1,4-Bis(1,1-dimethyl-prop-yl)-2,5-dimeth-oxy-benzene.

The title compound, C(18)H(30)O(2), was prepared by Friedel-Crafts alkyl-ation of 1,4-dimeth-oxy-benzene with 2-methyl-2-butanol. The complete mol-ecule is generated by the application of a crystallographic centre of inversion. The two meth-oxy groups are oriented in the same plane of the aromatic ring [C-C-O-C torsion angle = 9.14 (16)°]. While one methyl group of the tert-pentyl substituent is coplanar with the benzene ring [C-C-C-C = 0.45 (15)°] and lies towards the less-hindered H atom, the other methyl and ethyl groups are directed to either side of the benzene ring [C-C-C-C torsion angles = 118.78 (12) and 59.11 (14)°, respectively]. In the crystal, the hydro-phobic mol-ecules pack to form a brick-wall-like architecture.

Related literature

For the synthesis of the title compound, see: Polito et al. (2010 ▶) and for the synthesis of the analogous compound, 1,4-di-tert-butyl-2,5-dimeth­oxy­benzene, see: Williamson et al. (2006 ▶). For the unique crystal growth of 1,4-di-tert-butyl-2,5-dimeth­oxy­benzene, see: Blatchly & Hartshorne (1966 ▶). For the crystal structure of 1,4-di-tert-butyl-2,5-dimeth­oxy­benzene, see: Rosokha & Kochi (2007 ▶).

Experimental

Crystal data

C18H30O2

M = 278.42

Triclinic,

a = 6.456 (5) Å

b = 6.551 (5) Å

c = 10.800 (5) Å

α = 93.120 (5)°

β = 105.950 (5)°

γ = 108.460 (5)°

V = 411.5 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.07 mm−1

T = 90 K

0.4 × 0.2 × 0.1 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2009 ▶) T min = 0.972, T max = 0.993

2473 measured reflections

1888 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.10

1888 reflections

151 parameters

All H-atom parameters refined

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103772X/tk2787sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103772X/tk2787Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103772X/tk2787Isup3.cml

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

C18H30O2	Z = 1
Mr = 278.42	F(000) = 154
Triclinic, P1	Dx = 1.123 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.456 (5) Å	Cell parameters from 1654 reflections
b = 6.551 (5) Å	θ = 3.3–28.8°
c = 10.800 (5) Å	µ = 0.07 mm−1
α = 93.120 (5)°	T = 90 K
β = 105.950 (5)°	Plate, colourless
γ = 108.460 (5)°	0.4 × 0.2 × 0.1 mm
V = 411.5 (5) Å3

Bruker APEXII CCD area-detector diffractometer	1888 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 8.333 pixels mm-1	θmax = 29.0°, θmin = 2.0°
φ and ω scan	h = −8→5
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2009)'	k = −8→8
Tmin = 0.972, Tmax = 0.993	l = −12→14
2473 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1363P] where P = (Fo2 + 2Fc2)/3
1888 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.22 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
C1	0.66045 (17)	0.40800 (16)	0.56010 (10)	0.0142 (2)
C2	0.54020 (18)	0.34722 (16)	0.42749 (10)	0.0146 (2)
C3	0.37620 (17)	0.43475 (16)	0.36311 (10)	0.0134 (2)
C4	0.24450 (18)	0.36052 (16)	0.21713 (10)	0.0149 (2)
C5	0.28316 (19)	0.55446 (18)	0.13993 (10)	0.0186 (2)
C6	0.5309 (2)	0.7013 (2)	0.16805 (13)	0.0273 (3)
C7	0.3162 (2)	0.18507 (18)	0.15790 (11)	0.0199 (3)
C8	−0.01503 (19)	0.25829 (19)	0.19763 (11)	0.0203 (3)
C9	0.8811 (2)	0.17879 (18)	0.54390 (11)	0.0191 (2)
O1	0.81796 (14)	0.31572 (13)	0.62220 (7)	0.0203 (2)
H2	0.574 (3)	0.240 (2)	0.3790 (14)	0.025 (4)*
H5A	0.215 (3)	0.492 (2)	0.0462 (15)	0.023 (4)*
H5B	0.196 (2)	0.646 (2)	0.1572 (14)	0.021 (3)*
H6A	0.599 (3)	0.782 (3)	0.2639 (17)	0.036 (4)*
H6B	0.635 (3)	0.615 (3)	0.1542 (17)	0.037 (4)*
H6C	0.544 (3)	0.819 (3)	0.1069 (16)	0.034 (4)*
H7A	0.226 (3)	0.138 (2)	0.0662 (15)	0.025 (4)*
H7B	0.479 (3)	0.238 (3)	0.1626 (16)	0.030 (4)*
H7C	0.286 (2)	0.050 (2)	0.2014 (14)	0.023 (3)*
H8A	−0.073 (3)	0.360 (2)	0.2338 (14)	0.021 (3)*
H8B	−0.046 (3)	0.123 (3)	0.2390 (15)	0.028 (4)*
H8C	−0.097 (3)	0.216 (2)	0.1031 (15)	0.024 (4)*
H9A	0.744 (3)	0.043 (2)	0.5000 (14)	0.024 (4)*
H9B	1.000 (3)	0.144 (2)	0.6036 (15)	0.027 (4)*
H9C	0.940 (2)	0.256 (2)	0.4774 (14)	0.021 (3)*

	U11	U22	U33	U12	U13	U23
C1	0.0147 (5)	0.0146 (5)	0.0137 (5)	0.0060 (4)	0.0038 (4)	0.0032 (4)
C2	0.0169 (5)	0.0136 (5)	0.0134 (5)	0.0052 (4)	0.0052 (4)	0.0005 (4)
C3	0.0140 (5)	0.0128 (5)	0.0117 (5)	0.0025 (4)	0.0039 (4)	0.0012 (3)
C4	0.0161 (5)	0.0155 (5)	0.0113 (5)	0.0049 (4)	0.0027 (4)	0.0001 (4)
C5	0.0227 (6)	0.0191 (5)	0.0127 (5)	0.0061 (4)	0.0046 (4)	0.0025 (4)
C6	0.0246 (6)	0.0294 (6)	0.0248 (6)	0.0034 (5)	0.0089 (5)	0.0072 (5)
C7	0.0241 (6)	0.0199 (5)	0.0138 (5)	0.0087 (4)	0.0024 (4)	−0.0029 (4)
C8	0.0168 (5)	0.0222 (6)	0.0166 (5)	0.0028 (4)	0.0020 (4)	0.0005 (4)
C9	0.0215 (5)	0.0214 (5)	0.0179 (5)	0.0129 (4)	0.0056 (4)	0.0021 (4)
O1	0.0255 (4)	0.0258 (4)	0.0137 (4)	0.0173 (3)	0.0028 (3)	0.0007 (3)

C1—O1	1.3812 (14)	C6—H6A	1.043 (17)
C1—C2	1.3941 (15)	C6—H6B	1.037 (17)
C1—C3i	1.4051 (15)	C6—H6C	1.038 (18)
C2—C3	1.3988 (16)	C7—H7A	0.976 (15)
C2—H2	0.963 (15)	C7—H7B	0.984 (17)
C3—C1i	1.4051 (15)	C7—H7C	1.012 (16)
C3—C4	1.5371 (15)	C8—H8A	0.973 (15)
C4—C7	1.5376 (16)	C8—H8B	1.003 (17)
C4—C8	1.5428 (19)	C8—H8C	0.990 (15)
C4—C5	1.5494 (17)	C9—O1	1.4229 (14)
C5—C6	1.5172 (19)	C9—H9A	1.014 (16)
C5—H5A	0.991 (15)	C9—H9B	0.955 (16)
C5—H5B	0.985 (15)	C9—H9C	0.992 (15)
O1—C1—C2	121.95 (10)	H6A—C6—H6B	107.7 (13)
O1—C1—C3i	117.05 (9)	C5—C6—H6C	110.9 (9)
C2—C1—C3i	121.00 (10)	H6A—C6—H6C	107.8 (13)
C1—C2—C3	122.99 (10)	H6B—C6—H6C	107.0 (13)
C1—C2—H2	117.7 (9)	C4—C7—H7A	109.6 (9)
C3—C2—H2	119.3 (9)	C4—C7—H7B	112.6 (9)
C2—C3—C1i	116.02 (10)	H7A—C7—H7B	107.7 (13)
C2—C3—C4	121.35 (9)	C4—C7—H7C	112.1 (8)
C1i—C3—C4	122.63 (9)	H7A—C7—H7C	106.2 (12)
C3—C4—C7	111.63 (9)	H7B—C7—H7C	108.4 (12)
C3—C4—C8	109.87 (9)	C4—C8—H8A	111.4 (9)
C7—C4—C8	106.83 (9)	C4—C8—H8B	109.7 (9)
C3—C4—C5	111.30 (9)	H8A—C8—H8B	110.2 (13)
C7—C4—C5	108.72 (10)	C4—C8—H8C	108.6 (9)
C8—C4—C5	108.33 (9)	H8A—C8—H8C	108.9 (12)
C6—C5—C4	115.63 (10)	H8B—C8—H8C	107.9 (13)
C6—C5—H5A	110.5 (9)	O1—C9—H9A	109.7 (9)
C4—C5—H5A	106.6 (9)	O1—C9—H9B	104.8 (9)
C6—C5—H5B	107.9 (9)	H9A—C9—H9B	111.0 (12)
C4—C5—H5B	109.7 (9)	O1—C9—H9C	111.1 (8)
H5A—C5—H5B	106.2 (12)	H9A—C9—H9C	110.1 (12)
C5—C6—H6A	111.1 (10)	H9B—C9—H9C	110.1 (13)
C5—C6—H6B	112.1 (10)	C1—O1—C9	118.00 (9)