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Acta Cryst. (2007). E63, m1532    [ doi:10.1107/S1600536807020521 ]

Bis[1,3-dihydroxy-2-hydroxymethyl-2-(5-nitro-2-oxidobenzylideneamino)propane-[kappa]3N,O,O']zinc(II) trihydrate

H. M. Ali, S. Puvaneswary, B. Wan Jefrey and S. W. Ng

Abstract top

The Zn atom in the title compound, [Zn(C11H13N2O6)2]·3H2O, is chelated by the two terdentate Schiff base anions, resulting in a trans-ZnN2O4 octahedral geometry. The crystal packing is stabilized by O-H...O hydrogen bonds, leading to a three-dimensional network structure.

Comment top

A previous study (Ali et al., 2006) reported the structure of the complex ion found in the title compound as a bis-pyridine solvate. The use of DMSO as solvent yielded the title trihdrate (I) (Fig. 1). Two deprotonated Schiff-base ligands chelate through their phenoxy oxygen atoms, imino nitrogen and hydroxyl oxygen atoms (Table 1). The hydroxy groups of the ligands are engaged in extensive hydrogen bonding with the the uncoordinated water molecules to lead to a three-dimensional network (Table 2).

Related literature top

For the same metal complex as a pyridine solvate, see: Ali et al. (2006).

Experimental top

The Schiff base used to make the title compound was synthesized from tris(hydroxymethyl)aminomethane and 5-nitrosalicylaldehyde. The ligand (0.23 g, 0.85 mmol) was dissolved in ethanol (25 ml) and several drops of aqueous sodium hydroxide were added to raise the pH of the solution to about 8.5. Zinc acetate (0.09 g, 0.43 mmol) was then added and the mixture heated for 5 h. The solvent was removed and the product recrystallized from DMSO to yield faint yellow blocks of (I). The water in (I) was presumably incorporated from the atmosphere.

Refinement top

The carbon-bound H atoms were placed at calculated positions (C–H = 0.95–0.99 Å), and they were included in the refinement in the riding model approximation with Uiso(H) = 1.2Ueq(C). The hydroxy and water H atoms were located in a difference Fourier map, and were refined with a distance restraint (O–H = 0.84±0.01 Å); their Uiso values were freely refined.

Computing details top

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I). Displacement ellipsoids are drawn at the 70% probability level (H atoms are shown as spheres of arbitrary radius).
Bis[1,3-dihydroxy-2-hydroxymethyl-2-(5-nitro-2-oxidobenzylideneamino)propane- κ3N,O,O']zinc(II) trihydrate top
Crystal data top
[Zn(C11H13N2O6)2]·3H2OF(000) = 1368
Mr = 657.89Dx = 1.621 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8727 reflections
a = 10.7231 (2) Åθ = 2.5–34.6°
b = 11.7429 (2) ŵ = 0.99 mm−1
c = 21.7538 (3) ÅT = 173 K
β = 100.227 (1)°Irregular block, faint yellow
V = 2695.72 (8) Å30.52 × 0.35 × 0.35 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		6185 independent reflections
Radiation source: fine-focus sealed tube5696 reflections with I > 2σ(I)
graphiteRint = 0.029
φ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.590, Tmax = 0.722k = −15→15
55575 measured reflectionsl = −28→28
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2 + 1.457P]
where P = (Fo2 + 2Fc2)/3
6185 reflections(Δ/σ)max = 0.001
427 parametersΔρmax = 0.46 e Å−3
12 restraintsΔρmin = −0.27 e Å−3
Crystal data top
[Zn(C11H13N2O6)2]·3H2OV = 2695.72 (8) Å3
Mr = 657.89Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.7231 (2) ŵ = 0.99 mm−1
b = 11.7429 (2) ÅT = 173 K
c = 21.7538 (3) Å0.52 × 0.35 × 0.35 mm
β = 100.227 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		6185 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5696 reflections with I > 2σ(I)
Tmin = 0.590, Tmax = 0.722Rint = 0.029
55575 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069Δρmax = 0.46 e Å−3
S = 1.02Δρmin = −0.27 e Å−3
6185 reflectionsAbsolute structure: ?
427 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.484037 (13)0.450449 (12)0.344186 (6)0.01048 (5)
O10.56842 (9)0.36478 (8)0.27965 (4)0.01451 (18)
O20.37281 (9)0.56145 (8)0.39519 (4)0.01370 (18)
O30.28019 (9)0.73088 (8)0.22313 (5)0.0176 (2)
O40.02639 (9)0.55207 (9)0.31518 (5)0.0186 (2)
O50.55010 (11)0.32881 (12)−0.00644 (5)0.0315 (3)
O60.36276 (12)0.39495 (12)−0.00592 (5)0.0374 (3)
O70.38730 (9)0.31709 (8)0.37207 (4)0.01398 (18)
O80.60464 (9)0.59756 (8)0.34246 (4)0.01519 (19)
O90.97710 (9)0.50096 (9)0.42660 (5)0.0196 (2)
O100.77487 (9)0.53162 (9)0.53065 (4)0.01668 (19)
O110.39461 (11)−0.00756 (10)0.59767 (5)0.0300 (3)
O120.57778 (11)0.07193 (10)0.62595 (5)0.0273 (2)
O1W0.54356 (11)0.73526 (11)0.24683 (6)0.0280 (2)
O2W0.61738 (14)0.65040 (14)0.14354 (6)0.0417 (3)
O3W0.87436 (10)0.63095 (9)0.20693 (5)0.0229 (2)
N10.46896 (12)0.36639 (11)0.02166 (5)0.0201 (2)
N20.34315 (10)0.50587 (9)0.27214 (5)0.0106 (2)
N30.47816 (12)0.05985 (10)0.58859 (6)0.0180 (2)
N40.63672 (10)0.41467 (9)0.41535 (5)0.0112 (2)
C10.54691 (12)0.37682 (10)0.21976 (6)0.0125 (2)
C20.63983 (13)0.33967 (12)0.18453 (6)0.0166 (3)
H20.72010.31490.20610.020*
C30.61644 (13)0.33876 (12)0.12065 (6)0.0173 (3)
H30.67980.31390.09820.021*
C40.49776 (13)0.37499 (11)0.08866 (6)0.0159 (3)
C50.40829 (13)0.41975 (11)0.12047 (6)0.0147 (2)
H50.33010.44730.09790.018*
C60.43230 (12)0.42464 (11)0.18558 (6)0.0120 (2)
C70.33752 (12)0.48409 (11)0.21393 (6)0.0122 (2)
H70.26390.50940.18640.015*
C80.23991 (12)0.57477 (11)0.29063 (6)0.0116 (2)
C90.29593 (12)0.63565 (11)0.35181 (6)0.0143 (2)
H9A0.34790.70090.34240.017*
H9B0.22600.66600.37120.017*
C100.18367 (12)0.66386 (11)0.24237 (6)0.0136 (2)
H10A0.13390.62520.20560.016*
H10B0.12550.71400.26060.016*
C110.13271 (12)0.49241 (11)0.29965 (6)0.0145 (2)
H11A0.10550.44860.26070.017*
H11B0.16500.43780.33340.017*
C120.41320 (12)0.25775 (10)0.42287 (6)0.0117 (2)
C130.31940 (12)0.18237 (11)0.43848 (6)0.0153 (3)
H130.24010.17700.41110.018*
C140.33969 (13)0.11756 (11)0.49157 (6)0.0157 (3)
H140.27560.06800.50090.019*
C150.45667 (13)0.12566 (11)0.53189 (6)0.0147 (2)
C160.55135 (12)0.19657 (11)0.51877 (6)0.0141 (2)
H160.63020.19970.54670.017*
C170.53229 (12)0.26373 (11)0.46495 (6)0.0122 (2)
C180.63767 (12)0.33792 (11)0.45755 (6)0.0129 (2)
H180.71420.32870.48670.015*
C190.74779 (11)0.49089 (11)0.41778 (6)0.0118 (2)
C200.73077 (12)0.55311 (11)0.35481 (6)0.0137 (2)
H20A0.79310.61580.35660.016*
H20B0.74380.49970.32130.016*
C210.87318 (12)0.42490 (12)0.42665 (6)0.0155 (3)
H21A0.88500.38290.46670.019*
H21B0.87050.36870.39250.019*
C220.74665 (13)0.57977 (11)0.46974 (6)0.0145 (2)
H22A0.80960.63980.46590.017*
H22B0.66210.61610.46400.017*
H2O0.3294 (17)0.5271 (16)0.4177 (8)0.031 (5)*
H3O0.2450 (18)0.7667 (16)0.1918 (7)0.036 (5)*
H4O−0.0227 (18)0.5733 (19)0.2831 (7)0.042 (6)*
H8O0.5937 (19)0.6421 (15)0.3125 (7)0.033 (5)*
H9O0.9814 (19)0.5166 (18)0.3901 (5)0.032 (5)*
H10O0.8525 (9)0.5287 (18)0.5423 (10)0.034 (5)*
H1W10.5666 (18)0.7032 (15)0.2156 (7)0.028 (5)*
H1W20.4639 (9)0.735 (2)0.2426 (11)0.049 (7)*
H2W10.6926 (14)0.629 (3)0.1600 (13)0.079 (10)*
H2W20.609 (4)0.643 (4)0.1038 (5)0.131 (15)*
H3W10.887 (2)0.7015 (9)0.2026 (11)0.052 (7)*
H3W20.900 (2)0.601 (2)0.1756 (8)0.056 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.00938 (8)0.01265 (8)0.00889 (8)−0.00022 (5)0.00021 (5)0.00146 (5)
O10.0148 (4)0.0169 (4)0.0114 (4)0.0034 (3)0.0012 (3)0.0012 (3)
O20.0138 (4)0.0172 (4)0.0101 (4)0.0009 (3)0.0021 (3)0.0016 (3)
O30.0148 (5)0.0183 (5)0.0184 (5)−0.0012 (4)−0.0008 (4)0.0084 (4)
O40.0137 (5)0.0263 (5)0.0170 (5)0.0051 (4)0.0059 (4)0.0039 (4)
O50.0277 (6)0.0523 (7)0.0172 (5)0.0038 (5)0.0114 (4)−0.0083 (5)
O60.0385 (7)0.0569 (8)0.0141 (5)0.0253 (6)−0.0026 (5)−0.0056 (5)
O70.0144 (4)0.0158 (4)0.0105 (4)−0.0031 (3)−0.0013 (3)0.0025 (3)
O80.0119 (4)0.0175 (5)0.0154 (5)0.0004 (4)0.0003 (3)0.0065 (4)
O90.0102 (4)0.0335 (6)0.0152 (5)−0.0036 (4)0.0026 (4)0.0056 (4)
O100.0116 (5)0.0272 (5)0.0110 (4)−0.0020 (4)0.0012 (4)0.0021 (4)
O110.0308 (6)0.0332 (6)0.0245 (6)−0.0131 (5)0.0012 (5)0.0149 (5)
O120.0233 (5)0.0340 (6)0.0215 (5)−0.0036 (5)−0.0049 (4)0.0126 (5)
O1W0.0201 (5)0.0355 (6)0.0271 (6)0.0006 (5)0.0006 (5)0.0118 (5)
O2W0.0358 (7)0.0589 (9)0.0284 (7)0.0008 (6)0.0000 (6)−0.0022 (6)
O3W0.0245 (5)0.0215 (5)0.0221 (5)0.0005 (4)0.0024 (4)−0.0056 (4)
N10.0262 (6)0.0213 (6)0.0132 (5)0.0032 (5)0.0050 (5)−0.0015 (4)
N20.0094 (5)0.0112 (5)0.0114 (5)0.0005 (4)0.0020 (4)0.0005 (4)
N30.0196 (6)0.0183 (6)0.0158 (6)−0.0007 (4)0.0025 (5)0.0047 (4)
N40.0096 (5)0.0129 (5)0.0110 (5)−0.0014 (4)0.0021 (4)0.0000 (4)
C10.0133 (6)0.0114 (5)0.0128 (6)−0.0008 (4)0.0022 (5)−0.0002 (4)
C20.0134 (6)0.0191 (6)0.0174 (6)0.0039 (5)0.0032 (5)0.0004 (5)
C30.0180 (6)0.0181 (6)0.0176 (6)0.0030 (5)0.0076 (5)−0.0002 (5)
C40.0211 (7)0.0166 (6)0.0107 (6)0.0015 (5)0.0046 (5)−0.0004 (5)
C50.0160 (6)0.0147 (6)0.0127 (6)0.0020 (5)0.0009 (5)−0.0001 (5)
C60.0120 (6)0.0120 (5)0.0124 (6)0.0004 (4)0.0030 (5)−0.0004 (4)
C70.0101 (6)0.0132 (5)0.0126 (6)0.0005 (4)0.0001 (4)−0.0001 (5)
C80.0111 (6)0.0123 (5)0.0117 (6)0.0014 (4)0.0027 (4)−0.0001 (5)
C90.0168 (6)0.0139 (6)0.0118 (6)0.0024 (5)0.0013 (5)−0.0007 (5)
C100.0125 (6)0.0141 (6)0.0140 (6)0.0023 (5)0.0019 (5)0.0016 (5)
C110.0124 (6)0.0153 (6)0.0163 (6)0.0009 (5)0.0042 (5)0.0005 (5)
C120.0131 (6)0.0113 (5)0.0104 (5)−0.0001 (4)0.0014 (4)−0.0013 (4)
C130.0130 (6)0.0178 (6)0.0143 (6)−0.0033 (5)0.0002 (5)0.0005 (5)
C140.0155 (6)0.0158 (6)0.0163 (6)−0.0039 (5)0.0041 (5)0.0007 (5)
C150.0183 (6)0.0135 (6)0.0121 (6)−0.0004 (5)0.0026 (5)0.0032 (5)
C160.0140 (6)0.0147 (6)0.0128 (6)−0.0003 (5)−0.0001 (5)0.0009 (5)
C170.0129 (6)0.0120 (5)0.0118 (6)−0.0008 (4)0.0020 (5)0.0007 (4)
C180.0107 (6)0.0155 (6)0.0115 (6)−0.0004 (5)−0.0004 (4)0.0005 (5)
C190.0090 (5)0.0145 (6)0.0117 (6)−0.0021 (4)0.0012 (4)0.0014 (5)
C200.0101 (6)0.0175 (6)0.0132 (6)−0.0020 (5)0.0012 (5)0.0028 (5)
C210.0102 (6)0.0197 (6)0.0168 (6)−0.0004 (5)0.0025 (5)0.0020 (5)
C220.0153 (6)0.0161 (6)0.0117 (6)−0.0021 (5)0.0016 (5)0.0006 (5)
Geometric parameters (Å, °) top
Zn1—O12.062 (1)C2—C31.3676 (19)
Zn1—O22.196 (1)C2—H20.9500
Zn1—O72.030 (1)C3—C41.4038 (19)
Zn1—O82.162 (1)C3—H30.9500
Zn1—N22.079 (1)C4—C51.3825 (18)
Zn1—N42.087 (1)C5—C61.3952 (18)
O1—C11.2898 (15)C5—H50.9500
O2—C91.4329 (15)C6—C71.4570 (17)
O2—H2O0.837 (9)C7—H70.9500
O3—C101.4211 (16)C8—C101.5282 (17)
O3—H3O0.832 (9)C8—C91.5360 (17)
O4—C111.4288 (15)C8—C111.5412 (17)
O4—H4O0.834 (10)C9—H9A0.9900
O5—N11.2305 (16)C9—H9B0.9900
O6—N11.2355 (17)C10—H10A0.9900
O7—C121.2941 (15)C10—H10B0.9900
O8—C201.4300 (15)C11—H11A0.9900
O8—H8O0.828 (9)C11—H11B0.9900
O9—C211.4283 (16)C12—C131.4254 (18)
O9—H9O0.824 (9)C12—C171.4348 (17)
O10—C221.4229 (15)C13—C141.3679 (18)
O10—H10O0.826 (9)C13—H130.9500
O11—N31.2375 (16)C14—C151.4004 (18)
O12—N31.2301 (16)C14—H140.9500
O1W—H1W10.852 (9)C15—C161.3814 (18)
O1W—H1W20.843 (10)C16—C171.3964 (17)
O2W—H2W10.860 (10)C16—H160.9500
O2W—H2W20.857 (10)C17—C181.4581 (17)
O3W—H3W10.848 (10)C18—H180.9500
O3W—H3W20.851 (10)C19—C211.5341 (17)
N1—C41.4387 (17)C19—C201.5345 (17)
N2—C71.2828 (16)C19—C221.5402 (18)
N2—C81.4833 (16)C20—H20A0.9900
N3—C151.4391 (17)C20—H20B0.9900
N4—C181.2853 (17)C21—H21A0.9900
N4—C191.4833 (15)C21—H21B0.9900
C1—C21.4289 (18)C22—H22A0.9900
C1—C61.4332 (17)C22—H22B0.9900
O7—Zn1—O197.84 (4)N2—C8—C11107.55 (10)
O7—Zn1—N297.20 (4)C10—C8—C11107.75 (10)
O1—Zn1—N289.28 (4)C9—C8—C11111.57 (10)
O7—Zn1—N489.90 (4)O2—C9—C8112.23 (10)
O1—Zn1—N491.46 (4)O2—C9—H9A109.2
N2—Zn1—N4172.70 (4)C8—C9—H9A109.2
O7—Zn1—O8163.85 (4)O2—C9—H9B109.2
O1—Zn1—O892.40 (4)C8—C9—H9B109.2
N2—Zn1—O895.37 (4)H9A—C9—H9B107.9
N4—Zn1—O877.34 (4)O3—C10—C8111.24 (10)
O7—Zn1—O287.40 (4)O3—C10—H10A109.4
O1—Zn1—O2167.64 (4)C8—C10—H10A109.4
N2—Zn1—O278.92 (4)O3—C10—H10B109.4
N4—Zn1—O299.77 (4)C8—C10—H10B109.4
O8—Zn1—O285.11 (4)H10A—C10—H10B108.0
C1—O1—Zn1127.78 (8)O4—C11—C8111.52 (11)
C9—O2—Zn1109.20 (7)O4—C11—H11A109.3
C9—O2—H2O111.3 (14)C8—C11—H11A109.3
Zn1—O2—H2O114.8 (14)O4—C11—H11B109.3
C10—O3—H3O105.8 (14)C8—C11—H11B109.3
C11—O4—H4O111.2 (16)H11A—C11—H11B108.0
C12—O7—Zn1128.83 (8)O7—C12—C13118.97 (11)
C20—O8—Zn1104.71 (7)O7—C12—C17123.38 (11)
C20—O8—H8O112.1 (14)C13—C12—C17117.66 (11)
Zn1—O8—H8O121.1 (14)C14—C13—C12122.24 (12)
C21—O9—H9O108.4 (15)C14—C13—H13118.9
C22—O10—H10O109.7 (15)C12—C13—H13118.9
H1W1—O1W—H1W2110 (2)C13—C14—C15118.78 (12)
H2W1—O2W—H2W2108 (3)C13—C14—H14120.6
H3W1—O3W—H3W2103 (2)C15—C14—H14120.6
O5—N1—O6121.88 (12)C16—C15—C14121.40 (12)
O5—N1—C4119.00 (12)C16—C15—N3119.27 (12)
O6—N1—C4119.11 (12)C14—C15—N3119.32 (12)
C7—N2—C8118.03 (10)C15—C16—C17120.67 (12)
C7—N2—Zn1125.62 (9)C15—C16—H16119.7
C8—N2—Zn1116.35 (8)C17—C16—H16119.7
O12—N3—O11122.46 (12)C16—C17—C12119.24 (11)
O12—N3—C15119.50 (12)C16—C17—C18115.41 (11)
O11—N3—C15118.03 (12)C12—C17—C18125.33 (11)
C18—N4—C19119.55 (11)N4—C18—C17126.14 (12)
C18—N4—Zn1125.23 (9)N4—C18—H18116.9
C19—N4—Zn1115.10 (8)C17—C18—H18116.9
O1—C1—C2119.44 (11)N4—C19—C21112.33 (10)
O1—C1—C6123.37 (11)N4—C19—C20106.74 (10)
C2—C1—C6117.18 (12)C21—C19—C20108.39 (10)
C3—C2—C1121.86 (12)N4—C19—C22108.91 (10)
C3—C2—H2119.1C21—C19—C22111.78 (10)
C1—C2—H2119.1C20—C19—C22108.50 (10)
C2—C3—C4119.21 (12)O8—C20—C19107.46 (10)
C2—C3—H3120.4O8—C20—H20A110.2
C4—C3—H3120.4C19—C20—H20A110.2
C5—C4—C3121.04 (12)O8—C20—H20B110.2
C5—C4—N1119.38 (12)C19—C20—H20B110.2
C3—C4—N1119.58 (12)H20A—C20—H20B108.5
C4—C5—C6120.30 (12)O9—C21—C19110.52 (11)
C4—C5—H5119.8O9—C21—H21A109.5
C6—C5—H5119.9C19—C21—H21A109.5
C5—C6—C1119.82 (12)O9—C21—H21B109.5
C5—C6—C7115.63 (11)C19—C21—H21B109.5
C1—C6—C7124.51 (12)H21A—C21—H21B108.1
N2—C7—C6126.81 (12)O10—C22—C19112.71 (11)
N2—C7—H7116.6O10—C22—H22A109.0
C6—C7—H7116.6C19—C22—H22A109.0
N2—C8—C10114.18 (10)O10—C22—H22B109.0
N2—C8—C9107.04 (10)C19—C22—H22B109.0
C10—C8—C9108.81 (10)H22A—C22—H22B107.8
O7—Zn1—O1—C1112.03 (10)C5—C6—C7—N2−175.06 (13)
N2—Zn1—O1—C114.87 (11)C1—C6—C7—N22.4 (2)
N4—Zn1—O1—C1−157.87 (11)C7—N2—C8—C10−32.67 (16)
O8—Zn1—O1—C1−80.48 (10)Zn1—N2—C8—C10148.33 (9)
O2—Zn1—O1—C1−2.5 (2)C7—N2—C8—C9−153.16 (11)
O7—Zn1—O2—C9−116.17 (8)Zn1—N2—C8—C927.84 (12)
O1—Zn1—O2—C9−0.6 (2)C7—N2—C8—C1186.83 (13)
N2—Zn1—O2—C9−18.31 (8)Zn1—N2—C8—C11−92.17 (10)
N4—Zn1—O2—C9154.38 (8)Zn1—O2—C9—C839.50 (12)
O8—Zn1—O2—C978.15 (8)N2—C8—C9—O2−44.26 (13)
O1—Zn1—O7—C12103.45 (11)C10—C8—C9—O2−168.11 (10)
N2—Zn1—O7—C12−166.29 (10)C11—C8—C9—O273.15 (13)
N4—Zn1—O7—C1211.98 (11)N2—C8—C10—O3−50.24 (14)
O8—Zn1—O7—C12−25.4 (2)C9—C8—C10—O369.25 (13)
O2—Zn1—O7—C12−87.80 (11)C11—C8—C10—O3−169.64 (10)
O7—Zn1—O8—C2076.02 (16)N2—C8—C11—O4−177.65 (10)
O1—Zn1—O8—C20−53.45 (8)C10—C8—C11—O4−54.13 (13)
N2—Zn1—O8—C20−142.95 (8)C9—C8—C11—O465.25 (13)
N4—Zn1—O8—C2037.51 (8)Zn1—O7—C12—C13167.87 (9)
O2—Zn1—O8—C20138.68 (8)Zn1—O7—C12—C17−12.00 (18)
O7—Zn1—N2—C7−99.37 (11)O7—C12—C13—C14−179.56 (12)
O1—Zn1—N2—C7−1.56 (11)C17—C12—C13—C140.32 (19)
O8—Zn1—N2—C790.78 (11)C12—C13—C14—C150.0 (2)
O2—Zn1—N2—C7174.71 (11)C13—C14—C15—C16−0.6 (2)
O7—Zn1—N2—C879.54 (9)C13—C14—C15—N3178.61 (12)
O1—Zn1—N2—C8177.35 (9)O12—N3—C15—C163.6 (2)
O8—Zn1—N2—C8−90.31 (9)O11—N3—C15—C16−176.19 (13)
O2—Zn1—N2—C8−6.38 (8)O12—N3—C15—C14−175.59 (13)
O7—Zn1—N4—C18−4.94 (11)O11—N3—C15—C144.6 (2)
O1—Zn1—N4—C18−102.78 (11)C14—C15—C16—C170.8 (2)
O8—Zn1—N4—C18165.09 (11)N3—C15—C16—C17−178.35 (12)
O2—Zn1—N4—C1882.41 (11)C15—C16—C17—C12−0.51 (19)
O7—Zn1—N4—C19179.02 (8)C15—C16—C17—C18177.86 (12)
O1—Zn1—N4—C1981.18 (8)O7—C12—C17—C16179.82 (12)
O8—Zn1—N4—C19−10.95 (8)C13—C12—C17—C16−0.06 (18)
O2—Zn1—N4—C19−93.63 (8)O7—C12—C17—C181.6 (2)
Zn1—O1—C1—C2159.57 (9)C13—C12—C17—C18−178.24 (12)
Zn1—O1—C1—C6−21.42 (18)C19—N4—C18—C17174.09 (12)
O1—C1—C2—C3172.67 (13)Zn1—N4—C18—C17−1.78 (19)
C6—C1—C2—C3−6.40 (19)C16—C17—C18—N4−172.61 (12)
C1—C2—C3—C4−0.2 (2)C12—C17—C18—N45.6 (2)
C2—C3—C4—C55.1 (2)C18—N4—C19—C2149.08 (15)
C2—C3—C4—N1−175.41 (13)Zn1—N4—C19—C21−134.64 (9)
O5—N1—C4—C5178.41 (13)C18—N4—C19—C20167.74 (11)
O6—N1—C4—C5−2.9 (2)Zn1—N4—C19—C20−15.98 (12)
O5—N1—C4—C3−1.1 (2)C18—N4—C19—C22−75.30 (14)
O6—N1—C4—C3177.61 (14)Zn1—N4—C19—C22100.98 (10)
C3—C4—C5—C6−3.1 (2)Zn1—O8—C20—C19−57.53 (10)
N1—C4—C5—C6177.42 (12)N4—C19—C20—O848.97 (13)
C4—C5—C6—C1−3.77 (19)C21—C19—C20—O8170.18 (10)
C4—C5—C6—C7173.81 (12)C22—C19—C20—O8−68.25 (12)
O1—C1—C6—C5−170.72 (12)N4—C19—C21—O9178.03 (10)
C2—C1—C6—C58.31 (18)C20—C19—C21—O960.34 (13)
O1—C1—C6—C711.9 (2)C22—C19—C21—O9−59.19 (14)
C2—C1—C6—C7−169.05 (12)N4—C19—C22—O1070.23 (13)
C8—N2—C7—C6175.80 (12)C21—C19—C22—O10−54.47 (14)
Zn1—N2—C7—C6−5.30 (19)C20—C19—C22—O10−173.93 (10)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O10i0.84 (1)1.85 (1)2.686 (1)173 (2)
O3—H3o···O7ii0.83 (1)1.90 (1)2.687 (1)158 (2)
O4—H4o···O3wiii0.83 (1)1.94 (1)2.774 (2)175 (2)
O8—H8o···O1w0.83 (1)1.80 (1)2.625 (1)171 (2)
O9—H9o···O4iv0.82 (1)1.83 (1)2.640 (1)168 (2)
O10—H10o···O9v0.83 (1)1.87 (1)2.685 (1)171 (2)
O1w—H1w1···O2W0.85 (1)1.85 (1)2.702 (2)173 (2)
O1w—H1w2···O30.84 (1)1.94 (1)2.780 (2)174 (2)
O2w—H2w1···O3W0.86 (1)2.03 (1)2.863 (2)162 (3)
O2w—H2w2···O6vi0.86 (1)2.25 (1)3.085 (2)166 (4)
O3w—H3w1···O1vii0.85 (1)2.00 (1)2.817 (1)163 (2)
O3w—H3w2···O11viii0.85 (1)2.02 (1)2.825 (2)159 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x+1/2, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å) top
Zn1—O12.062 (1)Zn1—O82.162 (1)
Zn1—O22.196 (1)Zn1—N22.079 (1)
Zn1—O72.030 (1)Zn1—N42.087 (1)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O10i0.84 (1)1.85 (1)2.686 (1)173 (2)
O3—H3o···O7ii0.83 (1)1.90 (1)2.687 (1)158 (2)
O4—H4o···O3wiii0.83 (1)1.94 (1)2.774 (2)175 (2)
O8—H8o···O1w0.83 (1)1.80 (1)2.625 (1)171 (2)
O9—H9o···O4iv0.82 (1)1.83 (1)2.640 (1)168 (2)
O10—H10o···O9v0.83 (1)1.87 (1)2.685 (1)171 (2)
O1w—H1w1···O2W0.85 (1)1.85 (1)2.702 (2)173 (2)
O1w—H1w2···O30.84 (1)1.94 (1)2.780 (2)174 (2)
O2w—H2w1···O3W0.86 (1)2.03 (1)2.863 (2)162 (3)
O2w—H2w2···O6vi0.86 (1)2.25 (1)3.085 (2)166 (4)
O3w—H3w1···O1vii0.85 (1)2.00 (1)2.817 (1)163 (2)
O3w—H3w2···O11viii0.85 (1)2.02 (1)2.825 (2)159 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x+1/2, −y+1/2, z−1/2.
Acknowledgements top

TThe authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02–03–2031) and the Fundamental Research Grant Scheme (FP064/2006 A) for supporting this study.

references
References top

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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.