2,6-Dichloro-1-[(1E)-2-(phenyl­sulfon­yl)ethen­yl]benzene

South, M.S.; Obiako, A.J.; Sykora, R.E.; Forbes, D.C.

doi:10.1107/S1600536811011901

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1055

doi:10.1107/S1600536811011901

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2,6-Dichloro-1-[(1E)-2-(phenylsulfonyl)ethenyl]benzene

Michael S. South,^a Adirika J. Obiako,^a Richard E. Sykora ^a and David C. Forbes ^a ^*

^aDepartment of Chemistry, University of South Alabama, Mobile, AL 36688-0002 USA
^*Correspondence e-mail: dforbes@southalabama.edu

(Received 17 March 2011; accepted 30 March 2011; online 7 April 2011)

In the title compound, C₁₄H₁₀Cl₂O₂S, the product of a base-catalyzed condensation followed by decarboxylation of the carboxylate group of the sulfonyl derivative, the configuration of the alkene unit is E. The torsion angle between the alkene unit and the 2,6-dichlorophenyl ring system is −40.8 (3)°. The dihedral angle between the rings is 80.39 (7)°.

Related literature

For a review on the use of vinyl sulfones in organic chemistry, see: Simpkins (1990 ). For the use of phenylsulfonylacetic acid in the formation of vinyl sulfones, see: Baliah & Seshapathirao (1959 ). For a general review on the condensation of activated methylenes onto aryl aldehydes, see: Jones (1967 ). For the structure of the related phenyl vinyl sulfone, see: Briggs et al. (1998 ).

Experimental

Crystal data

C₁₄H₁₀Cl₂O₂S
M_r = 313.18
Triclinic, $[P \overline 1]$
a = 7.5924 (6) Å
b = 8.3060 (4) Å
c = 11.3360 (9) Å
α = 78.639 (5)°
β = 84.976 (7)°
γ = 77.497 (6)°
V = 683.49 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 290 K
0.52 × 0.34 × 0.06 mm

Data collection

Oxford Xcalibur E diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Abingdon, England.]$ ) T_min = 0.810, T_max = 0.961
4291 measured reflections
2491 independent reflections
1741 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.078
S = 0.95
2491 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS96 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL96 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011901/ng5134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011901/ng5134Isup2.hkl

checkCIF report

Comment top

We recently explored the use of commercially available phenylsulfonylacetic acid under base catalysis with the anticipation of observing the same mode of transfer using sulfonium salts; methylene transfer onto carbonyl derivatives. The use of not sulfonium but sulfonyl functionality does allow for one to explore catalysis, which is a realm of S-ylide chemistry yet to be fully explored. For this study, observed was not only methylene transfer but formation of the condensation adduct vinyl sulfone (an α,β-unsaturated sulfone). Under not base but acid catalysis, this type of condensation is common as previously reported by Baliah & Seshapathirao (1959) and Jones (1967). The title compound, C₁₄H₁₀Cl₂O₂S, was isolated as the major product in moderate yield and offered definitive evidence of the condensation of the 2,6-dichlorobenzaldehyde with phenylsulfonylacetic acid.

The C1–C2 bond distance of 1.320 (3) Å confirms the alkene moiety, the configuration of which is E. This distance is slightly elongated as compared with the comparable distance of 1.313 (3) Å in phenyl vinyl sulfone (PVS) reported by Briggs et al. (1998). Other geometric parameters in the title compound are similar but also subtly affected relative to PVS. For example, the average S=O bond lengths are 1.436 (2) Å in the title compound but 1.443 (1) Å in PVS. Also shortened are the S–C bonds in the title compound (1.7683 (19) and 1.748 (2) Å) relative to PVS (1.770 (2) and 1.755 (2) Å), the longer bond in both cases being to the phenyl moiety. The C–S–C bond is noticably more acute in the title compound (102.84 (9)°) relative to PVS (104.64 (8)°), while the O=S=O angle in PVS (118.79 (8)°) is slightly more acute than the comparable angle in the title compound (119.35 (10)°). The torsion angle between the alkene moiety and the 2,6-dichlorophenyl ring in the title compound is 40.8 (3)°.

Related literature top

For a review on the use of vinyl sulfones in organic chemistry, see: Simpkins (1990). For the use of phenylsulfonylacetic acid in the formation of vinyl sulfones, see: Baliah & Seshapathirao (1959). For a general review on the condensation of activated methylenes onto aryl aldehydes, see: Jones (1967). For the structure of the related phenyl vinyl sulfone, see: Briggs et al. (1998).

Experimental top

To a 0.125M THF solution of phenylsulfonylacetic acid (1 g, 4.99 mmol, 2.0 equiv) was added 439 mg of 2,6-dichlorobenzaldehyde (2.51 mmol, 1.0 equiv). A 40 wt% solution of benzyltrimethylammonium hydroxide in methanol was next added by syringe (2.1 ml, 4.99 mmol, 2.0 equiv). The 50 ml one-neck round bottomed flask equipped with a magnetic stir bar was fitted with a condenser and allowed to warm to reflux. After a period of 18 h, the solution was cooled to 60 °C and 15 ml of deionized water was added and allowed to stir at this temperature for a period of 1 h. The resulting mixture was allowed to cool to room temperature at which time the mixture was washed with approximately 20 ml of ethyl acetate. After partitioning the organic from the aqueous phase, the organic fraction was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification by column chromatography over silica gel (eluting with 9:1 hexanes/ethyl acetate) afforded the title compound (355 mg, 45% yield). White crystalline solid, mp: 78–82 °C. IR (KBr): 1628, 1446, 1307, 1147 cm^{-1. 1}H NMR (300 MHz; CDCl₃) δ 7.19 (2H, m), 7.35 (2H, s), 7.64 (2H, m), 7.84 (1H, d, J = 15.9 Hz), 7.98 (1H, brs); ¹³C NMR (300 MHz; CDCl₃) δ 128.4, 129.5, 129.9, 131.3, 133.9, 135.3, 135.9, 136.3, 140.1; EI—MS (m/z) 313 (M+); HRMS calcd for C₁₄H₁₀Cl₂O₂S (M+H) 312.9857, found 312.9858.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS96 (Sheldrick, 2008); program(s) used to refine structure: SHELXL96 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. A thermal ellipsoid plot (50%) of the title compound showing the labeling scheme.

2,6-Dichloro-1-[(1E)-2-(phenylsulfonyl)ethenyl]benzene top

Crystal data top

C₁₄H₁₀Cl₂O₂S	Z = 2
M_r = 313.18	F(000) = 320
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5924 (6) Å	Cell parameters from 2060 reflections
b = 8.3060 (4) Å	θ = 3.2–25.3°
c = 11.3360 (9) Å	µ = 0.62 mm⁻¹
α = 78.639 (5)°	T = 290 K
β = 84.976 (7)°	Plate, colorless
γ = 77.497 (6)°	0.52 × 0.34 × 0.06 mm
V = 683.49 (8) Å³

Data collection top

Oxford Xcalibur E diffractometer	2491 independent reflections
Radiation source: fine-focus sealed tube	1741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 16.0514 pixels mm^-1	θ_max = 25.4°, θ_min = 3.2°
ω scans	h = −9→9
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→10
T_min = 0.810, T_max = 0.961	l = −13→13
4291 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0394P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
2491 reflections	Δρ_max = 0.20 e Å⁻³
173 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (2)

Crystal data top

C₁₄H₁₀Cl₂O₂S	γ = 77.497 (6)°
M_r = 313.18	V = 683.49 (8) Å³
Triclinic, P1	Z = 2
a = 7.5924 (6) Å	Mo Kα radiation
b = 8.3060 (4) Å	µ = 0.62 mm⁻¹
c = 11.3360 (9) Å	T = 290 K
α = 78.639 (5)°	0.52 × 0.34 × 0.06 mm
β = 84.976 (7)°

Data collection top

Oxford Xcalibur E diffractometer	2491 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	1741 reflections with I > 2σ(I)
T_min = 0.810, T_max = 0.961	R_int = 0.017
4291 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 0.95	Δρ_max = 0.20 e Å⁻³
2491 reflections	Δρ_min = −0.22 e Å⁻³
173 parameters

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 > 2σ(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	0.09983 (8)	0.38328 (6)	0.16893 (5)	0.04924 (19)
Cl1	0.28536 (9)	0.37676 (7)	0.55021 (6)	0.0761 (2)
Cl2	0.22076 (8)	−0.20158 (6)	0.41978 (5)	0.0586 (2)
O1	0.2065 (2)	0.25879 (17)	0.10588 (14)	0.0635 (5)
O2	−0.0899 (2)	0.43654 (18)	0.14956 (15)	0.0668 (5)
C1	0.1250 (3)	0.3114 (2)	0.32340 (19)	0.0453 (5)
H1	0.0678	0.3793	0.3774	0.054*
C2	0.2236 (3)	0.1626 (2)	0.36487 (19)	0.0429 (5)
H2	0.2819	0.1011	0.3073	0.051*
C3	0.2521 (2)	0.0828 (2)	0.49086 (18)	0.0386 (5)
C4	0.2567 (3)	−0.0897 (2)	0.52656 (19)	0.0418 (5)
C5	0.2828 (3)	−0.1734 (3)	0.6421 (2)	0.0534 (6)
H5	0.2842	−0.2878	0.6616	0.064*
C6	0.3067 (3)	−0.0875 (3)	0.7290 (2)	0.0628 (7)
H6	0.3230	−0.1430	0.8082	0.075*
C7	0.3066 (3)	0.0818 (3)	0.6987 (2)	0.0601 (7)
H7	0.3249	0.1400	0.7572	0.072*
C8	0.2794 (3)	0.1645 (2)	0.5823 (2)	0.0489 (6)
C9	0.1980 (3)	0.5626 (2)	0.14040 (18)	0.0420 (5)
C10	0.0892 (3)	0.7191 (2)	0.1258 (2)	0.0552 (6)
H10	−0.0358	0.7315	0.1295	0.066*
C11	0.1671 (4)	0.8583 (3)	0.1055 (2)	0.0666 (7)
H11	0.0944	0.9651	0.0967	0.080*
C12	0.3499 (4)	0.8396 (3)	0.0984 (2)	0.0646 (7)
H12	0.4015	0.9338	0.0847	0.077*
C13	0.4585 (3)	0.6833 (3)	0.1112 (2)	0.0684 (7)
H13	0.5834	0.6716	0.1048	0.082*
C14	0.3827 (3)	0.5431 (3)	0.1335 (2)	0.0574 (6)
H14	0.4558	0.4364	0.1438	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0624 (4)	0.0385 (3)	0.0468 (4)	−0.0171 (3)	−0.0074 (3)	0.0017 (2)
Cl1	0.0899 (5)	0.0429 (3)	0.1012 (6)	−0.0076 (3)	−0.0297 (4)	−0.0227 (3)
Cl2	0.0746 (4)	0.0417 (3)	0.0626 (4)	−0.0171 (3)	−0.0078 (3)	−0.0088 (3)
O1	0.1015 (13)	0.0397 (8)	0.0520 (10)	−0.0200 (8)	0.0019 (9)	−0.0110 (7)
O2	0.0585 (10)	0.0693 (10)	0.0709 (12)	−0.0269 (8)	−0.0199 (9)	0.0141 (8)
C1	0.0487 (13)	0.0397 (11)	0.0445 (14)	−0.0069 (10)	0.0002 (10)	−0.0040 (10)
C2	0.0411 (12)	0.0379 (11)	0.0488 (14)	−0.0107 (9)	0.0018 (10)	−0.0047 (10)
C3	0.0321 (11)	0.0369 (10)	0.0441 (13)	−0.0055 (8)	−0.0011 (9)	−0.0031 (9)
C4	0.0359 (12)	0.0397 (11)	0.0488 (14)	−0.0095 (9)	−0.0015 (10)	−0.0042 (10)
C5	0.0530 (14)	0.0442 (12)	0.0578 (16)	−0.0106 (10)	−0.0052 (11)	0.0051 (11)
C6	0.0648 (17)	0.0724 (17)	0.0435 (16)	−0.0043 (13)	−0.0111 (12)	0.0009 (12)
C7	0.0566 (16)	0.0715 (16)	0.0539 (17)	−0.0025 (13)	−0.0132 (12)	−0.0226 (13)
C8	0.0426 (13)	0.0448 (12)	0.0593 (16)	−0.0020 (10)	−0.0073 (11)	−0.0147 (11)
C9	0.0524 (14)	0.0362 (11)	0.0372 (13)	−0.0095 (10)	−0.0051 (10)	−0.0043 (9)
C10	0.0523 (14)	0.0432 (12)	0.0685 (17)	−0.0047 (11)	−0.0138 (12)	−0.0070 (11)
C11	0.091 (2)	0.0358 (12)	0.0729 (19)	−0.0110 (13)	−0.0263 (16)	−0.0023 (11)
C12	0.096 (2)	0.0589 (16)	0.0488 (16)	−0.0414 (15)	−0.0048 (14)	−0.0056 (12)
C13	0.0584 (16)	0.0802 (18)	0.079 (2)	−0.0298 (14)	0.0101 (14)	−0.0331 (15)
C14	0.0552 (15)	0.0480 (12)	0.0706 (18)	−0.0073 (11)	−0.0029 (12)	−0.0187 (12)

Geometric parameters (Å, º) top

S1—O2	1.4353 (16)	C6—C7	1.380 (3)
S1—O1	1.4364 (15)	C6—H6	0.9300
S1—C1	1.748 (2)	C7—C8	1.373 (3)
S1—C9	1.7683 (19)	C7—H7	0.9300
Cl1—C8	1.738 (2)	C9—C10	1.369 (3)
Cl2—C4	1.736 (2)	C9—C14	1.373 (3)
C1—C2	1.320 (3)	C10—C11	1.381 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.464 (3)	C11—C12	1.360 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C8	1.398 (3)	C12—C13	1.367 (3)
C3—C4	1.404 (3)	C12—H12	0.9300
C4—C5	1.365 (3)	C13—C14	1.378 (3)
C5—C6	1.371 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300

O2—S1—O1	119.35 (10)	C8—C7—C6	120.1 (2)
O2—S1—C1	107.76 (10)	C8—C7—H7	119.9
O1—S1—C1	108.27 (9)	C6—C7—H7	119.9
O2—S1—C9	108.45 (9)	C7—C8—C3	122.2 (2)
O1—S1—C9	108.92 (9)	C7—C8—Cl1	117.54 (16)
C1—S1—C9	102.84 (9)	C3—C8—Cl1	120.25 (17)
C2—C1—S1	121.25 (17)	C10—C9—C14	120.77 (19)
C2—C1—H1	119.4	C10—C9—S1	119.66 (16)
S1—C1—H1	119.4	C14—C9—S1	119.57 (15)
C1—C2—C3	127.63 (19)	C9—C10—C11	119.2 (2)
C1—C2—H2	116.2	C9—C10—H10	120.4
C3—C2—H2	116.2	C11—C10—H10	120.4
C8—C3—C4	115.12 (19)	C12—C11—C10	120.2 (2)
C8—C3—C2	125.15 (17)	C12—C11—H11	119.9
C4—C3—C2	119.72 (17)	C10—C11—H11	119.9
C5—C4—C3	123.29 (18)	C11—C12—C13	120.5 (2)
C5—C4—Cl2	118.16 (15)	C11—C12—H12	119.7
C3—C4—Cl2	118.52 (16)	C13—C12—H12	119.7
C4—C5—C6	119.5 (2)	C12—C13—C14	120.0 (2)
C4—C5—H5	120.3	C12—C13—H13	120.0
C6—C5—H5	120.3	C14—C13—H13	120.0
C5—C6—C7	119.8 (2)	C9—C14—C13	119.3 (2)
C5—C6—H6	120.1	C9—C14—H14	120.3
C7—C6—H6	120.1	C13—C14—H14	120.3

O2—S1—C1—C2	128.08 (17)	C2—C3—C8—C7	−179.5 (2)
O1—S1—C1—C2	−2.3 (2)	C4—C3—C8—Cl1	177.68 (14)
C9—S1—C1—C2	−117.47 (18)	C2—C3—C8—Cl1	−1.1 (3)
S1—C1—C2—C3	−177.57 (14)	O2—S1—C9—C10	10.8 (2)
C1—C2—C3—C8	−40.8 (3)	O1—S1—C9—C10	142.12 (18)
C1—C2—C3—C4	140.4 (2)	C1—S1—C9—C10	−103.16 (19)
C8—C3—C4—C5	1.1 (3)	O2—S1—C9—C14	−169.41 (17)
C2—C3—C4—C5	179.93 (18)	O1—S1—C9—C14	−38.06 (19)
C8—C3—C4—Cl2	179.04 (14)	C1—S1—C9—C14	76.65 (18)
C2—C3—C4—Cl2	−2.1 (3)	C14—C9—C10—C11	−0.9 (3)
C3—C4—C5—C6	−0.3 (3)	S1—C9—C10—C11	178.95 (17)
Cl2—C4—C5—C6	−178.28 (17)	C9—C10—C11—C12	1.0 (3)
C4—C5—C6—C7	−0.8 (3)	C10—C11—C12—C13	0.0 (4)
C5—C6—C7—C8	1.1 (4)	C11—C12—C13—C14	−1.1 (4)
C6—C7—C8—C3	−0.3 (3)	C10—C9—C14—C13	−0.2 (3)
C6—C7—C8—Cl1	−178.79 (18)	S1—C9—C14—C13	179.95 (18)
C4—C3—C8—C7	−0.8 (3)	C12—C13—C14—C9	1.2 (4)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀Cl₂O₂S
M_r	313.18
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	7.5924 (6), 8.3060 (4), 11.3360 (9)
α, β, γ (°)	78.639 (5), 84.976 (7), 77.497 (6)
V (Å³)	683.49 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.52 × 0.34 × 0.06

Data collection
Diffractometer	Oxford Xcalibur E diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.810, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	4291, 2491, 1741
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.078, 0.95
No. of reflections	2491
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS96 (Sheldrick, 2008), SHELXL96 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010).

Acknowledgements

The authors gratefully acknowledge the National Science Foundation (NSF-CAREER grant to RES, CHE-0846680; NSF-RUI grant to DCF, CHE-0957482). DCF also gratefully acknowledges the NIGMS (NIH NIGMS 1R15GM085936) and the Camille and Henry Dreyfus Foundation (TH-06–008) for partial support of this work.

References

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