Literature DB >> 21200640

Poly[[tetra-aqua-bis[μ(3)-1-ethyl-6-fluoro-4-oxo-7-(piperazinium-1-yl)-1H-quinoline-3-carboxyl-ato]dinickel(II)] hydroxide nitrate].

Wen-Dong Song, Yi-Ling Wan, Peng-Zhi Hong, Seik Weng Ng.   

Abstract

In the title compound, [Ni(2)(C(16)H(18)FN(3)O(3))(2)(H(2)O)(4)](OH)(NO(3)), the cationic [Ni(2)(C(16)H(18)FN(3)O(3))(2)(H(2)O)(4)](2+) building units are linked through Ni-O(carboxyl-ate) and Ni-N(amino) bridges into a layer structure. The two independent nickel atoms lie on inversion centres: one adopts an NiO(6) octa-hedral geometry, the other a trans-NiN(2)O(4) 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.

Entities:  

Year:  2007        PMID: 21200640      PMCID: PMC2914950          DOI: 10.1107/S1600536807062885

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For related structures, see Barbas et al. (2007 ▶); Florence et al. (2000 ▶). For medical background on norfloxacin, see Goldstein (1987 ▶).

Experimental

Crystal data

[Ni2(C16H18FN3O3)2(H2O)4](NO3)(OH) M = 907.17 Triclinic, a = 8.9633 (2) Å b = 9.8121 (2) Å c = 13.2119 (3) Å α = 101.504 (2)° β = 106.301 (2)° γ = 113.528 (2)° V = 956.34 (4) Å3 Z = 1 Mo Kα radiation μ = 1.07 mm−1 T = 295 (2) K 0.18 × 0.16 × 0.15 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.686, T max = 0.856 11320 measured reflections 4304 independent reflections 2869 reflections with I > 2σ(I) R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.069 wR(F 2) = 0.219 S = 1.03 4304 reflections 280 parameters 34 restraints H-atom parameters constrained Δρmax = 1.65 e Å−3 Δρmin = −0.59 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062885/hb2663sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062885/hb2663Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ni2(C16H18FN3O3)2(H2O)4](NO3)(OH)Z = 1
Mr = 907.17F(000) = 472
Triclinic, P1Dx = 1.575 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9633 (2) ÅCell parameters from 2076 reflections
b = 9.8121 (2) Åθ = 2.6–28.0°
c = 13.2119 (3) ŵ = 1.07 mm1
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 diffractometer4304 independent reflections
Radiation source: medium-focus sealed tube2869 reflections with I > 2σ(I)
graphiteRint = 0.051
φ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.686, Tmax = 0.856k = −12→12
11320 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1076P)2 + 1.3612P] where P = (Fo2 + 2Fc2)/3
4304 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 1.65 e Å3
34 restraintsΔρmin = −0.59 e Å3
xyzUiso*/UeqOcc. (<1)
Ni10.50000.50000.50000.0328 (3)
Ni21.00001.00000.50000.0362 (3)
F10.8924 (5)1.1417 (4)0.0053 (3)0.0597 (10)
O10.5117 (4)0.6049 (4)0.3832 (3)0.0403 (9)
O20.7870 (5)0.8001 (5)0.4694 (3)0.0522 (11)
O30.9054 (5)0.9832 (5)0.3374 (3)0.0450 (10)
O1w0.7762 (5)0.5892 (5)0.5746 (3)0.0516 (10)
H1w10.81190.62310.64590.077*
H1w20.82800.66500.55370.077*
O2w1.4635 (5)0.9364 (5)0.4764 (3)0.079 (3)0.50
H2w1.41730.87420.40830.118*0.50
O3w1.1392 (8)0.8776 (7)0.4696 (5)0.0892 (17)
H3w11.22090.93260.45130.134*
H3w21.06780.78870.41630.134*
N10.4068 (5)0.6750 (5)0.0911 (3)0.0353 (9)
N20.5693 (6)0.9176 (6)−0.1764 (3)0.0445 (11)
H2n0.56241.0037−0.16160.053*
N30.5140 (6)0.7018 (5)−0.3881 (4)0.0399 (10)
H3n0.48860.7535−0.42940.048*
C10.6428 (6)0.7216 (6)0.3853 (4)0.0355 (11)
C20.6166 (6)0.7618 (6)0.2808 (4)0.0343 (11)
C30.4548 (7)0.6655 (6)0.1942 (4)0.0372 (11)
H30.37040.58650.20750.045*
C40.7510 (6)0.8857 (6)0.2651 (4)0.0330 (10)
C50.6994 (6)0.8949 (6)0.1519 (4)0.0324 (10)
C60.8197 (7)1.0130 (6)0.1263 (4)0.0378 (11)
H60.93071.08820.18240.045*
C70.7757 (7)1.0182 (6)0.0216 (4)0.0400 (12)
C80.6112 (7)0.9076 (6)−0.0698 (4)0.0367 (11)
C90.4899 (7)0.7932 (6)−0.0432 (4)0.0360 (11)
H90.37900.7186−0.09960.043*
C100.5301 (6)0.7878 (6)0.0651 (4)0.0328 (10)
C110.2248 (7)0.5575 (7)0.0058 (5)0.0445 (13)
H11A0.18460.6056−0.04570.053*
H11B0.14440.52870.04340.053*
C120.2190 (9)0.4110 (8)−0.0597 (6)0.0684 (19)
H12A0.09970.3378−0.11370.103*
H12B0.25690.3622−0.00910.103*
H12C0.29650.4389−0.09840.103*
C130.6999 (9)0.9619 (7)−0.2271 (5)0.0551 (16)
H13A0.81811.0297−0.16790.066*
H13B0.67581.0214−0.27390.066*
C140.6927 (7)0.8160 (7)−0.2977 (4)0.0481 (14)
H14A0.77760.8489−0.33190.058*
H14B0.72800.7627−0.24900.058*
C150.3826 (7)0.6632 (7)−0.3352 (4)0.0431 (12)
H15A0.40530.6045−0.28730.052*
H15B0.26380.5959−0.39380.052*
C160.3921 (8)0.8111 (8)−0.2659 (5)0.0489 (14)
H16A0.36230.8665−0.31470.059*
H16B0.30560.7812−0.23270.059*
O40.9439 (11)0.5634 (8)0.7796 (6)0.0490 (19)0.50
O51.0325 (17)0.4310 (17)0.6823 (12)0.126 (5)0.50
O60.8282 (11)0.3095 (10)0.7300 (8)0.063 (2)0.50
N40.9354 (9)0.4383 (9)0.7316 (5)0.046 (2)0.50
U11U22U33U12U13U23
Ni10.0328 (5)0.0316 (5)0.0269 (5)0.0082 (4)0.0117 (4)0.0128 (4)
Ni20.0337 (5)0.0332 (5)0.0259 (5)0.0042 (4)0.0075 (4)0.0122 (4)
F10.074 (2)0.0439 (19)0.0362 (17)0.0039 (17)0.0227 (16)0.0180 (15)
O10.0361 (19)0.040 (2)0.0340 (18)0.0079 (16)0.0113 (15)0.0198 (16)
O20.044 (2)0.050 (2)0.0309 (19)−0.0013 (18)0.0047 (16)0.0212 (18)
O30.0351 (19)0.045 (2)0.0303 (18)0.0017 (17)0.0050 (15)0.0163 (17)
O1w0.041 (2)0.051 (2)0.053 (2)0.0136 (19)0.0144 (18)0.024 (2)
O2w0.069 (7)0.093 (9)0.067 (7)0.037 (7)0.024 (6)0.024 (7)
O3w0.084 (4)0.093 (4)0.094 (4)0.050 (3)0.034 (3)0.028 (3)
N10.029 (2)0.041 (2)0.029 (2)0.0115 (18)0.0106 (16)0.0132 (18)
N20.064 (3)0.041 (3)0.028 (2)0.024 (2)0.018 (2)0.015 (2)
N30.046 (3)0.035 (2)0.034 (2)0.013 (2)0.0175 (19)0.0142 (19)
C10.037 (3)0.037 (3)0.028 (2)0.013 (2)0.013 (2)0.014 (2)
C20.035 (3)0.035 (3)0.027 (2)0.012 (2)0.0110 (19)0.013 (2)
C30.037 (3)0.040 (3)0.037 (3)0.015 (2)0.019 (2)0.020 (2)
C40.036 (3)0.033 (3)0.029 (2)0.015 (2)0.013 (2)0.014 (2)
C50.035 (2)0.033 (3)0.027 (2)0.013 (2)0.0120 (19)0.013 (2)
C60.035 (3)0.035 (3)0.031 (2)0.009 (2)0.012 (2)0.009 (2)
C70.048 (3)0.033 (3)0.034 (3)0.012 (2)0.018 (2)0.015 (2)
C80.048 (3)0.039 (3)0.031 (2)0.025 (2)0.017 (2)0.017 (2)
C90.037 (3)0.035 (3)0.027 (2)0.014 (2)0.0076 (19)0.010 (2)
C100.036 (3)0.034 (3)0.029 (2)0.017 (2)0.0125 (19)0.012 (2)
C110.029 (3)0.056 (3)0.037 (3)0.014 (2)0.007 (2)0.017 (3)
C120.056 (4)0.046 (4)0.069 (5)0.011 (3)0.009 (3)0.004 (3)
C130.072 (4)0.039 (3)0.031 (3)0.006 (3)0.022 (3)0.012 (2)
C140.045 (3)0.044 (3)0.033 (3)0.002 (3)0.019 (2)0.007 (2)
C150.044 (3)0.047 (3)0.033 (3)0.020 (3)0.015 (2)0.009 (2)
C160.062 (4)0.067 (4)0.032 (3)0.043 (3)0.017 (3)0.021 (3)
O40.062 (5)0.030 (4)0.038 (4)0.019 (3)0.006 (3)0.005 (3)
O50.126 (8)0.116 (8)0.138 (8)0.022 (5)0.098 (7)0.060 (7)
O60.057 (5)0.046 (5)0.080 (6)0.016 (4)0.029 (4)0.026 (4)
N40.044 (5)0.058 (5)0.048 (5)0.026 (4)0.018 (4)0.037 (4)
Ni1—O12.022 (3)C1—C21.492 (6)
Ni1—O1i2.022 (3)C2—C31.359 (7)
Ni1—O1w2.103 (4)C2—C41.430 (6)
Ni1—O1wi2.103 (4)C3—H30.9300
Ni1—N3ii2.157 (5)C4—C51.468 (6)
Ni1—N3iii2.157 (5)C5—C61.408 (6)
Ni2—O21.979 (4)C5—C101.411 (7)
Ni2—O2iv1.979 (4)C6—C71.345 (7)
Ni2—O3iv2.021 (3)C6—H60.9300
Ni2—O32.021 (3)C7—C81.418 (7)
Ni2—O3wiv2.108 (6)C8—C91.401 (7)
Ni2—O3w2.108 (6)C9—C101.390 (6)
F1—C71.352 (6)C9—H90.9300
O1—C11.260 (6)C11—C121.496 (10)
O2—C11.247 (6)C11—H11A0.9700
O3—C41.256 (6)C11—H11B0.9700
O1w—H1w10.8501C12—H12A0.9600
O1w—H1w20.8500C12—H12B0.9600
O2w—O2wv1.088 (8)C12—H12C0.9600
O2w—H2w0.8500C13—C141.511 (9)
O3w—H3w10.8501C13—H13A0.9700
O3w—H3w20.8501C13—H13B0.9700
N1—C31.343 (6)C14—H14A0.9700
N1—C101.398 (6)C14—H14B0.9700
N1—C111.486 (6)C15—C161.509 (8)
N2—C81.387 (6)C15—H15A0.9700
N2—C161.463 (7)C15—H15B0.9700
N2—C131.469 (7)C16—H16A0.9700
N2—H2n0.8600C16—H16B0.9700
N3—C141.485 (7)O4—N41.225 (8)
N3—C151.493 (7)O5—N41.241 (9)
N3—Ni1vi2.157 (5)O6—N41.237 (8)
N3—H3n0.8600
O1—Ni1—O1i180.000 (1)N1—C3—H3117.3
O1—Ni1—O1w94.08 (14)C2—C3—H3117.3
O1i—Ni1—O1w85.92 (14)O3—C4—C2126.4 (4)
O1—Ni1—O1wi85.92 (14)O3—C4—C5118.6 (4)
O1i—Ni1—O1wi94.08 (14)C2—C4—C5115.0 (4)
O1w—Ni1—O1wi180.0C6—C5—C10117.4 (4)
O1—Ni1—N3iii89.36 (15)C6—C5—C4120.4 (4)
O1i—Ni1—N3iii90.64 (15)C10—C5—C4122.2 (4)
O1w—Ni1—N3iii87.36 (16)C7—C6—C5120.7 (5)
O1wi—Ni1—N3iii92.64 (16)C7—C6—H6119.7
O1—Ni1—N3ii90.64 (15)C5—C6—H6119.7
O1i—Ni1—N3ii89.36 (15)C6—C7—F1117.3 (5)
O1w—Ni1—N3ii92.64 (16)C6—C7—C8123.8 (4)
O1wi—Ni1—N3ii87.36 (16)F1—C7—C8118.8 (4)
N3iii—Ni1—N3ii180.0 (2)N2—C8—C9122.3 (5)
O2iv—Ni2—O2180.0N2—C8—C7122.3 (4)
O2iv—Ni2—O3iv91.12 (14)C9—C8—C7115.3 (4)
O2—Ni2—O3iv88.88 (14)C10—C9—C8122.0 (5)
O2iv—Ni2—O388.88 (14)C10—C9—H9119.0
O2—Ni2—O391.12 (14)C8—C9—H9119.0
O3iv—Ni2—O3180.000 (1)C9—C10—N1121.5 (4)
O2iv—Ni2—O3wiv91.8 (2)C9—C10—C5120.7 (4)
O2—Ni2—O3wiv88.2 (2)N1—C10—C5117.8 (4)
O3iv—Ni2—O3wiv92.6 (2)N1—C11—C12111.7 (5)
O3—Ni2—O3wiv87.4 (2)N1—C11—H11A109.3
O2iv—Ni2—O3w88.2 (2)C12—C11—H11A109.3
O2—Ni2—O3w91.8 (2)N1—C11—H11B109.3
O3iv—Ni2—O3w87.4 (2)C12—C11—H11B109.3
O3—Ni2—O3w92.6 (2)H11A—C11—H11B107.9
O3wiv—Ni2—O3w180.000 (3)C11—C12—H12A109.5
C1—O1—Ni1128.4 (3)C11—C12—H12B109.5
C1—O2—Ni2130.1 (3)H12A—C12—H12B109.5
C4—O3—Ni2125.3 (3)C11—C12—H12C109.5
Ni1—O1w—H1w1109.5H12A—C12—H12C109.5
Ni1—O1w—H1w2109.5H12B—C12—H12C109.5
H1w1—O1w—H1w2109.5N2—C13—C14110.9 (4)
O2wv—O2w—H2w138.4N2—C13—H13A109.5
Ni2—O3w—H3w1109.5C14—C13—H13A109.5
Ni2—O3w—H3w2109.4N2—C13—H13B109.5
H3w1—O3w—H3w2109.5C14—C13—H13B109.5
C3—N1—C10119.8 (4)H13A—C13—H13B108.0
C3—N1—C11118.1 (4)N3—C14—C13113.3 (5)
C10—N1—C11122.0 (4)N3—C14—H14A108.9
C8—N2—C16120.9 (4)C13—C14—H14A108.9
C8—N2—C13122.5 (5)N3—C14—H14B108.9
C16—N2—C13109.1 (4)C13—C14—H14B108.9
C8—N2—H2n99.1H14A—C14—H14B107.7
C16—N2—H2n99.1N3—C15—C16111.8 (5)
C13—N2—H2n99.1N3—C15—H15A109.2
C14—N3—C15108.2 (4)C16—C15—H15A109.2
C14—N3—Ni1vi115.0 (4)N3—C15—H15B109.2
C15—N3—Ni1vi115.5 (3)C16—C15—H15B109.2
C14—N3—H3n105.7H15A—C15—H15B107.9
C15—N3—H3n105.7N2—C16—C15111.5 (5)
Ni1vi—N3—H3n105.7N2—C16—H16A109.3
O2—C1—O1122.5 (4)C15—C16—H16A109.3
O2—C1—C2121.2 (4)N2—C16—H16B109.3
O1—C1—C2116.2 (4)C15—C16—H16B109.3
C3—C2—C4119.6 (4)H16A—C16—H16B108.0
C3—C2—C1115.7 (4)O4—N4—O6121.5 (9)
C4—C2—C1124.6 (4)O4—N4—O5123.2 (10)
N1—C3—C2125.4 (4)O6—N4—O5115.3 (10)
O1w—Ni1—O1—C1−20.5 (5)C4—C5—C6—C7177.4 (5)
O1wi—Ni1—O1—C1159.5 (5)C5—C6—C7—F1175.2 (5)
N3iii—Ni1—O1—C1−107.8 (5)C5—C6—C7—C8−1.0 (9)
N3ii—Ni1—O1—C172.2 (5)C16—N2—C8—C92.1 (8)
O3iv—Ni2—O2—C1168.0 (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—C175.3 (6)C13—N2—C8—C739.5 (8)
O3w—Ni2—O2—C1−104.7 (6)C6—C7—C8—N2179.2 (5)
O2iv—Ni2—O3—C4−170.1 (5)F1—C7—C8—N23.0 (8)
O2—Ni2—O3—C49.9 (5)C6—C7—C8—C92.9 (8)
O3wiv—Ni2—O3—C4−78.3 (5)F1—C7—C8—C9−173.3 (5)
O3w—Ni2—O3—C4101.7 (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—C27.9 (8)C8—C9—C10—N1178.8 (5)
Ni1—O1—C1—O2−6.5 (8)C8—C9—C10—C5−2.6 (8)
Ni1—O1—C1—C2173.5 (3)C3—N1—C10—C9174.9 (5)
O2—C1—C2—C3178.7 (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—C42.5 (8)C11—N1—C10—C5179.7 (5)
O1—C1—C2—C4−177.5 (5)C6—C5—C10—C94.4 (7)
C10—N1—C3—C22.2 (8)C4—C5—C10—C9−175.7 (5)
C11—N1—C3—C2178.9 (5)C6—C5—C10—N1−177.0 (5)
C4—C2—C3—N10.3 (9)C4—C5—C10—N13.0 (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—C1287.5 (6)
Ni2—O3—C4—C5176.5 (3)C8—N2—C13—C1492.7 (6)
C3—C2—C4—O3179.8 (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—C13175.4 (3)
C1—C2—C4—C5175.1 (5)N2—C13—C14—N356.8 (6)
O3—C4—C5—C6−1.4 (8)C14—N3—C15—C1654.0 (6)
C2—C4—C5—C6179.3 (5)Ni1vi—N3—C15—C16−175.4 (3)
O3—C4—C5—C10178.6 (5)C8—N2—C16—C15−91.7 (6)
C2—C4—C5—C10−0.7 (7)C13—N2—C16—C1558.7 (6)
C10—C5—C6—C7−2.6 (8)N3—C15—C16—N2−58.6 (6)
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O40.852.162.820 (8)135
O1w—H1w2···O20.851.972.700 (5)143
O2w—H2w···O6vii0.852.172.90 (1)145
O3w—H3w1···O2w0.852.092.699 (7)128
O3w—H3w2···O5vii0.851.962.77 (2)161
N3—H3n···O2wviii0.862.433.277 (6)171
Table 1

Selected bond lengths (Å)

Ni1—O12.022 (3)
Ni1—O1w2.103 (4)
Ni1—N3i2.157 (5)
Ni2—O21.979 (4)
Ni2—O32.021 (3)
Ni2—O3w2.108 (6)

Symmetry code: (i) .

  2 in total

Review 1.  Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity.

Authors:  E J Goldstein
Journal:  Am J Med       Date:  1987-06-26       Impact factor: 4.965

2.  Norfloxacin dihydrate.

Authors:  A J Florence; A R Kennedy; N Shankland; E Wright; A Al-Rubayi
Journal:  Acta Crystallogr C       Date:  2000-11       Impact factor: 1.172

  2 in total

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