11β-Hy­droxy­medroxyprogesterone

Yusop, S.N.W.; Sultan, S.; Yamin, B.M.; Shah, S.A.A.; Naz, H.

doi:10.1107/S2414314616010750

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 7| July 2016| x161075

https://doi.org/10.1107/S2414314616010750

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11β-Hydroxymedroxyprogesterone

Sharifah Nurfazilah Wan Yusop,^a,^b Sadia Sultan,^a,^b Bohari M. Yamin,^c Syed Adnan Ali Shah ^a,^b and Humera Naz ^a,^b ^*

^aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia, ^bFaculty of Pharmacy, Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia, and ^cSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor D.E., Malaysia
^*Correspondence e-mail: humera@salam.uitm.edu.my

Edited by M. Zeller, Purdue University, USA (Received 30 May 2016; accepted 4 July 2016; online 12 July 2016)

The title compound, C₂₂H₃₂O₄, a fungal-transformed metabolite of medroxyprogesterone, comprises one cyclohexanone ring, two cyclohexane rings and one cyclopentane ring fused together. The cyclohexanone ring has a half-chair conformation, while the cyclohexane rings possess chair conformations and the cyclopentane ring has a twisted conformation on the fused C—C bond. In the crystal, molecules are linked by strong O—H⋯O and also C—H⋯O hydrogen bonds, creating a two-dimensional network parallel to (10-1).

Keywords: crystal structure; medroxyprogesterone; fungal-transformed metabolite.

CCDC reference: 1489720

Structure description

11β-Hydroxymedroxyprogesterone, is a steroid produced by biotransformation of medroxyprogesterone (MP). Medroxyprogesterone is known as a progesterone agonist which is important as a sex hormone. The progesterone agonist activity of MP is less effective than medroxyprogesterone acetate (MPA) (Pullen et al., 2006 ) which has been used for treatment of endometrial carcinoma (Fujiwara et al., 2012 ). In a continuation of our work on biotransformation of steroids (Sultan et al., 2014 ), we aimed to produce unique structurally modified derivatives of medroxyprogesterone that may be more effective than MPA. Herein we report the X-ray study of 11β-hydroxymedroxyprogesterone (Fig. 1), a biotransformation product of medroxyprogesterone.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

The molecule comprises four annelated rings. Ring A (C1–C5/C10) is a cyclohexanone having a half-chair conformation, while rings B (C5–C10) and C (C8/C9/C11–C14) are cyclohexane rings with chair conformations. The cyclopentane ring D (C13–C17) adopts a twisted conformation on the fused C—C bond, C13—C14.

In the crystal, the molecules are linked by strong O—H⋯O hydrogen bonds, O3—H3A⋯O1ⁱ and O4—H4A⋯O3ⁱⁱ, augmented by a C—H⋯O interaction, C18—H18C⋯O1ⁱ, forming a two-dimensional network parallel to (10 $[\overline1]$ ) (see Fig. 2 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.81 (3)	2.02 (4)	2.767 (5)	153 (4)
O4—H4A⋯O3ⁱⁱ	0.82 (5)	2.12 (5)	2.910 (5)	165 (6)
C18—H18C⋯O1ⁱ	0.96	2.47	3.411 (6)	165
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z]$ .

Figure 2
The crystal packing of the title compound viewed along the a ax1s. Dashed lines indicate hydrogen bonds.

Synthesis and crystallization

The title compound was obtained from the fungal transformation of medroxyprogesterone via Trichothecium roseum (ATCC 13411) after 8 d of fermentation. 56.6 mg of this compound was purified by recycling preparative HPLC. The compound was crystallized at room temperature from a mixture of chloroform and methanol.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The absolute configuration was not determined from the X-ray data but it could be determined through the comparison of similar compounds (Ouedraogo et al., 2013 , Karpinska et al., 2013 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₃₂O₄
M_r	360.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	302
a, b, c (Å)	6.8692 (12), 12.221 (2), 11.7933 (19)
β (°)	105.726 (5)
V (Å³)	952.9 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.50 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.959, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	16639, 3527, 3023
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.122, 1.09
No. of reflections	3527
No. of parameters	248
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1489720

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616010750/zl4009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616010750/zl4009Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

11β-Hydroxymedroxyprogesterone top

Crystal data top

C₂₂H₃₂O₄	D_x = 1.256 Mg m⁻³
M_r = 360.47	Melting point = 491–493 K
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.8692 (12) Å	Cell parameters from 9916 reflections
b = 12.221 (2) Å	θ = 3.1–25.5°
c = 11.7933 (19) Å	µ = 0.09 mm⁻¹
β = 105.726 (5)°	T = 302 K
V = 952.9 (3) Å³	Block, colourless
Z = 2	0.50 × 0.50 × 0.23 mm
F(000) = 392

Data collection top

Bruker APEXII CCD diffractometer	3527 independent reflections
Radiation source: fine-focus sealed tube	3023 reflections with I > 2σ(I)
Detector resolution: 83.66 pixels mm^-1	R_int = 0.074
φ and ω scans	θ_max = 25.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→7
T_min = 0.959, T_max = 0.981	k = −14→14
16639 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0268P)² + 0.6466P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.122	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.20 e Å⁻³
3527 reflections	Δρ_min = −0.21 e Å⁻³
248 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.023 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), ???? Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −1.3 (6)

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

	x	y	z	U_iso*/U_eq
O1	0.5345 (6)	0.5911 (3)	0.6547 (3)	0.0596 (10)
O2	−0.0798 (5)	0.7685 (3)	−0.2863 (3)	0.0510 (9)
O3	0.3276 (5)	0.9316 (2)	0.1760 (3)	0.0355 (7)
O4	−0.1195 (5)	0.6185 (3)	−0.0443 (3)	0.0380 (7)
C1	0.5080 (7)	0.8207 (3)	0.4627 (3)	0.0362 (10)
H1A	0.6215	0.8519	0.5215	0.043*
H1B	0.4134	0.8794	0.4319	0.043*
C2	0.4047 (8)	0.7364 (4)	0.5217 (4)	0.0440 (11)
H2A	0.3654	0.7701	0.5866	0.053*
H2B	0.2834	0.7096	0.4655	0.053*
C3	0.5459 (8)	0.6426 (4)	0.5667 (4)	0.0442 (11)
C4	0.6824 (7)	0.6123 (4)	0.4983 (4)	0.0424 (11)
H4B	0.7656	0.5520	0.5227	0.051*
C5	0.6970 (6)	0.6660 (3)	0.4012 (4)	0.0335 (10)
C6	0.8029 (6)	0.6207 (4)	0.3160 (4)	0.0373 (10)
H6A	0.8896	0.6785	0.2987	0.045*
C7	0.6362 (6)	0.5958 (4)	0.2015 (4)	0.0365 (10)
H7A	0.7004	0.5740	0.1412	0.044*
H7B	0.5571	0.5342	0.2158	0.044*
C8	0.4922 (6)	0.6912 (3)	0.1540 (3)	0.0265 (9)
H8A	0.5650	0.7475	0.1227	0.032*
C9	0.4091 (6)	0.7421 (3)	0.2508 (3)	0.0254 (8)
H9A	0.3372	0.6822	0.2773	0.030*
C10	0.5843 (6)	0.7738 (3)	0.3623 (3)	0.0287 (9)
C11	0.2469 (6)	0.8306 (3)	0.2052 (3)	0.0273 (9)
H11A	0.1829	0.8460	0.2683	0.033*
C12	0.0800 (6)	0.7922 (3)	0.0973 (3)	0.0276 (9)
H12A	−0.0024	0.7376	0.1221	0.033*
H12B	−0.0064	0.8538	0.0653	0.033*
C13	0.1637 (5)	0.7435 (3)	0.0004 (3)	0.0232 (8)
C14	0.3119 (6)	0.6509 (3)	0.0548 (3)	0.0270 (9)
H14A	0.2367	0.6000	0.0914	0.032*
C15	0.3503 (6)	0.5910 (3)	−0.0505 (4)	0.0356 (10)
H15A	0.3845	0.5149	−0.0318	0.043*
H15B	0.4589	0.6253	−0.0757	0.043*
C16	0.1477 (6)	0.6011 (4)	−0.1461 (3)	0.0329 (9)
H16A	0.1697	0.6308	−0.2179	0.039*
H16B	0.0847	0.5298	−0.1635	0.039*
C17	0.0112 (6)	0.6779 (3)	−0.0986 (3)	0.0287 (9)
C18	0.7350 (7)	0.8583 (3)	0.3368 (4)	0.0396 (11)
H18A	0.7588	0.8424	0.2619	0.059*
H18B	0.8603	0.8543	0.3975	0.059*
H18C	0.6793	0.9305	0.3351	0.059*
C19	0.2619 (6)	0.8320 (3)	−0.0585 (4)	0.0304 (9)
H19A	0.2880	0.8027	−0.1285	0.046*
H19B	0.3868	0.8551	−0.0050	0.046*
H19C	0.1722	0.8935	−0.0789	0.046*
C20	−0.1183 (6)	0.7539 (4)	−0.1932 (4)	0.0343 (10)
C21	−0.2902 (8)	0.8123 (5)	−0.1650 (5)	0.0603 (15)
H21A	−0.2766	0.8074	−0.0819	0.090*
H21B	−0.4155	0.7793	−0.2076	0.090*
H21C	−0.2892	0.8878	−0.1872	0.090*
C22	0.9346 (9)	0.5198 (4)	0.3577 (5)	0.0591 (15)
H22A	1.0038	0.5005	0.2999	0.089*
H22B	0.8508	0.4598	0.3681	0.089*
H22C	1.0319	0.5356	0.4312	0.089*
H3A	0.382 (6)	0.960 (4)	0.239 (2)	0.037 (13)*
H4A	−0.168 (9)	0.570 (4)	−0.091 (4)	0.07 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.094 (3)	0.0388 (19)	0.0452 (19)	−0.0059 (19)	0.0167 (19)	0.0157 (16)
O2	0.055 (2)	0.058 (2)	0.0376 (18)	−0.0016 (17)	0.0081 (16)	0.0057 (16)
O3	0.0448 (19)	0.0208 (14)	0.0333 (16)	−0.0006 (13)	−0.0022 (14)	−0.0014 (13)
O4	0.0393 (17)	0.0384 (17)	0.0399 (16)	−0.0183 (14)	0.0167 (14)	−0.0094 (14)
C1	0.050 (3)	0.029 (2)	0.0246 (19)	0.0046 (19)	0.0016 (19)	0.0002 (17)
C2	0.057 (3)	0.043 (3)	0.033 (2)	0.004 (2)	0.013 (2)	0.004 (2)
C3	0.058 (3)	0.033 (2)	0.036 (2)	−0.007 (2)	0.005 (2)	0.0028 (19)
C4	0.052 (3)	0.026 (2)	0.042 (2)	0.004 (2)	0.000 (2)	0.006 (2)
C5	0.034 (2)	0.026 (2)	0.033 (2)	0.0022 (18)	−0.0046 (18)	0.0011 (17)
C6	0.031 (2)	0.030 (2)	0.047 (2)	0.0080 (19)	0.0045 (19)	0.002 (2)
C7	0.036 (2)	0.032 (2)	0.040 (2)	0.0093 (19)	0.0081 (19)	−0.0035 (19)
C8	0.024 (2)	0.0233 (19)	0.033 (2)	0.0021 (16)	0.0085 (17)	0.0018 (16)
C9	0.031 (2)	0.0202 (17)	0.0263 (18)	0.0003 (16)	0.0092 (16)	0.0010 (15)
C10	0.031 (2)	0.0224 (19)	0.030 (2)	0.0036 (17)	0.0037 (17)	0.0022 (16)
C11	0.030 (2)	0.026 (2)	0.0268 (19)	0.0010 (17)	0.0092 (17)	−0.0018 (16)
C12	0.023 (2)	0.028 (2)	0.033 (2)	0.0023 (16)	0.0096 (17)	−0.0026 (17)
C13	0.0174 (18)	0.0231 (18)	0.0312 (19)	−0.0022 (16)	0.0100 (16)	−0.0007 (16)
C14	0.024 (2)	0.027 (2)	0.031 (2)	0.0008 (16)	0.0102 (16)	−0.0014 (16)
C15	0.035 (2)	0.031 (2)	0.041 (2)	0.0058 (18)	0.0120 (19)	−0.0074 (18)
C16	0.036 (2)	0.031 (2)	0.033 (2)	−0.0024 (18)	0.0121 (17)	−0.0082 (18)
C17	0.025 (2)	0.031 (2)	0.031 (2)	−0.0048 (17)	0.0090 (17)	−0.0065 (17)
C18	0.038 (3)	0.027 (2)	0.048 (3)	−0.0022 (18)	0.001 (2)	0.0003 (19)
C19	0.032 (2)	0.028 (2)	0.033 (2)	−0.0034 (17)	0.0119 (18)	0.0027 (17)
C20	0.027 (2)	0.037 (2)	0.035 (2)	−0.0028 (18)	0.0005 (18)	−0.0068 (18)
C21	0.046 (3)	0.074 (4)	0.057 (3)	0.017 (3)	0.008 (3)	0.000 (3)
C22	0.053 (3)	0.047 (3)	0.065 (3)	0.025 (3)	−0.003 (3)	−0.001 (2)

Geometric parameters (Å, º) top

O1—C3	1.235 (5)	C11—C12	1.537 (5)
O2—C20	1.210 (5)	C11—H11A	0.9800
O3—C11	1.433 (5)	C12—C13	1.532 (5)
O3—H3A	0.813 (14)	C12—H12A	0.9700
O4—C17	1.434 (5)	C12—H12B	0.9700
O4—H4A	0.818 (14)	C13—C19	1.537 (5)
C1—C2	1.523 (6)	C13—C14	1.540 (5)
C1—C10	1.530 (6)	C13—C17	1.562 (5)
C1—H1A	0.9700	C14—C15	1.526 (5)
C1—H1B	0.9700	C14—H14A	0.9800
C2—C3	1.502 (7)	C15—C16	1.540 (6)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—C4	1.441 (7)	C16—C17	1.535 (5)
C4—C5	1.346 (6)	C16—H16A	0.9700
C4—H4B	0.9300	C16—H16B	0.9700
C5—C6	1.497 (6)	C17—C20	1.537 (6)
C5—C10	1.534 (5)	C18—H18A	0.9600
C6—C22	1.530 (6)	C18—H18B	0.9600
C6—C7	1.546 (6)	C18—H18C	0.9600
C6—H6A	0.9800	C19—H19A	0.9600
C7—C8	1.533 (5)	C19—H19B	0.9600
C7—H7A	0.9700	C19—H19C	0.9600
C7—H7B	0.9700	C20—C21	1.493 (7)
C8—C14	1.536 (5)	C21—H21A	0.9600
C8—C9	1.539 (5)	C21—H21B	0.9600
C8—H8A	0.9800	C21—H21C	0.9600
C9—C11	1.542 (5)	C22—H22A	0.9600
C9—C10	1.571 (5)	C22—H22B	0.9600
C9—H9A	0.9800	C22—H22C	0.9600
C10—C18	1.548 (6)

C11—O3—H3A	105 (3)	C11—C12—H12A	109.0
C17—O4—H4A	105 (4)	C13—C12—H12B	109.0
C2—C1—C10	113.6 (3)	C11—C12—H12B	109.0
C2—C1—H1A	108.9	H12A—C12—H12B	107.8
C10—C1—H1A	108.9	C12—C13—C19	111.3 (3)
C2—C1—H1B	108.9	C12—C13—C14	108.3 (3)
C10—C1—H1B	108.9	C19—C13—C14	112.6 (3)
H1A—C1—H1B	107.7	C12—C13—C17	116.5 (3)
C3—C2—C1	109.9 (4)	C19—C13—C17	108.1 (3)
C3—C2—H2A	109.7	C14—C13—C17	99.7 (3)
C1—C2—H2A	109.7	C15—C14—C8	119.5 (3)
C3—C2—H2B	109.7	C15—C14—C13	104.7 (3)
C1—C2—H2B	109.7	C8—C14—C13	112.8 (3)
H2A—C2—H2B	108.2	C15—C14—H14A	106.3
O1—C3—C4	122.6 (4)	C8—C14—H14A	106.3
O1—C3—C2	120.3 (5)	C13—C14—H14A	106.3
C4—C3—C2	117.0 (4)	C14—C15—C16	103.6 (3)
C5—C4—C3	124.1 (4)	C14—C15—H15A	111.0
C5—C4—H4B	118.0	C16—C15—H15A	111.0
C3—C4—H4B	118.0	C14—C15—H15B	111.0
C4—C5—C6	123.6 (4)	C16—C15—H15B	111.0
C4—C5—C10	121.7 (4)	H15A—C15—H15B	109.0
C6—C5—C10	114.4 (4)	C17—C16—C15	107.6 (3)
C5—C6—C22	115.8 (4)	C17—C16—H16A	110.2
C5—C6—C7	106.2 (3)	C15—C16—H16A	110.2
C22—C6—C7	110.8 (4)	C17—C16—H16B	110.2
C5—C6—H6A	107.9	C15—C16—H16B	110.2
C22—C6—H6A	107.9	H16A—C16—H16B	108.5
C7—C6—H6A	107.9	O4—C17—C16	111.8 (3)
C8—C7—C6	114.9 (3)	O4—C17—C20	108.7 (3)
C8—C7—H7A	108.5	C16—C17—C20	113.3 (3)
C6—C7—H7A	108.5	O4—C17—C13	107.5 (3)
C8—C7—H7B	108.5	C16—C17—C13	103.5 (3)
C6—C7—H7B	108.5	C20—C17—C13	111.8 (3)
H7A—C7—H7B	107.5	C10—C18—H18A	109.5
C7—C8—C14	110.0 (3)	C10—C18—H18B	109.5
C7—C8—C9	111.6 (3)	H18A—C18—H18B	109.5
C14—C8—C9	108.1 (3)	C10—C18—H18C	109.5
C7—C8—H8A	109.1	H18A—C18—H18C	109.5
C14—C8—H8A	109.1	H18B—C18—H18C	109.5
C9—C8—H8A	109.1	C13—C19—H19A	109.5
C8—C9—C11	113.7 (3)	C13—C19—H19B	109.5
C8—C9—C10	111.5 (3)	H19A—C19—H19B	109.5
C11—C9—C10	115.9 (3)	C13—C19—H19C	109.5
C8—C9—H9A	104.8	H19A—C19—H19C	109.5
C11—C9—H9A	104.8	H19B—C19—H19C	109.5
C10—C9—H9A	104.8	O2—C20—C21	120.8 (4)
C1—C10—C5	109.9 (3)	O2—C20—C17	121.5 (4)
C1—C10—C18	106.7 (3)	C21—C20—C17	117.7 (4)
C5—C10—C18	108.7 (3)	C20—C21—H21A	109.5
C1—C10—C9	113.3 (3)	C20—C21—H21B	109.5
C5—C10—C9	104.4 (3)	H21A—C21—H21B	109.5
C18—C10—C9	113.7 (3)	C20—C21—H21C	109.5
O3—C11—C12	108.3 (3)	H21A—C21—H21C	109.5
O3—C11—C9	113.5 (3)	H21B—C21—H21C	109.5
C12—C11—C9	112.4 (3)	C6—C22—H22A	109.5
O3—C11—H11A	107.5	C6—C22—H22B	109.5
C12—C11—H11A	107.5	H22A—C22—H22B	109.5
C9—C11—H11A	107.5	C6—C22—H22C	109.5
C13—C12—C11	112.9 (3)	H22A—C22—H22C	109.5
C13—C12—H12A	109.0	H22B—C22—H22C	109.5

C10—C1—C2—C3	56.7 (5)	C10—C9—C11—C12	−179.2 (3)
C1—C2—C3—O1	149.7 (4)	O3—C11—C12—C13	75.8 (4)
C1—C2—C3—C4	−34.3 (5)	C9—C11—C12—C13	−50.4 (4)
O1—C3—C4—C5	179.2 (5)	C11—C12—C13—C19	−69.4 (4)
C2—C3—C4—C5	3.4 (7)	C11—C12—C13—C14	54.9 (4)
C3—C4—C5—C6	−165.8 (4)	C11—C12—C13—C17	166.1 (3)
C3—C4—C5—C10	7.1 (7)	C7—C8—C14—C15	−54.7 (5)
C4—C5—C6—C22	−12.7 (6)	C9—C8—C14—C15	−176.8 (3)
C10—C5—C6—C22	173.9 (4)	C7—C8—C14—C13	−178.3 (3)
C4—C5—C6—C7	110.8 (5)	C9—C8—C14—C13	59.6 (4)
C10—C5—C6—C7	−62.6 (4)	C12—C13—C14—C15	167.6 (3)
C5—C6—C7—C8	52.0 (5)	C19—C13—C14—C15	−68.9 (4)
C22—C6—C7—C8	178.5 (4)	C17—C13—C14—C15	45.5 (4)
C6—C7—C8—C14	−169.5 (3)	C12—C13—C14—C8	−60.9 (4)
C6—C7—C8—C9	−49.6 (5)	C19—C13—C14—C8	62.6 (4)
C7—C8—C9—C11	−174.1 (3)	C17—C13—C14—C8	176.9 (3)
C14—C8—C9—C11	−53.1 (4)	C8—C14—C15—C16	−160.5 (3)
C7—C8—C9—C10	52.6 (4)	C13—C14—C15—C16	−33.1 (4)
C14—C8—C9—C10	173.7 (3)	C14—C15—C16—C17	7.1 (4)
C2—C1—C10—C5	−46.4 (5)	C15—C16—C17—O4	−94.6 (4)
C2—C1—C10—C18	−164.1 (4)	C15—C16—C17—C20	142.1 (3)
C2—C1—C10—C9	70.0 (4)	C15—C16—C17—C13	20.8 (4)
C4—C5—C10—C1	14.6 (5)	C12—C13—C17—O4	−37.5 (4)
C6—C5—C10—C1	−171.9 (4)	C19—C13—C17—O4	−163.6 (3)
C4—C5—C10—C18	131.0 (4)	C14—C13—C17—O4	78.6 (3)
C6—C5—C10—C18	−55.4 (4)	C12—C13—C17—C16	−156.0 (3)
C4—C5—C10—C9	−107.2 (4)	C19—C13—C17—C16	77.9 (4)
C6—C5—C10—C9	66.3 (4)	C14—C13—C17—C16	−39.8 (4)
C8—C9—C10—C1	−177.8 (3)	C12—C13—C17—C20	81.7 (4)
C11—C9—C10—C1	50.0 (4)	C19—C13—C17—C20	−44.4 (4)
C8—C9—C10—C5	−58.2 (4)	C14—C13—C17—C20	−162.1 (3)
C11—C9—C10—C5	169.6 (3)	O4—C17—C20—O2	−141.2 (4)
C8—C9—C10—C18	60.1 (4)	C16—C17—C20—O2	−16.2 (6)
C11—C9—C10—C18	−72.1 (4)	C13—C17—C20—O2	100.3 (4)
C8—C9—C11—O3	−73.6 (4)	O4—C17—C20—C21	40.7 (5)
C10—C9—C11—O3	57.5 (4)	C16—C17—C20—C21	165.7 (4)
C8—C9—C11—C12	49.7 (4)	C13—C17—C20—C21	−77.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.81 (3)	2.02 (4)	2.767 (5)	153 (4)
O4—H4A···O3ⁱⁱ	0.82 (5)	2.12 (5)	2.910 (5)	165 (6)
C12—H12A···O4	0.97	2.40	2.816 (5)	105
C14—H14A···O4	0.98	2.54	2.903 (6)	101
C16—H16A···O2	0.97	2.38	2.822 (6)	107
C18—H18C···O1ⁱ	0.96	2.47	3.411 (6)	165
C19—H19B···O3	0.96	2.46	2.942 (6)	111

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

Acknowledgements

The authors would like to acknowledge the Ministry of Higher Education of Malaysia and Universiti Teknologi MARA for research grants Nos. 600-RMI/FRGS 5/3 (49/2014) and 600-RMI/DANA/5/3/LESTARI(92/2015).

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