organic papers
Acta Cryst.(2007). E63, o1899–o1901 doi:10.1107/S1600536807012834 Salaeet al. C
20H32O2
o1899
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
ent
-Kaur-16-ene-13,19-diol
Abdul Wahab Salae,aSuchada Chantrapromma,a‡ Hoong-Kun Funb* and Chanita
Ponglimanonta
aDepartment of Chemistry, Faculty of Science,
Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, andbX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
‡ Additional correspondence author, email: [email protected].
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 100 K
Mean(C–C) = 0.003 A˚ Rfactor = 0.043 wRfactor = 0.108
Data-to-parameter ratio = 12.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 11 March 2007 Accepted 19 March 2007
#2007 International Union of Crystallography All rights reserved
The title compound, C20H32O2, a diterpenoid, was isolated from the roots of Bruguiera cylindrica (Rhizophoraceae). There are two crystallographically independent molecules in the asymmetric unit. In both molecules, the cyclohexane rings adopt chair conformations and the cyclopentane ring has an envelope conformation. In the crystal structure, molecules are linked into a two-dimensional network by intermolecular O— H O hydrogen bonds.
Comment
The title diterpenoid compound, (I), which is known as ent -kaur-16-ene-13,19-diol (Subrahmanyanet al., 1999; Hanet al., 2004), was isolated from the roots of Bruguiera cylindrica
(Rhizophoraceae), a mangrove plant which is found in south-east Asia. In our continuing research on bioactive compounds from mangrove sources (Chantraprommaet al., 2006; Chum-kaew et al., 2006; Fun, Chantrapromma et al., 2006; Fun, Pakhathirathien et al., 2006), we have studied the chemical constituents from the roots of Bruguiera cylindrica (Rhizo-phoraceae). Our studies show that the CH2Cl2extract of the roots of this plant shows strong cytotoxic activity against MCF-7 (breast cancer) and HT-29 (colon cancer) cell lines. Previously, we have reported the isolation and crystal struc-ture of another compound, 3-feruloyltaraxerol, from this plant (Chantraprommaet al., 2003). We report here the crystal structure of (I).
The title compound crystallizes with two independent molecules,AandB, in the asymmetric unit. The two molecules have similar bond lengths but the O—C—C angles at C13 are slightly different (Table 1). The bond distances and angles are within normal ranges (Allenet al., 1987).
The molecule of (I) contains a fused four-ring systemA/B/ C/D(Fig. 1). TheA/Bring junction istrans-fused, andB/Cand
adopt chair conformations and the cyclopentane ring has an envelope conformation, with atom C14 displaced from the C9/
C13/C15/C16 plane by 0.301 (2) A˚ in molecule A and
0.299 (2) A˚ in moleculeB; the Cremer & Pople (1975) puck-ering parameters Q and are 0.465 (2) A˚ and 30.4 (3), respectively, in molecule A, and 0.464 (2) A˚ and 29.9 (3) in molecule B. The hydroxyl group is equatorially attached at atom C13. The methylene group is equatorially attached to the cyclopentane ring at atom C16. The hydroxymethyl group is axially attached to the cyclohexane ring Aat atom C5. The orientation of the hydroxymethyl group is described by the C4—C5—C19—O1 torsion angle, which is65.0 (2) in mol-ecule A [67.2 (2)in moleculeB].
The crystal packing of (I) is stabilized by intermolecular
O—H O hydrogen bonds (Table 2). The molecules are
linked into a two-dimensional network parallel to thebcplane (Fig. 2).
Experimental
The air-dried roots ofBruguiera cylindrica(6.0 kg) were chopped and extracted with CH2Cl2(222 l) for one week at room temperature.
Removal of the solvent from the CH2Cl2 extract under reduced
pressure gave a yellow viscous residue (38.5 g) which was subjected to quick column chromatography over silica gel using solvents of increasing polarity fromn-hexane to EtOAc to afford 14 fractions (F1–F14). Fraction F7 was further purified by quick column chro-matography using CHCl–acetone (20:1), yielding compound (I)
obtained by recrystallization from acetone after several days [m.p. 528–530 K].
Crystal data
C20H32O2 Mr= 304.46
Monoclinic,P21 a= 10.6496 (4) A˚ b= 7.8597 (3) A˚ c= 20.3159 (7) A˚
= 97.907 (2)
V= 1684.33 (11) A˚3 Z= 4
MoKradiation
= 0.08 mm1 T= 100.0 (1) K 0.560.240.12 mm
Data collection
Bruker SMART APEX II CCD area-detector diffractometer Absorption correction: multi-scan
(SADABS; Bruker, 2005) Tmin= 0.960,Tmax= 0.991
19242 measured reflections 5031 independent reflections 4395 reflections withI> 2(I) Rint= 0.038
Refinement
R[F2> 2(F2)] = 0.043 wR(F2) = 0.109 S= 1.05 5031 reflections 417 parameters 1 restraint
H atoms treated by a mixture of independent and constrained refinement
max= 0.31 e A˚ 3
[image:2.610.45.296.76.156.2]min=0.19 e A˚ 3
Table 1
Selected geometric parameters (A˚ ,).
O1A—C19A 1.440 (2) O2A—C13A 1.423 (2) C16A—C20A 1.320 (3)
O1B—C19B 1.431 (2) O2B—C13B 1.422 (3) C16B—C20B 1.325 (3)
O2A—C13A—C16A 113.08 (16) O2A—C13A—C14A 111.33 (18) O2A—C13A—C12A 111.87 (17) C20A—C16A—C15A 128.39 (19) C20A—C16A—C13A 124.30 (18) C15A—C16A—C13A 107.26 (16)
O2B—C13B—C16B 115.17 (17) O2B—C13B—C12B 106.76 (17) O2B—C13B—C14B 115.36 (18) C20B—C16B—C15B 127.6 (2) C20B—C16B—C13B 125.1 (2) C15B—C16B—C13B 107.28 (16)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1A—H1AA O2Bi
0.81 (3) 1.94 (3) 2.750 (2) 171 (4) O2A—H2AA O1B 0.86 (4) 1.86 (4) 2.711 (2) 172 (3) O1B—H1BA O1Aii
0.88 (4) 1.85 (4) 2.718 (3) 172 (3) O2B—H2BA O2Aiii
0.79 (4) 1.95 (4) 2.699 (2) 159 (3)
Symmetry codes: (i)x;y;z1; (ii)xþ1;y1
2;zþ1; (iii)xþ1;y 1 2;zþ2.
Hydroxyl H atoms were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 A˚ . TheUisovalues were constrained to be 1.5Ueqof
the carrier atom for methyl H atoms and 1.2Ueqfor the remaining H
atoms. A rotating group model was used for the methyl groups. In the absence of significant anomalous scattering effects, 4158 Friedel pairs were averaged.
Data collection:APEX2(Bruker, 2005); cell refinement:APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine
Figure 1
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed line indicates a hydrogen bond.
Figure 2
[image:2.610.46.290.220.369.2]to prepare material for publication:SHELXTLandPLATON(Spek, 2003).
Financial support from the Centre for Innovation in Chemistry: Postgraduate Education and Research Programme in Chemistry (PERCH-CIC), Commission on Higher Educa-tion, Ministry of EducaEduca-tion, Thailand, is gratefully acknowl-edged. The authors also thank the Prince of Songkla University, the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) No. 304/PFIZIK/653003/A118.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Bruker (2005).APEX2,SAINTandSADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Fun, H.-K., Razak, I. A., Laphookhieo, S. & Karalai, C. (2003).Acta Cryst.E59, o1864–o1866.
Chantrapromma, S., Pakathirathien, C., Fun, H.-K., Razak, I. A. & Karalai, C. (2006).Acta Cryst.E62, o1742–o1744.
Chumkaew, P., Kata, S. & Chantrapromma, K. (2006).Chem. Pharm. Bull.54, 1344–1346.
Cremer, D. & Pople, J. A. (1975).J. Am. Chem. Soc.97, 1354–1358. Fun, H.-K., Chantrapromma, S., Boonnak, N., Chaiyadej, K., Chantrapromma,
K. & Yu, X.-L. (2006).Acta Cryst.E62, o3725–o3727.
Fun, H.-K., Pakhathirathien, C., Chantrapromma, S., Karalai, C. & Chantrapromma, K. (2006).Acta Cryst.E62, o5539–o5541.
Han, L., Huang, X., Sattler, I., Dahse, H. M., Fu, H., Lin, W. & Grabley, S. (2004).J. Nat. Prod.67, 1620–1623.
Sheldrick, G. M. (1998).SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
Subrahmanyan, C., Rao, B. V., Ward, R. S., Hursthouse, M. B. & Hibbs, D. E. (1999).Phytochemistry,51, 83–90.
organic papers
Acta Cryst.(2007). E63, o1899–o1901 Salaeet al. C
supporting information
Acta Cryst. (2007). E63, o1899–o1901 [https://doi.org/10.1107/S1600536807012834]
ent
-Kaur-16-ene-13,19-diol
Abdul Wahab Salae, Suchada Chantrapromma, Hoong-Kun Fun and Chanita Ponglimanont
ent-Kaur-16-ene-13,19-diol
Crystal data
C20H32O2
Mr = 304.46 Monoclinic, P21
Hall symbol: P 2yb
a = 10.6496 (4) Å
b = 7.8597 (3) Å
c = 20.3159 (7) Å
β = 97.907 (2)°
V = 1684.33 (11) Å3
Z = 4
F(000) = 672
Dx = 1.201 Mg m−3
Melting point = 528–530 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4787 reflections
θ = 1.0–29.0°
µ = 0.08 mm−1
T = 100 K Needle, colourless 0.56 × 0.24 × 0.12 mm
Data collection
Bruker SMART APEX II CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 8.33 pixels mm-1
ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2005)
Tmin = 0.960, Tmax = 0.991
19242 measured reflections 5031 independent reflections 4395 reflections with I > 2σ(I)
Rint = 0.038
θmax = 29.6°, θmin = 1.0°
h = −11→14
k = −10→10
l = −28→24
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.043
wR(F2) = 0.109
S = 1.05 5031 reflections 417 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0583P)2 + 0.1985P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.31 e Å−3
supporting information
sup-2 Acta Cryst. (2007). E63, o1899–o1901
Special details
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. 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)
x y z Uiso*/Ueq
O1A 0.64178 (15) 0.1975 (2) 0.27673 (7) 0.0252 (3) O2A 0.56408 (14) 0.2230 (2) 0.71930 (7) 0.0243 (3) C1A 0.71855 (18) 0.0051 (3) 0.49586 (9) 0.0188 (4) C2A 0.7384 (2) −0.1775 (3) 0.47064 (10) 0.0245 (4)
H2AB 0.8256 −0.2111 0.4846 0.029*
H2AC 0.6843 −0.2550 0.4911 0.029*
C3A 0.7092 (2) −0.1946 (3) 0.39523 (10) 0.0282 (5)
H3AA 0.7267 −0.3102 0.3825 0.034*
H3AB 0.6198 −0.1724 0.3814 0.034*
C4A 0.7876 (2) −0.0717 (3) 0.35991 (10) 0.0272 (5)
H4AA 0.7618 −0.0820 0.3124 0.033*
H4AB 0.8759 −0.1053 0.3690 0.033*
C5A 0.77639 (19) 0.1157 (3) 0.37974 (9) 0.0215 (4) C6A 0.79664 (18) 0.1295 (3) 0.45731 (9) 0.0185 (4)
H6AA 0.8847 0.0936 0.4702 0.022*
C7A 0.7930 (2) 0.3104 (3) 0.48440 (9) 0.0214 (4)
H7AA 0.7058 0.3479 0.4825 0.026*
H7AB 0.8361 0.3872 0.4576 0.026*
C8A 0.85853 (19) 0.3139 (3) 0.55675 (9) 0.0228 (4)
H8AA 0.9468 0.2825 0.5577 0.027*
H8AB 0.8559 0.4289 0.5738 0.027*
C9A 0.79720 (18) 0.1939 (3) 0.60212 (9) 0.0182 (4) C10A 0.77826 (18) 0.0143 (3) 0.57104 (9) 0.0189 (4)
H10A 0.8644 −0.0299 0.5717 0.023*
C11A 0.7173 (2) −0.1050 (3) 0.61833 (10) 0.0216 (4)
H11A 0.6794 −0.2005 0.5926 0.026*
H11B 0.7841 −0.1498 0.6510 0.026*
C12A 0.6157 (2) −0.0244 (3) 0.65542 (10) 0.0224 (4)
H12A 0.5366 −0.0160 0.6255 0.027*
H12B 0.6014 −0.0973 0.6922 0.027*
C13A 0.65476 (18) 0.1520 (3) 0.68184 (9) 0.0199 (4) C14A 0.67345 (18) 0.2646 (3) 0.62293 (9) 0.0193 (4)
H14A 0.6827 0.3832 0.6360 0.023*
C15A 0.87961 (18) 0.1803 (3) 0.67138 (9) 0.0225 (4)
H15A 0.9406 0.0885 0.6717 0.027*
H15B 0.9251 0.2857 0.6824 0.027*
C16A 0.78785 (19) 0.1451 (3) 0.72028 (10) 0.0205 (4) C17A 0.57506 (18) 0.0422 (3) 0.48618 (10) 0.0208 (4)
H17A 0.5378 0.0025 0.4432 0.031*
H17B 0.5615 0.1625 0.4893 0.031*
H17C 0.5365 −0.0154 0.5200 0.031*
C18A 0.8833 (2) 0.2151 (4) 0.35268 (10) 0.0286 (5)
H18A 0.8828 0.1887 0.3065 0.043*
H18B 0.9636 0.1835 0.3771 0.043*
H18C 0.8700 0.3350 0.3576 0.043*
C19A 0.65014 (19) 0.1916 (3) 0.34806 (9) 0.0243 (5)
H19A 0.5810 0.1235 0.3603 0.029*
H19B 0.6416 0.3058 0.3650 0.029*
C20A 0.8130 (2) 0.1195 (3) 0.78496 (10) 0.0235 (4)
H20A 0.8964 0.1220 0.8058 0.028*
H20B 0.7474 0.0989 0.8097 0.028*
O1B 0.39586 (16) 0.0197 (3) 0.77040 (8) 0.0302 (4) O2B 0.42173 (16) 0.0349 (2) 1.22463 (8) 0.0264 (3) C1B 0.27791 (18) 0.1997 (3) 0.97099 (9) 0.0176 (4) C2B 0.2448 (2) 0.3767 (3) 0.93981 (11) 0.0235 (4)
H2BB 0.1553 0.3982 0.9403 0.028*
H2BC 0.2918 0.4627 0.9672 0.028*
C3B 0.2741 (2) 0.3949 (3) 0.86863 (11) 0.0277 (5)
H3BA 0.2461 0.5059 0.8516 0.033*
H3BB 0.3650 0.3879 0.8686 0.033*
C4B 0.2091 (2) 0.2576 (3) 0.82328 (10) 0.0264 (5)
H4BA 0.2336 0.2710 0.7793 0.032*
H4BB 0.1181 0.2737 0.8194 0.032*
C5B 0.24126 (19) 0.0758 (3) 0.84777 (10) 0.0205 (4) C6B 0.21579 (18) 0.0623 (3) 0.92142 (9) 0.0178 (4)
H6BA 0.1248 0.0851 0.9188 0.021*
C7B 0.23072 (19) −0.1156 (3) 0.95164 (10) 0.0195 (4)
H7BA 0.3198 −0.1397 0.9653 0.023*
H7BB 0.1976 −0.1995 0.9188 0.023*
C8B 0.15885 (19) −0.1265 (3) 1.01184 (10) 0.0200 (4)
H8BA 0.0692 −0.1093 0.9972 0.024*
H8BB 0.1694 −0.2397 1.0308 0.024*
C9B 0.20387 (18) 0.0039 (3) 1.06539 (9) 0.0174 (4) C10B 0.21090 (18) 0.1844 (3) 1.03498 (9) 0.0175 (4)
H10B 0.1224 0.2149 1.0200 0.021*
C11B 0.2555 (2) 0.3148 (3) 1.09064 (10) 0.0229 (4)
H11C 0.2888 0.4138 1.0704 0.027*
H11D 0.1821 0.3514 1.1104 0.027*
C12B 0.3564 (2) 0.2517 (3) 1.14638 (10) 0.0234 (4)
H12C 0.4385 0.2529 1.1308 0.028*
supporting information
sup-4 Acta Cryst. (2007). E63, o1899–o1901
C13B 0.3288 (2) 0.0720 (3) 1.16926 (10) 0.0205 (4) C14B 0.32863 (18) −0.0466 (3) 1.10936 (9) 0.0181 (4)
H14C 0.3275 −0.1652 1.1225 0.022*
H14D 0.4016 −0.0264 1.0867 0.022*
C15B 0.11238 (19) 0.0094 (3) 1.11891 (9) 0.0230 (4)
H15C 0.0449 0.0909 1.1066 0.028*
H15D 0.0750 −0.1017 1.1237 0.028*
C16B 0.1920 (2) 0.0620 (3) 1.18283 (10) 0.0228 (4) C17B 0.42266 (18) 0.1852 (3) 0.98662 (10) 0.0219 (4)
H17D 0.4609 0.2301 0.9502 0.033*
H17E 0.4460 0.0679 0.9933 0.033*
H17F 0.4517 0.2486 1.0262 0.033*
C18B 0.1541 (2) −0.0497 (3) 0.80514 (10) 0.0262 (5)
H18D 0.1470 −0.0164 0.7593 0.039*
H18E 0.0717 −0.0488 0.8192 0.039*
H18F 0.1893 −0.1621 0.8103 0.039*
C19B 0.3788 (2) 0.0310 (3) 0.83892 (10) 0.0263 (5)
H19C 0.4353 0.1173 0.8605 0.032*
H19D 0.4014 −0.0769 0.8605 0.032*
C20B 0.1534 (3) 0.0917 (3) 1.24102 (11) 0.0318 (5)
H20C 0.0680 0.0806 1.2456 0.038*
H20D 0.2116 0.1237 1.2773 0.038*
H1AA 0.581 (3) 0.139 (5) 0.2623 (17) 0.057 (11)* H2AA 0.510 (3) 0.154 (5) 0.7321 (17) 0.062 (11)* H1BA 0.376 (3) −0.083 (5) 0.7555 (15) 0.044 (9)* H2BA 0.408 (3) −0.059 (5) 1.2357 (14) 0.037 (8)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C17A 0.0180 (9) 0.0262 (11) 0.0183 (8) −0.0027 (8) 0.0031 (7) −0.0042 (8) C18A 0.0223 (10) 0.0464 (15) 0.0177 (9) 0.0025 (10) 0.0045 (8) 0.0032 (10) C19A 0.0209 (9) 0.0368 (13) 0.0148 (8) 0.0044 (9) 0.0010 (7) −0.0009 (9) C20A 0.0250 (10) 0.0267 (12) 0.0189 (9) 0.0026 (9) 0.0033 (8) 0.0010 (8) O1B 0.0367 (9) 0.0330 (10) 0.0243 (7) −0.0005 (8) 0.0164 (7) −0.0006 (7) O2B 0.0304 (8) 0.0242 (9) 0.0216 (7) −0.0046 (7) −0.0070 (6) 0.0028 (7) C1B 0.0167 (9) 0.0191 (10) 0.0171 (8) −0.0003 (8) 0.0024 (7) 0.0014 (8) C2B 0.0267 (10) 0.0199 (11) 0.0234 (10) 0.0029 (9) 0.0012 (8) 0.0035 (8) C3B 0.0342 (12) 0.0245 (12) 0.0240 (10) 0.0019 (10) 0.0031 (9) 0.0088 (9) C4B 0.0298 (11) 0.0313 (12) 0.0187 (9) 0.0070 (10) 0.0051 (8) 0.0064 (9) C5B 0.0207 (9) 0.0253 (11) 0.0157 (8) 0.0045 (8) 0.0036 (7) 0.0024 (8) C6B 0.0154 (9) 0.0217 (11) 0.0170 (8) 0.0024 (8) 0.0044 (7) 0.0001 (8) C7B 0.0212 (9) 0.0202 (10) 0.0175 (9) −0.0006 (8) 0.0042 (7) −0.0027 (8) C8B 0.0227 (9) 0.0198 (11) 0.0180 (9) −0.0057 (8) 0.0044 (7) −0.0019 (8) C9B 0.0174 (9) 0.0190 (10) 0.0159 (8) −0.0019 (8) 0.0031 (7) −0.0021 (8) C10B 0.0180 (9) 0.0175 (10) 0.0171 (8) 0.0023 (8) 0.0030 (7) −0.0010 (7) C11B 0.0291 (11) 0.0191 (10) 0.0195 (9) −0.0005 (9) 0.0000 (8) −0.0023 (8) C12B 0.0283 (10) 0.0200 (11) 0.0203 (9) −0.0055 (9) −0.0021 (8) −0.0010 (8) C13B 0.0233 (10) 0.0208 (10) 0.0163 (8) −0.0016 (8) −0.0011 (7) −0.0013 (8) C14B 0.0181 (9) 0.0175 (10) 0.0182 (9) −0.0010 (8) 0.0007 (7) 0.0006 (8) C15B 0.0199 (9) 0.0297 (12) 0.0204 (9) −0.0016 (9) 0.0066 (7) −0.0011 (9) C16B 0.0286 (10) 0.0203 (11) 0.0199 (9) 0.0006 (9) 0.0043 (8) 0.0003 (8) C17B 0.0181 (9) 0.0234 (11) 0.0242 (9) −0.0026 (8) 0.0026 (7) 0.0045 (9) C18B 0.0268 (11) 0.0324 (13) 0.0188 (9) 0.0049 (9) 0.0011 (8) −0.0020 (9) C19B 0.0248 (10) 0.0360 (13) 0.0195 (9) 0.0064 (10) 0.0083 (8) 0.0025 (9) C20B 0.0433 (13) 0.0313 (13) 0.0223 (10) 0.0022 (11) 0.0095 (9) −0.0041 (9)
Geometric parameters (Å, º)
O1A—C19A 1.440 (2) O1B—C19B 1.431 (2)
O1A—H1AA 0.81 (4) O1B—H1BA 0.88 (4)
O2A—C13A 1.423 (2) O2B—C13B 1.422 (3)
O2A—H2AA 0.85 (4) O2B—H2BA 0.79 (3)
C1A—C17A 1.541 (3) C1B—C17B 1.535 (3)
C1A—C2A 1.548 (3) C1B—C2B 1.548 (3)
C1A—C6A 1.562 (3) C1B—C6B 1.561 (3)
C1A—C10A 1.573 (3) C1B—C10B 1.571 (3)
C2A—C3A 1.527 (3) C2B—C3B 1.527 (3)
C2A—H2AB 0.97 C2B—H2BB 0.97
C2A—H2AC 0.97 C2B—H2BC 0.97
C3A—C4A 1.519 (3) C3B—C4B 1.522 (4)
C3A—H3AA 0.97 C3B—H3BA 0.97
C3A—H3AB 0.97 C3B—H3BB 0.97
C4A—C5A 1.536 (4) C4B—C5B 1.536 (3)
C4A—H4AA 0.97 C4B—H4BA 0.97
C4A—H4AB 0.97 C4B—H4BB 0.97
C5A—C19A 1.530 (3) C5B—C18B 1.537 (3)
supporting information
sup-6 Acta Cryst. (2007). E63, o1899–o1901
C5A—C6A 1.565 (3) C5B—C6B 1.561 (3)
C6A—C7A 1.527 (3) C6B—C7B 1.526 (3)
C6A—H6AA 0.98 C6B—H6BA 0.98
C7A—C8A 1.538 (3) C7B—C8B 1.532 (3)
C7A—H7AA 0.97 C7B—H7BA 0.97
C7A—H7AB 0.97 C7B—H7BB 0.97
C8A—C9A 1.527 (3) C8B—C9B 1.523 (3)
C8A—H8AA 0.97 C8B—H8BA 0.97
C8A—H8AB 0.97 C8B—H8BB 0.97
C9A—C14A 1.542 (3) C9B—C14B 1.547 (3)
C9A—C10A 1.548 (3) C9B—C10B 1.553 (3)
C9A—C15A 1.556 (3) C9B—C15B 1.557 (3)
C10A—C11A 1.548 (3) C10B—C11B 1.551 (3)
C10A—H10A 0.98 C10B—H10B 0.98
C11A—C12A 1.538 (3) C11B—C12B 1.532 (3)
C11A—H11A 0.97 C11B—H11C 0.97
C11A—H11B 0.97 C11B—H11D 0.97
C12A—C13A 1.524 (3) C12B—C13B 1.528 (3)
C12A—H12A 0.97 C12B—H12C 0.97
C12A—H12B 0.97 C12B—H12D 0.97
C13A—C16A 1.522 (3) C13B—C16B 1.522 (3)
C13A—C14A 1.523 (3) C13B—C14B 1.533 (3)
C14A—H14A 0.97 C14B—H14C 0.97
C14A—H14B 0.97 C14B—H14D 0.97
C15A—C16A 1.512 (3) C15B—C16B 1.508 (3)
C15A—H15A 0.97 C15B—H15C 0.97
C15A—H15B 0.97 C15B—H15D 0.97
C16A—C20A 1.320 (3) C16B—C20B 1.325 (3)
C17A—H17A 0.96 C17B—H17D 0.96
C17A—H17B 0.96 C17B—H17E 0.96
C17A—H17C 0.96 C17B—H17F 0.96
C18A—H18A 0.96 C18B—H18D 0.96
C18A—H18B 0.96 C18B—H18E 0.96
C18A—H18C 0.96 C18B—H18F 0.96
C19A—H19A 0.97 C19B—H19C 0.97
C19A—H19B 0.97 C19B—H19D 0.97
C20A—H20A 0.93 C20B—H20C 0.93
C20A—H20B 0.93 C20B—H20D 0.93
C3A—C2A—H2AB 108.9 C3B—C2B—H2BB 108.7
C1A—C2A—H2AB 108.9 C1B—C2B—H2BB 108.7
C3A—C2A—H2AC 108.9 C3B—C2B—H2BC 108.7
C1A—C2A—H2AC 108.9 C1B—C2B—H2BC 108.7
H2AB—C2A—H2AC 107.7 H2BB—C2B—H2BC 107.6
C4A—C3A—C2A 111.65 (19) C4B—C3B—C2B 111.82 (19)
C4A—C3A—H3AA 109.3 C4B—C3B—H3BA 109.3
C2A—C3A—H3AA 109.3 C2B—C3B—H3BA 109.3
C4A—C3A—H3AB 109.3 C4B—C3B—H3BB 109.3
C2A—C3A—H3AB 109.3 C2B—C3B—H3BB 109.3
H3AA—C3A—H3AB 108.0 H3BA—C3B—H3BB 107.9
C3A—C4A—C5A 114.71 (17) C3B—C4B—C5B 113.62 (17)
C3A—C4A—H4AA 108.6 C3B—C4B—H4BA 108.8
C5A—C4A—H4AA 108.6 C5B—C4B—H4BA 108.8
C3A—C4A—H4AB 108.6 C3B—C4B—H4BB 108.8
C5A—C4A—H4AB 108.6 C5B—C4B—H4BB 108.8
H4AA—C4A—H4AB 107.6 H4BA—C4B—H4BB 107.7
C19A—C5A—C4A 111.05 (19) C4B—C5B—C18B 108.90 (17) C19A—C5A—C18A 107.55 (18) C4B—C5B—C19B 110.36 (19) C4A—C5A—C18A 107.74 (18) C18B—C5B—C19B 107.29 (18) C19A—C5A—C6A 112.83 (16) C4B—C5B—C6B 108.28 (17) C4A—C5A—C6A 109.01 (18) C18B—C5B—C6B 108.99 (17) C18A—C5A—C6A 108.51 (17) C19B—C5B—C6B 112.94 (16) C7A—C6A—C1A 111.13 (15) C7B—C6B—C5B 115.21 (17) C7A—C6A—C5A 114.88 (17) C7B—C6B—C1B 111.29 (16) C1A—C6A—C5A 116.91 (17) C5B—C6B—C1B 117.21 (17)
C7A—C6A—H6AA 104.0 C7B—C6B—H6BA 103.7
C1A—C6A—H6AA 104.0 C5B—C6B—H6BA 103.7
C5A—C6A—H6AA 104.0 C1B—C6B—H6BA 103.7
C6A—C7A—C8A 109.27 (18) C6B—C7B—C8B 109.67 (16)
C6A—C7A—H7AA 109.8 C6B—C7B—H7BA 109.7
C8A—C7A—H7AA 109.8 C8B—C7B—H7BA 109.7
C6A—C7A—H7AB 109.8 C6B—C7B—H7BB 109.7
C8A—C7A—H7AB 109.8 C8B—C7B—H7BB 109.7
H7AA—C7A—H7AB 108.3 H7BA—C7B—H7BB 108.2
C9A—C8A—C7A 113.00 (17) C9B—C8B—C7B 112.94 (16)
C9A—C8A—H8AA 109.0 C9B—C8B—H8BA 109.0
C7A—C8A—H8AA 109.0 C7B—C8B—H8BA 109.0
C9A—C8A—H8AB 109.0 C9B—C8B—H8BB 109.0
C7A—C8A—H8AB 109.0 C7B—C8B—H8BB 109.0
H8AA—C8A—H8AB 107.8 H8BA—C8B—H8BB 107.8
supporting information
sup-8 Acta Cryst. (2007). E63, o1899–o1901
C11A—C10A—C1A 115.27 (17) C11B—C10B—C1B 115.08 (17) C9A—C10A—C1A 116.76 (17) C9B—C10B—C1B 116.84 (16) C11A—C10A—H10A 104.4 C11B—C10B—H10B 104.5
C9A—C10A—H10A 104.4 C9B—C10B—H10B 104.5
C1A—C10A—H10A 104.4 C1B—C10B—H10B 104.5
C12A—C11A—C10A 115.99 (18) C12B—C11B—C10B 116.00 (19) C12A—C11A—H11A 108.3 C12B—C11B—H11C 108.3 C10A—C11A—H11A 108.3 C10B—C11B—H11C 108.3 C12A—C11A—H11B 108.3 C12B—C11B—H11D 108.3 C10A—C11A—H11B 108.3 C10B—C11B—H11D 108.3 H11A—C11A—H11B 107.4 H11C—C11B—H11D 107.4 C13A—C12A—C11A 111.75 (17) C13B—C12B—C11B 112.33 (18) C13A—C12A—H12A 109.3 C13B—C12B—H12C 109.1 C11A—C12A—H12A 109.3 C11B—C12B—H12C 109.1 C13A—C12A—H12B 109.3 C13B—C12B—H12D 109.1 C11A—C12A—H12B 109.3 C11B—C12B—H12D 109.1 H12A—C12A—H12B 107.9 H12C—C12B—H12D 107.9 O2A—C13A—C16A 113.08 (16) O2B—C13B—C16B 115.17 (17) O2A—C13A—C14A 111.33 (18) O2B—C13B—C12B 106.76 (17) C16A—C13A—C14A 102.17 (16) C16B—C13B—C12B 109.34 (18) O2A—C13A—C12A 111.87 (17) O2B—C13B—C14B 115.36 (18) C16A—C13A—C12A 109.76 (18) C16B—C13B—C14B 102.45 (16) C14A—C13A—C12A 108.12 (16) C12B—C13B—C14B 107.46 (16) C13A—C14A—C9A 102.40 (16) C13B—C14B—C9B 102.09 (16) C13A—C14A—H14A 111.3 C13B—C14B—H14C 111.4
C9A—C14A—H14A 111.3 C9B—C14B—H14C 111.4
C13A—C14A—H14B 111.3 C13B—C14B—H14D 111.4
C9A—C14A—H14B 111.3 C9B—C14B—H14D 111.4
H14A—C14A—H14B 109.2 H14C—C14B—H14D 109.2 C16A—C15A—C9A 105.76 (16) C16B—C15B—C9B 106.11 (16) C16A—C15A—H15A 110.6 C16B—C15B—H15C 110.5
C9A—C15A—H15A 110.6 C9B—C15B—H15C 110.5
C16A—C15A—H15B 110.6 C16B—C15B—H15D 110.5
C9A—C15A—H15B 110.6 C9B—C15B—H15D 110.5
H15A—C15A—H15B 108.7 H15C—C15B—H15D 108.7 C20A—C16A—C15A 128.39 (19) C20B—C16B—C15B 127.6 (2) C20A—C16A—C13A 124.30 (18) C20B—C16B—C13B 125.1 (2) C15A—C16A—C13A 107.26 (16) C15B—C16B—C13B 107.28 (16)
C1A—C17A—H17A 109.5 C1B—C17B—H17D 109.5
C1A—C17A—H17B 109.5 C1B—C17B—H17E 109.5
H17A—C17A—H17B 109.5 H17D—C17B—H17E 109.5
C1A—C17A—H17C 109.5 C1B—C17B—H17F 109.5
H17A—C17A—H17C 109.5 H17D—C17B—H17F 109.5 H17B—C17A—H17C 109.5 H17E—C17B—H17F 109.5
C5A—C18A—H18A 109.5 C5B—C18B—H18D 109.5
C5A—C18A—H18B 109.5 C5B—C18B—H18E 109.5
H18A—C18A—H18B 109.5 H18D—C18B—H18E 109.5
H18A—C18A—H18C 109.5 H18D—C18B—H18F 109.5 H18B—C18A—H18C 109.5 H18E—C18B—H18F 109.5 O1A—C19A—C5A 111.40 (16) O1B—C19B—C5B 112.21 (17)
O1A—C19A—H19A 109.3 O1B—C19B—H19C 109.2
C5A—C19A—H19A 109.3 C5B—C19B—H19C 109.2
O1A—C19A—H19B 109.3 O1B—C19B—H19D 109.2
C5A—C19A—H19B 109.3 C5B—C19B—H19D 109.2
H19A—C19A—H19B 108.0 H19C—C19B—H19D 107.9 C16A—C20A—H20A 120.0 C16B—C20B—H20C 120.0 C16A—C20A—H20B 120.0 C16B—C20B—H20D 120.0 H20A—C20A—H20B 120.0 H20C—C20B—H20D 120.0
supporting information
sup-10 Acta Cryst. (2007). E63, o1899–o1901
C2A—C1A—C10A—C9A 166.34 (16) C2B—C1B—C10B—C9B 166.07 (16) C6A—C1A—C10A—C9A 50.6 (2) C6B—C1B—C10B—C9B 50.8 (2) C9A—C10A—C11A—C12A 38.2 (2) C9B—C10B—C11B—C12B 37.4 (2) C1A—C10A—C11A—C12A −96.3 (2) C1B—C10B—C11B—C12B −97.0 (2) C10A—C11A—C12A—C13A −42.8 (2) C10B—C11B—C12B—C13B −43.0 (2) C11A—C12A—C13A—O2A −176.78 (17) C11B—C12B—C13B—O2B −174.73 (17) C11A—C12A—C13A—C16A −50.4 (2) C11B—C12B—C13B—C16B −49.5 (2) C11A—C12A—C13A—C14A 60.3 (2) C11B—C12B—C13B—C14B 61.0 (2) O2A—C13A—C14A—C9A 164.88 (16) O2B—C13B—C14B—C9B 169.23 (17) C16A—C13A—C14A—C9A 43.90 (19) C16B—C13B—C14B—C9B 43.30 (19) C12A—C13A—C14A—C9A −71.85 (19) C12B—C13B—C14B—C9B −71.85 (19) C8A—C9A—C14A—C13A −163.74 (16) C8B—C9B—C14B—C13B −163.31 (16) C10A—C9A—C14A—C13A 69.79 (19) C10B—C9B—C14B—C13B 69.69 (19) C15A—C9A—C14A—C13A −45.92 (19) C15B—C9B—C14B—C13B −45.50 (19) C8A—C9A—C15A—C16A 150.37 (19) C8B—C9B—C15B—C16B 150.98 (18) C14A—C9A—C15A—C16A 30.6 (2) C14B—C9B—C15B—C16B 31.0 (2) C10A—C9A—C15A—C16A −86.92 (19) C10B—C9B—C15B—C16B −86.9 (2) C9A—C15A—C16A—C20A 178.2 (2) C9B—C15B—C16B—C20B 176.3 (2) C9A—C15A—C16A—C13A −4.4 (2) C9B—C15B—C16B—C13B −4.9 (2) O2A—C13A—C16A—C20A 33.5 (3) O2B—C13B—C16B—C20B 29.1 (3) C14A—C13A—C16A—C20A 153.3 (2) C12B—C13B—C16B—C20B −91.0 (3) C12A—C13A—C16A—C20A −92.2 (3) C14B—C13B—C16B—C20B 155.2 (2) O2A—C13A—C16A—C15A −144.01 (19) O2B—C13B—C16B—C15B −149.72 (19) C14A—C13A—C16A—C15A −24.2 (2) C12B—C13B—C16B—C15B 90.1 (2) C12A—C13A—C16A—C15A 90.3 (2) C14B—C13B—C16B—C15B −23.7 (2) C4A—C5A—C19A—O1A −65.0 (2) C4B—C5B—C19B—O1B −67.2 (2) C18A—C5A—C19A—O1A 52.7 (2) C18B—C5B—C19B—O1B 51.3 (3) C6A—C5A—C19A—O1A 172.30 (19) C6B—C5B—C19B—O1B 171.42 (19)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1A—H1AA···O2Bi 0.81 (3) 1.94 (3) 2.750 (2) 171 (4)
O2A—H2AA···O1B 0.86 (4) 1.86 (4) 2.711 (2) 172 (3) O1B—H1BA···O1Aii 0.88 (4) 1.85 (4) 2.718 (3) 172 (3)
O2B—H2BA···O2Aiii 0.79 (4) 1.95 (4) 2.699 (2) 159 (3)
