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Acta Cryst. (2011). E67, m799    [ doi:10.1107/S1600536811019106 ]

Poly[[mu]-aqua-aqua{[mu]-6-ethoxy-2-[(2-isonicotinoylhydrazinylidene)methyl]phenolato-[kappa]3O,N,O'}dioxidosodiumvanadate(V)\]

H. W. Wong, K. M. Lo and S. W. Ng

Abstract top

The VV atom in the polymeric title compound, [NaV(C15H13N3O3)O2(H2O)2]n, is O,N,O'-chelated by the Schiff base dianion and is five-coordinated in a trigonal-bipramidal coordination geometry. The oxide O atoms occupy the equatorial sites and one oxide O atom is connected to the NaI atom. The ligand simultaneously O,O'-chelates to the water-coordinated NaI atom; its coordination number is seven owing to an Na...Npyridyl bond. The two independent formula units, which are disposed about a false center of inversion, are connected into a layer. Adjacent layers are consolidated into a three-dimensional network by O-H...O and O-H...N hydrogen bonds.

Comment top

Schiff bases derived from condensation of isonicotinoyl hydrazide and o-vanillin type of aromatic aldehydes function as tridentate chelates towards a large number of metal ions. For the dioxovanadium(V) species in particularly, the dianionic nature of the deprotonated ligand requires a monocationic species to balance the charges. Isonicotinic acid (2-hydroxy-3-ethoxybenzylidene)hydrazide reacts with vanadyl(IV) sulfate in the presence of sodium acetate to yield the title vanadium(V) derivative, [NaVO2(H2O)2(C15H13N3O2)]n (Scheme I, Fig. 1). The VV atom is O,N,O'-chelated by the Schiff base dianion, and is five-coordinate in a trigonal bipramidal geometry. The oxo O atoms occupy equatorial sites; one oxo O atom is connected to the NaI atom. The ligand simultaneously O,O'-chelates to the water-coordinated NaI atom; its coordination number is seven owing to an Na···Npyridyl bond. The two independent formula units are connected into a layer. Adjacent layers are consolidated into a three-dimensional network by O–H···O and O–H···N hydrogen bonds (Table 1).

Dioxovanadates(V) based on similar Schiff bases whose negative charge is also balanced by a monovalent cation have been reported before (Lippold et al., 2000; Plass et al., 2000; Plass & Yozgatli; 2003).

Related literature top

For the synthesis of isonicotinic acid (2-hydroxy-3-ethoxybenzylidene)hydrazide, see: Georgieva & Gadjeva (2002). For related vanadates, see: Lippold et al. (2000); Plass et al. (2000); Plass & Yozgatli (2003).

Experimental top

The Schiff base was synthesized by using a literature procedure (Georgieva & Gadjeva, 2002) that involved condensing isonicotinic acid hydrazide (1 g, 7.5 mmol) and 3-ethoxysalicyldehyde (1.25 g, 7.5 mmol) in ethanol. The compound (1 g, 3.5 mmol), vanadyl(IV) sulfate (0.57 g, 3.5 mmol) and sodium acetate (0.3 g, 3.5 mmol) along with ethanol (100 ml) were were heated for 4 h. The solution was filtered and light brown crystals were obtained upon slow cooling of the solvent.

Refinement top

H atoms were placed in calculated positions (C—H 0.95 to 0.98, O—H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5 U(C,O). The water molecule that is connected to two Na atoms was treated as a methylene type whereas the water that is coordinated to only one Na atom was treated as a methyl type, but with the occupancy of one H atom being zero; H···H distances are a little longer than 2.0 Å.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the layer structure of [NaVO2(H2O)2(C15H13N3O2)]n at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram of the title structure.
Poly[µ-aqua-aqua{µ-6-ethoxy-2-[(2- isonicotinoylhydrazinylidene)methyl]phenolato- κ3O,N,O'}dioxidosodiumvanadate(V)] top
Crystal data top
[NaV(C15H13N3O3)O2(H2O)2]F(000) = 1744
Mr = 425.25Dx = 1.581 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9902 reflections
a = 19.1731 (2) Åθ = 2.6–28.4°
b = 14.6913 (2) ŵ = 0.62 mm−1
c = 13.2277 (2) ÅT = 100 K
β = 106.4902 (6)°Block, dark brown
V = 3572.69 (8) Å30.40 × 0.40 × 0.40 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		8084 independent reflections
Radiation source: fine-focus sealed tube6785 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −24→24
Tmin = 0.789, Tmax = 0.789k = −17→19
23057 measured reflectionsl = −14→17
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0684P)2 + 2.7411P]
where P = (Fo2 + 2Fc2)/3
8084 reflections(Δ/σ)max = 0.001
489 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.74 e Å−3
Crystal data top
[NaV(C15H13N3O3)O2(H2O)2]V = 3572.69 (8) Å3
Mr = 425.25Z = 8
Monoclinic, P21/cMo Kα radiation
a = 19.1731 (2) ŵ = 0.62 mm−1
b = 14.6913 (2) ÅT = 100 K
c = 13.2277 (2) Å0.40 × 0.40 × 0.40 mm
β = 106.4902 (6)°
Data collection top
Bruker SMART APEX
diffractometer		8084 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6785 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 0.789Rint = 0.020
23057 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.56 e Å−3
S = 1.04Δρmin = −0.74 e Å−3
8084 reflectionsAbsolute structure: ?
489 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.117273 (15)0.64283 (2)0.60824 (2)0.01136 (9)
V20.385383 (15)0.35452 (2)0.37870 (2)0.01121 (9)
Na10.26390 (4)0.49475 (5)0.64647 (6)0.01554 (16)
Na20.23922 (4)0.50365 (5)0.33801 (6)0.01598 (17)
O10.24513 (7)0.43456 (10)0.81471 (11)0.0192 (3)
O20.15035 (7)0.53002 (9)0.67556 (10)0.0146 (3)
O30.04859 (7)0.70200 (9)0.48708 (10)0.0156 (3)
O40.18565 (7)0.65269 (9)0.55605 (11)0.0158 (3)
O50.12649 (7)0.71610 (9)0.70224 (11)0.0189 (3)
O60.26740 (7)0.57022 (10)0.17087 (11)0.0196 (3)
O70.35533 (7)0.47021 (9)0.31652 (10)0.0146 (3)
O80.44973 (7)0.28505 (9)0.49566 (10)0.0160 (3)
O90.31480 (7)0.34343 (9)0.42565 (11)0.0155 (3)
O100.37743 (7)0.28683 (9)0.27927 (11)0.0177 (3)
O1w0.19031 (7)0.42958 (9)0.47312 (11)0.0168 (3)
H110.19540.37280.47220.025*
H120.14600.44160.46230.025*
O2w0.30731 (7)0.57278 (9)0.50975 (11)0.0170 (3)
H210.35230.56500.52090.026*
H220.29900.62890.50980.026*
O3w0.32561 (8)0.35904 (10)0.64240 (12)0.0233 (3)
H310.31000.31870.67540.035*
H320.31890.34260.57950.035*
O4w0.16471 (8)0.63013 (10)0.33428 (12)0.0240 (3)
H410.17050.64920.39600.036*
H420.17580.67140.29780.036*
N10.01291 (8)0.58117 (10)0.59125 (12)0.0129 (3)
N2−0.04650 (8)0.62497 (11)0.52086 (12)0.0131 (3)
N3−0.16486 (9)0.88260 (12)0.27671 (13)0.0196 (3)
N40.49119 (8)0.41490 (11)0.41014 (12)0.0128 (3)
N50.54804 (8)0.36662 (11)0.47984 (12)0.0137 (3)
N60.65617 (9)0.10161 (12)0.72044 (13)0.0208 (4)
C10.31672 (12)0.41932 (18)0.99966 (17)0.0331 (5)
H1A0.35470.38231.04720.050*
H1B0.27250.41721.02270.050*
H1C0.33350.48241.00100.050*
C20.30060 (11)0.38249 (14)0.88914 (16)0.0215 (4)
H2A0.34570.38330.86690.026*
H2B0.28440.31850.88840.026*
C30.17389 (10)0.41942 (13)0.81015 (15)0.0157 (4)
C40.14874 (11)0.35585 (13)0.86843 (16)0.0200 (4)
H40.18240.32100.92070.024*
C50.07381 (12)0.34254 (14)0.85081 (16)0.0225 (4)
H50.05700.29790.89020.027*
C60.02461 (11)0.39376 (14)0.77681 (16)0.0198 (4)
H6−0.02610.38420.76500.024*
C70.04927 (10)0.46034 (13)0.71855 (14)0.0144 (4)
C80.12410 (10)0.47349 (12)0.73408 (14)0.0136 (3)
C9−0.00366 (10)0.51195 (13)0.64041 (14)0.0146 (4)
H9−0.05330.49420.62420.018*
C10−0.02060 (9)0.68851 (12)0.47280 (14)0.0136 (3)
C11−0.07164 (10)0.75199 (13)0.40071 (14)0.0139 (4)
C12−0.04406 (11)0.82798 (14)0.36272 (16)0.0207 (4)
H12A0.00690.83670.37720.025*
C13−0.09251 (11)0.89082 (15)0.30320 (17)0.0232 (4)
H13−0.07290.94340.27960.028*
C14−0.19078 (10)0.80815 (14)0.31169 (15)0.0175 (4)
H14−0.24200.80010.29320.021*
C15−0.14690 (10)0.74169 (13)0.37369 (15)0.0162 (4)
H15−0.16800.69020.39710.019*
C160.14547 (12)0.57897 (18)0.0608 (2)0.0364 (6)
H16A0.11220.61130.00170.055*
H16B0.12800.58450.12340.055*
H16C0.14740.51460.04260.055*
C170.21980 (12)0.61956 (16)0.08341 (18)0.0295 (5)
H17A0.23780.61470.02050.035*
H17B0.21840.68470.10170.035*
C180.34010 (10)0.58845 (13)0.19174 (15)0.0171 (4)
C190.36960 (12)0.65790 (14)0.14579 (17)0.0227 (4)
H190.33870.69590.09400.027*
C200.44503 (12)0.67204 (14)0.17573 (17)0.0238 (4)
H200.46480.72080.14540.029*
C210.49049 (11)0.61638 (14)0.24814 (16)0.0204 (4)
H21A0.54160.62610.26740.025*
C220.46124 (10)0.54448 (13)0.29418 (15)0.0154 (4)
C230.38582 (10)0.53105 (12)0.26846 (14)0.0139 (4)
C240.51098 (10)0.48724 (13)0.36962 (15)0.0147 (4)
H240.56100.50340.39080.018*
C250.51939 (9)0.29891 (13)0.51815 (14)0.0140 (4)
C260.56794 (10)0.23195 (13)0.58868 (14)0.0153 (4)
C270.53878 (11)0.15123 (14)0.61331 (16)0.0215 (4)
H270.48820.13900.58630.026*
C280.58465 (11)0.08880 (15)0.67801 (17)0.0235 (4)
H280.56410.03340.69320.028*
C290.68389 (11)0.17940 (14)0.69501 (16)0.0203 (4)
H290.73460.18970.72310.024*
C300.64247 (10)0.24577 (14)0.62976 (15)0.0184 (4)
H300.66470.29950.61360.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.01057 (15)0.01037 (16)0.01223 (16)−0.00005 (10)0.00178 (12)0.00022 (11)
V20.01082 (15)0.01033 (16)0.01139 (16)−0.00039 (10)0.00139 (12)0.00012 (11)
Na10.0139 (3)0.0157 (4)0.0162 (4)−0.0009 (3)0.0030 (3)−0.0007 (3)
Na20.0147 (3)0.0154 (4)0.0169 (4)−0.0013 (3)0.0029 (3)−0.0016 (3)
O10.0161 (6)0.0189 (7)0.0204 (7)0.0038 (5)0.0016 (5)0.0059 (5)
O20.0142 (6)0.0132 (6)0.0162 (6)0.0016 (5)0.0042 (5)0.0041 (5)
O30.0115 (6)0.0176 (7)0.0166 (6)0.0000 (5)0.0022 (5)0.0046 (5)
O40.0145 (6)0.0144 (6)0.0182 (7)0.0016 (5)0.0041 (5)0.0029 (5)
O50.0191 (6)0.0175 (7)0.0180 (7)−0.0003 (5)0.0020 (5)−0.0040 (5)
O60.0197 (7)0.0181 (7)0.0182 (7)0.0040 (5)0.0007 (5)0.0049 (5)
O70.0151 (6)0.0126 (6)0.0161 (6)0.0011 (5)0.0042 (5)0.0033 (5)
O80.0117 (6)0.0178 (7)0.0166 (6)−0.0002 (5)0.0011 (5)0.0052 (5)
O90.0140 (6)0.0151 (6)0.0165 (6)0.0013 (5)0.0030 (5)0.0021 (5)
O100.0174 (6)0.0158 (7)0.0183 (7)0.0003 (5)0.0025 (5)−0.0028 (5)
O1w0.0142 (6)0.0146 (6)0.0210 (7)0.0001 (5)0.0038 (5)0.0004 (5)
O2w0.0132 (6)0.0154 (7)0.0218 (7)0.0003 (5)0.0038 (5)−0.0004 (5)
O3w0.0310 (8)0.0222 (8)0.0175 (7)0.0068 (6)0.0084 (6)0.0051 (6)
O4w0.0311 (8)0.0234 (8)0.0179 (7)0.0082 (6)0.0076 (6)0.0054 (6)
N10.0129 (7)0.0126 (7)0.0118 (7)0.0025 (6)0.0015 (6)0.0004 (6)
N20.0103 (7)0.0142 (7)0.0130 (7)0.0025 (6)0.0004 (6)0.0015 (6)
N30.0201 (8)0.0194 (8)0.0180 (8)0.0022 (7)0.0034 (6)0.0038 (7)
N40.0127 (7)0.0135 (7)0.0110 (7)0.0018 (6)0.0014 (6)0.0004 (6)
N50.0117 (7)0.0145 (7)0.0130 (7)0.0018 (6)0.0005 (6)−0.0001 (6)
N60.0209 (8)0.0222 (9)0.0186 (8)0.0049 (7)0.0045 (7)0.0049 (7)
C10.0264 (11)0.0473 (15)0.0218 (11)0.0035 (10)0.0005 (9)−0.0052 (10)
C20.0192 (9)0.0221 (10)0.0194 (10)0.0068 (8)−0.0007 (7)0.0029 (8)
C30.0164 (8)0.0150 (9)0.0144 (9)0.0011 (7)0.0023 (7)−0.0010 (7)
C40.0246 (10)0.0181 (10)0.0147 (9)0.0035 (7)0.0014 (8)0.0049 (7)
C50.0296 (11)0.0192 (10)0.0203 (10)−0.0014 (8)0.0094 (8)0.0074 (8)
C60.0214 (9)0.0191 (10)0.0193 (9)−0.0002 (8)0.0066 (8)0.0031 (8)
C70.0165 (8)0.0135 (9)0.0135 (8)0.0004 (7)0.0050 (7)0.0004 (7)
C80.0181 (8)0.0107 (8)0.0120 (8)0.0011 (7)0.0042 (7)0.0001 (6)
C90.0140 (8)0.0149 (9)0.0149 (9)0.0007 (7)0.0043 (7)−0.0003 (7)
C100.0145 (8)0.0134 (8)0.0122 (8)0.0019 (7)0.0027 (7)−0.0012 (7)
C110.0143 (8)0.0153 (9)0.0113 (8)0.0022 (7)0.0024 (7)0.0011 (7)
C120.0160 (9)0.0217 (10)0.0238 (10)−0.0010 (8)0.0047 (8)0.0068 (8)
C130.0198 (9)0.0228 (10)0.0252 (11)−0.0015 (8)0.0037 (8)0.0096 (8)
C140.0133 (8)0.0203 (10)0.0170 (9)0.0011 (7)0.0011 (7)0.0021 (7)
C150.0161 (8)0.0151 (9)0.0157 (9)−0.0002 (7)0.0017 (7)0.0023 (7)
C160.0281 (11)0.0395 (14)0.0341 (13)0.0074 (10)−0.0032 (10)0.0051 (11)
C170.0288 (11)0.0266 (12)0.0261 (11)0.0099 (9)−0.0036 (9)0.0086 (9)
C180.0220 (9)0.0140 (9)0.0153 (9)0.0024 (7)0.0054 (7)0.0003 (7)
C190.0328 (11)0.0173 (10)0.0187 (10)0.0050 (8)0.0086 (8)0.0058 (8)
C200.0341 (11)0.0173 (10)0.0231 (11)−0.0008 (8)0.0129 (9)0.0057 (8)
C210.0240 (10)0.0182 (10)0.0212 (10)−0.0016 (8)0.0098 (8)0.0010 (8)
C220.0198 (9)0.0118 (9)0.0156 (9)0.0008 (7)0.0066 (7)0.0002 (7)
C230.0187 (8)0.0104 (8)0.0126 (8)0.0010 (7)0.0043 (7)−0.0003 (6)
C240.0135 (8)0.0146 (9)0.0167 (9)−0.0020 (7)0.0052 (7)−0.0015 (7)
C250.0135 (8)0.0160 (9)0.0112 (8)0.0013 (7)0.0014 (6)−0.0009 (7)
C260.0153 (8)0.0172 (9)0.0127 (8)0.0017 (7)0.0029 (7)0.0016 (7)
C270.0154 (9)0.0247 (11)0.0228 (10)0.0003 (8)0.0026 (8)0.0074 (8)
C280.0228 (10)0.0217 (10)0.0258 (11)0.0008 (8)0.0066 (8)0.0093 (8)
C290.0171 (9)0.0235 (10)0.0183 (10)0.0023 (8)0.0018 (7)0.0025 (8)
C300.0165 (9)0.0198 (10)0.0166 (9)−0.0001 (7)0.0012 (7)0.0018 (8)
Geometric parameters (Å, °) top
V1—O51.6159 (14)C1—C21.506 (3)
V1—O41.6523 (13)C1—H1A0.9800
V1—O21.9029 (13)C1—H1B0.9800
V1—O31.9648 (13)C1—H1C0.9800
V1—N12.1494 (15)C2—H2A0.9900
V2—O101.6211 (14)C2—H2B0.9900
V2—O91.6496 (13)C3—C41.382 (3)
V2—O71.9048 (13)C3—C81.418 (2)
V2—O81.9682 (13)C4—C51.402 (3)
V2—N42.1439 (15)C4—H40.9500
Na1—O3w2.3268 (16)C5—C61.375 (3)
Na1—O22.3732 (14)C5—H50.9500
Na1—O2w2.4764 (15)C6—C71.408 (3)
Na1—O12.5136 (16)C6—H60.9500
Na1—O1w2.5157 (15)C7—C81.404 (2)
Na1—N6i2.5260 (18)C7—C91.441 (2)
Na1—O42.8368 (15)C9—H90.9500
Na2—O4w2.3357 (16)C10—C111.486 (2)
Na2—O72.3743 (15)C11—C121.389 (3)
Na2—O1w2.4918 (15)C11—C151.393 (2)
Na2—O2w2.4925 (15)C12—C131.386 (3)
Na2—N3ii2.5040 (18)C12—H12A0.9500
Na2—O62.6104 (16)C13—H130.9500
Na2—O92.8338 (15)C14—C151.394 (3)
O1—C31.368 (2)C14—H140.9500
O1—C21.446 (2)C15—H150.9500
O2—C81.328 (2)C16—C171.495 (3)
O3—C101.301 (2)C16—H16A0.9800
O6—C181.368 (2)C16—H16B0.9800
O6—C171.448 (2)C16—H16C0.9800
O7—C231.325 (2)C17—H17A0.9900
O8—C251.299 (2)C17—H17B0.9900
O1w—H110.8400C18—C191.388 (3)
O1w—H120.8400C18—C231.416 (3)
O2w—H210.8400C19—C201.402 (3)
O2w—H220.8400C19—H190.9500
O3w—H310.8400C20—C211.368 (3)
O3w—H320.8400C20—H200.9500
O4w—H410.8400C21—C221.412 (3)
O4w—H420.8400C21—H21A0.9500
N1—C91.294 (2)C22—C231.402 (3)
N1—N21.406 (2)C22—C241.440 (3)
N2—C101.304 (2)C24—H240.9500
N3—C141.337 (3)C25—C261.487 (2)
N3—C131.336 (3)C26—C271.389 (3)
N3—Na2iii2.5040 (18)C26—C301.392 (2)
N4—C241.295 (2)C27—C281.386 (3)
N4—N51.404 (2)C27—H270.9500
N5—C251.306 (2)C28—H280.9500
N6—C281.339 (3)C29—C301.392 (3)
N6—C291.343 (3)C29—H290.9500
N6—Na1iv2.5260 (18)C30—H300.9500
O5—V1—O4109.68 (7)C25—N5—N4107.82 (14)
O5—V1—O2105.72 (7)C28—N6—C29116.46 (17)
O4—V1—O294.20 (6)C28—N6—Na1iv123.45 (14)
O5—V1—O3103.57 (7)C29—N6—Na1iv119.90 (13)
O4—V1—O392.75 (6)C2—C1—H1A109.5
O2—V1—O3145.51 (6)C2—C1—H1B109.5
O5—V1—N1104.86 (7)H1A—C1—H1B109.5
O4—V1—N1144.96 (6)C2—C1—H1C109.5
O2—V1—N181.87 (6)H1A—C1—H1C109.5
O3—V1—N173.30 (6)H1B—C1—H1C109.5
O10—V2—O9110.28 (7)O1—C2—C1112.30 (17)
O10—V2—O7104.46 (6)O1—C2—H2A109.1
O9—V2—O794.06 (6)C1—C2—H2A109.1
O10—V2—O8102.31 (6)O1—C2—H2B109.1
O9—V2—O892.93 (6)C1—C2—H2B109.1
O7—V2—O8147.93 (6)H2A—C2—H2B107.9
O10—V2—N4106.09 (6)O1—C3—C4125.96 (17)
O9—V2—N4143.14 (6)O1—C3—C8113.76 (16)
O7—V2—N482.42 (6)C4—C3—C8120.22 (17)
O8—V2—N473.42 (6)C3—C4—C5120.31 (17)
O3w—Na1—O2133.37 (6)C3—C4—H4119.8
O3w—Na1—O2w95.81 (6)C5—C4—H4119.8
O2—Na1—O2w122.09 (5)C6—C5—C4120.37 (18)
O3w—Na1—O185.44 (5)C6—C5—H5119.8
O2—Na1—O164.20 (5)C4—C5—H5119.8
O2w—Na1—O1166.33 (5)C5—C6—C7120.06 (18)
O3w—Na1—O1w79.05 (5)C5—C6—H6120.0
O2—Na1—O1w85.86 (5)C7—C6—H6120.0
O2w—Na1—O1w74.23 (5)C8—C7—C6120.24 (17)
O1—Na1—O1w119.27 (5)C8—C7—C9121.00 (17)
O3w—Na1—N6i109.68 (6)C6—C7—C9118.72 (17)
O2—Na1—N6i98.88 (6)O2—C8—C7122.78 (16)
O2w—Na1—N6i87.60 (6)O2—C8—C3118.29 (16)
O1—Na1—N6i79.20 (6)C7—C8—C3118.76 (17)
O1w—Na1—N6i160.75 (6)N1—C9—C7123.39 (17)
O3w—Na1—O4154.51 (6)N1—C9—H9118.3
O2—Na1—O459.33 (4)C7—C9—H9118.3
O2w—Na1—O463.93 (4)O3—C10—N2123.49 (16)
O1—Na1—O4118.01 (5)O3—C10—C11117.15 (16)
O1w—Na1—O480.46 (5)N2—C10—C11119.31 (16)
N6i—Na1—O485.94 (5)C12—C11—C15117.88 (17)
O4w—Na2—O7138.65 (6)C12—C11—C10119.20 (16)
O4w—Na2—O1w90.58 (5)C15—C11—C10122.83 (17)
O7—Na2—O1w123.51 (5)C13—C12—C11118.59 (18)
O4w—Na2—O2w81.61 (5)C13—C12—H12A120.7
O7—Na2—O2w85.82 (5)C11—C12—H12A120.7
O1w—Na2—O2w74.38 (5)N3—C13—C12124.57 (19)
O4w—Na2—N3ii108.21 (6)N3—C13—H13117.7
O7—Na2—N3ii99.93 (6)C12—C13—H13117.7
O1w—Na2—N3ii81.90 (5)N3—C14—C15123.72 (17)
O2w—Na2—N3ii154.50 (6)N3—C14—H14118.1
O4w—Na2—O687.50 (5)C15—C14—H14118.1
O7—Na2—O663.23 (5)C11—C15—C14118.90 (18)
O1w—Na2—O6168.97 (5)C11—C15—H15120.5
O2w—Na2—O6116.01 (5)C14—C15—H15120.5
N3ii—Na2—O688.39 (6)C17—C16—H16A109.5
O4w—Na2—O9155.24 (6)C17—C16—H16B109.5
O7—Na2—O959.28 (4)H16A—C16—H16B109.5
O1w—Na2—O966.21 (4)C17—C16—H16C109.5
O2w—Na2—O983.74 (5)H16A—C16—H16C109.5
N3ii—Na2—O978.17 (5)H16B—C16—H16C109.5
O6—Na2—O9116.93 (5)O6—C17—C16107.99 (18)
C3—O1—C2118.43 (15)O6—C17—H17A110.1
C3—O1—Na1114.22 (11)C16—C17—H17A110.1
C2—O1—Na1121.76 (12)O6—C17—H17B110.1
C8—O2—V1133.34 (12)C16—C17—H17B110.1
C8—O2—Na1118.35 (11)H17A—C17—H17B108.4
V1—O2—Na1108.27 (6)O6—C18—C19125.03 (18)
C10—O3—V1118.08 (11)O6—C18—C23114.58 (17)
V1—O4—Na198.02 (6)C19—C18—C23120.37 (18)
C18—O6—C17115.98 (16)C18—C19—C20120.07 (19)
C18—O6—Na2110.26 (11)C18—C19—H19120.0
C17—O6—Na2128.99 (13)C20—C19—H19120.0
C23—O7—V2133.52 (12)C21—C20—C19120.69 (19)
C23—O7—Na2118.30 (11)C21—C20—H20119.7
V2—O7—Na2108.17 (6)C19—C20—H20119.7
C25—O8—V2118.22 (11)C20—C21—C22119.78 (19)
V2—O9—Na298.21 (6)C20—C21—H21A120.1
Na2—O1w—Na1105.05 (5)C22—C21—H21A120.1
Na2—O1w—H11110.7C23—C22—C21120.60 (17)
Na1—O1w—H11110.7C23—C22—C24121.37 (17)
Na2—O1w—H12110.7C21—C22—C24118.02 (17)
Na1—O1w—H12110.7O7—C23—C22122.92 (16)
H11—O1w—H12108.8O7—C23—C18118.56 (16)
Na1—O2w—Na2106.22 (5)C22—C23—C18118.43 (17)
Na1—O2w—H21110.5N4—C24—C22123.52 (17)
Na2—O2w—H21110.5N4—C24—H24118.2
Na1—O2w—H22110.5C22—C24—H24118.2
Na2—O2w—H22110.5O8—C25—N5123.27 (16)
H21—O2w—H22108.7O8—C25—C26117.36 (16)
Na1—O3w—H31109.5N5—C25—C26119.34 (16)
Na1—O3w—H32109.5C27—C26—C30118.03 (17)
H31—O3w—H32109.5C27—C26—C25119.35 (17)
Na2—O4w—H41109.5C30—C26—C25122.60 (17)
Na2—O4w—H42109.5C26—C27—C28118.89 (18)
H41—O4w—H42109.5C26—C27—H27120.6
C9—N1—N2115.09 (15)C28—C27—H27120.6
C9—N1—V1129.24 (12)N6—C28—C27124.10 (19)
N2—N1—V1115.57 (11)N6—C28—H28118.0
C10—N2—N1107.54 (14)C27—C28—H28118.0
C14—N3—C13116.31 (17)N6—C29—C30123.70 (18)
C14—N3—Na2iii125.95 (13)N6—C29—H29118.2
C13—N3—Na2iii117.70 (13)C30—C29—H29118.2
C24—N4—N5114.99 (15)C26—C30—C29118.79 (18)
C24—N4—V2129.18 (12)C26—C30—H30120.6
N5—N4—V2115.71 (11)C29—C30—H30120.6
O3w—Na1—O1—C3−116.11 (13)O6—Na2—O2w—Na1178.74 (5)
O2—Na1—O1—C327.38 (12)O9—Na2—O2w—Na1−64.29 (5)
O2w—Na1—O1—C3148.0 (2)O5—V1—N1—C9−87.20 (17)
O1w—Na1—O1—C3−41.36 (14)O4—V1—N1—C9102.71 (18)
N6i—Na1—O1—C3132.84 (13)O2—V1—N1—C917.00 (16)
O4—Na1—O1—C353.39 (13)O3—V1—N1—C9172.79 (17)
O3w—Na1—O1—C237.07 (14)O5—V1—N1—N289.02 (13)
O2—Na1—O1—C2−179.45 (15)O4—V1—N1—N2−81.06 (16)
O2w—Na1—O1—C2−58.8 (3)O2—V1—N1—N2−166.78 (12)
O1w—Na1—O1—C2111.82 (14)O3—V1—N1—N2−10.99 (11)
N6i—Na1—O1—C2−73.98 (14)C9—N1—N2—C10−175.67 (16)
O4—Na1—O1—C2−153.43 (13)V1—N1—N2—C107.56 (18)
O5—V1—O2—C869.85 (17)O10—V2—N4—C2487.21 (17)
O4—V1—O2—C8−178.35 (16)O9—V2—N4—C24−102.38 (18)
O3—V1—O2—C8−77.29 (19)O7—V2—N4—C24−15.73 (16)
N1—V1—O2—C8−33.38 (16)O8—V2—N4—C24−174.41 (18)
O5—V1—O2—Na1−107.86 (7)O10—V2—N4—N5−88.64 (13)
O4—V1—O2—Na13.95 (7)O9—V2—N4—N581.78 (16)
O3—V1—O2—Na1105.01 (10)O7—V2—N4—N5168.43 (13)
N1—V1—O2—Na1148.91 (7)O8—V2—N4—N59.74 (11)
O3w—Na1—O2—C827.16 (16)C24—N4—N5—C25176.69 (16)
O2w—Na1—O2—C8166.35 (12)V2—N4—N5—C25−6.87 (18)
O1—Na1—O2—C8−27.53 (12)C3—O1—C2—C1−79.2 (2)
O1w—Na1—O2—C897.88 (13)Na1—O1—C2—C1128.68 (16)
N6i—Na1—O2—C8−100.90 (13)C2—O1—C3—C4−2.3 (3)
O4—Na1—O2—C8179.23 (14)Na1—O1—C3—C4151.87 (17)
O3w—Na1—O2—V1−154.74 (7)C2—O1—C3—C8−179.53 (16)
O2w—Na1—O2—V1−15.55 (9)Na1—O1—C3—C8−25.40 (19)
O1—Na1—O2—V1150.57 (8)O1—C3—C4—C5−175.34 (19)
O1w—Na1—O2—V1−84.02 (6)C8—C3—C4—C51.8 (3)
N6i—Na1—O2—V177.20 (7)C3—C4—C5—C6−1.2 (3)
O4—Na1—O2—V1−2.67 (5)C4—C5—C6—C7−0.3 (3)
O5—V1—O3—C10−89.13 (14)C5—C6—C7—C81.3 (3)
O4—V1—O3—C10159.87 (13)C5—C6—C7—C9179.06 (19)
O2—V1—O3—C1058.37 (17)V1—O2—C8—C733.3 (3)
N1—V1—O3—C1012.58 (13)Na1—O2—C8—C7−149.21 (14)
O5—V1—O4—Na1105.19 (7)V1—O2—C8—C3−151.49 (14)
O2—V1—O4—Na1−3.17 (6)Na1—O2—C8—C326.0 (2)
O3—V1—O4—Na1−149.36 (5)C6—C7—C8—O2174.43 (17)
N1—V1—O4—Na1−85.00 (11)C9—C7—C8—O2−3.2 (3)
O3w—Na1—O4—V1130.65 (12)C6—C7—C8—C3−0.8 (3)
O2—Na1—O4—V12.94 (5)C9—C7—C8—C3−178.48 (17)
O2w—Na1—O4—V1170.81 (7)O1—C3—C8—O21.3 (2)
O1—Na1—O4—V1−24.39 (8)C4—C3—C8—O2−176.18 (17)
O1w—Na1—O4—V193.78 (6)O1—C3—C8—C7176.70 (16)
N6i—Na1—O4—V1−99.88 (7)C4—C3—C8—C7−0.7 (3)
O4w—Na2—O6—C18118.39 (12)N2—N1—C9—C7−177.61 (16)
O7—Na2—O6—C18−31.34 (11)V1—N1—C9—C7−1.4 (3)
O1w—Na2—O6—C18−161.4 (3)C8—C7—C9—N1−10.3 (3)
O2w—Na2—O6—C1838.97 (13)C6—C7—C9—N1172.02 (18)
N3ii—Na2—O6—C18−133.30 (12)V1—O3—C10—N2−13.9 (2)
O9—Na2—O6—C18−57.44 (13)V1—O3—C10—C11163.67 (12)
O4w—Na2—O6—C17−35.70 (17)N1—N2—C10—O33.3 (2)
O7—Na2—O6—C17174.58 (17)N1—N2—C10—C11−174.22 (15)
O1w—Na2—O6—C1744.5 (4)O3—C10—C11—C12−7.8 (3)
O2w—Na2—O6—C17−115.11 (16)N2—C10—C11—C12169.91 (18)
N3ii—Na2—O6—C1772.61 (17)O3—C10—C11—C15175.95 (17)
O9—Na2—O6—C17148.47 (16)N2—C10—C11—C15−6.4 (3)
O10—V2—O7—C23−73.90 (17)C15—C11—C12—C132.1 (3)
O9—V2—O7—C23173.94 (16)C10—C11—C12—C13−174.36 (18)
O8—V2—O7—C2371.8 (2)C14—N3—C13—C120.4 (3)
N4—V2—O7—C2330.84 (16)Na2iii—N3—C13—C12−177.51 (17)
O10—V2—O7—Na2107.11 (7)C11—C12—C13—N3−1.9 (3)
O9—V2—O7—Na2−5.05 (7)C13—N3—C14—C150.9 (3)
O8—V2—O7—Na2−107.14 (10)Na2iii—N3—C14—C15178.59 (14)
N4—V2—O7—Na2−148.15 (7)C12—C11—C15—C14−1.0 (3)
O4w—Na2—O7—C23−18.30 (17)C10—C11—C15—C14175.36 (17)
O1w—Na2—O7—C23−158.72 (12)N3—C14—C15—C11−0.6 (3)
O2w—Na2—O7—C23−90.57 (13)C18—O6—C17—C16169.99 (18)
N3ii—Na2—O7—C23114.48 (13)Na2—O6—C17—C16−37.1 (3)
O6—Na2—O7—C2331.39 (12)C17—O6—C18—C199.2 (3)
O9—Na2—O7—C23−175.76 (14)Na2—O6—C18—C19−148.61 (17)
O4w—Na2—O7—V2160.87 (7)C17—O6—C18—C23−172.29 (17)
O1w—Na2—O7—V220.45 (9)Na2—O6—C18—C2329.91 (19)
O2w—Na2—O7—V288.60 (6)O6—C18—C19—C20177.99 (19)
N3ii—Na2—O7—V2−66.35 (7)C23—C18—C19—C20−0.4 (3)
O6—Na2—O7—V2−149.44 (8)C18—C19—C20—C211.8 (3)
O9—Na2—O7—V23.41 (5)C19—C20—C21—C22−0.7 (3)
O10—V2—O8—C2592.32 (14)C20—C21—C22—C23−1.7 (3)
O9—V2—O8—C25−156.19 (14)C20—C21—C22—C24179.70 (19)
O7—V2—O8—C25−53.77 (18)V2—O7—C23—C22−31.7 (3)
N4—V2—O8—C25−11.03 (13)Na2—O7—C23—C22147.24 (15)
O10—V2—O9—Na2−102.99 (7)V2—O7—C23—C18151.86 (14)
O7—V2—O9—Na24.06 (6)Na2—O7—C23—C18−29.2 (2)
O8—V2—O9—Na2152.74 (5)C21—C22—C23—O7−173.52 (17)
N4—V2—O9—Na286.83 (10)C24—C22—C23—O75.0 (3)
O4w—Na2—O9—V2−146.59 (12)C21—C22—C23—C183.0 (3)
O7—Na2—O9—V2−3.78 (5)C24—C22—C23—C18−178.50 (17)
O1w—Na2—O9—V2−168.28 (7)O6—C18—C23—O7−3.8 (3)
O2w—Na2—O9—V2−92.62 (6)C19—C18—C23—O7174.75 (18)
N3ii—Na2—O9—V2105.45 (7)O6—C18—C23—C22179.53 (16)
O6—Na2—O9—V223.42 (8)C19—C18—C23—C22−1.9 (3)
O4w—Na2—O1w—Na1−83.78 (6)N5—N4—C24—C22178.13 (17)
O7—Na2—O1w—Na171.33 (7)V2—N4—C24—C222.3 (3)
O2w—Na2—O1w—Na1−2.65 (5)C23—C22—C24—N47.5 (3)
N3ii—Na2—O1w—Na1167.91 (6)C21—C22—C24—N4−173.93 (18)
O6—Na2—O1w—Na1−163.7 (3)V2—O8—C25—N512.0 (2)
O9—Na2—O1w—Na187.32 (5)V2—O8—C25—C26−166.18 (12)
O3w—Na1—O1w—Na2−96.64 (6)N4—N5—C25—O8−2.6 (2)
O2—Na1—O1w—Na2127.70 (6)N4—N5—C25—C26175.49 (15)
O2w—Na1—O1w—Na22.67 (5)O8—C25—C26—C2710.4 (3)
O1—Na1—O1w—Na2−175.03 (5)N5—C25—C26—C27−167.87 (18)
N6i—Na1—O1w—Na222.5 (2)O8—C25—C26—C30−171.11 (18)
O4—Na1—O1w—Na268.12 (5)N5—C25—C26—C3010.6 (3)
O3w—Na1—O2w—Na274.19 (6)C30—C26—C27—C280.6 (3)
O2—Na1—O2w—Na2−77.29 (7)C25—C26—C27—C28179.18 (19)
O1—Na1—O2w—Na2168.8 (2)C29—N6—C28—C27−1.8 (3)
O1w—Na1—O2w—Na2−2.69 (5)Na1iv—N6—C28—C27173.16 (17)
N6i—Na1—O2w—Na2−176.27 (6)C26—C27—C28—N61.0 (3)
O4—Na1—O2w—Na2−89.62 (5)C28—N6—C29—C301.0 (3)
O4w—Na2—O2w—Na195.68 (6)Na1iv—N6—C29—C30−174.16 (15)
O7—Na2—O2w—Na1−123.81 (6)C27—C26—C30—C29−1.3 (3)
O1w—Na2—O2w—Na12.71 (5)C25—C26—C30—C29−179.86 (18)
N3ii—Na2—O2w—Na1−19.44 (16)N6—C29—C30—C260.5 (3)
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H12···N2v0.842.212.894 (2)139
O2w—H21···N5vi0.842.162.879 (2)143
O3w—H32···O90.842.012.825 (2)162
O3w—H31···O10vii0.842.232.799 (2)126
O4w—H41···O40.842.052.865 (2)162
O4w—H42···O5viii0.842.132.822 (2)139
Symmetry codes: (v) −x, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x, −y+1/2, z+1/2; (viii) x, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H12···N2i0.842.212.894 (2)139
O2w—H21···N5ii0.842.162.879 (2)143
O3w—H32···O90.842.012.825 (2)162
O3w—H31···O10iii0.842.232.799 (2)126
O4w—H41···O40.842.052.865 (2)162
O4w—H42···O5iv0.842.132.822 (2)139
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
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