2-[4-(2,6-Dimeth-oxy-phen-yl)but-yl]-1,3-dimeth-oxy-benzene.

The title compound, C(20)H(26)O(4), crystallizes such that the alkyl chain adopts an all-anti conformation. The crystal packing displays edge-to-face arene-arene inter-actions with a dihedral angle of 87°. The complete molecule is generated by inversion symmetry.

Related literature

For related compounds containing tethered 2,6-dimeth­oxy­benzene fragments, see: Ionkin et al. (2003 ▶); Evans et al. (1991 ▶); Yoshimura et al. (2008 ▶); Shinohara et al. (2008 ▶); Ono et al. (2008 ▶). For a related structure, see: Fleck et al. (2005 ▶). For the synthesis and further studies, see: Lettré et al. (1952 ▶); Tanaka et al. (1989 ▶). The rather large crystal used for data collection was chosen in order to optimize data intensity. For weakly absorbing materials, SADABS is known to be effective at correcting for crystal sizes larger than the beam without introducing systematic errors, see, for example: Görbitz (1999 ▶).

Experimental

Crystal data

C20H26O4

M = 330.41

Orthorhombic,

a = 22.692 (2) Å

b = 5.5460 (5) Å

c = 13.7099 (13) Å

V = 1725.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.98 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.916, T max = 0.981

14196 measured reflections

2071 independent reflections

1853 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.05

2071 reflections

161 parameters

All H-atom parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.17 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: X-SEED and POV-RAY (Persistence of Vision, 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025420/ng2784sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025420/ng2784Isup2.hkl

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

C20H26O4	Dx = 1.272 Mg m−3
Mr = 330.41	Melting point = 429–431 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6702 reflections
a = 22.692 (2) Å	θ = 3.0–28.5°
b = 5.5460 (5) Å	µ = 0.09 mm−1
c = 13.7099 (13) Å	T = 100 K
V = 1725.4 (3) Å3	Prism, colorless
Z = 4	0.98 × 0.36 × 0.22 mm
F(000) = 712

Bruker SMART APEXII CCD diffractometer	2071 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −29→29
Tmin = 0.916, Tmax = 0.981	k = −7→7
14196 measured reflections	l = −17→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.4726P] where P = (Fo2 + 2Fc2)/3
2071 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.17 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	0.15557 (4)	0.35467 (17)	0.12621 (6)	0.0182 (2)
C2	0.19265 (4)	0.29025 (19)	0.20325 (7)	0.0225 (2)
C3	0.18839 (5)	0.4180 (2)	0.28983 (7)	0.0260 (2)
C4	0.14842 (5)	0.6043 (2)	0.30147 (7)	0.0257 (2)
C5	0.11173 (4)	0.66605 (18)	0.22332 (7)	0.0216 (2)
C6	0.11502 (4)	0.54382 (17)	0.13379 (6)	0.0182 (2)
C7	0.07619 (4)	0.61358 (17)	0.04894 (7)	0.0185 (2)
C8	0.01905 (4)	0.46605 (17)	0.04386 (7)	0.0190 (2)
C9	0.06764 (6)	0.9829 (2)	0.31571 (9)	0.0354 (3)
C10	0.19556 (4)	0.04010 (18)	0.02716 (8)	0.0229 (2)
H2	0.2201 (6)	0.161 (2)	0.1972 (9)	0.028 (3)*
H3	0.2143 (5)	0.375 (2)	0.3442 (10)	0.030 (3)*
H4	0.1459 (6)	0.689 (3)	0.3613 (10)	0.032 (3)*
H7A	0.0984 (5)	0.588 (2)	−0.0112 (9)	0.021 (3)*
H7B	0.0660 (5)	0.785 (2)	0.0535 (8)	0.021 (3)*
H8A	0.0292 (5)	0.292 (2)	0.0404 (8)	0.021 (3)*
H8B	−0.0035 (5)	0.491 (2)	0.1046 (8)	0.021 (3)*
H9A	0.1055 (6)	1.065 (2)	0.3276 (10)	0.031 (3)*
H9B	0.0560 (7)	0.878 (3)	0.3713 (12)	0.051 (4)*
H9C	0.0387 (7)	1.102 (3)	0.3050 (11)	0.043 (4)*
H10A	0.2369 (6)	0.091 (2)	0.0350 (8)	0.025 (3)*
H10B	0.1868 (6)	−0.085 (2)	0.0749 (10)	0.030 (3)*
H10C	0.1886 (6)	−0.025 (3)	−0.0395 (10)	0.035 (4)*
O1	0.15679 (3)	0.24072 (13)	0.03720 (5)	0.02170 (18)
O2	0.07098 (3)	0.84683 (14)	0.22717 (5)	0.0297 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0188 (4)	0.0210 (4)	0.0148 (4)	−0.0041 (3)	0.0011 (3)	0.0013 (3)
C2	0.0208 (5)	0.0261 (5)	0.0207 (5)	−0.0034 (4)	−0.0019 (3)	0.0060 (4)
C3	0.0280 (5)	0.0328 (5)	0.0171 (4)	−0.0109 (4)	−0.0043 (4)	0.0065 (4)
C4	0.0314 (5)	0.0309 (5)	0.0148 (4)	−0.0139 (4)	0.0026 (4)	−0.0024 (4)
C5	0.0209 (5)	0.0234 (5)	0.0205 (5)	−0.0075 (3)	0.0050 (3)	−0.0033 (4)
C6	0.0170 (4)	0.0210 (4)	0.0166 (4)	−0.0043 (3)	0.0009 (3)	0.0001 (3)
C7	0.0181 (4)	0.0181 (4)	0.0192 (4)	0.0000 (3)	−0.0007 (3)	−0.0007 (3)
C8	0.0179 (4)	0.0186 (4)	0.0207 (5)	0.0004 (3)	−0.0006 (3)	−0.0004 (3)
C9	0.0369 (6)	0.0351 (6)	0.0341 (6)	−0.0084 (5)	0.0121 (5)	−0.0179 (5)
C10	0.0225 (5)	0.0207 (5)	0.0254 (5)	0.0030 (4)	0.0008 (4)	0.0000 (4)
O1	0.0247 (4)	0.0241 (4)	0.0163 (3)	0.0066 (3)	−0.0014 (2)	−0.0015 (2)
O2	0.0281 (4)	0.0317 (4)	0.0293 (4)	0.0002 (3)	0.0044 (3)	−0.0139 (3)

O1—C1	1.3746 (11)	C7—H7B	0.979 (12)
O1—C10	1.4251 (11)	C7—H7A	0.976 (12)
O2—C5	1.3650 (13)	C10—H10A	0.986 (13)
O2—C9	1.4314 (12)	C10—H10C	0.995 (14)
C5—C4	1.3992 (14)	C10—H10B	0.975 (14)
C5—C6	1.4042 (13)	C4—C3	1.3844 (16)
C8—C8i	1.5283 (18)	C4—H4	0.947 (14)
C8—C7	1.5349 (12)	C2—C3	1.3857 (14)
C8—H8A	0.992 (12)	C2—H2	0.955 (13)
C8—H8B	0.987 (11)	C3—H3	0.979 (13)
C6—C1	1.3993 (13)	C9—H9A	0.985 (13)
C6—C7	1.5096 (12)	C9—H9B	0.994 (16)
C1—C2	1.3967 (13)	C9—H9C	0.943 (16)
C1—O1—C10	117.20 (7)	H7B—C7—H7A	108.5 (10)
C5—O2—C9	117.13 (9)	O1—C10—H10A	110.7 (7)
O2—C5—C4	123.58 (9)	O1—C10—H10C	105.8 (8)
O2—C5—C6	115.11 (8)	H10A—C10—H10C	110.8 (10)
C4—C5—C6	121.31 (9)	O1—C10—H10B	111.4 (8)
C8i—C8—C7	112.48 (9)	H10A—C10—H10B	109.1 (10)
C8i—C8—H8A	109.4 (7)	H10C—C10—H10B	109.0 (11)
C7—C8—H8A	109.0 (7)	C3—C4—C5	118.96 (9)
C8i—C8—H8B	109.6 (7)	C3—C4—H4	120.7 (8)
C7—C8—H8B	108.9 (7)	C5—C4—H4	120.4 (8)
H8A—C8—H8B	107.3 (10)	C3—C2—C1	118.36 (9)
C1—C6—C5	117.49 (8)	C3—C2—H2	120.4 (7)
C1—C6—C7	121.24 (8)	C1—C2—H2	121.3 (7)
C5—C6—C7	121.26 (8)	C4—C3—C2	121.73 (9)
O1—C1—C2	122.79 (9)	C4—C3—H3	119.2 (8)
O1—C1—C6	115.08 (8)	C2—C3—H3	119.1 (8)
C2—C1—C6	122.12 (9)	O2—C9—H9A	109.7 (8)
C6—C7—C8	113.04 (7)	O2—C9—H9B	110.9 (9)
C6—C7—H7B	109.7 (7)	H9A—C9—H9B	111.9 (12)
C8—C7—H7B	108.7 (7)	O2—C9—H9C	105.9 (9)
C6—C7—H7A	108.2 (7)	H9A—C9—H9C	108.2 (12)
C8—C7—H7A	108.6 (7)	H9B—C9—H9C	110.1 (12)