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Acta Crystallogr Sect E Struct Rep Online. 2011 November 1; 67(Pt 11): o3030.
Published online 2011 October 22. doi:  10.1107/S1600536811042851
PMCID: PMC3247425

2-(4-Chloro­phen­yl)-2-oxoethyl 4-methyl­benzoate

Abstract

In the title compound, C16H13ClO3, the dihedral angle between the benzene rings is 80.74 (8)°. In the crystal, C—H(...)O hydrogen bonds link the mol­ecules to form C(11) chains propagating in [010].

Related literature

For a related structure and background references to phenacyl benzoates, see: Fun et al. (2011 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-67-o3030-scheme1.jpg

Experimental

Crystal data

  • C16H13ClO3
  • M r = 288.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-o3030-efi1.jpg
  • a = 5.9132 (4) Å
  • b = 8.5044 (6) Å
  • c = 27.8767 (18) Å
  • β = 95.880 (1)°
  • V = 1394.49 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 297 K
  • 0.51 × 0.30 × 0.06 mm

Data collection

  • Bruker SMART APEXII DUO CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.871, T max = 0.983
  • 21275 measured reflections
  • 4070 independent reflections
  • 2628 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.144
  • S = 1.05
  • 4070 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042851/hb6454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042851/hb6454Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042851/hb6454Isup3.cml

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of the post of Research Officer under the Research University Grant (No. 1001/PFIZIK/811160). AMI thanks Professor Sandeep Sanchethi, Director of the National Institute of Technology-Karnataka, India for providing the research facilities. AMI also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India for the ‘Young Scientist’ award. MNS thanks the Department of Information Technology, Government of India for financial support.

supplementary crystallographic information

Comment

As part of our ongoing studies of phenacyl benzoates (Fun et al., 2011), we now report the synthesis and sturcture of the title compound, (I).

In the title compound (Fig. 1), the dihedral angle formed between the chloro-substituted (C1–C6) and the methyl-substituted (C10–C15) benzene rings is 80.74 (8)°. Bond lengths and angles are within the normal ranges and are comparable to a related structure (Fun et al., 2011).

In the crystal (Fig. 2), intermolecular C16—H16C···O1 hydrogen bonds (Table 1) link the molecules to form chains along the b axis.

Experimental

A mixture of 4-methylbenzoic acid (1.0 g, 0.0073 mol), potassium carbonate (1.10 g, 0.0080 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.70 g, 0.0073 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of the title compound began to separate out. They were collected by filtration and recrystallized from ethanol to yield colourless plates of (I). Yield: 1.95 g, 92.8%. M. p: 405–406 K.

Refinement

All H atoms were positioned geometrically and refined with a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) [C–H = 0.93 or 0.97 Å]. A rotating group model was applied to the methyl group.

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound, viewed along the showing the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C16H13ClO3F(000) = 600
Mr = 288.71Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4428 reflections
a = 5.9132 (4) Åθ = 2.8–28.1°
b = 8.5044 (6) ŵ = 0.28 mm1
c = 27.8767 (18) ÅT = 297 K
β = 95.880 (1)°Plate, colourless
V = 1394.49 (16) Å30.51 × 0.30 × 0.06 mm
Z = 4

Data collection

Bruker SMART APEXII DUO CCD diffractometer4070 independent reflections
Radiation source: fine-focus sealed tube2628 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −8→8
Tmin = 0.871, Tmax = 0.983k = −11→12
21275 measured reflectionsl = −39→39

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3124P] where P = (Fo2 + 2Fc2)/3
4070 reflections(Δ/σ)max = 0.002
182 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.42 e Å3

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
Cl11.34410 (11)0.75388 (9)1.047675 (19)0.0935 (2)
O10.5306 (2)0.69016 (17)0.86404 (5)0.0739 (4)
O20.6246 (2)0.50027 (17)0.79276 (4)0.0612 (3)
O30.3791 (2)0.35541 (15)0.83027 (4)0.0643 (3)
C10.8059 (3)0.7539 (2)0.94970 (7)0.0569 (4)
H1A0.66460.80270.94530.068*
C20.9496 (4)0.7851 (2)0.99053 (7)0.0646 (5)
H2A0.90560.85391.01380.078*
C31.1586 (3)0.7138 (2)0.99658 (6)0.0589 (4)
C41.2267 (3)0.6099 (2)0.96302 (6)0.0598 (4)
H4A1.36840.56170.96780.072*
C51.0808 (3)0.5784 (2)0.92215 (6)0.0530 (4)
H5A1.12480.50830.89920.064*
C60.8693 (3)0.65035 (18)0.91501 (5)0.0462 (3)
C70.7093 (3)0.62133 (19)0.87099 (6)0.0487 (4)
C80.7785 (3)0.5032 (2)0.83558 (6)0.0579 (4)
H8A0.92980.52830.82730.070*
H8B0.78420.39970.85030.070*
C90.4256 (3)0.42441 (19)0.79494 (6)0.0484 (4)
C100.2774 (3)0.43770 (17)0.74889 (5)0.0438 (3)
C110.3350 (3)0.53418 (19)0.71169 (6)0.0496 (4)
H11A0.47300.58760.71460.060*
C120.1863 (3)0.55014 (19)0.67042 (6)0.0523 (4)
H12A0.22640.61440.64560.063*
C13−0.0210 (3)0.47287 (18)0.66499 (5)0.0482 (4)
C14−0.0734 (3)0.3726 (2)0.70156 (6)0.0531 (4)
H14A−0.20930.31660.69820.064*
C150.0749 (3)0.3551 (2)0.74308 (6)0.0505 (4)
H15A0.03790.28730.76720.061*
C16−0.1878 (3)0.5006 (2)0.62043 (6)0.0604 (4)
H16A−0.11020.48920.59200.091*
H16B−0.24920.60490.62150.091*
H16C−0.30890.42520.61970.091*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0873 (4)0.1316 (6)0.0578 (3)−0.0190 (4)−0.0114 (3)−0.0225 (3)
O10.0601 (8)0.0737 (8)0.0831 (9)0.0200 (7)−0.0156 (7)−0.0148 (7)
O20.0487 (6)0.0890 (9)0.0452 (6)−0.0116 (6)0.0008 (5)−0.0060 (6)
O30.0746 (8)0.0656 (8)0.0513 (7)−0.0104 (7)−0.0006 (6)0.0087 (6)
C10.0517 (9)0.0576 (10)0.0617 (10)0.0007 (8)0.0071 (8)−0.0088 (8)
C20.0714 (12)0.0683 (11)0.0555 (10)−0.0103 (10)0.0130 (9)−0.0163 (8)
C30.0615 (10)0.0705 (11)0.0438 (8)−0.0165 (9)0.0011 (7)−0.0034 (8)
C40.0510 (9)0.0736 (11)0.0526 (9)0.0014 (8)−0.0044 (7)−0.0015 (8)
C50.0518 (9)0.0582 (9)0.0480 (8)0.0033 (7)0.0011 (7)−0.0065 (7)
C60.0466 (8)0.0462 (8)0.0457 (8)−0.0043 (6)0.0039 (6)−0.0001 (6)
C70.0452 (8)0.0482 (8)0.0518 (8)−0.0021 (7)−0.0002 (7)0.0017 (7)
C80.0470 (9)0.0747 (11)0.0503 (9)0.0005 (8)−0.0042 (7)−0.0102 (8)
C90.0497 (8)0.0485 (8)0.0469 (8)0.0006 (7)0.0046 (7)−0.0075 (7)
C100.0455 (8)0.0443 (7)0.0418 (7)−0.0007 (6)0.0059 (6)−0.0054 (6)
C110.0483 (8)0.0488 (8)0.0522 (8)−0.0082 (7)0.0071 (7)0.0001 (7)
C120.0617 (10)0.0492 (8)0.0467 (8)−0.0037 (7)0.0081 (7)0.0046 (7)
C130.0532 (9)0.0478 (8)0.0431 (8)0.0039 (7)0.0030 (6)−0.0083 (6)
C140.0483 (8)0.0598 (10)0.0508 (8)−0.0109 (7)0.0040 (7)−0.0052 (7)
C150.0518 (9)0.0555 (9)0.0449 (8)−0.0097 (7)0.0082 (7)0.0004 (7)
C160.0638 (11)0.0631 (10)0.0524 (9)0.0048 (9)−0.0030 (8)−0.0047 (8)

Geometric parameters (Å, °)

Cl1—C31.7400 (17)C8—H8A0.9700
O1—C71.2062 (19)C8—H8B0.9700
O2—C91.349 (2)C9—C101.483 (2)
O2—C81.4250 (18)C10—C151.383 (2)
O3—C91.203 (2)C10—C111.392 (2)
C1—C21.375 (2)C11—C121.381 (2)
C1—C61.387 (2)C11—H11A0.9300
C1—H1A0.9300C12—C131.385 (2)
C2—C31.371 (3)C12—H12A0.9300
C2—H2A0.9300C13—C141.388 (2)
C3—C41.377 (3)C13—C161.523 (2)
C4—C51.383 (2)C14—C151.387 (2)
C4—H4A0.9300C14—H14A0.9300
C5—C61.388 (2)C15—H15A0.9300
C5—H5A0.9300C16—H16A0.9600
C6—C71.491 (2)C16—H16B0.9600
C7—C81.495 (2)C16—H16C0.9600
C9—O2—C8117.12 (13)O3—C9—O2122.98 (15)
C2—C1—C6120.75 (17)O3—C9—C10125.56 (15)
C2—C1—H1A119.6O2—C9—C10111.46 (14)
C6—C1—H1A119.6C15—C10—C11119.15 (14)
C3—C2—C1119.28 (17)C15—C10—C9119.38 (14)
C3—C2—H2A120.4C11—C10—C9121.45 (14)
C1—C2—H2A120.4C12—C11—C10119.66 (15)
C2—C3—C4121.52 (16)C12—C11—H11A120.2
C2—C3—Cl1119.91 (15)C10—C11—H11A120.2
C4—C3—Cl1118.57 (15)C11—C12—C13121.67 (15)
C3—C4—C5118.90 (17)C11—C12—H12A119.2
C3—C4—H4A120.5C13—C12—H12A119.2
C5—C4—H4A120.5C12—C13—C14118.22 (14)
C4—C5—C6120.60 (16)C12—C13—C16120.48 (15)
C4—C5—H5A119.7C14—C13—C16121.28 (15)
C6—C5—H5A119.7C15—C14—C13120.59 (15)
C1—C6—C5118.94 (15)C15—C14—H14A119.7
C1—C6—C7118.97 (15)C13—C14—H14A119.7
C5—C6—C7122.08 (14)C10—C15—C14120.61 (15)
O1—C7—C6121.57 (15)C10—C15—H15A119.7
O1—C7—C8120.98 (15)C14—C15—H15A119.7
C6—C7—C8117.46 (13)C13—C16—H16A109.5
O2—C8—C7111.72 (14)C13—C16—H16B109.5
O2—C8—H8A109.3H16A—C16—H16B109.5
C7—C8—H8A109.3C13—C16—H16C109.5
O2—C8—H8B109.3H16A—C16—H16C109.5
C7—C8—H8B109.3H16B—C16—H16C109.5
H8A—C8—H8B107.9
C6—C1—C2—C30.6 (3)C8—O2—C9—O3−3.1 (2)
C1—C2—C3—C4−0.9 (3)C8—O2—C9—C10176.99 (14)
C1—C2—C3—Cl1179.20 (14)O3—C9—C10—C15−5.7 (2)
C2—C3—C4—C50.6 (3)O2—C9—C10—C15174.20 (14)
Cl1—C3—C4—C5−179.55 (14)O3—C9—C10—C11172.90 (16)
C3—C4—C5—C60.1 (3)O2—C9—C10—C11−7.2 (2)
C2—C1—C6—C50.0 (3)C15—C10—C11—C122.2 (2)
C2—C1—C6—C7−179.28 (16)C9—C10—C11—C12−176.38 (15)
C4—C5—C6—C1−0.4 (3)C10—C11—C12—C130.3 (3)
C4—C5—C6—C7178.91 (16)C11—C12—C13—C14−2.6 (2)
C1—C6—C7—O12.9 (3)C11—C12—C13—C16176.20 (15)
C5—C6—C7—O1−176.38 (18)C12—C13—C14—C152.3 (2)
C1—C6—C7—C8−177.07 (16)C16—C13—C14—C15−176.49 (15)
C5—C6—C7—C83.6 (2)C11—C10—C15—C14−2.5 (2)
C9—O2—C8—C7−77.7 (2)C9—C10—C15—C14176.13 (15)
O1—C7—C8—O27.0 (3)C13—C14—C15—C100.2 (3)
C6—C7—C8—O2−173.03 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16C···O1i0.962.463.383 (2)162

Symmetry codes: (i) −x, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6454).

References

  • Bruker (2009). APEX2, SAINT and SADABSBruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K., Loh, W.-S., Garudachari, B., Isloor, A. M. & Satyanarayana, M. N. (2011). Acta Cryst. E67, o2854. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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