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Acta Cryst. (2008). E64, m302    [ doi:10.1107/S1600536807068298 ]

Aquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato]zinc(II) dihydrate

W. Qi, J. Huang and Z. An

Abstract top

The title compound, [Zn(C17H19FN3O3)2(H2O)]·2H2O or [Zn(pef)2(H2O)]·2H2O, where pef is 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate, was synthesized under hydrothermal conditions. The ZnII atom exhibits a distorted ZnO5 square-pyramidal geometry defined by two bidentate O,O-bonded pef anions in the basal plane and one water molecule in the apical position. A network of O-H...O and O-H...N hydrogen bonds is formed between the ZnII complexes and the uncoordinated water molecules.

Comment top

Pefloxacin (Hpef, C17H20FN3O3, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The silver(I), manganese(II) and cobalt(II) complexes of the pefloxacin (pef) anion have been reported (Baenziger et al., 1986; An, Huang & Qi, 2007; An, Qi & Huang, 2007). The title zinc(II) complex is reported here.

The title structure of is built up from Zn2+ cations, pef ligands, one coordinated water molecule, and two uncoordinated water molecules (Fig. 1). The coordination geometry around ZnII is a slightly distorted square pyramid (Table 1). The components of the structure are linked by O—H···O and O—H···N hydrogen bonds involving all the potential donors (Table 2).

Related literature top

For AgI, MnII and CoII complexes of the pef anion, see: Baenziger et al. (1986); An, Huang & Qi (2007); An, Qi & Huang (2007). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996).

Experimental top

A mixture of Zn(CH3COO)2.2H2O (0.055 g, 0.25 mmol), Hpef (0.17 g, 0.5 mmol) and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colorless prisms of the title compound were obtained from the reaction mixture.

Refinement top

All H atoms on C atoms were generated geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of the coordinated water molecule were located from difference Fourier maps and refined with distance restraints of d(O—H) = 0.82 (1) Å and d(H···H) = 1.35 Å. H atoms of the lattice water molecules were placed so as to form a reasonable H-bond network and were refined as riding. Their positions are uncertain.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing the showing 50% displacement ellipsoids for non-H atoms.
Aquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo- 1,4-dihydroquinoline-3-carboxylato]zinc(II) dihydrate top
Crystal data top
[Zn(C17H19FN3O3)2(H2O)]·2H2OZ = 2
Mr = 784.12F000 = 820
Triclinic, P1Dx = 1.475 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.0046 (6) ÅCell parameters from 1700 reflections
b = 10.9372 (6) Åθ = 2.4–22.1º
c = 18.2738 (14) ŵ = 0.77 mm−1
α = 96.933 (2)ºT = 293 (2) K
β = 102.839 (1)ºBlock, colorless
γ = 111.699 (1)º0.43 × 0.22 × 0.18 mm
V = 1765.4 (2) Å3
Data collection top
Bruker SMART CCD
diffractometer		6138 independent reflections
Radiation source: fine-focus sealed tube4177 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 293(2) Kθmax = 25.0º
ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.733, Tmax = 0.874k = −11→12
9009 measured reflectionsl = −21→17
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)] = 0.056H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.160  w = 1/[σ2(Fo2) + (0.0881P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
6138 reflectionsΔρmax = 0.92 e Å−3
481 parametersΔρmin = −0.57 e Å−3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C17H19FN3O3)2(H2O)]·2H2Oγ = 111.699 (1)º
Mr = 784.12V = 1765.4 (2) Å3
Triclinic, P1Z = 2
a = 10.0046 (6) ÅMo Kα
b = 10.9372 (6) ŵ = 0.77 mm−1
c = 18.2738 (14) ÅT = 293 (2) K
α = 96.933 (2)º0.43 × 0.22 × 0.18 mm
β = 102.839 (1)º
Data collection top
Bruker SMART CCD
diffractometer		6138 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4177 reflections with I > 2σ(I)
Tmin = 0.733, Tmax = 0.874Rint = 0.029
9009 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05615 restraints
wR(F2) = 0.160H atoms treated by a mixture of
independent and constrained refinement
S = 1.01Δρmax = 0.92 e Å−3
6138 reflectionsΔρmin = −0.57 e Å−3
481 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.65571 (6)−0.35549 (5)0.62580 (3)0.0396 (2)
C10.9050 (6)−0.0856 (5)0.6456 (3)0.0441 (11)
C20.8074 (5)−0.0651 (4)0.5766 (2)0.0353 (10)
C30.6514 (5)−0.1506 (4)0.5394 (2)0.0356 (10)
C40.5825 (5)−0.1181 (4)0.4702 (2)0.0347 (10)
C50.6621 (5)−0.0074 (4)0.4427 (2)0.0329 (10)
C60.8756 (5)0.0422 (4)0.5464 (2)0.0404 (11)
H6A0.97530.09880.57230.048*
C70.9016 (5)0.1918 (4)0.4573 (3)0.0436 (11)
H7A0.88180.16850.40190.052*
H7B1.00740.21510.48070.052*
C80.8684 (7)0.3127 (5)0.4782 (3)0.0605 (15)
H8A0.92790.38610.45940.091*
H8B0.89230.33890.53320.091*
H8C0.76370.29030.45540.091*
C90.5920 (5)0.0196 (4)0.3743 (3)0.0409 (11)
H9A0.64620.09270.35620.049*
C100.4435 (5)−0.0614 (4)0.3337 (2)0.0387 (10)
C110.3675 (5)−0.1721 (4)0.3636 (3)0.0437 (11)
C120.4334 (5)−0.2002 (4)0.4280 (3)0.0382 (10)
H12A0.3792−0.27520.44470.046*
C130.4351 (6)0.0964 (5)0.2524 (3)0.0545 (13)
H13A0.52730.10770.23940.065*
H13B0.45990.16450.29830.065*
C140.3267 (7)0.1145 (5)0.1864 (3)0.0627 (15)
H14A0.23680.10780.20070.075*
H14B0.37290.20360.17670.075*
C150.3138 (6)−0.1427 (5)0.1982 (3)0.0574 (14)
H15A0.2586−0.22840.20950.069*
H15B0.3991−0.14810.18350.069*
C160.2144 (7)−0.1193 (6)0.1324 (3)0.0702 (17)
H16A0.1899−0.18740.08650.084*
H16B0.1214−0.12840.14370.084*
C170.1944 (9)0.0369 (7)0.0515 (4)0.103 (3)
H17A0.24960.12280.04160.154*
H17B0.10420.03610.06190.154*
H17C0.1687−0.03340.00730.154*
C180.3682 (5)−0.5979 (5)0.6171 (2)0.0400 (11)
C190.4394 (5)−0.6025 (4)0.6975 (2)0.0331 (10)
C200.5795 (5)−0.5029 (4)0.7459 (2)0.0335 (10)
C210.6207 (5)−0.5154 (4)0.8257 (2)0.0324 (10)
C220.5323 (5)−0.6236 (4)0.8515 (2)0.0307 (9)
C230.3610 (5)−0.7083 (4)0.7260 (2)0.0351 (10)
H23A0.2727−0.77540.69250.042*
C240.5761 (5)−0.6335 (4)0.9281 (2)0.0351 (10)
H24A0.5172−0.70740.94390.042*
C250.7051 (5)−0.5354 (4)0.9808 (2)0.0333 (10)
C260.7878 (5)−0.4248 (4)0.9528 (2)0.0345 (10)
C270.7521 (5)−0.4143 (4)0.8790 (2)0.0346 (10)
H27A0.8132−0.34130.86330.042*
C280.6444 (5)−0.6319 (5)1.0889 (3)0.0482 (12)
H28A0.6359−0.72241.07110.058*
H28B0.5461−0.63091.07100.058*
C290.7005 (6)−0.5917 (6)1.1766 (3)0.0615 (15)
H29A0.7050−0.50241.19380.074*
H29B0.6299−0.65451.19750.074*
C300.9536 (5)−0.4951 (5)1.1756 (3)0.0481 (12)
H30A1.0526−0.49431.19420.058*
H30B0.9602−0.40521.19330.058*
C310.9024 (5)−0.5326 (5)1.0887 (3)0.0460 (12)
H31A0.9727−0.46701.06900.055*
H31B0.9013−0.62031.07110.055*
C320.8983 (8)−0.5532 (9)1.2909 (3)0.103 (3)
H32A0.9915−0.56151.30960.154*
H32B0.8235−0.61201.31050.154*
H32C0.9123−0.46161.30780.154*
C330.3057 (5)−0.8432 (4)0.8210 (3)0.0437 (12)
H33A0.3692−0.87260.85620.052*
H33B0.2492−0.91600.77560.052*
C340.1988 (6)−0.8150 (6)0.8587 (3)0.0674 (16)
H34A0.1430−0.89360.87500.101*
H34B0.1306−0.79260.82260.101*
H34C0.2540−0.74070.90250.101*
F10.2212 (3)−0.2509 (3)0.32586 (17)0.0646 (9)
F20.9109 (3)−0.3219 (2)1.00377 (13)0.0482 (7)
N10.8111 (4)0.0726 (3)0.4827 (2)0.0377 (9)
N20.4017 (4)−0.7226 (3)0.79826 (19)0.0349 (8)
N30.3679 (4)−0.0365 (4)0.2670 (2)0.0454 (10)
N40.7503 (4)−0.5368 (3)1.05850 (19)0.0363 (9)
N50.8486 (5)−0.5911 (5)1.2059 (2)0.0573 (11)
N60.2865 (5)0.0144 (5)0.1179 (2)0.0587 (12)
O10.8523 (4)−0.1942 (3)0.66928 (18)0.0512 (9)
O21.0321 (4)0.0026 (4)0.6755 (2)0.0689 (11)
O30.5724 (3)−0.2508 (3)0.56177 (18)0.0441 (8)
O40.2415 (4)−0.6836 (3)0.58155 (18)0.0567 (9)
O50.4425 (4)−0.5024 (4)0.58903 (18)0.0594 (10)
O60.6706 (4)−0.4034 (3)0.72757 (16)0.0494 (9)
O70.7300 (4)−0.4547 (4)0.55184 (19)0.0488 (8)
H70.672 (5)−0.467 (6)0.5075 (15)0.08 (2)*
H80.814 (3)−0.394 (5)0.553 (3)0.10 (3)*
O80.9310 (10)−0.8323 (6)1.1768 (4)0.202 (4)
H8WA0.9083−0.76511.18440.302*
H8WB0.9920−0.82511.21930.302*
O90.5346 (9)−0.0015 (8)0.0726 (5)0.177 (3)
H9WA0.46060.00340.08630.266*
H9WB0.5699−0.00420.03440.266*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0441 (3)0.0411 (3)0.0264 (3)0.0110 (2)0.0057 (2)0.0112 (2)
C10.047 (3)0.046 (3)0.031 (3)0.015 (2)0.003 (2)0.007 (2)
C20.035 (2)0.033 (2)0.029 (2)0.0085 (19)0.0021 (19)0.0082 (18)
C30.035 (2)0.035 (2)0.037 (2)0.015 (2)0.010 (2)0.009 (2)
C40.033 (2)0.031 (2)0.035 (2)0.0106 (19)0.006 (2)0.0052 (18)
C50.029 (2)0.026 (2)0.038 (2)0.0061 (18)0.0050 (19)0.0091 (18)
C60.033 (2)0.037 (3)0.034 (2)0.003 (2)−0.003 (2)0.002 (2)
C70.031 (2)0.043 (3)0.044 (3)0.003 (2)0.005 (2)0.014 (2)
C80.075 (4)0.039 (3)0.050 (3)0.003 (3)0.017 (3)0.013 (2)
C90.042 (3)0.031 (2)0.041 (3)0.007 (2)0.007 (2)0.012 (2)
C100.038 (3)0.034 (2)0.035 (2)0.011 (2)0.000 (2)0.0052 (19)
C110.027 (2)0.041 (3)0.048 (3)0.005 (2)−0.001 (2)0.010 (2)
C120.029 (2)0.037 (2)0.040 (3)0.005 (2)0.008 (2)0.012 (2)
C130.062 (3)0.045 (3)0.045 (3)0.018 (3)0.000 (3)0.011 (2)
C140.064 (4)0.055 (3)0.064 (4)0.024 (3)0.003 (3)0.021 (3)
C150.057 (3)0.047 (3)0.051 (3)0.013 (3)0.000 (3)0.007 (2)
C160.061 (4)0.068 (4)0.050 (3)0.010 (3)−0.012 (3)0.008 (3)
C170.116 (6)0.100 (5)0.066 (4)0.044 (5)−0.026 (4)0.020 (4)
C180.045 (3)0.042 (3)0.028 (2)0.015 (2)0.007 (2)0.007 (2)
C190.031 (2)0.036 (2)0.025 (2)0.0098 (19)0.0027 (19)0.0014 (18)
C200.037 (2)0.032 (2)0.028 (2)0.011 (2)0.010 (2)0.0064 (18)
C210.031 (2)0.036 (2)0.023 (2)0.0097 (19)0.0040 (18)0.0026 (18)
C220.031 (2)0.029 (2)0.025 (2)0.0075 (18)0.0042 (18)0.0046 (17)
C230.032 (2)0.038 (2)0.023 (2)0.0083 (19)−0.0010 (19)−0.0006 (18)
C240.037 (2)0.031 (2)0.029 (2)0.0049 (19)0.009 (2)0.0075 (18)
C250.034 (2)0.037 (2)0.025 (2)0.0109 (19)0.0058 (19)0.0095 (18)
C260.031 (2)0.039 (2)0.023 (2)0.0079 (19)0.0018 (19)0.0027 (18)
C270.036 (2)0.030 (2)0.030 (2)0.0043 (19)0.009 (2)0.0082 (18)
C280.041 (3)0.058 (3)0.037 (3)0.011 (2)0.007 (2)0.020 (2)
C290.053 (3)0.088 (4)0.039 (3)0.017 (3)0.016 (3)0.030 (3)
C300.041 (3)0.064 (3)0.032 (3)0.020 (2)0.000 (2)0.009 (2)
C310.039 (3)0.063 (3)0.035 (3)0.018 (2)0.010 (2)0.017 (2)
C320.087 (5)0.172 (8)0.034 (3)0.036 (5)0.010 (3)0.041 (4)
C330.039 (3)0.034 (2)0.040 (3)−0.001 (2)0.002 (2)0.009 (2)
C340.058 (4)0.065 (4)0.081 (4)0.017 (3)0.035 (3)0.025 (3)
F10.0316 (15)0.0632 (19)0.0650 (19)−0.0069 (14)−0.0104 (14)0.0259 (15)
F20.0408 (15)0.0463 (15)0.0287 (14)−0.0043 (12)−0.0032 (12)0.0033 (11)
N10.030 (2)0.036 (2)0.033 (2)0.0028 (16)0.0018 (17)0.0088 (16)
N20.033 (2)0.0335 (19)0.0283 (19)0.0057 (16)0.0042 (16)0.0056 (15)
N30.047 (2)0.035 (2)0.037 (2)0.0076 (18)−0.0031 (19)0.0106 (17)
N40.031 (2)0.044 (2)0.0250 (19)0.0082 (17)0.0037 (16)0.0092 (16)
N50.057 (3)0.076 (3)0.036 (2)0.021 (2)0.008 (2)0.029 (2)
N60.066 (3)0.064 (3)0.036 (2)0.024 (2)−0.001 (2)0.012 (2)
O10.048 (2)0.050 (2)0.0382 (19)0.0058 (16)−0.0005 (16)0.0188 (16)
O20.045 (2)0.060 (2)0.056 (2)−0.0112 (18)−0.0173 (18)0.0176 (19)
O30.0338 (17)0.0449 (18)0.050 (2)0.0094 (15)0.0090 (15)0.0234 (16)
O40.044 (2)0.062 (2)0.0362 (19)0.0011 (18)−0.0042 (16)0.0091 (16)
O50.057 (2)0.062 (2)0.0329 (18)0.0001 (18)0.0008 (17)0.0185 (17)
O60.050 (2)0.0478 (19)0.0239 (16)−0.0036 (16)0.0012 (15)0.0107 (14)
O70.047 (2)0.059 (2)0.0323 (19)0.0187 (19)0.0018 (17)0.0074 (16)
O80.278 (8)0.100 (4)0.153 (5)0.064 (5)−0.051 (5)0.028 (4)
O90.205 (6)0.206 (6)0.208 (6)0.133 (5)0.109 (5)0.106 (5)
Geometric parameters (Å, °) top
Zn1—O61.981 (3)C18—O51.278 (5)
Zn1—O31.993 (3)C18—C191.499 (6)
Zn1—O12.004 (3)C19—C231.371 (6)
Zn1—O52.037 (3)C19—C201.422 (6)
Zn1—O72.061 (4)C20—O61.272 (5)
C1—O21.226 (5)C20—C211.461 (6)
C1—O11.280 (5)C21—C221.398 (6)
C1—C21.508 (6)C21—C271.413 (6)
C2—C61.371 (6)C22—N21.400 (5)
C2—C31.438 (6)C22—C241.401 (6)
C3—O31.267 (5)C23—N21.339 (5)
C3—C41.451 (6)C23—H23A0.930
C4—C121.399 (6)C24—C251.385 (6)
C4—C51.401 (6)C24—H24A0.930
C5—N11.385 (5)C25—N41.395 (5)
C5—C91.413 (6)C25—C261.416 (6)
C6—N11.342 (5)C26—C271.348 (6)
C6—H6A0.930C26—F21.365 (4)
C7—N11.481 (5)C27—H27A0.930
C7—C81.506 (7)C28—N41.448 (5)
C7—H7A0.970C28—C291.525 (6)
C7—H7B0.970C28—H28A0.970
C8—H8A0.960C28—H28B0.970
C8—H8B0.960C29—N51.457 (7)
C8—H8C0.960C29—H29A0.970
C9—C101.386 (6)C29—H29B0.970
C9—H9A0.930C30—N51.448 (6)
C10—N31.397 (5)C30—C311.508 (6)
C10—C111.416 (6)C30—H30A0.970
C11—C121.345 (6)C30—H30B0.970
C11—F11.354 (5)C31—N41.481 (6)
C12—H12A0.930C31—H31A0.970
C13—N31.446 (6)C31—H31B0.970
C13—C141.518 (7)C32—N51.477 (7)
C13—H13A0.970C32—H32A0.960
C13—H13B0.970C32—H32B0.960
C14—N61.431 (6)C32—H32C0.960
C14—H14A0.970C33—N21.486 (5)
C14—H14B0.970C33—C341.494 (7)
C15—N31.451 (6)C33—H33A0.970
C15—C161.494 (7)C33—H33B0.970
C15—H15A0.970C34—H34A0.960
C15—H15B0.970C34—H34B0.960
C16—N61.459 (7)C34—H34C0.960
C16—H16A0.970O7—H70.85 (1)
C16—H16B0.970O7—H80.85 (1)
C17—N61.458 (7)O8—H8WA0.85
C17—H17A0.960O8—H8WB0.85
C17—H17B0.960O9—H9WA0.85
C17—H17C0.960O9—H9WB0.85
C18—O41.231 (5)
O6—Zn1—O3141.09 (14)C22—C21—C27118.6 (4)
O6—Zn1—O190.79 (12)C22—C21—C20122.0 (4)
O3—Zn1—O190.58 (13)C27—C21—C20119.4 (4)
O6—Zn1—O587.57 (13)C21—C22—N2118.0 (4)
O3—Zn1—O585.48 (13)C21—C22—C24120.5 (4)
O1—Zn1—O5171.47 (15)N2—C22—C24121.4 (4)
O6—Zn1—O7115.15 (14)N2—C23—C19125.1 (4)
O3—Zn1—O7103.44 (13)N2—C23—H23A117.5
O1—Zn1—O795.14 (15)C19—C23—H23A117.5
O5—Zn1—O793.13 (15)C25—C24—C22121.4 (4)
O2—C1—O1123.3 (4)C25—C24—H24A119.3
O2—C1—C2117.9 (4)C22—C24—H24A119.3
O1—C1—C2118.8 (4)C24—C25—N4123.9 (4)
C6—C2—C3118.0 (4)C24—C25—C26116.1 (4)
C6—C2—C1116.6 (4)N4—C25—C26119.9 (4)
C3—C2—C1125.4 (4)C27—C26—F2117.8 (4)
O3—C3—C2125.3 (4)C27—C26—C25124.1 (4)
O3—C3—C4118.7 (4)F2—C26—C25118.1 (3)
C2—C3—C4116.0 (4)C26—C27—C21119.2 (4)
C12—C4—C5118.3 (4)C26—C27—H27A120.4
C12—C4—C3119.9 (4)C21—C27—H27A120.4
C5—C4—C3121.8 (4)N4—C28—C29108.7 (4)
N1—C5—C4118.9 (4)N4—C28—H28A110.0
N1—C5—C9120.8 (4)C29—C28—H28A110.0
C4—C5—C9120.2 (4)N4—C28—H28B110.0
N1—C6—C2125.7 (4)C29—C28—H28B110.0
N1—C6—H6A117.1H28A—C28—H28B108.3
C2—C6—H6A117.1N5—C29—C28111.8 (4)
N1—C7—C8112.8 (4)N5—C29—H29A109.3
N1—C7—H7A109.0C28—C29—H29A109.3
C8—C7—H7A109.0N5—C29—H29B109.3
N1—C7—H7B109.0C28—C29—H29B109.3
C8—C7—H7B109.0H29A—C29—H29B107.9
H7A—C7—H7B107.8N5—C30—C31110.1 (4)
C7—C8—H8A109.5N5—C30—H30A109.6
C7—C8—H8B109.5C31—C30—H30A109.6
H8A—C8—H8B109.5N5—C30—H30B109.6
C7—C8—H8C109.5C31—C30—H30B109.6
H8A—C8—H8C109.5H30A—C30—H30B108.2
H8B—C8—H8C109.5N4—C31—C30111.0 (4)
C10—C9—C5120.9 (4)N4—C31—H31A109.4
C10—C9—H9A119.6C30—C31—H31A109.4
C5—C9—H9A119.6N4—C31—H31B109.4
C9—C10—N3123.0 (4)C30—C31—H31B109.4
C9—C10—C11116.9 (4)H31A—C31—H31B108.0
N3—C10—C11120.1 (4)N5—C32—H32A109.5
C12—C11—F1119.1 (4)N5—C32—H32B109.5
C12—C11—C10122.9 (4)H32A—C32—H32B109.5
F1—C11—C10118.0 (4)N5—C32—H32C109.5
C11—C12—C4120.8 (4)H32A—C32—H32C109.5
C11—C12—H12A119.6H32B—C32—H32C109.5
C4—C12—H12A119.6N2—C33—C34112.1 (4)
N3—C13—C14109.9 (4)N2—C33—H33A109.2
N3—C13—H13A109.7C34—C33—H33A109.2
C14—C13—H13A109.7N2—C33—H33B109.2
N3—C13—H13B109.7C34—C33—H33B109.2
C14—C13—H13B109.7H33A—C33—H33B107.9
H13A—C13—H13B108.2C33—C34—H34A109.5
N6—C14—C13111.0 (4)C33—C34—H34B109.5
N6—C14—H14A109.4H34A—C34—H34B109.5
C13—C14—H14A109.4C33—C34—H34C109.5
N6—C14—H14B109.4H34A—C34—H34C109.5
C13—C14—H14B109.4H34B—C34—H34C109.5
H14A—C14—H14B108.0C6—N1—C5119.4 (4)
N3—C15—C16112.4 (4)C6—N1—C7118.8 (3)
N3—C15—H15A109.1C5—N1—C7121.8 (4)
C16—C15—H15A109.1C23—N2—C22119.9 (4)
N3—C15—H15B109.1C23—N2—C33119.2 (3)
C16—C15—H15B109.1C22—N2—C33120.9 (3)
H15A—C15—H15B107.9C10—N3—C13116.8 (4)
N6—C16—C15111.5 (4)C10—N3—C15115.3 (4)
N6—C16—H16A109.3C13—N3—C15112.3 (4)
C15—C16—H16A109.3C25—N4—C28118.1 (3)
N6—C16—H16B109.3C25—N4—C31116.8 (3)
C15—C16—H16B109.3C28—N4—C31110.2 (4)
H16A—C16—H16B108.0C30—N5—C29108.8 (4)
N6—C17—H17A109.5C30—N5—C32109.9 (4)
N6—C17—H17B109.5C29—N5—C32110.2 (5)
H17A—C17—H17B109.5C14—N6—C17112.5 (5)
N6—C17—H17C109.5C14—N6—C16109.2 (4)
H17A—C17—H17C109.5C17—N6—C16112.4 (5)
H17B—C17—H17C109.5C1—O1—Zn1130.2 (3)
O4—C18—O5122.9 (4)C3—O3—Zn1124.2 (3)
O4—C18—C19119.5 (4)C18—O5—Zn1133.8 (3)
O5—C18—C19117.6 (4)C20—O6—Zn1128.6 (3)
C23—C19—C20118.7 (4)Zn1—O7—H7105 (4)
C23—C19—C18117.1 (4)Zn1—O7—H8103 (5)
C20—C19—C18124.2 (4)H7—O7—H8105 (2)
O6—C20—C19127.0 (4)H8WA—O8—H8WB104.6
O6—C20—C21117.0 (4)H9WA—O9—H9WB143.6
C19—C20—C21116.0 (4)
O2—C1—C2—C68.5 (6)N5—C30—C31—N458.4 (5)
O1—C1—C2—C6−170.6 (4)C2—C6—N1—C51.0 (7)
O2—C1—C2—C3−173.3 (5)C2—C6—N1—C7−179.3 (4)
O1—C1—C2—C37.6 (7)C4—C5—N1—C60.2 (6)
C6—C2—C3—O3−177.9 (4)C9—C5—N1—C6−178.2 (4)
C1—C2—C3—O33.9 (7)C4—C5—N1—C7−179.5 (4)
C6—C2—C3—C42.9 (6)C9—C5—N1—C72.0 (6)
C1—C2—C3—C4−175.3 (4)C8—C7—N1—C6−101.6 (5)
O3—C3—C4—C12−2.7 (6)C8—C7—N1—C578.1 (5)
C2—C3—C4—C12176.6 (4)C19—C23—N2—C221.1 (7)
O3—C3—C4—C5178.8 (4)C19—C23—N2—C33−179.8 (4)
C2—C3—C4—C5−1.9 (6)C21—C22—N2—C23−3.3 (6)
C12—C4—C5—N1−178.2 (4)C24—C22—N2—C23178.3 (4)
C3—C4—C5—N10.3 (6)C21—C22—N2—C33177.5 (4)
C12—C4—C5—C90.3 (6)C24—C22—N2—C33−0.9 (6)
C3—C4—C5—C9178.8 (4)C34—C33—N2—C23−95.9 (5)
C3—C2—C6—N1−2.7 (7)C34—C33—N2—C2283.2 (5)
C1—C2—C6—N1175.7 (4)C9—C10—N3—C13−16.3 (7)
N1—C5—C9—C10179.2 (4)C11—C10—N3—C13162.5 (4)
C4—C5—C9—C100.7 (7)C9—C10—N3—C15119.0 (5)
C5—C9—C10—N3178.0 (4)C11—C10—N3—C15−62.3 (6)
C5—C9—C10—C11−0.8 (7)C14—C13—N3—C10−170.1 (4)
C9—C10—C11—C12−0.2 (7)C14—C13—N3—C1553.3 (6)
N3—C10—C11—C12−179.1 (4)C16—C15—N3—C10171.2 (4)
C9—C10—C11—F1178.6 (4)C16—C15—N3—C13−51.6 (6)
N3—C10—C11—F1−0.3 (7)C24—C25—N4—C28−11.3 (6)
F1—C11—C12—C4−177.5 (4)C26—C25—N4—C28164.6 (4)
C10—C11—C12—C41.3 (7)C24—C25—N4—C31123.7 (5)
C5—C4—C12—C11−1.3 (7)C26—C25—N4—C31−60.4 (5)
C3—C4—C12—C11−179.8 (4)C29—C28—N4—C25−165.5 (4)
N3—C13—C14—N6−58.7 (6)C29—C28—N4—C3156.7 (5)
N3—C15—C16—N653.0 (7)C30—C31—N4—C25163.9 (4)
O4—C18—C19—C233.3 (6)C30—C31—N4—C28−57.8 (5)
O5—C18—C19—C23−177.6 (4)C31—C30—N5—C29−58.7 (5)
O4—C18—C19—C20−174.7 (4)C31—C30—N5—C32−179.4 (5)
O5—C18—C19—C204.3 (7)C28—C29—N5—C3060.1 (6)
C23—C19—C20—O6175.3 (4)C28—C29—N5—C32−179.4 (5)
C18—C19—C20—O6−6.6 (7)C13—C14—N6—C17−174.2 (5)
C23—C19—C20—C21−6.0 (6)C13—C14—N6—C1660.2 (6)
C18—C19—C20—C21172.1 (4)C15—C16—N6—C14−57.2 (6)
O6—C20—C21—C22−177.3 (4)C15—C16—N6—C17177.2 (6)
C19—C20—C21—C223.8 (6)O2—C1—O1—Zn1−175.5 (4)
O6—C20—C21—C273.9 (6)C2—C1—O1—Zn13.5 (6)
C19—C20—C21—C27−174.9 (4)O6—Zn1—O1—C1−157.3 (4)
C27—C21—C22—N2179.5 (4)O3—Zn1—O1—C1−16.2 (4)
C20—C21—C22—N20.8 (6)O7—Zn1—O1—C187.4 (4)
C27—C21—C22—C24−2.1 (6)C2—C3—O3—Zn1−24.5 (6)
C20—C21—C22—C24179.2 (4)C4—C3—O3—Zn1154.6 (3)
C20—C19—C23—N23.8 (7)O6—Zn1—O3—C3118.0 (3)
C18—C19—C23—N2−174.4 (4)O1—Zn1—O3—C326.0 (3)
C21—C22—C24—C251.7 (6)O5—Zn1—O3—C3−161.5 (3)
N2—C22—C24—C25−179.9 (4)O7—Zn1—O3—C3−69.4 (3)
C22—C24—C25—N4176.9 (4)O4—C18—O5—Zn1−173.9 (3)
C22—C24—C25—C260.9 (6)C19—C18—O5—Zn17.1 (7)
C24—C25—C26—C27−3.4 (7)O6—Zn1—O5—C18−11.8 (5)
N4—C25—C26—C27−179.6 (4)O3—Zn1—O5—C18−153.5 (5)
C24—C25—C26—F2176.2 (4)O7—Zn1—O5—C18103.3 (5)
N4—C25—C26—F20.0 (6)C19—C20—O6—Zn1−2.7 (7)
F2—C26—C27—C21−176.5 (4)C21—C20—O6—Zn1178.6 (3)
C25—C26—C27—C213.1 (7)O3—Zn1—O6—C2088.7 (4)
C22—C21—C27—C26−0.3 (6)O1—Zn1—O6—C20−179.4 (4)
C20—C21—C27—C26178.5 (4)O5—Zn1—O6—C209.0 (4)
N4—C28—C29—N5−59.3 (6)O7—Zn1—O6—C20−83.4 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O5i0.85 (1)1.79 (1)2.638 (5)176 (6)
O8—H8WA···N50.852.213.063 (9)179
O8—H8WB···O1ii0.852.203.054 (7)179
O9—H9WA···N60.851.992.843 (9)180
Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) −x+2, −y−1, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O5i0.85 (1)1.79 (1)2.638 (5)176 (6)
O8—H8WA···N50.852.213.063 (9)179
O8—H8WB···O1ii0.852.203.054 (7)179
O9—H9WA···N60.851.992.843 (9)180
Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) −x+2, −y−1, −z+2.
Acknowledgements top

The authors thank the Innovation Science Foundation of Harbin Medical University for financial support (grant No. 060041).

references
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