1,4-Bis[2-(prop-1-en­yl)phen­oxy]butane

Bayramov, M.R.; Maharramov, A.M.; Mehdiyeva, G.M.; Hoseinzadeh, S.B.; Askerov, R.K.

doi:10.1107/S1600536811018538

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1478

doi:10.1107/S1600536811018538

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1,4-Bis[2-(prop-1-enyl)phenoxy]butane

Musa R. Bayramov,^a Abel M. Maharramov,^a Gunay M. Mehdiyeva,^a ^* Shahnaz B. Hoseinzadeh ^a and Rizvan K. Askerov ^a

^aBaku State University, Z. Khalilov St 23, Baku AZ-1148, Azerbaijan
^*Correspondence e-mail: mehdiyeva_gm@mail.ru

(Received 3 May 2011; accepted 16 May 2011; online 20 May 2011)

The molecule of the title compound, C₂₂H₂₆O₂, exhibits C_i molecular symmetry with a crystallographic inversion centre at the mid-point of the central C—C bond. A kink in the molecule 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_r = 322.43
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.151
S = 1.01
2404 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811018538/kp2326Isup3.cml

checkCIF report

Comment top

For giving the important operationalisation to cross-linked polymers reactions of copolymerisation of various monomers, multifunctional comonomers [1] are used. By applying this method, the hi-tech processes for the preparation of polymeric sorbents, photorezisting materials for microelectronics, the composites for the laser technics of a special purposes, fixation of metalcomplex of catalysts, etc were obtained (Crivello et al. 1994). In practice, for obtaining polymers of demanded functional properties, polymerical transformations are carried out. However, it is necessary to notice, that obtaining such cross-linked copolymers have some difficulties connected with high reactivity of cross-linking comonomers (for example, divinylbenzene), which is reflected in heterogeneity of their structure and other important physical and chemical properties. Therefore, to prepare multifunctional monomers, on the basis of alkenylphenols with two double bonds, is rather important. The molecule of the title compound, C₂₂H₂₆O₂ (I), is generated by a crystallographic inversion centre at the midpoint of the central C—C bond. A fold of the molecule is due to the twist in the central butylene bridge [O1—C10—C11—C11A torsion angle of 66.7 (2)°] (Fig. 1). Crystal packing is dominated by van der Waals interactions (Fig. 2).

Related literature top

For general background to the use of copolymerization reactions, see: Crivello et al. (1994). For related literature [on what subject(s)?], see: Roshupkin & Kurmaz (2004); Askadsky (1998).

Experimental top

2-Propenylphenol (0.015 mol, 2 g) and KOH (0.015 mol, 0.84 g) were dissolved in 5 mL 2-propanol, then to this solution 1,4-dibromebutane (0.0043 mol, 0.93 g) was added. This mixture was stirred at 353 K within 30 min. The desired compounds (with yield of 4.7 g, 98.1%) was filtered and washed with acetone and recrystallised to obtain colourless crystals. Tmp = 353 K. The structure of the reported compound - 1,4-bis{2(1-propenyl)phenoxy}butane, also was proved by NMR-spectroscopy. FT-NMR (acetone-d6,, p.p.m.), 1H: 1.91 d (6H,CH3); 2.03 t (4H,CH2); 4.1 t (4H, OCH2); 6.15 m (2H, CH=); 6.65–7.1 m (8H, 2Ar); 7.32 d (2H,CH=). 13 C: 18.9; 26.3; 67.6; 112.8; 121.7; 124.9; 126.1; 127.2; 127.3; 127.5; 156.4.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. Stacking of chains in the crystal packing.

1,4-Bis[2-(prop-1-enyl)phenoxy]butane top

Crystal data top

C₂₂H₂₆O₂	F(000) = 696
M_r = 322.43	D_x = 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

Data collection top

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

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.071P)² + 0.2P] where P = (F_o² + 2F_c²)/3
2404 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₂H₂₆O₂	V = 1887.9 (6) Å³
M_r = 322.43	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 5.4501 (10) Å	µ = 0.07 mm⁻¹
b = 15.825 (3) Å	T = 296 K
c = 21.889 (4) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2404 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1427 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.040
20262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
2404 reflections	Δρ_min = −0.11 e Å⁻³
110 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆O₂
M_r	322.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	5.4501 (10), 15.825 (3), 21.889 (4)
V (Å³)	1887.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	20262, 2404, 1427
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.151, 1.01
No. of reflections	2404
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.11

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help in this work.

References

Askadsky, A. A. (1998). Successes Chem. 67, 755–787. Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Crivello, J. V., Carter, A. M. & Bratslavsky, S. A. (1994). J. Polymer Sci. Part A Polymer Chem. 32, 2895–2909. CrossRef CAS Google Scholar
Roshupkin, V. P. & Kurmaz, S. V. (2004). Successes Chem. 73, 247–274. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar