2,9-Dimethyl-1,10-phenanthrolin-1-ium (6-carb-oxy-4-hy-droxy-pyridine-2-carboxyl-ato-κO,N,O)(4-hy-droxy-pyridine-2,6-dicarboxyl-ato-κO,N,O)nickelate(II) 2.35-hydrate: a proton-transfer compound.

The title proton-transfer compound, (C(14)H(13)N(2))[Ni(C(7)H(3)NO(5))(C(7)H(4)NO(5))]·2.35H(2)O, consists of an [Ni(hypydc)(hypydcH)](-) anion, a dmpH(+) cation and 2.35 uncoordinated water mol-ecules (where hypydcH(2) = 4-hy-droxy-pyridine-2,6-dicarb-oxy-lic acid and dmp = 2,9-dimethyl-1,10-phenanthroline). The Ni(II) atom is coordinated by two N atoms and four O atoms from the carboxyl-ate groups of the (hypydc)(2-) and (hypydcH)(-) ligands, forming a distorted octa-hedral environment. In the anion, the two pyridine rings are inclined to one another by 89.24 (10)°. In the crystal, cations are linked via O-H⋯O hydrogen bonds forming dimers, graph-set [R(2) (2)(16)], centered about inversion centers. These dimers are further linked by other cation O-H⋯O hydrogen bonds, graph-set [R(6) (6)(42)], forming a two-dimensional network in (011). Additional inter-molecular O-H⋯O, N-H⋯O, N-H⋯N, and weak C-H⋯O hydrogen bonds, and π-π inter-actions [shortest centroid-centroid distance = 3.5442 (14) Å], connect the two dimensional networks, forming a three-dimensional arrangement. The H atoms of one of the methyl groups are disordered over two sites with equal occupancy.

Related literature

For literature on some first-row transition metal complexes of 4-hy­droxy­n class="Chemical">pyridine-2,6-dicarboxlic acid and various bases, see: Aghabozorg, Roshan et al. (2008 ▶); Aghabozorg, Saadaty et al. (2008 ▶); Aghabozorg, Motyeian et al. (2008 ▶); Ghadermazi et al. (2009 ▶); Rafizadeh et al. (2008 ▶); Ramos Silva et al. (2008 ▶). For details of graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

(C14H13N2)[n class="Chemical">Ni(C7H3NO5)(C7H4NO5)]·2.35H2O

M = 673.53

Monoclinic,

a = 11.1663 (8) Å

b = 9.7296 (9) Å

c = 25.698 (2) Å

β = 94.330 (9)°

V = 2784.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 223 K

0.34 × 0.30 × 0.23 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.820, T max = 0.839

21508 measured reflections

5442 independent reflections

3321 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.071

S = 0.82

5442 reflections

439 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.49 e Å−3

Data collection: EXPOSE (Stoe & Cie, 2000 ▶); cell refinement: n class="Disease">CELL (Stoe & Cie, 2000 ▶); data reduction: INTEGRATE (Stoe & Cie, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031399/lh5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031399/lh5110Isup2.hkl

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

(C14H13N2)[Ni(C7H3NO5)(C7H4NO5)]·2.35H2O	F(000) = 1390
Mr = 673.53	Dx = 1.607 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 11.1663 (8) Å	θ = 2.2–26.1°
b = 9.7296 (9) Å	µ = 0.77 mm−1
c = 25.698 (2) Å	T = 223 K
β = 94.330 (9)°	Block, pale-blue
V = 2784.0 (4) Å3	0.34 × 0.30 × 0.23 mm
Z = 4

Stoe IPDS diffractometer	5442 independent reflections
Radiation source: fine-focus sealed tube	3321 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ rotation scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −13→12
Tmin = 0.820, Tmax = 0.839	k = −12→11
21508 measured reflections	l = −31→31

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82	(Δ/σ)max = 0.001
5442 reflections	Δρmax = 0.29 e Å−3
439 parameters	Δρmin = −0.49 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. The water H-atoms were refined with distance restraints of O-H = 0.84 (2) Å and Uiso(H) = 1.5Ueq(O). The OH, NH and C-bound H-atoms were included in calculated positions and treated as riding on their parent atom: O-H = 0.83 Å, N-H = 0.87 Å, C-H = 0.94 and 0.97 Å, for CH and CH3, respectively, with Uiso(H) = k × Ueq(O, N, or C), where k = 1.5 for CH3 H-atoms and 1.2 for all other H-atoms. The water molecule O3W was only partially occupied and was refined with an occupancy of 0.35. Methyl group C28 was treated as an idealized disordered methyl group with two positions rotated from each other by 60°; each H-atom occupancy was set to 0.5.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.14739 (3)	0.96793 (3)	0.15130 (1)	0.0260 (1)
O1	0.15046 (15)	1.07916 (16)	0.22542 (6)	0.0298 (5)
O2	0.25528 (15)	1.07951 (16)	0.30382 (6)	0.0290 (5)
O3	0.21156 (15)	0.82051 (17)	0.09837 (6)	0.0313 (6)
O4	0.34942 (19)	0.6562 (2)	0.09309 (8)	0.0662 (9)
O5	0.58914 (17)	0.7378 (2)	0.27078 (7)	0.0453 (7)
O6	0.01044 (16)	0.82870 (16)	0.17517 (6)	0.0308 (5)
O7	−0.18300 (17)	0.77766 (19)	0.15269 (7)	0.0428 (7)
O8	0.21250 (15)	1.14097 (17)	0.11129 (6)	0.0340 (6)
O9	0.15781 (17)	1.28829 (18)	0.04666 (7)	0.0472 (7)
O10	−0.25820 (15)	1.06177 (19)	−0.01149 (6)	0.0405 (7)
N1	0.28647 (17)	0.88779 (18)	0.19159 (7)	0.0232 (6)
N2	0.00840 (16)	1.02066 (19)	0.10486 (6)	0.0234 (6)
C1	0.3184 (2)	0.9328 (2)	0.23970 (8)	0.0226 (7)
C2	0.4179 (2)	0.8853 (2)	0.26876 (8)	0.0251 (7)
C3	0.4886 (2)	0.7856 (3)	0.24664 (9)	0.0295 (8)
C4	0.4526 (2)	0.7357 (2)	0.19695 (9)	0.0305 (8)
C5	0.3517 (2)	0.7890 (2)	0.17069 (8)	0.0276 (8)
C6	0.2335 (2)	1.0398 (2)	0.25655 (8)	0.0240 (7)
C7	0.3021 (2)	0.7496 (3)	0.11634 (9)	0.0333 (9)
C8	−0.0908 (2)	0.9446 (2)	0.10399 (8)	0.0239 (7)
C9	−0.1816 (2)	0.9572 (3)	0.06563 (8)	0.0282 (7)
C10	−0.1691 (2)	1.0544 (2)	0.02645 (8)	0.0277 (8)
C11	−0.0673 (2)	1.1354 (2)	0.02800 (8)	0.0254 (7)
C12	0.0207 (2)	1.1152 (2)	0.06783 (8)	0.0248 (7)
C13	−0.0863 (2)	0.8416 (2)	0.14803 (9)	0.0286 (8)
C14	0.1396 (2)	1.1890 (2)	0.07497 (9)	0.0315 (8)
N3	0.85534 (18)	0.40284 (19)	0.10413 (7)	0.0285 (6)
N4	0.64764 (19)	0.2613 (2)	0.08013 (8)	0.0378 (8)
C15	0.9561 (2)	0.4758 (3)	0.11221 (9)	0.0297 (7)
C16	1.0299 (2)	0.4506 (3)	0.15731 (9)	0.0378 (9)
C17	1.0007 (2)	0.3517 (3)	0.19177 (9)	0.0361 (9)
C18	0.8949 (2)	0.2752 (2)	0.18279 (9)	0.0305 (8)
C19	0.8601 (3)	0.1697 (3)	0.21716 (10)	0.0380 (9)
C20	0.7587 (3)	0.0981 (3)	0.20579 (10)	0.0404 (10)
C21	0.6824 (2)	0.1255 (3)	0.15974 (10)	0.0362 (9)
C22	0.5769 (3)	0.0533 (3)	0.14537 (12)	0.0522 (11)
C23	0.5108 (3)	0.0846 (3)	0.10047 (12)	0.0572 (11)
C24	0.5487 (3)	0.1909 (3)	0.06806 (11)	0.0481 (10)
C25	0.7134 (2)	0.2290 (3)	0.12506 (9)	0.0319 (8)
C26	0.8214 (2)	0.3034 (2)	0.13757 (9)	0.0277 (8)
C27	0.9852 (3)	0.5789 (3)	0.07223 (10)	0.0409 (9)
C28	0.4771 (3)	0.2259 (4)	0.01801 (12)	0.0692 (14)
O1W	0.7549 (2)	0.4759 (2)	0.00287 (7)	0.0628 (9)
O2W	0.3478 (2)	0.3691 (2)	0.14479 (9)	0.0670 (9)
O3W	0.5288 (6)	0.4962 (6)	0.1014 (2)	0.059 (2)	0.350
H2	0.43790	0.91880	0.30260	0.0300*
H2O	0.21100	1.14540	0.30970	0.0430*
H4	0.49690	0.66640	0.18170	0.0370*
H5O	0.60140	0.77650	0.29950	0.0680*
H9	−0.25060	0.90200	0.06560	0.0340*
H10O	−0.23970	1.11730	−0.03410	0.0610*
H11	−0.05830	1.20280	0.00240	0.0310*
H3	0.80880	0.41940	0.07610	0.0340*
H16	1.10050	0.50230	0.16410	0.0450*
H17	1.05200	0.33470	0.22180	0.0430*
H19	0.90830	0.15030	0.24790	0.0460*
H20	0.73740	0.02830	0.22860	0.0480*
H22	0.55160	−0.01730	0.16690	0.0630*
H23	0.43990	0.03570	0.09090	0.0690*
H27A	0.91230	0.62570	0.05920	0.0610*
H27B	1.02040	0.53280	0.04360	0.0610*
H27C	1.04180	0.64540	0.08780	0.0610*
H28A	0.48890	0.32200	0.00980	0.1040*	0.500
H28B	0.39260	0.20920	0.02190	0.1040*	0.500
H28C	0.50360	0.16920	−0.01000	0.1040*	0.500
H28D	0.43450	0.14490	0.00470	0.1040*	0.500
H28E	0.53080	0.25780	−0.00740	0.1040*	0.500
H28F	0.41980	0.29770	0.02440	0.1040*	0.500
H1WA	0.769 (4)	0.551 (2)	−0.0102 (14)	0.0940*
H1WB	0.715 (3)	0.426 (3)	−0.0187 (12)	0.0940*
H2WA	0.307 (3)	0.312 (3)	0.1262 (13)	0.1000*
H2WB	0.352 (4)	0.445 (2)	0.1319 (14)	0.1000*
H3WA	0.506 (9)	0.576 (5)	0.091 (4)	0.0880*	0.350
H3WB	0.568 (8)	0.470 (11)	0.077 (3)	0.0880*	0.350

	U11	U22	U33	U12	U13	U23
Ni1	0.0257 (2)	0.0274 (2)	0.0242 (2)	−0.0010 (2)	−0.0024 (1)	0.0008 (1)
O1	0.0285 (10)	0.0309 (9)	0.0290 (8)	0.0058 (7)	−0.0042 (8)	−0.0019 (7)
O2	0.0354 (10)	0.0282 (9)	0.0232 (8)	0.0086 (7)	0.0003 (7)	−0.0042 (7)
O3	0.0323 (11)	0.0367 (10)	0.0243 (8)	−0.0016 (8)	−0.0021 (8)	−0.0020 (7)
O4	0.0577 (15)	0.0876 (17)	0.0509 (12)	0.0291 (13)	−0.0117 (11)	−0.0451 (12)
O5	0.0437 (13)	0.0535 (12)	0.0366 (10)	0.0256 (10)	−0.0112 (9)	−0.0100 (9)
O6	0.0339 (11)	0.0323 (9)	0.0257 (8)	0.0008 (8)	−0.0002 (8)	0.0056 (7)
O7	0.0367 (12)	0.0463 (11)	0.0451 (11)	−0.0130 (9)	0.0020 (9)	0.0193 (9)
O8	0.0284 (10)	0.0358 (10)	0.0366 (10)	−0.0092 (8)	−0.0044 (8)	0.0017 (8)
O9	0.0497 (13)	0.0363 (11)	0.0551 (12)	−0.0168 (9)	0.0013 (10)	0.0150 (9)
O10	0.0315 (11)	0.0624 (14)	0.0265 (9)	−0.0060 (9)	−0.0059 (8)	0.0124 (8)
N1	0.0231 (11)	0.0243 (10)	0.0220 (10)	−0.0004 (8)	0.0006 (8)	−0.0015 (8)
N2	0.0249 (11)	0.0219 (9)	0.0231 (9)	−0.0007 (9)	0.0001 (8)	0.0001 (8)
C1	0.0248 (13)	0.0226 (12)	0.0206 (11)	−0.0019 (9)	0.0030 (10)	−0.0012 (9)
C2	0.0294 (14)	0.0252 (12)	0.0204 (11)	0.0012 (10)	−0.0007 (10)	0.0002 (9)
C3	0.0295 (15)	0.0299 (12)	0.0284 (12)	0.0061 (11)	−0.0021 (11)	0.0021 (10)
C4	0.0321 (15)	0.0297 (13)	0.0299 (13)	0.0089 (11)	0.0032 (11)	−0.0043 (10)
C5	0.0316 (15)	0.0271 (13)	0.0240 (12)	−0.0025 (11)	0.0021 (11)	−0.0039 (10)
C6	0.0256 (13)	0.0215 (11)	0.0247 (11)	−0.0025 (11)	0.0012 (10)	0.0008 (10)
C7	0.0313 (16)	0.0401 (16)	0.0282 (13)	0.0000 (12)	0.0007 (11)	−0.0057 (12)
C8	0.0230 (13)	0.0253 (13)	0.0235 (11)	−0.0025 (10)	0.0029 (10)	−0.0006 (9)
C9	0.0220 (13)	0.0364 (14)	0.0260 (11)	−0.0068 (11)	0.0015 (10)	0.0017 (11)
C10	0.0261 (14)	0.0361 (15)	0.0206 (11)	0.0042 (11)	0.0001 (10)	0.0015 (10)
C11	0.0277 (14)	0.0269 (13)	0.0218 (11)	0.0022 (11)	0.0029 (10)	0.0040 (9)
C12	0.0287 (14)	0.0193 (12)	0.0269 (12)	−0.0021 (10)	0.0050 (10)	−0.0005 (9)
C13	0.0339 (16)	0.0272 (13)	0.0247 (12)	−0.0012 (12)	0.0027 (12)	0.0021 (10)
C14	0.0311 (16)	0.0301 (14)	0.0334 (14)	−0.0032 (11)	0.0023 (12)	−0.0019 (11)
N3	0.0318 (12)	0.0292 (11)	0.0243 (10)	0.0022 (9)	0.0007 (9)	−0.0026 (8)
N4	0.0284 (13)	0.0515 (14)	0.0333 (12)	−0.0057 (11)	0.0021 (10)	−0.0028 (10)
C15	0.0296 (14)	0.0297 (12)	0.0299 (12)	−0.0017 (12)	0.0029 (10)	−0.0064 (11)
C16	0.0349 (16)	0.0407 (16)	0.0373 (14)	−0.0067 (13)	−0.0009 (12)	−0.0061 (12)
C17	0.0386 (17)	0.0383 (15)	0.0301 (13)	0.0061 (13)	−0.0061 (12)	−0.0049 (11)
C18	0.0362 (16)	0.0290 (13)	0.0266 (12)	0.0072 (11)	0.0051 (11)	−0.0043 (10)
C19	0.0487 (19)	0.0346 (15)	0.0314 (14)	0.0103 (13)	0.0069 (13)	0.0016 (11)
C20	0.056 (2)	0.0307 (14)	0.0364 (15)	0.0029 (14)	0.0161 (14)	0.0036 (12)
C21	0.0389 (17)	0.0351 (14)	0.0362 (14)	−0.0027 (12)	0.0137 (13)	−0.0034 (11)
C22	0.051 (2)	0.056 (2)	0.0519 (18)	−0.0163 (16)	0.0190 (15)	−0.0012 (15)
C23	0.0418 (19)	0.074 (2)	0.0570 (19)	−0.0245 (16)	0.0112 (16)	−0.0073 (16)
C24	0.0316 (17)	0.069 (2)	0.0441 (16)	−0.0098 (15)	0.0051 (13)	−0.0071 (14)
C25	0.0298 (15)	0.0364 (14)	0.0304 (13)	−0.0007 (11)	0.0081 (11)	−0.0047 (11)
C26	0.0304 (15)	0.0268 (13)	0.0267 (12)	0.0023 (11)	0.0066 (11)	−0.0038 (10)
C27	0.0492 (18)	0.0384 (15)	0.0354 (14)	−0.0116 (13)	0.0053 (13)	−0.0033 (11)
C28	0.037 (2)	0.112 (3)	0.057 (2)	−0.0174 (19)	−0.0064 (16)	−0.0023 (19)
O1W	0.0982 (19)	0.0473 (13)	0.0392 (11)	−0.0271 (13)	−0.0194 (11)	0.0131 (10)
O2W	0.0778 (18)	0.0594 (16)	0.0572 (14)	−0.0216 (13)	−0.0377 (12)	0.0033 (11)
O3W	0.061 (4)	0.048 (4)	0.066 (4)	0.019 (3)	−0.007 (3)	−0.007 (3)

Ni1—O1	2.1887 (16)	C8—C9	1.365 (3)
Ni1—O3	2.1373 (17)	C8—C13	1.510 (3)
Ni1—O6	2.1660 (17)	C9—C10	1.396 (3)
Ni1—O8	2.1291 (17)	C10—C11	1.381 (3)
Ni1—N1	1.9619 (19)	C11—C12	1.378 (3)
Ni1—N2	1.9536 (17)	C12—C14	1.508 (3)
O1—C6	1.239 (3)	C2—H2	0.9400
O2—C6	1.280 (3)	C4—H4	0.9400
O3—C7	1.281 (3)	C9—H9	0.9400
O4—C7	1.229 (3)	C11—H11	0.9400
O5—C3	1.325 (3)	C15—C16	1.392 (3)
O6—C13	1.247 (3)	C15—C27	1.489 (4)
O7—C13	1.260 (3)	C16—C17	1.364 (4)
O8—C14	1.280 (3)	C17—C18	1.401 (3)
O9—C14	1.235 (3)	C18—C19	1.427 (4)
O10—C10	1.341 (3)	C18—C26	1.398 (3)
O2—H2O	0.8300	C19—C20	1.343 (5)
O5—H5O	0.8300	C20—C21	1.430 (4)
O10—H10O	0.8300	C21—C22	1.397 (4)
O1W—H1WA	0.82 (2)	C21—C25	1.405 (4)
O1W—H1WB	0.84 (3)	C22—C23	1.357 (4)
O2W—H2WB	0.81 (2)	C23—C24	1.413 (4)
O2W—H2WA	0.84 (3)	C24—C28	1.501 (4)
O3W—H3WB	0.83 (8)	C25—C26	1.422 (3)
O3W—H3WA	0.85 (6)	C16—H16	0.9400
N1—C5	1.342 (3)	C17—H17	0.9400
N1—C1	1.335 (3)	C19—H19	0.9400
N2—C12	1.338 (3)	C20—H20	0.9400
N2—C8	1.331 (3)	C22—H22	0.9400
N3—C15	1.333 (3)	C23—H23	0.9400
N3—C26	1.367 (3)	C27—H27B	0.9700
N4—C24	1.317 (4)	C27—H27A	0.9700
N4—C25	1.358 (3)	C27—H27C	0.9700
N3—H3	0.8700	C28—H28F	0.9700
C1—C2	1.371 (3)	C28—H28A	0.9700
C1—C6	1.494 (3)	C28—H28B	0.9700
C2—C3	1.398 (3)	C28—H28C	0.9700
C3—C4	1.397 (3)	C28—H28D	0.9700
C4—C5	1.371 (3)	C28—H28E	0.9700
C5—C7	1.513 (3)
O1—Ni1—O3	154.38 (6)	C3—C2—H2	121.00
O1—Ni1—O6	91.59 (6)	C3—C4—H4	120.00
O1—Ni1—O8	92.62 (6)	C5—C4—H4	120.00
O1—Ni1—N1	77.14 (7)	C8—C9—H9	121.00
O1—Ni1—N2	111.18 (7)	C10—C9—H9	121.00
O3—Ni1—O6	92.20 (6)	C12—C11—H11	121.00
O3—Ni1—O8	94.60 (6)	C10—C11—H11	121.00
O3—Ni1—N1	77.24 (7)	C16—C15—C27	123.1 (2)
O3—Ni1—N2	94.39 (7)	N3—C15—C16	118.4 (2)
O6—Ni1—O8	154.88 (7)	N3—C15—C27	118.5 (2)
O6—Ni1—N1	98.61 (7)	C15—C16—C17	120.6 (2)
O6—Ni1—N2	77.99 (7)	C16—C17—C18	120.5 (2)
O8—Ni1—N1	106.47 (7)	C17—C18—C19	123.1 (2)
O8—Ni1—N2	77.40 (7)	C19—C18—C26	119.0 (2)
N1—Ni1—N2	170.92 (8)	C17—C18—C26	117.9 (2)
Ni1—O1—C6	111.77 (14)	C18—C19—C20	120.2 (2)
Ni1—O3—C7	115.18 (15)	C19—C20—C21	121.6 (3)
Ni1—O6—C13	112.27 (14)	C20—C21—C22	124.3 (3)
Ni1—O8—C14	114.80 (14)	C22—C21—C25	115.8 (2)
C6—O2—H2O	109.00	C20—C21—C25	119.9 (2)
C3—O5—H5O	109.00	C21—C22—C23	120.4 (3)
C10—O10—H10O	109.00	C22—C23—C24	119.9 (3)
H1WA—O1W—H1WB	111 (3)	N4—C24—C28	117.8 (3)
H2WA—O2W—H2WB	114 (3)	N4—C24—C23	121.7 (3)
H3WA—O3W—H3WB	102 (10)	C23—C24—C28	120.5 (3)
Ni1—N1—C1	120.26 (15)	N4—C25—C21	124.2 (2)
C1—N1—C5	119.38 (19)	C21—C25—C26	117.8 (2)
Ni1—N1—C5	120.35 (14)	N4—C25—C26	118.0 (2)
C8—N2—C12	120.02 (18)	C18—C26—C25	121.5 (2)
Ni1—N2—C8	119.08 (14)	N3—C26—C18	119.2 (2)
Ni1—N2—C12	119.71 (15)	N3—C26—C25	119.3 (2)
C15—N3—C26	123.4 (2)	C15—C16—H16	120.00
C24—N4—C25	118.1 (2)	C17—C16—H16	120.00
C15—N3—H3	118.00	C18—C17—H17	120.00
C26—N3—H3	118.00	C16—C17—H17	120.00
N1—C1—C6	111.48 (18)	C18—C19—H19	120.00
C2—C1—C6	125.65 (19)	C20—C19—H19	120.00
N1—C1—C2	122.87 (19)	C19—C20—H20	119.00
C1—C2—C3	118.13 (19)	C21—C20—H20	119.00
O5—C3—C4	118.8 (2)	C23—C22—H22	120.00
C2—C3—C4	118.7 (2)	C21—C22—H22	120.00
O5—C3—C2	122.5 (2)	C22—C23—H23	120.00
C3—C4—C5	119.2 (2)	C24—C23—H23	120.00
C4—C5—C7	126.1 (2)	C15—C27—H27B	110.00
N1—C5—C4	121.64 (19)	H27A—C27—H27C	109.00
N1—C5—C7	112.27 (19)	C15—C27—H27C	110.00
O1—C6—O2	126.8 (2)	H27A—C27—H27B	109.00
O1—C6—C1	119.26 (18)	C15—C27—H27A	109.00
O2—C6—C1	113.95 (18)	H27B—C27—H27C	109.00
O3—C7—C5	114.9 (2)	C24—C28—H28C	110.00
O4—C7—C5	119.7 (2)	C24—C28—H28E	109.00
O3—C7—O4	125.4 (2)	C24—C28—H28F	110.00
N2—C8—C9	122.3 (2)	C24—C28—H28D	109.00
C9—C8—C13	125.6 (2)	C24—C28—H28A	109.00
N2—C8—C13	112.08 (18)	C24—C28—H28B	109.00
C8—C9—C10	118.2 (2)	H28A—C28—H28E	56.00
C9—C10—C11	119.5 (2)	H28A—C28—H28F	56.00
O10—C10—C9	116.83 (19)	H28B—C28—H28C	110.00
O10—C10—C11	123.65 (19)	H28B—C28—H28D	56.00
C10—C11—C12	118.62 (19)	H28B—C28—H28E	141.00
N2—C12—C14	112.17 (18)	H28B—C28—H28F	56.00
N2—C12—C11	121.4 (2)	H28C—C28—H28D	56.00
C11—C12—C14	126.44 (19)	H28C—C28—H28E	56.00
O7—C13—C8	114.8 (2)	H28C—C28—H28F	141.00
O6—C13—O7	127.6 (2)	H28D—C28—H28E	110.00
O6—C13—C8	117.68 (19)	H28D—C28—H28F	109.00
O8—C14—C12	114.87 (18)	H28E—C28—H28F	109.00
O8—C14—O9	126.2 (2)	H28A—C28—H28B	109.00
O9—C14—C12	118.9 (2)	H28A—C28—H28C	109.00
C1—C2—H2	121.00	H28A—C28—H28D	141.00
O3—Ni1—O1—C6	−0.8 (2)	C24—N4—C25—C21	−0.3 (4)
O6—Ni1—O1—C6	97.65 (15)	C25—N4—C24—C23	0.0 (4)
O8—Ni1—O1—C6	−107.12 (15)	C25—N4—C24—C28	−179.3 (3)
N1—Ni1—O1—C6	−0.82 (15)	C24—N4—C25—C26	178.9 (2)
N2—Ni1—O1—C6	175.38 (14)	N1—C1—C2—C3	0.2 (3)
O1—Ni1—O3—C7	2.0 (3)	N1—C1—C6—O2	175.37 (18)
O6—Ni1—O3—C7	−96.33 (17)	C6—C1—C2—C3	−179.3 (2)
O8—Ni1—O3—C7	107.87 (17)	N1—C1—C6—O1	−3.4 (3)
N1—Ni1—O3—C7	2.00 (17)	C2—C1—C6—O1	176.1 (2)
N2—Ni1—O3—C7	−174.44 (17)	C2—C1—C6—O2	−5.2 (3)
O1—Ni1—O6—C13	114.42 (15)	C1—C2—C3—C4	−2.2 (3)
O3—Ni1—O6—C13	−90.93 (15)	C1—C2—C3—O5	177.0 (2)
O8—Ni1—O6—C13	14.8 (2)	C2—C3—C4—C5	2.2 (3)
N1—Ni1—O6—C13	−168.35 (15)	O5—C3—C4—C5	−177.1 (2)
N2—Ni1—O6—C13	3.09 (15)	C3—C4—C5—C7	178.3 (2)
O1—Ni1—O8—C14	−116.33 (15)	C3—C4—C5—N1	−0.1 (3)
O3—Ni1—O8—C14	88.27 (15)	N1—C5—C7—O3	3.5 (3)
O6—Ni1—O8—C14	−16.9 (2)	N1—C5—C7—O4	−176.9 (2)
N1—Ni1—O8—C14	166.30 (15)	C4—C5—C7—O4	4.5 (4)
N2—Ni1—O8—C14	−5.21 (15)	C4—C5—C7—O3	−175.1 (2)
O1—Ni1—N1—C1	−1.16 (16)	N2—C8—C9—C10	−0.5 (3)
O1—Ni1—N1—C5	−179.94 (17)	C13—C8—C9—C10	−177.3 (2)
O3—Ni1—N1—C1	178.86 (18)	N2—C8—C13—O6	−8.0 (3)
O3—Ni1—N1—C5	0.09 (16)	N2—C8—C13—O7	172.29 (19)
O6—Ni1—N1—C1	−90.83 (17)	C9—C8—C13—O6	169.1 (2)
O6—Ni1—N1—C5	90.40 (16)	C9—C8—C13—O7	−10.6 (3)
O8—Ni1—N1—C1	87.78 (17)	C8—C9—C10—O10	178.2 (2)
O8—Ni1—N1—C5	−90.99 (17)	C8—C9—C10—C11	−0.9 (3)
O1—Ni1—N2—C8	−95.09 (16)	C9—C10—C11—C12	1.6 (3)
O1—Ni1—N2—C12	97.40 (16)	O10—C10—C11—C12	−177.5 (2)
O3—Ni1—N2—C8	83.25 (16)	C10—C11—C12—C14	177.4 (2)
O3—Ni1—N2—C12	−84.27 (16)	C10—C11—C12—N2	−0.8 (3)
O6—Ni1—N2—C8	−8.07 (15)	N2—C12—C14—O8	6.5 (3)
O6—Ni1—N2—C12	−175.58 (17)	C11—C12—C14—O8	−171.8 (2)
O8—Ni1—N2—C8	176.99 (16)	C11—C12—C14—O9	8.8 (3)
O8—Ni1—N2—C12	9.48 (15)	N2—C12—C14—O9	−172.8 (2)
Ni1—O1—C6—O2	−176.12 (18)	N3—C15—C16—C17	1.3 (4)
Ni1—O1—C6—C1	2.5 (2)	C27—C15—C16—C17	−177.8 (3)
Ni1—O3—C7—O4	176.9 (2)	C15—C16—C17—C18	−1.0 (4)
Ni1—O3—C7—C5	−3.5 (3)	C16—C17—C18—C19	179.5 (2)
Ni1—O6—C13—O7	−178.64 (19)	C16—C17—C18—C26	0.2 (4)
Ni1—O6—C13—C8	1.7 (2)	C17—C18—C19—C20	−178.6 (3)
Ni1—O8—C14—O9	−179.95 (19)	C26—C18—C19—C20	0.6 (4)
Ni1—O8—C14—C12	0.8 (2)	C17—C18—C26—N3	0.3 (3)
Ni1—N1—C1—C2	−176.87 (16)	C17—C18—C26—C25	179.0 (2)
Ni1—N1—C1—C6	2.6 (2)	C19—C18—C26—N3	−179.0 (2)
C5—N1—C1—C2	1.9 (3)	C19—C18—C26—C25	−0.3 (3)
C5—N1—C1—C6	−178.60 (18)	C18—C19—C20—C21	−0.6 (4)
Ni1—N1—C5—C4	176.87 (16)	C19—C20—C21—C22	179.0 (3)
Ni1—N1—C5—C7	−1.8 (2)	C19—C20—C21—C25	0.3 (4)
C1—N1—C5—C4	−1.9 (3)	C20—C21—C22—C23	−178.9 (3)
C1—N1—C5—C7	179.42 (19)	C25—C21—C22—C23	−0.2 (4)
Ni1—N2—C8—C9	−166.20 (18)	C20—C21—C25—N4	179.2 (2)
Ni1—N2—C8—C13	11.0 (2)	C20—C21—C25—C26	0.0 (4)
C12—N2—C8—C9	1.3 (3)	C22—C21—C25—N4	0.4 (4)
C12—N2—C8—C13	178.47 (18)	C22—C21—C25—C26	−178.8 (2)
Ni1—N2—C12—C11	166.80 (16)	C21—C22—C23—C24	−0.1 (5)
Ni1—N2—C12—C14	−11.7 (2)	C22—C23—C24—N4	0.2 (5)
C8—N2—C12—C11	−0.6 (3)	C22—C23—C24—C28	179.5 (3)
C8—N2—C12—C14	−179.07 (18)	N4—C25—C26—N3	−0.5 (3)
C15—N3—C26—C18	0.0 (3)	N4—C25—C26—C18	−179.2 (2)
C26—N3—C15—C16	−0.8 (4)	C21—C25—C26—N3	178.7 (2)
C26—N3—C15—C27	178.4 (2)	C21—C25—C26—C18	0.0 (4)
C15—N3—C26—C25	−178.7 (2)

Cg1 is the centroid of the N1,C1–C5.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O9i	0.82 (2)	2.03 (3)	2.832 (3)	166 (4)
O1W—H1WB···O4ii	0.84 (3)	2.15 (3)	2.942 (3)	158 (3)
O2—H2O···O7iii	0.83	1.65	2.399 (2)	148
N3—H3···O1W	0.87	2.01	2.845 (3)	161
N3—H3···N4	0.87	2.38	2.728 (3)	105
O2W—H2WA···O8iv	0.84 (3)	1.99 (3)	2.785 (3)	156 (3)
O2W—H2WA···O9iv	0.84 (3)	2.55 (3)	3.267 (3)	144 (3)
O2W—H2WB···O4	0.81 (2)	2.28 (2)	3.094 (3)	176 (5)
O5—H5O···O2Wv	0.83	1.75	2.570 (3)	169
O10—H10O···O3vi	0.83	1.81	2.597 (2)	158
C27—H27C···O3vii	0.97	2.55	3.480 (4)	161
C22—H22···Cg1iv	0.94	2.76	3.635 (3)	155

CgI	CgJ	Centroid-to-Centroid
Cg1	Cg5i	3.7818 (14)
Cg2	Cg3ii	3.9022 (13)
Cg2	Cg4ii	3.8946 (15)
Cg2	Cg5ii	3.5442 (14)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1–C5.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O9i	0.82 (2)	2.03 (3)	2.832 (3)	166 (4)
O1W—H1WB⋯O4ii	0.84 (3)	2.15 (3)	2.942 (3)	158 (3)
O2—H2O⋯O7iii	0.83	1.65	2.399 (2)	148
N3—H3⋯O1W	0.87	2.01	2.845 (3)	161
N3—H3⋯N4	0.87	2.38	2.728 (3)	105
O2W—H2WA⋯O8iv	0.84 (3)	1.99 (3)	2.785 (3)	156 (3)
O2W—H2WA⋯O9iv	0.84 (3)	2.55 (3)	3.267 (3)	144 (3)
O2W—H2WB⋯O4	0.81 (2)	2.28 (2)	3.094 (3)	176 (5)
O5—H5O⋯O2Wv	0.83	1.75	2.570 (3)	169
O10—H10O⋯O3vi	0.83	1.81	2.597 (2)	158
C27—H27C⋯O3vii	0.97	2.55	3.480 (4)	161
C22—H22⋯Cg1iv	0.94	2.76	3.635 (3)	155

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