4-Allyl-2-meth­oxy­phenyl 3,4-dichloro­benzene­sulfonate

Ma, Y.-T.; Gao, Z.-F.; Liu, Q.-C.; Jin, G.; Gao, J.-M.

doi:10.1107/S1600536811044163

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3082

doi:10.1107/S1600536811044163

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4-Allyl-2-methoxyphenyl 3,4-dichlorobenzenesulfonate

Ya-Tuan Ma,^a Zhao-Feng Gao,^b Qi-Chao Liu,^b Gang Jin ^b and Jin-Ming Gao ^b ^*

^aCollege of Science and College of Life Sciences, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China
^*Correspondence e-mail: mnathantuan@yahoo.com

(Received 11 October 2011; accepted 24 October 2011; online 29 October 2011)

The title compound, C₁₆H₁₄Cl₂O₄S, was obtained by the reaction of eugenol (4-allyl-2-methoxyphenol) and 3,4-dichlorobenzenesulfonyl chloride. The dihedral angle between the benzene rings in the molecule is 40.53 (4)°. No significantly short intermolecular contacts are observed in the crystal structure.

Related literature

For the synthesis of eugenol derivatives, see: Sadeghian et al. (2008 ). For a related structure, see: Ma et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₄Cl₂O₄S
M_r = 373.23
Triclinic, $[P \overline 1]$
a = 8.8694 (8) Å
b = 9.7501 (9) Å
c = 10.3796 (11) Å
α = 83.369 (2)°
β = 76.196 (1)°
γ = 80.038 (1)°
V = 855.95 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.801, T_max = 0.860
4290 measured reflections
2967 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.02
2967 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811044163/bh2390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044163/bh2390Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044163/bh2390Isup3.cml

checkCIF report

Comment top

In this paper, we present the structure of the title compound (Fig. 1), which was synthesized by the reaction of eugenol and 3,4-dichlorobenzenesulfonyl chloride (Sadeghian et al., 2008). We previously reported a compound of this type (Ma et al., 2010). In the molecular structure, the bond lengths and angles are normal and the dihedral angle between the aromatic rings is 40.53 (4)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For the synthesis of eugenol derivatives, see: Sadeghian et al. (2008). For a related structure, see: Ma et al. (2010).

Experimental top

492 mg of eugenol (3 mmol), triethylamine (4 mmol), 3,4-dichlorobenzenesulfonyl chloride (3 mmol), and 40 ml of dichloromethane were mixed in a 100 ml flask. After 2 h under stirring at 278 K, the crude product was obtained. The crystals were obtained by recrystallization from methanol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram.

4-Allyl-2-methoxyphenyl 3,4-dichlorobenzenesulfonate top

Crystal data top

C₁₆H₁₄Cl₂O₄S	Z = 2
M_r = 373.23	F(000) = 384
Triclinic, P1	D_x = 1.448 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8694 (8) Å	Cell parameters from 1336 reflections
b = 9.7501 (9) Å	θ = 2.8–23.7°
c = 10.3796 (11) Å	µ = 0.52 mm⁻¹
α = 83.369 (2)°	T = 298 K
β = 76.196 (1)°	Prism, colourless
γ = 80.038 (1)°	0.45 × 0.40 × 0.30 mm
V = 855.95 (14) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2967 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.801, T_max = 0.860	k = −11→11
4290 measured reflections	l = −9→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0575P)² + 0.4401P] where P = (F_o² + 2F_c²)/3
2967 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³
0 constraints

Crystal data top

C₁₆H₁₄Cl₂O₄S	γ = 80.038 (1)°
M_r = 373.23	V = 855.95 (14) Å³
Triclinic, P1	Z = 2
a = 8.8694 (8) Å	Mo Kα radiation
b = 9.7501 (9) Å	µ = 0.52 mm⁻¹
c = 10.3796 (11) Å	T = 298 K
α = 83.369 (2)°	0.45 × 0.40 × 0.30 mm
β = 76.196 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2967 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1762 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.860	R_int = 0.017
4290 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
2967 reflections	Δρ_min = −0.33 e Å⁻³
209 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.82040 (13)	0.91886 (11)	1.44301 (11)	0.0879 (4)
Cl2	0.75166 (16)	1.04135 (13)	1.72255 (11)	0.0992 (4)
O1	0.5562 (2)	1.4568 (2)	1.2109 (2)	0.0595 (6)
O2	0.4219 (3)	1.2645 (3)	1.1872 (3)	0.0871 (9)
O3	0.2975 (3)	1.4507 (3)	1.3373 (3)	0.0915 (9)
O4	0.8069 (3)	1.4105 (3)	1.3153 (2)	0.0630 (6)
S1	0.43068 (11)	1.35611 (11)	1.28005 (11)	0.0703 (3)
C1	0.7014 (4)	1.3996 (3)	1.1322 (3)	0.0552 (9)
C2	0.8326 (4)	1.3787 (3)	1.1873 (3)	0.0548 (8)
C3	0.9776 (4)	1.3308 (4)	1.1077 (4)	0.0653 (10)
H3	1.0669	1.3146	1.1428	0.078*
C4	0.9901 (5)	1.3068 (4)	0.9758 (4)	0.0733 (11)
C5	0.8575 (6)	1.3299 (4)	0.9242 (4)	0.0807 (12)
H5	0.8659	1.3141	0.8359	0.097*
C6	0.7135 (5)	1.3759 (4)	1.0020 (4)	0.0716 (11)
H6	0.6244	1.3909	0.9669	0.086*
C7	0.9350 (5)	1.3767 (6)	1.3797 (4)	0.0961 (15)
H7A	0.9763	1.2793	1.3742	0.144*
H7B	0.8993	1.3964	1.4715	0.144*
H7C	1.0157	1.4315	1.3369	0.144*
C8	1.1522 (6)	1.2558 (5)	0.8904 (4)	0.0989 (16)
H8A	1.1523	1.2820	0.7973	0.119*
H8B	1.2304	1.3008	0.9136	0.119*
C9	1.1938 (7)	1.1033 (5)	0.9099 (4)	0.1003 (16)
H9	1.1251	1.0486	0.8940	0.120*
C10	1.3139 (8)	1.0416 (7)	0.9462 (5)	0.133 (2)
H10A	1.3855	1.0926	0.9632	0.159*
H10B	1.3318	0.9445	0.9563	0.159*
C11	0.5144 (4)	1.2605 (4)	1.4070 (3)	0.0578 (9)
C12	0.6161 (4)	1.1383 (4)	1.3789 (3)	0.0564 (9)
H12	0.6347	1.1026	1.2964	0.068*
C13	0.6895 (4)	1.0704 (4)	1.4771 (4)	0.0588 (9)
C14	0.6590 (4)	1.1249 (4)	1.6005 (4)	0.0651 (10)
C15	0.5542 (5)	1.2442 (4)	1.6267 (4)	0.0728 (11)
H15	0.5319	1.2779	1.7105	0.087*
C16	0.4817 (4)	1.3143 (4)	1.5303 (4)	0.0682 (10)
H16	0.4120	1.3965	1.5473	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0900 (8)	0.0784 (7)	0.0890 (8)	0.0078 (6)	−0.0208 (6)	−0.0102 (6)
Cl2	0.1245 (11)	0.1074 (9)	0.0685 (7)	−0.0214 (8)	−0.0319 (7)	0.0095 (6)
O1	0.0484 (14)	0.0575 (14)	0.0743 (16)	0.0003 (11)	−0.0208 (12)	−0.0098 (12)
O2	0.089 (2)	0.091 (2)	0.099 (2)	−0.0254 (16)	−0.0462 (17)	−0.0127 (16)
O3	0.0432 (15)	0.109 (2)	0.120 (2)	0.0058 (15)	−0.0224 (15)	−0.0165 (18)
O4	0.0466 (13)	0.0839 (17)	0.0603 (15)	−0.0047 (12)	−0.0146 (11)	−0.0154 (13)
S1	0.0509 (6)	0.0797 (7)	0.0867 (7)	−0.0086 (5)	−0.0258 (5)	−0.0125 (5)
C1	0.057 (2)	0.049 (2)	0.060 (2)	−0.0025 (16)	−0.0165 (17)	−0.0059 (16)
C2	0.054 (2)	0.049 (2)	0.060 (2)	−0.0053 (16)	−0.0118 (17)	−0.0059 (16)
C3	0.058 (2)	0.061 (2)	0.068 (2)	−0.0009 (18)	−0.0059 (19)	0.0014 (18)
C4	0.086 (3)	0.053 (2)	0.063 (3)	0.005 (2)	0.004 (2)	0.0011 (19)
C5	0.103 (4)	0.074 (3)	0.059 (2)	−0.001 (3)	−0.015 (2)	−0.008 (2)
C6	0.084 (3)	0.068 (3)	0.064 (2)	0.000 (2)	−0.026 (2)	−0.005 (2)
C7	0.057 (2)	0.158 (5)	0.082 (3)	−0.004 (3)	−0.034 (2)	−0.023 (3)
C8	0.101 (3)	0.076 (3)	0.086 (3)	0.011 (3)	0.023 (3)	0.002 (2)
C9	0.109 (4)	0.095 (4)	0.073 (3)	0.018 (3)	0.008 (3)	−0.017 (3)
C10	0.156 (6)	0.141 (5)	0.078 (3)	0.031 (5)	−0.014 (4)	−0.017 (3)
C11	0.048 (2)	0.062 (2)	0.066 (2)	−0.0153 (17)	−0.0104 (17)	−0.0087 (18)
C12	0.051 (2)	0.062 (2)	0.059 (2)	−0.0159 (18)	−0.0095 (17)	−0.0103 (17)
C13	0.054 (2)	0.057 (2)	0.065 (2)	−0.0165 (17)	−0.0068 (18)	−0.0049 (18)
C14	0.070 (2)	0.072 (3)	0.055 (2)	−0.026 (2)	−0.0103 (18)	0.0020 (19)
C15	0.081 (3)	0.076 (3)	0.059 (2)	−0.018 (2)	−0.002 (2)	−0.014 (2)
C16	0.062 (2)	0.066 (2)	0.071 (3)	−0.0100 (19)	0.001 (2)	−0.017 (2)

Geometric parameters (Å, º) top

Cl1—C13	1.729 (4)	C7—H7A	0.9600
Cl2—C14	1.724 (4)	C7—H7B	0.9600
O1—C1	1.411 (4)	C7—H7C	0.9600
O1—S1	1.598 (2)	C8—C9	1.471 (6)
O2—S1	1.411 (3)	C8—H8A	0.9700
O3—S1	1.419 (3)	C8—H8B	0.9700
O4—C2	1.356 (4)	C9—C10	1.247 (7)
O4—C7	1.424 (4)	C9—H9	0.9300
S1—C11	1.761 (4)	C10—H10A	0.9300
C1—C6	1.372 (5)	C10—H10B	0.9300
C1—C2	1.390 (4)	C11—C12	1.379 (4)
C2—C3	1.389 (5)	C11—C16	1.387 (5)
C3—C4	1.391 (5)	C12—C13	1.383 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (6)	C13—C14	1.391 (5)
C4—C8	1.531 (5)	C14—C15	1.367 (5)
C5—C6	1.371 (6)	C15—C16	1.371 (5)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300

C1—O1—S1	119.2 (2)	H7B—C7—H7C	109.5
C2—O4—C7	117.7 (3)	C9—C8—C4	111.4 (4)
O2—S1—O3	121.23 (17)	C9—C8—H8A	109.4
O2—S1—O1	109.01 (16)	C4—C8—H8A	109.4
O3—S1—O1	102.96 (16)	C9—C8—H8B	109.4
O2—S1—C11	109.38 (17)	C4—C8—H8B	109.4
O3—S1—C11	109.49 (18)	H8A—C8—H8B	108.0
O1—S1—C11	103.13 (14)	C10—C9—C8	125.2 (6)
C6—C1—C2	121.5 (3)	C10—C9—H9	117.4
C6—C1—O1	120.5 (3)	C8—C9—H9	117.4
C2—C1—O1	117.9 (3)	C9—C10—H10A	120.0
O4—C2—C3	125.6 (3)	C9—C10—H10B	120.0
O4—C2—C1	116.1 (3)	H10A—C10—H10B	120.0
C3—C2—C1	118.3 (3)	C12—C11—C16	122.1 (3)
C2—C3—C4	120.3 (4)	C12—C11—S1	119.1 (3)
C2—C3—H3	119.8	C16—C11—S1	118.7 (3)
C4—C3—H3	119.8	C11—C12—C13	118.1 (3)
C5—C4—C3	119.7 (4)	C11—C12—H12	121.0
C5—C4—C8	121.3 (4)	C13—C12—H12	121.0
C3—C4—C8	118.9 (4)	C12—C13—C14	120.1 (3)
C6—C5—C4	120.5 (4)	C12—C13—Cl1	118.9 (3)
C6—C5—H5	119.7	C14—C13—Cl1	121.0 (3)
C4—C5—H5	119.7	C15—C14—C13	120.5 (3)
C5—C6—C1	119.7 (4)	C15—C14—Cl2	119.3 (3)
C5—C6—H6	120.2	C13—C14—Cl2	120.2 (3)
C1—C6—H6	120.2	C14—C15—C16	120.4 (4)
O4—C7—H7A	109.5	C14—C15—H15	119.8
O4—C7—H7B	109.5	C16—C15—H15	119.8
H7A—C7—H7B	109.5	C15—C16—C11	118.8 (4)
O4—C7—H7C	109.5	C15—C16—H16	120.6
H7A—C7—H7C	109.5	C11—C16—H16	120.6

C1—O1—S1—O2	−44.3 (3)	C3—C4—C8—C9	83.8 (5)
C1—O1—S1—O3	−174.3 (2)	C4—C8—C9—C10	−123.3 (6)
C1—O1—S1—C11	71.8 (3)	O2—S1—C11—C12	27.3 (3)
S1—O1—C1—C6	82.4 (4)	O3—S1—C11—C12	162.3 (3)
S1—O1—C1—C2	−102.5 (3)	O1—S1—C11—C12	−88.6 (3)
C7—O4—C2—C3	−8.0 (5)	O2—S1—C11—C16	−155.9 (3)
C7—O4—C2—C1	173.5 (3)	O3—S1—C11—C16	−20.9 (3)
C6—C1—C2—O4	177.7 (3)	O1—S1—C11—C16	88.2 (3)
O1—C1—C2—O4	2.6 (5)	C16—C11—C12—C13	−1.5 (5)
C6—C1—C2—C3	−1.0 (5)	S1—C11—C12—C13	175.2 (2)
O1—C1—C2—C3	−176.0 (3)	C11—C12—C13—C14	0.6 (5)
O4—C2—C3—C4	−177.4 (3)	C11—C12—C13—Cl1	−178.8 (3)
C1—C2—C3—C4	1.0 (5)	C12—C13—C14—C15	1.2 (5)
C2—C3—C4—C5	−0.5 (6)	Cl1—C13—C14—C15	−179.4 (3)
C2—C3—C4—C8	179.2 (3)	C12—C13—C14—Cl2	−179.4 (3)
C3—C4—C5—C6	−0.2 (6)	Cl1—C13—C14—Cl2	−0.1 (4)
C8—C4—C5—C6	−179.9 (4)	C13—C14—C15—C16	−2.2 (6)
C4—C5—C6—C1	0.3 (6)	Cl2—C14—C15—C16	178.5 (3)
C2—C1—C6—C5	0.3 (6)	C14—C15—C16—C11	1.3 (6)
O1—C1—C6—C5	175.2 (3)	C12—C11—C16—C15	0.6 (5)
C5—C4—C8—C9	−96.5 (5)	S1—C11—C16—C15	−176.2 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄Cl₂O₄S
M_r	373.23
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.8694 (8), 9.7501 (9), 10.3796 (11)
α, β, γ (°)	83.369 (2), 76.196 (1), 80.038 (1)
V (Å³)	855.95 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.45 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.801, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	4290, 2967, 1762
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.02
No. of reflections	2967
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We acknowledge funding support from the National Natural Science Foundation of China (grant No. 30971882), Shaanxi Province Science and Technology (under contract No. 2011k02–07) and the Program of Northwest A&F University (No. Z111020908).

References

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