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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o50.
Published online 2009 December 4. doi:  10.1107/S160053680905096X
PMCID: PMC2980007

1-Benz­yloxy-4-chloro­benzene

Abstract

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 [triangle]); Shen et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00o50-scheme1.jpg

Experimental

Crystal data

  • C13H11ClO
  • M r = 218.67
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o50-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.115
  • S = 1.16
  • 2523 reflections
  • 137 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.48 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1161 Friedel pairs
  • Flack parameter: −0.08 (9)

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic) or 0.97 Å (methylene) and Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C13H11ClOF(000) = 456
Mr = 218.67Dx = 1.323 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2189 reflections
a = 11.485 (2) Åθ = 3.1–27.5°
b = 13.033 (3) ŵ = 0.32 mm1
c = 7.3333 (15) ÅT = 298 K
V = 1097.7 (4) Å3Bock, colourless
Z = 40.4 × 0.35 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer2523 independent reflections
Radiation source: fine-focus sealed tube2189 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −16→16
Tmin = 0.881, Tmax = 0.940l = −9→9
10943 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0118P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max = 0.001
S = 1.16Δρmax = 0.31 e Å3
2523 reflectionsΔρmin = −0.48 e Å3
137 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.073 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1161 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.08 (9)

Special details

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)

xyzUiso*/Ueq
Cl10.76032 (5)0.10633 (4)0.35041 (15)0.0662 (2)
C110.72273 (17)0.23611 (14)0.3557 (3)0.0450 (4)
C60.53613 (16)0.69777 (14)0.3347 (3)0.0400 (4)
C50.62546 (18)0.74952 (15)0.4233 (3)0.0472 (5)
H50.68960.71340.46630.057*
C120.79431 (18)0.30526 (17)0.4443 (3)0.0477 (5)
H120.86360.28330.49690.057*
O10.63588 (13)0.54166 (11)0.3941 (3)0.0610 (5)
C80.65937 (17)0.43950 (15)0.3727 (3)0.0443 (4)
C40.6193 (2)0.85449 (18)0.4478 (4)0.0555 (6)
H40.67910.88850.50850.067*
C100.62149 (18)0.26770 (16)0.2733 (3)0.0483 (5)
H100.57470.22060.21250.058*
C130.76238 (17)0.40660 (17)0.4542 (3)0.0468 (5)
H130.80960.45330.51530.056*
C90.58956 (18)0.37006 (16)0.2814 (3)0.0471 (5)
H90.52130.39200.22540.056*
C70.53952 (18)0.58411 (16)0.3009 (3)0.0480 (5)
H7A0.46810.55270.34410.058*
H7B0.54640.57080.17120.058*
C20.4370 (2)0.85864 (19)0.2956 (4)0.0603 (6)
H20.37360.89530.25140.072*
C10.44145 (19)0.75356 (17)0.2727 (3)0.0502 (5)
H10.38030.71990.21510.060*
C30.5254 (2)0.90919 (16)0.3831 (4)0.0587 (6)
H30.52210.97990.39870.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0683 (4)0.0468 (3)0.0835 (4)0.0071 (2)0.0070 (4)−0.0037 (4)
C110.0476 (10)0.0429 (9)0.0443 (10)0.0007 (8)0.0080 (10)−0.0011 (12)
C60.0392 (9)0.0465 (10)0.0344 (9)−0.0003 (7)0.0012 (8)0.0031 (8)
C50.0399 (10)0.0505 (12)0.0514 (13)−0.0016 (8)−0.0072 (8)0.0054 (10)
C120.0396 (10)0.0555 (13)0.0479 (11)0.0008 (9)−0.0008 (10)0.0078 (10)
O10.0647 (9)0.0431 (7)0.0752 (11)0.0053 (6)−0.0318 (8)−0.0081 (8)
C80.0474 (10)0.0428 (9)0.0426 (10)−0.0012 (8)−0.0041 (9)−0.0006 (10)
C40.0502 (12)0.0533 (12)0.0631 (14)−0.0104 (10)−0.0051 (11)−0.0005 (11)
C100.0460 (11)0.0518 (11)0.0471 (10)−0.0068 (9)−0.0001 (10)−0.0095 (10)
C130.0452 (11)0.0484 (12)0.0469 (12)−0.0071 (8)−0.0093 (10)0.0001 (9)
C90.0399 (10)0.0547 (11)0.0466 (11)0.0026 (8)−0.0082 (9)−0.0061 (10)
C70.0440 (10)0.0511 (11)0.0488 (13)−0.0004 (8)−0.0100 (9)−0.0008 (9)
C20.0518 (12)0.0606 (13)0.0686 (16)0.0148 (11)−0.0061 (11)0.0069 (12)
C10.0395 (10)0.0578 (13)0.0535 (11)0.0006 (8)−0.0077 (10)−0.0018 (10)
C30.0615 (14)0.0442 (10)0.0705 (17)0.0003 (9)0.0027 (13)0.0021 (12)

Geometric parameters (Å, °)

Cl1—C111.7460 (19)C4—C31.377 (3)
C11—C101.374 (3)C4—H40.93
C11—C121.382 (3)C10—C91.385 (3)
C6—C11.385 (3)C10—H100.93
C6—C51.389 (3)C13—H130.93
C6—C71.502 (3)C9—H90.93
C5—C41.382 (3)C7—H7A0.97
C5—H50.93C7—H7B0.97
C12—C131.373 (3)C2—C31.370 (3)
C12—H120.93C2—C11.381 (3)
O1—C81.367 (2)C2—H20.93
O1—C71.413 (2)C1—H10.93
C8—C91.382 (3)C3—H30.93
C8—C131.393 (3)
C10—C11—C12120.99 (19)C12—C13—C8120.0 (2)
C10—C11—Cl1119.34 (16)C12—C13—H13120.0
C12—C11—Cl1119.67 (17)C8—C13—H13120.0
C1—C6—C5118.59 (18)C8—C9—C10119.85 (19)
C1—C6—C7118.95 (17)C8—C9—H9120.1
C5—C6—C7122.45 (17)C10—C9—H9120.1
C4—C5—C6120.25 (19)O1—C7—C6109.07 (15)
C4—C5—H5119.9O1—C7—H7A109.9
C6—C5—H5119.9C6—C7—H7A109.9
C13—C12—C11119.55 (19)O1—C7—H7B109.9
C13—C12—H12120.2C6—C7—H7B109.9
C11—C12—H12120.2H7A—C7—H7B108.3
C8—O1—C7118.71 (15)C3—C2—C1120.4 (2)
O1—C8—C9125.35 (17)C3—C2—H2119.8
O1—C8—C13114.72 (17)C1—C2—H2119.8
C9—C8—C13119.93 (19)C2—C1—C6120.7 (2)
C3—C4—C5120.5 (2)C2—C1—H1119.7
C3—C4—H4119.7C6—C1—H1119.7
C5—C4—H4119.7C2—C3—C4119.5 (2)
C11—C10—C9119.62 (19)C2—C3—H3120.2
C11—C10—H10120.2C4—C3—H3120.2
C9—C10—H10120.2
C1—C6—C5—C4−0.2 (3)O1—C8—C9—C10−178.3 (2)
C7—C6—C5—C4178.7 (2)C13—C8—C9—C100.9 (3)
C10—C11—C12—C131.6 (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—C13173.7 (2)C5—C6—C7—O18.0 (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—C21.2 (3)
Cl1—C11—C10—C9178.22 (17)C7—C6—C1—C2−177.8 (2)
C11—C12—C13—C8−1.0 (3)C1—C2—C3—C40.2 (4)
O1—C8—C13—C12179.0 (2)C5—C4—C3—C20.7 (4)
C9—C8—C13—C12−0.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···Cg2i0.932.813.570 (3)140
C10—H10···Cg1i0.932.883.624 (3)138

Symmetry codes: (i) −x+1, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2976).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Liu, G.-H., Xue, Y.-N., Yao, M., Yu, H. & Fang, H.-B. (2006). Acta Cryst. E62, o2848–o2849.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shen, C. K. F., Duong, H. M., Sonmez, G. & Wudl, F. (2003). J. Am. Chem. Soc 125, 16206–16207. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography