1-Benz­yloxy-4-chloro­benzene

Wang, G.-X.

doi:10.1107/S160053680905096X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o50

doi:10.1107/S160053680905096X

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1-Benzyloxy-4-chlorobenzene

Guo-Xi Wang ^a ^*

^aDepartment of Chemical and Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
^*Correspondence e-mail: aywgx@yahoo.com.cn

(Received 23 November 2009; accepted 26 November 2009; online 4 December 2009)

In the title compound, C₁₃H₁₁ClO, the two benzene rings are close to coplanar, making a dihedral angle of 3.4 (1)° The crystal structure is stabilized by weak C—H⋯π interactions involving both benzene rings.

Related literature

For the chemistry and crystal structures of halogenated aromatic ether derivatives, see: Liu et al. (2006 ); Shen et al. (2003 ).

Experimental

Crystal data

C₁₃H₁₁ClO
M_r = 218.67
Orthorhombic, P n a 2₁
a = 11.485 (2) Å
b = 13.033 (3) Å
c = 7.3333 (15) Å
V = 1097.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.4 × 0.35 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.881, T_max = 0.940
10943 measured reflections
2523 independent reflections
2189 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.115
S = 1.16
2523 reflections
137 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ), 1161 Friedel pairs
Flack parameter: −0.08 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg2ⁱ	0.93	2.81	3.570 (3)	140
C10—H10⋯Cg1ⁱ	0.93	2.88	3.624 (3)	138
Symmetry code: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905096X/ci2976sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905096X/ci2976Isup2.hkl

checkCIF report

Comment top

Halogenated aromatic ether derivatives have found wide range of applications in industry and coordination chemistry as ligands. They are also used in medicine as drugs, such as antibiotics. Recently, a series of halogenated aromatic ether compounds have been reported (Liu et al., 2006; Shen et al., 2003). As an extension of these work on the structural characterization, we report here the crystal structure of the title compound, 1-(benzyloxy)-4-chlorobenzene.

The crystal data show that in the title compound (Fig.1), the two benzene rings are essentially coplanar and twisted from each other by a dihedral angle of 3.4 (1)°. All bond lengths are within the normal range. The crystal structure is stabilized by weak C—H···π interactions.

Related literature top

For the chemistry and crystal structures of halogenated aromatic ether derivatives, see: Liu et al. (2006); Shen et al. (2003). Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Experimental top

The commercial 1-(benzyloxy)-4-chlorobenzene (3 mmol, 648 mg) was dissolved in chloroform (20 ml). The solvent was slowly evaporated in air affording colourless block-shaped crystals of the title compound suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1-Benzyloxy-4-chlorobenzene top

Crystal data top

C₁₃H₁₁ClO	F(000) = 456
M_r = 218.67	D_x = 1.323 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2189 reflections
a = 11.485 (2) Å	θ = 3.1–27.5°
b = 13.033 (3) Å	µ = 0.32 mm⁻¹
c = 7.3333 (15) Å	T = 298 K
V = 1097.7 (4) Å³	Bock, colourless
Z = 4	0.4 × 0.35 × 0.2 mm

Data collection top

Rigaku Mercury2 diffractometer	2523 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.881, T_max = 0.940	l = −9→9
10943 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0637P)² + 0.0118P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.001
S = 1.16	Δρ_max = 0.31 e Å⁻³
2523 reflections	Δρ_min = −0.48 e Å⁻³
137 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.073 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1161 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.08 (9)

Crystal data top

C₁₃H₁₁ClO	V = 1097.7 (4) Å³
M_r = 218.67	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.485 (2) Å	µ = 0.32 mm⁻¹
b = 13.033 (3) Å	T = 298 K
c = 7.3333 (15) Å	0.4 × 0.35 × 0.2 mm

Data collection top

Rigaku Mercury2 diffractometer	2523 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2189 reflections with I > 2σ(I)
T_min = 0.881, T_max = 0.940	R_int = 0.039
10943 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.115	Δρ_max = 0.31 e Å⁻³
S = 1.16	Δρ_min = −0.48 e Å⁻³
2523 reflections	Absolute structure: Flack (1983), 1161 Friedel pairs
137 parameters	Absolute structure parameter: −0.08 (9)
1 restraint

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
Cl1	0.76032 (5)	0.10633 (4)	0.35041 (15)	0.0662 (2)
C11	0.72273 (17)	0.23611 (14)	0.3557 (3)	0.0450 (4)
C6	0.53613 (16)	0.69777 (14)	0.3347 (3)	0.0400 (4)
C5	0.62546 (18)	0.74952 (15)	0.4233 (3)	0.0472 (5)
H5	0.6896	0.7134	0.4663	0.057*
C12	0.79431 (18)	0.30526 (17)	0.4443 (3)	0.0477 (5)
H12	0.8636	0.2833	0.4969	0.057*
O1	0.63588 (13)	0.54166 (11)	0.3941 (3)	0.0610 (5)
C8	0.65937 (17)	0.43950 (15)	0.3727 (3)	0.0443 (4)
C4	0.6193 (2)	0.85449 (18)	0.4478 (4)	0.0555 (6)
H4	0.6791	0.8885	0.5085	0.067*
C10	0.62149 (18)	0.26770 (16)	0.2733 (3)	0.0483 (5)
H10	0.5747	0.2206	0.2125	0.058*
C13	0.76238 (17)	0.40660 (17)	0.4542 (3)	0.0468 (5)
H13	0.8096	0.4533	0.5153	0.056*
C9	0.58956 (18)	0.37006 (16)	0.2814 (3)	0.0471 (5)
H9	0.5213	0.3920	0.2254	0.056*
C7	0.53952 (18)	0.58411 (16)	0.3009 (3)	0.0480 (5)
H7A	0.4681	0.5527	0.3441	0.058*
H7B	0.5464	0.5708	0.1712	0.058*
C2	0.4370 (2)	0.85864 (19)	0.2956 (4)	0.0603 (6)
H2	0.3736	0.8953	0.2514	0.072*
C1	0.44145 (19)	0.75356 (17)	0.2727 (3)	0.0502 (5)
H1	0.3803	0.7199	0.2151	0.060*
C3	0.5254 (2)	0.90919 (16)	0.3831 (4)	0.0587 (6)
H3	0.5221	0.9799	0.3987	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0683 (4)	0.0468 (3)	0.0835 (4)	0.0071 (2)	0.0070 (4)	−0.0037 (4)
C11	0.0476 (10)	0.0429 (9)	0.0443 (10)	0.0007 (8)	0.0080 (10)	−0.0011 (12)
C6	0.0392 (9)	0.0465 (10)	0.0344 (9)	−0.0003 (7)	0.0012 (8)	0.0031 (8)
C5	0.0399 (10)	0.0505 (12)	0.0514 (13)	−0.0016 (8)	−0.0072 (8)	0.0054 (10)
C12	0.0396 (10)	0.0555 (13)	0.0479 (11)	0.0008 (9)	−0.0008 (10)	0.0078 (10)
O1	0.0647 (9)	0.0431 (7)	0.0752 (11)	0.0053 (6)	−0.0318 (8)	−0.0081 (8)
C8	0.0474 (10)	0.0428 (9)	0.0426 (10)	−0.0012 (8)	−0.0041 (9)	−0.0006 (10)
C4	0.0502 (12)	0.0533 (12)	0.0631 (14)	−0.0104 (10)	−0.0051 (11)	−0.0005 (11)
C10	0.0460 (11)	0.0518 (11)	0.0471 (10)	−0.0068 (9)	−0.0001 (10)	−0.0095 (10)
C13	0.0452 (11)	0.0484 (12)	0.0469 (12)	−0.0071 (8)	−0.0093 (10)	0.0001 (9)
C9	0.0399 (10)	0.0547 (11)	0.0466 (11)	0.0026 (8)	−0.0082 (9)	−0.0061 (10)
C7	0.0440 (10)	0.0511 (11)	0.0488 (13)	−0.0004 (8)	−0.0100 (9)	−0.0008 (9)
C2	0.0518 (12)	0.0606 (13)	0.0686 (16)	0.0148 (11)	−0.0061 (11)	0.0069 (12)
C1	0.0395 (10)	0.0578 (13)	0.0535 (11)	0.0006 (8)	−0.0077 (10)	−0.0018 (10)
C3	0.0615 (14)	0.0442 (10)	0.0705 (17)	0.0003 (9)	0.0027 (13)	0.0021 (12)

Geometric parameters (Å, º) top

Cl1—C11	1.7460 (19)	C4—C3	1.377 (3)
C11—C10	1.374 (3)	C4—H4	0.93
C11—C12	1.382 (3)	C10—C9	1.385 (3)
C6—C1	1.385 (3)	C10—H10	0.93
C6—C5	1.389 (3)	C13—H13	0.93
C6—C7	1.502 (3)	C9—H9	0.93
C5—C4	1.382 (3)	C7—H7A	0.97
C5—H5	0.93	C7—H7B	0.97
C12—C13	1.373 (3)	C2—C3	1.370 (3)
C12—H12	0.93	C2—C1	1.381 (3)
O1—C8	1.367 (2)	C2—H2	0.93
O1—C7	1.413 (2)	C1—H1	0.93
C8—C9	1.382 (3)	C3—H3	0.93
C8—C13	1.393 (3)

C10—C11—C12	120.99 (19)	C12—C13—C8	120.0 (2)
C10—C11—Cl1	119.34 (16)	C12—C13—H13	120.0
C12—C11—Cl1	119.67 (17)	C8—C13—H13	120.0
C1—C6—C5	118.59 (18)	C8—C9—C10	119.85 (19)
C1—C6—C7	118.95 (17)	C8—C9—H9	120.1
C5—C6—C7	122.45 (17)	C10—C9—H9	120.1
C4—C5—C6	120.25 (19)	O1—C7—C6	109.07 (15)
C4—C5—H5	119.9	O1—C7—H7A	109.9
C6—C5—H5	119.9	C6—C7—H7A	109.9
C13—C12—C11	119.55 (19)	O1—C7—H7B	109.9
C13—C12—H12	120.2	C6—C7—H7B	109.9
C11—C12—H12	120.2	H7A—C7—H7B	108.3
C8—O1—C7	118.71 (15)	C3—C2—C1	120.4 (2)
O1—C8—C9	125.35 (17)	C3—C2—H2	119.8
O1—C8—C13	114.72 (17)	C1—C2—H2	119.8
C9—C8—C13	119.93 (19)	C2—C1—C6	120.7 (2)
C3—C4—C5	120.5 (2)	C2—C1—H1	119.7
C3—C4—H4	119.7	C6—C1—H1	119.7
C5—C4—H4	119.7	C2—C3—C4	119.5 (2)
C11—C10—C9	119.62 (19)	C2—C3—H3	120.2
C11—C10—H10	120.2	C4—C3—H3	120.2
C9—C10—H10	120.2

C1—C6—C5—C4	−0.2 (3)	O1—C8—C9—C10	−178.3 (2)
C7—C6—C5—C4	178.7 (2)	C13—C8—C9—C10	0.9 (3)
C10—C11—C12—C13	1.6 (3)	C11—C10—C9—C8	−0.3 (3)
Cl1—C11—C12—C13	−177.57 (17)	C8—O1—C7—C6	−176.12 (18)
C7—O1—C8—C9	−7.0 (3)	C1—C6—C7—O1	−173.0 (2)
C7—O1—C8—C13	173.7 (2)	C5—C6—C7—O1	8.0 (3)
C6—C5—C4—C3	−0.7 (4)	C3—C2—C1—C6	−1.2 (4)
C12—C11—C10—C9	−1.0 (3)	C5—C6—C1—C2	1.2 (3)
Cl1—C11—C10—C9	178.22 (17)	C7—C6—C1—C2	−177.8 (2)
C11—C12—C13—C8	−1.0 (3)	C1—C2—C3—C4	0.2 (4)
O1—C8—C13—C12	179.0 (2)	C5—C4—C3—C2	0.7 (4)
C9—C8—C13—C12	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg2ⁱ	0.93	2.81	3.570 (3)	140
C10—H10···Cg1ⁱ	0.93	2.88	3.624 (3)	138

Symmetry code: (i) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁ClO
M_r	218.67
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	11.485 (2), 13.033 (3), 7.3333 (15)
V (Å³)	1097.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.4 × 0.35 × 0.2

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.881, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	10943, 2523, 2189
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.115, 1.16
No. of reflections	2523
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.48
Absolute structure	Flack (1983), 1161 Friedel pairs
Absolute structure parameter	−0.08 (9)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg2ⁱ	0.93	2.81	3.570 (3)	140
C10—H10···Cg1ⁱ	0.93	2.88	3.624 (3)	138

Symmetry code: (i) −x+1, −y+1, z−1/2.

Acknowledgements

This work was supported by a start-up grant from Anyang Institute of Technology.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, G.-H., Xue, Y.-N., Yao, M., Yu, H. & Fang, H.-B. (2006). Acta Cryst. E62, o2848–o2849. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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