement top

H atoms were placed in calculated positions with C—H = 0.97 Å and were included in the final cycles of refinement [Uiso(H) = 1.2Ueq(parent atom)].

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
5-Phenyl-1,3,4-thiadiazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-Glucopyranoside top
Crystal data top
C22H24N2O9S2F(000) = 1096.0
Mr = 524.56Dx = 1.440 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 7511 reflections
a = 8.010 (2) Åθ = 3.2–27.5°
b = 10.526 (2) ŵ = 0.28 mm1
c = 28.685 (6) ÅT = 173 K
V = 2418.7 (9) Å3Block, colourless
Z = 40.35 × 0.25 × 0.20 mm
Data collection top
Rigaku/MSC Mercury CCD area-detector
diffractometer
5151 reflections with F2 > 2σ(F2)
Detector resolution: 28.57 pixels mm-1Rint = 0.037
ω scansθmax = 27.5°
Absorption correction: multi-scan
TEXSAN (Molecular Structure Corporation, 1999)
h = 109
Tmin = 0.825, Tmax = 0.947k = 1113
19569 measured reflectionsl = 3737
5524 independent reflections
Refinement top
Refinement on F w = 1/[σ2(Fo) + 0.00063|Fo|2]
R[F2 > 2σ(F2)] = 0.033(Δ/σ)max = 0.001
wR(F2) = 0.046Δρmax = 0.25 e Å3
S = 1.06Δρmin = 0.24 e Å3
5499 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs
317 parametersAbsolute structure parameter: 0.00 (5)
H-atom parameters constrained
Crystal data top
C22H24N2O9S2V = 2418.7 (9) Å3
Mr = 524.56Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.010 (2) ŵ = 0.28 mm1
b = 10.526 (2) ÅT = 173 K
c = 28.685 (6) Å0.35 × 0.25 × 0.20 mm
Data collection top
Rigaku/MSC Mercury CCD area-detector
diffractometer
5524 independent reflections
Absorption correction: multi-scan
TEXSAN (Molecular Structure Corporation, 1999)
5151 reflections with F2 > 2σ(F2)
Tmin = 0.825, Tmax = 0.947Rint = 0.037
19569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.046Δρmax = 0.25 e Å3
S = 1.06Δρmin = 0.24 e Å3
5499 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs
317 parametersAbsolute structure parameter: 0.00 (5)
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.27622 (5)0.20966 (4)0.68265 (2)0.0300 (1)
S20.05465 (6)0.13378 (4)0.72770 (2)0.0343 (1)
O10.1245 (1)0.0409 (1)0.62962 (4)0.0259 (3)
O20.0702 (2)0.2128 (1)0.61743 (5)0.0377 (3)
O30.0567 (2)0.3742 (1)0.58108 (8)0.0690 (6)
O40.1401 (2)0.0523 (1)0.50689 (4)0.0268 (3)
O50.2289 (2)0.2543 (1)0.50827 (6)0.0525 (4)
O60.4793 (1)0.0391 (1)0.52769 (4)0.0245 (3)
O70.4833 (2)0.2033 (1)0.47712 (5)0.0378 (3)
O80.4728 (1)0.2408 (1)0.59405 (4)0.0261 (3)
O90.6921 (2)0.1407 (2)0.62615 (8)0.0667 (6)
N10.0320 (2)0.3625 (1)0.71316 (7)0.0439 (5)
N20.1200 (2)0.3682 (1)0.73523 (7)0.0466 (5)
C10.0629 (2)0.0035 (1)0.58570 (6)0.0241 (4)
C20.2089 (2)0.0298 (1)0.55251 (5)0.0224 (4)
C30.3279 (2)0.0825 (1)0.54928 (6)0.0221 (3)
C40.3733 (2)0.1283 (1)0.59786 (5)0.0222 (3)
C50.2145 (2)0.1563 (1)0.62533 (6)0.0237 (4)
C60.0385 (2)0.1212 (2)0.59557 (6)0.0332 (4)
C70.0485 (2)0.3363 (2)0.60692 (7)0.0343 (4)
C80.1716 (3)0.4169 (2)0.63204 (7)0.0472 (6)
C90.1569 (2)0.1711 (2)0.48867 (6)0.0290 (4)
C100.0727 (2)0.1824 (2)0.44275 (7)0.0383 (5)
C110.5506 (2)0.1125 (1)0.49426 (6)0.0246 (4)
C120.7215 (2)0.0655 (2)0.48357 (7)0.0316 (4)
C130.6316 (2)0.2361 (2)0.61116 (7)0.0350 (5)
C140.7128 (3)0.3628 (2)0.60825 (8)0.0471 (6)
C150.0809 (2)0.2461 (1)0.70673 (6)0.0255 (4)
C160.1812 (2)0.2566 (1)0.74498 (6)0.0251 (4)
C170.3421 (2)0.2403 (2)0.76863 (6)0.0266 (4)
C180.4251 (2)0.1241 (2)0.76842 (7)0.0355 (5)
C190.5789 (3)0.1125 (2)0.79038 (7)0.0432 (5)
C200.6484 (3)0.2145 (2)0.81284 (7)0.0467 (6)
C210.5659 (3)0.3302 (2)0.81388 (8)0.0474 (6)
C220.4124 (3)0.3431 (2)0.79225 (7)0.0380 (5)
H10.00890.06090.57220.0289*
H20.26930.10450.56290.0269*
H3)0.27830.15080.53130.0266*
H40.43680.06280.61370.0267*
H50.14780.22030.60970.0284*
H60.08220.15560.56670.0399*
H70.13030.10070.61630.0399*
H80.19140.49400.61440.0566*
H90.27560.37070.63560.0566*
H100.12800.43860.66260.0566*
H110.03790.14530.44460.0460*
H120.13750.13780.41930.0460*
H130.06360.27130.43430.0460*
H140.71980.02640.48120.0379*
H150.75880.10150.45420.0379*
H160.79720.09090.50830.0379*
H170.82460.35770.62110.0565*
H180.71870.38940.57590.0565*
H190.64800.42410.62590.0565*
H200.37560.05140.75290.0426*
H210.63740.03180.78980.0518*
H220.75590.20570.82810.0561*
H230.61570.40220.82980.0569*
H240.35360.42360.79350.0456*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0261 (2)0.0371 (2)0.0269 (2)0.0004 (2)0.0008 (2)0.0063 (2)
S20.0336 (2)0.0195 (2)0.0496 (3)0.0004 (2)0.0098 (2)0.0001 (2)
O10.0282 (6)0.0245 (5)0.0250 (6)0.0034 (5)0.0033 (5)0.0010 (4)
O20.0568 (8)0.0265 (6)0.0298 (6)0.0114 (6)0.0055 (6)0.0038 (5)
O30.0485 (9)0.0416 (8)0.117 (2)0.0038 (8)0.027 (1)0.0244 (10)
O40.0298 (6)0.0244 (5)0.0262 (6)0.0032 (5)0.0034 (5)0.0031 (4)
O50.086 (1)0.0249 (6)0.0467 (9)0.0127 (7)0.0112 (8)0.0048 (6)
O60.0257 (6)0.0205 (5)0.0274 (6)0.0032 (4)0.0062 (5)0.0022 (4)
O70.0398 (7)0.0314 (6)0.0422 (7)0.0059 (6)0.0084 (6)0.0143 (6)
O80.0254 (6)0.0207 (5)0.0323 (6)0.0035 (4)0.0004 (5)0.0018 (4)
O90.0392 (9)0.0521 (9)0.109 (2)0.0028 (7)0.0309 (9)0.020 (1)
N10.0446 (9)0.0257 (7)0.062 (1)0.0017 (7)0.0295 (8)0.0003 (7)
N20.0466 (10)0.0242 (7)0.069 (1)0.0010 (7)0.0314 (9)0.0031 (8)
C10.0233 (7)0.0225 (7)0.0264 (8)0.0022 (6)0.0004 (7)0.0013 (6)
C20.0232 (7)0.0207 (7)0.0234 (7)0.0014 (6)0.0009 (6)0.0007 (6)
C30.0238 (7)0.0169 (6)0.0257 (7)0.0043 (6)0.0022 (6)0.0012 (6)
C40.0241 (7)0.0164 (6)0.0261 (7)0.0004 (6)0.0012 (6)0.0015 (6)
C50.0240 (7)0.0221 (7)0.0249 (7)0.0001 (6)0.0002 (6)0.0006 (6)
C60.0309 (8)0.0331 (8)0.0358 (9)0.0075 (8)0.0034 (7)0.0019 (7)
C70.0356 (9)0.0294 (8)0.0378 (9)0.0112 (7)0.0117 (8)0.0036 (7)
C80.074 (2)0.0338 (9)0.0335 (10)0.0056 (10)0.003 (1)0.0040 (8)
C90.0280 (8)0.0265 (8)0.0327 (9)0.0041 (6)0.0058 (7)0.0063 (7)
C100.0312 (9)0.050 (1)0.0340 (9)0.0054 (8)0.0024 (8)0.0130 (8)
C110.0283 (7)0.0210 (7)0.0245 (7)0.0034 (6)0.0015 (6)0.0014 (6)
C120.0280 (8)0.0273 (8)0.0396 (9)0.0026 (7)0.0078 (8)0.0000 (7)
C130.0273 (8)0.0396 (10)0.0381 (10)0.0056 (8)0.0023 (8)0.0018 (8)
C140.040 (1)0.045 (1)0.056 (1)0.0165 (10)0.0018 (10)0.0071 (10)
C150.0294 (8)0.0239 (7)0.0233 (8)0.0012 (6)0.0030 (6)0.0016 (6)
C160.0295 (8)0.0220 (7)0.0237 (7)0.0015 (6)0.0013 (6)0.0001 (6)
C170.0280 (8)0.0291 (8)0.0227 (7)0.0003 (6)0.0008 (6)0.0041 (6)
C180.0385 (10)0.0379 (9)0.0301 (9)0.0099 (8)0.0003 (7)0.0036 (7)
C190.041 (1)0.053 (1)0.0354 (10)0.0194 (10)0.0014 (8)0.0008 (9)
C200.0342 (10)0.073 (1)0.0329 (10)0.010 (1)0.0070 (8)0.001 (1)
C210.043 (1)0.054 (1)0.045 (1)0.0030 (9)0.017 (1)0.0016 (9)
C220.040 (1)0.0340 (9)0.041 (1)0.0001 (8)0.0133 (8)0.0017 (8)
Geometric parameters (Å, º) top
S1—C51.807 (2)C17—C181.392 (2)
S1—C151.753 (2)C17—C221.396 (2)
S2—C151.715 (2)C18—C191.389 (3)
S2—C161.716 (2)C19—C201.370 (3)
O1—C11.431 (2)C20—C211.386 (3)
O1—C51.418 (2)C21—C221.384 (3)
O2—C61.442 (2)C1—H10.9700
O2—C71.346 (2)C2—H20.9700
O3—C71.191 (3)C3—H30.9700
O4—C21.440 (2)C4—H40.9700
O4—C91.362 (2)C5—H50.9700
O5—C91.190 (2)C6—H60.9700
O6—C31.436 (2)C6—H70.9700
O6—C111.357 (2)C8—H80.9700
O7—C111.202 (2)C8—H90.9700
O8—C41.433 (2)C8—H100.9700
O8—C131.364 (2)C10—H110.9700
O9—C131.195 (3)C10—H120.9700
N1—N21.374 (2)C10—H130.9700
N1—C151.299 (2)C12—H140.9700
N2—C161.303 (2)C12—H150.9700
C1—C21.533 (2)C12—H160.9700
C1—C61.509 (2)C14—H170.9700
C2—C31.521 (2)C14—H180.9700
C3—C41.518 (2)C14—H190.9700
C4—C51.525 (2)C18—H200.9700
C7—C81.487 (3)C19—H210.9700
C9—C101.484 (3)C20—H220.9700
C11—C121.487 (2)C21—H230.9700
C13—C141.486 (3)C22—H240.9700
C16—C171.467 (2)
S1···O83.0077 (14)C13···O63.394 (2)
S1···C133.519 (2)C13···S13.519 (2)
S1···C18i3.548 (2)C14···O3xi3.418 (3)
S1···C19i3.456 (2)C14···O7vii3.343 (3)
S2···O13.3061 (15)C17···C8viii3.567 (3)
S2···N22.5317 (13)C18···C8viii3.530 (3)
S2···N1ii3.3264 (17)C18···S1xii3.548 (2)
S2···N2ii3.3019 (16)C19···S1xii3.456 (2)
S1···H24ii3.1500C7···H22xiii3.0300
S2···H202.8100C9···H62.9500
O1···S23.3061 (15)C12···H8v2.9200
O1···O22.7281 (17)C12···H3vii3.0500
O2···O12.7281 (17)C14···H12vii3.0600
O3···C9iii3.081 (3)C17···H9viii3.0300
O3···C14iv3.418 (3)C18···H9viii3.0000
O3···C10iii3.104 (2)C21···H20x3.0500
O4···O62.9434 (19)C22···H20x3.0600
O5···C73.293 (3)H1···H52.3600
O5···C12iii3.285 (2)H1···H16xii2.4200
O5···C10v3.163 (2)H1···O7vi2.8600
O6···O42.9434 (19)H2···O22.5100
O6···C133.394 (2)H2···O52.2500
O6···O82.8520 (17)H3···O72.3300
O7···C14vi3.343 (3)H3···H52.5900
O7···C12vi3.405 (2)H3···O7vi2.8300
O8···C113.226 (2)H3···C12vi3.0500
O8···O62.8520 (17)H4···O92.2300
O8···S13.0077 (14)H5···H12.3600
O2···H22.5100H5···H32.5900
O3···H12iii2.4500H6···O32.3500
O3···H62.3500H6···O42.7000
O4···H62.7000H6···C92.9500
O5···H22.2500H6···O5iii2.8000
O5···H14iii2.3300H7···H23xiii2.5600
O5···H6v2.8000H8···C12iii2.9200
O5···H11v2.5400H8···H15iii2.3300
O7···H3vii2.8300H9···C17ii3.0300
O7···H1vii2.8600H9···C18ii3.0000
O7···H32.3300H10···N1xiv2.6600
O7···H16vi2.6600H11···H14xii2.5400
O7···H18vi2.7900H11···O5iii2.5400
O8···H15vi2.7600H12···O3v2.4500
O9···H42.2300H12···C14vi3.0600
O9···H23ii2.8800H12···H19vi2.6000
N1···S22.5400 (14)H14···H11i2.5400
N1···S2viii3.3264 (17)H14···O5v2.3300
N2···S22.5317 (13)H15···O8vii2.7600
N2···S2viii3.3019 (16)H15···H8v2.3300
N1···H10ix2.6600H16···H1i2.4200
N2···H242.5800H16···O7vii2.6600
N2···H21x2.6900H18···O7vii2.7900
C6···C93.483 (3)H19···H12vii2.6000
C7···O53.293 (3)H20···S22.8100
C8···C17ii3.567 (3)H20···C21xiii3.0500
C8···C18ii3.530 (3)H20···C22xiii3.0600
C9···C63.483 (3)H21···N2xiii2.6900
C9···O3v3.081 (3)H22···C7x3.0300
C10···O5iii3.163 (2)H23···O9viii2.8800
C10···O3v3.104 (2)H23···H7x2.5600
C11···O83.226 (2)H24···N22.5800
C12···O7vii3.405 (2)H24···S1viii3.1500
C12···O5v3.285 (2)
C5—S1—C15100.53 (8)C6—C1—H1109.00
C15—S2—C1687.45 (8)O4—C2—H2110.00
C1—O1—C5112.2 (1)C1—C2—H2110.00
C6—O2—C7118.0 (2)C3—C2—H2110.00
C2—O4—C9117.5 (1)O6—C3—H3111.00
C3—O6—C11118.6 (1)C2—C3—H3111.00
C4—O8—C13117.5 (1)C4—C3—H3111.00
N2—N1—C15112.0 (1)O8—C4—H4109.00
N1—N2—C16113.1 (1)C3—C4—H4109.00
O1—C1—C2110.0 (1)C5—C4—H4109.00
O1—C1—C6106.8 (1)S1—C5—H5111.00
C2—C1—C6112.3 (1)O1—C5—H5111.00
O4—C2—C1107.6 (1)C4—C5—H5111.00
O4—C2—C3108.2 (1)O2—C6—H6110.00
C1—C2—C3112.0 (1)O2—C6—H7110.00
O6—C3—C2108.0 (1)C1—C6—H6110.00
O6—C3—C4107.1 (1)C1—C6—H7110.00
C2—C3—C4109.9 (1)H6—C6—H7109.00
O8—C4—C3109.0 (1)C7—C8—H8109.00
O8—C4—C5110.1 (1)C7—C8—H9110.00
C3—C4—C5109.6 (1)C7—C8—H10109.00
S1—C5—O1109.1 (1)H8—C8—H9110.00
S1—C5—C4107.6 (1)H8—C8—H10109.00
O1—C5—C4107.7 (1)H9—C8—H10109.00
O2—C6—C1107.8 (1)C9—C10—H11110.00
O2—C7—O3123.7 (2)C9—C10—H12109.00
O2—C7—C8110.9 (2)C9—C10—H13109.00
O3—C7—C8125.4 (2)H11—C10—H12109.00
O4—C9—O5122.9 (2)H11—C10—H13109.00
O4—C9—C10111.6 (2)H12—C10—H13109.00
O5—C9—C10125.5 (2)C11—C12—H14109.00
O6—C11—O7123.5 (2)C11—C12—H15109.00
O6—C11—C12110.1 (1)C11—C12—H16109.00
O7—C11—C12126.4 (2)H14—C12—H15109.00
O8—C13—O9122.5 (2)H14—C12—H16110.00
O8—C13—C14110.8 (2)H15—C12—H16110.00
O9—C13—C14126.7 (2)C13—C14—H17109.00
S1—C15—S2123.53 (9)C13—C14—H18110.00
S1—C15—N1122.1 (1)C13—C14—H19109.00
S2—C15—N1114.2 (1)H17—C14—H18110.00
S2—C16—N2113.3 (1)H17—C14—H19109.00
S2—C16—C17124.4 (1)H18—C14—H19109.00
N2—C16—C17122.3 (1)C17—C18—H20120.00
C16—C17—C18121.4 (2)C19—C18—H20120.00
C16—C17—C22119.2 (1)C18—C19—H21120.00
C18—C17—C22119.4 (2)C20—C19—H21120.00
C17—C18—C19119.9 (2)C19—C20—H22120.00
C18—C19—C20120.3 (2)C21—C20—H22120.00
C19—C20—C21120.3 (2)C20—C21—H23120.00
C20—C21—C22120.0 (2)C22—C21—H23120.00
C17—C22—C21120.0 (2)C17—C22—H24120.00
O1—C1—H1109.00C21—C22—H24120.00
C2—C1—H1109.00
S1—C5—O1—C1176.6 (1)N2—C16—C17—C18163.6 (2)
S1—C5—C4—O860.2 (1)N2—C16—C17—C2217.1 (3)
S1—C5—C4—C3179.84 (10)C1—O1—C5—C467.0 (2)
S1—C15—S2—C16175.9 (1)C1—C2—O4—C9113.7 (1)
S1—C15—N1—N2176.0 (1)C1—C2—C3—C449.0 (2)
S2—C15—S1—C578.1 (1)C1—C6—O2—C7143.7 (2)
S2—C15—N1—N20.6 (2)C2—O4—C9—C10177.0 (1)
S2—C16—N2—N10.2 (2)C2—C1—O1—C561.4 (2)
S2—C16—C17—C1816.7 (2)C2—C3—O6—C11136.0 (1)
S2—C16—C17—C22162.6 (1)C2—C3—C4—C554.2 (2)
O1—C1—C2—O4170.1 (1)C3—O6—C11—C12168.3 (1)
O1—C1—C2—C351.3 (2)C3—C2—O4—C9125.0 (1)
O1—C1—C6—O259.6 (2)C3—C2—C1—C6170.1 (1)
O1—C5—S1—C1567.2 (1)C3—C4—O8—C13117.8 (2)
O1—C5—C4—O8177.7 (1)C4—O8—C13—C14175.2 (2)
O1—C5—C4—C362.4 (2)C4—C3—O6—C11105.7 (1)
O2—C6—C1—C261.0 (2)C4—C5—S1—C15176.3 (1)
O3—C7—O2—C61.0 (3)C5—O1—C1—C6176.6 (1)
O4—C2—C1—C671.1 (2)C5—C4—O8—C13121.9 (1)
O4—C2—C3—O676.1 (1)C6—O2—C7—C8179.4 (2)
O4—C2—C3—C4167.4 (1)C15—S2—C16—C17179.9 (2)
O5—C9—O4—C22.0 (2)C15—N1—N2—C160.2 (3)
O6—C3—C2—C1165.5 (1)C16—C17—C18—C19178.7 (2)
O6—C3—C4—O868.2 (1)C16—C17—C22—C21178.6 (2)
O6—C3—C4—C5171.2 (1)C17—C18—C19—C200.9 (3)
O7—C11—O6—C310.4 (2)C17—C22—C21—C201.2 (3)
O8—C4—C3—C2174.8 (1)C18—C17—C22—C212.1 (3)
O9—C13—O8—C44.8 (3)C18—C19—C20—C210.0 (3)
N1—N2—C16—C17179.9 (2)C19—C18—C17—C222.0 (3)
N1—C15—S1—C5107.0 (2)C19—C20—C21—C220.1 (4)
N1—C15—S2—C160.5 (2)C19—C20—C21—C220.1 (4)
N2—C16—S2—C150.4 (2)
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+3/2; (iii) x1/2, y1/2, z+1; (iv) x1, y1, z; (v) x+1/2, y1/2, z+1; (vi) x1/2, y+1/2, z+1; (vii) x+1/2, y+1/2, z+1; (viii) x, y+1/2, z+3/2; (ix) x, y+1, z; (x) x1, y+1/2, z+3/2; (xi) x+1, y+1, z; (xii) x1, y, z; (xiii) x1, y1/2, z+3/2; (xiv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC22H24N2O9S2
Mr524.56
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)8.010 (2), 10.526 (2), 28.685 (6)
V3)2418.7 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.35 × 0.25 × 0.20
Data collection
DiffractometerRigaku/MSC Mercury CCD area-detector
diffractometer
Absorption correctionMulti-scan
TEXSAN (Molecular Structure Corporation, 1999)
Tmin, Tmax0.825, 0.947
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
19569, 5524, 5151
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.046, 1.06
No. of reflections5499
No. of parameters317
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.24
Absolute structureFlack (1983), with how many Friedel pairs
Absolute structure parameter0.00 (5)

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), TEXSAN, ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
S1—C51.807 (2)N1—C151.299 (2)
S1—C151.753 (2)N2—C161.303 (2)
S2—C151.715 (2)C1—C21.533 (2)
S2—C161.716 (2)C1—C61.509 (2)
O1—C11.431 (2)C2—C31.521 (2)
O1—C51.418 (2)C3—C41.518 (2)
O2—C61.442 (2)C4—C51.525 (2)
O2—C71.346 (2)C7—C81.487 (3)
O3—C71.191 (3)C9—C101.484 (3)
O4—C21.440 (2)C11—C121.487 (2)
O4—C91.362 (2)C13—C141.486 (3)
O5—C91.190 (2)C16—C171.467 (2)
O6—C31.436 (2)C17—C181.392 (2)
O6—C111.357 (2)C17—C221.396 (2)
O7—C111.202 (2)C18—C191.389 (3)
O8—C41.433 (2)C19—C201.370 (3)
O8—C131.364 (2)C20—C211.386 (3)
O9—C131.195 (3)C21—C221.384 (3)
N1—N21.374 (2)
C5—S1—C15100.53 (8)O2—C7—C8110.9 (2)
C15—S2—C1687.45 (8)O3—C7—C8125.4 (2)
C1—O1—C5112.2 (1)O4—C9—O5122.9 (2)
C6—O2—C7118.0 (2)O4—C9—C10111.6 (2)
C2—O4—C9117.5 (1)O5—C9—C10125.5 (2)
C3—O6—C11118.6 (1)O6—C11—O7123.5 (2)
C4—O8—C13117.5 (1)O6—C11—C12110.1 (1)
N2—N1—C15112.0 (1)O7—C11—C12126.4 (2)
N1—N2—C16113.1 (1)O8—C13—O9122.5 (2)
O1—C1—C2110.0 (1)O8—C13—C14110.8 (2)
O1—C1—C6106.8 (1)O9—C13—C14126.7 (2)
C2—C1—C6112.3 (1)S1—C15—S2123.53 (9)
O4—C2—C1107.6 (1)S1—C15—N1122.1 (1)
O4—C2—C3108.2 (1)S2—C15—N1114.2 (1)
C1—C2—C3112.0 (1)S2—C16—N2113.3 (1)
O6—C3—C2108.0 (1)S2—C16—C17124.4 (1)
O6—C3—C4107.1 (1)N2—C16—C17122.3 (1)
C2—C3—C4109.9 (1)C16—C17—C18121.4 (2)
O8—C4—C3109.0 (1)C16—C17—C22119.2 (1)
O8—C4—C5110.1 (1)C18—C17—C22119.4 (2)
C3—C4—C5109.6 (1)C17—C18—C19119.9 (2)
S1—C5—O1109.1 (1)C18—C19—C20120.3 (2)
S1—C5—C4107.6 (1)C19—C20—C21120.3 (2)
O1—C5—C4107.7 (1)C20—C21—C22120.0 (2)
O2—C6—C1107.8 (1)C17—C22—C21120.0 (2)
O2—C7—O3123.7 (2)
S1—C5—O1—C1176.6 (1)N2—C16—C17—C18163.6 (2)
S1—C5—C4—O860.2 (1)N2—C16—C17—C2217.1 (3)
S1—C5—C4—C3179.84 (10)C1—O1—C5—C467.0 (2)
S1—C15—S2—C16175.9 (1)C1—C2—O4—C9113.7 (1)
S1—C15—N1—N2176.0 (1)C1—C2—C3—C449.0 (2)
S2—C15—S1—C578.1 (1)C1—C6—O2—C7143.7 (2)
S2—C15—N1—N20.6 (2)C2—O4—C9—C10177.0 (1)
S2—C16—N2—N10.2 (2)C2—C1—O1—C561.4 (2)
S2—C16—C17—C1816.7 (2)C2—C3—O6—C11136.0 (1)
S2—C16—C17—C22162.6 (1)C2—C3—C4—C554.2 (2)
O1—C1—C2—O4170.1 (1)C3—O6—C11—C12168.3 (1)
O1—C1—C2—C351.3 (2)C3—C2—O4—C9125.0 (1)
O1—C1—C6—O259.6 (2)C3—C2—C1—C6170.1 (1)
O1—C5—S1—C1567.2 (1)C3—C4—O8—C13117.8 (2)
O1—C5—C4—O8177.7 (1)C4—O8—C13—C14175.2 (2)
O1—C5—C4—C362.4 (2)C4—C3—O6—C11105.7 (1)
O2—C6—C1—C261.0 (2)C4—C5—S1—C15176.3 (1)
O3—C7—O2—C61.0 (3)C5—O1—C1—C6176.6 (1)
O4—C2—C1—C671.1 (2)C5—C4—O8—C13121.9 (1)
O4—C2—C3—O676.1 (1)C6—O2—C7—C8179.4 (2)
O4—C2—C3—C4167.4 (1)C15—S2—C16—C17179.9 (2)
O5—C9—O4—C22.0 (2)C15—N1—N2—C160.2 (3)
O6—C3—C2—C1165.5 (1)C16—C17—C18—C19178.7 (2)
O6—C3—C4—O868.2 (1)C16—C17—C22—C21178.6 (2)
O6—C3—C4—C5171.2 (1)C17—C18—C19—C200.9 (3)
O7—C11—O6—C310.4 (2)C17—C22—C21—C201.2 (3)
O8—C4—C3—C2174.8 (1)C18—C17—C22—C212.1 (3)
O9—C13—O8—C44.8 (3)C18—C19—C20—C210.0 (3)
N1—N2—C16—C17179.9 (2)C19—C18—C17—C222.0 (3)
N1—C15—S1—C5107.0 (2)C19—C20—C21—C220.1 (4)
N1—C15—S2—C160.5 (2)C19—C20—C21—C220.1 (4)
N2—C16—S2—C150.4 (2)
 

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