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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1587.
Published online 2008 July 26. doi:  10.1107/S1600536808022721
PMCID: PMC2962204

3-Chloro­phenyl benzoate

Abstract

The C=O group in the title compound, C13H9ClO2, is syn to the chloro group. The two aromatic rings are twisted by 56.88 (6)°. Adjacent mol­ecules are linked via weak C—H(...)O hydrogen bonding into a linear chain.

Related literature

For previous studies, see: Gowda et al. (2007a [triangle],b [triangle],c [triangle]); Nayak & Gowda (2008 [triangle]).

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Object name is e-64-o1587-scheme1.jpg

Experimental

Crystal data

  • C13H9ClO2
  • M r = 232.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1587-efi1.jpg
  • a = 6.0734 (6) Å
  • b = 8.389 (1) Å
  • c = 11.747 (2) Å
  • α = 107.89 (1)°
  • β = 102.98 (1)°
  • γ = 93.25 (1)°
  • V = 549.89 (13) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 2.92 mm−1
  • T = 299 (2) K
  • 0.60 × 0.55 × 0.50 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.197, T max = 0.233
  • 2143 measured reflections
  • 1947 independent reflections
  • 1872 reflections with I > 2σ(I)
  • R int = 0.086
  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.135
  • S = 1.10
  • 1947 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022721/ng2472sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022721/ng2472Isup2.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 structures of aryl benzoates (Gowda et al., 2007a, b, c), in the present work, the structure of 3-chlorophenyl benzoate (3CPBA) has been determined. The conformation of the C=O bond in 3CPBA is syn to the meta-chloro group in the phenolic benzene ring (Fig. 1), in contrast to the anti conformations of the C=O bond and the meta-methyl group in 3-methylphenyl benzoate (3MePBA) (Gowda et al., 2007a). The bond parameters in 3CPBA are similar to those of 3MePBA (Gowda et al., 2007a), 2,3-dichlorophenyl benzoate (23DCPBA)(Gowda et al., 2007c), 3,4-dichlorophenyl benzoate(34DCPBA) (Gowda et al., 2007b) and other aryl benzoates (Gowda et al., 2007a, b, c). The dihedral angle between the benzene and benzoyl rings in 3CPBA is 56.88 (6)°, compared to the values of 79.61 (6)° in 3MePBA, 50.16 (7)° in 23DCPBA and 53.77 (5)° in 34DCPBA. The packing diagram of the crystal structure in which the molecules are connected via intermolecular C—H—O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared according to the 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). The single crystals used in X-ray diffraction studies were obtained by the slow evaporation of an ethanolic solution of the title compound at room temperature.

Refinement

All H atoms were included in the riding-model approximation with C—H = 0.93 Å, and with Uiso(H) = 1.2xUeq(C).

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.
Molecular packing of the title compound.

Crystal data

C13H9ClO2Z = 2
Mr = 232.65F000 = 240
Triclinic, P1Dx = 1.405 Mg m3
Hall symbol: -P 1Cu Kα radiation λ = 1.54180 Å
a = 6.0734 (6) ÅCell parameters from 25 reflections
b = 8.389 (1) Åθ = 5.6–31.7º
c = 11.747 (2) ŵ = 2.92 mm1
α = 107.89 (1)ºT = 299 (2) K
β = 102.98 (1)ºPrism, colourless
γ = 93.25 (1)º0.60 × 0.55 × 0.50 mm
V = 549.89 (13) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.086
Radiation source: fine-focus sealed tubeθmax = 66.9º
Monochromator: graphiteθmin = 4.1º
T = 299(2) Kh = −7→1
ω/2θ scansk = −9→9
Absorption correction: ψ scan(North et al., 1968)l = −13→14
Tmin = 0.197, Tmax = 0.2333 standard reflections
2143 measured reflections every 120 min
1947 independent reflections intensity decay: 1.0%
1872 reflections with I > 2σ(I)

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046  w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1623P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max = 0.002
S = 1.10Δρmax = 0.30 e Å3
1947 reflectionsΔρmin = −0.34 e Å3
146 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.149 (8)
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
Cl10.29134 (10)0.17688 (7)−0.06457 (6)0.0678 (3)
O10.2384 (2)0.74790 (18)0.23750 (15)0.0565 (4)
O20.5777 (2)0.70473 (19)0.33852 (15)0.0587 (4)
C10.1614 (3)0.5746 (2)0.18489 (18)0.0474 (5)
C20.2647 (3)0.4730 (2)0.10218 (19)0.0477 (5)
H20.39620.51490.08690.057*
C30.1670 (3)0.3070 (3)0.04263 (19)0.0482 (5)
C4−0.0281 (3)0.2436 (3)0.0636 (2)0.0546 (5)
H4−0.09370.13210.02120.065*
C5−0.1247 (4)0.3482 (3)0.1485 (2)0.0593 (6)
H5−0.25490.30600.16470.071*
C6−0.0314 (3)0.5149 (3)0.2099 (2)0.0555 (5)
H6−0.09770.58530.26690.067*
C70.4554 (3)0.7994 (3)0.30835 (17)0.0458 (5)
C80.5176 (3)0.9840 (3)0.34208 (17)0.0457 (5)
C90.3622 (4)1.0902 (3)0.3149 (2)0.0568 (5)
H90.21091.04640.27400.068*
C100.4331 (5)1.2610 (3)0.3487 (2)0.0680 (7)
H100.32871.33230.33070.082*
C110.6556 (5)1.3268 (3)0.4086 (2)0.0692 (7)
H110.70181.44230.43150.083*
C120.8107 (5)1.2214 (3)0.4347 (2)0.0717 (7)
H120.96191.26580.47520.086*
C130.7428 (4)1.0512 (3)0.4013 (2)0.0602 (6)
H130.84860.98040.41840.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0704 (4)0.0528 (4)0.0800 (5)0.0084 (3)0.0358 (3)0.0095 (3)
O10.0472 (8)0.0453 (8)0.0692 (9)0.0134 (6)0.0057 (6)0.0131 (7)
O20.0543 (8)0.0553 (9)0.0681 (10)0.0198 (7)0.0096 (7)0.0247 (7)
C10.0436 (9)0.0457 (11)0.0534 (11)0.0114 (8)0.0092 (8)0.0183 (9)
C20.0429 (10)0.0475 (11)0.0581 (11)0.0066 (8)0.0177 (8)0.0215 (9)
C30.0471 (10)0.0478 (11)0.0560 (11)0.0098 (8)0.0179 (8)0.0218 (9)
C40.0502 (11)0.0492 (11)0.0667 (13)0.0021 (8)0.0140 (9)0.0241 (10)
C50.0447 (11)0.0721 (15)0.0711 (14)0.0048 (9)0.0210 (9)0.0335 (12)
C60.0464 (10)0.0671 (14)0.0574 (12)0.0162 (9)0.0192 (9)0.0211 (10)
C70.0452 (10)0.0506 (11)0.0456 (10)0.0152 (8)0.0148 (8)0.0176 (8)
C80.0498 (10)0.0493 (11)0.0412 (9)0.0133 (8)0.0146 (8)0.0161 (8)
C90.0574 (12)0.0549 (13)0.0593 (12)0.0174 (9)0.0124 (9)0.0202 (10)
C100.0885 (17)0.0525 (13)0.0701 (15)0.0255 (12)0.0225 (12)0.0254 (11)
C110.0935 (18)0.0520 (13)0.0634 (14)0.0038 (12)0.0272 (12)0.0169 (11)
C120.0675 (15)0.0653 (15)0.0712 (15)−0.0050 (11)0.0129 (11)0.0128 (12)
C130.0534 (12)0.0594 (13)0.0630 (13)0.0109 (10)0.0076 (9)0.0177 (11)

Geometric parameters (Å, °)

Cl1—C31.739 (2)C6—H60.9300
O1—C71.356 (2)C7—C81.479 (3)
O1—C11.399 (2)C8—C131.384 (3)
O2—C71.195 (2)C8—C91.387 (3)
C1—C21.374 (3)C9—C101.378 (3)
C1—C61.374 (3)C9—H90.9300
C2—C31.380 (3)C10—C111.370 (4)
C2—H20.9300C10—H100.9300
C3—C41.374 (3)C11—C121.376 (4)
C4—C51.376 (3)C11—H110.9300
C4—H40.9300C12—C131.371 (4)
C5—C61.379 (3)C12—H120.9300
C5—H50.9300C13—H130.9300
C7—O1—C1118.81 (14)O2—C7—C8125.42 (19)
C2—C1—C6122.04 (19)O1—C7—C8111.50 (15)
C2—C1—O1120.12 (18)C13—C8—C9119.3 (2)
C6—C1—O1117.55 (18)C13—C8—C7117.74 (18)
C1—C2—C3117.83 (17)C9—C8—C7122.95 (18)
C1—C2—H2121.1C10—C9—C8119.6 (2)
C3—C2—H2121.1C10—C9—H9120.2
C4—C3—C2121.76 (19)C8—C9—H9120.2
C4—C3—Cl1119.48 (17)C11—C10—C9120.7 (2)
C2—C3—Cl1118.73 (14)C11—C10—H10119.7
C3—C4—C5118.8 (2)C9—C10—H10119.7
C3—C4—H4120.6C10—C11—C12119.8 (2)
C5—C4—H4120.6C10—C11—H11120.1
C4—C5—C6120.99 (19)C12—C11—H11120.1
C4—C5—H5119.5C13—C12—C11120.2 (2)
C6—C5—H5119.5C13—C12—H12119.9
C1—C6—C5118.6 (2)C11—C12—H12119.9
C1—C6—H6120.7C12—C13—C8120.4 (2)
C5—C6—H6120.7C12—C13—H13119.8
O2—C7—O1123.08 (19)C8—C13—H13119.8
C7—O1—C1—C2−61.9 (2)C1—O1—C7—C8172.24 (16)
C7—O1—C1—C6124.2 (2)O2—C7—C8—C137.9 (3)
C6—C1—C2—C30.7 (3)O1—C7—C8—C13−172.14 (18)
O1—C1—C2—C3−172.97 (16)O2—C7—C8—C9−173.4 (2)
C1—C2—C3—C40.5 (3)O1—C7—C8—C96.6 (3)
C1—C2—C3—Cl1178.84 (14)C13—C8—C9—C10−1.0 (3)
C2—C3—C4—C5−1.5 (3)C7—C8—C9—C10−179.7 (2)
Cl1—C3—C4—C5−179.86 (16)C8—C9—C10—C110.2 (4)
C3—C4—C5—C61.4 (3)C9—C10—C11—C120.4 (4)
C2—C1—C6—C5−0.8 (3)C10—C11—C12—C13−0.2 (4)
O1—C1—C6—C5173.01 (18)C11—C12—C13—C8−0.6 (4)
C4—C5—C6—C1−0.3 (3)C9—C8—C13—C121.2 (3)
C1—O1—C7—O2−7.8 (3)C7—C8—C13—C12180.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.463.319 (3)154

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2472).

References

  • Enraf–Nonius (1996). CAD-4-PC Enraf–Nonius, Delft, The Netherlands.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3756.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007b). Acta Cryst. E63, o3801.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007c). Acta Cryst. E63, o4286.
  • Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63 In the press.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stoe & Cie (1987). REDU4 Stoe & Cie GmbH, Darmstadt, Germany.

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