PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m302.
Published online 2008 January 9. doi:  10.1107/S1600536807068298
PMCID: PMC2960459

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

Abstract

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 [triangle]); An, Huang & Qi (2007 [triangle]); An, Qi & Huang (2007 [triangle]). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m302-scheme1.jpg

Experimental

Crystal data

  • [Zn(C17H19FN3O3)2(H2O)]·2H2O
  • M r = 784.12
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m302-efi1.jpg
  • 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 [triangle]) T min = 0.733, T max = 0.874
  • 9009 measured reflections
  • 6138 independent reflections
  • 4177 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068298/bi2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068298/bi2272Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
The asymmetric unit of the title compound showing the showing 50% displacement ellipsoids for non-H atoms.

Crystal data

[Zn(C17H19FN3O3)2(H2O)]·2H2OZ = 2
Mr = 784.12F000 = 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 = 2.4–22.1º
c = 18.2738 (14) ŵ = 0.77 mm1
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

Bruker SMART CCD diffractometer6138 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

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 Å3
481 parametersΔρmin = −0.57 e Å3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2272).

References

  • An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009.
  • An, Z., Qi, W. & Huang, J. (2007). Acta Cryst. E63, m2084–m2085.
  • Baenziger, N. C., Fox, C. L. & Modak, S. L. (1986). Acta Cryst. C42, 1505–1509.
  • Bruker (1998). SMART, SAINT-Plus and SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother.37 Suppl. A, 41–45. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography