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Acta Cryst. (2007). E63, m2407-m2408    [ doi:10.1107/S1600536807040937 ]

Aquabis(5-chlorosalicylato-[kappa]O)(1,10-phenanthroline-[kappa]2N,N')zinc(II)

D. Wen and S. Ying

Abstract top

In the title complex, [Zn(C7H4ClO3)2(C12H8N2)(H2O)], the Zn atom is coordinated by two 5-chlorosalicylate anions, one 1,10-phenanthroline molecule and one water molecule, displaying a distorted trigonal-bipyramidal geometry. The crystal structure is stabilized by intra- and intermolecular O-H...O hydrogen bonds.

Comment top

A lot of attention has been paid to the metal salicylate owing to their intriguing structural features (Brownless et al., 1999; Lemoine et al., 2002; Zhu et al., 2003; Yin et al., 2004; Wen et al., 2007a,b,c) and biological applications (Lemoine et al., 2004). We report here the structure of a Zn (II) complex with 5-chloroosalicylate ligand (Melnik et al., 2001). The title complex, Zn(C7H4ClO3)2(C12H8N2)(H2O) was synthesized under hydrothermal conditions. The Zn atom is coordinated in a distorted trigonal bipyramid geometry by two O atoms from two 5-chlorosalicylate ligands, two N atoms from one 1,10-phenanthroline and one water O atom (Fig. 1). One Zn—N bond is significantly shorter than the other (Zn1—N1 = 2.099 (2) Å, Zn1—N2 = 2.160 (2) Å). These distances are comparable to the Zn—N bond lengths (Zn—N1 = 2.109 (3) Å, Zn—N2 = 2.178 (3) Å) in [Zn(ta)(phen)(H2O)]n (Sun et al., 2001). The complex has rich hydrogen bonds formed by the coordinated water molecule, hydroxy and carboxyl O atoms (Fig. 2). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds interactions (Fig. 3).

Related literature top

For related literature, see: Brownless et al. (1999); Lemoine et al. (2002, 2004); Melnik et al. (2001); Sun et al. (2001); Wen et al. (2007a,b,c); Yin et al. (2004); Zhu et al. (2003).

Experimental top

A mixture of Zn(NO3)2·6H2O (0.1 mmol), phen (0.1 mmol), 5-chlorosalicylic acid (0.2 mmol) and distilled water (10 ml) was put into a Teflon-lined autoclave (20 ml) and then heated at 413 K for 72 h. Colorless block-like crystals suitable for X-ray analysis were collected from the reaction mixture.

Refinement top

The aromatic H atoms were positioned geometrically and were included in the refinement in the riding-model approximation [C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C)]. The water H atoms were found in a difference Fourier map and were refined with distance restraints of O—H = 0.85 (1)Å and Uiso(H) = 1.2 Ueq(O).

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex with 30% probability ellipsoids.
[Figure 2] Fig. 2. Representation of hydrogen bonds (dashed lines) observed in the title compound.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the a axis. Hydrogen bonds are represented by dashed lines.
Aquabis(5-chlorosalicylato-κO)(1,10-phenanthroline-κ2N,N')zinc(II) top
Crystal data top
[Zn(C7H4ClO3)2(C12H8N2)(H2O)]Z = 2
Mr = 606.69F000 = 616
Triclinic, P1Dx = 1.644 Mg m−3
a = 8.681 (4) ÅMo Kα radiation
λ = 0.71073 Å
b = 11.777 (6) ÅCell parameters from 5553 reflections
c = 12.982 (9) Åθ = 3.2–27.5º
α = 72.06 (2)ºµ = 1.27 mm−1
β = 76.98 (2)ºT = 293 (2) K
γ = 81.592 (19)ºBlock, colourless
V = 1225.9 (12) Å30.28 × 0.26 × 0.25 mm
Data collection top
Rigaku R-AXIS RAPID Weissenberg IP
diffractometer		4462 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Monochromator: graphiteθmax = 27.5º
T = 293(2) Kθmin = 3.2º
ω scansh = −11→9
Absorption correction: nonek = −15→14
12131 measured reflectionsl = −16→16
5553 independent reflections
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) = 0.084  w = 1/[σ2(Fo2) + (0.0162P)2 + 0.2964P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
5553 reflectionsΔρmax = 0.54 e Å−3
355 parametersΔρmin = −0.44 e Å−3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C7H4ClO3)2(C12H8N2)(H2O)]γ = 81.592 (19)º
Mr = 606.69V = 1225.9 (12) Å3
Triclinic, P1Z = 2
a = 8.681 (4) ÅMo Kα
b = 11.777 (6) ŵ = 1.27 mm−1
c = 12.982 (9) ÅT = 293 (2) K
α = 72.06 (2)º0.28 × 0.26 × 0.25 mm
β = 76.98 (2)º
Data collection top
Rigaku R-AXIS RAPID Weissenberg IP
diffractometer		5553 independent reflections
Absorption correction: none4462 reflections with I > 2σ(I)
12131 measured reflectionsRint = 0.049
Refinement top
R[F2 > 2σ(F2)] = 0.0374 restraints
wR(F2) = 0.084H atoms treated by a mixture of
independent and constrained refinement
S = 1.04Δρmax = 0.54 e Å−3
5553 reflectionsΔρmin = −0.44 e Å−3
355 parameters
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
Zn10.64074 (3)0.98442 (2)0.813250 (19)0.03415 (9)
N10.5901 (2)1.07549 (15)0.65649 (14)0.0353 (4)
N20.8038 (2)0.88896 (14)0.71017 (14)0.0333 (4)
O10.7926 (2)1.09096 (14)0.81791 (15)0.0494 (4)
O20.7919 (2)1.05973 (15)0.99631 (15)0.0510 (4)
O30.9882 (2)1.15930 (17)1.05330 (15)0.0578 (5)
H3A0.917 (2)1.115 (2)1.058 (3)0.069*
O40.57974 (18)0.83560 (12)0.93499 (11)0.0373 (3)
O50.4509 (2)0.80266 (16)0.81983 (14)0.0563 (5)
O60.2744 (3)0.6264 (2)0.8834 (2)0.0726 (6)
H6A0.317 (4)0.6903 (18)0.843 (3)0.087*
C10.9516 (2)1.20453 (18)0.86614 (18)0.0348 (5)
C21.0224 (3)1.2225 (2)0.9464 (2)0.0418 (5)
C31.1299 (3)1.3083 (2)0.9158 (2)0.0527 (6)
H31.17881.31860.96880.063*
C41.1657 (3)1.3782 (2)0.8093 (3)0.0540 (7)
H41.23801.43580.79000.065*
C51.0934 (3)1.3625 (2)0.7307 (2)0.0423 (5)
C60.9881 (3)1.27671 (19)0.75859 (19)0.0385 (5)
H60.94071.26690.70470.046*
C70.8372 (2)1.11091 (19)0.8966 (2)0.0380 (5)
C80.4146 (2)0.67431 (18)1.00260 (18)0.0359 (5)
C90.3112 (3)0.6059 (2)0.9838 (2)0.0502 (6)
C100.2413 (3)0.5146 (2)1.0708 (3)0.0643 (8)
H100.17180.46931.05860.077*
C110.2734 (3)0.4907 (2)1.1739 (3)0.0660 (9)
H110.22610.42931.23150.079*
C120.3758 (3)0.5577 (2)1.1922 (2)0.0522 (7)
C130.4467 (3)0.64840 (19)1.10822 (18)0.0400 (5)
H130.51640.69261.12180.048*
C140.4861 (2)0.77654 (18)0.91259 (17)0.0356 (5)
C150.4887 (3)1.1706 (2)0.63063 (19)0.0463 (6)
H150.42871.20090.68680.056*
C160.4683 (3)1.2270 (2)0.5230 (2)0.0529 (6)
H160.39681.29420.50800.064*
C170.5538 (3)1.1834 (2)0.4396 (2)0.0501 (6)
H170.53981.21960.36740.060*
C180.6633 (3)1.0831 (2)0.46356 (18)0.0400 (5)
C190.7607 (3)1.0325 (2)0.38123 (19)0.0489 (6)
H190.75081.06550.30780.059*
C200.8664 (3)0.9377 (2)0.40863 (19)0.0497 (6)
H200.92880.90680.35360.060*
C210.8846 (3)0.8841 (2)0.52007 (18)0.0403 (5)
C220.9915 (3)0.7849 (2)0.5542 (2)0.0495 (6)
H221.05340.74830.50300.059*
C231.0045 (3)0.7421 (2)0.6625 (2)0.0481 (6)
H231.07620.67710.68540.058*
C240.9086 (3)0.79723 (19)0.73877 (19)0.0408 (5)
H240.91900.76830.81230.049*
C250.7908 (2)0.93152 (17)0.60344 (17)0.0324 (4)
C260.6781 (2)1.03261 (18)0.57349 (17)0.0331 (4)
Cl11.13591 (10)1.45253 (6)0.59530 (6)0.0686 (2)
Cl20.41211 (12)0.52968 (9)1.32473 (7)0.0937 (3)
O70.4401 (2)1.07947 (14)0.88416 (13)0.0429 (4)
H7B0.364 (2)1.0363 (18)0.915 (2)0.051*
H7A0.455 (3)1.108 (2)0.9330 (17)0.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04762 (15)0.03512 (13)0.01979 (12)−0.01181 (11)−0.00212 (10)−0.00721 (9)
N10.0421 (9)0.0392 (9)0.0238 (9)−0.0076 (9)−0.0023 (7)−0.0088 (7)
N20.0397 (9)0.0355 (9)0.0251 (9)−0.0125 (8)−0.0022 (7)−0.0080 (7)
O10.0595 (10)0.0475 (9)0.0518 (11)−0.0156 (8)−0.0167 (8)−0.0198 (8)
O20.0553 (10)0.0515 (9)0.0451 (11)−0.0131 (8)0.0009 (8)−0.0158 (8)
O30.0748 (13)0.0657 (11)0.0397 (10)−0.0093 (10)−0.0192 (9)−0.0176 (9)
O40.0483 (8)0.0349 (7)0.0252 (8)−0.0110 (7)−0.0010 (6)−0.0045 (6)
O50.0710 (11)0.0678 (11)0.0312 (9)−0.0140 (10)−0.0138 (8)−0.0091 (8)
O60.0778 (14)0.0823 (14)0.0773 (17)−0.0227 (12)−0.0165 (12)−0.0426 (13)
C10.0333 (10)0.0362 (10)0.0398 (12)0.0021 (10)−0.0085 (9)−0.0189 (9)
C20.0433 (12)0.0470 (12)0.0422 (13)0.0039 (11)−0.0148 (10)−0.0214 (10)
C30.0488 (13)0.0626 (15)0.0601 (18)−0.0070 (13)−0.0238 (13)−0.0262 (13)
C40.0394 (12)0.0540 (15)0.075 (2)−0.0095 (12)−0.0121 (13)−0.0238 (14)
C50.0390 (11)0.0421 (11)0.0443 (14)−0.0016 (11)−0.0036 (10)−0.0140 (10)
C60.0407 (11)0.0408 (11)0.0390 (13)0.0030 (10)−0.0111 (10)−0.0191 (9)
C70.0369 (11)0.0359 (11)0.0447 (13)0.0020 (10)−0.0072 (10)−0.0193 (10)
C80.0355 (10)0.0312 (10)0.0383 (12)−0.0037 (9)0.0003 (9)−0.0108 (9)
C90.0462 (13)0.0470 (13)0.0644 (18)−0.0048 (12)−0.0034 (12)−0.0308 (12)
C100.0592 (16)0.0442 (14)0.092 (2)−0.0211 (13)0.0075 (16)−0.0305 (15)
C110.0615 (17)0.0361 (12)0.080 (2)−0.0152 (13)0.0175 (16)−0.0048 (13)
C120.0478 (13)0.0418 (12)0.0498 (16)−0.0025 (12)0.0020 (12)0.0030 (11)
C130.0378 (11)0.0344 (10)0.0391 (13)−0.0056 (10)−0.0013 (10)−0.0010 (9)
C140.0403 (11)0.0352 (10)0.0278 (11)−0.0007 (10)0.0006 (9)−0.0101 (8)
C150.0538 (14)0.0479 (13)0.0333 (13)−0.0008 (12)−0.0040 (11)−0.0106 (10)
C160.0602 (15)0.0522 (13)0.0382 (14)0.0050 (13)−0.0103 (12)−0.0049 (11)
C170.0609 (15)0.0576 (14)0.0280 (12)−0.0115 (13)−0.0120 (11)−0.0013 (10)
C180.0502 (12)0.0466 (12)0.0243 (11)−0.0162 (11)−0.0030 (9)−0.0090 (9)
C190.0664 (15)0.0598 (14)0.0225 (11)−0.0184 (14)−0.0031 (11)−0.0123 (10)
C200.0644 (15)0.0596 (14)0.0286 (12)−0.0140 (14)0.0037 (11)−0.0228 (11)
C210.0490 (12)0.0443 (12)0.0314 (12)−0.0130 (11)0.0007 (10)−0.0179 (9)
C220.0536 (14)0.0497 (13)0.0484 (15)−0.0070 (12)0.0026 (12)−0.0265 (11)
C230.0503 (13)0.0420 (12)0.0535 (16)−0.0020 (12)−0.0094 (12)−0.0170 (11)
C240.0477 (12)0.0376 (11)0.0373 (13)−0.0105 (11)−0.0076 (10)−0.0081 (9)
C250.0376 (10)0.0357 (10)0.0261 (10)−0.0160 (9)0.0004 (8)−0.0110 (8)
C260.0401 (11)0.0382 (10)0.0228 (10)−0.0163 (10)−0.0012 (8)−0.0089 (8)
Cl10.0842 (5)0.0558 (4)0.0535 (4)−0.0097 (4)0.0007 (4)−0.0062 (3)
Cl20.1015 (6)0.1024 (6)0.0450 (4)−0.0271 (5)−0.0060 (4)0.0281 (4)
O70.0572 (10)0.0429 (8)0.0263 (8)−0.0089 (8)0.0018 (7)−0.0116 (6)
Geometric parameters (Å, °) top
Zn1—O11.9706 (18)C9—C101.390 (4)
Zn1—O42.0094 (17)C10—C111.364 (5)
Zn1—N12.099 (2)C10—H100.9300
Zn1—O72.1154 (17)C11—C121.373 (4)
Zn1—N22.1599 (18)C11—H110.9300
N1—C151.325 (3)C12—C131.372 (3)
N1—C261.361 (3)C12—Cl21.741 (3)
N2—C241.323 (3)C13—H130.9300
N2—C251.345 (3)C15—C161.389 (3)
O1—C71.265 (3)C15—H150.9300
O2—C71.247 (3)C16—C171.363 (3)
O3—C21.346 (3)C16—H160.9300
O3—H3A0.847 (10)C17—C181.404 (3)
O4—C141.275 (3)C17—H170.9300
O5—C141.244 (3)C18—C261.395 (3)
O6—C91.354 (4)C18—C191.432 (3)
O6—H6A0.854 (10)C19—C201.348 (3)
C1—C61.386 (3)C19—H190.9300
C1—C21.404 (3)C20—C211.424 (3)
C1—C71.494 (3)C20—H200.9300
C2—C31.383 (4)C21—C221.404 (3)
C3—C41.366 (4)C21—C251.410 (3)
C3—H30.9300C22—C231.365 (4)
C4—C51.382 (4)C22—H220.9300
C4—H40.9300C23—C241.400 (3)
C5—C61.372 (3)C23—H230.9300
C5—Cl11.738 (3)C24—H240.9300
C6—H60.9300C25—C261.439 (3)
C8—C131.393 (3)O7—H7B0.844 (10)
C8—C91.395 (3)O7—H7A0.847 (10)
C8—C141.492 (3)
O1—Zn1—O4123.68 (8)C10—C11—H11120.2
O1—Zn1—N198.46 (8)C12—C11—H11120.2
O4—Zn1—N1137.84 (7)C13—C12—C11121.0 (3)
O1—Zn1—O794.31 (8)C13—C12—Cl2119.5 (2)
O4—Zn1—O788.75 (7)C11—C12—Cl2119.5 (2)
N1—Zn1—O789.25 (7)C12—C13—C8120.1 (2)
O1—Zn1—N296.73 (8)C12—C13—H13120.0
O4—Zn1—N294.37 (7)C8—C13—H13120.0
N1—Zn1—N278.09 (8)O5—C14—O4122.4 (2)
O7—Zn1—N2164.28 (7)O5—C14—C8119.6 (2)
C15—N1—C26118.14 (19)O4—C14—C8117.99 (19)
C15—N1—Zn1127.30 (15)N1—C15—C16122.7 (2)
C26—N1—Zn1114.49 (14)N1—C15—H15118.6
C24—N2—C25118.49 (18)C16—C15—H15118.6
C24—N2—Zn1128.86 (15)C17—C16—C15119.6 (2)
C25—N2—Zn1112.65 (13)C17—C16—H16120.2
C7—O1—Zn1132.72 (17)C15—C16—H16120.2
C2—O3—H3A106 (2)C16—C17—C18119.4 (2)
C14—O4—Zn1113.35 (13)C16—C17—H17120.3
C9—O6—H6A106 (3)C18—C17—H17120.3
C6—C1—C2118.6 (2)C26—C18—C17117.4 (2)
C6—C1—C7120.8 (2)C26—C18—C19119.1 (2)
C2—C1—C7120.6 (2)C17—C18—C19123.4 (2)
O3—C2—C3118.3 (2)C20—C19—C18120.9 (2)
O3—C2—C1122.1 (2)C20—C19—H19119.5
C3—C2—C1119.5 (2)C18—C19—H19119.5
C4—C3—C2121.2 (2)C19—C20—C21121.4 (2)
C4—C3—H3119.4C19—C20—H20119.3
C2—C3—H3119.4C21—C20—H20119.3
C3—C4—C5119.3 (3)C22—C21—C25116.4 (2)
C3—C4—H4120.3C22—C21—C20124.2 (2)
C5—C4—H4120.3C25—C21—C20119.3 (2)
C6—C5—C4120.5 (2)C23—C22—C21120.1 (2)
C6—C5—Cl1119.76 (19)C23—C22—H22120.0
C4—C5—Cl1119.7 (2)C21—C22—H22120.0
C5—C6—C1120.8 (2)C22—C23—C24119.2 (2)
C5—C6—H6119.6C22—C23—H23120.4
C1—C6—H6119.6C24—C23—H23120.4
O2—C7—O1125.1 (2)N2—C24—C23122.5 (2)
O2—C7—C1118.2 (2)N2—C24—H24118.7
O1—C7—C1116.7 (2)C23—C24—H24118.7
C13—C8—C9119.0 (2)N2—C25—C21123.3 (2)
C13—C8—C14120.0 (2)N2—C25—C26117.74 (17)
C9—C8—C14121.0 (2)C21—C25—C26118.9 (2)
O6—C9—C10118.5 (3)N1—C26—C18122.7 (2)
O6—C9—C8122.1 (2)N1—C26—C25116.99 (19)
C10—C9—C8119.4 (3)C18—C26—C25120.32 (18)
C11—C10—C9120.9 (3)Zn1—O7—H7B112.3 (16)
C11—C10—H10119.6Zn1—O7—H7A115.6 (17)
C9—C10—H10119.6H7B—O7—H7A105 (3)
C10—C11—C12119.6 (3)
O1—Zn1—N1—C15−81.8 (2)C10—C11—C12—C13−0.1 (4)
O4—Zn1—N1—C1599.7 (2)C10—C11—C12—Cl2178.2 (2)
O7—Zn1—N1—C1512.4 (2)C11—C12—C13—C80.4 (3)
N2—Zn1—N1—C15−177.0 (2)Cl2—C12—C13—C8−177.89 (16)
O1—Zn1—N1—C2695.23 (15)C9—C8—C13—C12−0.8 (3)
O4—Zn1—N1—C26−83.21 (17)C14—C8—C13—C12177.21 (19)
O7—Zn1—N1—C26−170.52 (15)Zn1—O4—C14—O57.2 (2)
N2—Zn1—N1—C260.08 (14)Zn1—O4—C14—C8−171.40 (13)
O1—Zn1—N2—C2482.48 (19)C13—C8—C14—O5−176.59 (19)
O4—Zn1—N2—C24−42.21 (19)C9—C8—C14—O51.3 (3)
N1—Zn1—N2—C24179.75 (19)C13—C8—C14—O42.1 (3)
O7—Zn1—N2—C24−143.2 (2)C9—C8—C14—O4−179.99 (17)
O1—Zn1—N2—C25−98.22 (15)C26—N1—C15—C160.5 (4)
O4—Zn1—N2—C25137.10 (14)Zn1—N1—C15—C16177.5 (2)
N1—Zn1—N2—C25−0.95 (14)N1—C15—C16—C170.7 (4)
O7—Zn1—N2—C2536.1 (3)C15—C16—C17—C18−1.1 (4)
O4—Zn1—O1—C7−24.4 (2)C16—C17—C18—C260.3 (4)
N1—Zn1—O1—C7156.85 (18)C16—C17—C18—C19−178.7 (2)
O7—Zn1—O1—C766.96 (19)C26—C18—C19—C20−0.4 (4)
N2—Zn1—O1—C7−124.25 (19)C17—C18—C19—C20178.5 (2)
O1—Zn1—O4—C14−176.53 (12)C18—C19—C20—C210.4 (4)
N1—Zn1—O4—C141.62 (17)C19—C20—C21—C22179.5 (2)
O7—Zn1—O4—C1489.13 (14)C19—C20—C21—C25−0.4 (4)
N2—Zn1—O4—C14−75.44 (14)C25—C21—C22—C23−2.3 (3)
C6—C1—C2—O3177.31 (19)C20—C21—C22—C23177.7 (2)
C7—C1—C2—O3−1.7 (3)C21—C22—C23—C240.9 (4)
C6—C1—C2—C3−2.1 (3)C25—N2—C24—C23−0.9 (3)
C7—C1—C2—C3178.89 (19)Zn1—N2—C24—C23178.34 (17)
O3—C2—C3—C4−177.8 (2)C22—C23—C24—N20.8 (4)
C1—C2—C3—C41.7 (3)C24—N2—C25—C21−0.7 (3)
C2—C3—C4—C5−0.2 (4)Zn1—N2—C25—C21179.95 (16)
C3—C4—C5—C6−0.7 (3)C24—N2—C25—C26−178.95 (18)
C3—C4—C5—Cl1179.04 (18)Zn1—N2—C25—C261.7 (2)
C4—C5—C6—C10.3 (3)C22—C21—C25—N22.3 (3)
Cl1—C5—C6—C1−179.52 (15)C20—C21—C25—N2−177.8 (2)
C2—C1—C6—C51.2 (3)C22—C21—C25—C26−179.5 (2)
C7—C1—C6—C5−179.84 (17)C20—C21—C25—C260.5 (3)
Zn1—O1—C7—O22.0 (3)C15—N1—C26—C18−1.4 (3)
Zn1—O1—C7—C1−177.15 (13)Zn1—N1—C26—C18−178.73 (17)
C6—C1—C7—O2−170.38 (18)C15—N1—C26—C25178.12 (19)
C2—C1—C7—O28.6 (3)Zn1—N1—C26—C250.8 (2)
C6—C1—C7—O18.9 (3)C17—C18—C26—N11.0 (3)
C2—C1—C7—O1−172.16 (18)C19—C18—C26—N1180.0 (2)
C13—C8—C9—O6179.8 (2)C17—C18—C26—C25−178.5 (2)
C14—C8—C9—O61.9 (3)C19—C18—C26—C250.5 (3)
C13—C8—C9—C100.8 (3)N2—C25—C26—N1−1.7 (3)
C14—C8—C9—C10−177.2 (2)C21—C25—C26—N1179.96 (19)
O6—C9—C10—C11−179.5 (2)N2—C25—C26—C18177.8 (2)
C8—C9—C10—C11−0.5 (4)C21—C25—C26—C18−0.5 (3)
C9—C10—C11—C120.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.85 (1)1.78 (2)2.552 (3)151 (2)
O6—H6A···O50.85 (1)1.80 (2)2.577 (3)150 (2)
O7—H7A···O4i0.85 (1)1.97 (1)2.785 (3)162 (3)
O7—H7B···O2i0.84 (1)1.84 (1)2.672 (3)171 (2)
Symmetry codes: (i) −x+1, −y+2, −z+2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—O11.9706 (18)Zn1—O72.1154 (17)
Zn1—O42.0094 (17)Zn1—N22.1599 (18)
Zn1—N12.099 (2)
O1—Zn1—O4123.68 (8)N1—Zn1—O789.25 (7)
O1—Zn1—N198.46 (8)O1—Zn1—N296.73 (8)
O4—Zn1—N1137.84 (7)O4—Zn1—N294.37 (7)
O1—Zn1—O794.31 (8)N1—Zn1—N278.09 (8)
O4—Zn1—O788.75 (7)O7—Zn1—N2164.28 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.85 (1)1.78 (2)2.552 (3)151 (2)
O6—H6A···O50.85 (1)1.80 (2)2.577 (3)150 (2)
O7—H7A···O4i0.85 (1)1.97 (1)2.785 (3)162 (3)
O7—H7B···O2i0.84 (1)1.84 (1)2.672 (3)171 (2)
Symmetry codes: (i) −x+1, −y+2, −z+2.
Acknowledgements top

This work was supported financially by the Education Department of Fujian Province (No. JA02261) and Longyan Science & Technology Bureau (No. 2003LY03).

references
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