17β-Hy­droxy-17α-methyl­androsta-1,4-dien-3-one

Karpinska, J.; Erxleben, A.; McArdle, P.

doi:10.1107/S1600536812049860

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o60

https://doi.org/10.1107/S1600536812049860

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17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one

Jolanta Karpinska,^a Andrea Erxleben ^a and Patrick McArdle ^a ^*

^aSchool of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland
^*Correspondence e-mail: patrick.mcardle@nuigalway.ie

(Received 6 November 2012; accepted 5 December 2012; online 8 December 2012)

The title compound, C₂₀H₂₈O₂, is a steroid with strong anabolic properties. The present solvent-free form crystallizes with two molecules per asymmetric unit. In the crystal, both molecules are involved in the formation of O—H⋯O hydrogen-bonded chains which extend along the b-axis direction.

Related literature

For examples of other compounds with unused hydrogen-bonding capacity, see: Bhatt et al. (2006 ); Lewis et al. (2005 ); Desiraju et al. (2002 ). For related structures of other anabolic steroids, see: Verma et al. (2006 ). For related structures of steroid compounds with non-hydrogen-bonded OH or C=O motifs, see: Karpinska et al. (2011 ); Danaci et al. (1988 ); Chakrabarti et al. (1981 ); McPhail et al. (1977 ); Delettré et al. (1975 ). For applications of methandrostenolone, see: Druzhinina et al. (2008 ). For a previously reported mono hydrate (with no unused hydrogen-bonding capacity), see: Duax et al. (1982 ).

Experimental

Crystal data

C₂₀H₂₈O₂
M_r = 300.42
Monoclinic, C 2
a = 28.317 (2) Å
b = 9.4539 (5) Å
c = 13.7684 (10) Å
β = 111.017 (9)°
V = 3440.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.50 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis171; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.985, T_max = 1.000
7321 measured reflections
4697 independent reflections
2893 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.199
S = 1.03
4697 reflections
404 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O2⋯O4ⁱ	0.82	2.00	2.808 (7)	167
O4—H4O4⋯O3ⁱⁱ	0.82	2.09	2.858 (7)	156
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+1, y+1, -z+2.

Data collection: CrysAlis171 (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis171; data reduction: CrysAlis171; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995 ); software used to prepare material for publication: CIFTAB (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812049860/bg2491sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049860/bg2491Isup3.hkl

checkCIF report

Comment top

Methandrostenolone, commonly known as dianabol, is an anabolic steroid which is widely applied in medicine, particularly in surgery, endocrinology, therapeutics and paediatrics (Druzhinina et al., 2008)). As a part of our studies on unused hydrogen bonding capacity in steroid compounds the crystal structure of the solvent free form has been determined using crystals grown by sublimation.

Methandrostenolone is another example of a steroid type compound which does not use all of its good proton donors and acceptors in hydrogen bonding formation. The previously reported mono hydrate has no unused hydrogen bonding capacity (Duax et al., 1982). The OH and C=O groups occupy opposite ends of the molecule and both are used in the formation of one dimensional hydrogen bonded chains. The O4-H4O3..O3 (2.878 Å) interactions of one molecule form chains (blue molecules in Fig. 2), with the O2 of the hydroxyl groups of the other molecule acting only as donors to the basic chain in O2-H2O2..O4 (2.808 Å) interactions (red molecules in Fig. 2). The O1 atom of the carbonyl group of this second molecule is not involved in any hydrogen bonding interaction.

Related literature top

For examples of other compounds with unused hydrogen-bonding capacity, see: Bhatt et al. (2006); Lewis et al. (2005); Desiraju et al. (2002). For related structures of other anabolic steroids, see: Verma et al. (2006). For related structures of steroid compounds with non-hydrogen-bonded OH or C=O motifs, see: Karpinska et al. (2011); Danaci et al. (1988); Chakrabarti et al. (1981); McPhail et al. (1977); Delettré et al. (1975). For applications of methandrostenolone, see: Druzhinina et al. (2008). For a previously reported mono hydrate (with no unused hydrogen-bonding capacity), see: Duax et al. (1982).

Experimental top

The title compound of high purity (>98.8%) was obtained from TCI Europe. Colourless crystals were grown by low temperature gradient sublimation in the vacuum.

Structure description top

For examples of other compounds with unused hydrogen-bonding capacity, see: Bhatt et al. (2006); Lewis et al. (2005); Desiraju et al. (2002). For related structures of other anabolic steroids, see: Verma et al. (2006). For related structures of steroid compounds with non-hydrogen-bonded OH or C=O motifs, see: Karpinska et al. (2011); Danaci et al. (1988); Chakrabarti et al. (1981); McPhail et al. (1977); Delettré et al. (1975). For applications of methandrostenolone, see: Druzhinina et al. (2008). For a previously reported mono hydrate (with no unused hydrogen-bonding capacity), see: Duax et al. (1982).

Computing details top

Data collection: CrysAlis171 (Oxford Diffraction, 2010); cell refinement: CrysAlis171 (Oxford Diffraction, 2010); data reduction: CrysAlis171 (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: CIFTAB (Sheldrick, 2008).

Figures top

	Fig. 1. One-dimensional hydrogen bonded chains in the crystal structure of methandrostenolone.
	Fig. 2. Packing diagram showing the 1D motifs along b with molecules coloured by symmetry equivalence.

17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one top

Crystal data top

C₂₀H₂₈O₂	F(000) = 1312
M_r = 300.42	D_x = 1.160 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.7107 Å
a = 28.317 (2) Å	Cell parameters from 1944 reflections
b = 9.4539 (5) Å	θ = 2.9–29.2°
c = 13.7684 (10) Å	µ = 0.07 mm⁻¹
β = 111.017 (9)°	T = 298 K
V = 3440.7 (4) Å³	Parallelepiped, colourless
Z = 8	0.50 × 0.40 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4697 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2893 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1048 pixels mm^-1	θ_max = 25.4°, θ_min = 2.9°
ω scans	h = −34→21
Absorption correction: multi-scan (CrysAlis171; Oxford Diffraction, 2010)	k = −8→11
T_min = 0.985, T_max = 1.000	l = −16→18
7321 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.072	H-atom parameters constrained
wR(F²) = 0.199	w = 1/[σ²(F_o²) + (0.0874P)² + 2.2675P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4697 reflections	Δρ_max = 0.65 e Å⁻³
404 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (9)

Crystal data top

C₂₀H₂₈O₂	V = 3440.7 (4) Å³
M_r = 300.42	Z = 8
Monoclinic, C2	Mo Kα radiation
a = 28.317 (2) Å	µ = 0.07 mm⁻¹
b = 9.4539 (5) Å	T = 298 K
c = 13.7684 (10) Å	0.50 × 0.40 × 0.20 mm
β = 111.017 (9)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4697 independent reflections
Absorption correction: multi-scan (CrysAlis171; Oxford Diffraction, 2010)	2893 reflections with I > 2σ(I)
T_min = 0.985, T_max = 1.000	R_int = 0.034
7321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	1 restraint
wR(F²) = 0.199	H-atom parameters constrained
S = 1.03	Δρ_max = 0.65 e Å⁻³
4697 reflections	Δρ_min = −0.26 e Å⁻³
404 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7034 (2)	1.0649 (8)	−0.1279 (3)	0.147 (3)
O2	0.91191 (19)	0.6512 (8)	0.5818 (3)	0.138 (2)
H2O2	0.9258	0.5758	0.6046	0.180*
C1	0.7739 (2)	1.1398 (7)	0.1374 (5)	0.0760 (17)
H1	0.8022	1.1918	0.1767	0.099*
C2	0.7592 (3)	1.1452 (7)	0.0348 (6)	0.088 (2)
H2A	0.7769	1.2022	0.0046	0.115*
C3	0.7155 (3)	1.0635 (9)	−0.0328 (5)	0.091 (2)
C4	0.6873 (2)	0.9890 (7)	0.0178 (4)	0.0770 (18)
H4	0.6583	0.9413	−0.0231	0.100*
C5	0.70045 (18)	0.9839 (6)	0.1216 (4)	0.0621 (14)
C6	0.6729 (2)	0.8922 (8)	0.1723 (5)	0.090 (2)
H6A	0.6440	0.8490	0.1194	0.117*
H6B	0.6606	0.9495	0.2167	0.117*
C7	0.7077 (2)	0.7781 (8)	0.2364 (4)	0.0793 (18)
H7A	0.7147	0.7114	0.1898	0.103*
H7B	0.6904	0.7272	0.2751	0.103*
C8	0.75730 (19)	0.8347 (6)	0.3120 (4)	0.0619 (15)
H8	0.7501	0.8896	0.3655	0.081*
C9	0.7937 (2)	0.7179 (7)	0.3653 (4)	0.0685 (15)
H9	0.8012	0.6680	0.3100	0.089*
C10	0.7765 (3)	0.6027 (8)	0.4256 (5)	0.101 (2)
H10A	0.7585	0.6440	0.4667	0.132*
H10B	0.7550	0.5330	0.3786	0.132*
C11	0.8267 (3)	0.5370 (9)	0.4953 (5)	0.116 (3)
H11A	0.8290	0.4401	0.4744	0.151*
H11B	0.8288	0.5369	0.5671	0.151*
C12	0.8709 (3)	0.6272 (9)	0.4841 (5)	0.101 (3)
C13	0.8448 (2)	0.7699 (8)	0.4417 (4)	0.0765 (18)
C14	0.8693 (2)	0.8604 (8)	0.3831 (4)	0.0811 (19)
H14A	0.8769	0.8029	0.3322	0.105*
H14B	0.9010	0.8981	0.4312	0.105*
C15	0.8344 (2)	0.9834 (7)	0.3275 (4)	0.0780 (18)
H15A	0.8303	1.0470	0.3792	0.101*
H15B	0.8502	1.0361	0.2868	0.101*
C16	0.78270 (17)	0.9333 (6)	0.2564 (4)	0.0521 (13)
H16	0.7892	0.8740	0.2041	0.068*
C17	0.74705 (19)	1.0534 (6)	0.1933 (4)	0.0609 (14)
C18	0.7340 (2)	1.1561 (8)	0.2678 (5)	0.093 (2)
H18A	0.7112	1.2276	0.2279	0.121*
H18B	0.7645	1.1998	0.3136	0.121*
H18C	0.7183	1.1044	0.3081	0.121*
C19	0.8392 (3)	0.8526 (9)	0.5324 (4)	0.098 (2)
H19A	0.8719	0.8843	0.5778	0.128*
H19B	0.8246	0.7926	0.5704	0.128*
H19C	0.8176	0.9329	0.5060	0.128*
C20	0.8936 (3)	0.5518 (9)	0.4139 (5)	0.120 (3)
H20A	0.9214	0.6062	0.4095	0.156*
H20B	0.8683	0.5415	0.3457	0.156*
H20C	0.9055	0.4601	0.4421	0.156*
O4	0.47262 (19)	0.9195 (5)	0.6785 (4)	0.1069 (16)
H4O4	0.4754	0.9614	0.7324	0.139*
O3	0.5497 (3)	0.0511 (7)	1.1560 (6)	0.172 (3)
C21	0.6004 (2)	0.3797 (9)	1.1075 (5)	0.093 (2)
H21	0.6120	0.4643	1.1423	0.121*
C22	0.5869 (3)	0.2739 (10)	1.1603 (5)	0.097 (2)
H22	0.5911	0.2871	1.2299	0.126*
C23	0.5658 (3)	0.1402 (9)	1.1088 (7)	0.116 (3)
C24	0.5673 (3)	0.1263 (8)	1.0132 (6)	0.105 (3)
H24	0.5577	0.0385	0.9819	0.137*
C25	0.5807 (2)	0.2215 (6)	0.9574 (5)	0.0689 (16)
C26	0.5755 (3)	0.1940 (7)	0.8476 (5)	0.0845 (18)
H26A	0.5643	0.0975	0.8289	0.110*
H26B	0.6081	0.2057	0.8401	0.110*
C27	0.5373 (2)	0.2967 (6)	0.7756 (4)	0.0678 (15)
H27A	0.5039	0.2745	0.7756	0.088*
H27B	0.5367	0.2843	0.7052	0.088*
C28	0.54964 (18)	0.4516 (5)	0.8080 (3)	0.0475 (12)
H28	0.5808	0.4785	0.7971	0.062*
C29	0.50704 (18)	0.5476 (5)	0.7438 (3)	0.0482 (11)
H29	0.4773	0.5200	0.7601	0.063*
C30	0.4902 (2)	0.5470 (7)	0.6264 (4)	0.0693 (15)
H30A	0.4680	0.4676	0.5971	0.090*
H30B	0.5191	0.5415	0.6045	0.090*
C31	0.4621 (2)	0.6876 (7)	0.5924 (4)	0.0781 (18)
H31A	0.4267	0.6705	0.5520	0.101*
H31B	0.4767	0.7410	0.5499	0.101*
C32	0.4675 (2)	0.7705 (6)	0.6926 (4)	0.0695 (15)
C33	0.51633 (19)	0.7034 (5)	0.7731 (4)	0.0562 (13)
C34	0.5242 (3)	0.7212 (6)	0.8868 (4)	0.0762 (17)
H34A	0.4933	0.6968	0.8980	0.099*
H34B	0.5319	0.8194	0.9065	0.099*
C35	0.5670 (2)	0.6281 (6)	0.9545 (4)	0.0728 (16)
H35A	0.5705	0.6393	1.0268	0.095*
H35B	0.5985	0.6576	0.9476	0.095*
C36	0.55717 (19)	0.4725 (5)	0.9237 (4)	0.0517 (12)
H36	0.5249	0.4481	0.9307	0.067*
C37	0.59779 (19)	0.3678 (7)	0.9965 (4)	0.0630 (15)
C38	0.6512 (2)	0.3981 (7)	0.9955 (5)	0.0871 (19)
H38A	0.6607	0.4935	1.0178	0.113*
H38B	0.6512	0.3857	0.9263	0.113*
H38C	0.6750	0.3338	1.0418	0.113*
C39	0.5624 (2)	0.7593 (7)	0.7519 (5)	0.0883 (19)
H39A	0.5671	0.8576	0.7701	0.115*
H39B	0.5570	0.7481	0.6794	0.115*
H39C	0.5919	0.7071	0.7928	0.115*
C40	0.4201 (2)	0.7533 (8)	0.7211 (5)	0.094 (2)
H40A	0.4236	0.8097	0.7813	0.122*
H40B	0.4163	0.6557	0.7361	0.122*
H40C	0.3909	0.7837	0.6639	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.161 (5)	0.225 (7)	0.065 (3)	0.046 (5)	0.054 (3)	0.040 (4)
O2	0.128 (4)	0.197 (6)	0.066 (3)	0.054 (4)	0.007 (3)	0.033 (4)
C1	0.073 (4)	0.074 (4)	0.086 (4)	0.007 (3)	0.035 (3)	0.022 (4)
C2	0.089 (4)	0.086 (5)	0.104 (5)	0.026 (4)	0.052 (4)	0.046 (4)
C3	0.104 (5)	0.117 (6)	0.066 (4)	0.044 (5)	0.047 (4)	0.035 (4)
C4	0.058 (3)	0.106 (5)	0.059 (3)	0.016 (3)	0.011 (3)	0.004 (4)
C5	0.049 (3)	0.082 (4)	0.056 (3)	0.012 (3)	0.020 (3)	0.008 (3)
C6	0.058 (3)	0.134 (6)	0.083 (4)	−0.003 (4)	0.030 (3)	0.013 (5)
C7	0.060 (3)	0.110 (5)	0.072 (4)	−0.008 (4)	0.028 (3)	0.017 (4)
C8	0.056 (3)	0.089 (4)	0.045 (3)	0.007 (3)	0.024 (3)	0.006 (3)
C9	0.074 (4)	0.088 (4)	0.052 (3)	0.015 (3)	0.034 (3)	0.014 (3)
C10	0.114 (5)	0.103 (5)	0.097 (5)	0.008 (5)	0.050 (4)	0.035 (5)
C11	0.168 (8)	0.113 (6)	0.088 (5)	0.049 (6)	0.069 (6)	0.039 (5)
C12	0.116 (5)	0.133 (7)	0.055 (4)	0.057 (5)	0.032 (4)	0.029 (4)
C13	0.077 (4)	0.113 (5)	0.039 (3)	0.029 (4)	0.020 (3)	0.009 (3)
C14	0.053 (3)	0.124 (6)	0.060 (3)	0.006 (4)	0.011 (3)	0.011 (4)
C15	0.062 (3)	0.100 (5)	0.068 (4)	0.002 (3)	0.019 (3)	0.014 (4)
C16	0.043 (2)	0.068 (3)	0.046 (3)	0.005 (2)	0.018 (2)	0.007 (3)
C17	0.057 (3)	0.074 (4)	0.057 (3)	0.010 (3)	0.027 (3)	0.009 (3)
C18	0.095 (4)	0.096 (5)	0.090 (4)	0.027 (4)	0.036 (4)	−0.001 (4)
C19	0.109 (5)	0.123 (6)	0.061 (4)	0.027 (5)	0.027 (4)	−0.003 (4)
C20	0.141 (6)	0.145 (7)	0.080 (4)	0.064 (6)	0.048 (5)	0.020 (5)
O4	0.157 (4)	0.062 (3)	0.095 (3)	0.024 (3)	0.037 (3)	0.025 (3)
O3	0.244 (7)	0.123 (5)	0.217 (7)	0.044 (5)	0.166 (6)	0.085 (5)
C21	0.087 (4)	0.109 (6)	0.085 (4)	0.040 (4)	0.033 (4)	0.008 (5)
C22	0.098 (5)	0.144 (7)	0.058 (4)	0.040 (5)	0.040 (4)	0.036 (5)
C23	0.156 (7)	0.089 (6)	0.141 (7)	0.056 (6)	0.100 (7)	0.053 (6)
C24	0.132 (6)	0.077 (5)	0.146 (7)	0.040 (5)	0.096 (6)	0.049 (5)
C25	0.077 (4)	0.051 (3)	0.096 (4)	0.017 (3)	0.052 (4)	0.024 (3)
C26	0.114 (5)	0.047 (3)	0.100 (5)	0.007 (4)	0.049 (4)	0.003 (4)
C27	0.087 (4)	0.057 (4)	0.069 (4)	0.005 (3)	0.040 (3)	−0.008 (3)
C28	0.058 (3)	0.044 (3)	0.049 (3)	0.002 (2)	0.029 (2)	−0.002 (2)
C29	0.061 (3)	0.045 (3)	0.043 (2)	0.001 (3)	0.023 (2)	−0.002 (2)
C30	0.078 (4)	0.084 (4)	0.044 (3)	0.013 (3)	0.020 (3)	0.003 (3)
C31	0.090 (4)	0.104 (5)	0.040 (3)	0.033 (4)	0.024 (3)	0.013 (3)
C32	0.092 (4)	0.056 (3)	0.061 (3)	0.021 (3)	0.028 (3)	0.015 (3)
C33	0.070 (3)	0.049 (3)	0.053 (3)	0.008 (3)	0.025 (3)	0.010 (3)
C34	0.112 (5)	0.044 (3)	0.066 (4)	0.017 (3)	0.024 (4)	−0.007 (3)
C35	0.089 (4)	0.067 (4)	0.055 (3)	0.007 (4)	0.017 (3)	−0.012 (3)
C36	0.060 (3)	0.052 (3)	0.047 (3)	0.007 (2)	0.024 (2)	−0.004 (2)
C37	0.060 (3)	0.081 (4)	0.054 (3)	0.021 (3)	0.027 (3)	0.013 (3)
C38	0.080 (4)	0.086 (5)	0.101 (5)	0.011 (4)	0.039 (4)	0.007 (4)
C39	0.100 (5)	0.058 (4)	0.107 (5)	−0.014 (4)	0.037 (4)	0.015 (4)
C40	0.095 (4)	0.111 (5)	0.085 (4)	0.047 (4)	0.042 (4)	0.014 (4)

Geometric parameters (Å, º) top

O1—C3	1.228 (7)	O4—C32	1.436 (7)
O2—C12	1.445 (8)	O4—H4O4	0.8200
O2—H2O2	0.8200	O3—C23	1.246 (8)
C1—C2	1.322 (9)	C21—C22	1.370 (10)
C1—C17	1.504 (7)	C21—C37	1.507 (7)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.472 (9)	C22—C23	1.468 (12)
C2—H2A	0.9300	C22—H22	0.9300
C3—C4	1.420 (9)	C23—C24	1.339 (10)
C4—C5	1.343 (7)	C24—C25	1.325 (8)
C4—H4	0.9300	C24—H24	0.9300
C5—C17	1.488 (7)	C25—C26	1.488 (8)
C5—C6	1.495 (8)	C25—C37	1.499 (9)
C6—C7	1.513 (9)	C26—C27	1.526 (8)
C6—H6A	0.9700	C26—H26A	0.9700
C6—H6B	0.9700	C26—H26B	0.9700
C7—C8	1.515 (8)	C27—C28	1.534 (7)
C7—H7A	0.9700	C27—H27A	0.9700
C7—H7B	0.9700	C27—H27B	0.9700
C8—C9	1.510 (7)	C28—C29	1.515 (6)
C8—C16	1.539 (6)	C28—C36	1.542 (6)
C8—H8	0.9800	C28—H28	0.9800
C9—C13	1.532 (8)	C29—C30	1.513 (6)
C9—C10	1.551 (8)	C29—C33	1.525 (7)
C9—H9	0.9800	C29—H29	0.9800
C10—C11	1.531 (9)	C30—C31	1.534 (8)
C10—H10A	0.9700	C30—H30A	0.9700
C10—H10B	0.9700	C30—H30B	0.9700
C11—C12	1.568 (11)	C31—C32	1.545 (7)
C11—H11A	0.9700	C31—H31A	0.9700
C11—H11B	0.9700	C31—H31B	0.9700
C12—C20	1.516 (9)	C32—C40	1.537 (8)
C12—C13	1.549 (10)	C32—C33	1.564 (7)
C13—C14	1.507 (8)	C33—C34	1.509 (7)
C13—C19	1.529 (8)	C33—C39	1.530 (7)
C14—C15	1.541 (9)	C34—C35	1.518 (7)
C14—H14A	0.9700	C34—H34A	0.9700
C14—H14B	0.9700	C34—H34B	0.9700
C15—C16	1.516 (7)	C35—C36	1.529 (7)
C15—H15A	0.9700	C35—H35A	0.9700
C15—H15B	0.9700	C35—H35B	0.9700
C16—C17	1.560 (7)	C36—C37	1.575 (7)
C16—H16	0.9800	C36—H36	0.9800
C17—C18	1.550 (8)	C37—C38	1.545 (8)
C18—H18A	0.9600	C38—H38A	0.9600
C18—H18B	0.9600	C38—H38B	0.9600
C18—H18C	0.9600	C38—H38C	0.9600
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600

C12—O2—H2O2	109.5	C32—O4—H4O4	109.5
C2—C1—C17	123.0 (6)	C22—C21—C37	124.2 (7)
C2—C1—H1	118.5	C22—C21—H21	117.9
C17—C1—H1	118.5	C37—C21—H21	117.9
C1—C2—C3	121.8 (6)	C21—C22—C23	121.1 (6)
C1—C2—H2A	119.1	C21—C22—H22	119.5
C3—C2—H2A	119.1	C23—C22—H22	119.5
O1—C3—C4	122.5 (8)	O3—C23—C24	126.4 (10)
O1—C3—C2	121.2 (7)	O3—C23—C22	119.5 (8)
C4—C3—C2	116.2 (5)	C24—C23—C22	114.1 (7)
C5—C4—C3	123.4 (6)	C25—C24—C23	128.4 (8)
C5—C4—H4	118.3	C25—C24—H24	115.8
C3—C4—H4	118.3	C23—C24—H24	115.8
C4—C5—C17	122.1 (5)	C24—C25—C26	121.7 (6)
C4—C5—C6	121.7 (6)	C24—C25—C37	122.8 (6)
C17—C5—C6	115.7 (4)	C26—C25—C37	115.3 (5)
C5—C6—C7	110.3 (4)	C25—C26—C27	109.8 (5)
C5—C6—H6A	109.6	C25—C26—H26A	109.7
C7—C6—H6A	109.6	C27—C26—H26A	109.7
C5—C6—H6B	109.6	C25—C26—H26B	109.7
C7—C6—H6B	109.6	C27—C26—H26B	109.7
H6A—C6—H6B	108.1	H26A—C26—H26B	108.2
C6—C7—C8	113.5 (6)	C26—C27—C28	112.5 (5)
C6—C7—H7A	108.9	C26—C27—H27A	109.1
C8—C7—H7A	108.9	C28—C27—H27A	109.1
C6—C7—H7B	108.9	C26—C27—H27B	109.1
C8—C7—H7B	108.9	C28—C27—H27B	109.1
H7A—C7—H7B	107.7	H27A—C27—H27B	107.8
C9—C8—C7	112.3 (5)	C29—C28—C27	110.5 (4)
C9—C8—C16	108.9 (4)	C29—C28—C36	108.2 (3)
C7—C8—C16	110.8 (4)	C27—C28—C36	110.9 (4)
C9—C8—H8	108.2	C29—C28—H28	109.1
C7—C8—H8	108.2	C27—C28—H28	109.1
C16—C8—H8	108.2	C36—C28—H28	109.1
C8—C9—C13	114.3 (5)	C30—C29—C28	120.1 (4)
C8—C9—C10	118.8 (4)	C30—C29—C33	104.1 (4)
C13—C9—C10	105.0 (5)	C28—C29—C33	113.5 (4)
C8—C9—H9	105.9	C30—C29—H29	106.1
C13—C9—H9	105.9	C28—C29—H29	106.1
C10—C9—H9	105.9	C33—C29—H29	106.1
C11—C10—C9	102.8 (5)	C29—C30—C31	104.7 (4)
C11—C10—H10A	111.2	C29—C30—H30A	110.8
C9—C10—H10A	111.2	C31—C30—H30A	110.8
C11—C10—H10B	111.2	C29—C30—H30B	110.8
C9—C10—H10B	111.2	C31—C30—H30B	110.8
H10A—C10—H10B	109.1	H30A—C30—H30B	108.9
C10—C11—C12	108.2 (6)	C30—C31—C32	107.0 (4)
C10—C11—H11A	110.1	C30—C31—H31A	110.3
C12—C11—H11A	110.1	C32—C31—H31A	110.3
C10—C11—H11B	110.1	C30—C31—H31B	110.3
C12—C11—H11B	110.1	C32—C31—H31B	110.3
H11A—C11—H11B	108.4	H31A—C31—H31B	108.6
O2—C12—C20	106.6 (6)	O4—C32—C40	106.2 (5)
O2—C12—C13	109.3 (7)	O4—C32—C31	111.1 (5)
C20—C12—C13	115.0 (5)	C40—C32—C31	111.0 (5)
O2—C12—C11	113.4 (5)	O4—C32—C33	112.8 (5)
C20—C12—C11	110.1 (7)	C40—C32—C33	114.0 (4)
C13—C12—C11	102.7 (5)	C31—C32—C33	101.9 (4)
C14—C13—C19	110.5 (6)	C34—C33—C29	109.3 (4)
C14—C13—C9	108.5 (4)	C34—C33—C39	110.0 (5)
C19—C13—C9	112.1 (5)	C29—C33—C39	111.2 (4)
C14—C13—C12	116.5 (5)	C34—C33—C32	117.0 (4)
C19—C13—C12	108.2 (5)	C29—C33—C32	100.3 (4)
C9—C13—C12	100.7 (6)	C39—C33—C32	108.8 (4)
C13—C14—C15	110.9 (4)	C33—C34—C35	111.1 (4)
C13—C14—H14A	109.5	C33—C34—H34A	109.4
C15—C14—H14A	109.5	C35—C34—H34A	109.4
C13—C14—H14B	109.5	C33—C34—H34B	109.4
C15—C14—H14B	109.5	C35—C34—H34B	109.4
H14A—C14—H14B	108.0	H34A—C34—H34B	108.0
C16—C15—C14	112.6 (5)	C34—C35—C36	111.2 (4)
C16—C15—H15A	109.1	C34—C35—H35A	109.4
C14—C15—H15A	109.1	C36—C35—H35A	109.4
C16—C15—H15B	109.1	C34—C35—H35B	109.4
C14—C15—H15B	109.1	C36—C35—H35B	109.4
H15A—C15—H15B	107.8	H35A—C35—H35B	108.0
C15—C16—C8	112.6 (4)	C35—C36—C28	110.8 (4)
C15—C16—C17	114.5 (5)	C35—C36—C37	114.1 (4)
C8—C16—C17	113.2 (4)	C28—C36—C37	112.1 (4)
C15—C16—H16	105.2	C35—C36—H36	106.4
C8—C16—H16	105.2	C28—C36—H36	106.4
C17—C16—H16	105.2	C37—C36—H36	106.4
C5—C17—C1	113.0 (4)	C25—C37—C21	109.0 (5)
C5—C17—C18	110.6 (4)	C25—C37—C38	111.0 (5)
C1—C17—C18	106.4 (5)	C21—C37—C38	107.6 (5)
C5—C17—C16	106.9 (4)	C25—C37—C36	106.5 (4)
C1—C17—C16	109.6 (4)	C21—C37—C36	111.0 (4)
C18—C17—C16	110.3 (4)	C38—C37—C36	111.8 (4)
C17—C18—H18A	109.5	C37—C38—H38A	109.5
C17—C18—H18B	109.5	C37—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
C17—C18—H18C	109.5	C37—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
C13—C19—H19A	109.5	C33—C39—H39A	109.5
C13—C19—H19B	109.5	C33—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C13—C19—H19C	109.5	C33—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
C12—C20—H20A	109.5	C32—C40—H40A	109.5
C12—C20—H20B	109.5	C32—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C12—C20—H20C	109.5	C32—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5

C17—C1—C2—C3	−1.4 (9)	C37—C21—C22—C23	−3.2 (10)
C1—C2—C3—O1	−177.0 (7)	C21—C22—C23—O3	−173.6 (7)
C1—C2—C3—C4	5.6 (9)	C21—C22—C23—C24	7.9 (10)
O1—C3—C4—C5	178.6 (7)	O3—C23—C24—C25	174.8 (7)
C2—C3—C4—C5	−4.0 (9)	C22—C23—C24—C25	−6.9 (12)
C3—C4—C5—C17	−1.8 (9)	C23—C24—C25—C26	−173.8 (7)
C3—C4—C5—C6	−173.5 (6)	C23—C24—C25—C37	0.7 (11)
C4—C5—C6—C7	115.1 (6)	C24—C25—C26—C27	115.7 (6)
C17—C5—C6—C7	−57.1 (7)	C37—C25—C26—C27	−59.2 (6)
C5—C6—C7—C8	51.8 (7)	C25—C26—C27—C28	53.1 (6)
C6—C7—C8—C9	−172.9 (4)	C26—C27—C28—C29	−172.1 (4)
C6—C7—C8—C16	−50.8 (6)	C26—C27—C28—C36	−52.2 (6)
C7—C8—C9—C13	179.3 (4)	C27—C28—C29—C30	−56.9 (6)
C16—C8—C9—C13	56.1 (5)	C36—C28—C29—C30	−178.5 (4)
C7—C8—C9—C10	−55.8 (6)	C27—C28—C29—C33	179.0 (4)
C16—C8—C9—C10	−179.0 (5)	C36—C28—C29—C33	57.5 (5)
C8—C9—C10—C11	−162.1 (5)	C28—C29—C30—C31	−160.2 (5)
C13—C9—C10—C11	−32.8 (6)	C33—C29—C30—C31	−31.8 (5)
C9—C10—C11—C12	7.1 (7)	C29—C30—C31—C32	4.6 (6)
C10—C11—C12—O2	138.2 (6)	C30—C31—C32—O4	143.7 (5)
C10—C11—C12—C20	−102.5 (6)	C30—C31—C32—C40	−98.4 (6)
C10—C11—C12—C13	20.5 (7)	C30—C31—C32—C33	23.4 (6)
C8—C9—C13—C14	−59.4 (6)	C30—C29—C33—C34	169.8 (4)
C10—C9—C13—C14	168.6 (5)	C28—C29—C33—C34	−57.9 (5)
C8—C9—C13—C19	62.9 (6)	C30—C29—C33—C39	−68.7 (5)
C10—C9—C13—C19	−69.0 (7)	C28—C29—C33—C39	63.6 (5)
C8—C9—C13—C12	177.7 (4)	C30—C29—C33—C32	46.2 (4)
C10—C9—C13—C12	45.8 (5)	C28—C29—C33—C32	178.5 (4)
O2—C12—C13—C14	82.6 (6)	O4—C32—C33—C34	80.9 (6)
C20—C12—C13—C14	−37.2 (9)	C40—C32—C33—C34	−40.3 (7)
C11—C12—C13—C14	−156.7 (5)	C31—C32—C33—C34	−160.0 (5)
O2—C12—C13—C19	−42.6 (7)	O4—C32—C33—C29	−161.1 (4)
C20—C12—C13—C19	−162.4 (7)	C40—C32—C33—C29	77.7 (6)
C11—C12—C13—C19	78.1 (6)	C31—C32—C33—C29	−42.0 (5)
O2—C12—C13—C9	−160.3 (5)	O4—C32—C33—C39	−44.4 (6)
C20—C12—C13—C9	79.9 (7)	C40—C32—C33—C39	−165.6 (5)
C11—C12—C13—C9	−39.7 (6)	C31—C32—C33—C39	74.7 (5)
C19—C13—C14—C15	−67.1 (6)	C29—C33—C34—C35	56.0 (6)
C9—C13—C14—C15	56.3 (7)	C39—C33—C34—C35	−66.2 (6)
C12—C13—C14—C15	168.9 (6)	C32—C33—C34—C35	169.1 (5)
C13—C14—C15—C16	−55.1 (6)	C33—C34—C35—C36	−57.3 (7)
C14—C15—C16—C8	52.4 (6)	C34—C35—C36—C28	57.2 (6)
C14—C15—C16—C17	−176.5 (4)	C34—C35—C36—C37	−175.2 (4)
C9—C8—C16—C15	−51.5 (6)	C29—C28—C36—C35	−56.0 (5)
C7—C8—C16—C15	−175.6 (5)	C27—C28—C36—C35	−177.4 (4)
C9—C8—C16—C17	176.7 (4)	C29—C28—C36—C37	175.3 (4)
C7—C8—C16—C17	52.7 (6)	C27—C28—C36—C37	53.9 (5)
C4—C5—C17—C1	5.8 (8)	C24—C25—C37—C21	4.3 (7)
C6—C5—C17—C1	178.0 (5)	C26—C25—C37—C21	179.1 (5)
C4—C5—C17—C18	125.0 (6)	C24—C25—C37—C38	122.6 (6)
C6—C5—C17—C18	−62.8 (7)	C26—C25—C37—C38	−62.6 (6)
C4—C5—C17—C16	−114.9 (6)	C24—C25—C37—C36	−115.5 (6)
C6—C5—C17—C16	57.3 (6)	C26—C25—C37—C36	59.4 (6)
C2—C1—C17—C5	−4.2 (8)	C22—C21—C37—C25	−2.8 (8)
C2—C1—C17—C18	−125.7 (6)	C22—C21—C37—C38	−123.2 (6)
C2—C1—C17—C16	115.0 (6)	C22—C21—C37—C36	114.2 (6)
C15—C16—C17—C5	174.9 (4)	C35—C36—C37—C25	177.5 (4)
C8—C16—C17—C5	−54.3 (5)	C28—C36—C37—C25	−55.5 (5)
C15—C16—C17—C1	52.1 (6)	C35—C36—C37—C21	59.1 (6)
C8—C16—C17—C1	−177.1 (5)	C28—C36—C37—C21	−174.0 (5)
C15—C16—C17—C18	−64.8 (6)	C35—C36—C37—C38	−61.1 (6)
C8—C16—C17—C18	66.0 (6)	C28—C36—C37—C38	65.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O2···O4ⁱ	0.82	2.00	2.808 (7)	167
O4—H4O4···O3ⁱⁱ	0.82	2.09	2.858 (7)	156

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1, y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₈O₂
M_r	300.42
Crystal system, space group	Monoclinic, C2
Temperature (K)	298
a, b, c (Å)	28.317 (2), 9.4539 (5), 13.7684 (10)
β (°)	111.017 (9)
V (Å³)	3440.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis171; Oxford Diffraction, 2010)
T_min, T_max	0.985, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7321, 4697, 2893
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.199, 1.03
No. of reflections	4697
No. of parameters	404
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.26

Computer programs: CrysAlis171 (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEX (McArdle, 1995), CIFTAB (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O2···O4ⁱ	0.82	2.00	2.808 (7)	167.1
O4—H4O4···O3ⁱⁱ	0.82	2.09	2.858 (7)	156.1

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1, y+1, −z+2.

Acknowledgements

The authors thank the Science Foundation Ireland (SFI) for funding for the Solid State Pharmaceuticals Cluster (SSPC).

References

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