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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Pages m154-m155
https://doi.org/10.1107/S1600536807065221

Rubidium(I) monensinate dihydrate

Sema Öztürk Yıldırım,a Vickie McKee,b Fatim-Zahra Khardli,c Mostafa Mimounic and Taibi Ben Haddac*

aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Loughborough University, Leicestershire LE11 3TU, England, and cLaboratoire d'Activation Moléculaire, Faculté des Sciences, 60000 Oujda, Morocco
*Correspondence e-mail: tbenhadda@yahoo.fr

(Received 29 November 2007; accepted 3 December 2007; online 12 December 2007)

In the title complex, [Rb(C36H61O11)]·2H2O, the Rb+ cation is coordinated by seven O atoms of monensin. Rb—O distances range from 2.7870 (17) to 3.1429 (17) Å. Both O atoms of the carboxyl­ate group are involved in the coordination of Rb. The structure displays inter- and intra­molecular O—H⋯O and C—H⋯O hydrogen-bonding inter­actions.

Related literature

For the crystal structures of some metal and alkali-metal complexes of monensin, see: Agtarap et al. (1967[Agtarap, A., Chamberlin, J. W., Pinkerton, M. & Steinrauf, L. (1967). J. Am. Chem. Soc. 89, 5737-5739.]); Pinkerton & Steinrauf (1970[Pinkerton, M. & Steinrauf, L. K. (1970). J. Mol. Biol. 49, 533- -546.]); Walba et al. (1986[Walba, D. M., Hermsmeier, M., Haltiwanger, R. C. & Noordik, J. H. (1986). J. Org. Chem. 51, 245—247.]); Barrans et al. (1982[Barrans, Y., Alléaume, M. & Jéminet, G. (1982). Acta Cryst. B38, 1144-1149.]); Pangborn et al. (1987[Pangborn, W., Duax, W. & Langs, D. (1987). J. Am. Chem. Soc. 109, 2163-2165.]). For related literature, see: Euler et al. (2000[Euler, H., Barbier, B., Klumpp, S. & Kirfel, A. (2000). Z. Krist. New Cryst. Struct. 215, 473-476.]); Grinstein et al. (1989[Grinstein, S., Rotin, D. & Mason, M. J. (1989). Biochim. Biophys. Acta, 988, 73-93.]); Mollenhauer et al. (1990[Mollenhauer, H. H., Morre, D. J. & Rowe, L. D. (1990). Biochim. Biophys. Acta, 1031, 225-246.]); Pressman (1976[Pressman, B. C. (1976). Annu. Rev. Biochem. 45, 501-530.]); Singh et al. (2006[Singh, M., Kalla, N. R. & Sanyal, S. N. (2006). Exp. Toxicol. Pathol. 58, 203-208.]); Westley (1983[Westley, J. W. (1983). Polyether Antibiotics: Naturally Occurring Acid Ionophores, Vol. 2, pp. 51-86. New York: Marcel Dekker Inc..]); Zhu & Loh (1995[Zhu, W. H. & Loh, T. T. (1995). Biochim. Biophys. Acta, 1269, 122-128.]).

[Scheme 1]

Experimental

Crystal data

  • [Rb(C36H61O11)]·2H2O

  • Mr = 791.35

  • Orthorhombic, P 21 21 21

  • a = 12.5298 (15) Å

  • b = 16.361 (2) Å

  • c = 19.342 (2) Å

  • V = 3965.1 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.31 mm−1

  • T = 149 (2) K

  • 0.32 × 0.26 × 0.26 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.679, Tmax = 0.727

  • 39930 measured reflections

  • 9855 independent reflections

  • 8673 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.087

  • S = 1.01

  • 9855 reflections

  • 479 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.69 e Å−3

  • Δρmin = −0.42 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4380 Freidel pairs

  • Flack parameter: −0.011 (4)

Table 1
Selected bond lengths (Å)

Rb1—O1 3.1429 (17)
Rb1—O2 2.9182 (19)
Rb1—O3 2.9125 (15)
Rb1—O4 2.8178 (16)
Rb1—O5 2.8679 (16)
Rb1—O6 2.7993 (16)
Rb1—O8 2.7870 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O12—H1WA⋯O9i 0.78 (4) 2.20 (4) 2.959 (3) 167 (3)
O1—H1O⋯O11 0.86 (4) 1.82 (4) 2.651 (2) 162 (3)
O12—H1WB⋯O2 0.71 (3) 2.06 (3) 2.743 (3) 162 (4)
O2—H2O⋯O10 0.82 (4) 1.74 (4) 2.538 (3) 162 (3)
O13—H2WA⋯O1 0.92 (3) 1.93 (3) 2.807 (3) 158 (3)
O13—H2WB⋯O12ii 0.83 (4) 1.94 (4) 2.762 (3) 174 (3)
O8—H8O⋯O13 0.70 (3) 2.04 (3) 2.723 (3) 168 (3)
C10—H10B⋯O3 0.97 2.52 2.920 (3) 104
C17—H17A⋯O4 0.97 2.46 2.847 (3) 104
C18—H18A⋯O6 0.97 2.58 2.963 (3) 103
C21—H21B⋯O5 0.96 2.53 2.869 (3) 101
C29—H29⋯O6 0.98 2.60 2.924 (3) 100
C31—H31C⋯O7 0.96 2.44 2.787 (3) 101
C35—H35A⋯O9 0.96 2.43 2.813 (3) 103
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 (Version 2.1) and SAINT (Version 7.23A). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2 (Version 2.1) and SAINT (Version 7.23A). Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065221/bt2658sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065221/bt2658Isup2.hkl

checkCIF report


Comment top

Monensin is a carboxyl polyether ionophore produced by Streptomyces cinnamonensin (Mollenhauer et al., 1990). It has been known for many years in poultry industry for its useful effect as food additive. It is also well known as a Na+/H+ exchanger across biological and model membranes. Being an ionophoric antibiotic, monensin is able to form lipophilic complexes with monovalent cations, hence, can cause cation imbalances which are known to produce different biochemical and histological changes (Mollenhauer et al., 1990). We report here the synthesis and structure of a rubidium(I)-monensin complex (Fig. 1.).

The rubidium is sevenfold-coordinated via seven O atoms with Rb—O distances in the range from 2.7870 (17) Å to 3.1429 (17) Å. The oxygen atoms of the two water molecules do not coordinated to the Rb+ cation. The Rb—O distances compares with those in the range 3.06 - 3.08 reported by Euler et al. (2000).

The crystal structure is stabilized by inter- and intramolecular O—H···O and C—H···O hydrogen bonding interactions (Table 2).

Related literature top

For the crystal structures of some metal and alkali-metal complexes of monensin, see: Agtarap et al. (1967); Pinkerton & Steinrauf (1970); Walba et al. (1986); Barrans et al. (1982);Pangborn et al. (1987). For related literature, see: Euler et al. (2000); Grinstein et al. (1989); Mollenhauer et al. (1990); Pressman (1976); Singh et al. (2006); Westley (1983); Zhu & Loh (1995).

Experimental top

A mixture of monensin acid (500 mg, 0.75 mmol), and RbOCH3 (87.4 mg, 0.75 mmol) in methanol was stirred for 20 min. After this time, the solvent was evaporated under reduced pressure to dryness. The residue was dissolved in dried acetonitrile/toluene (v/v:1/2). The solution was allowed to evaporate at room temperature. After one week, crystals suitable for X-ray diffraction were obtained by recrystallization from a mixture of dried acetonitrile / toluene (v/v:1/:2).

Refinement top

The H atoms of the two water molecules and hydroxyl groups were located in a difference Fourier map and freely refined. All other H atoms were geometrically positioned and treated as riding on their parent atoms, with C—H = 0.96 (CH3), 0.97 (CH2) or 0.98 Å(CH), and with Uiso(H) = 1.5Ueq(CH3) or 1.2Ueq(CH2,CH).

Structure description top

Monensin is a carboxyl polyether ionophore produced by Streptomyces cinnamonensin (Mollenhauer et al., 1990). It has been known for many years in poultry industry for its useful effect as food additive. It is also well known as a Na+/H+ exchanger across biological and model membranes. Being an ionophoric antibiotic, monensin is able to form lipophilic complexes with monovalent cations, hence, can cause cation imbalances which are known to produce different biochemical and histological changes (Mollenhauer et al., 1990). We report here the synthesis and structure of a rubidium(I)-monensin complex (Fig. 1.).

The rubidium is sevenfold-coordinated via seven O atoms with Rb—O distances in the range from 2.7870 (17) Å to 3.1429 (17) Å. The oxygen atoms of the two water molecules do not coordinated to the Rb+ cation. The Rb—O distances compares with those in the range 3.06 - 3.08 reported by Euler et al. (2000).

The crystal structure is stabilized by inter- and intramolecular O—H···O and C—H···O hydrogen bonding interactions (Table 2).

For the crystal structures of some metal and alkali-metal complexes of monensin, see: Agtarap et al. (1967); Pinkerton & Steinrauf (1970); Walba et al. (1986); Barrans et al. (1982);Pangborn et al. (1987). For related literature, see: Euler et al. (2000); Grinstein et al. (1989); Mollenhauer et al. (1990); Pressman (1976); Singh et al. (2006); Westley (1983); Zhu & Loh (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 20% probability level. For clarity, H atoms have been omitted.
Rubidium(I) monensinate dihydrate top
Crystal data top
[Rb(C36H61O11)]·2H2OF(000) = 1688
Mr = 791.35Dx = 1.326 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 9933 reflections
a = 12.5298 (15) Åθ = 2.5–27.4°
b = 16.361 (2) ŵ = 1.31 mm−1
c = 19.342 (2) ÅT = 149 K
V = 3965.1 (8) Å3Wedge, colourless
Z = 40.32 × 0.26 × 0.26 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9855 independent reflections
Radiation source: sealed tube8673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −16→16
Tmin = 0.679, Tmax = 0.727k = −21→21
39930 measured reflectionsl = −25→25
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0519P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
9855 reflectionsΔρmax = 0.69 e Å−3
479 parametersΔρmin = −0.42 e Å−3
0 restraintsAbsolute structure: Flack (1983), 4380 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.011 (4)
Crystal data top
[Rb(C36H61O11)]·2H2OV = 3965.1 (8) Å3
Mr = 791.35Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.5298 (15) ŵ = 1.31 mm−1
b = 16.361 (2) ÅT = 149 K
c = 19.342 (2) Å0.32 × 0.26 × 0.26 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9855 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		8673 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.727Rint = 0.054
39930 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087Δρmax = 0.69 e Å−3
S = 1.01Δρmin = −0.42 e Å−3
9855 reflectionsAbsolute structure: Flack (1983), 4380 Freidel pairs
479 parametersAbsolute structure parameter: −0.011 (4)
0 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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) top
xyzUiso*/Ueq
Rb10.68058 (2)0.62540 (1)0.83254 (1)0.0275 (1)
O10.55574 (13)0.68922 (9)0.70235 (9)0.0251 (5)
O20.71406 (13)0.54905 (10)0.69792 (10)0.0308 (5)
O30.51155 (11)0.56050 (9)0.74496 (8)0.0223 (4)
O40.50828 (12)0.53649 (9)0.88830 (8)0.0259 (4)
O50.71541 (12)0.51248 (9)0.94368 (8)0.0242 (4)
O60.76779 (12)0.68235 (9)0.95677 (8)0.0239 (4)
O70.88292 (12)0.79223 (9)0.93511 (8)0.0236 (4)
O80.61547 (14)0.78001 (10)0.87589 (10)0.0302 (5)
O91.03489 (12)0.90146 (9)0.73048 (9)0.0295 (5)
O100.86292 (17)0.65349 (12)0.70870 (15)0.0650 (8)
O110.74847 (14)0.75533 (11)0.71053 (10)0.0382 (6)
C10.53415 (17)0.60717 (11)0.68444 (11)0.0226 (6)
C20.63005 (19)0.56494 (13)0.65155 (12)0.0281 (7)
C30.43701 (19)0.60519 (13)0.63593 (12)0.0279 (7)
C40.4544 (2)0.65092 (17)0.56827 (14)0.0429 (8)
C50.33877 (17)0.63550 (13)0.67509 (12)0.0291 (6)
C60.31882 (19)0.58736 (13)0.74052 (12)0.0280 (6)
C70.22450 (19)0.62327 (19)0.77985 (15)0.0419 (8)
C80.42073 (16)0.58663 (13)0.78455 (12)0.0227 (6)
C90.41327 (17)0.52918 (13)0.84666 (12)0.0266 (7)
C100.40360 (18)0.43782 (13)0.82942 (14)0.0302 (6)
C110.4651 (2)0.39624 (14)0.88795 (13)0.0320 (7)
C120.3948 (2)0.38367 (19)0.95158 (14)0.0473 (9)
C130.55770 (18)0.45711 (13)0.89552 (12)0.0258 (6)
C140.62747 (18)0.45782 (13)0.96051 (12)0.0271 (6)
C150.6740 (2)0.37246 (15)0.97546 (14)0.0400 (8)
C160.7465 (3)0.33811 (18)0.92008 (19)0.0537 (10)
C170.5754 (2)0.49580 (16)1.02467 (13)0.0343 (8)
C180.6482 (2)0.56660 (15)1.04553 (13)0.0348 (7)
C190.75078 (19)0.54845 (13)1.00711 (12)0.0260 (6)
C200.82715 (17)0.61938 (13)0.99252 (12)0.0288 (6)
C210.9200 (2)0.59105 (17)0.94769 (19)0.0488 (9)
C220.8648 (3)0.65952 (16)1.05960 (16)0.0471 (9)
C230.8526 (2)0.74925 (15)1.04981 (13)0.0388 (8)
C240.80195 (18)0.76179 (13)0.97872 (11)0.0254 (6)
C250.7057 (2)0.81916 (15)0.97967 (12)0.0315 (7)
C260.66921 (17)0.84601 (13)0.90796 (12)0.0251 (6)
C270.76439 (15)0.87581 (13)0.86451 (11)0.0230 (5)
C280.80635 (19)0.95721 (14)0.89261 (14)0.0331 (7)
C290.85077 (16)0.80908 (12)0.86470 (11)0.0211 (6)
C300.95440 (16)0.83083 (12)0.82654 (12)0.0229 (6)
C311.03786 (17)0.76331 (14)0.83467 (14)0.0310 (7)
C320.94094 (16)0.85553 (12)0.75006 (12)0.0236 (6)
C331.0276 (2)0.98639 (15)0.74268 (17)0.0426 (9)
C340.93353 (18)0.78700 (14)0.69649 (13)0.0286 (7)
C350.9230 (2)0.82303 (18)0.62323 (14)0.0415 (9)
C360.84047 (18)0.72763 (14)0.70674 (12)0.0275 (7)
O120.73374 (18)0.38982 (14)0.74038 (13)0.0476 (8)
O130.45804 (17)0.81107 (12)0.78250 (10)0.0396 (6)
H1O0.622 (3)0.7020 (17)0.6994 (16)0.044 (8)*
H2A0.606700.513700.631500.0340*
H2B0.656800.599000.614300.0340*
H2O0.758 (3)0.586 (2)0.6933 (17)0.052 (10)*
H30.424100.547800.624100.0330*
H4A0.516400.629500.545300.0640*
H4B0.464900.708000.577700.0640*
H4C0.393100.644100.539100.0640*
H5A0.348400.692700.686800.0350*
H5B0.276700.631300.645300.0350*
H60.301500.530900.727800.0340*
H7A0.212500.592200.821200.0630*
H7B0.161900.621200.751300.0630*
H7C0.239600.679000.791800.0630*
H80.434000.642200.801400.0270*
H8O0.578 (2)0.7943 (17)0.8520 (15)0.031 (8)*
H90.351600.545200.874700.0320*
H10A0.329500.420600.829000.0360*
H10B0.435400.425700.784900.0360*
H110.492600.343400.872000.0380*
H12A0.435700.357800.987400.0710*
H12B0.335200.349700.939600.0710*
H12C0.369500.435600.967700.0710*
H130.605100.449400.855800.0310*
H15A0.713700.375001.018500.0480*
H15B0.615300.334700.982300.0480*
H16A0.771500.285100.934000.0810*
H16B0.806300.374000.913600.0810*
H16C0.707700.333400.877500.0810*
H17A0.504300.515501.014000.0410*
H17B0.570400.456001.061700.0410*
H18A0.618300.618701.031300.0420*
H18B0.659800.567401.095100.0420*
H190.790000.506701.033200.0310*
H21A0.966800.636300.938800.0730*
H21B0.893200.570200.904700.0730*
H21C0.958600.548800.971300.0730*
H22A0.821900.641001.098300.0570*
H22B0.938800.645801.068700.0570*
H23A0.921700.776001.051900.0470*
H23B0.807400.772001.085600.0470*
H25A0.646800.791901.002700.0380*
H25B0.723600.867301.006500.0380*
H260.618800.891400.913200.0300*
H270.740200.884200.816800.0280*
H28A0.865700.975100.865100.0500*
H28B0.829000.950200.939600.0500*
H28C0.750700.997400.890700.0500*
H290.821000.759100.844500.0250*
H300.983500.878900.850100.0270*
H31A1.102000.778800.810900.0460*
H31B1.010800.713400.815400.0460*
H31C1.053100.755400.882800.0460*
H320.878100.890800.745700.0280*
H33A1.092701.012400.728500.0640*
H33B1.016200.996000.791100.0640*
H33C0.969001.008500.716800.0640*
H341.000000.755500.698400.0340*
H35A0.980600.860500.614900.0620*
H35B0.856200.851400.619300.0620*
H35C0.925600.779700.589800.0620*
H1WA0.795 (3)0.385 (2)0.7462 (19)0.059 (11)*
H1WB0.729 (3)0.433 (2)0.738 (2)0.057 (12)*
H2WA0.478 (3)0.776 (2)0.7474 (18)0.053 (9)*
H2WB0.401 (3)0.834 (2)0.7728 (18)0.051 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rb10.0285 (1)0.0310 (1)0.0231 (1)−0.0076 (1)−0.0049 (1)0.0030 (1)
O10.0241 (8)0.0192 (7)0.0319 (9)−0.0007 (6)0.0014 (7)−0.0050 (6)
O20.0241 (8)0.0246 (8)0.0437 (10)0.0021 (6)0.0034 (7)−0.0006 (7)
O30.0208 (7)0.0226 (7)0.0236 (8)0.0022 (5)0.0009 (6)−0.0009 (6)
O40.0265 (8)0.0252 (7)0.0260 (8)−0.0027 (6)−0.0048 (7)−0.0020 (6)
O50.0243 (7)0.0269 (7)0.0214 (8)−0.0056 (6)0.0004 (6)−0.0014 (6)
O60.0243 (8)0.0235 (7)0.0239 (8)−0.0007 (6)−0.0054 (6)0.0031 (6)
O70.0228 (7)0.0244 (7)0.0236 (8)0.0011 (6)−0.0073 (6)0.0013 (6)
O80.0205 (8)0.0322 (9)0.0380 (10)0.0009 (7)−0.0049 (8)0.0039 (7)
O90.0211 (7)0.0299 (8)0.0374 (10)−0.0057 (6)0.0018 (7)0.0054 (7)
O100.0373 (11)0.0296 (9)0.128 (2)−0.0031 (8)−0.0201 (13)0.0073 (12)
O110.0262 (8)0.0324 (9)0.0559 (12)−0.0054 (7)0.0093 (8)−0.0108 (8)
C10.0270 (10)0.0191 (10)0.0216 (10)0.0007 (7)0.0006 (8)−0.0028 (7)
C20.0322 (12)0.0260 (10)0.0260 (12)0.0011 (9)0.0066 (9)−0.0067 (8)
C30.0334 (12)0.0238 (11)0.0265 (11)−0.0017 (8)−0.0076 (10)−0.0038 (8)
C40.0530 (16)0.0439 (14)0.0317 (14)−0.0035 (12)−0.0150 (13)0.0051 (11)
C50.0285 (11)0.0257 (10)0.0331 (12)0.0006 (8)−0.0134 (10)−0.0007 (9)
C60.0223 (10)0.0264 (10)0.0352 (12)−0.0006 (9)−0.0032 (11)−0.0055 (9)
C70.0237 (11)0.0535 (15)0.0486 (15)0.0044 (12)−0.0045 (11)−0.0113 (14)
C80.0184 (9)0.0216 (10)0.0280 (11)0.0006 (8)0.0002 (9)−0.0050 (8)
C90.0208 (10)0.0316 (11)0.0274 (13)−0.0044 (8)−0.0008 (9)−0.0029 (9)
C100.0300 (11)0.0281 (10)0.0326 (12)−0.0089 (8)−0.0057 (11)−0.0004 (10)
C110.0362 (12)0.0273 (11)0.0326 (13)−0.0113 (9)−0.0064 (11)0.0023 (9)
C120.0438 (15)0.0568 (17)0.0414 (15)−0.0259 (14)−0.0036 (12)0.0145 (14)
C130.0287 (11)0.0247 (10)0.0241 (11)−0.0043 (9)−0.0030 (9)0.0005 (8)
C140.0281 (11)0.0272 (11)0.0260 (11)−0.0075 (9)0.0004 (9)0.0026 (9)
C150.0478 (14)0.0286 (11)0.0437 (14)−0.0091 (13)−0.0167 (12)0.0089 (11)
C160.0525 (18)0.0327 (14)0.076 (2)0.0074 (13)−0.0059 (17)0.0012 (14)
C170.0327 (13)0.0481 (14)0.0220 (12)−0.0100 (10)0.0021 (10)0.0009 (10)
C180.0443 (14)0.0371 (12)0.0231 (12)−0.0081 (10)0.0040 (10)−0.0031 (10)
C190.0307 (11)0.0249 (10)0.0223 (11)−0.0019 (8)−0.0097 (9)0.0033 (8)
C200.0239 (10)0.0271 (10)0.0355 (11)−0.0015 (10)−0.0118 (10)0.0070 (9)
C210.0253 (12)0.0362 (13)0.085 (2)0.0023 (10)0.0074 (14)0.0082 (14)
C220.0594 (18)0.0330 (12)0.0489 (17)−0.0097 (12)−0.0364 (15)0.0071 (12)
C230.0549 (16)0.0352 (12)0.0264 (13)0.0092 (11)−0.0099 (12)−0.0033 (10)
C240.0290 (12)0.0255 (10)0.0217 (10)0.0011 (8)−0.0014 (9)−0.0018 (8)
C250.0366 (13)0.0318 (11)0.0262 (12)0.0076 (9)0.0043 (10)0.0010 (9)
C260.0214 (10)0.0283 (10)0.0257 (11)0.0063 (8)0.0008 (9)0.0010 (8)
C270.0200 (9)0.0234 (9)0.0257 (10)0.0041 (9)−0.0031 (8)0.0030 (9)
C280.0300 (12)0.0250 (10)0.0444 (14)0.0049 (9)−0.0061 (11)−0.0017 (10)
C290.0184 (9)0.0210 (9)0.0240 (11)0.0012 (7)−0.0034 (8)0.0011 (8)
C300.0176 (9)0.0240 (10)0.0271 (11)−0.0008 (7)−0.0022 (9)0.0016 (9)
C310.0220 (10)0.0326 (11)0.0383 (13)0.0041 (8)0.0035 (11)0.0096 (11)
C320.0168 (9)0.0261 (11)0.0279 (11)−0.0013 (7)0.0006 (9)0.0051 (8)
C330.0358 (14)0.0265 (11)0.0654 (19)−0.0065 (10)0.0033 (13)0.0095 (12)
C340.0220 (11)0.0309 (11)0.0329 (13)−0.0020 (9)0.0036 (10)0.0000 (9)
C350.0443 (15)0.0494 (16)0.0308 (14)−0.0174 (12)0.0044 (12)0.0022 (12)
C360.0265 (12)0.0302 (11)0.0258 (12)−0.0038 (8)−0.0018 (9)−0.0004 (9)
O120.0313 (11)0.0356 (12)0.0760 (16)−0.0033 (8)−0.0084 (10)0.0165 (10)
O130.0387 (10)0.0425 (10)0.0375 (11)0.0157 (8)−0.0112 (9)−0.0140 (8)
Geometric parameters (Å, º) top
Rb1—O13.1429 (17)C32—C341.530 (3)
Rb1—O22.9182 (19)C34—C351.540 (4)
Rb1—O32.9125 (15)C34—C361.531 (3)
Rb1—O42.8178 (16)C2—H2B0.9700
Rb1—O52.8679 (16)C2—H2A0.9700
Rb1—O62.7993 (16)C3—H30.9800
Rb1—O82.7870 (17)C4—H4A0.9600
O1—C11.413 (2)C4—H4B0.9600
O2—C21.407 (3)C4—H4C0.9600
O3—C11.426 (3)C5—H5A0.9700
O3—C81.437 (3)C5—H5B0.9700
O4—C91.442 (3)C6—H60.9800
O4—C131.446 (3)C7—H7B0.9600
O5—C141.456 (3)C7—H7C0.9600
O5—C191.431 (3)C7—H7A0.9600
O6—C201.447 (3)C8—H80.9800
O6—C241.433 (3)C9—H90.9800
O7—C241.410 (3)C10—H10B0.9700
O7—C291.447 (3)C10—H10A0.9700
O8—C261.416 (3)C11—H110.9800
O9—C321.447 (3)C12—H12B0.9600
O9—C331.412 (3)C12—H12C0.9600
O10—C361.246 (3)C12—H12A0.9600
O11—C361.241 (3)C13—H130.9800
O1—H1O0.86 (4)C15—H15A0.9700
O2—H2O0.82 (4)C15—H15B0.9700
O8—H8O0.70 (3)C16—H16B0.9600
O12—H1WA0.78 (4)C16—H16C0.9600
O12—H1WB0.71 (3)C16—H16A0.9600
O13—H2WB0.83 (4)C17—H17A0.9700
O13—H2WA0.92 (3)C17—H17B0.9700
C1—C21.525 (3)C18—H18B0.9700
C1—C31.537 (3)C18—H18A0.9700
C3—C41.523 (4)C19—H190.9800
C3—C51.528 (3)C21—H21B0.9600
C5—C61.511 (3)C21—H21C0.9600
C6—C81.535 (3)C21—H21A0.9600
C6—C71.523 (4)C22—H22A0.9700
C8—C91.528 (3)C22—H22B0.9700
C9—C101.536 (3)C23—H23A0.9700
C10—C111.529 (4)C23—H23B0.9700
C11—C121.527 (4)C25—H25A0.9700
C11—C131.536 (3)C25—H25B0.9700
C13—C141.531 (3)C26—H260.9800
C14—C151.541 (3)C27—H270.9800
C14—C171.534 (3)C28—H28A0.9600
C15—C161.513 (4)C28—H28B0.9600
C17—C181.529 (4)C28—H28C0.9600
C18—C191.514 (3)C29—H290.9800
C19—C201.530 (3)C30—H300.9800
C20—C211.523 (4)C31—H31B0.9600
C20—C221.529 (4)C31—H31C0.9600
C22—C231.488 (4)C31—H31A0.9600
C23—C241.528 (3)C32—H320.9800
C24—C251.528 (3)C33—H33A0.9600
C25—C261.525 (3)C33—H33B0.9600
C26—C271.538 (3)C33—H33C0.9600
C27—C281.532 (3)C34—H340.9800
C27—C291.537 (3)C35—H35B0.9600
C29—C301.535 (3)C35—H35C0.9600
C30—C311.529 (3)C35—H35A0.9600
C30—C321.543 (3)
Rb1···O103.342 (3)H2WB···H1WBv2.31 (5)
Rb1···O113.2881 (19)H4A···C22.7100
Rb1···C293.737 (2)H4A···H2B2.2600
Rb1···C363.568 (2)H4B···H11v2.4800
Rb1···H21B3.1400H4B···O12.6800
Rb1···H292.8200H4B···H5A2.5800
Rb1···H33Ai3.5900H4B···H15Bv2.5800
O1···O23.033 (2)H4C···H5B2.5300
O1···O112.651 (2)H5A···H82.6000
O1···O132.807 (3)H5A···O12.6200
O2···O122.743 (3)H5A···H2WA2.4200
O2···C363.328 (3)H5A···H4B2.5800
O2···O32.702 (2)H5A···H7C2.4600
O2···O102.538 (3)H5B···H28Ciii2.3200
O2···O13.033 (2)H5B···H4C2.5300
O3···O22.702 (2)H5B···H7B2.5100
O3···C133.417 (3)H6···H28Ciii2.4500
O3···O42.801 (2)H6···C102.8000
O4···O52.835 (2)H6···H32.5400
O4···O32.801 (2)H6···C28iii2.9500
O5···O62.867 (2)H7A···H92.1700
O5···O42.835 (2)H7A···C92.7600
O6···O82.940 (2)H7B···H5B2.5100
O6···O52.867 (2)H7B···H33Ciii2.5400
O7···C213.333 (3)H7C···C31vii3.0000
O8···O132.723 (3)H7C···H5A2.4600
O8···O62.940 (2)H7C···H82.5200
O9···O12ii2.959 (3)H7C···H31Avii2.4000
O10···C33i3.200 (3)H8···O12.5700
O10···O22.538 (3)H8···O132.8000
O10···Rb13.342 (3)H8···H2WA2.4900
O11···Rb13.2881 (19)H8···H5A2.6000
O11···C293.363 (3)H8···H7C2.5200
O11···O12.651 (2)H8O···O132.04 (3)
O12···O22.743 (3)H8O···H2WA2.40 (5)
O12···C33i3.398 (3)H8O···H272.6000
O12···O9i2.959 (3)H8O···H22Biv2.5200
O12···O13iii2.762 (3)H9···C72.7400
O13···O82.723 (3)H9···C123.0800
O13···C22iv3.305 (4)H9···H7A2.1700
O13···O12v2.762 (3)H9···H12C2.5500
O13···O12.807 (3)H10A···H12B2.4300
O1···H2WA1.93 (3)H10B···O32.5200
O1···H5A2.6200H10B···H132.5600
O1···H82.5700H10B···O13iii2.6500
O1···H4B2.6800H11···C153.0700
O2···H1O2.76 (3)H11···H2WAiii2.5900
O2···H33Ai2.8700H11···H4Biii2.4800
O2···H1WB2.06 (3)H12A···C142.9500
O3···H10B2.5200H12A···C153.0000
O4···H12C2.8500H12A···C172.9500
O4···H17A2.4600H12A···H15B2.2800
O5···H21B2.5300H12B···H10A2.4300
O5···H16B2.6000H12C···O42.8500
O6···H18A2.5800H12C···C172.9700
O6···H292.6000H12C···H92.5500
O7···H31C2.4400H12C···C92.8500
O7···H21A2.7600H12C···H17A2.3200
O7···H28B2.6700H13···H10B2.5600
O8···H22Biv2.7400H13···H16C2.3300
O8···H292.6700H13···C162.8300
O9···H35A2.4300H15A···H17B2.3800
O9···H1WAii2.20 (4)H15A···H192.3700
O9···H31A2.6700H15A···C192.8800
O10···H2O1.74 (4)H15A···H2Bx2.5000
O10···H33Ai2.6700H15B···H12A2.2800
O11···H322.8300H15B···H17B2.5700
O11···H292.7500H15B···C112.8100
O11···H35B2.7200H15B···C122.9400
O11···H2O2.79 (3)H15B···H4Biii2.5800
O11···H1O1.82 (4)H16B···O52.6000
O12···H31Ai2.9200H16C···O122.8300
O12···H16C2.8300H16C···H132.3300
O12···H2WBiii1.94 (4)H16C···C132.7800
O12···H22Avi2.8800H17A···C122.8300
O13···H8O2.04 (3)H17A···O42.4600
O13···H82.8000H17A···H28Biv2.4400
O13···H10Bv2.6500H17A···H12C2.3200
C7···C31vii3.441 (4)H17B···H15A2.3800
C12···C153.533 (4)H17B···H15B2.5700
C12···C173.238 (4)H18A···O62.5800
C15···C123.533 (4)H18B···C223.0600
C17···C123.238 (4)H18B···H22A2.3600
C21···O73.333 (3)H19···H22A2.5600
C22···O13viii3.305 (4)H19···H21C2.5200
C29···C363.336 (3)H19···C152.8600
C29···O113.363 (3)H19···H15A2.3700
C29···Rb13.737 (2)H19···C2x2.7600
C31···C363.547 (3)H19···H2Ax2.3200
C31···C7ix3.441 (4)H19···H2Bx2.4300
C33···O12ii3.398 (3)H21A···O72.7600
C33···O10ii3.200 (3)H21A···C243.0100
C36···C293.336 (3)H21A···C313.0300
C36···C313.547 (3)H21A···H22B2.5400
C36···O23.328 (3)H21A···H31C2.4800
C36···Rb13.568 (2)H21B···Rb13.1400
C1···H2WA3.10 (3)H21B···O52.5300
C2···H1WB3.00 (4)H21C···H192.5200
C2···H19vi2.7600H21C···H22B2.4800
C2···H4A2.7100H22A···C182.6900
C3···H28Ciii2.9800H22A···H18B2.3600
C4···H2B2.8200H22A···H192.5600
C5···H28Ciii2.8300H22A···O12x2.8800
C6···H28Ciii3.0600H22B···H21A2.5400
C7···H92.7400H22B···H21C2.4800
C7···H31Avii3.0300H22B···O8viii2.7400
C7···H33Ciii3.0700H22B···C26viii2.9300
C9···H12C2.8500H22B···H8Oviii2.5200
C9···H7A2.7600H22B···H26viii2.3600
C10···H62.8000H23B···H25A2.5900
C11···H15B2.8100H23B···H25B2.4200
C12···H15B2.9400H25A···H23B2.5900
C12···H93.0800H25B···C282.8400
C12···H17A2.8300H25B···H23B2.4200
C13···H16C2.7800H25B···H28B2.2900
C14···H12A2.9500H26···H28C2.4300
C15···H192.8600H26···H22Biv2.3600
C15···H113.0700H27···C322.8700
C15···H12A3.0000H27···H8O2.6000
C16···H132.8300H27···H322.2100
C17···H12C2.9700H28A···C302.7100
C17···H12A2.9500H28A···H302.1800
C18···H22A2.6900H28A···H33B2.3900
C18···H30iv3.0200H28B···C252.7500
C19···H15A2.8800H28B···O72.6700
C22···H18B3.0600H28B···H25B2.2900
C24···H21A3.0100H28B···H17Aviii2.4400
C25···H28B2.7500H28C···H5Bv2.3200
C26···H22Biv2.9300H28C···H262.4300
C27···H322.7100H28C···C3v2.9800
C28···H25B2.8400H28C···C5v2.8300
C28···H6v2.9500H28C···C6v3.0600
C28···H302.6900H28C···H3v2.3600
C30···H28A2.7100H28C···H6v2.4500
C30···H33B2.8900H29···H31B2.5600
C31···H21A3.0300H29···Rb12.8200
C31···H342.6800H29···O62.6000
C31···H7Cix3.0000H29···O82.6700
C32···H272.8700H29···O112.7500
C33···H302.7800H29···C362.7200
C33···H1WAii2.78 (4)H30···H28A2.1800
C34···H31A3.0600H30···C282.6900
C34···H31B2.7700H30···C332.7800
C36···H31B3.0000H30···H33B2.2700
C36···H292.7200H30···C18viii3.0200
C36···H1O2.77 (4)H31A···H342.5500
C36···H2O2.55 (3)H31A···O92.6700
H1WA···O9i2.20 (4)H31A···C7ix3.0300
H1WA···H33Ai2.5600H31A···C343.0600
H1WA···C33i2.78 (4)H31A···H7Cix2.4000
H1WA···H31Ai2.4300H31A···O12ii2.9200
H1O···C362.77 (4)H31A···H1WAii2.4300
H1O···O111.82 (4)H31B···C342.7700
H1O···H2B2.4000H31B···C363.0000
H1O···H2O2.55 (5)H31B···H292.5600
H1O···H2WA2.36 (5)H31B···H342.3700
H1WB···C23.00 (4)H31C···O72.4400
H1WB···H2WBiii2.31 (5)H31C···H21A2.4800
H1WB···O22.06 (3)H32···O112.8300
H2A···H32.3600H32···C272.7100
H2A···H19vi2.3200H32···H272.2100
H2B···C42.8200H32···H33B2.5900
H2B···H1O2.4000H32···H33C2.3100
H2B···H4A2.2600H32···H35B2.5400
H2B···H15Avi2.5000H33A···Rb1ii3.5900
H2B···H19vi2.4300H33A···O2ii2.8700
H2O···C362.55 (3)H33A···O10ii2.6700
H2O···H1O2.55 (5)H33A···H1WAii2.5600
H2O···O101.74 (4)H33B···C302.8900
H2O···O112.79 (3)H33B···H28A2.3900
H3···H2A2.3600H33B···H302.2700
H3···H28Ciii2.3600H33B···H322.5900
H3···H62.5400H33C···H322.3100
H2WA···C13.10 (3)H33C···C7v3.0700
H2WA···O11.93 (3)H33C···H7Bv2.5400
H2WA···H8O2.40 (5)H34···C312.6800
H2WA···H11v2.5900H34···H31A2.5500
H2WA···H1O2.36 (5)H34···H31B2.3700
H2WA···H5A2.4200H35A···O92.4300
H2WA···H82.4900H35B···O112.7200
H2WB···O12v1.94 (4)H35B···H322.5400
O1—Rb1—O259.93 (4)C3—C4—H4A109.00
O1—Rb1—O345.03 (4)C3—C4—H4B110.00
O1—Rb1—O495.56 (4)H4B—C4—H4C110.00
O1—Rb1—O5152.91 (4)H4A—C4—H4C109.00
O1—Rb1—O6140.48 (4)H4A—C4—H4B109.00
O1—Rb1—O878.10 (5)C6—C5—H5A109.00
O2—Rb1—O355.22 (4)C6—C5—H5B109.00
O2—Rb1—O4103.34 (5)H5A—C5—H5B108.00
O2—Rb1—O5111.79 (5)C3—C5—H5B109.00
O2—Rb1—O6148.46 (5)C3—C5—H5A109.00
O2—Rb1—O8134.35 (5)C8—C6—H6108.00
O3—Rb1—O458.49 (4)C5—C6—H6109.00
O3—Rb1—O5108.17 (4)C7—C6—H6108.00
O3—Rb1—O6154.75 (4)C6—C7—H7C110.00
O3—Rb1—O8107.04 (5)H7A—C7—H7B109.00
O4—Rb1—O559.81 (4)H7A—C7—H7C109.00
O4—Rb1—O698.18 (4)H7B—C7—H7C109.00
O4—Rb1—O897.42 (5)C6—C7—H7A109.00
O5—Rb1—O660.76 (4)C6—C7—H7B109.00
O5—Rb1—O8113.81 (5)O3—C8—H8109.00
O6—Rb1—O863.51 (5)C9—C8—H8109.00
Rb1—O1—C188.63 (11)C6—C8—H8109.00
Rb1—O2—C2112.46 (13)C8—C9—H9109.00
Rb1—O3—C197.92 (11)C10—C9—H9109.00
Rb1—O3—C899.06 (11)O4—C9—H9109.00
C1—O3—C8115.82 (15)C11—C10—H10A111.00
Rb1—O4—C9117.48 (12)C9—C10—H10A111.00
Rb1—O4—C1399.94 (11)C9—C10—H10B111.00
C9—O4—C13109.45 (16)H10A—C10—H10B109.00
Rb1—O5—C14116.62 (12)C11—C10—H10B111.00
Rb1—O5—C19115.14 (12)C12—C11—H11110.00
C14—O5—C19107.17 (16)C10—C11—H11110.00
Rb1—O6—C20111.96 (12)C13—C11—H11110.00
Rb1—O6—C24132.29 (12)C11—C12—H12B109.00
C20—O6—C24110.54 (16)C11—C12—H12A109.00
C24—O7—C29115.47 (16)H12A—C12—H12C109.00
Rb1—O8—C26133.23 (13)H12B—C12—H12C110.00
C32—O9—C33114.49 (17)H12A—C12—H12B110.00
C1—O1—H1O113.6 (19)C11—C12—H12C109.00
Rb1—O1—H1O70 (2)C11—C13—H13107.00
Rb1—O2—H2O83 (2)O4—C13—H13107.00
C2—O2—H2O107 (2)C14—C13—H13107.00
Rb1—O8—H8O108 (2)C14—C15—H15B108.00
C26—O8—H8O111 (2)C14—C15—H15A108.00
H1WA—O12—H1WB101 (4)H15A—C15—H15B107.00
H2WA—O13—H2WB110 (3)C16—C15—H15A108.00
O3—C1—C3109.42 (17)C16—C15—H15B108.00
O3—C1—C2104.85 (16)C15—C16—H16A109.00
O1—C1—C3108.75 (16)H16A—C16—H16B110.00
O1—C1—C2112.46 (17)C15—C16—H16B110.00
O1—C1—O3110.22 (17)C15—C16—H16C109.00
C2—C1—C3111.08 (18)H16B—C16—H16C109.00
O2—C2—C1114.03 (19)H16A—C16—H16C109.00
C1—C3—C4113.63 (19)C14—C17—H17B111.00
C4—C3—C5112.44 (19)C18—C17—H17A111.00
C1—C3—C5109.18 (18)H17A—C17—H17B109.00
C3—C5—C6112.28 (18)C18—C17—H17B111.00
C7—C6—C8111.80 (19)C14—C17—H17A111.00
C5—C6—C7110.2 (2)C17—C18—H18A111.00
C5—C6—C8109.33 (18)C19—C18—H18B111.00
O3—C8—C9106.52 (16)H18A—C18—H18B109.00
C6—C8—C9112.96 (17)C17—C18—H18B111.00
O3—C8—C6111.44 (18)C19—C18—H18A111.00
O4—C9—C8109.72 (17)C20—C19—H19108.00
O4—C9—C10105.49 (17)O5—C19—H19108.00
C8—C9—C10115.6 (2)C18—C19—H19108.00
C9—C10—C11103.44 (19)C20—C21—H21C109.00
C10—C11—C1399.37 (18)H21A—C21—H21B109.00
C10—C11—C12111.5 (2)H21A—C21—H21C109.00
C12—C11—C13116.5 (2)H21B—C21—H21C109.00
O4—C13—C14108.49 (17)C20—C21—H21A110.00
C11—C13—C14120.96 (19)C20—C21—H21B110.00
O4—C13—C11104.46 (17)C20—C22—H22A110.00
O5—C14—C15108.20 (18)C23—C22—H22B110.00
C13—C14—C17115.12 (19)C20—C22—H22B110.00
O5—C14—C13104.67 (17)C23—C22—H22A110.00
C13—C14—C15111.30 (18)H22A—C22—H22B109.00
C15—C14—C17112.1 (2)C22—C23—H23B110.00
O5—C14—C17104.72 (17)C24—C23—H23A110.00
C14—C15—C16115.5 (2)H23A—C23—H23B109.00
C14—C17—C18105.5 (2)C24—C23—H23B110.00
C17—C18—C19103.20 (19)C22—C23—H23A110.00
O5—C19—C18103.80 (18)C24—C25—H25A109.00
O5—C19—C20110.33 (18)C26—C25—H25B109.00
C18—C19—C20118.20 (19)H25A—C25—H25B108.00
C19—C20—C22111.2 (2)C24—C25—H25B109.00
O6—C20—C19107.86 (17)C26—C25—H25A109.00
C19—C20—C21110.60 (19)O8—C26—H26108.00
C21—C20—C22112.2 (2)C25—C26—H26109.00
O6—C20—C21109.7 (2)C27—C26—H26108.00
O6—C20—C22104.97 (18)C26—C27—H27109.00
C20—C22—C23106.5 (2)C29—C27—H27109.00
C22—C23—C24106.8 (2)C28—C27—H27109.00
O7—C24—C25110.98 (17)C27—C28—H28B110.00
C23—C24—C25113.54 (19)C27—C28—H28A110.00
O6—C24—C23105.60 (17)H28A—C28—H28C109.00
O6—C24—C25108.96 (18)C27—C28—H28C109.00
O7—C24—C23106.67 (18)H28A—C28—H28B109.00
O6—C24—O7110.98 (17)H28B—C28—H28C109.00
C24—C25—C26113.74 (19)C30—C29—H29109.00
O8—C26—C25108.75 (18)O7—C29—H29109.00
C25—C26—C27110.84 (18)C27—C29—H29109.00
O8—C26—C27111.79 (18)C31—C30—H30106.00
C28—C27—C29112.03 (17)C29—C30—H30106.00
C26—C27—C29108.63 (17)C32—C30—H30106.00
C26—C27—C28110.36 (18)C30—C31—H31B109.00
O7—C29—C27109.49 (16)C30—C31—H31A109.00
O7—C29—C30105.14 (16)H31A—C31—H31C110.00
C27—C29—C30115.45 (16)H31B—C31—H31C109.00
C29—C30—C31111.19 (17)C30—C31—H31C109.00
C31—C30—C32111.26 (18)H31A—C31—H31B110.00
C29—C30—C32115.42 (17)C34—C32—H32109.00
O9—C32—C34104.64 (17)O9—C32—H32109.00
O9—C32—C30107.34 (17)C30—C32—H32109.00
C30—C32—C34117.66 (17)O9—C33—H33C109.00
C32—C34—C36115.07 (19)H33A—C33—H33B109.00
C32—C34—C35110.4 (2)H33A—C33—H33C110.00
C35—C34—C36107.26 (19)H33B—C33—H33C109.00
O11—C36—C34118.9 (2)O9—C33—H33B109.00
O10—C36—C34116.7 (2)O9—C33—H33A109.00
O10—C36—O11124.3 (2)C35—C34—H34108.00
O2—C2—H2A109.00C32—C34—H34108.00
C1—C2—H2B109.00C36—C34—H34108.00
O2—C2—H2B109.00C34—C35—H35B109.00
C1—C2—H2A109.00C34—C35—H35C110.00
H2A—C2—H2B108.00H35A—C35—H35C109.00
C4—C3—H3107.00H35B—C35—H35C109.00
C5—C3—H3107.00H35A—C35—H35B109.00
C1—C3—H3107.00C34—C35—H35A110.00
C3—C4—H4C109.00
O2—Rb1—O1—C145.16 (11)C24—O6—C20—C21−96.4 (2)
O3—Rb1—O1—C1−24.16 (10)Rb1—O6—C20—C22−177.83 (16)
O4—Rb1—O1—C1−57.05 (11)C20—O6—C24—C25−144.76 (17)
O5—Rb1—O1—C1−33.88 (16)Rb1—O6—C20—C19−59.13 (18)
O6—Rb1—O1—C1−167.10 (10)Rb1—O6—C24—C23−174.19 (13)
O8—Rb1—O1—C1−153.49 (12)Rb1—O6—C24—C2563.5 (2)
O1—Rb1—O2—C2−19.70 (12)C20—O6—C24—C23−22.5 (2)
O3—Rb1—O2—C233.98 (12)C29—O7—C24—O666.0 (2)
O4—Rb1—O2—C269.02 (14)C24—O7—C29—C30−173.25 (16)
O5—Rb1—O2—C2131.52 (13)C29—O7—C24—C25−55.3 (2)
O6—Rb1—O2—C2−159.23 (12)C29—O7—C24—C23−179.48 (16)
O8—Rb1—O2—C2−45.65 (16)C24—O7—C29—C2762.1 (2)
O1—Rb1—O3—C124.15 (10)Rb1—O8—C26—C2758.1 (2)
O2—Rb1—O3—C1−56.15 (10)Rb1—O8—C26—C25−64.6 (2)
O4—Rb1—O3—C1164.80 (12)C33—O9—C32—C30−88.8 (2)
O5—Rb1—O3—C1−160.49 (10)C33—O9—C32—C34145.5 (2)
O6—Rb1—O3—C1140.13 (12)O3—C1—C2—O2−49.1 (2)
O8—Rb1—O3—C176.49 (11)O1—C1—C3—C5−64.8 (2)
O1—Rb1—O3—C8−93.72 (12)O1—C1—C2—O270.7 (2)
O2—Rb1—O3—C8−174.02 (13)O3—C1—C3—C4−177.94 (18)
O4—Rb1—O3—C846.93 (11)C2—C1—C3—C5170.96 (17)
O5—Rb1—O3—C881.64 (12)C3—C1—C2—O2−167.20 (17)
O6—Rb1—O3—C822.26 (17)O3—C1—C3—C555.7 (2)
O8—Rb1—O3—C8−41.38 (12)O1—C1—C3—C461.6 (2)
O1—Rb1—O4—C97.54 (13)C2—C1—C3—C4−62.7 (2)
O2—Rb1—O4—C9−52.83 (13)C1—C3—C5—C6−55.6 (2)
O3—Rb1—O4—C9−19.25 (12)C4—C3—C5—C6177.33 (19)
O5—Rb1—O4—C9−160.49 (14)C3—C5—C6—C853.2 (2)
O6—Rb1—O4—C9150.39 (13)C3—C5—C6—C7176.45 (19)
O8—Rb1—O4—C986.23 (13)C7—C6—C8—O3−174.11 (19)
O1—Rb1—O4—C13125.72 (12)C7—C6—C8—C966.0 (2)
O2—Rb1—O4—C1365.35 (12)C5—C6—C8—C9−171.68 (18)
O3—Rb1—O4—C1398.93 (12)C5—C6—C8—O3−51.8 (2)
O5—Rb1—O4—C13−42.32 (11)O3—C8—C9—O461.7 (2)
O6—Rb1—O4—C13−91.43 (12)C6—C8—C9—O4−175.61 (17)
O8—Rb1—O4—C13−155.60 (12)O3—C8—C9—C10−57.4 (2)
O1—Rb1—O5—C14−15.42 (18)C6—C8—C9—C1065.3 (2)
O2—Rb1—O5—C14−81.62 (13)O4—C9—C10—C1124.3 (2)
O3—Rb1—O5—C14−22.65 (14)C8—C9—C10—C11145.68 (19)
O4—Rb1—O5—C1411.52 (12)C9—C10—C11—C1284.7 (2)
O6—Rb1—O5—C14132.48 (14)C9—C10—C11—C13−38.7 (2)
O8—Rb1—O5—C1496.16 (13)C12—C11—C13—O4−79.4 (2)
O1—Rb1—O5—C19−142.30 (13)C12—C11—C13—C1443.1 (3)
O2—Rb1—O5—C19151.50 (13)C10—C11—C13—O440.4 (2)
O3—Rb1—O5—C19−149.52 (13)C10—C11—C13—C14162.8 (2)
O4—Rb1—O5—C19−115.35 (14)C11—C13—C14—O5170.54 (18)
O6—Rb1—O5—C195.60 (13)O4—C13—C14—C1745.4 (2)
O8—Rb1—O5—C19−30.71 (15)O4—C13—C14—C15174.40 (18)
O1—Rb1—O6—C20−174.06 (11)O4—C13—C14—O5−69.0 (2)
O2—Rb1—O6—C20−56.05 (16)C11—C13—C14—C17−75.1 (3)
O3—Rb1—O6—C2097.85 (15)C11—C13—C14—C1553.9 (3)
O4—Rb1—O6—C2076.78 (13)O5—C14—C15—C16−52.7 (3)
O5—Rb1—O6—C2028.29 (12)C17—C14—C15—C16−167.7 (2)
O8—Rb1—O6—C20171.03 (14)C13—C14—C15—C1661.8 (3)
O1—Rb1—O6—C24−22.6 (2)O5—C14—C17—C18−6.7 (2)
O2—Rb1—O6—C2495.38 (18)C15—C14—C17—C18110.4 (2)
O3—Rb1—O6—C24−110.73 (18)C13—C14—C17—C18−121.0 (2)
O4—Rb1—O6—C24−131.80 (16)C14—C17—C18—C19−16.7 (2)
O5—Rb1—O6—C24179.71 (18)C17—C18—C19—C20157.2 (2)
O8—Rb1—O6—C24−37.55 (16)C17—C18—C19—O534.7 (2)
O1—Rb1—O8—C26−131.8 (2)O5—C19—C20—O664.6 (2)
O2—Rb1—O8—C26−109.08 (19)O5—C19—C20—C21−55.4 (3)
O3—Rb1—O8—C26−166.75 (18)C18—C19—C20—C21−174.5 (2)
O4—Rb1—O8—C26134.01 (19)C18—C19—C20—C2260.1 (3)
O5—Rb1—O8—C2673.8 (2)C18—C19—C20—O6−54.6 (3)
O6—Rb1—O8—C2638.53 (18)O5—C19—C20—C22179.2 (2)
Rb1—O1—C1—O339.06 (14)C21—C20—C22—C23102.9 (3)
Rb1—O1—C1—C2−77.54 (16)C19—C20—C22—C23−132.6 (2)
Rb1—O1—C1—C3159.00 (15)O6—C20—C22—C23−16.2 (3)
Rb1—O2—C2—C1−8.4 (2)C20—C22—C23—C243.2 (3)
C8—O3—C1—O160.8 (2)C22—C23—C24—C25130.5 (2)
Rb1—O3—C1—C277.91 (14)C22—C23—C24—O611.2 (3)
C8—O3—C1—C2−177.97 (16)C22—C23—C24—O7−107.0 (2)
Rb1—O3—C1—C3−162.87 (13)C23—C24—C25—C26167.94 (19)
C8—O3—C1—C3−58.8 (2)O6—C24—C25—C26−74.7 (2)
Rb1—O3—C8—C6160.65 (14)O7—C24—C25—C2647.8 (3)
C1—O3—C8—C657.2 (2)C24—C25—C26—O874.8 (2)
Rb1—O3—C1—O1−43.34 (16)C24—C25—C26—C27−48.5 (3)
C1—O3—C8—C9−179.16 (16)O8—C26—C27—C28168.45 (18)
Rb1—O3—C8—C9−75.74 (15)O8—C26—C27—C29−68.4 (2)
C9—O4—C13—C11−27.0 (2)C25—C26—C27—C28−70.1 (2)
Rb1—O4—C13—C11−150.96 (14)C25—C26—C27—C2953.1 (2)
C13—O4—C9—C101.7 (2)C28—C27—C29—C30−54.8 (2)
Rb1—O4—C9—C8−10.6 (2)C28—C27—C29—O763.6 (2)
C13—O4—C9—C8−123.50 (18)C26—C27—C29—C30−176.98 (18)
C9—O4—C13—C14−157.26 (17)C26—C27—C29—O7−58.6 (2)
Rb1—O4—C13—C1478.78 (16)O7—C29—C30—C3154.8 (2)
Rb1—O4—C9—C10114.64 (15)C27—C29—C30—C32−56.5 (2)
C14—O5—C19—C18−40.8 (2)O7—C29—C30—C32−177.30 (16)
Rb1—O5—C19—C1890.72 (16)C27—C29—C30—C31175.53 (18)
Rb1—O5—C19—C20−36.9 (2)C29—C30—C32—O9159.25 (16)
Rb1—O5—C14—C17−101.14 (16)C31—C30—C32—C3444.7 (2)
Rb1—O5—C14—C1320.36 (19)C29—C30—C32—C34−83.2 (2)
C19—O5—C14—C1729.6 (2)C31—C30—C32—O9−72.9 (2)
C19—O5—C14—C13151.08 (17)O9—C32—C34—C35−59.7 (2)
Rb1—O5—C14—C15139.13 (15)O9—C32—C34—C36178.77 (18)
C19—O5—C14—C15−90.2 (2)C30—C32—C34—C35−178.69 (18)
C14—O5—C19—C20−168.41 (17)C30—C32—C34—C3659.8 (3)
Rb1—O6—C24—O7−59.0 (2)C32—C34—C36—O10−127.2 (3)
C20—O6—C24—O792.8 (2)C32—C34—C36—O1154.9 (3)
C24—O6—C20—C2224.4 (2)C35—C34—C36—O10109.6 (3)
C24—O6—C20—C19143.07 (18)C35—C34—C36—O11−68.3 (3)
Rb1—O6—C20—C2161.40 (19)
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1/2, −y+3/2, −z+2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+3/2, −y+1, z−1/2; (vii) x−1, y, z; (viii) x+1/2, −y+3/2, −z+2; (ix) x+1, y, z; (x) −x+3/2, −y+1, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H1WA···O9i0.78 (4)2.20 (4)2.959 (3)167 (3)
O1—H1O···O110.86 (4)1.82 (4)2.651 (2)162 (3)
O12—H1WB···O20.71 (3)2.06 (3)2.743 (3)162 (4)
O2—H2O···O100.82 (4)1.74 (4)2.538 (3)162 (3)
O13—H2WA···O10.92 (3)1.93 (3)2.807 (3)158 (3)
O13—H2WB···O12v0.83 (4)1.94 (4)2.762 (3)174 (3)
O8—H8O···O130.70 (3)2.04 (3)2.723 (3)168 (3)
C10—H10B···O30.972.522.920 (3)104
C17—H17A···O40.972.462.847 (3)104
C18—H18A···O60.972.582.963 (3)103
C21—H21B···O50.962.532.869 (3)101
C29—H29···O60.982.602.924 (3)100
C31—H31C···O70.962.442.787 (3)101
C35—H35A···O90.962.432.813 (3)103
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula[Rb(C36H61O11)]·2H2O
Mr791.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)149
a, b, c (Å)12.5298 (15), 16.361 (2), 19.342 (2)
V (Å3)3965.1 (8)
Z4
Radiation typeMo Kα
µ (mm−1)1.31
Crystal size (mm)0.32 × 0.26 × 0.26
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.679, 0.727
No. of measured, independent and
observed [I > 2σ(I)] reflections		39930, 9855, 8673
Rint0.054
(sin θ/λ)max (Å−1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 1.01
No. of reflections9855
No. of parameters479
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.69, −0.42
Absolute structureFlack (1983), 4380 Freidel pairs
Absolute structure parameter−0.011 (4)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Rb1—O13.1429 (17)Rb1—O52.8679 (16)
Rb1—O22.9182 (19)Rb1—O62.7993 (16)
Rb1—O32.9125 (15)Rb1—O82.7870 (17)
Rb1—O42.8178 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H1WA···O9i0.78 (4)2.20 (4)2.959 (3)167 (3)
O1—H1O···O110.86 (4)1.82 (4)2.651 (2)162 (3)
O12—H1WB···O20.71 (3)2.06 (3)2.743 (3)162 (4)
O2—H2O···O100.82 (4)1.74 (4)2.538 (3)162 (3)
O13—H2WA···O10.92 (3)1.93 (3)2.807 (3)158 (3)
O13—H2WB···O12ii0.83 (4)1.94 (4)2.762 (3)174 (3)
O8—H8O···O130.70 (3)2.04 (3)2.723 (3)168 (3)
C10—H10B···O30.972.522.920 (3)104
C17—H17A···O40.972.462.847 (3)104
C18—H18A···O60.972.582.963 (3)103
C21—H21B···O50.962.532.869 (3)101
C29—H29···O60.982.602.924 (3)100
C31—H31C···O70.962.442.787 (3)101
C35—H35A···O90.962.432.813 (3)103
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2.
 

Acknowledgements

The authors acknowledge Professor Georges Jeminet and the Agence Universitaire de la Francophonie for sending us the ionophore ligands (lasalocid, monensin and calcimycin). This work was also supported by the Ministry of National Education of Morocco (grants PGR-BH-2005 and CUD-UMP-BH-2007).

References

First citationAgtarap, A., Chamberlin, J. W., Pinkerton, M. & Steinrauf, L. (1967). J. Am. Chem. Soc. 89, 5737–5739.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBarrans, Y., Alléaume, M. & Jéminet, G. (1982). Acta Cryst. B38, 1144–1149.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBruker (2005). APEX2 (Version 2.1) and SAINT (Version 7.23A). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationEuler, H., Barbier, B., Klumpp, S. & Kirfel, A. (2000). Z. Krist. New Cryst. Struct. 215, 473–476.  CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGrinstein, S., Rotin, D. & Mason, M. J. (1989). Biochim. Biophys. Acta, 988, 73–93.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationMollenhauer, H. H., Morre, D. J. & Rowe, L. D. (1990). Biochim. Biophys. Acta, 1031, 225–246.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationPangborn, W., Duax, W. & Langs, D. (1987). J. Am. Chem. Soc. 109, 2163–2165.  CSD CrossRef CAS Web of Science Google Scholar
 First citationPinkerton, M. & Steinrauf, L. K. (1970). J. Mol. Biol. 49, 533– -546.  Google Scholar
 First citationPressman, B. C. (1976). Annu. Rev. Biochem. 45, 501–530.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSingh, M., Kalla, N. R. & Sanyal, S. N. (2006). Exp. Toxicol. Pathol. 58, 203–208.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationWalba, D. M., Hermsmeier, M., Haltiwanger, R. C. & Noordik, J. H. (1986). J. Org. Chem. 51, 245—247.  CSD CrossRef Web of Science Google Scholar
 First citationWestley, J. W. (1983). Polyether Antibiotics: Naturally Occurring Acid Ionophores, Vol. 2, pp. 51–86. New York: Marcel Dekker Inc..  Google Scholar
 First citationZhu, W. H. & Loh, T. T. (1995). Biochim. Biophys. Acta, 1269, 122–128.  CrossRef PubMed Web of Science Google Scholar

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Volume 64| Part 1| January 2008| Pages m154-m155
https://doi.org/10.1107/S1600536807065221
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