Ethyl 2-(4-benzoyl-2,5-dimethyl­phen­oxy)acetate

Devarajegowda, H.C.; Khanum, S.A.; Jeyaseelan, S.; Eryani, W.A.; Shylajakumari, J.

doi:10.1107/S1600536809043190

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2854-o2855

https://doi.org/10.1107/S1600536809043190

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Ethyl 2-(4-benzoyl-2,5-dimethylphenoxy)acetate

H. C. Devarajegowda,^a ^* Shaukath Ara Khanum,^b S. Jeyaseelan,^a Waleed Al Eryani ^a and J. Shylajakumari ^c

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Chemistry, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^cDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 7 October 2009; accepted 20 October 2009; online 28 October 2009)

The title compound, C₁₉H₂₀O₄, was synthesized via a Fries rearrangement of hydroxy benzophenone. The dihedral angle between the least-squares planes of the two benzene rings is 69.04 (11)°. The molecular structure displays an intramolecular non-classical C—H⋯O hydrogen bond.

Related literature

hydroxy benzophenones may obtained from natural products, see: Henry et al. (1999 ); Vidya et al. (2003 ); Cuesta-Rubio et al. (2002 ) and by synthetic methods, see: Hsieh et al. (2003 ); Revesz et al. (2004 ); Schlitzer et al. (2002 ). For their biological activity, see: Jiri et al. (1991 ); Palomer et al. (2000 , 2002 ); Palaska et al. (2002 ); Khanum et al. (2004a ,b ). Benzophenone analogues with nitro substituents exhibit significant in vivo antitumor activity and they have been reported to show activity as immunomodulators, see: Leonard (1997 ). Nitro benzophenone derivatives show strong cytotoxic activity while the corresponding aminobenzophenone derivatives show weak activity, see: Kumazawa et al. (1997 ). For the antimicobial activity of benzophenone derivatives, see: Selvi et al. (2003 ).

Experimental

Crystal data

C₁₉H₂₀O₄
M_r = 312.35
Triclinic, $[P \overline 1]$
a = 8.148 (4) Å
b = 8.635 (4) Å
c = 13.029 (7) Å
α = 84.054 (8)°
β = 81.176 (8)°
γ = 66.559 (7)°
V = 830.2 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.21 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.982, T_max = 0.991
8847 measured reflections
3391 independent reflections
2630 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.173
S = 1.05
3391 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2	0.96	2.28	2.751 (3)	110

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809043190/rk2174sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043190/rk2174Isup2.hkl

checkCIF report

Comment top

Hydroxy benzophenones are achieved from natural products (Henry et al., 1999; Vidya et al., 2003; Cuesta-Rubio et al., 2002) as well as by synthetic methods (Hsieh et al., 2003; Schlitzer et al., 2002; Revesz et al., 2004). The great importance of these substances is essentially due to the diverse biological and chemical properties they acquire. Benzophenone analogues possess a high analgesic (Jiri et al., 1991) efficacy and also endowed with anti-inflammatory property (Palomer et al., 2000; Palomer et al., 2002; Palaska et al., 2002; Khanum et al., 2004a,b).

Benzophenone analogues with nitro substituent exhibit significant in vivo antitumor activity and they have been reported to show activity as immunomodulators (Leonard, 1997). Based on these report, in vitro and in vivo studies of a series of novel nitro- and amino-substituted benzophenones have been investigated as potential anticancer agents. Nitro benzophenone derivative showed strong cytotoxic activity while the corresponding aminobenzophenone derivatives showed weak activity (Kumazawa et al., 1997). Besides benzophenone derivatives endowed with anti-microbial activity, for instance isoprenylated benzophenone, at its lower concentration of 500 to 1000 p.p.m. inhibits aflatoxin production in Aspergillus flavus, relatively greater than inhibition growth of the fungus - Selvi et al., (2003).

The molecular structure of title compound is shown on Fig.1. The dihedral angle between least-squares planes (two phenyl rings) is 69.04 (11)°. The intramolecular non-classical C–H···O hydrogen bond (Table 1) is observed.

Related literature top

For background to hydroxy benzophenones, see: Henry et al. (1999); Vidya et al. (2003); Cuesta-Rubio et al. (2002); Jiri et al. (1991); Palomer et al. (2000, 2002); Palaska et al. (2002); Khanum et al. (2004a,b); Leonard (1997); Kumazawa et al. (1997); Selvi et al. (2003). For related syntheses, see: Hsieh et al. (2003); Revesz et al. (2004); Schlitzer et al. (2002).

Experimental top

2,5-Dimethyl phenyl benzoate was synthesized from 2,5-dimethyl phenol and benzoyl chloride in presence of 10% sodium hydroxide. 4-Hydroxy-2,5-dimethyl benzophenone was achieved from 2,5-dimethyl phenyl benzoate by Fries rearrangement.

In a typical procedure, a mixture of 4-hydroxy-2,5-dimethylbenzophenone (4.5 g, 0.02 mol) and ethylchloroacetate (2.4 g, 0.02 mol) in dry acetone (60 ml) and anhydrous potassium carbonate (2.8 g, 0.02 mol) was refluxed for 6 h then cooled and the solvent removed under reduced pressure. The residual mass was triturated with ice water to remove potassium carbonate and extracted with ether (3 × 50ml) and the ether layer was washed with 10% sodium hydroxide solution (3 × 30ml) followed by water (3 × 30ml) and then dried over anhydrous sodium sulfate and evaporated to dryness to get crude solid, which on recrystallization with ethanol gave 4-benzoyl-2,5-dimethyl phenoxy ethyl acetate.

M.p. 329 K; IR (Nujol): 1740 (ester, C═O), 1665 cm^-1 (C═O). ¹H NMR (CDCl₃): δ 1.2 (t, J=7 Hz, 3H, CH₃ of ester), 2.2-2.3 (d, 6H, 2Ar-CH₃), 4.25 (q, J=6 Hz, 2H, CH₂ of ester), 4.45 (s, 2H, OCH₂), 7.2-7.8 (bm, 7H, Ar–H); Anal. Cal. for C₁₉H₂₀O₄: C, 72.61%; H, 6.36%. Found: C, 72.29%; H, 6.15%.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Ethyl 2-(4-benzoyl-2,5-dimethylphenoxy)acetate top

Crystal data top

C₁₉H₂₀O₄	Z = 2
M_r = 312.35	F(000) = 332
Triclinic, P1	D_x = 1.250 Mg m⁻³
Hall symbol: -P 1	Melting point: 329 K
a = 8.148 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.635 (4) Å	Cell parameters from 3391 reflections
c = 13.029 (7) Å	θ = 1.6–26.4°
α = 84.054 (8)°	µ = 0.09 mm⁻¹
β = 81.176 (8)°	T = 295 K
γ = 66.559 (7)°	Plate, colourless
V = 830.2 (7) Å³	0.21 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	3391 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 26.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.982, T_max = 0.991	k = −10→10
8847 measured reflections	l = −16→16

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0848P)² + 0.2822P] where P = (F_o² + 2F_c²)/3
3391 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₂₀O₄	γ = 66.559 (7)°
M_r = 312.35	V = 830.2 (7) Å³
Triclinic, P1	Z = 2
a = 8.148 (4) Å	Mo Kα radiation
b = 8.635 (4) Å	µ = 0.09 mm⁻¹
c = 13.029 (7) Å	T = 295 K
α = 84.054 (8)°	0.21 × 0.20 × 0.10 mm
β = 81.176 (8)°

Data collection top

Bruker SMART CCD diffractometer	3391 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2630 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.991	R_int = 0.025
8847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
3391 reflections	Δρ_min = −0.25 e Å⁻³
209 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	0.4354 (3)	0.82563 (19)	0.84149 (12)	0.0691 (5)
O2	0.14909 (19)	1.14174 (17)	0.41431 (11)	0.0546 (4)
O3	0.1127 (2)	1.37122 (19)	0.24885 (14)	0.0715 (5)
O4	0.1339 (2)	1.16785 (19)	0.14867 (12)	0.0662 (5)
C1	0.4303 (3)	0.5733 (2)	0.79154 (15)	0.0462 (5)
C2	0.5409 (3)	0.4695 (3)	0.86317 (18)	0.0642 (6)
H2	0.6073	0.5104	0.8967	0.077*
C3	0.5525 (4)	0.3051 (3)	0.8849 (2)	0.0760 (7)
H3	0.6276	0.2356	0.9324	0.091*
C4	0.4536 (4)	0.2448 (3)	0.8364 (2)	0.0731 (7)
H4	0.4611	0.1347	0.8516	0.088*
C5	0.3435 (4)	0.3461 (3)	0.7654 (2)	0.0667 (6)
H5	0.2761	0.3047	0.7331	0.080*
C6	0.3327 (3)	0.5103 (3)	0.74180 (17)	0.0537 (5)
H6	0.2600	0.5780	0.6927	0.064*
C7	0.4101 (3)	0.7530 (2)	0.77353 (15)	0.0476 (5)
C8	0.3509 (2)	0.8461 (2)	0.67388 (15)	0.0425 (4)
C9	0.4344 (2)	0.7866 (2)	0.57555 (14)	0.0413 (4)
C10	0.3660 (2)	0.8849 (2)	0.48841 (14)	0.0432 (4)
H10	0.4193	0.8466	0.4225	0.052*
C11	0.2199 (2)	1.0389 (2)	0.49763 (15)	0.0437 (4)
C12	0.1369 (2)	1.1014 (2)	0.59520 (16)	0.0449 (4)
C13	0.2055 (3)	1.0032 (2)	0.68133 (15)	0.0457 (4)
H13	0.1531	1.0430	0.7470	0.055*
C14	0.6014 (3)	0.6268 (2)	0.56025 (16)	0.0490 (5)
H14A	0.6369	0.6093	0.4872	0.074*
H14B	0.5765	0.5326	0.5935	0.074*
H14C	0.6970	0.6368	0.5902	0.074*
C15	−0.0212 (3)	1.2694 (2)	0.60437 (19)	0.0596 (6)
H15A	−0.0484	1.3174	0.5362	0.089*
H15B	0.0086	1.3446	0.6403	0.089*
H15C	−0.1241	1.2532	0.6425	0.089*
C16	0.2201 (3)	1.0816 (3)	0.31397 (16)	0.0523 (5)
H16A	0.1847	0.9904	0.3029	0.063*
H16B	0.3507	1.0388	0.3062	0.063*
C17	0.1474 (3)	1.2266 (3)	0.23580 (17)	0.0519 (5)
C18	0.0828 (4)	1.2910 (3)	0.06180 (19)	0.0752 (7)
H18A	0.1834	1.3212	0.0322	0.090*
H18B	−0.0173	1.3927	0.0856	0.090*
C19	0.0308 (5)	1.2153 (4)	−0.0163 (2)	0.0967 (10)
H19A	−0.0037	1.2947	−0.0742	0.145*
H19B	−0.0689	1.1860	0.0136	0.145*
H19C	0.1310	1.1153	−0.0398	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1070 (13)	0.0530 (9)	0.0549 (9)	−0.0327 (9)	−0.0290 (9)	−0.0015 (7)
O2	0.0530 (8)	0.0449 (8)	0.0511 (8)	−0.0028 (6)	−0.0123 (6)	0.0043 (6)
O3	0.0911 (12)	0.0458 (9)	0.0748 (11)	−0.0189 (8)	−0.0288 (9)	0.0057 (8)
O4	0.0907 (12)	0.0566 (9)	0.0522 (9)	−0.0281 (8)	−0.0194 (8)	0.0076 (7)
C1	0.0514 (11)	0.0412 (10)	0.0429 (10)	−0.0149 (8)	−0.0053 (8)	−0.0019 (8)
C2	0.0795 (16)	0.0530 (12)	0.0612 (13)	−0.0237 (11)	−0.0233 (12)	0.0062 (10)
C3	0.0950 (19)	0.0504 (13)	0.0734 (16)	−0.0189 (13)	−0.0212 (14)	0.0142 (11)
C4	0.0944 (19)	0.0442 (12)	0.0723 (16)	−0.0254 (12)	0.0105 (14)	−0.0030 (11)
C5	0.0800 (16)	0.0592 (13)	0.0688 (15)	−0.0373 (12)	0.0026 (12)	−0.0127 (11)
C6	0.0568 (12)	0.0522 (11)	0.0534 (12)	−0.0226 (10)	−0.0058 (9)	−0.0036 (9)
C7	0.0524 (11)	0.0426 (10)	0.0468 (11)	−0.0158 (9)	−0.0092 (9)	−0.0043 (8)
C8	0.0451 (10)	0.0354 (9)	0.0472 (10)	−0.0142 (8)	−0.0103 (8)	−0.0026 (7)
C9	0.0379 (9)	0.0346 (9)	0.0494 (10)	−0.0105 (7)	−0.0088 (8)	−0.0029 (7)
C10	0.0412 (10)	0.0391 (9)	0.0437 (10)	−0.0088 (8)	−0.0064 (8)	−0.0038 (8)
C11	0.0412 (9)	0.0384 (9)	0.0489 (11)	−0.0118 (8)	−0.0113 (8)	0.0027 (8)
C12	0.0402 (9)	0.0350 (9)	0.0552 (11)	−0.0092 (8)	−0.0066 (8)	−0.0044 (8)
C13	0.0491 (10)	0.0374 (9)	0.0473 (10)	−0.0132 (8)	−0.0018 (8)	−0.0084 (8)
C14	0.0439 (10)	0.0415 (10)	0.0532 (11)	−0.0060 (8)	−0.0095 (8)	−0.0038 (8)
C15	0.0524 (12)	0.0397 (10)	0.0711 (14)	−0.0017 (9)	−0.0052 (10)	−0.0056 (10)
C16	0.0562 (12)	0.0454 (10)	0.0509 (12)	−0.0142 (9)	−0.0131 (9)	0.0035 (9)
C17	0.0492 (11)	0.0502 (11)	0.0550 (12)	−0.0166 (9)	−0.0143 (9)	0.0045 (9)
C18	0.103 (2)	0.0683 (15)	0.0531 (13)	−0.0326 (15)	−0.0191 (13)	0.0145 (11)
C19	0.130 (3)	0.108 (2)	0.0701 (18)	−0.061 (2)	−0.0400 (18)	0.0194 (16)

Geometric parameters (Å, º) top

O1—C7	1.222 (2)	C9—C14	1.508 (2)
O2—C11	1.373 (2)	C10—C11	1.389 (3)
O2—C16	1.408 (3)	C10—H10	0.9300
O3—C17	1.190 (3)	C11—C12	1.397 (3)
O4—C17	1.327 (3)	C12—C13	1.382 (3)
O4—C18	1.459 (3)	C12—C15	1.510 (3)
C1—C6	1.387 (3)	C13—H13	0.9300
C1—C2	1.389 (3)	C14—H14A	0.9600
C1—C7	1.491 (3)	C14—H14B	0.9600
C2—C3	1.387 (3)	C14—H14C	0.9600
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.370 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.375 (4)	C16—C17	1.512 (3)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.390 (3)	C16—H16B	0.9700
C5—H5	0.9300	C18—C19	1.461 (4)
C6—H6	0.9300	C18—H18A	0.9700
C7—C8	1.494 (3)	C18—H18B	0.9700
C8—C9	1.400 (3)	C19—H19A	0.9600
C8—C13	1.402 (3)	C19—H19B	0.9600
C9—C10	1.392 (3)	C19—H19C	0.9600

C11—O2—C16	117.92 (15)	C11—C12—C15	120.57 (18)
C17—O4—C18	116.19 (18)	C12—C13—C8	122.77 (18)
C6—C1—C2	119.25 (19)	C12—C13—H13	118.6
C6—C1—C7	120.90 (18)	C8—C13—H13	118.6
C2—C1—C7	119.76 (18)	C9—C14—H14A	109.5
C3—C2—C1	120.2 (2)	C9—C14—H14B	109.5
C3—C2—H2	119.9	H14A—C14—H14B	109.5
C1—C2—H2	119.9	C9—C14—H14C	109.5
C4—C3—C2	120.1 (2)	H14A—C14—H14C	109.5
C4—C3—H3	119.9	H14B—C14—H14C	109.5
C2—C3—H3	119.9	C12—C15—H15A	109.5
C3—C4—C5	120.3 (2)	C12—C15—H15B	109.5
C3—C4—H4	119.8	H15A—C15—H15B	109.5
C5—C4—H4	119.8	C12—C15—H15C	109.5
C4—C5—C6	120.1 (2)	H15A—C15—H15C	109.5
C4—C5—H5	119.9	H15B—C15—H15C	109.5
C6—C5—H5	119.9	O2—C16—C17	108.12 (16)
C1—C6—C5	120.0 (2)	O2—C16—H16A	110.1
C1—C6—H6	120.0	C17—C16—H16A	110.1
C5—C6—H6	120.0	O2—C16—H16B	110.1
O1—C7—C1	120.15 (18)	C17—C16—H16B	110.1
O1—C7—C8	120.08 (17)	H16A—C16—H16B	108.4
C1—C7—C8	119.71 (16)	O3—C17—O4	124.87 (19)
C9—C8—C13	119.31 (17)	O3—C17—C16	125.4 (2)
C9—C8—C7	123.67 (16)	O4—C17—C16	109.72 (18)
C13—C8—C7	117.01 (17)	O4—C18—C19	108.2 (2)
C10—C9—C8	118.21 (16)	O4—C18—H18A	110.1
C10—C9—C14	118.84 (17)	C19—C18—H18A	110.1
C8—C9—C14	122.83 (16)	O4—C18—H18B	110.1
C11—C10—C9	121.49 (17)	C19—C18—H18B	110.1
C11—C10—H10	119.3	H18A—C18—H18B	108.4
C9—C10—H10	119.3	C18—C19—H19A	109.5
O2—C11—C10	123.79 (17)	C18—C19—H19B	109.5
O2—C11—C12	115.21 (16)	H19A—C19—H19B	109.5
C10—C11—C12	120.99 (17)	C18—C19—H19C	109.5
C13—C12—C11	117.21 (16)	H19A—C19—H19C	109.5
C13—C12—C15	122.22 (18)	H19B—C19—H19C	109.5

C6—C1—C2—C3	−0.3 (4)	C8—C9—C10—C11	0.6 (3)
C7—C1—C2—C3	176.3 (2)	C14—C9—C10—C11	−175.62 (17)
C1—C2—C3—C4	−0.6 (4)	C16—O2—C11—C10	4.9 (3)
C2—C3—C4—C5	0.5 (4)	C16—O2—C11—C12	−176.40 (17)
C3—C4—C5—C6	0.4 (4)	C9—C10—C11—O2	179.02 (17)
C2—C1—C6—C5	1.3 (3)	C9—C10—C11—C12	0.4 (3)
C7—C1—C6—C5	−175.3 (2)	O2—C11—C12—C13	−179.07 (16)
C4—C5—C6—C1	−1.3 (3)	C10—C11—C12—C13	−0.4 (3)
C6—C1—C7—O1	151.5 (2)	O2—C11—C12—C15	1.0 (3)
C2—C1—C7—O1	−25.1 (3)	C10—C11—C12—C15	179.66 (18)
C6—C1—C7—C8	−25.8 (3)	C11—C12—C13—C8	−0.7 (3)
C2—C1—C7—C8	157.6 (2)	C15—C12—C13—C8	179.29 (18)
O1—C7—C8—C9	130.0 (2)	C9—C8—C13—C12	1.7 (3)
C1—C7—C8—C9	−52.7 (3)	C7—C8—C13—C12	−179.52 (17)
O1—C7—C8—C13	−48.7 (3)	C11—O2—C16—C17	−169.54 (16)
C1—C7—C8—C13	128.6 (2)	C18—O4—C17—O3	3.8 (3)
C13—C8—C9—C10	−1.6 (3)	C18—O4—C17—C16	−174.0 (2)
C7—C8—C9—C10	179.72 (16)	O2—C16—C17—O3	32.4 (3)
C13—C8—C9—C14	174.45 (17)	O2—C16—C17—O4	−149.82 (18)
C7—C8—C9—C14	−4.3 (3)	C17—O4—C18—C19	−165.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.96	2.28	2.751 (3)	110

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₄
M_r	312.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.148 (4), 8.635 (4), 13.029 (7)
α, β, γ (°)	84.054 (8), 81.176 (8), 66.559 (7)
V (Å³)	830.2 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.982, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8847, 3391, 2630
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.173, 1.05
No. of reflections	3391
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.96	2.280	2.751 (3)	110.00

Acknowledgements

The authors thank Professor T. N Guru Row and Miss Brinda Selvaraj, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

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