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The title compound, C15H20O4S2, crystallizes in a chiral space group although it contains mirror symmetry. The tropone ring is inclined at an angle of 50.3 (1)° to the crown ether ring. The planarity of the tropone ring system itself is diminished by as much as 20.8 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010489/qa0358sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010489/qa0358Isup2.hkl
Contains datablock I

CCDC reference: 150734

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C15H20O4S2Dx = 1.346 Mg m3
Mr = 328.43Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 9.682 (5) Åθ = 10.6–18.3°
b = 18.654 (5) ŵ = 0.34 mm1
c = 8.977 (5) ÅT = 296 K
V = 1621.3 (13) Å3Prism, yellow
Z = 40.40 × 0.30 × 0.30 mm
F(000) = 696
Data collection top
Enraf-Nonius FR590
diffractometer
1420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.0°, θmin = 3.0°
ω–2θ scansh = 120
Absorption correction: empirical (using intensity measurements)
via ψ scans (North et al., 1968)
k = 023
Tmin = 0.879, Tmax = 0.903l = 011
2032 measured reflections3 standard reflections every 120 min
2032 independent reflections intensity decay: 1.3%
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.040P)2 + 0.4494P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2032 reflectionsΔρmax = 0.32 e Å3
190 parametersΔρmin = 0.23 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (17)
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
S10.75578 (12)0.16943 (6)0.60467 (12)0.0591 (3)
S20.95524 (10)0.09292 (5)0.10713 (12)0.0540 (3)
O10.9491 (3)0.13814 (13)0.3976 (3)0.0542 (6)
O20.4435 (4)0.14195 (19)0.5079 (3)0.0756 (9)
O30.4211 (4)0.0656 (2)0.2297 (4)0.0883 (11)
O40.6484 (3)0.06549 (15)0.0091 (4)0.0651 (8)
C10.8522 (4)0.16703 (18)0.3311 (4)0.0439 (8)
C20.8465 (4)0.16256 (19)0.1680 (4)0.0453 (9)
C30.7810 (4)0.2084 (2)0.0728 (4)0.0552 (11)
H30.80350.20250.02710.066*
C40.6852 (4)0.2629 (2)0.1020 (6)0.0638 (12)
H40.65990.29130.02120.077*
C50.6254 (5)0.2791 (2)0.2333 (5)0.0627 (12)
H50.56140.31620.22980.075*
C60.6449 (4)0.2487 (2)0.3737 (5)0.0576 (10)
H60.58360.26380.44700.069*
C70.7418 (4)0.19962 (18)0.4185 (4)0.0485 (9)
C80.5926 (5)0.1886 (3)0.6934 (5)0.0699 (13)
H8A0.60650.18930.80040.084*
H8B0.56300.23620.66350.084*
C90.4805 (5)0.1370 (3)0.6584 (5)0.0765 (15)
H9A0.51140.08860.68020.092*
H9B0.40070.14710.72020.092*
C100.3329 (5)0.0971 (3)0.4689 (6)0.0782 (14)
H10A0.25010.11150.52190.094*
H10B0.35390.04790.49560.094*
C110.3104 (5)0.1028 (3)0.3059 (6)0.0874 (17)
H11A0.22220.08150.27960.105*
H11B0.30910.15280.27640.105*
C120.4169 (6)0.0725 (3)0.0787 (7)0.0918 (17)
H12A0.43180.12220.05140.110*
H12B0.32690.05810.04210.110*
C130.5264 (5)0.0266 (3)0.0098 (6)0.0753 (14)
H13A0.54390.01460.07310.090*
H13B0.49470.00920.08610.090*
C140.7572 (5)0.0237 (2)0.0672 (5)0.0638 (11)
H14A0.73330.00720.16640.077*
H14B0.77160.01800.00460.077*
C150.8873 (4)0.0674 (2)0.0737 (4)0.0554 (10)
H15A0.86930.11050.13080.066*
H15B0.95730.04010.12640.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0616 (6)0.0642 (6)0.0515 (5)0.0118 (6)0.0143 (6)0.0011 (6)
S20.0479 (5)0.0586 (5)0.0555 (5)0.0060 (5)0.0054 (5)0.0073 (6)
O10.0480 (14)0.0583 (14)0.0563 (15)0.0093 (13)0.0171 (16)0.0036 (15)
O20.067 (2)0.102 (2)0.0584 (17)0.005 (2)0.0026 (18)0.0070 (18)
O30.095 (3)0.107 (3)0.063 (2)0.040 (2)0.010 (2)0.0088 (19)
O40.0577 (17)0.0521 (16)0.085 (2)0.0055 (15)0.0012 (18)0.0075 (16)
C10.0410 (19)0.0362 (17)0.054 (2)0.0059 (17)0.0140 (18)0.0061 (17)
C20.0435 (19)0.0393 (18)0.053 (2)0.0056 (17)0.0086 (18)0.0060 (17)
C30.065 (3)0.049 (2)0.051 (2)0.0000 (19)0.014 (2)0.0096 (19)
C40.073 (3)0.050 (2)0.068 (3)0.007 (2)0.026 (3)0.017 (2)
C50.061 (3)0.048 (2)0.079 (3)0.014 (2)0.016 (3)0.011 (2)
C60.055 (2)0.053 (2)0.065 (3)0.009 (2)0.009 (2)0.001 (2)
C70.051 (2)0.0424 (18)0.052 (2)0.0023 (18)0.013 (2)0.0018 (18)
C80.080 (3)0.082 (3)0.048 (2)0.021 (3)0.008 (2)0.013 (2)
C90.069 (3)0.111 (4)0.050 (2)0.020 (3)0.006 (2)0.010 (3)
C100.054 (3)0.099 (4)0.082 (3)0.002 (3)0.007 (3)0.018 (3)
C110.061 (3)0.111 (4)0.090 (4)0.025 (3)0.016 (3)0.022 (4)
C120.088 (4)0.078 (3)0.110 (5)0.002 (3)0.007 (4)0.007 (4)
C130.076 (3)0.067 (3)0.083 (3)0.012 (3)0.008 (3)0.004 (3)
C140.072 (3)0.057 (2)0.063 (3)0.005 (3)0.008 (3)0.005 (2)
C150.059 (2)0.063 (2)0.044 (2)0.002 (2)0.002 (2)0.0044 (19)
Geometric parameters (Å, º) top
S1—C71.769 (4)C1—C71.459 (5)
S1—C81.805 (5)C1—C21.467 (5)
S2—C21.760 (4)C2—C31.365 (5)
S2—C151.815 (4)C3—C41.401 (5)
O1—C11.236 (4)C4—C51.348 (6)
O2—C91.401 (5)C5—C61.394 (6)
O2—C101.404 (6)C6—C71.371 (5)
O3—C121.362 (6)C8—C91.485 (6)
O3—C111.448 (6)C10—C111.483 (7)
O4—C131.396 (5)C12—C131.497 (7)
O4—C141.411 (5)C14—C151.502 (6)
C7—S1—C8106.6 (2)C4—C5—C6129.9 (4)
C2—S2—C15104.76 (19)C7—C6—C5129.0 (4)
C9—O2—C10113.3 (4)C6—C7—C1128.4 (4)
C12—O3—C11113.8 (4)C6—C7—S1122.9 (3)
C13—O4—C14112.9 (3)C1—C7—S1108.6 (3)
O1—C1—C7118.5 (3)C9—C8—S1114.7 (3)
O1—C1—C2119.1 (4)O2—C9—C8110.4 (4)
C7—C1—C2122.2 (3)O2—C10—C11108.4 (5)
C3—C2—C1127.3 (4)O3—C11—C10108.8 (4)
C3—C2—S2123.1 (3)O3—C12—C13109.7 (5)
C1—C2—S2109.2 (3)O4—C13—C12110.6 (4)
C2—C3—C4130.2 (4)O4—C14—C15109.9 (3)
C5—C4—C3127.6 (4)C14—C15—S2114.3 (3)
O1—C1—C2—C3155.7 (4)C2—C1—C7—S1160.8 (3)
C7—C1—C2—C329.2 (6)C8—S1—C7—C619.8 (4)
O1—C1—C2—S217.7 (4)C8—S1—C7—C1163.4 (3)
C7—C1—C2—S2157.4 (3)C7—S1—C8—C978.8 (4)
C15—S2—C2—C329.8 (4)C10—O2—C9—C8176.9 (4)
C15—S2—C2—C1156.5 (3)S1—C8—C9—O266.9 (5)
C1—C2—C3—C412.1 (7)C9—O2—C10—C11175.7 (4)
S2—C2—C3—C4175.3 (3)C12—O3—C11—C10174.8 (5)
C2—C3—C4—C56.2 (8)O2—C10—C11—O373.0 (6)
C3—C4—C5—C62.3 (8)C11—O3—C12—C13174.4 (4)
C4—C5—C6—C78.3 (8)C14—O4—C13—C12177.1 (4)
C5—C6—C7—C11.1 (7)O3—C12—C13—O491.7 (6)
C5—C6—C7—S1177.3 (4)C13—O4—C14—C15175.8 (4)
O1—C1—C7—C6162.2 (4)O4—C14—C15—S266.2 (4)
C2—C1—C7—C622.6 (6)C2—S2—C15—C1475.7 (3)
O1—C1—C7—S114.4 (4)
 

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