catena-Poly[[diaqua-[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ato-κO,O']nickel(II)]-μ-4,4'-oxydibenzoato-κO:O'].

In the title compound, [Ni(C(16)H(18)FN(3)O(3))(C(14)H(8)O(5))(H(2)O)(2)](n), the Ni(II) atom exhibits a distorted octa-hedral geometry that is defined by four O atoms and two water mol-ecules. 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-H⋯O hydrogen bonding to form a three-dimensional supra-molecular network.

Related literature

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

Experimental

Crystal data

[Ni(C16H18FN3O3)(C14H8O5)(H2O)2]

M = 670.28

Triclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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.

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

[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

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) ; (v) .