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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1265

(E)-1-(5-Hy­dr­oxy-2,2-di­methyl-2H-chromen-6-yl)-3-(3,4,5-trimeth­­oxy­phen­yl)prop-2-en-1-one

aDepartment of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, and bDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
*Correspondence e-mail: wanggch123@163.com

(Received 23 March 2011; accepted 22 April 2011; online 29 April 2011)

The title compound, C23H24O6, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 9.4 (10) and 12.96 (13)°, respectively, in mol­ecule A and 1.40 (17) and 4.44 (17)°, respectively, in mol­ecule B. The two meth­oxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = 6.2 (3) and −1.4 (3)° in mol­ecule A and −4.2 (4) and 3.7 (3)° in mol­ecule B], whereas the third meth­oxy group, at the para position, is (+)-anti­clinal with respect to the benzene ring [C—O—C—C = 81.7 (3)°] in mol­ecule A and is (−)-synclinal with respect to the benzene ring [C—O—C—C = −103.2 (3)°] in mol­ecule B. In both independent mol­ecules, the hy­droxy group is involved in an intra­molecular O—H⋯O hydrogen bond.

Related literature

For the synthesis of related compounds, see: Krohn et al. (2002[Krohn, K., Steingrover, K. & Rao, M. S. (2002). Phytochemistry, 61, 931-936.]). For the biological activity of related compounds, see: Tran et al. (2009[Tran, T. D., Park, H., Kim, H. P., Ecker, G. F. & Thai, K. M. (2009). Bioorg. Med. Chem. Lett. 19, 1650-1653.]); Nerya et al. (2004[Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochemistry, 65, 1389-1395.]). For related structures, see: Ranjith et al. (2010[Ranjith, S., Thirunarayanan, A., Raja, S., Rajakumar, P. & SubbiahPandi, A. (2010). Acta Cryst. E66, o2261-o2262.]); Jasinski et al. (2009[Jasinski, J. P., Butcher, R. J., Veena, K., Narayana, B. & Yathirajan, H. S. (2009). Acta Cryst. E65, o1965-o1966.], 2010[Jasinski, J. P., Butcher, R. J., Veena, K., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o1676.]); Fun et al.(2010[Fun, H.-K., Suwunwong, T., Chantrapromma, S. & Karalai, C. (2010). Acta Cryst. E66, o3070-o3071.]); Asiri et al.(2010[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010). Acta Cryst. E66, o2358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24O6

  • Mr = 396.42

  • Triclinic, [P \overline 1]

  • a = 9.9470 (9) Å

  • b = 13.9419 (13) Å

  • c = 16.1187 (11) Å

  • α = 72.681 (7)°

  • β = 89.487 (7)°

  • γ = 73.173 (8)°

  • V = 2035.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.22 × 0.15 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.952, Tmax = 1.0

  • 17082 measured reflections

  • 8314 independent reflections

  • 5047 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.148

  • S = 1.01

  • 8314 reflections

  • 541 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.91 (3) 1.67 (3) 2.509 (2) 152 (3)
O8—H8⋯O9 0.98 (3) 1.64 (3) 2.536 (2) 149 (3)

Data collection: CrysAlis PRO (Oxford Diffraction,2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

Chalcones (1,3-diaryl-2-propen-1-one) are natural or synthetic flavonoids displaying an impressive array of biological properties (Tran et al., 2009; Nerya et al.,2004). The title compound, (I), is one of our synthetic chalcone derivatives which have shown anti-inflammation activity. The crystal structures of related compounds: (E)-1-[4-(Prop-2-yn-1-yloxy)phenyl]-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Ranjith et al., 2010), (2E)-1-(2-Bromophenyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski et al., 2010), (E)-1-(2-Furyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Fun et al., 2010), (2E)-1-(4-fluorophenyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski et al., 2009), and (2E)-1-(2,5-Dimethyl-3- thienyl)-3-(2-methoxyphenyl)prop-2-en-1-one (Asiri et al., 2010) have been reported. We report here the crystal structure of (I), a new chalcone.

(I) crystallizes with two independent molecules (A and B) in the asymmetric unit (Fig. 1). In one molecule, the dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 9.42 (99) and 12.96 (13)°. The two methoxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = 6.2 (3) and -1.4 (3)°], whereas the third methoxy group, at the para position, is (+)-anticlinal with respect to the benzene ring [C—O—C—C = 81.7 (3)°]. In the second molecule, the dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 1.40 (17) and 4.44 (17)°. The two methoxy groups at the meta positions of the benzene ring are also close to being coplanar with the ring [C—O—C—C = -4.2 (4) and 3.7 (3)°], whereas the third methoxy group, at the para position, is (-)-synclinal with respect to the benzene ring [C—O—C—C = -103.2 (3)°]. In both independent molecules, the hydroxy group is involved in an intramolecular O—H···O hydrogen bond.

The crystal packing is shown in Fig. 2.

Related literature top

For the synthesis of related compounds, see: Krohn et al. (2002). For the biological activity of related compounds, see: Tran et al. (2009); Nerya et al. (2004). For related structures, see: Ranjith et al. (2010); Jasinski et al. (2009, 2010); Fun et al.(2010); Asiri et al.(2010).

Experimental top

1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)ethanone(2.182 g,10 mmol), 3,4,5-trimethoxybenzaldehyde(1.962 g,10 mmol) in ethanol was added KOH (20% w/v aqueous solution) and the mixture was stirred at 273 K for 10 h. Then the crude product was recrystallized from ethanol to give (I). Single crystals suitable for X-ray structure determination were grown by slow evaporation of an ethyl ether solution of (II)) at room temperature.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction,2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.The intramolecular hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. A crystal packing diagram of the title compound, viewed down the a axis.
(E)-1-(5-Hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4,5- trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C23H24O6Z = 4
Mr = 396.42F(000) = 840
Triclinic, P1Dx = 1.294 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 9.9470 (9) ÅCell parameters from 4923 reflections
b = 13.9419 (13) Åθ = 3.0–29.1°
c = 16.1187 (11) ŵ = 0.09 mm1
α = 72.681 (7)°T = 293 K
β = 89.487 (7)°Block, yellow
γ = 73.173 (8)°0.22 × 0.15 × 0.15 mm
V = 2035.3 (3) Å3
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
8314 independent reflections
Radiation source: fine-focus sealed tube5047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 16.0874 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 1717
Tmin = 0.952, Tmax = 1.0l = 2020
17082 measured reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0596P)2 + 0.3044P]
where P = (Fo2 + 2Fc2)/3
8314 reflections(Δ/σ)max < 0.001
541 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C23H24O6γ = 73.173 (8)°
Mr = 396.42V = 2035.3 (3) Å3
Triclinic, P1Z = 4
a = 9.9470 (9) ÅMo Kα radiation
b = 13.9419 (13) ŵ = 0.09 mm1
c = 16.1187 (11) ÅT = 293 K
α = 72.681 (7)°0.22 × 0.15 × 0.15 mm
β = 89.487 (7)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
8314 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
5047 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 1.0Rint = 0.025
17082 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.45 e Å3
8314 reflectionsΔρmin = 0.24 e Å3
541 parameters
Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O10.95861 (16)0.58077 (12)0.27494 (11)0.0589 (4)
O20.9670 (2)0.38689 (15)0.07853 (14)0.0811 (6)
H20.905 (3)0.386 (2)0.038 (2)0.109 (12)*
O30.75683 (19)0.44108 (14)0.02863 (12)0.0787 (6)
O40.27493 (17)0.69344 (13)0.41625 (10)0.0615 (4)
O50.11331 (19)0.87351 (13)0.39207 (11)0.0719 (5)
O60.11793 (16)0.90604 (13)0.23882 (11)0.0643 (5)
O70.14385 (15)0.83524 (12)0.20823 (10)0.0534 (4)
O80.58354 (16)0.66635 (13)0.37529 (12)0.0640 (5)
H80.630 (3)0.670 (2)0.427 (2)0.100 (10)*
O90.62958 (17)0.72834 (13)0.50207 (11)0.0678 (5)
O100.67922 (18)0.92060 (15)0.87490 (12)0.0742 (5)
O110.45780 (18)1.09188 (13)0.84452 (11)0.0668 (5)
O120.25878 (18)1.14008 (14)0.71618 (12)0.0754 (5)
C11.0710 (2)0.49482 (18)0.33362 (15)0.0525 (6)
C21.1603 (2)0.4292 (2)0.28400 (17)0.0645 (7)
H2A1.25430.39380.30400.077*
C31.1095 (2)0.4202 (2)0.21254 (18)0.0649 (7)
H31.16550.37510.18480.078*
C40.9655 (2)0.48070 (17)0.17680 (15)0.0489 (5)
C50.8962 (2)0.56160 (17)0.20991 (15)0.0482 (5)
C60.7635 (2)0.62990 (19)0.17363 (16)0.0590 (6)
H60.71820.68400.19600.071*
C70.7014 (2)0.61607 (18)0.10495 (15)0.0545 (6)
H70.61330.66230.08070.065*
C80.7642 (2)0.53521 (17)0.06891 (14)0.0470 (5)
C90.8980 (2)0.46652 (17)0.10828 (15)0.0521 (6)
C101.1532 (3)0.5489 (2)0.37303 (18)0.0699 (7)
H10A1.09090.59330.40160.105*
H10C1.19430.59090.32780.105*
H10B1.22650.49680.41470.105*
C111.0012 (3)0.4300 (2)0.40235 (19)0.0855 (9)
H11B0.93750.47500.42980.128*
H11C1.07180.37710.44530.128*
H11A0.94990.39680.37560.128*
C120.7010 (2)0.52044 (18)0.00538 (15)0.0535 (6)
C130.5738 (2)0.59855 (17)0.05740 (15)0.0518 (6)
H130.52420.65420.03790.062*
C140.5293 (2)0.59073 (17)0.13112 (16)0.0534 (6)
H140.58090.53110.14490.064*
C150.4117 (2)0.66076 (17)0.19463 (15)0.0479 (5)
C160.3968 (2)0.63920 (17)0.27196 (15)0.0503 (6)
H160.45680.57840.28010.060*
C170.2941 (2)0.70666 (17)0.33708 (14)0.0474 (5)
C180.2040 (2)0.79777 (17)0.32491 (15)0.0491 (5)
C190.2145 (2)0.81708 (17)0.24562 (15)0.0474 (5)
C200.3182 (2)0.74967 (17)0.18115 (15)0.0490 (5)
H200.32550.76360.12870.059*
C210.3577 (3)0.5985 (2)0.42989 (18)0.0713 (7)
H21B0.33190.59790.48690.107*
H21A0.34150.53940.38670.107*
H21C0.45570.59390.42520.107*
C220.0125 (3)0.8552 (3)0.4090 (3)0.1229 (15)
H22C0.07260.91650.45170.184*
H22B0.05870.84060.35620.184*
H22A0.00700.79610.43090.184*
C230.1245 (3)0.9282 (2)0.15864 (17)0.0744 (8)
H23C0.05710.99500.16300.112*
H23B0.21750.93060.14620.112*
H23A0.10340.87400.11260.112*
C240.1940 (2)0.79416 (17)0.13636 (14)0.0474 (5)
C250.3172 (2)0.69796 (19)0.16716 (15)0.0543 (6)
H250.33550.64910.13660.065*
C260.4013 (2)0.67979 (18)0.23656 (15)0.0510 (6)
H260.48160.62160.25170.061*
C270.3689 (2)0.75053 (15)0.28944 (13)0.0404 (5)
C280.2387 (2)0.82697 (16)0.27187 (13)0.0402 (5)
C290.1963 (2)0.89413 (18)0.32266 (15)0.0514 (6)
H290.10850.94490.31040.062*
C300.2853 (2)0.88433 (17)0.39039 (14)0.0480 (5)
H300.25630.92900.42420.058*
C310.4182 (2)0.80980 (16)0.41102 (13)0.0411 (5)
C320.4584 (2)0.74255 (16)0.35879 (14)0.0425 (5)
C330.0677 (2)0.7725 (2)0.10253 (17)0.0644 (7)
H33A0.09150.74700.05350.097*
H33C0.00970.83630.08480.097*
H33B0.04120.72040.14780.097*
C340.2363 (3)0.8798 (2)0.06837 (16)0.0701 (7)
H34A0.27320.85420.02120.105*
H34C0.30710.89880.09440.105*
H34B0.15530.94040.04660.105*
C350.5126 (2)0.79805 (17)0.48459 (14)0.0465 (5)
C360.4706 (2)0.86664 (17)0.53995 (14)0.0478 (5)
H360.38580.92070.52480.057*
C370.5486 (2)0.85463 (17)0.61035 (14)0.0486 (5)
H370.63400.80130.62190.058*
C380.5175 (2)0.91464 (16)0.67238 (14)0.0435 (5)
C390.6137 (2)0.88655 (17)0.74345 (15)0.0492 (5)
H390.69440.82950.75140.059*
C400.5909 (2)0.94278 (18)0.80282 (15)0.0512 (6)
C410.4718 (2)1.02935 (18)0.78994 (15)0.0525 (6)
C420.3737 (2)1.05527 (18)0.72055 (15)0.0516 (6)
C430.3958 (2)0.99901 (17)0.66142 (14)0.0475 (5)
H430.32971.01750.61450.057*
C440.7986 (3)0.8291 (2)0.8931 (2)0.0882 (10)
H44B0.85890.83700.84630.132*
H44A0.76770.76840.89870.132*
H44C0.84950.82010.94660.132*
C450.3649 (3)1.0768 (3)0.9084 (2)0.0914 (10)
H45B0.27021.10240.88160.137*
H45C0.37331.11440.94820.137*
H45A0.38691.00300.93950.137*
C460.1505 (3)1.1689 (2)0.6485 (2)0.0857 (9)
H46B0.18761.18870.59290.129*
H46C0.07481.22730.65390.129*
H46A0.11581.11020.65310.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0550 (9)0.0592 (10)0.0562 (10)0.0011 (8)0.0128 (8)0.0235 (8)
O20.0698 (12)0.0721 (12)0.0853 (15)0.0268 (9)0.0305 (11)0.0468 (11)
O30.0773 (12)0.0658 (12)0.0781 (13)0.0178 (9)0.0324 (10)0.0376 (10)
O40.0753 (11)0.0568 (10)0.0480 (10)0.0085 (9)0.0086 (8)0.0204 (8)
O50.0784 (12)0.0620 (11)0.0579 (11)0.0006 (9)0.0273 (9)0.0123 (9)
O60.0626 (10)0.0598 (10)0.0558 (11)0.0107 (8)0.0178 (8)0.0241 (8)
O70.0457 (8)0.0642 (10)0.0484 (9)0.0021 (7)0.0095 (7)0.0283 (8)
O80.0503 (9)0.0636 (11)0.0725 (12)0.0095 (8)0.0180 (9)0.0380 (10)
O90.0580 (10)0.0694 (11)0.0691 (12)0.0064 (9)0.0233 (9)0.0351 (10)
O100.0670 (11)0.0868 (13)0.0653 (12)0.0053 (10)0.0223 (9)0.0452 (10)
O110.0750 (11)0.0725 (12)0.0665 (12)0.0252 (10)0.0109 (10)0.0384 (10)
O120.0628 (11)0.0735 (12)0.0735 (13)0.0130 (9)0.0105 (10)0.0308 (10)
C10.0502 (13)0.0545 (14)0.0468 (14)0.0119 (11)0.0081 (11)0.0101 (11)
C20.0459 (13)0.0719 (17)0.0665 (18)0.0027 (12)0.0136 (12)0.0219 (14)
C30.0475 (13)0.0687 (17)0.0689 (18)0.0069 (12)0.0110 (13)0.0307 (14)
C40.0393 (11)0.0520 (13)0.0470 (14)0.0011 (10)0.0049 (10)0.0149 (11)
C50.0443 (12)0.0519 (13)0.0449 (14)0.0088 (10)0.0012 (11)0.0151 (11)
C60.0480 (13)0.0599 (15)0.0621 (16)0.0059 (11)0.0063 (12)0.0296 (13)
C70.0407 (12)0.0547 (14)0.0567 (15)0.0063 (10)0.0077 (11)0.0203 (12)
C80.0422 (11)0.0460 (13)0.0437 (13)0.0016 (10)0.0049 (10)0.0118 (10)
C90.0476 (12)0.0474 (13)0.0509 (14)0.0034 (10)0.0036 (11)0.0171 (11)
C100.0663 (16)0.0778 (18)0.0654 (18)0.0228 (14)0.0100 (14)0.0203 (15)
C110.093 (2)0.094 (2)0.069 (2)0.0460 (19)0.0043 (17)0.0074 (17)
C120.0508 (13)0.0474 (14)0.0524 (15)0.0002 (11)0.0072 (11)0.0150 (12)
C130.0476 (13)0.0453 (13)0.0532 (15)0.0013 (10)0.0076 (11)0.0136 (11)
C140.0537 (13)0.0445 (13)0.0525 (15)0.0017 (11)0.0104 (12)0.0134 (11)
C150.0467 (12)0.0436 (12)0.0474 (14)0.0095 (10)0.0071 (11)0.0088 (10)
C160.0539 (13)0.0407 (12)0.0521 (15)0.0075 (10)0.0060 (11)0.0143 (11)
C170.0549 (13)0.0469 (13)0.0390 (13)0.0167 (11)0.0036 (11)0.0097 (10)
C180.0509 (13)0.0418 (12)0.0447 (13)0.0076 (10)0.0121 (11)0.0046 (10)
C190.0441 (12)0.0445 (13)0.0480 (14)0.0065 (10)0.0066 (10)0.0127 (11)
C200.0490 (12)0.0503 (13)0.0421 (13)0.0081 (11)0.0064 (11)0.0126 (11)
C210.0831 (18)0.0686 (18)0.0656 (18)0.0154 (15)0.0047 (15)0.0327 (14)
C220.083 (2)0.097 (3)0.174 (4)0.0011 (19)0.067 (2)0.043 (3)
C230.0760 (18)0.0733 (18)0.0635 (18)0.0056 (14)0.0130 (15)0.0328 (15)
C240.0526 (13)0.0534 (13)0.0388 (13)0.0123 (11)0.0047 (10)0.0216 (11)
C250.0590 (14)0.0584 (14)0.0539 (15)0.0146 (12)0.0008 (12)0.0325 (12)
C260.0492 (12)0.0503 (13)0.0543 (15)0.0053 (11)0.0029 (11)0.0265 (12)
C270.0415 (11)0.0403 (12)0.0395 (12)0.0102 (9)0.0020 (10)0.0145 (10)
C280.0415 (11)0.0439 (12)0.0327 (11)0.0094 (9)0.0029 (9)0.0114 (9)
C290.0438 (12)0.0546 (14)0.0503 (14)0.0021 (10)0.0065 (11)0.0244 (12)
C300.0509 (12)0.0487 (13)0.0416 (13)0.0022 (10)0.0052 (11)0.0222 (11)
C310.0435 (11)0.0408 (11)0.0360 (12)0.0084 (9)0.0038 (10)0.0114 (9)
C320.0393 (11)0.0396 (12)0.0443 (13)0.0040 (9)0.0026 (10)0.0140 (10)
C330.0624 (15)0.0742 (18)0.0652 (17)0.0236 (14)0.0076 (13)0.0306 (14)
C340.0864 (19)0.0762 (18)0.0512 (16)0.0344 (16)0.0058 (14)0.0146 (14)
C350.0496 (13)0.0448 (12)0.0431 (13)0.0099 (11)0.0065 (11)0.0147 (10)
C360.0503 (12)0.0458 (13)0.0444 (13)0.0086 (10)0.0075 (11)0.0152 (10)
C370.0529 (13)0.0452 (13)0.0463 (14)0.0110 (10)0.0074 (11)0.0152 (11)
C380.0477 (12)0.0445 (12)0.0397 (12)0.0139 (10)0.0036 (10)0.0146 (10)
C390.0455 (12)0.0519 (13)0.0500 (14)0.0058 (10)0.0065 (11)0.0238 (11)
C400.0493 (13)0.0611 (15)0.0455 (14)0.0110 (11)0.0082 (11)0.0248 (12)
C410.0538 (13)0.0570 (14)0.0523 (15)0.0127 (12)0.0046 (12)0.0289 (12)
C420.0465 (12)0.0526 (14)0.0508 (15)0.0069 (11)0.0002 (11)0.0164 (11)
C430.0481 (12)0.0519 (13)0.0405 (13)0.0137 (11)0.0055 (10)0.0123 (11)
C440.0618 (16)0.112 (2)0.082 (2)0.0119 (16)0.0299 (15)0.0532 (19)
C450.101 (2)0.119 (3)0.074 (2)0.041 (2)0.031 (2)0.053 (2)
C460.0573 (16)0.091 (2)0.083 (2)0.0113 (15)0.0130 (16)0.0219 (18)
Geometric parameters (Å, º) top
O1—C11.466 (3)C19—C201.379 (3)
O1—C51.353 (3)C20—H200.9300
O2—H20.91 (3)C21—H21B0.9600
O2—C91.343 (3)C21—H21A0.9600
O3—C121.249 (3)C21—H21C0.9600
O4—C171.365 (3)C22—H22C0.9600
O4—C211.421 (3)C22—H22B0.9600
O5—C181.373 (3)C22—H22A0.9600
O5—C221.392 (3)C23—H23C0.9600
O6—C191.365 (2)C23—H23B0.9600
O6—C231.422 (3)C23—H23A0.9600
O7—C241.462 (2)C24—C251.486 (3)
O7—C281.356 (2)C24—C331.516 (3)
O8—H80.98 (3)C24—C341.518 (3)
O8—C321.349 (2)C25—H250.9300
O9—C351.251 (2)C25—C261.320 (3)
O10—C401.365 (3)C26—H260.9300
O10—C441.425 (3)C26—C271.454 (3)
O11—C411.392 (2)C27—C281.386 (3)
O11—C451.387 (3)C27—C321.393 (3)
O12—C421.371 (3)C28—C291.395 (3)
O12—C461.422 (3)C29—H290.9300
C1—C21.489 (3)C29—C301.361 (3)
C1—C101.514 (3)C30—H300.9300
C1—C111.510 (3)C30—C311.395 (3)
C2—H2A0.9300C31—C321.412 (3)
C2—C31.316 (3)C31—C351.459 (3)
C3—H30.9300C33—H33A0.9600
C3—C41.456 (3)C33—H33C0.9600
C4—C51.391 (3)C33—H33B0.9600
C4—C91.389 (3)C34—H34A0.9600
C5—C61.394 (3)C34—H34C0.9600
C6—H60.9300C34—H34B0.9600
C6—C71.361 (3)C35—C361.468 (3)
C7—H70.9300C36—H360.9300
C7—C81.405 (3)C36—C371.320 (3)
C8—C91.417 (3)C37—H370.9300
C8—C121.452 (3)C37—C381.462 (3)
C10—H10A0.9600C38—C391.385 (3)
C10—H10C0.9600C38—C431.391 (3)
C10—H10B0.9600C39—H390.9300
C11—H11B0.9600C39—C401.386 (3)
C11—H11C0.9600C40—C411.390 (3)
C11—H11A0.9600C41—C421.382 (3)
C12—C131.472 (3)C42—C431.383 (3)
C13—H130.9300C43—H430.9300
C13—C141.317 (3)C44—H44B0.9600
C14—H140.9300C44—H44A0.9600
C14—C151.461 (3)C44—H44C0.9600
C15—C161.385 (3)C45—H45B0.9600
C15—C201.392 (3)C45—H45C0.9600
C16—H160.9300C45—H45A0.9600
C16—C171.380 (3)C46—H46B0.9600
C17—C181.393 (3)C46—H46C0.9600
C18—C191.393 (3)C46—H46A0.9600
O1—C1—C2110.25 (19)C16—C15—C14118.3 (2)
O1—C1—C10104.90 (18)C16—C15—C20119.4 (2)
O1—C1—C11107.28 (19)C16—C17—C18119.6 (2)
O1—C5—C4121.15 (19)C17—O4—C21117.74 (19)
O1—C5—C6117.6 (2)C17—C16—C15121.0 (2)
O2—C9—C4117.3 (2)C17—C16—H16119.5
O2—C9—C8121.0 (2)C18—O5—C22116.4 (2)
O3—C12—C8120.1 (2)C19—O6—C23116.84 (18)
O3—C12—C13117.8 (2)C19—C18—C17119.5 (2)
O4—C17—C16124.9 (2)C19—C20—C15120.0 (2)
O4—C17—C18115.5 (2)C19—C20—H20120.0
O4—C21—H21B109.5C20—C15—C14122.2 (2)
O4—C21—H21A109.5C20—C19—C18120.4 (2)
O4—C21—H21C109.5H21B—C21—H21A109.5
O5—C18—C17121.2 (2)H21B—C21—H21C109.5
O5—C18—C19119.0 (2)H21A—C21—H21C109.5
O5—C22—H22C109.5H22C—C22—H22B109.5
O5—C22—H22B109.5H22C—C22—H22A109.5
O5—C22—H22A109.5H22B—C22—H22A109.5
O6—C19—C18115.08 (19)H23C—C23—H23B109.5
O6—C19—C20124.5 (2)H23C—C23—H23A109.5
O6—C23—H23C109.5H23B—C23—H23A109.5
O6—C23—H23B109.5C24—C25—H25119.0
O6—C23—H23A109.5C24—C33—H33A109.5
O7—C24—C25110.89 (17)C24—C33—H33C109.5
O7—C24—C33104.36 (17)C24—C33—H33B109.5
O7—C24—C34107.41 (17)C24—C34—H34A109.5
O7—C28—C27121.41 (17)C24—C34—H34C109.5
O7—C28—C29117.22 (18)C24—C34—H34B109.5
O8—C32—C27117.30 (18)C25—C24—C33112.52 (19)
O8—C32—C31121.38 (19)C25—C24—C34109.83 (19)
O9—C35—C31120.40 (19)C25—C26—H26119.9
O9—C35—C36119.13 (19)C25—C26—C27120.1 (2)
O10—C40—C39124.7 (2)C26—C25—C24121.94 (19)
O10—C40—C41115.59 (19)C26—C25—H25119.0
O10—C44—H44B109.5C27—C26—H26119.9
O10—C44—H44A109.5C27—C28—C29121.25 (19)
O10—C44—H44C109.5C27—C32—C31121.30 (18)
O11—C45—H45B109.5C28—O7—C24119.13 (16)
O11—C45—H45C109.5C28—C27—C26117.70 (19)
O11—C45—H45A109.5C28—C27—C32118.56 (18)
O12—C42—C41114.28 (19)C28—C29—H29120.5
O12—C42—C43125.0 (2)C29—C30—H30118.7
O12—C46—H46B109.5C29—C30—C31122.55 (19)
O12—C46—H46C109.5C30—C29—C28119.1 (2)
O12—C46—H46A109.5C30—C29—H29120.5
C1—C2—H2A119.2C30—C31—C32117.26 (19)
C1—C10—H10A109.5C30—C31—C35122.54 (18)
C1—C10—H10C109.5C31—C30—H30118.7
C1—C10—H10B109.5C31—C35—C36120.46 (19)
C1—C11—H11B109.5C32—O8—H8106.4 (17)
C1—C11—H11C109.5C32—C27—C26123.67 (19)
C1—C11—H11A109.5C32—C31—C35120.18 (19)
C2—C1—C10112.1 (2)C33—C24—C34111.6 (2)
C2—C1—C11110.8 (2)H33A—C33—H33C109.5
C2—C3—H3120.0H33A—C33—H33B109.5
C2—C3—C4120.1 (2)H33C—C33—H33B109.5
C3—C2—C1121.6 (2)H34A—C34—H34C109.5
C3—C2—H2A119.2H34A—C34—H34B109.5
C4—C3—H3120.0H34C—C34—H34B109.5
C4—C5—C6121.1 (2)C35—C36—H36118.7
C4—C9—C8121.7 (2)C36—C37—H37115.9
C5—O1—C1118.74 (17)C36—C37—C38128.2 (2)
C5—C4—C3117.4 (2)C37—C36—C35122.6 (2)
C5—C6—H6120.5C37—C36—H36118.7
C6—C7—H7118.5C38—C37—H37115.9
C6—C7—C8123.1 (2)C38—C39—H39119.7
C7—C6—C5118.9 (2)C38—C39—C40120.6 (2)
C7—C6—H6120.5C38—C43—H43120.1
C7—C8—C9116.4 (2)C39—C38—C37118.4 (2)
C7—C8—C12123.9 (2)C39—C38—C43119.57 (19)
C8—C7—H7118.5C39—C40—C41119.7 (2)
C8—C12—C13122.0 (2)C40—O10—C44117.36 (18)
C9—O2—H2105 (2)C40—C39—H39119.7
C9—C4—C3123.7 (2)C40—C41—O11119.1 (2)
C9—C4—C5118.7 (2)C41—C42—C43120.7 (2)
C9—C8—C12119.74 (19)C42—O12—C46117.54 (19)
H10A—C10—H10C109.5C42—C41—O11121.2 (2)
H10A—C10—H10B109.5C42—C41—C40119.64 (19)
H10C—C10—H10B109.5C42—C43—C38119.7 (2)
C11—C1—C10111.3 (2)C42—C43—H43120.1
H11B—C11—H11C109.5C43—C38—C37122.0 (2)
H11B—C11—H11A109.5H44B—C44—H44A109.5
H11C—C11—H11A109.5H44B—C44—H44C109.5
C12—C13—H13119.5H44A—C44—H44C109.5
C13—C14—H14114.9C45—O11—C41115.46 (19)
C13—C14—C15130.3 (2)H45B—C45—H45C109.5
C14—C13—C12121.0 (2)H45B—C45—H45A109.5
C14—C13—H13119.5H45C—C45—H45A109.5
C15—C14—H14114.9H46B—C46—H46C109.5
C15—C16—H16119.5H46B—C46—H46A109.5
C15—C20—H20120.0H46C—C46—H46A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.91 (3)1.67 (3)2.509 (2)152 (3)
O8—H8···O90.98 (3)1.64 (3)2.536 (2)149 (3)

Experimental details

Crystal data
Chemical formulaC23H24O6
Mr396.42
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.9470 (9), 13.9419 (13), 16.1187 (11)
α, β, γ (°)72.681 (7), 89.487 (7), 73.173 (8)
V3)2035.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.22 × 0.15 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.952, 1.0
No. of measured, independent and
observed [I > 2σ(I)] reflections
17082, 8314, 5047
Rint0.025
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.148, 1.01
No. of reflections8314
No. of parameters541
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.24

Computer programs: CrysAlis PRO (Oxford Diffraction,2010), CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.91 (3)1.67 (3)2.509 (2)152 (3)
O8—H8···O90.98 (3)1.64 (3)2.536 (2)149 (3)
 

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

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Volume 67| Part 5| May 2011| Page o1265
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