Acta Cryst. (2008). E64, m70 [ doi:10.1107/S1600536807062885 ]
3-1-ethyl-6-fluoro-4-oxo-7-(piperazinium-1-yl)-1H-quinoline-3-carboxylato]dinickel(II)] hydroxide nitrate]In the title compound, [Ni2(C16H18FN3O3)2(H2O)4](OH)(NO3), the cationic [Ni2(C16H18FN3O3)2(H2O)4]2+ building units are linked through Ni-Ocarboxylate and Ni-Namino bridges into a layer structure. The two independent nickel atoms lie on inversion centres: one adopts an NiO6 octahedral geometry, the other a trans-NiN2O4 octahedral arrangement. The charge-balancing hydroxide and nitrate ions are of half site occupancy each. A network of O-H
O and N-H
O hydrogen bonds helps to establish the packing.
Nickel nitrate (1.0 mmol), 2,2'-bipyridine (1.0 mmol), norfloxacin (1 mmol) and water (10 ml) were hydrothermally treated in a Parr bomb at K22 K for 48 h. The bomb was cooled (5 K h-1) to room temperature to furnish blue blocks of (I).
The divalent cation in (I) requires two negative charges for charge balance. As the hydroxide [OH]- group lies near a special position, the occupancy of the O2w atom (arbitrarily labeled with a w) should be only half. Consequently, the nitrate [NO3]- group occupancy should also be half. Attempts to refine this group with full occupancy led to high displacement factors. The group was refined with a distance restraint of N–O 1.24±0.01 Å; the four atoms were restrained to lie on a plane. The Uij values of the four atoms as well as those of the O2w atom were restrained to be nearly isotropic.
The carbon- and nitrogen-bound H atoms were placed at calculated positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier). The hydroxy and water H atoms were placed in chemically reasonable positions with O—H = 0.85Å and refined as riding with Uiso(H) = 1.5Ueq(O).
The final difference Fourier map had two large peaks in the vicinity of the diordered groups.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
| [Ni2(C16H18FN3O3)2(H2O)4](NO3)(OH) | Z = 1 |
| Mr = 907.17 | F(000) = 472 |
| Triclinic, P1 | Dx = 1.575 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.9633 (2) Å | Cell parameters from 2076 reflections |
| b = 9.8121 (2) Å | θ = 2.6–28.0° |
| c = 13.2119 (3) Å | µ = 1.07 mm−1 |
| α = 101.504 (2)° | T = 295 K |
| β = 106.301 (2)° | Block, blue |
| γ = 113.528 (2)° | 0.18 × 0.16 × 0.15 mm |
| V = 956.34 (4) Å3 |
| Bruker APEXII diffractometer | 4304 independent reflections |
| Radiation source: medium-focus sealed tube | 2869 reflections with I > 2σ(I) |
| graphite | Rint = 0.051 |
| φ and ω scans | θmax = 27.5°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.686, Tmax = 0.856 | k = −12→12 |
| 11320 measured reflections | l = −17→17 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.219 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.1076P)2 + 1.3612P] where P = (Fo2 + 2Fc2)/3 |
| 4304 reflections | (Δ/σ)max = 0.001 |
| 280 parameters | Δρmax = 1.65 e Å−3 |
| 34 restraints | Δρmin = −0.59 e Å−3 |
| [Ni2(C16H18FN3O3)2(H2O)4](NO3)(OH) | γ = 113.528 (2)° |
| Mr = 907.17 | V = 956.34 (4) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 8.9633 (2) Å | Mo Kα radiation |
| b = 9.8121 (2) Å | µ = 1.07 mm−1 |
| c = 13.2119 (3) Å | T = 295 K |
| α = 101.504 (2)° | 0.18 × 0.16 × 0.15 mm |
| β = 106.301 (2)° |
| Bruker APEXII diffractometer | 2869 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | Rint = 0.051 |
| Tmin = 0.686, Tmax = 0.856 | θmax = 27.5° |
| 11320 measured reflections | Standard reflections: 0 |
| 4304 independent reflections |
| R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
| wR(F2) = 0.219 | Δρmax = 1.65 e Å−3 |
| S = 1.03 | Δρmin = −0.59 e Å−3 |
| 4304 reflections | Absolute structure: ? |
| 280 parameters | Flack parameter: ? |
| 34 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0328 (3) | |
| Ni2 | 1.0000 | 1.0000 | 0.5000 | 0.0362 (3) | |
| F1 | 0.8924 (5) | 1.1417 (4) | 0.0053 (3) | 0.0597 (10) | |
| O1 | 0.5117 (4) | 0.6049 (4) | 0.3832 (3) | 0.0403 (9) | |
| O2 | 0.7870 (5) | 0.8001 (5) | 0.4694 (3) | 0.0522 (11) | |
| O3 | 0.9054 (5) | 0.9832 (5) | 0.3374 (3) | 0.0450 (10) | |
| O1w | 0.7762 (5) | 0.5892 (5) | 0.5746 (3) | 0.0516 (10) | |
| H1w1 | 0.8119 | 0.6231 | 0.6459 | 0.077* | |
| H1w2 | 0.8280 | 0.6650 | 0.5537 | 0.077* | |
| O2w | 1.4635 (5) | 0.9364 (5) | 0.4764 (3) | 0.079 (3) | 0.50 |
| H2w | 1.4173 | 0.8742 | 0.4083 | 0.118* | 0.50 |
| O3w | 1.1392 (8) | 0.8776 (7) | 0.4696 (5) | 0.0892 (17) | |
| H3w1 | 1.2209 | 0.9326 | 0.4513 | 0.134* | |
| H3w2 | 1.0678 | 0.7887 | 0.4163 | 0.134* | |
| N1 | 0.4068 (5) | 0.6750 (5) | 0.0911 (3) | 0.0353 (9) | |
| N2 | 0.5693 (6) | 0.9176 (6) | −0.1764 (3) | 0.0445 (11) | |
| H2n | 0.5624 | 1.0037 | −0.1616 | 0.053* | |
| N3 | 0.5140 (6) | 0.7018 (5) | −0.3881 (4) | 0.0399 (10) | |
| H3n | 0.4886 | 0.7535 | −0.4294 | 0.048* | |
| C1 | 0.6428 (6) | 0.7216 (6) | 0.3853 (4) | 0.0355 (11) | |
| C2 | 0.6166 (6) | 0.7618 (6) | 0.2808 (4) | 0.0343 (11) | |
| C3 | 0.4548 (7) | 0.6655 (6) | 0.1942 (4) | 0.0372 (11) | |
| H3 | 0.3704 | 0.5865 | 0.2075 | 0.045* | |
| C4 | 0.7510 (6) | 0.8857 (6) | 0.2651 (4) | 0.0330 (10) | |
| C5 | 0.6994 (6) | 0.8949 (6) | 0.1519 (4) | 0.0324 (10) | |
| C6 | 0.8197 (7) | 1.0130 (6) | 0.1263 (4) | 0.0378 (11) | |
| H6 | 0.9307 | 1.0882 | 0.1824 | 0.045* | |
| C7 | 0.7757 (7) | 1.0182 (6) | 0.0216 (4) | 0.0400 (12) | |
| C8 | 0.6112 (7) | 0.9076 (6) | −0.0698 (4) | 0.0367 (11) | |
| C9 | 0.4899 (7) | 0.7932 (6) | −0.0432 (4) | 0.0360 (11) | |
| H9 | 0.3790 | 0.7186 | −0.0996 | 0.043* | |
| C10 | 0.5301 (6) | 0.7878 (6) | 0.0651 (4) | 0.0328 (10) | |
| C11 | 0.2248 (7) | 0.5575 (7) | 0.0058 (5) | 0.0445 (13) | |
| H11A | 0.1846 | 0.6056 | −0.0457 | 0.053* | |
| H11B | 0.1444 | 0.5287 | 0.0434 | 0.053* | |
| C12 | 0.2190 (9) | 0.4110 (8) | −0.0597 (6) | 0.0684 (19) | |
| H12A | 0.0997 | 0.3378 | −0.1137 | 0.103* | |
| H12B | 0.2569 | 0.3622 | −0.0091 | 0.103* | |
| H12C | 0.2965 | 0.4389 | −0.0984 | 0.103* | |
| C13 | 0.6999 (9) | 0.9619 (7) | −0.2271 (5) | 0.0551 (16) | |
| H13A | 0.8181 | 1.0297 | −0.1679 | 0.066* | |
| H13B | 0.6758 | 1.0214 | −0.2739 | 0.066* | |
| C14 | 0.6927 (7) | 0.8160 (7) | −0.2977 (4) | 0.0481 (14) | |
| H14A | 0.7776 | 0.8489 | −0.3319 | 0.058* | |
| H14B | 0.7280 | 0.7627 | −0.2490 | 0.058* | |
| C15 | 0.3826 (7) | 0.6632 (7) | −0.3352 (4) | 0.0431 (12) | |
| H15A | 0.4053 | 0.6045 | −0.2873 | 0.052* | |
| H15B | 0.2638 | 0.5959 | −0.3938 | 0.052* | |
| C16 | 0.3921 (8) | 0.8111 (8) | −0.2659 (5) | 0.0489 (14) | |
| H16A | 0.3623 | 0.8665 | −0.3147 | 0.059* | |
| H16B | 0.3056 | 0.7812 | −0.2327 | 0.059* | |
| O4 | 0.9439 (11) | 0.5634 (8) | 0.7796 (6) | 0.0490 (19) | 0.50 |
| O5 | 1.0325 (17) | 0.4310 (17) | 0.6823 (12) | 0.126 (5) | 0.50 |
| O6 | 0.8282 (11) | 0.3095 (10) | 0.7300 (8) | 0.063 (2) | 0.50 |
| N4 | 0.9354 (9) | 0.4383 (9) | 0.7316 (5) | 0.046 (2) | 0.50 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0328 (5) | 0.0316 (5) | 0.0269 (5) | 0.0082 (4) | 0.0117 (4) | 0.0128 (4) |
| Ni2 | 0.0337 (5) | 0.0332 (5) | 0.0259 (5) | 0.0042 (4) | 0.0075 (4) | 0.0122 (4) |
| F1 | 0.074 (2) | 0.0439 (19) | 0.0362 (17) | 0.0039 (17) | 0.0227 (16) | 0.0180 (15) |
| O1 | 0.0361 (19) | 0.040 (2) | 0.0340 (18) | 0.0079 (16) | 0.0113 (15) | 0.0198 (16) |
| O2 | 0.044 (2) | 0.050 (2) | 0.0309 (19) | −0.0013 (18) | 0.0047 (16) | 0.0212 (18) |
| O3 | 0.0351 (19) | 0.045 (2) | 0.0303 (18) | 0.0017 (17) | 0.0050 (15) | 0.0163 (17) |
| O1w | 0.041 (2) | 0.051 (2) | 0.053 (2) | 0.0136 (19) | 0.0144 (18) | 0.024 (2) |
| O2w | 0.069 (7) | 0.093 (9) | 0.067 (7) | 0.037 (7) | 0.024 (6) | 0.024 (7) |
| O3w | 0.084 (4) | 0.093 (4) | 0.094 (4) | 0.050 (3) | 0.034 (3) | 0.028 (3) |
| N1 | 0.029 (2) | 0.041 (2) | 0.029 (2) | 0.0115 (18) | 0.0106 (16) | 0.0132 (18) |
| N2 | 0.064 (3) | 0.041 (3) | 0.028 (2) | 0.024 (2) | 0.018 (2) | 0.015 (2) |
| N3 | 0.046 (3) | 0.035 (2) | 0.034 (2) | 0.013 (2) | 0.0175 (19) | 0.0142 (19) |
| C1 | 0.037 (3) | 0.037 (3) | 0.028 (2) | 0.013 (2) | 0.013 (2) | 0.014 (2) |
| C2 | 0.035 (3) | 0.035 (3) | 0.027 (2) | 0.012 (2) | 0.0110 (19) | 0.013 (2) |
| C3 | 0.037 (3) | 0.040 (3) | 0.037 (3) | 0.015 (2) | 0.019 (2) | 0.020 (2) |
| C4 | 0.036 (3) | 0.033 (3) | 0.029 (2) | 0.015 (2) | 0.013 (2) | 0.014 (2) |
| C5 | 0.035 (2) | 0.033 (3) | 0.027 (2) | 0.013 (2) | 0.0120 (19) | 0.013 (2) |
| C6 | 0.035 (3) | 0.035 (3) | 0.031 (2) | 0.009 (2) | 0.012 (2) | 0.009 (2) |
| C7 | 0.048 (3) | 0.033 (3) | 0.034 (3) | 0.012 (2) | 0.018 (2) | 0.015 (2) |
| C8 | 0.048 (3) | 0.039 (3) | 0.031 (2) | 0.025 (2) | 0.017 (2) | 0.017 (2) |
| C9 | 0.037 (3) | 0.035 (3) | 0.027 (2) | 0.014 (2) | 0.0076 (19) | 0.010 (2) |
| C10 | 0.036 (3) | 0.034 (3) | 0.029 (2) | 0.017 (2) | 0.0125 (19) | 0.012 (2) |
| C11 | 0.029 (3) | 0.056 (3) | 0.037 (3) | 0.014 (2) | 0.007 (2) | 0.017 (3) |
| C12 | 0.056 (4) | 0.046 (4) | 0.069 (5) | 0.011 (3) | 0.009 (3) | 0.004 (3) |
| C13 | 0.072 (4) | 0.039 (3) | 0.031 (3) | 0.006 (3) | 0.022 (3) | 0.012 (2) |
| C14 | 0.045 (3) | 0.044 (3) | 0.033 (3) | 0.002 (3) | 0.019 (2) | 0.007 (2) |
| C15 | 0.044 (3) | 0.047 (3) | 0.033 (3) | 0.020 (3) | 0.015 (2) | 0.009 (2) |
| C16 | 0.062 (4) | 0.067 (4) | 0.032 (3) | 0.043 (3) | 0.017 (3) | 0.021 (3) |
| O4 | 0.062 (5) | 0.030 (4) | 0.038 (4) | 0.019 (3) | 0.006 (3) | 0.005 (3) |
| O5 | 0.126 (8) | 0.116 (8) | 0.138 (8) | 0.022 (5) | 0.098 (7) | 0.060 (7) |
| O6 | 0.057 (5) | 0.046 (5) | 0.080 (6) | 0.016 (4) | 0.029 (4) | 0.026 (4) |
| N4 | 0.044 (5) | 0.058 (5) | 0.048 (5) | 0.026 (4) | 0.018 (4) | 0.037 (4) |
| Ni1—O1 | 2.022 (3) | C1—C2 | 1.492 (6) |
| Ni1—O1i | 2.022 (3) | C2—C3 | 1.359 (7) |
| Ni1—O1w | 2.103 (4) | C2—C4 | 1.430 (6) |
| Ni1—O1wi | 2.103 (4) | C3—H3 | 0.9300 |
| Ni1—N3ii | 2.157 (5) | C4—C5 | 1.468 (6) |
| Ni1—N3iii | 2.157 (5) | C5—C6 | 1.408 (6) |
| Ni2—O2 | 1.979 (4) | C5—C10 | 1.411 (7) |
| Ni2—O2iv | 1.979 (4) | C6—C7 | 1.345 (7) |
| Ni2—O3iv | 2.021 (3) | C6—H6 | 0.9300 |
| Ni2—O3 | 2.021 (3) | C7—C8 | 1.418 (7) |
| Ni2—O3wiv | 2.108 (6) | C8—C9 | 1.401 (7) |
| Ni2—O3w | 2.108 (6) | C9—C10 | 1.390 (6) |
| F1—C7 | 1.352 (6) | C9—H9 | 0.9300 |
| O1—C1 | 1.260 (6) | C11—C12 | 1.496 (10) |
| O2—C1 | 1.247 (6) | C11—H11A | 0.9700 |
| O3—C4 | 1.256 (6) | C11—H11B | 0.9700 |
| O1w—H1w1 | 0.8501 | C12—H12A | 0.9600 |
| O1w—H1w2 | 0.8500 | C12—H12B | 0.9600 |
| O2w—O2wv | 1.088 (8) | C12—H12C | 0.9600 |
| O2w—H2w | 0.8500 | C13—C14 | 1.511 (9) |
| O3w—H3w1 | 0.8501 | C13—H13A | 0.9700 |
| O3w—H3w2 | 0.8501 | C13—H13B | 0.9700 |
| N1—C3 | 1.343 (6) | C14—H14A | 0.9700 |
| N1—C10 | 1.398 (6) | C14—H14B | 0.9700 |
| N1—C11 | 1.486 (6) | C15—C16 | 1.509 (8) |
| N2—C8 | 1.387 (6) | C15—H15A | 0.9700 |
| N2—C16 | 1.463 (7) | C15—H15B | 0.9700 |
| N2—C13 | 1.469 (7) | C16—H16A | 0.9700 |
| N2—H2n | 0.8600 | C16—H16B | 0.9700 |
| N3—C14 | 1.485 (7) | O4—N4 | 1.225 (8) |
| N3—C15 | 1.493 (7) | O5—N4 | 1.241 (9) |
| N3—Ni1vi | 2.157 (5) | O6—N4 | 1.237 (8) |
| N3—H3n | 0.8600 | ||
| O1—Ni1—O1i | 180.000 (1) | N1—C3—H3 | 117.3 |
| O1—Ni1—O1w | 94.08 (14) | C2—C3—H3 | 117.3 |
| O1i—Ni1—O1w | 85.92 (14) | O3—C4—C2 | 126.4 (4) |
| O1—Ni1—O1wi | 85.92 (14) | O3—C4—C5 | 118.6 (4) |
| O1i—Ni1—O1wi | 94.08 (14) | C2—C4—C5 | 115.0 (4) |
| O1w—Ni1—O1wi | 180.0 | C6—C5—C10 | 117.4 (4) |
| O1—Ni1—N3iii | 89.36 (15) | C6—C5—C4 | 120.4 (4) |
| O1i—Ni1—N3iii | 90.64 (15) | C10—C5—C4 | 122.2 (4) |
| O1w—Ni1—N3iii | 87.36 (16) | C7—C6—C5 | 120.7 (5) |
| O1wi—Ni1—N3iii | 92.64 (16) | C7—C6—H6 | 119.7 |
| O1—Ni1—N3ii | 90.64 (15) | C5—C6—H6 | 119.7 |
| O1i—Ni1—N3ii | 89.36 (15) | C6—C7—F1 | 117.3 (5) |
| O1w—Ni1—N3ii | 92.64 (16) | C6—C7—C8 | 123.8 (4) |
| O1wi—Ni1—N3ii | 87.36 (16) | F1—C7—C8 | 118.8 (4) |
| N3iii—Ni1—N3ii | 180.0 (2) | N2—C8—C9 | 122.3 (5) |
| O2iv—Ni2—O2 | 180.0 | N2—C8—C7 | 122.3 (4) |
| O2iv—Ni2—O3iv | 91.12 (14) | C9—C8—C7 | 115.3 (4) |
| O2—Ni2—O3iv | 88.88 (14) | C10—C9—C8 | 122.0 (5) |
| O2iv—Ni2—O3 | 88.88 (14) | C10—C9—H9 | 119.0 |
| O2—Ni2—O3 | 91.12 (14) | C8—C9—H9 | 119.0 |
| O3iv—Ni2—O3 | 180.000 (1) | C9—C10—N1 | 121.5 (4) |
| O2iv—Ni2—O3wiv | 91.8 (2) | C9—C10—C5 | 120.7 (4) |
| O2—Ni2—O3wiv | 88.2 (2) | N1—C10—C5 | 117.8 (4) |
| O3iv—Ni2—O3wiv | 92.6 (2) | N1—C11—C12 | 111.7 (5) |
| O3—Ni2—O3wiv | 87.4 (2) | N1—C11—H11A | 109.3 |
| O2iv—Ni2—O3w | 88.2 (2) | C12—C11—H11A | 109.3 |
| O2—Ni2—O3w | 91.8 (2) | N1—C11—H11B | 109.3 |
| O3iv—Ni2—O3w | 87.4 (2) | C12—C11—H11B | 109.3 |
| O3—Ni2—O3w | 92.6 (2) | H11A—C11—H11B | 107.9 |
| O3wiv—Ni2—O3w | 180.000 (3) | C11—C12—H12A | 109.5 |
| C1—O1—Ni1 | 128.4 (3) | C11—C12—H12B | 109.5 |
| C1—O2—Ni2 | 130.1 (3) | H12A—C12—H12B | 109.5 |
| C4—O3—Ni2 | 125.3 (3) | C11—C12—H12C | 109.5 |
| Ni1—O1w—H1w1 | 109.5 | H12A—C12—H12C | 109.5 |
| Ni1—O1w—H1w2 | 109.5 | H12B—C12—H12C | 109.5 |
| H1w1—O1w—H1w2 | 109.5 | N2—C13—C14 | 110.9 (4) |
| O2wv—O2w—H2w | 138.4 | N2—C13—H13A | 109.5 |
| Ni2—O3w—H3w1 | 109.5 | C14—C13—H13A | 109.5 |
| Ni2—O3w—H3w2 | 109.4 | N2—C13—H13B | 109.5 |
| H3w1—O3w—H3w2 | 109.5 | C14—C13—H13B | 109.5 |
| C3—N1—C10 | 119.8 (4) | H13A—C13—H13B | 108.0 |
| C3—N1—C11 | 118.1 (4) | N3—C14—C13 | 113.3 (5) |
| C10—N1—C11 | 122.0 (4) | N3—C14—H14A | 108.9 |
| C8—N2—C16 | 120.9 (4) | C13—C14—H14A | 108.9 |
| C8—N2—C13 | 122.5 (5) | N3—C14—H14B | 108.9 |
| C16—N2—C13 | 109.1 (4) | C13—C14—H14B | 108.9 |
| C8—N2—H2n | 99.1 | H14A—C14—H14B | 107.7 |
| C16—N2—H2n | 99.1 | N3—C15—C16 | 111.8 (5) |
| C13—N2—H2n | 99.1 | N3—C15—H15A | 109.2 |
| C14—N3—C15 | 108.2 (4) | C16—C15—H15A | 109.2 |
| C14—N3—Ni1vi | 115.0 (4) | N3—C15—H15B | 109.2 |
| C15—N3—Ni1vi | 115.5 (3) | C16—C15—H15B | 109.2 |
| C14—N3—H3n | 105.7 | H15A—C15—H15B | 107.9 |
| C15—N3—H3n | 105.7 | N2—C16—C15 | 111.5 (5) |
| Ni1vi—N3—H3n | 105.7 | N2—C16—H16A | 109.3 |
| O2—C1—O1 | 122.5 (4) | C15—C16—H16A | 109.3 |
| O2—C1—C2 | 121.2 (4) | N2—C16—H16B | 109.3 |
| O1—C1—C2 | 116.2 (4) | C15—C16—H16B | 109.3 |
| C3—C2—C4 | 119.6 (4) | H16A—C16—H16B | 108.0 |
| C3—C2—C1 | 115.7 (4) | O4—N4—O6 | 121.5 (9) |
| C4—C2—C1 | 124.6 (4) | O4—N4—O5 | 123.2 (10) |
| N1—C3—C2 | 125.4 (4) | O6—N4—O5 | 115.3 (10) |
| O1w—Ni1—O1—C1 | −20.5 (5) | C4—C5—C6—C7 | 177.4 (5) |
| O1wi—Ni1—O1—C1 | 159.5 (5) | C5—C6—C7—F1 | 175.2 (5) |
| N3iii—Ni1—O1—C1 | −107.8 (5) | C5—C6—C7—C8 | −1.0 (9) |
| N3ii—Ni1—O1—C1 | 72.2 (5) | C16—N2—C8—C9 | 2.1 (8) |
| O3iv—Ni2—O2—C1 | 168.0 (5) | C13—N2—C8—C9 | −144.4 (5) |
| O3—Ni2—O2—C1 | −12.0 (5) | C16—N2—C8—C7 | −174.0 (5) |
| O3wiv—Ni2—O2—C1 | 75.3 (6) | C13—N2—C8—C7 | 39.5 (8) |
| O3w—Ni2—O2—C1 | −104.7 (6) | C6—C7—C8—N2 | 179.2 (5) |
| O2iv—Ni2—O3—C4 | −170.1 (5) | F1—C7—C8—N2 | 3.0 (8) |
| O2—Ni2—O3—C4 | 9.9 (5) | C6—C7—C8—C9 | 2.9 (8) |
| O3wiv—Ni2—O3—C4 | −78.3 (5) | F1—C7—C8—C9 | −173.3 (5) |
| O3w—Ni2—O3—C4 | 101.7 (5) | N2—C8—C9—C10 | −177.4 (5) |
| Ni2—O2—C1—O1 | −172.1 (4) | C7—C8—C9—C10 | −1.0 (8) |
| Ni2—O2—C1—C2 | 7.9 (8) | C8—C9—C10—N1 | 178.8 (5) |
| Ni1—O1—C1—O2 | −6.5 (8) | C8—C9—C10—C5 | −2.6 (8) |
| Ni1—O1—C1—C2 | 173.5 (3) | C3—N1—C10—C9 | 174.9 (5) |
| O2—C1—C2—C3 | 178.7 (5) | C11—N1—C10—C9 | −1.6 (8) |
| O1—C1—C2—C3 | −1.2 (7) | C3—N1—C10—C5 | −3.7 (7) |
| O2—C1—C2—C4 | 2.5 (8) | C11—N1—C10—C5 | 179.7 (5) |
| O1—C1—C2—C4 | −177.5 (5) | C6—C5—C10—C9 | 4.4 (7) |
| C10—N1—C3—C2 | 2.2 (8) | C4—C5—C10—C9 | −175.7 (5) |
| C11—N1—C3—C2 | 178.9 (5) | C6—C5—C10—N1 | −177.0 (5) |
| C4—C2—C3—N1 | 0.3 (9) | C4—C5—C10—N1 | 3.0 (7) |
| C1—C2—C3—N1 | −176.1 (5) | C3—N1—C11—C12 | −89.1 (6) |
| Ni2—O3—C4—C2 | −4.4 (8) | C10—N1—C11—C12 | 87.5 (6) |
| Ni2—O3—C4—C5 | 176.5 (3) | C8—N2—C13—C14 | 92.7 (6) |
| C3—C2—C4—O3 | 179.8 (5) | C16—N2—C13—C14 | −57.2 (6) |
| C1—C2—C4—O3 | −4.1 (9) | C15—N3—C14—C13 | −53.8 (5) |
| C3—C2—C4—C5 | −1.0 (7) | Ni1vi—N3—C14—C13 | 175.4 (3) |
| C1—C2—C4—C5 | 175.1 (5) | N2—C13—C14—N3 | 56.8 (6) |
| O3—C4—C5—C6 | −1.4 (8) | C14—N3—C15—C16 | 54.0 (6) |
| C2—C4—C5—C6 | 179.3 (5) | Ni1vi—N3—C15—C16 | −175.4 (3) |
| O3—C4—C5—C10 | 178.6 (5) | C8—N2—C16—C15 | −91.7 (6) |
| C2—C4—C5—C10 | −0.7 (7) | C13—N2—C16—C15 | 58.7 (6) |
| C10—C5—C6—C7 | −2.6 (8) | N3—C15—C16—N2 | −58.6 (6) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+2, −z+1; (v) −x+3, −y+2, −z+1; (vi) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1w—H1w1···O4 | 0.85 | 2.16 | 2.820 (8) | 135 |
| O1w—H1w2···O2 | 0.85 | 1.97 | 2.700 (5) | 143 |
| O2w—H2w···O6vii | 0.85 | 2.17 | 2.90 (1) | 145 |
| O3w—H3w1···O2w | 0.85 | 2.09 | 2.699 (7) | 128 |
| O3w—H3w2···O5vii | 0.85 | 1.96 | 2.77 (2) | 161 |
| N3—H3n···O2wviii | 0.86 | 2.43 | 3.277 (6) | 171 |
| Symmetry codes: (vii) −x+2, −y+1, −z+1; (viii) x−1, y, z−1. |
| Ni1—O1 | 2.022 (3) | Ni2—O2 | 1.979 (4) |
| Ni1—O1w | 2.103 (4) | Ni2—O3 | 2.021 (3) |
| Ni1—N3i | 2.157 (5) | Ni2—O3w | 2.108 (6) |
| Symmetry codes: (i) x, y, z+1. |
We thank Guangdong Ocean University and the University of Malaya for supporting this study.
Barbas, R., Prohens, R. & Puigjaner, C. (2007). J. Therm. Anal. Calor. 89, 687–692.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2004). APEX2 (Version 2.0.23A) and SMART (Version 7.23A). Bruker AXS Inc, Madison, Wisconsin, USA.
Florence, A. J., Kennedy, A. R., Shankland, N., Wright, E. & Al-Rubayi, A. (2000). Acta Cryst. C56, 1372–1373.
Goldstein, E. (1987). Am. J. Med. 82, 3–17.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.
Westrip, S. P. (2007). publCIF. In preparation.
The drug norfloxacin has been used in the synthesis of metal complexes as it is a carboxylic acid. There are many crystal structure reports of transition metal derivatives (Cambridge Structural Database Version 5.28, Nov. 2006) but all these have the compound in the mono-deprotonated form, in which the piperazinyl group is a neutral substitutent. In the title compound (I), the substituent is protonated (Fig. 1). There are two nickel ions in the asymmetric unit of (I), both with site symmety 1. One adopts an NiO6 geometry, the other a trans-NiN2O4 arrangement (Table 1). A network of O—H···O and N—H···O hydrogen bonds (Table 2) helps to establish the packing.
For related structures, see Barbas et al. (2007) and Florence et al. (2000). For medical background on norfloxacin, see Goldstein (1987).