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Acta Cryst. (2007). E63, m2321-m2322    [ doi:10.1107/S1600536807039220 ]

Poly[[pentaaqua[[mu]4-(5-carboxylato-m-phenylenedioxy)diacetato]cadmium(II)sodium(I)] tetrahydrate]

Y.-H. Wen and S. W. Ng

Abstract top

In the crystal structure of the title compound, [CdNa(C11H7O8)(H2O)5]·4H2O, the carboxylate trianion binds to a triaquacadmium unit through one O atom of its 5-carboxylate group. It also chelates through two O atoms of the 5-oxyacetate group to an adjacent triaquacadmium unit to form a linear chain. The diaquasodium unit is chelated by the 1-oxyacetate [-O-CH2-C(O)O-] group of one trianion and by the 3-oxyacetate group of another trianion. Both cadmium and sodium have six-coordinate octahedral geometries in a ribbon structure. The ribbons are linked into a three-dimensional network by hydrogen bonds.

Comment top

There is a number of metal derivatives of 3-carboxyphenoxyacetic acid, a carboxylic acid whose deprotonated dianion is regarded as a flexible dianion. The phenoxy linkage in the dianion is also capable of bonding, and this feature is noted in some of the calcium (Gao & Ng, 2006), cadmium (Gao, Huo, Deng & Ng, 2005; Zhao, Gu, Gao, Huo & Liu, 2005), cobalt (Li et al., 2004; Zhao, Gu, Huo et al., 2005), copper (Gao, Gu, Huo et al., 2004a, Gao, Gu, Huo et al., 2004b; Gao, Gu, Zhao et al., 2004), manganese (Gao, Huo, Cheng et al., 2005), nickel (Gu et al., 2005) and zinc (Gao, Huo, Liu et al., 2005; Zhao, Gu, Huo et al., 2005) derivatives. There is a similar number of divalent metal derivatives of the "two-armed" (and much more flexible) acid, benzene-1,3-dioxyacetic acid in the crystallographic literature (CSD Version 5.28, May 2007). Curiously, there is almost no crystallographic mention of the related tricarboxylic acid, 5-carboxy-1,3-diphenoxyacetic acid, the sole mention possibly being a patent claim for antibaterial properties (Leslie et al., 2004) only.

In the crystal structure of pentaaqua(5-carboxy-1,3-phenoxydiacetato)cadmiumsodium tetrahydrate, the carboxylate trianion binds to a triaquacadmium unit through one oxygen atom of its 5-carboxyl group. It also chelates through two oxygen atoms of the 5-oxyacetate group to an adjacent triaquacadmium unit to form a linear chain. Meanwhile, the diaquasodium unit is chelated by the 1-oxyacetate [–O–CH2–C(O)O–] group of one trianion and as well as by the 3-oxyacetate group of another trianion. Both cadmium and sodium sites exist six-coordinate octahedral geometries in the ribbon structure. The ribbons are linked into a three-dimensional network by extensive hydrogen bonds.

The lattice water molecules occupy the space within the ribbon; however, their contribution to the total volume is small as their exclusion is not seen in any significant voids in the unit cell.

Related literature top

For the crystal structures of metal derivatives of 3-carboxyphenoxyacetic acids, see Gao & Ng (2006); Gao, Huo, Deng et al. (2005); Zhao, Huo, Gao et al. (2005); Li et al. (2004); Zhao, Gu, Gao et al. (2005); Gao, Gu, Huo et al. (2004a); Gao, Gu, Huo et al. (2004b); Gao, Gu, Zhao et al. (2004); Gao, Huo, Cheng et al. (2005); Gu et al. (2005); Gao, Huo, Liu et al. (2005); Zhao, Gu, Huo et al. (2005). For the sole reference to 5-carboxy-1,3-diphenoxyacetic acid, see the patent for antibaterial properties by Leslie et al. (2004).

Experimental top

Sodium hydroxide was added to an aqueous soluiton consisting of 3 molar equivalents of chloroacetic acid and one equivalent of 3,5-dihydroxybenzoic acid until the solution was basic (pH approximately 11). The solution was heated for 3 h. The cool solution was neutralized with concentrated hydrochloric acid to a pH of about 3. The light-yellow solid that was precipitated was collected and dried.

5-Carboxy-1,3-diphenoxyacetic acid (0.282 g, 1 mol) and cadmium acetate dihydrate (0.266 g, 1 mol) were mixed in 20 ml e thanol-water (1:1, v/v) solution. The pH value was adjusted to 7 by sodium carbonate solution. The filtered solution was set aside for the growth of crystals after a week.

Refinement top

The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.85±0.01 Å and H.·H 1.39 + 00.01 Å); their displacement parameters were freely refined. The carbon-bound H-atoms were generated geometrically (C–H 0.93 to 0.97 Å); they were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot depicting the coordination geometries of cadmium and sodium; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. The lattice water molecules are not shown. [Translational/symmery code (i) 1 + x, y − 1, z; (ii) 1 − x, 1 − y, 2 − z.]
[Figure 2] Fig. 2. OLEX (Dolomanov et al., 2003) depiction of the ribbon motif, shown projected against the unit cell. The lattice water molecules are not shown.
Poly[[pentaaqua[µ4-(5-carboxylato-m-\ phenylenedioxy)diacetato]cadmium(II)sodium(I)] tetrahydrate] top
Crystal data top
[CdNa(C11H7O8)(H2O)5]·4H2OZ = 2
Mr = 564.70F000 = 572
Triclinic, P1Dx = 1.820 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.2853 (2) ÅCell parameters from 3652 reflections
b = 11.1525 (3) Åθ = 2.7–26.2º
c = 14.0096 (3) ŵ = 1.16 mm−1
α = 70.123 (1)ºT = 295 (2) K
β = 78.582 (1)ºBlock, colourless
γ = 75.987 (1)º0.18 × 0.08 × 0.05 mm
V = 1030.23 (5) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		4627 independent reflections
Radiation source: fine-focus sealed tube3861 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 295(2) Kθmax = 27.4º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.832, Tmax = 0.944k = −14→14
12790 measured reflectionsl = −18→18
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)] = 0.037H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3078P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4627 reflectionsΔρmax = 0.76 e Å−3
325 parametersΔρmin = −0.55 e Å−3
32 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[CdNa(C11H7O8)(H2O)5]·4H2Oγ = 75.987 (1)º
Mr = 564.70V = 1030.23 (5) Å3
Triclinic, P1Z = 2
a = 7.2853 (2) ÅMo Kα
b = 11.1525 (3) ŵ = 1.16 mm−1
c = 14.0096 (3) ÅT = 295 (2) K
α = 70.123 (1)º0.18 × 0.08 × 0.05 mm
β = 78.582 (1)º
Data collection top
Bruker APEXII area-detector
diffractometer		4627 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3861 reflections with I > 2σ(I)
Tmin = 0.832, Tmax = 0.944Rint = 0.032
12790 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03732 restraints
wR(F2) = 0.101H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.76 e Å−3
4627 reflectionsΔρmin = −0.55 e Å−3
325 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd11.28299 (4)0.23883 (2)0.62583 (2)0.0322 (1)
Na10.2853 (3)0.8385 (2)0.8649 (1)0.0524 (4)
O11.1165 (4)0.2998 (2)0.75921 (18)0.0397 (6)
O20.9974 (4)0.4538 (2)0.62858 (16)0.0334 (5)
O30.5501 (4)1.0908 (2)0.58968 (18)0.0408 (6)
O40.3957 (4)1.0247 (2)0.74276 (19)0.0385 (6)
O50.6126 (4)0.4270 (2)1.31888 (17)0.0352 (5)
O60.7003 (5)0.2613 (2)1.25572 (19)0.0490 (7)
O70.6542 (4)0.8090 (2)0.79807 (17)0.0355 (6)
O80.7473 (4)0.4093 (2)1.06632 (16)0.0320 (5)
O1w1.0518 (4)0.1510 (3)0.6042 (2)0.0460 (7)
O2w1.3042 (4)0.3643 (3)0.46121 (18)0.0437 (7)
O3w1.5094 (4)0.3321 (2)0.6562 (2)0.0400 (6)
O4w0.3611 (7)0.8572 (5)1.0106 (3)0.0911 (13)
O5w−0.0312 (9)0.8991 (6)0.8870 (6)0.136 (2)
O6w1.1643 (4)−0.0793 (3)0.5740 (2)0.0481 (7)
O7w0.7948 (4)0.3467 (3)0.49288 (19)0.0388 (6)
O8w0.7747 (7)0.1473 (6)0.7873 (3)0.1127 (17)
O9w−0.2894 (7)0.8524 (4)1.0663 (3)0.0920 (13)
C10.9022 (4)0.4805 (3)0.7950 (2)0.0244 (6)
C20.8351 (5)0.6139 (3)0.7571 (2)0.0248 (6)
C30.7358 (5)0.6791 (3)0.8258 (2)0.0256 (7)
C40.7065 (5)0.6153 (3)0.9298 (2)0.0263 (7)
C50.7738 (5)0.4826 (3)0.9658 (2)0.0243 (6)
C60.8721 (5)0.4156 (3)0.8980 (2)0.0256 (6)
C71.0108 (5)0.4069 (3)0.7223 (2)0.0268 (7)
C80.6719 (5)0.8809 (3)0.6921 (3)0.0330 (8)
C90.5281 (5)1.0077 (3)0.6758 (2)0.0288 (7)
C100.6691 (5)0.4765 (3)1.1399 (2)0.0263 (7)
C110.6619 (5)0.3788 (3)1.2460 (2)0.0291 (7)
H1w11.101 (5)0.085 (3)0.586 (3)0.069*
H1w20.985 (5)0.207 (2)0.561 (3)0.069*
H2w11.4081 (18)0.379 (4)0.4243 (19)0.066*
H2w21.212 (2)0.421 (3)0.4350 (19)0.066*
H3w11.604 (4)0.340 (3)0.609 (2)0.060*
H3w21.463 (4)0.405 (2)0.666 (3)0.060*
H4w10.291 (5)0.838 (8)1.0682 (15)0.137*
H4w20.477 (2)0.844 (8)1.022 (3)0.137*
H5w1−0.045 (12)0.966 (6)0.834 (4)0.204*
H5w2−0.043 (12)0.926 (9)0.939 (4)0.204*
H6w11.238 (5)−0.070 (5)0.5176 (17)0.072*
H6w21.226 (5)−0.132 (4)0.622 (2)0.072*
H7w10.841 (6)0.415 (3)0.475 (3)0.058*
H7w20.743 (6)0.345 (4)0.444 (2)0.058*
H8w10.680 (7)0.195 (8)0.757 (5)0.169*
H8w20.877 (6)0.151 (9)0.746 (5)0.169*
H9w1−0.410 (2)0.862 (8)1.070 (5)0.138*
H9w2−0.256 (10)0.807 (7)1.125 (3)0.138*
H20.85650.65800.68760.030*
H40.64230.66100.97500.032*
H60.91750.32670.92220.031*
H8a0.64860.83090.65250.040*
H8b0.80010.89860.66950.040*
H10a0.54160.52421.12680.032*
H10b0.74740.53791.13480.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03883 (16)0.02743 (14)0.02517 (14)0.00241 (10)−0.00134 (10)−0.00911 (10)
Na10.0671 (11)0.0479 (9)0.0390 (8)−0.0109 (8)0.0015 (8)−0.0138 (7)
O10.0479 (15)0.0292 (12)0.0302 (12)0.0144 (11)0.0000 (11)−0.0119 (10)
O20.0450 (14)0.0313 (12)0.0192 (11)−0.0005 (10)0.0011 (10)−0.0095 (9)
O30.0540 (16)0.0247 (12)0.0284 (12)0.0046 (11)0.0006 (11)−0.0003 (10)
O40.0446 (15)0.0265 (12)0.0347 (13)0.0042 (10)0.0004 (11)−0.0076 (10)
O50.0476 (15)0.0379 (13)0.0206 (11)−0.0089 (11)−0.0005 (10)−0.0110 (10)
O60.090 (2)0.0276 (13)0.0242 (12)−0.0078 (13)−0.0079 (13)−0.0036 (10)
O70.0548 (16)0.0202 (11)0.0235 (11)0.0070 (10)−0.0038 (11)−0.0072 (9)
O80.0479 (15)0.0248 (11)0.0153 (10)0.0017 (10)0.0019 (10)−0.0050 (8)
O1w0.0441 (16)0.0383 (14)0.0569 (17)−0.0003 (12)−0.0147 (14)−0.0169 (13)
O2w0.0364 (14)0.0544 (17)0.0240 (12)0.0018 (13)−0.0015 (11)0.0001 (11)
O3w0.0438 (15)0.0390 (14)0.0390 (14)−0.0078 (12)0.0015 (12)−0.0181 (12)
O4w0.106 (3)0.115 (3)0.072 (3)−0.032 (3)0.002 (2)−0.054 (3)
O5w0.089 (4)0.140 (5)0.146 (5)−0.001 (4)−0.004 (4)−0.023 (4)
O6w0.0618 (19)0.0391 (15)0.0342 (14)0.0004 (13)−0.0062 (13)−0.0063 (12)
O7w0.0451 (16)0.0401 (14)0.0340 (13)−0.0101 (12)−0.0102 (12)−0.0107 (11)
O8w0.077 (3)0.159 (5)0.068 (3)−0.014 (3)−0.008 (2)0.003 (3)
O9w0.113 (4)0.074 (3)0.079 (3)0.016 (3)−0.044 (3)−0.017 (2)
C10.0245 (15)0.0221 (14)0.0240 (15)0.0008 (12)−0.0011 (12)−0.0086 (12)
C20.0301 (16)0.0234 (15)0.0171 (14)−0.0008 (12)−0.0015 (12)−0.0053 (11)
C30.0304 (17)0.0195 (14)0.0240 (15)0.0015 (12)−0.0045 (13)−0.0066 (12)
C40.0317 (17)0.0235 (15)0.0219 (14)0.0032 (13)−0.0036 (13)−0.0107 (12)
C50.0280 (16)0.0241 (15)0.0169 (14)−0.0002 (12)−0.0035 (12)−0.0046 (11)
C60.0285 (16)0.0216 (14)0.0212 (14)0.0035 (12)−0.0036 (12)−0.0051 (11)
C70.0298 (17)0.0250 (15)0.0242 (15)−0.0041 (13)0.0014 (13)−0.0095 (12)
C80.041 (2)0.0202 (15)0.0286 (16)0.0027 (14)−0.0032 (15)−0.0027 (13)
C90.0374 (19)0.0195 (14)0.0272 (16)−0.0010 (13)−0.0061 (14)−0.0061 (12)
C100.0293 (16)0.0279 (16)0.0208 (14)−0.0017 (13)−0.0018 (12)−0.0096 (12)
C110.0343 (18)0.0325 (17)0.0187 (14)−0.0076 (14)−0.0026 (13)−0.0052 (13)
Geometric parameters (Å, °) top
Cd1—O12.234 (2)O4w—H4w10.86 (1)
Cd1—O3i2.322 (2)O4w—H4w20.86 (1)
Cd1—O4i2.446 (2)O5w—H5w10.86 (1)
Cd1—O1w2.256 (3)O5w—H5w20.86 (1)
Cd1—O2w2.251 (2)O6w—H6w10.85 (1)
Cd1—O3w2.323 (3)O6w—H6w20.85 (1)
Na1—O42.395 (3)O7w—H7w10.85 (1)
Na1—O6ii2.292 (3)O7w—H7w20.85 (1)
Na1—O72.645 (3)O8w—H8w10.85 (1)
Na1—O8ii2.653 (3)O8w—H8w20.85 (1)
Na1—O4w2.304 (4)O9w—H9w10.86 (1)
Na1—O5w2.230 (7)O9w—H9w20.85 (1)
O1—C71.257 (4)C1—C61.376 (4)
O2—C71.251 (4)C1—C21.396 (4)
O3—C91.256 (4)C1—C71.508 (4)
O4—C91.233 (4)C2—C31.388 (4)
O5—C111.263 (4)C3—C41.385 (4)
O6—C111.237 (4)C4—C51.387 (4)
O7—C31.376 (4)C5—C61.389 (4)
O7—C81.424 (4)C8—C91.519 (4)
O8—C51.369 (4)C10—C111.515 (4)
O8—C101.426 (4)C2—H20.93
O1w—H1w10.84 (1)C4—H40.93
O1w—H1w20.85 (1)C6—H60.93
O2w—H2w10.85 (1)C8—H8a0.97
O2w—H2w20.85 (1)C8—H8b0.97
O3w—H3w10.85 (1)C10—H10a0.97
O3w—H3w20.85 (1)C10—H10b0.97
O1—Cd1—O3i139.6 (1)O8—C5—C4124.2 (3)
O1—Cd1—O4i89.5 (1)O8—C5—C6115.9 (3)
O1—Cd1—O1w94.8 (1)C4—C5—C6120.0 (3)
O1—Cd1—O2w126.1 (1)C1—C6—C5120.1 (3)
O1—Cd1—O3w81.9 (1)O2—C7—O1122.2 (3)
O3i—Cd1—O4i54.5 (1)O2—C7—C1120.2 (3)
O3i—Cd1—O1w100.0 (1)O1—C7—C1117.5 (3)
O3i—Cd1—O2w91.0 (1)O7—C8—C9109.0 (3)
O3i—Cd1—O3w82.7 (1)O4—C9—O3122.9 (3)
O4i—Cd1—O1w86.4 (1)O4—C9—C8121.3 (3)
O4i—Cd1—O2w144.4 (1)O3—C9—C8115.8 (3)
O4i—Cd1—O3w93.5 (1)O8—C10—C11109.1 (2)
O1w—Cd1—O2w91.7 (1)O6—C11—O5125.1 (3)
O1w—Cd1—O3w176.7 (1)O6—C11—C10119.6 (3)
O2w—Cd1—O3w90.3 (1)O5—C11—C10115.3 (3)
O4—Na1—O6ii93.7 (1)Cd1—O1w—H1w1110 (2)
O4—Na1—O763.4 (1)Cd1—O1w—H1w2109 (2)
O4—Na1—O8ii154.1 (1)H1w1—O1w—H1w2112 (2)
O4—Na1—O4w98.7 (2)Cd1—O2w—H2w1124 (1)
O4—Na1—O5w104.7 (2)Cd1—O2w—H2w2123 (1)
O6ii—Na1—O779.3 (1)H2w1—O2w—H2w2110 (2)
O6ii—Na1—O8ii63.3 (1)Cd1—O3w—H3w1113 (2)
O6ii—Na1—O4w155.4 (2)Cd1—O3w—H3w2113 (2)
O6ii—Na1—O5w96.8 (2)H3w1—O3w—H3w2110 (2)
O7—Na1—O8ii98.9 (1)Na1—O4w—H4w1122 (2)
O7—Na1—O4w87.3 (2)Na1—O4w—H4w2122 (2)
O7—Na1—O5w166.9 (2)H4w1—O4w—H4w2108 (2)
O8ii—Na1—O4w99.1 (2)Na1—O5w—H5w1100 (6)
O8ii—Na1—O5w90.4 (2)Na1—O5w—H5w299 (6)
O4w—Na1—O5w100.4 (2)H5w1—O5w—H5w2108 (2)
C7—O1—Cd1106.1 (2)H6w1—O6w—H6w2109 (2)
C9—O3—Cd1iii93.9 (2)H7w1—O7w—H7w2110 (2)
C9—O4—Na1118.4 (2)H8w1—O8w—H8w2110 (2)
C9—O4—Cd1iii88.7 (2)H9w1—O9w—H9w2109 (2)
Na1—O4—Cd1iii142.2 (1)C3—C2—H2120.9
C11—O6—Na1ii128.3 (2)C1—C2—H2120.9
C3—O7—C8118.0 (2)C3—C4—H4120.3
C3—O7—Na1109.8 (2)C5—C4—H4120.3
C8—O7—Na1106.7 (2)C1—C6—H6119.9
C5—O8—C10117.5 (2)C5—C6—H6119.9
C5—O8—Na1ii126.2 (2)O7—C8—H8a109.9
C10—O8—Na1ii113.1 (2)C9—C8—H8a109.9
C6—C1—C2120.9 (3)O7—C8—H8b109.9
C6—C1—C7119.6 (3)C9—C8—H8b109.9
C2—C1—C7119.5 (3)H8a—C8—H8b108.3
C3—C2—C1118.2 (3)O8—C10—H10a109.9
O7—C3—C4114.4 (3)C11—C10—H10a109.9
O7—C3—C2124.1 (3)O8—C10—H10b109.9
C4—C3—C2121.5 (3)C11—C10—H10b109.9
C3—C4—C5119.3 (3)H10a—C10—H10b108.3
O2w—Cd1—O1—C712.3 (3)C2—C3—C4—C5−1.6 (5)
O1w—Cd1—O1—C7−83.4 (2)C10—O8—C5—C4−9.0 (5)
O3i—Cd1—O1—C7165.2 (2)Na1ii—O8—C5—C4149.0 (3)
O3w—Cd1—O1—C796.7 (2)C10—O8—C5—C6172.2 (3)
O4i—Cd1—O1—C7−169.8 (2)Na1ii—O8—C5—C6−29.8 (4)
O5w—Na1—O4—C9−140.2 (3)C3—C4—C5—O8−177.7 (3)
O6ii—Na1—O4—C9−42.1 (3)C3—C4—C5—C61.0 (5)
O4w—Na1—O4—C9116.5 (3)C2—C1—C6—C50.0 (5)
O7—Na1—O4—C934.0 (2)C7—C1—C6—C5179.4 (3)
O8ii—Na1—O4—C9−16.4 (4)O8—C5—C6—C1178.7 (3)
O5w—Na1—O4—Cd1iii−9.4 (3)C4—C5—C6—C1−0.2 (5)
O6ii—Na1—O4—Cd1iii88.7 (2)Cd1—O1—C7—O27.0 (4)
O4w—Na1—O4—Cd1iii−112.7 (2)Cd1—O1—C7—C1−171.4 (2)
O7—Na1—O4—Cd1iii164.8 (2)C6—C1—C7—O2161.1 (3)
O8ii—Na1—O4—Cd1iii114.5 (3)C2—C1—C7—O2−19.4 (5)
O5w—Na1—O7—C3−141.6 (9)C6—C1—C7—O1−20.4 (5)
O6ii—Na1—O7—C3−67.5 (2)C2—C1—C7—O1159.0 (3)
O4w—Na1—O7—C391.7 (2)C3—O7—C8—C9164.0 (3)
O4—Na1—O7—C3−167.1 (2)Na1—O7—C8—C939.9 (3)
O8ii—Na1—O7—C3−7.0 (2)Na1—O4—C9—O3152.2 (3)
O5w—Na1—O7—C8−12.6 (9)Cd1iii—O4—C9—O3−0.1 (4)
O6ii—Na1—O7—C861.5 (2)Na1—O4—C9—C8−25.5 (4)
O4w—Na1—O7—C8−139.3 (2)Cd1iii—O4—C9—C8−177.8 (3)
O4—Na1—O7—C8−38.1 (2)Cd1iii—O3—C9—O40.1 (4)
O8ii—Na1—O7—C8122.0 (2)Cd1iii—O3—C9—C8178.0 (3)
C6—C1—C2—C3−0.5 (5)O7—C8—C9—O4−14.3 (5)
C7—C1—C2—C3−180.0 (3)O7—C8—C9—O3167.8 (3)
C8—O7—C3—C4−177.9 (3)C5—O8—C10—C11−176.8 (3)
Na1—O7—C3—C4−55.4 (3)Na1ii—O8—C10—C1122.3 (3)
C8—O7—C3—C20.3 (5)Na1ii—O6—C11—O5162.4 (3)
Na1—O7—C3—C2122.8 (3)Na1ii—O6—C11—C10−16.3 (5)
C1—C2—C3—O7−176.7 (3)O8—C10—C11—O6−7.7 (5)
C1—C2—C3—C41.4 (5)O8—C10—C11—O5173.4 (3)
O7—C3—C4—C5176.6 (3)
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O6w0.84 (1)1.83 (2)2.651 (4)165 (5)
O1w—H1w2···O7w0.85 (1)1.92 (1)2.750 (4)165 (4)
O2w—H2w1···O5iv0.85 (1)1.92 (1)2.748 (4)168 (2)
O2w—H2w2···O2v0.85 (1)1.93 (1)2.780 (3)178 (5)
O3w—H3w1···O7wvi0.85 (1)1.91 (1)2.759 (4)171 (3)
O3w—H3w2···O5vii0.85 (1)1.89 (1)2.736 (4)173 (3)
O4w—H4w1···O8wii0.86 (1)2.04 (3)2.796 (6)147 (4)
O4w—H4w2···O9wvi0.86 (1)1.96 (2)2.790 (7)164 (6)
O5w—H5w1···O8wiii0.86 (1)2.09 (5)2.805 (8)140 (7)
O5w—H5w2···O9w0.86 (1)2.35 (9)2.798 (9)113 (8)
O6w—H6w1···O3v0.85 (1)1.96 (2)2.790 (4)165 (4)
O6w—H6w2···O6viii0.85 (1)1.90 (2)2.730 (4)165 (4)
O7w—H7w1···O2v0.85 (1)2.09 (2)2.859 (4)152 (4)
O7w—H7w2···O5ix0.85 (1)1.99 (2)2.780 (3)154 (4)
O8w—H8w1···O3wx0.85 (1)2.04 (3)2.874 (5)165 (8)
O8w—H8w2···O1w0.85 (1)2.13 (4)2.929 (6)155 (8)
O9w—H9w1···O4wx0.86 (1)2.02 (4)2.790 (7)150 (7)
O9w—H9w2···O1ii0.85 (1)1.96 (2)2.794 (4)166 (7)
Symmetry codes: (iv) x+1, y, z−1; (v) −x+2, −y+1, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z; (viii) −x+2, −y, −z+2; (ix) x, y, z−1; (x) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O6w0.84 (1)1.83 (2)2.651 (4)165 (5)
O1w—H1w2···O7w0.85 (1)1.92 (1)2.750 (4)165 (4)
O2w—H2w1···O5i0.85 (1)1.92 (1)2.748 (4)168 (2)
O2w—H2w2···O2ii0.85 (1)1.93 (1)2.780 (3)178 (5)
O3w—H3w1···O7wiii0.85 (1)1.91 (1)2.759 (4)171 (3)
O3w—H3w2···O5iv0.85 (1)1.89 (1)2.736 (4)173 (3)
O4w—H4w1···O8wv0.86 (1)2.04 (3)2.796 (6)147 (4)
O4w—H4w2···O9wiii0.86 (1)1.96 (2)2.790 (7)164 (6)
O5w—H5w1···O8wvi0.86 (1)2.09 (5)2.805 (8)140 (7)
O5w—H5w2···O9w0.86 (1)2.35 (9)2.798 (9)113 (8)
O6w—H6w1···O3ii0.85 (1)1.96 (2)2.790 (4)165 (4)
O6w—H6w2···O6vii0.85 (1)1.90 (2)2.730 (4)165 (4)
O7w—H7w1···O2ii0.85 (1)2.09 (2)2.859 (4)152 (4)
O7w—H7w2···O5viii0.85 (1)1.99 (2)2.780 (3)154 (4)
O8w—H8w1···O3wix0.85 (1)2.04 (3)2.874 (5)165 (8)
O8w—H8w2···O1w0.85 (1)2.13 (4)2.929 (6)155 (8)
O9w—H9w1···O4wix0.86 (1)2.02 (4)2.790 (7)150 (7)
O9w—H9w2···O1v0.85 (1)1.96 (2)2.794 (4)166 (7)
Symmetry codes: (i) x+1, y, z−1; (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+1, −z+2; (vi) x−1, y+1, z; (vii) −x+2, −y, −z+2; (viii) x, y, z−1; (ix) x−1, y, z.
Acknowledgements top

We thank the Foundation of the Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces (No. 0506) and the University of Malaya for supporting this study.

references
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