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The title compound, C20H20OS2, crystallizes in the monoclinic space group P21/c. The S-side chain at the 2-position of the tetra­hydro­pyran (THP) group is axial with a C-O-C-S torsion angle of 66.77 (19)°. The C-S-C-S torsion angle at the THP side of the di­thio­acetal group is 78.31 (12)° and at the phenanthrene side is -176.73 (10)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006542/cv6107sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006542/cv6107Isup2.hkl
Contains datablock I

CCDC reference: 189313

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.099
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: WinGX (Farrugia, 1999); 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.

2-(phenanthren-9-ylthiomethylthio)tetrahydropyran top
Crystal data top
C20H20OS2F(000) = 720
Mr = 340.48Dx = 1.344 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
a = 12.793 (3) ÅCell parameters from 25 reflections
b = 14.890 (3) Åθ = 4–12°
c = 8.9570 (18) ŵ = 2.87 mm1
β = 99.42 (3)°T = 193 K
V = 1683.2 (6) Å3Prism, colourless
Z = 40.21 × 0.20 × 0.19 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.065
Radiation source: fine-focus sealed tubeθmax = 67.8°, θmin = 3.5°
Graphite monochromatorh = 1515
ω/2θ scansk = 117
5817 measured reflectionsl = 1010
2995 independent reflections3 standard reflections every 100 reflections
2427 reflections with I > 2σ(I) intensity decay: none
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.5652P]
where P = (Fo2 + 2Fc2)/3
2995 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
O0.86501 (11)0.81451 (9)0.45082 (15)0.0448 (3)
S10.72832 (4)1.04354 (4)0.31959 (6)0.04932 (16)
C10.34993 (18)0.92378 (15)0.1111 (2)0.0481 (5)
H1A0.38250.88190.05330.058*
S20.89634 (4)0.93130 (4)0.22843 (6)0.04928 (17)
C20.24204 (19)0.92351 (16)0.1017 (3)0.0539 (6)
H2A0.20010.88180.03760.065*
C30.19404 (18)0.98479 (16)0.1867 (3)0.0533 (6)
H3A0.11910.98520.17920.064*
C40.25368 (17)1.04420 (15)0.2804 (2)0.0464 (5)
H4A0.21941.08450.33890.056*
C50.38945 (19)1.17406 (14)0.4789 (2)0.0487 (5)
H5A0.31481.17860.47280.058*
C60.4540 (2)1.23054 (15)0.5733 (3)0.0587 (6)
H6A0.42351.27380.63120.070*
C70.5632 (2)1.22525 (15)0.5852 (2)0.0556 (6)
H7A0.60731.26390.65260.067*
C80.60745 (19)1.16391 (14)0.4993 (2)0.0470 (5)
H8A0.68231.16090.50710.056*
C90.58913 (16)1.04156 (13)0.3063 (2)0.0382 (4)
C100.52523 (16)0.98509 (14)0.2134 (2)0.0416 (5)
H10A0.55630.94420.15190.050*
C110.41325 (16)0.98521 (13)0.2053 (2)0.0385 (4)
C120.36497 (16)1.04736 (13)0.2927 (2)0.0368 (4)
C130.43170 (16)1.10909 (13)0.3902 (2)0.0379 (4)
C140.54329 (16)1.10551 (13)0.3998 (2)0.0375 (4)
C150.75555 (17)0.94369 (15)0.2172 (2)0.0466 (5)
H15A0.72610.89030.26150.056*
H15B0.72160.94870.11000.056*
C160.93230 (16)0.88494 (14)0.4210 (2)0.0435 (5)
H16A0.92600.93440.49450.052*
C170.87337 (18)0.73456 (15)0.3628 (2)0.0508 (5)
H17A0.84970.74820.25440.061*
H17B0.82580.68780.39280.061*
C180.98513 (19)0.69871 (15)0.3841 (3)0.0513 (5)
H18A0.98870.64730.31500.062*
H18B1.00570.67700.48930.062*
C191.06218 (17)0.77151 (15)0.3518 (2)0.0499 (5)
H19A1.04950.78610.24240.060*
H19B1.13590.74950.37900.060*
C201.04724 (17)0.85562 (15)0.4433 (2)0.0472 (5)
H20A1.07200.84350.55200.057*
H20B1.09100.90490.41210.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0485 (8)0.0413 (8)0.0471 (7)0.0018 (6)0.0155 (6)0.0001 (6)
S10.0397 (3)0.0543 (3)0.0528 (3)0.0021 (2)0.0040 (2)0.0063 (2)
C10.0538 (13)0.0426 (12)0.0466 (11)0.0026 (10)0.0044 (9)0.0044 (9)
S20.0436 (3)0.0556 (3)0.0506 (3)0.0097 (2)0.0137 (2)0.0117 (2)
C20.0519 (13)0.0543 (14)0.0527 (12)0.0134 (11)0.0000 (10)0.0044 (10)
C30.0421 (12)0.0619 (15)0.0558 (12)0.0044 (10)0.0082 (10)0.0152 (11)
C40.0457 (12)0.0479 (12)0.0479 (11)0.0044 (9)0.0143 (9)0.0112 (9)
C50.0623 (14)0.0393 (12)0.0486 (11)0.0072 (10)0.0213 (10)0.0016 (9)
C60.0898 (19)0.0393 (13)0.0522 (12)0.0059 (12)0.0269 (12)0.0068 (10)
C70.0849 (18)0.0373 (12)0.0448 (11)0.0098 (11)0.0114 (11)0.0058 (9)
C80.0584 (13)0.0410 (12)0.0406 (10)0.0071 (10)0.0054 (9)0.0017 (9)
C90.0394 (10)0.0379 (11)0.0374 (9)0.0037 (8)0.0066 (8)0.0028 (8)
C100.0460 (11)0.0399 (11)0.0393 (10)0.0057 (9)0.0079 (8)0.0041 (8)
C110.0441 (11)0.0336 (11)0.0371 (9)0.0011 (8)0.0049 (8)0.0037 (8)
C120.0441 (11)0.0319 (10)0.0350 (9)0.0032 (8)0.0086 (8)0.0078 (8)
C130.0497 (11)0.0311 (10)0.0345 (9)0.0038 (8)0.0115 (8)0.0056 (8)
C140.0490 (11)0.0307 (10)0.0334 (9)0.0004 (8)0.0082 (8)0.0048 (7)
C150.0421 (11)0.0493 (13)0.0488 (11)0.0058 (9)0.0082 (9)0.0020 (9)
C160.0493 (11)0.0401 (11)0.0420 (10)0.0012 (9)0.0102 (9)0.0015 (9)
C170.0549 (13)0.0467 (13)0.0506 (11)0.0069 (10)0.0076 (10)0.0057 (10)
C180.0608 (14)0.0427 (12)0.0510 (11)0.0039 (10)0.0113 (10)0.0011 (10)
C190.0449 (12)0.0543 (14)0.0514 (11)0.0106 (10)0.0102 (9)0.0091 (10)
C200.0450 (11)0.0494 (13)0.0456 (11)0.0069 (10)0.0030 (9)0.0058 (9)
Geometric parameters (Å, º) top
O—C161.410 (2)C8—H8A0.9500
O—C171.441 (3)C9—C101.358 (3)
S1—C91.765 (2)C9—C141.453 (3)
S1—C151.810 (2)C10—C111.423 (3)
C1—C21.369 (3)C10—H10A0.9500
C1—C111.407 (3)C11—C121.418 (3)
C1—H1A0.9500C12—C131.446 (3)
S2—C151.797 (2)C13—C141.417 (3)
S2—C161.845 (2)C15—H15A0.9900
C2—C31.394 (3)C15—H15B0.9900
C2—H2A0.9500C16—C201.515 (3)
C3—C41.364 (3)C16—H16A1.0000
C3—H3A0.9500C17—C181.509 (3)
C4—C121.411 (3)C17—H17A0.9900
C4—H4A0.9500C17—H17B0.9900
C5—C61.369 (3)C18—C191.525 (3)
C5—C131.414 (3)C18—H18A0.9900
C5—H5A0.9500C18—H18B0.9900
C6—C71.386 (4)C19—C201.526 (3)
C6—H6A0.9500C19—H19A0.9900
C7—C81.375 (3)C19—H19B0.9900
C7—H7A0.9500C20—H20A0.9900
C8—C141.409 (3)C20—H20B0.9900
C16—O—C17114.09 (15)C14—C13—C12120.14 (17)
C9—S1—C15103.17 (10)C8—C14—C13119.49 (19)
C2—C1—C11121.0 (2)C8—C14—C9121.36 (19)
C2—C1—H1A119.5C13—C14—C9119.15 (18)
C11—C1—H1A119.5S2—C15—S1109.29 (12)
C15—S2—C16100.66 (10)S2—C15—H15A109.8
C1—C2—C3119.6 (2)S1—C15—H15A109.8
C1—C2—H2A120.2S2—C15—H15B109.8
C3—C2—H2A120.2S1—C15—H15B109.8
C4—C3—C2120.6 (2)H15A—C15—H15B108.3
C4—C3—H3A119.7O—C16—C20111.72 (17)
C2—C3—H3A119.7O—C16—S2112.90 (14)
C3—C4—C12121.7 (2)C20—C16—S2108.63 (14)
C3—C4—H4A119.1O—C16—H16A107.8
C12—C4—H4A119.1C20—C16—H16A107.8
C6—C5—C13121.3 (2)S2—C16—H16A107.8
C6—C5—H5A119.3O—C17—C18112.13 (17)
C13—C5—H5A119.3O—C17—H17A109.2
C5—C6—C7120.7 (2)C18—C17—H17A109.2
C5—C6—H6A119.6O—C17—H17B109.2
C7—C6—H6A119.6C18—C17—H17B109.2
C8—C7—C6119.8 (2)H17A—C17—H17B107.9
C8—C7—H7A120.1C17—C18—C19110.68 (18)
C6—C7—H7A120.1C17—C18—H18A109.5
C7—C8—C14120.9 (2)C19—C18—H18A109.5
C7—C8—H8A119.6C17—C18—H18B109.5
C14—C8—H8A119.6C19—C18—H18B109.5
C10—C9—C14119.96 (19)H18A—C18—H18B108.1
C10—C9—S1123.42 (15)C18—C19—C20109.86 (17)
C14—C9—S1116.61 (15)C18—C19—H19A109.7
C9—C10—C11122.04 (18)C20—C19—H19A109.7
C9—C10—H10A119.0C18—C19—H19B109.7
C11—C10—H10A119.0C20—C19—H19B109.7
C1—C11—C12119.68 (19)H19A—C19—H19B108.2
C1—C11—C10120.39 (19)C16—C20—C19111.70 (17)
C12—C11—C10119.93 (18)C16—C20—H20A109.3
C4—C12—C11117.40 (19)C19—C20—H20A109.3
C4—C12—C13123.86 (19)C16—C20—H20B109.3
C11—C12—C13118.73 (18)C19—C20—H20B109.3
C5—C13—C14117.75 (19)H20A—C20—H20B107.9
C5—C13—C12122.11 (19)
C11—C1—C2—C30.1 (3)C4—C12—C13—C14177.71 (17)
C1—C2—C3—C40.8 (3)C11—C12—C13—C141.5 (3)
C2—C3—C4—C121.3 (3)C7—C8—C14—C131.1 (3)
C13—C5—C6—C70.4 (3)C7—C8—C14—C9178.82 (18)
C5—C6—C7—C81.3 (3)C5—C13—C14—C81.9 (3)
C6—C7—C8—C140.6 (3)C12—C13—C14—C8177.74 (17)
C15—S1—C9—C1011.0 (2)C5—C13—C14—C9177.95 (17)
C15—S1—C9—C14169.89 (14)C12—C13—C14—C92.4 (3)
C14—C9—C10—C110.9 (3)C10—C9—C14—C8178.89 (18)
S1—C9—C10—C11179.97 (15)S1—C9—C14—C82.0 (2)
C2—C1—C11—C120.5 (3)C10—C9—C14—C131.2 (3)
C2—C1—C11—C10179.7 (2)S1—C9—C14—C13177.92 (14)
C9—C10—C11—C1178.01 (18)C16—S2—C15—S178.31 (12)
C9—C10—C11—C121.8 (3)C9—S1—C15—S2176.73 (10)
C3—C4—C12—C110.9 (3)C17—O—C16—C2056.0 (2)
C3—C4—C12—C13179.92 (18)C17—O—C16—S266.77 (19)
C1—C11—C12—C40.0 (3)C15—S2—C16—O46.56 (16)
C10—C11—C12—C4179.85 (17)C15—S2—C16—C20171.05 (14)
C1—C11—C12—C13179.21 (17)C16—O—C17—C1856.9 (2)
C10—C11—C12—C130.6 (3)O—C17—C18—C1954.1 (2)
C6—C5—C13—C141.3 (3)C17—C18—C19—C2052.0 (2)
C6—C5—C13—C12178.41 (19)O—C16—C20—C1953.7 (2)
C4—C12—C13—C51.9 (3)S2—C16—C20—C1971.50 (19)
C11—C12—C13—C5178.89 (17)C18—C19—C20—C1651.9 (2)
 

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