2,5-Dihexyl-thio-phene 1,1-dioxide.

In the title mol-ecule, C16H28O2S, the two n-hexyl groups are in all-trans conformations. Their C atoms are situated close to the plane of the thio-phene ring with a maximum deviation of 0.718 (6) Å for one of the terminal methyl groups. In the crystal, a short C-H⋯O contact is observed between thio-phene 1,1-dioxide groups.

Related literature

For the preparation of the title compound, see: Barbarella et al. (1998 ▶). For a review on thio­phene-1,1-dioxide derivatives and their applications, see: Nakayama et al. (1999 ▶). For the biological activity of sulfone compounds, see: Naesens et al. (2006 ▶); Kim et al. (2008 ▶); Sagardoy et al. (2010 ▶).

Experimental

Crystal data

C16H28O2S

M = 284.44

Monoclinic,

a = 5.8249 (11) Å

b = 11.248 (2) Å

c = 27.207 (6) Å

β = 91.770 (8)°

V = 1781.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

1.00 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2008 ▶) T min = 0.841, T max = 0.982

18944 measured reflections

3149 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.167

S = 1.07

3149 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶) and WinGX (Farrugia 2012) ▶; program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046867/gk2532sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046867/gk2532Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046867/gk2532Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H28O2S	F(000) = 624
Mr = 284.44	Dx = 1.060 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4797 reflections
a = 5.8249 (11) Å	θ = 2.4–23.1°
b = 11.248 (2) Å	µ = 0.18 mm−1
c = 27.207 (6) Å	T = 293 K
β = 91.770 (8)°	Needle, colourless
V = 1781.7 (6) Å3	1.00 × 0.30 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	3149 independent reflections
Radiation source: sealed tube	2207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker 2008)	h = −6→5
Tmin = 0.841, Tmax = 0.982	k = −13→13
18944 measured reflections	l = −32→32

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.6152P] where P = (Fo2 + 2Fc2)/3
3149 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. Crystal was mounted and automatically centered on a Bruker SMART X2S bench top crystallographic system. Data were collected at 20°C with 60 s/frame exposure time (total of 1260, width 0.5°) covering up to θ = 25.11° and 99.9% completeness accomplished.

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.

	x	y	z	Uiso*/Ueq
S1	0.46906 (11)	1.12674 (5)	0.21332 (3)	0.0601 (3)
O1	0.3088 (3)	1.17815 (16)	0.17855 (8)	0.0747 (6)
O2	0.6195 (3)	1.20741 (15)	0.23951 (8)	0.0810 (7)
C1	0.3264 (5)	1.0326 (2)	0.25486 (11)	0.0626 (7)
C2	0.4059 (5)	0.9226 (2)	0.24780 (11)	0.0694 (8)
H2	0.3564	0.8578	0.2659	0.083*
C3	0.5755 (5)	0.9109 (2)	0.20979 (12)	0.0723 (9)
H3	0.6418	0.8382	0.2022	0.087*
C4	0.6296 (5)	1.0103 (2)	0.18666 (11)	0.0607 (7)
C5	0.7877 (5)	1.0372 (2)	0.14685 (13)	0.0754 (9)
H5A	0.8910	1.1002	0.1577	0.090*
H5B	0.6990	1.0664	0.1186	0.090*
C6	0.9293 (6)	0.9312 (3)	0.13111 (14)	0.0841 (9)
H6A	1.0245	0.9051	0.1589	0.101*
H6B	0.8260	0.8666	0.1222	0.101*
C7	1.0796 (6)	0.9554 (3)	0.08902 (15)	0.0989 (11)
H7A	1.1824	1.0204	0.0977	0.119*
H7B	0.9846	0.9806	0.0610	0.119*
C8	1.2227 (7)	0.8481 (4)	0.07397 (17)	0.1131 (13)
H8A	1.3208	0.8246	0.1017	0.136*
H8B	1.1196	0.7824	0.0665	0.136*
C9	1.3646 (10)	0.8683 (5)	0.0321 (2)	0.157 (2)
H9A	1.4668	0.9344	0.0396	0.189*
H9B	1.2660	0.8918	0.0044	0.189*
C10	1.5056 (10)	0.7652 (6)	0.0169 (2)	0.174 (2)
H10A	1.6233	0.7500	0.0416	0.261*
H10B	1.5751	0.7827	−0.0138	0.261*
H10C	1.4093	0.6963	0.0131	0.261*
C11	0.1562 (5)	1.0832 (2)	0.28819 (12)	0.0699 (8)
H11A	0.0457	1.1296	0.2689	0.084*
H11B	0.2345	1.1368	0.3110	0.084*
C12	0.0284 (6)	0.9910 (3)	0.31714 (13)	0.0772 (9)
H12A	−0.0550	0.9395	0.2942	0.093*
H12B	0.1395	0.9423	0.3352	0.093*
C13	−0.1368 (6)	1.0412 (3)	0.35249 (13)	0.0923 (10)
H13A	−0.2437	1.0931	0.3348	0.111*
H13B	−0.0528	1.0889	0.3767	0.111*
C14	−0.2728 (7)	0.9448 (4)	0.37919 (16)	0.1160 (14)
H14A	−0.3549	0.8971	0.3547	0.139*
H14B	−0.1644	0.8929	0.3964	0.139*
C15	−0.4357 (10)	0.9875 (5)	0.4140 (2)	0.155 (2)
H15A	−0.5433	1.0410	0.3974	0.186*
H15B	−0.3547	1.0321	0.4396	0.186*
C16	−0.5686 (10)	0.8855 (7)	0.4373 (2)	0.192 (3)
H16A	−0.6504	0.8417	0.4121	0.288*
H16B	−0.6758	0.9174	0.4600	0.288*
H16C	−0.4630	0.8336	0.4545	0.288*

	U11	U22	U33	U12	U13	U23
S1	0.0592 (4)	0.0319 (3)	0.0888 (5)	−0.0010 (3)	−0.0051 (4)	0.0004 (3)
O1	0.0735 (12)	0.0499 (10)	0.0999 (15)	0.0105 (9)	−0.0096 (11)	0.0143 (10)
O2	0.0808 (13)	0.0438 (10)	0.1173 (17)	−0.0150 (9)	−0.0117 (12)	−0.0124 (10)
C1	0.0659 (17)	0.0403 (13)	0.0810 (19)	−0.0032 (12)	−0.0056 (15)	0.0016 (12)
C2	0.081 (2)	0.0363 (13)	0.091 (2)	−0.0026 (13)	0.0022 (17)	0.0073 (13)
C3	0.0754 (19)	0.0374 (13)	0.103 (2)	0.0078 (13)	−0.0057 (18)	−0.0004 (14)
C4	0.0541 (15)	0.0411 (13)	0.0864 (19)	0.0029 (12)	−0.0040 (15)	−0.0038 (13)
C5	0.0680 (19)	0.0589 (16)	0.099 (2)	0.0019 (15)	−0.0018 (18)	−0.0043 (16)
C6	0.073 (2)	0.075 (2)	0.104 (2)	0.0089 (17)	0.0018 (19)	−0.0114 (19)
C7	0.088 (2)	0.100 (3)	0.109 (3)	0.008 (2)	0.014 (2)	−0.013 (2)
C8	0.103 (3)	0.119 (3)	0.118 (3)	0.013 (3)	0.022 (3)	−0.011 (3)
C9	0.147 (4)	0.176 (6)	0.150 (5)	0.038 (4)	0.033 (4)	−0.011 (4)
C10	0.158 (5)	0.202 (6)	0.164 (5)	0.069 (4)	0.033 (4)	−0.040 (5)
C11	0.0752 (19)	0.0464 (14)	0.088 (2)	−0.0014 (14)	0.0038 (16)	−0.0020 (14)
C12	0.081 (2)	0.0609 (17)	0.090 (2)	−0.0078 (15)	0.0033 (18)	0.0062 (16)
C13	0.099 (3)	0.086 (2)	0.093 (2)	−0.007 (2)	0.013 (2)	0.009 (2)
C14	0.108 (3)	0.135 (4)	0.106 (3)	−0.004 (3)	0.019 (3)	0.021 (3)
C15	0.147 (4)	0.189 (6)	0.130 (4)	−0.039 (4)	0.022 (4)	0.009 (4)
C16	0.152 (5)	0.277 (8)	0.149 (5)	−0.087 (5)	0.016 (4)	0.075 (5)

S1—O1	1.4306 (19)	C9—H9A	0.9700
S1—O2	1.4353 (19)	C9—H9B	0.9700
S1—C1	1.774 (3)	C10—H10A	0.9600
S1—C4	1.777 (3)	C10—H10B	0.9600
C1—C2	1.337 (4)	C10—H10C	0.9600
C1—C11	1.478 (4)	C11—C12	1.512 (4)
C2—C3	1.458 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.325 (4)	C12—C13	1.492 (5)
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.475 (4)	C12—H12B	0.9700
C5—C6	1.519 (4)	C13—C14	1.539 (5)
C5—H5A	0.9700	C13—H13A	0.9700
C5—H5B	0.9700	C13—H13B	0.9700
C6—C7	1.488 (5)	C14—C15	1.443 (6)
C6—H6A	0.9700	C14—H14A	0.9700
C6—H6B	0.9700	C14—H14B	0.9700
C7—C8	1.529 (5)	C15—C16	1.533 (7)
C7—H7A	0.9700	C15—H15A	0.9700
C7—H7B	0.9700	C15—H15B	0.9700
C8—C9	1.446 (7)	C16—H16A	0.9600
C8—H8A	0.9700	C16—H16B	0.9600
C8—H8B	0.9700	C16—H16C	0.9600
C9—C10	1.487 (7)
O1—S1—O2	116.66 (12)	C8—C9—H9B	108.4
O1—S1—C1	110.71 (13)	C10—C9—H9B	108.4
O2—S1—C1	110.61 (13)	H9A—C9—H9B	107.5
O1—S1—C4	111.64 (13)	C9—C10—H10A	109.5
O2—S1—C4	110.35 (13)	C9—C10—H10B	109.5
C1—S1—C4	94.74 (13)	H10A—C10—H10B	109.5
C2—C1—C11	133.4 (3)	C9—C10—H10C	109.5
C2—C1—S1	106.8 (2)	H10A—C10—H10C	109.5
C11—C1—S1	119.78 (19)	H10B—C10—H10C	109.5
C1—C2—C3	115.5 (2)	C1—C11—C12	113.9 (2)
C1—C2—H2	122.3	C1—C11—H11A	108.8
C3—C2—H2	122.3	C12—C11—H11A	108.8
C4—C3—C2	115.9 (2)	C1—C11—H11B	108.8
C4—C3—H3	122.0	C12—C11—H11B	108.8
C2—C3—H3	122.0	H11A—C11—H11B	107.7
C3—C4—C5	133.2 (3)	C13—C12—C11	114.4 (3)
C3—C4—S1	107.0 (2)	C13—C12—H12A	108.6
C5—C4—S1	119.80 (19)	C11—C12—H12A	108.6
C4—C5—C6	113.8 (3)	C13—C12—H12B	108.6
C4—C5—H5A	108.8	C11—C12—H12B	108.6
C6—C5—H5A	108.8	H12A—C12—H12B	107.6
C4—C5—H5B	108.8	C12—C13—C14	112.9 (3)
C6—C5—H5B	108.8	C12—C13—H13A	109.0
H5A—C5—H5B	107.7	C14—C13—H13A	109.0
C7—C6—C5	114.3 (3)	C12—C13—H13B	109.0
C7—C6—H6A	108.7	C14—C13—H13B	109.0
C5—C6—H6A	108.7	H13A—C13—H13B	107.8
C7—C6—H6B	108.7	C15—C14—C13	115.7 (4)
C5—C6—H6B	108.7	C15—C14—H14A	108.4
H6A—C6—H6B	107.6	C13—C14—H14A	108.4
C6—C7—C8	113.6 (3)	C15—C14—H14B	108.4
C6—C7—H7A	108.8	C13—C14—H14B	108.4
C8—C7—H7A	108.8	H14A—C14—H14B	107.4
C6—C7—H7B	108.8	C14—C15—C16	111.9 (5)
C8—C7—H7B	108.8	C14—C15—H15A	109.2
H7A—C7—H7B	107.7	C16—C15—H15A	109.2
C9—C8—C7	114.6 (4)	C14—C15—H15B	109.2
C9—C8—H8A	108.6	C16—C15—H15B	109.2
C7—C8—H8A	108.6	H15A—C15—H15B	107.9
C9—C8—H8B	108.6	C15—C16—H16A	109.5
C7—C8—H8B	108.6	C15—C16—H16B	109.5
H8A—C8—H8B	107.6	H16A—C16—H16B	109.5
C8—C9—C10	115.5 (5)	C15—C16—H16C	109.5
C8—C9—H9A	108.4	H16A—C16—H16C	109.5
C10—C9—H9A	108.4	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.54	3.186 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.54	3.186 (3)	126

Symmetry code: (i) .