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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 66| Part 8| August 2010| Page o2003
https://doi.org/10.1107/S1600536810026516

3β,11α-Dihy­dr­oxy-17a-oxa-D-homoandrost-5-en-17-one

Alina Świzdor,a Agata Białońska,b* Teresa Kołeka and Anna Paneka

aDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, 25. Norwida, 50-375 Wrocław, Poland, and bFaculty of Chemistry, University of Wrocław, 14. F. Joliot-Curie, 50-383 Wrocław, Poland
*Correspondence e-mail: bialonsk@eto.wchuwr.pl

(Received 29 June 2010; accepted 5 July 2010; online 14 July 2010)

The title compound, C19H28O4, was prepared from DHEA (dehydro­epiandrosterone) by its biotransformation using whole cells of the filamentous fungus Beauveria bassiana. The asymmetric unit contains two mol­ecules. The lactone ring is trans-positioned to the neighboring six-membered ring. In the crystal structure, O—H⋯O hydrogen bonds form layers, which are linked to each other by O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background information on steroidal lactones and their properties, see: Braunstein (1999[Braunstein, G. D. (1999). Endocr. Relat. Cancer, 6, 315-324.]); Brodie & Njar (1998[Brodie, A. M. H. & Njar, V. C. O. (1998). J. Steroid Biochem. Mol. Biol. 66, 1-10.]); Bydal et al. (2009[Bydal, P., Luu-The, V., Labrie, F. & Poirier, D. (2009). Eur. J. Med. Chem. 44, 632-644.]); Feuillan et al. (1999[Feuillan, P. P., Merke, D., Leschek, E. W. & Cutler, G. B. (1999). Endocr. Relat. Cancer, 6, 303-306.]); Li & Parish (1996[Li, S. & Parish, E. J. (1996). JAOCS, 73, 1435-1451.]); Dunkel (2006[Dunkel, L. (2006). Mol. Cell. Endocrinol. 254-255, 207-216.]); Penov Gaši et al. (2001[Penov Gaši, K., Stanković, S. M., Csanádi, J. J., Djurendić, E. A., Sakač, M. N., Medić Mijačević, L., Arcson, O. N., Stojanović, S. Z., Andrić, S., Molnar Gabor, D. & Kovačević, R. (2001). Steroids, 66, 645-653.], 2005[Penov Gaši, K., Stojanović, S. Z., Sakač, M. N., Popsavin, M., Jovanovič Šanta, S., Stanković, S. M., Klisurić, O. R., Andrić, S. & Kovačević, R. (2005). Steroids, 70, 47-53.]). For the general method of preparation of the title compound, see: Kołek et al. (2008[Kołek, T., Szpineter, A. & Świzdor, A. (2008). Steroids, 73, 1441-1445.]).

[Scheme 1]

Experimental

Crystal data

  • C19H28O4

  • Mr = 320.41

  • Monoclinic, P 21

  • a = 11.915 (3) Å

  • b = 9.854 (2) Å

  • c = 14.246 (3) Å

  • β = 102.66 (3)°

  • V = 1632.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.12 × 0.08 × 0.07 mm
Data collection

  • Kuma KM-4 CCD diffractometer

  • 8286 measured reflections

  • 2921 independent reflections

  • 2062 reflections with I > 2σ(I)

  • Rint = 0.118
Refinement

  • R[F2 > 2σ(F2)] = 0.092

  • wR(F2) = 0.167

  • S = 1.13

  • 2921 reflections

  • 415 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H31⋯O17Ai 0.84 2.04 2.773 (8) 145
O11—H111⋯O17ii 0.84 2.02 2.861 (8) 180
O3A—H31A⋯O11Aiii 0.84 2.14 2.970 (8) 170
O11A—H112⋯O3iv 0.91 2.01 2.918 (8) 179
C16—H16B⋯O3v 0.99 2.47 3.418 (10) 161
C18A—H18E⋯O3Av 0.98 2.48 3.443 (9) 167
Symmetry codes: (i) x+1, y-1, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+2]; (iii) [-x+2, y-{\script{1\over 2}}, -z+1]; (iv) [-x+2, y+{\script{1\over 2}}, -z+1]; (v) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: XP (Bruker, 1999[Bruker (1999). XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026516/wn2398sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026516/wn2398Isup2.hkl

checkCIF report


Comment top

A number of steroidal compounds possess anti-aromatase activity and thereby may contribute to the prevention of estrogen-dependent tumors, such as breast cancer (Brodie & Njar, 1998), endometrial cancer (Bydal et al., 2009), prostatic hyperplasia and prostate cancer (Li & Parish, 1996). Among these structures, D-homo lactones of the androstane series represent compounds with promising potency towards human aromatase inhibition (Penov Gaši et al., 2001, 2005). Testolactone (17a-oxa-D-homo-androsta-1,4-diene-3,17-dione) is used as a pharmaceutical agent in disorders caused by imbalance between estrogen and androgen action, e.g. gynecomastia (Braunstein, 1999) or precocious puberty (Feuillan et al., 1999; Dunkel, 2006).

As a part of our ongoing investigation of the biosynthesis of steroidal lactones, the title compound was obtained.

There are two molecules of the title compound in the asymmetric unit (Fig. 1). O11—H11···O17(-x + 1, y - 1/2, -z + 2) hydrogen bonds are found, also O3A—H31A···O11a(-x + 2, y - 1/2, -z + 1) hydrogen bonds, resulting in chains extended along the [010] direction (Table 1). The hydroxyl O11A and O3(-x + 2, y + 1/2, -z + 1) atoms of neighboring chains form hydrogen bonds resulting in layers extended along the [101] direction (Fig. 2). Consecutive layers are linked to each other by O—H···O and C—H···O hydrogen bonds. The hydroxyl O3 and the carbonyl O17A(x + 1, y - 1, z) atoms participate in the O—H···O hydrogen bonds as donor and acceptor, respectively. In the C—H···O interactions the C16 and C18A atoms are donors, and the O3(x - 1, y, z) and O3A(x - 1, y, z) atoms are their acceptors, respectively.

Related literature top

For background information on steroidal lactones and their properties, see: Braunstein (1999); Brodie & Njar (1998); Bydal et al. (2009); Feuillan et al. (1999); Li & Parish (1996); Dunkel (2006); Penov Gaši et al. (2001, 2005). For the preparation of the title compound, see: Kołek et al. (2008).

Experimental top

The title compound was prepared from DHEA (dehydroepiandrosterone) by its biotransformation using whole-cells of filamentous fungus Beauveria bassiana, according to the general procedure described in (Kołek et al., 2008). The crude extract of reaction products was subjected to silica gel column chromatography using a mixture of ethyl acetate/dichloromethane/acetone/2-propanol (3:1:0.5:0.15) as eluent. The product of this biotransformation was identified by interpretation of its IR, 1H NMR and 13C NMR spectroscopic data. 1H-NMR: δ (p.p.m.) in CD3OD: 1.20 (s, 19-H3); 1.38 (s, 18-H3); 3.45 (m, 3α-H); 3.88 (m, 11β-H); 5.46 (d, J = 5.7 Hz); 13C-NMR: δ (p.p.m.) in CD3OD: 174.4 (C-17); 142.7 (C-5); 121.4 (C-6); 83.6 (C-13); 72.5 (C-3); 69.0 (C-11); 56.9 (C-9); 50.3 (C-12); 47.0 (C-14); 43.3 (C-4); 40.4 (C-1); 39.5 (C-10), 35.5 (C-2); 32.3 (C-7); 32.2 (C-8); 29.4 (C-16); 21.1 (C-18); 20.8 (C-15); 19.2 (C-19); IR νmax (cm-1): 3440, 1716. Single crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow evaporation from methanol after two weeks at room temperature.

Refinement top

All H atoms bonded to O atoms were located in a difference map and then placed in idealised calculated positions with O—H distances of 0.84 Å. All H atoms bonded to C atoms were placed in calculated positions with C—H distances of 0.95 - 1.00 Å. All H atoms were refined as riding. In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration of the title compound was assigned on the basis of the known absolute configuration of particular substrates (commercially available)

Structure description top

A number of steroidal compounds possess anti-aromatase activity and thereby may contribute to the prevention of estrogen-dependent tumors, such as breast cancer (Brodie & Njar, 1998), endometrial cancer (Bydal et al., 2009), prostatic hyperplasia and prostate cancer (Li & Parish, 1996). Among these structures, D-homo lactones of the androstane series represent compounds with promising potency towards human aromatase inhibition (Penov Gaši et al., 2001, 2005). Testolactone (17a-oxa-D-homo-androsta-1,4-diene-3,17-dione) is used as a pharmaceutical agent in disorders caused by imbalance between estrogen and androgen action, e.g. gynecomastia (Braunstein, 1999) or precocious puberty (Feuillan et al., 1999; Dunkel, 2006).

As a part of our ongoing investigation of the biosynthesis of steroidal lactones, the title compound was obtained.

There are two molecules of the title compound in the asymmetric unit (Fig. 1). O11—H11···O17(-x + 1, y - 1/2, -z + 2) hydrogen bonds are found, also O3A—H31A···O11a(-x + 2, y - 1/2, -z + 1) hydrogen bonds, resulting in chains extended along the [010] direction (Table 1). The hydroxyl O11A and O3(-x + 2, y + 1/2, -z + 1) atoms of neighboring chains form hydrogen bonds resulting in layers extended along the [101] direction (Fig. 2). Consecutive layers are linked to each other by O—H···O and C—H···O hydrogen bonds. The hydroxyl O3 and the carbonyl O17A(x + 1, y - 1, z) atoms participate in the O—H···O hydrogen bonds as donor and acceptor, respectively. In the C—H···O interactions the C16 and C18A atoms are donors, and the O3(x - 1, y, z) and O3A(x - 1, y, z) atoms are their acceptors, respectively.

For background information on steroidal lactones and their properties, see: Braunstein (1999); Brodie & Njar (1998); Bydal et al. (2009); Feuillan et al. (1999); Li & Parish (1996); Dunkel (2006); Penov Gaši et al. (2001, 2005). For the preparation of the title compound, see: Kołek et al. (2008).

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1999); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the two crystallographically unrelated 3β,11α-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one molecules together with the numbering scheme employed (30% probability displacement parameters).
[Figure 2] Fig. 2. Molecular packing of the title compound, viewed along the [010] direction. Hydrogen atoms are omitted for clarity. Dashed lines indicate hydrogen bonds.
3β,11α-Dihydroxy-17a-oxa-D-homoandrost-5-en-17-one top
Crystal data top
C19H28O4F(000) = 696
Mr = 320.41Dx = 1.304 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1957 reflections
a = 11.915 (3) Åθ = 3.1–28.6°
b = 9.854 (2) ŵ = 0.09 mm−1
c = 14.246 (3) ÅT = 100 K
β = 102.66 (3)°Needle, colorless
V = 1632.0 (6) Å30.12 × 0.08 × 0.07 mm
Z = 4
Data collection top
Kuma KM-4 CCD
diffractometer		2062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.118
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
ω scanh = −13→14
8286 measured reflectionsk = −11→11
2921 independent reflectionsl = −16→16
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)] = 0.092Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0609P)2]
where P = (Fo2 + 2Fc2)/3
2921 reflections(Δ/σ)max = 0.002
415 parametersΔρmax = 0.26 e Å−3
1 restraintΔρmin = −0.28 e Å−3
Crystal data top
C19H28O4V = 1632.0 (6) Å3
Mr = 320.41Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.915 (3) ŵ = 0.09 mm−1
b = 9.854 (2) ÅT = 100 K
c = 14.246 (3) Å0.12 × 0.08 × 0.07 mm
β = 102.66 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer		2062 reflections with I > 2σ(I)
8286 measured reflectionsRint = 0.118
2921 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0921 restraint
wR(F2) = 0.167H-atom parameters constrained
S = 1.13Δρmax = 0.26 e Å−3
2921 reflectionsΔρmin = −0.28 e Å−3
415 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
C10.9668 (6)−0.0351 (9)0.8744 (7)0.027 (2)
H1A0.9251−0.11580.84330.033*
H1B0.9861−0.05140.94460.033*
C21.0803 (7)−0.0189 (9)0.8385 (7)0.029 (2)
H2A1.12560.05720.87310.035*
H2B1.1267−0.10270.85290.035*
C31.0566 (7)0.0076 (9)0.7341 (7)0.025 (2)
H31.0206−0.07510.69940.031*
O31.1595 (4)0.0405 (6)0.7006 (4)0.0286 (16)
H311.1968−0.03080.69670.043*
C40.9758 (7)0.1260 (9)0.7066 (7)0.029 (2)
H4A0.95380.13200.63550.035*
H4B1.01690.21070.73060.035*
C50.8679 (7)0.1160 (8)0.7455 (7)0.024 (2)
C60.7672 (8)0.1263 (10)0.6882 (7)0.037 (3)
H60.76430.12840.62100.045*
C70.6540 (6)0.1352 (9)0.7199 (6)0.023 (2)
H7A0.61090.04930.70420.028*
H7B0.60700.20970.68490.028*
C80.6749 (6)0.1611 (8)0.8280 (6)0.0162 (19)
H80.70600.25530.84040.019*
C90.7686 (6)0.0604 (8)0.8813 (6)0.019 (2)
H90.7440−0.03210.85610.023*
C100.8868 (6)0.0897 (8)0.8531 (6)0.0157 (19)
C110.7781 (6)0.0549 (9)0.9891 (6)0.023 (2)
H110.82030.13821.01730.027*
O110.8426 (4)−0.0592 (6)1.0332 (4)0.0259 (14)
H1110.8013−0.12901.02350.039*
C120.6615 (6)0.0549 (9)1.0183 (7)0.024 (2)
H12A0.6226−0.03301.00010.029*
H12B0.67440.06431.08910.029*
C130.5839 (6)0.1694 (8)0.9707 (6)0.020 (2)
C140.5621 (6)0.1529 (9)0.8640 (6)0.020 (2)
H140.53120.05910.84930.024*
C150.4689 (7)0.2504 (8)0.8136 (7)0.027 (2)
H15A0.49640.34510.82480.033*
H15B0.45150.23320.74350.033*
C160.3611 (6)0.2308 (9)0.8522 (6)0.024 (2)
H16A0.31520.31520.83960.028*
H16B0.31520.15770.81430.028*
C170.3752 (7)0.1970 (8)0.9557 (7)0.023 (2)
O170.2973 (5)0.2021 (6)0.9997 (4)0.0292 (15)
C180.6319 (7)0.3083 (9)1.0075 (7)0.032 (2)
H18A0.58090.37980.97460.048*
H18B0.70880.31980.99460.048*
H18C0.63660.31421.07700.048*
O180.4780 (4)0.1528 (5)1.0074 (4)0.0214 (14)
C190.9460 (7)0.2132 (8)0.9097 (6)0.025 (2)
H19A1.01970.23030.89200.038*
H19B0.95950.19460.97890.038*
H19C0.89650.29320.89430.038*
C1A1.0080 (6)0.6562 (8)0.5599 (6)0.0179 (19)
H1C0.97210.67340.49140.022*
H1D1.02040.74530.59270.022*
C2A1.1250 (6)0.5893 (8)0.5655 (6)0.019 (2)
H2C1.11470.50520.52650.023*
H2D1.17480.65140.53820.023*
C3A1.1829 (6)0.5553 (9)0.6679 (6)0.023 (2)
H3A1.19850.64260.70420.027*
O3A1.2915 (4)0.4876 (5)0.6748 (4)0.0249 (15)
H31A1.28070.41290.64580.037*
C4A1.1040 (6)0.4710 (8)0.7157 (6)0.0159 (19)
H4C1.09660.37900.68720.019*
H4D1.13970.46170.78500.019*
C5A0.9847 (6)0.5318 (7)0.7051 (6)0.018 (2)
C6A0.9427 (7)0.5484 (8)0.7832 (6)0.022 (2)
H6A0.99100.52590.84350.026*
C7A0.8240 (6)0.6003 (8)0.7828 (6)0.021 (2)
H7C0.82990.69270.81070.025*
H7D0.78790.54100.82400.025*
C8A0.7465 (6)0.6047 (8)0.6807 (6)0.017 (2)
H8A0.71970.51050.66170.021*
C9A0.8139 (6)0.6586 (8)0.6069 (5)0.0151 (19)
H9A0.84120.75190.62810.018*
C10A0.9220 (6)0.5721 (8)0.6053 (6)0.0154 (19)
O11A0.7782 (4)0.7336 (5)0.4348 (4)0.0206 (13)
H1120.79820.67340.39320.031*
C11A0.7297 (6)0.6732 (8)0.5095 (6)0.023 (2)
H11A0.69930.58120.48750.028*
C12A0.6271 (7)0.7661 (8)0.5166 (6)0.020 (2)
H12C0.65590.85770.53810.024*
H12D0.57510.77490.45240.024*
C13A0.5615 (6)0.7080 (8)0.5867 (6)0.0151 (19)
C14A0.6422 (6)0.6918 (8)0.6842 (6)0.0163 (19)
H14A0.67140.78440.70560.020*
C15A0.5714 (6)0.6418 (8)0.7560 (6)0.019 (2)
H15C0.54300.54890.73810.023*
H15D0.62160.63780.82130.023*
C16A0.4701 (7)0.7344 (9)0.7573 (6)0.026 (2)
H16C0.40690.67820.77150.031*
H16D0.49330.79890.81130.031*
C17A0.4230 (7)0.8149 (9)0.6678 (7)0.026 (2)
O17A0.3402 (5)0.8891 (6)0.6618 (5)0.0392 (18)
C18A0.4953 (6)0.5794 (9)0.5487 (6)0.027 (2)
H18D0.44600.59770.48530.041*
H18E0.44770.55120.59330.041*
H18F0.54980.50700.54310.041*
O18A0.4727 (4)0.8118 (6)0.5927 (4)0.0279 (16)
C19A0.8888 (7)0.4390 (8)0.5463 (6)0.021 (2)
H19D0.83440.38680.57440.031*
H19E0.95810.38470.54790.031*
H19F0.85310.46210.47950.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.017 (5)0.029 (5)0.037 (6)0.006 (4)0.008 (4)0.004 (5)
C20.015 (4)0.028 (5)0.046 (7)0.005 (4)0.013 (4)−0.002 (5)
C30.019 (5)0.029 (5)0.030 (6)−0.003 (4)0.010 (4)−0.007 (4)
O30.019 (3)0.030 (4)0.041 (4)0.001 (3)0.016 (3)−0.005 (3)
C40.028 (5)0.032 (6)0.028 (6)0.005 (4)0.008 (4)−0.001 (5)
C50.016 (4)0.019 (5)0.044 (7)−0.001 (4)0.022 (4)−0.006 (4)
C60.036 (6)0.049 (7)0.033 (7)−0.001 (5)0.021 (5)0.007 (5)
C70.022 (5)0.024 (5)0.025 (6)−0.001 (4)0.009 (4)0.001 (4)
C80.015 (4)0.017 (4)0.015 (5)0.000 (3)−0.001 (4)−0.007 (4)
C90.018 (4)0.017 (5)0.022 (6)0.003 (4)0.005 (4)−0.006 (4)
C100.014 (4)0.012 (4)0.022 (6)−0.004 (3)0.006 (4)0.004 (4)
C110.016 (4)0.022 (5)0.033 (6)0.006 (4)0.011 (4)0.001 (4)
O110.021 (3)0.026 (3)0.031 (4)0.002 (3)0.006 (3)0.014 (3)
C120.014 (4)0.028 (5)0.033 (6)0.005 (4)0.010 (4)0.009 (4)
C130.012 (4)0.024 (5)0.026 (6)0.000 (4)0.007 (4)0.005 (4)
C140.022 (5)0.023 (5)0.013 (5)0.004 (4)0.003 (4)0.003 (4)
C150.027 (5)0.017 (4)0.038 (7)0.001 (4)0.009 (4)0.003 (4)
C160.016 (4)0.031 (5)0.023 (6)0.002 (4)0.002 (4)0.004 (4)
C170.020 (5)0.016 (4)0.033 (6)−0.001 (4)0.006 (4)−0.010 (4)
O170.027 (3)0.027 (3)0.036 (4)0.001 (3)0.011 (3)0.005 (3)
C180.027 (5)0.030 (5)0.039 (7)−0.003 (4)0.005 (5)−0.003 (5)
O180.015 (3)0.025 (3)0.027 (4)0.004 (3)0.009 (3)0.005 (3)
C190.028 (5)0.020 (5)0.030 (6)−0.005 (4)0.012 (4)−0.006 (4)
C1A0.024 (5)0.009 (4)0.024 (5)0.001 (4)0.013 (4)0.000 (4)
C2A0.008 (4)0.019 (4)0.031 (6)0.002 (3)0.007 (4)0.004 (4)
C3A0.012 (4)0.032 (5)0.022 (6)0.006 (4)−0.001 (4)−0.007 (4)
O3A0.013 (3)0.025 (3)0.038 (4)0.003 (3)0.010 (3)0.000 (3)
C4A0.013 (4)0.015 (5)0.018 (5)−0.007 (4)0.002 (4)0.005 (4)
C5A0.011 (4)0.005 (4)0.037 (6)−0.003 (3)0.008 (4)0.004 (4)
C6A0.022 (5)0.019 (5)0.025 (6)−0.007 (4)0.008 (4)0.006 (4)
C7A0.008 (4)0.024 (5)0.032 (6)−0.003 (4)0.006 (4)0.000 (4)
C8A0.017 (4)0.009 (4)0.028 (6)0.001 (3)0.009 (4)0.006 (4)
C9A0.012 (4)0.024 (5)0.009 (5)0.002 (4)0.000 (3)0.000 (4)
C10A0.016 (4)0.009 (4)0.023 (5)−0.001 (3)0.007 (4)−0.001 (4)
O11A0.022 (3)0.025 (3)0.019 (3)0.007 (3)0.012 (3)0.007 (3)
C11A0.024 (5)0.017 (5)0.033 (6)−0.005 (4)0.016 (4)−0.001 (4)
C12A0.019 (4)0.021 (5)0.016 (5)0.003 (4)−0.004 (4)−0.001 (4)
C13A0.007 (4)0.015 (4)0.023 (5)−0.001 (3)0.003 (4)0.005 (4)
C14A0.013 (4)0.019 (4)0.018 (5)−0.005 (3)0.005 (4)−0.005 (4)
C15A0.011 (4)0.024 (5)0.021 (6)0.002 (4)−0.002 (4)−0.005 (4)
C16A0.017 (4)0.030 (5)0.032 (6)−0.005 (4)0.008 (4)−0.004 (5)
C17A0.011 (4)0.028 (5)0.044 (7)−0.002 (4)0.015 (4)−0.002 (5)
O17A0.030 (4)0.044 (4)0.049 (5)0.019 (3)0.020 (3)0.007 (4)
C18A0.020 (5)0.033 (5)0.027 (6)−0.002 (4)0.000 (4)−0.004 (4)
O18A0.016 (3)0.028 (4)0.043 (5)0.011 (3)0.014 (3)0.008 (3)
C19A0.025 (5)0.018 (4)0.023 (5)−0.001 (4)0.015 (4)−0.005 (4)
Geometric parameters (Å, º) top
C1—C101.545 (10)C1A—C2A1.528 (10)
C1—C21.554 (10)C1A—C10A1.564 (10)
C1—H1A0.9900C1A—H1C0.9900
C1—H1B0.9900C1A—H1D0.9900
C2—C31.474 (12)C2A—C3A1.509 (11)
C2—H2A0.9900C2A—H2C0.9900
C2—H2B0.9900C2A—H2D0.9900
C3—O31.447 (9)C3A—O3A1.440 (8)
C3—C41.509 (11)C3A—C4A1.522 (10)
C3—H31.0000C3A—H3A1.0000
O3—H310.8400O3A—H31A0.8400
C4—C51.512 (10)C4A—C5A1.519 (10)
C4—H4A0.9900C4A—H4C0.9900
C4—H4B0.9900C4A—H4D0.9900
C5—C61.298 (12)C5A—C6A1.325 (10)
C5—C101.522 (12)C5A—C10A1.508 (11)
C6—C71.516 (10)C6A—C7A1.503 (10)
C6—H60.9500C6A—H6A0.9500
C7—C81.526 (10)C7A—C8A1.543 (11)
C7—H7A0.9900C7A—H7C0.9900
C7—H7B0.9900C7A—H7D0.9900
C8—C141.542 (10)C8A—C14A1.521 (10)
C8—C91.560 (10)C8A—C9A1.549 (10)
C8—H81.0000C8A—H8A1.0000
C9—C111.516 (11)C9A—C11A1.530 (11)
C9—C101.574 (9)C9A—C10A1.549 (10)
C9—H91.0000C9A—H9A1.0000
C10—C191.543 (10)C10A—C19A1.561 (10)
C11—O111.427 (9)O11A—C11A1.446 (9)
C11—C121.535 (10)O11A—H1120.9069
C11—H111.0000C11A—C12A1.549 (10)
O11—H1110.8400C11A—H11A1.0000
C12—C131.520 (11)C12A—C13A1.510 (10)
C12—H12A0.9900C12A—H12C0.9900
C12—H12B0.9900C12A—H12D0.9900
C13—O181.477 (8)C13A—O18A1.487 (9)
C13—C141.494 (11)C13A—C14A1.514 (10)
C13—C181.531 (12)C13A—C18A1.528 (11)
C14—C151.524 (11)C14A—C15A1.543 (10)
C14—H141.0000C14A—H14A1.0000
C15—C161.516 (10)C15A—C16A1.517 (10)
C15—H15A0.9900C15A—H15C0.9900
C15—H15B0.9900C15A—H15D0.9900
C16—C171.484 (11)C16A—C17A1.503 (12)
C16—H16A0.9900C16A—H16C0.9900
C16—H16B0.9900C16A—H16D0.9900
C17—O171.230 (9)C17A—O17A1.216 (9)
C17—O181.356 (9)C17A—O18A1.331 (10)
C18—H18A0.9800C18A—H18D0.9800
C18—H18B0.9800C18A—H18E0.9800
C18—H18C0.9800C18A—H18F0.9800
C19—H19A0.9800C19A—H19D0.9800
C19—H19B0.9800C19A—H19E0.9800
C19—H19C0.9800C19A—H19F0.9800
C10—C1—C2113.4 (7)C2A—C1A—C10A115.0 (7)
C10—C1—H1A108.9C2A—C1A—H1C108.5
C2—C1—H1A108.9C10A—C1A—H1C108.5
C10—C1—H1B108.9C2A—C1A—H1D108.5
C2—C1—H1B108.9C10A—C1A—H1D108.5
H1A—C1—H1B107.7H1C—C1A—H1D107.5
C3—C2—C1111.2 (7)C3A—C2A—C1A111.4 (6)
C3—C2—H2A109.4C3A—C2A—H2C109.3
C1—C2—H2A109.4C1A—C2A—H2C109.3
C3—C2—H2B109.4C3A—C2A—H2D109.3
C1—C2—H2B109.4C1A—C2A—H2D109.3
H2A—C2—H2B108.0H2C—C2A—H2D108.0
O3—C3—C2112.6 (7)O3A—C3A—C2A112.5 (6)
O3—C3—C4106.2 (6)O3A—C3A—C4A110.6 (7)
C2—C3—C4111.7 (7)C2A—C3A—C4A110.9 (6)
O3—C3—H3108.8O3A—C3A—H3A107.6
C2—C3—H3108.8C2A—C3A—H3A107.6
C4—C3—H3108.8C4A—C3A—H3A107.6
C3—O3—H31109.5C3A—O3A—H31A109.5
C3—C4—C5113.6 (7)C5A—C4A—C3A113.4 (6)
C3—C4—H4A108.9C5A—C4A—H4C108.9
C5—C4—H4A108.9C3A—C4A—H4C108.9
C3—C4—H4B108.9C5A—C4A—H4D108.9
C5—C4—H4B108.9C3A—C4A—H4D108.9
H4A—C4—H4B107.7H4C—C4A—H4D107.7
C6—C5—C4120.4 (8)C6A—C5A—C10A124.0 (7)
C6—C5—C10124.0 (7)C6A—C5A—C4A118.9 (8)
C4—C5—C10115.5 (7)C10A—C5A—C4A117.2 (7)
C5—C6—C7125.2 (9)C5A—C6A—C7A124.5 (8)
C5—C6—H6117.4C5A—C6A—H6A117.7
C7—C6—H6117.4C7A—C6A—H6A117.7
C6—C7—C8110.6 (7)C6A—C7A—C8A112.4 (7)
C6—C7—H7A109.5C6A—C7A—H7C109.1
C8—C7—H7A109.5C8A—C7A—H7C109.1
C6—C7—H7B109.5C6A—C7A—H7D109.1
C8—C7—H7B109.5C8A—C7A—H7D109.1
H7A—C7—H7B108.1H7C—C7A—H7D107.9
C7—C8—C14111.4 (6)C14A—C8A—C7A108.1 (6)
C7—C8—C9109.0 (6)C14A—C8A—C9A112.2 (6)
C14—C8—C9112.8 (6)C7A—C8A—C9A111.0 (6)
C7—C8—H8107.8C14A—C8A—H8A108.5
C14—C8—H8107.8C7A—C8A—H8A108.5
C9—C8—H8107.8C9A—C8A—H8A108.5
C11—C9—C8113.8 (6)C11A—C9A—C8A108.3 (6)
C11—C9—C10113.1 (6)C11A—C9A—C10A114.8 (6)
C8—C9—C10110.1 (6)C8A—C9A—C10A112.2 (6)
C11—C9—H9106.4C11A—C9A—H9A107.1
C8—C9—H9106.4C8A—C9A—H9A107.1
C10—C9—H9106.4C10A—C9A—H9A107.1
C5—C10—C19110.0 (6)C5A—C10A—C9A111.9 (6)
C5—C10—C1106.4 (7)C5A—C10A—C19A107.6 (6)
C19—C10—C1109.5 (6)C9A—C10A—C19A110.9 (6)
C5—C10—C9110.2 (6)C5A—C10A—C1A107.2 (6)
C19—C10—C9110.1 (6)C9A—C10A—C1A109.7 (6)
C1—C10—C9110.7 (6)C19A—C10A—C1A109.5 (6)
O11—C11—C9112.8 (6)C11A—O11A—H112114.6
O11—C11—C12108.2 (6)O11A—C11A—C9A114.7 (6)
C9—C11—C12113.8 (7)O11A—C11A—C12A104.6 (6)
O11—C11—H11107.2C9A—C11A—C12A111.4 (6)
C9—C11—H11107.2O11A—C11A—H11A108.6
C12—C11—H11107.2C9A—C11A—H11A108.6
C11—O11—H111109.5C12A—C11A—H11A108.6
C13—C12—C11112.2 (7)C13A—C12A—C11A110.5 (6)
C13—C12—H12A109.2C13A—C12A—H12C109.6
C11—C12—H12A109.2C11A—C12A—H12C109.6
C13—C12—H12B109.2C13A—C12A—H12D109.6
C11—C12—H12B109.2C11A—C12A—H12D109.6
H12A—C12—H12B107.9H12C—C12A—H12D108.1
O18—C13—C14112.1 (6)O18A—C13A—C12A104.8 (6)
O18—C13—C12104.1 (6)O18A—C13A—C14A109.7 (6)
C14—C13—C12109.1 (7)C12A—C13A—C14A109.3 (6)
O18—C13—C18105.1 (6)O18A—C13A—C18A105.8 (6)
C14—C13—C18114.5 (7)C12A—C13A—C18A112.4 (7)
C12—C13—C18111.5 (7)C14A—C13A—C18A114.3 (7)
C13—C14—C15110.9 (7)C13A—C14A—C8A112.9 (6)
C13—C14—C8111.3 (6)C13A—C14A—C15A108.2 (6)
C15—C14—C8114.1 (6)C8A—C14A—C15A114.2 (7)
C13—C14—H14106.7C13A—C14A—H14A107.0
C15—C14—H14106.7C8A—C14A—H14A107.0
C8—C14—H14106.7C15A—C14A—H14A107.0
C16—C15—C14109.7 (7)C16A—C15A—C14A111.6 (7)
C16—C15—H15A109.7C16A—C15A—H15C109.3
C14—C15—H15A109.7C14A—C15A—H15C109.3
C16—C15—H15B109.7C16A—C15A—H15D109.3
C14—C15—H15B109.7C14A—C15A—H15D109.3
H15A—C15—H15B108.2H15C—C15A—H15D108.0
C17—C16—C15117.9 (7)C17A—C16A—C15A117.2 (7)
C17—C16—H16A107.8C17A—C16A—H16C108.0
C15—C16—H16A107.8C15A—C16A—H16C108.0
C17—C16—H16B107.8C17A—C16A—H16D108.0
C15—C16—H16B107.8C15A—C16A—H16D108.0
H16A—C16—H16B107.2H16C—C16A—H16D107.2
O17—C17—O18115.4 (8)O17A—C17A—O18A117.0 (9)
O17—C17—C16124.3 (7)O17A—C17A—C16A121.6 (8)
O18—C17—C16120.3 (7)O18A—C17A—C16A121.4 (7)
C13—C18—H18A109.5C13A—C18A—H18D109.5
C13—C18—H18B109.5C13A—C18A—H18E109.5
H18A—C18—H18B109.5H18D—C18A—H18E109.5
C13—C18—H18C109.5C13A—C18A—H18F109.5
H18A—C18—H18C109.5H18D—C18A—H18F109.5
H18B—C18—H18C109.5H18E—C18A—H18F109.5
C17—O18—C13120.8 (6)C17A—O18A—C13A120.6 (6)
C10—C19—H19A109.5C10A—C19A—H19D109.5
C10—C19—H19B109.5C10A—C19A—H19E109.5
H19A—C19—H19B109.5H19D—C19A—H19E109.5
C10—C19—H19C109.5C10A—C19A—H19F109.5
H19A—C19—H19C109.5H19D—C19A—H19F109.5
H19B—C19—H19C109.5H19E—C19A—H19F109.5
C10—C1—C2—C3−57.8 (10)C10A—C1A—C2A—C3A−56.1 (9)
C1—C2—C3—O3172.5 (6)C1A—C2A—C3A—O3A177.9 (7)
C1—C2—C3—C453.2 (9)C1A—C2A—C3A—C4A53.5 (9)
O3—C3—C4—C5−173.8 (7)O3A—C3A—C4A—C5A−176.0 (7)
C2—C3—C4—C5−50.7 (10)C2A—C3A—C4A—C5A−50.5 (9)
C3—C4—C5—C6−126.5 (10)C3A—C4A—C5A—C6A−128.5 (8)
C3—C4—C5—C1051.8 (10)C3A—C4A—C5A—C10A50.5 (9)
C4—C5—C6—C7−172.1 (7)C10A—C5A—C6A—C7A4.5 (12)
C10—C5—C6—C79.7 (15)C4A—C5A—C6A—C7A−176.7 (7)
C5—C6—C7—C812.2 (12)C5A—C6A—C7A—C8A11.9 (11)
C6—C7—C8—C14−172.9 (7)C6A—C7A—C8A—C14A−165.1 (6)
C6—C7—C8—C9−47.9 (9)C6A—C7A—C8A—C9A−41.8 (9)
C7—C8—C9—C11−167.3 (7)C14A—C8A—C9A—C11A−53.8 (8)
C14—C8—C9—C11−43.0 (9)C7A—C8A—C9A—C11A−174.7 (6)
C7—C8—C9—C1064.6 (8)C14A—C8A—C9A—C10A178.5 (7)
C14—C8—C9—C10−171.2 (7)C7A—C8A—C9A—C10A57.5 (8)
C6—C5—C10—C19−115.1 (9)C6A—C5A—C10A—C9A10.6 (10)
C4—C5—C10—C1966.7 (8)C4A—C5A—C10A—C9A−168.3 (7)
C6—C5—C10—C1126.5 (9)C6A—C5A—C10A—C19A−111.4 (8)
C4—C5—C10—C1−51.7 (8)C4A—C5A—C10A—C19A69.7 (8)
C6—C5—C10—C96.5 (11)C6A—C5A—C10A—C1A130.9 (8)
C4—C5—C10—C9−171.7 (6)C4A—C5A—C10A—C1A−48.0 (8)
C2—C1—C10—C554.3 (9)C11A—C9A—C10A—C5A−165.2 (6)
C2—C1—C10—C19−64.5 (9)C8A—C9A—C10A—C5A−41.1 (8)
C2—C1—C10—C9174.0 (7)C11A—C9A—C10A—C19A−45.2 (9)
C11—C9—C10—C5−171.1 (7)C8A—C9A—C10A—C19A79.0 (8)
C8—C9—C10—C5−42.6 (8)C11A—C9A—C10A—C1A75.9 (8)
C11—C9—C10—C19−49.6 (9)C8A—C9A—C10A—C1A−159.9 (6)
C8—C9—C10—C1979.0 (8)C2A—C1A—C10A—C5A50.9 (9)
C11—C9—C10—C171.6 (9)C2A—C1A—C10A—C9A172.6 (7)
C8—C9—C10—C1−159.9 (7)C2A—C1A—C10A—C19A−65.5 (9)
C8—C9—C11—O11165.7 (6)C8A—C9A—C11A—O11A175.0 (6)
C10—C9—C11—O11−67.7 (8)C10A—C9A—C11A—O11A−58.8 (9)
C8—C9—C11—C1241.9 (9)C8A—C9A—C11A—C12A56.3 (8)
C10—C9—C11—C12168.4 (6)C10A—C9A—C11A—C12A−177.5 (6)
O11—C11—C12—C13−177.2 (7)O11A—C11A—C12A—C13A175.2 (6)
C9—C11—C12—C13−50.9 (10)C9A—C11A—C12A—C13A−60.3 (8)
C11—C12—C13—O18−179.8 (7)C11A—C12A—C13A—O18A175.4 (6)
C11—C12—C13—C1460.3 (9)C11A—C12A—C13A—C14A57.9 (8)
C11—C12—C13—C18−67.0 (9)C11A—C12A—C13A—C18A−70.2 (8)
O18—C13—C14—C1555.6 (8)O18A—C13A—C14A—C8A−170.7 (6)
C12—C13—C14—C15170.3 (6)C12A—C13A—C14A—C8A−56.4 (8)
C18—C13—C14—C15−64.1 (8)C18A—C13A—C14A—C8A70.7 (8)
O18—C13—C14—C8−176.2 (6)O18A—C13A—C14A—C15A61.8 (8)
C12—C13—C14—C8−61.5 (8)C12A—C13A—C14A—C15A176.2 (6)
C18—C13—C14—C864.1 (8)C18A—C13A—C14A—C15A−56.8 (8)
C7—C8—C14—C13176.3 (7)C7A—C8A—C14A—C13A177.9 (6)
C9—C8—C14—C1353.4 (8)C9A—C8A—C14A—C13A55.3 (8)
C7—C8—C14—C15−57.3 (9)C7A—C8A—C14A—C15A−57.9 (8)
C9—C8—C14—C15179.8 (7)C9A—C8A—C14A—C15A179.5 (6)
C13—C14—C15—C16−55.1 (9)C13A—C14A—C15A—C16A−54.4 (8)
C8—C14—C15—C16178.3 (7)C8A—C14A—C15A—C16A178.9 (7)
C14—C15—C16—C1735.3 (11)C14A—C15A—C16A—C17A25.9 (10)
C15—C16—C17—O17166.5 (8)C15A—C16A—C17A—O17A178.2 (8)
C15—C16—C17—O18−15.8 (11)C15A—C16A—C17A—O18A−4.2 (12)
O17—C17—O18—C13−166.7 (7)O17A—C17A—O18A—C13A−169.8 (7)
C16—C17—O18—C1315.4 (11)C16A—C17A—O18A—C13A12.5 (11)
C14—C13—O18—C17−35.6 (9)C12A—C13A—O18A—C17A−159.4 (7)
C12—C13—O18—C17−153.4 (7)C14A—C13A—O18A—C17A−42.2 (9)
C18—C13—O18—C1789.3 (8)C18A—C13A—O18A—C17A81.6 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O17Ai0.842.042.773 (8)145
O11—H111···O17ii0.842.022.861 (8)180
O3A—H31A···O11Aiii0.842.142.970 (8)170
O11A—H112···O3iv0.912.012.918 (8)179
C16—H16B···O3v0.992.473.418 (10)161
C18A—H18E···O3Av0.982.483.443 (9)167
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y−1/2, −z+2; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC19H28O4
Mr320.41
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)11.915 (3), 9.854 (2), 14.246 (3)
β (°) 102.66 (3)
V (Å3)1632.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.12 × 0.08 × 0.07
Data collection
DiffractometerKuma KM-4 CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		8286, 2921, 2062
Rint0.118
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.092, 0.167, 1.13
No. of reflections2921
No. of parameters415
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.26, −0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1999), SHELXTL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H31···O17Ai0.842.042.773 (8)145
O11—H111···O17ii0.842.022.861 (8)180
O3A—H31A···O11Aiii0.842.142.970 (8)170
O11A—H112···O3iv0.912.012.918 (8)179
C16—H16B···O3v0.992.473.418 (10)161
C18A—H18E···O3Av0.982.483.443 (9)167
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y−1/2, −z+2; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) x−1, y, z.
 

Acknowledgements

This work was financially supported by the European Union within the European Regional Development Fund (grant No. POIG.01.03.01–00-158/09–00).

References

First citationBraunstein, G. D. (1999). Endocr. Relat. Cancer, 6, 315–324.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBrodie, A. M. H. & Njar, V. C. O. (1998). J. Steroid Biochem. Mol. Biol. 66, 1–10.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationBruker (1999). XP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBydal, P., Luu-The, V., Labrie, F. & Poirier, D. (2009). Eur. J. Med. Chem. 44, 632–644.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationDunkel, L. (2006). Mol. Cell. Endocrinol. 254–255, 207–216.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationFeuillan, P. P., Merke, D., Leschek, E. W. & Cutler, G. B. (1999). Endocr. Relat. Cancer, 6, 303–306.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKołek, T., Szpineter, A. & Świzdor, A. (2008). Steroids, 73, 1441–1445.  Web of Science PubMed Google Scholar
 First citationLi, S. & Parish, E. J. (1996). JAOCS, 73, 1435–1451.  CrossRef CAS Web of Science Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationPenov Gaši, K., Stanković, S. M., Csanádi, J. J., Djurendić, E. A., Sakač, M. N., Medić Mijačević, L., Arcson, O. N., Stojanović, S. Z., Andrić, S., Molnar Gabor, D. & Kovačević, R. (2001). Steroids, 66, 645–653.  PubMed Google Scholar
 First citationPenov Gaši, K., Stojanović, S. Z., Sakač, M. N., Popsavin, M., Jovanovič Šanta, S., Stanković, S. M., Klisurić, O. R., Andrić, S. & Kovačević, R. (2005). Steroids, 70, 47–53.  Web of Science PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2003
https://doi.org/10.1107/S1600536810026516
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