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The title compound, C9H20O4S2, has been obtained as an unexpected product when attempting to prepare a zinc(II) complex with the disulfoxide ligand 1,5-bis(ethylsulfinyl)pentane. The average S-C and S=O bond lengths are 1.781 (3) and 1.436 (2) Å, respectively. The two O-S-O angles [118.0 (1) and 117.2 (1)°] are nearly equivalent, with an average value of 117.6 (1)°. The molecular skeleton is almost fully extended in the crystalline state.
Supporting information
CCDC reference: 203009
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.112
- Data-to-parameter ratio = 13.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
1,5-Bis(ethylsulfonyl)-pentane
top
Crystal data top
C9H20O4S2 | Z = 2 |
Mr = 256.37 | F(000) = 276 |
Triclinic, P1 | Dx = 1.371 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.545 (2) Å | Cell parameters from 925 reflections |
b = 8.187 (3) Å | θ = 2.8–26.3° |
c = 13.867 (5) Å | µ = 0.42 mm−1 |
α = 96.463 (6)° | T = 293 K |
β = 96.731 (6)° | Block, colourless |
γ = 91.288 (6)° | 0.40 × 0.35 × 0.20 mm |
V = 620.8 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2181 independent reflections |
Radiation source: fine-focus sealed tube | 1766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −6→6 |
Tmin = 0.849, Tmax = 0.920 | k = −9→4 |
2545 measured reflections | l = −16→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | Only H-atom displacement parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0553P)2 + 0.4839P] where P = (Fo2 + 2Fc2)/3 |
2181 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
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 | −0.06241 (11) | 0.20340 (8) | −0.20886 (4) | 0.0307 (2) | |
S2 | 0.83285 (11) | 0.31040 (8) | 0.29007 (4) | 0.0312 (2) | |
O1 | −0.1714 (4) | 0.0582 (3) | −0.18103 (16) | 0.0526 (6) | |
O2 | −0.1698 (4) | 0.3590 (2) | −0.18320 (15) | 0.0474 (5) | |
O3 | 0.7289 (4) | 0.1653 (3) | 0.32199 (15) | 0.0496 (5) | |
O4 | 0.7359 (4) | 0.4639 (3) | 0.32120 (17) | 0.0591 (6) | |
C1 | −0.3016 (6) | 0.1620 (5) | −0.3927 (2) | 0.0614 (10) | |
H1A | −0.2931 | 0.1474 | −0.4618 | 0.087 (13)* | |
H1B | −0.3869 | 0.2599 | −0.3760 | 0.082 (13)* | |
H1C | −0.3862 | 0.0688 | −0.3745 | 0.089 (14)* | |
C2 | −0.0473 (5) | 0.1767 (4) | −0.33692 (19) | 0.0404 (7) | |
H2A | 0.0387 | 0.2692 | −0.3553 | 0.045 (8)* | |
H2B | 0.0394 | 0.0795 | −0.3538 | 0.043 (8)* | |
C3 | 0.2477 (4) | 0.2175 (3) | −0.15707 (18) | 0.0326 (6) | |
H3A | 0.3278 | 0.1195 | −0.1782 | 0.047 (8)* | |
H3B | 0.3282 | 0.3095 | −0.1783 | 0.040 (8)* | |
C4 | 0.2643 (5) | 0.2395 (4) | −0.04584 (19) | 0.0372 (6) | |
H4A | 0.1848 | 0.3378 | −0.0248 | 0.050 (9)* | |
H4B | 0.1825 | 0.1478 | −0.0248 | 0.058 (10)* | |
C5 | 0.5270 (5) | 0.2516 (3) | 0.00284 (19) | 0.0352 (6) | |
H5A | 0.6063 | 0.1533 | −0.0183 | 0.047 (8)* | |
H5B | 0.6087 | 0.3432 | −0.0183 | 0.041 (8)* | |
C6 | 0.5442 (5) | 0.2742 (3) | 0.11372 (18) | 0.0336 (6) | |
H6A | 0.4657 | 0.3728 | 0.1350 | 0.038 (8)* | |
H6B | 0.4622 | 0.1827 | 0.1350 | 0.054 (9)* | |
C7 | 0.8087 (5) | 0.2847 (3) | 0.15993 (18) | 0.0326 (6) | |
H7A | 0.8902 | 0.3755 | 0.1378 | 0.042 (8)* | |
H7B | 0.8863 | 0.1858 | 0.1385 | 0.061 (10)* | |
C8 | 1.1538 (5) | 0.3176 (4) | 0.32330 (19) | 0.0357 (6) | |
H8A | 1.2197 | 0.2185 | 0.2951 | 0.040 (8)* | |
H8B | 1.2241 | 0.4084 | 0.2969 | 0.037 (7)* | |
C9 | 1.2192 (6) | 0.3349 (5) | 0.4329 (2) | 0.0596 (10) | |
H9A | 1.3927 | 0.3384 | 0.4479 | 0.093 (13)* | |
H9B | 1.1515 | 0.2432 | 0.4594 | 0.094 (15)* | |
H9C | 1.1560 | 0.4349 | 0.4612 | 0.094 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0277 (4) | 0.0340 (4) | 0.0297 (4) | 0.0012 (3) | −0.0008 (3) | 0.0053 (3) |
S2 | 0.0260 (3) | 0.0397 (4) | 0.0276 (4) | 0.0032 (3) | 0.0011 (3) | 0.0039 (3) |
O1 | 0.0484 (12) | 0.0525 (13) | 0.0572 (14) | −0.0038 (10) | 0.0067 (10) | 0.0086 (10) |
O2 | 0.0433 (11) | 0.0474 (12) | 0.0525 (13) | 0.0109 (9) | 0.0070 (10) | 0.0074 (9) |
O3 | 0.0433 (12) | 0.0587 (13) | 0.0489 (12) | −0.0018 (10) | 0.0057 (10) | 0.0156 (10) |
O4 | 0.0515 (13) | 0.0635 (15) | 0.0595 (14) | 0.0101 (11) | 0.0055 (11) | −0.0050 (11) |
C1 | 0.057 (2) | 0.080 (3) | 0.0421 (19) | −0.001 (2) | −0.0182 (16) | 0.0064 (17) |
C2 | 0.0436 (16) | 0.0461 (17) | 0.0305 (14) | 0.0022 (13) | 0.0001 (12) | 0.0045 (12) |
C3 | 0.0269 (13) | 0.0410 (15) | 0.0294 (14) | 0.0023 (11) | −0.0002 (10) | 0.0050 (11) |
C4 | 0.0311 (14) | 0.0507 (17) | 0.0289 (14) | 0.0018 (13) | 0.0007 (11) | 0.0040 (12) |
C5 | 0.0309 (14) | 0.0449 (16) | 0.0293 (14) | 0.0019 (12) | 0.0015 (11) | 0.0039 (11) |
C6 | 0.0305 (14) | 0.0429 (16) | 0.0266 (13) | 0.0009 (12) | 0.0005 (11) | 0.0031 (11) |
C7 | 0.0304 (13) | 0.0399 (15) | 0.0264 (13) | 0.0006 (11) | 0.0000 (11) | 0.0021 (11) |
C8 | 0.0263 (13) | 0.0480 (17) | 0.0321 (14) | 0.0036 (12) | 0.0022 (11) | 0.0021 (12) |
C9 | 0.0401 (18) | 0.101 (3) | 0.0334 (17) | 0.0104 (19) | −0.0056 (14) | −0.0001 (18) |
Geometric parameters (Å, º) top
S1—O1 | 1.433 (2) | C4—C5 | 1.528 (4) |
S1—O2 | 1.444 (2) | C4—H4A | 0.9595 |
S1—C2 | 1.777 (3) | C4—H4B | 0.9595 |
S1—C3 | 1.780 (3) | C5—C6 | 1.519 (4) |
S2—O4 | 1.420 (2) | C5—H5A | 0.9589 |
S2—O3 | 1.445 (2) | C5—H5B | 0.9591 |
S2—C7 | 1.782 (3) | C6—C7 | 1.527 (3) |
S2—C8 | 1.783 (3) | C6—H6A | 0.9593 |
C1—C2 | 1.522 (4) | C6—H6B | 0.9597 |
C1—H1A | 0.9595 | C7—H7A | 0.9594 |
C1—H1B | 0.9593 | C7—H7B | 0.9594 |
C1—H1C | 0.9593 | C8—C9 | 1.511 (4) |
C2—H2A | 0.9593 | C8—H8A | 0.9594 |
C2—H2B | 0.9596 | C8—H8B | 0.9595 |
C3—C4 | 1.524 (3) | C9—H9A | 0.9589 |
C3—H3A | 0.9594 | C9—H9B | 0.9597 |
C3—H3B | 0.9593 | C9—H9C | 0.9589 |
| | | |
O1—S1—O2 | 118.02 (13) | C3—C4—H4B | 109.2 |
O1—S1—C2 | 109.15 (14) | C5—C4—H4B | 108.8 |
O2—S1—C2 | 108.85 (13) | H4A—C4—H4B | 108.3 |
O1—S1—C3 | 107.97 (13) | C6—C5—C4 | 112.5 (2) |
O2—S1—C3 | 108.09 (13) | C6—C5—H5A | 109.6 |
C2—S1—C3 | 103.85 (13) | C4—C5—H5A | 108.6 |
O4—S2—O3 | 117.19 (14) | C6—C5—H5B | 109.0 |
O4—S2—C7 | 108.70 (13) | C4—C5—H5B | 108.7 |
O3—S2—C7 | 108.66 (13) | H5A—C5—H5B | 108.3 |
O4—S2—C8 | 109.90 (13) | C5—C6—C7 | 111.1 (2) |
O3—S2—C8 | 109.19 (13) | C5—C6—H6A | 109.7 |
C7—S2—C8 | 102.12 (12) | C7—C6—H6A | 109.3 |
C2—C1—H1A | 110.4 | C5—C6—H6B | 109.2 |
C2—C1—H1B | 109.3 | C7—C6—H6B | 109.2 |
H1A—C1—H1B | 109.5 | H6A—C6—H6B | 108.3 |
C2—C1—H1C | 108.7 | C6—C7—S2 | 111.81 (18) |
H1A—C1—H1C | 109.4 | C6—C7—H7A | 108.9 |
H1B—C1—H1C | 109.5 | S2—C7—H7A | 109.7 |
C1—C2—S1 | 110.5 (2) | C6—C7—H7B | 109.0 |
C1—C2—H2A | 109.1 | S2—C7—H7B | 109.3 |
S1—C2—H2A | 109.7 | H7A—C7—H7B | 108.2 |
C1—C2—H2B | 109.7 | C9—C8—S2 | 111.7 (2) |
S1—C2—H2B | 109.5 | C9—C8—H8A | 109.1 |
H2A—C2—H2B | 108.3 | S2—C8—H8A | 109.1 |
C4—C3—S1 | 109.98 (18) | C9—C8—H8B | 109.8 |
C4—C3—H3A | 109.5 | S2—C8—H8B | 109.0 |
S1—C3—H3A | 109.9 | H8A—C8—H8B | 108.0 |
C4—C3—H3B | 109.3 | C8—C9—H9A | 109.2 |
S1—C3—H3B | 109.8 | C8—C9—H9B | 110.0 |
H3A—C3—H3B | 108.4 | H9A—C9—H9B | 109.4 |
C3—C4—C5 | 112.4 (2) | C8—C9—H9C | 109.3 |
C3—C4—H4A | 109.4 | H9A—C9—H9C | 109.5 |
C5—C4—H4A | 108.7 | H9B—C9—H9C | 109.5 |
| | | |
O1—S1—C2—C1 | 64.9 (3) | C4—C5—C6—C7 | 179.6 (2) |
O2—S1—C2—C1 | −65.2 (3) | C5—C6—C7—S2 | −179.77 (19) |
C3—S1—C2—C1 | 179.9 (2) | O4—S2—C7—C6 | −64.2 (2) |
O1—S1—C3—C4 | −63.7 (2) | O3—S2—C7—C6 | 64.4 (2) |
O2—S1—C3—C4 | 65.0 (2) | C8—S2—C7—C6 | 179.71 (19) |
C2—S1—C3—C4 | −179.53 (19) | O4—S2—C8—C9 | 66.2 (3) |
S1—C3—C4—C5 | 179.75 (19) | O3—S2—C8—C9 | −63.6 (3) |
C3—C4—C5—C6 | 179.8 (2) | C7—S2—C8—C9 | −178.5 (2) |
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