Bis(4-eth-oxy-phen-yl) sulfoxide.

In the title compound, C(16)H(18)O(3)S, the dihedral angle between the benzene rings is 82.7 (2)°. The O atom of the sulfoxide group is disordered over two orientations with refined occupancy factors of 0.563 (3):0.437 (3). In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For background to Friedel–Crafts acyl­ation, see: Edward & Sibelle (1963 ▶); DeHaan et al. (1979 ▶); Fillion & Fishlock (2005 ▶); Nishimoto et al. (2008 ▶). For the structures of related aryl­sulfoxides, see: Casarini et al. (2004 ▶); Noland & Kedrowski (2000 ▶).

Experimental

Crystal data

C16H18O3S

M = 290.36

Triclinic,

a = 8.2052 (16) Å

b = 9.856 (2) Å

c = 10.196 (2) Å

α = 64.71 (3)°

β = 83.78 (3)°

γ = 82.88 (3)°

V = 738.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.957, T max = 0.974

6624 measured reflections

3450 independent reflections

2590 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.06

3450 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks I, global. DOI: 10.1107/S1600536811013213/rz2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013213/rz2577Isup2.hkl

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

C16H18O3S	Z = 2
Mr = 290.36	F(000) = 308
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2052 (16) Å	Cell parameters from 2289 reflections
b = 9.856 (2) Å	θ = 2.2–27.9°
c = 10.196 (2) Å	µ = 0.22 mm−1
α = 64.71 (3)°	T = 113 K
β = 83.78 (3)°	Block, colourless
γ = 82.88 (3)°	0.20 × 0.16 × 0.12 mm
V = 738.4 (3) Å3

Rigaku Saturn CCD area-detector diffractometer	3450 independent reflections
Radiation source: rotating anode	2590 reflections with I > 2σ(I)
confocal	Rint = 0.022
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −12→9
Tmin = 0.957, Tmax = 0.974	l = −13→12
6624 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.2002P] where P = (Fo2 + 2Fc2)/3
3450 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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	Occ. (<1)
S1	−0.00304 (4)	0.50094 (4)	0.73977 (4)	0.02589 (12)
O1	0.32089 (14)	−0.11895 (11)	0.97342 (11)	0.0264 (2)
O2A	−0.0884 (2)	0.5328 (2)	0.8531 (2)	0.0284 (5)	0.563 (3)
O2B	−0.0815 (3)	0.5217 (3)	0.6188 (3)	0.0274 (7)	0.437 (3)
O3	0.60436 (12)	0.81887 (11)	0.56357 (10)	0.0237 (2)
C1	0.4363 (2)	−0.35101 (18)	1.14478 (18)	0.0316 (4)
H1A	0.4553	−0.4098	1.2457	0.047*
H1B	0.5396	−0.3364	1.0887	0.047*
H1C	0.3694	−0.4028	1.1126	0.047*
C2	0.34927 (19)	−0.20046 (16)	1.12487 (15)	0.0248 (3)
H2A	0.2456	−0.2138	1.1827	0.030*
H2B	0.4167	−0.1460	1.1551	0.030*
C3	0.24360 (17)	0.02257 (15)	0.92796 (15)	0.0205 (3)
C4	0.18830 (19)	0.09277 (17)	1.01871 (16)	0.0247 (3)
H4	0.2018	0.0426	1.1180	0.030*
C5	0.11249 (18)	0.23851 (17)	0.96065 (16)	0.0252 (3)
H5	0.0752	0.2862	1.0211	0.030*
C6	0.09267 (17)	0.31234 (15)	0.81312 (16)	0.0211 (3)
C7	0.14640 (19)	0.24226 (17)	0.72137 (16)	0.0261 (3)
H7	0.1315	0.2921	0.6223	0.031*
C8	0.2223 (2)	0.09749 (17)	0.77930 (16)	0.0259 (3)
H8	0.2592	0.0499	0.7188	0.031*
C9	0.17993 (17)	0.59829 (15)	0.68666 (16)	0.0217 (3)
C10	0.23615 (18)	0.64787 (16)	0.78032 (16)	0.0223 (3)
H10	0.1784	0.6310	0.8688	0.027*
C11	0.37828 (17)	0.72262 (15)	0.74289 (15)	0.0211 (3)
H11	0.4161	0.7561	0.8057	0.025*
C12	0.46333 (17)	0.74683 (15)	0.61065 (15)	0.0191 (3)
C13	0.40644 (19)	0.69756 (16)	0.51575 (15)	0.0240 (3)
H13	0.4643	0.7141	0.4274	0.029*
C14	0.26404 (18)	0.62420 (16)	0.55302 (16)	0.0240 (3)
H14	0.2248	0.5924	0.4895	0.029*
C15	0.67526 (18)	0.85931 (17)	0.66294 (16)	0.0235 (3)
H15A	0.6960	0.7712	0.7529	0.028*
H15B	0.6014	0.9326	0.6850	0.028*
C16	0.83409 (18)	0.92527 (18)	0.58926 (17)	0.0278 (3)
H16A	0.8900	0.9472	0.6550	0.042*
H16B	0.8110	1.0164	0.5043	0.042*
H16C	0.9025	0.8543	0.5616	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.01736 (17)	0.02001 (18)	0.0400 (2)	0.00022 (12)	−0.00217 (15)	−0.01266 (16)
O1	0.0373 (6)	0.0221 (5)	0.0180 (5)	0.0067 (4)	−0.0050 (4)	−0.0082 (4)
O2A	0.0233 (10)	0.0257 (10)	0.0363 (12)	−0.0013 (7)	0.0091 (8)	−0.0159 (9)
O2B	0.0276 (13)	0.0241 (13)	0.0301 (14)	−0.0007 (10)	−0.0155 (10)	−0.0081 (11)
O3	0.0258 (5)	0.0279 (6)	0.0200 (5)	−0.0089 (4)	0.0021 (4)	−0.0116 (4)
C1	0.0339 (9)	0.0257 (8)	0.0287 (9)	0.0021 (6)	−0.0069 (7)	−0.0054 (7)
C2	0.0304 (8)	0.0239 (7)	0.0173 (7)	−0.0016 (6)	−0.0049 (6)	−0.0054 (6)
C3	0.0223 (7)	0.0193 (7)	0.0199 (7)	−0.0006 (5)	−0.0017 (5)	−0.0082 (6)
C4	0.0310 (8)	0.0258 (8)	0.0171 (7)	−0.0021 (6)	0.0006 (6)	−0.0093 (6)
C5	0.0278 (8)	0.0259 (8)	0.0245 (8)	−0.0015 (6)	0.0049 (6)	−0.0150 (6)
C6	0.0161 (6)	0.0194 (7)	0.0279 (8)	−0.0025 (5)	−0.0005 (5)	−0.0101 (6)
C7	0.0338 (8)	0.0233 (7)	0.0210 (7)	0.0008 (6)	−0.0064 (6)	−0.0089 (6)
C8	0.0360 (8)	0.0239 (7)	0.0201 (7)	0.0036 (6)	−0.0034 (6)	−0.0127 (6)
C9	0.0189 (7)	0.0163 (6)	0.0284 (8)	0.0012 (5)	−0.0031 (6)	−0.0081 (6)
C10	0.0217 (7)	0.0224 (7)	0.0240 (7)	0.0001 (5)	0.0027 (6)	−0.0124 (6)
C11	0.0229 (7)	0.0216 (7)	0.0218 (7)	−0.0009 (5)	−0.0012 (6)	−0.0124 (6)
C12	0.0212 (7)	0.0154 (6)	0.0195 (7)	−0.0012 (5)	−0.0017 (5)	−0.0061 (5)
C13	0.0302 (8)	0.0241 (7)	0.0171 (7)	−0.0043 (6)	−0.0010 (6)	−0.0076 (6)
C14	0.0301 (8)	0.0219 (7)	0.0213 (7)	−0.0029 (6)	−0.0066 (6)	−0.0090 (6)
C15	0.0221 (7)	0.0291 (8)	0.0225 (7)	−0.0045 (6)	−0.0014 (6)	−0.0134 (6)
C16	0.0231 (7)	0.0342 (8)	0.0285 (8)	−0.0065 (6)	−0.0001 (6)	−0.0149 (7)

S1—O2B	1.379 (2)	C6—C7	1.391 (2)
S1—O2A	1.4156 (18)	C7—C8	1.383 (2)
S1—C9	1.7902 (15)	C7—H7	0.9300
S1—C6	1.7913 (16)	C8—H8	0.9300
O1—C3	1.3619 (17)	C9—C10	1.383 (2)
O1—C2	1.4338 (17)	C9—C14	1.393 (2)
O3—C12	1.3659 (17)	C10—C11	1.3873 (19)
O3—C15	1.4331 (16)	C10—H10	0.9300
C1—C2	1.505 (2)	C11—C12	1.387 (2)
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C13	1.3949 (19)
C1—H1C	0.9600	C13—C14	1.382 (2)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.385 (2)	C15—C16	1.505 (2)
C3—C8	1.394 (2)	C15—H15A	0.9700
C4—C5	1.390 (2)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.381 (2)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
O2B—S1—O2A	120.99 (14)	C6—C7—H7	120.4
O2B—S1—C9	110.29 (12)	C7—C8—C3	120.34 (13)
O2A—S1—C9	107.71 (9)	C7—C8—H8	119.8
O2B—S1—C6	107.72 (11)	C3—C8—H8	119.8
O2A—S1—C6	109.65 (10)	C10—C9—C14	120.52 (13)
C9—S1—C6	98.07 (7)	C10—C9—S1	118.90 (11)
C3—O1—C2	118.08 (11)	C14—C9—S1	120.58 (11)
C12—O3—C15	117.39 (11)	C9—C10—C11	120.32 (13)
C2—C1—H1A	109.5	C9—C10—H10	119.8
C2—C1—H1B	109.5	C11—C10—H10	119.8
H1A—C1—H1B	109.5	C12—C11—C10	119.24 (13)
C2—C1—H1C	109.5	C12—C11—H11	120.4
H1A—C1—H1C	109.5	C10—C11—H11	120.4
H1B—C1—H1C	109.5	O3—C12—C11	123.89 (12)
O1—C2—C1	107.09 (12)	O3—C12—C13	115.57 (12)
O1—C2—H2A	110.3	C11—C12—C13	120.54 (13)
C1—C2—H2A	110.3	C14—C13—C12	120.01 (13)
O1—C2—H2B	110.3	C14—C13—H13	120.0
C1—C2—H2B	110.3	C12—C13—H13	120.0
H2A—C2—H2B	108.6	C13—C14—C9	119.37 (13)
O1—C3—C4	124.36 (13)	C13—C14—H14	120.3
O1—C3—C8	115.56 (12)	C9—C14—H14	120.3
C4—C3—C8	120.08 (13)	O3—C15—C16	106.61 (11)
C3—C4—C5	119.69 (13)	O3—C15—H15A	110.4
C3—C4—H4	120.2	C16—C15—H15A	110.4
C5—C4—H4	120.2	O3—C15—H15B	110.4
C6—C5—C4	119.88 (13)	C16—C15—H15B	110.4
C6—C5—H5	120.1	H15A—C15—H15B	108.6
C4—C5—H5	120.1	C15—C16—H16A	109.5
C5—C6—C7	120.83 (14)	C15—C16—H16B	109.5
C5—C6—S1	119.31 (11)	H16A—C16—H16B	109.5
C7—C6—S1	119.86 (12)	C15—C16—H16C	109.5
C8—C7—C6	119.17 (14)	H16A—C16—H16C	109.5
C8—C7—H7	120.4	H16B—C16—H16C	109.5
C3—O1—C2—C1	−179.66 (12)	O2B—S1—C9—C10	152.14 (15)
C2—O1—C3—C4	−0.9 (2)	O2A—S1—C9—C10	18.17 (15)
C2—O1—C3—C8	178.78 (13)	C6—S1—C9—C10	−95.51 (12)
O1—C3—C4—C5	179.25 (13)	O2B—S1—C9—C14	−27.63 (17)
C8—C3—C4—C5	−0.4 (2)	O2A—S1—C9—C14	−161.60 (13)
C3—C4—C5—C6	0.0 (2)	C6—S1—C9—C14	84.72 (13)
C4—C5—C6—C7	0.6 (2)	C14—C9—C10—C11	−0.7 (2)
C4—C5—C6—S1	−179.25 (11)	S1—C9—C10—C11	179.49 (11)
O2B—S1—C6—C5	−150.37 (15)	C9—C10—C11—C12	−0.1 (2)
O2A—S1—C6—C5	−16.90 (15)	C15—O3—C12—C11	5.76 (19)
C9—S1—C6—C5	95.24 (13)	C15—O3—C12—C13	−174.52 (12)
O2B—S1—C6—C7	29.81 (17)	C10—C11—C12—O3	−179.91 (13)
O2A—S1—C6—C7	163.29 (13)	C10—C11—C12—C13	0.4 (2)
C9—S1—C6—C7	−84.58 (13)	O3—C12—C13—C14	−179.60 (13)
C5—C6—C7—C8	−0.8 (2)	C11—C12—C13—C14	0.1 (2)
S1—C6—C7—C8	179.03 (11)	C12—C13—C14—C9	−0.9 (2)
C6—C7—C8—C3	0.4 (2)	C10—C9—C14—C13	1.2 (2)
O1—C3—C8—C7	−179.49 (13)	S1—C9—C14—C13	−178.98 (11)
C4—C3—C8—C7	0.2 (2)	C12—O3—C15—C16	175.76 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.51	3.3013 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.51	3.3013 (18)	143

Symmetry code: (i) .