organic papers
o532
Shi-Ping Yanget al. 2C23H22O6C2H4O2 DOI: 10.1107/S1600536804004817 Acta Cryst.(2004). E60, o532±o534 Acta Crystallographica Section EStructure Reports
Online ISSN 1600-5368
Rotenone±acetic acid (2/1)
Shi-Ping Yang,a* Hong-Mei
Chen,aFan Zhang,aQiong-Qiong
Chen,aXi-Bin Yu,aJi-Guang
Huangband Han-Hong Xub
aSchool of Chemistry, Shanghai Teachers'
University, Shanghai 200234, People's Republic of China, andbLaboratory of Insect Toxicology,
South China Agricultural University, Guangzhou 510642, People's Republic of China
Correspondence e-mail: shipingy@shtu.edu.cn
Key indicators Single-crystal X-ray study T= 293 K
Mean(C±C) = 0.007 AÊ Rfactor = 0.060 wRfactor = 0.146 Data-to-parameter ratio = 8.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The structure determination of the title compound, a 2:1 adduct of rotenone and acetic acid, 2C23H22O6C2H4O2,
con®rms that the rotenone molecule has an approximately V-shaped structure.
Comment
Rotenone is a naturally occurring heterocyclic compound widely used as an insecticide. It exerts its effects mainly by blocking oxidative phosphorylation and/or mitosis in cells through apparently separate pathways (Lof¯er & Schneider, 1982). Information on the mode of action and selectivity of rotenone is important so that the compound may be used safely and ef®ciently. The three-dimensional structure of most biologically active molecules plays a role in governing their interactions and activities. Thus, in the course of a systematic study of the relation between the structure and bioactivity of rotenone, we have isolated the 2:1 adduct of rotenone and acetic acid, (I), and report here its preparation and structure.
Received 30 January 2004 Accepted 2 March 2004 Online 13 March 2004
Figure 1
The X-ray diffraction analysis of (I) shows that there are two rotenone molecules and one acetic acid molecule in the asymmetric unit, as shown in Fig. 1. The distances and angles within the two rotenone molecules agree with those of related molecules (Begleyet al., 1989, 1993).
The two rotenone molecules in (I) are very similar, with two nearly ¯at regions (rings I and II, and rings III, IV and V). In each rotenone molecule, ring II can be regarded as having an envelope conformation, whereas ring III adopts a 1,2-diplanar conformation (Bucourt, 1974), as indicated by the torsion angles (Table 1). The torsion angles in the ®ve-membered ring V (Table 1) indicate an envelope conformation (Bucourt, 1974), with the isopropenyl group equatorial, as proposed earlier (BuÈchiet al., 1961; Carlsonet al., 1973).
Except for the isopropenyl group, the non-H atoms of (I) lie close to the plane of aromatic rings I and IV, resulting in an approximately V-shaped molecule, with dihedral angles of
74.7 (1) and 74.8 (1) between rings I and IV in the two
molecules.
The acetic acid molecule is linked through OÐH O
hydrogen bonding to one of the rotenone molecules (Table 2). The packing of the molecules is governed by weak van der Waals interactions.
Experimental
Rotenone (5 g) in ethanoic acid (50 ml) was re¯uxed for 2 h. After cooling and ®ltration, the solution was allowed to stand in air at room temperature for two months, after which time a single crystal was obtained suitable for X-ray analysis.
Crystal data
2C23H22O6C2H4O2
Mr= 848.86
Monoclinic,P21
a= 9.1356 (16) AÊ
b= 15.359 (3) AÊ
c= 15.082 (3) AÊ
= 92.652 (4)
V= 2113.9 (7) AÊ3
Z= 2
Dx= 1.334 Mg mÿ3
MoKradiation Cell parameters from 2045
re¯ections
= 5.1±39.9 = 0.10 mmÿ1
T= 293 (2) K Block, colourless 0.510.200.06 mm
Data collection
Bruker SMART CCD area-detector diffractometer
'and!scans
Absorption correction: multi-scan (SADABS; Bruker, 1998)
Tmin= 0.952,Tmax= 0.994
12 858 measured re¯ections
5099 independent re¯ections 3945 re¯ections withI> 2(I)
Rint= 0.052 max= 28.3
h=ÿ11!12
k=ÿ20!10
l=ÿ19!19
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.060
wR(F2) = 0.146
S= 0.95 5099 re¯ections 566 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0596P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.009 max= 0.39 e AÊÿ3 min=ÿ0.31 e AÊÿ3
Table 1
Selected torsion angles ().
O3ÐC5ÐC6ÐC7 ÿ0.6 (6)
C5ÐC6ÐC7ÐC8 13.9 (6)
C6ÐC7ÐC8ÐC9 ÿ41.7 (5)
C7ÐC8ÐC9ÐO3 59.9 (5)
C8ÐC9ÐO3ÐC5 ÿ46.6 (5)
C9ÐO3ÐC5ÐC6 17.1 (6)
O2ÐC8ÐC7ÐC10 ÿ49.9 (5)
C8ÐC7ÐC10ÐC11 27.0 (5)
C7ÐC10ÐC11ÐC12 ÿ0.4 (6) C10ÐC11ÐC12ÐO2 ÿ4.9 (6) C11ÐC12ÐO2ÐC8 ÿ18.7 (5)
C12ÐO2ÐC8ÐC7 46.5 (5)
O9ÐC28ÐC29ÐC30 ÿ0.6 (7) C28ÐC29ÐC30ÐC31 15.1 (6) C29ÐC30ÐC31ÐC32 ÿ42.4 (5) C30ÐC31ÐC32ÐO9 58.0 (5) C31ÐC32ÐO9ÐC28 ÿ43.5 (5)
C32ÐO9ÐC28ÐC29 15.2 (6) O8ÐC30ÐC31ÐC33 50.1 (5) C30ÐC31ÐC33ÐC34 ÿ152.5 (5) C31ÐC33ÐC34ÐC35 9.9 (4) C33ÐC34ÐC35ÐO8 1.7 (6) C34ÐC35ÐO8ÐC30 2.1 (4) C35ÐO8ÐC30ÐC31 ÿ139.4 (4) O4ÐC13ÐC14ÐC17 ÿ0.9 (6) C13ÐC14ÐC17ÐC18 167.0 (5)
C14ÐC7ÐC18ÐO4 0.9 (2)
C7ÐC18ÐO4ÐC13 5.85 (13)
C18ÐO4ÐC13ÐC14 ÿ168.3 (5) O10ÐC36ÐC37ÐC40 1.0 (6) C36ÐC37ÐC38ÐC39 ÿ0.4 (8) C37ÐC38ÐC39ÐO10 0.6 (4) C38ÐC39ÐO10ÐC36 ÿ179.4 (8) C39ÐO10ÐC36ÐC37 0.7 (4)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O13ÐH13 O7 0.82 2.01 2.776 (7) 155
Owing to the lack of atoms heavier than O, the absolute con®g-uration of (I) could not be determined by X-ray analysis and the Friedel pairs were merged. The con®guration was then assigned on the basis of the con®guration of the starting rotenone (Rossiet al., 1988). All H atoms were positioned geometrically and re®ned using a riding model.
Data collection:SMART(Bruker, 1998); cell re®nement:SMART; data reduction:SAINT (Bruker, 1998) andSHELXTL (Sheldrick, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3 for Windows(Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication:SHELXTL.
We acknowledge ®nancial support from the NSFC (grant No. 30100118) and the Science Grant of SHTU (grant No. 870).
Figure 2
organic papers
o534
Shi-Ping Yanget al. 2C23H22O6C2H4O2 Acta Cryst.(2004). E60, o532±o534References
Begley, M. J., Crombie, L., Hadi, A. H. bin A. & Josephs, J. L. (1989).J. Chem. Soc. Perkin Trans.1, pp. 204±208.
Begley, M. J., Crombie, L., Hadi, A. H. bin A. & Josephs, J. L. (1993).J. Chem. Soc. Perkin Trans.1, pp. 2605±2609.
Bruker (1998).SMART(Version 5.0),SAINT (Version 4.0) andSADABS
(Version 2.0). Bruker AXS Inc., Madison, Wisconsin, USA.
BuÈchi, G., Crombie, L., Godin, P. J., Kaltenbronn, J. S., Siddalingaiah, K. S. & Whiting, D. A. (1961).J. Chem. Soc.pp. 2843±2860.
Bucourt, R. (1974).Top. Stereochem.8, 159±175.
Carlson, D. G., Weisleder, D. & Tallent, W. H. (1973).Tetrahedron,29, 2731± 2735.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Lof¯er, M. & Schneider, F. (1982).Mol. Cell. Biochem.48, 77±90.
Rossi, M., Fule, P. Z. & Taylor, M. R. (1988). Bioorg. Chem. 16, 376± 387.
Sheldrick, G. M. (1995).SHELXTL.Version 5.0. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
supporting information
Acta Cryst. (2004). E60, o532–o534 [https://doi.org/10.1107/S1600536804004817]
Rotenone
–
acetic acid (2/1)
Shi-Ping Yang, Hong-Mei Chen, Fan Zhang, Qiong-Qiong Chen, Xi-Bin Yu, Ji-Guang Huang and
Han-Hong Xu
Rotenone–acetic acid (2/1)
Crystal data
2C23H22O6·C2H4O2
Mr = 848.86 Monoclinic, P21
Hall symbol: P 2yb a = 9.1356 (16) Å b = 15.359 (3) Å c = 15.082 (3) Å β = 92.652 (4)° V = 2113.9 (7) Å3
Z = 2
F(000) = 896 Dx = 1.334 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2045 reflections θ = 5.1–39.9°
µ = 0.10 mm−1
T = 293 K Block, colourless 0.51 × 0.20 × 0.06 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 1998) Tmin = 0.952, Tmax = 0.994
12858 measured reflections 5099 independent reflections 3945 reflections with I > 2σ(I) Rint = 0.052
θmax = 28.3°, θmin = 1.9°
h = −11→12 k = −20→10 l = −19→19
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.060
wR(F2) = 0.146
S = 0.95 5048 reflections 566 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-atom parameters constrained w = 1/[σ2(F
o2) + (0.0596P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.009
Δρmax = 0.39 e Å−3
Δρmin = −0.31 e Å−3
Special details
supporting information
sup-2 Acta Cryst. (2004). E60, o532–o534
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
O1 0.9153 (5) 0.0213 (2) 0.3699 (2) 0.0682 (11) O2 0.8380 (3) 0.27909 (19) 0.31431 (19) 0.0455 (8) O3 0.8033 (3) 0.33043 (19) 0.4907 (2) 0.0474 (8) O4 1.1258 (4) 0.2753 (2) 0.0722 (2) 0.0587 (9) O5 1.1954 (4) 0.1033 (2) 0.6567 (2) 0.0584 (9) O6 1.1735 (4) 0.2630 (2) 0.7136 (2) 0.0611 (10) O7 0.6209 (4) 0.1117 (2) 0.6224 (2) 0.0603 (9) O8 0.6269 (3) −0.1255 (2) 0.49791 (19) 0.0452 (7) O9 0.7096 (3) −0.22307 (19) 0.6511 (2) 0.0503 (8) O10 0.2809 (4) −0.0438 (3) 0.2837 (2) 0.0651 (10) O11 0.3899 (4) −0.0374 (3) 0.8873 (3) 0.0746 (11) O12 0.4032 (4) −0.2048 (2) 0.8978 (2) 0.0693 (11) O13 0.7921 (8) 0.1707 (4) 0.7670 (5) 0.155 (3)
H13 0.7511 0.1390 0.7298 0.233*
O14 0.9080 (9) 0.0560 (5) 0.7822 (5) 0.170 (3) C1 1.0108 (5) 0.1297 (3) 0.5387 (3) 0.0421 (10)
H1 1.0204 0.0730 0.5180 0.051*
C2 1.0959 (5) 0.1561 (3) 0.6102 (3) 0.0431 (11) C3 1.0854 (5) 0.2418 (3) 0.6400 (3) 0.0459 (12) C4 0.9863 (5) 0.2978 (3) 0.5990 (3) 0.0435 (11)
H4 0.9778 0.3547 0.6191 0.052*
C5 0.8989 (4) 0.2687 (3) 0.5274 (3) 0.0392 (10) C6 0.9094 (5) 0.1853 (3) 0.4954 (3) 0.0409 (11) C7 0.8127 (5) 0.1555 (3) 0.4164 (3) 0.0418 (11)
H7 0.7344 0.1199 0.4399 0.050*
C8 0.7405 (5) 0.2315 (3) 0.3692 (3) 0.0429 (11)
H8 0.6569 0.2103 0.3322 0.051*
C9 0.6873 (5) 0.2966 (3) 0.4343 (3) 0.0485 (12)
H9A 0.6396 0.3443 0.4022 0.058*
H9B 0.6152 0.2693 0.4705 0.058*
C10 0.8949 (5) 0.0982 (3) 0.3538 (3) 0.0465 (12) C11 0.9482 (5) 0.1421 (3) 0.2749 (3) 0.0395 (10) C12 0.9214 (5) 0.2304 (3) 0.2613 (3) 0.0373 (10) C13 0.9852 (5) 0.2728 (3) 0.1928 (3) 0.0418 (10) C14 1.0712 (5) 0.2259 (3) 0.1371 (3) 0.0481 (12) C15 1.0980 (6) 0.1383 (3) 0.1470 (3) 0.0579 (14)
H15 1.1563 0.1082 0.1084 0.069*
C16 1.0351 (5) 0.0972 (3) 0.2164 (3) 0.0528 (13)
H16 1.0507 0.0378 0.2247 0.063*
H17A 0.9985 0.4057 0.2102 0.064*
H17B 0.8831 0.3788 0.1335 0.064*
C18 1.1001 (6) 0.3669 (3) 0.0942 (3) 0.0546 (13)
H18 1.1894 0.3908 0.1234 0.065*
C19 1.0670 (6) 0.4164 (3) 0.0102 (3) 0.0560 (13) C20 0.9266 (7) 0.4032 (5) −0.0367 (4) 0.093 (2)
H20A 0.9272 0.4310 −0.0937 0.140*
H20B 0.8504 0.4280 −0.0029 0.140*
H20C 0.9093 0.3420 −0.0444 0.140*
C21 1.1675 (8) 0.4707 (5) −0.0174 (5) 0.098 (2)
H21A 1.1497 0.5027 −0.0691 0.117*
H21B 1.2561 0.4769 0.0150 0.117*
C22 1.1848 (6) 0.0131 (3) 0.6392 (4) 0.0569 (13)
H22A 1.0854 −0.0056 0.6449 0.085*
H22B 1.2477 −0.0181 0.6809 0.085*
H22C 1.2141 0.0016 0.5801 0.085*
C23 1.1554 (7) 0.3471 (4) 0.7485 (4) 0.089 (2)
H23A 1.1807 0.3896 0.7051 0.133*
H23B 1.2179 0.3540 0.8009 0.133*
H23C 1.0551 0.3551 0.7632 0.133*
C24 0.5445 (5) −0.0350 (3) 0.7596 (3) 0.0460 (12)
H24 0.5372 0.0253 0.7547 0.055*
C25 0.4739 (5) −0.0772 (3) 0.8255 (3) 0.0504 (12) C26 0.4799 (5) −0.1672 (4) 0.8319 (3) 0.0505 (13) C27 0.5627 (5) −0.2134 (3) 0.7738 (3) 0.0453 (11)
H27 0.5709 −0.2735 0.7791 0.054*
C28 0.6341 (5) −0.1696 (3) 0.7072 (3) 0.0393 (11) C29 0.6271 (5) −0.0813 (3) 0.6998 (3) 0.0411 (11) C30 0.7061 (5) −0.0344 (3) 0.6270 (3) 0.0426 (11)
H30 0.7962 −0.0097 0.6544 0.051*
C31 0.7511 (5) −0.0987 (3) 0.5562 (3) 0.0451 (11)
H31 0.8256 −0.0717 0.5204 0.054*
C32 0.8122 (5) −0.1817 (3) 0.5968 (3) 0.0516 (13)
H32A 0.8380 −0.2212 0.5498 0.062*
H32B 0.9007 −0.1685 0.6322 0.062*
C33 0.6176 (5) 0.0400 (3) 0.5878 (3) 0.0465 (12) C34 0.5262 (5) 0.0206 (3) 0.5075 (3) 0.0416 (11) C35 0.5385 (5) −0.0605 (3) 0.4675 (3) 0.0398 (10) C36 0.4521 (5) −0.0796 (3) 0.3917 (3) 0.0444 (11) C37 0.3572 (5) −0.0167 (3) 0.3587 (3) 0.0517 (13) C38 0.3425 (6) 0.0647 (4) 0.3960 (4) 0.0626 (15)
H38 0.2774 0.1057 0.3716 0.075*
C39 0.4277 (5) 0.0821 (3) 0.4703 (3) 0.0509 (12)
H39 0.4205 0.1363 0.4972 0.061*
C40 0.4385 (6) −0.1592 (3) 0.3343 (3) 0.0522 (12)
H40A 0.3892 −0.2060 0.3640 0.063*
H40B 0.5336 −0.1793 0.3168 0.063*
supporting information
sup-4 Acta Cryst. (2004). E60, o532–o534
H41 0.2669 −0.1667 0.2401 0.069*
C42 0.4296 (7) −0.1102 (5) 0.1741 (4) 0.0754 (17) C43 0.4633 (10) −0.0320 (6) 0.1476 (6) 0.131 (3)
H43A 0.4345 0.0164 0.1794 0.157*
H43B 0.5162 −0.0248 0.0968 0.157*
C44 0.4748 (9) −0.1916 (6) 0.1281 (5) 0.120 (3)
H44A 0.5352 −0.1769 0.0799 0.180*
H44B 0.3891 −0.2220 0.1055 0.180*
H44C 0.5289 −0.2283 0.1695 0.180*
C45 0.3868 (8) 0.0541 (4) 0.8858 (5) 0.095 (2)
H45A 0.4846 0.0762 0.8949 0.142*
H45B 0.3273 0.0749 0.9321 0.142*
H45C 0.3463 0.0736 0.8294 0.142*
C46 0.4079 (8) −0.2962 (4) 0.9069 (4) 0.091 (2)
H46A 0.3781 −0.3229 0.8514 0.137*
H46B 0.3428 −0.3139 0.9517 0.137*
H46C 0.5060 −0.3140 0.9238 0.137*
C47 0.8792 (10) 0.1287 (5) 0.8118 (7) 0.112 (3) C48 0.9771 (12) 0.1576 (6) 0.8839 (6) 0.154 (4)
H48A 1.0500 0.1956 0.8612 0.231*
H48B 1.0241 0.1081 0.9117 0.231*
H48C 0.9223 0.1884 0.9268 0.231*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C9 0.037 (2) 0.059 (3) 0.049 (3) 0.006 (2) 0.003 (2) 0.009 (2) C10 0.051 (3) 0.045 (3) 0.043 (3) −0.006 (2) −0.010 (2) −0.001 (2) C11 0.043 (2) 0.036 (2) 0.039 (2) 0.000 (2) −0.013 (2) −0.0058 (19) C12 0.040 (2) 0.037 (2) 0.034 (2) 0.005 (2) −0.008 (2) −0.0041 (19) C13 0.050 (3) 0.038 (2) 0.037 (2) 0.007 (2) −0.003 (2) 0.000 (2) C14 0.056 (3) 0.051 (3) 0.037 (3) 0.008 (2) −0.003 (2) −0.002 (2) C15 0.073 (4) 0.055 (3) 0.045 (3) 0.016 (3) 0.001 (3) −0.010 (3) C16 0.073 (3) 0.038 (3) 0.046 (3) 0.007 (3) −0.010 (3) −0.003 (2) C17 0.075 (3) 0.043 (3) 0.043 (3) 0.009 (3) 0.010 (2) −0.001 (2) C18 0.071 (3) 0.051 (3) 0.042 (3) 0.001 (3) 0.005 (2) 0.002 (2) C19 0.072 (3) 0.055 (3) 0.042 (3) 0.008 (3) 0.012 (3) 0.009 (2) C20 0.105 (5) 0.118 (6) 0.056 (4) 0.005 (5) −0.014 (4) 0.013 (4) C21 0.101 (5) 0.118 (6) 0.075 (5) −0.013 (5) 0.020 (4) 0.040 (4) C22 0.060 (3) 0.049 (3) 0.061 (3) 0.009 (3) −0.004 (3) 0.011 (3) C23 0.107 (5) 0.073 (4) 0.082 (4) 0.017 (4) −0.037 (4) −0.030 (3) C24 0.052 (3) 0.046 (3) 0.040 (3) 0.004 (2) 0.002 (2) −0.003 (2) C25 0.053 (3) 0.059 (3) 0.040 (3) 0.002 (3) 0.005 (2) −0.008 (2) C26 0.048 (3) 0.069 (4) 0.035 (3) −0.007 (3) −0.003 (2) 0.002 (2) C27 0.048 (3) 0.048 (3) 0.038 (2) −0.004 (2) −0.009 (2) 0.003 (2) C28 0.038 (2) 0.043 (3) 0.036 (2) 0.003 (2) −0.005 (2) 0.003 (2) C29 0.036 (2) 0.047 (3) 0.040 (3) −0.003 (2) −0.002 (2) 0.002 (2) C30 0.038 (2) 0.046 (3) 0.044 (3) −0.006 (2) 0.000 (2) 0.003 (2) C31 0.038 (2) 0.054 (3) 0.043 (3) −0.002 (2) 0.005 (2) 0.006 (2) C32 0.043 (3) 0.065 (3) 0.046 (3) 0.014 (2) 0.000 (2) 0.003 (2) C33 0.047 (3) 0.044 (3) 0.050 (3) −0.010 (2) 0.013 (2) 0.004 (2) C34 0.041 (2) 0.037 (2) 0.047 (3) −0.002 (2) 0.005 (2) 0.008 (2) C35 0.039 (2) 0.036 (2) 0.044 (3) −0.001 (2) 0.011 (2) 0.010 (2) C36 0.044 (3) 0.050 (3) 0.039 (2) 0.001 (2) 0.002 (2) 0.011 (2) C37 0.045 (3) 0.056 (3) 0.053 (3) 0.001 (2) −0.004 (2) 0.014 (3) C38 0.054 (3) 0.049 (3) 0.084 (4) 0.013 (3) −0.010 (3) 0.020 (3) C39 0.052 (3) 0.045 (3) 0.056 (3) 0.003 (2) 0.005 (2) 0.006 (2) C40 0.058 (3) 0.055 (3) 0.043 (3) 0.009 (3) 0.004 (2) 0.004 (2) C41 0.055 (3) 0.072 (4) 0.046 (3) 0.002 (3) −0.006 (2) 0.003 (3) C42 0.071 (4) 0.095 (5) 0.058 (4) 0.008 (4) −0.008 (3) 0.009 (4) C43 0.153 (8) 0.138 (8) 0.107 (7) 0.032 (7) 0.050 (6) 0.058 (6) C44 0.115 (6) 0.172 (8) 0.073 (5) −0.009 (6) 0.006 (4) −0.056 (5) C45 0.111 (5) 0.092 (5) 0.083 (5) 0.014 (4) 0.035 (4) −0.036 (4) C46 0.131 (6) 0.082 (5) 0.062 (4) −0.030 (4) 0.026 (4) 0.011 (4) C47 0.114 (6) 0.043 (4) 0.177 (10) −0.004 (4) −0.021 (6) 0.035 (5) C48 0.221 (11) 0.126 (8) 0.109 (7) −0.052 (8) −0.059 (8) 0.008 (6)
Geometric parameters (Å, º)
O1—C10 1.219 (5) C20—H20B 0.9600
O2—C12 1.355 (5) C20—H20C 0.9600
O2—C8 1.444 (5) C21—H21A 0.9300
O3—C5 1.387 (5) C21—H21B 0.9300
supporting information
sup-6 Acta Cryst. (2004). E60, o532–o534
O4—C14 1.351 (6) C22—H22B 0.9600
O4—C18 1.467 (6) C22—H22C 0.9600
O5—C2 1.384 (5) C23—H23A 0.9600
O5—C22 1.413 (6) C23—H23B 0.9600
O6—C3 1.379 (5) C23—H23C 0.9600
O6—C23 1.407 (6) C24—C25 1.373 (7)
O7—C33 1.218 (5) C24—C29 1.398 (6)
O8—C35 1.350 (5) C24—H24 0.9300
O8—C31 1.461 (5) C25—C26 1.386 (7)
O9—C28 1.385 (5) C26—C27 1.380 (7)
O9—C32 1.423 (6) C27—C28 1.396 (6)
O10—C37 1.366 (6) C27—H27 0.9300
O10—C41 1.457 (7) C28—C29 1.362 (6)
O11—C25 1.378 (6) C29—C30 1.522 (6)
O11—C45 1.405 (7) C30—C33 1.505 (6)
O12—C26 1.370 (6) C30—C31 1.526 (6)
O12—C46 1.411 (7) C30—H30 0.9800
O13—C47 1.207 (8) C31—C32 1.510 (6)
O13—H13 0.8200 C31—H31 0.9800
O14—C47 1.236 (10) C32—H32A 0.9700
C1—C2 1.361 (6) C32—H32B 0.9700
C1—C6 1.400 (6) C33—C34 1.469 (6)
C1—H1 0.9300 C34—C35 1.391 (6)
C2—C3 1.396 (7) C34—C39 1.404 (6)
C3—C4 1.375 (6) C35—C36 1.390 (6)
C4—C5 1.387 (6) C36—C37 1.376 (6)
C4—H4 0.9300 C36—C40 1.499 (7)
C5—C6 1.373 (6) C37—C38 1.381 (7)
C6—C7 1.520 (6) C38—C39 1.361 (7)
C7—C8 1.503 (6) C38—H38 0.9300
C7—C10 1.516 (7) C39—H39 0.9300
C7—H7 0.9800 C40—C41 1.533 (6)
C8—C9 1.498 (7) C40—H40A 0.9700
C8—H8 0.9800 C40—H40B 0.9700
C9—H9A 0.9700 C41—C42 1.481 (8)
C9—H9B 0.9700 C41—H41 0.9800
C10—C11 1.469 (6) C42—C43 1.307 (10)
C11—C12 1.391 (6) C42—C44 1.498 (10)
C11—C16 1.396 (6) C43—H43A 0.9300
C12—C13 1.373 (6) C43—H43B 0.9300
C13—C14 1.380 (6) C44—H44A 0.9600
C13—C17 1.496 (7) C44—H44B 0.9600
C14—C15 1.375 (7) C44—H44C 0.9600
C15—C16 1.371 (7) C45—H45A 0.9600
C15—H15 0.9300 C45—H45B 0.9600
C16—H16 0.9300 C45—H45C 0.9600
C17—C18 1.544 (7) C46—H46A 0.9600
C17—H17B 0.9700 C46—H46C 0.9600
C18—C19 1.497 (7) C47—C48 1.446 (11)
C18—H18 0.9800 C48—H48A 0.9600
C19—C21 1.322 (8) C48—H48B 0.9600
C19—C20 1.449 (7) C48—H48C 0.9600
C20—H20A 0.9600
C12—O2—C8 116.0 (3) H23B—C23—H23C 109.5
C5—O3—C9 115.2 (3) C25—C24—C29 120.8 (5)
C14—O4—C18 107.9 (4) C25—C24—H24 119.6
C2—O5—C22 116.2 (4) C29—C24—H24 119.6
C3—O6—C23 116.3 (4) C24—C25—O11 125.1 (5)
C35—O8—C31 115.6 (3) C24—C25—C26 120.2 (5) C28—O9—C32 116.5 (3) O11—C25—C26 114.7 (5) C37—O10—C41 108.2 (4) O12—C26—C27 123.9 (5) C25—O11—C45 116.4 (5) O12—C26—C25 116.8 (5) C26—O12—C46 118.4 (5) C27—C26—C25 119.3 (5)
C47—O13—H13 109.5 C26—C27—C28 119.9 (4)
C2—C1—C6 121.9 (4) C26—C27—H27 120.1
C2—C1—H1 119.1 C28—C27—H27 120.1
C6—C1—H1 119.1 C29—C28—O9 124.2 (4)
C1—C2—O5 124.4 (4) C29—C28—C27 121.1 (5)
C1—C2—C3 119.4 (4) O9—C28—C27 114.6 (4)
O5—C2—C3 116.2 (4) C28—C29—C24 118.6 (5)
C4—C3—O6 124.2 (4) C28—C29—C30 120.6 (4)
C4—C3—C2 119.8 (4) C24—C29—C30 120.8 (4)
O6—C3—C2 115.9 (4) C33—C30—C29 112.3 (4)
C3—C4—C5 119.5 (4) C33—C30—C31 111.9 (4)
C3—C4—H4 120.2 C29—C30—C31 110.5 (4)
C5—C4—H4 120.2 C33—C30—H30 107.3
C6—C5—O3 123.4 (4) C29—C30—H30 107.3
C6—C5—C4 121.8 (4) C31—C30—H30 107.3
O3—C5—C4 114.8 (4) O8—C31—C32 105.5 (4)
C5—C6—C1 117.5 (4) O8—C31—C30 112.1 (3)
C5—C6—C7 120.6 (4) C32—C31—C30 111.7 (4)
C1—C6—C7 121.9 (4) O8—C31—H31 109.1
C8—C7—C10 112.0 (4) C32—C31—H31 109.1
C8—C7—C6 111.3 (4) C30—C31—H31 109.1
C10—C7—C6 112.1 (4) O9—C32—C31 111.7 (4)
C8—C7—H7 107.0 O9—C32—H32A 109.3
C10—C7—H7 107.0 C31—C32—H32A 109.3
C6—C7—H7 107.0 O9—C32—H32B 109.3
O2—C8—C9 105.4 (4) C31—C32—H32B 109.3
O2—C8—C7 113.3 (3) H32A—C32—H32B 107.9
C9—C8—C7 110.9 (4) O7—C33—C34 122.6 (4)
O2—C8—H8 109.1 O7—C33—C30 121.0 (4)
C9—C8—H8 109.1 C34—C33—C30 116.3 (4)
supporting information
sup-8 Acta Cryst. (2004). E60, o532–o534
O3—C9—C8 112.3 (3) C35—C34—C33 119.1 (4)
O3—C9—H9A 109.1 C39—C34—C33 121.5 (4)
C8—C9—H9A 109.1 O8—C35—C36 115.6 (4)
O3—C9—H9B 109.1 O8—C35—C34 125.0 (4)
C8—C9—H9B 109.1 C36—C35—C34 119.4 (4)
H9A—C9—H9B 107.9 C37—C36—C35 118.3 (5)
O1—C10—C11 123.6 (5) C37—C36—C40 109.2 (4)
O1—C10—C7 120.9 (4) C35—C36—C40 132.5 (4)
C11—C10—C7 115.5 (4) O10—C37—C36 112.0 (4) C12—C11—C16 119.3 (4) O10—C37—C38 123.9 (5) C12—C11—C10 120.2 (4) C36—C37—C38 124.1 (5) C16—C11—C10 120.3 (4) C39—C38—C37 116.7 (5)
O2—C12—C13 116.8 (4) C39—C38—H38 121.6
O2—C12—C11 123.4 (4) C37—C38—H38 121.6
C13—C12—C11 119.7 (4) C38—C39—C34 122.0 (5)
C12—C13—C14 118.9 (4) C38—C39—H39 119.0
C12—C13—C17 132.3 (4) C34—C39—H39 119.0
C14—C13—C17 108.8 (4) C36—C40—C41 101.7 (4)
O4—C14—C15 124.0 (5) C36—C40—H40A 111.4
O4—C14—C13 112.8 (4) C41—C40—H40A 111.4
C15—C14—C13 123.2 (5) C36—C40—H40B 111.4
C16—C15—C14 117.1 (5) C41—C40—H40B 111.4
C16—C15—H15 121.5 H40A—C40—H40B 109.3
C14—C15—H15 121.5 O10—C41—C42 110.4 (5)
C15—C16—C11 121.7 (5) O10—C41—C40 105.8 (4)
C15—C16—H16 119.1 C42—C41—C40 114.0 (4)
C11—C16—H16 119.1 O10—C41—H41 108.8
C13—C17—C18 101.5 (4) C42—C41—H41 108.8
C13—C17—H17A 111.5 C40—C41—H41 108.8
C18—C17—H17A 111.5 C43—C42—C41 122.0 (7)
C13—C17—H17B 111.5 C43—C42—C44 123.5 (7)
C18—C17—H17B 111.5 C41—C42—C44 114.5 (6)
H17A—C17—H17B 109.3 C42—C43—H43A 120.0
O4—C18—C19 108.9 (4) C42—C43—H43B 120.0
O4—C18—C17 105.1 (4) H43A—C43—H43B 120.0
C19—C18—C17 116.3 (4) C42—C44—H44A 109.5
O4—C18—H18 108.8 C42—C44—H44B 109.5
C19—C18—H18 108.8 H44A—C44—H44B 109.5
C17—C18—H18 108.8 C42—C44—H44C 109.5
C21—C19—C20 123.2 (6) H44A—C44—H44C 109.5 C21—C19—C18 118.1 (5) H44B—C44—H44C 109.5
C20—C19—C18 118.8 (5) O11—C45—H45A 109.5
C19—C20—H20A 109.5 O11—C45—H45B 109.5
C19—C20—H20B 109.5 H45A—C45—H45B 109.5
H20A—C20—H20B 109.5 O11—C45—H45C 109.5
C19—C20—H20C 109.5 H45A—C45—H45C 109.5
H20A—C20—H20C 109.5 H45B—C45—H45C 109.5
C19—C21—H21A 120.0 O12—C46—H46B 109.5
C19—C21—H21B 120.0 H46A—C46—H46B 109.5
H21A—C21—H21B 120.0 O12—C46—H46C 109.5
O5—C22—H22A 109.5 H46A—C46—H46C 109.5
O5—C22—H22B 109.5 H46B—C46—H46C 109.5
H22A—C22—H22B 109.5 O13—C47—O14 115.2 (10)
O5—C22—H22C 109.5 O13—C47—C48 128.7 (9)
H22A—C22—H22C 109.5 O14—C47—C48 114.5 (9)
H22B—C22—H22C 109.5 C47—C48—H48A 109.5
O6—C23—H23A 109.5 C47—C48—H48B 109.5
O6—C23—H23B 109.5 H48A—C48—H48B 109.5
H23A—C23—H23B 109.5 C47—C48—H48C 109.5
O6—C23—H23C 109.5 H48A—C48—H48C 109.5
H23A—C23—H23C 109.5 H48B—C48—H48C 109.5
O3—C5—C6—C7 −0.6 (6) C32—O9—C28—C29 15.2 (6) C5—C6—C7—C8 13.9 (6) O8—C30—C31—C33 50.1 (5) C6—C7—C8—C9 −41.7 (5) C30—C31—C33—C34 −152.5 (5) C7—C8—C9—O3 59.9 (5) C31—C33—C34—C35 9.9 (4) C8—C9—O3—C5 −46.6 (5) C33—C34—C35—O8 1.7 (6) C9—O3—C5—C6 17.1 (6) C34—C35—O8—C30 2.1 (4) O2—C8—C7—C10 −49.9 (5) C35—O8—C30—C31 −139.4 (4) C8—C7—C10—C11 27.0 (5) O4—C13—C14—C17 −0.9 (6) C7—C10—C11—C12 −0.4 (6) C13—C14—C17—C18 167.0 (5) C10—C11—C12—O2 −4.9 (6) C14—C7—C18—O4 0.9 (2) C11—C12—O2—C8 −18.7 (5) C7—C18—O4—C13 5.85 (13) C12—O2—C8—C7 46.5 (5) C18—O4—C13—C14 −168.3 (5) O9—C28—C29—C30 −0.6 (7) O10—C36—C37—C40 1.0 (6) C28—C29—C30—C31 15.1 (6) C36—C37—C38—C39 −0.4 (8) C29—C30—C31—C32 −42.4 (5) C37—C38—C39—O10 0.6 (4) C30—C31—C32—O9 58.0 (5) C38—C39—O10—C36 −179.4 (8) C31—C32—O9—C28 −43.5 (5) C39—O10—C36—C37 0.7 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
