1,5-Bis­(ethyl­sulfonyl)­pentane

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	Only H-atom displacement parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.4839P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)