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The title compound crystallizes in the space group P21/n and may be described by a partial ordering of a 1:1 disordered P21/a parent structure with the c axis halved. The pentasulfane chain completes a full turn of a helix, which gives molecules containing left- or right-handed helices similar spatial requirements and allows them to be interchanged. The structure can be redescribed as containing 0.732 (1) of an ordered P21/n structure and 0.268 (1) of a 1:1 disordered P21/a structure, implying that 0.134 (1) of the molecule sites contain molecules of the opposite hand to that predicted by an ordered P21/n structure. It is found that the average molecular position in the asymmetric unit is not the same for each component and that these structural differences must be recognized to obtain a satisfactory refinement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104010699/ck5003sup1.cif
Contains datablocks IV-a, IV-b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104010699/ck5003IV-asup2.hkl
Contains datablocks IV-a, vcif WARNING: Line 0: length exceeds internal buffer size (4096) - rest discarded

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104010699/ck5003IV-bsup3.hkl
Contains datablocks IV-b, vcif WARNING: Line 0: length exceeds internal buffer size (4096) - rest discarded

CCDC reference: 248459

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for IV-a; RAELS00 (Rae, 2000) for IV-b. Molecular graphics: ORTEPII (Johnson, 1976) for IV-a; PLATON (Spek, 2003) for IV-b. Software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003) for IV-a; RAELS00 and manual editing for IV-b.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
(IV-a) bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutyl)pentasulfane top
Crystal data top
C16H24Cl2O2S5F(000) = 1000
Mr = 479.57Dx = 1.428 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.6666 (1) ÅCell parameters from 39932 reflections
b = 8.1343 (1) Åθ = 2.0–30.0°
c = 23.8366 (2) ŵ = 0.77 mm1
β = 99.6985 (6)°T = 160 K
V = 2229.75 (4) Å3Prism, colourless
Z = 40.25 × 0.22 × 0.17 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
6525 independent reflections
Radiation source: Nonius FR590 sealed tube generator4992 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.053
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.7°
ω scans with κ offsetsh = 1616
Absorption correction: multi-scan
(Blessing, 1995)
k = 1111
Tmin = 0.811, Tmax = 0.880l = 3333
53514 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0396P)2 + 0.5412P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6523 reflectionsΔρmax = 0.31 e Å3
298 parametersΔρmin = 0.29 e Å3
0 restraints
Crystal data top
C16H24Cl2O2S5V = 2229.75 (4) Å3
Mr = 479.57Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.6666 (1) ŵ = 0.77 mm1
b = 8.1343 (1) ÅT = 160 K
c = 23.8366 (2) Å0.25 × 0.22 × 0.17 mm
β = 99.6985 (6)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6525 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
4992 reflections with I > 2σ(I)
Tmin = 0.811, Tmax = 0.880Rint = 0.053
53514 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å3
6523 reflectionsΔρmin = 0.29 e Å3
298 parameters
Special details top

Experimental. Solvent used: hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.440 (1) Frames collected: 629 Seconds exposure per frame: 26 Degrees rotation per frame: 1.3 Crystal-Detector distance (mm): 37.0

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*/UeqOcc. (<1)
Cl1A0.33632 (5)1.03916 (8)0.10305 (3)0.03214 (13)0.8537 (10)
Cl2A0.75370 (6)1.24679 (9)0.30670 (3)0.03523 (15)0.8537 (10)
S1A0.29062 (5)0.78998 (8)0.18470 (3)0.02642 (12)0.8537 (10)
S2A0.33802 (4)0.96808 (6)0.244104 (17)0.03399 (12)0.8537 (10)
S3A0.50805 (5)1.02907 (8)0.24015 (2)0.03531 (14)0.8537 (10)
S4A0.60827 (4)0.88265 (5)0.299657 (17)0.02906 (11)0.8537 (10)
S5A0.64206 (6)1.01331 (9)0.37350 (3)0.02420 (13)0.8537 (10)
O10.04528 (8)0.86186 (14)0.05261 (5)0.0389 (3)
C10.22528 (11)0.90502 (16)0.12333 (5)0.0234 (3)
C20.10502 (11)0.99627 (17)0.12484 (6)0.0249 (3)
C30.05230 (11)0.87918 (17)0.07755 (6)0.0256 (3)
C40.16556 (11)0.79051 (17)0.07283 (5)0.0228 (3)
C50.09905 (14)1.17574 (19)0.10552 (7)0.0357 (3)
H510.12821.18510.06940.054*
H520.14691.24350.13440.054*
H530.01821.21370.10030.054*
C60.05086 (14)0.9757 (2)0.17847 (7)0.0392 (4)
H610.03091.00930.17050.059*
H620.09281.04430.20900.059*
H630.05590.86020.19030.059*
C70.20316 (13)0.8211 (2)0.01533 (6)0.0349 (3)
H710.15360.75730.01420.052*
H720.28430.78710.01720.052*
H730.19570.93830.00600.052*
C80.16229 (13)0.60658 (17)0.08510 (7)0.0327 (3)
H810.13290.58900.12080.049*
H820.24090.56100.08840.049*
H830.11100.55170.05390.049*
Cl2B0.6560 (4)0.9719 (5)0.39170 (17)0.0343 (9)0.1463 (10)
Cl1B0.2475 (3)0.7590 (5)0.19091 (15)0.0347 (8)0.1463 (10)
S5B0.7081 (3)1.2243 (4)0.31238 (15)0.0280 (7)0.1463 (10)
S4B0.6507 (2)1.0538 (4)0.25178 (10)0.0358 (7)0.1463 (10)
S3B0.4812 (3)0.9944 (5)0.25876 (16)0.0405 (9)0.1463 (10)
S2B0.3774 (2)1.1335 (3)0.19852 (11)0.0342 (7)0.1463 (10)
S1B0.3510 (3)1.0016 (5)0.12447 (15)0.0281 (7)0.1463 (10)
O21.04804 (9)1.12079 (15)0.43930 (5)0.0425 (3)
C90.77769 (11)1.10972 (17)0.36784 (5)0.0232 (3)
C100.83894 (11)1.20318 (17)0.42319 (5)0.0244 (3)
C110.94877 (11)1.10965 (18)0.41590 (6)0.0269 (3)
C120.89018 (12)1.00020 (17)0.36748 (6)0.0262 (3)
C130.84895 (14)1.38945 (19)0.42016 (7)0.0384 (4)
H1310.89801.43000.45490.058*
H1320.77141.43860.41670.058*
H1330.88391.41960.38700.058*
C140.79614 (13)1.1516 (2)0.47797 (6)0.0337 (3)
H1410.79481.03130.48040.051*
H1420.71761.19470.47760.051*
H1430.84871.19570.51090.051*
C150.94744 (15)1.0034 (2)0.31442 (7)0.0428 (4)
H1510.95931.11760.30370.064*
H1520.89710.94750.28310.064*
H1531.02270.94700.32240.064*
C160.88098 (14)0.82255 (19)0.38789 (7)0.0377 (4)
H1610.95890.77450.39690.057*
H1620.83370.75800.35780.057*
H1630.84440.82170.42200.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0277 (3)0.0339 (3)0.0352 (3)0.0101 (2)0.0065 (2)0.0033 (2)
Cl2A0.0358 (3)0.0400 (3)0.0278 (2)0.0058 (3)0.0009 (2)0.01356 (19)
S1A0.0267 (3)0.0267 (3)0.0232 (2)0.0007 (2)0.0033 (2)0.00277 (19)
S2A0.0303 (2)0.0463 (3)0.0234 (2)0.00314 (19)0.00119 (16)0.00881 (18)
S3A0.0348 (3)0.0419 (3)0.0253 (3)0.0082 (2)0.0061 (2)0.0003 (2)
S4A0.0281 (2)0.0307 (2)0.0266 (2)0.00383 (17)0.00066 (15)0.00619 (16)
S5A0.0196 (2)0.0325 (3)0.0202 (3)0.0048 (2)0.0028 (2)0.0017 (2)
O10.0201 (5)0.0417 (7)0.0511 (6)0.0001 (5)0.0045 (4)0.0002 (5)
C10.0201 (6)0.0233 (7)0.0253 (6)0.0002 (5)0.0000 (5)0.0003 (5)
C20.0222 (6)0.0252 (7)0.0270 (6)0.0035 (5)0.0030 (5)0.0003 (5)
C30.0212 (6)0.0247 (7)0.0299 (7)0.0005 (5)0.0014 (5)0.0036 (5)
C40.0194 (6)0.0241 (7)0.0233 (6)0.0006 (5)0.0011 (5)0.0018 (5)
C50.0403 (9)0.0262 (8)0.0397 (8)0.0058 (6)0.0043 (7)0.0005 (6)
C60.0345 (8)0.0516 (10)0.0342 (8)0.0071 (7)0.0135 (7)0.0033 (7)
C70.0329 (8)0.0471 (10)0.0237 (7)0.0079 (7)0.0019 (6)0.0026 (6)
C80.0319 (8)0.0243 (7)0.0398 (8)0.0005 (6)0.0002 (6)0.0042 (6)
Cl2B0.0269 (17)0.039 (2)0.037 (2)0.0126 (14)0.0065 (16)0.0016 (15)
Cl1B0.040 (2)0.0341 (18)0.0275 (14)0.0052 (15)0.0029 (14)0.0123 (11)
S5B0.0350 (19)0.0193 (14)0.0256 (14)0.0021 (14)0.0071 (14)0.0006 (10)
S4B0.0336 (14)0.0474 (17)0.0240 (12)0.0026 (12)0.0020 (10)0.0099 (11)
S3B0.041 (2)0.046 (2)0.0297 (19)0.0080 (15)0.0070 (14)0.0032 (15)
S2B0.0322 (13)0.0325 (14)0.0344 (13)0.0038 (11)0.0048 (10)0.0059 (10)
S1B0.0215 (14)0.0350 (19)0.0282 (18)0.0071 (12)0.0052 (13)0.0001 (13)
O20.0211 (5)0.0507 (7)0.0513 (7)0.0005 (5)0.0066 (5)0.0012 (6)
C90.0214 (6)0.0245 (7)0.0223 (6)0.0010 (5)0.0005 (5)0.0023 (5)
C100.0212 (6)0.0256 (7)0.0241 (6)0.0003 (5)0.0027 (5)0.0025 (5)
C110.0215 (6)0.0277 (7)0.0304 (7)0.0011 (5)0.0008 (5)0.0031 (6)
C120.0218 (6)0.0267 (7)0.0307 (7)0.0008 (5)0.0063 (5)0.0012 (5)
C130.0383 (8)0.0263 (8)0.0485 (9)0.0039 (7)0.0012 (7)0.0069 (7)
C140.0331 (8)0.0443 (9)0.0221 (6)0.0064 (7)0.0001 (6)0.0007 (6)
C150.0356 (8)0.0571 (11)0.0395 (9)0.0042 (8)0.0168 (7)0.0077 (8)
C160.0351 (8)0.0263 (8)0.0520 (9)0.0057 (6)0.0081 (7)0.0020 (7)
Geometric parameters (Å, º) top
Cl1A—C11.8204 (14)C8—H820.9800
Cl2A—C91.8188 (14)C8—H830.9800
S1A—C11.7946 (14)Cl2B—C91.966 (4)
S1A—S2A2.0361 (7)S5B—C91.707 (4)
S2A—S3A2.0623 (8)S5B—S4B2.033 (4)
S3A—S4A2.0589 (8)S4B—S3B2.070 (5)
S4A—S5A2.0370 (8)S3B—S2B2.054 (5)
S5A—C91.7914 (15)S2B—S1B2.044 (4)
O1—C31.2004 (16)O2—C111.2012 (16)
C1—C41.5873 (18)C9—C101.5847 (18)
C1—C21.5930 (18)C9—C121.5874 (18)
C1—S1B1.660 (4)C10—C131.522 (2)
C1—Cl1B1.983 (4)C10—C111.5251 (19)
C2—C31.5240 (19)C10—C141.5331 (19)
C2—C61.528 (2)C11—C121.5251 (19)
C2—C51.529 (2)C12—C151.527 (2)
C3—C41.5261 (18)C12—C161.534 (2)
C4—C81.5262 (19)C13—H1310.9800
C4—C71.5282 (18)C13—H1320.9800
C5—H510.9800C13—H1330.9800
C5—H520.9800C14—H1410.9800
C5—H530.9800C14—H1420.9800
C6—H610.9800C14—H1430.9800
C6—H620.9800C15—H1510.9800
C6—H630.9800C15—H1520.9800
C7—H710.9800C15—H1530.9800
C7—H720.9800C16—H1610.9800
C7—H730.9800C16—H1620.9800
C8—H810.9800C16—H1630.9800
C1—S1A—S2A102.95 (5)C9—S5B—S4B103.56 (19)
S1A—S2A—S3A106.86 (3)S5B—S4B—S3B107.85 (19)
S4A—S3A—S2A105.56 (3)S2B—S3B—S4B105.9 (2)
S5A—S4A—S3A107.35 (3)S1B—S2B—S3B107.46 (19)
C9—S5A—S4A102.02 (5)C1—S1B—S2B105.5 (2)
C4—C1—C290.85 (9)C10—C9—C1290.94 (9)
C4—C1—S1B124.33 (15)C10—C9—S5B118.15 (15)
C2—C1—S1B123.92 (17)C12—C9—S5B126.02 (16)
C4—C1—S1A112.59 (9)C10—C9—S5A115.31 (9)
C2—C1—S1A118.64 (9)C12—C9—S5A119.75 (10)
C4—C1—Cl1A113.04 (9)C10—C9—Cl2A111.10 (9)
C2—C1—Cl1A113.30 (9)C12—C9—Cl2A110.82 (9)
S1A—C1—Cl1A107.79 (7)S5A—C9—Cl2A108.06 (7)
C4—C1—Cl1B104.20 (14)C10—C9—Cl2B106.19 (15)
C2—C1—Cl1B104.83 (14)C12—C9—Cl2B108.63 (16)
S1B—C1—Cl1B106.02 (17)S5B—C9—Cl2B105.24 (18)
C3—C2—C6112.21 (12)C13—C10—C11114.74 (12)
C3—C2—C5112.44 (11)C13—C10—C14110.58 (12)
C6—C2—C5110.64 (12)C11—C10—C14111.16 (11)
C3—C2—C186.53 (9)C13—C10—C9117.74 (11)
C6—C2—C1117.25 (11)C11—C10—C986.31 (10)
C5—C2—C1115.70 (12)C14—C10—C9114.32 (11)
O1—C3—C2132.11 (13)O2—C11—C10132.24 (13)
O1—C3—C4131.96 (13)O2—C11—C12132.04 (14)
C2—C3—C495.93 (10)C10—C11—C1295.70 (10)
C3—C4—C8113.53 (11)C11—C12—C15114.47 (12)
C3—C4—C7111.85 (11)C11—C12—C16110.87 (12)
C8—C4—C7110.57 (12)C15—C12—C16110.02 (13)
C3—C4—C186.66 (9)C11—C12—C986.21 (10)
C8—C4—C1116.86 (11)C15—C12—C9118.19 (12)
C7—C4—C1115.42 (11)C16—C12—C9115.14 (11)
C2—C5—H51109.5C10—C13—H131109.5
C2—C5—H52109.5C10—C13—H132109.5
H51—C5—H52109.5H131—C13—H132109.5
C2—C5—H53109.5C10—C13—H133109.5
H51—C5—H53109.5H131—C13—H133109.5
H52—C5—H53109.5H132—C13—H133109.5
C2—C6—H61109.5C10—C14—H141109.5
C2—C6—H62109.5C10—C14—H142109.5
H61—C6—H62109.5H141—C14—H142109.5
C2—C6—H63109.5C10—C14—H143109.5
H61—C6—H63109.5H141—C14—H143109.5
H62—C6—H63109.5H142—C14—H143109.5
C4—C7—H71109.5C12—C15—H151109.5
C4—C7—H72109.5C12—C15—H152109.5
H71—C7—H72109.5H151—C15—H152109.5
C4—C7—H73109.5C12—C15—H153109.5
H71—C7—H73109.5H151—C15—H153109.5
H72—C7—H73109.5H152—C15—H153109.5
C4—C8—H81109.5C12—C16—H161109.5
C4—C8—H82109.5C12—C16—H162109.5
H81—C8—H82109.5H161—C16—H162109.5
C4—C8—H83109.5C12—C16—H163109.5
H81—C8—H83109.5H161—C16—H163109.5
H82—C8—H83109.5H162—C16—H163109.5
C1—S1A—S2A—S3A93.20 (5)C4—C1—S1B—S2B178.09 (13)
S1A—S2A—S3A—S4A92.85 (4)C2—C1—S1B—S2B59.4 (2)
S2A—S3A—S4A—S5A93.34 (4)Cl1B—C1—S1B—S2B61.6 (2)
S3A—S4A—S5A—C992.40 (6)S3B—S2B—S1B—C195.3 (2)
S2A—S1A—C1—C4172.41 (8)S4B—S5B—C9—C10177.81 (14)
S2A—S1A—C1—C268.21 (10)S4B—S5B—C9—C1263.5 (2)
S2A—S1A—C1—Cl1A62.23 (7)S4B—S5B—C9—Cl2B63.9 (2)
C4—C1—C2—C31.55 (9)S4A—S5A—C9—C10171.78 (8)
S1B—C1—C2—C3135.15 (18)S4A—S5A—C9—C1264.84 (10)
S1A—C1—C2—C3114.92 (10)S4A—S5A—C9—Cl2A63.26 (7)
Cl1A—C1—C2—C3117.18 (9)C12—C9—C10—C13122.89 (13)
Cl1B—C1—C2—C3103.39 (14)S5B—C9—C10—C139.6 (2)
C4—C1—C2—C6114.80 (13)S5A—C9—C10—C13113.27 (13)
S1B—C1—C2—C6111.6 (2)Cl2A—C9—C10—C1310.09 (15)
S1A—C1—C2—C61.67 (17)Cl2B—C9—C10—C13127.39 (18)
Cl1A—C1—C2—C6129.57 (12)C12—C9—C10—C116.80 (10)
Cl1B—C1—C2—C69.87 (18)S5B—C9—C10—C11125.72 (18)
C4—C1—C2—C5111.73 (12)S5A—C9—C10—C11130.63 (10)
S1B—C1—C2—C521.9 (2)Cl2A—C9—C10—C11106.00 (10)
S1A—C1—C2—C5131.80 (11)Cl2B—C9—C10—C11116.52 (16)
Cl1A—C1—C2—C53.90 (15)C12—C9—C10—C14104.78 (12)
Cl1B—C1—C2—C5143.34 (15)S5B—C9—C10—C14122.71 (19)
C6—C2—C3—O160.0 (2)S5A—C9—C10—C1419.06 (15)
C5—C2—C3—O165.5 (2)Cl2A—C9—C10—C14142.43 (10)
C1—C2—C3—O1178.07 (16)Cl2B—C9—C10—C144.95 (19)
C6—C2—C3—C4119.69 (12)C13—C10—C11—O252.4 (2)
C5—C2—C3—C4114.81 (12)C14—C10—C11—O274.0 (2)
C1—C2—C3—C41.62 (10)C9—C10—C11—O2171.35 (17)
O1—C3—C4—C860.1 (2)C13—C10—C11—C12126.04 (13)
C2—C3—C4—C8119.54 (12)C14—C10—C11—C12107.57 (12)
O1—C3—C4—C765.8 (2)C9—C10—C11—C127.11 (10)
C2—C3—C4—C7114.47 (12)O2—C11—C12—C1552.0 (2)
O1—C3—C4—C1178.07 (16)C10—C11—C12—C15126.44 (13)
C2—C3—C4—C11.62 (10)O2—C11—C12—C1673.1 (2)
C2—C1—C4—C31.54 (9)C10—C11—C12—C16108.39 (12)
S1B—C1—C4—C3134.86 (19)O2—C11—C12—C9171.37 (17)
S1A—C1—C4—C3120.14 (9)C10—C11—C12—C97.10 (10)
Cl1A—C1—C4—C3117.41 (10)C10—C9—C12—C116.80 (10)
Cl1B—C1—C4—C3103.98 (14)S5B—C9—C12—C11119.74 (18)
C2—C1—C4—C8116.30 (12)S5A—C9—C12—C11126.92 (10)
S1B—C1—C4—C8110.4 (2)Cl2A—C9—C12—C11106.25 (10)
S1A—C1—C4—C85.39 (15)Cl2B—C9—C12—C11114.25 (16)
Cl1A—C1—C4—C8127.83 (11)C10—C9—C12—C15122.61 (13)
Cl1B—C1—C4—C810.77 (18)S5B—C9—C12—C153.9 (2)
C2—C1—C4—C7111.10 (12)S5A—C9—C12—C15117.27 (13)
S1B—C1—C4—C722.2 (2)Cl2A—C9—C12—C159.57 (16)
S1A—C1—C4—C7127.21 (11)Cl2B—C9—C12—C15129.94 (17)
Cl1A—C1—C4—C74.76 (14)C10—C9—C12—C16104.50 (13)
Cl1B—C1—C4—C7143.37 (16)S5B—C9—C12—C16128.96 (19)
C9—S5B—S4B—S3B94.6 (2)S5A—C9—C12—C1615.62 (16)
S5B—S4B—S3B—S2B97.6 (2)Cl2A—C9—C12—C16142.46 (11)
S4B—S3B—S2B—S1B88.6 (2)Cl2B—C9—C12—C162.9 (2)
(IV-b) bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutyl)pentasulfane top
Crystal data top
C16H24Cl2O2S5F(000) = 1000
Mr = 479.57Dx = 1.428 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.6666 (1) ÅCell parameters from 39932 reflections
b = 8.1343 (1) Åθ = 2.0–30.0°
c = 23.8366 (2) ŵ = 0.77 mm1
β = 99.6985 (6)°T = 160 K
V = 2229.75 (4) Å3Prism, colourless
Z = 40.25 × 0.22 × 0.17 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
6524 independent reflections
Radiation source: Nonius FR590 sealed tube generator4595 reflections with I > 3σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.053
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.7°
ω scans with κ offsetsh = 1616
Absorption correction: multi-scan
(Blessing, 1995)
k = 1111
Tmin = 0.811, Tmax = 0.880l = 3333
53514 measured reflections
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo) + (0.03Fo)2]
S = 1.42(Δ/σ)max = 0.05
4595 reflectionsΔρmax = 0.51 e Å3
188 parametersΔρmin = 0.78 e Å3
Crystal data top
C16H24Cl2O2S5V = 2229.75 (4) Å3
Mr = 479.57Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.6666 (1) ŵ = 0.77 mm1
b = 8.1343 (1) ÅT = 160 K
c = 23.8366 (2) Å0.25 × 0.22 × 0.17 mm
β = 99.6985 (6)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6524 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
4595 reflections with I > 3σ(I)
Tmin = 0.811, Tmax = 0.880Rint = 0.053
53514 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039188 parameters
wR(F2) = 0.059H-atom parameters constrained
S = 1.42Δρmax = 0.51 e Å3
4595 reflectionsΔρmin = 0.78 e Å3
Special details top

Experimental. Solvent used: hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.440 (1) Frames collected: 629 Seconds exposure per frame: 26 Degrees rotation per frame: 1.3 Crystal-Detector distance (mm): 37.0

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
CL10.3358 (1)0.5403 (1)0.1026 (1)0.0322 (2)0.732 (1)
CL20.7529 (1)0.7474 (1)0.3062 (1)0.0345 (2)0.732 (1)
S10.2893 (1)0.2919 (1)0.1845 (1)0.0261 (1)0.732 (1)
S20.3362 (1)0.4715 (1)0.2435 (1)0.0321 (2)0.732 (1)
S30.5063 (1)0.5328 (1)0.2400 (1)0.0335 (2)0.732 (1)
S40.6059 (1)0.3850 (1)0.2993 (1)0.0279 (2)0.732 (1)
S50.6411 (1)0.5150 (1)0.3734 (1)0.0232 (1)0.732 (1)
O10.0447 (1)0.3611 (2)0.0512 (1)0.035 (1)0.732 (1)
O21.0484 (1)0.6168 (2)0.4383 (1)0.035 (1)0.732 (1)
C10.2254 (2)0.4079 (3)0.1218 (1)0.020 (1)0.732 (1)
C20.1046 (2)0.4969 (3)0.1232 (1)0.022 (1)0.732 (1)
C30.0524 (2)0.3790 (3)0.0762 (1)0.023 (1)0.732 (1)
C40.1660 (2)0.2897 (3)0.0723 (1)0.021 (1)0.732 (1)
C50.0975 (2)0.6771 (3)0.1040 (1)0.032 (1)0.732 (1)
C60.0505 (2)0.4746 (3)0.1772 (1)0.036 (1)0.732 (1)
C70.2029 (2)0.3180 (3)0.0144 (1)0.028 (1)0.732 (1)
C80.1627 (2)0.1069 (3)0.0861 (1)0.031 (1)0.732 (1)
C90.7779 (2)0.6115 (3)0.3666 (1)0.020 (1)0.732 (1)
C100.8890 (2)0.4985 (3)0.3665 (1)0.022 (1)0.732 (1)
C110.9487 (2)0.6068 (3)0.4148 (1)0.023 (1)0.732 (1)
C120.8399 (2)0.7024 (3)0.4224 (1)0.021 (1)0.732 (1)
C130.8771 (2)0.3210 (3)0.3872 (1)0.032 (1)0.732 (1)
C140.9471 (2)0.4991 (3)0.3138 (1)0.036 (1)0.732 (1)
C150.7957 (2)0.6491 (3)0.4770 (1)0.028 (1)0.732 (1)
C160.8513 (2)0.8889 (3)0.4204 (1)0.031 (1)0.732 (1)
CL110.3385 (2)0.5317 (2)0.1059 (1)0.0322 (2)0.134 (1)
CL210.7548 (2)0.7406 (3)0.3096 (1)0.0345 (2)0.134 (1)
S110.2969 (1)0.2767 (2)0.1865 (1)0.0261 (1)0.134 (1)
S210.3494 (2)0.4467 (4)0.2482 (1)0.0321 (2)0.134 (1)
S310.5180 (2)0.5064 (5)0.2410 (2)0.0335 (2)0.134 (1)
S410.6222 (3)0.3688 (3)0.3019 (1)0.0279 (2)0.134 (1)
S510.6475 (2)0.5002 (3)0.3758 (1)0.0232 (1)0.134 (1)
O110.0396 (2)0.3425 (4)0.0545 (1)0.035 (1)0.134 (1)
O211.0537 (2)0.6123 (4)0.4401 (1)0.035 (1)0.134 (1)
C0110.2304 (2)0.3943 (3)0.1247 (1)0.020 (1)0.134 (1)
C0210.1085 (2)0.4789 (4)0.1270 (1)0.022 (1)0.134 (1)
C0310.0575 (2)0.3622 (4)0.0794 (1)0.023 (1)0.134 (1)
C0410.1722 (2)0.2772 (4)0.0746 (1)0.021 (1)0.134 (1)
C0510.0985 (3)0.6601 (4)0.1088 (1)0.032 (1)0.134 (1)
C0610.0555 (3)0.4514 (4)0.1810 (1)0.036 (1)0.134 (1)
C0710.2079 (3)0.3103 (4)0.0167 (1)0.028 (1)0.134 (1)
C0810.1719 (3)0.0934 (4)0.0873 (1)0.031 (1)0.134 (1)
C0910.7826 (3)0.6019 (4)0.3691 (1)0.020 (1)0.134 (1)
C1010.8952 (3)0.4929 (4)0.3680 (1)0.022 (1)0.134 (1)
C1110.9539 (3)0.6002 (4)0.4168 (1)0.023 (1)0.134 (1)
C1210.8440 (3)0.6915 (4)0.4253 (1)0.021 (1)0.134 (1)
C1310.8862 (3)0.3138 (4)0.3877 (1)0.032 (1)0.134 (1)
C1410.9524 (3)0.4987 (5)0.3151 (1)0.036 (1)0.134 (1)
C1510.8014 (3)0.6334 (4)0.4799 (1)0.028 (1)0.134 (1)
C1610.8526 (3)0.8785 (4)0.4245 (1)0.031 (1)0.134 (1)
CL120.3385 (2)0.5317 (2)0.6059 (1)0.0322 (2)0.134 (1)
CL220.7548 (2)0.7406 (3)0.8096 (1)0.0345 (2)0.134 (1)
S120.2969 (1)0.2767 (2)0.6865 (1)0.0261 (1)0.134 (1)
S220.3494 (2)0.4467 (4)0.7482 (1)0.0321 (2)0.134 (1)
S320.5180 (2)0.5064 (5)0.7410 (2)0.0335 (2)0.134 (1)
S420.6222 (3)0.3688 (3)0.8019 (1)0.0279 (2)0.134 (1)
S520.6475 (2)0.5002 (3)0.8758 (1)0.0232 (1)0.134 (1)
O120.0396 (2)0.3425 (4)0.5545 (1)0.035 (1)0.134 (1)
O221.0537 (2)0.6123 (4)0.9401 (1)0.035 (1)0.134 (1)
C0120.2304 (2)0.3943 (3)0.6247 (1)0.020 (1)0.134 (1)
C0220.1085 (2)0.4789 (4)0.6270 (1)0.022 (1)0.134 (1)
C0320.0575 (2)0.3622 (4)0.5794 (1)0.023 (1)0.134 (1)
C0420.1722 (2)0.2772 (4)0.5746 (1)0.021 (1)0.134 (1)
C0520.0985 (3)0.6601 (4)0.6088 (1)0.032 (1)0.134 (1)
C0620.0555 (3)0.4514 (4)0.6810 (1)0.036 (1)0.134 (1)
C0720.2079 (3)0.3103 (4)0.5167 (1)0.028 (1)0.134 (1)
C0820.1719 (3)0.0934 (4)0.5873 (1)0.031 (1)0.134 (1)
C0920.7826 (3)0.6019 (4)0.8691 (1)0.020 (1)0.134 (1)
C1020.8952 (3)0.4929 (4)0.8680 (1)0.022 (1)0.134 (1)
C1120.9539 (3)0.6002 (4)0.9168 (1)0.023 (1)0.134 (1)
C1220.8440 (3)0.6915 (4)0.9253 (1)0.021 (1)0.134 (1)
C1320.8862 (3)0.3138 (4)0.8877 (1)0.032 (1)0.134 (1)
C1420.9524 (3)0.4987 (5)0.8151 (1)0.036 (1)0.134 (1)
C1520.8014 (3)0.6334 (4)0.9799 (1)0.028 (1)0.134 (1)
C1620.8526 (3)0.8785 (4)0.9245 (1)0.031 (1)0.134 (1)
H510.13310.68900.06880.0320.732
H520.01420.71220.09560.0320.732
H530.14050.74780.13490.0320.732
H610.05590.35650.18900.0360.732
H620.09330.54420.20840.0360.732
H630.03310.50860.16920.0360.732
H710.20430.43860.00650.0280.732
H720.28230.27100.01490.0280.732
H730.14640.26280.01600.0280.732
H810.13840.09210.12410.0310.732
H820.10590.05020.05630.0310.732
H830.24180.05840.08710.0310.732
H1310.83890.32200.42170.0320.732
H1320.82860.25580.35640.0320.732
H1330.95590.27010.39680.0320.732
H1410.95440.61480.30070.0360.732
H1421.02610.44850.32320.0360.732
H1430.89880.43420.28280.0360.732
H1510.78870.52670.47770.0280.732
H1520.85190.68640.51100.0280.732
H1530.71790.69980.47780.0280.732
H1610.88010.92150.38480.0310.732
H1620.77370.94050.42090.0310.732
H1630.90770.92710.45420.0310.732
H5110.13340.67530.07360.0320.134
H5210.01470.69270.10090.0320.134
H5310.14090.73020.14000.0320.134
H6110.06290.33290.19210.0360.134
H6210.09770.52060.21260.0360.134
H6310.02850.48300.17350.0360.134
H7110.20730.43140.00950.0280.134
H7210.28780.26600.01660.0280.134
H7310.15180.25500.01390.0280.134
H8110.14830.07550.12530.0310.134
H8210.11550.03670.05730.0310.134
H8310.25160.04770.08770.0310.134
H13110.84860.31130.42240.0320.134
H13210.83830.24880.35660.0320.134
H13310.96580.26500.39680.0320.134
H14110.95790.61550.30260.0360.134
H14211.03220.45030.32400.0360.134
H14310.90470.43420.28390.0360.134
H15110.79620.51060.47980.0280.134
H15210.85740.67040.51400.0280.134
H15310.72290.68130.48120.0280.134
H16110.88030.91420.38890.0310.134
H16210.77430.92730.42560.0310.134
H16310.90880.91650.45840.0310.134
H5120.13340.67530.57360.0320.134
H5220.01470.69270.60090.0320.134
H5320.14090.73020.64000.0320.134
H6120.06290.33290.69210.0360.134
H6220.09770.52060.71260.0360.134
H6320.02850.48300.67350.0360.134
H7120.20730.43140.50950.0280.134
H7220.28780.26600.51660.0280.134
H7320.15180.25500.48610.0280.134
H8120.14830.07550.62530.0310.134
H8220.11550.03670.55730.0310.134
H8320.25160.04770.58770.0310.134
H13120.84860.31130.92240.0320.134
H13220.83830.24880.85660.0320.134
H13320.96580.26500.89680.0320.134
H14120.95790.61550.80260.0360.134
H14221.03220.45030.82400.0360.134
H14320.90470.43420.78390.0360.134
H15120.79620.51060.97980.0280.134
H15220.85740.67041.01400.0280.134
H15320.72290.68130.98120.0280.134
H16120.88030.91420.88890.0310.134
H16220.77430.92730.92560.0310.134
H16320.90880.91650.95840.0310.134
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL10.0278 (3)0.0336 (3)0.0352 (3)0.0097 (2)0.0053 (2)0.0042 (2)
CL20.0367 (3)0.0387 (4)0.0261 (3)0.0044 (3)0.0008 (2)0.0135 (2)
S10.0263 (3)0.0257 (3)0.0234 (3)0.0027 (2)0.0042 (2)0.0029 (2)
S20.0283 (3)0.0427 (4)0.0226 (3)0.0070 (3)0.0033 (2)0.0061 (3)
S30.0335 (4)0.0370 (4)0.0260 (3)0.0050 (3)0.0065 (3)0.0002 (3)
S40.0247 (3)0.0296 (4)0.0272 (3)0.0006 (3)0.0019 (2)0.0050 (2)
S50.0177 (3)0.0309 (3)0.0205 (3)0.0035 (2)0.0017 (2)0.0014 (2)
O10.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
O20.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
C10.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C20.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C30.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C40.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C50.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C60.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C70.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C80.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
C90.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C100.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C110.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C120.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C130.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C140.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C150.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C160.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
CL110.0278 (3)0.0336 (3)0.0352 (3)0.0097 (2)0.0053 (2)0.0042 (2)
CL210.0367 (3)0.0387 (4)0.0261 (3)0.0044 (3)0.0008 (2)0.0135 (2)
S110.0263 (3)0.0257 (3)0.0234 (3)0.0027 (2)0.0042 (2)0.0029 (2)
S210.0283 (3)0.0427 (4)0.0226 (3)0.0070 (3)0.0033 (2)0.0061 (3)
S310.0335 (4)0.0370 (4)0.0260 (3)0.0050 (3)0.0065 (3)0.0002 (3)
S410.0247 (3)0.0296 (4)0.0272 (3)0.0006 (3)0.0019 (2)0.0050 (2)
S510.0177 (3)0.0309 (3)0.0205 (3)0.0035 (2)0.0017 (2)0.0014 (2)
O110.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
O210.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
C0110.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C0210.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C0310.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C0410.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C0510.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C0610.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C0710.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C0810.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
C0910.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C1010.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C1110.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C1210.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C1310.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C1410.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C1510.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C1610.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
CL120.0278 (3)0.0336 (3)0.0352 (3)0.0097 (2)0.0053 (2)0.0042 (2)
CL220.0367 (3)0.0387 (4)0.0261 (3)0.0044 (3)0.0008 (2)0.0135 (2)
S120.0263 (3)0.0257 (3)0.0234 (3)0.0027 (2)0.0042 (2)0.0029 (2)
S220.0283 (3)0.0427 (4)0.0226 (3)0.0070 (3)0.0033 (2)0.0061 (3)
S320.0335 (4)0.0370 (4)0.0260 (3)0.0050 (3)0.0065 (3)0.0002 (3)
S420.0247 (3)0.0296 (4)0.0272 (3)0.0006 (3)0.0019 (2)0.0050 (2)
S520.0177 (3)0.0309 (3)0.0205 (3)0.0035 (2)0.0017 (2)0.0014 (2)
O120.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
O220.019 (1)0.036 (1)0.048 (1)0.004 (1)0.003 (1)0.005 (1)
C0120.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C0220.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C0320.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C0420.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C0520.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C0620.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C0720.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C0820.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
C0920.019 (1)0.021 (1)0.019 (1)0.000 (1)0.002 (1)0.004 (1)
C1020.022 (1)0.021 (1)0.025 (1)0.002 (1)0.004 (1)0.003 (1)
C1120.020 (1)0.019 (1)0.028 (1)0.002 (1)0.002 (1)0.002 (1)
C1220.017 (1)0.021 (1)0.023 (1)0.004 (1)0.001 (1)0.002 (1)
C1320.032 (1)0.021 (1)0.043 (1)0.003 (1)0.004 (1)0.000 (1)
C1420.036 (1)0.041 (1)0.034 (1)0.003 (1)0.016 (1)0.005 (1)
C1520.033 (1)0.031 (1)0.020 (1)0.011 (1)0.001 (1)0.002 (1)
C1620.028 (1)0.020 (1)0.040 (1)0.002 (1)0.005 (1)0.002 (1)
H510.0320.0210.0430.0030.0040.000
H520.0320.0210.0430.0030.0040.000
H530.0320.0210.0430.0030.0040.000
H610.0360.0410.0340.0030.0160.005
H620.0360.0410.0340.0030.0160.005
H630.0360.0410.0340.0030.0160.005
H710.0330.0310.0200.0110.0010.002
H720.0330.0310.0200.0110.0010.002
H730.0330.0310.0200.0110.0010.002
H810.0280.0200.0400.0020.0050.002
H820.0280.0200.0400.0020.0050.002
H830.0280.0200.0400.0020.0050.002
H1310.0320.0210.0430.0030.0040.000
H1320.0320.0210.0430.0030.0040.000
H1330.0320.0210.0430.0030.0040.000
H1410.0360.0410.0340.0030.0160.005
H1420.0360.0410.0340.0030.0160.005
H1430.0360.0410.0340.0030.0160.005
H1510.0330.0310.0200.0110.0010.002
H1520.0330.0310.0200.0110.0010.002
H1530.0330.0310.0200.0110.0010.002
H1610.0280.0200.0400.0020.0050.002
H1620.0280.0200.0400.0020.0050.002
H1630.0280.0200.0400.0020.0050.002
H5110.0320.0210.0430.0030.0040.000
H5210.0320.0210.0430.0030.0040.000
H5310.0320.0210.0430.0030.0040.000
H6110.0360.0410.0340.0030.0160.005
H6210.0360.0410.0340.0030.0160.005
H6310.0360.0410.0340.0030.0160.005
H7110.0330.0310.0200.0110.0010.002
H7210.0330.0310.0200.0110.0010.002
H7310.0330.0310.0200.0110.0010.002
H8110.0280.0200.0400.0020.0050.002
H8210.0280.0200.0400.0020.0050.002
H8310.0280.0200.0400.0020.0050.002
H13110.0320.0210.0430.0030.0040.000
H13210.0320.0210.0430.0030.0040.000
H13310.0320.0210.0430.0030.0040.000
H14110.0360.0410.0340.0030.0160.005
H14210.0360.0410.0340.0030.0160.005
H14310.0360.0410.0340.0030.0160.005
H15110.0330.0310.0200.0110.0010.002
H15210.0330.0310.0200.0110.0010.002
H15310.0330.0310.0200.0110.0010.002
H16110.0280.0200.0400.0020.0050.002
H16210.0280.0200.0400.0020.0050.002
H16310.0280.0200.0400.0020.0050.002
H5120.0320.0210.0430.0030.0040.000
H5220.0320.0210.0430.0030.0040.000
H5320.0320.0210.0430.0030.0040.000
H6120.0360.0410.0340.0030.0160.005
H6220.0360.0410.0340.0030.0160.005
H6320.0360.0410.0340.0030.0160.005
H7120.0330.0310.0200.0110.0010.002
H7220.0330.0310.0200.0110.0010.002
H7320.0330.0310.0200.0110.0010.002
H8120.0280.0200.0400.0020.0050.002
H8220.0280.0200.0400.0020.0050.002
H8320.0280.0200.0400.0020.0050.002
H13120.0320.0210.0430.0030.0040.000
H13220.0320.0210.0430.0030.0040.000
H13320.0320.0210.0430.0030.0040.000
H14120.0360.0410.0340.0030.0160.005
H14220.0360.0410.0340.0030.0160.005
H14320.0360.0410.0340.0030.0160.005
H15120.0330.0310.0200.0110.0010.002
H15220.0330.0310.0200.0110.0010.002
H15320.0330.0310.0200.0110.0010.002
H16120.0280.0200.0400.0020.0050.002
H16220.0280.0200.0400.0020.0050.002
H16320.0280.0200.0400.0020.0050.002
Geometric parameters (Å, º) top
S1—S22.038 (1)C3—C41.527 (3)
S4—S52.040 (1)C10—C111.522 (3)
S2—S32.061 (1)C11—C121.525 (3)
S3—S42.059 (1)C2—C51.535 (3)
S1—C11.817 (2)C2—C61.536 (3)
S5—C91.811 (2)C4—C71.531 (3)
CL1—C11.797 (2)C4—C81.525 (3)
CL2—C91.799 (2)C10—C131.539 (3)
C1—C21.589 (3)C10—C141.525 (3)
C1—C41.588 (3)C12—C151.542 (3)
C9—C101.589 (3)C12—C161.524 (3)
C9—C121.586 (3)S11—S212.038 (1)
O1—C31.197 (2)S41—S512.040 (1)
O2—C111.206 (2)S21—S312.061 (1)
C2—C31.522 (3)S31—S412.059 (1)
CL1—C1—S1108.0 (1)C1—C4—C7115.2 (2)
CL2—C9—S5108.2 (1)C9—C12—C16117.9 (2)
CL1—C1—C2114.1 (1)C1—C4—C8117.0 (2)
CL2—C9—C10112.2 (1)C9—C12—C15114.0 (2)
CL1—C1—C4114.5 (1)C3—C4—C7111.3 (2)
CL2—C9—C12112.0 (1)C11—C12—C16115.2 (2)
S1—C1—C2117.5 (1)C3—C4—C8113.4 (2)
S5—C9—C10118.7 (1)C11—C12—C15111.1 (2)
S1—C1—C4111.3 (1)C7—C4—C8111.2 (2)
S5—C9—C12114.3 (1)C15—C12—C16110.4 (2)
C2—C1—C490.8 (1)O1—C3—C2132.2 (2)
C10—C9—C1290.8 (1)O2—C11—C10132.4 (2)
C1—C2—C386.8 (1)O1—C3—C4132.1 (2)
C9—C10—C1186.2 (1)O2—C11—C12131.9 (2)
C1—C4—C386.7 (1)C2—C3—C495.8 (2)
C9—C12—C1186.2 (1)C10—C11—C1295.8 (2)
C1—C2—C5115.6 (2)S2—S1—C1102.7 (1)
C9—C10—C14118.3 (2)S4—S5—C9101.5 (1)
C1—C2—C6117.1 (2)S1—S2—S3107.1 (1)
C9—C10—C13115.1 (2)S3—S4—S5107.4 (1)
C3—C2—C5112.8 (2)S2—S3—S4105.5 (1)
C11—C10—C14114.3 (2)S21—S11—C011105.3 (1)
C3—C2—C6111.9 (2)S41—S51—C09199.5 (1)
C11—C10—C13110.8 (2)S11—S21—S31105.9 (2)
C5—C2—C6110.7 (2)S31—S41—S51107.8 (2)
C13—C10—C14110.1 (2)S21—S31—S41105.8 (2)
C1—S1—S2—S392.6 (1)C9—C10—C11—C127.8 (2)
C9—S5—S4—S391.8 (1)C2—C3—C4—C10.6 (2)
S1—S2—S3—S491.9 (1)C10—C11—C12—C97.8 (2)
S5—S4—S3—S294.1 (1)C3—C4—C1—C20.6 (1)
CL1—C1—S1—S261.6 (1)C11—C12—C9—C107.4 (1)
CL2—C9—S5—S463.3 (1)C4—C1—C2—C30.6 (1)
C2—C1—S1—S269.3 (2)C12—C9—C10—C117.4 (1)
C10—C9—S5—S465.9 (1)O1—C3—C2—C1178.8 (3)
C4—C1—S1—S2171.9 (1)O2—C11—C10—C9170.7 (2)
C12—C9—S5—S4171.2 (1)O1—C3—C4—C1178.8 (2)
C3—C2—C1—CL1118.0 (1)O2—C11—C12—C9170.7 (2)
C11—C10—C9—CL2106.7 (1)O1—C3—C2—C564.7 (3)
C5—C2—C1—CL14.2 (2)O2—C11—C10—C1451.2 (3)
C13—C10—C9—CL2142.0 (2)O1—C3—C4—C765.4 (3)
C6—C2—C1—CL1129.0 (2)O2—C11—C12—C1651.5 (3)
C14—C10—C9—CL28.9 (2)O1—C3—C2—C660.9 (3)
C3—C2—C1—S1114.1 (2)O2—C11—C10—C1373.9 (3)
C11—C10—C9—S5125.9 (1)O1—C3—C4—C860.8 (3)
C5—C2—C1—S1132.1 (2)O2—C11—C12—C1575.0 (3)
C13—C10—C9—S514.6 (2)C011—S11—S21—S3191.1 (2)
C6—C2—C1—S11.1 (3)C091—S51—S41—S3193.6 (2)
C14—C10—C9—S5118.5 (2)S11—S21—S31—S4198.4 (2)
C3—C4—C1—CL1117.7 (2)S51—S41—S31—S2188.1 (2)
C11—C12—C9—CL2106.9 (1)CL11—C011—S11—S2159.8 (1)
C7—C4—C1—CL15.7 (2)CL21—C091—S51—S4165.8 (1)
C15—C12—C9—CL2141.6 (2)C021—C011—S11—S2171.0 (2)
C8—C4—C1—CL1127.7 (2)C101—C091—S51—S4163.5 (2)
C16—C12—C9—CL29.6 (2)C041—C011—S11—S21173.7 (1)
C1—C2—C3—C40.6 (2)C121—C091—S51—S41168.8 (2)

Experimental details

(IV-a)(IV-b)
Crystal data
Chemical formulaC16H24Cl2O2S5C16H24Cl2O2S5
Mr479.57479.57
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)160160
a, b, c (Å)11.6666 (1), 8.1343 (1), 23.8366 (2)11.6666 (1), 8.1343 (1), 23.8366 (2)
β (°) 99.6985 (6) 99.6985 (6)
V3)2229.75 (4)2229.75 (4)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.770.77
Crystal size (mm)0.25 × 0.22 × 0.170.25 × 0.22 × 0.17
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Multi-scan
(Blessing, 1995)
Tmin, Tmax0.811, 0.8800.811, 0.880
No. of measured, independent and
observed reflections
53514, 6525, 4992 [I > 2σ(I)]53514, 6524, 4595 [I > 3σ(I)]
Rint0.0530.053
(sin θ/λ)max1)0.7040.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.086, 1.04 0.039, 0.059, 1.42
No. of reflections65234595
No. of parameters298188
No. of restraints0?
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.290.51, 0.78

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), RAELS00 (Rae, 2000), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003), RAELS00 and manual editing.

 

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