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2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol, C
20H
24O
2S
2, was synthesized as a mixture of four diastereoisomers. An isomer which crystallizes in the centrosymmetric monoclinic space group
P2
1/
c with the relative configuration (1
S*,2
R*,2′R*) is presented. Intermolecular hydrogen bonds between the hydroxyl group and the O atom of the tetrahydropyran ring of a neighbouring molecule [O
O 2.751 (2) Å] form zigzag chains in the
c-axis direction. The tetrahydropyran ring has a chair conformation with an axial S-side chain.
Supporting information
CCDC reference: 162821
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.107
- Data-to-parameter ratio = 15.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol was synthesized as
a mixture of four diastereoisomers according to a procedure reported
previously (Kansikas et al., 1995). The diastereoisomers
(1S*,2R*,2'R*)-2-phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol, (I), and
(1S*,2S*,2'R*)-2-phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol, (II) (Kansikas et al., 1995), were separated by
high-pressure liquid chromatography (HPLC) from the crude product and
recrystallized from absolute ethanol. The relative amounts of the
diastereoisomers in elution order were: 31% (II) and 19% (I). The remaining
two diastereoisomers (50% of the total amount) could not be separated by this
procedure. HPLC separation was performed with an ISCO 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 Merck Lichrocart Si 60 (250 ×
10 mm ID), 5 µm, the mobile phase 2% ethyl acetate in dichloromethane; flow
rate 7 ml min-1. The NMR spectra were recorded on a Varian Gemini 200
spectrometer using tetramethylsilane as an internal standard. The assignments
are based on chemical-shift data and DEPT measurements. 1H NMR (200 MHz,
CDCl3): δ 1.4–1.9 (6H, m; CH2), 1.80 (s, CH3), 3.4–3.6 and
3.6–3.7 (2H, m; OCH2), 4.7 (1H, s, SCHS), 4.9 (1H, s,
OH), 5.5–5.3 (1H, m, OCHS), 7.2–7.6 (10H, m; arom·H).
13C NMR (50 MHz; CDCl3): δ 21.7 and 25.1 and 30.7 (CH2), 29.5 (CH3),
65.1 (OCH2), 68.5 (SCHS), 78.2 (CPh), 80.1 (OCS), 125.1–147.3 (aromatic C).
Data collection: AFC-7S software; cell refinement: AFC-7S software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
Crystal data top
C20H24O2S2 | F(000) = 768 |
Mr = 360.51 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2440 (18) Å | Cell parameters from 25 reflections |
b = 19.239 (4) Å | θ = 4–10° |
c = 10.682 (2) Å | µ = 0.29 mm−1 |
β = 93.37 (3)° | T = 193 K |
V = 1896.5 (6) Å3 | Prismatic, colourless |
Z = 4 | 0.36 × 0.30 × 0.25 mm |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.029 |
Radiation source: fine-focus sealed tube | θmax = 25.3°, θmin = 2.9° |
Graphite monochromator | h = 0→11 |
ω/2θ scans | k = 0→23 |
3637 measured reflections | l = −12→12 |
3418 independent reflections | 3 standard reflections every 100 reflections |
2438 reflections with I > 2σ(I) | intensity decay: <0.1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1099P] where P = (Fo2 + 2Fc2)/3 |
3418 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
C20H24O2S2 | V = 1896.5 (6) Å3 |
Mr = 360.51 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.2440 (18) Å | µ = 0.29 mm−1 |
b = 19.239 (4) Å | T = 193 K |
c = 10.682 (2) Å | 0.36 × 0.30 × 0.25 mm |
β = 93.37 (3)° | |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.029 |
3637 measured reflections | 3 standard reflections every 100 reflections |
3418 independent reflections | intensity decay: <0.1% |
2438 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.28 e Å−3 |
3418 reflections | Δρmin = −0.29 e Å−3 |
217 parameters | |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.61079 (7) | 0.30678 (4) | 0.07364 (6) | 0.0355 (2) | |
O1 | 0.39674 (19) | 0.21467 (9) | −0.04576 (15) | 0.0329 (4) | |
H1A | 0.3562 | 0.1792 | −0.0773 | 0.049* | |
C1 | 0.4319 (3) | 0.28763 (12) | 0.1302 (2) | 0.0252 (5) | |
H1B | 0.4395 | 0.2883 | 0.2239 | 0.030* | |
S2 | 0.31071 (7) | 0.35720 (3) | 0.07562 (6) | 0.02717 (17) | |
O2 | 0.2771 (2) | 0.39432 (9) | 0.31726 (15) | 0.0333 (4) | |
C2 | 0.3857 (3) | 0.21387 (13) | 0.0866 (2) | 0.0272 (6) | |
C3 | 0.4888 (3) | 0.15934 (14) | 0.1449 (3) | 0.0379 (7) | |
H3A | 0.4579 | 0.1130 | 0.1160 | 0.057* | |
H3B | 0.4875 | 0.1616 | 0.2365 | 0.057* | |
H3C | 0.5873 | 0.1684 | 0.1197 | 0.057* | |
C4 | 0.6601 (3) | 0.37767 (14) | 0.1741 (2) | 0.0320 (6) | |
C5 | 0.6929 (3) | 0.36759 (14) | 0.3006 (3) | 0.0360 (6) | |
H5A | 0.6862 | 0.3224 | 0.3358 | 0.043* | |
C6 | 0.7355 (3) | 0.42303 (15) | 0.3758 (3) | 0.0425 (7) | |
H6A | 0.7576 | 0.4160 | 0.4629 | 0.051* | |
C7 | 0.7461 (3) | 0.48869 (15) | 0.3253 (3) | 0.0427 (7) | |
H7A | 0.7761 | 0.5268 | 0.3772 | 0.051* | |
C8 | 0.7132 (3) | 0.49868 (15) | 0.1999 (3) | 0.0432 (7) | |
H8A | 0.7210 | 0.5438 | 0.1650 | 0.052* | |
C9 | 0.6686 (3) | 0.44362 (14) | 0.1235 (3) | 0.0368 (7) | |
H9A | 0.6440 | 0.4511 | 0.0370 | 0.044* | |
C10 | 0.2298 (3) | 0.20079 (12) | 0.1215 (2) | 0.0249 (5) | |
C11 | 0.1150 (3) | 0.21167 (14) | 0.0344 (2) | 0.0326 (6) | |
H11A | 0.1334 | 0.2230 | −0.0497 | 0.039* | |
C12 | −0.0263 (3) | 0.20616 (15) | 0.0692 (3) | 0.0419 (7) | |
H12A | −0.1040 | 0.2148 | 0.0091 | 0.050* | |
C13 | −0.0558 (3) | 0.18841 (15) | 0.1891 (3) | 0.0429 (7) | |
H13A | −0.1532 | 0.1852 | 0.2123 | 0.051* | |
C14 | 0.0581 (3) | 0.17519 (14) | 0.2764 (3) | 0.0365 (7) | |
H14A | 0.0390 | 0.1612 | 0.3591 | 0.044* | |
C15 | 0.1994 (3) | 0.18243 (13) | 0.2426 (2) | 0.0296 (6) | |
H15A | 0.2770 | 0.1747 | 0.3034 | 0.036* | |
C16 | 0.1978 (3) | 0.36796 (13) | 0.2092 (2) | 0.0280 (6) | |
H16A | 0.1601 | 0.3210 | 0.2310 | 0.034* | |
C17 | 0.0689 (3) | 0.41334 (14) | 0.1720 (3) | 0.0354 (6) | |
H17A | −0.0033 | 0.4099 | 0.2366 | 0.043* | |
H17B | 0.0228 | 0.3965 | 0.0917 | 0.043* | |
C18 | 0.1132 (3) | 0.48914 (14) | 0.1576 (3) | 0.0381 (7) | |
H18A | 0.1735 | 0.4941 | 0.0845 | 0.046* | |
H18B | 0.0257 | 0.5184 | 0.1429 | 0.046* | |
C19 | 0.1978 (3) | 0.51272 (14) | 0.2754 (3) | 0.0436 (7) | |
H19A | 0.1335 | 0.5131 | 0.3463 | 0.052* | |
H19B | 0.2336 | 0.5606 | 0.2636 | 0.052* | |
C20 | 0.3249 (3) | 0.46461 (14) | 0.3054 (3) | 0.0388 (7) | |
H20A | 0.3936 | 0.4676 | 0.2379 | 0.047* | |
H20B | 0.3765 | 0.4795 | 0.3848 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0289 (4) | 0.0361 (4) | 0.0426 (4) | −0.0044 (3) | 0.0115 (3) | −0.0118 (3) |
O1 | 0.0407 (11) | 0.0316 (10) | 0.0269 (9) | −0.0069 (8) | 0.0051 (8) | −0.0079 (7) |
C1 | 0.0232 (13) | 0.0273 (13) | 0.0252 (12) | 0.0006 (11) | 0.0036 (10) | −0.0018 (10) |
S2 | 0.0316 (4) | 0.0249 (3) | 0.0253 (3) | 0.0022 (3) | 0.0036 (3) | 0.0002 (3) |
O2 | 0.0419 (11) | 0.0317 (10) | 0.0263 (9) | 0.0086 (9) | 0.0011 (8) | 0.0008 (8) |
C2 | 0.0286 (14) | 0.0266 (14) | 0.0266 (13) | 0.0003 (11) | 0.0026 (11) | −0.0027 (10) |
C3 | 0.0352 (16) | 0.0291 (15) | 0.0494 (17) | 0.0053 (12) | 0.0028 (13) | −0.0003 (13) |
C4 | 0.0226 (13) | 0.0331 (15) | 0.0408 (15) | −0.0034 (11) | 0.0056 (12) | −0.0052 (12) |
C5 | 0.0343 (15) | 0.0297 (15) | 0.0438 (16) | −0.0028 (12) | 0.0002 (12) | 0.0025 (12) |
C6 | 0.0430 (17) | 0.0411 (17) | 0.0429 (17) | −0.0051 (14) | −0.0012 (14) | −0.0047 (14) |
C7 | 0.0336 (16) | 0.0357 (17) | 0.059 (2) | −0.0050 (13) | 0.0040 (14) | −0.0177 (14) |
C8 | 0.0376 (17) | 0.0299 (15) | 0.063 (2) | −0.0031 (13) | 0.0084 (15) | 0.0021 (14) |
C9 | 0.0334 (15) | 0.0349 (16) | 0.0429 (16) | −0.0053 (13) | 0.0080 (12) | 0.0029 (13) |
C10 | 0.0279 (13) | 0.0164 (12) | 0.0300 (13) | −0.0019 (10) | −0.0011 (11) | −0.0042 (10) |
C11 | 0.0341 (15) | 0.0342 (15) | 0.0290 (13) | −0.0005 (12) | −0.0027 (11) | −0.0025 (11) |
C12 | 0.0286 (15) | 0.0449 (18) | 0.0509 (18) | −0.0024 (13) | −0.0087 (13) | −0.0026 (14) |
C13 | 0.0291 (15) | 0.0401 (17) | 0.0602 (19) | −0.0096 (13) | 0.0091 (14) | −0.0063 (15) |
C14 | 0.0443 (17) | 0.0285 (15) | 0.0378 (15) | −0.0107 (13) | 0.0109 (13) | 0.0004 (12) |
C15 | 0.0329 (14) | 0.0239 (13) | 0.0316 (14) | −0.0033 (11) | −0.0011 (11) | 0.0007 (10) |
C16 | 0.0310 (14) | 0.0239 (13) | 0.0299 (13) | −0.0015 (11) | 0.0074 (11) | 0.0009 (10) |
C17 | 0.0261 (14) | 0.0385 (16) | 0.0418 (16) | 0.0026 (13) | 0.0029 (12) | −0.0037 (13) |
C18 | 0.0357 (16) | 0.0329 (16) | 0.0456 (16) | 0.0115 (13) | 0.0012 (13) | 0.0066 (13) |
C19 | 0.0459 (18) | 0.0239 (15) | 0.061 (2) | 0.0025 (13) | 0.0037 (15) | −0.0067 (14) |
C20 | 0.0420 (17) | 0.0331 (16) | 0.0402 (16) | 0.0013 (14) | −0.0059 (13) | −0.0103 (12) |
Geometric parameters (Å, º) top
S1—C4 | 1.778 (3) | C6—C7 | 1.380 (4) |
S1—C1 | 1.831 (2) | C7—C8 | 1.369 (4) |
O1—C2 | 1.423 (3) | C8—C9 | 1.385 (4) |
C1—C2 | 1.546 (3) | C10—C11 | 1.385 (3) |
C1—S2 | 1.819 (2) | C10—C15 | 1.386 (3) |
S2—C16 | 1.828 (2) | C11—C12 | 1.383 (4) |
O2—C16 | 1.424 (3) | C12—C13 | 1.367 (4) |
O2—C20 | 1.431 (3) | C13—C14 | 1.388 (4) |
C2—C3 | 1.525 (4) | C14—C15 | 1.383 (4) |
C2—C10 | 1.531 (3) | C16—C17 | 1.512 (3) |
C4—C5 | 1.381 (4) | C17—C18 | 1.525 (4) |
C4—C9 | 1.383 (4) | C18—C19 | 1.512 (4) |
C5—C6 | 1.379 (4) | C19—C20 | 1.515 (4) |
| | | |
C4—S1—C1 | 99.20 (11) | C7—C8—C9 | 120.7 (3) |
C2—C1—S2 | 115.16 (17) | C4—C9—C8 | 119.5 (3) |
C2—C1—S1 | 108.91 (16) | C11—C10—C15 | 118.4 (2) |
S2—C1—S1 | 107.30 (12) | C11—C10—C2 | 120.5 (2) |
C1—S2—C16 | 101.66 (11) | C15—C10—C2 | 121.0 (2) |
C16—O2—C20 | 114.32 (19) | C12—C11—C10 | 120.4 (3) |
O1—C2—C3 | 109.5 (2) | C13—C12—C11 | 120.9 (3) |
O1—C2—C10 | 111.5 (2) | C12—C13—C14 | 119.3 (3) |
C3—C2—C10 | 111.2 (2) | C15—C14—C13 | 119.8 (3) |
O1—C2—C1 | 104.76 (19) | C14—C15—C10 | 121.0 (2) |
C3—C2—C1 | 110.7 (2) | O2—C16—C17 | 111.6 (2) |
C10—C2—C1 | 108.95 (19) | O2—C16—S2 | 112.52 (16) |
C5—C4—C9 | 119.8 (2) | C17—C16—S2 | 109.73 (17) |
C5—C4—S1 | 121.1 (2) | C16—C17—C18 | 111.5 (2) |
C9—C4—S1 | 119.1 (2) | C19—C18—C17 | 109.4 (2) |
C6—C5—C4 | 120.0 (3) | C18—C19—C20 | 110.5 (2) |
C5—C6—C7 | 120.3 (3) | O2—C20—C19 | 110.9 (2) |
C8—C7—C6 | 119.6 (3) | | |
| | | |
C4—S1—C1—C2 | −162.48 (17) | C1—C2—C10—C11 | 96.1 (3) |
C4—S1—C1—S2 | 72.25 (15) | O1—C2—C10—C15 | 165.3 (2) |
C2—C1—S2—C16 | 96.02 (18) | C3—C2—C10—C15 | 42.7 (3) |
S1—C1—S2—C16 | −142.57 (12) | C1—C2—C10—C15 | −79.6 (3) |
S2—C1—C2—O1 | 66.0 (2) | C15—C10—C11—C12 | 1.8 (4) |
S1—C1—C2—O1 | −54.5 (2) | C2—C10—C11—C12 | −173.9 (2) |
S2—C1—C2—C3 | −176.06 (17) | C10—C11—C12—C13 | −1.5 (4) |
S1—C1—C2—C3 | 63.4 (2) | C11—C12—C13—C14 | −0.6 (4) |
S2—C1—C2—C10 | −53.4 (2) | C12—C13—C14—C15 | 2.2 (4) |
S1—C1—C2—C10 | −173.97 (16) | C13—C14—C15—C10 | −1.9 (4) |
C1—S1—C4—C5 | 70.4 (2) | C11—C10—C15—C14 | −0.1 (4) |
C1—S1—C4—C9 | −111.0 (2) | C2—C10—C15—C14 | 175.6 (2) |
C9—C4—C5—C6 | −0.7 (4) | C20—O2—C16—C17 | −55.7 (3) |
S1—C4—C5—C6 | 177.9 (2) | C20—O2—C16—S2 | 68.2 (2) |
C4—C5—C6—C7 | −0.3 (4) | C1—S2—C16—O2 | 67.04 (18) |
C5—C6—C7—C8 | 0.4 (5) | C1—S2—C16—C17 | −168.11 (18) |
C6—C7—C8—C9 | 0.3 (4) | O2—C16—C17—C18 | 52.9 (3) |
C5—C4—C9—C8 | 1.5 (4) | S2—C16—C17—C18 | −72.5 (2) |
S1—C4—C9—C8 | −177.1 (2) | C16—C17—C18—C19 | −53.0 (3) |
C7—C8—C9—C4 | −1.3 (4) | C17—C18—C19—C20 | 54.6 (3) |
O1—C2—C10—C11 | −19.1 (3) | C16—O2—C20—C19 | 57.6 (3) |
C3—C2—C10—C11 | −141.6 (2) | C18—C19—C20—O2 | −56.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.84 | 1.92 | 2.751 (2) | 168 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C20H24O2S2 |
Mr | 360.51 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 9.2440 (18), 19.239 (4), 10.682 (2) |
β (°) | 93.37 (3) |
V (Å3) | 1896.5 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.36 × 0.30 × 0.25 |
|
Data collection |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3637, 3418, 2438 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.600 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.107, 1.05 |
No. of reflections | 3418 |
No. of parameters | 217 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.29 |
Selected geometric parameters (Å, º) topS1—C4 | 1.778 (3) | C1—S2 | 1.819 (2) |
S1—C1 | 1.831 (2) | S2—C16 | 1.828 (2) |
O1—C2 | 1.423 (3) | O2—C16 | 1.424 (3) |
C1—C2 | 1.546 (3) | O2—C20 | 1.431 (3) |
| | | |
C4—S1—C1 | 99.20 (11) | C1—S2—C16 | 101.66 (11) |
C2—C1—S2 | 115.16 (17) | C16—O2—C20 | 114.32 (19) |
C2—C1—S1 | 108.91 (16) | O1—C2—C1 | 104.76 (19) |
S2—C1—S1 | 107.30 (12) | O2—C16—S2 | 112.52 (16) |
| | | |
C4—S1—C1—C2 | −162.48 (17) | S1—C1—C2—O1 | −54.5 (2) |
C4—S1—C1—S2 | 72.25 (15) | S2—C1—C2—C3 | −176.06 (17) |
C2—C1—S2—C16 | 96.02 (18) | S1—C1—C2—C3 | 63.4 (2) |
S1—C1—S2—C16 | −142.57 (12) | S1—C1—C2—C10 | −173.97 (16) |
S2—C1—C2—O1 | 66.0 (2) | C1—S2—C16—O2 | 67.04 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.84 | 1.92 | 2.751 (2) | 167.7 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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According to the crystallographic atomic labelling of 2-phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol (Fig. 1), the C atom bearing the S-side chain in the tetrahydropyran ring is C16 and thus the relative configuration of the title compound may also be named (1S*,2R*,16R*), (I). We have earlier reported the structure of another diastereoisomer (1S*,2S*,16R*), (II) (Kansikas et al., 1995). A very closely related compound 1-phenyl-2-phenylthio-2-(tetrahydropyran-2-ylthio)ethanol, (C19H22O2S2), where the methyl group is replaced by an H atom, also forms four diastereoisomers. Applying the above labelling scheme, atom C15 is now in the tetrahydropyran ring bonded to S. Three of the ethanol diastereoisomers crystallize in non-centrosymmetric space groups as conglomerates of enantiomeric crystals with the configurations (1S,2S,15R), (III) (Kansikas et al., 1996), (1R,2S,15S), (IV), and (1S,2S,15S), (V) (Kansikas and Sipilä, 2000). The fourth diastereoisomer crystallizes in a centrosymmetric space group with the relative configuration (1R*,2S*,15R*), (VI) (Sipilä et al., 2001). Some interatomic distances, angles and torsion angles for (I) are listed in Table 1. The S—C distances fall well within the values found in the compounds (II)–(VI), but the C1—S1—C4 angle of 99.21 (1)° is the smallest among them. Torsion angles around the S atoms in compounds (I)–(VI) vary considerably and that gives rise to very different appearances of these otherwise rather similar molecules. In the compound (I) the hydroxyl group forms an intermolecular hydrogen bond to the O atom of the tetrahydropyran ring of the neighbouring molecule at the equivalent position (x, 1/2 - y, z - 1/2) (Fig. 2 and Table 2). A comparable intermolecular hydrogen bond, but between the molecules with the symmetry code (x, y, z - 1), is found in the ethanol derivative (V). The O···O distances are 2.751 (2) Å for (I) and 2.764 (3) Å for (V). The title isomer (I) crystallizes in the space group P21/c (No. 14), whereas the ethanol derivative (IV) with the same relative configuration crystallizes in the non-centrosymmetric space group P212121 (No. 19) and possesses an intramolecular hydrogen bond between the hydroxyl group and the O atom of the tetrahydropyran ring similar to (II) and (III).