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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 6| June 2011| Page o1432
doi:10.1107/S1600536811017788

(E)-1-(4-Meth­­oxy­phen­yl)-3-(2,4,6-trimeth­­oxy­phen­yl)prop-2-en-1-one

Yuepiao Cai,a Zhankun Wang,b Zhe Li,c Meiling Zhanga* and Jianzhang Wua

aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, bPhysical Education Department, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and cLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China
*Correspondence e-mail: wjzwzmc@126.com

(Received 23 April 2011; accepted 11 May 2011; online 14 May 2011)

In the title compound, C19H20O5, the dihedral angle between the two aromatic rings is 18.23 (4)°. The crystal structure exhibits only weak C—H⋯π and C—H⋯O contacts between the mol­ecules.

Related literature

For related structures, see: Wu et al. (2011[Wu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2011). Med. Chem. Res. doi:10.1007/s00044-011-9549-9.]); Peng et al. (2010[Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.]); Huang et al. (2010[Huang, T., Zhang, D., Yang, Q., Wei, X. & Wu, J. (2010). Acta Cryst. E66, o2518.]); Zhao et al. (2010[Zhao, C. G., Yang, J., Wang, Y., Liang, D. L., Yang, X. Y., Li, X. X., Wu, J. Z., Wu, X. P., Yang, S. L., Li, X. K. & Liang, G. (2010). Bioorg. Med. Chem. 18, 2388-2393.]). For background and applications of chalcones, see: Wu et al. (2010[Wu, J. Z., Wang, C., Cai, Y. P., Yang, S. L., Zheng, X. Y., Qiu, P. H., Peng, J., Wu, X. P., Liang, G. & Li, X. K. (2010). Chin. J. Org. Chem. 30, 884-889.], 2011)[Wu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2011). Med. Chem. Res. doi:10.1007/s00044-011-9549-9.]; Liu et al. (2008[Liu, X. L., Xu, Y. J. & Go, M. L. (2008). Eur. J. Med. Chem. 43, 1681-1687.]); Zhao et al. (2010[Zhao, C. G., Yang, J., Wang, Y., Liang, D. L., Yang, X. Y., Li, X. X., Wu, J. Z., Wu, X. P., Yang, S. L., Li, X. K. & Liang, G. (2010). Bioorg. Med. Chem. 18, 2388-2393.]); Nielsen et al. (2005[Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667-2677.]).

[Scheme 1]

Experimental

Crystal data

  • C19H20O5

  • Mr = 328.35

  • Orthorhombic, P b c a

  • a = 7.3339 (6) Å

  • b = 16.8260 (14) Å

  • c = 26.677 (2) Å

  • V = 3291.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 133 K

  • 0.35 × 0.33 × 0.31 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.971

  • 22257 measured reflections

  • 3593 independent reflections

  • 3380 reflections with I > 2σ(I)

  • Rint = 0.020
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.108

  • S = 1.02

  • 3593 reflections

  • 221 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯Cg2i 0.95 2.89 3.6744 (12) 140
C4—H4⋯Cg1ii 0.95 2.94 3.6921 (12) 137
C17—H17a⋯Cg1iii 0.98 2.96 3.8913 (13) 159
C19—H19a⋯Cg2iv 0.98 2.82 3.4705 (13) 125
C16—H16c⋯O3v 0.98 2.51 3.4074 (16) 152
C18—H18a⋯O5vi 0.98 2.48 3.1578 (16) 126
Symmetry codes: (i) [x-{\script{3\over 2}}, y-1, -z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y, z+{\script{3\over 2}}]; (iii) [x-{\script{1\over 2}}, y, -z-{\script{1\over 2}}]; (iv) [-x-{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (v) -x, -y+1, -z+1; (vi) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017788/ff2009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017788/ff2009Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017788/ff2009Isup3.cml

checkCIF report


Comment top

Chalcones, with the common skeleton of 1,3-diaryl-2-propen-1-one, are essential compounds in flavonoid biosynthesis in plants. They consist of two aromatic rings linked by a three-carbon α,β-unsaturated carbonyl system (Peng et al., 2010; Huang et al., 2010; Zhao et al., 2010.).

Both natural and synthetic chalcones have active biological properties such as antiinflammatory, antitumoral, antioxidant, antibacterial (Wu et al. 2011; Liu et al., 2008; Wu et al. 2010; Zhao, et al. 2010; Nielsen et al. 2005).

In order to investigate activity of chalcones, the title compound has been synthesised. Subsequently, its single-crystal X-ray study was carried out.

The dihedral angle between the two aromatic rings is 18.23 (4)°. There are weak C—H···π and C—H···O intermolecular interactions in the crystal structure. One of the methoxy groups in ortho position of 2,4,6-trimethoxyphenyl ring is slightly bent out of the ring plane [C14-C15-O4-C9 = 16.90 (16)°] while the other methoxy groups are almost coplanar with their parent ring planes [C-C-O-CH3 = 176.37 (10)°, 176.22 (9)° and -174.09 (10)°].

Related literature top

For related structures, see: Wu et al. (2011); Peng et al. (2010); Huang et al. (2010); Zhao et al. (2010). For background to and applications of chalcones, see: Wu et al. (2010, 2011); Liu et al. (2008); Zhao et al. (2010); Nielsen et al. (2005).

Experimental top

2,4,6-trimethoxybenzaldehyde (2 mmol) and 1-(4-dimethoxyphenyl)ethanone (2 mmol) were dissolved in ehanol (15 ml). The reaction temperature were about 305 K. The reaction was catalyzed by NaOH (20%, 5 drops). The reaction was monitored by thin-layer chromatography. After 10 h, 15 ml H2O was added and a yellow solid precipitated. The solid was washed with the mixture of water and cold ethanol, and dried. The pure compound was obtained by column chromatography on silica gel (yield: 67%). Single crystals of the compound were grown in a CH2Cl2/CH3CH2OH mixture (1:1 v/v) at 277 K.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model approximation, with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2–1.5 times Ueq(C).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
(E)-1-(4-Methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C19H20O5F(000) = 1392
Mr = 328.35Dx = 1.325 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9911 reflections
a = 7.3339 (6) Åθ = 2.5–27.5°
b = 16.8260 (14) ŵ = 0.10 mm−1
c = 26.677 (2) ÅT = 133 K
V = 3291.9 (5) Å3Block, colourless
Z = 80.35 × 0.33 × 0.31 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		3593 independent reflections
Radiation source: fine-focus sealed tube3380 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ϕ and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −9→8
Tmin = 0.967, Tmax = 0.971k = −21→21
22257 measured reflectionsl = −34→33
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0656P)2 + 1.0603P]
where P = (Fo2 + 2Fc2)/3
3593 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C19H20O5V = 3291.9 (5) Å3
Mr = 328.35Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.3339 (6) ŵ = 0.10 mm−1
b = 16.8260 (14) ÅT = 133 K
c = 26.677 (2) Å0.35 × 0.33 × 0.31 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		3593 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3380 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.971Rint = 0.020
22257 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.02Δρmax = 0.22 e Å−3
3593 reflectionsΔρmin = −0.24 e Å−3
221 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
xyzUiso*/Ueq
O1−0.11440 (12)0.09104 (5)0.52298 (3)0.0306 (2)
O20.09328 (11)0.52918 (4)0.42318 (3)0.02358 (18)
O30.15756 (13)0.77278 (5)0.33786 (3)0.0297 (2)
O4−0.01580 (13)0.53324 (5)0.24951 (3)0.0297 (2)
O5−0.12136 (16)0.28670 (6)0.32160 (3)0.0432 (3)
C1−0.17359 (15)0.18362 (6)0.40208 (4)0.0236 (2)
H1−0.23340.17160.37140.028*
C2−0.18310 (15)0.13044 (6)0.44147 (4)0.0249 (2)
H2−0.24960.08230.43780.030*
C3−0.09526 (15)0.14727 (6)0.48666 (4)0.0231 (2)
C40.00426 (15)0.21720 (6)0.49199 (4)0.0237 (2)
H40.06600.22850.52250.028*
C50.01209 (15)0.27031 (6)0.45199 (4)0.0228 (2)
H50.07970.31810.45560.027*
C6−0.07673 (14)0.25507 (6)0.40679 (4)0.0217 (2)
C7−0.07394 (16)0.31067 (7)0.36306 (4)0.0255 (2)
C8−0.01821 (16)0.39334 (7)0.37223 (4)0.0250 (2)
H80.01550.40910.40510.030*
C9−0.01402 (15)0.44698 (7)0.33494 (4)0.0238 (2)
H9−0.04860.42730.30290.029*
C100.03548 (14)0.53061 (6)0.33628 (4)0.0212 (2)
C110.08965 (14)0.57253 (6)0.37997 (4)0.0206 (2)
C120.13343 (15)0.65221 (6)0.37886 (4)0.0227 (2)
H120.17260.67840.40850.027*
C130.11981 (15)0.69401 (6)0.33384 (4)0.0231 (2)
C140.07144 (15)0.65615 (7)0.28945 (4)0.0239 (2)
H140.06530.68470.25880.029*
C150.03215 (15)0.57507 (7)0.29121 (4)0.0226 (2)
C16−0.0194 (2)0.10198 (8)0.56923 (5)0.0365 (3)
H16A0.11160.10670.56260.055*
H16B−0.04160.05630.59120.055*
H16C−0.06310.15050.58560.055*
C170.15775 (17)0.56770 (7)0.46741 (4)0.0274 (2)
H17A0.28260.58660.46190.041*
H17B0.15630.53000.49540.041*
H17C0.07870.61300.47520.041*
C180.1300 (2)0.82163 (7)0.29468 (5)0.0364 (3)
H18A0.20940.80340.26750.055*
H18B0.15950.87690.30290.055*
H18C0.00240.81810.28400.055*
C190.02210 (17)0.56754 (7)0.20163 (4)0.0286 (3)
H19A−0.05310.61510.19700.043*
H19B−0.00590.52890.17520.043*
H19C0.15130.58210.19980.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0364 (5)0.0276 (4)0.0278 (4)−0.0038 (3)−0.0007 (3)0.0050 (3)
O20.0312 (4)0.0216 (4)0.0179 (4)−0.0018 (3)−0.0029 (3)−0.0002 (3)
O30.0428 (5)0.0211 (4)0.0253 (4)−0.0041 (3)−0.0032 (3)0.0026 (3)
O40.0398 (5)0.0312 (4)0.0182 (4)−0.0090 (4)−0.0033 (3)0.0003 (3)
O50.0722 (7)0.0338 (5)0.0238 (4)−0.0168 (5)−0.0113 (4)−0.0003 (3)
C10.0224 (5)0.0244 (5)0.0240 (5)−0.0017 (4)−0.0004 (4)−0.0042 (4)
C20.0225 (5)0.0223 (5)0.0299 (6)−0.0043 (4)0.0014 (4)−0.0021 (4)
C30.0218 (5)0.0223 (5)0.0251 (5)0.0029 (4)0.0040 (4)0.0012 (4)
C40.0238 (5)0.0245 (5)0.0229 (5)0.0009 (4)−0.0014 (4)−0.0034 (4)
C50.0238 (5)0.0203 (5)0.0241 (5)−0.0022 (4)0.0005 (4)−0.0034 (4)
C60.0220 (5)0.0210 (5)0.0222 (5)−0.0001 (4)0.0021 (4)−0.0032 (4)
C70.0296 (6)0.0251 (5)0.0219 (5)−0.0029 (4)−0.0009 (4)−0.0017 (4)
C80.0289 (5)0.0245 (5)0.0218 (5)−0.0022 (4)−0.0001 (4)−0.0026 (4)
C90.0240 (5)0.0245 (5)0.0228 (5)−0.0017 (4)−0.0008 (4)−0.0029 (4)
C100.0192 (5)0.0228 (5)0.0216 (5)0.0000 (4)0.0004 (4)0.0001 (4)
C110.0179 (5)0.0243 (5)0.0195 (5)0.0020 (4)0.0011 (4)0.0011 (4)
C120.0238 (5)0.0236 (5)0.0207 (5)0.0001 (4)0.0003 (4)−0.0015 (4)
C130.0218 (5)0.0216 (5)0.0258 (5)−0.0006 (4)0.0018 (4)0.0007 (4)
C140.0239 (5)0.0270 (5)0.0206 (5)−0.0003 (4)−0.0003 (4)0.0026 (4)
C150.0202 (5)0.0275 (5)0.0202 (5)−0.0007 (4)−0.0007 (4)−0.0013 (4)
C160.0475 (8)0.0368 (7)0.0252 (6)−0.0010 (6)−0.0025 (5)0.0057 (5)
C170.0367 (6)0.0252 (5)0.0204 (5)−0.0020 (5)−0.0060 (4)−0.0009 (4)
C180.0507 (8)0.0267 (6)0.0319 (6)−0.0080 (5)−0.0088 (6)0.0085 (5)
C190.0315 (6)0.0354 (6)0.0189 (5)−0.0007 (5)−0.0016 (4)0.0014 (4)
Geometric parameters (Å, º) top
O1—C31.3615 (13)C9—C101.4538 (15)
O1—C161.4287 (15)C9—H90.9500
O2—C111.3643 (12)C10—C151.4163 (14)
O2—C171.4269 (12)C10—C111.4191 (14)
O3—C131.3584 (13)C11—C121.3789 (15)
O3—C181.4294 (13)C12—C131.3954 (15)
O4—C151.3623 (13)C12—H120.9500
O4—C191.4290 (13)C13—C141.3907 (15)
O5—C71.2275 (14)C14—C151.3951 (16)
C1—C21.3818 (15)C14—H140.9500
C1—C61.4021 (15)C16—H16A0.9800
C1—H10.9500C16—H16B0.9800
C2—C31.3959 (16)C16—H16C0.9800
C2—H20.9500C17—H17A0.9800
C3—C41.3919 (15)C17—H17B0.9800
C4—C51.3931 (15)C17—H17C0.9800
C4—H40.9500C18—H18A0.9800
C5—C61.3941 (15)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.4955 (15)C19—H19A0.9800
C7—C81.4703 (15)C19—H19B0.9800
C8—C91.3435 (15)C19—H19C0.9800
C8—H80.9500
C3—O1—C16118.34 (9)C11—C12—C13119.46 (10)
C11—O2—C17117.53 (8)C11—C12—H12120.3
C13—O3—C18117.94 (9)C13—C12—H12120.3
C15—O4—C19118.10 (9)O3—C13—C14124.49 (10)
C2—C1—C6120.84 (10)O3—C13—C12114.15 (9)
C2—C1—H1119.6C14—C13—C12121.36 (10)
C6—C1—H1119.6C13—C14—C15118.16 (10)
C1—C2—C3120.13 (10)C13—C14—H14120.9
C1—C2—H2119.9C15—C14—H14120.9
C3—C2—H2119.9O4—C15—C14122.07 (10)
O1—C3—C4124.67 (10)O4—C15—C10115.14 (9)
O1—C3—C2115.22 (10)C14—C15—C10122.78 (10)
C4—C3—C2120.11 (10)O1—C16—H16A109.5
C3—C4—C5119.05 (10)O1—C16—H16B109.5
C3—C4—H4120.5H16A—C16—H16B109.5
C5—C4—H4120.5O1—C16—H16C109.5
C4—C5—C6121.69 (10)H16A—C16—H16C109.5
C4—C5—H5119.2H16B—C16—H16C109.5
C6—C5—H5119.2O2—C17—H17A109.5
C5—C6—C1118.16 (10)O2—C17—H17B109.5
C5—C6—C7123.58 (10)H17A—C17—H17B109.5
C1—C6—C7118.26 (9)O2—C17—H17C109.5
O5—C7—C8122.65 (10)H17A—C17—H17C109.5
O5—C7—C6119.56 (10)H17B—C17—H17C109.5
C8—C7—C6117.76 (9)O3—C18—H18A109.5
C9—C8—C7121.24 (10)O3—C18—H18B109.5
C9—C8—H8119.4H18A—C18—H18B109.5
C7—C8—H8119.4O3—C18—H18C109.5
C8—C9—C10129.63 (10)H18A—C18—H18C109.5
C8—C9—H9115.2H18B—C18—H18C109.5
C10—C9—H9115.2O4—C19—H19A109.5
C15—C10—C11116.08 (9)O4—C19—H19B109.5
C15—C10—C9119.08 (9)H19A—C19—H19B109.5
C11—C10—C9124.83 (9)O4—C19—H19C109.5
O2—C11—C12122.24 (9)H19A—C19—H19C109.5
O2—C11—C10115.70 (9)H19B—C19—H19C109.5
C12—C11—C10122.06 (10)
C6—C1—C2—C3−0.21 (16)C10—C11—O2—C17176.22 (9)
C16—O1—C3—C4−3.10 (16)C15—C10—C11—O2−179.71 (9)
C2—C3—O1—C16176.37 (10)C9—C10—C11—O2−0.21 (15)
C1—C2—C3—O1179.65 (10)C15—C10—C11—C121.10 (15)
C1—C2—C3—C4−0.85 (16)C9—C10—C11—C12−179.40 (10)
O1—C3—C4—C5−179.52 (10)O2—C11—C12—C13−177.37 (10)
C2—C3—C4—C51.03 (16)C10—C11—C12—C131.76 (16)
C3—C4—C5—C6−0.17 (16)C18—O3—C13—C145.92 (17)
C4—C5—C6—C1−0.86 (16)C12—C13—O3—C18−174.09 (10)
C4—C5—C6—C7179.29 (10)C11—C12—C13—O3176.86 (10)
C2—C1—C6—C51.04 (16)C11—C12—C13—C14−3.16 (16)
C2—C1—C6—C7−179.09 (10)O3—C13—C14—C15−178.47 (10)
C5—C6—C7—O5164.74 (12)C12—C13—C14—C151.56 (17)
C1—C6—C7—O5−15.12 (16)C14—C15—O4—C1916.90 (16)
C5—C6—C7—C8−16.87 (16)C19—O4—C15—C10−164.29 (10)
C1—C6—C7—C8163.27 (10)C13—C14—C15—O4−179.79 (10)
O5—C7—C8—C9−1.00 (19)C13—C14—C15—C101.49 (17)
C6—C7—C8—C9−179.34 (10)C11—C10—C15—O4178.43 (9)
C7—C8—C9—C10179.64 (11)C9—C10—C15—O4−1.10 (15)
C8—C9—C10—C15178.89 (11)C11—C10—C15—C14−2.77 (16)
C8—C9—C10—C11−0.59 (19)C9—C10—C15—C14177.70 (10)
C17—O2—C11—C12−4.60 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1···Cg2i0.952.893.6744 (12)140
C4—H4···Cg1ii0.952.943.6921 (12)137
C17—H17a···Cg1iii0.982.963.8913 (13)159
C19—H19a···Cg2iv0.982.823.4705 (13)125
C16—H16c···O3v0.982.513.4074 (16)152
C18—H18a···O5vi0.982.483.1578 (16)126
Symmetry codes: (i) x−3/2, y−1, −z−1/2; (ii) −x+1/2, −y, z+3/2; (iii) x−1/2, y, −z−1/2; (iv) −x−3/2, y−1/2, z; (v) −x, −y+1, −z+1; (vi) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC19H20O5
Mr328.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)133
a, b, c (Å)7.3339 (6), 16.8260 (14), 26.677 (2)
V (Å3)3291.9 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.35 × 0.33 × 0.31
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.967, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections		22257, 3593, 3380
Rint0.020
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.108, 1.02
No. of reflections3593
No. of parameters221
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1···Cg2i0.952.893.6744 (12)140
C4—H4···Cg1ii0.952.943.6921 (12)137
C17—H17a···Cg1iii0.982.963.8913 (13)159
C19—H19a···Cg2iv0.982.823.4705 (13)125
C16—H16c···O3v0.982.513.4074 (16)152
C18—H18a···O5vi0.982.483.1578 (16)126
Symmetry codes: (i) x−3/2, y−1, −z−1/2; (ii) −x+1/2, −y, z+3/2; (iii) x−1/2, y, −z−1/2; (iv) −x−3/2, y−1/2, z; (v) −x, −y+1, −z+1; (vi) −x, y+1/2, −z+1/2.
 

Acknowledgements

The authors are grateful for financial support from the Project of Wenzhou Sci. & Tech. Bureau (S20100045), Zhejiang Provincial Natural Science Foundation of China (Y2101108 & Y4090379) and the University Students in Zhejiang science and technology innovation projects (2010R413018).

References

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ISSN: 2056-9890
Volume 67| Part 6| June 2011| Page o1432
doi:10.1107/S1600536811017788
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