2,5-Dihexyl­thio­phene 1,1-dioxide

Van Tonder, J.; Gohain, M.; Loganathan, N.; Bezuidenhoudt, B.C.B.

doi:10.1107/S1600536812046867

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3437

doi:10.1107/S1600536812046867

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2,5-Dihexylthiophene 1,1-dioxide

Johannes Van Tonder,^a Mukut Gohain,^a Nagarajan Loganathan ^a ^* and Barend C. B. Bezuidenhoudt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: nagagold@gmail.com

(Received 29 October 2012; accepted 14 November 2012; online 24 November 2012)

In the title molecule, C₁₆H₂₈O₂S, the two n-hexyl groups are in all-trans conformations. Their C atoms are situated close to the plane of the thiophene 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 thiophene 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_r = 284.44
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.167
S = 1.07
3149 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046867/gk2532sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812046867/gk2532Isup3.cml

checkCIF report

Comment top

Tetrahydrothiophene 1,1-dioxide otherwise known as sulfolane, is an important industrial solvent used in the purification of natural gas, particularly for the extraction of aromatic hydrocarbon from the other hydrocarbon mixtures. Thiophene 1,1-dioxide is an important intermediate in the synthesis of various class of organic compounds. This class of compound is also known for their bioapplications (Nakayama et al., 1999; Naesens et al., 2006; Kim et al., 2008; Sagardoy et al., 2010). For example, some of them have been found to be effective inhibitors of hepatitis C virus polymerase (Kim et al., 2008).

The title compound, 2,5-dihexyl-thiophene-1,1-dioxide, was synthesized by the procedure of Barbarella et al. (1998).

Related literature top

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 top

A mixture of 2,5-dihexylthiophene (0.500 g; 2.0 mmol) and NaHCO₃ (0.667 g; 7.9 mmol; 4.0 eq) was taken in dichloromethane(30 ml) at 0 °C and allowed to stir vigorously for a few minutes. To which a freshly recrystallized (from dichloromethane) solid of m-chloroperbenzoic acid (1.411 g; 8.2 mmol; 4.1 eq.) was added in portion over 60 min. After 16hrs of stirring, the precipitate was removed by filtration and successively washed with dichloromethane (2 x 5 ml). The collective filtrate was then evaporated to dryness. Crystals of title compound were obtained as white needles from n-pentane. Yield: 0.304 g; 53.9%. ¹H NMR (600 MHz, CDCl3) δ 6.28 – 6.24 (2H, m, H-3,4), 2.46 (4H, t, J = 7.7 Hz, H-1'), 1.68 – 1.61 (4H, m, H-2'), 1.41 – 1.34 (4H, m, H-3'), 1.33 – 1.26 (8H, m, H-4',5'), 0.91 – 0.86 (6H, m, H-6'). 13 C NMR (151 MHz, CDCl3) δ 144.08 (C-2,5), 121.80 (C-3,4), 31.51 (C-4',5'), 28.91 (C-3'), 26.67 (C-2'), 24.41 (C-1'), 22.63 (C-4',5'), 14.16 (C-6'). EI—MS m/z: 284.10 (35.47%; M+), 165.10 (78.57), 95.10 (100.00), 81.05 (83.06).

Computing details top

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

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids shown at the 50% probability level.

2,5-Dihexylthiophene 1,1-dioxide top

Crystal data top

C₁₆H₂₈O₂S	F(000) = 624
M_r = 284.44	D_x = 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

Data collection top

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

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0703P)² + 0.6152P] where P = (F_o² + 2F_c²)/3
3149 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₂₈O₂S	V = 1781.7 (6) Å³
M_r = 284.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8249 (11) Å	µ = 0.18 mm⁻¹
b = 11.248 (2) Å	T = 293 K
c = 27.207 (6) Å	1.00 × 0.30 × 0.10 mm
β = 91.770 (8)°

Data collection top

Bruker APEXII CCD diffractometer	3149 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2008)	2207 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.982	R_int = 0.072
18944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
3149 reflections	Δρ_min = −0.20 e Å⁻³
174 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₈O₂S
M_r	284.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.8249 (11), 11.248 (2), 27.207 (6)
β (°)	91.770 (8)
V (Å³)	1781.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	1.00 × 0.30 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2008)
T_min, T_max	0.841, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	18944, 3149, 2207
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.167, 1.07
No. of reflections	3149
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXTL (Sheldrick, 2008) and WinGX (Farrugia 2012), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The University of the Free State and Sasol Ltd are gratefully acknowledged for the financial support. Special thanks to Professor Andreas Roodt.

References

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