organic compounds
Ethyl 2-[4-(2-chlorobenzoyl)-2,6-dimethylphenoxy]ethanoate
aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, bDepartment of Studies in Physics, University of Mysore, Mysore 570 006, India, and cPost-Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: vivek_gupta2k2@hotmail.com
The 19H19ClO4, contains two independent molecules. The dihedral angles between the benzene rings are 63.41 (8) and 61.41 (9)°. Adjacent molecules of different types are interconnected in pairs through π–π interactions between their central benzene rings [centroid–centroid separation = 3.801 (2) Å, interplanar spacing = 3.605 (2) Å, centroid shift = 1.204 (2) Å]. Finally, C—H⋯O hydrogen bonds link these dimers into bilayers parallel to (100).
of the title compound, CRelated literature
For general background to phenoxyethanoic acid, see: Dahiya & Kaur (2007); Esbenshade et al. (1990). For biological activity, see: Prabhakar et al. (2006); Sudha et al. (2003); Ma et al. (2011); Khanum et al. (2010). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812030693/bg2469sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030693/bg2469Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030693/bg2469Isup3.cml
[4-(2-chlorobenzoyl)-2,6-dimethylphenoxy]ethanoic acid was obtained by refluxing a mixture of(2-Chloro-phenyl)-(4-hydroxy-3,5-dimethyl-phenyl)-methanone (1 g, 0.0038 mol) and ethyl chloroacetate (1.41 g, 0.011 mol) in dry acetone (50 ml) and anhydrous potassium carbonate (1.59 g, 0.0114 mol) for 14 hrs. The reaction mixture was cooled, and the solvent was removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 X 50 ml). The ether layer was washed with a 10% sodium hydroxide solution (3 X 50 ml), followed by water (3 X 30 ml), and then dried over anhydrous sodium sulfate and evaporated to dryness to obtain the product. Which on recrystallization with ethanol, gave [4-(2-chlorobenzoyl)-2,6-dimethylphenoxy]ethanoic acid with 85% yield. M.p.70–72°C; IR (Nujol): 1745 (ester, C O), 1665 cm-1 (C O); 1H NMR (CDCl3): δ 1.2 (t, J = 7 Hz, 3H, CH3 of ester), 2.3 (s, 6H, 2Ar-CH3), 4.25 (q, J = 6 Hz, 2H, CH2 of ester), 4.45 (s, 2H, OCH2), 7.2–7.8 (bm, 6H, Ar—H). Anal. Cal. for C19H19ClO4 (346.10): C, 65.80; H, 5.52; Found: C, 65.85; H, 5.58%.
All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).
Analogues of phenoxy ethanoic acid are considered to be very important compounds in the field of medicinal chemistry, and the compounds were found to have good antifungal activity against pathogenic fungi and posses moderate activity against gram negative bacteria in comparison to standard ciprofloxacin (Dahiya & Kaur 2007). Resent studies shows that changes in the chemical and stereoisomeric structures of phenoxy ethanoic acid alter
proliferation (Esbenshade et al., 1990). The anti-inflammatory activity results revealed a significant anti-inflammatory activity (up to 63.4%, 62.0%, 64.1% and 62.5% edema inhibition, respectively), as compared to the standard drug diclofenac (67.0%). Pathological investigation has shown that the analogues of phenoxy ethanoic acid compounds have higher anti hyperlipidmeic effect and caused appropriate modulation in HDL levels and some compounds showed a good potential for obesity-associated hyperlipidemia (Khanum et al., 2010).The phenoxy acetic acid analogues show very good antitumor activity on Ehrlich asites tumor cells (Prabhakar et al., 2006) and also show the anti ulcerogenic activity, cyclooxygenase activity, anticonvulsant activity (Sudha et al., 2003) and anti microbial activities (Ma et al., 2011). We were interested in obtaining these type of compounds to evaluate their biological activity; for this purpose, the title compound,[4-(2-chlorobenzoyl)-2,6-dimethylphenoxy].ethanoic acid (I) was synthesized.The π-π interactions between their central phenyl rings (C1-C6) [ centroid separation = 3.801 (2)Å, = 3.605Å, centroid shift = 1.204Å]. Finally, C—H···O hydrogen bonds (Table 1) link these dimeric entities into bilayered structures parallel to (100).
of (I) comprises two crystallographically independent molecules, A and B,respectively (Fig. 1). The geometry of both independent molecules indicates a high degree of similarity in terms of bond distances and angles. The average aromatic bond length in the phenyl ring is 1.381 (3) Å and 1.380 (3) Å for A, B, respectively. Remaining bond distances are within normal ranges (Allen et al., 1987). The dihedral angle between the phenyl rings is 63.41 (8)° for molecule A and 61.41 (9)° for molecule B. Adjacent molecules of different type (A,B) are interconnected in pairs, throughFor general background to phenoxyethanoic acid, see: Dahiya & Kaur (2007); Esbenshade et al. (1990). For biological activity, see: Prabhakar et al. (2006); Sudha et al. (2003); Ma et al., (2011); Khanum et al. (2010). For bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The thermal ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. |
C19H19ClO4 | F(000) = 1456 |
Mr = 346.79 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5654 reflections |
a = 16.4082 (8) Å | θ = 3.5–28.9° |
b = 14.7290 (6) Å | µ = 0.23 mm−1 |
c = 15.4470 (8) Å | T = 293 K |
β = 107.268 (5)° | Block-shaped, white |
V = 3564.9 (3) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 8 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 6997 independent reflections |
Radiation source: fine-focus sealed tube | 3576 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 0 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scans | h = −20→18 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −18→17 |
Tmin = 0.912, Tmax = 1.000 | l = −12→19 |
17025 measured reflections |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0686P)2 + 0.8701P] where P = (Fo2 + 2Fc2)/3 |
6997 reflections | (Δ/σ)max = 0.001 |
439 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C19H19ClO4 | V = 3564.9 (3) Å3 |
Mr = 346.79 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.4082 (8) Å | µ = 0.23 mm−1 |
b = 14.7290 (6) Å | T = 293 K |
c = 15.4470 (8) Å | 0.30 × 0.20 × 0.20 mm |
β = 107.268 (5)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 6997 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3576 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 1.000 | Rint = 0.039 |
17025 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.46 e Å−3 |
6997 reflections | Δρmin = −0.36 e Å−3 |
439 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) 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 | ||
Cl1A | 0.46159 (6) | 0.21534 (6) | 0.22421 (7) | 0.0684 (3) | |
Cl1B | −0.03423 (6) | 0.22771 (7) | −0.02662 (7) | 0.0685 (3) | |
O16A | 0.28452 (14) | 0.50209 (13) | −0.06982 (16) | 0.0558 (6) | |
O16B | −0.20126 (16) | 0.51127 (14) | −0.31401 (17) | 0.0647 (7) | |
O9A | 0.21270 (14) | 0.22608 (16) | 0.21320 (16) | 0.0665 (7) | |
C4A | 0.27950 (18) | 0.33354 (18) | 0.1437 (2) | 0.0394 (7) | |
C9A | 0.27483 (19) | 0.2738 (2) | 0.2186 (2) | 0.0440 (8) | |
C10A | 0.34554 (19) | 0.27262 (18) | 0.3070 (2) | 0.0401 (7) | |
O9B | −0.28615 (15) | 0.23574 (18) | −0.03864 (17) | 0.0755 (8) | |
C15B | −0.0681 (2) | 0.25322 (19) | 0.0673 (2) | 0.0437 (8) | |
C10B | −0.15203 (19) | 0.27675 (19) | 0.0581 (2) | 0.0411 (7) | |
C5A | 0.21687 (18) | 0.32661 (19) | 0.0610 (2) | 0.0450 (8) | |
H5A | 0.1738 | 0.2837 | 0.0541 | 0.054* | |
O19A | 0.36454 (17) | 0.50616 (15) | −0.25734 (17) | 0.0687 (7) | |
C15A | 0.4298 (2) | 0.24726 (19) | 0.3174 (2) | 0.0456 (8) | |
C9B | −0.22215 (19) | 0.2815 (2) | −0.0310 (2) | 0.0472 (8) | |
C1B | −0.2065 (2) | 0.4546 (2) | −0.2440 (2) | 0.0497 (8) | |
C1A | 0.28278 (19) | 0.44450 (19) | 0.0007 (2) | 0.0441 (8) | |
C4B | −0.21539 (18) | 0.34356 (19) | −0.1037 (2) | 0.0419 (7) | |
C5B | −0.27603 (19) | 0.3376 (2) | −0.1884 (2) | 0.0492 (8) | |
H5B | −0.3195 | 0.2950 | −0.1971 | 0.059* | |
C2B | −0.1455 (2) | 0.46487 (19) | −0.1604 (2) | 0.0491 (8) | |
C2A | 0.34656 (19) | 0.45378 (19) | 0.0823 (2) | 0.0457 (8) | |
C6A | 0.21651 (18) | 0.3816 (2) | −0.0115 (2) | 0.0458 (8) | |
C3A | 0.34300 (19) | 0.39839 (19) | 0.1539 (2) | 0.0457 (8) | |
H3A | 0.3841 | 0.4049 | 0.2098 | 0.055* | |
C6B | −0.2738 (2) | 0.3923 (2) | −0.2594 (2) | 0.0525 (9) | |
C3B | −0.15142 (18) | 0.40863 (19) | −0.0898 (2) | 0.0462 (8) | |
H3B | −0.1120 | 0.4148 | −0.0327 | 0.055* | |
O19B | −0.1394 (2) | 0.49360 (17) | −0.5120 (2) | 0.0873 (9) | |
C14A | 0.4899 (2) | 0.2435 (2) | 0.4019 (3) | 0.0575 (10) | |
H14A | 0.5462 | 0.2283 | 0.4076 | 0.069* | |
O18A | 0.3528 (2) | 0.61754 (18) | −0.1649 (2) | 0.1018 (11) | |
C11A | 0.3232 (2) | 0.2926 (2) | 0.3852 (2) | 0.0532 (9) | |
H11A | 0.2675 | 0.3101 | 0.3803 | 0.064* | |
C11B | −0.1756 (2) | 0.2909 (2) | 0.1363 (2) | 0.0550 (9) | |
H11B | −0.2318 | 0.3056 | 0.1317 | 0.066* | |
C14B | −0.0086 (2) | 0.2459 (2) | 0.1512 (3) | 0.0548 (9) | |
H14B | 0.0475 | 0.2302 | 0.1563 | 0.066* | |
C8A | 0.1461 (2) | 0.3761 (3) | −0.1005 (2) | 0.0692 (11) | |
H8A1 | 0.1649 | 0.3402 | −0.1427 | 0.104* | |
H8A2 | 0.1320 | 0.4362 | −0.1245 | 0.104* | |
H8A3 | 0.0965 | 0.3486 | −0.0906 | 0.104* | |
C12B | −0.1167 (3) | 0.2836 (2) | 0.2201 (3) | 0.0658 (10) | |
H12B | −0.1332 | 0.2932 | 0.2720 | 0.079* | |
C18B | −0.1566 (3) | 0.5337 (3) | −0.4445 (3) | 0.0716 (12) | |
C18A | 0.3471 (2) | 0.5397 (2) | −0.1853 (3) | 0.0555 (9) | |
O18B | −0.1572 (3) | 0.6142 (2) | −0.4361 (3) | 0.1385 (16) | |
C12A | 0.3822 (3) | 0.2869 (2) | 0.4696 (3) | 0.0679 (11) | |
H12A | 0.3662 | 0.2994 | 0.5213 | 0.081* | |
C13A | 0.4648 (3) | 0.2625 (3) | 0.4770 (3) | 0.0699 (11) | |
H13A | 0.5045 | 0.2589 | 0.5341 | 0.084* | |
C17A | 0.3229 (2) | 0.4645 (2) | −0.1325 (2) | 0.0577 (9) | |
H17A | 0.2832 | 0.4236 | −0.1733 | 0.069* | |
H17B | 0.3732 | 0.4302 | −0.1004 | 0.069* | |
C17B | −0.1633 (3) | 0.4689 (3) | −0.3750 (3) | 0.0862 (14) | |
H17C | −0.1977 | 0.4174 | −0.4036 | 0.103* | |
H17D | −0.1070 | 0.4468 | −0.3420 | 0.103* | |
C13B | −0.0333 (2) | 0.2619 (2) | 0.2274 (3) | 0.0662 (11) | |
H13B | 0.0067 | 0.2581 | 0.2844 | 0.079* | |
C7A | 0.4158 (2) | 0.5230 (2) | 0.0931 (3) | 0.0693 (11) | |
H7A1 | 0.4576 | 0.5006 | 0.0662 | 0.104* | |
H7A2 | 0.4425 | 0.5343 | 0.1564 | 0.104* | |
H7A3 | 0.3917 | 0.5784 | 0.0637 | 0.104* | |
C7B | −0.0761 (2) | 0.5349 (2) | −0.1455 (3) | 0.0763 (12) | |
H7B1 | −0.0352 | 0.5161 | −0.1753 | 0.115* | |
H7B2 | −0.0482 | 0.5414 | −0.0817 | 0.115* | |
H7B3 | −0.1005 | 0.5920 | −0.1700 | 0.115* | |
C8B | −0.3420 (2) | 0.3872 (3) | −0.3487 (3) | 0.0811 (12) | |
H8B1 | −0.3215 | 0.3529 | −0.3908 | 0.122* | |
H8B2 | −0.3567 | 0.4475 | −0.3718 | 0.122* | |
H8B3 | −0.3916 | 0.3580 | −0.3406 | 0.122* | |
C20A | 0.3913 (3) | 0.5703 (3) | −0.3153 (3) | 0.0890 (14) | |
H20A | 0.3461 | 0.6137 | −0.3406 | 0.107* | |
H20B | 0.4413 | 0.6034 | −0.2801 | 0.107* | |
C21A | 0.4110 (4) | 0.5209 (3) | −0.3876 (3) | 0.130 (2) | |
H21A | 0.4581 | 0.4806 | −0.3622 | 0.195* | |
H21B | 0.4260 | 0.5629 | −0.4278 | 0.195* | |
H21C | 0.3621 | 0.4862 | −0.4205 | 0.195* | |
C21B | −0.1070 (4) | 0.4990 (3) | −0.6498 (4) | 0.138 (2) | |
H21D | −0.0524 | 0.4718 | −0.6219 | 0.208* | |
H21E | −0.1033 | 0.5380 | −0.6983 | 0.208* | |
H21F | −0.1484 | 0.4523 | −0.6735 | 0.208* | |
C20B | −0.1313 (4) | 0.5491 (3) | −0.5865 (3) | 0.1206 (19) | |
H20C | −0.1855 | 0.5783 | −0.6155 | 0.145* | |
H20D | −0.0894 | 0.5963 | −0.5629 | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0703 (6) | 0.0780 (6) | 0.0640 (7) | 0.0168 (5) | 0.0309 (5) | −0.0039 (5) |
Cl1B | 0.0679 (6) | 0.0860 (7) | 0.0604 (7) | 0.0089 (5) | 0.0325 (5) | −0.0015 (5) |
O16A | 0.0690 (15) | 0.0503 (13) | 0.0549 (16) | 0.0154 (11) | 0.0288 (12) | 0.0158 (11) |
O16B | 0.0882 (17) | 0.0547 (14) | 0.0625 (18) | 0.0231 (12) | 0.0395 (14) | 0.0205 (12) |
O9A | 0.0536 (14) | 0.0836 (17) | 0.0555 (18) | −0.0271 (13) | 0.0059 (12) | 0.0114 (13) |
C4A | 0.0405 (16) | 0.0386 (16) | 0.0380 (19) | −0.0016 (13) | 0.0098 (14) | −0.0001 (13) |
C9A | 0.0446 (18) | 0.0472 (18) | 0.040 (2) | −0.0020 (15) | 0.0119 (15) | 0.0025 (14) |
C10A | 0.0467 (17) | 0.0334 (15) | 0.039 (2) | −0.0034 (13) | 0.0113 (15) | 0.0009 (13) |
O9B | 0.0594 (16) | 0.0992 (19) | 0.0598 (19) | −0.0345 (14) | 0.0054 (14) | 0.0160 (14) |
C15B | 0.0485 (18) | 0.0441 (18) | 0.040 (2) | −0.0042 (14) | 0.0154 (16) | 0.0005 (13) |
C10B | 0.0467 (18) | 0.0394 (17) | 0.036 (2) | −0.0062 (14) | 0.0111 (15) | 0.0020 (13) |
C5A | 0.0452 (17) | 0.0465 (18) | 0.044 (2) | −0.0042 (14) | 0.0132 (15) | −0.0002 (15) |
O19A | 0.0955 (19) | 0.0601 (15) | 0.0593 (18) | −0.0042 (13) | 0.0369 (15) | 0.0092 (12) |
C15A | 0.0504 (19) | 0.0429 (18) | 0.043 (2) | −0.0025 (14) | 0.0138 (17) | −0.0053 (14) |
C9B | 0.0463 (18) | 0.0508 (19) | 0.044 (2) | −0.0057 (15) | 0.0130 (16) | 0.0009 (15) |
C1B | 0.057 (2) | 0.0479 (19) | 0.049 (2) | 0.0156 (16) | 0.0243 (17) | 0.0142 (16) |
C1A | 0.0502 (18) | 0.0387 (17) | 0.047 (2) | 0.0072 (14) | 0.0201 (16) | 0.0057 (15) |
C4B | 0.0386 (16) | 0.0462 (18) | 0.040 (2) | −0.0020 (14) | 0.0102 (14) | 0.0013 (14) |
C5B | 0.0445 (17) | 0.059 (2) | 0.044 (2) | −0.0072 (15) | 0.0115 (16) | 0.0003 (16) |
C2B | 0.0501 (18) | 0.0399 (17) | 0.060 (2) | 0.0015 (15) | 0.0198 (17) | 0.0027 (16) |
C2A | 0.0481 (18) | 0.0373 (17) | 0.052 (2) | −0.0021 (14) | 0.0157 (16) | 0.0009 (15) |
C6A | 0.0417 (17) | 0.0555 (19) | 0.040 (2) | 0.0054 (15) | 0.0113 (15) | 0.0025 (15) |
C3A | 0.0443 (17) | 0.0463 (18) | 0.044 (2) | −0.0013 (15) | 0.0088 (15) | −0.0032 (14) |
C6B | 0.052 (2) | 0.064 (2) | 0.040 (2) | 0.0098 (17) | 0.0119 (16) | 0.0027 (16) |
C3B | 0.0420 (17) | 0.0493 (19) | 0.043 (2) | −0.0022 (14) | 0.0053 (15) | 0.0021 (15) |
O19B | 0.136 (3) | 0.0667 (17) | 0.076 (2) | −0.0011 (16) | 0.058 (2) | 0.0106 (15) |
C14A | 0.050 (2) | 0.057 (2) | 0.058 (3) | 0.0012 (16) | 0.004 (2) | 0.0032 (17) |
O18A | 0.148 (3) | 0.0523 (16) | 0.142 (3) | −0.0045 (17) | 0.101 (2) | 0.0005 (17) |
C11A | 0.058 (2) | 0.058 (2) | 0.046 (2) | −0.0006 (16) | 0.0203 (18) | −0.0063 (16) |
C11B | 0.064 (2) | 0.058 (2) | 0.047 (2) | 0.0021 (17) | 0.0223 (18) | 0.0008 (17) |
C14B | 0.051 (2) | 0.057 (2) | 0.051 (3) | 0.0015 (16) | 0.0078 (19) | 0.0062 (16) |
C8A | 0.058 (2) | 0.096 (3) | 0.047 (2) | −0.005 (2) | 0.0058 (18) | 0.007 (2) |
C12B | 0.084 (3) | 0.079 (3) | 0.038 (2) | 0.002 (2) | 0.024 (2) | −0.0026 (19) |
C18B | 0.093 (3) | 0.053 (2) | 0.086 (3) | 0.018 (2) | 0.054 (3) | 0.019 (2) |
C18A | 0.055 (2) | 0.047 (2) | 0.070 (3) | 0.0069 (16) | 0.0275 (19) | 0.0076 (18) |
O18B | 0.237 (4) | 0.072 (2) | 0.160 (4) | 0.033 (2) | 0.141 (3) | 0.031 (2) |
C12A | 0.082 (3) | 0.080 (3) | 0.042 (2) | −0.008 (2) | 0.020 (2) | −0.0121 (19) |
C13A | 0.070 (3) | 0.080 (3) | 0.046 (3) | −0.008 (2) | −0.004 (2) | 0.0036 (19) |
C17A | 0.073 (2) | 0.052 (2) | 0.053 (2) | 0.0069 (17) | 0.0262 (19) | 0.0067 (17) |
C17B | 0.128 (4) | 0.070 (3) | 0.086 (3) | 0.024 (2) | 0.070 (3) | 0.023 (2) |
C13B | 0.070 (3) | 0.074 (2) | 0.041 (3) | −0.001 (2) | −0.003 (2) | 0.0093 (18) |
C7A | 0.068 (2) | 0.064 (2) | 0.074 (3) | −0.0168 (19) | 0.018 (2) | 0.007 (2) |
C7B | 0.072 (2) | 0.064 (2) | 0.094 (3) | −0.011 (2) | 0.026 (2) | 0.015 (2) |
C8B | 0.075 (3) | 0.112 (3) | 0.048 (3) | 0.005 (2) | 0.006 (2) | 0.010 (2) |
C20A | 0.124 (4) | 0.077 (3) | 0.082 (3) | 0.006 (3) | 0.054 (3) | 0.029 (2) |
C21A | 0.228 (7) | 0.103 (4) | 0.093 (4) | −0.009 (4) | 0.097 (4) | 0.014 (3) |
C21B | 0.245 (7) | 0.112 (4) | 0.078 (4) | 0.033 (4) | 0.079 (5) | 0.019 (3) |
C20B | 0.192 (6) | 0.105 (4) | 0.083 (4) | −0.006 (4) | 0.069 (4) | 0.032 (3) |
Cl1A—C15A | 1.736 (3) | O18A—C18A | 1.186 (4) |
Cl1B—C15B | 1.742 (3) | C11A—C12A | 1.377 (4) |
O16A—C1A | 1.387 (3) | C11A—H11A | 0.9300 |
O16A—C17A | 1.414 (4) | C11B—C12B | 1.370 (5) |
O16B—C1B | 1.389 (4) | C11B—H11B | 0.9300 |
O16B—C17B | 1.419 (4) | C14B—C13B | 1.374 (5) |
O9A—C9A | 1.220 (3) | C14B—H14B | 0.9300 |
C4A—C5A | 1.386 (4) | C8A—H8A1 | 0.9600 |
C4A—C3A | 1.388 (4) | C8A—H8A2 | 0.9600 |
C4A—C9A | 1.474 (4) | C8A—H8A3 | 0.9600 |
C9A—C10A | 1.507 (4) | C12B—C13B | 1.378 (5) |
C10A—C15A | 1.394 (4) | C12B—H12B | 0.9300 |
C10A—C11A | 1.394 (4) | C18B—O18B | 1.193 (4) |
O9B—C9B | 1.224 (3) | C18B—C17B | 1.464 (5) |
C15B—C14B | 1.376 (4) | C18A—C17A | 1.498 (4) |
C15B—C10B | 1.385 (4) | C12A—C13A | 1.374 (5) |
C10B—C11B | 1.388 (4) | C12A—H12A | 0.9300 |
C10B—C9B | 1.511 (4) | C13A—H13A | 0.9300 |
C5A—C6A | 1.381 (4) | C17A—H17A | 0.9700 |
C5A—H5A | 0.9300 | C17A—H17B | 0.9700 |
O19A—C18A | 1.323 (4) | C17B—H17C | 0.9700 |
O19A—C20A | 1.457 (4) | C17B—H17D | 0.9700 |
C15A—C14A | 1.384 (4) | C13B—H13B | 0.9300 |
C9B—C4B | 1.477 (4) | C7A—H7A1 | 0.9600 |
C1B—C2B | 1.388 (4) | C7A—H7A2 | 0.9600 |
C1B—C6B | 1.400 (4) | C7A—H7A3 | 0.9600 |
C1A—C2A | 1.385 (4) | C7B—H7B1 | 0.9600 |
C1A—C6A | 1.398 (4) | C7B—H7B2 | 0.9600 |
C4B—C3B | 1.390 (4) | C7B—H7B3 | 0.9600 |
C4B—C5B | 1.392 (4) | C8B—H8B1 | 0.9600 |
C5B—C6B | 1.370 (4) | C8B—H8B2 | 0.9600 |
C5B—H5B | 0.9300 | C8B—H8B3 | 0.9600 |
C2B—C3B | 1.396 (4) | C20A—C21A | 1.448 (6) |
C2B—C7B | 1.502 (4) | C20A—H20A | 0.9700 |
C2A—C3A | 1.389 (4) | C20A—H20B | 0.9700 |
C2A—C7A | 1.499 (4) | C21A—H21A | 0.9600 |
C6A—C8A | 1.512 (4) | C21A—H21B | 0.9600 |
C3A—H3A | 0.9300 | C21A—H21C | 0.9600 |
C6B—C8B | 1.498 (4) | C21B—C20B | 1.376 (6) |
C3B—H3B | 0.9300 | C21B—H21D | 0.9600 |
O19B—C18B | 1.300 (4) | C21B—H21E | 0.9600 |
O19B—C20B | 1.450 (5) | C21B—H21F | 0.9600 |
C14A—C13A | 1.369 (5) | C20B—H20C | 0.9700 |
C14A—H14A | 0.9300 | C20B—H20D | 0.9700 |
C1A—O16A—C17A | 114.5 (2) | H8A1—C8A—H8A3 | 109.5 |
C1B—O16B—C17B | 113.2 (2) | H8A2—C8A—H8A3 | 109.5 |
C5A—C4A—C3A | 118.8 (3) | C11B—C12B—C13B | 120.1 (4) |
C5A—C4A—C9A | 118.9 (3) | C11B—C12B—H12B | 120.0 |
C3A—C4A—C9A | 122.3 (3) | C13B—C12B—H12B | 120.0 |
O9A—C9A—C4A | 121.8 (3) | O18B—C18B—O19B | 123.3 (4) |
O9A—C9A—C10A | 117.3 (3) | O18B—C18B—C17B | 124.3 (4) |
C4A—C9A—C10A | 120.9 (3) | O19B—C18B—C17B | 111.9 (3) |
C15A—C10A—C11A | 117.6 (3) | O18A—C18A—O19A | 124.4 (3) |
C15A—C10A—C9A | 125.3 (3) | O18A—C18A—C17A | 125.6 (4) |
C11A—C10A—C9A | 116.9 (3) | O19A—C18A—C17A | 109.9 (3) |
C14B—C15B—C10B | 121.4 (3) | C13A—C12A—C11A | 119.6 (4) |
C14B—C15B—Cl1B | 117.1 (3) | C13A—C12A—H12A | 120.2 |
C10B—C15B—Cl1B | 121.5 (3) | C11A—C12A—H12A | 120.2 |
C15B—C10B—C11B | 118.2 (3) | C14A—C13A—C12A | 121.4 (4) |
C15B—C10B—C9B | 124.7 (3) | C14A—C13A—H13A | 119.3 |
C11B—C10B—C9B | 116.9 (3) | C12A—C13A—H13A | 119.3 |
C6A—C5A—C4A | 121.9 (3) | O16A—C17A—C18A | 109.1 (3) |
C6A—C5A—H5A | 119.1 | O16A—C17A—H17A | 109.9 |
C4A—C5A—H5A | 119.1 | C18A—C17A—H17A | 109.9 |
C18A—O19A—C20A | 117.0 (3) | O16A—C17A—H17B | 109.9 |
C14A—C15A—C10A | 121.6 (3) | C18A—C17A—H17B | 109.9 |
C14A—C15A—Cl1A | 117.8 (3) | H17A—C17A—H17B | 108.3 |
C10A—C15A—Cl1A | 120.6 (3) | O16B—C17B—C18B | 110.0 (3) |
O9B—C9B—C4B | 121.6 (3) | O16B—C17B—H17C | 109.7 |
O9B—C9B—C10B | 117.5 (3) | C18B—C17B—H17C | 109.7 |
C4B—C9B—C10B | 120.8 (3) | O16B—C17B—H17D | 109.7 |
C2B—C1B—O16B | 117.6 (3) | C18B—C17B—H17D | 109.7 |
C2B—C1B—C6B | 123.0 (3) | H17C—C17B—H17D | 108.2 |
O16B—C1B—C6B | 119.3 (3) | C14B—C13B—C12B | 120.5 (3) |
C2A—C1A—O16A | 117.9 (3) | C14B—C13B—H13B | 119.8 |
C2A—C1A—C6A | 122.4 (3) | C12B—C13B—H13B | 119.8 |
O16A—C1A—C6A | 119.7 (3) | C2A—C7A—H7A1 | 109.5 |
C3B—C4B—C5B | 119.0 (3) | C2A—C7A—H7A2 | 109.5 |
C3B—C4B—C9B | 122.2 (3) | H7A1—C7A—H7A2 | 109.5 |
C5B—C4B—C9B | 118.8 (3) | C2A—C7A—H7A3 | 109.5 |
C6B—C5B—C4B | 122.3 (3) | H7A1—C7A—H7A3 | 109.5 |
C6B—C5B—H5B | 118.9 | H7A2—C7A—H7A3 | 109.5 |
C4B—C5B—H5B | 118.9 | C2B—C7B—H7B1 | 109.5 |
C1B—C2B—C3B | 117.6 (3) | C2B—C7B—H7B2 | 109.5 |
C1B—C2B—C7B | 121.5 (3) | H7B1—C7B—H7B2 | 109.5 |
C3B—C2B—C7B | 120.9 (3) | C2B—C7B—H7B3 | 109.5 |
C1A—C2A—C3A | 117.9 (3) | H7B1—C7B—H7B3 | 109.5 |
C1A—C2A—C7A | 120.8 (3) | H7B2—C7B—H7B3 | 109.5 |
C3A—C2A—C7A | 121.3 (3) | C6B—C8B—H8B1 | 109.5 |
C5A—C6A—C1A | 117.6 (3) | C6B—C8B—H8B2 | 109.5 |
C5A—C6A—C8A | 121.6 (3) | H8B1—C8B—H8B2 | 109.5 |
C1A—C6A—C8A | 120.8 (3) | C6B—C8B—H8B3 | 109.5 |
C4A—C3A—C2A | 121.4 (3) | H8B1—C8B—H8B3 | 109.5 |
C4A—C3A—H3A | 119.3 | H8B2—C8B—H8B3 | 109.5 |
C2A—C3A—H3A | 119.3 | C21A—C20A—O19A | 109.0 (3) |
C5B—C6B—C1B | 117.2 (3) | C21A—C20A—H20A | 109.9 |
C5B—C6B—C8B | 121.2 (3) | O19A—C20A—H20A | 109.9 |
C1B—C6B—C8B | 121.7 (3) | C21A—C20A—H20B | 109.9 |
C4B—C3B—C2B | 120.9 (3) | O19A—C20A—H20B | 109.9 |
C4B—C3B—H3B | 119.5 | H20A—C20A—H20B | 108.3 |
C2B—C3B—H3B | 119.5 | C20A—C21A—H21A | 109.5 |
C18B—O19B—C20B | 118.3 (3) | C20A—C21A—H21B | 109.5 |
C13A—C14A—C15A | 118.8 (3) | H21A—C21A—H21B | 109.5 |
C13A—C14A—H14A | 120.6 | C20A—C21A—H21C | 109.5 |
C15A—C14A—H14A | 120.6 | H21A—C21A—H21C | 109.5 |
C12A—C11A—C10A | 121.0 (3) | H21B—C21A—H21C | 109.5 |
C12A—C11A—H11A | 119.5 | C20B—C21B—H21D | 109.5 |
C10A—C11A—H11A | 119.5 | C20B—C21B—H21E | 109.5 |
C12B—C11B—C10B | 120.6 (3) | H21D—C21B—H21E | 109.5 |
C12B—C11B—H11B | 119.7 | C20B—C21B—H21F | 109.5 |
C10B—C11B—H11B | 119.7 | H21D—C21B—H21F | 109.5 |
C13B—C14B—C15B | 119.1 (3) | H21E—C21B—H21F | 109.5 |
C13B—C14B—H14B | 120.4 | C21B—C20B—O19B | 112.1 (4) |
C15B—C14B—H14B | 120.4 | C21B—C20B—H20C | 109.2 |
C6A—C8A—H8A1 | 109.5 | O19B—C20B—H20C | 109.2 |
C6A—C8A—H8A2 | 109.5 | C21B—C20B—H20D | 109.2 |
H8A1—C8A—H8A2 | 109.5 | O19B—C20B—H20D | 109.2 |
C6A—C8A—H8A3 | 109.5 | H20C—C20B—H20D | 107.9 |
C5A—C4A—C9A—O9A | −8.5 (5) | O16A—C1A—C6A—C5A | −179.1 (3) |
C3A—C4A—C9A—O9A | 169.5 (3) | C2A—C1A—C6A—C8A | 177.5 (3) |
C5A—C4A—C9A—C10A | 174.3 (3) | O16A—C1A—C6A—C8A | −0.6 (5) |
C3A—C4A—C9A—C10A | −7.6 (4) | C5A—C4A—C3A—C2A | −2.3 (5) |
O9A—C9A—C10A—C15A | 120.5 (4) | C9A—C4A—C3A—C2A | 179.7 (3) |
C4A—C9A—C10A—C15A | −62.2 (4) | C1A—C2A—C3A—C4A | 2.2 (5) |
O9A—C9A—C10A—C11A | −54.9 (4) | C7A—C2A—C3A—C4A | −179.3 (3) |
C4A—C9A—C10A—C11A | 122.4 (3) | C4B—C5B—C6B—C1B | 1.0 (5) |
C14B—C15B—C10B—C11B | −1.4 (4) | C4B—C5B—C6B—C8B | −177.3 (3) |
Cl1B—C15B—C10B—C11B | 176.3 (2) | C2B—C1B—C6B—C5B | −2.5 (5) |
C14B—C15B—C10B—C9B | −176.6 (3) | O16B—C1B—C6B—C5B | 179.7 (3) |
Cl1B—C15B—C10B—C9B | 1.0 (4) | C2B—C1B—C6B—C8B | 175.8 (3) |
C3A—C4A—C5A—C6A | 0.7 (5) | O16B—C1B—C6B—C8B | −2.0 (5) |
C9A—C4A—C5A—C6A | 178.8 (3) | C5B—C4B—C3B—C2B | −2.6 (5) |
C11A—C10A—C15A—C14A | −1.2 (4) | C9B—C4B—C3B—C2B | 178.5 (3) |
C9A—C10A—C15A—C14A | −176.5 (3) | C1B—C2B—C3B—C4B | 1.2 (5) |
C11A—C10A—C15A—Cl1A | 176.5 (2) | C7B—C2B—C3B—C4B | −179.7 (3) |
C9A—C10A—C15A—Cl1A | 1.2 (4) | C10A—C15A—C14A—C13A | 2.0 (5) |
C15B—C10B—C9B—O9B | 124.0 (4) | Cl1A—C15A—C14A—C13A | −175.7 (3) |
C11B—C10B—C9B—O9B | −51.3 (4) | C15A—C10A—C11A—C12A | −0.4 (4) |
C15B—C10B—C9B—C4B | −59.7 (4) | C9A—C10A—C11A—C12A | 175.3 (3) |
C11B—C10B—C9B—C4B | 125.0 (3) | C15B—C10B—C11B—C12B | 1.3 (4) |
C17B—O16B—C1B—C2B | 100.3 (4) | C9B—C10B—C11B—C12B | 176.9 (3) |
C17B—O16B—C1B—C6B | −81.8 (4) | C10B—C15B—C14B—C13B | 0.2 (5) |
C17A—O16A—C1A—C2A | 97.0 (3) | Cl1B—C15B—C14B—C13B | −177.5 (3) |
C17A—O16A—C1A—C6A | −84.8 (4) | C10B—C11B—C12B—C13B | 0.0 (5) |
O9B—C9B—C4B—C3B | 167.1 (3) | C20B—O19B—C18B—O18B | −8.1 (7) |
C10B—C9B—C4B—C3B | −9.1 (5) | C20B—O19B—C18B—C17B | 179.7 (4) |
O9B—C9B—C4B—C5B | −11.8 (5) | C20A—O19A—C18A—O18A | −0.9 (6) |
C10B—C9B—C4B—C5B | 172.0 (3) | C20A—O19A—C18A—C17A | −178.6 (3) |
C3B—C4B—C5B—C6B | 1.5 (5) | C10A—C11A—C12A—C13A | 1.1 (5) |
C9B—C4B—C5B—C6B | −179.6 (3) | C15A—C14A—C13A—C12A | −1.3 (5) |
O16B—C1B—C2B—C3B | 179.2 (3) | C11A—C12A—C13A—C14A | −0.2 (6) |
C6B—C1B—C2B—C3B | 1.4 (5) | C1A—O16A—C17A—C18A | −161.4 (3) |
O16B—C1B—C2B—C7B | 0.2 (5) | O18A—C18A—C17A—O16A | 16.7 (5) |
C6B—C1B—C2B—C7B | −177.6 (3) | O19A—C18A—C17A—O16A | −165.6 (3) |
O16A—C1A—C2A—C3A | 177.7 (3) | C1B—O16B—C17B—C18B | −177.6 (3) |
C6A—C1A—C2A—C3A | −0.5 (5) | O18B—C18B—C17B—O16B | 21.5 (7) |
O16A—C1A—C2A—C7A | −0.9 (4) | O19B—C18B—C17B—O16B | −166.3 (4) |
C6A—C1A—C2A—C7A | −179.1 (3) | C15B—C14B—C13B—C12B | 1.1 (5) |
C4A—C5A—C6A—C1A | 0.9 (5) | C11B—C12B—C13B—C14B | −1.2 (5) |
C4A—C5A—C6A—C8A | −177.6 (3) | C18A—O19A—C20A—C21A | 177.5 (4) |
C2A—C1A—C6A—C5A | −1.0 (5) | C18B—O19B—C20B—C21B | 175.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11A—H11A···O18Bi | 0.93 | 2.49 | 3.346 (6) | 153 |
C11B—H11B···O18Ai | 0.93 | 2.47 | 3.351 (5) | 159 |
C14B—H14B···O9A | 0.93 | 2.59 | 3.482 (4) | 161 |
C20A—H20A···O9Bii | 0.97 | 2.57 | 3.420 (5) | 147 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H19ClO4 |
Mr | 346.79 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.4082 (8), 14.7290 (6), 15.4470 (8) |
β (°) | 107.268 (5) |
V (Å3) | 3564.9 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.912, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17025, 6997, 3576 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.191, 1.02 |
No. of reflections | 6997 |
No. of parameters | 439 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.36 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C11A—H11A···O18Bi | 0.93 | 2.49 | 3.346 (6) | 153 |
C11B—H11B···O18Ai | 0.93 | 2.47 | 3.351 (5) | 159 |
C14B—H14B···O9A | 0.93 | 2.59 | 3.482 (4) | 161 |
C20A—H20A···O9Bii | 0.97 | 2.57 | 3.420 (5) | 147 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y+1/2, −z−1/2. |
Acknowledgements
SAK and TP are grateful to the University Grants Commission, New Delhi, for financial assistance under the Major Research project scheme. VLR and MKU thank the Department of Science and Technology, New Delhi, for the award of INSPIRE Fellowships. One of the authors (RK) acknowledges the Department of Science and Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
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Analogues of phenoxy ethanoic acid are considered to be very important compounds in the field of medicinal chemistry, and the compounds were found to have good antifungal activity against pathogenic fungi and posses moderate activity against gram negative bacteria in comparison to standard ciprofloxacin (Dahiya & Kaur 2007). Resent studies shows that changes in the chemical and stereoisomeric structures of phenoxy ethanoic acid alter peroxisome proliferation (Esbenshade et al., 1990). The anti-inflammatory activity results revealed a significant anti-inflammatory activity (up to 63.4%, 62.0%, 64.1% and 62.5% edema inhibition, respectively), as compared to the standard drug diclofenac (67.0%). Pathological investigation has shown that the analogues of phenoxy ethanoic acid compounds have higher anti hyperlipidmeic effect and caused appropriate modulation in HDL levels and some compounds showed a good potential for obesity-associated hyperlipidemia (Khanum et al., 2010).The phenoxy acetic acid analogues show very good antitumor activity on Ehrlich asites tumor cells (Prabhakar et al., 2006) and also show the anti ulcerogenic activity, cyclooxygenase activity, anticonvulsant activity (Sudha et al., 2003) and anti microbial activities (Ma et al., 2011). We were interested in obtaining these type of compounds to evaluate their biological activity; for this purpose, the title compound,[4-(2-chlorobenzoyl)-2,6-dimethylphenoxy].ethanoic acid (I) was synthesized.
The asymmetric unit of (I) comprises two crystallographically independent molecules, A and B,respectively (Fig. 1). The geometry of both independent molecules indicates a high degree of similarity in terms of bond distances and angles. The average aromatic bond length in the phenyl ring is 1.381 (3) Å and 1.380 (3) Å for A, B, respectively. Remaining bond distances are within normal ranges (Allen et al., 1987). The dihedral angle between the phenyl rings is 63.41 (8)° for molecule A and 61.41 (9)° for molecule B. Adjacent molecules of different type (A,B) are interconnected in pairs, through π-π interactions between their central phenyl rings (C1-C6) [ centroid separation = 3.801 (2)Å, interplanar spacing = 3.605Å, centroid shift = 1.204Å]. Finally, C—H···O hydrogen bonds (Table 1) link these dimeric entities into bilayered structures parallel to (100).