organic papers
o648
Jeffrey R. Deschampset al. C19H18O4 DOI: 10.1107/S1600536801010273 Acta Cryst.(2001). E57, o648±o649 Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
A new
Cryptocarya
lactone
Jeffrey R. Deschamps,a* Clifford
George,aJudith L.
Flippen-Andersonaand Gayland
Spencerb
aLaboratory for the Structure of Matter, Naval
Research Laboratory, Washington, DC 20375, USA, andbNational Center for Agricultural
Utilization Research, Agriculture Research Service, United States Department of Agriculture, 1815 N. University St., Peoria, IL 61604, USA
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study T= 153 K
Mean(C±C) = 0.007 AÊ Disorder in main residue Rfactor = 0.057 wRfactor = 0.164 Data-to-parameter ratio = 5.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound 6-({4-oxo-6-[(1E
)-2-phenylvinyl]-2H-3,5,6-trihydropyran-2-yl}methyl)-5H-6-hydropyran-2-one, C19H24O4, is a germination inhibitor isolated from the seeds
ofCryptocarya wightiana.
Comment
Some extracts of seeds of plants in the genera Cryptocarya
have antigermination properties. A study by Spencer et al.
(1984) described (ÿ)-cryptocaryalactone {1-[(6-oxo-2H -3-hydropyran-2-yl)methyl]-3-phenylpropyl acetate} and (ÿ
)-deacetyl-cryptocaryalactone
[6-(2-hydroxy-4-phenylbutyl)-5H-6-hydropyran-2-one], germination inhibitors from Cryp-tocarya moschata seeds (i.e. Brazilian nutmeg). Both (ÿ
)-cryptocaryalactone and (ÿ)-deacetylcryptocaryalactone
inhibit the germination of Abutilon theophrasti (velvetleaf), with the deacetyl compound being more effective. Under conditions that were lethal to velvetleaf (i.e.94% inhibition of germination), corn was virtually unaffected, and soybeans were only minimally affected (i.e. 21% inhibition of germi-nation). Based on these results, a project was initiated to identify other natural products that inhibit seed germination of problem weed seeds (such as velvetleaf).
Extracts were prepared from a series ofCryptocaryaseeds collected in Sri Lanka. An extract from the seeds of Crypto-carya wightiana showed antigermination properties. This extract was fractionated further and the active component identi®ed as 6-({4-oxo-6-[(1E)-2-phenylvinyl]-2H -3,5,6-tri-hydropyran-2-yl}methyl)-5H-6-hydropyran-2-one, (I).
Two molecules comprise the asymmetric unit of (I) (Fig. 1). Both molecules have disordered phenyl rings with the two alternative positions at approximately 90 to each other and
approximately equal occupancy of the two positions.
Experimental
The Cryptocarya wightianaseed extract was fractionated by chro-matography on silica eluted with mixtures of hexane and ethyl
acetate. The ethyl acetate fraction was further separated by preparative HPLC on ODS with CH3CN/H2O/EtOH (1/1/4).
Crystal data C19H18O4 Mr= 310.33
Monoclinic,P21 a= 5.2472 (1) AÊ b= 5.2528 (1) AÊ c= 58.726 (1) AÊ
= 92.543 (1)
V= 1617.04 (5) AÊ3 Z= 4
Dx= 1.275 Mg mÿ3
CuKradiation Cell parameters from 5137
re¯ections
= 3.8±56.4
= 0.73 mmÿ1 T= 153 (2) K Prism, colorless 0.840.350.09 mm Data collection
Bruker SMART 1000 CCD diffractometer
!scans
Absorption correction: empirical (SADABS; Bruker, 2000) Tmin= 0.712,Tmax= 0.937 5150 measured re¯ections
2890 independent re¯ections 2868 re¯ections withI> 2(I) Rint= 0.033
max= 56.4 h=ÿ5!4 k=ÿ4!5 l=ÿ58!62 Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.057 wR(F2) = 0.164 S= 0.99 2890 re¯ections 489 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.1336P)2
+ 0.581P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.015
max= 0.44 e AÊÿ3
min=ÿ0.16 e AÊÿ3
Absolute structure: Flack (1983); 906 Friedel pairs
Flack parameter = 0.0 (4)
Data were collected at three settings of 2. With the detector at 95, 2data extend to about 113 [i.e.sin(max)/= 0.5402].
Unfor-tunately, the data crystal for this compound is no longer available so additional data can not be collected. The experimental restriction accounts for, in part, the relatively low data/parameter ratio. H atoms were re®ned with the riding model.
Data collection:SMART(Bruker, 1999); cell re®nement:SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure:XS(Sheldrick, 1990); program(s) used to re®ne structure:
SHELXTL(Sheldrick, 1997); molecular graphics:XP(Bruker, 1997); software used to prepare material for publication:SHELXTL.
The authors would like to thank Ronald D. Plattner of the United States Department of Agriculture (USDA) for his assistance in locating supporting materials used in preparing this manuscript. This research was supported in part by the United States Department of Agriculture (USDA) and the Naval Research Laboratory (NRL).
References
Bruker (1997).XP. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999).SMART. Version 5.059. Bruker AXS Inc., Madison, Wisconsin,
USA.
Bruker (2000).SADABS(Version 2.01) andSAINT(Version 6.02A). Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983).Acta Cryst.A39, 876±881. Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.
Sheldrick, G. M. (1997).SHELXTL.Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Spencer, G. F., England, R. E. & Wolf, R. B. (1984).Phytochemistry,23, 2499± 2500.
Figure 1
supporting information
sup-1
Acta Cryst. (2001). E57, o648–o649
supporting information
Acta Cryst. (2001). E57, o648–o649 [doi:10.1107/S1600536801010273]
A new
Cryptocarya
lactone
Jeffrey R. Deschamps, Clifford George, Judith L. Flippen-Anderson and Gayland Spencer
S1. Comment
Some extracts of seeds of plants in the genera Cryptocarya have antigermination properties. A study by Spencer et al.
(1984) described (-)-cryptocaryalactone {1-[(6-oxo-2H-3-hydropyran-2-yl)methyl]-3-phenylpropyl acetate} and
(-)-de-acetyl-cryptocaryalactone [6-(2-hydroxy-4-phenylbutyl)-5H-6-hydropyran-2-one], germination inhibitors from
Cryptocarya Moschata seeds (i.e. Brazilian nutmeg). Both (-)-cryptocaryalactone and (-)-deacetylcryptocaryalactone
inhibit the germination of Abutilon theophrasti (velvetleaf), with the deacetyl compound being more effective. Under
conditions that that were lethal to velvetleaf (i.e. 94% inhibition of germination), corn was virtually unaffected, and
soybeans were only minimally affected (i.e. 21% inhibition of germination). Based on these results, a project was
initiated to identify other natural products that inhibit seed germination of problem weed seeds (such as velvetleaf).
Extracts were prepared from a series of Cryptocarya seeds collected in Sri Lanka. An extract from the seeds of
Cryptocarya Wightiana showed antigermination properties. This extract was fractionated further and the active
component identified as 6-({4-oxo-6-[(1E)-2-phenylvinyl]-2H-3,5,6-trihydropyran-2-yl}methyl)-5H-
6-hydropyran-2-one, (I).
Two molecules comprise the asymmetric unit of (I) (Fig. 1). Both molecules have disordered phenyl rings with the two
alternate positions at approximately 90° to each other and approximately equal occupancy of the two positions.
S2. Experimental
The cryptocarya cightiana seed extract was fractionated by chromatography on silica eluted with mixtures of hexane and
ethyl acetate. The ethyl acetate fraction was further separated by preparative HPLC on ODS with CH3CN/H2O/EtOH
(1/1/4).
S3. Refinement
Data was collected at three settings of 2θ. With the detector at 95°, 2θ data extend to about 113° [i.e. sin(θmax)/λ =
0.5402]. Unfortunately, the data crystal for this compound is no longer available so additional data can not be collected.
The experimental restriction accounts for, in part, the relatively low data/parameter ratio. H atoms were refined with the
Figure 1
Displacement ellipsoid plot (Bruker, 1997) of (I) showing the ellipsoids at the 30% probability level. H atoms are shown
as small circles of an arbitrary radii. Atom labels for the alternate conformation of the disordered phenyl rings have been
omitted for clarity.
(I)
Crystal data C19H18O4
Mr = 310.33 Monoclinic, P21
a = 5.2472 (1) Å b = 5.2528 (1) Å c = 58.726 (1) Å β = 92.543 (1)° V = 1617.04 (5) Å3
Z = 4
F(000) = 656 Dx = 1.275 Mg m−3
Cu Kα radiation, λ = 1.54178 Å Cell parameters from 5137 reflections θ = 3.8–56.4°
µ = 0.73 mm−1
T = 153 K Prism, colorless 0.84 × 0.35 × 0.09 mm
Data collection
Bruker SMART 1000 CCD diffractometer
Radiation source: rotating anode Gobel optics monochromator ω scans
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2000) Tmin = 0.712, Tmax = 0.937
5150 measured reflections 2890 independent reflections 2868 reflections with I > 2σ(I) Rint = 0.033
θmax = 56.4°, θmin = 3.8°
h = −5→4 k = −4→5 l = −58→62
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.057
wR(F2) = 0.164
S = 0.99 2890 reflections 489 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.1336P)2 + 0.581P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.015
Δρmax = 0.44 e Å−3
Δρmin = −0.16 e Å−3
Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
supporting information
sup-3
Acta Cryst. (2001). E57, o648–o649 Special details
Experimental. Final cell refinement and decay correction applied after integration as part of merge process in SAINT v6.02 A.
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 Occ. (<1)
C1 0.2934 (12) 1.2065 (17) 0.76835 (10) 0.091 (2)
H1A 0.3429 1.2671 0.7543 0.109*
C2 0.471 (2) 1.154 (3) 0.7848 (2) 0.085 (4) 0.502 (7)
H2A 0.6421 1.1688 0.7817 0.102* 0.502 (7)
C3 0.4085 (19) 1.080 (2) 0.80548 (17) 0.067 (3) 0.502 (7)
H3A 0.5371 1.0725 0.8169 0.080* 0.502 (7)
C5 −0.0327 (19) 1.088 (2) 0.79383 (14) 0.066 (3) 0.502 (7)
H5A −0.2026 1.0779 0.7976 0.079* 0.502 (7)
C6 0.0280 (18) 1.170 (2) 0.77219 (14) 0.063 (3) 0.502 (7)
H6A −0.0973 1.2004 0.7608 0.076* 0.502 (7)
C4 0.1709 (8) 1.0158 (12) 0.81086 (7) 0.0617 (14)
C2′ 0.276 (2) 1.349 (3) 0.7861 (2) 0.098 (5) 0.498 (7)
H2′A 0.3026 1.5229 0.7843 0.117* 0.498 (7)
C3′ 0.221 (2) 1.263 (3) 0.8076 (2) 0.087 (4) 0.498 (7)
H3′A 0.2178 1.3761 0.8197 0.104* 0.498 (7)
C5′ 0.2214 (18) 0.847 (2) 0.79213 (14) 0.063 (3) 0.498 (7)
H5′A 0.2150 0.6715 0.7942 0.075* 0.498 (7)
C6′ 0.279 (2) 0.946 (3) 0.77136 (17) 0.075 (3) 0.498 (7)
H6′A 0.3076 0.8374 0.7592 0.090* 0.498 (7)
C7 0.1111 (9) 0.9008 (13) 0.83232 (7) 0.0687 (14)
H7A 0.2060 0.9529 0.8452 0.082*
C8 −0.0663 (13) 0.7288 (17) 0.83506 (8) 0.111 (3)
H8A −0.1650 0.6826 0.8222 0.133*
C9 −0.1234 (10) 0.6036 (14) 0.85631 (8) 0.0804 (17) C10 −0.3074 (10) 0.4313 (15) 0.85807 (8) 0.089 (2)
H10A −0.4289 0.4158 0.8461 0.107*
C11 −0.3270 (9) 0.2685 (11) 0.87749 (8) 0.0680 (14) O3 −0.4936 (8) 0.1093 (8) 0.87971 (7) 0.0942 (13) C12 −0.1216 (9) 0.3183 (10) 0.89557 (8) 0.0644 (13)
H12A −0.1875 0.2798 0.9104 0.077*
H12B 0.0202 0.2041 0.8932 0.077*
C13 −0.0255 (8) 0.5870 (10) 0.89574 (7) 0.0543 (11)
O2 0.0434 (6) 0.6687 (7) 0.87367 (4) 0.0668 (10) C14 0.2076 (8) 0.6300 (11) 0.91144 (7) 0.0605 (12)
H14A 0.3290 0.4945 0.9090 0.073*
H14B 0.2871 0.7889 0.9072 0.073*
C15 0.1557 (7) 0.6395 (9) 0.93609 (6) 0.0526 (11)
H15A 0.0410 0.4993 0.9397 0.063*
O1 0.0258 (5) 0.8835 (7) 0.94013 (5) 0.0597 (8) C16 −0.0078 (10) 0.9599 (12) 0.96170 (8) 0.0670 (14) O4 −0.1491 (8) 1.1397 (9) 0.96459 (6) 0.0901 (12) C17 0.1388 (11) 0.8355 (12) 0.97991 (8) 0.0740 (15)
H17A 0.0951 0.8598 0.9949 0.089*
C18 0.3319 (12) 0.6895 (14) 0.97550 (8) 0.0872 (18)
H18A 0.4324 0.6249 0.9876 0.105*
C19 0.3970 (9) 0.6229 (14) 0.95181 (8) 0.0793 (16)
H19A 0.4661 0.4517 0.9515 0.095*
H19B 0.5253 0.7394 0.9466 0.095*
C1A 0.7919 (12) 0.6937 (15) 0.73040 (10) 0.0876 (19)
H1AA 0.8559 0.7464 0.7446 0.105*
C2A 0.738 (2) 0.868 (2) 0.71397 (17) 0.076 (3) 0.515 (7)
H2AA 0.7645 1.0410 0.7168 0.091* 0.515 (7)
C3A 0.6455 (17) 0.786 (2) 0.69322 (19) 0.071 (3) 0.515 (7)
H3AA 0.6261 0.9064 0.6816 0.085* 0.515 (7)
C5A 0.6602 (16) 0.356 (2) 0.70547 (13) 0.062 (3) 0.515 (7)
H5AA 0.6476 0.1842 0.7019 0.074* 0.515 (7)
C6A 0.7507 (18) 0.426 (2) 0.72604 (14) 0.068 (3) 0.515 (7)
H6AA 0.7864 0.3053 0.7373 0.082* 0.515 (7)
C4A 0.5798 (9) 0.5451 (11) 0.68826 (7) 0.0626 (14)
C2A′ 0.533 (2) 0.670 (2) 0.72763 (16) 0.077 (3) 0.485 (7)
H2AB 0.4328 0.6968 0.7401 0.092* 0.485 (7)
C3A′ 0.4193 (18) 0.610 (2) 0.70721 (14) 0.063 (3) 0.485 (7)
H3AB 0.2425 0.6090 0.7053 0.076* 0.485 (7)
C5A′ 0.831 (2) 0.607 (3) 0.6913 (2) 0.086 (4) 0.485 (7)
H5AB 0.9341 0.6121 0.6788 0.103* 0.485 (7)
C6A′ 0.935 (2) 0.662 (3) 0.71270 (19) 0.081 (4) 0.485 (7)
H6AB 1.1107 0.6775 0.7147 0.097* 0.485 (7)
C7A 0.4507 (9) 0.4785 (11) 0.66674 (8) 0.0699 (14)
H7AA 0.4939 0.5695 0.6539 0.084*
C8A 0.2766 (12) 0.2988 (16) 0.66401 (9) 0.108 (3)
H8AA 0.2366 0.2053 0.6768 0.129*
C9A 0.1454 (10) 0.2362 (12) 0.64308 (7) 0.0774 (17) C10A −0.0310 (11) 0.0469 (13) 0.64090 (8) 0.0870 (18)
H10B −0.0424 −0.0702 0.6527 0.104*
C11A −0.1997 (8) 0.0206 (11) 0.62118 (8) 0.0670 (14) O3A −0.3607 (7) −0.1467 (9) 0.61901 (7) 0.0932 (14) C12A −0.1626 (8) 0.2154 (11) 0.60358 (8) 0.0661 (14)
H12C −0.2759 0.3574 0.6062 0.079*
H12D −0.2096 0.1438 0.5888 0.079*
supporting information
sup-5
Acta Cryst. (2001). E57, o648–o649
H13B 0.2181 0.1753 0.5981 0.068*
O2A 0.2012 (5) 0.3893 (7) 0.62540 (5) 0.0667 (9) C14A 0.1435 (9) 0.5403 (10) 0.58798 (7) 0.0598 (12)
H14C 0.0066 0.6601 0.5904 0.072*
H14D 0.3027 0.6239 0.5925 0.072*
C15A 0.1463 (7) 0.4796 (9) 0.56311 (7) 0.0534 (11)
H15B 0.0039 0.3650 0.5591 0.064*
O1A 0.3864 (5) 0.3476 (7) 0.55923 (5) 0.0586 (9) C16A 0.4604 (9) 0.3093 (11) 0.53773 (7) 0.0592 (13) O4A 0.6348 (7) 0.1650 (9) 0.53516 (6) 0.0844 (12) C17A 0.3325 (10) 0.4532 (14) 0.51979 (8) 0.0764 (16)
H17B 0.3531 0.4070 0.5047 0.092*
C18A 0.1886 (11) 0.6470 (14) 0.52429 (8) 0.0840 (18)
H18B 0.1233 0.7465 0.5123 0.101*
C19A 0.1249 (10) 0.7145 (12) 0.54802 (8) 0.0753 (15)
H19C −0.0473 0.7816 0.5481 0.090*
H19D 0.2410 0.8450 0.5539 0.090*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1A 0.098 (4) 0.099 (6) 0.065 (3) −0.027 (4) −0.006 (3) −0.005 (3) C2A 0.110 (8) 0.044 (7) 0.074 (7) −0.015 (6) 0.009 (5) −0.020 (6) C3A 0.053 (6) 0.065 (8) 0.094 (8) −0.003 (5) 0.010 (5) 0.010 (6) C5A 0.072 (6) 0.061 (7) 0.052 (5) −0.017 (5) −0.002 (4) 0.003 (4) C6A 0.084 (6) 0.081 (9) 0.040 (5) −0.011 (5) 0.012 (4) 0.006 (5) C4A 0.073 (3) 0.063 (4) 0.052 (3) −0.014 (2) 0.003 (2) 0.007 (2) C2A′ 0.116 (9) 0.066 (9) 0.048 (5) −0.021 (6) 0.003 (5) −0.001 (5) C3A′ 0.068 (6) 0.078 (8) 0.044 (5) −0.027 (5) 0.009 (4) 0.006 (5) C5A′ 0.070 (8) 0.101 (11) 0.091 (8) −0.003 (7) 0.038 (6) 0.023 (7) C6A′ 0.061 (6) 0.110 (11) 0.070 (8) −0.011 (7) −0.009 (6) 0.007 (7) C7A 0.086 (3) 0.064 (4) 0.060 (3) −0.009 (3) 0.007 (2) 0.002 (2) C8A 0.128 (5) 0.141 (7) 0.053 (3) −0.072 (5) −0.011 (3) 0.025 (3) C9A 0.097 (3) 0.094 (5) 0.041 (2) −0.036 (3) 0.000 (2) 0.004 (3) C10A 0.115 (4) 0.088 (5) 0.059 (3) −0.041 (4) 0.007 (3) 0.008 (3) C11A 0.054 (3) 0.079 (4) 0.068 (3) −0.016 (3) 0.013 (2) −0.004 (3) O3A 0.076 (2) 0.101 (4) 0.103 (3) −0.045 (2) 0.0073 (17) 0.009 (2) C12A 0.046 (2) 0.081 (4) 0.071 (3) −0.014 (2) 0.0007 (19) −0.009 (3) C13A 0.062 (2) 0.057 (4) 0.049 (2) −0.012 (2) −0.0067 (18) 0.000 (2) O2A 0.0762 (18) 0.068 (2) 0.0552 (17) −0.0213 (17) −0.0065 (13) 0.0002 (17) C14A 0.069 (3) 0.049 (3) 0.060 (3) −0.012 (2) −0.0095 (19) 0.001 (2) C15A 0.048 (2) 0.050 (3) 0.061 (2) −0.0081 (19) −0.0082 (17) 0.007 (2) O1A 0.0573 (16) 0.065 (2) 0.0531 (17) 0.0003 (14) −0.0087 (12) 0.0039 (15) C16A 0.058 (3) 0.070 (4) 0.050 (3) −0.011 (3) 0.002 (2) −0.009 (2) O4A 0.074 (2) 0.098 (3) 0.081 (2) 0.007 (2) 0.0021 (16) −0.013 (2) C17A 0.082 (3) 0.100 (5) 0.048 (3) −0.010 (3) 0.001 (2) 0.006 (3) C18A 0.098 (4) 0.095 (6) 0.058 (3) −0.008 (4) −0.013 (3) 0.027 (3) C19A 0.086 (3) 0.066 (4) 0.074 (3) 0.007 (3) −0.004 (2) 0.022 (3)
Geometric parameters (Å, º)
C1—C2′ 1.291 (17) C1A—C6A′ 1.318 (13)
C1—C2 1.340 (13) C1A—C2A 1.352 (13)
C1—C6′ 1.382 (15) C1A—C2A′ 1.365 (13)
C1—C6 1.433 (11) C1A—C6A 1.444 (15)
C2—C3 1.329 (14) C2A—C3A 1.362 (15)
C3—C4 1.343 (11) C3A—C4A 1.342 (13)
C5—C6 1.393 (13) C5A—C6A 1.330 (13)
C5—C4 1.480 (10) C5A—C4A 1.464 (11)
C4—C3′ 1.339 (16) C4A—C5A′ 1.363 (13)
C4—C7 1.444 (7) C4A—C7A 1.450 (7)
C4—C5′ 1.446 (11) C4A—C3A′ 1.465 (12)
C2′—C3′ 1.382 (18) C2A′—C3A′ 1.354 (13)
C5′—C6′ 1.372 (15) C5A′—C6A′ 1.378 (15)
C7—C8 1.312 (9) C7A—C8A 1.318 (8)
C8—C9 1.454 (8) C8A—C9A 1.420 (7)
C9—C10 1.331 (8) C9A—O2A 1.356 (6)
supporting information
sup-7
Acta Cryst. (2001). E57, o648–o649
C11—O3 1.221 (6) C11A—O3A 1.222 (6)
C11—C12 1.502 (6) C11A—C12A 1.473 (7)
C12—C13 1.499 (7) C12A—C13A 1.518 (6)
C13—O2 1.427 (5) C13A—O2A 1.420 (5)
C13—C14 1.516 (5) C13A—C14A 1.509 (7)
C14—C15 1.485 (6) C14A—C15A 1.496 (6)
C15—O1 1.476 (6) C15A—O1A 1.465 (5)
C15—C19 1.536 (5) C15A—C19A 1.520 (7)
O1—C16 1.348 (6) O1A—C16A 1.353 (5)
C16—O4 1.217 (7) C16A—O4A 1.203 (6)
C16—C17 1.445 (7) C16A—C17A 1.438 (7)
C17—C18 1.306 (8) C17A—C18A 1.301 (8)
C18—C19 1.489 (8) C18A—C19A 1.490 (8)
C2′—C1—C2 67.0 (8) C6A′—C1A—C2A 68.3 (8)
C2′—C1—C6′ 117.7 (10) C6A′—C1A—C2A′ 119.4 (7)
C2—C1—C6′ 75.1 (9) C2A—C1A—C2A′ 78.6 (7)
C2′—C1—C6 81.1 (7) C6A′—C1A—C6A 79.9 (9)
C2—C1—C6 120.5 (8) C2A—C1A—C6A 120.7 (7)
C6′—C1—C6 77.8 (8) C2A′—C1A—C6A 75.6 (8)
C3—C2—C1 121.9 (9) C1A—C2A—C3A 118.5 (11)
C2—C3—C4 123.8 (8) C4A—C3A—C2A 124.9 (10)
C6—C5—C4 120.6 (8) C6A—C5A—C4A 121.5 (10)
C5—C6—C1 116.6 (7) C5A—C6A—C1A 118.2 (9)
C3′—C4—C3 62.2 (8) C3A—C4A—C5A′ 60.6 (9)
C3′—C4—C7 125.7 (7) C3A—C4A—C7A 121.5 (6)
C3—C4—C7 123.4 (6) C5A′—C4A—C7A 125.7 (6)
C3′—C4—C5′ 116.1 (8) C3A—C4A—C5A 115.2 (7)
C3—C4—C5′ 76.8 (6) C5A′—C4A—C5A 79.9 (7)
C7—C4—C5′ 117.5 (7) C7A—C4A—C5A 123.2 (6)
C3′—C4—C5 78.1 (8) C3A—C4A—C3A′ 76.5 (7)
C3—C4—C5 115.3 (7) C5A′—C4A—C3A′ 115.6 (8)
C7—C4—C5 121.2 (5) C7A—C4A—C3A′ 117.1 (5)
C5′—C4—C5 78.1 (6) C5A—C4A—C3A′ 77.9 (6)
C1—C2′—C3′ 124.8 (14) C3A′—C2A′—C1A 121.6 (10) C4—C3′—C2′ 120.1 (11) C2A′—C3A′—C4A 118.8 (9) C6′—C5′—C4 119.9 (11) C4A—C5A′—C6A′ 120.5 (9) C5′—C6′—C1 120.3 (10) C1A—C6A′—C5A′ 122.1 (9)
C8—C7—C4 125.3 (4) C8A—C7A—C4A 125.0 (5)
C7—C8—C9 126.3 (5) C7A—C8A—C9A 125.3 (5)
C10—C9—O2 124.0 (5) O2A—C9A—C10A 122.1 (4)
C10—C9—C8 123.5 (4) O2A—C9A—C8A 114.4 (5)
O2—C9—C8 112.3 (5) C10A—C9A—C8A 123.5 (5)
