Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060813/hb2657sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060813/hb2657Isup2.hkl |
CCDC reference: 672754
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 90%
- Disorder in solvent or counterion
- R factor = 0.035
- wR factor = 0.108
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1W .. O2 .. 2.80 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2W .. 2.79 Ang.
Alert level C CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O1 .. 5.39 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O1W PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O2W PLAT411_ALERT_2_C Short Inter H...H Contact H5 .. H14B .. 2.11 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C32 H38 F2 N6 Ni1 O8 Atom count from the _atom_site data: C32 H34 F2 N6 Ni1 O8 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C32 H38 F2 N6 Ni O8 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 64.00 64.00 0.00 H 76.00 68.00 8.00 F 4.00 4.00 0.00 N 12.00 12.00 0.00 Ni 2.00 2.00 0.00 O 16.00 16.00 0.00 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the cadmium and zinc complexes of the norf anion, see: Chen et al. (2001); Wang et al.(2004). For background on the medicinal uses of Norfloxacin, see: Mizuki et al. (1996).
A mixture of Ni(NO3)2.6H2O (0.07 g, 0.25 mmol), Hnorf (0.16 g, 0.5 mmol), and water (12 ml) was stirred for 20 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. After cooling, green prisms of (I) were obtained from the reaction mixture.
The carbon-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2Ueq(C). The H on Nitrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.86 (1) /%A and with Uiso(H) = 1.2Ueq(N).
The water molecules is disordered over two sites in a 0.771 (7):0.229 (7) ratio. The water H atoms could not be located in the present study.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Ni(C16H17FN3O3)2]·2H2O | F(000) = 756 |
Mr = 727.36 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8072 reflections |
a = 5.8389 (2) Å | θ = 1.8–25.5° |
b = 21.5704 (8) Å | µ = 0.66 mm−1 |
c = 13.2408 (4) Å | T = 295 K |
β = 100.763 (1)° | Prism, green |
V = 1638.31 (10) Å3 | 0.32 × 0.26 × 0.18 mm |
Z = 2 |
Bruker SMART CCD diffractometer | 3037 independent reflections |
Radiation source: fine-focus sealed tube | 2766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→7 |
Tmin = 0.816, Tmax = 0.890 | k = −26→20 |
8473 measured reflections | l = −16→13 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0692P)2 + 1.1691P] where P = (Fo2 + 2Fc2)/3 |
3037 reflections | (Δ/σ)max < 0.001 |
232 parameters | Δρmax = 0.66 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
[Ni(C16H17FN3O3)2]·2H2O | V = 1638.31 (10) Å3 |
Mr = 727.36 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.8389 (2) Å | µ = 0.66 mm−1 |
b = 21.5704 (8) Å | T = 295 K |
c = 13.2408 (4) Å | 0.32 × 0.26 × 0.18 mm |
β = 100.763 (1)° |
Bruker SMART CCD diffractometer | 3037 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2766 reflections with I > 2σ(I) |
Tmin = 0.816, Tmax = 0.890 | Rint = 0.023 |
8473 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.66 e Å−3 |
3037 reflections | Δρmin = −0.36 e Å−3 |
232 parameters |
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. #============================================================================== # 8. REFINEMENT DATA _refine_special_details |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1W | −0.212 (3) | 0.5083 (3) | 0.9619 (4) | 0.269 (7) | 0.771 (7) |
O2W | −0.530 (7) | 0.4676 (10) | 0.9199 (13) | 0.269 (7) | 0.229 (7) |
Ni1 | 0.0000 | 0.5000 | 0.5000 | 0.02183 (14) | |
F1 | 0.6987 (2) | 0.25278 (6) | 0.66313 (11) | 0.0456 (4) | |
O1 | −0.2244 (3) | 0.50862 (6) | 0.60039 (12) | 0.0278 (3) | |
O2 | −0.3489 (4) | 0.50317 (7) | 0.74766 (15) | 0.0507 (5) | |
O3 | 0.1702 (2) | 0.43116 (6) | 0.59199 (10) | 0.0270 (3) | |
N1 | −0.0082 (3) | 0.34446 (8) | 0.84271 (12) | 0.0288 (4) | |
N2 | 0.5781 (3) | 0.18573 (8) | 0.82650 (13) | 0.0282 (4) | |
N3 | 0.7581 (3) | 0.06548 (7) | 0.90923 (13) | 0.0260 (4) | |
H3N | 0.633 (3) | 0.0444 (11) | 0.893 (2) | 0.046 (7)* | |
C1 | −0.2232 (4) | 0.48474 (9) | 0.68784 (16) | 0.0276 (4) | |
C2 | −0.0695 (3) | 0.42936 (8) | 0.72119 (14) | 0.0259 (4) | |
C3 | 0.1112 (3) | 0.40744 (8) | 0.67023 (14) | 0.0236 (4) | |
C4 | 0.2286 (3) | 0.35113 (8) | 0.71319 (14) | 0.0244 (4) | |
C5 | 0.4086 (3) | 0.32589 (9) | 0.66939 (15) | 0.0279 (4) | |
H5 | 0.4551 | 0.3462 | 0.6146 | 0.034* | |
C6 | 0.5158 (3) | 0.27262 (9) | 0.70514 (16) | 0.0281 (4) | |
C7 | 0.4534 (3) | 0.23790 (9) | 0.78697 (15) | 0.0260 (4) | |
C8 | 0.2748 (3) | 0.26310 (9) | 0.83045 (15) | 0.0285 (4) | |
H8 | 0.2258 | 0.2419 | 0.8838 | 0.034* | |
C9 | 0.1661 (3) | 0.31940 (9) | 0.79669 (15) | 0.0257 (4) | |
C10 | −0.1149 (3) | 0.39704 (9) | 0.80463 (15) | 0.0285 (4) | |
H10 | −0.2294 | 0.4129 | 0.8377 | 0.034* | |
C11 | −0.0729 (4) | 0.31627 (11) | 0.93573 (17) | 0.0370 (5) | |
H11A | −0.0875 | 0.2718 | 0.9260 | 0.044* | |
H11B | −0.2239 | 0.3321 | 0.9438 | 0.044* | |
C12 | 0.1007 (6) | 0.32911 (15) | 1.0321 (2) | 0.0613 (8) | |
H12A | 0.2522 | 0.3153 | 1.0236 | 0.092* | |
H12B | 0.0557 | 0.3074 | 1.0886 | 0.092* | |
H12C | 0.1054 | 0.3728 | 1.0459 | 0.092* | |
C13 | 0.5224 (5) | 0.16096 (11) | 0.92160 (18) | 0.0445 (6) | |
H13A | 0.3755 | 0.1387 | 0.9065 | 0.053* | |
H13B | 0.5053 | 0.1948 | 0.9678 | 0.053* | |
C14 | 0.7127 (5) | 0.11770 (11) | 0.97288 (17) | 0.0428 (6) | |
H14A | 0.8555 | 0.1413 | 0.9925 | 0.051* | |
H14B | 0.6702 | 0.1017 | 1.0353 | 0.051* | |
C15 | 0.6156 (4) | 0.13449 (10) | 0.75747 (16) | 0.0351 (5) | |
H15A | 0.6624 | 0.1512 | 0.6964 | 0.042* | |
H15B | 0.4710 | 0.1119 | 0.7362 | 0.042* | |
C16 | 0.8036 (4) | 0.09047 (10) | 0.81179 (16) | 0.0353 (5) | |
H16A | 0.8185 | 0.0562 | 0.7661 | 0.042* | |
H16B | 0.9515 | 0.1123 | 0.8250 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1W | 0.64 (2) | 0.116 (4) | 0.061 (3) | 0.061 (7) | 0.082 (6) | −0.012 (3) |
O2W | 0.64 (2) | 0.116 (4) | 0.061 (3) | 0.061 (7) | 0.082 (6) | −0.012 (3) |
Ni1 | 0.0265 (2) | 0.0140 (2) | 0.0229 (2) | −0.00066 (11) | −0.00080 (14) | 0.00301 (11) |
F1 | 0.0492 (8) | 0.0390 (7) | 0.0566 (8) | 0.0183 (6) | 0.0304 (7) | 0.0168 (6) |
O1 | 0.0312 (8) | 0.0212 (7) | 0.0292 (8) | 0.0046 (5) | 0.0007 (6) | 0.0038 (5) |
O2 | 0.0658 (13) | 0.0475 (11) | 0.0436 (11) | 0.0328 (8) | 0.0230 (9) | 0.0142 (7) |
O3 | 0.0312 (7) | 0.0203 (7) | 0.0287 (7) | 0.0025 (5) | 0.0036 (5) | 0.0078 (5) |
N1 | 0.0328 (9) | 0.0266 (9) | 0.0280 (8) | 0.0069 (7) | 0.0085 (7) | 0.0076 (7) |
N2 | 0.0378 (9) | 0.0207 (8) | 0.0262 (8) | 0.0095 (7) | 0.0062 (7) | 0.0048 (6) |
N3 | 0.0290 (9) | 0.0182 (8) | 0.0291 (8) | 0.0020 (6) | 0.0009 (7) | 0.0012 (6) |
C1 | 0.0309 (10) | 0.0218 (9) | 0.0288 (10) | 0.0043 (8) | 0.0022 (8) | 0.0000 (8) |
C2 | 0.0293 (9) | 0.0198 (9) | 0.0264 (9) | 0.0036 (7) | −0.0005 (7) | 0.0014 (7) |
C3 | 0.0266 (9) | 0.0190 (9) | 0.0226 (9) | −0.0014 (7) | −0.0016 (7) | 0.0001 (7) |
C4 | 0.0274 (9) | 0.0200 (9) | 0.0246 (9) | 0.0020 (7) | 0.0015 (7) | 0.0029 (7) |
C5 | 0.0331 (10) | 0.0245 (10) | 0.0269 (10) | 0.0014 (8) | 0.0075 (8) | 0.0063 (8) |
C6 | 0.0293 (10) | 0.0253 (10) | 0.0308 (10) | 0.0056 (8) | 0.0086 (8) | 0.0034 (8) |
C7 | 0.0303 (10) | 0.0207 (9) | 0.0254 (10) | 0.0017 (7) | 0.0011 (8) | 0.0028 (7) |
C8 | 0.0342 (10) | 0.0247 (10) | 0.0272 (10) | 0.0048 (8) | 0.0074 (8) | 0.0082 (8) |
C9 | 0.0288 (10) | 0.0226 (9) | 0.0249 (9) | 0.0028 (7) | 0.0030 (7) | 0.0035 (7) |
C10 | 0.0313 (10) | 0.0252 (10) | 0.0288 (10) | 0.0064 (8) | 0.0048 (8) | 0.0013 (8) |
C11 | 0.0414 (12) | 0.0368 (12) | 0.0365 (12) | 0.0077 (9) | 0.0171 (9) | 0.0132 (9) |
C12 | 0.076 (2) | 0.071 (2) | 0.0359 (13) | 0.0055 (16) | 0.0105 (13) | 0.0087 (13) |
C13 | 0.0620 (15) | 0.0395 (13) | 0.0373 (12) | 0.0287 (11) | 0.0227 (11) | 0.0183 (10) |
C14 | 0.0663 (15) | 0.0355 (12) | 0.0274 (11) | 0.0278 (11) | 0.0113 (10) | 0.0083 (9) |
C15 | 0.0493 (13) | 0.0261 (10) | 0.0279 (10) | 0.0076 (9) | 0.0026 (9) | 0.0011 (8) |
C16 | 0.0465 (12) | 0.0287 (11) | 0.0312 (11) | 0.0124 (9) | 0.0089 (9) | 0.0022 (9) |
Ni1—O1i | 2.0415 (15) | C4—C9 | 1.405 (3) |
Ni1—O1 | 2.0415 (15) | C5—C6 | 1.351 (3) |
Ni1—O3 | 2.0552 (13) | C5—H5 | 0.9300 |
Ni1—O3i | 2.0552 (13) | C6—C7 | 1.419 (3) |
Ni1—N3ii | 2.1908 (16) | C7—C8 | 1.392 (3) |
Ni1—N3iii | 2.1908 (16) | C8—C9 | 1.404 (3) |
F1—C6 | 1.362 (2) | C8—H8 | 0.9300 |
O1—C1 | 1.266 (3) | C10—H10 | 0.9300 |
O2—C1 | 1.241 (3) | C11—C12 | 1.500 (4) |
O3—C3 | 1.260 (2) | C11—H11A | 0.9700 |
N1—C10 | 1.346 (2) | C11—H11B | 0.9700 |
N1—C9 | 1.389 (2) | C12—H12A | 0.9600 |
N1—C11 | 1.484 (2) | C12—H12B | 0.9600 |
N2—C7 | 1.389 (2) | C12—H12C | 0.9600 |
N2—C13 | 1.460 (3) | C13—C14 | 1.512 (3) |
N2—C15 | 1.476 (3) | C13—H13A | 0.9700 |
N3—C14 | 1.461 (3) | C13—H13B | 0.9700 |
N3—C16 | 1.468 (3) | C14—H14A | 0.9700 |
N3—Ni1iv | 2.1908 (16) | C14—H14B | 0.9700 |
N3—H3N | 0.852 (10) | C15—C16 | 1.526 (3) |
C1—C2 | 1.510 (3) | C15—H15A | 0.9700 |
C2—C10 | 1.373 (3) | C15—H15B | 0.9700 |
C2—C3 | 1.435 (3) | C16—H16A | 0.9700 |
C3—C4 | 1.457 (3) | C16—H16B | 0.9700 |
C4—C5 | 1.401 (3) | ||
O1i—Ni1—O1 | 180.0 | N2—C7—C6 | 121.60 (18) |
O1i—Ni1—O3 | 91.26 (5) | C8—C7—C6 | 115.36 (18) |
O1—Ni1—O3 | 88.74 (5) | C7—C8—C9 | 122.36 (18) |
O1i—Ni1—O3i | 88.74 (5) | C7—C8—H8 | 118.8 |
O1—Ni1—O3i | 91.26 (5) | C9—C8—H8 | 118.8 |
O3—Ni1—O3i | 180.0 | N1—C9—C8 | 121.44 (17) |
O1i—Ni1—N3ii | 90.60 (6) | N1—C9—C4 | 118.35 (17) |
O1—Ni1—N3ii | 89.40 (6) | C8—C9—C4 | 120.20 (18) |
O3—Ni1—N3ii | 92.88 (6) | N1—C10—C2 | 125.71 (18) |
O3i—Ni1—N3ii | 87.12 (6) | N1—C10—H10 | 117.1 |
O1i—Ni1—N3iii | 89.40 (6) | C2—C10—H10 | 117.1 |
O1—Ni1—N3iii | 90.60 (6) | N1—C11—C12 | 113.2 (2) |
O3—Ni1—N3iii | 87.12 (6) | N1—C11—H11A | 108.9 |
O3i—Ni1—N3iii | 92.88 (6) | C12—C11—H11A | 108.9 |
N3ii—Ni1—N3iii | 180.0 | N1—C11—H11B | 108.9 |
C1—O1—Ni1 | 131.60 (13) | C12—C11—H11B | 108.9 |
C3—O3—Ni1 | 127.19 (12) | H11A—C11—H11B | 107.8 |
C10—N1—C9 | 119.29 (16) | C11—C12—H12A | 109.5 |
C10—N1—C11 | 118.96 (16) | C11—C12—H12B | 109.5 |
C9—N1—C11 | 121.70 (16) | H12A—C12—H12B | 109.5 |
C7—N2—C13 | 115.85 (16) | C11—C12—H12C | 109.5 |
C7—N2—C15 | 120.08 (16) | H12A—C12—H12C | 109.5 |
C13—N2—C15 | 110.05 (17) | H12B—C12—H12C | 109.5 |
C14—N3—C16 | 107.83 (16) | N2—C13—C14 | 110.48 (18) |
C14—N3—Ni1iv | 110.40 (12) | N2—C13—H13A | 109.6 |
C16—N3—Ni1iv | 121.00 (13) | C14—C13—H13A | 109.6 |
C14—N3—H3N | 108.2 (18) | N2—C13—H13B | 109.6 |
C16—N3—H3N | 105.5 (18) | C14—C13—H13B | 109.6 |
Ni1iv—N3—H3N | 103.1 (18) | H13A—C13—H13B | 108.1 |
O2—C1—O1 | 123.41 (18) | N3—C14—C13 | 114.48 (19) |
O2—C1—C2 | 117.17 (18) | N3—C14—H14A | 108.6 |
O1—C1—C2 | 119.38 (18) | C13—C14—H14A | 108.6 |
C10—C2—C3 | 118.71 (17) | N3—C14—H14B | 108.6 |
C10—C2—C1 | 116.33 (17) | C13—C14—H14B | 108.6 |
C3—C2—C1 | 124.92 (17) | H14A—C14—H14B | 107.6 |
O3—C3—C2 | 126.23 (17) | N2—C15—C16 | 110.53 (16) |
O3—C3—C4 | 118.58 (17) | N2—C15—H15A | 109.5 |
C2—C3—C4 | 115.15 (16) | C16—C15—H15A | 109.5 |
C5—C4—C9 | 117.48 (17) | N2—C15—H15B | 109.5 |
C5—C4—C3 | 119.79 (17) | C16—C15—H15B | 109.5 |
C9—C4—C3 | 122.71 (17) | H15A—C15—H15B | 108.1 |
C6—C5—C4 | 121.30 (18) | N3—C16—C15 | 114.23 (17) |
C6—C5—H5 | 119.4 | N3—C16—H16A | 108.7 |
C4—C5—H5 | 119.4 | C15—C16—H16A | 108.7 |
C5—C6—F1 | 118.13 (17) | N3—C16—H16B | 108.7 |
C5—C6—C7 | 123.23 (19) | C15—C16—H16B | 108.7 |
F1—C6—C7 | 118.58 (17) | H16A—C16—H16B | 107.6 |
N2—C7—C8 | 122.76 (18) | ||
O3—Ni1—O1—C1 | 7.83 (18) | F1—C6—C7—N2 | 1.9 (3) |
N3ii—Ni1—O1—C1 | 100.72 (18) | C5—C6—C7—C8 | −1.2 (3) |
N3iii—Ni1—O1—C1 | −79.28 (18) | F1—C6—C7—C8 | 176.00 (17) |
O1i—Ni1—O3—C3 | −174.28 (15) | N2—C7—C8—C9 | 173.20 (18) |
O1—Ni1—O3—C3 | 5.72 (15) | C6—C7—C8—C9 | −0.8 (3) |
N3ii—Ni1—O3—C3 | −83.62 (15) | C10—N1—C9—C8 | −176.91 (19) |
N3iii—Ni1—O3—C3 | 96.38 (15) | C11—N1—C9—C8 | 5.8 (3) |
Ni1—O1—C1—O2 | 166.39 (17) | C10—N1—C9—C4 | 1.7 (3) |
Ni1—O1—C1—C2 | −16.1 (3) | C11—N1—C9—C4 | −175.62 (18) |
O2—C1—C2—C10 | 12.3 (3) | C7—C8—C9—N1 | −178.50 (19) |
O1—C1—C2—C10 | −165.38 (19) | C7—C8—C9—C4 | 2.9 (3) |
O2—C1—C2—C3 | −170.1 (2) | C5—C4—C9—N1 | 178.51 (17) |
O1—C1—C2—C3 | 12.2 (3) | C3—C4—C9—N1 | −2.9 (3) |
Ni1—O3—C3—C2 | −9.7 (3) | C5—C4—C9—C8 | −2.9 (3) |
Ni1—O3—C3—C4 | 168.14 (12) | C3—C4—C9—C8 | 175.70 (18) |
C10—C2—C3—O3 | 178.57 (18) | C9—N1—C10—C2 | 0.8 (3) |
C1—C2—C3—O3 | 1.0 (3) | C11—N1—C10—C2 | 178.1 (2) |
C10—C2—C3—C4 | 0.7 (3) | C3—C2—C10—N1 | −2.0 (3) |
C1—C2—C3—C4 | −176.88 (17) | C1—C2—C10—N1 | 175.80 (19) |
O3—C3—C4—C5 | 2.2 (3) | C10—N1—C11—C12 | −101.8 (2) |
C2—C3—C4—C5 | −179.76 (17) | C9—N1—C11—C12 | 75.5 (3) |
O3—C3—C4—C9 | −176.37 (17) | C7—N2—C13—C14 | −163.1 (2) |
C2—C3—C4—C9 | 1.7 (3) | C15—N2—C13—C14 | 56.5 (3) |
C9—C4—C5—C6 | 0.9 (3) | C16—N3—C14—C13 | 53.9 (3) |
C3—C4—C5—C6 | −177.74 (19) | Ni1iv—N3—C14—C13 | −171.88 (17) |
C4—C5—C6—F1 | −176.03 (18) | N2—C13—C14—N3 | −57.8 (3) |
C4—C5—C6—C7 | 1.2 (3) | C7—N2—C15—C16 | 166.05 (18) |
C13—N2—C7—C8 | −4.2 (3) | C13—N2—C15—C16 | −55.5 (2) |
C15—N2—C7—C8 | 131.9 (2) | C14—N3—C16—C15 | −52.7 (2) |
C13—N2—C7—C6 | 169.5 (2) | Ni1iv—N3—C16—C15 | 178.92 (14) |
C15—N2—C7—C6 | −54.4 (3) | N2—C15—C16—N3 | 55.4 (2) |
C5—C6—C7—N2 | −175.37 (18) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2v | 0.85 (1) | 2.43 (2) | 3.159 (2) | 145 (2) |
Symmetry code: (v) −x, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C16H17FN3O3)2]·2H2O |
Mr | 727.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 5.8389 (2), 21.5704 (8), 13.2408 (4) |
β (°) | 100.763 (1) |
V (Å3) | 1638.31 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.32 × 0.26 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.816, 0.890 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8473, 3037, 2766 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.108, 0.97 |
No. of reflections | 3037 |
No. of parameters | 232 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.66, −0.36 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
Ni1—O1 | 2.0415 (15) | Ni1—N3i | 2.1908 (16) |
Ni1—O3 | 2.0552 (13) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2ii | 0.852 (10) | 2.425 (17) | 3.159 (2) | 145 (2) |
Symmetry code: (ii) −x, y−1/2, −z+3/2. |
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Norfloxacin (Hnorf, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl) -3-quinoline carboxylic acid) is member of the class of quinolones that is used to treat infections (Mizuki et al., 1996). Cadmium(II) and zinc(II) derivatives of norf have been reported (Chen et al., 2001; Wang et al., 2004). The title nickel(II) derivative, (I), a two-dimensional coordination polymer in which the anion acts in a bridging mode, is reported here (Fig. 1).
The Ni(II) atom in (I) is coordinated by four oxygen atoms and two N atoms from four norfloxacin ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (100) (Fig. 2). The disordered, uncoordinated, water molecules occupy the cavities.