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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o88.
Published online 2007 December 6. doi:  10.1107/S1600536807062137
PMCID: PMC2915044

4-Methyl­phenyl 4-chloro­benzoate

Abstract

The crystal structure of the title compound, C14H11ClO2, is similar to those of phenyl benzoate, 4-methyl­phenyl benzoate and 4-methyl­phenyl 4-methyl­benzoate. The dihedral angle between the phenyl and benzene rings is 51.86 (4)°. The mol­ecules crystallize in planes parallel to (An external file that holds a picture, illustration, etc.
Object name is e-64-00o88-efi1.jpg02).

Related literature

For related literature, see: Adams & Morsi (1976 [triangle]); Gowda, Foro, Babitha & Fuess (2007a [triangle],b [triangle],c [triangle],d [triangle],e [triangle]); Gowda, Foro, Nayak & Fuess (2007a [triangle],b [triangle]); Nayak & Gowda (2007 [triangle]).

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Object name is e-64-00o88-scheme1.jpg

Experimental

Crystal data

  • C14H11ClO2
  • M r = 246.68
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o88-efi2.jpg
  • a = 14.6932 (4) Å
  • b = 11.3269 (3) Å
  • c = 7.2386 (2) Å
  • β = 101.050 (3)°
  • V = 1182.37 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 100 (2) K
  • 0.40 × 0.28 × 0.08 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.887, T max = 0.976
  • 17127 measured reflections
  • 2407 independent reflections
  • 1889 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.096
  • S = 1.04
  • 2407 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 1.04 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek 2003 [triangle]) and ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062137/bt2647sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062137/bt2647Isup2.hkl

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of 4-methylphenyl 4-chlorobenzoate (4MP4CBA) has been determined, as part of a study of substituent effects on the structures of industrially significant compounds (Gowda, Foro, Babitha & Fuess, 2007a, 2007b; Gowda, Foro, Nayak & Fuess, 2007a, 2007b). The structure of 4MP4CBA (Fig. 1) resembles those of phenyl benzoate (PBA)(Adams & Morsi, 1976), 4-methylphenyl benzoate (4MPBA) (Gowda, Foro, Nayak & Fuess, 2007b), 4-methylphenyl 4-methylbenzoate (4MP4MBA)(Gowda, Foro, Babitha & Fuess, 2007b) and other aryl benzoates (Gowda, Foro, Babitha & Fuess, 2007a; Gowda, Foro, Nayak & Fuess, 2007a). The bond parameters in 4MP4CBA are similar to those in PBA, 4MPBA, 4MP4MBA and other benzoates (Gowda, Foro, Babitha & Fuess, 2007a, 2007b; Gowda, Foro, Nayak & Fuess, 2007a, 2007b). The molecules in the title compound are packed into plane parallel to (-1 0 2) (Fig. 2).

Experimental

The title compound was prepared according to a literature method (Nayak & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2007). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement

The H atoms of the methyl groups were positioned with idealized geometry using a riding model with C—H = 0.98 Å. The other H atoms were located in difference map and their positions refined.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
Fig. 2.
Molecular packing of the title compound.

Crystal data

C14H11ClO2F000 = 512
Mr = 246.68Dx = 1.386 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 5716 reflections
a = 14.6932 (4) Åθ = 2.2–26.9º
b = 11.3269 (3) ŵ = 0.31 mm1
c = 7.2386 (2) ÅT = 100 (2) K
β = 101.050 (3)ºPrism, colourless
V = 1182.37 (6) Å30.40 × 0.28 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector2407 independent reflections
Radiation source: Enhance (Mo) X-ray Source1889 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
Detector resolution: 8.4012 pixels mm-1θmax = 26.4º
T = 100(2) Kθmin = 2.3º
Rotation method data acquisition using ω scans.h = −18→18
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2006)k = −13→14
Tmin = 0.887, Tmax = 0.976l = −9→9
17127 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.096  w = 1/[σ2(Fo2) + (0.0437P)2 + 0.873P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2407 reflectionsΔρmax = 1.04 e Å3
155 parametersΔρmin = −0.29 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cl1−0.39495 (3)0.43951 (5)0.00266 (7)0.03131 (16)
O10.06211 (8)0.40950 (10)0.28512 (17)0.0203 (3)
O20.02463 (9)0.23571 (11)0.40524 (18)0.0264 (3)
C1−0.27915 (12)0.40681 (16)0.0929 (2)0.0204 (4)
C2−0.25731 (12)0.30158 (16)0.1886 (2)0.0214 (4)
H2−0.30450.24730.20430.026*
C3−0.16463 (12)0.27738 (15)0.2611 (2)0.0193 (4)
H3−0.14810.20580.32750.023*
C4−0.09585 (11)0.35718 (15)0.2371 (2)0.0172 (3)
C5−0.11937 (12)0.46239 (15)0.1393 (2)0.0184 (4)
H5−0.07230.51670.12240.022*
C6−0.21182 (12)0.48738 (15)0.0668 (2)0.0196 (4)
H6−0.22870.55880.00020.024*
C70.00171 (12)0.32497 (15)0.3186 (2)0.0188 (4)
C80.15790 (11)0.38716 (16)0.3334 (2)0.0185 (4)
C90.19650 (12)0.28504 (15)0.2769 (2)0.0197 (4)
H90.15830.22450.21230.024*
C100.29215 (12)0.27312 (15)0.3169 (2)0.0208 (4)
H100.31930.20280.28060.025*
C110.34947 (12)0.36115 (16)0.4084 (2)0.0222 (4)
C120.30820 (12)0.46299 (16)0.4619 (2)0.0224 (4)
H120.34620.52440.52430.027*
C130.21257 (12)0.47634 (15)0.4254 (2)0.0199 (4)
H130.18510.54600.46330.024*
C140.45367 (13)0.34475 (18)0.4483 (3)0.0327 (5)
H14A0.46830.26030.45810.049*
H14B0.48050.38400.56690.049*
H14C0.47970.37940.34570.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0190 (2)0.0368 (3)0.0365 (3)0.00206 (19)0.00115 (18)0.0060 (2)
O10.0181 (6)0.0181 (6)0.0245 (6)−0.0002 (5)0.0033 (5)0.0019 (5)
O20.0240 (7)0.0247 (7)0.0303 (7)0.0022 (5)0.0044 (5)0.0110 (6)
C10.0170 (8)0.0249 (9)0.0192 (9)0.0012 (7)0.0032 (7)−0.0033 (7)
C20.0224 (9)0.0220 (9)0.0200 (9)−0.0038 (7)0.0049 (7)−0.0003 (7)
C30.0254 (9)0.0158 (8)0.0168 (8)−0.0002 (7)0.0043 (7)0.0003 (7)
C40.0206 (8)0.0167 (8)0.0149 (8)0.0011 (7)0.0052 (6)−0.0018 (7)
C50.0221 (8)0.0160 (8)0.0184 (8)−0.0012 (7)0.0070 (7)−0.0010 (7)
C60.0239 (9)0.0168 (8)0.0190 (8)0.0033 (7)0.0062 (7)0.0012 (7)
C70.0215 (8)0.0184 (9)0.0171 (8)−0.0022 (7)0.0051 (7)−0.0016 (7)
C80.0183 (8)0.0209 (9)0.0167 (8)0.0008 (7)0.0047 (7)0.0041 (7)
C90.0252 (9)0.0173 (9)0.0166 (8)−0.0010 (7)0.0043 (7)0.0000 (7)
C100.0265 (9)0.0178 (9)0.0200 (8)0.0031 (7)0.0087 (7)0.0009 (7)
C110.0221 (9)0.0234 (9)0.0226 (9)0.0010 (7)0.0080 (7)0.0037 (7)
C120.0241 (9)0.0200 (9)0.0231 (9)−0.0041 (7)0.0045 (7)−0.0005 (7)
C130.0239 (9)0.0166 (8)0.0205 (9)0.0013 (7)0.0074 (7)−0.0002 (7)
C140.0221 (9)0.0310 (11)0.0448 (12)0.0012 (8)0.0061 (8)0.0015 (9)

Geometric parameters (Å, °)

Cl1—C11.7414 (17)C8—C131.380 (2)
O1—C71.359 (2)C8—C91.384 (2)
O1—C81.407 (2)C9—C101.386 (2)
O2—C71.203 (2)C9—H90.9500
C1—C21.385 (3)C10—C111.389 (3)
C1—C61.385 (3)C10—H100.9500
C2—C31.390 (2)C11—C121.392 (3)
C2—H20.9500C11—C141.514 (2)
C3—C41.391 (2)C12—C131.387 (2)
C3—H30.9500C12—H120.9500
C4—C51.395 (2)C13—H130.9500
C4—C71.487 (2)C14—H14A0.9800
C5—C61.388 (2)C14—H14B0.9800
C5—H50.9500C14—H14C0.9800
C6—H60.9500
C7—O1—C8119.05 (13)C13—C8—O1116.77 (15)
C2—C1—C6122.14 (16)C9—C8—O1121.61 (15)
C2—C1—Cl1119.12 (14)C8—C9—C10118.44 (16)
C6—C1—Cl1118.74 (14)C8—C9—H9120.8
C1—C2—C3118.36 (16)C10—C9—H9120.8
C1—C2—H2120.8C9—C10—C11121.84 (16)
C3—C2—H2120.8C9—C10—H10119.1
C2—C3—C4120.50 (16)C11—C10—H10119.1
C2—C3—H3119.8C10—C11—C12118.09 (16)
C4—C3—H3119.8C10—C11—C14120.10 (16)
C3—C4—C5120.19 (16)C12—C11—C14121.81 (17)
C3—C4—C7117.33 (15)C13—C12—C11121.12 (17)
C5—C4—C7122.48 (15)C13—C12—H12119.4
C6—C5—C4119.67 (16)C11—C12—H12119.4
C6—C5—H5120.2C8—C13—C12119.11 (16)
C4—C5—H5120.2C8—C13—H13120.4
C1—C6—C5119.14 (16)C12—C13—H13120.4
C1—C6—H6120.4C11—C14—H14A109.5
C5—C6—H6120.4C11—C14—H14B109.5
O2—C7—O1123.92 (15)H14A—C14—H14B109.5
O2—C7—C4124.41 (15)C11—C14—H14C109.5
O1—C7—C4111.66 (14)H14A—C14—H14C109.5
C13—C8—C9121.39 (16)H14B—C14—H14C109.5
C6—C1—C2—C30.4 (3)C3—C4—C7—O1179.72 (14)
Cl1—C1—C2—C3−179.45 (13)C5—C4—C7—O1−0.1 (2)
C1—C2—C3—C4−0.2 (3)C7—O1—C8—C13−134.88 (16)
C2—C3—C4—C5−0.2 (3)C7—O1—C8—C950.6 (2)
C2—C3—C4—C7−179.97 (15)C13—C8—C9—C100.8 (3)
C3—C4—C5—C60.3 (2)O1—C8—C9—C10174.97 (14)
C7—C4—C5—C6−179.89 (15)C8—C9—C10—C11−1.1 (3)
C2—C1—C6—C5−0.2 (3)C9—C10—C11—C120.6 (3)
Cl1—C1—C6—C5179.59 (13)C9—C10—C11—C14−179.67 (17)
C4—C5—C6—C1−0.1 (3)C10—C11—C12—C130.2 (3)
C8—O1—C7—O27.9 (2)C14—C11—C12—C13−179.55 (17)
C8—O1—C7—C4−172.71 (14)C9—C8—C13—C120.0 (3)
C3—C4—C7—O2−0.9 (3)O1—C8—C13—C12−174.50 (15)
C5—C4—C7—O2179.27 (17)C11—C12—C13—C8−0.5 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2647).

References

  • Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3801.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007b). Acta Cryst. E63, o3867.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007c). Acta Cryst. E63, o3876.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007d). Acta Cryst. E63, o3877.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007e). Acta Cryst. E63, o4286.
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  • Nayak, R. & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62 In the press.
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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography