metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aSchool of Pharmaceutical Science, Harbin Medical University, Harbin 150086, People's Republic of China
*Correspondence e-mail: anzhe6409@sina.com

(Received 6 December 2007; accepted 24 December 2007; online 9 January 2008)

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.

Related literature

For AgI, MnII and CoII complexes of the pef anion, see: Baenziger et al. (1986[Baenziger, N. C., Fox, C. L. & Modak, S. L. (1986). Acta Cryst. C42, 1505-1509.]); An, Huang & Qi (2007[An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009.]); An, Qi & Huang (2007[An, Z., Qi, W. & Huang, J. (2007). Acta Cryst. E63, m2084-m2085.]). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996[Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41-45.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C17H19FN3O3)2(H2O)]·2H2O

  • Mr = 784.12

  • Triclinic, [P \overline 1]

  • a = 10.0046 (6) Å

  • b = 10.9372 (6) Å

  • c = 18.2738 (14) Å

  • α = 96.933 (2)°

  • β = 102.839 (1)°

  • γ = 111.699 (1)°

  • V = 1765.4 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 293 (2) K

  • 0.43 × 0.22 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.733, Tmax = 0.874

  • 9009 measured reflections

  • 6138 independent reflections

  • 4177 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.160

  • S = 1.01

  • 6138 reflections

  • 481 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.92 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O7—H7⋯O5i 0.85 (1) 1.79 (1) 2.638 (5) 176 (6)
O8—H8WA⋯N5 0.85 2.21 3.063 (9) 179
O8—H8WB⋯O1ii 0.85 2.20 3.054 (7) 179
O9—H9WA⋯N6 0.85 1.99 2.843 (9) 180
Symmetry codes: (i) -x+1, -y-1, -z+1; (ii) -x+2, -y-1, -z+2.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Bruker, 1998[Bruker (1998). SMART, SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 = 784.12F(000) = 820
Triclinic, P1Dx = 1.475 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0046 (6) ÅCell parameters from 1700 reflections
b = 10.9372 (6) Åθ = 2.4–22.1°
c = 18.2738 (14) ŵ = 0.77 mm1
α = 96.933 (2)°T = 293 K
β = 102.839 (1)°Block, colorless
γ = 111.699 (1)°0.43 × 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)
Graphite monochromatorRint = 0.029
ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.733, Tmax = 0.874k = 1112
9009 measured reflectionsl = 2117
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0881P)2]
where P = (Fo2 + 2Fc2)/3
6138 reflections(Δ/σ)max < 0.001
481 parametersΔρmax = 0.92 e Å3
15 restraintsΔρmin = 0.57 e Å3
Crystal data top
[Zn(C17H19FN3O3)2(H2O)]·2H2Oγ = 111.699 (1)°
Mr = 784.12V = 1765.4 (2) Å3
Triclinic, P1Z = 2
a = 10.0046 (6) ÅMo Kα radiation
b = 10.9372 (6) ŵ = 0.77 mm1
c = 18.2738 (14) ÅT = 293 K
α = 96.933 (2)°0.43 × 0.22 × 0.18 mm
β = 102.839 (1)°
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 Å3
6138 reflectionsΔρmin = 0.57 e Å3
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)
H12A0.37920.27520.44470.046*
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)
H15A0.25860.22840.20950.069*
H15B0.39910.14810.18350.069*
C160.2144 (7)0.1193 (6)0.1324 (3)0.0702 (17)
H16A0.18990.18740.08650.084*
H16B0.12140.12840.14370.084*
C170.1944 (9)0.0369 (7)0.0515 (4)0.103 (3)
H17A0.24960.12280.04160.154*
H17B0.10420.03610.06190.154*
H17C0.16870.03340.00730.154*
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)
H23A0.27270.77540.69250.042*
C240.5761 (5)0.6335 (4)0.9281 (2)0.0351 (10)
H24A0.51720.70740.94390.042*
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)
H27A0.81320.34130.86330.042*
C280.6444 (5)0.6319 (5)1.0889 (3)0.0482 (12)
H28A0.63590.72241.07110.058*
H28B0.54610.63091.07100.058*
C290.7005 (6)0.5917 (6)1.1766 (3)0.0615 (15)
H29A0.70500.50241.19380.074*
H29B0.62990.65451.19750.074*
C300.9536 (5)0.4951 (5)1.1756 (3)0.0481 (12)
H30A1.05260.49431.19420.058*
H30B0.96020.40521.19330.058*
C310.9024 (5)0.5326 (5)1.0887 (3)0.0460 (12)
H31A0.97270.46701.06900.055*
H31B0.90130.62031.07110.055*
C320.8983 (8)0.5532 (9)1.2909 (3)0.103 (3)
H32A0.99150.56151.30960.154*
H32B0.82350.61201.31050.154*
H32C0.91230.46161.30780.154*
C330.3057 (5)0.8432 (4)0.8210 (3)0.0437 (12)
H33A0.36920.87260.85620.052*
H33B0.24920.91600.77560.052*
C340.1988 (6)0.8150 (6)0.8587 (3)0.0674 (16)
H34A0.14300.89360.87500.101*
H34B0.13060.79260.82260.101*
H34C0.25400.74070.90250.101*
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)
H8WA0.90830.76511.18440.302*
H8WB0.99200.82511.21930.302*
O90.5346 (9)0.0015 (8)0.0726 (5)0.177 (3)
H9WA0.46060.00340.08630.266*
H9WB0.56990.00420.03440.266*
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, º) 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—C6170.6 (4)C2—C6—N1—C51.0 (7)
O2—C1—C2—C3173.3 (5)C2—C6—N1—C7179.3 (4)
O1—C1—C2—C37.6 (7)C4—C5—N1—C60.2 (6)
C6—C2—C3—O3177.9 (4)C9—C5—N1—C6178.2 (4)
C1—C2—C3—O33.9 (7)C4—C5—N1—C7179.5 (4)
C6—C2—C3—C42.9 (6)C9—C5—N1—C72.0 (6)
C1—C2—C3—C4175.3 (4)C8—C7—N1—C6101.6 (5)
O3—C3—C4—C122.7 (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—C33179.8 (4)
C2—C3—C4—C51.9 (6)C21—C22—N2—C233.3 (6)
C12—C4—C5—N1178.2 (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—C330.9 (6)
C3—C4—C5—C9178.8 (4)C34—C33—N2—C2395.9 (5)
C3—C2—C6—N12.7 (7)C34—C33—N2—C2283.2 (5)
C1—C2—C6—N1175.7 (4)C9—C10—N3—C1316.3 (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—C1562.3 (6)
C5—C9—C10—C110.8 (7)C14—C13—N3—C10170.1 (4)
C9—C10—C11—C120.2 (7)C14—C13—N3—C1553.3 (6)
N3—C10—C11—C12179.1 (4)C16—C15—N3—C10171.2 (4)
C9—C10—C11—F1178.6 (4)C16—C15—N3—C1351.6 (6)
N3—C10—C11—F10.3 (7)C24—C25—N4—C2811.3 (6)
F1—C11—C12—C4177.5 (4)C26—C25—N4—C28164.6 (4)
C10—C11—C12—C41.3 (7)C24—C25—N4—C31123.7 (5)
C5—C4—C12—C111.3 (7)C26—C25—N4—C3160.4 (5)
C3—C4—C12—C11179.8 (4)C29—C28—N4—C25165.5 (4)
N3—C13—C14—N658.7 (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—C2857.8 (5)
O5—C18—C19—C23177.6 (4)C31—C30—N5—C2958.7 (5)
O4—C18—C19—C20174.7 (4)C31—C30—N5—C32179.4 (5)
O5—C18—C19—C204.3 (7)C28—C29—N5—C3060.1 (6)
C23—C19—C20—O6175.3 (4)C28—C29—N5—C32179.4 (5)
C18—C19—C20—O66.6 (7)C13—C14—N6—C17174.2 (5)
C23—C19—C20—C216.0 (6)C13—C14—N6—C1660.2 (6)
C18—C19—C20—C21172.1 (4)C15—C16—N6—C1457.2 (6)
O6—C20—C21—C22177.3 (4)C15—C16—N6—C17177.2 (6)
C19—C20—C21—C223.8 (6)O2—C1—O1—Zn1175.5 (4)
O6—C20—C21—C273.9 (6)C2—C1—O1—Zn13.5 (6)
C19—C20—C21—C27174.9 (4)O6—Zn1—O1—C1157.3 (4)
C27—C21—C22—N2179.5 (4)O3—Zn1—O1—C116.2 (4)
C20—C21—C22—N20.8 (6)O7—Zn1—O1—C187.4 (4)
C27—C21—C22—C242.1 (6)C2—C3—O3—Zn124.5 (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—N2174.4 (4)O1—Zn1—O3—C326.0 (3)
C21—C22—C24—C251.7 (6)O5—Zn1—O3—C3161.5 (3)
N2—C22—C24—C25179.9 (4)O7—Zn1—O3—C369.4 (3)
C22—C24—C25—N4176.9 (4)O4—C18—O5—Zn1173.9 (3)
C22—C24—C25—C260.9 (6)C19—C18—O5—Zn17.1 (7)
C24—C25—C26—C273.4 (7)O6—Zn1—O5—C1811.8 (5)
N4—C25—C26—C27179.6 (4)O3—Zn1—O5—C18153.5 (5)
C24—C25—C26—F2176.2 (4)O7—Zn1—O5—C18103.3 (5)
N4—C25—C26—F20.0 (6)C19—C20—O6—Zn12.7 (7)
F2—C26—C27—C21176.5 (4)C21—C20—O6—Zn1178.6 (3)
C25—C26—C27—C213.1 (7)O3—Zn1—O6—C2088.7 (4)
C22—C21—C27—C260.3 (6)O1—Zn1—O6—C20179.4 (4)
C20—C21—C27—C26178.5 (4)O5—Zn1—O6—C209.0 (4)
N4—C28—C29—N559.3 (6)O7—Zn1—O6—C2083.4 (4)
Hydrogen-bond geometry (Å, º) 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, y1, z+1; (ii) x+2, y1, z+2.

Experimental details

Crystal data
Chemical formula[Zn(C17H19FN3O3)2(H2O)]·2H2O
Mr784.12
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.0046 (6), 10.9372 (6), 18.2738 (14)
α, β, γ (°)96.933 (2), 102.839 (1), 111.699 (1)
V3)1765.4 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.77
Crystal size (mm)0.43 × 0.22 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.733, 0.874
No. of measured, independent and
observed [I > 2σ(I)] reflections
9009, 6138, 4177
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.160, 1.01
No. of reflections6138
No. of parameters481
No. of restraints15
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.92, 0.57

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) 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)179.1
O8—H8WB···O1ii0.852.203.054 (7)179.0
O9—H9WA···N60.851.992.843 (9)179.7
Symmetry codes: (i) x+1, y1, z+1; (ii) x+2, y1, z+2.
 

Acknowledgements

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

References

First citationAn, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAn, Z., Qi, W. & Huang, J. (2007). Acta Cryst. E63, m2084–m2085.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBaenziger, N. C., Fox, C. L. & Modak, S. L. (1986). Acta Cryst. C42, 1505–1509.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBruker (1998). SMART, SAINT-Plus and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41–45.  CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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