Ethyl 2-[4-(2-chloro­benzo­yl)-2,6-di­methyl­phen­oxy]ethano­ate

Prashanth, T.; Ranganatha, V.L.; Usha, M.K.; Khanum, S.A.; Revannasiddaiah, D.; Anthal, S.; Kant, R.; Gupta, V.K.

doi:10.1107/S1600536812030693

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2435

https://doi.org/10.1107/S1600536812030693

Open

access

Ethyl 2-[4-(2-chlorobenzoyl)-2,6-dimethylphenoxy]ethanoate

T. Prashanth,^a V. Lakshmi Ranganatha,^a M. K. Usha,^b Shaukath Ara Khanum,^a D. Revannasiddaiah,^b Sumati Anthal,^c Rajni Kant ^c and Vivek K. Gupta ^c ^*

^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

(Received 13 June 2012; accepted 5 July 2012; online 14 July 2012)

The asymmetric unit of the title compound, C₁₉H₁₉ClO₄, 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).

Related 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

C₁₉H₁₉ClO₄
M_r = 346.79
Monoclinic, P 2₁ /c
a = 16.4082 (8) Å
b = 14.7290 (6) Å
c = 15.4470 (8) Å
β = 107.268 (5)°
V = 3564.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.912, T_max = 1.000
17025 measured reflections
6997 independent reflections
3576 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.191
S = 1.02
6997 reflections
439 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812030693/bg2469sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

[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%.

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: 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).

Figures top

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.

Ethyl 2-[4-(2-Chlorobenzoyl)-2,6-dimethylphenoxy]ethanoate top

Crystal data top

C₁₉H₁₉ClO₄	F(000) = 1456
M_r = 346.79	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	6997 independent reflections
Radiation source: fine-focus sealed tube	3576 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 0 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −20→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −18→17
T_min = 0.912, T_max = 1.000	l = −12→19
17025 measured reflections

Refinement top

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(F_o²) + (0.0686P)² + 0.8701P] where P = (F_o² + 2F_c²)/3
6997 reflections	(Δ/σ)_max = 0.001
439 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₁₉ClO₄	V = 3564.9 (3) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	6997 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3576 reflections with I > 2σ(I)
T_min = 0.912, T_max = 1.000	R_int = 0.039
17025 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.02	Δρ_max = 0.46 e Å⁻³
6997 reflections	Δρ_min = −0.36 e Å⁻³
439 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.912, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17025, 6997, 3576
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Dahiya, R. & Kaur, R. (2007). Aust. J. Basic Appl. Sci. 1, 525–532. CAS Google Scholar
Esbenshade, T. A., Kamann, V. S., Newman, H. A. I., Tortorella, V., Witiak, D. T. & Feller, D. R. (1990). Biochem. Pharmacol. 40, 263–274. CrossRef Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Khanum, S. A., Begum, B. A., Girish, V. & Khanum, N. F. (2010). Int. J. Biomed. Sci. 6, 60–65. CAS PubMed Google Scholar
Ma, X.-D., Zhang, X., Dai, H.-F., Yang, S. Q., Yang, L.-M., Gu, S.-X., Zheng, Y.-T., He, Q.-Q. & Chen, F.-E. (2011). Bioorg. Med. Chem. 19, 4601–4607. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Prabhakar, B. T., Khanum, S. A., Jayashree, K., Salimath, B. P. & Shashikanth, S. (2006). Bioorg. Med. Chem. 14, 435–446. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sudha, B. S., Shashikanth, S., Khanum, S. A. & Shriharsha, S. N. (2003). Indian J. Pharm. Sci. 65, 465–470. CAS Google Scholar