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

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ISSN: 2414-3146

(10R,13R)-17-(6-Hy­dr­oxy-5-methyl­heptan-2-yl)-10,13-di­methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phen­anthren-3-ol hemihydrate: a bioactive steroid isolated from the Indian herb Artemisia reticulata

aBio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085, India, bInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and cAccident and Emergency Department, Franco Vietnamese Hospital, 7 Nguyen Luong Bang Street, Ho Chi Minh City, Vietnam
*Correspondence e-mail: nguyendonhuquynh@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 July 2017; accepted 24 July 2017; online 1 August 2017)

The title tetra­cyclic steroidal compound, C27H46O2·0.5H2O, crystallized as a monohydrate with two independent mol­ecules (1 and 2) in the asymmetric unit. In both mol­ecules, the conformations of the three cyclo­hexane rings (A, B and C) are chair, half-chair and chair, respectively. The fourth ring, D, has a twisted conformation on the bond linking the D and C rings. The crystal structure is stabilized by hydrogen bonding with the two independent mol­ecules being linked through the solvent water mol­ecule via various O—H⋯O hydrogen bonds, forming layers parallel to (-101).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound was isolated from a methanol extract of the herb A. reticulata (in local dialect Kirmani aajowan) by column chromatography (CC) over SiO2 gel by gradient solvent elution. This herb has been credited with different kinds of pharmacological activities, and has been used as a folklore medicine for conventional therapy against various ailments: malaria (Klayman et al., 1984[Klayman, D. L., Lin, A., Acton, N., Scovill, J. P., Hoch, J. M., Milhous, W. K., Theoharides, A. D. & Dobek, A. S. (1984). J. Nat. Prod. 47, 715-717.]; Malagon et al., 1997[Malagon, F., Vazquez, J., Delgado, G. & Ruiz, A. (1997). Parasitolgia, 39, 3-7.]; Newton & White, 1999[Newton, P. & White, N. (1999). Annu. Rev. Med. 50, 179-192.]), cancer (Efferth et al., 2001[Efferth, T., Dunstan, H., Sauerbrey, A., Miyachi, H. & Chitambar, C. R. (2001). Int. J. Oncol. 18, 767-773.]; Lai & Singh, 1995[Lai, H. & Singh, N. P. (1995). Cancer Lett. 91, 41-46.]), cardiovascular (Guantai & Addae-Mensah, 1999[Guantai, A. N. & Addae-Mensah, I. (1999). Pharm. Biol. 37, 351-356.]), vasodilatory (Walker, 1996[Walker, A. F. (1996). Biologist, 43, 177-180.]), hepatitis (Aniya et al., 2000[Aniya, Y., Shimabukuro, M., Shimoji, M., Kohatsu, M., Gyamfi, M. A., Miyagi, C., Kunii, D., Takayama, F. & Egashira, T. (2000). Biol. Pharm. Bull. 23, 309-312.]) and diabetes (Iriadam et al., 2006[Iriadam, M., Musa, D., Gumushan, H. & Baba, F. (2006). J. Cell. Mol. Biol. 5, 19-24.]). It is found as a major constituent in many ayurvedic and herbal drug preparations, such as forkolin, Afsanteen and others, in Indian traditional medicinal systems (Nadkarni, 1954[Nadkarni, A. K. (1954). Indian Materia Medica, 3rd ed. Bombay: Popular Prakashan.]; Satyavati et al., 1987[Satyavati, G. V., Gupta, A. & Tandon, N. (1987). Medicinal plants of India. New Delhi: ICMR.]; Subramoniam et al., 1996[Subramoniam, A., Pushpangadan, P., Rajasekharan, S., Evans, D. A., Latha, P. G. & Valsaraj, R. (1996). J. Ethnopharmacol. 50, 13-17.]; Drury, 1978[Drury, C. H. (1978). The Useful Plants of India (with notices of their chief value in commerce, medicine & the arts). London: William H. Allen & Co.]). The Artemisia species are a rich source of bioactive sesquiterpenenoids (Klayman et al., 1984[Klayman, D. L., Lin, A., Acton, N., Scovill, J. P., Hoch, J. M., Milhous, W. K., Theoharides, A. D. & Dobek, A. S. (1984). J. Nat. Prod. 47, 715-717.]), such as artemisin and artemisinin, and secondary metabolites isolated from A. annua (Klayman, 1985[Klayman, D. L. (1985). Science, 228, 1049-1055.]) exhibit anti­plasmodial activity (Li et al., 1982[Li, G., Guo, X., Jin, R., Wang, Z., Jian, H. & Li, Z. (1982). J. Tradit. Chin. Med. 2, 125-130.]). It is also under clinical trials to eradicate malaria.

We are looking for alternative abundant sources of artemisin and artemisinin from other varieties of Artemisia species. Unfortunately, phytochemical investigations revealed that the species of A. reticulata used by us did not possess the aforesaid terpenoids. Instead of that, a colourless solid substance was isolated as a minor constituent by column chromatographic separation. Herein, we report on the extraction and crystal structure of this minor colourless solid constituent assigned as a tetra­cyclic steroid based on chemical evidence. This solid substanti­ated the LB test (Liebermann Burchard Test), and a colour reaction on spraying with 10% aqueous H2SO4 onto a micro TLC plate followed by heating at 393 K for 5 min developed a pink-coloured spot on the TLC. These chemical tests revealed that the compound is a steroid. It shows a very close structural resemblance to the cyclo­penteno perhydro­phenanthreen skeleton viz. cholesterol (Craven, 1976[Craven, B. M. (1976). Nature, 260, 727-729.]; Marc, 1979[Marc, S. (1979). Ger. Offen. DE2732749 B219790628.]; Naora et al., 1986[Naora (nee Namikawa), M., Murae, T., Tsuyuki, T. & Takahashi, T. (1986). Bull. Chem. Soc. Jpn, 59, 1767-1976.]), but with different substituents.

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. It crystallizes as a monohydrate with two independent mol­ecules (1 and 2) in the asymmetric unit. The two mol­ecules are almost identical (Fig. 2[link]) and here the geometry will be described for mol­ecule 1 only. It has an alkyl (1-hy­droxy-2-iso­propyl­hex­yl) side chain located at atom C17 of the cyclo­pentane D ring. This side chain undergoes considerable thermal liberation and bond strain. The mol­ecule is composed of a series of fused rings (A, B, C and D). Rings A and C have chair conformations while ring B has a half-chair conformation, and the five-membered ring D is twisted on bond C13—C14. In addition to the tetra­cyclic moiety, two –CH3 groups are present at positions C5 and C13, at ring junctures A/B and C/D, respectively. At atom C2 in ring A there is an –OH group and in ring D the alkyl side chain, (1-hy­droxy-2-iso­propyl­hex­yl), at atom C17.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2]
Figure 2
An AutoMolFit view of mol­ecule 2 (red) on mol­ecule 1 (black).

There is total of eleven asymmetric centres in the title mol­ecule at various positions, such as C2, C5, C9, C10, C13, C14, C17, C20, C24 and C25. Among them, five asymmetric centres located at carbon atoms C2, C9, C10, C14, C25, and the remaining six chiral centres located at atoms C5, C13, C17, C20, C24, have relative S and R configurations, respectively; see Fig. 3[link].

[Figure 3]
Figure 3
A view of the chiral centres by symmetry equivalence of the two mol­ecules.

In the crystal, mol­ecules are linked via O—H⋯Owater, Owater—H⋯O and other O—H⋯O hydrogen bonds, forming layers lying parallel to ([\overline{1}]01); see Table 1[link] and Figs. 4[link] and 5[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3O⋯O1W 0.84 2.48 3.282 (11) 161
O1W—H11W⋯O3 0.91 (8) 2.45 (9) 3.282 (11) 151 (10)
O1W—H12W⋯O3i 0.87 (7) 2.07 (9) 2.834 (9) 147 (10)
O1—H1O⋯O3ii 0.84 1.94 2.766 (9) 169
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+1]; (ii) [-x+2, y-{\script{1\over 2}}, -z+1].
[Figure 4]
Figure 4
A view along the b axis of the crystal packing of the title compound (mol­ecule 1 blue, mol­ecule 2 red). The O—H⋯O hydrogen bonds are shown as dashed lines (Table 1[link]) and only the water mol­ecule and hy­droxy H atoms have been included.
[Figure 5]
Figure 5
A view along the a axis of the crystal packing of the title compound (mol­ecule 1 blue, mol­ecule 2 red). The O—H⋯O hydrogen bonds are shown as dashed lines (Table 1[link]), and only the water mol­ecule and hy­droxy H atoms have been included.

Synthesis and crystallization

The title steroid was isolated as a colourless solid from a methanol extract of A. reticulata by means of CC/SiO2 gel by gradient elution with a mixture of a binary solvent system, hexane and ethyl acetate. The desired compound was purified by reverse-phase high-pressure liquid chromatography. Suitable crystals for X-ray diffraction were obtained after being recrystallized three times from ethyl acetate:hexane (1:4) at room temperature by slow evaporation of the solvents.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. In both mol­ecules the alkyl (1-hy­droxy-2-iso­propyl­hex­yl) side chain located at atom C17 of the cyclo­pentane D ring undergoes considerable thermal liberation and bond strain, and it was necessary to use a number of ISOR, DELU and DFIX restraints during the refinement process. Nevertheless, the final R factors are still relatively high: R[F2 > 2σ(F2)] = 0.11 and wR(F2) = 0.32.

Table 2
Experimental details

Crystal data
Chemical formula C27H46O2·0.5H2O
Mr 411.64
Crystal system, space group Monoclinic, P21
Temperature (K) 150
a, b, c (Å) 9.4107 (8), 7.5175 (6), 36.979 (3)
β (°) 93.375 (8)
V3) 2611.5 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.06
Crystal size (mm) 0.32 × 0.28 × 0.12
 
Data collection
Diffractometer Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction Multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.])
Tmin, Tmax 0.980, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections 10852, 6720, 4382
Rint 0.048
(sin θ/λ)max−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.110, 0.319, 1.06
No. of reflections 6720
No. of parameters 538
No. of restraints 70
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.86, −0.40
Absolute structure Flack x determined using 911 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.1 (10)
Computer programs: CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]), SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(10R,13R)-17-(6-Hydroxy-5-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol hemihydrate top
Crystal data top
C27H46O2·0.5H2OF(000) = 916
Mr = 411.64Dx = 1.047 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.4107 (8) ÅCell parameters from 2353 reflections
b = 7.5175 (6) Åθ = 2.5–28.0°
c = 36.979 (3) ŵ = 0.06 mm1
β = 93.375 (8)°T = 150 K
V = 2611.5 (4) Å3Prism, colourless
Z = 40.32 × 0.28 × 0.12 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
4382 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.048
Rotation method data acquisition using ω scansθmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1110
Tmin = 0.980, Tmax = 0.992k = 69
10852 measured reflectionsl = 4443
6720 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.110H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.319 w = 1/[σ2(Fo2) + (0.1665P)2 + 5.0834P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6720 reflectionsΔρmax = 0.86 e Å3
538 parametersΔρmin = 0.40 e Å3
70 restraintsAbsolute structure: Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (10)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.2212 (7)0.5959 (10)0.51417 (15)0.0389 (17)
H1O1.29070.53400.52200.047*
O20.823 (2)0.891 (3)0.1325 (4)0.199 (8)
H2O0.77060.98080.12870.239*
C11.0884 (10)0.6980 (13)0.4597 (2)0.033 (2)
H1A1.10430.82390.46670.039*
H1B0.99960.65790.47030.039*
C21.2097 (9)0.5885 (13)0.4751 (2)0.030 (2)
H21.29990.63560.46580.036*
C31.1923 (10)0.3970 (14)0.4635 (2)0.034 (2)
H3A1.10500.34690.47320.041*
H3B1.27470.32640.47330.041*
C41.1819 (8)0.3852 (12)0.4217 (2)0.022 (2)
H4A1.16500.25970.41460.027*
H4B1.27440.42140.41260.027*
C51.0630 (8)0.5016 (11)0.4032 (2)0.0200 (18)
C61.0707 (9)0.6856 (13)0.4193 (2)0.028 (2)
C71.0664 (8)0.8326 (12)0.3990 (2)0.027 (2)
H71.07200.94370.41120.032*
C81.0535 (9)0.8360 (12)0.3582 (2)0.0228 (19)
H8A1.14730.86510.34890.027*
H8B0.98570.93050.35010.027*
C91.0025 (8)0.6589 (12)0.3425 (2)0.0208 (18)
H90.89900.64510.34660.025*
C101.0854 (8)0.5048 (11)0.3617 (2)0.0180 (18)
H101.18850.53110.35940.022*
C111.0569 (9)0.3277 (12)0.3426 (2)0.027 (2)
H11A0.95930.28850.34730.033*
H11B1.12380.23800.35340.033*
C121.0716 (8)0.3307 (12)0.3014 (2)0.0228 (19)
H12A1.04400.21350.29100.027*
H12B1.17220.35330.29630.027*
C130.9762 (8)0.4771 (13)0.2835 (2)0.026 (2)
C141.0230 (8)0.6501 (12)0.3018 (2)0.0221 (19)
H141.12790.65850.29920.027*
C150.9558 (10)0.7972 (12)0.2775 (2)0.030 (2)
H15A1.01220.90830.27970.036*
H15B0.85700.82230.28380.036*
C160.9591 (11)0.7173 (14)0.2386 (3)0.037 (2)
H16A0.86410.72800.22580.044*
H16B1.02880.78230.22450.044*
C171.0020 (9)0.5190 (12)0.2424 (2)0.025 (2)
H171.10660.51050.23930.030*
C180.9162 (8)0.4185 (14)0.4110 (2)0.031 (2)
H18A0.90970.29840.40070.038*
H18B0.90700.41230.43730.038*
H18C0.83970.49250.40000.038*
C190.8177 (8)0.4387 (13)0.2871 (2)0.028 (2)
H19A0.79250.32630.27490.033*
H19B0.79840.43000.31270.033*
H19C0.76090.53530.27580.033*
C200.9263 (10)0.4050 (14)0.2131 (2)0.033 (2)
H200.82220.41140.21690.039*
C210.9678 (11)0.2102 (14)0.2151 (2)0.041 (3)
H21A0.91570.14470.19560.049*
H21B1.07040.19860.21230.049*
H21C0.94420.16140.23850.049*
C220.9471 (12)0.4818 (16)0.1754 (2)0.045 (3)
H22A0.99360.59890.17920.054*
H22B1.01690.40420.16410.054*
C230.8380 (15)0.507 (2)0.1502 (3)0.080 (4)
H23A0.77250.59230.16100.095*
H23B0.78640.39200.14830.095*
C240.8551 (17)0.569 (2)0.1118 (3)0.082 (4)
H240.95870.58730.10840.099*
C250.778 (2)0.748 (3)0.1070 (4)0.107 (6)
H250.67570.72370.11120.129*
C260.780 (2)0.818 (3)0.0665 (5)0.146 (8)
H26A0.75020.72180.04970.175*
H26B0.71490.91860.06300.175*
H26C0.87690.85550.06160.175*
C270.798 (3)0.423 (3)0.0849 (5)0.195 (11)
H27A0.80860.46230.06000.234*
H27B0.85140.31230.08930.234*
H27C0.69670.40100.08850.234*
O30.5647 (7)0.8560 (10)0.46662 (15)0.0392 (17)
H3O0.56450.74920.47330.047*
O40.297 (4)0.608 (6)0.0743 (10)0.45 (2)
H4O0.34960.63160.09280.535*
C280.5988 (11)0.7558 (14)0.4054 (2)0.039 (3)
H28A0.59390.62990.41310.047*
H28B0.69940.79400.40830.047*
C290.5111 (10)0.8677 (13)0.4296 (2)0.030 (2)
H290.41150.82090.42790.036*
C300.5077 (10)1.0581 (13)0.4164 (2)0.028 (2)
H30A0.60501.10850.41860.033*
H30B0.44661.12990.43170.033*
C310.4496 (8)1.0675 (12)0.3768 (2)0.0229 (19)
H31A0.44991.19320.36880.027*
H31B0.34951.02610.37540.027*
C320.5349 (8)0.9554 (12)0.3506 (2)0.0191 (19)
C330.5488 (10)0.7694 (12)0.3656 (2)0.028 (2)
C340.5214 (9)0.6197 (12)0.3461 (2)0.027 (2)
H340.53250.50780.35790.032*
C350.4745 (8)0.6239 (11)0.3068 (2)0.0215 (19)
H35A0.52430.52830.29420.026*
H35B0.37120.59820.30430.026*
C360.5019 (9)0.7967 (12)0.2887 (2)0.0225 (19)
H360.60660.80820.28610.027*
C370.4521 (8)0.9557 (12)0.3122 (2)0.0194 (18)
H370.34960.93400.31650.023*
C380.4590 (9)1.1335 (12)0.2924 (2)0.0233 (19)
H38A0.41301.22600.30680.028*
H38B0.56001.16760.29070.028*
C390.3867 (10)1.1291 (13)0.2544 (2)0.030 (2)
H39A0.39861.24610.24270.036*
H39B0.28351.10810.25610.036*
C400.4477 (8)0.9850 (13)0.2310 (2)0.026 (2)
C410.4258 (9)0.8085 (13)0.2510 (2)0.027 (2)
H410.32160.80070.25480.033*
C420.4571 (11)0.6626 (16)0.2235 (2)0.042 (3)
H42A0.40690.55060.22880.050*
H42B0.56050.63880.22320.050*
C430.3979 (12)0.7470 (14)0.1874 (3)0.046 (3)
H43A0.31070.68340.17840.056*
H43B0.46930.73690.16890.056*
C440.3630 (10)0.9462 (15)0.1939 (2)0.038 (2)
H440.25920.95500.19800.046*
C450.6833 (8)1.0364 (15)0.3488 (2)0.032 (2)
H45A0.67501.15740.33910.038*
H45B0.73001.04020.37320.038*
H45C0.73990.96360.33300.038*
C460.6025 (9)1.0197 (14)0.2246 (2)0.034 (2)
H46A0.63860.92460.20950.041*
H46B0.61131.13410.21220.041*
H46C0.65801.02280.24780.041*
C470.3906 (10)1.0561 (15)0.1608 (2)0.036 (2)
H470.49241.03800.15530.044*
C480.3685 (15)1.2558 (16)0.1667 (3)0.061 (4)
H48A0.38771.32050.14450.073*
H48B0.27001.27740.17270.073*
H48C0.43361.29710.18660.073*
C490.2989 (12)0.9932 (19)0.1280 (2)0.056 (3)
H49A0.27390.86790.13290.068*
H49B0.20921.06180.12810.068*
C500.3399 (17)0.998 (3)0.0938 (3)0.122 (8)
H50A0.43250.93510.09400.146*
H50B0.35981.12420.08840.146*
C510.252 (2)0.927 (3)0.0612 (4)0.110 (6)
H510.15060.91380.06760.132*
C520.306 (4)0.749 (4)0.0484 (9)0.210 (14)
H520.40630.76210.04140.253*
C530.215 (4)0.667 (6)0.0166 (9)0.30 (2)
H53A0.20980.74930.00390.359*
H53B0.25780.55460.00940.359*
H53C0.11830.64380.02430.359*
C540.259 (3)1.059 (4)0.0312 (7)0.241 (14)
H54A0.22461.17490.03920.290*
H54B0.35821.07140.02460.290*
H54C0.20011.01890.01010.290*
O1W0.6405 (9)0.4363 (12)0.4827 (2)0.055 (2)
H11W0.618 (11)0.552 (11)0.487 (3)0.066*
H12W0.566 (10)0.385 (14)0.491 (3)0.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.054 (4)0.043 (5)0.019 (3)0.005 (4)0.003 (3)0.000 (3)
O20.225 (14)0.192 (16)0.179 (13)0.031 (13)0.006 (11)0.043 (12)
C10.048 (6)0.030 (6)0.020 (4)0.005 (5)0.003 (4)0.006 (4)
C20.032 (5)0.030 (6)0.028 (5)0.001 (4)0.002 (4)0.003 (4)
C30.041 (5)0.034 (6)0.025 (5)0.002 (5)0.001 (4)0.002 (4)
C40.029 (5)0.019 (5)0.019 (4)0.003 (4)0.004 (3)0.001 (4)
C50.018 (4)0.010 (4)0.032 (4)0.005 (3)0.001 (3)0.001 (4)
C60.025 (5)0.023 (5)0.035 (5)0.001 (4)0.004 (4)0.000 (4)
C70.027 (5)0.016 (5)0.039 (5)0.002 (4)0.003 (4)0.010 (4)
C80.020 (4)0.018 (5)0.030 (4)0.002 (4)0.001 (3)0.004 (4)
C90.015 (4)0.013 (5)0.035 (5)0.003 (4)0.004 (3)0.002 (4)
C100.014 (4)0.011 (4)0.029 (4)0.001 (3)0.001 (3)0.001 (4)
C110.029 (5)0.013 (5)0.039 (5)0.003 (4)0.003 (4)0.002 (4)
C120.020 (4)0.018 (5)0.030 (4)0.006 (4)0.000 (3)0.001 (4)
C130.018 (4)0.030 (6)0.030 (5)0.003 (4)0.000 (3)0.001 (4)
C140.014 (4)0.025 (5)0.027 (4)0.003 (4)0.001 (3)0.007 (4)
C150.040 (5)0.014 (5)0.035 (5)0.009 (4)0.001 (4)0.004 (4)
C160.040 (6)0.034 (6)0.037 (5)0.002 (5)0.001 (4)0.008 (5)
C170.022 (4)0.029 (6)0.025 (4)0.000 (4)0.009 (3)0.004 (4)
C180.026 (5)0.044 (6)0.025 (4)0.002 (5)0.009 (3)0.004 (5)
C190.026 (5)0.029 (5)0.029 (4)0.005 (4)0.008 (4)0.004 (4)
C200.036 (5)0.040 (6)0.023 (4)0.004 (5)0.000 (4)0.003 (4)
C210.058 (7)0.040 (7)0.023 (5)0.008 (5)0.010 (4)0.000 (5)
C220.074 (7)0.037 (7)0.025 (5)0.012 (6)0.002 (5)0.006 (5)
C230.103 (11)0.090 (12)0.044 (7)0.002 (9)0.004 (7)0.010 (8)
C240.096 (8)0.101 (9)0.049 (6)0.007 (8)0.011 (6)0.004 (7)
C250.136 (10)0.112 (11)0.073 (8)0.008 (9)0.003 (8)0.013 (8)
C260.208 (17)0.143 (17)0.085 (11)0.000 (15)0.002 (11)0.011 (12)
C270.32 (2)0.19 (2)0.080 (11)0.030 (18)0.003 (14)0.006 (14)
O30.057 (4)0.038 (4)0.022 (3)0.005 (4)0.001 (3)0.010 (3)
O40.45 (3)0.45 (3)0.43 (3)0.03 (2)0.00 (2)0.03 (2)
C280.065 (7)0.021 (6)0.028 (5)0.002 (5)0.011 (5)0.009 (4)
C290.036 (5)0.032 (6)0.023 (4)0.009 (4)0.004 (4)0.000 (4)
C300.035 (5)0.023 (5)0.026 (4)0.003 (4)0.005 (4)0.003 (4)
C310.027 (4)0.014 (5)0.028 (4)0.008 (4)0.009 (3)0.004 (4)
C320.015 (4)0.022 (5)0.020 (4)0.007 (4)0.003 (3)0.001 (4)
C330.046 (5)0.017 (5)0.019 (4)0.001 (4)0.003 (4)0.007 (4)
C340.031 (5)0.006 (5)0.042 (5)0.007 (4)0.001 (4)0.004 (4)
C350.021 (4)0.014 (5)0.030 (4)0.006 (4)0.002 (3)0.000 (4)
C360.032 (5)0.013 (5)0.023 (4)0.002 (4)0.002 (4)0.010 (4)
C370.017 (4)0.020 (5)0.022 (4)0.001 (4)0.008 (3)0.006 (4)
C380.036 (5)0.013 (5)0.021 (4)0.011 (4)0.005 (3)0.001 (4)
C390.044 (5)0.022 (5)0.024 (4)0.008 (5)0.004 (4)0.007 (4)
C400.021 (4)0.032 (6)0.025 (4)0.008 (4)0.001 (3)0.002 (4)
C410.026 (5)0.024 (5)0.031 (5)0.001 (4)0.006 (4)0.007 (4)
C420.055 (6)0.040 (7)0.030 (5)0.004 (6)0.001 (4)0.012 (5)
C430.067 (7)0.034 (7)0.036 (5)0.000 (6)0.012 (5)0.009 (5)
C440.041 (6)0.039 (6)0.033 (5)0.003 (5)0.008 (4)0.004 (5)
C450.020 (4)0.053 (7)0.023 (4)0.001 (5)0.003 (3)0.004 (5)
C460.037 (5)0.034 (6)0.030 (5)0.003 (5)0.003 (4)0.000 (4)
C470.040 (6)0.041 (7)0.029 (5)0.006 (5)0.006 (4)0.002 (5)
C480.098 (10)0.045 (8)0.039 (6)0.020 (7)0.004 (6)0.007 (6)
C490.076 (8)0.064 (9)0.027 (5)0.018 (7)0.013 (5)0.000 (6)
C500.109 (12)0.22 (3)0.039 (7)0.054 (15)0.007 (7)0.017 (11)
C510.133 (10)0.127 (11)0.068 (8)0.000 (9)0.016 (7)0.005 (8)
C520.217 (16)0.211 (17)0.200 (16)0.007 (11)0.012 (11)0.008 (11)
C530.32 (3)0.30 (3)0.27 (3)0.03 (2)0.02 (2)0.00 (2)
C540.33 (2)0.23 (2)0.164 (18)0.06 (2)0.052 (17)0.005 (18)
O1W0.069 (5)0.046 (5)0.052 (4)0.006 (5)0.021 (4)0.014 (4)
Geometric parameters (Å, º) top
O1—C21.442 (9)O3—H3O0.8400
O1—H1O0.8400O4—C521.43 (2)
O2—C251.479 (17)O4—H4O0.8400
O2—H2O0.8400C28—C291.508 (13)
C1—C21.493 (12)C28—C331.520 (11)
C1—C61.500 (11)C28—H28A0.9900
C1—H1A0.9900C28—H28B0.9900
C1—H1B0.9900C29—C301.511 (13)
C2—C31.510 (13)C29—H291.0000
C2—H21.0000C30—C311.534 (11)
C3—C41.543 (10)C30—H30A0.9900
C3—H3A0.9900C30—H30B0.9900
C3—H3B0.9900C31—C321.545 (11)
C4—C51.548 (11)C31—H31A0.9900
C4—H4A0.9900C31—H31B0.9900
C4—H4B0.9900C32—C331.508 (12)
C5—C61.504 (12)C32—C451.528 (11)
C5—C181.559 (11)C32—C371.579 (10)
C5—C101.561 (11)C33—C341.353 (12)
C6—C71.335 (12)C34—C351.495 (11)
C7—C81.504 (11)C34—H340.9500
C7—H70.9500C35—C361.491 (12)
C8—C91.518 (12)C35—H35A0.9900
C8—H8A0.9900C35—H35B0.9900
C8—H8B0.9900C36—C411.531 (11)
C9—C141.532 (11)C36—C371.566 (11)
C9—C101.546 (11)C36—H361.0000
C9—H91.0000C37—C381.528 (11)
C10—C111.524 (12)C37—H371.0000
C10—H101.0000C38—C391.526 (11)
C11—C121.537 (11)C38—H38A0.9900
C11—H11A0.9900C38—H38B0.9900
C11—H11B0.9900C39—C401.519 (12)
C12—C131.545 (12)C39—H39A0.9900
C12—H12A0.9900C39—H39B0.9900
C12—H12B0.9900C40—C461.513 (12)
C13—C141.519 (13)C40—C411.538 (13)
C13—C191.532 (11)C40—C441.574 (11)
C13—C171.585 (11)C41—C421.536 (13)
C14—C151.537 (11)C41—H411.0000
C14—H141.0000C42—C431.553 (13)
C15—C161.560 (13)C42—H42A0.9900
C15—H15A0.9900C42—H42B0.9900
C15—H15B0.9900C43—C441.555 (15)
C16—C171.549 (13)C43—H43A0.9900
C16—H16A0.9900C43—H43B0.9900
C16—H16B0.9900C44—C471.513 (13)
C17—C201.525 (12)C44—H441.0000
C17—H171.0000C45—H45A0.9800
C18—H18A0.9800C45—H45B0.9800
C18—H18B0.9800C45—H45C0.9800
C18—H18C0.9800C46—H46A0.9800
C19—H19A0.9800C46—H46B0.9800
C19—H19B0.9800C46—H46C0.9800
C19—H19C0.9800C47—C491.520 (13)
C20—C211.516 (14)C47—C481.533 (15)
C20—C221.530 (13)C47—H471.0000
C20—H201.0000C48—H48A0.9800
C21—H21A0.9800C48—H48B0.9800
C21—H21B0.9800C48—H48C0.9800
C21—H21C0.9800C49—C501.346 (15)
C22—C231.358 (15)C49—H49A0.9900
C22—H22A0.9900C49—H49B0.9900
C22—H22B0.9900C50—C511.52 (2)
C23—C241.514 (17)C50—H50A0.9900
C23—H23A0.9900C50—H50B0.9900
C23—H23B0.9900C51—C541.496 (19)
C24—C271.559 (18)C51—C521.51 (2)
C24—C251.54 (2)C51—H511.0000
C24—H241.0000C52—C531.54 (2)
C25—C261.59 (2)C52—H521.0000
C25—H251.0000C53—H53A0.9800
C26—H26A0.9800C53—H53B0.9800
C26—H26B0.9800C53—H53C0.9800
C26—H26C0.9800C54—H54A0.9800
C27—H27A0.9800C54—H54B0.9800
C27—H27B0.9800C54—H54C0.9800
C27—H27C0.9800O1W—H11W0.91 (8)
O3—C291.435 (10)O1W—H12W0.87 (7)
C2—O1—H1O109.5C52—O4—H4O109.5
C25—O2—H2O109.5C29—C28—C33112.7 (8)
C2—C1—C6112.6 (7)C29—C28—H28A109.0
C2—C1—H1A109.1C33—C28—H28A109.0
C6—C1—H1A109.1C29—C28—H28B109.0
C2—C1—H1B109.1C33—C28—H28B109.0
C6—C1—H1B109.1H28A—C28—H28B107.8
H1A—C1—H1B107.8O3—C29—C28111.0 (7)
O1—C2—C1111.8 (7)O3—C29—C30111.4 (7)
O1—C2—C3108.9 (8)C28—C29—C30109.9 (7)
C1—C2—C3110.4 (8)O3—C29—H29108.2
O1—C2—H2108.6C28—C29—H29108.2
C1—C2—H2108.6C30—C29—H29108.2
C3—C2—H2108.6C29—C30—C31110.5 (7)
C2—C3—C4109.9 (8)C29—C30—H30A109.6
C2—C3—H3A109.7C31—C30—H30A109.6
C4—C3—H3A109.7C29—C30—H30B109.6
C2—C3—H3B109.7C31—C30—H30B109.6
C4—C3—H3B109.7H30A—C30—H30B108.1
H3A—C3—H3B108.2C30—C31—C32113.9 (7)
C3—C4—C5114.3 (7)C30—C31—H31A108.8
C3—C4—H4A108.7C32—C31—H31A108.8
C5—C4—H4A108.7C30—C31—H31B108.8
C3—C4—H4B108.7C32—C31—H31B108.8
C5—C4—H4B108.7H31A—C31—H31B107.7
H4A—C4—H4B107.6C33—C32—C45109.0 (7)
C6—C5—C18108.6 (7)C33—C32—C31108.1 (7)
C6—C5—C4109.2 (7)C45—C32—C31108.7 (7)
C18—C5—C4108.5 (7)C33—C32—C37111.1 (7)
C6—C5—C10111.5 (7)C45—C32—C37111.4 (6)
C18—C5—C10111.1 (6)C31—C32—C37108.5 (6)
C4—C5—C10107.9 (6)C34—C33—C28119.8 (8)
C7—C6—C1120.5 (9)C34—C33—C32124.4 (7)
C7—C6—C5122.7 (8)C28—C33—C32115.7 (8)
C1—C6—C5116.8 (8)C33—C34—C35122.5 (8)
C6—C7—C8125.1 (8)C33—C34—H34118.8
C6—C7—H7117.5C35—C34—H34118.8
C8—C7—H7117.5C36—C35—C34114.0 (7)
C7—C8—C9111.9 (7)C36—C35—H35A108.8
C7—C8—H8A109.2C34—C35—H35A108.8
C9—C8—H8A109.2C36—C35—H35B108.8
C7—C8—H8B109.2C34—C35—H35B108.8
C9—C8—H8B109.2H35A—C35—H35B107.7
H8A—C8—H8B107.9C35—C36—C41112.1 (7)
C8—C9—C14111.1 (7)C35—C36—C37110.5 (6)
C8—C9—C10110.0 (6)C41—C36—C37108.8 (7)
C14—C9—C10109.3 (6)C35—C36—H36108.5
C8—C9—H9108.8C41—C36—H36108.5
C14—C9—H9108.8C37—C36—H36108.5
C10—C9—H9108.8C38—C37—C36112.3 (6)
C11—C10—C9111.8 (6)C38—C37—C32113.5 (7)
C11—C10—C5114.4 (7)C36—C37—C32110.5 (6)
C9—C10—C5111.7 (6)C38—C37—H37106.7
C11—C10—H10106.1C36—C37—H37106.7
C9—C10—H10106.1C32—C37—H37106.7
C5—C10—H10106.1C39—C38—C37113.2 (7)
C10—C11—C12115.0 (7)C39—C38—H38A108.9
C10—C11—H11A108.5C37—C38—H38A108.9
C12—C11—H11A108.5C39—C38—H38B108.9
C10—C11—H11B108.5C37—C38—H38B108.9
C12—C11—H11B108.5H38A—C38—H38B107.8
H11A—C11—H11B107.5C38—C39—C40112.1 (7)
C11—C12—C13110.7 (7)C38—C39—H39A109.2
C11—C12—H12A109.5C40—C39—H39A109.2
C13—C12—H12A109.5C38—C39—H39B109.2
C11—C12—H12B109.5C40—C39—H39B109.2
C13—C12—H12B109.5H39A—C39—H39B107.9
H12A—C12—H12B108.1C46—C40—C39111.5 (8)
C14—C13—C19112.4 (7)C46—C40—C41112.5 (7)
C14—C13—C12105.8 (6)C39—C40—C41106.0 (7)
C19—C13—C12111.9 (8)C46—C40—C44109.7 (7)
C14—C13—C17101.5 (7)C39—C40—C44116.0 (7)
C19—C13—C17109.0 (6)C41—C40—C44100.6 (7)
C12—C13—C17115.8 (7)C42—C41—C36117.6 (8)
C13—C14—C9115.2 (7)C42—C41—C40105.2 (7)
C13—C14—C15104.9 (6)C36—C41—C40114.7 (7)
C9—C14—C15118.2 (7)C42—C41—H41106.2
C13—C14—H14105.9C36—C41—H41106.2
C9—C14—H14105.9C40—C41—H41106.2
C15—C14—H14105.9C41—C42—C43101.8 (8)
C14—C15—C16103.4 (7)C41—C42—H42A111.4
C14—C15—H15A111.1C43—C42—H42A111.4
C16—C15—H15A111.1C41—C42—H42B111.4
C14—C15—H15B111.1C43—C42—H42B111.4
C16—C15—H15B111.1H42A—C42—H42B109.3
H15A—C15—H15B109.1C42—C43—C44109.2 (8)
C17—C16—C15107.9 (7)C42—C43—H43A109.8
C17—C16—H16A110.1C44—C43—H43A109.8
C15—C16—H16A110.1C42—C43—H43B109.8
C17—C16—H16B110.1C44—C43—H43B109.8
C15—C16—H16B110.1H43A—C43—H43B108.3
H16A—C16—H16B108.4C47—C44—C43110.6 (8)
C20—C17—C16111.7 (7)C47—C44—C40120.2 (9)
C20—C17—C13118.6 (7)C43—C44—C40102.3 (8)
C16—C17—C13102.9 (7)C47—C44—H44107.7
C20—C17—H17107.7C43—C44—H44107.7
C16—C17—H17107.7C40—C44—H44107.7
C13—C17—H17107.7C32—C45—H45A109.5
C5—C18—H18A109.5C32—C45—H45B109.5
C5—C18—H18B109.5H45A—C45—H45B109.5
H18A—C18—H18B109.5C32—C45—H45C109.5
C5—C18—H18C109.5H45A—C45—H45C109.5
H18A—C18—H18C109.5H45B—C45—H45C109.5
H18B—C18—H18C109.5C40—C46—H46A109.5
C13—C19—H19A109.5C40—C46—H46B109.5
C13—C19—H19B109.5H46A—C46—H46B109.5
H19A—C19—H19B109.5C40—C46—H46C109.5
C13—C19—H19C109.5H46A—C46—H46C109.5
H19A—C19—H19C109.5H46B—C46—H46C109.5
H19B—C19—H19C109.5C44—C47—C49111.0 (9)
C21—C20—C17113.6 (7)C44—C47—C48112.8 (9)
C21—C20—C22111.3 (8)C49—C47—C48110.0 (10)
C17—C20—C22110.8 (8)C44—C47—H47107.6
C21—C20—H20106.9C49—C47—H47107.6
C17—C20—H20106.9C48—C47—H47107.6
C22—C20—H20106.9C47—C48—H48A109.5
C20—C21—H21A109.5C47—C48—H48B109.5
C20—C21—H21B109.5H48A—C48—H48B109.5
H21A—C21—H21B109.5C47—C48—H48C109.5
C20—C21—H21C109.5H48A—C48—H48C109.5
H21A—C21—H21C109.5H48B—C48—H48C109.5
H21B—C21—H21C109.5C50—C49—C47124.1 (12)
C23—C22—C20123.0 (11)C50—C49—H49A106.3
C23—C22—H22A106.6C47—C49—H49A106.3
C20—C22—H22A106.6C50—C49—H49B106.3
C23—C22—H22B106.6C47—C49—H49B106.3
C20—C22—H22B106.6H49A—C49—H49B106.4
H22A—C22—H22B106.5C49—C50—C51124.3 (14)
C22—C23—C24124.6 (13)C49—C50—H50A106.2
C22—C23—H23A106.2C51—C50—H50A106.2
C24—C23—H23A106.2C49—C50—H50B106.2
C22—C23—H23B106.2C51—C50—H50B106.2
C24—C23—H23B106.2H50A—C50—H50B106.4
H23A—C23—H23B106.4C54—C51—C52109 (2)
C27—C24—C23109.2 (14)C54—C51—C50107.9 (18)
C27—C24—C25113.6 (14)C52—C51—C50112 (2)
C23—C24—C25107.7 (13)C54—C51—H51109.2
C27—C24—H24108.7C52—C51—H51109.2
C23—C24—H24108.7C50—C51—H51109.2
C25—C24—H24108.7O4—C52—C51114 (3)
O2—C25—C26110.1 (17)O4—C52—C5399 (3)
O2—C25—C24116.7 (14)C51—C52—C53114 (3)
C26—C25—C24111.5 (15)O4—C52—H52109.6
O2—C25—H25106.0C51—C52—H52109.6
C26—C25—H25106.0C53—C52—H52109.6
C24—C25—H25106.0C52—C53—H53A109.5
C25—C26—H26A109.5C52—C53—H53B109.5
C25—C26—H26B109.5H53A—C53—H53B109.5
H26A—C26—H26B109.5C52—C53—H53C109.5
C25—C26—H26C109.5H53A—C53—H53C109.5
H26A—C26—H26C109.5H53B—C53—H53C109.5
H26B—C26—H26C109.5C51—C54—H54A109.5
C24—C27—H27A109.5C51—C54—H54B109.5
C24—C27—H27B109.5H54A—C54—H54B109.5
H27A—C27—H27B109.5C51—C54—H54C109.5
C24—C27—H27C109.5H54A—C54—H54C109.5
H27A—C27—H27C109.5H54B—C54—H54C109.5
H27B—C27—H27C109.5H11W—O1W—H12W99 (8)
C29—O3—H3O109.5
C6—C1—C2—O1177.4 (8)C33—C28—C29—O3178.0 (8)
C6—C1—C2—C356.1 (11)C33—C28—C29—C3054.3 (11)
O1—C2—C3—C4179.2 (6)O3—C29—C30—C31179.8 (6)
C1—C2—C3—C457.7 (10)C28—C29—C30—C3156.8 (10)
C2—C3—C4—C555.2 (10)C29—C30—C31—C3257.6 (10)
C3—C4—C5—C647.6 (10)C30—C31—C32—C3351.7 (9)
C3—C4—C5—C1870.6 (9)C30—C31—C32—C4566.6 (9)
C3—C4—C5—C10169.0 (7)C30—C31—C32—C37172.2 (7)
C2—C1—C6—C7126.5 (10)C29—C28—C33—C34128.1 (10)
C2—C1—C6—C551.6 (11)C29—C28—C33—C3252.5 (11)
C18—C5—C6—C7109.5 (9)C45—C32—C33—C34110.2 (10)
C4—C5—C6—C7132.4 (8)C31—C32—C33—C34131.8 (9)
C10—C5—C6—C713.2 (11)C37—C32—C33—C3412.9 (12)
C18—C5—C6—C172.4 (9)C45—C32—C33—C2869.1 (10)
C4—C5—C6—C145.7 (10)C31—C32—C33—C2848.9 (10)
C10—C5—C6—C1164.9 (7)C37—C32—C33—C28167.8 (7)
C1—C6—C7—C8178.1 (7)C28—C33—C34—C35178.9 (8)
C5—C6—C7—C80.1 (13)C32—C33—C34—C350.3 (14)
C6—C7—C8—C916.8 (11)C33—C34—C35—C3617.4 (12)
C7—C8—C9—C14166.8 (6)C34—C35—C36—C41168.3 (7)
C7—C8—C9—C1045.6 (9)C34—C35—C36—C3746.9 (9)
C8—C9—C10—C11170.0 (7)C35—C36—C37—C38172.1 (7)
C14—C9—C10—C1147.8 (9)C41—C36—C37—C3848.7 (9)
C8—C9—C10—C560.4 (8)C35—C36—C37—C3260.0 (9)
C14—C9—C10—C5177.4 (6)C41—C36—C37—C32176.6 (7)
C6—C5—C10—C11171.2 (7)C33—C32—C37—C38169.0 (7)
C18—C5—C10—C1150.0 (9)C45—C32—C37—C3847.2 (9)
C4—C5—C10—C1168.8 (9)C31—C32—C37—C3872.3 (8)
C6—C5—C10—C943.0 (9)C33—C32—C37—C3641.8 (9)
C18—C5—C10—C978.3 (9)C45—C32—C37—C3680.0 (9)
C4—C5—C10—C9162.9 (6)C31—C32—C37—C36160.5 (7)
C9—C10—C11—C1249.0 (9)C36—C37—C38—C3950.1 (9)
C5—C10—C11—C12177.3 (6)C32—C37—C38—C39176.4 (6)
C10—C11—C12—C1354.7 (9)C37—C38—C39—C4056.3 (10)
C11—C12—C13—C1457.5 (8)C38—C39—C40—C4664.1 (10)
C11—C12—C13—C1965.1 (9)C38—C39—C40—C4158.7 (9)
C11—C12—C13—C17169.1 (7)C38—C39—C40—C44169.4 (8)
C19—C13—C14—C960.0 (9)C35—C36—C41—C4256.5 (11)
C12—C13—C14—C962.3 (8)C37—C36—C41—C42178.9 (8)
C17—C13—C14—C9176.3 (6)C35—C36—C41—C40179.1 (7)
C19—C13—C14—C1571.7 (8)C37—C36—C41—C4056.7 (9)
C12—C13—C14—C15166.0 (7)C46—C40—C41—C4269.9 (9)
C17—C13—C14—C1544.6 (8)C39—C40—C41—C42167.9 (7)
C8—C9—C14—C13179.5 (6)C44—C40—C41—C4246.7 (8)
C10—C9—C14—C1358.0 (8)C46—C40—C41—C3660.8 (9)
C8—C9—C14—C1555.4 (9)C39—C40—C41—C3661.3 (9)
C10—C9—C14—C15176.9 (7)C44—C40—C41—C36177.5 (7)
C13—C14—C15—C1634.1 (8)C36—C41—C42—C43164.7 (8)
C9—C14—C15—C16164.0 (7)C40—C41—C42—C4335.7 (9)
C14—C15—C16—C179.8 (9)C41—C42—C43—C4410.8 (11)
C15—C16—C17—C20145.0 (7)C42—C43—C44—C47146.2 (9)
C15—C16—C17—C1316.7 (9)C42—C43—C44—C4017.0 (11)
C14—C13—C17—C20160.9 (7)C46—C40—C44—C4742.0 (12)
C19—C13—C17—C2042.1 (11)C39—C40—C44—C4785.5 (11)
C12—C13—C17—C2085.1 (9)C41—C40—C44—C47160.7 (9)
C14—C13—C17—C1637.1 (8)C46—C40—C44—C4381.0 (10)
C19—C13—C17—C1681.6 (9)C39—C40—C44—C43151.6 (9)
C12—C13—C17—C16151.1 (8)C41—C40—C44—C4337.7 (9)
C16—C17—C20—C21178.6 (8)C43—C44—C47—C4960.2 (11)
C13—C17—C20—C2162.1 (11)C40—C44—C47—C49179.0 (9)
C16—C17—C20—C2252.5 (10)C43—C44—C47—C48175.8 (9)
C13—C17—C20—C22171.8 (8)C40—C44—C47—C4856.9 (13)
C21—C20—C22—C23101.2 (14)C44—C47—C49—C50146.9 (16)
C17—C20—C22—C23131.5 (13)C48—C47—C49—C5087.5 (18)
C20—C22—C23—C24175.1 (13)C47—C49—C50—C51176.9 (17)
C22—C23—C24—C27118.7 (18)C49—C50—C51—C54137 (2)
C22—C23—C24—C25117.5 (17)C49—C50—C51—C52103 (3)
C27—C24—C25—O2177.7 (17)C54—C51—C52—O4177 (3)
C23—C24—C25—O257 (2)C50—C51—C52—O464 (4)
C27—C24—C25—C2655 (2)C54—C51—C52—C5364 (3)
C23—C24—C25—C26175.8 (14)C50—C51—C52—C53177 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O1W0.842.483.282 (11)161
O1W—H11W···O30.91 (8)2.45 (9)3.282 (11)151 (10)
O1W—H12W···O3i0.87 (7)2.07 (9)2.834 (9)147 (10)
O1—H1O···O3ii0.841.942.766 (9)169
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+2, y1/2, z+1.
 

Acknowledgements

The authors thank Professor Dr Hartmut, FG Strukturforschung, Material-und Geowissenschaften, Technische Universit at Darmstadt, and Professor Kingston, Department of Chemistry, Virginia Polytechnic Institute and State University, USA, for their kind co-operation to record XRD of the crystal, for providing diffractometer time and for carrying out the anti­proliferative bioassay against the cancer cell line.

References

First citationAniya, Y., Shimabukuro, M., Shimoji, M., Kohatsu, M., Gyamfi, M. A., Miyagi, C., Kunii, D., Takayama, F. & Egashira, T. (2000). Biol. Pharm. Bull. 23, 309–312.  CrossRef PubMed CAS Google Scholar
First citationCraven, B. M. (1976). Nature, 260, 727–729.  CrossRef PubMed CAS Web of Science Google Scholar
First citationDrury, C. H. (1978). The Useful Plants of India (with notices of their chief value in commerce, medicine & the arts). London: William H. Allen & Co.  Google Scholar
First citationEfferth, T., Dunstan, H., Sauerbrey, A., Miyachi, H. & Chitambar, C. R. (2001). Int. J. Oncol. 18, 767–773.  Web of Science PubMed CAS Google Scholar
First citationGuantai, A. N. & Addae-Mensah, I. (1999). Pharm. Biol. 37, 351–356.  Web of Science CrossRef CAS Google Scholar
First citationIriadam, M., Musa, D., Gumushan, H. & Baba, F. (2006). J. Cell. Mol. Biol. 5, 19–24.  Google Scholar
First citationKlayman, D. L. (1985). Science, 228, 1049–1055.  CrossRef CAS PubMed Web of Science Google Scholar
First citationKlayman, D. L., Lin, A., Acton, N., Scovill, J. P., Hoch, J. M., Milhous, W. K., Theoharides, A. D. & Dobek, A. S. (1984). J. Nat. Prod. 47, 715–717.  CrossRef CAS PubMed Web of Science Google Scholar
First citationLai, H. & Singh, N. P. (1995). Cancer Lett. 91, 41–46.  CrossRef CAS PubMed Web of Science Google Scholar
First citationLi, G., Guo, X., Jin, R., Wang, Z., Jian, H. & Li, Z. (1982). J. Tradit. Chin. Med. 2, 125–130.  CAS PubMed Google Scholar
First citationMalagon, F., Vazquez, J., Delgado, G. & Ruiz, A. (1997). Parasitolgia, 39, 3–7.  CAS Google Scholar
First citationMarc, S. (1979). Ger. Offen. DE2732749 B219790628.  Google Scholar
First citationNadkarni, A. K. (1954). Indian Materia Medica, 3rd ed. Bombay: Popular Prakashan.  Google Scholar
First citationNaora (nee Namikawa), M., Murae, T., Tsuyuki, T. & Takahashi, T. (1986). Bull. Chem. Soc. Jpn, 59, 1767–1976.  Google Scholar
First citationNewton, P. & White, N. (1999). Annu. Rev. Med. 50, 179–192.  CrossRef PubMed CAS Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSatyavati, G. V., Gupta, A. & Tandon, N. (1987). Medicinal plants of India. New Delhi: ICMR.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSubramoniam, A., Pushpangadan, P., Rajasekharan, S., Evans, D. A., Latha, P. G. & Valsaraj, R. (1996). J. Ethnopharmacol. 50, 13–17.  CrossRef CAS PubMed Web of Science Google Scholar
First citationWalker, A. F. (1996). Biologist, 43, 177–180.  Google Scholar

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