Acta Cryst. (2007). E63, m2965 [ doi:10.1107/S1600536807055274 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-4-carboxybenzene-1,2-dicarboxylato)-1:2![[kappa]](/logos/entities/kappa_rmgif.gif)
3O3,O4:O3;1:23O3:O3,O4-bis[1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylato-2O,O']dizinc(II) hexahydrateIn the crystal structure of the title compound, [Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O, the ZnII atoms are each coordinated by five O atoms within a distorted trigonal biyramid. The two ZnII atoms are connected by two symmetry-related carboxylate O atoms into dimers, which are located on centres of inversion. These dimers are linked by N-H
O and O-HO hydrogen bonding.
A mixture of ZnNO3·6H2O (0.5 mmol), norfloxacin (0.5 mmol), benzene-1,2,4-tricarboxylic acid (0.8 mmol) were stirred for 20 min in 10 ml of water) and then transferred into a 23 ml Teflon reactor. The reactor was kept at 433 K for 120 h under autogenous pressure. Single crystals of (I) were obtained after cooling to room temperature.
H atoms were placed in calculated positions with C—H = 0.93, 0.96 and 0.97 Å, N—H = 0.9 Å, and O—H = 0.82 Å and refined in riding mode with Uiso(H) = 1.2Ueq(C,N), H atoms of water molecule were located in difference maps and refined isotropically with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O)
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
![[Figure 1]](./nc2071fig1thm.gif)
| Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = −x,-y + 1,-z |
| [Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O | Z = 1 |
| Mr = 1293.75 | F000 = 668 |
| Triclinic, P1 | Dx = 1.631 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 11.296 (2) Å | Cell parameters from 13057 reflections |
| b = 11.764 (2) Å | θ = 3.1–27.5º |
| c = 12.398 (3) Å | µ = 1.01 mm−1 |
| α = 66.95 (3)º | T = 298 (2) K |
| β = 87.62 (3)º | Block, colourless |
| γ = 61.97 (3)º | 0.31 × 0.25 × 0.19 mm |
| V = 1317.3 (5) Å3 |
| Bruker APEX CCD area-detector diffractometer | 5989 independent reflections |
| Radiation source: fine-focus sealed tube | 5274 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.029 |
| T = 298(2) K | θmax = 27.5º |
| ω scans | θmin = 3.1º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
| Tmin = 0.744, Tmax = 0.831 | k = −13→15 |
| 13057 measured reflections | l = −15→16 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.9168P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max = 0.007 |
| 5989 reflections | Δρmax = 0.46 e Å−3 |
| 379 parameters | Δρmin = −0.31 e Å−3 |
| 9 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O | γ = 61.97 (3)º |
| Mr = 1293.75 | V = 1317.3 (5) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 11.296 (2) Å | Mo Kα |
| b = 11.764 (2) Å | µ = 1.01 mm−1 |
| c = 12.398 (3) Å | T = 298 (2) K |
| α = 66.95 (3)º | 0.31 × 0.25 × 0.19 mm |
| β = 87.62 (3)º |
| Bruker APEX CCD area-detector diffractometer | 5989 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5274 reflections with I > 2σ(I) |
| Tmin = 0.744, Tmax = 0.831 | Rint = 0.029 |
| 13057 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | 9 restraints |
| wR(F2) = 0.104 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.46 e Å−3 |
| 5989 reflections | Δρmin = −0.31 e Å−3 |
| 379 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| Zn1 | −0.11988 (5) | 0.52096 (5) | 0.08633 (4) | 0.01963 (17) | |
| F1 | 0.3341 (3) | −0.0548 (3) | 0.5724 (2) | 0.0315 (6) | |
| O1 | −0.0390 (4) | 0.8105 (4) | 0.0927 (3) | 0.0382 (9) | |
| O2 | −0.1451 (3) | 0.6892 (3) | 0.1040 (3) | 0.0269 (7) | |
| O3 | 0.0951 (3) | 0.4928 (3) | 0.0671 (3) | 0.0252 (6) | |
| O4 | 0.2887 (4) | 0.2983 (4) | 0.1743 (3) | 0.0340 (8) | |
| O5 | 0.4119 (4) | 0.1723 (4) | 0.5979 (3) | 0.0443 (10) | |
| O6 | 0.3091 (6) | 0.3438 (5) | 0.6612 (4) | 0.0649 (15) | |
| H6B | 0.3732 | 0.2937 | 0.7171 | 0.078* | |
| O7 | −0.3011 (3) | 0.5376 (3) | 0.1017 (3) | 0.0272 (7) | |
| O8 | −0.4599 (3) | 0.5006 (4) | 0.1932 (3) | 0.0307 (7) | |
| O9 | −0.0314 (3) | 0.3377 (3) | 0.2322 (2) | 0.0227 (6) | |
| N1 | −0.2222 (3) | 0.2296 (4) | 0.5123 (3) | 0.0204 (7) | |
| N2 | 0.2171 (4) | −0.1024 (4) | 0.7755 (3) | 0.0209 (7) | |
| N3 | 0.3583 (4) | −0.2514 (4) | 1.0164 (3) | 0.0232 (7) | |
| H3B | 0.4190 | −0.3326 | 1.0768 | 0.028* | |
| H3C | 0.3249 | −0.1821 | 1.0419 | 0.028* | |
| C1 | 0.0529 (4) | 0.5859 (4) | 0.2505 (4) | 0.0212 (8) | |
| C2 | 0.1611 (4) | 0.4548 (4) | 0.2613 (3) | 0.0195 (8) | |
| C3 | 0.2508 (4) | 0.3620 (4) | 0.3700 (4) | 0.0221 (8) | |
| H3A | 0.3238 | 0.2758 | 0.3775 | 0.027* | |
| C4 | 0.2330 (5) | 0.3960 (5) | 0.4663 (4) | 0.0246 (9) | |
| C5 | 0.1253 (5) | 0.5263 (5) | 0.4544 (4) | 0.0291 (10) | |
| H5A | 0.1127 | 0.5501 | 0.5188 | 0.035* | |
| C6 | 0.0375 (5) | 0.6198 (5) | 0.3478 (4) | 0.0273 (9) | |
| H6A | −0.0334 | 0.7072 | 0.3404 | 0.033* | |
| C7 | 0.1867 (4) | 0.4086 (4) | 0.1619 (4) | 0.0203 (8) | |
| C8 | −0.0487 (4) | 0.7019 (4) | 0.1383 (4) | 0.0232 (8) | |
| C9 | 0.3269 (5) | 0.2930 (5) | 0.5819 (4) | 0.0282 (9) | |
| C10 | −0.2389 (4) | 0.3663 (4) | 0.3046 (3) | 0.0187 (8) | |
| C11 | −0.2937 (4) | 0.3236 (4) | 0.4033 (4) | 0.0210 (8) | |
| H11A | −0.3879 | 0.3632 | 0.3935 | 0.025* | |
| C12 | −0.0811 (4) | 0.1636 (4) | 0.5312 (3) | 0.0174 (7) | |
| C13 | −0.0176 (4) | 0.1976 (4) | 0.4332 (3) | 0.0171 (7) | |
| C14 | −0.0954 (4) | 0.3054 (4) | 0.3155 (3) | 0.0170 (7) | |
| C15 | −0.0041 (4) | 0.0677 (4) | 0.6455 (3) | 0.0189 (8) | |
| H15A | −0.0486 | 0.0519 | 0.7101 | 0.023* | |
| C16 | 0.1367 (4) | −0.0038 (4) | 0.6641 (3) | 0.0193 (8) | |
| C17 | 0.1978 (4) | 0.0240 (4) | 0.5611 (4) | 0.0201 (8) | |
| C18 | 0.1255 (4) | 0.1228 (4) | 0.4512 (4) | 0.0200 (8) | |
| H18A | 0.1706 | 0.1413 | 0.3875 | 0.024* | |
| C19 | 0.1459 (4) | −0.1380 (5) | 0.8740 (4) | 0.0233 (9) | |
| H19A | 0.0787 | −0.1562 | 0.8492 | 0.028* | |
| H19B | 0.0987 | −0.0583 | 0.8950 | 0.028* | |
| C20 | 0.2463 (4) | −0.2687 (5) | 0.9821 (4) | 0.0247 (9) | |
| H20A | 0.1986 | −0.2852 | 1.0485 | 0.030* | |
| H20B | 0.2838 | −0.3510 | 0.9643 | 0.030* | |
| C21 | 0.4275 (5) | −0.2153 (5) | 0.9146 (4) | 0.0287 (10) | |
| H21A | 0.4691 | −0.2926 | 0.8903 | 0.034* | |
| H21B | 0.4987 | −0.2014 | 0.9383 | 0.034* | |
| C22 | 0.3252 (5) | −0.0811 (5) | 0.8118 (4) | 0.0278 (10) | |
| H22A | 0.2854 | −0.0032 | 0.8354 | 0.033* | |
| H22B | 0.3705 | −0.0571 | 0.7452 | 0.033* | |
| C23 | −0.3403 (4) | 0.4758 (4) | 0.1921 (3) | 0.0201 (8) | |
| C24 | −0.3002 (5) | 0.2042 (5) | 0.6093 (4) | 0.0296 (10) | |
| H24A | −0.2451 | 0.1091 | 0.6712 | 0.035* | |
| H24B | −0.3814 | 0.2101 | 0.5785 | 0.035* | |
| C25 | −0.3403 (7) | 0.3091 (7) | 0.6615 (5) | 0.0502 (15) | |
| H25A | −0.3902 | 0.2891 | 0.7242 | 0.075* | |
| H25B | −0.3966 | 0.4032 | 0.6008 | 0.075* | |
| H25C | −0.2601 | 0.3026 | 0.6931 | 0.075* | |
| O1W | 0.3947 (4) | 0.0289 (4) | 0.1959 (3) | 0.0403 (9) | |
| H1 | 0.3596 | 0.1155 | 0.1839 | 0.060* | |
| H2 | 0.4260 | −0.0044 | 0.2692 | 0.060* | |
| O2W | −0.7730 (4) | 0.9659 (4) | 0.0955 (3) | 0.0421 (9) | |
| H3 | −0.8331 | 1.0442 | 0.0418 | 0.063* | |
| H4 | −0.7165 | 0.9879 | 0.1117 | 0.063* | |
| O3W | −0.4213 (4) | 0.8368 (5) | 0.1153 (4) | 0.0521 (11) | |
| H6 | −0.3461 | 0.8208 | 0.0908 | 0.078* | |
| H5 | −0.4603 | 0.9196 | 0.1161 | 0.078* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.0200 (3) | 0.0207 (3) | 0.0132 (2) | −0.0084 (2) | 0.00266 (17) | −0.00461 (19) |
| F1 | 0.0135 (12) | 0.0362 (15) | 0.0273 (13) | −0.0031 (11) | −0.0007 (10) | −0.0082 (12) |
| O1 | 0.036 (2) | 0.0218 (17) | 0.041 (2) | −0.0139 (15) | −0.0076 (16) | 0.0022 (15) |
| O2 | 0.0198 (15) | 0.0249 (15) | 0.0318 (16) | −0.0061 (12) | 0.0001 (12) | −0.0137 (14) |
| O3 | 0.0205 (15) | 0.0325 (17) | 0.0163 (13) | −0.0084 (13) | 0.0016 (11) | −0.0103 (13) |
| O4 | 0.0289 (18) | 0.0305 (18) | 0.0294 (17) | −0.0016 (14) | 0.0006 (14) | −0.0163 (15) |
| O5 | 0.042 (2) | 0.037 (2) | 0.0328 (19) | −0.0095 (17) | −0.0129 (16) | −0.0050 (17) |
| O6 | 0.093 (4) | 0.056 (3) | 0.029 (2) | −0.021 (3) | −0.016 (2) | −0.020 (2) |
| O7 | 0.0211 (15) | 0.0306 (17) | 0.0157 (13) | −0.0104 (13) | −0.0008 (11) | 0.0006 (13) |
| O8 | 0.0156 (14) | 0.0338 (18) | 0.0228 (15) | −0.0083 (13) | −0.0024 (12) | 0.0022 (14) |
| O9 | 0.0174 (14) | 0.0249 (15) | 0.0166 (13) | −0.0080 (12) | 0.0038 (11) | −0.0033 (12) |
| N1 | 0.0155 (16) | 0.0231 (17) | 0.0154 (15) | −0.0083 (14) | 0.0021 (12) | −0.0030 (14) |
| N2 | 0.0184 (17) | 0.0223 (17) | 0.0149 (15) | −0.0094 (14) | −0.0032 (13) | −0.0014 (14) |
| N3 | 0.0201 (17) | 0.0212 (17) | 0.0164 (15) | −0.0055 (14) | −0.0045 (13) | −0.0021 (14) |
| C1 | 0.020 (2) | 0.0194 (19) | 0.0216 (19) | −0.0093 (16) | 0.0017 (16) | −0.0069 (17) |
| C2 | 0.0190 (19) | 0.0211 (19) | 0.0173 (18) | −0.0092 (16) | 0.0021 (15) | −0.0078 (16) |
| C3 | 0.0198 (19) | 0.021 (2) | 0.0211 (19) | −0.0081 (16) | 0.0000 (15) | −0.0065 (17) |
| C4 | 0.028 (2) | 0.025 (2) | 0.0188 (19) | −0.0138 (18) | 0.0004 (16) | −0.0059 (17) |
| C5 | 0.039 (3) | 0.031 (2) | 0.023 (2) | −0.018 (2) | 0.0070 (19) | −0.0163 (19) |
| C6 | 0.029 (2) | 0.023 (2) | 0.030 (2) | −0.0105 (18) | 0.0052 (18) | −0.0145 (19) |
| C7 | 0.0189 (19) | 0.022 (2) | 0.0175 (18) | −0.0086 (16) | 0.0025 (15) | −0.0077 (16) |
| C8 | 0.019 (2) | 0.020 (2) | 0.024 (2) | −0.0046 (16) | 0.0023 (16) | −0.0088 (17) |
| C9 | 0.033 (2) | 0.033 (2) | 0.021 (2) | −0.019 (2) | −0.0004 (18) | −0.0093 (19) |
| C10 | 0.0173 (18) | 0.0180 (18) | 0.0143 (17) | −0.0060 (15) | −0.0013 (14) | −0.0039 (15) |
| C11 | 0.0150 (18) | 0.021 (2) | 0.0184 (18) | −0.0056 (15) | 0.0006 (14) | −0.0044 (16) |
| C12 | 0.0166 (18) | 0.0159 (18) | 0.0164 (17) | −0.0067 (15) | 0.0000 (14) | −0.0052 (15) |
| C13 | 0.0158 (18) | 0.0170 (18) | 0.0149 (17) | −0.0069 (15) | −0.0001 (14) | −0.0045 (15) |
| C14 | 0.0189 (19) | 0.0163 (18) | 0.0138 (17) | −0.0075 (15) | 0.0014 (14) | −0.0059 (15) |
| C15 | 0.0179 (19) | 0.0188 (19) | 0.0148 (17) | −0.0083 (15) | −0.0002 (14) | −0.0030 (16) |
| C16 | 0.0190 (19) | 0.0171 (18) | 0.0169 (18) | −0.0079 (15) | −0.0026 (15) | −0.0033 (16) |
| C17 | 0.0137 (18) | 0.022 (2) | 0.0219 (19) | −0.0067 (15) | 0.0010 (15) | −0.0091 (17) |
| C18 | 0.0178 (19) | 0.021 (2) | 0.0178 (18) | −0.0089 (16) | 0.0025 (15) | −0.0061 (16) |
| C19 | 0.0181 (19) | 0.025 (2) | 0.0191 (18) | −0.0100 (17) | −0.0027 (15) | −0.0019 (17) |
| C20 | 0.024 (2) | 0.023 (2) | 0.0174 (18) | −0.0107 (17) | −0.0022 (16) | −0.0010 (17) |
| C21 | 0.020 (2) | 0.038 (3) | 0.0194 (19) | −0.0142 (19) | −0.0037 (16) | −0.0041 (19) |
| C22 | 0.026 (2) | 0.033 (2) | 0.0197 (19) | −0.0184 (19) | −0.0054 (17) | −0.0001 (18) |
| C23 | 0.0168 (19) | 0.0189 (19) | 0.0176 (18) | −0.0053 (15) | −0.0012 (15) | −0.0052 (16) |
| C24 | 0.019 (2) | 0.035 (2) | 0.0193 (19) | −0.0109 (18) | 0.0050 (16) | −0.0003 (19) |
| C25 | 0.049 (3) | 0.045 (3) | 0.036 (3) | −0.012 (3) | 0.023 (3) | −0.013 (3) |
| O1W | 0.041 (2) | 0.0298 (18) | 0.044 (2) | −0.0130 (16) | −0.0025 (17) | −0.0144 (17) |
| O2W | 0.047 (2) | 0.0273 (18) | 0.0373 (19) | −0.0107 (16) | −0.0111 (17) | −0.0079 (16) |
| O3W | 0.032 (2) | 0.063 (3) | 0.049 (2) | −0.0019 (19) | −0.0005 (17) | −0.039 (2) |
| Zn1—O2 | 1.962 (3) | C5—H5A | 0.9300 |
| Zn1—O3i | 1.969 (3) | C6—H6A | 0.9300 |
| Zn1—O7 | 1.970 (3) | C10—C11 | 1.371 (6) |
| Zn1—O9 | 1.998 (3) | C10—C14 | 1.417 (6) |
| Zn1—O3 | 2.307 (3) | C10—C23 | 1.501 (5) |
| F1—C17 | 1.351 (5) | C11—H11A | 0.9300 |
| O1—C8 | 1.236 (6) | C12—C15 | 1.402 (5) |
| O2—C8 | 1.277 (5) | C12—C13 | 1.403 (5) |
| O3—C7 | 1.289 (5) | C13—C18 | 1.406 (6) |
| O3—Zn1i | 1.969 (3) | C13—C14 | 1.456 (5) |
| O4—C7 | 1.219 (5) | C15—C16 | 1.383 (6) |
| O5—C9 | 1.221 (6) | C15—H15A | 0.9300 |
| O6—C9 | 1.302 (6) | C16—C17 | 1.423 (6) |
| O6—H6B | 0.8200 | C17—C18 | 1.355 (6) |
| O7—C23 | 1.267 (5) | C18—H18A | 0.9300 |
| O8—C23 | 1.242 (5) | C19—C20 | 1.523 (6) |
| O9—C14 | 1.274 (5) | C19—H19A | 0.9700 |
| N1—C11 | 1.335 (5) | C19—H19B | 0.9700 |
| N1—C12 | 1.387 (5) | C20—H20A | 0.9700 |
| N1—C24 | 1.480 (5) | C20—H20B | 0.9700 |
| N2—C16 | 1.392 (5) | C21—C22 | 1.511 (6) |
| N2—C19 | 1.466 (5) | C21—H21A | 0.9700 |
| N2—C22 | 1.474 (5) | C21—H21B | 0.9700 |
| N3—C20 | 1.475 (6) | C22—H22A | 0.9700 |
| N3—C21 | 1.481 (6) | C22—H22B | 0.9700 |
| N3—H3B | 0.9000 | C24—C25 | 1.492 (8) |
| N3—H3C | 0.9000 | C24—H24A | 0.9700 |
| C1—C6 | 1.392 (6) | C24—H24B | 0.9700 |
| C1—C2 | 1.404 (6) | C25—H25A | 0.9600 |
| C1—C8 | 1.513 (6) | C25—H25B | 0.9600 |
| C2—C3 | 1.397 (6) | C25—H25C | 0.9600 |
| C2—C7 | 1.498 (6) | O1W—H1 | 0.8503 |
| C3—C4 | 1.380 (6) | O1W—H2 | 0.8500 |
| C3—H3A | 0.9300 | O2W—H3 | 0.8500 |
| C4—C5 | 1.392 (7) | O2W—H4 | 0.8499 |
| C4—C9 | 1.485 (6) | O3W—H6 | 0.8500 |
| C5—C6 | 1.373 (7) | O3W—H5 | 0.8643 |
| O2—Zn1—O3i | 121.12 (14) | N1—C12—C13 | 118.1 (3) |
| O2—Zn1—O7 | 101.54 (14) | C15—C12—C13 | 120.9 (4) |
| O3i—Zn1—O7 | 101.61 (14) | C12—C13—C18 | 117.9 (3) |
| O2—Zn1—O9 | 116.22 (13) | C12—C13—C14 | 122.0 (4) |
| O3i—Zn1—O9 | 116.25 (13) | C18—C13—C14 | 120.1 (4) |
| O7—Zn1—O9 | 91.84 (13) | O9—C14—C10 | 125.6 (4) |
| O2—Zn1—O3 | 80.92 (13) | O9—C14—C13 | 118.7 (4) |
| O3i—Zn1—O3 | 76.93 (13) | C10—C14—C13 | 115.7 (3) |
| O7—Zn1—O3 | 177.54 (13) | C16—C15—C12 | 121.2 (4) |
| O9—Zn1—O3 | 87.08 (12) | C16—C15—H15A | 119.4 |
| C8—O2—Zn1 | 124.5 (3) | C12—C15—H15A | 119.4 |
| C7—O3—Zn1i | 123.5 (3) | C15—C16—N2 | 123.1 (4) |
| C7—O3—Zn1 | 116.3 (3) | C15—C16—C17 | 116.3 (4) |
| Zn1i—O3—Zn1 | 103.07 (13) | N2—C16—C17 | 120.5 (4) |
| C9—O6—H6B | 112.1 | F1—C17—C18 | 118.1 (4) |
| C23—O7—Zn1 | 128.9 (3) | F1—C17—C16 | 118.6 (3) |
| C14—O9—Zn1 | 122.5 (3) | C18—C17—C16 | 123.2 (4) |
| C11—N1—C12 | 120.0 (3) | C17—C18—C13 | 120.0 (4) |
| C11—N1—C24 | 117.2 (3) | C17—C18—H18A | 120.0 |
| C12—N1—C24 | 122.9 (3) | C13—C18—H18A | 120.0 |
| C16—N2—C19 | 116.8 (3) | N2—C19—C20 | 110.6 (3) |
| C16—N2—C22 | 116.0 (3) | N2—C19—H19A | 109.5 |
| C19—N2—C22 | 111.1 (3) | C20—C19—H19A | 109.5 |
| C20—N3—C21 | 111.0 (3) | N2—C19—H19B | 109.5 |
| C20—N3—H3B | 109.4 | C20—C19—H19B | 109.5 |
| C21—N3—H3B | 109.4 | H19A—C19—H19B | 108.1 |
| C20—N3—H3C | 109.4 | N3—C20—C19 | 111.6 (3) |
| C21—N3—H3C | 109.4 | N3—C20—H20A | 109.3 |
| H3B—N3—H3C | 108.0 | C19—C20—H20A | 109.3 |
| C6—C1—C2 | 119.4 (4) | N3—C20—H20B | 109.3 |
| C6—C1—C8 | 114.7 (4) | C19—C20—H20B | 109.3 |
| C2—C1—C8 | 125.9 (4) | H20A—C20—H20B | 108.0 |
| C3—C2—C1 | 118.8 (4) | N3—C21—C22 | 109.6 (4) |
| C3—C2—C7 | 117.8 (4) | N3—C21—H21A | 109.7 |
| C1—C2—C7 | 123.4 (4) | C22—C21—H21A | 109.7 |
| C4—C3—C2 | 121.3 (4) | N3—C21—H21B | 109.7 |
| C4—C3—H3A | 119.3 | C22—C21—H21B | 109.7 |
| C2—C3—H3A | 119.3 | H21A—C21—H21B | 108.2 |
| C3—C4—C5 | 119.4 (4) | N2—C22—C21 | 109.8 (4) |
| C3—C4—C9 | 120.1 (4) | N2—C22—H22A | 109.7 |
| C5—C4—C9 | 120.6 (4) | C21—C22—H22A | 109.7 |
| C6—C5—C4 | 120.2 (4) | N2—C22—H22B | 109.7 |
| C6—C5—H5A | 119.9 | C21—C22—H22B | 109.7 |
| C4—C5—H5A | 119.9 | H22A—C22—H22B | 108.2 |
| C5—C6—C1 | 121.0 (4) | O8—C23—O7 | 123.3 (4) |
| C5—C6—H6A | 119.5 | O8—C23—C10 | 117.3 (4) |
| C1—C6—H6A | 119.5 | O7—C23—C10 | 119.4 (4) |
| O4—C7—O3 | 124.8 (4) | N1—C24—C25 | 111.8 (4) |
| O4—C7—C2 | 120.0 (4) | N1—C24—H24A | 109.2 |
| O3—C7—C2 | 115.2 (4) | C25—C24—H24A | 109.2 |
| O1—C8—O2 | 124.3 (4) | N1—C24—H24B | 109.2 |
| O1—C8—C1 | 115.6 (4) | C25—C24—H24B | 109.2 |
| O2—C8—C1 | 119.7 (4) | H24A—C24—H24B | 107.9 |
| O5—C9—O6 | 124.7 (4) | C24—C25—H25A | 109.5 |
| O5—C9—C4 | 121.3 (4) | C24—C25—H25B | 109.5 |
| O6—C9—C4 | 113.9 (4) | H25A—C25—H25B | 109.5 |
| C11—C10—C14 | 119.0 (4) | C24—C25—H25C | 109.5 |
| C11—C10—C23 | 115.3 (4) | H25A—C25—H25C | 109.5 |
| C14—C10—C23 | 125.7 (4) | H25B—C25—H25C | 109.5 |
| N1—C11—C10 | 125.0 (4) | H1—O1W—H2 | 95.1 |
| N1—C11—H11A | 117.5 | H3—O2W—H4 | 102.2 |
| C10—C11—H11A | 117.5 | H6—O3W—H5 | 109.3 |
| N1—C12—C15 | 120.9 (4) |
| Symmetry codes: (i) −x, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H1···O4 | 0.85 | 1.86 | 2.711 (5) | 174 |
| O3W—H6···O2 | 0.85 | 2.03 | 2.799 (5) | 151 |
| O1W—H2···O5ii | 0.85 | 2.07 | 2.789 (5) | 142 |
| O2W—H3···O1iii | 0.85 | 1.85 | 2.688 (5) | 167 |
| N3—H3B···O8iv | 0.90 | 1.80 | 2.696 (5) | 177 |
| N3—H3C···O2Wiv | 0.90 | 1.93 | 2.824 (6) | 171 |
| Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x−1, −y+2, −z; (iv) x+1, y−1, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H1···O4 | 0.85 | 1.86 | 2.711 (5) | 174 |
| O3W—H6···O2 | 0.85 | 2.03 | 2.799 (5) | 151 |
| O1W—H2···O5i | 0.85 | 2.07 | 2.789 (5) | 142 |
| O2W—H3···O1ii | 0.85 | 1.85 | 2.688 (5) | 167 |
| N3—H3B···O8iii | 0.90 | 1.80 | 2.696 (5) | 177 |
| N3—H3C···O2Wiii | 0.90 | 1.93 | 2.824 (6) | 171 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1, −y+2, −z; (iii) x+1, y−1, z+1. |
The author expresses thanks to Dr Li [Of which establishment?] for the refinement of the crystal structure.
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Xiao, D.-R., Wang, E.-B., An, H.-Y., Su, Z.-M., Li, Y.-G., Gao, L., Sun, C.-Y. & Xu, L. (2005). Chem. Eur. J. 11, 6673–6686.
Norfloxacin [1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid] is a member of a class of quinolones that is used to treat infections (Xiao et al. 2005; An et al. 2005), As a part of our ongoing investigations in this field we report here the crystal structure of the title compound.
In the crystal structure of the title compound the Zn atoms are coordinated by two oxygen atoms of one 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7- (piperazin-1-yl)quinoline-3-carboxylato-O,O')anion and three oxygen atoms of two 4-carboxybenzene-1,2-dicarboxylato-O,O' dianions within a distorted trigonal biyramid geometry (Fig. 1). Two of these octahedra are connected via common edges into dimers, which are located on centres of inversion. These dinuclear dimers are connected by N—H···O and O—H···O hydrogen bonding into a three-dimensional network (Table 1).