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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o475.
Published online 2008 January 18. doi:  10.1107/S1600536808001086
PMCID: PMC2960367

1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative

Abstract

In the search for cancer chemopreventive agents, we have studied the Diels–Alder reaction of trans-communic acid with tetra­cyano­ethyl­ene in the presence of SiO2 as catalyst. The title cycloadduct, C26H30N4O2, was obtained in 75% yield. The mol­ecules are arranged in pairs through O—H(...)O hydrogen bonds, forming an R 2 2(8) ring motif. Both the fused cyclohexyl rings adopt a chair conformation, whereas the nonfused ring adopts a half-chair conformation.

Related literature

For literature on anti-tumour activity, see: Bouhal et al. (1988 [triangle]); Iwamoto et al. (2001 [triangle]). For structural analyses, see: Etter et al. (1990 [triangle]); Bernstein et al. (1995 [triangle]); Cremer & Pople (1975 [triangle]). For the treatment of disordered solvent, see: Spek (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o475-scheme1.jpg

Experimental

Crystal data

  • C26H30N4O2
  • M r = 430.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o475-efi1.jpg
  • a = 30.664 (4) Å
  • b = 11.8233 (19) Å
  • c = 7.1857 (10) Å
  • β = 93.260 (12)°
  • V = 2600.9 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 180 (2) K
  • 0.52 × 0.08 × 0.07 mm

Data collection

  • Oxford Diffraction Xcalibur Sapphire-I diffractometer
  • Absorption correction: none
  • 5114 measured reflections
  • 2615 independent reflections
  • 1302 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.085
  • S = 0.82
  • 2615 reflections
  • 293 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001086/er2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001086/er2042Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Juniperus oxycedrus has been used in traditional folk medicine for the treatment of chronic eczema and other several skin diseases (Bouhal et al., 1988). Trans communic acid 1 is one of the compounds which were isolated from Juniperusoxycedrus and known by its moderate anti-tumor activity (Iwamoto et al., 2001). In the search for cancer chemo preventive agents with strong activity, we have studied the Diels-Alder reaction of trans communic acid 1 with tetracyanoethylene 2 in the presence of SiO2 as catalyst (Fig.1). One cycloadduct 3 was obtained in 75% yield.

Its structure was identified as 1,4a-Dimethyl-6-methylene-5-(5,5,6,6-tetracyano-2-methylcyclohex-2-\ enylmethyl)-decahydronaphthalene-1-carboxylic acid using spectral methods including 1H and 13C NMR and confirmed by an X-ray crystallographic analysis. The 1H NMR spectrum of 3 exhibits three methyl singlets at 1.96, 1.29 and 0.69 p.p.m., a triplet (J=3 Hz, at 5.57ppm) due to proton H-3' and two singlets (at 4.50 and 5.08 p.p.m.) assigned to methylenic protons at 13 position. The 13C NMR spectra reveals twenty six signals including specially a carbonyl group at 183.36 p.p.m. and four cyano group signals at 109.19; 110.07; 110.94 and 111.54ppm.

The molecule is build up by two fused six cyclohexyl rings linked linked through a CH2 spacer to a tetracyano-2-methylcyclohexyl ring (Fig. 2). The fused cyclohexyl rings, C1 to C8a and C4A to C8A, adopt a chair conformation as indicated by the puckering parameters [Q= 0.533 (6)°, 0.576 (6)° and θ= 0. 0(6)°, 0.4 (6)°, Cremer & Pople, (1975)]. The non fused cyclohexyl ring adopt a half-chair conformation[Q= 0.510 (6)° and θ= 50.7 (5)°]. The occurrence of O—H···O hydrogen bonds form pairs of molecules through a R22(8) ring motif (Etter et al., 1990; Bernstein et al., 1995) (Fig. 3).

Experimental

To a solution of Compound 1(1 g, 2.5 mmol) in 20 ml of dichloromethane, was added tetracyanoethylene (TCNE)(0.32 g, 2.5 mmol). The mixture was refluxed for 72 h. After cooling, the solvent was removed by evaporation under reduced pressure. The obtained residue was purified by chromatography on silica gel column (eluent: hexane/ethyl acetate 90/10), then the isolated product was recrystallized from ethyl acetate to give compound 3(750 mg, 75%).

Colourless crystal, mp=208–210°C (ethyl acetate). 1H NMR (300 MHz, CDCl3)δ (p.p.m.): 5.57 (t, 1H, J=4.45 Hz); 5.08 (s, 1H); 4.50 (s,1H); 3.28 (br d,1H, J=11.5 Hz); 3.00 (m, 2H); 2.48 (br d, 1H, J=11.5 Hz); 2.29–1.96 (m, 5H); 1.92 (s, 3H); 1.81 (m, 3H); 1.62 (m, 1H); 1.45 (dd, 1H, J=12.21 and 2.60); 1.29 (s, 3H); 1.26 (m, 2H); 1.15 (m, 1H); 0.69 (s, 3H). 13C NMR δ (p.p.m.) CDCl3: 12.64 C11, 19.85 C3, 21.78 C7, 25.59 C8, 26.13 C4, 29.01 C9, 31.75 C12, 37.70 C2, 38.07 C4', 38.58 C7, 39.56 C4a, 41.37 C6', 41.74 C1', 43.41 C5', 44.29 C1, 51.63 C5, 56.47 C8a, 107.59 C13, 109.19 C8', 110.07 C9', 110.94 C10', 111.54 C11', 116.37 C3', 135.27 C6, 147.14 C2', 183.36 C10

Refinement

All H atoms attached to C atoms and 0 atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.99 Å (methylene), 0.98(methyl), 1.0Å (methine) and O—H = 0.84Å with Uiso(H) = 1.2Ueq(aromatic, methine, methylene) and Uiso(H) = 1.5Ueq(methyl & hydroxyl). In the absence of significant anomalous scattering, the absolute configuration could not be reliably determined and then the Friedel pairs were merged and any references to the Flack parameter were removed. Some residual electron density were difficult to modelize and therefore, the SQUEEZE function of PLATON (Spek, 2003) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was employed for the final refinement. There are two cavities of 158 Å3 per unit cell. PLATON estimated that each cavity contains about 11 electrons. Owing to the solvent used for crystallization, one may estimate that the voids contain 0.25 ethyl acetate molecule.

Figures

Fig. 1.
Scheme showing the synthetic pathway for the title compound.
Fig. 2.
Molecular view of compound 3 with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 3.
Partial packing view showing pair of molecules connected by O—H···O hydrogen bonds and forming a R22(8) ring motif. Hydrogen bonds are shown as dashed lines. Hydrogen not involved in hydrogen bonding have been omitted for ...

Crystal data

C26H30N4O2F000 = 920
Mr = 430.54Dx = 1.099 Mg m3
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 907 reflections
a = 30.664 (4) Åθ = 3.1–26.4º
b = 11.8233 (19) ŵ = 0.07 mm1
c = 7.1857 (10) ÅT = 180 (2) K
β = 93.260 (12)ºNeedle, colorless
V = 2600.9 (6) Å30.52 × 0.08 × 0.07 mm
Z = 4

Data collection

Oxford-Diffraction Xcalibur Sapphire-I diffractometer2615 independent reflections
Radiation source: fine-focus sealed tube1302 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
Detector resolution: 8.2632 pixels mm-1θmax = 26.4º
T = 180(2) Kθmin = 3.1º
ω and [var phi] scansh = −23→38
Absorption correction: nonek = −11→14
5114 measured reflectionsl = −7→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.085  w = 1/[σ2(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.003
2615 reflectionsΔρmax = 0.13 e Å3
293 parametersΔρmin = −0.12 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C10.59538 (10)0.4362 (3)0.2817 (5)0.0536 (10)
C1'0.64958 (9)−0.0975 (3)0.2534 (4)0.0364 (9)
H1'0.6284−0.12630.15370.044*
C2'0.65560 (10)−0.1895 (3)0.3989 (4)0.0398 (9)
C20.63385 (10)0.4539 (3)0.4201 (6)0.0623 (11)
H2A0.66080.46050.35090.075*
H2B0.62980.52620.48640.075*
C3'0.69097 (10)−0.2504 (3)0.4250 (4)0.0507 (10)
H3'0.6914−0.30520.52170.061*
C30.63991 (10)0.3605 (3)0.5617 (5)0.0592 (11)
H3A0.61470.35970.64160.071*
H3B0.66650.37570.64240.071*
C40.64403 (10)0.2457 (3)0.4706 (5)0.0495 (10)
H4A0.64580.18690.56890.059*
H4B0.67160.24330.40550.059*
C4'0.73066 (10)−0.2407 (3)0.3154 (5)0.0529 (10)
H4'A0.7427−0.31700.29380.063*
H4'B0.7532−0.19600.38650.063*
C4A0.60575 (9)0.2174 (3)0.3301 (4)0.0361 (9)
C50.61843 (9)0.1098 (3)0.2159 (4)0.0351 (8)
H50.64570.12940.15290.042*
C5'0.71920 (10)−0.1833 (3)0.1284 (5)0.0481 (10)
C60.58379 (11)0.0870 (4)0.0639 (5)0.0494 (10)
C6'0.69273 (9)−0.0707 (3)0.1609 (5)0.0417 (9)
C7'0.61661 (10)−0.2127 (3)0.5115 (5)0.0564 (11)
H7'A0.6219−0.28110.58660.085*
H7'B0.5907−0.22390.42720.085*
H7'C0.6118−0.14840.59390.085*
C70.57720 (12)0.1836 (4)−0.0693 (5)0.0692 (13)
H7A0.55350.1652−0.16360.083*
H7B0.60430.1966−0.13500.083*
C8'0.69222 (12)−0.2582 (4)0.0066 (6)0.0508 (10)
C80.56546 (11)0.2901 (3)0.0358 (5)0.0593 (12)
H8A0.53660.27970.08870.071*
H8B0.56310.3545−0.05230.071*
C8A0.59952 (10)0.3178 (3)0.1931 (5)0.0472 (10)
H80.62770.32130.12970.057*
C90.55363 (10)0.4563 (3)0.3803 (6)0.0470 (10)
C9'0.75865 (11)−0.1575 (4)0.0316 (5)0.0602 (11)
C10'0.72097 (11)0.0021 (3)0.2844 (6)0.0548 (11)
C100.59748 (14)0.5294 (3)0.1310 (6)0.0858 (16)
H10A0.57100.52660.04820.129*
H10B0.62310.51700.05810.129*
H10C0.59970.60370.19130.129*
C110.56460 (9)0.1932 (3)0.4331 (4)0.0438 (9)
H11A0.57000.12980.51900.066*
H11B0.54060.17390.34280.066*
H11C0.55670.26050.50350.066*
C11'0.68511 (11)−0.0140 (3)−0.0200 (6)0.0486 (10)
C120.62924 (10)0.0071 (3)0.3388 (4)0.0403 (9)
H12A0.6019−0.01720.39370.048*
H12B0.64930.03260.44310.048*
C130.55899 (11)−0.0039 (4)0.0508 (5)0.0696 (13)
H13A0.5364−0.0090−0.04480.084*
H13B0.5637−0.06420.13680.084*
N8'0.67137 (11)−0.3154 (3)−0.0892 (5)0.0749 (11)
N9'0.78989 (10)−0.1379 (4)−0.0408 (5)0.0974 (14)
N10'0.74280 (11)0.0563 (3)0.3805 (5)0.0864 (13)
N11'0.68067 (11)0.0254 (3)−0.1637 (5)0.0767 (11)
O90.51784 (7)0.4467 (2)0.2691 (3)0.0616 (8)
H90.49580.45890.33030.092*
O9'0.55236 (7)0.4807 (2)0.5443 (4)0.0569 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.042 (2)0.056 (3)0.065 (3)0.0049 (18)0.023 (2)0.014 (2)
C1'0.0289 (17)0.047 (2)0.034 (2)−0.0031 (15)0.0035 (16)−0.0048 (18)
C2'0.043 (2)0.044 (2)0.032 (2)−0.0001 (17)0.0037 (15)−0.0009 (19)
C20.0362 (19)0.046 (3)0.106 (3)−0.0033 (18)0.020 (2)−0.002 (3)
C3'0.057 (2)0.060 (3)0.035 (2)0.008 (2)0.0042 (18)0.008 (2)
C30.041 (2)0.056 (3)0.079 (3)−0.0013 (19)−0.0142 (19)−0.016 (3)
C40.0387 (19)0.058 (3)0.051 (2)0.0003 (18)−0.0047 (16)−0.001 (2)
C4'0.047 (2)0.071 (3)0.041 (2)0.0157 (19)−0.0008 (17)0.009 (2)
C4A0.0301 (17)0.046 (2)0.033 (2)0.0065 (15)0.0034 (15)0.0118 (18)
C50.0336 (18)0.045 (2)0.027 (2)0.0009 (15)0.0025 (15)0.0057 (19)
C5'0.0338 (19)0.065 (3)0.046 (2)0.0010 (19)0.0073 (17)0.000 (2)
C60.042 (2)0.071 (3)0.035 (2)0.011 (2)0.0020 (18)−0.005 (2)
C6'0.0365 (18)0.049 (2)0.040 (2)−0.0049 (17)0.0040 (16)0.002 (2)
C7'0.053 (2)0.071 (3)0.046 (2)0.0026 (18)0.0139 (17)0.016 (2)
C70.074 (3)0.105 (4)0.029 (2)0.036 (2)0.0067 (18)0.007 (3)
C8'0.053 (3)0.057 (3)0.043 (3)0.005 (2)0.013 (2)0.009 (2)
C80.064 (2)0.086 (3)0.028 (2)0.033 (2)0.0061 (18)0.014 (2)
C8A0.0355 (18)0.065 (3)0.043 (2)0.0142 (17)0.0170 (16)0.009 (2)
C90.039 (2)0.043 (2)0.059 (3)0.0040 (16)0.006 (2)0.020 (2)
C9'0.049 (2)0.082 (3)0.050 (3)0.006 (2)0.0087 (19)−0.001 (2)
C10'0.039 (2)0.060 (3)0.067 (3)−0.0105 (19)0.013 (2)−0.007 (2)
C100.100 (3)0.060 (3)0.104 (4)0.018 (2)0.059 (3)0.047 (3)
C110.042 (2)0.060 (3)0.030 (2)−0.0030 (17)0.0069 (16)−0.001 (2)
C11'0.052 (2)0.046 (3)0.049 (3)0.0067 (18)0.017 (2)0.010 (2)
C120.0415 (18)0.048 (2)0.031 (2)−0.0010 (16)0.0030 (15)0.0012 (18)
C130.046 (2)0.099 (4)0.062 (3)0.011 (3)−0.015 (2)−0.004 (3)
N8'0.089 (3)0.084 (3)0.053 (2)−0.013 (2)0.016 (2)−0.005 (2)
N9'0.057 (2)0.143 (4)0.095 (3)0.001 (2)0.032 (2)0.004 (3)
N10'0.063 (2)0.101 (3)0.095 (3)−0.031 (2)0.008 (2)−0.042 (3)
N11'0.094 (3)0.088 (3)0.051 (2)0.023 (2)0.028 (2)0.019 (2)
O90.0462 (14)0.092 (2)0.0471 (15)0.0210 (14)0.0064 (12)0.0007 (16)
O9'0.0444 (13)0.075 (2)0.0519 (16)−0.0021 (12)0.0105 (13)−0.0057 (16)

Geometric parameters (Å, °)

C1—C21.513 (5)C5'—C6'1.584 (5)
C1—C91.517 (5)C6—C131.316 (5)
C1—C8A1.546 (5)C6—C71.497 (5)
C1—C101.549 (5)C6'—C11'1.470 (5)
C1'—C2'1.513 (4)C6'—C10'1.480 (5)
C1'—C121.529 (4)C7'—H7'A0.9800
C1'—C6'1.547 (4)C7'—H7'B0.9800
C1'—H1'1.0000C7'—H7'C0.9800
C2'—C3'1.306 (4)C7—C81.521 (5)
C2'—C7'1.506 (4)C7—H7A0.9900
C2—C31.506 (5)C7—H7B0.9900
C2—H2A0.9900C8'—N8'1.136 (5)
C2—H2B0.9900C8—C8A1.530 (5)
C3'—C4'1.491 (4)C8—H8A0.9900
C3'—H3'0.9500C8—H8B0.9900
C3—C41.516 (5)C8A—H81.0000
C3—H3A0.9900C9—O9'1.216 (4)
C3—H3B0.9900C9—O91.325 (4)
C4—C4A1.541 (4)C9'—N9'1.139 (4)
C4—H4A0.9900C10'—N10'1.133 (4)
C4—H4B0.9900C10—H10A0.9800
C4'—C5'1.528 (5)C10—H10B0.9800
C4'—H4'A0.9900C10—H10C0.9800
C4'—H4'B0.9900C11—H11A0.9800
C4A—C111.526 (4)C11—H11B0.9800
C4A—C8A1.547 (4)C11—H11C0.9800
C4A—C51.574 (4)C11'—N11'1.134 (4)
C5—C61.504 (4)C12—H12A0.9900
C5—C121.527 (4)C12—H12B0.9900
C5—H51.0000C13—H13A0.9500
C5'—C9'1.462 (5)C13—H13B0.9500
C5'—C8'1.466 (5)O9—H90.8400
C2—C1—C9108.6 (3)C13—C6—C5125.4 (4)
C2—C1—C8A108.5 (3)C7—C6—C5113.1 (3)
C9—C1—C8A115.2 (3)C11'—C6'—C10'108.8 (3)
C2—C1—C10107.4 (3)C11'—C6'—C1'112.1 (3)
C9—C1—C10106.5 (3)C10'—C6'—C1'110.3 (3)
C8A—C1—C10110.4 (3)C11'—C6'—C5'108.0 (3)
C2'—C1'—C12109.9 (2)C10'—C6'—C5'106.9 (3)
C2'—C1'—C6'111.7 (2)C1'—C6'—C5'110.5 (3)
C12—C1'—C6'112.7 (3)C2'—C7'—H7'A109.5
C2'—C1'—H1'107.4C2'—C7'—H7'B109.5
C12—C1'—H1'107.4H7'A—C7'—H7'B109.5
C6'—C1'—H1'107.4C2'—C7'—H7'C109.5
C3'—C2'—C7'120.0 (3)H7'A—C7'—H7'C109.5
C3'—C2'—C1'124.3 (3)H7'B—C7'—H7'C109.5
C7'—C2'—C1'115.7 (3)C6—C7—C8110.0 (3)
C3—C2—C1113.8 (3)C6—C7—H7A109.7
C3—C2—H2A108.8C8—C7—H7A109.7
C1—C2—H2A108.8C6—C7—H7B109.7
C3—C2—H2B108.8C8—C7—H7B109.7
C1—C2—H2B108.8H7A—C7—H7B108.2
H2A—C2—H2B107.7N8'—C8'—C5'179.3 (4)
C2'—C3'—C4'125.3 (3)C7—C8—C8A111.9 (3)
C2'—C3'—H3'117.3C7—C8—H8A109.2
C4'—C3'—H3'117.3C8A—C8—H8A109.2
C2—C3—C4112.0 (3)C7—C8—H8B109.2
C2—C3—H3A109.2C8A—C8—H8B109.2
C4—C3—H3A109.2H8A—C8—H8B107.9
C2—C3—H3B109.2C8—C8A—C4A111.1 (3)
C4—C3—H3B109.2C8—C8A—C1115.4 (3)
H3A—C3—H3B107.9C4A—C8A—C1116.3 (3)
C3—C4—C4A113.5 (3)C8—C8A—H8104.1
C3—C4—H4A108.9C4A—C8A—H8104.1
C4A—C4—H4A108.9C1—C8A—H8104.1
C3—C4—H4B108.9O9'—C9—O9122.3 (3)
C4A—C4—H4B108.9O9'—C9—C1124.4 (3)
H4A—C4—H4B107.7O9—C9—C1113.4 (3)
C3'—C4'—C5'110.2 (3)N9'—C9'—C5'178.7 (4)
C3'—C4'—H4'A109.6N10'—C10'—C6'178.9 (5)
C5'—C4'—H4'A109.6C1—C10—H10A109.5
C3'—C4'—H4'B109.6C1—C10—H10B109.5
C5'—C4'—H4'B109.6H10A—C10—H10B109.5
H4'A—C4'—H4'B108.1C1—C10—H10C109.5
C11—C4A—C4110.1 (3)H10A—C10—H10C109.5
C11—C4A—C8A112.1 (2)H10B—C10—H10C109.5
C4—C4A—C8A108.2 (3)C4A—C11—H11A109.5
C11—C4A—C5109.7 (3)C4A—C11—H11B109.5
C4—C4A—C5108.4 (2)H11A—C11—H11B109.5
C8A—C4A—C5108.3 (2)C4A—C11—H11C109.5
C6—C5—C12113.5 (3)H11A—C11—H11C109.5
C6—C5—C4A109.8 (3)H11B—C11—H11C109.5
C12—C5—C4A113.2 (2)N11'—C11'—C6'176.2 (4)
C6—C5—H5106.6C5—C12—C1'119.4 (2)
C12—C5—H5106.6C5—C12—H12A107.5
C4A—C5—H5106.6C1'—C12—H12A107.5
C9'—C5'—C8'107.2 (3)C5—C12—H12B107.5
C9'—C5'—C4'110.8 (3)C1'—C12—H12B107.5
C8'—C5'—C4'110.5 (3)H12A—C12—H12B107.0
C9'—C5'—C6'109.9 (3)C6—C13—H13A120.0
C8'—C5'—C6'108.6 (3)C6—C13—H13B120.0
C4'—C5'—C6'109.7 (3)H13A—C13—H13B120.0
C13—C6—C7121.4 (4)C9—O9—H9109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O9—H9···O9'i0.841.792.631 (3)178

Symmetry codes: (i) −x+1, y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ER2042).

References

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