Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100438X/om6010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680100438X/om6010Isup2.hkl |
CCDC reference: 162821
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.
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 |
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 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 |
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)° |
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) |
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 |
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. |
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* |
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) |
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) |
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 |
Computer programs: AFC-7S software, TEXSAN (Molecular Structure Corporation, 1993), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXL97.
S1—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) |
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. |
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).