1,4-Bis[2-(prop-1-en-yl)phen-oxy]butane.

The mol-ecule of the title compound, C(22)H(26)O(2), exhibits C(i) mol-ecular symmetry with a crystallographic inversion centre at the mid-point of the central C-C bond. A kink in the mol-ecule is defined by the torsion angle of 66.7 (2)° about this central bond of the alkyl bridge.

Related literature

For general background to the use of copolymerization reactions, see: Crivello et al. (1994 ▶); Roshupkin & Kurmaz (2004 ▶); Askadsky (1998 ▶).

Experimental

Crystal data

C22H26O2

M = 322.43

Orthorhombic,

a = 5.4501 (10) Å

b = 15.825 (3) Å

c = 21.889 (4) Å

V = 1887.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.979, T max = 0.986

20262 measured reflections

2404 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.151

S = 1.01

2404 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018538/kp2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018538/kp2326Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018538/kp2326Isup3.cml

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

C22H26O2	F(000) = 696
Mr = 322.43	Dx = 1.134 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4034 reflections
a = 5.4501 (10) Å	θ = 2.6–23.1°
b = 15.825 (3) Å	µ = 0.07 mm−1
c = 21.889 (4) Å	T = 296 K
V = 1887.9 (6) Å3	Prism, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	2404 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 28.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.979, Tmax = 0.986	k = −21→21
20262 measured reflections	l = −29→29

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) = 0.151	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.071P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3
2404 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.11 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
O1	0.1929 (2)	0.12834 (6)	0.05285 (5)	0.0764 (3)
C1	0.1981 (3)	0.19881 (9)	0.08887 (6)	0.0641 (4)
C2	0.3717 (2)	0.19780 (9)	0.13598 (6)	0.0614 (4)
C3	0.3831 (3)	0.26839 (11)	0.17357 (8)	0.0805 (5)
H3A	0.4969	0.2696	0.2052	0.097*
C4	0.2297 (4)	0.33659 (12)	0.16510 (10)	0.0964 (6)
H4A	0.2408	0.3832	0.1909	0.116*
C5	0.0609 (4)	0.33587 (12)	0.11879 (11)	0.0958 (6)
H5A	−0.0436	0.3817	0.1134	0.115*
C6	0.0455 (3)	0.26750 (11)	0.08014 (8)	0.0826 (5)
H6A	−0.0673	0.2675	0.0483	0.099*
C7	0.5292 (3)	0.12253 (10)	0.14476 (7)	0.0655 (4)
H7A	0.4863	0.0747	0.1225	0.079*
C8	0.7203 (3)	0.11548 (10)	0.17993 (7)	0.0729 (4)
H8A	0.7671	0.1632	0.2018	0.088*
C9	0.8691 (3)	0.03876 (12)	0.18816 (7)	0.0789 (5)
H9A	0.8709	0.0234	0.2306	0.118*
H9B	1.0338	0.0494	0.1746	0.118*
H9C	0.7998	−0.0065	0.1646	0.118*
C10	0.0059 (3)	0.12144 (11)	0.00726 (8)	0.0791 (5)
H10A	0.0261	0.1653	−0.0233	0.095*
H10B	−0.1549	0.1277	0.0257	0.095*
C11	0.0297 (4)	0.03563 (11)	−0.02174 (7)	0.0827 (5)
H11A	0.1962	0.0286	−0.0366	0.099*
H11B	−0.0797	0.0325	−0.0566	0.099*

	U11	U22	U33	U12	U13	U23
O1	0.0798 (7)	0.0745 (7)	0.0750 (7)	0.0052 (5)	−0.0182 (5)	−0.0066 (5)
C1	0.0641 (8)	0.0616 (8)	0.0665 (8)	−0.0057 (6)	0.0061 (7)	0.0056 (6)
C2	0.0609 (8)	0.0622 (8)	0.0611 (8)	−0.0133 (6)	0.0091 (6)	0.0018 (6)
C3	0.0864 (11)	0.0742 (10)	0.0807 (10)	−0.0152 (8)	0.0078 (9)	−0.0079 (8)
C4	0.1190 (15)	0.0636 (10)	0.1066 (14)	−0.0128 (10)	0.0252 (13)	−0.0162 (10)
C5	0.1026 (13)	0.0663 (11)	0.1185 (16)	0.0098 (9)	0.0153 (13)	0.0074 (10)
C6	0.0802 (10)	0.0741 (11)	0.0936 (12)	0.0050 (8)	0.0000 (9)	0.0135 (9)
C7	0.0640 (8)	0.0719 (9)	0.0605 (8)	−0.0116 (7)	−0.0001 (6)	−0.0039 (7)
C8	0.0725 (9)	0.0806 (10)	0.0657 (9)	−0.0124 (8)	−0.0047 (7)	−0.0068 (7)
C9	0.0681 (9)	0.0978 (12)	0.0708 (9)	0.0015 (8)	−0.0044 (7)	0.0010 (8)
C10	0.0803 (10)	0.0902 (11)	0.0666 (9)	−0.0064 (8)	−0.0164 (8)	0.0109 (8)
C11	0.0945 (12)	0.0979 (12)	0.0558 (8)	−0.0157 (10)	−0.0108 (8)	0.0026 (7)

O1—C1	1.3659 (17)	C7—C8	1.300 (2)
O1—C10	1.4305 (19)	C7—H7A	0.9300
C1—C6	1.382 (2)	C8—C9	1.471 (2)
C1—C2	1.399 (2)	C8—H8A	0.9300
C2—C3	1.389 (2)	C9—H9A	0.9600
C2—C7	1.481 (2)	C9—H9B	0.9600
C3—C4	1.378 (3)	C9—H9C	0.9600
C3—H3A	0.9300	C10—C11	1.505 (2)
C4—C5	1.369 (3)	C10—H10A	0.9700
C4—H4A	0.9300	C10—H10B	0.9700
C5—C6	1.376 (3)	C11—C11i	1.511 (3)
C5—H5A	0.9300	C11—H11A	0.9700
C6—H6A	0.9300	C11—H11B	0.9700
C1—O1—C10	118.67 (12)	C7—C8—C9	125.81 (15)
O1—C1—C6	123.36 (14)	C7—C8—H8A	117.1
O1—C1—C2	115.47 (12)	C9—C8—H8A	117.1
C6—C1—C2	121.17 (15)	C8—C9—H9A	109.5
C3—C2—C1	117.23 (14)	C8—C9—H9B	109.5
C3—C2—C7	122.96 (14)	H9A—C9—H9B	109.5
C1—C2—C7	119.78 (12)	C8—C9—H9C	109.5
C4—C3—C2	121.55 (18)	H9A—C9—H9C	109.5
C4—C3—H3A	119.2	H9B—C9—H9C	109.5
C2—C3—H3A	119.2	O1—C10—C11	107.57 (13)
C5—C4—C3	120.05 (17)	O1—C10—H10A	110.2
C5—C4—H4A	120.0	C11—C10—H10A	110.2
C3—C4—H4A	120.0	O1—C10—H10B	110.2
C4—C5—C6	120.20 (18)	C11—C10—H10B	110.2
C4—C5—H5A	119.9	H10A—C10—H10B	108.5
C6—C5—H5A	119.9	C10—C11—C11i	112.91 (17)
C5—C6—C1	119.78 (18)	C10—C11—H11A	109.0
C5—C6—H6A	120.1	C11i—C11—H11A	109.0
C1—C6—H6A	120.1	C10—C11—H11B	109.0
C8—C7—C2	127.62 (14)	C11i—C11—H11B	109.0
C8—C7—H7A	116.2	H11A—C11—H11B	107.8
C2—C7—H7A	116.2
C10—O1—C1—C6	−5.9 (2)	C3—C4—C5—C6	−0.7 (3)
C10—O1—C1—C2	174.45 (13)	C4—C5—C6—C1	1.1 (3)
O1—C1—C2—C3	179.89 (13)	O1—C1—C6—C5	179.48 (15)
C6—C1—C2—C3	0.3 (2)	C2—C1—C6—C5	−0.9 (2)
O1—C1—C2—C7	−1.52 (18)	C3—C2—C7—C8	−12.1 (2)
C6—C1—C2—C7	178.86 (14)	C1—C2—C7—C8	169.40 (15)
C1—C2—C3—C4	0.2 (2)	C2—C7—C8—C9	178.78 (15)
C7—C2—C3—C4	−178.36 (15)	C1—O1—C10—C11	−175.35 (13)
C2—C3—C4—C5	0.0 (3)	O1—C10—C11—C11i	66.7 (2)