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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1546.
Published online 2008 July 19. doi:  10.1107/S1600536808022290
PMCID: PMC2962170

2-Chloro­phenyl 4-methyl­benzoate

Abstract

The conformation of the C=O bond in the title compound, C14H11ClO2, is anti to the Cl atom, similar to what was observed in 2-methyl­phenyl 4-methyl­benzoate. The dihedral angle between the two aromatic rings is 59.36 (7)°.

Related literature

For related literature, see: Gowda et al. (2008a [triangle],b [triangle],c [triangle]); Nayak & Gowda (2008 [triangle]).

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Object name is e-64-o1546-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-o1546-efi1.jpg
  • a = 4.0538 (8) Å
  • b = 13.661 (3) Å
  • c = 10.975 (2) Å
  • β = 91.70 (2)°
  • V = 607.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 299 (2) K
  • 0.48 × 0.24 × 0.16 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.869, T max = 0.954
  • 4160 measured reflections
  • 2238 independent reflections
  • 1632 reflections with I > 2σ(I)
  • R int = 0.012

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.116
  • S = 1.15
  • 2238 reflections
  • 155 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.34 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 957 Friedel pairs
  • Flack parameter: −0.09 (9)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022290/bt2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022290/bt2750Isup2.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

As part of a study of the substituent effects on the crystal structures of aryl benzoates (Gowda et al., 2008a, 2008b, 2008c), in the present work, the structure of 2-chlorophenyl 4-methylbenzoate (2CP4MBA) has been determined. The conformation of the C=O bond in 2CP4MBA is anti to the ortho-chloro group in the phenolic benzene ring (Fig. 1), similar to what is observed in 2-methylphenyl 4-methylbenzoate (2MP4MBA) (Gowda et al., 2008c). The dihedral angle between the benzene and benzoyl rings in 2CP4MBA is 59.36 (7)°, compared with the values of 71.75 (7)° in 3CP4MBA (Gowda et al., 2008a), 63.89 (8)° in 4CP4MBA (Gowda et al., 2008b) and 73.04 (8)° in 2MP4MBA (Gowda et al., 2008c). Further, the bond parameters in 2CP4MBA are similar to those in 2MP4MBA and other aryl benzoates (Gowda et al., 2008a, b, c). The packing diagram is shown in Fig. 2.

Experimental

The title compound was prepared according to a method of Nayak & Gowda (2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2008). Single crystals used in X-ray diffraction studies were obtained by slow evaporation of ethanolic solution of the title compound.

Refinement

The H atoms were positioned with idealized geometry and refined using a riding model with Caromatic—H = 0.93Å or Cmethyl—H = 0.96 Å and with isotropic displacement parameters set to 1.2 Ueq(C) or 1.5Ueq(Cmethyl). The methyl group was allowed to rotate but not to tip.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Packing diagram of the title compound.

Crystal data

C14H11ClO2F000 = 256
Mr = 246.68Dx = 1.349 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1136 reflections
a = 4.0538 (8) Åθ = 2.4–27.8º
b = 13.661 (3) ŵ = 0.30 mm1
c = 10.975 (2) ÅT = 299 (2) K
β = 91.70 (2)ºLong needle, colourless
V = 607.5 (2) Å30.48 × 0.24 × 0.16 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2238 independent reflections
Radiation source: fine-focus sealed tube1632 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.012
T = 299(2) Kθmax = 26.4º
Rotation method data acquisition using ω and [var phi] scansθmin = 2.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)h = −5→5
Tmin = 0.869, Tmax = 0.954k = −17→15
4160 measured reflectionsl = −13→7

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035  w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0085P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.018
S = 1.15Δρmax = 0.36 e Å3
2238 reflectionsΔρmin = −0.34 e Å3
155 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 957 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.09 (9)
Secondary atom site location: difference Fourier map

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
C10.7402 (8)0.6625 (2)0.2945 (2)0.0525 (7)
C20.5813 (7)0.6919 (2)0.3974 (2)0.0570 (8)
C30.5373 (9)0.7904 (3)0.4209 (3)0.0699 (10)
H30.43500.81040.49140.084*
C40.6454 (10)0.8581 (3)0.3396 (3)0.0801 (11)
H40.61070.92430.35440.096*
C50.8047 (9)0.8300 (3)0.2364 (4)0.0751 (10)
H50.87960.87650.18190.090*
C60.8512 (9)0.7319 (3)0.2154 (3)0.0677 (8)
H60.96000.71220.14610.081*
C70.6657 (7)0.5173 (2)0.1796 (2)0.0513 (7)
C80.7526 (7)0.4132 (2)0.1815 (2)0.0460 (6)
C90.9317 (7)0.3687 (2)0.2745 (2)0.0527 (7)
H91.00840.40570.34060.063*
C100.9986 (7)0.2701 (2)0.2709 (3)0.0579 (7)
H101.12160.24170.33450.069*
C110.8878 (7)0.2126 (2)0.1756 (3)0.0548 (7)
C120.7055 (7)0.2569 (2)0.0806 (2)0.0562 (8)
H120.62760.21920.01530.067*
C130.6405 (7)0.3554 (2)0.0827 (2)0.0552 (7)
H130.52160.38410.01840.066*
C140.9603 (8)0.1054 (3)0.1717 (3)0.0726 (8)
H14A1.10200.08800.23990.087*
H14B1.06770.09000.09730.087*
H14C0.75770.06930.17540.087*
O10.7986 (5)0.56428 (14)0.27927 (18)0.0615 (6)
O20.4938 (7)0.55841 (16)0.1064 (2)0.0776 (7)
Cl10.4406 (2)0.60598 (9)0.49831 (7)0.0834 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0659 (17)0.0460 (19)0.0452 (14)0.0061 (14)−0.0050 (12)−0.0011 (12)
C20.0682 (19)0.055 (2)0.0468 (15)−0.0031 (15)−0.0084 (13)−0.0042 (13)
C30.088 (2)0.067 (3)0.0541 (17)0.0134 (19)−0.0046 (16)−0.0151 (16)
C40.103 (3)0.047 (2)0.089 (2)0.008 (2)−0.022 (2)−0.008 (2)
C50.092 (3)0.050 (2)0.082 (2)−0.0120 (19)−0.0133 (19)0.0066 (17)
C60.083 (2)0.061 (2)0.0597 (16)−0.0017 (17)−0.0004 (15)−0.0015 (15)
C70.0616 (17)0.0522 (19)0.0397 (12)−0.0047 (14)−0.0037 (12)−0.0034 (13)
C80.0517 (15)0.0460 (18)0.0405 (12)−0.0052 (12)0.0039 (11)−0.0023 (11)
C90.0592 (18)0.054 (2)0.0442 (12)−0.0002 (14)−0.0031 (12)0.0047 (12)
C100.0649 (18)0.055 (2)0.0529 (15)0.0061 (15)−0.0060 (13)0.0039 (13)
C110.0583 (15)0.046 (2)0.0602 (16)−0.0030 (14)0.0119 (13)−0.0024 (12)
C120.0686 (18)0.057 (2)0.0431 (14)−0.0091 (15)0.0048 (13)−0.0107 (13)
C130.0638 (18)0.0587 (19)0.0427 (12)−0.0029 (16)−0.0052 (12)−0.0060 (14)
C140.080 (2)0.054 (2)0.084 (2)0.000 (2)0.0041 (16)−0.0060 (19)
O10.0858 (15)0.0461 (12)0.0514 (11)0.0094 (10)−0.0167 (10)−0.0022 (8)
O20.1052 (17)0.0570 (14)0.0686 (13)0.0119 (13)−0.0286 (13)−0.0011 (11)
Cl10.1042 (7)0.0856 (6)0.0608 (4)−0.0113 (6)0.0082 (4)0.0093 (4)

Geometric parameters (Å, °)

C1—C61.370 (5)C8—C91.376 (4)
C1—O11.374 (3)C8—C131.406 (4)
C1—C21.376 (4)C9—C101.375 (4)
C2—C31.382 (4)C9—H90.9300
C2—Cl11.723 (3)C10—C111.373 (4)
C3—C41.366 (5)C10—H100.9300
C3—H30.9300C11—C121.398 (4)
C4—C51.375 (6)C11—C141.495 (5)
C4—H40.9300C12—C131.372 (4)
C5—C61.373 (5)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300C14—H14A0.9600
C7—O21.188 (3)C14—H14B0.9600
C7—O11.365 (3)C14—H14C0.9600
C7—C81.465 (4)
C6—C1—O1122.5 (3)C13—C8—C7117.5 (2)
C6—C1—C2119.3 (3)C10—C9—C8120.8 (3)
O1—C1—C2118.1 (3)C10—C9—H9119.6
C1—C2—C3120.2 (3)C8—C9—H9119.6
C1—C2—Cl1120.1 (2)C11—C10—C9121.5 (3)
C3—C2—Cl1119.7 (2)C11—C10—H10119.3
C4—C3—C2119.4 (3)C9—C10—H10119.3
C4—C3—H3120.3C10—C11—C12118.3 (3)
C2—C3—H3120.3C10—C11—C14121.5 (3)
C3—C4—C5121.1 (4)C12—C11—C14120.2 (3)
C3—C4—H4119.5C13—C12—C11120.6 (2)
C5—C4—H4119.5C13—C12—H12119.7
C6—C5—C4118.8 (4)C11—C12—H12119.7
C6—C5—H5120.6C12—C13—C8120.4 (2)
C4—C5—H5120.6C12—C13—H13119.8
C1—C6—C5121.3 (3)C8—C13—H13119.8
C1—C6—H6119.4C11—C14—H14A109.5
C5—C6—H6119.4C11—C14—H14B109.5
O2—C7—O1121.9 (3)H14A—C14—H14B109.5
O2—C7—C8127.2 (2)C11—C14—H14C109.5
O1—C7—C8110.8 (2)H14A—C14—H14C109.5
C9—C8—C13118.3 (3)H14B—C14—H14C109.5
C9—C8—C7124.1 (2)C7—O1—C1119.4 (2)
C6—C1—C2—C3−0.6 (4)C13—C8—C9—C10−0.2 (4)
O1—C1—C2—C3175.5 (3)C7—C8—C9—C10178.8 (3)
C6—C1—C2—Cl1−179.8 (2)C8—C9—C10—C11−0.5 (4)
O1—C1—C2—Cl1−3.7 (4)C9—C10—C11—C120.5 (4)
C1—C2—C3—C41.7 (5)C9—C10—C11—C14−180.0 (3)
Cl1—C2—C3—C4−179.1 (3)C10—C11—C12—C130.2 (4)
C2—C3—C4—C5−1.7 (5)C14—C11—C12—C13−179.3 (3)
C3—C4—C5—C60.6 (5)C11—C12—C13—C8−0.9 (4)
O1—C1—C6—C5−176.4 (3)C9—C8—C13—C120.9 (4)
C2—C1—C6—C5−0.4 (5)C7—C8—C13—C12−178.2 (3)
C4—C5—C6—C10.4 (5)O2—C7—O1—C1−1.7 (4)
O2—C7—C8—C9−174.5 (3)C8—C7—O1—C1−179.1 (3)
O1—C7—C8—C92.7 (4)C6—C1—O1—C7−64.4 (4)
O2—C7—C8—C134.5 (5)C2—C1—O1—C7119.6 (3)
O1—C7—C8—C13−178.3 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2750).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1390. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1518. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64 Submitted. [PMC free article] [PubMed]
  • Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63 In the press.
  • Oxford Diffraction (2004). CrysAlis CCD Oxford Diffraction Ltd, Köln, Germany.
  • Oxford Diffraction (2007). CrysAlis RED Oxford Diffraction Ltd, Köln, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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