1-(2-Hy­droxy-4-meth­oxy­phen­yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Thippeswamy, G.B.; Vijay Kumar, D.; Jayashree, B.S.; Sridhar, M.A.; Shashidhara Prasad, J.

doi:10.1107/S1600536811007586

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o829

doi:10.1107/S1600536811007586

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1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one

G. B. Thippeswamy,^a D. Vijay Kumar,^b B. S. Jayashree,^b M. A. Sridhar ^a ^* and J. Shashidhara Prasad ^a

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Pharmaceutical Chemistry, Manipal college of Pharmaceutical Sciences, Manipal 576 104, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 1 December 2010; accepted 28 February 2011; online 9 March 2011)

The molecule of the title compound, C₁₇H₁₆O₃, exists in the E conformation with respect to the central C=C bond, is almost planar(r.m.s. deviation = 0.003 Å) and has an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, molecules are linked by C—H⋯O interactions.

Related literature

For the biological activity of compounds with a chalcone backbone, see: Jayashree et al. (2009 ); Epifano et al. (2007 ); Onyilagna et al. (1997 ); Satyanarayana et al. (2004 ); Deshpande et al. (1999 ); Hsieh et al. (2000 ); Khatib et al. (2005 ); Barford et al. (2002 ); Nielsen et al. (1995 ); Severi et al. (1998 ); Siva Kumar et al. (2007 ). For a related structure, see: Thippeswamy et al. (2010 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₆O₃
M_r = 268.30
Monoclinic, P 2₁ /c
a = 11.340 (2) Å
b = 6.8350 (7) Å
c = 20.449 (4) Å
β = 117.710 (4)°
V = 1403.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.22 mm

Data collection

MacScience DIPLabo 32001 diffractometer
4137 measured reflections
2346 independent reflections
1502 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.184
S = 1.05
2346 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O11	0.82	1.77	2.502 (3)	148
C13—H13⋯O18ⁱ	0.93	2.56	3.282 (3)	135
Symmetry code: (i) x, y-1, z.

Data collection: XPRESS (MacScience, 2002 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and ORTEPII (Johnson, 1976 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007586/jh2240sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007586/jh2240Isup2.hkl

checkCIF report

Comment top

Chalcones (1,3-diarylpropenones) are well known intermediates for the synthesis of various heterocyclic compounds. The compounds with chalcone backbone have been reported to possess various biological activities such as anti-oxidant (Jayashree et al., 2009), anti-inflammatory (Hsieh et al., 2000), anti-cancer (Epifano et al., 2007), anti-hyperglycemic (Satyanarayana et al., 2004), anti-viral (Onyilagna et al., 1997), anti-leishmanial (Nielsen et al.,1995), anti-tubercular (Siva Kumar et al., 2007), immunomodulatory (Barford et al., 2002), inhibition of various enzymes like leukotriene B (Deshpande et al., 1999), tyrosinase kinase (Khatib et al., 2005) and aldose reductase (Severi et al., 1998) etc. The presence of a reactive alph, beta-unsaturated ketone function in chalcones is found to be responsible for their activity. In the present communication, we report the synthesis and crystal structure of substituted 2-hydroxy-chalcone. In the title compound, C17H16O3, the dihedral angle between the ring systems is 9.57 (13)°. The central prop-2-en-1-oneunit is planar (r.m.s. deviation = 0.003 Å) and is oriented at a dihedral angle of 2.46 (10)° with respect to the methoxyphenyl ring and at 7.46 (10)° with respect to the methylphenyl ring. The angles C2—C1—O11, C12—C1—O11 and C2—C1—C12 are 118.5 (3)°, 119.9 (2)° and 121.5 (2)° respectively which indicate that the position of C1 atom is nearly in trigonal geometry. The bond lengths and bond angles of the molecule are comparable with the values reported for 1-(2-hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl) prop-2-en-1-one (Thippeswamy et al.,2010). The atoms C4, C7 in methylphenyl ring deviate by -0.018 (2) Å, -0.014 (3) Å, and the atoms C12, C15 in methoxyphenyl ring deviate by -0.002 (2) Å, -0.003 (3)Å respectively from Cremer and Pople plane (Cremer et al.,1975) which show that the two six-membered rings are in planar conformation. The packing of the molecules is characterized by intramolecular hydrogen bond of type O–H–O.

Related literature top

For the biological activity of compounds with a chalcone backbone, see: Jayashree et al. (2009); Epifano et al. (2007); Onyilagna et al. (1997); Satyanarayana et al. (2004); Deshpande et al. (1999); Hsieh et al. (2000); Khatib et al. (2005); Barford et al. (2002); Nielsen et al. (1995); Severi et al. (1998); Siva Kumar et al. (2007). For a related structure, see: Thippeswamy et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared by dissolving 2-hydroxy-4- methoxyacetophenone 0.05 m mol in 15 ml of ethanol taken in a conical flask. To this 5 ml of 20° aqueous sodium hydroxide was added and kept for stirring at room temperature. To this mixture, 4-methylbenzaldehyde 0.05 m mol was added and continued stirring till the completion of reaction. The progress of the reaction was monitored by TLC using n-hexane and ethyl acetate as solvent system. After completion of the reaction, the mixture was poured into ice cold water, mixed properly and acidified with dilute hydrochloric acid. The title compound separates as precipitate which was collected by filtration and crystallized from methanol. The compound was chafacterized by spectroscope technique. The IR spectrum was recorded in KBr on FTIR-8400 (Shimadzu). The 1H NMR spectrum was recorded in CdCl3 solution at 400 MHz on AMX 400 MHz High Resolution Multinuclear FT-NMR Spectrometer (Bruker) with tetramethylsilane (TMS) as internal standard.

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Crystal structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The packing of the title compound, viewed down the b axis.

1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₆O₃	F(000) = 568
M_r = 268.30	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4137 reflections
a = 11.340 (2) Å	θ = 2.2–25.0°
b = 6.8350 (7) Å	µ = 0.09 mm⁻¹
c = 20.449 (4) Å	T = 293 K
β = 117.710 (4)°	Block, yellow
V = 1403.2 (4) Å³	0.26 × 0.24 × 0.22 mm
Z = 4

Data collection top

MacScience DIPLabo 32001 diffractometer	1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −13→13
ω scans	k = −7→7
4137 measured reflections	l = −24→24
2346 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.1052P)² + 0.0529P]
S = 1.05	(Δ/σ)_max = 0.010
2346 reflections	Δρ_max = 0.15 e Å⁻³
184 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (8)

Crystal data top

C₁₇H₁₆O₃	V = 1403.2 (4) Å³
M_r = 268.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.340 (2) Å	µ = 0.09 mm⁻¹
b = 6.8350 (7) Å	T = 293 K
c = 20.449 (4) Å	0.26 × 0.24 × 0.22 mm
β = 117.710 (4)°

Data collection top

MacScience DIPLabo 32001 diffractometer	1502 reflections with I > 2σ(I)
4137 measured reflections	R_int = 0.029
2346 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
2346 reflections	Δρ_min = −0.15 e Å⁻³
184 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O11	0.22698 (19)	0.0248 (2)	0.50576 (11)	0.1003 (8)
O18	0.4503 (2)	0.1776 (2)	0.58182 (12)	0.1010 (8)
O19	0.82822 (19)	−0.2381 (3)	0.68536 (10)	0.0952 (8)
C1	0.2778 (3)	−0.1418 (3)	0.51232 (13)	0.0769 (9)
C2	0.1894 (3)	−0.3084 (4)	0.47598 (14)	0.0781 (9)
C3	0.0588 (3)	−0.2910 (4)	0.44711 (13)	0.0788 (9)
C4	−0.0439 (2)	−0.4376 (4)	0.40885 (12)	0.0745 (9)
C5	−0.0165 (3)	−0.6329 (4)	0.40093 (13)	0.0771 (9)
C6	−0.1187 (3)	−0.7615 (4)	0.36199 (14)	0.0829 (10)
C7	−0.2504 (3)	−0.7042 (4)	0.33000 (13)	0.0853 (10)
C8	−0.2767 (3)	−0.5123 (5)	0.34017 (15)	0.0941 (11)
C9	−0.1758 (3)	−0.3830 (4)	0.37904 (14)	0.0876 (10)
C10	−0.3608 (3)	−0.8452 (5)	0.28614 (16)	0.1111 (14)
C12	0.4201 (2)	−0.1668 (3)	0.55578 (12)	0.0695 (8)
C13	0.4837 (3)	−0.3491 (3)	0.56897 (14)	0.0777 (9)
C14	0.6169 (3)	−0.3701 (3)	0.61167 (14)	0.0833 (10)
C15	0.6964 (3)	−0.2045 (4)	0.64370 (14)	0.0771 (9)
C16	0.6383 (3)	−0.0211 (3)	0.63231 (14)	0.0775 (10)
C17	0.5025 (3)	−0.0035 (3)	0.58930 (13)	0.0735 (9)
C20	0.9130 (3)	−0.0751 (4)	0.71775 (17)	0.1034 (12)
H2	0.22610	−0.42800	0.47330	0.0940*
H3	0.02810	−0.16830	0.45180	0.0950*
H5	0.07130	−0.67620	0.42210	0.0920*
H6	−0.09840	−0.89080	0.35710	0.0990*
H8	−0.36460	−0.47010	0.32020	0.1130*
H9	−0.19680	−0.25530	0.38550	0.1050*
H10A	−0.42770	−0.83800	0.30230	0.1670*
H10B	−0.32560	−0.97570	0.29340	0.1670*
H10C	−0.39960	−0.81220	0.23470	0.1670*
H13	0.43250	−0.45980	0.54770	0.0930*
H14	0.65550	−0.49360	0.61970	0.1000*
H16	0.69040	0.08900	0.65340	0.0930*
H18	0.36950	0.17260	0.55550	0.1510*
H20A	0.90600	0.01340	0.67960	0.1550*
H20B	1.00340	−0.11930	0.74500	0.1550*
H20C	0.88710	−0.00910	0.75050	0.1550*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0982 (14)	0.0672 (11)	0.1254 (16)	0.0151 (9)	0.0435 (12)	0.0038 (10)
O18	0.1048 (15)	0.0578 (10)	0.1353 (16)	0.0064 (9)	0.0516 (12)	0.0001 (9)
O19	0.0834 (14)	0.0929 (13)	0.1058 (14)	0.0051 (10)	0.0411 (11)	−0.0085 (10)
C1	0.0879 (18)	0.0692 (14)	0.0771 (15)	0.0051 (12)	0.0414 (14)	0.0029 (11)
C2	0.0831 (18)	0.0705 (14)	0.0819 (16)	0.0012 (12)	0.0393 (13)	−0.0014 (11)
C3	0.0831 (19)	0.0788 (15)	0.0731 (15)	0.0096 (13)	0.0352 (14)	0.0036 (12)
C4	0.0741 (17)	0.0851 (16)	0.0634 (14)	0.0081 (12)	0.0313 (12)	0.0052 (11)
C5	0.0742 (16)	0.0832 (16)	0.0737 (15)	0.0129 (12)	0.0343 (13)	0.0039 (12)
C6	0.0848 (19)	0.0857 (16)	0.0788 (16)	−0.0035 (14)	0.0385 (14)	−0.0054 (13)
C7	0.0818 (19)	0.1053 (19)	0.0654 (15)	−0.0058 (15)	0.0314 (13)	0.0042 (13)
C8	0.0705 (17)	0.114 (2)	0.0881 (18)	0.0105 (15)	0.0288 (14)	0.0126 (16)
C9	0.0760 (18)	0.0920 (17)	0.0909 (18)	0.0163 (14)	0.0355 (15)	0.0095 (14)
C10	0.096 (2)	0.141 (3)	0.0857 (19)	−0.0278 (19)	0.0334 (16)	−0.0083 (18)
C12	0.0817 (17)	0.0599 (12)	0.0743 (14)	0.0020 (11)	0.0426 (13)	0.0004 (10)
C13	0.0884 (18)	0.0621 (13)	0.0843 (16)	0.0032 (11)	0.0415 (14)	−0.0045 (11)
C14	0.096 (2)	0.0649 (14)	0.0892 (17)	0.0089 (12)	0.0433 (15)	−0.0031 (12)
C15	0.0809 (18)	0.0813 (15)	0.0758 (15)	0.0040 (13)	0.0420 (14)	−0.0022 (12)
C16	0.0836 (19)	0.0677 (14)	0.0885 (17)	−0.0030 (12)	0.0461 (15)	−0.0061 (12)
C17	0.0923 (19)	0.0577 (13)	0.0832 (15)	0.0049 (11)	0.0514 (14)	0.0018 (11)
C20	0.087 (2)	0.112 (2)	0.107 (2)	−0.0097 (17)	0.0417 (17)	−0.0209 (17)

Geometric parameters (Å, º) top

O11—C1	1.255 (3)	C14—C15	1.405 (4)
O18—C17	1.350 (3)	C15—C16	1.385 (4)
O19—C15	1.352 (4)	C16—C17	1.378 (5)
O19—C20	1.419 (4)	C2—H2	0.9300
O18—H18	0.8200	C3—H3	0.9300
C1—C2	1.470 (4)	C5—H5	0.9300
C1—C12	1.445 (4)	C6—H6	0.9300
C2—C3	1.320 (5)	C8—H8	0.9300
C3—C4	1.458 (4)	C9—H9	0.9300
C4—C9	1.379 (4)	C10—H10A	0.9600
C4—C5	1.397 (4)	C10—H10B	0.9600
C5—C6	1.375 (4)	C10—H10C	0.9600
C6—C7	1.380 (5)	C13—H13	0.9300
C7—C8	1.382 (4)	C14—H14	0.9300
C7—C10	1.502 (4)	C16—H16	0.9300
C8—C9	1.370 (5)	C20—H20A	0.9600
C12—C17	1.412 (3)	C20—H20B	0.9600
C12—C13	1.402 (3)	C20—H20C	0.9600
C13—C14	1.356 (5)

O11···O18	2.502 (3)	H2···C5	2.8200
O18···O11	2.502 (3)	H2···C13	2.7100
O18···C13ⁱ	3.282 (3)	H2···H5	2.3100
O11···H3	2.3900	H2···H13	2.1300
O11···H9ⁱⁱ	2.8700	H3···O11	2.3900
O11···H5ⁱ	2.7200	H3···H9	2.3400
O11···H18	1.7700	H5···O11^v	2.7200
O18···H13ⁱ	2.5600	H5···C2	2.8200
C1···C7ⁱⁱⁱ	3.540 (4)	H5···H2	2.3100
C3···C5ⁱⁱⁱ	3.398 (4)	H6···H10B	2.3600
C3···C4ⁱⁱⁱ	3.551 (4)	H8···H10A	2.5900
C4···C4ⁱⁱⁱ	3.488 (3)	H8···C10^viii	2.9800
C4···C3ⁱⁱⁱ	3.551 (4)	H9···H3	2.3400
C5···C3ⁱⁱⁱ	3.398 (4)	H9···O11ⁱⁱ	2.8700
C6···C20^iv	3.590 (5)	H10A···H8	2.5900
C7···C1ⁱⁱⁱ	3.540 (4)	H10A···C12ⁱⁱⁱ	2.8600
C10···C12ⁱⁱⁱ	3.596 (4)	H10A···C17ⁱⁱⁱ	2.9200
C12···C10ⁱⁱⁱ	3.596 (4)	H10B···H6	2.3600
C13···O18^v	3.282 (3)	H13···O18^v	2.5600
C20···C6^iv	3.590 (5)	H13···C2	2.6600
C1···H18	2.3700	H13···H2	2.1300
C2···H13	2.6600	H16···C20	2.5000
C2···H5	2.8200	H16···H20A	2.3100
C4···H20C^vi	2.9800	H16···H20C	2.2900
C5···H2	2.8200	H18···O11	1.7700
C5···H20C^vi	2.9100	H18···C1	2.3700
C6···H20C^vi	2.9600	H20A···C16	2.7300
C7···H20C^vi	3.0900	H20A···H16	2.3100
C10···H8^vii	2.9800	H20C···C16	2.7300
C12···H10Aⁱⁱⁱ	2.8600	H20C···H16	2.2900
C13···H2	2.7100	H20C···C4^ix	2.9800
C16···H20A	2.7300	H20C···C5^ix	2.9100
C16···H20C	2.7300	H20C···C6^ix	2.9600
C17···H10Aⁱⁱⁱ	2.9200	H20C···C7^ix	3.0900
C20···H16	2.5000

C15—O19—C20	118.1 (2)	C3—C2—H2	119.00
C17—O18—H18	109.00	C2—C3—H3	116.00
O11—C1—C2	118.5 (3)	C4—C3—H3	116.00
O11—C1—C12	119.9 (2)	C4—C5—H5	120.00
C2—C1—C12	121.5 (2)	C6—C5—H5	120.00
C1—C2—C3	121.1 (3)	C5—C6—H6	119.00
C2—C3—C4	128.9 (3)	C7—C6—H6	119.00
C3—C4—C9	118.9 (3)	C7—C8—H8	119.00
C5—C4—C9	117.5 (3)	C9—C8—H8	119.00
C3—C4—C5	123.6 (3)	C4—C9—H9	119.00
C4—C5—C6	120.3 (3)	C8—C9—H9	119.00
C5—C6—C7	121.9 (3)	C7—C10—H10A	110.00
C6—C7—C8	117.4 (3)	C7—C10—H10B	109.00
C6—C7—C10	121.3 (3)	C7—C10—H10C	109.00
C8—C7—C10	121.4 (3)	H10A—C10—H10B	109.00
C7—C8—C9	121.3 (3)	H10A—C10—H10C	109.00
C4—C9—C8	121.6 (3)	H10B—C10—H10C	109.00
C1—C12—C13	123.4 (2)	C12—C13—H13	119.00
C1—C12—C17	120.2 (2)	C14—C13—H13	119.00
C13—C12—C17	116.4 (2)	C13—C14—H14	120.00
C12—C13—C14	122.5 (2)	C15—C14—H14	120.00
C13—C14—C15	119.8 (2)	C15—C16—H16	120.00
O19—C15—C16	124.1 (3)	C17—C16—H16	120.00
C14—C15—C16	119.9 (3)	O19—C20—H20A	109.00
O19—C15—C14	116.0 (3)	O19—C20—H20B	109.00
C15—C16—C17	119.3 (2)	O19—C20—H20C	110.00
O18—C17—C16	117.0 (2)	H20A—C20—H20B	109.00
C12—C17—C16	122.1 (2)	H20A—C20—H20C	110.00
O18—C17—C12	120.9 (3)	H20B—C20—H20C	109.00
C1—C2—H2	119.00

C20—O19—C15—C16	−1.9 (4)	C5—C6—C7—C10	178.6 (3)
C20—O19—C15—C14	178.8 (3)	C10—C7—C8—C9	−178.8 (3)
C12—C1—C2—C3	168.4 (3)	C6—C7—C8—C9	1.5 (4)
O11—C1—C12—C13	176.6 (3)	C7—C8—C9—C4	0.9 (4)
C2—C1—C12—C13	−2.5 (4)	C17—C12—C13—C14	0.2 (4)
C2—C1—C12—C17	179.3 (3)	C1—C12—C13—C14	−178.0 (3)
O11—C1—C12—C17	−1.7 (4)	C13—C12—C17—O18	−178.0 (2)
O11—C1—C2—C3	−10.7 (4)	C13—C12—C17—C16	0.4 (4)
C1—C2—C3—C4	179.5 (2)	C1—C12—C17—O18	0.4 (4)
C2—C3—C4—C9	−176.0 (3)	C1—C12—C17—C16	178.8 (3)
C2—C3—C4—C5	4.5 (4)	C12—C13—C14—C15	−0.9 (4)
C3—C4—C5—C6	−177.9 (3)	C13—C14—C15—C16	0.8 (4)
C5—C4—C9—C8	−2.9 (4)	C13—C14—C15—O19	−179.9 (3)
C9—C4—C5—C6	2.6 (4)	O19—C15—C16—C17	−179.4 (3)
C3—C4—C9—C8	177.6 (3)	C14—C15—C16—C17	−0.2 (4)
C4—C5—C6—C7	−0.4 (4)	C15—C16—C17—O18	178.0 (3)
C5—C6—C7—C8	−1.7 (4)	C15—C16—C17—C12	−0.5 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x, −y, −z+1; (iii) −x, −y−1, −z+1; (iv) −x+1, −y−1, −z+1; (v) x, y−1, z; (vi) x−1, −y−1/2, z−1/2; (vii) −x−1, y−1/2, −z+1/2; (viii) −x−1, y+1/2, −z+1/2; (ix) x+1, −y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11	0.82	1.77	2.502 (3)	148
C3—H3···O11	0.93	2.39	2.758 (3)	103
C13—H13···O18^v	0.93	2.56	3.282 (3)	135

Symmetry code: (v) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃
M_r	268.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.340 (2), 6.8350 (7), 20.449 (4)
β (°)	117.710 (4)
V (Å³)	1403.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	MacScience DIPLabo 32001 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4137, 2346, 1502
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.184, 1.05
No. of reflections	2346
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: XPRESS (MacScience, 2002), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ORTEPII (Johnson, 1976), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11	0.82	1.77	2.502 (3)	148
C13—H13···O18ⁱ	0.93	2.56	3.282 (3)	135

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors are grateful to the DST/CSIR, New Delhi, for financial support under projects SP/I2/FOO/93 and 01/1904/03/EMR-II 2004. The authors duly acknowledge Manipal College of Pharmaceutical Sciences, Manipal, for providing facilities to carry out the synthetic work.

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