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access2-Chlorophenyl 4-methylbenzoate
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
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)°.
![[Scheme 1]](bt2750scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2004![[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]](../../../../../../logos/arrows/e_arr.gif "Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.")
); cell CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536808022290/bt2750sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808022290/bt2750Isup2.hkl
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.
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.
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./bt2750fig1thm.gif) | 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. |
![[Figure 2]](./bt2750fig2thm.gif) | Fig. 2. Packing diagram of the title compound. |
| C14H11ClO2 | F(000) = 256 |
| Mr = 246.68 | Dx = 1.349 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 1136 reflections |
| a = 4.0538 (8) Å | θ = 2.4–27.8° |
| b = 13.661 (3) Å | µ = 0.30 mm−1 |
| c = 10.975 (2) Å | T = 299 K |
| β = 91.70 (2)° | Long needle, colourless |
| V = 607.5 (2) Å3 | 0.48 × 0.24 × 0.16 mm |
| Z = 2 |
| Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2238 independent reflections |
| Radiation source: fine-focus sealed tube | 1632 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.012 |
| Rotation method data acquisition using ω and ϕ scans | θmax = 26.4°, θmin = 2.4° |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | h = −5→5 |
| Tmin = 0.869, Tmax = 0.954 | k = −17→15 |
| 4160 measured reflections | l = −13→7 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0085P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.15 | (Δ/σ)max = 0.018 |
| 2238 reflections | Δρmax = 0.36 e Å−3 |
| 155 parameters | Δρmin = −0.34 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 957 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.09 (9) |
| C14H11ClO2 | V = 607.5 (2) Å3 |
| Mr = 246.68 | Z = 2 |
| Monoclinic, P21 | Mo Kα radiation |
| a = 4.0538 (8) Å | µ = 0.30 mm−1 |
| b = 13.661 (3) Å | T = 299 K |
| c = 10.975 (2) Å | 0.48 × 0.24 × 0.16 mm |
| β = 91.70 (2)° |
| Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2238 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1632 reflections with I > 2σ(I) |
| Tmin = 0.869, Tmax = 0.954 | Rint = 0.012 |
| 4160 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.116 | Δρmax = 0.36 e Å−3 |
| S = 1.15 | Δρmin = −0.34 e Å−3 |
| 2238 reflections | Absolute structure: Flack (1983), 957 Friedel pairs |
| 155 parameters | Absolute structure parameter: −0.09 (9) |
| 1 restraint |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.7402 (8) | 0.6625 (2) | 0.2945 (2) | 0.0525 (7) | |
| C2 | 0.5813 (7) | 0.6919 (2) | 0.3974 (2) | 0.0570 (8) | |
| C3 | 0.5373 (9) | 0.7904 (3) | 0.4209 (3) | 0.0699 (10) | |
| H3 | 0.4350 | 0.8104 | 0.4914 | 0.084* | |
| C4 | 0.6454 (10) | 0.8581 (3) | 0.3396 (3) | 0.0801 (11) | |
| H4 | 0.6107 | 0.9243 | 0.3544 | 0.096* | |
| C5 | 0.8047 (9) | 0.8300 (3) | 0.2364 (4) | 0.0751 (10) | |
| H5 | 0.8796 | 0.8765 | 0.1819 | 0.090* | |
| C6 | 0.8512 (9) | 0.7319 (3) | 0.2154 (3) | 0.0677 (8) | |
| H6 | 0.9600 | 0.7122 | 0.1461 | 0.081* | |
| C7 | 0.6657 (7) | 0.5173 (2) | 0.1796 (2) | 0.0513 (7) | |
| C8 | 0.7526 (7) | 0.4132 (2) | 0.1815 (2) | 0.0460 (6) | |
| C9 | 0.9317 (7) | 0.3687 (2) | 0.2745 (2) | 0.0527 (7) | |
| H9 | 1.0084 | 0.4057 | 0.3406 | 0.063* | |
| C10 | 0.9986 (7) | 0.2701 (2) | 0.2709 (3) | 0.0579 (7) | |
| H10 | 1.1216 | 0.2417 | 0.3345 | 0.069* | |
| C11 | 0.8878 (7) | 0.2126 (2) | 0.1756 (3) | 0.0548 (7) | |
| C12 | 0.7055 (7) | 0.2569 (2) | 0.0806 (2) | 0.0562 (8) | |
| H12 | 0.6276 | 0.2192 | 0.0153 | 0.067* | |
| C13 | 0.6405 (7) | 0.3554 (2) | 0.0827 (2) | 0.0552 (7) | |
| H13 | 0.5216 | 0.3841 | 0.0184 | 0.066* | |
| C14 | 0.9603 (8) | 0.1054 (3) | 0.1717 (3) | 0.0726 (8) | |
| H14A | 1.1020 | 0.0880 | 0.2399 | 0.087* | |
| H14B | 1.0677 | 0.0900 | 0.0973 | 0.087* | |
| H14C | 0.7577 | 0.0693 | 0.1754 | 0.087* | |
| O1 | 0.7986 (5) | 0.56428 (14) | 0.27927 (18) | 0.0615 (6) | |
| O2 | 0.4938 (7) | 0.55841 (16) | 0.1064 (2) | 0.0776 (7) | |
| Cl1 | 0.4406 (2) | 0.60598 (9) | 0.49831 (7) | 0.0834 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0659 (17) | 0.0460 (19) | 0.0452 (14) | 0.0061 (14) | −0.0050 (12) | −0.0011 (12) |
| C2 | 0.0682 (19) | 0.055 (2) | 0.0468 (15) | −0.0031 (15) | −0.0084 (13) | −0.0042 (13) |
| C3 | 0.088 (2) | 0.067 (3) | 0.0541 (17) | 0.0134 (19) | −0.0046 (16) | −0.0151 (16) |
| C4 | 0.103 (3) | 0.047 (2) | 0.089 (2) | 0.008 (2) | −0.022 (2) | −0.008 (2) |
| C5 | 0.092 (3) | 0.050 (2) | 0.082 (2) | −0.0120 (19) | −0.0133 (19) | 0.0066 (17) |
| C6 | 0.083 (2) | 0.061 (2) | 0.0597 (16) | −0.0017 (17) | −0.0004 (15) | −0.0015 (15) |
| C7 | 0.0616 (17) | 0.0522 (19) | 0.0397 (12) | −0.0047 (14) | −0.0037 (12) | −0.0034 (13) |
| C8 | 0.0517 (15) | 0.0460 (18) | 0.0405 (12) | −0.0052 (12) | 0.0039 (11) | −0.0023 (11) |
| C9 | 0.0592 (18) | 0.054 (2) | 0.0442 (12) | −0.0002 (14) | −0.0031 (12) | 0.0047 (12) |
| C10 | 0.0649 (18) | 0.055 (2) | 0.0529 (15) | 0.0061 (15) | −0.0060 (13) | 0.0039 (13) |
| C11 | 0.0583 (15) | 0.046 (2) | 0.0602 (16) | −0.0030 (14) | 0.0119 (13) | −0.0024 (12) |
| C12 | 0.0686 (18) | 0.057 (2) | 0.0431 (14) | −0.0091 (15) | 0.0048 (13) | −0.0107 (13) |
| C13 | 0.0638 (18) | 0.0587 (19) | 0.0427 (12) | −0.0029 (16) | −0.0052 (12) | −0.0060 (14) |
| C14 | 0.080 (2) | 0.054 (2) | 0.084 (2) | 0.000 (2) | 0.0041 (16) | −0.0060 (19) |
| O1 | 0.0858 (15) | 0.0461 (12) | 0.0514 (11) | 0.0094 (10) | −0.0167 (10) | −0.0022 (8) |
| O2 | 0.1052 (17) | 0.0570 (14) | 0.0686 (13) | 0.0119 (13) | −0.0286 (13) | −0.0011 (11) |
| Cl1 | 0.1042 (7) | 0.0856 (6) | 0.0608 (4) | −0.0113 (6) | 0.0082 (4) | 0.0093 (4) |
| C1—C6 | 1.370 (5) | C8—C9 | 1.376 (4) |
| C1—O1 | 1.374 (3) | C8—C13 | 1.406 (4) |
| C1—C2 | 1.376 (4) | C9—C10 | 1.375 (4) |
| C2—C3 | 1.382 (4) | C9—H9 | 0.9300 |
| C2—Cl1 | 1.723 (3) | C10—C11 | 1.373 (4) |
| C3—C4 | 1.366 (5) | C10—H10 | 0.9300 |
| C3—H3 | 0.9300 | C11—C12 | 1.398 (4) |
| C4—C5 | 1.375 (6) | C11—C14 | 1.495 (5) |
| C4—H4 | 0.9300 | C12—C13 | 1.372 (4) |
| C5—C6 | 1.373 (5) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | C13—H13 | 0.9300 |
| C6—H6 | 0.9300 | C14—H14A | 0.9600 |
| C7—O2 | 1.188 (3) | C14—H14B | 0.9600 |
| C7—O1 | 1.365 (3) | C14—H14C | 0.9600 |
| C7—C8 | 1.465 (4) | ||
| C6—C1—O1 | 122.5 (3) | C13—C8—C7 | 117.5 (2) |
| C6—C1—C2 | 119.3 (3) | C10—C9—C8 | 120.8 (3) |
| O1—C1—C2 | 118.1 (3) | C10—C9—H9 | 119.6 |
| C1—C2—C3 | 120.2 (3) | C8—C9—H9 | 119.6 |
| C1—C2—Cl1 | 120.1 (2) | C11—C10—C9 | 121.5 (3) |
| C3—C2—Cl1 | 119.7 (2) | C11—C10—H10 | 119.3 |
| C4—C3—C2 | 119.4 (3) | C9—C10—H10 | 119.3 |
| C4—C3—H3 | 120.3 | C10—C11—C12 | 118.3 (3) |
| C2—C3—H3 | 120.3 | C10—C11—C14 | 121.5 (3) |
| C3—C4—C5 | 121.1 (4) | C12—C11—C14 | 120.2 (3) |
| C3—C4—H4 | 119.5 | C13—C12—C11 | 120.6 (2) |
| C5—C4—H4 | 119.5 | C13—C12—H12 | 119.7 |
| C6—C5—C4 | 118.8 (4) | C11—C12—H12 | 119.7 |
| C6—C5—H5 | 120.6 | C12—C13—C8 | 120.4 (2) |
| C4—C5—H5 | 120.6 | C12—C13—H13 | 119.8 |
| C1—C6—C5 | 121.3 (3) | C8—C13—H13 | 119.8 |
| C1—C6—H6 | 119.4 | C11—C14—H14A | 109.5 |
| C5—C6—H6 | 119.4 | C11—C14—H14B | 109.5 |
| O2—C7—O1 | 121.9 (3) | H14A—C14—H14B | 109.5 |
| O2—C7—C8 | 127.2 (2) | C11—C14—H14C | 109.5 |
| O1—C7—C8 | 110.8 (2) | H14A—C14—H14C | 109.5 |
| C9—C8—C13 | 118.3 (3) | H14B—C14—H14C | 109.5 |
| C9—C8—C7 | 124.1 (2) | C7—O1—C1 | 119.4 (2) |
| C6—C1—C2—C3 | −0.6 (4) | C13—C8—C9—C10 | −0.2 (4) |
| O1—C1—C2—C3 | 175.5 (3) | C7—C8—C9—C10 | 178.8 (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—C12 | 0.5 (4) |
| C1—C2—C3—C4 | 1.7 (5) | C9—C10—C11—C14 | −180.0 (3) |
| Cl1—C2—C3—C4 | −179.1 (3) | C10—C11—C12—C13 | 0.2 (4) |
| C2—C3—C4—C5 | −1.7 (5) | C14—C11—C12—C13 | −179.3 (3) |
| C3—C4—C5—C6 | 0.6 (5) | C11—C12—C13—C8 | −0.9 (4) |
| O1—C1—C6—C5 | −176.4 (3) | C9—C8—C13—C12 | 0.9 (4) |
| C2—C1—C6—C5 | −0.4 (5) | C7—C8—C13—C12 | −178.2 (3) |
| C4—C5—C6—C1 | 0.4 (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—C9 | 2.7 (4) | C6—C1—O1—C7 | −64.4 (4) |
| O2—C7—C8—C13 | 4.5 (5) | C2—C1—O1—C7 | 119.6 (3) |
| O1—C7—C8—C13 | −178.3 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C14H11ClO2 |
| Mr | 246.68 |
| Crystal system, space group | Monoclinic, P21 |
| Temperature (K) | 299 |
| a, b, c (Å) | 4.0538 (8), 13.661 (3), 10.975 (2) |
| β (°) | 91.70 (2) |
| V (Å3) | 607.5 (2) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.30 |
| Crystal size (mm) | 0.48 × 0.24 × 0.16 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
| Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
| Tmin, Tmax | 0.869, 0.954 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4160, 2238, 1632 |
| Rint | 0.012 |
| (sin θ/λ)max (Å−1) | 0.625 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.116, 1.15 |
| No. of reflections | 2238 |
| No. of parameters | 155 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.36, −0.34 |
| Absolute structure | Flack (1983), 957 Friedel pairs |
| Absolute structure parameter | −0.09 (9) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
Acknowledgements
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
References
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1390. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64. Submitted. CrossRef IUCr Journals Google Scholar
Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63. In the press. Google Scholar
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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.