4-Allyl-2-meth-oxy-phenyl 3,4-dichloro-benzene-sulfonate.

The title compound, C(16)H(14)Cl(2)O(4)S, was obtained by the reaction of eugenol (4-allyl-2-meth-oxy-phenol) and 3,4-dichloro-benzene-sulfonyl chloride. The dihedral angle between the benzene rings in the mol-ecule is 40.53 (4)°. No significantly short inter-molecular 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 = 373.23

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.02

2967 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044163/bh2390sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811044163/bh2390Isup3.cml

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

C16H14Cl2O4S	Z = 2
Mr = 373.23	F(000) = 384
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0575P)2 + 0.4401P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.33 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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*

	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)

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)