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

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ISSN: 2414-3146

11β-Hy­dr­oxy­medroxyprogesterone

CROSSMARK_Color_square_no_text.svg

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).

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

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[Pullen, M. A., Laping, N., Edwards, R. & Bray, J. (2006). Steroids, 71, 792-798.]) which has been used for treatment of endometrial carcinoma (Fujiwara et al., 2012[Fujiwara, H., Jobo, T., Takei, Y., Saga, Y., Imai, M., Arai, T., Taneichi, A., Machida, S., Takahashi, Y. & Suzuki, M. (2012). Oncol. Lett. 3, 1002-1006.]). In a continuation of our work on biotransformation of steroids (Sultan et al., 2014[Sultan, S., Noor, M. Z. B. M., Anouar, el H., Shah, S. A. A., Salim, F., Rahim, R., Al Trabolsy, Z. B. & Weber, J. F. F. (2014). Molecules, 19, 13775-13787.]), 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[link]), a biotransformation product of medroxyprogesterone.

[Figure 1]
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[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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]
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[link]. 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[Ouedraogo, Y. P., Huang, L., Torrente, M. P., Proni, G., Chadwick, E., Wehmschulte, R. J. & Nesnas, N. (2013). Chirality, 25, 575-581.], Karpinska et al., 2013[Karpinska, J., Erxleben, A. & McArdle, P. (2013). Acta Cryst. E69, o60.]).

Table 2
Experimental details

Crystal data
Chemical formula C22H32O4
Mr 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)
V3) 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.959, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 16639, 3527, 3023
Rint 0.074
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.20, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (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: 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
C22H32O4Dx = 1.256 Mg m3
Mr = 360.47Melting point = 491–493 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.8692 (12) ÅCell parameters from 9916 reflections
b = 12.221 (2) Åθ = 3.1–25.5°
c = 11.7933 (19) ŵ = 0.09 mm1
β = 105.726 (5)°T = 302 K
V = 952.9 (3) Å3Block, colourless
Z = 20.50 × 0.50 × 0.23 mm
F(000) = 392
Data collection top
Bruker APEXII CCD
diffractometer
3527 independent reflections
Radiation source: fine-focus sealed tube3023 reflections with I > 2σ(I)
Detector resolution: 83.66 pixels mm-1Rint = 0.074
φ and ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 87
Tmin = 0.959, Tmax = 0.981k = 1414
16639 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0268P)2 + 0.6466P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.20 e Å3
3527 reflectionsΔρmin = 0.21 e Å3
248 parametersExtinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.023 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), ???? Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
O10.5345 (6)0.5911 (3)0.6547 (3)0.0596 (10)
O20.0798 (5)0.7685 (3)0.2863 (3)0.0510 (9)
O30.3276 (5)0.9316 (2)0.1760 (3)0.0355 (7)
O40.1195 (5)0.6185 (3)0.0443 (3)0.0380 (7)
C10.5080 (7)0.8207 (3)0.4627 (3)0.0362 (10)
H1A0.62150.85190.52150.043*
H1B0.41340.87940.43190.043*
C20.4047 (8)0.7364 (4)0.5217 (4)0.0440 (11)
H2A0.36540.77010.58660.053*
H2B0.28340.70960.46550.053*
C30.5459 (8)0.6426 (4)0.5667 (4)0.0442 (11)
C40.6824 (7)0.6123 (4)0.4983 (4)0.0424 (11)
H4B0.76560.55200.52270.051*
C50.6970 (6)0.6660 (3)0.4012 (4)0.0335 (10)
C60.8029 (6)0.6207 (4)0.3160 (4)0.0373 (10)
H6A0.88960.67850.29870.045*
C70.6362 (6)0.5958 (4)0.2015 (4)0.0365 (10)
H7A0.70040.57400.14120.044*
H7B0.55710.53420.21580.044*
C80.4922 (6)0.6912 (3)0.1540 (3)0.0265 (9)
H8A0.56500.74750.12270.032*
C90.4091 (6)0.7421 (3)0.2508 (3)0.0254 (8)
H9A0.33720.68220.27730.030*
C100.5843 (6)0.7738 (3)0.3623 (3)0.0287 (9)
C110.2469 (6)0.8306 (3)0.2052 (3)0.0273 (9)
H11A0.18290.84600.26830.033*
C120.0800 (6)0.7922 (3)0.0973 (3)0.0276 (9)
H12A0.00240.73760.12210.033*
H12B0.00640.85380.06530.033*
C130.1637 (5)0.7435 (3)0.0004 (3)0.0232 (8)
C140.3119 (6)0.6509 (3)0.0548 (3)0.0270 (9)
H14A0.23670.60000.09140.032*
C150.3503 (6)0.5910 (3)0.0505 (4)0.0356 (10)
H15A0.38450.51490.03180.043*
H15B0.45890.62530.07570.043*
C160.1477 (6)0.6011 (4)0.1461 (3)0.0329 (9)
H16A0.16970.63080.21790.039*
H16B0.08470.52980.16350.039*
C170.0112 (6)0.6779 (3)0.0986 (3)0.0287 (9)
C180.7350 (7)0.8583 (3)0.3368 (4)0.0396 (11)
H18A0.75880.84240.26190.059*
H18B0.86030.85430.39750.059*
H18C0.67930.93050.33510.059*
C190.2619 (6)0.8320 (3)0.0585 (4)0.0304 (9)
H19A0.28800.80270.12850.046*
H19B0.38680.85510.00500.046*
H19C0.17220.89350.07890.046*
C200.1183 (6)0.7539 (4)0.1932 (4)0.0343 (10)
C210.2902 (8)0.8123 (5)0.1650 (5)0.0603 (15)
H21A0.27660.80740.08190.090*
H21B0.41550.77930.20760.090*
H21C0.28920.88780.18720.090*
C220.9346 (9)0.5198 (4)0.3577 (5)0.0591 (15)
H22A1.00380.50050.29990.089*
H22B0.85080.45980.36810.089*
H22C1.03190.53560.43120.089*
H3A0.382 (6)0.960 (4)0.239 (2)0.037 (13)*
H4A0.168 (9)0.570 (4)0.091 (4)0.07 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.094 (3)0.0388 (19)0.0452 (19)0.0059 (19)0.0167 (19)0.0157 (16)
O20.055 (2)0.058 (2)0.0376 (18)0.0016 (17)0.0081 (16)0.0057 (16)
O30.0448 (19)0.0208 (14)0.0333 (16)0.0006 (13)0.0022 (14)0.0014 (13)
O40.0393 (17)0.0384 (17)0.0399 (16)0.0183 (14)0.0167 (14)0.0094 (14)
C10.050 (3)0.029 (2)0.0246 (19)0.0046 (19)0.0016 (19)0.0002 (17)
C20.057 (3)0.043 (3)0.033 (2)0.004 (2)0.013 (2)0.004 (2)
C30.058 (3)0.033 (2)0.036 (2)0.007 (2)0.005 (2)0.0028 (19)
C40.052 (3)0.026 (2)0.042 (2)0.004 (2)0.000 (2)0.006 (2)
C50.034 (2)0.026 (2)0.033 (2)0.0022 (18)0.0046 (18)0.0011 (17)
C60.031 (2)0.030 (2)0.047 (2)0.0080 (19)0.0045 (19)0.002 (2)
C70.036 (2)0.032 (2)0.040 (2)0.0093 (19)0.0081 (19)0.0035 (19)
C80.024 (2)0.0233 (19)0.033 (2)0.0021 (16)0.0085 (17)0.0018 (16)
C90.031 (2)0.0202 (17)0.0263 (18)0.0003 (16)0.0092 (16)0.0010 (15)
C100.031 (2)0.0224 (19)0.030 (2)0.0036 (17)0.0037 (17)0.0022 (16)
C110.030 (2)0.026 (2)0.0268 (19)0.0010 (17)0.0092 (17)0.0018 (16)
C120.023 (2)0.028 (2)0.033 (2)0.0023 (16)0.0096 (17)0.0026 (17)
C130.0174 (18)0.0231 (18)0.0312 (19)0.0022 (16)0.0100 (16)0.0007 (16)
C140.024 (2)0.027 (2)0.031 (2)0.0008 (16)0.0102 (16)0.0014 (16)
C150.035 (2)0.031 (2)0.041 (2)0.0058 (18)0.0120 (19)0.0074 (18)
C160.036 (2)0.031 (2)0.033 (2)0.0024 (18)0.0121 (17)0.0082 (18)
C170.025 (2)0.031 (2)0.031 (2)0.0048 (17)0.0090 (17)0.0065 (17)
C180.038 (3)0.027 (2)0.048 (3)0.0022 (18)0.001 (2)0.0003 (19)
C190.032 (2)0.028 (2)0.033 (2)0.0034 (17)0.0119 (18)0.0027 (17)
C200.027 (2)0.037 (2)0.035 (2)0.0028 (18)0.0005 (18)0.0068 (18)
C210.046 (3)0.074 (4)0.057 (3)0.017 (3)0.008 (3)0.000 (3)
C220.053 (3)0.047 (3)0.065 (3)0.025 (3)0.003 (3)0.001 (2)
Geometric parameters (Å, º) top
O1—C31.235 (5)C11—C121.537 (5)
O2—C201.210 (5)C11—H11A0.9800
O3—C111.433 (5)C12—C131.532 (5)
O3—H3A0.813 (14)C12—H12A0.9700
O4—C171.434 (5)C12—H12B0.9700
O4—H4A0.818 (14)C13—C191.537 (5)
C1—C21.523 (6)C13—C141.540 (5)
C1—C101.530 (6)C13—C171.562 (5)
C1—H1A0.9700C14—C151.526 (5)
C1—H1B0.9700C14—H14A0.9800
C2—C31.502 (7)C15—C161.540 (6)
C2—H2A0.9700C15—H15A0.9700
C2—H2B0.9700C15—H15B0.9700
C3—C41.441 (7)C16—C171.535 (5)
C4—C51.346 (6)C16—H16A0.9700
C4—H4B0.9300C16—H16B0.9700
C5—C61.497 (6)C17—C201.537 (6)
C5—C101.534 (5)C18—H18A0.9600
C6—C221.530 (6)C18—H18B0.9600
C6—C71.546 (6)C18—H18C0.9600
C6—H6A0.9800C19—H19A0.9600
C7—C81.533 (5)C19—H19B0.9600
C7—H7A0.9700C19—H19C0.9600
C7—H7B0.9700C20—C211.493 (7)
C8—C141.536 (5)C21—H21A0.9600
C8—C91.539 (5)C21—H21B0.9600
C8—H8A0.9800C21—H21C0.9600
C9—C111.542 (5)C22—H22A0.9600
C9—C101.571 (5)C22—H22B0.9600
C9—H9A0.9800C22—H22C0.9600
C10—C181.548 (6)
C11—O3—H3A105 (3)C11—C12—H12A109.0
C17—O4—H4A105 (4)C13—C12—H12B109.0
C2—C1—C10113.6 (3)C11—C12—H12B109.0
C2—C1—H1A108.9H12A—C12—H12B107.8
C10—C1—H1A108.9C12—C13—C19111.3 (3)
C2—C1—H1B108.9C12—C13—C14108.3 (3)
C10—C1—H1B108.9C19—C13—C14112.6 (3)
H1A—C1—H1B107.7C12—C13—C17116.5 (3)
C3—C2—C1109.9 (4)C19—C13—C17108.1 (3)
C3—C2—H2A109.7C14—C13—C1799.7 (3)
C1—C2—H2A109.7C15—C14—C8119.5 (3)
C3—C2—H2B109.7C15—C14—C13104.7 (3)
C1—C2—H2B109.7C8—C14—C13112.8 (3)
H2A—C2—H2B108.2C15—C14—H14A106.3
O1—C3—C4122.6 (4)C8—C14—H14A106.3
O1—C3—C2120.3 (5)C13—C14—H14A106.3
C4—C3—C2117.0 (4)C14—C15—C16103.6 (3)
C5—C4—C3124.1 (4)C14—C15—H15A111.0
C5—C4—H4B118.0C16—C15—H15A111.0
C3—C4—H4B118.0C14—C15—H15B111.0
C4—C5—C6123.6 (4)C16—C15—H15B111.0
C4—C5—C10121.7 (4)H15A—C15—H15B109.0
C6—C5—C10114.4 (4)C17—C16—C15107.6 (3)
C5—C6—C22115.8 (4)C17—C16—H16A110.2
C5—C6—C7106.2 (3)C15—C16—H16A110.2
C22—C6—C7110.8 (4)C17—C16—H16B110.2
C5—C6—H6A107.9C15—C16—H16B110.2
C22—C6—H6A107.9H16A—C16—H16B108.5
C7—C6—H6A107.9O4—C17—C16111.8 (3)
C8—C7—C6114.9 (3)O4—C17—C20108.7 (3)
C8—C7—H7A108.5C16—C17—C20113.3 (3)
C6—C7—H7A108.5O4—C17—C13107.5 (3)
C8—C7—H7B108.5C16—C17—C13103.5 (3)
C6—C7—H7B108.5C20—C17—C13111.8 (3)
H7A—C7—H7B107.5C10—C18—H18A109.5
C7—C8—C14110.0 (3)C10—C18—H18B109.5
C7—C8—C9111.6 (3)H18A—C18—H18B109.5
C14—C8—C9108.1 (3)C10—C18—H18C109.5
C7—C8—H8A109.1H18A—C18—H18C109.5
C14—C8—H8A109.1H18B—C18—H18C109.5
C9—C8—H8A109.1C13—C19—H19A109.5
C8—C9—C11113.7 (3)C13—C19—H19B109.5
C8—C9—C10111.5 (3)H19A—C19—H19B109.5
C11—C9—C10115.9 (3)C13—C19—H19C109.5
C8—C9—H9A104.8H19A—C19—H19C109.5
C11—C9—H9A104.8H19B—C19—H19C109.5
C10—C9—H9A104.8O2—C20—C21120.8 (4)
C1—C10—C5109.9 (3)O2—C20—C17121.5 (4)
C1—C10—C18106.7 (3)C21—C20—C17117.7 (4)
C5—C10—C18108.7 (3)C20—C21—H21A109.5
C1—C10—C9113.3 (3)C20—C21—H21B109.5
C5—C10—C9104.4 (3)H21A—C21—H21B109.5
C18—C10—C9113.7 (3)C20—C21—H21C109.5
O3—C11—C12108.3 (3)H21A—C21—H21C109.5
O3—C11—C9113.5 (3)H21B—C21—H21C109.5
C12—C11—C9112.4 (3)C6—C22—H22A109.5
O3—C11—H11A107.5C6—C22—H22B109.5
C12—C11—H11A107.5H22A—C22—H22B109.5
C9—C11—H11A107.5C6—C22—H22C109.5
C13—C12—C11112.9 (3)H22A—C22—H22C109.5
C13—C12—H12A109.0H22B—C22—H22C109.5
C10—C1—C2—C356.7 (5)C10—C9—C11—C12179.2 (3)
C1—C2—C3—O1149.7 (4)O3—C11—C12—C1375.8 (4)
C1—C2—C3—C434.3 (5)C9—C11—C12—C1350.4 (4)
O1—C3—C4—C5179.2 (5)C11—C12—C13—C1969.4 (4)
C2—C3—C4—C53.4 (7)C11—C12—C13—C1454.9 (4)
C3—C4—C5—C6165.8 (4)C11—C12—C13—C17166.1 (3)
C3—C4—C5—C107.1 (7)C7—C8—C14—C1554.7 (5)
C4—C5—C6—C2212.7 (6)C9—C8—C14—C15176.8 (3)
C10—C5—C6—C22173.9 (4)C7—C8—C14—C13178.3 (3)
C4—C5—C6—C7110.8 (5)C9—C8—C14—C1359.6 (4)
C10—C5—C6—C762.6 (4)C12—C13—C14—C15167.6 (3)
C5—C6—C7—C852.0 (5)C19—C13—C14—C1568.9 (4)
C22—C6—C7—C8178.5 (4)C17—C13—C14—C1545.5 (4)
C6—C7—C8—C14169.5 (3)C12—C13—C14—C860.9 (4)
C6—C7—C8—C949.6 (5)C19—C13—C14—C862.6 (4)
C7—C8—C9—C11174.1 (3)C17—C13—C14—C8176.9 (3)
C14—C8—C9—C1153.1 (4)C8—C14—C15—C16160.5 (3)
C7—C8—C9—C1052.6 (4)C13—C14—C15—C1633.1 (4)
C14—C8—C9—C10173.7 (3)C14—C15—C16—C177.1 (4)
C2—C1—C10—C546.4 (5)C15—C16—C17—O494.6 (4)
C2—C1—C10—C18164.1 (4)C15—C16—C17—C20142.1 (3)
C2—C1—C10—C970.0 (4)C15—C16—C17—C1320.8 (4)
C4—C5—C10—C114.6 (5)C12—C13—C17—O437.5 (4)
C6—C5—C10—C1171.9 (4)C19—C13—C17—O4163.6 (3)
C4—C5—C10—C18131.0 (4)C14—C13—C17—O478.6 (3)
C6—C5—C10—C1855.4 (4)C12—C13—C17—C16156.0 (3)
C4—C5—C10—C9107.2 (4)C19—C13—C17—C1677.9 (4)
C6—C5—C10—C966.3 (4)C14—C13—C17—C1639.8 (4)
C8—C9—C10—C1177.8 (3)C12—C13—C17—C2081.7 (4)
C11—C9—C10—C150.0 (4)C19—C13—C17—C2044.4 (4)
C8—C9—C10—C558.2 (4)C14—C13—C17—C20162.1 (3)
C11—C9—C10—C5169.6 (3)O4—C17—C20—O2141.2 (4)
C8—C9—C10—C1860.1 (4)C16—C17—C20—O216.2 (6)
C11—C9—C10—C1872.1 (4)C13—C17—C20—O2100.3 (4)
C8—C9—C11—O373.6 (4)O4—C17—C20—C2140.7 (5)
C10—C9—C11—O357.5 (4)C16—C17—C20—C21165.7 (4)
C8—C9—C11—C1249.7 (4)C13—C17—C20—C2177.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.81 (3)2.02 (4)2.767 (5)153 (4)
O4—H4A···O3ii0.82 (5)2.12 (5)2.910 (5)165 (6)
C12—H12A···O40.972.402.816 (5)105
C14—H14A···O40.982.542.903 (6)101
C16—H16A···O20.972.382.822 (6)107
C18—H18C···O1i0.962.473.411 (6)165
C19—H19B···O30.962.462.942 (6)111
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y1/2, 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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