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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m17.
Published online 2007 December 6. doi:  10.1107/S1600536807062216
PMCID: PMC2914909

catena-Poly[[diaqua­[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato-κ2 O,O′]nickel(II)]-μ-4,4′-oxydibenzoato-κ2 O:O′]

Abstract

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 [An external file that holds a picture, illustration, etc.
Object name is e-64-00m17-efi1.jpg30] direction. In the crystal structure, the one-dimensional chains are connected via N—H(...)O and O—H(...)O hydrogen bonding to form a three-dimensional supra­molecular network.

Related literature

For general background, see: Xiao et al. (2005 [triangle]). For a related structure, see: An et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00m17-scheme1.jpg

Experimental

Crystal data

  • [Ni(C16H18FN3O3)(C14H8O5)(H2O)2]
  • M r = 670.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m17-efi2.jpg
  • a = 10.105 (2) Å
  • b = 12.230 (2) Å
  • c = 13.052 (3) Å
  • α = 72.50 (3)°
  • β = 73.13 (3)°
  • γ = 77.57 (3)°
  • V = 1457.7 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.74 mm−1
  • T = 298 (2) K
  • 0.32 × 0.24 × 0.22 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.798, T max = 0.855
  • 11571 measured reflections
  • 5134 independent reflections
  • 4210 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.112
  • S = 1.02
  • 5134 reflections
  • 406 parameters
  • H-atom parameters constrained
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062216/im2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062216/im2047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author thanks Jilin Normal University for supporting this work.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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)

Figures

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

Crystal data

[Ni(C16H18F1N3O3)(C14H8O5)(H2O)2]Z = 2
Mr = 670.28F000 = 696
Triclinic, P1Dx = 1.527 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.105 (2) ÅCell parameters from 11571 reflections
b = 12.230 (2) Åθ = 3.0–25.0º
c = 13.052 (3) ŵ = 0.74 mm1
α = 72.50 (3)ºT = 298 (2) K
β = 73.13 (3)ºBlock, green
γ = 77.57 (3)º0.32 × 0.24 × 0.22 mm
V = 1457.7 (5) Å3

Data collection

Bruker APEX CCD area-detector diffractometer5134 independent reflections
Radiation source: fine-focus sealed tube4210 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 298(2) Kθmax = 25.0º
ω scansθmin = 3.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.798, Tmax = 0.855k = −14→14
11571 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 0.73 e Å3
406 parametersΔρmin = −0.42 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ni10.55118 (3)0.06895 (3)0.29346 (3)0.02717 (12)
F10.11227 (19)0.57062 (15)0.2085 (2)0.0690 (7)
C10.1138 (3)0.1404 (2)0.3988 (2)0.0293 (6)
C2−0.0181 (3)0.1367 (3)0.3899 (3)0.0407 (7)
H2A−0.02970.08640.35320.049*
C3−0.1329 (3)0.2070 (3)0.4349 (3)0.0409 (7)
H3A−0.22160.20370.42950.049*
C4−0.1139 (3)0.2818 (2)0.4879 (2)0.0339 (6)
C50.0162 (3)0.2876 (2)0.4971 (3)0.0390 (7)
H5A0.02760.33960.53220.047*
C60.1296 (3)0.2156 (2)0.4539 (2)0.0351 (6)
H6A0.21750.21750.46180.042*
C70.2412 (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−0.41200.50510.60210.043*
C10−0.3900 (3)0.6506 (2)0.4779 (3)0.0376 (7)
H10A−0.46150.69790.51390.045*
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−0.15540.65410.25000.044*
C13−0.1759 (3)0.5093 (2)0.3730 (3)0.0401 (7)
H13A−0.10350.46220.33750.048*
C14−0.3468 (3)0.8187 (2)0.3084 (2)0.0338 (6)
C150.7543 (3)0.4092 (2)0.1121 (3)0.0388 (7)
H15A0.85110.40140.08840.047*
C160.6950 (3)0.3094 (2)0.1539 (2)0.0302 (6)
C170.5467 (3)0.3187 (2)0.1938 (2)0.0285 (6)
C180.4717 (3)0.4358 (2)0.1767 (2)0.0299 (6)
C190.5390 (3)0.5341 (2)0.1316 (2)0.0317 (6)
C200.7920 (3)0.1960 (2)0.1557 (2)0.0291 (6)
C210.3258 (3)0.4520 (2)0.2061 (3)0.0380 (7)
H21A0.27800.38820.23770.046*
C220.2540 (3)0.5596 (2)0.1887 (3)0.0406 (7)
C230.3163 (3)0.6614 (2)0.1475 (2)0.0317 (6)
C240.4612 (3)0.6458 (2)0.1191 (2)0.0340 (6)
H24A0.50800.71020.09140.041*
C250.1290 (3)0.7917 (2)0.2333 (2)0.0378 (7)
H25A0.17510.80830.28150.045*
H25B0.08420.72330.27340.045*
C260.0199 (3)0.8933 (2)0.2016 (3)0.0389 (7)
H26A−0.02830.87610.15520.047*
H26B−0.04830.90740.26760.047*
C270.1966 (3)0.9750 (2)0.0411 (2)0.0391 (7)
H27A0.24391.04250.00340.047*
H27B0.15150.9616−0.00950.047*
C280.3032 (3)0.8699 (2)0.0731 (2)0.0363 (7)
H28A0.36980.85450.00690.044*
H28B0.35390.88560.11860.044*
C290.7665 (4)0.6173 (3)0.0620 (3)0.0503 (9)
H29A0.71790.67500.10240.060*
H29B0.85690.59050.07950.060*
C300.7883 (5)0.6721 (4)−0.0552 (4)0.0830 (14)
H30A0.84120.7348−0.07380.124*
H30B0.69960.7015−0.07330.124*
H30C0.83850.6165−0.09630.124*
N10.6856 (3)0.51763 (19)0.1020 (2)0.0386 (6)
N20.2331 (2)0.76972 (18)0.13355 (19)0.0316 (5)
N30.0891 (2)0.99712 (18)0.14108 (18)0.0300 (5)
H3B0.12981.01510.18560.036*
H3C0.02521.05750.12070.036*
O10.34733 (19)0.05291 (16)0.38500 (15)0.0317 (4)
O20.2384 (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)
O60.4769 (2)0.23599 (15)0.23930 (18)0.0385 (5)
O70.7459 (2)0.10163 (15)0.20642 (17)0.0360 (5)
O80.9162 (2)0.20092 (16)0.10377 (18)0.0407 (5)
O1W0.5830 (2)0.10404 (15)0.43009 (15)0.0325 (4)
H10.63920.05650.46550.049*
H20.52040.10360.48990.049*
O2W0.5096 (2)0.03404 (17)0.16040 (15)0.0380 (5)
H30.5639−0.02870.15530.057*
H40.43420.00660.19660.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0245 (2)0.01742 (18)0.0365 (2)0.00159 (13)−0.00766 (14)−0.00538 (14)
F10.0262 (10)0.0311 (10)0.138 (2)0.0047 (8)−0.0149 (11)−0.0157 (12)
C10.0265 (14)0.0263 (13)0.0341 (14)0.0016 (11)−0.0103 (11)−0.0071 (12)
C20.0313 (16)0.0398 (17)0.0594 (19)0.0024 (13)−0.0171 (14)−0.0244 (15)
C30.0245 (15)0.0416 (17)0.0572 (19)0.0005 (13)−0.0128 (14)−0.0143 (15)
C40.0314 (16)0.0246 (13)0.0334 (14)0.0030 (11)−0.0005 (12)−0.0012 (12)
C50.0419 (18)0.0313 (15)0.0444 (16)−0.0016 (13)−0.0073 (14)−0.0162 (13)
C60.0284 (15)0.0361 (15)0.0440 (16)−0.0022 (12)−0.0107 (13)−0.0149 (13)
C70.0252 (14)0.0247 (13)0.0373 (14)−0.0033 (11)−0.0074 (12)−0.0061 (12)
C80.0299 (15)0.0236 (13)0.0380 (15)0.0003 (11)−0.0072 (12)−0.0080 (12)
C90.0347 (16)0.0298 (14)0.0351 (15)−0.0009 (12)0.0019 (12)−0.0078 (12)
C100.0341 (16)0.0254 (14)0.0486 (17)0.0035 (12)−0.0003 (13)−0.0172 (13)
C110.0313 (15)0.0215 (13)0.0414 (15)−0.0003 (11)−0.0100 (12)−0.0104 (12)
C120.0378 (16)0.0288 (14)0.0343 (15)0.0023 (12)−0.0025 (13)−0.0044 (12)
C130.0377 (17)0.0283 (14)0.0440 (17)0.0081 (12)−0.0015 (13)−0.0112 (13)
C140.0296 (15)0.0248 (13)0.0421 (16)0.0007 (11)−0.0047 (12)−0.0084 (13)
C150.0280 (15)0.0281 (14)0.0558 (18)0.0033 (12)−0.0069 (13)−0.0125 (14)
C160.0296 (14)0.0203 (13)0.0385 (14)0.0036 (11)−0.0100 (12)−0.0076 (11)
C170.0298 (15)0.0220 (13)0.0315 (13)0.0013 (11)−0.0093 (11)−0.0051 (11)
C180.0297 (15)0.0196 (13)0.0366 (14)0.0027 (11)−0.0086 (12)−0.0056 (11)
C190.0293 (15)0.0236 (13)0.0378 (15)0.0043 (11)−0.0062 (12)−0.0091 (12)
C200.0275 (15)0.0218 (13)0.0384 (14)0.0050 (11)−0.0124 (12)−0.0098 (12)
C210.0292 (16)0.0205 (13)0.0578 (18)0.0000 (11)−0.0088 (14)−0.0046 (13)
C220.0243 (15)0.0273 (15)0.065 (2)0.0028 (12)−0.0099 (14)−0.0092 (14)
C230.0355 (16)0.0207 (13)0.0325 (14)0.0049 (11)−0.0063 (12)−0.0058 (11)
C240.0320 (16)0.0210 (13)0.0423 (15)0.0006 (11)−0.0040 (12)−0.0062 (12)
C250.0360 (16)0.0260 (14)0.0393 (15)0.0028 (12)−0.0004 (13)−0.0042 (13)
C260.0301 (16)0.0286 (15)0.0543 (18)0.0039 (12)−0.0087 (14)−0.0123 (14)
C270.0502 (19)0.0229 (14)0.0338 (15)0.0068 (13)−0.0050 (13)−0.0053 (12)
C280.0371 (16)0.0234 (14)0.0365 (15)0.0039 (12)0.0016 (13)−0.0064 (12)
C290.0393 (18)0.0307 (16)0.074 (2)−0.0037 (13)−0.0025 (17)−0.0153 (16)
C300.088 (3)0.074 (3)0.079 (3)−0.038 (3)−0.003 (3)−0.006 (2)
N10.0310 (13)0.0212 (11)0.0551 (15)0.0002 (10)−0.0009 (11)−0.0092 (11)
N20.0316 (13)0.0190 (11)0.0361 (12)0.0060 (9)−0.0057 (10)−0.0046 (10)
N30.0279 (12)0.0234 (11)0.0384 (12)0.0072 (9)−0.0133 (10)−0.0096 (10)
O10.0242 (10)0.0338 (10)0.0353 (10)0.0003 (8)−0.0091 (8)−0.0073 (8)
O20.0320 (11)0.0685 (15)0.0625 (14)0.0049 (11)−0.0154 (10)−0.0441 (13)
O30.0400 (12)0.0256 (10)0.0474 (12)0.0098 (9)0.0040 (10)−0.0032 (9)
O40.0358 (11)0.0200 (9)0.0412 (10)0.0031 (8)−0.0084 (9)−0.0097 (8)
O50.0719 (16)0.0305 (11)0.0384 (12)0.0122 (11)−0.0074 (11)−0.0107 (10)
O60.0259 (10)0.0200 (9)0.0609 (13)0.0017 (8)−0.0084 (9)−0.0030 (9)
O70.0287 (10)0.0183 (9)0.0529 (12)0.0031 (8)−0.0060 (9)−0.0054 (9)
O80.0239 (11)0.0249 (10)0.0624 (13)0.0040 (8)−0.0038 (10)−0.0069 (10)
O1W0.0312 (10)0.0279 (10)0.0402 (10)−0.0021 (8)−0.0123 (9)−0.0095 (9)
O2W0.0382 (12)0.0347 (11)0.0350 (10)−0.0016 (9)−0.0046 (9)−0.0067 (9)

Geometric parameters (Å, °)

Ni1—O62.0039 (19)C17—C181.455 (3)
Ni1—O72.022 (2)C18—C191.396 (4)
Ni1—O4i2.0663 (19)C18—C211.397 (4)
Ni1—O12.077 (2)C19—N11.404 (4)
Ni1—O1W2.0786 (19)C19—C241.410 (4)
Ni1—O2W2.079 (2)C20—O81.246 (3)
F1—C221.363 (3)C20—O71.257 (3)
C1—C21.382 (4)C21—C221.347 (4)
C1—C61.384 (4)C21—H21A0.9300
C1—C71.496 (4)C22—C231.406 (4)
C2—C31.381 (4)C23—C241.387 (4)
C2—H2A0.9300C23—N21.400 (3)
C3—C41.372 (4)C24—H24A0.9300
C3—H3A0.9300C25—N21.473 (3)
C4—C51.373 (4)C25—C261.516 (4)
C4—O31.398 (3)C25—H25A0.9700
C5—C61.377 (4)C25—H25B0.9700
C5—H5A0.9300C26—N31.477 (4)
C6—H6A0.9300C26—H26A0.9700
C7—O21.257 (3)C26—H26B0.9700
C7—O11.259 (3)C27—N31.490 (3)
C8—O31.381 (3)C27—C281.526 (4)
C8—C131.381 (4)C27—H27A0.9700
C8—C91.381 (4)C27—H27B0.9700
C9—C101.382 (4)C28—N21.447 (4)
C9—H9AA0.9300C28—H28A0.9700
C10—C111.393 (4)C28—H28B0.9700
C10—H10A0.9300C29—C301.446 (6)
C11—C121.379 (4)C29—N11.492 (4)
C11—C141.488 (4)C29—H29A0.9700
C12—C131.379 (4)C29—H29B0.9700
C12—H12A0.9300C30—H30A0.9600
C13—H13A0.9300C30—H30B0.9600
C14—O51.253 (4)C30—H30C0.9600
C14—O41.273 (3)N3—H3B0.9000
C15—N11.345 (4)N3—H3C0.9000
C15—C161.368 (4)O4—Ni1ii2.0663 (19)
C15—H15A0.9300O1W—H10.8500
C16—C171.428 (4)O1W—H20.8501
C16—C201.515 (3)O2W—H30.8500
C17—O61.255 (3)O2W—H40.8499
O6—Ni1—O789.94 (8)O8—C20—C16117.4 (2)
O6—Ni1—O4i173.89 (8)O7—C20—C16120.1 (2)
O7—Ni1—O4i95.85 (8)C22—C21—C18120.3 (3)
O6—Ni1—O184.98 (8)C22—C21—H21A119.9
O7—Ni1—O1173.98 (7)C18—C21—H21A119.9
O4i—Ni1—O189.13 (8)C21—C22—F1118.1 (3)
O6—Ni1—O1W90.05 (8)C21—C22—C23124.1 (3)
O7—Ni1—O1W90.44 (8)F1—C22—C23117.8 (2)
O4i—Ni1—O1W87.94 (8)C24—C23—N2124.1 (3)
O1—Ni1—O1W86.35 (8)C24—C23—C22115.7 (2)
O6—Ni1—O2W89.40 (9)N2—C23—C22120.1 (3)
O7—Ni1—O2W92.15 (9)C23—C24—C19121.3 (3)
O4i—Ni1—O2W92.34 (8)C23—C24—H24A119.3
O1—Ni1—O2W91.02 (8)C19—C24—H24A119.3
O1W—Ni1—O2W177.35 (7)N2—C25—C26110.2 (2)
C2—C1—C6119.0 (2)N2—C25—H25A109.6
C2—C1—C7122.3 (2)C26—C25—H25A109.6
C6—C1—C7118.6 (2)N2—C25—H25B109.6
C3—C2—C1120.8 (3)C26—C25—H25B109.6
C3—C2—H2A119.6H25A—C25—H25B108.1
C1—C2—H2A119.6N3—C26—C25109.2 (2)
C2—C3—C4118.9 (3)N3—C26—H26A109.8
C2—C3—H3A120.5C25—C26—H26A109.8
C4—C3—H3A120.5N3—C26—H26B109.8
C5—C4—C3121.3 (3)C25—C26—H26B109.8
C5—C4—O3119.9 (3)H26A—C26—H26B108.3
C3—C4—O3118.8 (3)N3—C27—C28110.7 (2)
C4—C5—C6119.3 (3)N3—C27—H27A109.5
C4—C5—H5A120.3C28—C27—H27A109.5
C6—C5—H5A120.3N3—C27—H27B109.5
C5—C6—C1120.6 (3)C28—C27—H27B109.5
C5—C6—H6A119.7H27A—C27—H27B108.1
C1—C6—H6A119.7N2—C28—C27110.0 (2)
O2—C7—O1123.9 (2)N2—C28—H28A109.7
O2—C7—C1119.1 (2)C27—C28—H28A109.7
O1—C7—C1116.9 (2)N2—C28—H28B109.7
O3—C8—C13123.3 (2)C27—C28—H28B109.7
O3—C8—C9116.5 (2)H28A—C28—H28B108.2
C13—C8—C9120.3 (3)C30—C29—N1114.9 (3)
C8—C9—C10119.8 (3)C30—C29—H29A108.5
C8—C9—H9AA120.1N1—C29—H29A108.5
C10—C9—H9AA120.1C30—C29—H29B108.5
C9—C10—C11120.8 (2)N1—C29—H29B108.5
C9—C10—H10A119.6H29A—C29—H29B107.5
C11—C10—H10A119.6C29—C30—H30A109.5
C12—C11—C10118.0 (3)C29—C30—H30B109.5
C12—C11—C14119.1 (3)H30A—C30—H30B109.5
C10—C11—C14122.9 (2)C29—C30—H30C109.5
C13—C12—C11122.0 (3)H30A—C30—H30C109.5
C13—C12—H12A119.0H30B—C30—H30C109.5
C11—C12—H12A119.0C15—N1—C19119.0 (2)
C12—C13—C8119.2 (3)C15—N1—C29119.4 (3)
C12—C13—H13A120.4C19—N1—C29121.5 (2)
C8—C13—H13A120.4C23—N2—C28117.2 (2)
O5—C14—O4124.8 (3)C23—N2—C25115.8 (2)
O5—C14—C11117.4 (2)C28—N2—C25110.8 (2)
O4—C14—C11117.9 (2)C26—N3—C27110.1 (2)
N1—C15—C16126.1 (3)C26—N3—H3B109.6
N1—C15—H15A116.9C27—N3—H3B109.6
C16—C15—H15A116.9C26—N3—H3C109.6
C15—C16—C17118.2 (2)C27—N3—H3C109.6
C15—C16—C20117.5 (2)H3B—N3—H3C108.2
C17—C16—C20124.4 (2)C7—O1—Ni1126.74 (17)
O6—C17—C16126.2 (2)C8—O3—C4116.6 (2)
O6—C17—C18118.1 (2)C14—O4—Ni1ii124.49 (18)
C16—C17—C18115.7 (2)C17—O6—Ni1126.84 (18)
C19—C18—C21117.9 (2)C20—O7—Ni1130.58 (17)
C19—C18—C17122.9 (2)Ni1—O1W—H1118.9
C21—C18—C17119.2 (2)Ni1—O1W—H2123.4
C18—C19—N1117.8 (2)H1—O1W—H290.7
C18—C19—C24120.6 (3)Ni1—O2W—H3102.1
N1—C19—C24121.6 (3)Ni1—O2W—H496.0
O8—C20—O7122.5 (2)H3—O2W—H499.5

Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2W—H4···O20.851.932.695 (3)149
O2W—H4···O10.852.552.965 (3)111
N3—H3B···O2iii0.901.822.714 (3)170
N3—H3C···O8ii0.901.852.719 (3)162
O1W—H1···O1iv0.852.032.761 (3)144
O1W—H2···O4v0.851.992.834 (3)173
O2W—H3···O5i0.851.822.615 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2047).

References

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  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
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