Tris(1,10-phenanthroline-κN,N')nickel(II) bis-(2,4,5-tricarb-oxy-benzo-ate) monohydrate.

In the title compound, [Ni(C(12)H(8)N(2))(3)](C(10)H(5)O(8))(2)·H(2)O, the Ni(II) cation is coordinated by six N atoms of the three bidentate chelating 1,10-phenanthroline ligands in a slightly distorted octa-hedral coordination geometry. The Ni-N bond lengths range from 2.074 (2) to 2.094 (2) Å. The dihedral angles between the three chelating NCCN groups to each other are 85.71 (3), 73.75 (2) and 85.71 (3)°, respectively. The Ni cation, the phenyl ring of the 1,10-phenanthroline ligand and the lattice water molecule are located on special positions (site symmetry 2). In the crystal, the uncoordinated 2,4,5-tricarb-oxy-benzeno-ate anions join with each other through O-H⋯O hydrogen bonds, forming a two-dimensional hydrogen-bonded layer structure along the bc plane. The layers are further linked via additional O-H⋯O inter-actions between water and carboxyl groups, resulting in a three-dimensional supra-molecular network.

Related literature

For structures of complexes with six-coordinate nickel atoms and background references, see: Li et al. (2003 ▶); Fu et al. (2004 ▶); Fabelo et al. (2008 ▶); Zhong et al. (2009 ▶); Ni et al. (2010 ▶). For background to phenanthroline complexes, see: Wang & Zhong (2011 ▶); Zhu et al. (2006 ▶); Cui et al. (2010 ▶); Zhong (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

[Ni(C12H8N2)3](C10H5O8)2·H2O

M = 1123.62

Monoclinic,

a = 24.2009 (11) Å

b = 14.1546 (5) Å

c = 15.8347 (7) Å

β = 116.271 (5)°

V = 4864.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 295 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009 ▶) T min = 0.829, T max = 0.868

12270 measured reflections

4977 independent reflections

3050 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.054

S = 1.02

4977 reflections

369 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048914/bq2318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048914/bq2318Isup2.hkl

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

[Ni(C12H8N2)3](C10H5O8)2·H2O	F(000) = 2312
Mr = 1123.62	Dx = 1.534 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4069 reflections
a = 24.2009 (11) Å	θ = 2.8–29.2°
b = 14.1546 (5) Å	µ = 0.49 mm−1
c = 15.8347 (7) Å	T = 295 K
β = 116.271 (5)°	Block, orange
V = 4864.0 (4) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4977 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3050 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 15.9149 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −30→29
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009)	k = −14→17
Tmin = 0.829, Tmax = 0.868	l = −14→19
12270 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0092P)2] where P = (Fo2 + 2Fc2)/3
4977 reflections	(Δ/σ)max < 0.001
369 parameters	Δρmax = 0.52 e Å−3
3 restraints	Δρmin = −0.42 e Å−3

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	1.0000	0.31042 (3)	0.7500	0.03040 (12)
N1	1.02407 (7)	0.21222 (12)	0.67422 (11)	0.0312 (5)
N2	0.91737 (7)	0.30145 (13)	0.62879 (11)	0.0326 (4)
N3	0.97131 (7)	0.42419 (13)	0.80545 (10)	0.0318 (5)
O1	0.68321 (7)	0.46426 (12)	0.52192 (11)	0.0511 (4)
H5	0.7152	0.4948	0.5473	0.077*
O1W	0.5000	0.5789 (3)	0.2500	0.1201 (14)
H1WA	0.4734 (13)	0.541 (2)	0.223 (3)	0.169 (19)*
O2	0.59675 (7)	0.46988 (12)	0.39080 (11)	0.0560 (5)
O3	0.70784 (6)	0.44147 (11)	0.35063 (10)	0.0452 (4)
O4	0.74751 (8)	0.53534 (11)	0.27810 (12)	0.0556 (5)
H4	0.7555	0.4850	0.2603	0.083*
O5	0.73100 (7)	0.86793 (11)	0.28224 (11)	0.0593 (5)
O6	0.71141 (6)	0.94807 (11)	0.38534 (10)	0.0459 (4)
O7	0.64163 (8)	0.93250 (12)	0.45856 (13)	0.0661 (5)
H7	0.6652	0.9388	0.4344	0.099*
O8	0.60196 (8)	0.81822 (13)	0.50512 (13)	0.0807 (6)
C1	1.07715 (9)	0.16650 (16)	0.69809 (14)	0.0398 (6)
H1	1.1077	0.1718	0.7597	0.048*
C2	1.08895 (10)	0.11114 (17)	0.63505 (17)	0.0456 (6)
H2	1.1267	0.0809	0.6543	0.055*
C3	1.04430 (10)	0.10193 (16)	0.54458 (17)	0.0424 (6)
H3	1.0517	0.0658	0.5016	0.051*
C4	0.98738 (9)	0.14703 (15)	0.51668 (15)	0.0344 (6)
C5	0.93748 (11)	0.13995 (16)	0.42380 (15)	0.0437 (6)
H9	0.9429	0.1063	0.3775	0.052*
C6	0.88307 (10)	0.18152 (17)	0.40309 (14)	0.0456 (6)
H8	0.8508	0.1735	0.3433	0.055*
C7	0.87341 (10)	0.23763 (16)	0.47020 (14)	0.0347 (6)
C8	0.81794 (10)	0.28303 (17)	0.45171 (15)	0.0481 (7)
H10	0.7846	0.2781	0.3925	0.058*
C9	0.81285 (10)	0.33462 (17)	0.52063 (17)	0.0483 (7)
H11	0.7759	0.3641	0.5093	0.058*
C10	0.86370 (10)	0.34262 (16)	0.60827 (15)	0.0416 (6)
H12	0.8598	0.3785	0.6545	0.050*
C11	0.92208 (9)	0.24801 (15)	0.56050 (14)	0.0284 (5)
C12	0.97938 (8)	0.20154 (15)	0.58436 (13)	0.0287 (5)
C13	0.94314 (9)	0.42376 (17)	0.86098 (14)	0.0423 (6)
H13	0.9339	0.3659	0.8795	0.051*
C14	0.92679 (10)	0.50594 (19)	0.89267 (17)	0.0535 (7)
H14	0.9068	0.5024	0.9311	0.064*
C15	0.94016 (10)	0.59170 (18)	0.86711 (16)	0.0543 (7)
H15	0.9296	0.6470	0.8882	0.065*
C16	0.97025 (9)	0.59569 (17)	0.80814 (15)	0.0383 (6)
C17	0.98481 (8)	0.50971 (16)	0.77988 (13)	0.0288 (5)
C18	0.98564 (9)	0.68215 (17)	0.77834 (14)	0.0504 (7)
H18	0.9760	0.7392	0.7978	0.061*
C19	0.66694 (8)	0.59686 (16)	0.41710 (14)	0.0303 (5)
C20	0.64826 (8)	0.67726 (16)	0.44598 (14)	0.0365 (6)
H20	0.6259	0.6701	0.4805	0.044*
C21	0.66067 (9)	0.76847 (16)	0.42678 (14)	0.0302 (5)
C22	0.69433 (8)	0.77913 (15)	0.37392 (13)	0.0273 (5)
C23	0.71376 (8)	0.69725 (17)	0.34589 (12)	0.0280 (5)
H23	0.7367	0.7037	0.3122	0.034*
C24	0.70075 (8)	0.60660 (16)	0.36553 (13)	0.0270 (5)
C25	0.71945 (9)	0.51885 (18)	0.33192 (14)	0.0325 (6)
C26	0.64675 (11)	0.50354 (17)	0.44011 (17)	0.0394 (6)
C27	0.63255 (10)	0.84283 (18)	0.46660 (17)	0.0454 (6)
C28	0.71315 (9)	0.87133 (16)	0.34430 (16)	0.0351 (6)

	U11	U22	U33	U12	U13	U23
Ni1	0.0374 (2)	0.0251 (3)	0.0303 (2)	0.000	0.01641 (19)	0.000
N1	0.0359 (10)	0.0267 (13)	0.0322 (10)	0.0028 (9)	0.0161 (9)	0.0017 (9)
N2	0.0349 (10)	0.0291 (12)	0.0354 (10)	0.0031 (9)	0.0171 (9)	0.0028 (10)
N3	0.0416 (10)	0.0303 (13)	0.0327 (10)	−0.0019 (9)	0.0248 (9)	0.0017 (10)
O1	0.0665 (11)	0.0350 (12)	0.0542 (10)	−0.0138 (9)	0.0289 (10)	0.0063 (10)
O1W	0.112 (3)	0.062 (3)	0.127 (3)	0.000	−0.001 (3)	0.000
O2	0.0499 (10)	0.0400 (12)	0.0752 (12)	−0.0150 (9)	0.0251 (10)	0.0019 (11)
O3	0.0644 (10)	0.0244 (10)	0.0554 (10)	0.0035 (9)	0.0343 (9)	0.0033 (9)
O4	0.0908 (12)	0.0336 (11)	0.0732 (12)	0.0046 (10)	0.0643 (10)	−0.0030 (10)
O5	0.1064 (13)	0.0326 (11)	0.0727 (11)	−0.0077 (10)	0.0704 (11)	0.0013 (10)
O6	0.0653 (10)	0.0225 (9)	0.0604 (10)	−0.0061 (8)	0.0373 (9)	−0.0044 (9)
O7	0.0981 (14)	0.0290 (12)	0.1078 (15)	0.0010 (11)	0.0788 (12)	−0.0063 (12)
O8	0.1316 (15)	0.0434 (13)	0.1301 (16)	−0.0002 (12)	0.1151 (14)	−0.0050 (13)
C1	0.0394 (13)	0.0362 (17)	0.0406 (13)	0.0039 (12)	0.0147 (12)	−0.0007 (13)
C2	0.0487 (15)	0.0356 (17)	0.0616 (16)	0.0055 (13)	0.0327 (14)	−0.0006 (15)
C3	0.0641 (16)	0.0268 (15)	0.0555 (16)	−0.0045 (13)	0.0438 (15)	−0.0063 (14)
C4	0.0463 (14)	0.0269 (15)	0.0367 (13)	−0.0076 (11)	0.0246 (13)	−0.0005 (12)
C5	0.0723 (17)	0.0308 (16)	0.0377 (14)	−0.0149 (14)	0.0331 (15)	−0.0078 (13)
C6	0.0570 (15)	0.0426 (18)	0.0281 (12)	−0.0147 (14)	0.0106 (12)	−0.0014 (14)
C7	0.0457 (14)	0.0275 (15)	0.0303 (13)	−0.0064 (12)	0.0163 (12)	0.0056 (12)
C8	0.0427 (15)	0.046 (2)	0.0409 (14)	−0.0040 (13)	0.0051 (12)	0.0069 (14)
C9	0.0388 (14)	0.0433 (19)	0.0552 (15)	0.0050 (12)	0.0141 (14)	0.0066 (15)
C10	0.0451 (14)	0.0346 (17)	0.0469 (15)	0.0052 (12)	0.0220 (13)	0.0028 (13)
C11	0.0390 (13)	0.0206 (14)	0.0283 (12)	−0.0020 (10)	0.0175 (11)	0.0025 (11)
C12	0.0374 (12)	0.0224 (14)	0.0297 (12)	−0.0040 (11)	0.0180 (11)	0.0014 (11)
C13	0.0556 (14)	0.0351 (17)	0.0463 (14)	−0.0044 (13)	0.0318 (13)	0.0006 (14)
C14	0.0743 (17)	0.046 (2)	0.0668 (17)	0.0042 (15)	0.0549 (15)	−0.0026 (17)
C15	0.0809 (17)	0.0329 (17)	0.0708 (17)	0.0069 (15)	0.0533 (16)	−0.0060 (16)
C16	0.0501 (14)	0.0302 (16)	0.0444 (14)	0.0013 (12)	0.0298 (13)	−0.0029 (13)
C17	0.0332 (13)	0.0258 (14)	0.0302 (13)	−0.0002 (10)	0.0165 (11)	−0.0007 (12)
C18	0.0761 (17)	0.0225 (14)	0.0686 (18)	0.0042 (13)	0.0465 (14)	−0.0031 (15)
C19	0.0350 (12)	0.0241 (14)	0.0345 (13)	−0.0021 (11)	0.0177 (11)	−0.0004 (12)
C20	0.0473 (13)	0.0304 (16)	0.0461 (13)	−0.0033 (12)	0.0338 (12)	−0.0007 (14)
C21	0.0369 (12)	0.0248 (15)	0.0339 (12)	0.0003 (11)	0.0201 (11)	−0.0010 (12)
C22	0.0313 (12)	0.0238 (15)	0.0258 (12)	−0.0019 (10)	0.0117 (10)	0.0007 (11)
C23	0.0308 (11)	0.0329 (15)	0.0235 (11)	−0.0006 (11)	0.0149 (9)	−0.0003 (12)
C24	0.0332 (12)	0.0230 (14)	0.0256 (11)	0.0025 (10)	0.0136 (10)	−0.0012 (11)
C25	0.0355 (13)	0.0333 (16)	0.0285 (13)	0.0013 (12)	0.0140 (11)	−0.0007 (13)
C26	0.0517 (16)	0.0263 (16)	0.0506 (16)	0.0014 (13)	0.0320 (15)	−0.0006 (15)
C27	0.0636 (16)	0.0265 (16)	0.0581 (16)	0.0019 (13)	0.0380 (14)	−0.0019 (15)
C28	0.0419 (13)	0.0239 (14)	0.0392 (14)	0.0008 (11)	0.0176 (12)	0.0037 (11)

Ni1—N2i	2.0740 (15)	C6—C7	1.426 (3)
Ni1—N2	2.0740 (15)	C6—H8	0.9300
Ni1—N1	2.0809 (16)	C7—C8	1.398 (3)
Ni1—N1i	2.0809 (16)	C7—C11	1.401 (2)
Ni1—N3i	2.0943 (17)	C8—C9	1.363 (3)
Ni1—N3	2.0943 (17)	C8—H10	0.9300
N1—C1	1.335 (2)	C9—C10	1.393 (3)
N1—C12	1.362 (2)	C9—H11	0.9300
N2—C10	1.326 (2)	C10—H12	0.9300
N2—C11	1.365 (2)	C11—C12	1.426 (2)
N3—C13	1.330 (2)	C13—C14	1.392 (3)
N3—C17	1.361 (2)	C13—H13	0.9300
O1—C26	1.324 (2)	C14—C15	1.363 (3)
O1—H5	0.8200	C14—H14	0.9300
O1W—H1WA	0.80 (2)	C15—C16	1.417 (3)
O2—C26	1.210 (2)	C15—H15	0.9300
O3—C25	1.200 (2)	C16—C17	1.395 (3)
O4—C25	1.324 (2)	C16—C18	1.419 (3)
O4—H4	0.8200	C17—C17i	1.433 (3)
O5—C28	1.237 (2)	C18—C18i	1.357 (3)
O6—C28	1.276 (2)	C18—H18	0.9300
O7—C27	1.304 (3)	C19—C20	1.375 (3)
O7—H7	0.8200	C19—C24	1.395 (2)
O8—C27	1.200 (2)	C19—C26	1.508 (3)
C1—C2	1.394 (3)	C20—C21	1.389 (3)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.366 (3)	C21—C22	1.411 (2)
C2—H2	0.9300	C21—C27	1.532 (3)
C3—C4	1.400 (3)	C22—C23	1.395 (3)
C3—H3	0.9300	C22—C28	1.523 (3)
C4—C12	1.402 (2)	C23—C24	1.389 (3)
C4—C5	1.435 (3)	C23—H23	0.9300
C5—C6	1.344 (3)	C24—C25	1.498 (3)
C5—H9	0.9300
N2i—Ni1—N2	172.98 (11)	C9—C10—H12	118.5
N2i—Ni1—N1	95.24 (6)	N2—C11—C7	122.64 (18)
N2—Ni1—N1	80.02 (7)	N2—C11—C12	117.26 (18)
N2i—Ni1—N1i	80.02 (7)	C7—C11—C12	120.10 (19)
N2—Ni1—N1i	95.24 (6)	N1—C12—C4	123.05 (18)
N1—Ni1—N1i	96.17 (9)	N1—C12—C11	117.05 (18)
N2i—Ni1—N3i	94.15 (6)	C4—C12—C11	119.90 (18)
N2—Ni1—N3i	91.25 (6)	N3—C13—C14	123.0 (2)
N1—Ni1—N3i	92.43 (6)	N3—C13—H13	118.5
N1i—Ni1—N3i	170.00 (7)	C14—C13—H13	118.5
N2i—Ni1—N3	91.25 (6)	C15—C14—C13	119.6 (2)
N2—Ni1—N3	94.15 (6)	C15—C14—H14	120.2
N1—Ni1—N3	170.00 (7)	C13—C14—H14	120.2
N1i—Ni1—N3	92.44 (6)	C14—C15—C16	119.3 (2)
N3i—Ni1—N3	79.49 (9)	C14—C15—H15	120.3
C1—N1—C12	117.49 (17)	C16—C15—H15	120.3
C1—N1—Ni1	129.83 (14)	C17—C16—C15	117.0 (2)
C12—N1—Ni1	112.40 (13)	C17—C16—C18	120.33 (19)
C10—N2—C11	117.75 (17)	C15—C16—C18	122.7 (2)
C10—N2—Ni1	129.68 (15)	N3—C17—C16	123.54 (18)
C11—N2—Ni1	112.50 (12)	N3—C17—C17i	117.22 (11)
C13—N3—C17	117.48 (19)	C16—C17—C17i	119.24 (13)
C13—N3—Ni1	129.48 (16)	C18i—C18—C16	120.44 (12)
C17—N3—Ni1	113.03 (12)	C18i—C18—H18	119.8
C26—O1—H5	109.5	C16—C18—H18	119.8
C25—O4—H4	109.5	C20—C19—C24	118.5 (2)
C27—O7—H7	109.5	C20—C19—C26	117.07 (18)
N1—C1—C2	123.10 (19)	C24—C19—C26	124.4 (2)
N1—C1—H1	118.5	C19—C20—C21	124.15 (19)
C2—C1—H1	118.5	C19—C20—H20	117.9
C3—C2—C1	119.1 (2)	C21—C20—H20	117.9
C3—C2—H2	120.4	C20—C21—C22	117.8 (2)
C1—C2—H2	120.4	C20—C21—C27	111.71 (17)
C2—C3—C4	119.9 (2)	C22—C21—C27	130.5 (2)
C2—C3—H3	120.1	C23—C22—C21	117.7 (2)
C4—C3—H3	120.1	C23—C22—C28	115.15 (18)
C3—C4—C12	117.33 (19)	C21—C22—C28	127.2 (2)
C3—C4—C5	123.7 (2)	C24—C23—C22	123.67 (17)
C12—C4—C5	118.92 (19)	C24—C23—H23	118.2
C6—C5—C4	120.6 (2)	C22—C23—H23	118.2
C6—C5—H9	119.7	C23—C24—C19	118.2 (2)
C4—C5—H9	119.7	C23—C24—C25	123.52 (19)
C5—C6—C7	121.9 (2)	C19—C24—C25	118.3 (2)
C5—C6—H8	119.1	O3—C25—O4	124.2 (2)
C7—C6—H8	119.1	O3—C25—C24	121.9 (2)
C8—C7—C11	117.5 (2)	O4—C25—C24	113.8 (2)
C8—C7—C6	124.0 (2)	O2—C26—O1	120.6 (2)
C11—C7—C6	118.55 (19)	O2—C26—C19	121.8 (2)
C9—C8—C7	119.8 (2)	O1—C26—C19	117.2 (2)
C9—C8—H10	120.1	O8—C27—O7	120.0 (2)
C7—C8—H10	120.1	O8—C27—C21	119.7 (2)
C8—C9—C10	119.2 (2)	O7—C27—C21	120.2 (2)
C8—C9—H11	120.4	O5—C28—O6	122.7 (2)
C10—C9—H11	120.4	O5—C28—C22	117.9 (2)
N2—C10—C9	123.1 (2)	O6—C28—C22	119.40 (19)
N2—C10—H12	118.5
N2i—Ni1—N1—C1	−3.79 (18)	Ni1—N1—C12—C11	−7.6 (2)
N2—Ni1—N1—C1	−178.55 (18)	C3—C4—C12—N1	0.2 (3)
N1i—Ni1—N1—C1	−84.29 (18)	C5—C4—C12—N1	179.90 (19)
N3i—Ni1—N1—C1	90.60 (18)	C3—C4—C12—C11	−179.05 (18)
N3—Ni1—N1—C1	126.5 (4)	C5—C4—C12—C11	0.6 (3)
N2i—Ni1—N1—C12	−177.45 (13)	N2—C11—C12—N1	1.8 (3)
N2—Ni1—N1—C12	7.79 (13)	C7—C11—C12—N1	−177.96 (19)
N1i—Ni1—N1—C12	102.05 (14)	N2—C11—C12—C4	−178.87 (17)
N3i—Ni1—N1—C12	−83.05 (13)	C7—C11—C12—C4	1.3 (3)
N3—Ni1—N1—C12	−47.1 (4)	C17—N3—C13—C14	0.6 (3)
N2i—Ni1—N2—C10	128.53 (18)	Ni1—N3—C13—C14	179.91 (17)
N1—Ni1—N2—C10	176.55 (19)	N3—C13—C14—C15	−0.5 (4)
N1i—Ni1—N2—C10	81.19 (18)	C13—C14—C15—C16	0.4 (4)
N3i—Ni1—N2—C10	−91.19 (18)	C14—C15—C16—C17	−0.3 (3)
N3—Ni1—N2—C10	−11.64 (19)	C14—C15—C16—C18	179.9 (2)
N2i—Ni1—N2—C11	−54.87 (13)	C13—N3—C17—C16	−0.5 (3)
N1—Ni1—N2—C11	−6.84 (13)	Ni1—N3—C17—C16	180.00 (16)
N1i—Ni1—N2—C11	−102.20 (13)	C13—N3—C17—C17i	179.96 (18)
N3i—Ni1—N2—C11	85.41 (14)	Ni1—N3—C17—C17i	0.5 (3)
N3—Ni1—N2—C11	164.96 (13)	C15—C16—C17—N3	0.4 (3)
N2i—Ni1—N3—C13	−85.57 (16)	C18—C16—C17—N3	−179.79 (19)
N2—Ni1—N3—C13	89.94 (16)	C15—C16—C17—C17i	179.9 (2)
N1—Ni1—N3—C13	143.9 (3)	C18—C16—C17—C17i	−0.3 (4)
N1i—Ni1—N3—C13	−5.50 (16)	C17—C16—C18—C18i	0.4 (4)
N3i—Ni1—N3—C13	−179.55 (19)	C15—C16—C18—C18i	−179.9 (2)
N2i—Ni1—N3—C17	93.81 (14)	C24—C19—C20—C21	0.3 (3)
N2—Ni1—N3—C17	−90.68 (14)	C26—C19—C20—C21	−177.1 (2)
N1—Ni1—N3—C17	−36.8 (4)	C19—C20—C21—C22	0.3 (3)
N1i—Ni1—N3—C17	173.87 (14)	C19—C20—C21—C27	178.78 (19)
N3i—Ni1—N3—C17	−0.18 (10)	C20—C21—C22—C23	−1.1 (3)
C12—N1—C1—C2	1.6 (3)	C27—C21—C22—C23	−179.2 (2)
Ni1—N1—C1—C2	−171.78 (16)	C20—C21—C22—C28	179.9 (2)
N1—C1—C2—C3	−0.6 (3)	C27—C21—C22—C28	1.7 (3)
C1—C2—C3—C4	−0.7 (3)	C21—C22—C23—C24	1.3 (3)
C2—C3—C4—C12	0.8 (3)	C28—C22—C23—C24	−179.49 (18)
C2—C3—C4—C5	−178.8 (2)	C22—C23—C24—C19	−0.8 (3)
C3—C4—C5—C6	176.8 (2)	C22—C23—C24—C25	177.38 (18)
C12—C4—C5—C6	−2.8 (3)	C20—C19—C24—C23	−0.1 (3)
C4—C5—C6—C7	3.0 (3)	C26—C19—C24—C23	177.1 (2)
C5—C6—C7—C8	179.3 (2)	C20—C19—C24—C25	−178.30 (19)
C5—C6—C7—C11	−1.0 (3)	C26—C19—C24—C25	−1.2 (3)
C11—C7—C8—C9	−0.2 (3)	C23—C24—C25—O3	179.5 (2)
C6—C7—C8—C9	179.5 (2)	C19—C24—C25—O3	−2.4 (3)
C7—C8—C9—C10	1.2 (3)	C23—C24—C25—O4	−2.7 (3)
C11—N2—C10—C9	−0.8 (3)	C19—C24—C25—O4	175.48 (17)
Ni1—N2—C10—C9	175.62 (17)	C20—C19—C26—O2	83.8 (3)
C8—C9—C10—N2	−0.6 (3)	C24—C19—C26—O2	−93.4 (3)
C10—N2—C11—C7	1.8 (3)	C20—C19—C26—O1	−89.2 (2)
Ni1—N2—C11—C7	−175.25 (16)	C24—C19—C26—O1	93.6 (2)
C10—N2—C11—C12	−177.99 (18)	C20—C21—C27—O8	−2.9 (3)
Ni1—N2—C11—C12	5.0 (2)	C22—C21—C27—O8	175.3 (2)
C8—C7—C11—N2	−1.3 (3)	C20—C21—C27—O7	177.2 (2)
C6—C7—C11—N2	179.00 (18)	C22—C21—C27—O7	−4.5 (4)
C8—C7—C11—C12	178.51 (18)	C23—C22—C28—O5	15.8 (3)
C6—C7—C11—C12	−1.2 (3)	C21—C22—C28—O5	−165.12 (18)
C1—N1—C12—C4	−1.4 (3)	C23—C22—C28—O6	−162.56 (18)
Ni1—N1—C12—C4	173.10 (15)	C21—C22—C28—O6	16.5 (3)
C1—N1—C12—C11	177.87 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ii	0.82	1.87	2.690 (2)	177.
O1—H5···O6iii	0.82	1.81	2.624 (2)	173.
O7—H7···O6	0.82	1.63	2.4450 (19)	178.
O1W—H1WA···O2iv	0.80 (2)	2.10 (3)	2.866 (3)	158 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.82	1.87	2.690 (2)	177
O1—H5⋯O6ii	0.82	1.81	2.624 (2)	173
O7—H7⋯O6	0.82	1.63	2.4450 (19)	178
O1W—H1WA⋯O2iii	0.80 (2)	2.10 (3)	2.866 (3)	158 (4)

Symmetry codes: (i) ; (ii) ; (iii) .