Aqua-(1,10-phenanthroline)(pyridine-2,6-dicarboxyl-ato)nickel(II) pyridine-2,6-di-carboxylic acid solvate tetra-hydrate.

The title compound, [Ni(C(7)H(3)NO(4))(C(12)H(8)N(2))(H(2)O)]·C(7)H(5)NO(4)·4H(2)O or [Ni(pydc)(phen)(H(2)O)].pydcH(2)·4H(2)O, was obtained by the reaction of nickel(II) nitrate hexa-hydrate with the proton-transfer compound (phenH)(2)(pydc) (phen is 1,10-phenanothroline and pydcH(2) is pyridine-2,6-dicarboxylic acid) in aqueous solution. Both the cationic and anionic portions of the starting proton-transfer compound are involved in the complexation. The Ni(II) atom has a distorted octa-hedral geometry and is hexa-coordinated by three O atoms and three N atoms from one phen fragment (as a bidentate ligand), one (pydc)(2-) unit (as a tridentate ligand) and one water mol-ecule. In the crystal structure, extensive O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds with D⋯A distances ranging from 2.573 (2) to 3.385 (2) Å, π-π inter-actions between the phen ring systems [with centroid-centroid distances of 3.4694 (12), 3.4781 (11) and 3.8310 (11) Å] and inter-molecular C-O⋯π inter-actions [C⋯π distances of 3.4812 (17), 3.5784 (16) and 3.5926 (16) Å] connect the various components together.

Related literature

For proton-transfer compounds see: Aghabozorg et al. (2007 ▶); Aghabozorg, Manteghi & Sheshmani (2008 ▶); Aghabozorg, Motyeian et al. (2008 ▶); Aharif et al. (2007 ▶). For the isostructural Co complex see: Su et al. (2005 ▶).

Experimental

Crystal data

[Ni(C7H3NO4)(C12H8N2)(H2O)]·C7H5NO4·4H2O

M = 661.22

Triclinic,

a = 9.9454 (7) Å

b = 11.3524 (7) Å

c = 12.7687 (10) Å

α = 76.527 (2)°

β = 81.252 (2)°

γ = 76.131 (2)°

V = 1354.00 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.80 mm−1

T = 100 (2) K

0.41 × 0.32 × 0.26 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.736, T max = 0.820

14769 measured reflections

6485 independent reflections

5910 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.01

6485 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039378/om2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039378/om2263Isup2.hkl

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

[Ni(C7H3NO4)(C12H8N2)(H2O)]·C7H5NO4·4H2O	Z = 2
Mr = 661.22	F(000) = 684
Triclinic, P1	Dx = 1.622 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9454 (7) Å	Cell parameters from 2738 reflections
b = 11.3524 (7) Å	θ = 2.6–34.7°
c = 12.7687 (10) Å	µ = 0.80 mm−1
α = 76.527 (2)°	T = 100 K
β = 81.252 (2)°	Prism, blue
γ = 76.131 (2)°	0.41 × 0.32 × 0.26 mm
V = 1354.00 (17) Å3

Bruker SMART APEXII diffractometer	6485 independent reflections
Radiation source: fine-focus sealed tube	5910 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.736, Tmax = 0.820	k = −14→14
14769 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: mixed
wR(F2) = 0.092	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.04P)2 + 1.76P] where P = (Fo2 + 2Fc2)/3
6485 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.51 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	0.14557 (2)	0.61408 (2)	0.219863 (18)	0.01073 (7)
O1	0.27282 (14)	0.74827 (12)	0.17880 (10)	0.0147 (3)
O2	0.42638 (15)	0.81778 (13)	0.24813 (11)	0.0200 (3)
O3	0.06221 (13)	0.46491 (12)	0.32080 (10)	0.0135 (3)
O4	0.07765 (14)	0.33692 (12)	0.48273 (11)	0.0154 (3)
O5	0.32914 (16)	1.18635 (13)	0.32094 (11)	0.0203 (3)
H5A	0.2927	1.1262	0.3229	0.024*
O6	0.43646 (15)	1.24853 (13)	0.43060 (12)	0.0204 (3)
O7	0.08261 (14)	0.88178 (12)	0.42880 (11)	0.0163 (3)
O8	0.06159 (14)	0.77645 (12)	0.59989 (11)	0.0171 (3)
H8A	0.0140	0.7401	0.5742	0.021*
N1	0.23864 (15)	0.58307 (14)	0.35305 (12)	0.0116 (3)
N2	0.05900 (16)	0.65260 (14)	0.07697 (12)	0.0129 (3)
N3	0.29117 (16)	0.49314 (14)	0.13877 (12)	0.0127 (3)
N4	0.24313 (16)	1.01566 (14)	0.48213 (12)	0.0134 (3)
C1	0.32172 (18)	0.65734 (16)	0.35902 (14)	0.0121 (3)
C2	0.37457 (19)	0.65049 (17)	0.45478 (15)	0.0146 (3)
H2A	0.4327	0.7041	0.4592	0.018*
C3	0.33980 (19)	0.56227 (18)	0.54497 (15)	0.0155 (4)
H3A	0.3740	0.5560	0.6120	0.019*
C4	0.25558 (19)	0.48366 (17)	0.53718 (15)	0.0139 (3)
H4B	0.2330	0.4222	0.5975	0.017*
C5	0.20561 (18)	0.49817 (16)	0.43806 (14)	0.0116 (3)
C6	0.34375 (19)	0.74912 (16)	0.25348 (15)	0.0137 (3)
C7	0.10751 (18)	0.42734 (16)	0.41213 (14)	0.0118 (3)
C8	−0.05952 (19)	0.72987 (17)	0.04897 (15)	0.0152 (3)
H8B	−0.1158	0.7734	0.1008	0.018*
C9	−0.1049 (2)	0.74989 (18)	−0.05366 (15)	0.0172 (4)
H9A	−0.1902	0.8060	−0.0704	0.021*
C10	−0.0251 (2)	0.68771 (18)	−0.12991 (15)	0.0171 (4)
H10A	−0.0540	0.7010	−0.2001	0.021*
C11	0.1005 (2)	0.60376 (18)	−0.10257 (15)	0.0154 (4)
C12	0.1883 (2)	0.53061 (19)	−0.17468 (15)	0.0185 (4)
H12A	0.1647	0.5407	−0.2461	0.022*
C13	0.3046 (2)	0.44706 (19)	−0.14207 (16)	0.0186 (4)
H13A	0.3606	0.3991	−0.1909	0.022*
C14	0.34446 (19)	0.42989 (17)	−0.03512 (15)	0.0150 (3)
C15	0.4619 (2)	0.34293 (17)	0.00459 (16)	0.0175 (4)
H15A	0.5207	0.2914	−0.0402	0.021*
C16	0.4904 (2)	0.33338 (17)	0.10809 (16)	0.0168 (4)
H16A	0.5691	0.2750	0.1357	0.020*
C17	0.40235 (19)	0.41079 (17)	0.17342 (15)	0.0149 (3)
H17A	0.4235	0.4036	0.2450	0.018*
C18	0.26186 (19)	0.50255 (16)	0.03579 (14)	0.0130 (3)
C19	0.13779 (19)	0.58987 (16)	0.00219 (14)	0.0131 (3)
C20	0.32109 (19)	1.08231 (17)	0.50875 (15)	0.0138 (3)
C21	0.3586 (2)	1.06598 (18)	0.61277 (16)	0.0175 (4)
H21A	0.4139	1.1161	0.6285	0.021*
C22	0.3128 (2)	0.97428 (19)	0.69244 (16)	0.0189 (4)
H22A	0.3371	0.9596	0.7642	0.023*
C23	0.2307 (2)	0.90385 (18)	0.66607 (15)	0.0167 (4)
H23A	0.1978	0.8406	0.7194	0.020*
C24	0.19803 (18)	0.92821 (16)	0.56006 (15)	0.0131 (3)
C25	0.36731 (19)	1.17943 (17)	0.41766 (15)	0.0157 (4)
C26	0.10791 (18)	0.86000 (16)	0.52254 (15)	0.0133 (3)
O1W	−0.02250 (14)	0.73999 (12)	0.28080 (11)	0.0162 (3)
H1	−0.0342	0.7339	0.3490	0.024*
H2	−0.0089	0.8098	0.2446	0.024*
O2W	0.20162 (16)	1.03365 (13)	0.25314 (11)	0.0206 (3)
H3	0.2729	0.9812	0.2350	0.031*
H4	0.1654	0.9911	0.3094	0.031*
O3W	0.00061 (15)	0.96907 (14)	0.14753 (12)	0.0238 (3)
H5	0.0484	1.0092	0.1701	0.036*
H6	0.0279	0.9587	0.0833	0.036*
O4W	−0.2328 (2)	1.09864 (16)	0.03141 (15)	0.0428 (5)
H7	−0.2480	1.1528	−0.0263	0.064*
H8	−0.2752	1.0400	0.0390	0.064*
O5W	0.5989 (2)	0.92774 (19)	0.06799 (16)	0.0443 (5)
H9	0.5842	0.8595	0.1070	0.066*
H10	0.5340	0.9780	0.0964	0.066*

	U11	U22	U33	U12	U13	U23
Ni1	0.01194 (12)	0.01138 (12)	0.00901 (11)	−0.00305 (8)	−0.00187 (8)	−0.00123 (8)
O1	0.0164 (6)	0.0140 (6)	0.0136 (6)	−0.0047 (5)	−0.0022 (5)	−0.0008 (5)
O2	0.0198 (7)	0.0206 (7)	0.0217 (7)	−0.0116 (6)	−0.0009 (5)	−0.0020 (6)
O3	0.0145 (6)	0.0154 (6)	0.0113 (6)	−0.0053 (5)	−0.0023 (5)	−0.0013 (5)
O4	0.0178 (6)	0.0146 (6)	0.0139 (6)	−0.0068 (5)	−0.0018 (5)	0.0004 (5)
O5	0.0295 (8)	0.0183 (7)	0.0165 (7)	−0.0131 (6)	−0.0065 (6)	0.0006 (5)
O6	0.0236 (7)	0.0193 (7)	0.0218 (7)	−0.0110 (6)	−0.0049 (6)	−0.0026 (6)
O7	0.0174 (6)	0.0177 (6)	0.0147 (6)	−0.0067 (5)	−0.0028 (5)	−0.0015 (5)
O8	0.0207 (7)	0.0167 (6)	0.0161 (6)	−0.0099 (5)	−0.0029 (5)	−0.0009 (5)
N1	0.0111 (7)	0.0117 (7)	0.0119 (7)	−0.0023 (5)	−0.0011 (5)	−0.0028 (5)
N2	0.0151 (7)	0.0126 (7)	0.0115 (7)	−0.0050 (6)	−0.0021 (6)	−0.0009 (5)
N3	0.0148 (7)	0.0121 (7)	0.0121 (7)	−0.0057 (6)	−0.0012 (6)	−0.0013 (5)
N4	0.0136 (7)	0.0131 (7)	0.0138 (7)	−0.0034 (6)	−0.0020 (6)	−0.0023 (6)
C1	0.0102 (8)	0.0115 (8)	0.0144 (8)	−0.0015 (6)	−0.0009 (6)	−0.0034 (6)
C2	0.0121 (8)	0.0163 (8)	0.0171 (9)	−0.0038 (7)	−0.0020 (7)	−0.0056 (7)
C3	0.0137 (8)	0.0196 (9)	0.0139 (8)	−0.0016 (7)	−0.0043 (6)	−0.0048 (7)
C4	0.0133 (8)	0.0153 (8)	0.0119 (8)	−0.0018 (7)	−0.0024 (6)	−0.0009 (6)
C5	0.0109 (8)	0.0113 (8)	0.0123 (8)	−0.0012 (6)	−0.0015 (6)	−0.0027 (6)
C6	0.0134 (8)	0.0123 (8)	0.0146 (8)	−0.0016 (6)	0.0001 (6)	−0.0032 (6)
C7	0.0117 (8)	0.0119 (8)	0.0121 (8)	−0.0026 (6)	0.0009 (6)	−0.0038 (6)
C8	0.0165 (9)	0.0143 (8)	0.0145 (9)	−0.0040 (7)	−0.0027 (7)	−0.0007 (7)
C9	0.0171 (9)	0.0178 (9)	0.0159 (9)	−0.0050 (7)	−0.0053 (7)	0.0017 (7)
C10	0.0194 (9)	0.0207 (9)	0.0122 (8)	−0.0081 (7)	−0.0046 (7)	0.0010 (7)
C11	0.0167 (9)	0.0184 (9)	0.0126 (8)	−0.0079 (7)	−0.0010 (7)	−0.0021 (7)
C12	0.0218 (9)	0.0244 (10)	0.0123 (8)	−0.0098 (8)	−0.0003 (7)	−0.0055 (7)
C13	0.0194 (9)	0.0244 (10)	0.0148 (9)	−0.0098 (8)	0.0033 (7)	−0.0077 (7)
C14	0.0159 (8)	0.0161 (8)	0.0145 (8)	−0.0075 (7)	0.0014 (7)	−0.0035 (7)
C15	0.0166 (9)	0.0158 (9)	0.0205 (9)	−0.0058 (7)	0.0044 (7)	−0.0060 (7)
C16	0.0140 (8)	0.0146 (8)	0.0202 (9)	−0.0029 (7)	−0.0001 (7)	−0.0016 (7)
C17	0.0157 (8)	0.0141 (8)	0.0148 (8)	−0.0051 (7)	−0.0007 (7)	−0.0012 (7)
C18	0.0149 (8)	0.0134 (8)	0.0117 (8)	−0.0072 (7)	−0.0002 (6)	−0.0009 (6)
C19	0.0149 (8)	0.0136 (8)	0.0116 (8)	−0.0065 (7)	−0.0007 (6)	−0.0012 (6)
C20	0.0125 (8)	0.0136 (8)	0.0153 (8)	−0.0024 (6)	−0.0021 (6)	−0.0028 (7)
C21	0.0177 (9)	0.0189 (9)	0.0190 (9)	−0.0062 (7)	−0.0039 (7)	−0.0060 (7)
C22	0.0218 (9)	0.0226 (9)	0.0135 (9)	−0.0056 (8)	−0.0044 (7)	−0.0038 (7)
C23	0.0188 (9)	0.0167 (9)	0.0146 (9)	−0.0053 (7)	−0.0021 (7)	−0.0012 (7)
C24	0.0119 (8)	0.0120 (8)	0.0151 (8)	−0.0021 (6)	−0.0011 (6)	−0.0030 (6)
C25	0.0157 (8)	0.0144 (8)	0.0172 (9)	−0.0033 (7)	−0.0026 (7)	−0.0028 (7)
C26	0.0121 (8)	0.0113 (8)	0.0163 (8)	−0.0019 (6)	−0.0009 (6)	−0.0031 (6)
O1W	0.0178 (6)	0.0170 (6)	0.0126 (6)	−0.0011 (5)	−0.0008 (5)	−0.0037 (5)
O2W	0.0291 (8)	0.0170 (7)	0.0158 (7)	−0.0069 (6)	−0.0043 (6)	−0.0001 (5)
O3W	0.0238 (7)	0.0283 (8)	0.0233 (8)	−0.0102 (6)	−0.0030 (6)	−0.0081 (6)
O4W	0.0644 (13)	0.0272 (9)	0.0417 (11)	−0.0193 (9)	−0.0339 (10)	0.0116 (8)
O5W	0.0342 (10)	0.0487 (11)	0.0398 (11)	−0.0134 (9)	0.0049 (8)	0.0100 (9)

Ni1—N1	1.9790 (15)	C9—H9A	0.9500
Ni1—N2	2.0462 (15)	C10—C11	1.414 (3)
Ni1—N3	2.0754 (16)	C10—H10A	0.9500
Ni1—O1W	2.1023 (13)	C11—C19	1.406 (3)
Ni1—O1	2.1325 (13)	C11—C12	1.436 (3)
Ni1—O3	2.1325 (13)	C12—C13	1.360 (3)
O1—C6	1.272 (2)	C12—H12A	0.9500
O2—C6	1.246 (2)	C13—C14	1.436 (3)
O3—C7	1.257 (2)	C13—H13A	0.9500
O4—C7	1.260 (2)	C14—C18	1.404 (3)
O5—C25	1.326 (2)	C14—C15	1.411 (3)
O5—H5A	0.8400	C15—C16	1.368 (3)
O6—C25	1.212 (2)	C15—H15A	0.9500
O7—C26	1.217 (2)	C16—C17	1.409 (3)
O8—C26	1.312 (2)	C16—H16A	0.9500
O8—H8A	0.8400	C17—H17A	0.9500
N1—C5	1.331 (2)	C18—C19	1.437 (3)
N1—C1	1.335 (2)	C20—C21	1.393 (3)
N2—C8	1.332 (2)	C20—C25	1.504 (3)
N2—C19	1.362 (2)	C21—C22	1.385 (3)
N3—C17	1.324 (2)	C21—H21A	0.9500
N3—C18	1.364 (2)	C22—C23	1.394 (3)
N4—C20	1.331 (2)	C22—H22A	0.9500
N4—C24	1.339 (2)	C23—C24	1.389 (3)
C1—C2	1.382 (3)	C23—H23A	0.9500
C1—C6	1.522 (2)	C24—C26	1.506 (3)
C2—C3	1.399 (3)	O1W—H1	0.8500
C2—H2A	0.9500	O1W—H2	0.8501
C3—C4	1.390 (3)	O2W—H3	0.8500
C3—H3A	0.9500	O2W—H4	0.8500
C4—C5	1.390 (2)	O3W—H5	0.8501
C4—H4B	0.9500	O3W—H6	0.8501
C5—C7	1.519 (2)	O4W—H7	0.8499
C8—C9	1.402 (3)	O4W—H8	0.8500
C8—H8B	0.9500	O5W—H9	0.8500
C9—C10	1.376 (3)	O5W—H10	0.8500
N1—Ni1—N2	176.22 (6)	C9—C10—H10A	120.4
N1—Ni1—N3	98.32 (6)	C11—C10—H10A	120.4
N2—Ni1—N3	80.66 (6)	C19—C11—C10	117.33 (17)
N1—Ni1—O1W	91.23 (6)	C19—C11—C12	119.15 (17)
N2—Ni1—O1W	89.89 (6)	C10—C11—C12	123.49 (17)
N3—Ni1—O1W	170.36 (6)	C13—C12—C11	120.85 (18)
N1—Ni1—O1	78.03 (6)	C13—C12—H12A	119.6
N2—Ni1—O1	98.33 (6)	C11—C12—H12A	119.6
N3—Ni1—O1	91.53 (5)	C12—C13—C14	121.23 (18)
O1W—Ni1—O1	91.76 (5)	C12—C13—H13A	119.4
N1—Ni1—O3	77.62 (6)	C14—C13—H13A	119.4
N2—Ni1—O3	106.01 (5)	C18—C14—C15	117.11 (17)
N3—Ni1—O3	91.48 (5)	C18—C14—C13	118.81 (17)
O1W—Ni1—O3	89.24 (5)	C15—C14—C13	124.07 (18)
O1—Ni1—O3	155.65 (5)	C16—C15—C14	119.53 (17)
C6—O1—Ni1	114.67 (11)	C16—C15—H15A	120.2
C7—O3—Ni1	114.38 (11)	C14—C15—H15A	120.2
C25—O5—H5A	109.5	C15—C16—C17	119.54 (18)
C26—O8—H8A	109.5	C15—C16—H16A	120.2
C5—N1—C1	121.56 (16)	C17—C16—H16A	120.2
C5—N1—Ni1	119.38 (12)	N3—C17—C16	122.47 (17)
C1—N1—Ni1	118.66 (12)	N3—C17—H17A	118.8
C8—N2—C19	117.89 (16)	C16—C17—H17A	118.8
C8—N2—Ni1	128.89 (13)	N3—C18—C14	123.15 (17)
C19—N2—Ni1	113.21 (12)	N3—C18—C19	116.67 (16)
C17—N3—C18	118.21 (16)	C14—C18—C19	120.16 (17)
C17—N3—Ni1	129.43 (13)	N2—C19—C11	123.22 (17)
C18—N3—Ni1	112.35 (12)	N2—C19—C18	116.97 (16)
C20—N4—C24	117.95 (16)	C11—C19—C18	119.77 (17)
N1—C1—C2	121.05 (16)	N4—C20—C21	123.74 (17)
N1—C1—C6	113.02 (15)	N4—C20—C25	115.21 (16)
C2—C1—C6	125.88 (16)	C21—C20—C25	121.05 (17)
C1—C2—C3	117.96 (17)	C22—C21—C20	117.81 (17)
C1—C2—H2A	121.0	C22—C21—H21A	121.1
C3—C2—H2A	121.0	C20—C21—H21A	121.1
C4—C3—C2	120.48 (17)	C21—C22—C23	119.22 (18)
C4—C3—H3A	119.8	C21—C22—H22A	120.4
C2—C3—H3A	119.8	C23—C22—H22A	120.4
C5—C4—C3	117.65 (17)	C24—C23—C22	118.47 (17)
C5—C4—H4B	121.2	C24—C23—H23A	120.8
C3—C4—H4B	121.2	C22—C23—H23A	120.8
N1—C5—C4	121.29 (16)	N4—C24—C23	122.80 (17)
N1—C5—C7	111.82 (15)	N4—C24—C26	113.94 (16)
C4—C5—C7	126.87 (16)	C23—C24—C26	123.26 (16)
O2—C6—O1	126.39 (17)	O6—C25—O5	120.81 (17)
O2—C6—C1	118.29 (16)	O6—C25—C20	122.40 (17)
O1—C6—C1	115.32 (16)	O5—C25—C20	116.79 (16)
O3—C7—O4	125.29 (17)	O7—C26—O8	124.45 (17)
O3—C7—C5	116.47 (15)	O7—C26—C24	121.99 (16)
O4—C7—C5	118.24 (16)	O8—C26—C24	113.56 (16)
N2—C8—C9	122.90 (18)	Ni1—O1W—H1	116.7
N2—C8—H8B	118.6	Ni1—O1W—H2	102.9
C9—C8—H8B	118.6	H1—O1W—H2	114.9
C10—C9—C8	119.48 (18)	H3—O2W—H4	101.8
C10—C9—H9A	120.3	H5—O3W—H6	113.4
C8—C9—H9A	120.3	H7—O4W—H8	113.0
C9—C10—C11	119.17 (17)	H9—O5W—H10	99.9
N1—Ni1—O1—C6	−1.09 (12)	N1—C5—C7—O4	173.91 (15)
N2—Ni1—O1—C6	179.94 (12)	C4—C5—C7—O4	−7.9 (3)
N3—Ni1—O1—C6	−99.28 (13)	C19—N2—C8—C9	−0.7 (3)
O1W—Ni1—O1—C6	89.79 (13)	Ni1—N2—C8—C9	178.26 (13)
O3—Ni1—O1—C6	−2.3 (2)	N2—C8—C9—C10	0.1 (3)
N1—Ni1—O3—C7	−0.40 (12)	C8—C9—C10—C11	0.7 (3)
N2—Ni1—O3—C7	178.50 (12)	C9—C10—C11—C19	−0.8 (3)
N3—Ni1—O3—C7	97.79 (13)	C9—C10—C11—C12	177.34 (18)
O1W—Ni1—O3—C7	−91.82 (12)	C19—C11—C12—C13	1.2 (3)
O1—Ni1—O3—C7	0.8 (2)	C10—C11—C12—C13	−176.87 (18)
N3—Ni1—N1—C5	−93.15 (14)	C11—C12—C13—C14	−0.6 (3)
O1W—Ni1—N1—C5	85.50 (13)	C12—C13—C14—C18	−0.9 (3)
O1—Ni1—N1—C5	177.05 (14)	C12—C13—C14—C15	178.47 (18)
O3—Ni1—N1—C5	−3.45 (13)	C18—C14—C15—C16	−0.3 (3)
N3—Ni1—N1—C1	94.01 (13)	C13—C14—C15—C16	−179.67 (18)
O1W—Ni1—N1—C1	−87.35 (13)	C14—C15—C16—C17	−0.2 (3)
O1—Ni1—N1—C1	4.20 (13)	C18—N3—C17—C16	0.0 (3)
O3—Ni1—N1—C1	−176.30 (14)	Ni1—N3—C17—C16	178.89 (13)
N3—Ni1—N2—C8	177.64 (16)	C15—C16—C17—N3	0.3 (3)
O1W—Ni1—N2—C8	−0.40 (16)	C17—N3—C18—C14	−0.5 (3)
O1—Ni1—N2—C8	−92.17 (16)	Ni1—N3—C18—C14	−179.59 (14)
O3—Ni1—N2—C8	88.78 (16)	C17—N3—C18—C19	177.93 (16)
N3—Ni1—N2—C19	−3.34 (12)	Ni1—N3—C18—C19	−1.15 (19)
O1W—Ni1—N2—C19	178.62 (12)	C15—C14—C18—N3	0.7 (3)
O1—Ni1—N2—C19	86.85 (12)	C13—C14—C18—N3	−179.93 (16)
O3—Ni1—N2—C19	−92.20 (12)	C15—C14—C18—C19	−177.73 (16)
N1—Ni1—N3—C17	7.14 (16)	C13—C14—C18—C19	1.7 (3)
N2—Ni1—N3—C17	−176.54 (16)	C8—N2—C19—C11	0.6 (3)
O1—Ni1—N3—C17	85.27 (16)	Ni1—N2—C19—C11	−178.56 (14)
O3—Ni1—N3—C17	−70.56 (16)	C8—N2—C19—C18	−177.09 (16)
N1—Ni1—N3—C18	−173.91 (12)	Ni1—N2—C19—C18	3.77 (19)
N2—Ni1—N3—C18	2.41 (12)	C10—C11—C19—N2	0.2 (3)
O1—Ni1—N3—C18	−95.78 (12)	C12—C11—C19—N2	−178.06 (17)
O3—Ni1—N3—C18	108.39 (12)	C10—C11—C19—C18	177.79 (16)
C5—N1—C1—C2	−1.3 (3)	C12—C11—C19—C18	−0.4 (3)
Ni1—N1—C1—C2	171.37 (13)	N3—C18—C19—N2	−1.7 (2)
C5—N1—C1—C6	−178.88 (15)	C14—C18—C19—N2	176.74 (16)
Ni1—N1—C1—C6	−6.2 (2)	N3—C18—C19—C11	−179.51 (16)
N1—C1—C2—C3	0.8 (3)	C14—C18—C19—C11	−1.0 (3)
C6—C1—C2—C3	178.04 (17)	C24—N4—C20—C21	0.2 (3)
C1—C2—C3—C4	0.6 (3)	C24—N4—C20—C25	−179.58 (16)
C2—C3—C4—C5	−1.4 (3)	N4—C20—C21—C22	0.6 (3)
C1—N1—C5—C4	0.4 (3)	C25—C20—C21—C22	−179.68 (17)
Ni1—N1—C5—C4	−172.21 (13)	C20—C21—C22—C23	−0.7 (3)
C1—N1—C5—C7	178.71 (15)	C21—C22—C23—C24	0.2 (3)
Ni1—N1—C5—C7	6.08 (19)	C20—N4—C24—C23	−0.8 (3)
C3—C4—C5—N1	0.9 (3)	C20—N4—C24—C26	178.62 (16)
C3—C4—C5—C7	−177.09 (17)	C22—C23—C24—N4	0.6 (3)
Ni1—O1—C6—O2	179.10 (15)	C22—C23—C24—C26	−178.76 (17)
Ni1—O1—C6—C1	−1.73 (19)	N4—C20—C25—O6	178.52 (18)
N1—C1—C6—O2	−175.69 (16)	C21—C20—C25—O6	−1.3 (3)
C2—C1—C6—O2	6.9 (3)	N4—C20—C25—O5	−1.7 (2)
N1—C1—C6—O1	5.1 (2)	C21—C20—C25—O5	178.54 (17)
C2—C1—C6—O1	−172.37 (17)	N4—C24—C26—O7	1.8 (3)
Ni1—O3—C7—O4	−176.60 (14)	C23—C24—C26—O7	−178.84 (18)
Ni1—O3—C7—C5	3.63 (19)	N4—C24—C26—O8	−178.54 (15)
N1—C5—C7—O3	−6.3 (2)	C23—C24—C26—O8	0.9 (3)
C4—C5—C7—O3	171.87 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2W	0.84	1.96	2.730 (2)	151
O8—H8A···O4i	0.84	1.73	2.573 (2)	177
O1W—H1···O4i	0.85	2.13	2.946 (2)	161
O1W—H2···O3W	0.85	1.95	2.796 (2)	171
O2W—H3···O2	0.85	2.09	2.900 (2)	159
O2W—H4···O7	0.85	1.94	2.788 (2)	174
O3W—H5···O2W	0.85	2.09	2.887 (2)	157
O3W—H6···O4Wii	0.85	2.37	3.083 (3)	142
O4W—H7···O1ii	0.85	2.03	2.864 (3)	168
O4W—H8···O5Wiii	0.85	1.93	2.772 (3)	169
O5W—H9···O2	0.85	2.24	2.878 (3)	131
O2W—H4···N4	0.85	2.54	2.968 (2)	112
O5—H5A···N4	0.84	2.18	2.669 (2)	117
C2—H2A···O6iv	0.95	2.28	3.105 (2)	144
C8—H8B···O1W	0.95	2.52	3.070 (2)	117
C12—H12A···O3v	0.95	2.60	3.317 (2)	132
C15—H15A···O1vi	0.95	2.52	3.385 (2)	151

Ni1—N1	1.9790 (15)
Ni1—N2	2.0462 (15)
Ni1—N3	2.0754 (16)
Ni1—O1W	2.1023 (13)
Ni1—O1	2.1325 (13)
Ni1—O3	2.1325 (13)

N1—Ni1—N2	176.22 (6)
N1—Ni1—N3	98.32 (6)
N2—Ni1—N3	80.66 (6)
N1—Ni1—O1W	91.23 (6)
N2—Ni1—O1W	89.89 (6)
O1—Ni1—O3	155.65 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2W	0.84	1.96	2.730 (2)	151
O8—H8A⋯O4i	0.84	1.73	2.573 (2)	177
O1W—H1⋯O4i	0.85	2.13	2.946 (2)	161
O1W—H2⋯O3W	0.85	1.95	2.796 (2)	171
O2W—H3⋯O2	0.85	2.09	2.900 (2)	159
O2W—H4⋯O7	0.85	1.94	2.788 (2)	174
O3W—H5⋯O2W	0.85	2.09	2.887 (2)	157
O3W—H6⋯O4Wii	0.85	2.37	3.083 (3)	142
O4W—H7⋯O1ii	0.85	2.03	2.864 (3)	168
O4W—H8⋯O5Wiii	0.85	1.93	2.772 (3)	169
O5W—H9⋯O2	0.85	2.24	2.878 (3)	131
O2W—H4⋯N4	0.85	2.54	2.968 (2)	112
O5—H5A⋯N4	0.84	2.18	2.669 (2)	117
C2—H2A⋯O6iv	0.95	2.28	3.105 (2)	144
C8—H8B⋯O1W	0.95	2.52	3.070 (2)	117
C12—H12A⋯O3v	0.95	2.60	3.317 (2)	132
C15—H15A⋯O1vi	0.95	2.52	3.385 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .