Acta Cryst. (2008). E64, m17 [ doi:10.1107/S1600536807062216 ]
![[kappa]](/logos/entities/kappa_rmgif.gif)
2O,O']nickel(II)]-![[mu]](/logos/entities/mu_rmgif.gif)
-4,4'-oxydibenzoato-2O:O']In the title compound, [Ni(C16H18FN3O3)(C14H8O5)(H2O)2]n, the NiII atom exhibits a distorted octahedral geometry that is defined by four O atoms and two water molecules. Ni atoms are connected via the 4,4'-oxydibenzoate anions into a one-dimensional chain running along the crystallographic [
30] direction. In the crystal structure, the one-dimensional chains are connected via N-H
O and O-HO hydrogen bonding to form a three-dimensional supramolecular network.
Compound (I) was prepared by a hydrothermal method. A mixture of Ni(NO3)2.6H2O (0.15 g 0.5 mmol), norfloxacin (0.16 g 0.5 mmol), 4,4'-oxy-bisbenzoic acid (0.13 g 0.5 mmol) and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 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 and N—H = 0.90 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C, N, O), H atoms of water molecule were located in difference maps and refined isotropically with O - H = 0.85 Å and Uiso(H) = 1.5 Ueq(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]](./im2047fig1thm.gif)
| Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = x + 1,y - 1,z |
| [Ni(C16H18F1N3O3)(C14H8O5)(H2O)2] | Z = 2 |
| Mr = 670.28 | F000 = 696 |
| Triclinic, P1 | Dx = 1.527 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 10.105 (2) Å | Cell parameters from 11571 reflections |
| b = 12.230 (2) Å | θ = 3.0–25.0º |
| c = 13.052 (3) Å | µ = 0.74 mm−1 |
| α = 72.50 (3)º | T = 298 (2) K |
| β = 73.13 (3)º | Block, green |
| γ = 77.57 (3)º | 0.32 × 0.24 × 0.22 mm |
| V = 1457.7 (5) Å3 |
| Bruker APEX CCD area-detector diffractometer | 5134 independent reflections |
| Radiation source: fine-focus sealed tube | 4210 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.027 |
| T = 298(2) K | θmax = 25.0º |
| ω scans | θmin = 3.0º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
| Tmin = 0.798, Tmax = 0.855 | k = −14→14 |
| 11571 measured reflections | l = −15→15 |
| 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)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0674P)2 + 0.5873P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 5134 reflections | Δρmax = 0.73 e Å−3 |
| 406 parameters | Δρmin = −0.42 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Ni(C16H18F1N3O3)(C14H8O5)(H2O)2] | γ = 77.57 (3)º |
| Mr = 670.28 | V = 1457.7 (5) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.105 (2) Å | Mo Kα |
| b = 12.230 (2) Å | µ = 0.74 mm−1 |
| c = 13.052 (3) Å | T = 298 (2) K |
| α = 72.50 (3)º | 0.32 × 0.24 × 0.22 mm |
| β = 73.13 (3)º |
| Bruker APEX CCD area-detector diffractometer | 5134 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4210 reflections with I > 2σ(I) |
| Tmin = 0.798, Tmax = 0.855 | Rint = 0.027 |
| 11571 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | 406 parameters |
| wR(F2) = 0.112 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.73 e Å−3 |
| 5134 reflections | Δρmin = −0.42 e Å−3 |
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 | ||
| Ni1 | 0.55118 (3) | 0.06895 (3) | 0.29346 (3) | 0.02717 (12) | |
| F1 | 0.11227 (19) | 0.57062 (15) | 0.2085 (2) | 0.0690 (7) | |
| C1 | 0.1138 (3) | 0.1404 (2) | 0.3988 (2) | 0.0293 (6) | |
| C2 | −0.0181 (3) | 0.1367 (3) | 0.3899 (3) | 0.0407 (7) | |
| H2A | −0.0297 | 0.0864 | 0.3532 | 0.049* | |
| C3 | −0.1329 (3) | 0.2070 (3) | 0.4349 (3) | 0.0409 (7) | |
| H3A | −0.2216 | 0.2037 | 0.4295 | 0.049* | |
| C4 | −0.1139 (3) | 0.2818 (2) | 0.4879 (2) | 0.0339 (6) | |
| C5 | 0.0162 (3) | 0.2876 (2) | 0.4971 (3) | 0.0390 (7) | |
| H5A | 0.0276 | 0.3396 | 0.5322 | 0.047* | |
| C6 | 0.1296 (3) | 0.2156 (2) | 0.4539 (2) | 0.0351 (6) | |
| H6A | 0.2175 | 0.2175 | 0.4618 | 0.042* | |
| C7 | 0.2412 (3) | 0.0689 (2) | 0.3475 (2) | 0.0296 (6) | |
| C8 | −0.2530 (3) | 0.4649 (2) | 0.4784 (2) | 0.0314 (6) | |
| C9 | −0.3601 (3) | 0.5352 (2) | 0.5311 (2) | 0.0362 (7) | |
| H9AA | −0.4120 | 0.5051 | 0.6021 | 0.043* | |
| C10 | −0.3900 (3) | 0.6506 (2) | 0.4779 (3) | 0.0376 (7) | |
| H10A | −0.4615 | 0.6979 | 0.5139 | 0.045* | |
| C11 | −0.3143 (3) | 0.6967 (2) | 0.3712 (2) | 0.0311 (6) | |
| C12 | −0.2076 (3) | 0.6244 (2) | 0.3210 (2) | 0.0370 (7) | |
| H12A | −0.1554 | 0.6541 | 0.2500 | 0.044* | |
| C13 | −0.1759 (3) | 0.5093 (2) | 0.3730 (3) | 0.0401 (7) | |
| H13A | −0.1035 | 0.4622 | 0.3375 | 0.048* | |
| C14 | −0.3468 (3) | 0.8187 (2) | 0.3084 (2) | 0.0338 (6) | |
| C15 | 0.7543 (3) | 0.4092 (2) | 0.1121 (3) | 0.0388 (7) | |
| H15A | 0.8511 | 0.4014 | 0.0884 | 0.047* | |
| C16 | 0.6950 (3) | 0.3094 (2) | 0.1539 (2) | 0.0302 (6) | |
| C17 | 0.5467 (3) | 0.3187 (2) | 0.1938 (2) | 0.0285 (6) | |
| C18 | 0.4717 (3) | 0.4358 (2) | 0.1767 (2) | 0.0299 (6) | |
| C19 | 0.5390 (3) | 0.5341 (2) | 0.1316 (2) | 0.0317 (6) | |
| C20 | 0.7920 (3) | 0.1960 (2) | 0.1557 (2) | 0.0291 (6) | |
| C21 | 0.3258 (3) | 0.4520 (2) | 0.2061 (3) | 0.0380 (7) | |
| H21A | 0.2780 | 0.3882 | 0.2377 | 0.046* | |
| C22 | 0.2540 (3) | 0.5596 (2) | 0.1887 (3) | 0.0406 (7) | |
| C23 | 0.3163 (3) | 0.6614 (2) | 0.1475 (2) | 0.0317 (6) | |
| C24 | 0.4612 (3) | 0.6458 (2) | 0.1191 (2) | 0.0340 (6) | |
| H24A | 0.5080 | 0.7102 | 0.0914 | 0.041* | |
| C25 | 0.1290 (3) | 0.7917 (2) | 0.2333 (2) | 0.0378 (7) | |
| H25A | 0.1751 | 0.8083 | 0.2815 | 0.045* | |
| H25B | 0.0842 | 0.7233 | 0.2734 | 0.045* | |
| C26 | 0.0199 (3) | 0.8933 (2) | 0.2016 (3) | 0.0389 (7) | |
| H26A | −0.0283 | 0.8761 | 0.1552 | 0.047* | |
| H26B | −0.0483 | 0.9074 | 0.2676 | 0.047* | |
| C27 | 0.1966 (3) | 0.9750 (2) | 0.0411 (2) | 0.0391 (7) | |
| H27A | 0.2439 | 1.0425 | 0.0034 | 0.047* | |
| H27B | 0.1515 | 0.9616 | −0.0095 | 0.047* | |
| C28 | 0.3032 (3) | 0.8699 (2) | 0.0731 (2) | 0.0363 (7) | |
| H28A | 0.3698 | 0.8545 | 0.0069 | 0.044* | |
| H28B | 0.3539 | 0.8856 | 0.1186 | 0.044* | |
| C29 | 0.7665 (4) | 0.6173 (3) | 0.0620 (3) | 0.0503 (9) | |
| H29A | 0.7179 | 0.6750 | 0.1024 | 0.060* | |
| H29B | 0.8569 | 0.5905 | 0.0795 | 0.060* | |
| C30 | 0.7883 (5) | 0.6721 (4) | −0.0552 (4) | 0.0830 (14) | |
| H30A | 0.8412 | 0.7348 | −0.0738 | 0.124* | |
| H30B | 0.6996 | 0.7015 | −0.0733 | 0.124* | |
| H30C | 0.8385 | 0.6165 | −0.0963 | 0.124* | |
| N1 | 0.6856 (3) | 0.51763 (19) | 0.1020 (2) | 0.0386 (6) | |
| N2 | 0.2331 (2) | 0.76972 (18) | 0.13355 (19) | 0.0316 (5) | |
| N3 | 0.0891 (2) | 0.99712 (18) | 0.14108 (18) | 0.0300 (5) | |
| H3B | 0.1298 | 1.0151 | 0.1856 | 0.036* | |
| H3C | 0.0252 | 1.0575 | 0.1207 | 0.036* | |
| O1 | 0.34733 (19) | 0.05291 (16) | 0.38500 (15) | 0.0317 (4) | |
| O2 | 0.2384 (2) | 0.0318 (2) | 0.26830 (19) | 0.0491 (6) | |
| O3 | −0.2308 (2) | 0.35044 (16) | 0.53603 (17) | 0.0446 (5) | |
| O4 | −0.3916 (2) | 0.89556 (15) | 0.36257 (16) | 0.0332 (4) | |
| O5 | −0.3263 (3) | 0.83834 (18) | 0.20552 (17) | 0.0509 (6) | |
| O6 | 0.4769 (2) | 0.23599 (15) | 0.23930 (18) | 0.0385 (5) | |
| O7 | 0.7459 (2) | 0.10163 (15) | 0.20642 (17) | 0.0360 (5) | |
| O8 | 0.9162 (2) | 0.20092 (16) | 0.10377 (18) | 0.0407 (5) | |
| O1W | 0.5830 (2) | 0.10404 (15) | 0.43009 (15) | 0.0325 (4) | |
| H1 | 0.6392 | 0.0565 | 0.4655 | 0.049* | |
| H2 | 0.5204 | 0.1036 | 0.4899 | 0.049* | |
| O2W | 0.5096 (2) | 0.03404 (17) | 0.16040 (15) | 0.0380 (5) | |
| H3 | 0.5639 | −0.0287 | 0.1553 | 0.057* | |
| H4 | 0.4342 | 0.0066 | 0.1966 | 0.057* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0245 (2) | 0.01742 (18) | 0.0365 (2) | 0.00159 (13) | −0.00766 (14) | −0.00538 (14) |
| F1 | 0.0262 (10) | 0.0311 (10) | 0.138 (2) | 0.0047 (8) | −0.0149 (11) | −0.0157 (12) |
| C1 | 0.0265 (14) | 0.0263 (13) | 0.0341 (14) | 0.0016 (11) | −0.0103 (11) | −0.0071 (12) |
| C2 | 0.0313 (16) | 0.0398 (17) | 0.0594 (19) | 0.0024 (13) | −0.0171 (14) | −0.0244 (15) |
| C3 | 0.0245 (15) | 0.0416 (17) | 0.0572 (19) | 0.0005 (13) | −0.0128 (14) | −0.0143 (15) |
| C4 | 0.0314 (16) | 0.0246 (13) | 0.0334 (14) | 0.0030 (11) | −0.0005 (12) | −0.0012 (12) |
| C5 | 0.0419 (18) | 0.0313 (15) | 0.0444 (16) | −0.0016 (13) | −0.0073 (14) | −0.0162 (13) |
| C6 | 0.0284 (15) | 0.0361 (15) | 0.0440 (16) | −0.0022 (12) | −0.0107 (13) | −0.0149 (13) |
| C7 | 0.0252 (14) | 0.0247 (13) | 0.0373 (14) | −0.0033 (11) | −0.0074 (12) | −0.0061 (12) |
| C8 | 0.0299 (15) | 0.0236 (13) | 0.0380 (15) | 0.0003 (11) | −0.0072 (12) | −0.0080 (12) |
| C9 | 0.0347 (16) | 0.0298 (14) | 0.0351 (15) | −0.0009 (12) | 0.0019 (12) | −0.0078 (12) |
| C10 | 0.0341 (16) | 0.0254 (14) | 0.0486 (17) | 0.0035 (12) | −0.0003 (13) | −0.0172 (13) |
| C11 | 0.0313 (15) | 0.0215 (13) | 0.0414 (15) | −0.0003 (11) | −0.0100 (12) | −0.0104 (12) |
| C12 | 0.0378 (16) | 0.0288 (14) | 0.0343 (15) | 0.0023 (12) | −0.0025 (13) | −0.0044 (12) |
| C13 | 0.0377 (17) | 0.0283 (14) | 0.0440 (17) | 0.0081 (12) | −0.0015 (13) | −0.0112 (13) |
| C14 | 0.0296 (15) | 0.0248 (13) | 0.0421 (16) | 0.0007 (11) | −0.0047 (12) | −0.0084 (13) |
| C15 | 0.0280 (15) | 0.0281 (14) | 0.0558 (18) | 0.0033 (12) | −0.0069 (13) | −0.0125 (14) |
| C16 | 0.0296 (14) | 0.0203 (13) | 0.0385 (14) | 0.0036 (11) | −0.0100 (12) | −0.0076 (11) |
| C17 | 0.0298 (15) | 0.0220 (13) | 0.0315 (13) | 0.0013 (11) | −0.0093 (11) | −0.0051 (11) |
| C18 | 0.0297 (15) | 0.0196 (13) | 0.0366 (14) | 0.0027 (11) | −0.0086 (12) | −0.0056 (11) |
| C19 | 0.0293 (15) | 0.0236 (13) | 0.0378 (15) | 0.0043 (11) | −0.0062 (12) | −0.0091 (12) |
| C20 | 0.0275 (15) | 0.0218 (13) | 0.0384 (14) | 0.0050 (11) | −0.0124 (12) | −0.0098 (12) |
| C21 | 0.0292 (16) | 0.0205 (13) | 0.0578 (18) | 0.0000 (11) | −0.0088 (14) | −0.0046 (13) |
| C22 | 0.0243 (15) | 0.0273 (15) | 0.065 (2) | 0.0028 (12) | −0.0099 (14) | −0.0092 (14) |
| C23 | 0.0355 (16) | 0.0207 (13) | 0.0325 (14) | 0.0049 (11) | −0.0063 (12) | −0.0058 (11) |
| C24 | 0.0320 (16) | 0.0210 (13) | 0.0423 (15) | 0.0006 (11) | −0.0040 (12) | −0.0062 (12) |
| C25 | 0.0360 (16) | 0.0260 (14) | 0.0393 (15) | 0.0028 (12) | −0.0004 (13) | −0.0042 (13) |
| C26 | 0.0301 (16) | 0.0286 (15) | 0.0543 (18) | 0.0039 (12) | −0.0087 (14) | −0.0123 (14) |
| C27 | 0.0502 (19) | 0.0229 (14) | 0.0338 (15) | 0.0068 (13) | −0.0050 (13) | −0.0053 (12) |
| C28 | 0.0371 (16) | 0.0234 (14) | 0.0365 (15) | 0.0039 (12) | 0.0016 (13) | −0.0064 (12) |
| C29 | 0.0393 (18) | 0.0307 (16) | 0.074 (2) | −0.0037 (13) | −0.0025 (17) | −0.0153 (16) |
| C30 | 0.088 (3) | 0.074 (3) | 0.079 (3) | −0.038 (3) | −0.003 (3) | −0.006 (2) |
| N1 | 0.0310 (13) | 0.0212 (11) | 0.0551 (15) | 0.0002 (10) | −0.0009 (11) | −0.0092 (11) |
| N2 | 0.0316 (13) | 0.0190 (11) | 0.0361 (12) | 0.0060 (9) | −0.0057 (10) | −0.0046 (10) |
| N3 | 0.0279 (12) | 0.0234 (11) | 0.0384 (12) | 0.0072 (9) | −0.0133 (10) | −0.0096 (10) |
| O1 | 0.0242 (10) | 0.0338 (10) | 0.0353 (10) | 0.0003 (8) | −0.0091 (8) | −0.0073 (8) |
| O2 | 0.0320 (11) | 0.0685 (15) | 0.0625 (14) | 0.0049 (11) | −0.0154 (10) | −0.0441 (13) |
| O3 | 0.0400 (12) | 0.0256 (10) | 0.0474 (12) | 0.0098 (9) | 0.0040 (10) | −0.0032 (9) |
| O4 | 0.0358 (11) | 0.0200 (9) | 0.0412 (10) | 0.0031 (8) | −0.0084 (9) | −0.0097 (8) |
| O5 | 0.0719 (16) | 0.0305 (11) | 0.0384 (12) | 0.0122 (11) | −0.0074 (11) | −0.0107 (10) |
| O6 | 0.0259 (10) | 0.0200 (9) | 0.0609 (13) | 0.0017 (8) | −0.0084 (9) | −0.0030 (9) |
| O7 | 0.0287 (10) | 0.0183 (9) | 0.0529 (12) | 0.0031 (8) | −0.0060 (9) | −0.0054 (9) |
| O8 | 0.0239 (11) | 0.0249 (10) | 0.0624 (13) | 0.0040 (8) | −0.0038 (10) | −0.0069 (10) |
| O1W | 0.0312 (10) | 0.0279 (10) | 0.0402 (10) | −0.0021 (8) | −0.0123 (9) | −0.0095 (9) |
| O2W | 0.0382 (12) | 0.0347 (11) | 0.0350 (10) | −0.0016 (9) | −0.0046 (9) | −0.0067 (9) |
| Ni1—O6 | 2.0039 (19) | C17—C18 | 1.455 (3) |
| Ni1—O7 | 2.022 (2) | C18—C19 | 1.396 (4) |
| Ni1—O4i | 2.0663 (19) | C18—C21 | 1.397 (4) |
| Ni1—O1 | 2.077 (2) | C19—N1 | 1.404 (4) |
| Ni1—O1W | 2.0786 (19) | C19—C24 | 1.410 (4) |
| Ni1—O2W | 2.079 (2) | C20—O8 | 1.246 (3) |
| F1—C22 | 1.363 (3) | C20—O7 | 1.257 (3) |
| C1—C2 | 1.382 (4) | C21—C22 | 1.347 (4) |
| C1—C6 | 1.384 (4) | C21—H21A | 0.9300 |
| C1—C7 | 1.496 (4) | C22—C23 | 1.406 (4) |
| C2—C3 | 1.381 (4) | C23—C24 | 1.387 (4) |
| C2—H2A | 0.9300 | C23—N2 | 1.400 (3) |
| C3—C4 | 1.372 (4) | C24—H24A | 0.9300 |
| C3—H3A | 0.9300 | C25—N2 | 1.473 (3) |
| C4—C5 | 1.373 (4) | C25—C26 | 1.516 (4) |
| C4—O3 | 1.398 (3) | C25—H25A | 0.9700 |
| C5—C6 | 1.377 (4) | C25—H25B | 0.9700 |
| C5—H5A | 0.9300 | C26—N3 | 1.477 (4) |
| C6—H6A | 0.9300 | C26—H26A | 0.9700 |
| C7—O2 | 1.257 (3) | C26—H26B | 0.9700 |
| C7—O1 | 1.259 (3) | C27—N3 | 1.490 (3) |
| C8—O3 | 1.381 (3) | C27—C28 | 1.526 (4) |
| C8—C13 | 1.381 (4) | C27—H27A | 0.9700 |
| C8—C9 | 1.381 (4) | C27—H27B | 0.9700 |
| C9—C10 | 1.382 (4) | C28—N2 | 1.447 (4) |
| C9—H9AA | 0.9300 | C28—H28A | 0.9700 |
| C10—C11 | 1.393 (4) | C28—H28B | 0.9700 |
| C10—H10A | 0.9300 | C29—C30 | 1.446 (6) |
| C11—C12 | 1.379 (4) | C29—N1 | 1.492 (4) |
| C11—C14 | 1.488 (4) | C29—H29A | 0.9700 |
| C12—C13 | 1.379 (4) | C29—H29B | 0.9700 |
| C12—H12A | 0.9300 | C30—H30A | 0.9600 |
| C13—H13A | 0.9300 | C30—H30B | 0.9600 |
| C14—O5 | 1.253 (4) | C30—H30C | 0.9600 |
| C14—O4 | 1.273 (3) | N3—H3B | 0.9000 |
| C15—N1 | 1.345 (4) | N3—H3C | 0.9000 |
| C15—C16 | 1.368 (4) | O4—Ni1ii | 2.0663 (19) |
| C15—H15A | 0.9300 | O1W—H1 | 0.8500 |
| C16—C17 | 1.428 (4) | O1W—H2 | 0.8501 |
| C16—C20 | 1.515 (3) | O2W—H3 | 0.8500 |
| C17—O6 | 1.255 (3) | O2W—H4 | 0.8499 |
| O6—Ni1—O7 | 89.94 (8) | O8—C20—C16 | 117.4 (2) |
| O6—Ni1—O4i | 173.89 (8) | O7—C20—C16 | 120.1 (2) |
| O7—Ni1—O4i | 95.85 (8) | C22—C21—C18 | 120.3 (3) |
| O6—Ni1—O1 | 84.98 (8) | C22—C21—H21A | 119.9 |
| O7—Ni1—O1 | 173.98 (7) | C18—C21—H21A | 119.9 |
| O4i—Ni1—O1 | 89.13 (8) | C21—C22—F1 | 118.1 (3) |
| O6—Ni1—O1W | 90.05 (8) | C21—C22—C23 | 124.1 (3) |
| O7—Ni1—O1W | 90.44 (8) | F1—C22—C23 | 117.8 (2) |
| O4i—Ni1—O1W | 87.94 (8) | C24—C23—N2 | 124.1 (3) |
| O1—Ni1—O1W | 86.35 (8) | C24—C23—C22 | 115.7 (2) |
| O6—Ni1—O2W | 89.40 (9) | N2—C23—C22 | 120.1 (3) |
| O7—Ni1—O2W | 92.15 (9) | C23—C24—C19 | 121.3 (3) |
| O4i—Ni1—O2W | 92.34 (8) | C23—C24—H24A | 119.3 |
| O1—Ni1—O2W | 91.02 (8) | C19—C24—H24A | 119.3 |
| O1W—Ni1—O2W | 177.35 (7) | N2—C25—C26 | 110.2 (2) |
| C2—C1—C6 | 119.0 (2) | N2—C25—H25A | 109.6 |
| C2—C1—C7 | 122.3 (2) | C26—C25—H25A | 109.6 |
| C6—C1—C7 | 118.6 (2) | N2—C25—H25B | 109.6 |
| C3—C2—C1 | 120.8 (3) | C26—C25—H25B | 109.6 |
| C3—C2—H2A | 119.6 | H25A—C25—H25B | 108.1 |
| C1—C2—H2A | 119.6 | N3—C26—C25 | 109.2 (2) |
| C2—C3—C4 | 118.9 (3) | N3—C26—H26A | 109.8 |
| C2—C3—H3A | 120.5 | C25—C26—H26A | 109.8 |
| C4—C3—H3A | 120.5 | N3—C26—H26B | 109.8 |
| C5—C4—C3 | 121.3 (3) | C25—C26—H26B | 109.8 |
| C5—C4—O3 | 119.9 (3) | H26A—C26—H26B | 108.3 |
| C3—C4—O3 | 118.8 (3) | N3—C27—C28 | 110.7 (2) |
| C4—C5—C6 | 119.3 (3) | N3—C27—H27A | 109.5 |
| C4—C5—H5A | 120.3 | C28—C27—H27A | 109.5 |
| C6—C5—H5A | 120.3 | N3—C27—H27B | 109.5 |
| C5—C6—C1 | 120.6 (3) | C28—C27—H27B | 109.5 |
| C5—C6—H6A | 119.7 | H27A—C27—H27B | 108.1 |
| C1—C6—H6A | 119.7 | N2—C28—C27 | 110.0 (2) |
| O2—C7—O1 | 123.9 (2) | N2—C28—H28A | 109.7 |
| O2—C7—C1 | 119.1 (2) | C27—C28—H28A | 109.7 |
| O1—C7—C1 | 116.9 (2) | N2—C28—H28B | 109.7 |
| O3—C8—C13 | 123.3 (2) | C27—C28—H28B | 109.7 |
| O3—C8—C9 | 116.5 (2) | H28A—C28—H28B | 108.2 |
| C13—C8—C9 | 120.3 (3) | C30—C29—N1 | 114.9 (3) |
| C8—C9—C10 | 119.8 (3) | C30—C29—H29A | 108.5 |
| C8—C9—H9AA | 120.1 | N1—C29—H29A | 108.5 |
| C10—C9—H9AA | 120.1 | C30—C29—H29B | 108.5 |
| C9—C10—C11 | 120.8 (2) | N1—C29—H29B | 108.5 |
| C9—C10—H10A | 119.6 | H29A—C29—H29B | 107.5 |
| C11—C10—H10A | 119.6 | C29—C30—H30A | 109.5 |
| C12—C11—C10 | 118.0 (3) | C29—C30—H30B | 109.5 |
| C12—C11—C14 | 119.1 (3) | H30A—C30—H30B | 109.5 |
| C10—C11—C14 | 122.9 (2) | C29—C30—H30C | 109.5 |
| C13—C12—C11 | 122.0 (3) | H30A—C30—H30C | 109.5 |
| C13—C12—H12A | 119.0 | H30B—C30—H30C | 109.5 |
| C11—C12—H12A | 119.0 | C15—N1—C19 | 119.0 (2) |
| C12—C13—C8 | 119.2 (3) | C15—N1—C29 | 119.4 (3) |
| C12—C13—H13A | 120.4 | C19—N1—C29 | 121.5 (2) |
| C8—C13—H13A | 120.4 | C23—N2—C28 | 117.2 (2) |
| O5—C14—O4 | 124.8 (3) | C23—N2—C25 | 115.8 (2) |
| O5—C14—C11 | 117.4 (2) | C28—N2—C25 | 110.8 (2) |
| O4—C14—C11 | 117.9 (2) | C26—N3—C27 | 110.1 (2) |
| N1—C15—C16 | 126.1 (3) | C26—N3—H3B | 109.6 |
| N1—C15—H15A | 116.9 | C27—N3—H3B | 109.6 |
| C16—C15—H15A | 116.9 | C26—N3—H3C | 109.6 |
| C15—C16—C17 | 118.2 (2) | C27—N3—H3C | 109.6 |
| C15—C16—C20 | 117.5 (2) | H3B—N3—H3C | 108.2 |
| C17—C16—C20 | 124.4 (2) | C7—O1—Ni1 | 126.74 (17) |
| O6—C17—C16 | 126.2 (2) | C8—O3—C4 | 116.6 (2) |
| O6—C17—C18 | 118.1 (2) | C14—O4—Ni1ii | 124.49 (18) |
| C16—C17—C18 | 115.7 (2) | C17—O6—Ni1 | 126.84 (18) |
| C19—C18—C21 | 117.9 (2) | C20—O7—Ni1 | 130.58 (17) |
| C19—C18—C17 | 122.9 (2) | Ni1—O1W—H1 | 118.9 |
| C21—C18—C17 | 119.2 (2) | Ni1—O1W—H2 | 123.4 |
| C18—C19—N1 | 117.8 (2) | H1—O1W—H2 | 90.7 |
| C18—C19—C24 | 120.6 (3) | Ni1—O2W—H3 | 102.1 |
| N1—C19—C24 | 121.6 (3) | Ni1—O2W—H4 | 96.0 |
| O8—C20—O7 | 122.5 (2) | H3—O2W—H4 | 99.5 |
| Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2W—H4···O2 | 0.85 | 1.93 | 2.695 (3) | 149 |
| O2W—H4···O1 | 0.85 | 2.55 | 2.965 (3) | 111 |
| N3—H3B···O2iii | 0.90 | 1.82 | 2.714 (3) | 170 |
| N3—H3C···O8ii | 0.90 | 1.85 | 2.719 (3) | 162 |
| O1W—H1···O1iv | 0.85 | 2.03 | 2.761 (3) | 144 |
| O1W—H2···O4v | 0.85 | 1.99 | 2.834 (3) | 173 |
| O2W—H3···O5i | 0.85 | 1.82 | 2.615 (3) | 155 |
| Symmetry codes: (iii) x, y+1, z; (ii) x−1, y+1, z; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (i) x+1, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2W—H4···O2 | 0.85 | 1.93 | 2.695 (3) | 149 |
| O2W—H4···O1 | 0.85 | 2.55 | 2.965 (3) | 111 |
| N3—H3B···O2i | 0.90 | 1.82 | 2.714 (3) | 170 |
| N3—H3C···O8ii | 0.90 | 1.85 | 2.719 (3) | 162 |
| O1W—H1···O1iii | 0.85 | 2.03 | 2.761 (3) | 144 |
| O1W—H2···O4iv | 0.85 | 1.99 | 2.834 (3) | 173 |
| O2W—H3···O5v | 0.85 | 1.82 | 2.615 (3) | 155 |
| Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) −x+1, −y, −z+1; (iv) −x, −y+1, −z+1; (v) x+1, y−1, z. |
An, Z., Huang, J., Zhao, & Qi, W. (2005). Acta Cryst. E61, m2009–?. Reference not found – please check. Do you mean An, Z. Huang, J & Qi, W. (2007). Acta Cryst. E63, m2009?
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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, Hcf] 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 Ni atoms are coordinated by three oxygen atoms of two Hcf ligand and one 4,4'-oxy-bisbenzoate, one oxygen atom from one symmetry related 4,4'-oxy-bisbenzoate and two water molecules within a distorted octahedral geometry (Figure 1). The nickel atoms are linked by the 4,4'-oxy-bisbenzoate anions into a one-dimensional chain running along crystallographic [-1, 1.5, 0] direction. The adjacent chains are further extended into a two-dimensional supramolecular network by N—H···O and O—H···O hydrogen bonds(Tab. 1).