1,2-Bis(4-methyl­phen­oxy)ethane

Wang, L.; Yang, W.; Zhu, J.; Wang, K.; Hu, Y.

doi:10.1107/S1600536810042613

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3000

https://doi.org/10.1107/S1600536810042613

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1,2-Bis(4-methylphenoxy)ethane

Lu-lu Wang,^a Wen-ge Yang,^a ^* Jing Zhu,^a Kai Wang ^a and Yong-hong Hu ^b

^aState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: chemywg@126.com

(Received 13 September 2010; accepted 20 October 2010; online 31 October 2010)

In the title compound, C₁₆H₁₈O₂, the two aromatic rings are almost orthogonal, making a dihedral angle of 89.41 (2)°. There is a C—H⋯π contact between the methylene group and the 4-methylphenyl ring. The molecule exhibits twofold symmetry..

Related literature

For background to the uses of the title compound and further synthetic details, see: Xiao et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₈O₂
M_r = 242.30
Monoclinic, C 2/c
a = 27.173 (5) Å
b = 5.5510 (11) Å
c = 9.2780 (19) Å
β = 93.55 (3)°
V = 1396.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.978, T_max = 0.996
2542 measured reflections
1276 independent reflections
636 reflections with I > 2σ(I)
R_int = 0.083
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.131
S = 1.00
1276 reflections
82 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the 4-methylphenyl ring (C1–C6).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cg1	0.97	2.85	3.664 (3)	142

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810042613/ng5032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042613/ng5032Isup2.hkl

checkCIF report

Related literature top

For general background [to what?], see: Xiao et al. (2007).

Experimental top

p-Cresol (30.3 g,0.28 mol) was added to a stirred solution of sodium hydroxide(16 g,0.4 mol) in 200 ml of ethanol at room temperature. After stirring for 1 h, ethylene dibromide(28.1 g,0.15 mol) was added. The reaction mixture was stirred and heated under refluxing for another 15 h and then poured into a 5% aqueous solution of NaOH (500 ml). The resulting mixture was cooled to room temperature and filtered. The remaining solid was washed with water(2 x 50 ml) and ethanol(2 x 40 ml),and then dried in vacuo to give the products 13.6 g as white solids (40.1%) (Xiao et al., 2007) Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Structure description top

For general background [to what?], see: Xiao et al. (2007).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.
	Fig. 2. A practical packing diagram of the title compound. There is no intramolecular or intermolecular hydrogen bonds in the crystal.

1-methyl-4-[2-(4-methylphenoxy)ethoxy]benzene top

Crystal data top

C₁₆H₁₈O₂	F(000) = 520
M_r = 242.30	D_x = 1.152 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.173 (5) Å	Cell parameters from 25 reflections
b = 5.5510 (11) Å	θ = 9–12°
c = 9.2780 (19) Å	µ = 0.08 mm⁻¹
β = 93.55 (3)°	T = 293 K
V = 1396.8 (5) Å³	Prism, colorless
Z = 4	0.30 × 0.30 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.083
Graphite monochromator	θ_max = 25.3°, θ_min = 1.5°
ω/2θ scans	h = −32→32
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
T_min = 0.978, T_max = 0.996	l = −11→11
2542 measured reflections	3 standard reflections every 200 reflections
1276 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.022P)²] where P = (F_o² + 2F_c²)/3
1276 reflections	(Δ/σ)_max < 0.001
82 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₆H₁₈O₂	V = 1396.8 (5) Å³
M_r = 242.30	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 27.173 (5) Å	µ = 0.08 mm⁻¹
b = 5.5510 (11) Å	T = 293 K
c = 9.2780 (19) Å	0.30 × 0.30 × 0.05 mm
β = 93.55 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	636 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.083
T_min = 0.978, T_max = 0.996	3 standard reflections every 200 reflections
2542 measured reflections	intensity decay: 1%
1276 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	Δρ_max = 0.13 e Å⁻³
1276 reflections	Δρ_min = −0.14 e Å⁻³
82 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 > 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.

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

	x	y	z	U_iso*/U_eq
O	0.52863 (6)	0.2044 (3)	0.12559 (15)	0.0667 (6)
C1	0.65274 (9)	0.1203 (6)	−0.0026 (3)	0.0768 (9)
H1A	0.6793	0.0147	0.0075	0.092*
C2	0.61155 (9)	0.0757 (5)	0.0739 (2)	0.0660 (7)
H2A	0.6105	−0.0578	0.1342	0.079*
C3	0.57211 (9)	0.2313 (5)	0.0597 (2)	0.0543 (6)
C4	0.57452 (9)	0.4268 (5)	−0.0305 (2)	0.0635 (7)
H4A	0.5479	0.5321	−0.0411	0.076*
C5	0.61569 (10)	0.4681 (5)	−0.1049 (3)	0.0704 (8)
H5A	0.6166	0.6022	−0.1647	0.085*
C6	0.65576 (10)	0.3158 (6)	−0.0932 (3)	0.0752 (9)
C7	0.70126 (10)	0.3646 (6)	−0.1759 (3)	0.1183 (13)
H7A	0.7254	0.2418	−0.1539	0.177*
H7B	0.7147	0.5190	−0.1485	0.177*
H7C	0.6924	0.3637	−0.2777	0.177*
C8	0.52487 (8)	0.0048 (5)	0.2210 (2)	0.0663 (8)
H8A	0.5499	0.0169	0.2998	0.080*
H8B	0.5300	−0.1444	0.1696	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0811 (12)	0.0665 (12)	0.0532 (9)	0.0140 (11)	0.0085 (9)	0.0125 (11)
C1	0.0708 (18)	0.082 (2)	0.0774 (18)	0.0161 (17)	0.0044 (15)	−0.001 (2)
C2	0.0797 (17)	0.0638 (18)	0.0538 (14)	0.0115 (17)	−0.0030 (13)	0.0044 (16)
C3	0.0670 (16)	0.0574 (16)	0.0382 (12)	0.0066 (15)	−0.0003 (12)	−0.0046 (13)
C4	0.0806 (18)	0.0546 (17)	0.0548 (13)	0.0090 (15)	0.0012 (13)	0.0019 (16)
C5	0.0858 (19)	0.0658 (19)	0.0595 (15)	−0.0035 (17)	0.0023 (15)	0.0060 (17)
C6	0.0771 (19)	0.087 (2)	0.0617 (16)	−0.0028 (19)	0.0093 (15)	−0.006 (2)
C7	0.088 (2)	0.152 (4)	0.118 (2)	−0.005 (2)	0.0279 (19)	0.008 (3)
C8	0.0914 (19)	0.0611 (16)	0.0462 (12)	0.0077 (15)	0.0023 (12)	0.0064 (14)

Geometric parameters (Å, º) top

O—C3	1.372 (2)	C5—C6	1.377 (4)
O—C8	1.426 (3)	C5—H5A	0.9300
C1—C6	1.378 (4)	C6—C7	1.519 (3)
C1—C2	1.384 (3)	C7—H7A	0.9600
C1—H1A	0.9300	C7—H7B	0.9600
C2—C3	1.376 (3)	C7—H7C	0.9600
C2—H2A	0.9300	C8—C8ⁱ	1.485 (4)
C3—C4	1.375 (3)	C8—H8A	0.9700
C4—C5	1.370 (3)	C8—H8B	0.9700
C4—H4A	0.9300

C3—O—C8	117.25 (18)	C1—C6—C5	117.0 (3)
C6—C1—C2	122.3 (3)	C1—C6—C7	122.0 (3)
C6—C1—H1A	118.9	C5—C6—C7	121.0 (3)
C2—C1—H1A	118.9	C6—C7—H7A	109.5
C3—C2—C1	119.2 (3)	C6—C7—H7B	109.5
C3—C2—H2A	120.4	H7A—C7—H7B	109.5
C1—C2—H2A	120.4	C6—C7—H7C	109.5
O—C3—C4	115.6 (2)	H7A—C7—H7C	109.5
O—C3—C2	125.2 (2)	H7B—C7—H7C	109.5
C4—C3—C2	119.2 (2)	O—C8—C8ⁱ	109.05 (18)
C5—C4—C3	120.7 (3)	O—C8—H8A	109.9
C5—C4—H4A	119.7	C8ⁱ—C8—H8A	109.9
C3—C4—H4A	119.7	O—C8—H8B	109.9
C4—C5—C6	121.6 (3)	C8ⁱ—C8—H8B	109.9
C4—C5—H5A	119.2	H8A—C8—H8B	108.3
C6—C5—H5A	119.2

C6—C1—C2—C3	−0.1 (4)	C3—C4—C5—C6	0.5 (4)
C8—O—C3—C4	−179.46 (19)	C2—C1—C6—C5	0.1 (4)
C8—O—C3—C2	2.8 (3)	C2—C1—C6—C7	179.5 (2)
C1—C2—C3—O	177.9 (2)	C4—C5—C6—C1	−0.3 (4)
C1—C2—C3—C4	0.2 (3)	C4—C5—C6—C7	−179.7 (3)
O—C3—C4—C5	−178.3 (2)	C3—O—C8—C8ⁱ	−179.03 (19)
C2—C3—C4—C5	−0.4 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg1	0.97	2.85	3.664 (3)	142

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈O₂
M_r	242.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.173 (5), 5.5510 (11), 9.2780 (19)
β (°)	93.55 (3)
V (Å³)	1396.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	2542, 1276, 636
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.131, 1.00
No. of reflections	1276
No. of parameters	82
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg1	0.97	2.85	3.664 (3)	142

Acknowledgements

This research work was supported financially by the Department of Science and Technology of Jiangsu Province (BE200830457) and `863' project (2007 A A02Z211) of the Ministry of Science and Technology.

References

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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