supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, m753    [ doi:10.1107/S1600536809021394 ]

catena-Poly[[(ethanol-[kappa]O)sodium(I)]-di-[mu]-aqua-[(rac-2'-hydroxy-1,1'-binaphthyl-2-yl phosphato-[kappa]O)sodium]-tri-[mu]-aqua]

Y. Tachibana and Y. Maeda

Abstract top

The asymmetric unit of the polymeric title compound, [Na2(C20H13O5P)(C2H6O)(H2O)5]n, consists of two NaI ions, one 2'-hydroxy-1,1'-binaphthyl-2-yl phosphate anion, one ethanol ligand and five water molecules of crysallization. Each NaI ion has a distorted octahedral coordination geometry. The phosphate anion coordinates to one NaI ion and the ethanol molecule coordinates to the other. The five water molecules bridge the NaI ions, forming an inorganic chain structure along the b axis. The chains are connected by O-H...O hydrogen bonds into an organic-inorganic hybrid layer parallel to (001).

Comment top

In recent years, studies on organic-inorganic hybrid layered materials have received a great deal of attention as electrical, magnetic and/or optical materials (Eckert & Ward, 2001). Some combinations are studied to form layered structure. Phosphate ester can form organic-inorganic hybrid network (Vioux et al., 2004).

The title compound has inorganic layer formed with two sodium cation, phosphate anion and five waters, and organic layer formed by binaphthyl unit. The phosphate anion coordinates to one NaI atom and the ethanol molecule coordinates to the other NaI atom as shown in Fig. 1. Sodium ions in the compound are bridged by three water molecules, and one sodium ion connected to adjoining sodium ion through two water molecules to form a one-dimensional zigzag chain structure along the b axis as shown in Fig. 2. The chains build two-dimensional network along the a-b plane by hydrogen bonding, and form inorganic layer. Organic layers, build up with binaphthyl moiety, and inorganic layers form bilayered structure in the crystal. Then, three-dimensional organic-inorganic hybrid layered material is formed by self-assembly as shown in Fig. 3.

Related literature top

For organic–inorganic hybrid materials, see: Eckert & Ward (2001). For phosphate derivatives, see: Vioux et al. (2004).

Experimental top

Sodium hydride (1.5 g, 63 mmol) was dispersed into tetrahydrofuran (50 ml). (rac)-1,1'-Binaphtyl-2,2'-diyl hydrogenphosphate (1.0 g, 2.9 mmol) was added to the dispersion and stirred for 2 h at room temperature. The resulting mixture was filtrated and evaporated in vacuo. The residue was recrystallized from H2O/ethanol.

Refinement top

All C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). O-bound H atoms were located in a difference Fourier map and the positional parameters were refined, with distance restraints of O—H = 0.850 (5) Å, and with Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top
[Figure 1] Fig. 1. A view of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The one dimensional chain structure of the title compound bridged between sodium cations and water molecules. Hydrogen atoms have been omitted for clarity.
[Figure 3] Fig. 3. The layered structure of the title compound. Hydrogen atoms have been omitted for clarity.
catena-Poly[[(ethanol-κO)sodium(I)]-di-µ-aqua- [(rac-2'-hydroxy-1,1'-binaphthyl-2-yl phosphato-κO)sodium]- tri-µ-aqua] top
Crystal data top
[Na2(C20H13O5P)(C2H6O)(H2O)5]F(000) = 1144
Mr = 546.40Dx = 1.417 Mg m−3
Monoclinic, P21/aMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yabCell parameters from 19717 reflections
a = 13.121 (4) Åθ = 3.1–27.5°
b = 9.816 (3) ŵ = 0.20 mm−1
c = 20.198 (7) ÅT = 293 K
β = 100.033 (13)°Platelet, colourless
V = 2561.7 (14) Å30.60 × 0.50 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5829 independent reflections
Radiation source: fine-focus sealed tube5045 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 5.00 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −16→16
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −12→12
Tmin = 0.874, Tmax = 0.980l = −26→26
24950 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0682P)2 + 0.7208P]
where P = (Fo2 + 2Fc2)/3
5829 reflections(Δ/σ)max = 0.006
326 parametersΔρmax = 0.36 e Å−3
12 restraintsΔρmin = −0.46 e Å−3
Crystal data top
[Na2(C20H13O5P)(C2H6O)(H2O)5]V = 2561.7 (14) Å3
Mr = 546.40Z = 4
Monoclinic, P21/aMo Kα radiation
a = 13.121 (4) ŵ = 0.20 mm−1
b = 9.816 (3) ÅT = 293 K
c = 20.198 (7) Å0.60 × 0.50 × 0.10 mm
β = 100.033 (13)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5829 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		5045 reflections with I > 2σ(I)
Tmin = 0.874, Tmax = 0.980Rint = 0.035
24950 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114Δρmax = 0.36 e Å−3
S = 1.05Δρmin = −0.46 e Å−3
5829 reflectionsAbsolute structure: ?
326 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
P10.57919 (3)−0.04823 (4)0.124182 (17)0.02333 (10)
Na10.66932 (5)0.48279 (7)0.07453 (3)0.03971 (17)
Na20.74134 (4)0.17009 (6)0.04642 (3)0.03330 (15)
O10.40206 (9)0.09598 (13)0.21979 (6)0.0394 (3)
H10.4489 (12)0.098 (2)0.1958 (9)0.047*
O20.61673 (8)−0.09564 (10)0.20212 (5)0.0282 (2)
O30.50549 (8)−0.16097 (12)0.09628 (5)0.0350 (2)
O40.52559 (9)0.08848 (11)0.12794 (5)0.0338 (2)
O50.67384 (8)−0.03767 (11)0.09123 (5)0.0318 (2)
O60.89693 (9)0.06153 (12)0.03525 (6)0.0361 (3)
H20.9272 (14)0.0031 (16)0.0631 (8)0.043*
H30.9421 (12)0.1229 (15)0.0342 (10)0.043*
O70.82327 (8)0.39178 (13)0.03833 (6)0.0352 (2)
H40.8329 (15)0.410 (2)−0.0014 (4)0.042*
H50.8815 (8)0.408 (2)0.0629 (9)0.042*
O80.72026 (10)0.30040 (13)0.14616 (6)0.0392 (3)
H60.7723 (11)0.322 (2)0.1753 (8)0.047*
H70.6828 (13)0.2551 (19)0.1684 (9)0.047*
O90.56093 (8)0.26022 (11)0.02832 (6)0.0326 (2)
H80.5482 (14)0.2058 (16)0.0587 (7)0.039*
H90.5390 (14)0.2237 (19)−0.0097 (5)0.039*
O100.77621 (10)0.69039 (13)0.08084 (7)0.0434 (3)
H100.7540 (16)0.7654 (13)0.0938 (11)0.052*
H110.8397 (6)0.685 (2)0.0986 (11)0.052*
O110.53790 (10)0.58034 (12)0.13535 (7)0.0420 (3)
H120.5281 (17)0.6642 (8)0.1257 (11)0.050*
C10.40429 (11)−0.01837 (17)0.25947 (8)0.0318 (3)
C20.30914 (12)−0.0869 (2)0.25809 (9)0.0424 (4)
H130.2496−0.05410.23100.051*
C30.30408 (13)−0.2003 (2)0.29597 (9)0.0437 (4)
H140.2409−0.24410.29460.052*
C40.39363 (13)−0.25268 (17)0.33747 (8)0.0350 (3)
C50.39111 (16)−0.37427 (19)0.37466 (9)0.0443 (4)
H150.3285−0.41920.37380.053*
C60.47905 (18)−0.4266 (2)0.41165 (10)0.0522 (5)
H160.4769−0.50890.43420.063*
C70.57301 (17)−0.3559 (2)0.41573 (10)0.0518 (5)
H170.6325−0.39080.44210.062*
C80.57852 (13)−0.23620 (18)0.38149 (8)0.0387 (4)
H180.6412−0.19010.38550.046*
C90.48927 (11)−0.18220 (16)0.34002 (7)0.0296 (3)
C100.49298 (11)−0.06224 (15)0.30036 (7)0.0273 (3)
C110.59188 (10)0.01444 (15)0.30256 (7)0.0266 (3)
C120.62733 (11)0.10678 (16)0.35622 (7)0.0314 (3)
C130.57337 (15)0.1248 (2)0.41085 (9)0.0479 (4)
H190.51300.07600.41190.057*
C140.60945 (19)0.2133 (3)0.46178 (11)0.0629 (6)
H200.57420.22250.49770.076*
C150.6995 (2)0.2907 (3)0.46050 (11)0.0657 (6)
H210.72240.35200.49500.079*
C160.75278 (17)0.2760 (2)0.40923 (11)0.0552 (5)
H220.81220.32760.40900.066*
C170.71954 (13)0.18328 (17)0.35570 (8)0.0366 (3)
C180.77548 (12)0.16267 (18)0.30267 (9)0.0378 (4)
H230.83560.21240.30180.045*
C190.74264 (11)0.07110 (16)0.25277 (8)0.0324 (3)
H240.78150.05630.21910.039*
C200.64935 (10)−0.00130 (14)0.25234 (7)0.0254 (3)
C210.50869 (18)0.5732 (2)0.20062 (11)0.0533 (5)
H25A0.43740.60270.19740.064*
H25B0.55200.63430.23110.064*
C220.5196 (2)0.4332 (3)0.22760 (13)0.0656 (6)
H26A0.47970.37190.19630.098*
H26B0.49520.42980.26970.098*
H26C0.59120.40690.23440.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.02712 (18)0.02280 (18)0.02071 (17)0.00115 (12)0.00595 (13)0.00013 (12)
Na10.0399 (3)0.0389 (4)0.0434 (4)0.0078 (3)0.0157 (3)0.0124 (3)
Na20.0303 (3)0.0315 (3)0.0398 (3)0.0013 (2)0.0108 (2)−0.0015 (2)
O10.0335 (6)0.0470 (7)0.0395 (6)0.0102 (5)0.0115 (5)0.0121 (5)
O20.0382 (5)0.0252 (5)0.0213 (4)0.0023 (4)0.0055 (4)0.0011 (4)
O30.0374 (6)0.0348 (6)0.0310 (5)−0.0085 (5)0.0014 (4)−0.0008 (4)
O40.0436 (6)0.0302 (5)0.0298 (5)0.0115 (4)0.0129 (4)0.0058 (4)
O50.0348 (5)0.0337 (6)0.0298 (5)0.0000 (4)0.0140 (4)−0.0013 (4)
O60.0301 (5)0.0311 (6)0.0471 (7)0.0012 (4)0.0069 (5)0.0030 (5)
O70.0312 (5)0.0442 (7)0.0317 (5)−0.0035 (5)0.0094 (4)0.0010 (5)
O80.0485 (7)0.0384 (6)0.0303 (6)−0.0044 (5)0.0061 (5)0.0050 (5)
O90.0353 (5)0.0310 (6)0.0316 (5)−0.0027 (4)0.0060 (4)0.0041 (4)
O100.0425 (6)0.0415 (7)0.0460 (7)0.0006 (5)0.0072 (5)−0.0023 (6)
O110.0536 (7)0.0299 (6)0.0456 (7)−0.0019 (5)0.0174 (6)−0.0030 (5)
C10.0301 (7)0.0380 (8)0.0288 (7)0.0010 (6)0.0090 (6)0.0006 (6)
C20.0279 (7)0.0583 (11)0.0403 (9)−0.0027 (7)0.0040 (6)0.0043 (8)
C30.0341 (8)0.0551 (11)0.0430 (9)−0.0138 (7)0.0097 (7)−0.0037 (8)
C40.0441 (8)0.0363 (8)0.0269 (7)−0.0080 (6)0.0128 (6)−0.0057 (6)
C50.0632 (11)0.0386 (9)0.0338 (8)−0.0153 (8)0.0160 (8)−0.0045 (7)
C60.0842 (14)0.0346 (9)0.0402 (9)−0.0060 (9)0.0172 (10)0.0040 (7)
C70.0646 (12)0.0474 (11)0.0419 (10)0.0110 (9)0.0050 (9)0.0099 (8)
C80.0402 (8)0.0425 (9)0.0335 (8)0.0031 (7)0.0067 (6)0.0035 (7)
C90.0350 (7)0.0322 (7)0.0233 (6)−0.0012 (6)0.0100 (5)−0.0029 (5)
C100.0280 (6)0.0321 (7)0.0233 (6)−0.0007 (5)0.0082 (5)−0.0026 (5)
C110.0265 (6)0.0290 (7)0.0240 (6)0.0011 (5)0.0038 (5)0.0011 (5)
C120.0334 (7)0.0329 (8)0.0274 (7)0.0030 (6)0.0036 (6)−0.0035 (6)
C130.0491 (10)0.0577 (11)0.0386 (9)0.0016 (8)0.0127 (8)−0.0150 (8)
C140.0748 (14)0.0704 (15)0.0446 (11)0.0068 (12)0.0132 (10)−0.0261 (10)
C150.0786 (15)0.0637 (14)0.0491 (12)0.0000 (12)−0.0043 (11)−0.0303 (10)
C160.0561 (11)0.0489 (11)0.0544 (11)−0.0094 (9)−0.0077 (9)−0.0139 (9)
C170.0384 (8)0.0325 (8)0.0359 (8)−0.0015 (6)−0.0022 (6)−0.0021 (6)
C180.0322 (7)0.0380 (9)0.0413 (9)−0.0078 (6)0.0014 (6)0.0058 (7)
C190.0301 (7)0.0378 (8)0.0305 (7)−0.0010 (6)0.0087 (6)0.0065 (6)
C200.0278 (6)0.0251 (6)0.0226 (6)0.0022 (5)0.0027 (5)0.0022 (5)
C210.0634 (12)0.0490 (11)0.0548 (11)0.0026 (9)0.0304 (10)−0.0034 (9)
C220.0689 (14)0.0647 (14)0.0716 (15)0.0061 (11)0.0359 (12)0.0165 (12)
Geometric parameters (Å, °) top
P1—O51.5112 (11)C3—H140.9300
P1—O31.5124 (11)C4—C51.414 (2)
P1—O41.5231 (11)C4—C91.426 (2)
P1—O21.6330 (11)C5—C61.361 (3)
Na1—O82.3256 (14)C5—H150.9300
Na1—O6i2.3660 (16)C6—C71.405 (3)
Na1—O72.4347 (14)C6—H160.9300
Na1—O102.4645 (16)C7—C81.371 (3)
Na1—O112.4773 (15)C7—H170.9300
Na1—O92.6842 (15)C8—C91.418 (2)
Na2—O62.3484 (14)C8—H180.9300
Na2—O82.4423 (15)C9—C101.430 (2)
Na2—O72.4453 (15)C10—C111.494 (2)
Na2—O52.4581 (14)C11—C201.374 (2)
Na2—O92.4937 (14)C11—C121.427 (2)
Na2—O10ii2.5483 (17)C12—C171.426 (2)
O1—C11.377 (2)C12—C131.422 (2)
O1—H10.847 (17)C13—C141.366 (3)
O2—C201.3850 (17)C13—H190.9300
O6—H20.852 (16)C14—C151.408 (4)
O6—H30.848 (16)C14—H200.9300
O7—H40.853 (11)C15—C161.354 (3)
O7—H50.851 (14)C15—H210.9300
O8—H60.847 (16)C16—C171.423 (2)
O8—H70.847 (18)C16—H220.9300
O9—H80.852 (15)C17—C181.415 (3)
O9—H90.851 (12)C18—C191.363 (2)
O10—H100.850 (15)C18—H230.9300
O10—H110.849 (12)C19—C201.414 (2)
O11—C211.437 (2)C19—H240.9300
O11—H120.851 (9)C21—C221.476 (3)
C1—C101.374 (2)C21—H25A0.9700
C1—C21.414 (2)C21—H25B0.9700
C2—C31.359 (3)C22—H26A0.9600
C2—H130.9300C22—H26B0.9600
C3—C41.416 (3)C22—H26C0.9600
Na1···Na23.2900 (13)Na2···H32.728 (17)
Na1···Na2i3.4236 (12)Na2···H82.612 (18)
O5—P1—O3114.03 (7)C10—C1—O1122.37 (14)
O5—P1—O4112.55 (6)C10—C1—C2121.02 (15)
O3—P1—O4113.11 (7)O1—C1—C2116.57 (14)
O5—P1—O2108.12 (6)C3—C2—C1120.54 (16)
O3—P1—O2102.51 (6)C3—C2—H13119.7
O4—P1—O2105.51 (6)C1—C2—H13119.7
O8—Na1—O6i148.58 (5)C2—C3—C4120.93 (15)
O8—Na1—O774.98 (5)C2—C3—H14119.5
O6i—Na1—O791.55 (5)C4—C3—H14119.5
O8—Na1—O10120.34 (5)C3—C4—C5121.83 (16)
O6i—Na1—O1083.76 (5)C3—C4—C9118.65 (15)
O7—Na1—O1079.89 (5)C5—C4—C9119.49 (16)
O8—Na1—O1197.96 (5)C6—C5—C4120.94 (18)
O6i—Na1—O1199.48 (5)C6—C5—H15119.5
O7—Na1—O11167.51 (5)C4—C5—H15119.5
O10—Na1—O1195.38 (5)C5—C6—C7119.82 (18)
O8—Na1—O970.56 (5)C5—C6—H16120.1
O6i—Na1—O981.61 (4)C7—C6—H16120.1
O7—Na1—O990.80 (5)C8—C7—C6121.10 (18)
O10—Na1—O9162.42 (5)C8—C7—H17119.5
O11—Na1—O996.58 (5)C6—C7—H17119.5
O6—Na2—O8122.83 (5)C7—C8—C9120.48 (17)
O6—Na2—O789.87 (5)C7—C8—H18119.8
O8—Na2—O772.74 (5)C9—C8—H18119.8
O6—Na2—O591.94 (5)C8—C9—C4118.09 (15)
O8—Na2—O591.78 (5)C8—C9—C10122.24 (14)
O7—Na2—O5162.52 (5)C4—C9—C10119.66 (14)
O6—Na2—O9164.98 (5)C1—C10—C9119.15 (14)
O8—Na2—O972.19 (4)C1—C10—C11120.03 (14)
O7—Na2—O995.26 (5)C9—C10—C11120.82 (13)
O5—Na2—O987.40 (4)C20—C11—C12118.94 (13)
O6—Na2—O10ii82.29 (5)C20—C11—C10120.45 (13)
O8—Na2—O10ii141.97 (5)C12—C11—C10120.60 (13)
O7—Na2—O10ii80.01 (4)C17—C12—C13118.56 (15)
O5—Na2—O10ii117.47 (5)C17—C12—C11119.58 (14)
O9—Na2—O10ii84.71 (5)C13—C12—C11121.87 (15)
C1—O1—H1113.9 (15)C14—C13—C12120.6 (2)
C20—O2—P1121.22 (9)C14—C13—H19119.7
P1—O5—Na2126.55 (6)C12—C13—H19119.7
Na2—O6—Na1ii93.14 (5)C13—C14—C15120.7 (2)
Na2—O6—H2123.8 (14)C13—C14—H20119.6
Na1ii—O6—H2116.8 (15)C15—C14—H20119.6
Na2—O6—H3107.7 (14)C16—C15—C14120.21 (18)
Na1ii—O6—H3110.7 (14)C16—C15—H21119.9
H2—O6—H3104.2 (19)C14—C15—H21119.9
Na1—O7—Na284.78 (4)C15—C16—C17121.2 (2)
Na1—O7—H4118.2 (14)C15—C16—H22119.4
Na2—O7—H4112.7 (14)C17—C16—H22119.4
Na1—O7—H5117.6 (14)C18—C17—C12118.90 (14)
Na2—O7—H5119.4 (14)C18—C17—C16122.43 (17)
H4—O7—H5104.1 (19)C12—C17—C16118.66 (17)
Na1—O8—Na287.23 (5)C19—C18—C17121.02 (14)
Na1—O8—H6110.2 (15)C19—C18—H23119.5
Na2—O8—H6120.8 (15)C17—C18—H23119.5
Na1—O8—H7127.1 (14)C18—C19—C20119.86 (14)
Na2—O8—H7108.8 (15)C18—C19—H24120.1
H6—O8—H7104 (2)C20—C19—H24120.1
Na2—O9—Na178.81 (4)C11—C20—O2118.46 (12)
Na2—O9—H888.3 (13)C11—C20—C19121.64 (13)
Na1—O9—H8114.7 (13)O2—C20—C19119.82 (13)
Na2—O9—H998.4 (13)O11—C21—C22111.06 (17)
Na1—O9—H9137.1 (14)O11—C21—H25A109.4
H8—O9—H9107.9 (19)C22—C21—H25A109.4
Na1—O10—Na2i86.13 (5)O11—C21—H25B109.4
Na1—O10—H10120.7 (15)C22—C21—H25B109.4
Na2i—O10—H10113.8 (16)H25A—C21—H25B108.0
Na1—O10—H11118.5 (15)C21—C22—H26A109.5
Na2i—O10—H11109.3 (16)C21—C22—H26B109.5
H10—O10—H11107 (2)H26A—C22—H26B109.5
C21—O11—Na1139.11 (12)C21—C22—H26C109.5
C21—O11—H12101.7 (16)H26A—C22—H26C109.5
Na1—O11—H12110.5 (15)H26B—C22—H26C109.5
O5—P1—O2—C2085.95 (11)O9—Na1—O11—C2188.50 (18)
O3—P1—O2—C20−153.29 (10)C10—C1—C2—C3−1.8 (3)
O4—P1—O2—C20−34.69 (12)O1—C1—C2—C3−179.66 (16)
O3—P1—O5—Na2130.38 (8)C1—C2—C3—C4−0.2 (3)
O4—P1—O5—Na2−0.19 (10)C2—C3—C4—C5−176.76 (17)
O2—P1—O5—Na2−116.33 (7)C2—C3—C4—C91.4 (3)
O6—Na2—O5—P1168.16 (8)C3—C4—C5—C6176.72 (17)
O8—Na2—O5—P145.22 (8)C9—C4—C5—C6−1.5 (3)
O7—Na2—O5—P172.42 (18)C4—C5—C6—C73.1 (3)
O9—Na2—O5—P1−26.85 (8)C5—C6—C7—C8−1.8 (3)
O10ii—Na2—O5—P1−109.52 (8)C6—C7—C8—C9−1.1 (3)
O8—Na2—O6—Na1ii−178.06 (5)C7—C8—C9—C42.7 (2)
O7—Na2—O6—Na1ii−108.82 (5)C7—C8—C9—C10−176.16 (16)
O5—Na2—O6—Na1ii88.57 (5)C3—C4—C9—C8−179.63 (15)
O9—Na2—O6—Na1ii1.4 (2)C5—C4—C9—C8−1.4 (2)
O10ii—Na2—O6—Na1ii−28.89 (5)C3—C4—C9—C10−0.8 (2)
O8—Na1—O7—Na245.99 (4)C5—C4—C9—C10177.46 (14)
O6i—Na1—O7—Na2−105.25 (4)O1—C1—C10—C9−179.85 (13)
O10—Na1—O7—Na2171.38 (5)C2—C1—C10—C92.4 (2)
O11—Na1—O7—Na2102.7 (2)O1—C1—C10—C11−0.4 (2)
O9—Na1—O7—Na2−23.62 (4)C2—C1—C10—C11−178.07 (15)
O6—Na2—O7—Na1−168.48 (5)C8—C9—C10—C1177.67 (15)
O8—Na2—O7—Na1−43.84 (4)C4—C9—C10—C1−1.1 (2)
O5—Na2—O7—Na1−72.42 (15)C8—C9—C10—C11−1.8 (2)
O9—Na2—O7—Na125.66 (4)C4—C9—C10—C11179.38 (13)
O10ii—Na2—O7—Na1109.33 (5)C1—C10—C11—C20−78.74 (19)
O6i—Na1—O8—Na221.43 (11)C9—C10—C11—C20100.74 (17)
O7—Na1—O8—Na2−45.89 (4)C1—C10—C11—C12100.25 (17)
O10—Na1—O8—Na2−114.32 (6)C9—C10—C11—C12−80.28 (18)
O11—Na1—O8—Na2144.64 (5)C20—C11—C12—C171.8 (2)
O9—Na1—O8—Na250.43 (4)C10—C11—C12—C17−177.24 (14)
O6—Na2—O8—Na1124.57 (5)C20—C11—C12—C13−178.02 (15)
O7—Na2—O8—Na146.30 (4)C10—C11—C12—C133.0 (2)
O5—Na2—O8—Na1−141.97 (5)C17—C12—C13—C14−0.2 (3)
O9—Na2—O8—Na1−55.27 (4)C11—C12—C13—C14179.57 (19)
O10ii—Na2—O8—Na10.10 (9)C12—C13—C14—C151.4 (4)
O6—Na2—O9—Na1−133.02 (18)C13—C14—C15—C16−1.4 (4)
O8—Na2—O9—Na146.47 (4)C14—C15—C16—C170.2 (4)
O7—Na2—O9—Na1−23.50 (4)C13—C12—C17—C18177.98 (16)
O5—Na2—O9—Na1139.18 (4)C11—C12—C17—C18−1.8 (2)
O10ii—Na2—O9—Na1−102.92 (4)C13—C12—C17—C16−1.0 (2)
Na1ii—Na2—O9—Na1−131.92 (3)C11—C12—C17—C16179.20 (16)
O8—Na1—O9—Na2−50.24 (4)C15—C16—C17—C18−177.9 (2)
O6i—Na1—O9—Na2114.95 (4)C15—C16—C17—C121.0 (3)
O7—Na1—O9—Na223.51 (4)C12—C17—C18—C19−0.2 (2)
O10—Na1—O9—Na281.01 (16)C16—C17—C18—C19178.72 (17)
O11—Na1—O9—Na2−146.40 (5)C17—C18—C19—C202.3 (2)
O8—Na1—O10—Na2i131.19 (5)C12—C11—C20—O2177.15 (12)
O6i—Na1—O10—Na2i−27.34 (4)C10—C11—C20—O2−3.9 (2)
O7—Na1—O10—Na2i65.36 (4)C12—C11—C20—C190.3 (2)
O11—Na1—O10—Na2i−126.32 (5)C10—C11—C20—C19179.30 (13)
O9—Na1—O10—Na2i6.41 (17)P1—O2—C20—C11115.23 (13)
O8—Na1—O11—C2117.30 (18)P1—O2—C20—C19−67.86 (16)
O6i—Na1—O11—C21171.05 (18)C18—C19—C20—C11−2.3 (2)
O7—Na1—O11—C21−37.4 (3)C18—C19—C20—O2−179.16 (13)
O10—Na1—O11—C21−104.40 (18)Na1—O11—C21—C22−38.2 (3)
Symmetry codes: (i) −x+3/2, y+1/2, −z; (ii) −x+3/2, y−1/2, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.85 (2)1.84 (2)2.6687 (19)166 (2)
O6—H2···O11iii0.85 (2)2.04 (2)2.854 (2)159 (2)
O6—H3···O9iii0.85 (2)1.96 (2)2.7958 (19)171 (2)
O7—H4···O5i0.85 (1)1.87 (1)2.7136 (18)168 (2)
O7—H5···O4iii0.85 (1)2.11 (1)2.9473 (19)170 (2)
O8—H6···O1iii0.85 (2)1.96 (2)2.775 (2)163 (2)
O9—H8···O40.85 (2)1.88 (2)2.7259 (18)178 (1)
O9—H9···O3iv0.85 (1)1.85 (1)2.6978 (18)174 (2)
O10—H10···O5v0.85 (2)2.20 (2)3.012 (2)161 (2)
O10—H11···O3iii0.85 (1)2.20 (1)2.984 (2)154 (2)
O11—H12···O3v0.85 (1)1.82 (1)2.6711 (19)174 (2)
Symmetry codes: (iii) x+1/2, −y+1/2, z; (i) −x+3/2, y+1/2, −z; (iv) −x+1, −y, −z; (v) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.85 (2)1.84 (2)2.6687 (19)166 (2)
O6—H2···O11i0.85 (2)2.04 (2)2.854 (2)159 (2)
O6—H3···O9i0.85 (2)1.96 (2)2.7958 (19)171 (2)
O7—H4···O5ii0.85 (1)1.87 (1)2.7136 (18)168 (2)
O7—H5···O4i0.85 (1)2.11 (1)2.9473 (19)170 (2)
O8—H6···O1i0.85 (2)1.96 (2)2.775 (2)163 (2)
O9—H8···O40.85 (2)1.88 (2)2.7259 (18)178 (1)
O9—H9···O3iii0.85 (1)1.85 (1)2.6978 (18)174 (2)
O10—H10···O5iv0.85 (2)2.20 (2)3.012 (2)161 (2)
O10—H11···O3i0.85 (1)2.20 (1)2.984 (2)154 (2)
O11—H12···O3iv0.85 (1)1.82 (1)2.6711 (19)174 (2)
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, −z; (iii) −x+1, −y, −z; (iv) x, y+1, z.
references
References top

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Eckert, H. & Ward, M. (2001). Chem. Mater. 13, 3059–3060.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Vioux, A., Bideau, J.-L., Mutin, P. H. & Leclercq, D. (2004). Top. Curr. Chem. 232, 145–174.