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access3,5-Dichlorophenyl 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 structure of the title compound, C14H10Cl2O2, resembles those of 3-chlorophenyl 4-methylbenzoate, 2,6-dichlorophenyl 4-methylbenzoate and 2,4-dichlorophenyl 4-methylbenzoate, with similar bond parameters. The dihedral angle between the benzene and benzoyl rings is 48.81 (6)°.
![[Scheme 1]](bx2159scheme1.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/S1600536808022277/bx2159sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808022277/bx2159Isup2.hkl
The title compound was prepared according to a literature 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 of the title compound used for X-ray diffraction studies were obtained by a slow evaporation of an ethanolic solution at room temperature.
The H atoms of the methyl group were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in difference map, and its positional parameters were refined freely [C—H = 0.89 (3)–1.02 (3) Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
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]](./bx2159fig1thm.gif) | Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. The Displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii. |
![[Figure 2]](./bx2159fig2thm.gif) | Fig. 2. Molecular packing of the title compound. |
| C14H10Cl2O2 | F(000) = 576 |
| Mr = 281.12 | Dx = 1.433 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3406 reflections |
| a = 3.9273 (6) Å | θ = 2.3–27.9° |
| b = 28.412 (4) Å | µ = 0.49 mm−1 |
| c = 11.705 (1) Å | T = 299 K |
| β = 94.06 (1)° | Plate, colourless |
| V = 1302.8 (3) Å3 | 0.48 × 0.40 × 0.08 mm |
| Z = 4 |
| Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2621 independent reflections |
| Radiation source: fine-focus sealed tube | 1755 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.025 |
| Rotation method data acquisition using ω and ϕ scans | θmax = 26.4°, θmin = 2.3° |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | h = −4→4 |
| Tmin = 0.800, Tmax = 0.962 | k = −35→34 |
| 7613 measured reflections | l = −14→14 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.0783P)2] where P = (Fo2 + 2Fc2)/3 |
| 2621 reflections | (Δ/σ)max = 0.001 |
| 184 parameters | Δρmax = 0.32 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
| C14H10Cl2O2 | V = 1302.8 (3) Å3 |
| Mr = 281.12 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 3.9273 (6) Å | µ = 0.49 mm−1 |
| b = 28.412 (4) Å | T = 299 K |
| c = 11.705 (1) Å | 0.48 × 0.40 × 0.08 mm |
| β = 94.06 (1)° |
| Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2621 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1755 reflections with I > 2σ(I) |
| Tmin = 0.800, Tmax = 0.962 | Rint = 0.025 |
| 7613 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
| wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.11 | Δρmax = 0.32 e Å−3 |
| 2621 reflections | Δρmin = −0.24 e Å−3 |
| 184 parameters |
Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 | 0.4042 (6) | 0.15541 (8) | −0.1194 (2) | 0.0418 (6) | |
| C2 | 0.2829 (6) | 0.13459 (9) | −0.0235 (2) | 0.0444 (6) | |
| H2 | 0.200 (6) | 0.1519 (9) | 0.035 (2) | 0.053* | |
| C3 | 0.2772 (6) | 0.08640 (9) | −0.01881 (19) | 0.0419 (6) | |
| C4 | 0.3809 (6) | 0.05839 (9) | −0.1061 (2) | 0.0442 (6) | |
| H4 | 0.373 (5) | 0.0228 (10) | −0.0960 (19) | 0.053* | |
| C5 | 0.4990 (6) | 0.08058 (9) | −0.20047 (19) | 0.0413 (6) | |
| C6 | 0.5140 (6) | 0.12902 (9) | −0.2088 (2) | 0.0432 (6) | |
| H6 | 0.583 (6) | 0.1444 (9) | −0.270 (2) | 0.052* | |
| C7 | 0.5453 (6) | 0.23217 (9) | −0.0486 (2) | 0.0450 (6) | |
| C8 | 0.4837 (6) | 0.28221 (8) | −0.0721 (2) | 0.0405 (6) | |
| C9 | 0.3278 (7) | 0.29931 (10) | −0.1734 (2) | 0.0492 (7) | |
| H9 | 0.260 (7) | 0.2789 (10) | −0.231 (2) | 0.059* | |
| C10 | 0.2734 (7) | 0.34658 (10) | −0.1884 (2) | 0.0506 (7) | |
| H10 | 0.164 (6) | 0.3558 (9) | −0.263 (2) | 0.061* | |
| C11 | 0.3722 (6) | 0.37871 (9) | −0.1031 (2) | 0.0437 (6) | |
| C12 | 0.5333 (7) | 0.36165 (10) | −0.0028 (2) | 0.0477 (7) | |
| H12 | 0.607 (6) | 0.3843 (9) | 0.049 (2) | 0.057* | |
| C13 | 0.5880 (7) | 0.31429 (9) | 0.0140 (2) | 0.0464 (7) | |
| H13 | 0.689 (6) | 0.3038 (9) | 0.079 (2) | 0.056* | |
| C14 | 0.3049 (8) | 0.43029 (10) | −0.1188 (3) | 0.0598 (8) | |
| H14A | 0.5179 | 0.4468 | −0.1197 | 0.072* | |
| H14B | 0.1808 | 0.4417 | −0.0567 | 0.072* | |
| H14C | 0.1729 | 0.4354 | −0.1899 | 0.072* | |
| O1 | 0.3978 (5) | 0.20416 (6) | −0.13445 (15) | 0.0544 (5) | |
| O2 | 0.7075 (5) | 0.21609 (6) | 0.03319 (17) | 0.0650 (6) | |
| Cl1 | 0.13414 (18) | 0.05912 (3) | 0.10169 (6) | 0.0602 (3) | |
| Cl2 | 0.6296 (2) | 0.04648 (2) | −0.31227 (6) | 0.0605 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0491 (15) | 0.0345 (15) | 0.0402 (13) | 0.0037 (11) | −0.0078 (11) | −0.0019 (10) |
| C2 | 0.0466 (15) | 0.0452 (16) | 0.0408 (14) | 0.0089 (12) | −0.0020 (11) | −0.0037 (11) |
| C3 | 0.0391 (13) | 0.0472 (16) | 0.0389 (13) | 0.0018 (11) | 0.0000 (10) | 0.0042 (11) |
| C4 | 0.0464 (15) | 0.0382 (15) | 0.0473 (15) | 0.0007 (11) | −0.0014 (11) | 0.0021 (11) |
| C5 | 0.0436 (14) | 0.0397 (14) | 0.0402 (13) | 0.0001 (11) | −0.0003 (10) | −0.0035 (11) |
| C6 | 0.0460 (14) | 0.0445 (16) | 0.0384 (13) | −0.0056 (12) | −0.0014 (11) | 0.0015 (11) |
| C7 | 0.0496 (15) | 0.0404 (15) | 0.0443 (14) | 0.0022 (12) | −0.0024 (12) | −0.0045 (11) |
| C8 | 0.0396 (13) | 0.0399 (15) | 0.0414 (13) | 0.0021 (11) | 0.0000 (10) | −0.0020 (11) |
| C9 | 0.0616 (17) | 0.0426 (16) | 0.0425 (15) | −0.0007 (13) | −0.0017 (12) | −0.0020 (12) |
| C10 | 0.0597 (17) | 0.0440 (17) | 0.0468 (15) | 0.0019 (12) | −0.0043 (13) | 0.0081 (12) |
| C11 | 0.0448 (14) | 0.0384 (15) | 0.0493 (15) | 0.0026 (11) | 0.0122 (11) | 0.0029 (11) |
| C12 | 0.0562 (16) | 0.0397 (16) | 0.0470 (15) | −0.0010 (12) | 0.0016 (12) | −0.0072 (12) |
| C13 | 0.0540 (16) | 0.0407 (16) | 0.0433 (15) | 0.0034 (12) | −0.0059 (12) | −0.0013 (12) |
| C14 | 0.0715 (19) | 0.0452 (18) | 0.0641 (19) | 0.0082 (14) | 0.0148 (14) | 0.0106 (13) |
| O1 | 0.0802 (13) | 0.0341 (11) | 0.0465 (10) | 0.0014 (9) | −0.0120 (9) | −0.0001 (8) |
| O2 | 0.0828 (14) | 0.0442 (11) | 0.0635 (12) | 0.0109 (10) | −0.0274 (11) | −0.0019 (9) |
| Cl1 | 0.0681 (5) | 0.0635 (5) | 0.0504 (4) | −0.0026 (3) | 0.0136 (3) | 0.0100 (3) |
| Cl2 | 0.0806 (5) | 0.0503 (5) | 0.0521 (4) | 0.0015 (4) | 0.0149 (3) | −0.0108 (3) |
| C1—C6 | 1.382 (3) | C8—C9 | 1.383 (4) |
| C1—C2 | 1.382 (3) | C8—C13 | 1.398 (3) |
| C1—O1 | 1.396 (3) | C9—C10 | 1.369 (4) |
| C2—C3 | 1.371 (3) | C9—H9 | 0.91 (3) |
| C2—H2 | 0.92 (3) | C10—C11 | 1.387 (4) |
| C3—C4 | 1.379 (3) | C10—H10 | 0.98 (3) |
| C3—Cl1 | 1.737 (2) | C11—C12 | 1.382 (3) |
| C4—C5 | 1.381 (3) | C11—C14 | 1.498 (3) |
| C4—H4 | 1.02 (3) | C12—C13 | 1.375 (4) |
| C5—C6 | 1.382 (3) | C12—H12 | 0.91 (3) |
| C5—Cl2 | 1.735 (2) | C13—H13 | 0.89 (3) |
| C6—H6 | 0.89 (3) | C14—H14A | 0.9600 |
| C7—O2 | 1.202 (3) | C14—H14B | 0.9600 |
| C7—O1 | 1.377 (3) | C14—H14C | 0.9600 |
| C7—C8 | 1.465 (3) | ||
| C6—C1—C2 | 121.8 (2) | C13—C8—C7 | 117.5 (2) |
| C6—C1—O1 | 116.5 (2) | C10—C9—C8 | 120.7 (2) |
| C2—C1—O1 | 121.5 (2) | C10—C9—H9 | 119.5 (18) |
| C3—C2—C1 | 117.9 (2) | C8—C9—H9 | 119.9 (18) |
| C3—C2—H2 | 119.8 (16) | C9—C10—C11 | 121.3 (3) |
| C1—C2—H2 | 122.3 (16) | C9—C10—H10 | 115.5 (16) |
| C2—C3—C4 | 122.7 (2) | C11—C10—H10 | 123.2 (16) |
| C2—C3—Cl1 | 119.06 (19) | C12—C11—C10 | 117.9 (2) |
| C4—C3—Cl1 | 118.25 (19) | C12—C11—C14 | 120.9 (2) |
| C3—C4—C5 | 117.6 (2) | C10—C11—C14 | 121.2 (2) |
| C3—C4—H4 | 118.3 (13) | C13—C12—C11 | 121.5 (3) |
| C5—C4—H4 | 124.1 (13) | C13—C12—H12 | 123.8 (17) |
| C4—C5—C6 | 122.0 (2) | C11—C12—H12 | 114.7 (17) |
| C4—C5—Cl2 | 118.88 (19) | C12—C13—C8 | 120.0 (2) |
| C6—C5—Cl2 | 119.10 (18) | C12—C13—H13 | 120.5 (17) |
| C5—C6—C1 | 118.0 (2) | C8—C13—H13 | 119.5 (17) |
| C5—C6—H6 | 124.0 (17) | C11—C14—H14A | 109.5 |
| C1—C6—H6 | 117.9 (17) | C11—C14—H14B | 109.5 |
| O2—C7—O1 | 122.2 (2) | H14A—C14—H14B | 109.5 |
| O2—C7—C8 | 126.1 (2) | C11—C14—H14C | 109.5 |
| O1—C7—C8 | 111.6 (2) | H14A—C14—H14C | 109.5 |
| C9—C8—C13 | 118.6 (2) | H14B—C14—H14C | 109.5 |
| C9—C8—C7 | 124.0 (2) | C7—O1—C1 | 118.56 (18) |
| C6—C1—C2—C3 | 0.6 (4) | O1—C7—C8—C13 | 173.3 (2) |
| O1—C1—C2—C3 | 175.7 (2) | C13—C8—C9—C10 | −0.8 (4) |
| C1—C2—C3—C4 | −1.2 (4) | C7—C8—C9—C10 | 178.9 (2) |
| C1—C2—C3—Cl1 | 178.75 (18) | C8—C9—C10—C11 | 0.0 (4) |
| C2—C3—C4—C5 | 0.9 (4) | C9—C10—C11—C12 | 1.1 (4) |
| Cl1—C3—C4—C5 | −179.01 (18) | C9—C10—C11—C14 | −178.5 (2) |
| C3—C4—C5—C6 | −0.1 (4) | C10—C11—C12—C13 | −1.5 (4) |
| C3—C4—C5—Cl2 | −179.67 (18) | C14—C11—C12—C13 | 178.1 (2) |
| C4—C5—C6—C1 | −0.4 (4) | C11—C12—C13—C8 | 0.8 (4) |
| Cl2—C5—C6—C1 | 179.14 (18) | C9—C8—C13—C12 | 0.3 (4) |
| C2—C1—C6—C5 | 0.2 (4) | C7—C8—C13—C12 | −179.3 (2) |
| O1—C1—C6—C5 | −175.2 (2) | O2—C7—O1—C1 | 7.5 (4) |
| O2—C7—C8—C9 | 172.5 (3) | C8—C7—O1—C1 | −173.6 (2) |
| O1—C7—C8—C9 | −6.3 (4) | C6—C1—O1—C7 | −131.0 (2) |
| O2—C7—C8—C13 | −7.9 (4) | C2—C1—O1—C7 | 53.6 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C14H10Cl2O2 |
| Mr | 281.12 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 299 |
| a, b, c (Å) | 3.9273 (6), 28.412 (4), 11.705 (1) |
| β (°) | 94.06 (1) |
| V (Å3) | 1302.8 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.49 |
| Crystal size (mm) | 0.48 × 0.40 × 0.08 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
| Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
| Tmin, Tmax | 0.800, 0.962 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7613, 2621, 1755 |
| Rint | 0.025 |
| (sin θ/λ)max (Å−1) | 0.625 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.139, 1.11 |
| No. of reflections | 2621 |
| No. of parameters | 184 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.32, −0.24 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), 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
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3877. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o843. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1390. Web of Science CSD 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 |
In the present work, as part of a study of the substituent effects on the structures of chemically and industrially significant compounds (Gowda et al., 2007, 2008a, b), the structure of 3,5-dichlorophenyl 4-methylbenzoate (35DCP4MeBA) has been determined. The structure of 35DCP4MeBA (Fig. 1) resembles those of 3-chlorophenyl 4-methylbenzoate (3CP4MeBA)(Gowda et al., 2008b), 2,6-dichlorophenyl 4-methylbenzoate (26DCP4MeBA)(Gowda et al., 2008a), 2,4-dichlorophenyl 4-methyl benzoate (24DCP4MeBA) and other aryl benzoates (Gowda et al., 2007). The bond parameters in 35DCP4MeBA are similar to those in 3CP4MeBA, 26DCP4MeBA, 24DCP4MeBA and other benzoates. The dihedral angle between the benzene and benzoyl rings in 35DCP4MeBA is 48.81 (6)°, compared to the values of 71.75 (7)° in 3CP4MeBA (Gowda et al., 2008b), 77.97 (9)° in 26DCP4MeBA (Gowda et al., 2008a) and 48.13 (5)° in 24DCP4MeBA) (Gowda et al., 2007). The molecular packing in the crystal structure of 35DCP4MeBA is shown in Fig. 2.