Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2014 Feb 19;70(Pt 3):o317. doi: 10.1107/S1600536814002748

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl acetate

Radouane Oubabi a, Aziz Auhmani a, My Youssef Ait Itto a,*, Abdelwahed Auhmani a, Jean-Claude Daran b
PMCID: PMC3998421  PMID: 24765017

Abstract

The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetyl­ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa­hydro­phen­an­thren-2-ol]. The mol­ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [−0.10 (6)] allowed this absolute configuration to be confirmed.

Related literature  

For the synthesis, see: Short & Stromberg (1937 ▶). For biological properties of totarol, see: Barrero et al. (2003 ▶); Bernabeu et al. (2002 ▶); Haraguchi et al. (1996 ▶); Marcos et al. (2003 ▶); Tacon et al. (2012 ▶). For related structures, see: Zeroual et al. (2008 ▶); Pettit et al. (2004 ▶). For structural discussion, see: Cremer & Pople (1975 ▶); Flack (1983 ▶); Flack & Bernardinelli (2000 ▶); Spek (2009 ▶).graphic file with name e-70-0o317-scheme1.jpg

Experimental  

Crystal data  

  • C22H32O2

  • M r = 328.47

  • Monoclinic, Inline graphic

  • a = 7.4250 (2) Å

  • b = 10.5716 (3) Å

  • c = 12.0747 (3) Å

  • β = 90.124 (2)°

  • V = 947.79 (4) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.55 mm−1

  • T = 180 K

  • 0.38 × 0.38 × 0.14 mm

Data collection  

  • Agilent Xcalibur (Eos, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) ▶ T min = 0.860, T max = 1.000

  • 4370 measured reflections

  • 2511 independent reflections

  • 2490 reflections with I > 2σ(I)

  • R int = 0.012

  • θmax = 60.7°

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.029

  • wR(F 2) = 0.075

  • S = 1.04

  • 2511 reflections

  • 225 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.14 e Å−3

  • Absolute structure: Refined as an inversion twin.

  • Absolute structure parameter: 0.0 (3)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL2013.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002748/xu5767sup1.cif

e-70-0o317-sup1.cif (27.2KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002748/xu5767Isup2.hkl

e-70-0o317-Isup2.hkl (138KB, hkl)
Click here for additional data file. (7.7KB, cml)

Supporting information file. DOI: 10.1107/S1600536814002748/xu5767Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=985421

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

1. Comment

The hemisynthesis of the title compound C22H32O2 2 was carried out through direct acetylation reaction of naturally occurred Totarol (1). Totarol (1) is a naturally produced diterpene isolated from a several plants such as Podocarpus totara (Short & Stromberg, 1937) Tetraclinis articulata (Barrero et al., 2003). It has been attracting great interest because of its biological properties ranging from Antimicrobial (Haraguchi et al., 1996), anti-oxidant (Bernabeu et al., 2002), Anti-inflammatory, analgesic, anti-tumoral (Marcos et al., 2003) to Anti-plasmodial (Tacon et al., 2012).

In the aim of preparing totarol derivatives, we report here, the hemisynthesis of (4bS,8aS)-1-isopropyl-4 b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate 2 from naturally occurred Totarol (1). Thus, treatment of (1) with acetic anhydride in pyridine provides (2) as colorless crystals in 97% yield. Its structure was fully characterized by its mass and NMR spectroscopic data. Furthermore, an X-ray single-crystal structure analysis allowed us to confirm unambiguously its full structure.

Compound (2) is built up from three fused six membered rings, a saturated one and two unsaturated (Fig. 1). The central unsaturated ring has an half chair conformation with puckering parameters: Q = 0.531 (2) Å, θ= 50.4 (2)° and φ= 120.1 (4)° (Cremer & Pople, 1975), whereas the second insaturated six-membered ring displays a chair conformation with puckering parameters: Q = 0.535 (3) Å, θ= 173.2 (3) (2)° and φ= 289 (2)°. Similar conformation for the three fused rings has been reported previously with hydroxyl substituent in place of the acetate in the title compound (Zeroual et al., 2008) and with either an hydroxyl or a methoxy substituent on the central ring (Pettit et al., 2004).

The absolute configuration (4S,8S) deduced from the chemical pathway is supported by the refinement of the Flack parameter, 0.0 (3), (Flack, 1983; Flack & Bernardinelli, 2000) and confirmed by the refinement of the Hooft parameter, -0.10 (6) (Spek, 2009).

2. Experimental

A solution of totarol (1) (90 mg, 0.314 mmol) in acetic anhydride (20 ml) and pyridine (20 ml) was heated under reflux for 24 h. After cooling, the mixture was acidified with 1N HCl solution then extracted with ether (3 × 20 ml). The organic layer was washed with water, dried on anhydrous Na2SO4 and then evaporated under reduced pressure. The obtained residue was chromatographied on silica gel column using hexane and ethyl acetate (97/3) as eluent, to give (4bS,8aS)-1-isopropyl-4 b,8,8-trimethyl-4 b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate (2) (100 mg) in 97% yield.

3. Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (methylene), 0.98 Å (methyl), 1.0 Å (methine) with Uiso(H) = 1.2Ueq(CH and CH2) or Uiso(H) = 1.5Ueq(CH3).

Although the standard deviation on the Flack's parameter, 0.0 (3), is rather high, the value of the Hooft's parameter, -0.10 (6), is more reliable and allows to confirm the absolute configuration. It is interesting to point out that inverting the configuration gives values of Hooft and Flack parameter close to 1.0 with similar standard deviation.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

: Molecular view of compound (2) with the atom labeling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Crystal data

C22H32O2 F(000) = 360
Mr = 328.47 Dx = 1.151 Mg m−3
Monoclinic, P21 Cu Kα radiation, λ = 1.54184 Å
a = 7.4250 (2) Å Cell parameters from 3311 reflections
b = 10.5716 (3) Å θ = 3.7–60.6°
c = 12.0747 (3) Å µ = 0.55 mm−1
β = 90.124 (2)° T = 180 K
V = 947.79 (4) Å3 Box, colourless
Z = 2 0.38 × 0.38 × 0.14 mm
Open in a new tab

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer 2511 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source 2490 reflections with I > 2σ(I)
Mirror monochromator Rint = 0.012
Detector resolution: 16.1978 pixels mm-1 θmax = 60.7°, θmin = 3.7°
ω scans h = −7→8
Absorption correction: multi-scan Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (CrysAlis PRO, Agilent, 2012) k = −11→11
Tmin = 0.860, Tmax = 1.000 l = −13→13
4370 measured reflections
Open in a new tab

Refinement

Refinement on F2 H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0433P)2 + 0.168P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.029 (Δ/σ)max < 0.001
wR(F2) = 0.075 Δρmax = 0.13 e Å−3
S = 1.04 Δρmin = −0.14 e Å−3
2511 reflections Extinction correction: SHELXL2013 (Sheldrick, 2013), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
225 parameters Extinction coefficient: 0.050 (2)
1 restraint Absolute structure: Refined as an inversion twin.
Hydrogen site location: inferred from neighbouring sites Absolute structure parameter: 0.0 (3)
Open in a new tab

Special details

Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (CrysAlis PRO; Agilent Technologies, 2012)
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. Refined as a 2-component inversion twin.
Open in a new tab

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

x y z Uiso*/Ueq
C1 0.6487 (3) 0.6992 (2) 0.17276 (16) 0.0270 (5)
C2 0.4780 (3) 0.7203 (2) 0.13012 (17) 0.0283 (5)
C3 0.3461 (3) 0.7823 (2) 0.18816 (19) 0.0334 (5)
H3 0.2304 0.7948 0.1562 0.040*
C4 0.3833 (3) 0.8262 (2) 0.29347 (18) 0.0319 (5)
H4 0.2916 0.8682 0.3341 0.038*
C4A 0.5533 (3) 0.81000 (19) 0.34131 (17) 0.0244 (5)
C4B 0.5942 (3) 0.8675 (2) 0.45589 (18) 0.0258 (5)
C5 0.4239 (3) 0.8711 (3) 0.52884 (19) 0.0346 (6)
H5A 0.3376 0.9327 0.4972 0.041*
H5B 0.3659 0.7868 0.5276 0.041*
C6 0.4646 (3) 0.9074 (3) 0.6486 (2) 0.0406 (6)
H6A 0.5144 0.9942 0.6509 0.049*
H6B 0.3515 0.9067 0.6919 0.049*
C7 0.5980 (3) 0.8167 (3) 0.70024 (18) 0.0371 (6)
H7A 0.5427 0.7315 0.7033 0.045*
H7B 0.6222 0.8438 0.7773 0.045*
C8 0.7773 (3) 0.8075 (2) 0.63830 (18) 0.0338 (5)
C8A 0.7386 (3) 0.7834 (2) 0.51303 (17) 0.0275 (5)
H8A 0.6896 0.6954 0.5093 0.033*
C9 0.9073 (3) 0.7813 (3) 0.44192 (19) 0.0372 (6)
H9A 0.9521 0.8687 0.4322 0.045*
H9B 1.0022 0.7319 0.4801 0.045*
C10 0.8707 (3) 0.7233 (3) 0.32926 (18) 0.0366 (6)
H10A 0.9617 0.7561 0.2768 0.044*
H10B 0.8890 0.6307 0.3351 0.044*
C10A 0.6862 (3) 0.74630 (19) 0.28005 (17) 0.0261 (5)
C11 0.7945 (3) 0.6336 (2) 0.10479 (18) 0.0343 (6)
H11 0.8978 0.6181 0.1562 0.041*
C12 0.7413 (4) 0.5048 (3) 0.0572 (2) 0.0540 (8)
H12A 0.8501 0.4562 0.0400 0.081*
H12B 0.6704 0.5170 −0.0105 0.081*
H12C 0.6691 0.4585 0.1117 0.081*
C13 0.8634 (4) 0.7225 (3) 0.0150 (2) 0.0518 (7)
H13A 0.9103 0.7998 0.0492 0.078*
H13B 0.7644 0.7440 −0.0355 0.078*
H13C 0.9597 0.6807 −0.0266 0.078*
C14 0.6541 (4) 1.0050 (2) 0.4337 (2) 0.0433 (6)
H14A 0.5590 1.0497 0.3933 0.065*
H14B 0.7647 1.0047 0.3895 0.065*
H14C 0.6768 1.0478 0.5044 0.065*
C15 0.8902 (4) 0.9257 (3) 0.6616 (2) 0.0489 (7)
H15A 0.9251 0.9270 0.7399 0.073*
H15B 0.8193 1.0013 0.6444 0.073*
H15C 0.9986 0.9243 0.6154 0.073*
C16 0.8803 (4) 0.6933 (3) 0.6843 (2) 0.0561 (8)
H16A 0.8152 0.6154 0.6657 0.084*
H16B 0.8905 0.7008 0.7649 0.084*
H16C 1.0009 0.6905 0.6516 0.084*
C17 0.3222 (3) 0.5899 (2) 0.00169 (19) 0.0345 (6)
C18 0.3010 (4) 0.5659 (3) −0.1197 (2) 0.0460 (7)
H18A 0.1878 0.5206 −0.1331 0.069*
H18B 0.4021 0.5146 −0.1461 0.069*
H18C 0.2991 0.6467 −0.1594 0.069*
O1 0.4419 (2) 0.68523 (16) 0.01943 (11) 0.0338 (4)
O2 0.2470 (2) 0.53449 (19) 0.07423 (14) 0.0491 (5)
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0302 (12) 0.0261 (11) 0.0248 (11) 0.0012 (10) 0.0028 (9) 0.0023 (9)
C2 0.0305 (12) 0.0316 (12) 0.0230 (10) −0.0026 (10) 0.0004 (9) 0.0014 (9)
C3 0.0244 (12) 0.0444 (13) 0.0315 (12) 0.0021 (11) −0.0022 (9) 0.0002 (10)
C4 0.0269 (12) 0.0355 (12) 0.0333 (12) 0.0060 (10) 0.0031 (9) −0.0010 (10)
C4A 0.0256 (11) 0.0205 (10) 0.0271 (11) 0.0010 (9) 0.0026 (8) 0.0024 (9)
C4B 0.0262 (11) 0.0221 (10) 0.0290 (11) 0.0006 (9) 0.0022 (9) −0.0022 (9)
C5 0.0302 (12) 0.0422 (13) 0.0314 (12) 0.0063 (11) 0.0022 (10) −0.0072 (10)
C6 0.0327 (13) 0.0533 (17) 0.0357 (13) 0.0027 (12) 0.0065 (10) −0.0129 (12)
C7 0.0413 (14) 0.0448 (14) 0.0253 (11) −0.0082 (12) 0.0023 (10) −0.0068 (11)
C8 0.0342 (12) 0.0386 (13) 0.0286 (11) 0.0002 (11) −0.0037 (9) −0.0071 (10)
C8A 0.0269 (11) 0.0271 (11) 0.0286 (11) −0.0019 (10) −0.0001 (9) −0.0041 (9)
C9 0.0276 (12) 0.0497 (14) 0.0343 (13) 0.0040 (11) −0.0011 (9) −0.0077 (11)
C10 0.0280 (12) 0.0513 (15) 0.0305 (12) 0.0089 (11) 0.0005 (10) −0.0047 (11)
C10A 0.0261 (11) 0.0259 (11) 0.0263 (11) 0.0000 (9) 0.0031 (9) 0.0028 (9)
C11 0.0322 (12) 0.0457 (14) 0.0251 (11) 0.0109 (11) 0.0018 (9) −0.0012 (10)
C12 0.0587 (19) 0.0487 (17) 0.0546 (17) 0.0163 (14) 0.0060 (14) −0.0166 (13)
C13 0.0399 (15) 0.0696 (19) 0.0460 (15) 0.0121 (14) 0.0175 (12) 0.0119 (14)
C14 0.0599 (17) 0.0281 (13) 0.0421 (14) −0.0045 (12) −0.0035 (12) 0.0017 (11)
C15 0.0363 (14) 0.0662 (18) 0.0441 (15) −0.0116 (13) −0.0023 (11) −0.0189 (14)
C16 0.068 (2) 0.0664 (18) 0.0338 (13) 0.0231 (17) −0.0133 (13) −0.0045 (14)
C17 0.0352 (13) 0.0364 (13) 0.0319 (12) 0.0016 (11) −0.0017 (10) −0.0013 (10)
C18 0.0489 (16) 0.0560 (17) 0.0332 (13) −0.0039 (13) −0.0023 (11) −0.0089 (12)
O1 0.0341 (9) 0.0432 (9) 0.0239 (8) −0.0036 (8) −0.0002 (6) −0.0011 (7)
O2 0.0587 (12) 0.0514 (11) 0.0372 (9) −0.0160 (10) 0.0039 (9) −0.0001 (9)
Open in a new tab

Geometric parameters (Å, º)

C1—C2 1.385 (3) C9—H9A 0.9900
C1—C10A 1.415 (3) C9—H9B 0.9900
C1—C11 1.526 (3) C10—C10A 1.512 (3)
C2—C3 1.372 (3) C10—H10A 0.9900
C2—O1 1.412 (3) C10—H10B 0.9900
C3—C4 1.381 (3) C11—C13 1.524 (4)
C3—H3 0.9500 C11—C12 1.530 (4)
C4—C4A 1.398 (3) C11—H11 1.0000
C4—H4 0.9500 C12—H12A 0.9800
C4A—C10A 1.406 (3) C12—H12B 0.9800
C4A—C4B 1.541 (3) C12—H12C 0.9800
C4B—C5 1.543 (3) C13—H13A 0.9800
C4B—C14 1.544 (3) C13—H13B 0.9800
C4B—C8A 1.553 (3) C13—H13C 0.9800
C5—C6 1.526 (3) C14—H14A 0.9800
C5—H5A 0.9900 C14—H14B 0.9800
C5—H5B 0.9900 C14—H14C 0.9800
C6—C7 1.512 (4) C15—H15A 0.9800
C6—H6A 0.9900 C15—H15B 0.9800
C6—H6B 0.9900 C15—H15C 0.9800
C7—C8 1.532 (3) C16—H16A 0.9800
C7—H7A 0.9900 C16—H16B 0.9800
C7—H7B 0.9900 C16—H16C 0.9800
C8—C15 1.530 (4) C17—O2 1.193 (3)
C8—C16 1.533 (4) C17—O1 1.361 (3)
C8—C8A 1.560 (3) C17—C18 1.496 (3)
C8A—C9 1.520 (3) C18—H18A 0.9800
C8A—H8A 1.0000 C18—H18B 0.9800
C9—C10 1.516 (3) C18—H18C 0.9800
C2—C1—C10A 117.49 (18) H9A—C9—H9B 108.0
C2—C1—C11 121.51 (18) C10A—C10—C9 116.61 (19)
C10A—C1—C11 120.92 (19) C10A—C10—H10A 108.1
C3—C2—C1 122.74 (18) C9—C10—H10A 108.1
C3—C2—O1 118.32 (18) C10A—C10—H10B 108.1
C1—C2—O1 118.77 (18) C9—C10—H10B 108.1
C2—C3—C4 119.29 (19) H10A—C10—H10B 107.3
C2—C3—H3 120.4 C4A—C10A—C1 120.89 (19)
C4—C3—H3 120.4 C4A—C10A—C10 120.43 (18)
C3—C4—C4A 121.18 (19) C1—C10A—C10 118.65 (18)
C3—C4—H4 119.4 C13—C11—C1 110.0 (2)
C4A—C4—H4 119.4 C13—C11—C12 111.6 (2)
C4—C4A—C10A 118.38 (18) C1—C11—C12 115.1 (2)
C4—C4A—C4B 119.92 (18) C13—C11—H11 106.5
C10A—C4A—C4B 121.63 (18) C1—C11—H11 106.5
C4A—C4B—C5 111.23 (17) C12—C11—H11 106.5
C4A—C4B—C14 105.79 (18) C11—C12—H12A 109.5
C5—C4B—C14 108.22 (19) C11—C12—H12B 109.5
C4A—C4B—C8A 107.92 (17) H12A—C12—H12B 109.5
C5—C4B—C8A 109.04 (17) C11—C12—H12C 109.5
C14—C4B—C8A 114.6 (2) H12A—C12—H12C 109.5
C6—C5—C4B 112.74 (18) H12B—C12—H12C 109.5
C6—C5—H5A 109.0 C11—C13—H13A 109.5
C4B—C5—H5A 109.0 C11—C13—H13B 109.5
C6—C5—H5B 109.0 H13A—C13—H13B 109.5
C4B—C5—H5B 109.0 C11—C13—H13C 109.5
H5A—C5—H5B 107.8 H13A—C13—H13C 109.5
C7—C6—C5 111.0 (2) H13B—C13—H13C 109.5
C7—C6—H6A 109.4 C4B—C14—H14A 109.5
C5—C6—H6A 109.4 C4B—C14—H14B 109.5
C7—C6—H6B 109.4 H14A—C14—H14B 109.5
C5—C6—H6B 109.4 C4B—C14—H14C 109.5
H6A—C6—H6B 108.0 H14A—C14—H14C 109.5
C6—C7—C8 114.08 (19) H14B—C14—H14C 109.5
C6—C7—H7A 108.7 C8—C15—H15A 109.5
C8—C7—H7A 108.7 C8—C15—H15B 109.5
C6—C7—H7B 108.7 H15A—C15—H15B 109.5
C8—C7—H7B 108.7 C8—C15—H15C 109.5
H7A—C7—H7B 107.6 H15A—C15—H15C 109.5
C15—C8—C7 109.6 (2) H15B—C15—H15C 109.5
C15—C8—C16 107.7 (2) C8—C16—H16A 109.5
C7—C8—C16 107.9 (2) C8—C16—H16B 109.5
C15—C8—C8A 114.3 (2) H16A—C16—H16B 109.5
C7—C8—C8A 109.00 (17) C8—C16—H16C 109.5
C16—C8—C8A 108.25 (19) H16A—C16—H16C 109.5
C9—C8A—C4B 109.05 (18) H16B—C16—H16C 109.5
C9—C8A—C8 113.59 (17) O2—C17—O1 123.7 (2)
C4B—C8A—C8 117.57 (17) O2—C17—C18 126.0 (2)
C9—C8A—H8A 105.2 O1—C17—C18 110.3 (2)
C4B—C8A—H8A 105.2 C17—C18—H18A 109.5
C8—C8A—H8A 105.2 C17—C18—H18B 109.5
C10—C9—C8A 111.51 (18) H18A—C18—H18B 109.5
C10—C9—H9A 109.3 C17—C18—H18C 109.5
C8A—C9—H9A 109.3 H18A—C18—H18C 109.5
C10—C9—H9B 109.3 H18B—C18—H18C 109.5
C8A—C9—H9B 109.3 C17—O1—C2 117.79 (16)
Open in a new tab

Footnotes

Supporting information for this paper is available from the IUCr electronic archives (Reference: XU5767).

References

  1. Agilent (2012). CrysAlis PRO Agilent Technologies Ltd, Abingdon, England.
  2. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.
  3. Barrero, A. F., Quílez del Moral, J. F., Lucas, R., Payá, M., Akssira, M., Akaad, S. & Mellouki, F. (2003). J. Nat. Prod. 66, 844–50. [DOI] [PubMed]
  4. Bernabeu, A., Shapiro, S. & Villalain, J. (2002). Chem. Phys. Lipids, 119, 33–39. [DOI] [PubMed]
  5. Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  6. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  7. Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
  8. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  9. Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148.
  10. Haraguchi, H., Oike, S., Muroi, H. & Kubo, I. (1996). Planta Med. 62, 122–125. [DOI] [PubMed]
  11. Marcos, I. S., Cubillo, M. A. & Moro, R. F. (2003). Tetrahedron Lett. 44, 8831–8835.
  12. Pettit, G. R., Tan, R., Northen, J. S., Herald, D. L., Chapuis, J.-C. & Pettit, R. K. (2004). J. Nat. Prod. 67, 1476–1482. [DOI] [PubMed]
  13. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  14. Short, W. F. & Stromberg, H. (1937). J. Chem. Soc. pp. 516–520.
  15. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  16. Tacon, C., Drguantaieric, M., Smith, P. J. & Chibale, K. (2012). Bioorg. Med. Chem. 20, 893–902. [DOI] [PubMed]
  17. Zeroual, A., Mazoir, N., Daran, J.-C., Akssira, M. & Benharref, A. (2008). Acta Cryst. E64, o604–o605. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002748/xu5767sup1.cif

e-70-0o317-sup1.cif (27.2KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002748/xu5767Isup2.hkl

e-70-0o317-Isup2.hkl (138KB, hkl)
Click here for additional data file. (7.7KB, cml)

Supporting information file. DOI: 10.1107/S1600536814002748/xu5767Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=985421

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES