1,2-Bis(4-meth-oxy-phen-oxy)ethane.

The whole mol-ecule of the title compound, C16H18O4, is generated by twofold rotational symmetry; the twofold axis bis-ects the central C-C bond. The O-C-C-O torsion angle about the central C-C bond is 69.45 (16)°. Symmetry-related benzene rings are inclined to one another by 64.91 (8)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis, uses and properties of the title compound, see: Saito et al. (1988 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H18O4

M = 274.32

Monoclinic,

a = 26.073 (4) Å

b = 5.5538 (8) Å

c = 9.7591 (14) Å

β = 102.211 (3)°

V = 1381.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.981, T max = 0.986

3780 measured reflections

1277 independent reflections

976 reflections with I > 2σ(I)

R int = 0.023

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.224

S = 1.10

1277 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, gobal. DOI: 10.1107/S1600536813007009/su2572sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007009/su2572Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007009/su2572Isup3.cml

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

C16H18O4	F(000) = 584
Mr = 274.32	Dx = 1.319 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1571 reflections
a = 26.073 (4) Å	θ = 3.2–30.3°
b = 5.5538 (8) Å	µ = 0.09 mm−1
c = 9.7591 (14) Å	T = 293 K
β = 102.211 (3)°	Block, colourless
V = 1381.2 (4) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.5°, θmin = 1.6°
ω/2θ scans	h = −31→24
Absorption correction: ψ scan (North et al., 1968)	k = −6→5
Tmin = 0.981, Tmax = 0.986	l = −11→11
3780 measured reflections	3 standard reflections every 200 reflections
1277 independent reflections	intensity decay: 1%

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.224	w = 1/[σ2(Fo2) + (0.168P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1277 reflections	Δρmax = 0.26 e Å−3
93 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (6)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.20123 (6)	0.7928 (2)	0.33002 (13)	0.0496 (5)
O2	0.02888 (5)	0.7020 (2)	−0.10672 (11)	0.0412 (5)
C1	0.20477 (9)	0.9943 (3)	0.42124 (19)	0.0545 (8)
C2	0.15790 (7)	0.7773 (3)	0.22314 (17)	0.0332 (6)
C3	0.15573 (7)	0.5837 (3)	0.13368 (16)	0.0364 (6)
C4	0.11377 (7)	0.5526 (3)	0.02195 (16)	0.0343 (6)
C5	0.07272 (7)	0.7183 (3)	−0.00101 (16)	0.0316 (5)
C6	0.07499 (7)	0.9113 (3)	0.08874 (15)	0.0352 (6)
C7	0.11697 (7)	0.9435 (3)	0.20009 (16)	0.0361 (6)
C8	0.02601 (7)	0.5040 (3)	−0.20015 (15)	0.0369 (6)
H1A	0.20640	1.13950	0.36900	0.0820*
H1B	0.23590	0.98070	0.49380	0.0820*
H1C	0.17450	0.99880	0.46250	0.0820*
H3	0.18300	0.47210	0.14870	0.0440*
H4	0.11300	0.42150	−0.03770	0.0410*
H6	0.04770	1.02230	0.07400	0.0420*
H7	0.11790	1.07540	0.25930	0.0430*
H8A	0.03060	0.35460	−0.14740	0.0440*
H8B	0.05390	0.51580	−0.25180	0.0440*

	U11	U22	U33	U12	U13	U23
O1	0.0415 (9)	0.0576 (10)	0.0417 (9)	0.0100 (6)	−0.0089 (6)	−0.0100 (6)
O2	0.0360 (9)	0.0484 (9)	0.0342 (8)	0.0108 (5)	−0.0037 (6)	−0.0086 (5)
C1	0.0498 (13)	0.0594 (14)	0.0457 (12)	0.0018 (9)	−0.0094 (9)	−0.0141 (8)
C2	0.0324 (10)	0.0394 (11)	0.0261 (9)	0.0017 (7)	0.0024 (7)	0.0032 (6)
C3	0.0336 (11)	0.0408 (11)	0.0340 (10)	0.0103 (7)	0.0052 (7)	0.0028 (7)
C4	0.0373 (11)	0.0348 (10)	0.0307 (9)	0.0061 (7)	0.0067 (7)	−0.0021 (6)
C5	0.0302 (10)	0.0388 (10)	0.0250 (8)	0.0028 (6)	0.0041 (7)	0.0024 (6)
C6	0.0339 (10)	0.0355 (10)	0.0345 (10)	0.0087 (7)	0.0037 (8)	0.0003 (7)
C7	0.0393 (11)	0.0346 (10)	0.0335 (9)	0.0039 (7)	0.0054 (8)	−0.0039 (6)
C8	0.0375 (11)	0.0425 (11)	0.0286 (9)	0.0043 (6)	0.0024 (8)	−0.0033 (6)

O1—C1	1.421 (2)	C8—C8i	1.493 (2)
O1—C2	1.369 (2)	C1—H1A	0.9600
O2—C5	1.371 (2)	C1—H1B	0.9600
O2—C8	1.4203 (19)	C1—H1C	0.9600
C2—C3	1.379 (2)	C3—H3	0.9300
C2—C7	1.393 (3)	C4—H4	0.9300
C3—C4	1.382 (2)	C6—H6	0.9300
C4—C5	1.393 (3)	C7—H7	0.9300
C5—C6	1.378 (2)	C8—H8A	0.9700
C6—C7	1.381 (2)	C8—H8B	0.9700
C1—O1—C2	117.44 (15)	H1A—C1—H1B	109.00
C5—O2—C8	117.16 (13)	H1A—C1—H1C	110.00
O1—C2—C3	116.64 (15)	H1B—C1—H1C	110.00
O1—C2—C7	124.21 (15)	C2—C3—H3	119.00
C3—C2—C7	119.16 (16)	C4—C3—H3	119.00
C2—C3—C4	121.10 (16)	C3—C4—H4	120.00
C3—C4—C5	119.81 (15)	C5—C4—H4	120.00
O2—C5—C4	124.55 (14)	C5—C6—H6	119.00
O2—C5—C6	116.53 (15)	C7—C6—H6	119.00
C4—C5—C6	118.91 (15)	C2—C7—H7	120.00
C5—C6—C7	121.42 (16)	C6—C7—H7	120.00
C2—C7—C6	119.60 (15)	O2—C8—H8A	110.00
O2—C8—C8i	109.61 (14)	O2—C8—H8B	110.00
O1—C1—H1A	109.00	H8A—C8—H8B	108.00
O1—C1—H1B	109.00	C8i—C8—H8A	110.00
O1—C1—H1C	109.00	C8i—C8—H8B	110.00
C1—O1—C2—C3	178.49 (16)	C3—C2—C7—C6	0.2 (3)
C1—O1—C2—C7	−1.2 (2)	C2—C3—C4—C5	−0.3 (3)
C8—O2—C5—C4	−1.2 (2)	C3—C4—C5—O2	−178.66 (16)
C8—O2—C5—C6	179.96 (15)	C3—C4—C5—C6	0.2 (3)
C5—O2—C8—C8i	175.16 (13)	O2—C5—C6—C7	179.05 (15)
O1—C2—C3—C4	−179.60 (16)	C4—C5—C6—C7	0.1 (2)
C7—C2—C3—C4	0.1 (3)	C5—C6—C7—C2	−0.3 (3)
O1—C2—C7—C6	179.87 (16)	O2—C8—C8i—O2i	69.45 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ii	0.96	2.60	3.453 (2)	148
C6—H6···O2iii	0.93	2.59	3.490 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.96	2.60	3.453 (2)	148
C6—H6⋯O2ii	0.93	2.59	3.490 (2)	163

Symmetry codes: (i) ; (ii) .