(E)-3-(2,4-Dimeth­oxy­phen­yl)-1-(3,4-dimeth­oxy­phen­yl)prop-2-en-1-one

Wu, X.; Cai, X.; Zheng, X.; Zhang, Z.; Ye, X.

doi:10.1107/S1600536810043606

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3015

https://doi.org/10.1107/S1600536810043606

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(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

Xiaokai Wu,^a Xiaoqing Cai,^b Xianan Zheng,^a Zhennan Zhang ^a and Xiaoqin Ye ^a ^*

^aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang 325035, People's Republic of China, and ^bCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China
^*Correspondence e-mail: wujianzhang6@163.com

(Received 17 September 2010; accepted 26 October 2010; online 31 October 2010)

The title compound, C₁₉H₂₀O₅, is approximately planar; the dihedral angle between the benzene rings is 3.82 (8)°, and the central propenone C(=O)—C=C plane makes dihedral angles of 1.95 (10) and 3.17 (11)° with the two benzene rings. In the crystal structure, intra- and intermolecular C—H⋯O hydrogen bonds are observed.

Related literature

For related structures, see: Huang et al. (2010 ); Peng et al. (2010 ); Yathirajan et al. (2006 ); Zhao et al. (2010 ). For background to and applications of chalcones, see: Liang et al. (2007 ); Liu et al. (2008 ); Mojzisa et al. (2008 ); Nielsen et al. (2005 ); Nowakowska (2007 ); Selvakumar et al. (2007 ); Wu et al. (2010 ); Wu, Chen et al. (2009 ); Wu, Qiu et al. (2009 ); Wu, Zhang et al. (2009 ).

Experimental

Crystal data

C₁₉H₂₀O₅
M_r = 328.35
Monoclinic, P 2₁ /n
a = 9.031 (5) Å
b = 7.962 (5) Å
c = 23.631 (14) Å
β = 92.827 (10)°
V = 1697.0 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.47 × 0.35 × 0.31 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.958, T_max = 0.972
8581 measured reflections
2981 independent reflections
2407 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.04
2981 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.46	3.363 (3)	162
C8—H8B⋯O4ⁱⁱ	0.96	2.60	3.537 (3)	166
C10—H10⋯O2	0.93	2.25	2.846 (3)	121
C19—H19A⋯O1ⁱⁱⁱ	0.96	2.54	3.443 (3)	157
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810043606/is2604sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043606/is2604Isup2.hkl

checkCIF report

Comment top

Chalcones have the common skeleton of 1,3-diaryl-2-propen-1-ones and belong to the flavonoid family. Chalcones distribute widespread in fruits, vegetables and so on. Like as other flavonoids, chalcones have been reported to possess wide-range biological activities, including antimicrobial, antitumor, anti-inflammatory, antifungal, antioxidant activities and so on (Nowakowska, 2007; Liu et al., 2008; Wu et al., 2010). Moreover, Chalcones belong to nature products and have low toxicity. Owing to its varied pharmacological activities and low toxicity, it has attracted more and more scientists attention and therefore several strategies have been developed to synthesize them (Nowakowska, 2007; Selvakumar et al., 2007; Wu, Chen et al., 2009; Wu, Qiu et al., 2009; Wu, Zhang et al., 2009).

In our effort to develop Chalcones activity, we have synthesized the title chalcone. In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Two rings of molecule is approximately planar and the dihedral angle between the two rings is 3.82 (4)°. The average value of exocyclic bond angles [120.8 (5)°] and the bond distances [1.384 (2) Å] in the phenyl rings agree well with the normal values reported in the literature for some analogous structures (Peng et al., 2010; Wu, Chen et al., 2009; Wu, Qiu et al., 2009; Wu, Zhang et al., 2009; Huang et al., 2010; Yathirajan et al., 2006).

Related literature top

For related structures, see: Huang et al. (2010); Peng et al. (2010); Yathirajan et al. (2006); Zhao et al. (2010). For background to and applications of chalcones, see: Liang et al. (2007); Liu et al. (2008); Mojzisa et al. (2008); Nielsen et al. (2005); Nowakowska (2007); Selvakumar et al. (2007); Wu et al. (2010); Wu, Chen et al. (2009); Wu, Qiu et al. (2009); Wu, Zhang et al. (2009).

Experimental top

The title compound was synthesized by Claisene–Schmidt condensation between 2,4-dimethoxybenzaldehyde and 1-(3,4-dimethoxyphenyl)ethanone. 2,4-Dimethoxybenzaldehyde (1 mmol) and 1-(3,4-dimethoxyphenyl)ethanone (1 mmol) were dissolved in ethanol (15 ml). The mixture were controlled at 279 K and then 5 drops NaOH (20%) was added. The reaction was monitored by thin-layer chromatography. 15 ml H₂O was added after 10 h and the yellow solid precipitated was washed with water and cold ethanol. It was then dried and purified by column chromatography on silica gel. Single crystals of the title compound were grown in a CH₂Cl₂/CH₃CH₂OH mixture (1:1) solution at 279 K.

Structure description top

For related structures, see: Huang et al. (2010); Peng et al. (2010); Yathirajan et al. (2006); Zhao et al. (2010). For background to and applications of chalcones, see: Liang et al. (2007); Liu et al. (2008); Mojzisa et al. (2008); Nielsen et al. (2005); Nowakowska (2007); Selvakumar et al. (2007); Wu et al. (2010); Wu, Chen et al. (2009); Wu, Qiu et al. (2009); Wu, Zhang et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids at the 50% probability level.

(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₂₀O₅	F(000) = 696
M_r = 328.35	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3028 reflections
a = 9.031 (5) Å	θ = 2.4–25.4°
b = 7.962 (5) Å	µ = 0.09 mm⁻¹
c = 23.631 (14) Å	T = 298 K
β = 92.827 (10)°	Block, colourless
V = 1697.0 (17) Å³	0.47 × 0.35 × 0.31 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.958, T_max = 0.972	k = −7→9
8581 measured reflections	l = −28→21

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0641P)² + 0.1943P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2981 reflections	Δρ_max = 0.14 e Å⁻³
222 parameters	Δρ_min = −0.16 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: 0.0093 (16)

Crystal data top

C₁₉H₂₀O₅	V = 1697.0 (17) Å³
M_r = 328.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.031 (5) Å	µ = 0.09 mm⁻¹
b = 7.962 (5) Å	T = 298 K
c = 23.631 (14) Å	0.47 × 0.35 × 0.31 mm
β = 92.827 (10)°

Data collection top

Bruker APEX area-detector diffractometer	2981 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2407 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.972	R_int = 0.021
8581 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
2981 reflections	Δρ_min = −0.16 e Å⁻³
222 parameters

Special details top

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
O1	0.28103 (12)	0.90184 (19)	0.42954 (5)	0.0819 (4)
O2	0.70723 (11)	0.80481 (15)	0.32588 (5)	0.0638 (3)
O3	1.12815 (14)	0.4756 (2)	0.43350 (6)	0.0919 (5)
O4	1.56960 (12)	0.36084 (15)	0.31617 (5)	0.0671 (4)
O5	1.51234 (12)	0.49882 (14)	0.21947 (5)	0.0609 (3)
C1	0.2027 (2)	0.8905 (3)	0.48040 (9)	0.0961 (7)
H1A	0.1911	0.7746	0.4905	0.144*
H1B	0.1068	0.9414	0.4746	0.144*
H1C	0.2574	0.9479	0.5104	0.144*
C2	0.42024 (16)	0.8369 (2)	0.42967 (7)	0.0580 (4)
C3	0.49109 (19)	0.7598 (3)	0.47532 (7)	0.0698 (5)
H3	0.4444	0.7487	0.5093	0.084*
C4	0.63289 (18)	0.6990 (2)	0.46998 (7)	0.0652 (5)
H4	0.6801	0.6467	0.5011	0.078*
C5	0.70830 (16)	0.71205 (19)	0.42044 (7)	0.0509 (4)
C6	0.63254 (15)	0.79194 (18)	0.37421 (6)	0.0482 (4)
C7	0.49051 (16)	0.8529 (2)	0.37918 (7)	0.0535 (4)
H7	0.4417	0.9052	0.3484	0.064*
C8	0.63986 (18)	0.8895 (2)	0.27838 (7)	0.0652 (5)
H8A	0.5486	0.8345	0.2670	0.098*
H8B	0.7055	0.8875	0.2476	0.098*
H8C	0.6199	1.0038	0.2884	0.098*
C9	0.85599 (16)	0.6388 (2)	0.41978 (7)	0.0556 (4)
H9	0.8906	0.5935	0.4542	0.067*
C10	0.94973 (16)	0.6258 (2)	0.37837 (7)	0.0560 (4)
H10	0.9239	0.6703	0.3429	0.067*
C11	1.09404 (17)	0.5415 (2)	0.38803 (7)	0.0577 (4)
C12	1.19894 (16)	0.53612 (18)	0.34148 (6)	0.0490 (4)
C13	1.17154 (16)	0.61029 (19)	0.28937 (7)	0.0534 (4)
H13	1.0832	0.6682	0.2822	0.064*
C14	1.27305 (17)	0.60041 (19)	0.24734 (7)	0.0557 (4)
H14	1.2519	0.6506	0.2123	0.067*
C15	1.40530 (16)	0.51638 (18)	0.25735 (7)	0.0504 (4)
C16	1.43577 (15)	0.44187 (18)	0.31052 (6)	0.0493 (4)
C17	1.33443 (16)	0.45188 (19)	0.35158 (7)	0.0515 (4)
H17	1.3555	0.4022	0.3867	0.062*
C18	1.61263 (19)	0.2977 (2)	0.37027 (8)	0.0669 (5)
H18A	1.6114	0.3869	0.3976	0.100*
H18B	1.7109	0.2520	0.3696	0.100*
H18C	1.5449	0.2111	0.3805	0.100*
C19	1.4842 (2)	0.5671 (3)	0.16424 (7)	0.0703 (5)
H19A	1.3940	0.5204	0.1478	0.105*
H19B	1.5650	0.5401	0.1409	0.105*
H19C	1.4745	0.6869	0.1668	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0504 (7)	0.1228 (11)	0.0734 (9)	0.0280 (7)	0.0114 (6)	−0.0078 (8)
O2	0.0466 (6)	0.0894 (9)	0.0563 (7)	0.0110 (5)	0.0110 (5)	0.0148 (6)
O3	0.0720 (8)	0.1376 (13)	0.0679 (9)	0.0480 (8)	0.0213 (7)	0.0313 (8)
O4	0.0547 (7)	0.0841 (8)	0.0635 (8)	0.0250 (6)	0.0118 (6)	0.0059 (6)
O5	0.0566 (7)	0.0690 (7)	0.0584 (7)	0.0066 (5)	0.0163 (5)	0.0010 (5)
C1	0.0587 (12)	0.152 (2)	0.0797 (14)	0.0236 (12)	0.0227 (10)	−0.0226 (14)
C2	0.0426 (8)	0.0710 (10)	0.0609 (10)	0.0082 (7)	0.0086 (7)	−0.0105 (8)
C3	0.0573 (10)	0.0980 (14)	0.0555 (10)	0.0150 (9)	0.0167 (8)	0.0014 (9)
C4	0.0584 (10)	0.0837 (12)	0.0541 (10)	0.0146 (9)	0.0096 (8)	0.0066 (9)
C5	0.0459 (8)	0.0538 (9)	0.0534 (9)	0.0033 (7)	0.0081 (7)	−0.0011 (7)
C6	0.0417 (8)	0.0509 (8)	0.0526 (9)	−0.0013 (6)	0.0072 (7)	−0.0032 (7)
C7	0.0446 (8)	0.0592 (9)	0.0564 (9)	0.0043 (7)	0.0001 (7)	−0.0016 (7)
C8	0.0560 (10)	0.0859 (12)	0.0536 (10)	0.0003 (9)	0.0032 (8)	0.0061 (9)
C9	0.0493 (9)	0.0599 (9)	0.0578 (10)	0.0071 (7)	0.0041 (7)	0.0040 (7)
C10	0.0471 (9)	0.0633 (10)	0.0578 (10)	0.0086 (7)	0.0059 (7)	0.0015 (8)
C11	0.0508 (9)	0.0665 (10)	0.0561 (10)	0.0120 (7)	0.0068 (7)	0.0032 (8)
C12	0.0435 (8)	0.0489 (8)	0.0548 (9)	0.0034 (6)	0.0044 (7)	−0.0046 (7)
C13	0.0450 (8)	0.0538 (9)	0.0616 (10)	0.0088 (7)	0.0045 (7)	0.0006 (7)
C14	0.0555 (9)	0.0579 (9)	0.0539 (9)	0.0054 (7)	0.0050 (7)	0.0048 (7)
C15	0.0486 (9)	0.0483 (8)	0.0549 (9)	−0.0010 (6)	0.0103 (7)	−0.0056 (7)
C16	0.0437 (8)	0.0475 (8)	0.0570 (9)	0.0067 (6)	0.0059 (7)	−0.0046 (7)
C17	0.0491 (8)	0.0540 (9)	0.0515 (9)	0.0065 (7)	0.0032 (7)	−0.0009 (7)
C18	0.0581 (10)	0.0706 (11)	0.0717 (12)	0.0165 (8)	0.0009 (8)	0.0029 (9)
C19	0.0722 (11)	0.0831 (12)	0.0566 (10)	0.0015 (10)	0.0141 (8)	0.0019 (9)

Geometric parameters (Å, º) top

O1—C2	1.3593 (19)	C8—H8B	0.9600
O1—C1	1.427 (2)	C8—H8C	0.9600
O2—C6	1.3586 (18)	C9—C10	1.329 (2)
O2—C8	1.420 (2)	C9—H9	0.9300
O3—C11	1.222 (2)	C10—C11	1.473 (2)
O4—C16	1.3707 (18)	C10—H10	0.9300
O4—C18	1.410 (2)	C11—C12	1.487 (2)
O5—C15	1.3567 (17)	C12—C13	1.377 (2)
O5—C19	1.425 (2)	C12—C17	1.405 (2)
C1—H1A	0.9600	C13—C14	1.387 (2)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.379 (2)
C2—C3	1.372 (3)	C14—H14	0.9300
C2—C7	1.385 (2)	C15—C16	1.404 (2)
C3—C4	1.381 (2)	C16—C17	1.369 (2)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.387 (2)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.412 (2)	C18—H18C	0.9600
C5—C9	1.456 (2)	C19—H19A	0.9600
C6—C7	1.382 (2)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—H8A	0.9600

C2—O1—C1	118.09 (15)	C9—C10—C11	120.80 (15)
C6—O2—C8	119.28 (12)	C9—C10—H10	119.6
C16—O4—C18	117.28 (12)	C11—C10—H10	119.6
C15—O5—C19	117.65 (13)	O3—C11—C10	120.98 (14)
O1—C1—H1A	109.5	O3—C11—C12	119.72 (14)
O1—C1—H1B	109.5	C10—C11—C12	119.30 (14)
H1A—C1—H1B	109.5	C13—C12—C17	118.23 (14)
O1—C1—H1C	109.5	C13—C12—C11	123.79 (14)
H1A—C1—H1C	109.5	C17—C12—C11	117.98 (14)
H1B—C1—H1C	109.5	C12—C13—C14	121.35 (14)
O1—C2—C3	124.58 (15)	C12—C13—H13	119.3
O1—C2—C7	115.21 (15)	C14—C13—H13	119.3
C3—C2—C7	120.21 (14)	C15—C14—C13	120.14 (15)
C2—C3—C4	118.93 (16)	C15—C14—H14	119.9
C2—C3—H3	120.5	C13—C14—H14	119.9
C4—C3—H3	120.5	O5—C15—C14	125.17 (15)
C3—C4—C5	123.17 (16)	O5—C15—C16	115.61 (13)
C3—C4—H4	118.4	C14—C15—C16	119.23 (13)
C5—C4—H4	118.4	C17—C16—O4	125.14 (14)
C4—C5—C6	116.59 (14)	C17—C16—C15	120.09 (14)
C4—C5—C9	117.84 (14)	O4—C16—C15	114.77 (12)
C6—C5—C9	125.54 (14)	C16—C17—C12	120.96 (15)
O2—C6—C7	123.12 (14)	C16—C17—H17	119.5
O2—C6—C5	116.28 (13)	C12—C17—H17	119.5
C7—C6—C5	120.60 (14)	O4—C18—H18A	109.5
C6—C7—C2	120.51 (15)	O4—C18—H18B	109.5
C6—C7—H7	119.7	H18A—C18—H18B	109.5
C2—C7—H7	119.7	O4—C18—H18C	109.5
O2—C8—H8A	109.5	H18A—C18—H18C	109.5
O2—C8—H8B	109.5	H18B—C18—H18C	109.5
H8A—C8—H8B	109.5	O5—C19—H19A	109.5
O2—C8—H8C	109.5	O5—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19B	109.5
H8B—C8—H8C	109.5	O5—C19—H19C	109.5
C10—C9—C5	131.00 (16)	H19A—C19—H19C	109.5
C10—C9—H9	114.5	H19B—C19—H19C	109.5
C5—C9—H9	114.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.46	3.363 (3)	162
C8—H8B···O4ⁱⁱ	0.96	2.60	3.537 (3)	166
C10—H10···O2	0.93	2.25	2.846 (3)	121
C19—H19A···O1ⁱⁱⁱ	0.96	2.54	3.443 (3)	157

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₅
M_r	328.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.031 (5), 7.962 (5), 23.631 (14)
β (°)	92.827 (10)
V (Å³)	1697.0 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.35 × 0.31

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.958, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	8581, 2981, 2407
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.04
No. of reflections	2981
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.46	3.363 (3)	162
C8—H8B···O4ⁱⁱ	0.96	2.60	3.537 (3)	166
C10—H10···O2	0.93	2.25	2.846 (3)	121
C19—H19A···O1ⁱⁱⁱ	0.96	2.54	3.443 (3)	157

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge financial support from the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. Y200907137).

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