(E)-1-(4-Meth­oxy­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Carvalho-Jr, P.S.; Sallum, L.O.; Cidade, A.F.; Aquino, G.L.B.; Napolitano, H.B.

doi:10.1107/S1600536811028984

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2126

doi:10.1107/S1600536811028984

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(E)-1-(4-Methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

P. S. Carvalho-Jr,^a ^* L. O. Sallum,^a A. F. Cidade,^a G. L. B. Aquino ^a and H. B. Napolitano ^a

^aDepartment of Chemistry, State University of Goias, Anapolis, Brazil
^*Correspondence e-mail: paulo.junior@ueg.br

(Received 2 June 2011; accepted 18 July 2011; online 23 July 2011)

The title compound, C₁₉H₂₀O₅, was synthesized by reaction of 4-methoxyacetophenone and 3,4,5-trimethoxy-benzaldehyde. The aromatic rings form a dihedral angle of 36.39 (7)°. Two intramolecular C—H⋯O hydrogen bonds occur. The crystal packing features weak C—H⋯O interactions.

Related literature

For background to chalcones and the biological activity and derivatives, see: Dhar (1981 ); Dimmock et al. (1999 ). For their applications as organic non-linear optical materials, see: Sarojini et al. (2006 ) and for their choleretic and hepatoprotective activity, see: Ni et al. (2004 ). For the synthesis of chalcones, see: Patil et al. (2009 ). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999 ). For related structures, see: Sathiya Moorthi et al. (2005 ); Cai et al. (2011 ); Vijay Kumar et al. (2011 ); Bibila Mayaya Bisseyou et al. (2007 ). The title compound wss prepared by an aldol Claisen–Schmidt condensation reaction, see: Bandgar et al. (2009 , 2010 ); Hathaway (1987 ).

Experimental

Crystal data

C₁₉H₂₀O₅
M_r = 328.35
Monoclinic, P 2₁ /c
a = 7.5770 (1) Å
b = 16.2530 (3) Å
c = 14.0850 (3) Å
β = 107.528 (1)°
V = 1654.02 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.2 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
27371 measured reflections
3733 independent reflections
2907 reflections with I > 2σ(I)
R_int = 0.130

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.174
S = 1.02
3733 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2	0.93	2.51	3.415 (2)	165
C16—H16A⋯O2	0.96	2.55	3.484 (2)	165
C18—H18C⋯O1ⁱ	0.96	2.53	3.332 (2)	142
Symmetry code: (i) x, y, z-1.

Data collection: COLLECT (Hooft, 1998 ); 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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028984/zj2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028984/zj2014Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028984/zj2014Isup3.cml

checkCIF report

Comment top

Chalcones are a medicinally important class of compounds and are known for possessing various biological activities such as antibacterial, antiviral, anthelmintic, amoebicidal, antiulcer, insecticidal, antiprotozoal, anticancer, cytotoxic, immunosuppressive activities and other bioactivities (Dhar, 1981; Dimmock et al., 1999). Recently, some chalcones were approved for therapeutical use, such as methoxychalcone (E)-3-(4-methoxyphenyl)-1-(2,4-methoxyphenyl)prop-2-en-1-one, marketed in France and Italy, with choleretic and hepatoprotective activities (Ni et al., 2004). Moreover, a literature survey showed dimethoxy and trimethoxychalcone derivatives as effective anti-inflammatory agents (Bandgar et al., 2010).

The (E)-3-(3,4,5-trimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one is a methoxychalcone which the structure shows two aromatic rings linked by prop-2-en-1-one group. The refined molecular structure is shown in Fig. 1. Due to p-π conjugation, the C_sp²—O bonds [O2—C7 = 1.2249 (2) Å] are significantly shorter than the C_sp³—O bonds [O1—C19 = 1.4240 (2) Å; O3—C18 = 1.415 (2) Å; O4—C17 = 1.413 (2) Å and O5—C16 = 1.4294 (2) Å]. The methoxy substituted groups around the benzene rings are almost planar and the dihedral angles C5—C6—C7—C8, C6—C7—C8—C9, C7—C8—C9—C10 and C8—C9—C10—C11 are -23.0 (2)°, 169.3 (2)°, 177.7 (2)° and -4.4 (2)°, respectively, indicating the molecule has a non-planar conformation.

The crystal structure is stabilized by C—H···O contacts (Table 1). There is intermolecular hydrogen bonding involving C9 acting as H-bond donor, via H9, to O2 in the adjacent molecules at -x+1, -y+1, -z resulting in a dimer.

Related literature top

For background to chalcones and the biological activity and derivatives, see: Dhar (1981); Dimmock et al. (1999). For their applications as organic non-linear optical materials, see: Sarojini et al. (2006) and for their choleretic and hepatoprotective activity, see: Ni et al. (2004). For the synthesis of chalcones, see: Patil et al. (2009). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999). For related structures, see: Sathiya Moorthi et al. (2005); Cai et al.(2011); Vijay Kumar et al. (2011); Bibila Mayaya Bisseyou et al. (2007). The title compound wss prepared by the aldol Claisen–Schmidt condensation, see: Bandgar et al. (2009, 2010); Hathaway (1987).

Experimental top

The title compound, C₁₉H₂₀O₅, has been prepared by the aldol Claisen-Schmidt condensation (Hathaway, 1987; Bandgar et al., 2009) by the reaction of a mixture of 4-methoxy-acetophenone (0,3 mg; 2 mmol) and 3,4,5-trimethoxy-benzaldehyde (0,39 mg; 2 mmol) and NaOH (50% p/v) at 257 K for 24 h. The light yellow solid (m.p. 404.25 - 405.65 K) thus obtained was filtered, washed with water and dried. Crystals of suitable quality for single crystal X-ray diffraction were grown in methanol.

Computing details top

Data collection: COLLECT (Hooft, 1998); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structre showing 30% probability displacement ellipsoids.
	Fig. 2. The packing viewed along c axis with C—H···O interactions, indicating the dimer

(E)-1-(4-Methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₂₀O₅	F(000) = 696
M_r = 328.35	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5770 (1) Å	Cell parameters from 14574 reflections
b = 16.2530 (3) Å	θ = 2.6–27.5°
c = 14.0850 (3) Å	µ = 0.10 mm⁻¹
β = 107.528 (1)°	T = 293 K
V = 1654.02 (5) Å³	Prism, pale yellow
Z = 4	0.2 × 0.1 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	2907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.130
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
CCD scans	h = −9→8
27371 measured reflections	k = −20→21
3733 independent reflections	l = −18→17

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.115P)² + 0.1311P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
3733 reflections	Δρ_max = 0.27 e Å⁻³
222 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (10)

Crystal data top

C₁₉H₂₀O₅	V = 1654.02 (5) Å³
M_r = 328.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5770 (1) Å	µ = 0.10 mm⁻¹
b = 16.2530 (3) Å	T = 293 K
c = 14.0850 (3) Å	0.2 × 0.1 × 0.1 mm
β = 107.528 (1)°

Data collection top

Nonius KappaCCD diffractometer	2907 reflections with I > 2σ(I)
27371 measured reflections	R_int = 0.130
3733 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
3733 reflections	Δρ_min = −0.27 e Å⁻³
222 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 > 2σ(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
C6	0.28843 (19)	0.01968 (8)	0.72913 (10)	0.0440 (3)
C3	0.2444 (2)	0.01579 (9)	0.91868 (10)	0.0478 (4)
O5	−0.33915 (16)	0.26263 (7)	0.32667 (8)	0.0592 (3)
C7	0.3073 (2)	0.01831 (8)	0.62695 (11)	0.0465 (3)
O1	0.21258 (17)	0.01994 (7)	1.00875 (8)	0.0613 (3)
O3	0.06505 (17)	0.22341 (7)	0.13696 (8)	0.0594 (3)
C13	−0.1306 (2)	0.24141 (9)	0.23514 (10)	0.0496 (4)
O2	0.41266 (17)	−0.03016 (7)	0.60508 (9)	0.0623 (3)
C14	0.0304 (2)	0.20629 (8)	0.22489 (9)	0.0472 (3)
C11	−0.0614 (2)	0.18197 (9)	0.39957 (10)	0.0478 (3)
H11	−0.0896	0.1757	0.459	0.057*
C1	0.3390 (2)	−0.04924 (8)	0.78977 (11)	0.0475 (3)
H1	0.3901	−0.0943	0.7669	0.057*
C9	0.21256 (19)	0.09013 (9)	0.46478 (10)	0.0464 (3)
H9	0.3105	0.0638	0.4504	0.056*
C15	0.1421 (2)	0.15689 (9)	0.29994 (10)	0.0471 (3)
H15	0.2474	0.1324	0.2917	0.057*
C10	0.09579 (19)	0.14423 (8)	0.38773 (9)	0.0451 (3)
C5	0.2205 (2)	0.08797 (9)	0.76692 (11)	0.0501 (4)
H5	0.1881	0.1351	0.728	0.06*
O4	−0.24822 (19)	0.28028 (7)	0.15454 (8)	0.0700 (4)
C12	−0.1763 (2)	0.22889 (9)	0.32326 (10)	0.0475 (4)
C4	0.2007 (2)	0.08672 (9)	0.86115 (11)	0.0528 (4)
H4	0.1583	0.1332	0.8861	0.063*
C2	0.3152 (2)	−0.05237 (9)	0.88338 (10)	0.0502 (4)
H2	0.3463	−0.0996	0.9221	0.06*
C8	0.1902 (2)	0.07561 (9)	0.55307 (10)	0.0503 (4)
H8	0.0955	0.103	0.5694	0.06*
C17	−0.2865 (3)	0.36460 (11)	0.16310 (12)	0.0693 (5)
H17A	−0.3621	0.3708	0.2064	0.104*
H17B	−0.3508	0.3863	0.0985	0.104*
H17C	−0.1724	0.394	0.1902	0.104*
C16	−0.3984 (2)	0.24404 (11)	0.41148 (12)	0.0602 (4)
H16A	−0.4186	0.1859	0.4141	0.09*
H16B	−0.5116	0.2728	0.4064	0.09*
H16C	−0.3049	0.261	0.4709	0.09*
C18	0.2381 (3)	0.19903 (12)	0.12726 (13)	0.0702 (5)
H18A	0.3358	0.22	0.1825	0.105*
H18B	0.2513	0.2205	0.0663	0.105*
H18C	0.2446	0.1401	0.1265	0.105*
C19	0.2388 (3)	−0.05277 (12)	1.06778 (12)	0.0666 (5)
H19A	0.1621	−0.096	1.0306	0.1*
H19B	0.2058	−0.0421	1.1273	0.1*
H19C	0.3663	−0.0692	1.0852	0.1*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C6	0.0425 (7)	0.0436 (7)	0.0430 (7)	−0.0002 (5)	0.0086 (5)	0.0042 (5)
C3	0.0491 (8)	0.0517 (8)	0.0401 (7)	−0.0033 (6)	0.0098 (6)	0.0043 (5)
O5	0.0536 (7)	0.0738 (7)	0.0466 (6)	0.0147 (5)	0.0095 (5)	0.0039 (5)
C7	0.0463 (7)	0.0433 (7)	0.0502 (8)	0.0004 (6)	0.0150 (6)	0.0046 (5)
O1	0.0772 (8)	0.0628 (7)	0.0459 (6)	0.0058 (5)	0.0215 (5)	0.0096 (4)
O3	0.0722 (8)	0.0672 (7)	0.0393 (5)	0.0078 (5)	0.0175 (5)	0.0058 (4)
C13	0.0562 (9)	0.0490 (7)	0.0348 (7)	0.0022 (6)	0.0006 (6)	−0.0041 (5)
O2	0.0736 (8)	0.0566 (6)	0.0648 (7)	0.0189 (5)	0.0331 (6)	0.0119 (5)
C14	0.0581 (8)	0.0468 (7)	0.0336 (6)	−0.0044 (6)	0.0090 (6)	−0.0039 (5)
C11	0.0491 (8)	0.0547 (8)	0.0367 (6)	0.0003 (6)	0.0087 (5)	−0.0003 (5)
C1	0.0497 (8)	0.0413 (7)	0.0470 (7)	0.0024 (6)	0.0078 (6)	0.0017 (5)
C9	0.0444 (7)	0.0478 (7)	0.0452 (7)	0.0016 (5)	0.0109 (6)	0.0023 (5)
C15	0.0495 (7)	0.0492 (7)	0.0409 (7)	−0.0006 (6)	0.0112 (6)	−0.0008 (5)
C10	0.0459 (7)	0.0467 (7)	0.0382 (6)	−0.0028 (6)	0.0057 (5)	−0.0002 (5)
C5	0.0577 (8)	0.0432 (7)	0.0489 (7)	0.0076 (6)	0.0152 (6)	0.0092 (6)
O4	0.0862 (9)	0.0722 (8)	0.0379 (6)	0.0246 (6)	−0.0021 (5)	−0.0010 (5)
C12	0.0463 (8)	0.0503 (8)	0.0407 (7)	0.0023 (6)	0.0050 (6)	−0.0043 (5)
C4	0.0623 (9)	0.0463 (7)	0.0494 (8)	0.0075 (6)	0.0163 (7)	0.0041 (6)
C2	0.0556 (8)	0.0428 (7)	0.0462 (7)	0.0006 (6)	0.0062 (6)	0.0096 (5)
C8	0.0484 (8)	0.0562 (8)	0.0453 (7)	0.0087 (6)	0.0125 (6)	0.0053 (6)
C17	0.0765 (11)	0.0667 (10)	0.0584 (9)	0.0204 (9)	0.0110 (8)	0.0105 (8)
C16	0.0577 (9)	0.0657 (10)	0.0594 (9)	0.0082 (7)	0.0210 (8)	0.0027 (7)
C18	0.0911 (13)	0.0769 (11)	0.0506 (9)	0.0143 (9)	0.0333 (9)	0.0034 (7)
C19	0.0736 (11)	0.0730 (11)	0.0529 (9)	0.0016 (8)	0.0188 (8)	0.0205 (7)

Geometric parameters (Å, º) top

C6—C1	1.3906 (19)	C9—C10	1.4682 (19)
C6—C5	1.395 (2)	C9—H9	0.93
C6—C7	1.4889 (19)	C15—C10	1.3986 (19)
C3—O1	1.3626 (17)	C15—H15	0.93
C3—C2	1.387 (2)	C5—C4	1.380 (2)
C3—C4	1.3906 (19)	C5—H5	0.93
O5—C12	1.3645 (18)	O4—C17	1.413 (2)
O5—C16	1.4294 (19)	C4—H4	0.93
C7—O2	1.2249 (18)	C2—H2	0.93
C7—C8	1.4771 (19)	C8—H8	0.93
O1—C19	1.4240 (19)	C17—H17A	0.96
O3—C14	1.3699 (16)	C17—H17B	0.96
O3—C18	1.415 (2)	C17—H17C	0.96
C13—O4	1.3685 (17)	C16—H16A	0.96
C13—C14	1.393 (2)	C16—H16B	0.96
C13—C12	1.400 (2)	C16—H16C	0.96
C14—C15	1.393 (2)	C18—H18A	0.96
C11—C12	1.390 (2)	C18—H18B	0.96
C11—C10	1.394 (2)	C18—H18C	0.96
C11—H11	0.93	C19—H19A	0.96
C1—C2	1.384 (2)	C19—H19B	0.96
C1—H1	0.93	C19—H19C	0.96
C9—C8	1.326 (2)

C1—C6—C5	118.15 (13)	O5—C12—C11	123.77 (13)
C1—C6—C7	119.52 (12)	O5—C12—C13	116.13 (12)
C5—C6—C7	122.33 (12)	C11—C12—C13	120.06 (13)
O1—C3—C2	124.72 (12)	C5—C4—C3	119.79 (13)
O1—C3—C4	115.06 (13)	C5—C4—H4	120.1
C2—C3—C4	120.22 (13)	C3—C4—H4	120.1
C12—O5—C16	117.36 (12)	C1—C2—C3	119.18 (12)
O2—C7—C8	121.82 (14)	C1—C2—H2	120.4
O2—C7—C6	120.82 (12)	C3—C2—H2	120.4
C8—C7—C6	117.33 (12)	C9—C8—C7	123.60 (13)
C3—O1—C19	118.02 (13)	C9—C8—H8	118.2
C14—O3—C18	117.77 (12)	C7—C8—H8	118.2
O4—C13—C14	118.37 (13)	O4—C17—H17A	109.5
O4—C13—C12	121.95 (14)	O4—C17—H17B	109.5
C14—C13—C12	119.36 (12)	H17A—C17—H17B	109.5
O3—C14—C15	124.40 (13)	O4—C17—H17C	109.5
O3—C14—C13	115.01 (12)	H17A—C17—H17C	109.5
C15—C14—C13	120.59 (13)	H17B—C17—H17C	109.5
C12—C11—C10	120.51 (12)	O5—C16—H16A	109.5
C12—C11—H11	119.7	O5—C16—H16B	109.5
C10—C11—H11	119.7	H16A—C16—H16B	109.5
C2—C1—C6	121.57 (13)	O5—C16—H16C	109.5
C2—C1—H1	119.2	H16A—C16—H16C	109.5
C6—C1—H1	119.2	H16B—C16—H16C	109.5
C8—C9—C10	125.52 (13)	O3—C18—H18A	109.5
C8—C9—H9	117.2	O3—C18—H18B	109.5
C10—C9—H9	117.2	H18A—C18—H18B	109.5
C14—C15—C10	119.90 (13)	O3—C18—H18C	109.5
C14—C15—H15	120	H18A—C18—H18C	109.5
C10—C15—H15	120	H18B—C18—H18C	109.5
C11—C10—C15	119.49 (12)	O1—C19—H19A	109.5
C11—C10—C9	121.44 (12)	O1—C19—H19B	109.5
C15—C10—C9	119.06 (13)	H19A—C19—H19B	109.5
C4—C5—C6	120.99 (12)	O1—C19—H19C	109.5
C4—C5—H5	119.5	H19A—C19—H19C	109.5
C6—C5—H5	119.5	H19B—C19—H19C	109.5
C13—O4—C17	118.42 (12)

C1—C6—C7—O2	−21.4 (2)	C1—C6—C5—C4	−1.2 (2)
C5—C6—C7—O2	158.90 (15)	C7—C6—C5—C4	178.5 (2)
C1—C6—C7—C8	156.7 (2)	C14—C13—O4—C17	−120.1 (2)
C5—C6—C7—C8	−23.0 (2)	C12—C13—O4—C17	66.4 (2)
C2—C3—O1—C19	−5.5 (2)	C16—O5—C12—C11	−3.9 (2)
C4—C3—O1—C19	174.5 (2)	C16—O5—C12—C13	173.9 (2)
C18—O3—C14—C15	−9.2 (2)	C10—C11—C12—O5	175.0 (2)
C18—O3—C14—C13	171.6 (2)	C10—C11—C12—C13	−2.6 (2)
O4—C13—C14—O3	7.7 (2)	O4—C13—C12—O5	−4.4 (2)
C12—C13—C14—O3	−178.7 (2)	C14—C13—C12—O5	−177.7 (2)
O4—C13—C14—C15	−171.4 (2)	O4—C13—C12—C11	173.5 (2)
C12—C13—C14—C15	2.1 (2)	C14—C13—C12—C11	0.1 (2)
C5—C6—C1—C2	3.0 (2)	C6—C5—C4—C3	−1.7 (2)
C7—C6—C1—C2	−176.6 (2)	O1—C3—C4—C5	−177.3 (2)
O3—C14—C15—C10	179.0 (2)	C2—C3—C4—C5	2.8 (2)
C13—C14—C15—C10	−1.9 (2)	C6—C1—C2—C3	−2.0 (2)
C12—C11—C10—C15	2.9 (2)	O1—C3—C2—C1	179.1 (2)
C12—C11—C10—C9	−176.0 (2)	C4—C3—C2—C1	−1.0 (2)
C14—C15—C10—C11	−0.6 (2)	C10—C9—C8—C7	177.7 (2)
C14—C15—C10—C9	178.3 (2)	O2—C7—C8—C9	−12.8 (2)
C8—C9—C10—C11	−4.4 (2)	C6—C7—C8—C9	169.1 (2)
C8—C9—C10—C15	176.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.93	2.51	3.415 (2)	165
C16—H16A···O2	0.96	2.55	3.484 (2)	165
C18—H18C···O1ⁱ	0.96	2.53	3.332 (2)	142

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₅
M_r	328.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5770 (1), 16.2530 (3), 14.0850 (3)
β (°)	107.528 (1)
V (Å³)	1654.02 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27371, 3733, 2907
R_int	0.130
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.174, 1.02
No. of reflections	3733
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: COLLECT (Hooft, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.93	2.51	3.415 (2)	165
C16—H16A···O2	0.96	2.55	3.484 (2)	165
C18—H18C···O1ⁱ	0.96	2.53	3.332 (2)	142

Symmetry code: (i) x, y, z−1.

Acknowledgements

The authors thank the Brazilian Federal Agency CAPES.

References

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