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In the synthesis of 1-phenyl-2-phenyl­thio-2-(tetra­hydro­pyran-2-yl­thio)­ethanol, C19H22O2S2, four diastereoisomers are formed. Two non-centrosymmetric enantiomeric forms which crystallize in space groups P212121 and Pna21 are presented. The former has an intramolecular hydrogen bond between the hydroxyl group and the O atom of the tetra­hydro­pyran ring. In the latter isomer, the hydroxyl group forms an intermolecular hydrogen bond to the O atom of the tetra­hydro­pyran­yl group of a neighbouring mol­ecule, joining the mol­ecules into chains in the c-axis direction; the O...O distances are 2.962 (4) and 2.764 (3) Å, respectively. The tetra­hydro­pyran rings are in chair conformations in both isomers and the S side chain has an equatorial orientation in the former, but an axial orientation in the latter mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011161/os1121sup1.cif
Contains datablocks I, II, etoh1068

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011161/os1121Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011161/os1121IIsup3.hkl
Contains datablock II

CCDC references: 153914; 153915

Computing details top

For both compounds, data collection: AFC7S Software (Molecular Structure Corporation, 1996); cell refinement: AFC7S Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C19H22O2S2Dx = 1.301 Mg m3
Mr = 346.49Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 5.3170 (11) Åθ = 4–10°
b = 16.642 (3) ŵ = 0.31 mm1
c = 19.998 (4) ÅT = 193 K
V = 1769.5 (6) Å3Prismatic, colourless
Z = 40.31 × 0.22 × 0.16 mm
F(000) = 736
Data collection top
Rigaku AFC7S
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 26.5°, θmin = 2.7°
Graphite monochromatorh = 06
ω/2θ scansk = 020
2057 measured reflectionsl = 024
2057 independent reflections3 standard reflections every 100 reflections
1850 reflections with I > 2σ(I) intensity decay: none
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.105Calculated w = 1/[σ2(Fo2) + (0.0549P)2 + 0.7649P]
where P = (Fo2 + 2Fc2)/3'
S = 1.03(Δ/σ)max < 0.001
2057 reflectionsΔρmax = 0.29 e Å3
208 parametersΔρmin = 0.22 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.22 (13)
Special details top

Experimental. The HPLC separation experiments were performed with an ISCO model 2350 liquid chromatograph equipped with a Shimadzu SPD-6 A UV spectrophotometric detector and a Shimadzu C—R6A Chromatopac. Components were monitored measuring the absorption at 254 nm. The column used was Lichrocart Si 60 (250 × 10 mm ID), 5 µm. The mobile phase was 2% ethyl acetate in dichloromethane; flow rate, 7 ml min-1.

1H, 13C and DEPT spectra were taken for samples in CDCl3 with a Varian Gemini 200 and the HMQC spectra with Varian INOVA 300 spectrometer with SiMe4 as an internal reference. The assigments are based on chemical shift data and DEPT and HMQC measurements. The melting points were determined in an open capillary tube with an Electrothermal apparatus and are uncorrected.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.26462 (17)0.47735 (5)0.00516 (4)0.0363 (2)
S20.88768 (19)0.60495 (5)0.04884 (4)0.0384 (2)
O10.7835 (7)0.48305 (15)0.15859 (12)0.0597 (9)
H1A0.80640.53030.17210.090*
O21.0779 (6)0.63379 (14)0.16727 (12)0.0482 (7)
C10.9723 (6)0.49922 (18)0.04820 (15)0.0304 (7)
H1B0.83630.47050.02320.036*
C20.9880 (8)0.45946 (19)0.11838 (15)0.0366 (8)
H2A1.14790.47660.14050.044*
C31.1852 (6)0.50034 (18)0.07910 (14)0.0308 (7)
C41.3445 (8)0.5496 (2)0.11490 (17)0.0402 (8)
H4A1.48590.57350.09380.048*
C51.2957 (9)0.5638 (2)0.18224 (19)0.0496 (10)
H5A1.40790.59620.20760.060*
C61.0872 (8)0.5315 (2)0.21240 (16)0.0439 (9)
H6A1.05220.54280.25800.053*
C70.9292 (8)0.4827 (2)0.17626 (17)0.0437 (9)
H7A0.78460.46030.19700.052*
C80.9795 (7)0.4658 (2)0.10961 (16)0.0392 (8)
H8A0.87280.43070.08520.047*
C90.9842 (7)0.36797 (19)0.11338 (16)0.0351 (8)
C100.7932 (8)0.3282 (2)0.0798 (2)0.0482 (10)
H10A0.66190.35780.05910.058*
C110.7943 (9)0.2447 (2)0.0765 (2)0.0530 (10)
H11A0.66580.21760.05240.064*
C120.9786 (8)0.2013 (2)0.1076 (2)0.0481 (10)
H12A0.97450.14420.10630.058*
C131.1693 (9)0.2400 (2)0.1406 (2)0.0536 (11)
H13A1.29920.20980.16150.064*
C141.1722 (8)0.3240 (2)0.14358 (17)0.0427 (9)
H14A1.30430.35090.16650.051*
C151.1346 (8)0.6476 (2)0.09864 (17)0.0384 (8)
H15A1.29740.62080.08730.046*
C161.1559 (9)0.7374 (2)0.08451 (18)0.0495 (10)
H16A1.20220.74600.03710.059*
H16B0.99180.76380.09270.059*
C171.3556 (10)0.7739 (2)0.1299 (2)0.0594 (11)
H17A1.52330.75370.11660.071*
H17B1.35560.83310.12450.071*
C181.3075 (11)0.7532 (2)0.2021 (2)0.0634 (13)
H18A1.15390.78100.21780.076*
H18B1.45050.77150.22990.076*
C191.2748 (12)0.6630 (2)0.2097 (2)0.0631 (14)
H19A1.43440.63570.19820.076*
H19B1.23440.65030.25680.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0327 (4)0.0421 (4)0.0340 (4)0.0067 (4)0.0005 (4)0.0015 (4)
S20.0409 (5)0.0312 (4)0.0431 (4)0.0064 (4)0.0027 (4)0.0017 (3)
O10.089 (2)0.0382 (13)0.0519 (14)0.0061 (18)0.0324 (17)0.0001 (12)
O20.072 (2)0.0333 (12)0.0394 (12)0.0010 (15)0.0013 (15)0.0010 (10)
C10.0284 (16)0.0301 (15)0.0327 (15)0.0046 (14)0.0016 (14)0.0008 (13)
C20.050 (2)0.0276 (16)0.0323 (15)0.0022 (17)0.0043 (17)0.0010 (13)
C30.0342 (18)0.0276 (14)0.0306 (14)0.0073 (14)0.0028 (13)0.0019 (12)
C40.039 (2)0.0384 (18)0.0428 (17)0.0074 (17)0.0002 (17)0.0015 (15)
C50.059 (3)0.043 (2)0.0464 (18)0.006 (2)0.010 (2)0.0096 (16)
C60.054 (2)0.0451 (19)0.0325 (15)0.004 (2)0.0005 (18)0.0005 (15)
C70.045 (2)0.048 (2)0.0381 (16)0.003 (2)0.0038 (17)0.0099 (16)
C80.040 (2)0.0385 (18)0.0396 (17)0.0101 (17)0.0044 (17)0.0017 (14)
C90.043 (2)0.0299 (16)0.0326 (15)0.0017 (16)0.0030 (16)0.0008 (13)
C100.039 (2)0.0381 (19)0.067 (2)0.0046 (19)0.008 (2)0.0081 (17)
C110.045 (2)0.043 (2)0.072 (2)0.008 (2)0.007 (2)0.0025 (18)
C120.052 (2)0.0294 (17)0.063 (2)0.0003 (18)0.002 (2)0.0012 (17)
C130.062 (3)0.0367 (19)0.062 (2)0.007 (2)0.008 (2)0.0010 (18)
C140.052 (3)0.0338 (17)0.0424 (17)0.0026 (18)0.0079 (19)0.0009 (14)
C150.041 (2)0.0314 (16)0.0426 (17)0.0022 (17)0.0024 (18)0.0012 (14)
C160.061 (3)0.0361 (18)0.051 (2)0.006 (2)0.004 (2)0.0064 (16)
C170.057 (3)0.039 (2)0.082 (3)0.001 (2)0.014 (3)0.002 (2)
C180.082 (4)0.040 (2)0.069 (3)0.001 (2)0.021 (3)0.0125 (19)
C190.097 (4)0.039 (2)0.053 (2)0.010 (3)0.022 (3)0.0084 (17)
Geometric parameters (Å, º) top
S1—C31.779 (3)C6—C71.374 (5)
S1—C11.814 (3)C7—C81.388 (5)
S2—C151.794 (4)C9—C141.378 (5)
S2—C11.816 (3)C9—C101.386 (5)
O1—C21.408 (5)C10—C111.391 (5)
O2—C151.424 (4)C11—C121.367 (6)
O2—C191.433 (5)C12—C131.371 (6)
C1—C21.554 (4)C13—C141.400 (5)
C2—C91.526 (4)C15—C161.525 (5)
C3—C81.378 (5)C16—C171.523 (6)
C3—C41.379 (5)C17—C181.508 (6)
C4—C51.392 (5)C18—C191.518 (5)
C5—C61.372 (6)
C3—S1—C1101.71 (15)C3—C8—C7119.6 (3)
C15—S2—C1101.86 (16)C14—C9—C10119.4 (3)
C15—O2—C19111.2 (3)C14—C9—C2119.4 (3)
C2—C1—S1107.3 (2)C10—C9—C2121.2 (3)
C2—C1—S2114.8 (2)C9—C10—C11119.8 (4)
S1—C1—S2114.20 (17)C12—C11—C10120.6 (4)
O1—C2—C9107.8 (3)C11—C12—C13120.1 (4)
O1—C2—C1110.8 (3)C12—C13—C14119.9 (4)
C9—C2—C1111.4 (3)C9—C14—C13120.2 (4)
C8—C3—C4120.4 (3)O2—C15—C16110.6 (3)
C8—C3—S1121.2 (3)O2—C15—S2108.4 (3)
C4—C3—S1118.3 (3)C16—C15—S2109.8 (3)
C3—C4—C5119.3 (4)C17—C16—C15109.4 (3)
C6—C5—C4120.6 (4)C18—C17—C16111.2 (4)
C5—C6—C7119.6 (3)C17—C18—C19110.0 (3)
C6—C7—C8120.5 (4)O2—C19—C18111.1 (4)
C3—S1—C1—C2164.2 (2)O1—C2—C9—C1067.3 (4)
C3—S1—C1—S267.4 (2)C1—C2—C9—C1054.5 (5)
C15—S2—C1—C258.9 (3)C14—C9—C10—C110.5 (6)
C15—S2—C1—S165.6 (2)C2—C9—C10—C11179.6 (4)
S1—C1—C2—O1171.7 (2)C9—C10—C11—C121.7 (7)
S2—C1—C2—O143.6 (4)C10—C11—C12—C132.1 (6)
S1—C1—C2—C968.3 (3)C11—C12—C13—C141.3 (6)
S2—C1—C2—C9163.6 (3)C10—C9—C14—C130.4 (6)
C1—S1—C3—C854.0 (3)C2—C9—C14—C13178.8 (3)
C1—S1—C3—C4130.3 (3)C12—C13—C14—C90.0 (6)
C8—C3—C4—C50.2 (5)C19—O2—C15—C1662.4 (4)
S1—C3—C4—C5175.5 (3)C19—O2—C15—S2177.2 (2)
C3—C4—C5—C62.1 (6)C1—S2—C15—O280.0 (3)
C4—C5—C6—C72.0 (6)C1—S2—C15—C16159.1 (3)
C5—C6—C7—C80.1 (6)O2—C15—C16—C1757.1 (5)
C4—C3—C8—C71.8 (5)S2—C15—C16—C17176.8 (3)
S1—C3—C8—C7177.4 (3)C15—C16—C17—C1852.5 (5)
C6—C7—C8—C32.0 (6)C16—C17—C18—C1952.1 (6)
O1—C2—C9—C14111.8 (4)C15—O2—C19—C1861.9 (5)
C1—C2—C9—C14126.4 (4)C17—C18—C19—O256.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.842.252.962 (4)143
(II) top
Crystal data top
C19H22O2S2Dx = 1.326 Mg m3
Mr = 346.49Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 25 reflections
a = 16.699 (3) Åθ = 4–10°
b = 18.507 (4) ŵ = 0.31 mm1
c = 5.6150 (11) ÅT = 193 K
V = 1735.3 (6) Å3Prismatic, colourless
Z = 40.38 × 0.26 × 0.22 mm
F(000) = 736
Data collection top
Rigaku AFC7S
diffractometer
Rint = 0.070
Radiation source: fine-focus sealed tubeθmax = 26.5°, θmin = 2.5°
Graphite monochromatorh = 2020
ω/2θ scansk = 2323
7318 measured reflectionsl = 07
1955 independent reflections3 standard reflections every 100 reflections
1842 reflections with I > 2σ(I) intensity decay: none
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083Calculated w = 1/[σ2(Fo2) + (0.0535P)2 + 0.1178P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1955 reflectionsΔρmax = 0.25 e Å3
212 parametersΔρmin = 0.43 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (8)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.23623 (4)0.70736 (3)0.17049 (13)0.03011 (16)
S20.38132 (4)0.64424 (3)0.39707 (13)0.02748 (16)
O10.37724 (12)0.79253 (10)0.0716 (4)0.0320 (5)
H1B0.4084 (19)0.7668 (18)0.035 (8)0.046 (10)*
O20.46600 (11)0.71428 (8)0.7459 (3)0.0290 (4)
C10.31414 (13)0.72258 (11)0.3906 (5)0.0245 (5)
H1C0.28920.72920.55110.029*
C20.35963 (15)0.79237 (12)0.3199 (5)0.0252 (5)
H2A0.41120.79400.41010.030*
C30.16364 (14)0.65281 (11)0.3183 (5)0.0242 (5)
C40.17452 (15)0.61730 (13)0.5342 (5)0.0285 (5)
H4B0.22350.62190.61890.034*
C50.11303 (15)0.57505 (14)0.6243 (5)0.0346 (6)
H5A0.12040.55050.77130.041*
C60.04094 (16)0.56805 (14)0.5035 (6)0.0378 (6)
H6A0.00090.53930.56770.045*
C70.03066 (16)0.60348 (13)0.2885 (6)0.0339 (6)
H7B0.01830.59860.20380.041*
C80.09133 (15)0.64597 (12)0.1964 (5)0.0300 (6)
H8B0.08370.67060.04960.036*
C90.31300 (14)0.86086 (11)0.3734 (5)0.0240 (5)
C100.26004 (14)0.89072 (13)0.2068 (5)0.0286 (5)
H10C0.25100.86700.05920.034*
C110.22089 (16)0.95500 (14)0.2578 (6)0.0338 (6)
H11C0.18470.97490.14510.041*
C120.23407 (16)0.99016 (14)0.4702 (6)0.0357 (7)
H12B0.20761.03450.50220.043*
C130.28526 (16)0.96144 (13)0.6358 (5)0.0356 (6)
H13B0.29360.98560.78290.043*
C140.32537 (16)0.89631 (13)0.5884 (5)0.0296 (6)
H14B0.36090.87650.70330.036*
C150.42028 (15)0.65086 (12)0.7034 (5)0.0262 (5)
H15B0.37280.65300.81180.031*
C160.46675 (16)0.58295 (13)0.7683 (6)0.0346 (6)
H16B0.47220.58020.94360.041*
H16C0.43620.54000.71500.041*
C170.54955 (15)0.58140 (13)0.6559 (7)0.0382 (6)
H17B0.54450.57550.48130.046*
H17C0.58010.53970.71870.046*
C180.59453 (16)0.65137 (15)0.7110 (7)0.0403 (7)
H18C0.60550.65480.88390.048*
H18D0.64630.65220.62500.048*
C190.54267 (15)0.71439 (13)0.6321 (5)0.0324 (6)
H19A0.57060.76020.66930.039*
H19B0.53510.71200.45740.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0326 (3)0.0331 (3)0.0247 (3)0.0056 (2)0.0049 (3)0.0032 (3)
S20.0314 (3)0.0225 (3)0.0286 (3)0.0036 (2)0.0006 (3)0.0045 (3)
O10.0367 (11)0.0294 (9)0.0298 (10)0.0070 (8)0.0112 (9)0.0004 (8)
O20.0349 (9)0.0249 (8)0.0272 (9)0.0041 (7)0.0015 (8)0.0063 (7)
C10.0269 (11)0.0226 (10)0.0240 (11)0.0027 (8)0.0024 (11)0.0020 (10)
C20.0264 (12)0.0246 (11)0.0247 (12)0.0014 (9)0.0011 (10)0.0004 (10)
C30.0267 (12)0.0189 (10)0.0269 (12)0.0005 (8)0.0003 (10)0.0032 (10)
C40.0330 (13)0.0271 (12)0.0253 (12)0.0054 (10)0.0037 (11)0.0021 (11)
C50.0409 (14)0.0296 (12)0.0331 (15)0.0063 (10)0.0034 (12)0.0036 (12)
C60.0355 (14)0.0287 (13)0.0492 (17)0.0020 (10)0.0081 (14)0.0006 (13)
C70.0290 (13)0.0285 (12)0.0443 (16)0.0009 (10)0.0066 (12)0.0069 (12)
C80.0341 (13)0.0257 (12)0.0301 (14)0.0030 (9)0.0035 (12)0.0030 (11)
C90.0266 (11)0.0207 (10)0.0245 (12)0.0022 (8)0.0030 (10)0.0015 (10)
C100.0322 (12)0.0287 (11)0.0251 (14)0.0017 (9)0.0019 (11)0.0002 (11)
C110.0360 (13)0.0311 (13)0.0344 (14)0.0061 (10)0.0025 (12)0.0071 (11)
C120.0412 (15)0.0226 (12)0.0434 (17)0.0013 (10)0.0184 (13)0.0005 (12)
C130.0507 (15)0.0283 (12)0.0278 (14)0.0076 (11)0.0107 (13)0.0065 (11)
C140.0370 (14)0.0308 (12)0.0210 (12)0.0042 (10)0.0022 (10)0.0010 (10)
C150.0261 (12)0.0259 (11)0.0267 (12)0.0022 (8)0.0024 (10)0.0013 (10)
C160.0362 (14)0.0286 (12)0.0389 (15)0.0002 (10)0.0033 (13)0.0086 (12)
C170.0371 (13)0.0287 (12)0.0490 (16)0.0101 (10)0.0005 (15)0.0048 (13)
C180.0273 (13)0.0441 (16)0.0496 (19)0.0008 (10)0.0027 (13)0.0059 (14)
C190.0355 (13)0.0297 (12)0.0319 (14)0.0087 (9)0.0049 (12)0.0031 (11)
Geometric parameters (Å, º) top
S1—C31.783 (2)C6—C71.385 (5)
S1—C11.816 (3)C7—C81.383 (4)
S2—C11.834 (2)C9—C141.389 (4)
S2—C151.843 (3)C9—C101.401 (4)
O1—C21.425 (3)C10—C111.387 (4)
O2—C151.420 (3)C11—C121.376 (4)
O2—C191.431 (3)C12—C131.370 (4)
C1—C21.550 (3)C13—C141.404 (3)
C2—C91.518 (3)C15—C161.521 (3)
C3—C41.391 (4)C16—C171.520 (4)
C3—C81.394 (4)C17—C181.529 (4)
C4—C51.386 (4)C18—C191.519 (4)
C5—C61.388 (4)
C3—S1—C1104.95 (12)C7—C8—C3120.2 (3)
C1—S2—C15100.48 (12)C14—C9—C10119.2 (2)
C15—O2—C19114.04 (18)C14—C9—C2119.3 (2)
C2—C1—S1107.81 (18)C10—C9—C2121.4 (2)
C2—C1—S2111.34 (16)C11—C10—C9119.9 (3)
S1—C1—S2109.22 (12)C12—C11—C10120.6 (3)
O1—C2—C9107.3 (2)C13—C12—C11120.3 (2)
O1—C2—C1110.7 (2)C12—C13—C14120.1 (3)
C9—C2—C1113.2 (2)C9—C14—C13119.9 (2)
C4—C3—C8119.9 (2)O2—C15—C16111.6 (2)
C4—C3—S1125.77 (19)O2—C15—S2113.66 (17)
C8—C3—S1114.3 (2)C16—C15—S2110.40 (18)
C3—C4—C5119.2 (2)C17—C16—C15112.4 (2)
C6—C5—C4121.1 (3)C16—C17—C18110.3 (2)
C5—C6—C7119.3 (3)C19—C18—C17108.1 (2)
C8—C7—C6120.3 (3)O2—C19—C18112.3 (2)
C3—S1—C1—C2156.81 (15)O1—C2—C9—C1033.5 (3)
C3—S1—C1—S282.08 (15)C1—C2—C9—C1088.9 (3)
C15—S2—C1—C286.5 (2)C14—C9—C10—C110.1 (4)
C15—S2—C1—S1154.53 (13)C2—C9—C10—C11177.3 (2)
S1—C1—C2—O145.4 (2)C9—C10—C11—C120.5 (4)
S2—C1—C2—O174.4 (3)C10—C11—C12—C131.0 (4)
S1—C1—C2—C975.2 (2)C11—C12—C13—C140.8 (4)
S2—C1—C2—C9165.03 (19)C10—C9—C14—C130.3 (3)
C1—S1—C3—C412.9 (2)C2—C9—C14—C13177.2 (2)
C1—S1—C3—C8168.43 (18)C12—C13—C14—C90.1 (4)
C8—C3—C4—C50.4 (3)C19—O2—C15—C1654.1 (3)
S1—C3—C4—C5178.25 (19)C19—O2—C15—S271.6 (2)
C3—C4—C5—C60.4 (4)C1—S2—C15—O264.06 (18)
C4—C5—C6—C70.5 (4)C1—S2—C15—C16169.66 (17)
C5—C6—C7—C80.7 (4)O2—C15—C16—C1750.8 (3)
C6—C7—C8—C30.7 (4)S2—C15—C16—C1776.7 (3)
C4—C3—C8—C70.6 (4)C15—C16—C17—C1852.1 (4)
S1—C3—C8—C7178.24 (19)C16—C17—C18—C1954.3 (4)
O1—C2—C9—C14143.9 (2)C15—O2—C19—C1859.2 (3)
C1—C2—C9—C1493.6 (3)C17—C18—C19—O257.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.74 (3)2.12 (4)2.764 (3)146 (4)
Symmetry code: (i) x, y, z1.
 

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