supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, o3927    [ doi:10.1107/S1600536807035520 ]

Loureirin A

S.-Y. Yang, Y.-B. Lu, Q.-T. Zheng and Y. Lu

Abstract top

The asymmetric unit of the title compound [systematic name: 3-(2,4-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one], C17H18O4, contains two independent molecules; these have different conformations with respect to the relative orientation of the aromatic ring planes. The dihedral angles formed by the dimethoxyphenyl and hydroxyphenyl rings in the two molecules are 19.61 (10) and 66.37 (9)°. In the crystal structure, intermolecular O-H...O hydrogen-bonding interactions link the molecules into one-dimensional chains running parallel to the c axis.

Comment top

We have recently published the crystal structure of loureirin B (Lu et al., 2006). As a continuation of our studies on the components of Sanguis draxonis, we report here the crystal structure of loureirin A, which was crystallized from a DMF:water (1:1 v/v) solution.

In the asymmetric unit of the title compound there are two independent molecules (Fig. 1) with different conformations. The main difference between the two molecules relates to the relative orientation of the aromatic ring planes, as indicated by the dihedral angles formed by the dimethoxyphenyl and hydroxyphenyl rings [19.61 (10) and 66.37 (9)°] and by the values of the C4—C7—C8—C9 torsion angles [83.9 (4) and 179.3 (2)°]. In this orientation, intramolecular C—H···O hydrogen bonds stabilizing the conformation are observed only in one molecule (Table 1). In the crystal packing, the molecules are linked by intermolecular O—H···O hydrogen bonding interactions (Table 1) into one-dimensional chains running parallel to the c axis (Fig. 2).

Related literature top

For the extraction of the components of Sanguis draxonis see: Zhou et al. (2001). For the crystal structure of loureirin B see: Lu et al. (2006).

Experimental top

The title compound was extracted according to the literature method (Zhou et al., 2001) from the herb Sanguis draxonis. Colourless block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of as DMF:water (1:1 v/v) solution at 298 K over a period of one month.

Refinement top

The hydroxy and aromatic H atoms were located in a difference Fourier map and refined freely with Uiso(H) = 1.2Ueq(C, O). The methyl H atoms were constrained to an ideal geometry with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. The methylene H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of loureirin A showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. The molecular packing of loureirin A viewed down the a axis. Dashed lines indicate intermolecular C—H···O hydrogen bonding interactions.
3-(2,4-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one top
Crystal data top
C17H18O4Z = 4
Mr = 286.31F(000) = 608
Triclinic, P1Dx = 1.283 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1750 (7) ÅCell parameters from 5366 reflections
b = 12.8971 (8) Åθ = 2.5–25.6°
c = 15.2410 (6) ŵ = 0.09 mm−1
α = 73.509 (10)°T = 295 K
β = 86.259 (12)°Block, colourless
γ = 74.206 (10)°0.20 × 0.20 × 0.10 mm
V = 1482.5 (2) Å3
Data collection top
MAC DIP 2030K
diffractometer		3408 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.049
graphiteθmax = 25.6°, θmin = 2.5°
Detector resolution: 0 pixels mm-1h = −9→9
ω scansk = −14→15
10182 measured reflectionsl = −18→18
5366 independent 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) = 0.189H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1025P)2 + 0.2205P]
where P = (Fo2 + 2Fc2)/3
5366 reflections(Δ/σ)max < 0.001
431 parametersΔρmax = 0.29 e Å−3
3 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C17H18O4γ = 74.206 (10)°
Mr = 286.31V = 1482.5 (2) Å3
Triclinic, P1Z = 4
a = 8.1750 (7) ÅMo Kα radiation
b = 12.8971 (8) ŵ = 0.09 mm−1
c = 15.2410 (6) ÅT = 295 K
α = 73.509 (10)°0.20 × 0.20 × 0.10 mm
β = 86.259 (12)°
Data collection top
MAC DIP 2030K
diffractometer		3408 reflections with I > 2σ(I)
10182 measured reflectionsRint = 0.049
5366 independent reflectionsθmax = 25.6°
Refinement top
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189Δρmax = 0.29 e Å−3
S = 1.02Δρmin = −0.20 e Å−3
5366 reflectionsAbsolute structure: ?
431 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
O10.8504 (3)−0.0889 (2)0.31936 (15)0.0893 (8)
H1A0.895 (6)−0.045 (4)0.282 (3)0.134*
O20.6352 (4)−0.05071 (19)0.71439 (14)0.0959 (8)
O30.7430 (3)0.34222 (18)0.52269 (14)0.0849 (7)
O40.5812 (3)0.64527 (17)0.65600 (14)0.0780 (6)
C10.8119 (4)−0.0571 (3)0.39738 (19)0.0663 (8)
C20.7716 (4)−0.1363 (3)0.4721 (2)0.0675 (8)
H2A0.769 (4)−0.208 (3)0.463 (2)0.081*
C30.7254 (4)−0.1091 (2)0.5530 (2)0.0663 (8)
H3A0.694 (4)−0.162 (3)0.604 (2)0.080*
C40.7268 (4)−0.0048 (2)0.56262 (19)0.0663 (8)
C50.7722 (5)0.0726 (3)0.4876 (2)0.0778 (9)
H5A0.780 (4)0.149 (3)0.493 (2)0.093*
C60.8117 (5)0.0463 (3)0.4060 (2)0.0763 (9)
H6A0.839 (4)0.098 (3)0.358 (2)0.092*
C70.6835 (5)0.0173 (3)0.6527 (2)0.0793 (9)
C80.7015 (5)0.1266 (3)0.6695 (2)0.0869 (10)
H8A0.71630.11590.73440.104*
H8B0.80000.14670.63790.104*
C90.5417 (5)0.2186 (3)0.6340 (2)0.0843 (9)
H9A0.44400.19930.66720.101*
H9B0.52480.22700.56970.101*
C100.5596 (4)0.3302 (3)0.6468 (2)0.0768 (9)
C110.4803 (5)0.3731 (3)0.7163 (2)0.0816 (10)
H11A0.417 (5)0.333 (3)0.759 (2)0.098*
C120.4845 (4)0.4774 (3)0.7244 (2)0.0697 (8)
H12A0.431 (4)0.499 (3)0.776 (2)0.084*
C130.5740 (4)0.5393 (2)0.65944 (18)0.0604 (7)
C140.6624 (4)0.4961 (3)0.59190 (19)0.0624 (7)
H14A0.719 (4)0.542 (3)0.550 (2)0.075*
C150.6579 (4)0.3920 (3)0.58686 (19)0.0677 (8)
C160.8440 (5)0.3992 (3)0.4582 (2)0.0955 (11)
H16A0.89760.35370.41890.143*
H16B0.92950.41370.48980.143*
H16C0.77340.46890.42220.143*
C170.4891 (5)0.6949 (3)0.7225 (2)0.0896 (11)
H17A0.50320.76890.71230.134*
H17B0.53110.65000.78250.134*
H17C0.37070.69940.71770.134*
O1A0.4963 (3)1.16103 (19)1.12874 (15)0.0815 (7)
H1B0.468 (6)1.120 (4)1.172 (3)0.122*
O2A0.9855 (2)0.99444 (15)0.83152 (12)0.0637 (5)
O3A1.2335 (3)0.58212 (16)0.97268 (12)0.0666 (5)
O4A1.0914 (3)0.32784 (16)0.83785 (14)0.0760 (6)
C1A0.5971 (4)1.1025 (2)1.07499 (18)0.0584 (7)
C2A0.6605 (4)1.1639 (2)0.9963 (2)0.0664 (8)
H2B0.628 (4)1.240 (3)0.981 (2)0.080*
C3A0.7646 (4)1.1097 (2)0.93961 (19)0.0613 (7)
H3B0.807 (4)1.154 (3)0.888 (2)0.074*
C4A0.8053 (3)0.9935 (2)0.95884 (16)0.0519 (6)
C5A0.7388 (4)0.9331 (2)1.03753 (17)0.0564 (7)
H5B0.773 (4)0.853 (3)1.0537 (18)0.068*
C6A0.6373 (4)0.9868 (2)1.09567 (18)0.0587 (7)
H6B0.592 (4)0.944 (2)1.1526 (19)0.070*
C7A0.9191 (3)0.9379 (2)0.89583 (17)0.0534 (6)
C8A0.9471 (4)0.8144 (2)0.90919 (18)0.0589 (7)
H8C0.83830.79910.90590.071*
H8D0.99510.77420.96980.071*
C9A1.0642 (4)0.7713 (2)0.83885 (18)0.0620 (7)
H9C1.02880.82170.77870.074*
H9D1.17840.77350.85030.074*
C10A1.0694 (3)0.6541 (2)0.83781 (17)0.0550 (7)
C11A0.9883 (4)0.6345 (2)0.76959 (18)0.0618 (7)
H11B0.925 (4)0.699 (3)0.722 (2)0.074*
C12A0.9910 (4)0.5275 (2)0.76584 (19)0.0599 (7)
H12B0.928 (4)0.518 (2)0.719 (2)0.072*
C13A1.0773 (4)0.4372 (2)0.83321 (17)0.0574 (7)
C14A1.1586 (4)0.4520 (2)0.90420 (18)0.0570 (7)
H14B1.217 (4)0.389 (3)0.9520 (19)0.068*
C15A1.1545 (3)0.5599 (2)0.90622 (16)0.0519 (6)
C16A1.3028 (4)0.4903 (3)1.04937 (19)0.0733 (8)
H16D1.35000.51661.09230.110*
H16E1.39050.43571.02930.110*
H16F1.21470.45661.07820.110*
C17A1.0131 (6)0.3063 (3)0.7664 (2)0.0924 (11)
H17D1.03360.22680.77680.139*
H17E1.06010.33740.70860.139*
H17F0.89280.34010.76550.139*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1167 (19)0.0998 (18)0.0703 (14)−0.0473 (15)0.0337 (13)−0.0426 (13)
O20.118 (2)0.0785 (15)0.0748 (13)−0.0372 (15)0.0304 (14)−0.0242 (11)
O30.1130 (18)0.0782 (14)0.0746 (13)−0.0331 (13)0.0349 (13)−0.0389 (11)
O40.0961 (16)0.0659 (13)0.0831 (13)−0.0318 (12)0.0251 (12)−0.0335 (11)
C10.0682 (18)0.072 (2)0.0625 (16)−0.0219 (15)0.0137 (14)−0.0250 (14)
C20.083 (2)0.0628 (18)0.0662 (17)−0.0297 (16)0.0144 (15)−0.0250 (14)
C30.082 (2)0.0545 (17)0.0628 (16)−0.0264 (15)0.0137 (15)−0.0119 (13)
C40.080 (2)0.0550 (16)0.0636 (16)−0.0191 (14)0.0125 (15)−0.0170 (13)
C50.109 (3)0.0528 (17)0.0726 (18)−0.0291 (17)0.0264 (18)−0.0175 (15)
C60.099 (2)0.0647 (19)0.0604 (17)−0.0256 (17)0.0238 (17)−0.0112 (14)
C70.099 (2)0.0748 (19)0.0734 (19)−0.0200 (17)0.0268 (18)−0.0228 (16)
C80.101 (3)0.086 (2)0.0711 (19)−0.018 (2)0.0080 (18)−0.0226 (17)
C90.081 (2)0.076 (3)0.0724 (19)−0.0160 (19)0.0010 (17)−0.0250 (18)
C100.087 (2)0.0630 (19)0.088 (2)−0.0130 (16)0.0184 (18)−0.0231 (16)
C110.100 (2)0.067 (2)0.083 (2)−0.0328 (18)0.0380 (19)−0.0268 (17)
C120.079 (2)0.0667 (19)0.0702 (18)−0.0232 (16)0.0210 (16)−0.0307 (15)
C130.0681 (18)0.0556 (16)0.0599 (15)−0.0184 (13)0.0074 (13)−0.0194 (13)
C140.0677 (18)0.0640 (18)0.0591 (15)−0.0223 (14)0.0059 (14)−0.0189 (13)
C150.078 (2)0.0697 (19)0.0620 (16)−0.0219 (15)0.0143 (15)−0.0290 (14)
C160.110 (3)0.100 (3)0.079 (2)−0.029 (2)0.033 (2)−0.036 (2)
C170.115 (3)0.065 (2)0.092 (2)−0.0213 (19)0.033 (2)−0.0362 (18)
O1A0.1072 (18)0.0697 (14)0.0769 (14)−0.0298 (13)0.0361 (13)−0.0369 (11)
O2A0.0785 (13)0.0529 (11)0.0602 (10)−0.0220 (9)0.0176 (9)−0.0155 (9)
O3A0.0773 (13)0.0637 (12)0.0616 (11)−0.0219 (10)0.0006 (9)−0.0186 (9)
O4A0.1073 (17)0.0479 (11)0.0773 (13)−0.0210 (11)−0.0013 (11)−0.0235 (10)
C1A0.0665 (17)0.0570 (16)0.0572 (14)−0.0181 (13)0.0074 (13)−0.0240 (12)
C2A0.087 (2)0.0434 (15)0.0725 (17)−0.0185 (15)0.0161 (15)−0.0238 (13)
C3A0.0778 (19)0.0455 (15)0.0631 (16)−0.0210 (13)0.0066 (14)−0.0156 (12)
C4A0.0604 (15)0.0437 (14)0.0518 (13)−0.0146 (12)0.0011 (11)−0.0127 (11)
C5A0.0694 (17)0.0450 (14)0.0528 (14)−0.0155 (13)0.0048 (12)−0.0108 (11)
C6A0.0664 (17)0.0540 (16)0.0563 (14)−0.0182 (13)0.0083 (13)−0.0157 (12)
C7A0.0582 (15)0.0478 (14)0.0541 (13)−0.0159 (12)0.0000 (12)−0.0121 (11)
C8A0.0657 (17)0.0482 (15)0.0648 (15)−0.0161 (13)0.0127 (13)−0.0203 (12)
C9A0.0787 (19)0.0484 (15)0.0606 (15)−0.0200 (14)0.0144 (14)−0.0178 (12)
C10A0.0653 (16)0.0462 (14)0.0528 (14)−0.0142 (12)0.0169 (12)−0.0166 (11)
C11A0.0764 (19)0.0529 (16)0.0507 (14)−0.0118 (14)0.0081 (13)−0.0126 (12)
C12A0.0727 (19)0.0578 (17)0.0535 (14)−0.0195 (14)0.0037 (13)−0.0207 (13)
C13A0.0731 (18)0.0466 (14)0.0555 (14)−0.0193 (13)0.0161 (13)−0.0191 (12)
C14A0.0636 (17)0.0468 (15)0.0552 (14)−0.0103 (12)0.0100 (13)−0.0118 (12)
C15A0.0554 (15)0.0523 (15)0.0493 (13)−0.0141 (12)0.0113 (11)−0.0189 (11)
C16A0.0719 (19)0.087 (2)0.0608 (16)−0.0233 (17)−0.0011 (14)−0.0180 (15)
C17A0.133 (3)0.069 (2)0.093 (2)−0.041 (2)0.007 (2)−0.0393 (19)
Geometric parameters (Å, °) top
O1—C11.356 (3)O1A—C1A1.358 (3)
O1—H1A0.82 (4)O1A—H1B0.79 (4)
O2—C71.217 (3)O2A—C7A1.236 (3)
O3—C151.370 (3)O3A—C15A1.370 (3)
O3—C161.415 (4)O3A—C16A1.423 (4)
O4—C131.369 (3)O4A—C13A1.365 (3)
O4—C171.418 (3)O4A—C17A1.426 (4)
C1—C61.375 (4)C1A—C6A1.384 (4)
C1—C21.387 (4)C1A—C2A1.392 (4)
C2—C31.378 (4)C2A—C3A1.373 (4)
C2—H2A0.98 (3)C2A—H2B0.91 (3)
C3—C41.396 (4)C3A—C4A1.390 (4)
C3—H3A0.96 (3)C3A—H3B0.94 (3)
C4—C51.393 (4)C4A—C5A1.398 (3)
C4—C71.482 (4)C4A—C7A1.488 (3)
C5—C61.376 (4)C5A—C6A1.375 (4)
C5—H5A1.03 (3)C5A—H5B0.95 (3)
C6—H6A0.90 (3)C6A—H6B1.00 (3)
C7—C81.548 (5)C7A—C8A1.501 (3)
C8—C91.514 (5)C8A—C9A1.514 (3)
C8—H8A0.9700C8A—H8C0.9700
C8—H8B0.9700C8A—H8D0.9700
C9—C101.552 (5)C9A—C10A1.506 (3)
C9—H9A0.9700C9A—H9C0.9700
C9—H9B0.9700C9A—H9D0.9700
C10—C111.377 (4)C10A—C11A1.383 (4)
C10—C151.398 (4)C10A—C15A1.400 (4)
C11—C121.395 (4)C11A—C12A1.392 (4)
C11—H11A0.93 (3)C11A—H11B0.98 (3)
C12—C131.389 (4)C12A—C13A1.370 (4)
C12—H12A0.94 (3)C12A—H12B0.96 (3)
C13—C141.379 (4)C13A—C14A1.389 (4)
C14—C151.376 (4)C14A—C15A1.392 (4)
C14—H14A0.93 (3)C14A—H14B0.96 (3)
C16—H16A0.9600C16A—H16D0.9600
C16—H16B0.9600C16A—H16E0.9600
C16—H16C0.9600C16A—H16F0.9600
C17—H17A0.9600C17A—H17D0.9600
C17—H17B0.9600C17A—H17E0.9600
C17—H17C0.9600C17A—H17F0.9600
C1—O1—H1A111 (3)C1A—O1A—H1B110 (3)
C15—O3—C16118.8 (2)C15A—O3A—C16A117.1 (2)
C13—O4—C17117.5 (2)C13A—O4A—C17A117.5 (2)
O1—C1—C6124.3 (3)O1A—C1A—C6A122.7 (2)
O1—C1—C2116.1 (3)O1A—C1A—C2A117.2 (2)
C6—C1—C2119.6 (3)C6A—C1A—C2A120.1 (2)
C3—C2—C1119.6 (3)C3A—C2A—C1A120.1 (3)
C3—C2—H2A123.0 (18)C3A—C2A—H2B120.1 (19)
C1—C2—H2A117.3 (18)C1A—C2A—H2B119.8 (19)
C2—C3—C4121.1 (3)C2A—C3A—C4A120.7 (2)
C2—C3—H3A120.4 (18)C2A—C3A—H3B117.1 (18)
C4—C3—H3A118.5 (18)C4A—C3A—H3B122.2 (18)
C5—C4—C3118.4 (3)C3A—C4A—C5A118.6 (2)
C5—C4—C7123.2 (3)C3A—C4A—C7A119.0 (2)
C3—C4—C7118.4 (2)C5A—C4A—C7A122.4 (2)
C6—C5—C4120.1 (3)C6A—C5A—C4A121.0 (3)
C6—C5—H5A119.3 (18)C6A—C5A—H5B119.6 (16)
C4—C5—H5A120.6 (18)C4A—C5A—H5B119.1 (16)
C1—C6—C5121.2 (3)C5A—C6A—C1A119.6 (2)
C1—C6—H6A120 (2)C5A—C6A—H6B121.3 (16)
C5—C6—H6A119 (2)C1A—C6A—H6B119.1 (16)
O2—C7—C4120.4 (3)O2A—C7A—C4A119.6 (2)
O2—C7—C8119.4 (3)O2A—C7A—C8A120.8 (2)
C4—C7—C8120.2 (3)C4A—C7A—C8A119.6 (2)
C9—C8—C7108.2 (3)C7A—C8A—C9A113.0 (2)
C9—C8—H8A110.1C7A—C8A—H8C109.0
C7—C8—H8A110.1C9A—C8A—H8C109.0
C9—C8—H8B110.1C7A—C8A—H8D109.0
C7—C8—H8B110.1C9A—C8A—H8D109.0
H8A—C8—H8B108.4H8C—C8A—H8D107.8
C8—C9—C10109.1 (3)C10A—C9A—C8A114.8 (2)
C8—C9—H9A109.9C10A—C9A—H9C108.6
C10—C9—H9A109.9C8A—C9A—H9C108.6
C8—C9—H9B109.9C10A—C9A—H9D108.6
C10—C9—H9B109.9C8A—C9A—H9D108.6
H9A—C9—H9B108.3H9C—C9A—H9D107.5
C11—C10—C15117.1 (3)C11A—C10A—C15A116.9 (2)
C11—C10—C9122.3 (3)C11A—C10A—C9A121.4 (2)
C15—C10—C9120.6 (3)C15A—C10A—C9A121.7 (3)
C10—C11—C12122.8 (3)C10A—C11A—C12A123.1 (3)
C10—C11—H11A119 (2)C10A—C11A—H11B118.2 (18)
C12—C11—H11A118 (2)C12A—C11A—H11B118.7 (18)
C13—C12—C11117.9 (3)C13A—C12A—C11A118.4 (3)
C13—C12—H12A124.9 (19)C13A—C12A—H12B121.4 (18)
C11—C12—H12A117.1 (19)C11A—C12A—H12B120.1 (18)
O4—C13—C14115.2 (2)O4A—C13A—C12A124.7 (3)
O4—C13—C12124.2 (2)O4A—C13A—C14A114.4 (3)
C14—C13—C12120.6 (3)C12A—C13A—C14A120.9 (3)
C15—C14—C13119.9 (3)C13A—C14A—C15A119.6 (3)
C15—C14—H14A123.2 (19)C13A—C14A—H14B120.8 (17)
C13—C14—H14A116.8 (19)C15A—C14A—H14B119.6 (17)
O3—C15—C14123.8 (2)O3A—C15A—C14A123.5 (2)
O3—C15—C10114.8 (3)O3A—C15A—C10A115.4 (2)
C14—C15—C10121.3 (3)C14A—C15A—C10A121.1 (3)
O3—C16—H16A109.5O3A—C16A—H16D109.5
O3—C16—H16B109.5O3A—C16A—H16E109.5
H16A—C16—H16B109.5H16D—C16A—H16E109.5
O3—C16—H16C109.5O3A—C16A—H16F109.5
H16A—C16—H16C109.5H16D—C16A—H16F109.5
H16B—C16—H16C109.5H16E—C16A—H16F109.5
O4—C17—H17A109.5O4A—C17A—H17D109.5
O4—C17—H17B109.5O4A—C17A—H17E109.5
H17A—C17—H17B109.5H17D—C17A—H17E109.5
O4—C17—H17C109.5O4A—C17A—H17F109.5
H17A—C17—H17C109.5H17D—C17A—H17F109.5
H17B—C17—H17C109.5H17E—C17A—H17F109.5
O1—C1—C2—C3−177.8 (3)O1A—C1A—C2A—C3A179.3 (3)
C6—C1—C2—C32.5 (5)C6A—C1A—C2A—C3A−0.7 (5)
C1—C2—C3—C4−3.2 (5)C1A—C2A—C3A—C4A1.3 (5)
C2—C3—C4—C51.5 (5)C2A—C3A—C4A—C5A−0.5 (4)
C2—C3—C4—C7−177.2 (3)C2A—C3A—C4A—C7A−179.8 (3)
C3—C4—C5—C61.1 (5)C3A—C4A—C5A—C6A−0.9 (4)
C7—C4—C5—C6179.6 (3)C7A—C4A—C5A—C6A178.4 (3)
O1—C1—C6—C5−179.6 (3)C4A—C5A—C6A—C1A1.5 (4)
C2—C1—C6—C50.0 (5)O1A—C1A—C6A—C5A179.3 (3)
C4—C5—C6—C1−1.8 (6)C2A—C1A—C6A—C5A−0.7 (4)
C5—C4—C7—O2175.7 (4)C3A—C4A—C7A—O2A5.3 (4)
C3—C4—C7—O2−5.7 (5)C5A—C4A—C7A—O2A−174.0 (3)
C5—C4—C7—C8−5.0 (5)C3A—C4A—C7A—C8A−172.6 (3)
C3—C4—C7—C8173.6 (3)C5A—C4A—C7A—C8A8.1 (4)
O2—C7—C8—C9−96.8 (4)O2A—C7A—C8A—C9A1.4 (4)
C4—C7—C8—C983.8 (4)C4A—C7A—C8A—C9A179.3 (2)
C7—C8—C9—C10−177.9 (3)C7A—C8A—C9A—C10A−168.6 (2)
C8—C9—C10—C11−102.6 (4)C8A—C9A—C10A—C11A105.0 (3)
C8—C9—C10—C1577.7 (4)C8A—C9A—C10A—C15A−74.2 (3)
C15—C10—C11—C124.8 (6)C15A—C10A—C11A—C12A−1.2 (4)
C9—C10—C11—C12−174.9 (3)C9A—C10A—C11A—C12A179.6 (2)
C10—C11—C12—C13−0.4 (6)C10A—C11A—C12A—C13A0.4 (4)
C17—O4—C13—C14178.5 (3)C17A—O4A—C13A—C12A1.2 (4)
C17—O4—C13—C12−0.9 (5)C17A—O4A—C13A—C14A−179.1 (3)
C11—C12—C13—O4176.3 (3)C11A—C12A—C13A—O4A−179.6 (2)
C11—C12—C13—C14−3.1 (5)C11A—C12A—C13A—C14A0.7 (4)
O4—C13—C14—C15−177.4 (3)O4A—C13A—C14A—C15A179.3 (2)
C12—C13—C14—C152.0 (5)C12A—C13A—C14A—C15A−0.9 (4)
C16—O3—C15—C141.0 (5)C16A—O3A—C15A—C14A−8.8 (3)
C16—O3—C15—C10179.2 (3)C16A—O3A—C15A—C10A172.3 (2)
C13—C14—C15—O3−179.4 (3)C13A—C14A—C15A—O3A−178.8 (2)
C13—C14—C15—C102.6 (5)C13A—C14A—C15A—C10A0.0 (4)
C11—C10—C15—O3175.9 (3)C11A—C10A—C15A—O3A180.0 (2)
C9—C10—C15—O3−4.4 (5)C9A—C10A—C15A—O3A−0.8 (3)
C11—C10—C15—C14−5.9 (5)C11A—C10A—C15A—C14A1.0 (3)
C9—C10—C15—C14173.8 (3)C9A—C10A—C15A—C14A−179.8 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2Ai0.82 (4)1.96 (4)2.733 (3)155 (5)
O1A—H1B···O2ii0.79 (4)1.96 (4)2.732 (3)166 (5)
C5—H5A···O31.03 (3)2.60 (4)3.609 (4)168 (3)
C8—H8B···O30.972.573.120 (4)116
C8—H8A···O2Aiii0.972.593.255 (4)126
C5A—H5B···O4Aiv0.96 (4)2.46 (3)3.322 (3)150
C17A—H17D···O1v0.962.573.317 (5)135
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2Ai0.82 (4)1.96 (4)2.733 (3)155 (5)
O1A—H1B···O2ii0.79 (4)1.96 (4)2.732 (3)166 (5)
C5—H5A···O31.03 (3)2.60 (4)3.609 (4)168 (3)
C8—H8B···O30.972.573.120 (4)116
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.
Acknowledgements top

We acknowledge the financial support of the International Centre for Diffraction Data, Pennsylvania, USA.

references
References top

Lu, Y.-B., Zheng, Q.-T. & Lu, Y. (2006). Acta Cryst. E62, o469–o470.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2001). PLATON. University of Utrecht, The Netherlands.

Zhou, Z. H., Wang, J. L. & Yang, C. R. (2001). Chin. Tradit. Herb. Drugs, 32, 484–486.