1,4-Bis(hex­yloxy)benzene

Cheng, H.

doi:10.1107/S1600536813029024

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1721

doi:10.1107/S1600536813029024

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1,4-Bis(hexyloxy)benzene

Hua Cheng ^a ^*

^aCollege of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, People's Republic of China
^*Correspondence e-mail: wqwang2008@163.com

(Received 15 October 2013; accepted 22 October 2013; online 31 October 2013)

The asymmetric unit of the title compound, C₁₈H₃₀O₂, contains one half-molecule situated on an inversion center. The alkyl chain adopts a fully extended all-trans conformation. The C atoms of the alkyl chain are almost coplanar, with a maximum deviation of 0.042 (6) Å from the mean plane,which is inclined to the central benzene ring by 6.80 (9)°. The crystal packing exhibits no short intermolecular contacts.

CCDC reference: 967740

Related literature

For the synthesis and applications of the title compound, see: Ramesh & Thomas (2010 ); Mayor & Didschies (2003 ); Choi et al. (2006 ). For the crystal structures of related compounds, see: Li et al. (2008 ); Thevenet et al. (2010 ).

Experimental

Crystal data

C₁₈H₃₀O₂
M_r = 278.42
Monoclinic, P 2₁ /c
a = 18.853 (12) Å
b = 7.512 (5) Å
c = 6.364 (4) Å
β = 95.674 (10)°
V = 896.9 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.06 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.996, T_max = 0.997
6024 measured reflections
1552 independent reflections
760 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.238
S = 0.99
1552 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 967740

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813029024/cv5434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029024/cv5434Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029024/cv5434Isup3.cml

checkCIF report

Comment top

The title compound is an important intermediate in the synthesis of conjugated polymers (Mayor & Didschies, 2003; Choi et al., 2006) and supramolecular networks (Ramesh & Thomas, 2010). Herein we report its crystal structure.

In the molecule (Fig. 1), the alkyl chain adopts a fully extended all-trans conformation. The C-atoms of the alkyl chain are almost coplanar with the maximum deviation of 0.042 (6) Å from the mean plane, and this mean plane is inclined to the central benzene ring by 6.80 (9)°. The crystal packing exhibits no short intermolecular contacts.

Related literature top

For the synthesis and applications of the title compound, see: Ramesh & Thomas (2010); Mayor & Didschies (2003); Choi et al. (2006). For the crystal structures of related compounds, see: Li et al. (2008); Thevenet et al. (2010).

Experimental top

The title compound was synthesized according to the known method (Ramesh & Thomas, 2010). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of the solution in hexane-MeOH (5:1).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The title molecule with the atom-numbering scheme and 50% probability displacement ellipsoids [symmetry code: (a) -x, 1 -y, 2 -z].

1,4-Bis(hexyloxy)benzene top

Crystal data top

C₁₈H₃₀O₂	F(000) = 308
M_r = 278.42	D_x = 1.031 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 885 reflections
a = 18.853 (12) Å	θ = 2.2–21.8°
b = 7.512 (5) Å	µ = 0.07 mm⁻¹
c = 6.364 (4) Å	T = 298 K
β = 95.674 (10)°	Block, colourless
V = 896.9 (11) Å³	0.06 × 0.05 × 0.04 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	1552 independent reflections
Radiation source: fine-focus sealed tube	760 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −22→21
T_min = 0.996, T_max = 0.997	k = −8→8
6024 measured reflections	l = −7→7

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1237P)²] where P = (F_o² + 2F_c²)/3
1552 reflections	(Δ/σ)_max < 0.001
92 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₃₀O₂	V = 896.9 (11) Å³
M_r = 278.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.853 (12) Å	µ = 0.07 mm⁻¹
b = 7.512 (5) Å	T = 298 K
c = 6.364 (4) Å	0.06 × 0.05 × 0.04 mm
β = 95.674 (10)°

Data collection top

Bruker APEXII CCD diffractometer	1552 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	760 reflections with I > 2σ(I)
T_min = 0.996, T_max = 0.997	R_int = 0.099
6024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.238	H-atom parameters constrained
S = 0.99	Δρ_max = 0.17 e Å⁻³
1552 reflections	Δρ_min = −0.15 e Å⁻³
92 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
C1	0.01445 (17)	0.4133 (3)	0.8176 (4)	0.0693 (9)
H1	0.0241	0.3542	0.6952	0.083*
C2	0.06718 (16)	0.5102 (3)	0.9318 (4)	0.0664 (8)
C3	0.05200 (17)	0.5954 (4)	1.1147 (4)	0.0700 (8)
H3	0.0876	0.6597	1.1928	0.084*
C4	0.15191 (16)	0.4640 (4)	0.6777 (4)	0.0795 (9)
H4A	0.1171	0.5055	0.5661	0.095*
H4B	0.1514	0.3348	0.6782	0.095*
C5	0.22423 (18)	0.5306 (5)	0.6427 (5)	0.0905 (10)
H5A	0.2228	0.6595	0.6360	0.109*
H5B	0.2571	0.4978	0.7634	0.109*
C6	0.25233 (18)	0.4623 (5)	0.4483 (5)	0.0959 (11)
H6A	0.2207	0.4996	0.3269	0.115*
H6B	0.2520	0.3332	0.4520	0.115*
C7	0.3266 (2)	0.5246 (5)	0.4201 (6)	0.1107 (13)
H7A	0.3262	0.6535	0.4098	0.133*
H7B	0.3576	0.4929	0.5452	0.133*
C8	0.3570 (3)	0.4521 (8)	0.2347 (7)	0.1542 (19)
H8A	0.3263	0.4849	0.1095	0.185*
H8B	0.3569	0.3232	0.2443	0.185*
C9	0.4300 (3)	0.5113 (10)	0.2076 (9)	0.202 (3)
H9A	0.4313	0.6389	0.2018	0.303*
H9B	0.4444	0.4631	0.0787	0.303*
H9C	0.4619	0.4704	0.3245	0.303*
O1	0.13529 (11)	0.5307 (3)	0.8769 (3)	0.0818 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.106 (2)	0.0549 (16)	0.0456 (15)	−0.0004 (15)	0.0022 (15)	−0.0034 (12)
C2	0.089 (2)	0.0570 (17)	0.0516 (15)	−0.0033 (13)	−0.0020 (13)	0.0104 (13)
C3	0.103 (2)	0.0531 (16)	0.0516 (15)	−0.0086 (14)	−0.0060 (13)	0.0021 (12)
C4	0.099 (2)	0.0787 (19)	0.0600 (18)	0.0063 (16)	0.0020 (14)	−0.0041 (15)
C5	0.105 (2)	0.085 (2)	0.081 (2)	0.0025 (18)	0.0044 (16)	−0.0080 (17)
C6	0.100 (3)	0.102 (3)	0.086 (2)	0.0084 (19)	0.0097 (17)	−0.0030 (19)
C7	0.108 (3)	0.116 (3)	0.108 (3)	0.002 (2)	0.013 (2)	−0.002 (2)
C8	0.140 (4)	0.200 (5)	0.127 (4)	0.002 (4)	0.041 (3)	−0.017 (4)
C9	0.140 (4)	0.272 (9)	0.205 (6)	−0.003 (4)	0.070 (4)	−0.004 (5)
O1	0.0997 (16)	0.0855 (15)	0.0591 (12)	−0.0089 (11)	0.0017 (10)	−0.0092 (10)

Geometric parameters (Å, º) top

C1—C3ⁱ	1.366 (4)	C5—H5B	0.9700
C1—C2	1.380 (4)	C6—C7	1.505 (5)
C1—H1	0.9300	C6—H6A	0.9700
C2—O1	1.372 (3)	C6—H6B	0.9700
C2—C3	1.383 (4)	C7—C8	1.467 (5)
C3—C1ⁱ	1.366 (4)	C7—H7A	0.9700
C3—H3	0.9300	C7—H7B	0.9700
C4—O1	1.427 (3)	C8—C9	1.472 (6)
C4—C5	1.490 (4)	C8—H8A	0.9700
C4—H4A	0.9700	C8—H8B	0.9700
C4—H4B	0.9700	C9—H9A	0.9600
C5—C6	1.484 (4)	C9—H9B	0.9600
C5—H5A	0.9700	C9—H9C	0.9600

C3ⁱ—C1—C2	119.7 (3)	C7—C6—H6A	108.8
C3ⁱ—C1—H1	120.2	C5—C6—H6B	108.8
C2—C1—H1	120.2	C7—C6—H6B	108.8
O1—C2—C1	124.7 (3)	H6A—C6—H6B	107.7
O1—C2—C3	116.0 (2)	C8—C7—C6	115.0 (4)
C1—C2—C3	119.3 (3)	C8—C7—H7A	108.5
C1ⁱ—C3—C2	121.1 (2)	C6—C7—H7A	108.5
C1ⁱ—C3—H3	119.5	C8—C7—H7B	108.5
C2—C3—H3	119.5	C6—C7—H7B	108.5
O1—C4—C5	107.4 (3)	H7A—C7—H7B	107.5
O1—C4—H4A	110.2	C7—C8—C9	115.2 (5)
C5—C4—H4A	110.2	C7—C8—H8A	108.5
O1—C4—H4B	110.2	C9—C8—H8A	108.5
C5—C4—H4B	110.2	C7—C8—H8B	108.5
H4A—C4—H4B	108.5	C9—C8—H8B	108.5
C6—C5—C4	114.6 (3)	H8A—C8—H8B	107.5
C6—C5—H5A	108.6	C8—C9—H9A	109.5
C4—C5—H5A	108.6	C8—C9—H9B	109.5
C6—C5—H5B	108.6	H9A—C9—H9B	109.5
C4—C5—H5B	108.6	C8—C9—H9C	109.5
H5A—C5—H5B	107.6	H9A—C9—H9C	109.5
C5—C6—C7	113.9 (3)	H9B—C9—H9C	109.5
C5—C6—H6A	108.8	C2—O1—C4	118.7 (2)

C3ⁱ—C1—C2—O1	−178.8 (2)	C5—C6—C7—C8	177.1 (4)
C3ⁱ—C1—C2—C3	0.7 (4)	C6—C7—C8—C9	−179.4 (4)
O1—C2—C3—C1ⁱ	178.9 (2)	C1—C2—O1—C4	6.9 (4)
C1—C2—C3—C1ⁱ	−0.7 (4)	C3—C2—O1—C4	−172.7 (2)
O1—C4—C5—C6	175.7 (2)	C5—C4—O1—C2	170.4 (2)
C4—C5—C6—C7	−177.6 (3)

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₃₀O₂
M_r	278.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	18.853 (12), 7.512 (5), 6.364 (4)
β (°)	95.674 (10)
V (Å³)	896.9 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.06 × 0.05 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.996, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	6024, 1552, 760
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.238, 0.99
No. of reflections	1552
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is grateful to Hubei University of Arts and Science for financial support.

References

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