(1S*,2R*,2′R*) 2 Phenyl 1 phenyl­thio 1 (tetra­hydro­pyran 2 yl­thio)­propan 2 ol at 193 K

Acta Cryst.(2001). E57, o335±o337 DOI: 101107/S160053680100438X Jarno Kansikaset al. C₂₀H₂₄O₂S₂

o335

organic papers

Acta Crystallographica Section E

Structure Reports

Online ISSN 1600-5368

(1

S

*,2

R

*,2

_R

*)-2-Phenyl-1-phenylthio-1-(tetrahydro-pyran-2-ylthio)propan-2-ol at 193 K

Jarno Kansikasa_{* and Kaija SipilaÈ}b

a_{Department of Chemistry, Laboratory of}

Inor-ganic Chemistry, PO Box 55, 00014 University of Helsinki, Finland, andb_{Department of}

Chemistry, Laboratory of Organic Chemistry, PO Box 55, 00014 University of Helsinki, Finland

Correspondence e-mail: jarno.kansikas@helsinki.fi

Key indicators Single-crystal X-ray study

T= 193 K

Mean(C±C) = 0.004 AÊ

Rfactor = 0.046

wRfactor = 0.107

Data-to-parameter ratio = 15.8

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved

2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol, C20H24O2S2, was synthesized as a mixture of four diastereoisomers. An isomer which crystallizes in the centro-symmetric monoclinic space group P21/c with the relative con®guration (1S*,2R*,20_{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) AÊ] form zigzag chains in thec-axis direction. The tetrahydropyran ring has a chair conformation with an axial S-side chain.

Comment

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 tetra-hydropyran ring is C16 and thus the relative con®guration of the title compound may also be named (1S*,2R*,16R*), (I).

We have earlier reported the structure of another diaster-eoisomer (1S*,2S*,16R*), (II) (Kansikaset al., 1995). A very closely related compound 1-phenyl-2-phenylthio-2-(tetra-hydropyran-2-ylthio)ethanol, (C19H22O2S2), where the methyl group is replaced by an H atom, also forms four diastereoi-somers. 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 con®gurations (1S,2S,15R), (III) (Kansikas et al., 1996), (1R,2S,15S), (IV), and (1S,2S,15S), (V) (Kansikas & SipilaÈ, 2000). The fourth diastereoisomer crystallizes in a centro-symmetric space group with the relative con®guration (1R*,2S*,15R*), (VI) (SipilaÈ et al., 2001). Some interatomic distances, angles and torsion angles for (I) are listed in Table 1. The SÐC distances fall well within the values found in the compounds (II)±(VI), but the C1ÐS1ÐC4 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

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o336

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 tetra-hydropyran ring of the neighbouring molecule at the equiva-lent position (x, 1

2ÿy, zÿ12) (Fig. 2 and Table 2). A comparable intermolecular hydrogen bond, but between the molecules with the symmetry code (x,y, zÿ1), is found in the ethanol derivative (V). The O O distances are 2.751 (2) AÊ for (I) and 2.764 (3) AÊ for (V). The title isomer (I) crystallizes in the space groupP21/c(No. 14), whereas the ethanol deri-vative (IV) with the same relative con®guration 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).

Experimental

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 di-astereoisomers (1S*,2R*,20_R

*)-2-phenyl-1-phenylthio-1-(tetrahydro-pyran-2-ylthio)propan-2-ol, (I), and (1S*,2S*,20_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 diastereoi-somers (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-6A UV spec-trophotometric detector and a Shimadzu C-R6A Chromatopac. Components were monitored measuring the absorption at 254 nm. The column used was Merck Lichrocart Si 60 (25010 mm ID), 5mm, the mobile phase 2% ethyl acetate in dichloromethane; ¯ow rate 7 ml minÿ1_{. 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 measure-ments.1_{H NMR (200 MHz, CDCl}

3):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), 5.2±5.3 (1H,m, OCHS), 7.2±7.6 (10H,m; aromatic H).13_C NMR (50 MHz; CDCl3):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).

Crystal data

C20H24O2S2 Mr= 360.51

Monoclinic,P21/c a= 9.2440 (18) AÊ

b= 19.239 (4) AÊ

c= 10.682 (2) AÊ = 93.37 (3)

V= 1896.5 (6) AÊ3 Z= 4

Dx= 1.263 Mg mÿ3

MoKradiation Cell parameters from 25

re¯ections = 4±10

= 0.29 mmÿ1 T= 193 (2) K Prismatic, colourless 0.360.300.25 mm

Data collection

Rigaku AFC-7Sdiffractometer !/2scans

3637 measured re¯ections 3418 independent re¯ections 2438 re¯ections withI> 2(I)

Rint= 0.029

max= 25.3

h= 0!11

k= 0!23

l=ÿ12!12 3 standard re¯ections

every 100 re¯ections intensity decay: <0.1%

Re®nement

Re®nement onF2 R[F2_{> 2(F}2_{)] = 0.046} wR(F2_{) = 0.107} S= 1.05 3418 re¯ections 217 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0501P)2

+ 0.1099P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001 max= 0.28 e AÊÿ3 min=ÿ0.29 e AÊÿ3

Figure 1

View of (I) showing the crystallographic atom labelling. Displacement

ellipsoids are drawn at the 50% probability level. _{Figure 2}

Table 1

Selected geometric parameters (AÊ,_).

S1ÐC4 1.778 (3)

S1ÐC1 1.831 (2)

O1ÐC2 1.423 (3)

C1ÐC2 1.546 (3)

C1ÐS2 1.819 (2)

S2ÐC16 1.828 (2)

O2ÐC16 1.424 (3)

O2ÐC20 1.431 (3)

C4ÐS1ÐC1 99.20 (11)

C2ÐC1ÐS2 115.16 (17)

C2ÐC1ÐS1 108.91 (16)

S2ÐC1ÐS1 107.30 (12)

C1ÐS2ÐC16 101.66 (11)

C16ÐO2ÐC20 114.32 (19)

O1ÐC2ÐC1 104.76 (19)

O2ÐC16ÐS2 112.52 (16)

C4ÐS1ÐC1ÐC2 ÿ162.48 (17)

C4ÐS1ÐC1ÐS2 72.25 (15)

C2ÐC1ÐS2ÐC16 96.02 (18) S1ÐC1ÐS2ÐC16 ÿ142.57 (12)

S2ÐC1ÐC2ÐO1 66.0 (2)

S1ÐC1ÐC2ÐO1 ÿ54.5 (2) S2ÐC1ÐC2ÐC3 ÿ176.06 (17)

S1ÐC1ÐC2ÐC3 63.4 (2)

S1ÐC1ÐC2ÐC10 ÿ173.97 (16) C1ÐS2ÐC16ÐO2 67.04 (18)

Table 2

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

O1ÐH1A O2i _{0.84 1.92 2.751 (2) 168}

Symmetry codes: (i)x;1 2ÿy;zÿ12.

Data collection: AFC-7Ssoftware; cell re®nement: AFC-7S soft-ware; data reduction: TEXSAN(Molecular Structure Corporation, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:SHELXTL(Bruker, 1997); software used to prepare material for publication:SHELXL97.

References

Bruker (1997). SHELXTL. Release 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Kansikas, J., LeskelaÈ, M., SipilaÈ, K. & Hase, T. (1995).Acta Chem. Scand.49, 809±812.

Kansikas, J. & SipilaÈ, K. (2000).Acta Cryst.C56, 1383±1385.

Kansikas, J., SipilaÈ, K. & Hase, T. (1996). Acta Chem. Scand. 50, 1147± 1152.

Molecular Structure Corporation (1993).TEXSAN.Version 1.6b. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.

Sheldrick, G. M. (1997).SHELXS97 andSHELXL97. University of GoÈtt-ingen, Germany.

SipilaÈ, K., Hase, T., Kansikas, J. & Koskimies, J. (2001). Unpublished results.

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Acta Cryst. (2001). E57, o335–o337

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Acta Cryst. (2001). E57, o335–o337 [doi:10.1107/S160053680100438X]

(1

S

*,2

R

*,2

′

R

*)-2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol

at 193

K

Jarno Kansikas and Kaija Sipil

ä

S1. Comment

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-(tetrahydro-pyran-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

tetrahydro-pyran ring similar to (II) and (III).

S2. Experimental

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

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Acta Cryst. (2001). E57, o335–o337

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). 13_{C NMR (50 MHz; CDCl} 3): 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).

Figure 1

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Acta Cryst. (2001). E57, o335–o337

Figure 2

Fraction of the molecular packing showing the hydrogen-bond scheme of (I) in the c axis direction.

(I)

Crystal data

C20H24O2S2

Mr = 360.51 Monoclinic, P21/c

a = 9.2440 (18) Å

b = 19.239 (4) Å

c = 10.682 (2) Å

β = 93.37 (3)°

V = 1896.5 (6) Å3

Z = 4

F(000) = 768

Dx = 1.263 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections

θ = 4–10°

µ = 0.29 mm−1

T = 193 K

Prismatic, colourless 0.36 × 0.30 × 0.25 mm

Data collection

Rigaku AFC-7S diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω/2θ scans

3637 measured reflections 3418 independent reflections 2438 reflections with I > 2σ(I)

Rint = 0.029

θmax = 25.3°, θmin = 2.9°

h = 0→11

k = 0→23

l = −12→12

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Acta Cryst. (2001). E57, o335–o337

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.046}

wR(F2_{) = 0.107}

S = 1.05 3418 reflections 217 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0501P)2 + 0.1099P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Special details

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

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*

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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₎

U11 _U22 _U33 _U12 _U13 _U23

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Acta Cryst. (2001). E57, o335–o337

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)

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)

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sup-7

Acta Cryst. (2001). E57, o335–o337

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)

D—H···A D—H H···A D···A D—H···A

O1—H1A···O2i _{0.84 1.92 2.751 (2) 168}