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Acta Cryst. (2007). E63, m2378-m2379    [ doi:10.1107/S1600536807040093 ]

catena-Poly[hexaaquazinc(II) bis[[triaquazincate(II)]-[mu]-(5-carboxylato-m-phenylenedioxy)diacetato-[kappa]2O1:O5] heptahydrate]

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

Abstract top

The reaction of zinc cations and (5-carboxy-m-phenylenedioxy)diacetate anions in water yields the title salt, {[Zn(H2O)6][Zn(C11H7O8)(H2O)3]2·7H2O}n. The cation has the Zn atom surrounded octahedrally by six water molecules. The anion exists as a linear carboxylate-bridged chain, as it uses the carboxy and one of the two oxyacetate arms of the trianion to connect the triaquazincate species. The Zn atoms in the two independent polyanionic chains exist in trigonal-bipyramidal geometries. The cation and anions are linked by extensive hydrogen bonds into a three-dimensional network structure.

Comment top

The reaction of zinc cations and (5-carboxy-m-phenylenedioxy)diacetate anions in water yields the salt, [Zn(H2O)6]2+ 2[Zn(C11H7O8)(H2O)3]−.7H2O. The cation has the zinc atom surrounded octahedrally by six water molecules. The anion exists as a linear, carboxylate-bridged chain as it uses the carboxy and one of the two oxyacetate arms of the trianion to connect the triaquazinc species. The zinc atom in the two independent polyanionic chains exists in trigonal-bipyramidal geometries. The cation and anions are linked by extensive hydrogen bonds into a three-dimensional network structure.

Related literature top

There is currently only one other structure report of a metal (5-carboxy-m-phenylenedioxy)diacetate, namely a cadmium–sodium compound (Wen & Ng, 2007).

Experimental top

(5-Carboxy-m-phenylenedioxy)diacetic acid (0.282 g, 1 mol) and zinc nitrate hexahydrate (0.298 g, 1 mmol) 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 were placed in chemically sensible positions on the basis of hydrogen bonds but they were not refined. Their temperature factors tied to those of the oxygen atoms by a factor of 1.5. 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); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot depicting the coordination geometries the zinc atoms of [Zn(H2O)6]2+2[Zn(C11H7O8)(H2O)3]−·7H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. The lattice water molecules are not shown. [Translational code: (i) x – 1, y, z; (ii) 1 + x, y – 1, z.]
catena-Poly[hexaaquazinc(II) bis[[triaquazincate(II)]-µ-(5-carboxylato-m-phenylenedioxy)diacetato- κ2O1:O5] heptahydrate] top
Crystal data top
[Zn(H2O)6][Zn(C11H7O8)(H2O)3]2·7H2OZ = 1
Mr = 1072.75F000 = 554
Triclinic, P1Dx = 1.779 Mg m−3
Hall symbol: P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.2044 (1) ÅCell parameters from 9439 reflections
b = 11.2959 (1) Åθ = 2.8–27.5º
c = 13.6932 (2) ŵ = 1.90 mm−1
α = 70.872 (1)ºT = 295 (2) K
β = 76.436 (1)ºPrism, colourless
γ = 74.589 (1)º0.53 × 0.13 × 0.06 mm
V = 1001.59 (2) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		7671 independent reflections
Radiation source: fine-focus sealed tube7353 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 295(2) Kθmax = 27.5º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→9
Tmin = 0.796, Tmax = 1.000k = −14→14
14916 measured reflectionsl = −17→17
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030  w = 1/[σ2(Fo2) + (0.0617P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.52 e Å−3
7671 reflectionsΔρmin = −0.61 e Å−3
542 parametersExtinction correction: none
3 restraintsAbsolute structure: Flack (1983), with 3182 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.150 (6)
Secondary atom site location: difference Fourier map
Crystal data top
[Zn(H2O)6][Zn(C11H7O8)(H2O)3]2·7H2Oγ = 74.589 (1)º
Mr = 1072.75V = 1001.59 (2) Å3
Triclinic, P1Z = 1
a = 7.2044 (1) ÅMo Kα
b = 11.2959 (1) ŵ = 1.90 mm−1
c = 13.6932 (2) ÅT = 295 (2) K
α = 70.872 (1)º0.53 × 0.13 × 0.06 mm
β = 76.436 (1)º
Data collection top
Bruker APEXII area-detector
diffractometer		7671 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7353 reflections with I > 2σ(I)
Tmin = 0.796, Tmax = 1.000Rint = 0.016
14916 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.082Δρmax = 0.52 e Å−3
S = 1.04Δρmin = −0.61 e Å−3
7671 reflectionsAbsolute structure: Flack (1983), with 3182 Friedel pairs
542 parametersFlack parameter: 0.150 (6)
3 restraints
Special details top

Experimental. A somewhat long crystal was used in the measurements as attempts to cut the larger ones ended up shattering the crystal. The growth of crystals could not be easily reproduced either.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50020 (4)0.49999 (3)0.50000 (2)0.02494 (9)
Zn21.09107 (4)−0.01775 (3)0.75462 (2)0.02540 (9)
Zn30.83895 (6)−0.22965 (4)1.16257 (3)0.03107 (9)
O10.6895 (3)0.4346 (2)0.38485 (17)0.0275 (5)
O20.8194 (3)0.2799 (2)0.51287 (16)0.0291 (5)
O31.1508 (4)−0.07046 (19)0.32384 (17)0.0303 (5)
O41.2618 (4)−0.3575 (2)0.5234 (2)0.0387 (6)
O51.3998 (4)−0.2917 (2)0.3622 (2)0.0428 (7)
O61.0672 (4)0.3287 (2)0.06085 (16)0.0298 (5)
O71.1763 (4)0.3157 (2)−0.20182 (18)0.0332 (5)
O81.0586 (5)0.4765 (2)−0.1298 (2)0.0483 (8)
O90.9041 (3)0.05406 (19)0.86500 (17)0.0273 (5)
O100.7751 (4)0.2131 (2)0.73999 (16)0.0305 (5)
O110.4494 (4)0.55586 (19)0.93352 (17)0.0276 (5)
O120.3162 (4)0.8365 (2)0.73159 (19)0.0320 (5)
O130.1907 (4)0.7768 (2)0.8983 (2)0.0422 (6)
O140.5828 (4)0.1589 (2)1.19514 (16)0.0293 (5)
O150.4309 (4)0.1582 (2)1.45986 (17)0.0312 (5)
O160.5407 (5)0.0034 (2)1.3813 (2)0.0493 (8)
O1W0.4777 (4)0.3952 (2)0.65198 (18)0.0347 (6)
H1A0.56760.33260.67570.052*
H1B0.37170.38750.69490.052*
O2W0.7069 (4)0.5919 (2)0.5134 (2)0.0326 (6)
H2A0.78990.54590.55270.049*
H2B0.67190.66670.52180.049*
O3W0.3050 (4)0.4050 (2)0.4675 (2)0.0353 (6)
H3A0.20630.41050.51410.053*
H3B0.33980.33150.45840.053*
O4W1.1147 (4)0.0933 (3)0.60334 (19)0.0406 (6)
H4A1.22570.09590.56530.061*
H4B1.02590.13970.56830.061*
O5W0.8840 (4)−0.1083 (3)0.7440 (3)0.0451 (7)
H5A0.9317−0.17000.71740.068*
H5B0.7843−0.06210.71600.068*
O6W1.2974 (4)0.0640 (3)0.7922 (2)0.0358 (6)
H6A1.26800.13510.80510.054*
H6B1.40650.05460.75340.054*
O7W0.5925 (4)−0.1146 (3)1.2179 (2)0.0450 (7)
H7A0.5077−0.15671.26090.068*
H7B0.6092−0.06321.24710.068*
O8W0.6677 (4)−0.3664 (2)1.18827 (19)0.0334 (5)
H8A0.6994−0.42461.24390.050*
H8B0.7241−0.39931.13890.050*
O9W0.9205 (5)−0.3172 (3)1.3127 (2)0.0508 (7)
H9A0.8392−0.34651.36510.076*
H9B1.0280−0.37051.31140.076*
O10W1.0768 (4)−0.3539 (3)1.1004 (2)0.0399 (6)
H10A1.0713−0.39191.05760.060*
H10B1.1789−0.38931.12850.060*
O11W1.0123 (5)−0.1048 (3)1.1442 (2)0.0496 (8)
H11A1.0628−0.12811.19970.074*
H11B0.9395−0.02921.13920.074*
O12W0.7652 (4)−0.1549 (2)1.01018 (18)0.0327 (5)
H12A0.7790−0.20920.97660.049*
H12B0.8172−0.09310.97020.049*
O13W−0.0153 (4)0.4100 (2)0.6226 (2)0.0352 (6)
H13A0.00810.41510.67940.053*
H13B−0.05820.34110.63770.053*
O14W1.5912 (6)−0.1901 (3)0.5556 (2)0.0608 (9)
H14A1.4965−0.19130.60620.091*
H14B1.5590−0.13030.50220.091*
O15W1.6115 (4)0.0755 (2)0.6342 (2)0.0371 (6)
H15A1.63900.14260.63610.056*
H15B1.55410.09060.58300.056*
O16W0.3399 (5)−0.0597 (4)1.0130 (3)0.0642 (9)
H16A0.3490−0.13841.04550.096*
H16B0.3618−0.05000.94700.096*
O17W0.9701 (5)−0.3302 (3)0.6995 (3)0.0577 (8)
H17A1.0121−0.38880.75110.087*
H17B1.0556−0.32670.64490.087*
O18W1.2910 (5)−0.4540 (3)1.2606 (3)0.0584 (8)
H18A1.3785−0.40621.23770.088*
H18B1.3035−0.49561.32470.088*
O19W0.7759 (4)0.6085 (3)0.9927 (2)0.0436 (6)
H19A0.68120.60800.96640.065*
H19B0.88220.57330.96210.065*
C10.9180 (4)0.2574 (3)0.3402 (2)0.0189 (6)
C20.9824 (4)0.1244 (3)0.3748 (2)0.0223 (6)
H20.95910.07990.44540.027*
C31.0815 (5)0.0614 (3)0.3009 (2)0.0213 (6)
C41.1186 (4)0.1252 (3)0.1949 (2)0.0221 (6)
H41.18900.08090.14680.026*
C51.0486 (4)0.2556 (3)0.1624 (2)0.0213 (6)
C60.9513 (5)0.3224 (3)0.2356 (2)0.0232 (6)
H60.90900.41080.21360.028*
C70.8031 (4)0.3279 (3)0.4184 (2)0.0201 (6)
C81.1374 (5)−0.1446 (3)0.4299 (2)0.0280 (7)
H811.0049−0.15700.45750.034*
H821.1717−0.10080.47130.034*
C91.2758 (5)−0.2724 (3)0.4360 (3)0.0287 (7)
C101.1395 (5)0.2647 (3)−0.0181 (2)0.0228 (6)
H1011.06510.2002−0.00750.027*
H1021.27500.2226−0.01520.027*
C111.1210 (5)0.3627 (3)−0.1237 (2)0.0255 (6)
C120.7946 (4)0.1633 (3)0.8330 (2)0.0205 (6)
C130.6929 (4)0.2321 (3)0.9140 (2)0.0192 (6)
C140.6166 (4)0.3631 (3)0.8811 (2)0.0204 (6)
H140.62610.40680.81010.024*
C150.5266 (5)0.4270 (3)0.9558 (2)0.0203 (6)
C160.5108 (5)0.3619 (3)1.0628 (2)0.0216 (6)
H160.44860.40551.11240.026*
C170.5881 (4)0.2331 (3)1.0936 (2)0.0215 (6)
C180.6809 (4)0.1668 (3)1.0196 (2)0.0214 (6)
H180.73420.07971.04100.026*
C190.4421 (5)0.6258 (3)0.8262 (2)0.0255 (6)
H1910.39490.57890.79240.031*
H1920.57160.63770.78980.031*
C200.3055 (5)0.7552 (3)0.8218 (3)0.0257 (7)
C210.4896 (5)0.2183 (3)1.2755 (2)0.0230 (6)
H2110.35690.26101.26510.028*
H2120.55910.28181.27400.028*
C220.4887 (5)0.1164 (3)1.3797 (2)0.0262 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02845 (19)0.02098 (16)0.01952 (17)0.00165 (13)0.00168 (14)−0.00723 (13)
Zn20.02831 (19)0.02057 (16)0.02017 (17)0.00396 (13)0.00093 (14)−0.00687 (13)
Zn30.0371 (2)0.02793 (17)0.02684 (18)−0.01000 (14)0.00251 (14)−0.00877 (13)
O10.0334 (13)0.0195 (10)0.0208 (11)0.0062 (9)−0.0004 (9)−0.0062 (9)
O20.0397 (14)0.0252 (11)0.0163 (11)0.0034 (9)−0.0037 (10)−0.0065 (9)
O30.0503 (15)0.0132 (10)0.0197 (11)0.0030 (9)−0.0022 (10)−0.0047 (8)
O40.0476 (16)0.0192 (11)0.0351 (15)0.0032 (10)−0.0090 (12)0.0045 (10)
O50.0424 (15)0.0254 (12)0.0460 (16)0.0034 (11)0.0103 (12)−0.0114 (11)
O60.0452 (14)0.0215 (10)0.0134 (10)0.0004 (9)0.0024 (9)−0.0036 (8)
O70.0444 (15)0.0360 (13)0.0164 (11)−0.0086 (11)−0.0006 (10)−0.0066 (10)
O80.084 (2)0.0280 (14)0.0199 (13)−0.0001 (13)−0.0008 (13)−0.0032 (10)
O90.0327 (12)0.0171 (10)0.0193 (11)0.0057 (9)0.0029 (9)−0.0018 (8)
O100.0385 (14)0.0295 (12)0.0164 (11)0.0041 (10)−0.0020 (9)−0.0077 (9)
O110.0410 (14)0.0171 (10)0.0186 (10)0.0053 (9)−0.0065 (9)−0.0050 (8)
O120.0373 (14)0.0198 (11)0.0272 (13)0.0067 (9)−0.0037 (11)−0.0023 (9)
O130.0489 (16)0.0269 (12)0.0340 (14)0.0117 (11)0.0027 (12)−0.0086 (11)
O140.0470 (14)0.0187 (9)0.0111 (10)0.0038 (9)0.0006 (9)−0.0017 (8)
O150.0392 (14)0.0345 (12)0.0169 (11)−0.0066 (10)0.0007 (9)−0.0077 (9)
O160.093 (2)0.0216 (12)0.0236 (13)−0.0081 (13)−0.0045 (14)0.0007 (10)
O1W0.0258 (13)0.0400 (14)0.0219 (12)0.0024 (10)0.0001 (10)0.0027 (10)
O2W0.0360 (14)0.0248 (12)0.0333 (14)−0.0025 (10)−0.0044 (11)−0.0074 (10)
O3W0.0371 (15)0.0339 (13)0.0348 (14)−0.0057 (10)−0.0012 (11)−0.0141 (11)
O4W0.0324 (14)0.0428 (15)0.0239 (13)0.0048 (11)−0.0001 (10)0.0074 (11)
O5W0.0414 (17)0.0362 (15)0.060 (2)−0.0015 (12)−0.0167 (14)−0.0154 (13)
O6W0.0339 (14)0.0367 (13)0.0378 (14)−0.0052 (10)0.0033 (11)−0.0196 (11)
O7W0.0497 (17)0.0349 (14)0.0484 (17)−0.0135 (12)0.0128 (13)−0.0196 (12)
O8W0.0423 (14)0.0256 (12)0.0296 (13)−0.0075 (10)−0.0002 (11)−0.0078 (10)
O9W0.0516 (18)0.0645 (19)0.0272 (14)−0.0151 (14)0.0012 (12)−0.0038 (13)
O10W0.0406 (15)0.0420 (15)0.0324 (14)−0.0018 (11)−0.0030 (11)−0.0117 (11)
O11W0.063 (2)0.0506 (17)0.0454 (17)−0.0336 (15)0.0003 (14)−0.0165 (14)
O12W0.0400 (14)0.0274 (11)0.0269 (12)−0.0050 (9)0.0011 (10)−0.0088 (9)
O13W0.0367 (14)0.0407 (14)0.0301 (13)−0.0129 (11)−0.0093 (11)−0.0060 (11)
O14W0.101 (3)0.0296 (14)0.0300 (15)0.0064 (15)0.0015 (16)−0.0034 (12)
O15W0.0386 (15)0.0384 (14)0.0353 (14)−0.0088 (11)−0.0077 (11)−0.0098 (11)
O16W0.055 (2)0.086 (2)0.0464 (18)−0.0137 (18)−0.0028 (15)−0.0156 (17)
O17W0.082 (2)0.0383 (16)0.0396 (17)0.0001 (15)−0.0097 (16)−0.0034 (13)
O18W0.058 (2)0.064 (2)0.0541 (19)−0.0144 (15)−0.0220 (15)−0.0067 (15)
O19W0.0484 (16)0.0448 (15)0.0449 (16)−0.0082 (12)−0.0049 (12)−0.0251 (12)
C10.0202 (15)0.0184 (13)0.0162 (13)0.0018 (10)−0.0030 (11)−0.0068 (11)
C20.0277 (16)0.0172 (13)0.0181 (14)0.0000 (11)−0.0027 (12)−0.0041 (11)
C30.0257 (16)0.0150 (13)0.0196 (14)−0.0007 (11)−0.0042 (12)−0.0026 (11)
C40.0246 (16)0.0215 (14)0.0179 (14)0.0005 (11)−0.0008 (12)−0.0086 (11)
C50.0248 (16)0.0202 (13)0.0156 (13)−0.0018 (11)−0.0046 (11)−0.0021 (10)
C60.0313 (17)0.0156 (12)0.0196 (14)−0.0010 (11)−0.0039 (12)−0.0039 (11)
C70.0235 (15)0.0155 (12)0.0166 (14)0.0007 (11)0.0017 (11)−0.0058 (11)
C80.0371 (19)0.0176 (14)0.0206 (15)0.0016 (12)−0.0016 (13)−0.0019 (12)
C90.0315 (18)0.0187 (15)0.0320 (19)−0.0011 (12)−0.0038 (15)−0.0061 (13)
C100.0281 (16)0.0219 (14)0.0155 (14)−0.0012 (11)−0.0019 (11)−0.0057 (11)
C110.0295 (17)0.0266 (15)0.0168 (14)−0.0059 (12)0.0011 (12)−0.0046 (12)
C120.0221 (15)0.0179 (13)0.0166 (14)−0.0035 (11)0.0014 (11)−0.0022 (11)
C130.0197 (15)0.0183 (13)0.0160 (13)0.0000 (10)−0.0013 (11)−0.0045 (11)
C140.0242 (15)0.0179 (13)0.0142 (13)−0.0010 (11)−0.0033 (11)−0.0009 (10)
C150.0249 (15)0.0146 (13)0.0198 (14)−0.0003 (11)−0.0043 (11)−0.0052 (11)
C160.0279 (16)0.0177 (13)0.0176 (13)−0.0003 (11)−0.0027 (11)−0.0071 (11)
C170.0235 (15)0.0213 (14)0.0166 (13)−0.0021 (11)−0.0024 (11)−0.0036 (11)
C180.0221 (15)0.0167 (13)0.0192 (14)0.0041 (11)−0.0022 (11)−0.0041 (11)
C190.0325 (18)0.0150 (13)0.0209 (15)0.0051 (11)−0.0050 (13)−0.0019 (11)
C200.0322 (18)0.0155 (13)0.0264 (17)−0.0011 (12)−0.0060 (14)−0.0042 (12)
C210.0272 (16)0.0222 (14)0.0171 (14)−0.0011 (11)−0.0001 (12)−0.0079 (11)
C220.0289 (17)0.0281 (16)0.0182 (15)−0.0058 (13)−0.0031 (12)−0.0025 (12)
Geometric parameters (Å, °) top
Zn1—O1W2.022 (2)O9W—H9A0.85
Zn1—O12.028 (2)O9W—H9B0.85
Zn1—O4i2.063 (3)O10W—H10A0.85
Zn1—O2W2.099 (3)O10W—H10B0.85
Zn1—O3W2.176 (3)O11W—H11A0.85
Zn2—O92.006 (2)O11W—H11B0.87
Zn2—O12ii2.030 (2)O12W—H12A0.85
Zn2—O4W2.034 (2)O12W—H12B0.85
Zn2—O5W2.075 (3)O13W—H13A0.86
Zn2—O6W2.174 (3)O13W—H13B0.86
Zn3—O11W2.042 (3)O14W—H14A0.85
Zn3—O7W2.050 (3)O14W—H14B0.85
Zn3—O10W2.110 (3)O15W—H15A0.84
Zn3—O9W2.115 (3)O15W—H15B0.84
Zn3—O12W2.116 (2)O16W—H16A0.85
Zn3—O8W2.118 (2)O16W—H16B0.86
O1—C71.274 (4)O17W—H17A0.85
O2—C71.249 (4)O17W—H17B0.85
O3—C31.392 (3)O18W—H18A0.87
O3—C81.414 (4)O18W—H18B0.86
O4—C91.268 (4)O19W—H19A0.85
O4—Zn1ii2.063 (3)O19W—H19B0.85
O5—C91.218 (4)C1—C61.375 (4)
O6—C51.361 (4)C1—C21.401 (4)
O6—C101.418 (3)C1—C71.503 (4)
O7—C111.283 (4)C2—C31.380 (4)
O8—C111.225 (4)C2—H20.9300
O9—C121.275 (4)C3—C41.390 (4)
O10—C121.237 (4)C4—C51.380 (4)
O11—C151.371 (3)C4—H40.9300
O11—C191.429 (4)C5—C61.396 (4)
O12—C201.274 (4)C6—H60.9300
O12—Zn2i2.030 (2)C8—C91.510 (4)
O13—C201.224 (4)C8—H810.9700
O14—C171.365 (4)C8—H820.9700
O14—C211.418 (3)C10—C111.515 (4)
O15—C221.273 (4)C10—H1010.9700
O16—C221.226 (4)C10—H1020.9700
O1W—H1A0.85C12—C131.502 (4)
O1W—H1B0.85C13—C181.385 (4)
O2W—H2A0.85C13—C141.393 (4)
O2W—H2B0.85C14—C151.383 (4)
O3W—H3A0.84C14—H140.9300
O3W—H3B0.84C15—C161.400 (4)
O4W—H4A0.85C16—C171.372 (4)
O4W—H4B0.85C16—H160.9300
O5W—H5A0.85C17—C181.395 (4)
O5W—H5B0.86C18—H180.9300
O6W—H6A0.84C19—C201.521 (4)
O6W—H6B0.84C19—H1910.9700
O7W—H7A0.87C19—H1920.9700
O7W—H7B0.85C21—C221.512 (4)
O8W—H8A0.86C21—H2110.9700
O8W—H8B0.85C21—H2120.9700
O1W—Zn1—O1122.32 (9)H16A—O16W—H16B109.5
O1W—Zn1—O4i95.06 (10)H17A—O17W—H17B110.7
O1—Zn1—O4i141.81 (10)H18A—O18W—H18B106.2
O1W—Zn1—O2W93.32 (11)H19A—O19W—H19B110.3
O1—Zn1—O2W90.19 (10)C6—C1—C2120.8 (3)
O4i—Zn1—O2W95.59 (10)C6—C1—C7120.1 (3)
O1W—Zn1—O3W92.18 (11)C2—C1—C7119.1 (3)
O1—Zn1—O3W83.45 (10)C3—C2—C1117.9 (3)
O4i—Zn1—O3W87.95 (11)C3—C2—H2121.0
O2W—Zn1—O3W173.18 (10)C1—C2—H2121.0
O9—Zn2—O12ii143.70 (9)C2—C3—C4122.3 (3)
O9—Zn2—O4W118.87 (10)C2—C3—O3124.1 (3)
O12ii—Zn2—O4W96.70 (10)C4—C3—O3113.6 (2)
O9—Zn2—O5W90.34 (11)C5—C4—C3118.6 (3)
O12ii—Zn2—O5W93.23 (11)C5—C4—H4120.7
O4W—Zn2—O5W95.78 (12)C3—C4—H4120.7
O9—Zn2—O6W83.78 (9)O6—C5—C4124.6 (3)
O12ii—Zn2—O6W87.55 (10)O6—C5—C6115.0 (2)
O4W—Zn2—O6W93.03 (12)C4—C5—C6120.3 (3)
O5W—Zn2—O6W171.00 (12)C1—C6—C5120.0 (3)
O11W—Zn3—O7W93.29 (12)C1—C6—H6120.0
O11W—Zn3—O10W91.01 (12)C5—C6—H6120.0
O7W—Zn3—O10W175.05 (13)O2—C7—O1122.6 (3)
O11W—Zn3—O9W85.82 (13)O2—C7—C1119.6 (3)
O7W—Zn3—O9W92.96 (13)O1—C7—C1117.8 (3)
O10W—Zn3—O9W89.80 (11)O3—C8—C9108.5 (3)
O11W—Zn3—O12W96.39 (11)O3—C8—H81110.0
O7W—Zn3—O12W90.34 (11)C9—C8—H81110.0
O10W—Zn3—O12W86.74 (10)O3—C8—H82110.0
O9W—Zn3—O12W175.92 (12)C9—C8—H82110.0
O11W—Zn3—O8W176.81 (13)H81—C8—H82108.4
O7W—Zn3—O8W87.98 (10)O5—C9—O4121.4 (3)
O10W—Zn3—O8W87.86 (10)O5—C9—C8122.0 (3)
O9W—Zn3—O8W91.18 (11)O4—C9—C8116.6 (3)
O12W—Zn3—O8W86.53 (10)O6—C10—C11108.4 (2)
C7—O1—Zn1113.75 (19)O6—C10—H101110.0
C3—O3—C8118.9 (2)C11—C10—H101110.0
C9—O4—Zn1ii102.3 (2)O6—C10—H102110.0
C5—O6—C10117.7 (2)C11—C10—H102110.0
C12—O9—Zn2116.53 (19)H101—C10—H102108.4
C15—O11—C19117.6 (2)O8—C11—O7125.1 (3)
C20—O12—Zn2i102.0 (2)O8—C11—C10120.5 (3)
C17—O14—C21118.0 (2)O7—C11—C10114.4 (3)
Zn1—O1W—H1A122.6O10—C12—O9122.7 (3)
Zn1—O1W—H1B125.9O10—C12—C13120.7 (3)
H1A—O1W—H1B108.2O9—C12—C13116.5 (3)
Zn1—O2W—H2A115.8C18—C13—C14120.8 (3)
Zn1—O2W—H2B120.4C18—C13—C12120.3 (2)
H2A—O2W—H2B109.8C14—C13—C12118.8 (3)
Zn1—O3W—H3A104.6C15—C14—C13118.8 (3)
Zn1—O3W—H3B123.5C15—C14—H14120.6
H3A—O3W—H3B112.1C13—C14—H14120.6
Zn2—O4W—H4A120.5O11—C15—C14124.3 (3)
Zn2—O4W—H4B129.4O11—C15—C16114.6 (2)
H4A—O4W—H4B110.1C14—C15—C16121.0 (3)
Zn2—O5W—H5A113.7C17—C16—C15119.3 (3)
Zn2—O5W—H5B118.3C17—C16—H16120.3
H5A—O5W—H5B109.0C15—C16—H16120.3
Zn2—O6W—H6A123.4O14—C17—C16125.0 (3)
Zn2—O6W—H6B111.8O14—C17—C18114.3 (3)
H6A—O6W—H6B111.5C16—C17—C18120.7 (3)
Zn3—O7W—H7A113.4C13—C18—C17119.3 (3)
Zn3—O7W—H7B116.6C13—C18—H18120.3
H7A—O7W—H7B107.0C17—C18—H18120.3
Zn3—O8W—H8A104.7O11—C19—C20108.5 (2)
Zn3—O8W—H8B100.3O11—C19—H191110.0
H8A—O8W—H8B104.5C20—C19—H191110.0
Zn3—O9W—H9A121.0O11—C19—H192110.0
Zn3—O9W—H9B112.6C20—C19—H192110.0
H9A—O9W—H9B110.3H191—C19—H192108.4
Zn3—O10W—H10A124.6O13—C20—O12123.3 (3)
Zn3—O10W—H10B123.1O13—C20—C19122.1 (3)
H10A—O10W—H10B109.9O12—C20—C19114.5 (3)
Zn3—O11W—H11A107.3O14—C21—C22108.5 (2)
Zn3—O11W—H11B108.5O14—C21—H211110.0
H11A—O11W—H11B108.0C22—C21—H211110.0
Zn3—O12W—H12A116.3O14—C21—H212110.0
Zn3—O12W—H12B115.6C22—C21—H212110.0
H12A—O12W—H12B108.5H211—C21—H212108.4
H13A—O13W—H13B107.3O16—C22—O15125.6 (3)
H14A—O14W—H14B109.8O16—C22—C21119.3 (3)
H15A—O15W—H15B110.8O15—C22—C21115.2 (3)
O1W—Zn1—O1—C7−6.0 (3)O3—C8—C9—O4−170.1 (3)
O4i—Zn1—O1—C7−172.6 (2)C5—O6—C10—C11172.2 (3)
O2W—Zn1—O1—C788.0 (2)O6—C10—C11—O82.4 (4)
O3W—Zn1—O1—C7−94.4 (2)O6—C10—C11—O7−177.9 (3)
O12ii—Zn2—O9—C12173.6 (2)Zn2—O9—C12—O1013.3 (4)
O4W—Zn2—O9—C126.3 (3)Zn2—O9—C12—C13−164.87 (19)
O5W—Zn2—O9—C12−90.5 (2)O10—C12—C13—C18166.3 (3)
O6W—Zn2—O9—C1296.3 (2)O9—C12—C13—C18−15.5 (4)
C6—C1—C2—C30.7 (5)O10—C12—C13—C14−15.7 (4)
C7—C1—C2—C3177.7 (3)O9—C12—C13—C14162.5 (3)
C1—C2—C3—C40.0 (5)C18—C13—C14—C15−0.7 (5)
C1—C2—C3—O3−178.9 (3)C12—C13—C14—C15−178.7 (3)
C8—O3—C3—C2−6.6 (5)C19—O11—C15—C147.4 (5)
C8—O3—C3—C4174.4 (3)C19—O11—C15—C16−173.6 (3)
C2—C3—C4—C5−1.9 (5)C13—C14—C15—O11178.7 (3)
O3—C3—C4—C5177.1 (3)C13—C14—C15—C16−0.3 (5)
C10—O6—C5—C49.0 (5)O11—C15—C16—C17−178.3 (3)
C10—O6—C5—C6−171.2 (3)C14—C15—C16—C170.8 (5)
C3—C4—C5—O6−177.1 (3)C21—O14—C17—C160.4 (5)
C3—C4—C5—C63.1 (5)C21—O14—C17—C18−179.5 (3)
C2—C1—C6—C50.6 (5)C15—C16—C17—O14179.8 (3)
C7—C1—C6—C5−176.4 (3)C15—C16—C17—C18−0.3 (5)
O6—C5—C6—C1177.7 (3)C14—C13—C18—C171.2 (5)
C4—C5—C6—C1−2.5 (5)C12—C13—C18—C17179.1 (3)
Zn1—O1—C7—O2−11.9 (4)O14—C17—C18—C13179.2 (3)
Zn1—O1—C7—C1167.1 (2)C16—C17—C18—C13−0.7 (5)
C6—C1—C7—O2−159.5 (3)C15—O11—C19—C20165.0 (3)
C2—C1—C7—O223.4 (4)Zn2i—O12—C20—O13−5.1 (4)
C6—C1—C7—O121.5 (4)Zn2i—O12—C20—C19172.5 (2)
C2—C1—C7—O1−155.5 (3)O11—C19—C20—O13−15.8 (4)
C3—O3—C8—C9−162.0 (3)O11—C19—C20—O12166.5 (3)
Zn1ii—O4—C9—O55.4 (4)C17—O14—C21—C22175.8 (3)
Zn1ii—O4—C9—C8−171.9 (2)O14—C21—C22—O16−8.7 (4)
O3—C8—C9—O512.7 (5)O14—C21—C22—O15171.7 (3)
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O100.851.902.742 (3)170
O1W—H1B···O7iii0.851.892.711 (3)162
O2W—H2A···O13Wiv0.851.942.769 (4)165
O2W—H2B···O14Wi0.851.742.591 (4)173
O3W—H3A···O13W0.841.912.747 (4)176
O3W—H3B···O15v0.841.892.722 (3)171
O4W—H4A···O15vi0.851.912.726 (3)161
O4W—H4B···O20.851.952.765 (3)163
O5W—H5A···O17W0.851.842.651 (4)159
O5W—H5B···O15Wvii0.861.932.756 (4)163
O6W—H6A···O7viii0.841.952.767 (4)164
O6W—H6B···O15W0.841.922.737 (4)162
O7W—H7A···O5iii0.871.902.726 (4)161
O7W—H7B···O160.852.122.868 (4)147
O8W—H8A···O1ix0.862.062.893 (3)163
O8W—H8B···O19Wx0.851.932.694 (4)151
O9W—H9A···O2Wix0.852.012.825 (4)162
O9W—H9B···O18W0.851.962.768 (5)161
O10W—H10B···O18W0.851.992.739 (4)146
O11W—H11A···O3viii0.852.273.029 (4)148
O11W—H11A···O3viii0.852.273.029 (4)148
O12W—H12A···O19Wx0.852.002.740 (3)144
O12W—H12B···O90.851.952.788 (3)171
O13W—H13A···O7iii0.862.092.814 (3)142
O13W—H13B···O10vii0.862.072.849 (3)150
O14W—H14A···O12ii0.851.962.782 (4)164
O14W—H14B···O16vi0.851.842.678 (4)168
O15W—H15A···O2iv0.842.302.914 (3)131
O15W—H15B···O15vi0.841.932.759 (4)169
O16W—H16B···O6Wvii0.862.172.937 (5)149
O17W—H17A···O8ix0.851.862.693 (4)170
O17W—H17B···O40.852.012.845 (4)168
O18W—H18A···O8Wiv0.872.152.975 (4)156
O18W—H18B···O3Wxi0.861.912.769 (4)173
O19W—H19A···O110.852.102.915 (4)164
O19W—H19B···O8viii0.851.952.759 (4)159
Symmetry codes: (iii) x−1, y, z+1; (iv) x+1, y, z; (i) x−1, y+1, z; (v) x, y, z−1; (vi) x+1, y, z−1; (vii) x−1, y, z; (viii) x, y, z+1; (ix) x, y−1, z+1; (x) x, y−1, z; (ii) x+1, y−1, z; (xi) x+1, y−1, z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O100.851.902.742 (3)170
O1W—H1B···O7i0.851.892.711 (3)162
O2W—H2A···O13Wii0.851.942.769 (4)165
O2W—H2B···O14Wiii0.851.742.591 (4)173
O3W—H3A···O13W0.841.912.747 (4)176
O3W—H3B···O15iv0.841.892.722 (3)171
O4W—H4A···O15v0.851.912.726 (3)161
O4W—H4B···O20.851.952.765 (3)163
O5W—H5A···O17W0.851.842.651 (4)159
O5W—H5B···O15Wvi0.861.932.756 (4)163
O6W—H6A···O7vii0.841.952.767 (4)164
O6W—H6B···O15W0.841.922.737 (4)162
O7W—H7A···O5i0.871.902.726 (4)161
O7W—H7B···O160.852.122.868 (4)147
O8W—H8A···O1viii0.862.062.893 (3)163
O8W—H8B···O19Wix0.851.932.694 (4)151
O9W—H9A···O2Wviii0.852.012.825 (4)162
O9W—H9B···O18W0.851.962.768 (5)161
O10W—H10B···O18W0.851.992.739 (4)146
O11W—H11A···O3vii0.852.273.029 (4)148
O11W—H11A···O3vii0.852.273.029 (4)148
O12W—H12A···O19Wix0.852.002.740 (3)144
O12W—H12B···O90.851.952.788 (3)171
O13W—H13A···O7i0.862.092.814 (3)142
O13W—H13B···O10vi0.862.072.849 (3)150
O14W—H14A···O12x0.851.962.782 (4)164
O14W—H14B···O16v0.851.842.678 (4)168
O15W—H15A···O2ii0.842.302.914 (3)131
O15W—H15B···O15v0.841.932.759 (4)169
O16W—H16B···O6Wvi0.862.172.937 (5)149
O17W—H17A···O8viii0.851.862.693 (4)170
O17W—H17B···O40.852.012.845 (4)168
O18W—H18A···O8Wii0.872.152.975 (4)156
O18W—H18B···O3Wxi0.861.912.769 (4)173
O19W—H19A···O110.852.102.915 (4)164
O19W—H19B···O8vii0.851.952.759 (4)159
Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z; (iii) x−1, y+1, z; (iv) x, y, z−1; (v) x+1, y, z−1; (vi) x−1, y, z; (vii) x, y, z+1; (viii) x, y−1, z+1; (ix) x, y−1, z; (x) x+1, y−1, z; (xi) x+1, y−1, z+1.
Acknowledgements top

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

references
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