Acta Cryst.(2002). E58, m197±m199 DOI: 10.1107/S1600536802005809 Sheth, Jr and Grant 2Na+2C19H15O4ÿC3H8O
m197
metal-organic papers
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Warfarin sodium 2-propanol solvate
Agam R. Sheth,aVictor G.
Young Jrband David J. W.
Granta*
aDepartment of Pharmaceutics, College of
Pharmacy, University of Minnesota, Weaver-Densford Hall, 308 Harvard Street SE, Minneapolis, MN 55455-0343, USA, and
bDepartment of Chemistry, University of
Minnesota, Smith Hall, 207 Pleasant St. SE, Minneapolis, MN 55455-0431, USA Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 173 K
Mean(C±C) = 0.007 AÊ Disorder in solvent or counterion
Rfactor = 0.069
wRfactor = 0.225
Data-to-parameter ratio = 13.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The crystal structure of the title compound, R-(Na+
-C19H15O4ÿ)S-(Na+C19H15O4ÿ)C3H8O, the 2-propanol
sol-vate of the sodium salt of
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one, i.e. bis(sodium
2-oxo-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-4-olate) 2-propanol solvate, is composed of in®nite sheets in theabplane, separated only by van der Waals contacts. The hydroxycoumarin fragments display rotational rigid-body motion. The 2-propanol mol-ecule is rotationally disordered and was modeled as two components. Each of the two sodium ions is associated with four O atoms that form a distorted tetrahedron bridging the two warfarin anions.
Comment
Warfarin sodium is a pharmaceutical anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagula-tion factors (Majerus et al., 1996). The parent compound is warfarin, which exists in two enantiomeric forms. Its sodium derivative can be puri®ed by crystallization from 2-propanol as a warfarin sodium 2-propanol complex (Schroeder & Link, 1963). Previously, it has been found that (ÿ)-(S)-warfarin [Valente et al., 1975; Cambridge Structural Database (CSD; Allen & Kennard, 1993) reference code WARFAR10] and
racemic warfarin (Bravic et al., 1973; CSD reference code
WARFIN) crystallized from acetone and methanol, respec-tively, as an intramolecular cyclic hemiketal which was formed by reaction between the side-chain keto function and the phenolic hydroxyl at the 4-position of the coumarin ring system. These structures do not contain warfarin molecules themselves, but instead consist of covalently cyclized mol-ecules of warfarin, which may be described as (2S,4S)-2,3H -2-methyl-4-phenyl-5-oxobenzopyrano[3,4-e]dihydropyran-2-ol.
The results of the present work, however, show that warfarin sodium crystallizes from 2-propanol as a solvate, in which the asymmetric unit contains two molecules of warfarin
sodium (one each of theRandSenantiomer) and one
mol-ecule of 2-propanol. Although the unit-cell parameters and
the space group have previously been reported (Hiskey & Melnitchenko, 1965; CSD reference code ZZZKXG), the single-crystal structure has hitherto not been completely solved. Few reports of the physical properties of this compound have been published (Hiskey & Melnitchenko, 1965; Gao & Maurin, 2001). In the present study, the complete crystal structure of warfarin sodium 2-propanol solvate is solved and described for the ®rst time.
Currently, the warfarin sodium 2-propanol adduct is commercially available as a pharmaceutical and described as a clathrate (Haleblian, 1975). Clathrates are crystalline mole-cular inclusion adducts consisting of two distinct components, a relatively rigid host and a quite mobile guest. Within clath-rates the guest molecules lie trapped in closed, three-dimen-sional cavities or cages formed by the crystalline structure of the host (Andreeti, 1984; Mandelcorn, 1959). The term `clathrate' was introduced by Powell (1948) from the Latin wordclathratus, which means enclosed by the bars of a grating. The term `clathration' is used instead of `solvation' when there is no speci®c, chemical interaction between the solvent and solute (Lipkowski, 1996). In the crystal structure of warfarin sodium 2-propanol solvate in the present work, the guest molecules of 2-propanol are not enclosed in a cage-like structure of the host molecules of warfarin sodium. Indeed, the 2-propanol molecule is strongly coordinated to the sodium atom of warfarin sodium with one molecule of 2-propanol to two molecules of warfarin sodium in the asymmetric unit. Hence, the crystal structure solved in the present work is a solvate, but not a clathrate.
Experimental
`Warfarin sodium clathrate' was obtained from Sigma Chemical Co. (St Louis, MO). Single crystals were prepared from warfarin sodium clathrate and 2-propanol (Hiskey & Melnitchenko, 1965). Every precaution was taken to exclude water from the system during crystallization. The compound was dried in a vacuum oven at about
was dried by ®rst re¯uxing with calcium oxide (200 g lÿ1) in a
round-bottomed ¯ask for several hours. The distillate was further dried using 3 AÊ molecular sieves (Perrin & Armarego, 1988). Then, 90 mg of anhydrous `warfarin sodium clathrate' was dissolved in 9 ml of 2-propanol during re¯uxing. When the solid had dissolved, re¯uxing was stopped and the ¯ask was allowed to stand undisturbed under a drying tube to exclude moisture. After a few days, as 2-propanol slowly evaporated, crystals of warfarin sodium 2-propanol solvate appeared.
Crystal data
2Na+2C
19H15O4ÿC3H8O Mr= 720.69
Monoclinic,P21=c a= 15.393 (2) AÊ
b= 11.2392 (17) AÊ
c= 22.124 (3) AÊ
= 107.424 (3) V= 3651.9 (9) AÊ3 Z= 4
Dx= 1.311 Mg mÿ3
MoKradiation Cell parameters from 3390
re¯ections
= 1.4±25.1 = 0.11 mmÿ1 T= 173 (2) K
Irregular plate, colorless 0.400.230.11 mm
Data collection
Bruker CCD area-detector diffractometer
'and!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)
Tmin= 0.970,Tmax= 0.988
26991 measured re¯ections
6472 independent re¯ections 3895 re¯ections withI> 2(I)
Rint= 0.060 max= 25.1 h=ÿ18!18
k=ÿ13!13
l=ÿ26!26
Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.069 wR(F2) = 0.225 S= 1.04 6472 re¯ections 487 parameters
w= 1/[2(F
o2) + (0.0999P)2
+ 5.7631P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.010 max= 0.95 e AÊÿ3 min=ÿ0.48 e AÊÿ3 Figure 1
The atomic numbering scheme of warfarin sodium 2-propanol solvate in this work. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O1SÐH1SA O2Bi 0.84 2.26 3.049 (5) 156
O1SÐH1SA O3Bi 0.84 2.56 3.049 (4) 118 Symmetry code: (i)ÿx;1
2y;12ÿz.
The 2-propanol molecule was found to be disordered. It was re®ned with 20 restraints to force similar bond lengths and angles to maintain chemically reasonable values. In addition to the disorder of 2-propanol, a number of peaks were found in the difference Fourier map in the region of C5AÐC8A. These peaks suggest a possible rotation around the C1AÐC2A bond. Attempts to model any chemically reasonable disorder in this region failed.
Data collection:SMART(Bruker, 2000); cell re®nement:SAINT
(Bruker, 2000); data reduction: SAINT; program(s) used to solve structure:SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL/PC(Bruker, 1997); software used to prepare material for publication:SHELXTL/PC.
References
Allen, F. H. & Kennard, O. (1993).Chem. Des. Autom. News,8, 1, 31±37. Andreeti, G. D. (1984).Inclusion Compounds, edited by J. L. Atwood, J. E. D.
Davies and D. D. MacNicol, Vol. 3, pp. 129±146. London: Academic Press Inc. Ltd.
Bravic, G., Gaultier, J. & Hauw, C. (1973).C. R. Acad. Sci. Paris Ser. C,277, 1215±1218.
Bruker (1997)SHELXTL/PC. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2000).SMARTandSAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
Gao, D. & Maurin, M. B. (2001). AAPSPharmSci, 3 (URL: http:// www.pharmsci.org).
Haleblian, J. K. (1975).J. Pharm. Sci.64, 1269±1288.
Hiskey, C. F. & Melnitchenko, V. (1965).J. Pharm. Sci.54, 1298±1302. Lipkowski, J. (1996).NATO ASI Ser. C,480, 265±283.
Majerus, P. W., Broze, G. J., Miletich, J. P. & Tollefsen, D. M. (1996).Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed., edited by J. G. Hardman and L. E. Limbird, pp. 1346±1350. New York: McGraw-Hill. Mandelcorn, L. (1959).Chem. Rev.59, 827±839.
Perrin, D. D. & Armarego, W. L. F. (1988). Puri®cation of Laboratory Chemicals, 3rd ed., pp. 207. Oxford: Pergamon Press.
Powell, H. M. (1948).J. Chem. Soc.pp. 61±73.
Schroeder, C. H. & Link, K. P. (1963). US Patent 3 077 481. Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.
Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Sheldrick, G. M. (2000).SADABS. Bruker AXS Inc., Madison, Wisconsin,
USA.
Valente, E. J., Trager, W. F. & Jensen, L. H. (1975).Acta Cryst.B31, 954±960.
supporting information
Acta Cryst. (2002). E58, m197–m199 [doi:10.1107/S1600536802005809]
Warfarin sodium 2-propanol solvate
Agam R. Sheth, Victor G. Young and David J. W. Grant
S1. Comment
Warfarin sodium is a pharmaceutical anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent
coagulation factors (Majerus et al., 1996). The parent compound is warfarin, which exists in two enantiomeric forms. Its
sodium derivative can be purified by crystallization from 2-propanol as a warfarin sodium 2-propanol complex
(Schoreder & Link, 1963). Previously, it has been found that (-)-(S)-warfarin [Valente et al., 1975; Cambridge Structural
Database (CSD; Allen & Kennard, 1993) reference code WARFAR10] and racemic warfarin (Bravic et al., 1973; CSD
reference code WARFIN) crystallized from acetone and methanol, respectively, as an intramolecular cyclic hemiketal
which was formed by reaction between the side-chain keto function and the phenolic hydroxyl at the 4-position of the
coumarin ring system. These structures do not contain warfarin molecules themselves, but instead consist of covalently
cyclized molecules of warfarin, which may be described as (2S,4S)-2,3H-2-methyl-4-phenyl-5-oxobenzopyrano[3,4-e
]di-hydropyran-2-ol. The results of the present work, however, show that warfarin sodium crystallizes from 2-propanol as a
solvate, in which the asymmetric unit contains two molecules of warfarin sodium (one each of the R and S enantiomer)
and one molecule of 2-propanol. Although the unit-cell parameters and the space group have previously been reported
(Hiskey & Melnitchenko, 1965; CSD reference code ZZZKXG), the single-crystal structure has hitherto not been
completely solved. Few reports of the physical properties of this compound have been published (Hiskey &
Melnitchenko, 1965; Gao & Maurin, 2001). In the present study, the complete crystal structure of warfarin sodium
2-propanol solvate is solved and described for the first time.
Currently, the warfarin sodium 2-propanol adduct is commercially available as a pharmaceutical and described as a
clathrate (Haleblian, 1975). Clathrates are crystalline molecular inclusion adducts consisting of two distinct components,
a relatively rigid host and a quite mobile guest. Within clathrates the guest molecules lie trapped in closed,
three-dimensional cavities or cages formed by the crystalline structure of the host (Andreeti, 1984; Mandelcorn, 1959). The
term `clathrate′ was introduced by Powell (1948) from the Latin word clathratus, which means enclosed by the bars of a
grating. The term `clathration′ is used instead of 'solvation′ when there is no specific, chemical interaction between the
solvent and solute (Lipkowski, 1996). In the crystal structure of warfarin sodium 2-propanol solvate in the present work,
the guest molecules of 2-propanol are not enclosed in a cage-like structure of the host molecules of warfarin sodium.
Indeed, the propanol molecule is strongly coordinated to the sodium atom of warfarin sodium with one molecule of
2-propanol to two molecules of warfarin sodium in the asymmetric unit. Hence, the crystal structure solved in the present
work is a solvate, but not a clathrate.
S2. Experimental
Warfarin sodium clathrate was obtained from Sigma Chemical Co. (St Louis, MO). Single crystals were prepared from
warfarin sodium clathrate and 2-propanol (Hiskey & Melnitchenko, 1965). Every precaution was taken to exclude water
supporting information
sup-2
Acta Cryst. (2002). E58, m197–m199remove the surface moisture. 2-Propanol was dried by first refluxing with calcium oxide (200 g l-1) in a round-bottomed
flask for several hours. The distillate was further dried using 3 Å molecular sieves (Perrin & Armarego, 1988). Then, 90
mg of anhydrous warfarin sodium clathrate was dissolved in 9 ml of 2-propanol during refluxing. When the solid had
dissolved, refluxing was stopped and the flask was allowed to stand undisturbed under a drying tube to exclude moisture.
After a few days, as 2-propanol slowly evaporated, crystals of warfarin sodium 2-propanol solvate appeared.
S3. Refinement
The 2-propanol molecule was found to be disordered. It was refined with 20 restraints to force similar bond lengths and
angles to maintain chemically reasonable values. In addition to the disorder of 2-propanol, a number of peaks were found
in the difference Fourier map in the region of C5A–C8A. These peaks suggest a possible rotation around the C1A—C2A
[image:5.610.111.498.237.488.2]bond. Attempts to model any chemically reasonable disorder in this region failed.
Figure 1
The atomic numbering scheme of warfarin sodium 2-propanol solvate in this work. Displacement ellipsoids are drawn at
Figure 2
Warfarin sodium 2-propanol solvate, 3 × 3 × 3 unit cells, looking down the b axis showing molecular sheets in the ab
plane. Individual sheets are separated only by van der Waals contacts.
2-propanol solvate of the sodium salt of 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one
Crystal data
2Na+·2C
38H30O8−·C3H8O Mr = 720.69
Monoclinic, P21/c a = 15.393 (2) Å
b = 11.2392 (17) Å
c = 22.124 (3) Å
β = 107.424 (3)°
V = 3651.9 (9) Å3 Z = 4
F(000) = 1512
Dx = 1.311 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3390 reflections
θ = 1.4–25.1°
µ = 0.11 mm−1 T = 173 K
Irregular plate, colorless 0.40 × 0.23 × 0.11 mm
Data collection
Bruker CCD area-detector diffractometer
Radiation source: normal-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)
supporting information
sup-4
Acta Cryst. (2002). E58, m197–m1993895 reflections with I > 2σ(I)
Rint = 0.060
θmax = 25.1°, θmin = 1.4°
h = −18→18
k = −13→13
l = −26→26
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.069 wR(F2) = 0.225 S = 1.04 6472 reflections 487 parameters 20 restraints
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) + (0.0999P)2 + 5.7631P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.010 Δρmax = 0.95 e Å−3 Δρmin = −0.48 e Å−3
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)
x y z Uiso*/Ueq Occ. (<1)
Na1 0.28289 (10) 0.48410 (14) 0.21456 (9) 0.0496 (5)
Na2 0.19189 (10) 0.76079 (13) 0.20748 (8) 0.0425 (4)
O1A 0.4218 (2) 0.4289 (3) 0.26762 (16) 0.0539 (8)
O2A 0.6052 (2) 0.1870 (3) 0.37154 (15) 0.0563 (9)
O3A 0.67354 (18) 0.1725 (2) 0.29947 (16) 0.0499 (8)
O4A 0.7297 (2) 0.4382 (2) 0.26860 (16) 0.0528 (8)
C1A 0.5533 (3) 0.3356 (4) 0.21103 (19) 0.0431 (10)
H1AA 0.6059 0.2890 0.2057 0.052*
C2A 0.5481 (2) 0.3066 (3) 0.27707 (17) 0.0309 (8)
C3A 0.4815 (3) 0.3588 (3) 0.2996 (2) 0.0383 (9)
C4A 0.4819 (3) 0.3279 (4) 0.3638 (2) 0.0525 (13)
C5A 0.4266 (4) 0.3773 (6) 0.3954 (3) 0.0776 (17)
H5AA 0.3848 0.4374 0.3747 0.093*
C6A 0.4287 (5) 0.3447 (7) 0.4544 (3) 0.093 (2)
H6AA 0.3917 0.3847 0.4755 0.112*
C7A 0.4858 (4) 0.2517 (7) 0.4846 (3) 0.0827 (19)
H7AA 0.4832 0.2262 0.5250 0.099*
C8A 0.5448 (5) 0.1958 (6) 0.4586 (3) 0.087 (2)
H8AA 0.5839 0.1332 0.4794 0.104*
C9A 0.5431 (4) 0.2399 (5) 0.3968 (2) 0.0555 (13)
C10A 0.6102 (3) 0.2235 (3) 0.3131 (2) 0.0370 (9)
C12A 0.4604 (3) 0.1683 (4) 0.1495 (2) 0.0559 (12)
H12A 0.5071 0.1162 0.1727 0.067*
C13A 0.3841 (4) 0.1221 (5) 0.1045 (2) 0.0676 (15)
H13A 0.3787 0.0386 0.0979 0.081*
C14A 0.3164 (4) 0.1961 (5) 0.0695 (2) 0.0676 (15)
H14A 0.2644 0.1639 0.0390 0.081*
C15A 0.3246 (3) 0.3162 (5) 0.0789 (2) 0.0629 (14)
H15A 0.2787 0.3679 0.0544 0.075*
C16A 0.3999 (3) 0.3634 (4) 0.1244 (2) 0.0512 (11)
H16A 0.4043 0.4470 0.1309 0.061*
C17A 0.5746 (3) 0.4650 (4) 0.2028 (2) 0.0501 (11)
H17A 0.5660 0.4800 0.1573 0.060*
H17B 0.5302 0.5150 0.2157 0.060*
C18A 0.6683 (3) 0.5037 (4) 0.2395 (2) 0.0426 (10)
C19A 0.6822 (4) 0.6363 (4) 0.2399 (3) 0.0665 (14)
H19A 0.7462 0.6535 0.2441 0.100*
H19B 0.6662 0.6714 0.2757 0.100*
H19C 0.6435 0.6703 0.2002 0.100*
O1B 0.17373 (19) 0.5785 (2) 0.24931 (16) 0.0520 (8)
O2B 0.03431 (19) 0.4232 (3) 0.36036 (14) 0.0473 (7)
O3B −0.06410 (18) 0.3416 (3) 0.27758 (14) 0.0452 (7)
O4B 0.1739 (2) 0.3400 (3) 0.17109 (17) 0.0589 (9)
C1B 0.0110 (3) 0.4410 (4) 0.1850 (2) 0.0414 (10)
H1BA 0.0503 0.4885 0.1653 0.050*
C2B 0.0500 (2) 0.4597 (3) 0.2557 (2) 0.0373 (9)
C3B 0.1285 (3) 0.5284 (3) 0.2815 (2) 0.0409 (10)
C4B 0.1596 (3) 0.5416 (3) 0.3513 (2) 0.0469 (11)
C5B 0.2384 (3) 0.6060 (4) 0.3833 (3) 0.0646 (15)
H5BA 0.2744 0.6416 0.3600 0.078*
C6B 0.2637 (4) 0.6175 (5) 0.4484 (3) 0.0786 (19)
H6BA 0.3179 0.6593 0.4696 0.094*
C7B 0.2108 (4) 0.5689 (5) 0.4831 (3) 0.0776 (18)
H7BA 0.2275 0.5802 0.5277 0.093*
C8B 0.1343 (4) 0.5044 (4) 0.4531 (2) 0.0619 (13)
H8BA 0.0983 0.4698 0.4766 0.074*
C9B 0.1103 (3) 0.4904 (4) 0.3877 (2) 0.0476 (11)
C10B 0.0033 (3) 0.4055 (4) 0.2948 (2) 0.0393 (10)
C11B −0.0849 (3) 0.4929 (4) 0.15855 (19) 0.0402 (9)
C12B −0.0953 (3) 0.6152 (4) 0.1560 (2) 0.0571 (12)
H12B −0.0437 0.6648 0.1730 0.069*
C13B −0.1800 (4) 0.6664 (5) 0.1291 (3) 0.0746 (17)
H13B −0.1858 0.7506 0.1275 0.090*
C14B −0.2558 (3) 0.5962 (6) 0.1047 (3) 0.0693 (15)
H14B −0.3136 0.6315 0.0855 0.083*
C15B −0.2467 (3) 0.4744 (5) 0.1084 (2) 0.0660 (14)
H15B −0.2988 0.4252 0.0926 0.079*
C16B −0.1621 (3) 0.4233 (4) 0.1349 (2) 0.0542 (12)
supporting information
sup-6
Acta Cryst. (2002). E58, m197–m199C17B 0.0177 (3) 0.3122 (4) 0.1642 (2) 0.0475 (11)
H17C 0.0001 0.2590 0.1943 0.057*
H17D −0.0274 0.3008 0.1221 0.057*
C18B 0.1090 (3) 0.2740 (4) 0.1604 (2) 0.0482 (11)
C19B 0.1155 (3) 0.1475 (4) 0.1394 (3) 0.0701 (15)
H19D 0.1685 0.1395 0.1239 0.105*
H19E 0.0601 0.1272 0.1054 0.105*
H19F 0.1220 0.0936 0.1753 0.105*
O1S 0.1022 (3) 0.7687 (4) 0.10006 (17) 0.0797 (12) 0.667 (13)
H1SA 0.0547 0.7924 0.1076 0.120* 0.667 (13)
C1S 0.0783 (6) 0.7120 (9) 0.0392 (5) 0.067 (3) 0.667 (13)
H1SB 0.0816 0.7726 0.0069 0.101* 0.667 (13)
C2S 0.1500 (13) 0.619 (3) 0.0426 (14) 0.090 (3) 0.667 (13)
H2SA 0.1474 0.5583 0.0738 0.136* 0.667 (13)
H2SB 0.2103 0.6565 0.0552 0.136* 0.667 (13)
H2SC 0.1391 0.5818 0.0009 0.136* 0.667 (13)
C3S −0.0168 (7) 0.6638 (12) 0.0214 (6) 0.076 (3) 0.667 (13)
H3SA −0.0210 0.6030 0.0522 0.114* 0.667 (13)
H3SB −0.0320 0.6284 −0.0209 0.114* 0.667 (13)
H3SC −0.0594 0.7285 0.0215 0.114* 0.667 (13)
O1S′ 0.1022 (3) 0.7687 (4) 0.10006 (17) 0.0797 (12) 0.333 (13)
H1SD 0.0696 0.8275 0.0843 0.120* 0.333 (13)
C1S′ 0.0726 (14) 0.6670 (16) 0.0605 (8) 0.067 (3) 0.333 (13)
H1SC 0.0546 0.6014 0.0849 0.101* 0.333 (13)
C2S′ 0.151 (3) 0.628 (6) 0.038 (3) 0.090 (3) 0.333 (13)
H2SD 0.1644 0.6905 0.0107 0.136* 0.333 (13)
H2SE 0.1355 0.5544 0.0137 0.136* 0.333 (13)
H2SF 0.2051 0.6155 0.0744 0.136* 0.333 (13)
C3S′ −0.0085 (17) 0.709 (2) 0.0081 (11) 0.076 (3) 0.333 (13)
H3SD −0.0558 0.7371 0.0261 0.114* 0.333 (13)
H3SE −0.0324 0.6438 −0.0214 0.114* 0.333 (13)
H3SF 0.0098 0.7750 −0.0147 0.114* 0.333 (13)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Na1 0.0321 (8) 0.0326 (9) 0.0875 (13) 0.0005 (7) 0.0231 (8) 0.0061 (8)
Na2 0.0311 (8) 0.0289 (8) 0.0685 (11) 0.0007 (6) 0.0165 (7) −0.0022 (7)
O1A 0.0395 (17) 0.0399 (17) 0.082 (2) 0.0108 (14) 0.0175 (16) −0.0092 (16)
O2A 0.0509 (19) 0.0496 (19) 0.060 (2) −0.0091 (15) 0.0038 (16) 0.0101 (16)
O3A 0.0307 (15) 0.0303 (15) 0.091 (2) 0.0018 (12) 0.0212 (15) −0.0036 (15)
O4A 0.0406 (17) 0.0299 (15) 0.086 (2) 0.0039 (13) 0.0164 (16) 0.0090 (15)
C1A 0.046 (2) 0.040 (2) 0.045 (2) −0.0049 (19) 0.0161 (19) 0.0008 (19)
C2A 0.0272 (19) 0.0273 (19) 0.040 (2) −0.0022 (15) 0.0125 (16) −0.0016 (16)
C3A 0.030 (2) 0.029 (2) 0.057 (3) −0.0021 (17) 0.0143 (19) −0.0115 (19)
C4A 0.051 (3) 0.060 (3) 0.064 (3) −0.029 (2) 0.044 (2) −0.033 (3)
C5A 0.082 (4) 0.078 (4) 0.086 (4) −0.010 (3) 0.043 (3) −0.020 (3)
C7A 0.076 (4) 0.117 (6) 0.062 (4) −0.041 (4) 0.031 (3) −0.011 (4)
C8A 0.087 (4) 0.098 (5) 0.068 (4) −0.043 (4) 0.015 (3) −0.016 (3)
C9A 0.065 (3) 0.061 (3) 0.041 (3) −0.034 (3) 0.015 (2) −0.004 (2)
C10A 0.028 (2) 0.029 (2) 0.054 (3) −0.0075 (16) 0.0125 (18) 0.0017 (18)
C11A 0.045 (2) 0.044 (2) 0.038 (2) −0.0060 (19) 0.0159 (19) −0.0010 (18)
C12A 0.064 (3) 0.046 (3) 0.052 (3) −0.008 (2) 0.009 (2) −0.001 (2)
C13A 0.083 (4) 0.052 (3) 0.063 (3) −0.017 (3) 0.016 (3) −0.016 (3)
C14A 0.057 (3) 0.080 (4) 0.058 (3) −0.012 (3) 0.004 (3) −0.023 (3)
C15A 0.058 (3) 0.072 (4) 0.055 (3) 0.010 (3) 0.010 (2) −0.012 (3)
C16A 0.053 (3) 0.051 (3) 0.050 (3) 0.001 (2) 0.016 (2) −0.010 (2)
C17A 0.053 (3) 0.045 (3) 0.054 (3) −0.002 (2) 0.020 (2) 0.009 (2)
C18A 0.037 (2) 0.042 (2) 0.053 (3) −0.004 (2) 0.019 (2) 0.003 (2)
C19A 0.069 (3) 0.040 (3) 0.086 (4) 0.006 (2) 0.016 (3) 0.010 (3)
O1B 0.0362 (16) 0.0323 (16) 0.094 (2) −0.0027 (13) 0.0294 (16) 0.0045 (15)
O2B 0.0440 (17) 0.0441 (17) 0.0516 (18) −0.0019 (14) 0.0112 (14) 0.0047 (14) O3B 0.0336 (15) 0.0443 (17) 0.0593 (18) −0.0079 (13) 0.0161 (13) 0.0086 (14)
O4B 0.0401 (17) 0.0387 (17) 0.103 (3) −0.0028 (14) 0.0298 (17) −0.0034 (17)
C1B 0.035 (2) 0.035 (2) 0.057 (3) −0.0030 (17) 0.0192 (19) 0.0021 (19)
C2B 0.027 (2) 0.031 (2) 0.055 (3) 0.0014 (16) 0.0140 (18) 0.0050 (18)
C3B 0.030 (2) 0.024 (2) 0.071 (3) 0.0051 (16) 0.019 (2) 0.0031 (19)
C4B 0.034 (2) 0.025 (2) 0.074 (3) 0.0082 (17) 0.005 (2) −0.004 (2)
C5B 0.039 (3) 0.034 (2) 0.104 (4) 0.002 (2) −0.003 (3) −0.007 (3)
C6B 0.058 (3) 0.048 (3) 0.099 (5) 0.006 (3) −0.023 (3) −0.021 (3)
C7B 0.082 (4) 0.049 (3) 0.083 (4) 0.015 (3) −0.003 (3) −0.011 (3)
C8B 0.067 (3) 0.048 (3) 0.060 (3) 0.014 (3) 0.003 (3) 0.000 (2)
C9B 0.042 (2) 0.035 (2) 0.058 (3) 0.007 (2) 0.003 (2) 0.000 (2)
C10B 0.031 (2) 0.035 (2) 0.051 (3) 0.0053 (18) 0.0095 (18) 0.0060 (18)
C11B 0.038 (2) 0.041 (2) 0.043 (2) −0.0002 (18) 0.0152 (18) 0.0044 (19)
C12B 0.045 (3) 0.046 (3) 0.081 (3) −0.001 (2) 0.022 (2) 0.012 (2)
C13B 0.055 (3) 0.056 (3) 0.116 (5) 0.014 (3) 0.031 (3) 0.032 (3)
C14B 0.043 (3) 0.089 (4) 0.071 (4) 0.014 (3) 0.011 (2) 0.020 (3)
C15B 0.042 (3) 0.082 (4) 0.069 (3) 0.001 (3) 0.009 (2) −0.012 (3)
C16B 0.040 (3) 0.051 (3) 0.070 (3) −0.002 (2) 0.015 (2) −0.008 (2)
C17B 0.040 (2) 0.045 (3) 0.059 (3) −0.0020 (19) 0.017 (2) −0.001 (2)
C18B 0.041 (2) 0.041 (2) 0.063 (3) 0.001 (2) 0.015 (2) 0.003 (2)
C19B 0.052 (3) 0.042 (3) 0.115 (5) 0.001 (2) 0.022 (3) −0.014 (3)
O1S 0.072 (3) 0.103 (3) 0.062 (2) 0.020 (2) 0.0153 (19) −0.022 (2)
C1S 0.079 (5) 0.062 (7) 0.063 (6) −0.010 (5) 0.025 (5) −0.009 (5)
C2S 0.095 (5) 0.096 (6) 0.091 (6) −0.004 (4) 0.044 (4) −0.029 (5)
C3S 0.089 (5) 0.076 (10) 0.066 (6) −0.007 (6) 0.027 (5) 0.002 (5)
O1S′ 0.072 (3) 0.103 (3) 0.062 (2) 0.020 (2) 0.0153 (19) −0.022 (2)
C1S′ 0.079 (5) 0.062 (7) 0.063 (6) −0.010 (5) 0.025 (5) −0.009 (5)
C2S′ 0.095 (5) 0.096 (6) 0.091 (6) −0.004 (4) 0.044 (4) −0.029 (5)
supporting information
sup-8
Acta Cryst. (2002). E58, m197–m199Geometric parameters (Å, º)
Na1—O1A 2.198 (3) O4B—C18B 1.209 (5)
Na1—O3Ai 2.271 (3) C1B—C2B 1.513 (6)
Na1—O1B 2.305 (3) C1B—C11B 1.530 (6)
Na1—O4B 2.323 (3) C1B—C17B 1.531 (6)
Na1—Na2 3.395 (2) C1B—H1BA 1.0000
Na2—O3Bii 2.279 (3) C2B—C3B 1.404 (6)
Na2—O1B 2.299 (3) C2B—C10B 1.418 (6)
Na2—O4Ai 2.309 (3) C3B—C4B 1.481 (6)
Na2—O3Ai 2.343 (3) C4B—C9B 1.386 (7)
O1A—C3A 1.256 (5) C4B—C5B 1.408 (6)
O2A—C9A 1.378 (6) C5B—C6B 1.379 (8)
O2A—C10A 1.380 (5) C5B—H5BA 0.9500
O3A—C10A 1.244 (5) C6B—C7B 1.389 (9)
O3A—Na1iii 2.271 (3) C6B—H6BA 0.9500
O3A—Na2iii 2.343 (3) C7B—C8B 1.373 (8)
O4A—C18A 1.219 (5) C7B—H7BA 0.9500
O4A—Na2iii 2.309 (3) C8B—C9B 1.389 (7)
C1A—C17A 1.513 (6) C8B—H8BA 0.9500
C1A—C2A 1.522 (5) C11B—C12B 1.384 (6)
C1A—C11A 1.528 (6) C11B—C16B 1.388 (6)
C1A—H1AA 1.0000 C12B—C13B 1.387 (7)
C2A—C3A 1.397 (5) C12B—H12B 0.9500
C2A—C10A 1.402 (5) C13B—C14B 1.377 (8)
C3A—C4A 1.460 (6) C13B—H13B 0.9500
C4A—C5A 1.370 (7) C14B—C15B 1.376 (8)
C4A—C9A 1.409 (7) C14B—H14B 0.9500
C5A—C6A 1.348 (8) C15B—C16B 1.383 (7)
C5A—H5AA 0.9500 C15B—H15B 0.9500
C6A—C7A 1.399 (9) C16B—H16B 0.9500
C6A—H6AA 0.9500 C17B—C18B 1.496 (6)
C7A—C8A 1.366 (9) C17B—H17C 0.9900
C7A—H7AA 0.9500 C17B—H17D 0.9900
C8A—C9A 1.447 (8) C18B—C19B 1.509 (6)
C8A—H8AA 0.9500 C19B—H19D 0.9800
C11A—C12A 1.385 (6) C19B—H19E 0.9800
C11A—C16A 1.394 (6) C19B—H19F 0.9800
C12A—C13A 1.392 (7) O1S—C1S 1.434 (8)
C12A—H12A 0.9500 O1S—H1SA 0.8400
C13A—C14A 1.377 (8) C1S—C3S 1.498 (11)
C13A—H13A 0.9500 C1S—C2S 1.506 (15)
C14A—C15A 1.367 (7) C1S—H1SB 1.0000
C14A—H14A 0.9500 C2S—H2SA 0.9800
C15A—C16A 1.392 (6) C2S—H2SB 0.9800
C15A—H15A 0.9500 C2S—H2SC 0.9800
C16A—H16A 0.9500 C3S—H3SA 0.9800
C17A—H17A 0.9900 C3S—H3SC 0.9800
C17A—H17B 0.9900 C1S′—C3S′ 1.505 (16)
C18A—C19A 1.505 (6) C1S′—C2S′ 1.507 (18)
C19A—H19A 0.9800 C1S′—H1SC 1.0000
C19A—H19B 0.9800 C2S′—H2SD 0.9800
C19A—H19C 0.9800 C2S′—H2SE 0.9800
O1B—C3B 1.268 (5) C2S′—H2SF 0.9800
O2B—C9B 1.372 (5) C3S′—H3SD 0.9800
O2B—C10B 1.398 (5) C3S′—H3SE 0.9800
O3B—C10B 1.224 (5) C3S′—H3SF 0.9800
O3B—Na2iv 2.279 (3)
O1A—Na1—O3Ai 93.22 (12) C3B—O1B—Na1 124.2 (2)
O1A—Na1—O1B 129.90 (15) Na2—O1B—Na1 95.01 (12)
O3Ai—Na1—O1B 83.74 (11) C9B—O2B—C10B 121.2 (3)
O1A—Na1—O4B 119.39 (13) C10B—O3B—Na2iv 151.1 (3)
O3Ai—Na1—O4B 143.13 (14) C18B—O4B—Na1 163.8 (3)
O1B—Na1—O4B 87.19 (11) C2B—C1B—C11B 112.4 (3)
O1A—Na1—Na2 127.23 (10) C2B—C1B—C17B 113.6 (3)
O3Ai—Na1—Na2 43.45 (8) C11B—C1B—C17B 112.9 (3)
O1B—Na1—Na2 42.43 (8) C2B—C1B—H1BA 105.7
O4B—Na1—Na2 112.51 (9) C11B—C1B—H1BA 105.7
O3Bii—Na2—O1B 94.74 (12) C17B—C1B—H1BA 105.7
O3Bii—Na2—O4Ai 92.14 (11) C3B—C2B—C10B 121.3 (4)
O1B—Na2—O4Ai 142.70 (14) C3B—C2B—C1B 121.6 (4)
O3Bii—Na2—O3Ai 175.43 (14) C10B—C2B—C1B 117.1 (3)
O1B—Na2—O3Ai 82.27 (11) O1B—C3B—C2B 124.5 (4)
O4Ai—Na2—O3Ai 88.20 (11) O1B—C3B—C4B 118.8 (4)
O3Bii—Na2—Na1 136.11 (10) C2B—C3B—C4B 116.7 (4)
O1B—Na2—Na1 42.56 (8) C9B—C4B—C5B 117.4 (5)
O4Ai—Na2—Na1 126.88 (9) C9B—C4B—C3B 120.2 (4)
O3Ai—Na2—Na1 41.80 (8) C5B—C4B—C3B 122.4 (5)
C3A—O1A—Na1 155.3 (3) C6B—C5B—C4B 120.3 (6)
C9A—O2A—C10A 119.5 (3) C6B—C5B—H5BA 119.9
C10A—O3A—Na1iii 138.4 (2) C4B—C5B—H5BA 119.9
C10A—O3A—Na2iii 126.4 (2) C5B—C6B—C7B 120.8 (5)
Na1iii—O3A—Na2iii 94.75 (11) C5B—C6B—H6BA 119.6
C18A—O4A—Na2iii 155.8 (3) C7B—C6B—H6BA 119.6
C17A—C1A—C2A 113.3 (3) C8B—C7B—C6B 120.0 (6)
C17A—C1A—C11A 113.8 (4) C8B—C7B—H7BA 120.0
C2A—C1A—C11A 110.7 (3) C6B—C7B—H7BA 120.0
C17A—C1A—H1AA 106.1 C7B—C8B—C9B 119.1 (6)
C2A—C1A—H1AA 106.1 C7B—C8B—H8BA 120.5
C11A—C1A—H1AA 106.1 C9B—C8B—H8BA 120.5
C3A—C2A—C10A 121.6 (4) O2B—C9B—C4B 121.0 (4)
C3A—C2A—C1A 120.5 (3) O2B—C9B—C8B 116.6 (4)
C10A—C2A—C1A 117.8 (3) C4B—C9B—C8B 122.4 (4)
supporting information
sup-10
Acta Cryst. (2002). E58, m197–m199O1A—C3A—C4A 119.1 (4) O3B—C10B—C2B 126.7 (4)
C2A—C3A—C4A 117.3 (4) O2B—C10B—C2B 119.6 (4)
C5A—C4A—C9A 116.2 (5) C12B—C11B—C16B 118.0 (4)
C5A—C4A—C3A 125.2 (5) C12B—C11B—C1B 118.7 (4)
C9A—C4A—C3A 118.6 (4) C16B—C11B—C1B 123.3 (4)
C6A—C5A—C4A 123.0 (7) C11B—C12B—C13B 120.8 (5)
C6A—C5A—H5AA 118.5 C11B—C12B—H12B 119.6
C4A—C5A—H5AA 118.5 C13B—C12B—H12B 119.6
C5A—C6A—C7A 119.7 (7) C14B—C13B—C12B 120.5 (5)
C5A—C6A—H6AA 120.2 C14B—C13B—H13B 119.7
C7A—C6A—H6AA 120.2 C12B—C13B—H13B 119.7
C8A—C7A—C6A 123.0 (6) C15B—C14B—C13B 119.2 (5)
C8A—C7A—H7AA 118.5 C15B—C14B—H14B 120.4
C6A—C7A—H7AA 118.5 C13B—C14B—H14B 120.4
C7A—C8A—C9A 114.5 (7) C14B—C15B—C16B 120.3 (5)
C7A—C8A—H8AA 122.8 C14B—C15B—H15B 119.9
C9A—C8A—H8AA 122.8 C16B—C15B—H15B 119.9
O2A—C9A—C4A 122.0 (4) C15B—C16B—C11B 121.1 (5)
O2A—C9A—C8A 114.6 (5) C15B—C16B—H16B 119.4
C4A—C9A—C8A 123.4 (5) C11B—C16B—H16B 119.4
O3A—C10A—O2A 111.0 (4) C18B—C17B—C1B 115.9 (4)
O3A—C10A—C2A 128.3 (4) C18B—C17B—H17C 108.3
O2A—C10A—C2A 120.8 (4) C1B—C17B—H17C 108.3
C12A—C11A—C16A 118.0 (4) C18B—C17B—H17D 108.3
C12A—C11A—C1A 118.4 (4) C1B—C17B—H17D 108.3
C16A—C11A—C1A 123.6 (4) H17C—C17B—H17D 107.4
C11A—C12A—C13A 120.5 (5) O4B—C18B—C17B 123.3 (4)
C11A—C12A—H12A 119.7 O4B—C18B—C19B 120.7 (4)
C13A—C12A—H12A 119.7 C17B—C18B—C19B 115.9 (4)
C14A—C13A—C12A 120.8 (5) C18B—C19B—H19D 109.5
C14A—C13A—H13A 119.6 C18B—C19B—H19E 109.5
C12A—C13A—H13A 119.6 H19D—C19B—H19E 109.5
C15A—C14A—C13A 119.3 (5) C18B—C19B—H19F 109.5
C15A—C14A—H14A 120.3 H19D—C19B—H19F 109.5
C13A—C14A—H14A 120.3 H19E—C19B—H19F 109.5
C14A—C15A—C16A 120.4 (5) O1S—C1S—C3S 111.3 (8)
C14A—C15A—H15A 119.8 O1S—C1S—C2S 106.5 (11)
C16A—C15A—H15A 119.8 C3S—C1S—C2S 114.0 (15)
C15A—C16A—C11A 121.0 (4) O1S—C1S—H1SB 108.3
C15A—C16A—H16A 119.5 C3S—C1S—H1SB 108.3
C11A—C16A—H16A 119.5 C2S—C1S—H1SB 108.3
C18A—C17A—C1A 115.1 (4) C3S′—C1S′—C2S′ 113 (2)
C18A—C17A—H17A 108.5 C3S′—C1S′—H1SC 110.4
C1A—C17A—H17A 108.5 C2S′—C1S′—H1SC 110.4
C18A—C17A—H17B 108.5 C1S′—C2S′—H2SD 109.5
C1A—C17A—H17B 108.5 C1S′—C2S′—H2SE 109.5
H17A—C17A—H17B 107.5 H2SD—C2S′—H2SE 109.5
O4A—C18A—C19A 120.5 (4) H2SD—C2S′—H2SF 109.5
C17A—C18A—C19A 113.9 (4) H2SE—C2S′—H2SF 109.5
C18A—C19A—H19A 109.5 C1S′—C3S′—H3SD 109.5
C18A—C19A—H19B 109.5 C1S′—C3S′—H3SE 109.5
H19A—C19A—H19B 109.5 H3SD—C3S′—H3SE 109.5
C18A—C19A—H19C 109.5 C1S′—C3S′—H3SF 109.5
H19A—C19A—H19C 109.5 H3SD—C3S′—H3SF 109.5
H19B—C19A—H19C 109.5 H3SE—C3S′—H3SF 109.5
C3B—O1B—Na2 140.8 (3)
O1A—Na1—Na2—O3Bii −128.41 (18) O3Bii—Na2—O1B—C3B −13.5 (5)
O3Ai—Na1—Na2—O3Bii −174.0 (2) O4Ai—Na2—O1B—C3B 86.3 (5)
O1B—Na1—Na2—O3Bii −17.13 (18) O3Ai—Na2—O1B—C3B 163.0 (5)
O4B—Na1—Na2—O3Bii 40.7 (2) Na1—Na2—O1B—C3B 178.3 (5)
O1A—Na1—Na2—O1B −111.3 (2) O3Bii—Na2—O1B—Na1 168.17 (12)
O3Ai—Na1—Na2—O1B −156.89 (19) O4Ai—Na2—O1B—Na1 −92.0 (2)
O4B—Na1—Na2—O1B 57.86 (16) O3Ai—Na2—O1B—Na1 −15.31 (13)
O1A—Na1—Na2—O4Ai 19.5 (2) O1A—Na1—O1B—C3B −74.0 (4)
O3Ai—Na1—Na2—O4Ai −26.10 (18) O3Ai—Na1—O1B—C3B −163.0 (4)
O1B—Na1—Na2—O4Ai 130.78 (19) O4B—Na1—O1B—C3B 52.8 (3)
O4B—Na1—Na2—O4Ai −171.36 (16) Na2—Na1—O1B—C3B −178.7 (4)
O1A—Na1—Na2—O3Ai 45.62 (18) O1A—Na1—O1B—Na2 104.73 (17)
O1B—Na1—Na2—O3Ai 156.89 (19) O3Ai—Na1—O1B—Na2 15.76 (13)
O4B—Na1—Na2—O3Ai −145.25 (18) O4B—Na1—O1B—Na2 −128.45 (14)
O3Ai—Na1—O1A—C3A 174.8 (7) O1A—Na1—O4B—C18B 108.0 (11)
O1B—Na1—O1A—C3A 90.2 (7) O3Ai—Na1—O4B—C18B −102.9 (12)
O4B—Na1—O1A—C3A −23.2 (8) O1B—Na1—O4B—C18B −27.2 (11)
Na2—Na1—O1A—C3A 145.3 (6) Na2—Na1—O4B—C18B −62.1 (12)
C17A—C1A—C2A—C3A 63.5 (5) C11B—C1B—C2B—C3B −117.3 (4)
C11A—C1A—C2A—C3A −65.8 (5) C17B—C1B—C2B—C3B 113.0 (4)
C17A—C1A—C2A—C10A −118.6 (4) C11B—C1B—C2B—C10B 62.3 (5)
C11A—C1A—C2A—C10A 112.1 (4) C17B—C1B—C2B—C10B −67.4 (5)
Na1—O1A—C3A—C2A 111.1 (7) Na2—O1B—C3B—C2B 98.9 (5)
Na1—O1A—C3A—C4A −68.1 (8) Na1—O1B—C3B—C2B −83.1 (4)
C10A—C2A—C3A—O1A −176.2 (4) Na2—O1B—C3B—C4B −81.4 (5)
C1A—C2A—C3A—O1A 1.7 (6) Na1—O1B—C3B—C4B 96.6 (4)
C10A—C2A—C3A—C4A 3.0 (5) C10B—C2B—C3B—O1B 179.4 (4)
C1A—C2A—C3A—C4A −179.1 (3) C1B—C2B—C3B—O1B −1.0 (6)
O1A—C3A—C4A—C5A −6.1 (6) C10B—C2B—C3B—C4B −0.2 (5)
C2A—C3A—C4A—C5A 174.6 (4) C1B—C2B—C3B—C4B 179.3 (3)
O1A—C3A—C4A—C9A 173.5 (4) O1B—C3B—C4B—C9B 178.4 (4)
C2A—C3A—C4A—C9A −5.8 (5) C2B—C3B—C4B—C9B −1.9 (5)
C9A—C4A—C5A—C6A −0.5 (8) O1B—C3B—C4B—C5B −1.1 (6)
C3A—C4A—C5A—C6A 179.2 (5) C2B—C3B—C4B—C5B 178.6 (4)
C4A—C5A—C6A—C7A −3.7 (10) C9B—C4B—C5B—C6B −0.7 (6)
C5A—C6A—C7A—C8A 4.3 (10) C3B—C4B—C5B—C6B 178.8 (4)
C6A—C7A—C8A—C9A −0.6 (8) C4B—C5B—C6B—C7B −1.7 (7)
supporting information
sup-12
Acta Cryst. (2002). E58, m197–m199C10A—O2A—C9A—C8A −179.1 (4) C6B—C7B—C8B—C9B −1.0 (7)
C5A—C4A—C9A—O2A −177.0 (4) C10B—O2B—C9B—C4B −0.9 (6)
C3A—C4A—C9A—O2A 3.3 (6) C10B—O2B—C9B—C8B 178.8 (4)
C5A—C4A—C9A—C8A 4.4 (7) C5B—C4B—C9B—O2B −178.0 (4)
C3A—C4A—C9A—C8A −175.3 (4) C3B—C4B—C9B—O2B 2.5 (6)
C7A—C8A—C9A—O2A 177.5 (4) C5B—C4B—C9B—C8B 2.4 (6)
C7A—C8A—C9A—C4A −3.8 (7) C3B—C4B—C9B—C8B −177.1 (4)
Na1iii—O3A—C10A—O2A 59.4 (5) C7B—C8B—C9B—O2B 178.8 (4)
Na2iii—O3A—C10A—O2A −111.3 (3) C7B—C8B—C9B—C4B −1.6 (7)
Na1iii—O3A—C10A—C2A −119.9 (4) Na2iv—O3B—C10B—O2B 24.2 (7)
Na2iii—O3A—C10A—C2A 69.4 (5) Na2iv—O3B—C10B—C2B −156.0 (4)
C9A—O2A—C10A—O3A 175.5 (3) C9B—O2B—C10B—O3B 178.6 (3)
C9A—O2A—C10A—C2A −5.1 (5) C9B—O2B—C10B—C2B −1.3 (5)
C3A—C2A—C10A—O3A −178.3 (4) C3B—C2B—C10B—O3B −178.0 (4)
C1A—C2A—C10A—O3A 3.8 (6) C1B—C2B—C10B—O3B 2.4 (6)
C3A—C2A—C10A—O2A 2.4 (5) C3B—C2B—C10B—O2B 1.8 (6)
C1A—C2A—C10A—O2A −175.5 (3) C1B—C2B—C10B—O2B −177.7 (3)
C17A—C1A—C11A—C12A 157.9 (4) C2B—C1B—C11B—C12B 70.2 (5)
C2A—C1A—C11A—C12A −73.1 (5) C17B—C1B—C11B—C12B −159.7 (4)
C17A—C1A—C11A—C16A −21.8 (6) C2B—C1B—C11B—C16B −112.0 (5)
C2A—C1A—C11A—C16A 107.3 (4) C17B—C1B—C11B—C16B 18.1 (6)
C16A—C11A—C12A—C13A −1.3 (7) C16B—C11B—C12B—C13B −1.7 (7)
C1A—C11A—C12A—C13A 179.1 (4) C1B—C11B—C12B—C13B 176.2 (5)
C11A—C12A—C13A—C14A 1.0 (8) C11B—C12B—C13B—C14B 0.5 (8)
C12A—C13A—C14A—C15A 0.2 (8) C12B—C13B—C14B—C15B 1.2 (9)
C13A—C14A—C15A—C16A −1.2 (8) C13B—C14B—C15B—C16B −1.6 (8)
C14A—C15A—C16A—C11A 0.9 (7) C14B—C15B—C16B—C11B 0.3 (8)
C12A—C11A—C16A—C15A 0.3 (7) C12B—C11B—C16B—C15B 1.3 (7)
C1A—C11A—C16A—C15A 180.0 (4) C1B—C11B—C16B—C15B −176.5 (4)
C2A—C1A—C17A—C18A 68.3 (5) C2B—C1B—C17B—C18B −78.5 (5)
C11A—C1A—C17A—C18A −164.0 (4) C11B—C1B—C17B—C18B 152.1 (4)
Na2iii—O4A—C18A—C17A 24.3 (10) Na1—O4B—C18B—C17B 41.1 (14)
Na2iii—O4A—C18A—C19A −157.6 (6) Na1—O4B—C18B—C19B −141.6 (9)
C1A—C17A—C18A—O4A 8.6 (7) C1B—C17B—C18B—O4B −2.0 (7)
C1A—C17A—C18A—C19A −169.6 (4) C1B—C17B—C18B—C19B −179.5 (4)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1S—H1SA···O2Bii 0.84 2.26 3.049 (5) 156
O1S—H1SA···O3Bii 0.84 2.56 3.049 (4) 118
