Bis(8-hy-droxy-2-methyl-quinolinium) bis-(pyridine-2,6-dicarboxyl-ato)-nickelate(II) methanol monosolvate monohydrate.

In the title compound, (C(10)H(10)NO)(2)[Ni(C(7)H(3)NO(4))(2)]·CH(3)OH·H(2)O, the coordination geometry of the Ni(II) atom can be described as distorted octa-hedral. In the crystal, noncovalent inter-actions play an important role in the stabilization of the structure, involving O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds and π-π stacking inter-actions between the pyridine rings of the pyridine-2,6-dicarboxyl-ate ligands [centroid-centroid distance = 3.7138 (15) Å] and between the 8-hy-droxy-2-methyl-quinolinium cations [centroid-centroid distances = 3.6737 (15), 3.4434 (14), 3.6743 (15), 3.7541 (16), 3.5020 (15) and 3.7947 (15) Å].

Related literature

For general background to proton transfer compounds based on carb­oxy­lic acid derivatives, see: Aghabozorg et al. (2008 ▶); Eshtiagh-Hosseini, Aghabozorg et al. (2010 ▶); Eshtiagh-Hosseini, Alfi et al. (2010 ▶); Eshtiagh-Hosseini, Yousefi et al. (2010 ▶). For related structures, see: Aghabozorg et al. (2011 ▶); Pasdar et al. (2011 ▶).

Experimental

Crystal data

(C10H10NO)2[Ni(C7H3NO4)2]·CH4O·H2O

M = 759.34

Triclinic,

a = 10.100 (2) Å

b = 12.733 (3) Å

c = 14.638 (3) Å

α = 115.45 (3)°

β = 98.73 (3)°

γ = 95.89 (3)°

V = 1650.2 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.66 mm−1

T = 120 K

0.50 × 0.50 × 0.23 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.723, T max = 0.856

18115 measured reflections

8795 independent reflections

7132 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.05

8795 reflections

492 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.35 e Å−3

Δρmin = −1.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021015/hy2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021015/hy2430Isup2.hkl

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

(C10H10NO)2[Ni(C7H3NO4)2]·CH4O·H2O	Z = 2
Mr = 759.34	F(000) = 788
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.100 (2) Å	Cell parameters from 8795 reflections
b = 12.733 (3) Å	θ = 2.1–29.1°
c = 14.638 (3) Å	µ = 0.66 mm−1
α = 115.45 (3)°	T = 120 K
β = 98.73 (3)°	Block, green
γ = 95.89 (3)°	0.50 × 0.50 × 0.23 mm
V = 1650.2 (8) Å3

Stoe IPDS II diffractometer	8795 independent reflections
Radiation source: fine-focus sealed tube	7132 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 29.1°, θmin = 2.1°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −13→13
Tmin = 0.723, Tmax = 0.856	k = −17→17
18115 measured reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
8795 reflections	(Δ/σ)max < 0.001
492 parameters	Δρmax = 1.35 e Å−3
4 restraints	Δρmin = −1.17 e Å−3

	x	y	z	Uiso*/Ueq
Ni1	0.48763 (3)	0.22447 (2)	0.253563 (19)	0.01440 (9)
O1	0.31109 (16)	0.28626 (14)	0.21116 (11)	0.0203 (3)
O2	0.10747 (16)	0.21828 (15)	0.10010 (13)	0.0251 (3)
O3	0.61797 (15)	0.09757 (14)	0.23722 (12)	0.0213 (3)
O4	0.62645 (19)	−0.09259 (16)	0.13845 (14)	0.0307 (4)
O5	0.39775 (15)	0.19150 (14)	0.36350 (12)	0.0199 (3)
O6	0.42156 (16)	0.25518 (16)	0.53527 (13)	0.0253 (3)
O7	0.61440 (16)	0.32453 (13)	0.20438 (11)	0.0198 (3)
O8	0.77752 (18)	0.48837 (15)	0.26964 (13)	0.0286 (4)
O9	0.83619 (15)	−0.06433 (14)	0.67019 (13)	0.0220 (3)
H9A	0.7626	−0.1060	0.6597	0.033*
O10	−0.02135 (18)	0.58541 (16)	0.83206 (14)	0.0277 (4)
H10A	−0.0602	0.6421	0.8462	0.042*
O11	0.87763 (18)	0.13711 (17)	0.34025 (16)	0.0314 (4)
O12	0.4661 (4)	0.3460 (3)	0.0331 (3)	0.0818 (10)
N1	0.38462 (18)	0.08308 (15)	0.12842 (13)	0.0163 (3)
N2	0.58956 (17)	0.35510 (15)	0.38661 (13)	0.0148 (3)
N3	1.04662 (17)	0.04876 (16)	0.63184 (13)	0.0158 (3)
N4	0.11624 (18)	0.42168 (16)	0.84640 (14)	0.0188 (3)
C1	0.2237 (2)	0.20798 (19)	0.13492 (16)	0.0186 (4)
C2	0.2634 (2)	0.08790 (19)	0.08134 (15)	0.0178 (4)
C3	0.1854 (2)	−0.0107 (2)	−0.00518 (17)	0.0254 (5)
H3	0.1011	−0.0070	−0.0382	0.030*
C4	0.2365 (3)	−0.1150 (2)	−0.04118 (17)	0.0275 (5)
H4	0.1863	−0.1823	−0.0990	0.033*
C5	0.3623 (3)	−0.11857 (19)	0.00914 (17)	0.0247 (5)
H5	0.3977	−0.1878	−0.0143	0.030*
C6	0.4345 (2)	−0.01672 (18)	0.09532 (16)	0.0179 (4)
C7	0.5721 (2)	−0.00531 (19)	0.16093 (17)	0.0207 (4)
C8	0.4523 (2)	0.26155 (19)	0.45925 (16)	0.0177 (4)
C9	0.5642 (2)	0.36054 (18)	0.47561 (15)	0.0156 (4)
C10	0.6345 (2)	0.45077 (19)	0.57041 (16)	0.0187 (4)
H10	0.6156	0.4548	0.6319	0.022*
C11	0.7344 (2)	0.5355 (2)	0.57129 (16)	0.0219 (4)
H11	0.7840	0.5967	0.6339	0.026*
C12	0.7593 (2)	0.5279 (2)	0.47794 (17)	0.0222 (4)
H12	0.8257	0.5838	0.4773	0.027*
C13	0.6835 (2)	0.43572 (18)	0.38596 (15)	0.0169 (4)
C14	0.6943 (2)	0.41509 (19)	0.27724 (16)	0.0195 (4)
C15	1.2834 (2)	0.0523 (2)	0.61385 (17)	0.0207 (4)
H15A	1.3271	0.0745	0.6842	0.031*
H15B	1.3431	0.0846	0.5832	0.031*
H15C	1.2632	−0.0324	0.5752	0.031*
C16	1.1540 (2)	0.09952 (19)	0.61216 (15)	0.0171 (4)
C17	1.1436 (2)	0.1982 (2)	0.59303 (16)	0.0211 (4)
H17	1.2167	0.2331	0.5775	0.025*
C18	1.0255 (2)	0.2424 (2)	0.59747 (17)	0.0216 (4)
H18	1.0197	0.3083	0.5859	0.026*
C19	0.9126 (2)	0.18995 (18)	0.61924 (16)	0.0182 (4)
C20	0.7884 (2)	0.2320 (2)	0.62389 (17)	0.0226 (4)
H20	0.7787	0.2982	0.6136	0.027*
C21	0.6821 (2)	0.1746 (2)	0.64367 (18)	0.0233 (4)
H21	0.6005	0.2025	0.6468	0.028*
C22	0.6949 (2)	0.0737 (2)	0.65937 (17)	0.0216 (4)
H22	0.6214	0.0359	0.6722	0.026*
C23	0.8152 (2)	0.03039 (18)	0.65586 (15)	0.0176 (4)
C24	0.9258 (2)	0.08958 (18)	0.63603 (15)	0.0166 (4)
C25	0.3355 (2)	0.3609 (2)	0.8390 (2)	0.0311 (5)
H25A	0.3341	0.3696	0.7769	0.047*
H25B	0.3731	0.2925	0.8327	0.047*
H25C	0.3906	0.4301	0.8972	0.047*
C26	0.1934 (2)	0.3462 (2)	0.85504 (16)	0.0219 (4)
C27	0.1390 (2)	0.2585 (2)	0.87963 (17)	0.0239 (4)
H27	0.1915	0.2046	0.8850	0.029*
C28	0.0084 (2)	0.2513 (2)	0.89586 (16)	0.0227 (4)
H28	−0.0273	0.1921	0.9113	0.027*
C29	−0.0716 (2)	0.33329 (19)	0.88931 (15)	0.0192 (4)
C30	−0.2050 (2)	0.3338 (2)	0.90747 (18)	0.0251 (4)
H30	−0.2452	0.2779	0.9248	0.030*
C31	−0.2747 (2)	0.4172 (2)	0.89942 (18)	0.0259 (5)
H31	−0.3625	0.4169	0.9116	0.031*
C32	−0.2177 (2)	0.5032 (2)	0.87334 (17)	0.0234 (4)
H32	−0.2679	0.5583	0.8680	0.028*
C33	−0.0865 (2)	0.50617 (19)	0.85547 (16)	0.0199 (4)
C34	−0.0139 (2)	0.42021 (19)	0.86331 (15)	0.0171 (4)
C35	0.9526 (3)	0.2250 (3)	0.3241 (3)	0.0370 (6)
H35A	0.9536	0.1951	0.2518	0.056*
H35B	1.0444	0.2461	0.3638	0.056*
H35C	0.9107	0.2937	0.3456	0.056*
H3A	1.060 (3)	−0.010 (3)	0.640 (2)	0.030 (8)*
H4A	0.154 (3)	0.468 (3)	0.825 (3)	0.040 (9)*
H11A	0.794 (4)	0.117 (3)	0.304 (3)	0.051 (10)*
H12A	0.516 (4)	0.350 (4)	0.085 (3)	0.076*
H12B	0.419 (4)	0.291 (3)	−0.020 (2)	0.076*

	U11	U22	U33	U12	U13	U23
Ni1	0.01386 (13)	0.01242 (13)	0.01467 (13)	−0.00045 (9)	0.00241 (9)	0.00496 (10)
O1	0.0209 (7)	0.0180 (7)	0.0190 (7)	0.0041 (6)	0.0015 (6)	0.0063 (6)
O2	0.0182 (7)	0.0275 (8)	0.0287 (8)	0.0042 (6)	0.0006 (6)	0.0135 (7)
O3	0.0185 (7)	0.0215 (8)	0.0239 (7)	0.0048 (6)	0.0046 (6)	0.0101 (6)
O4	0.0376 (10)	0.0272 (9)	0.0353 (9)	0.0177 (8)	0.0153 (8)	0.0164 (8)
O5	0.0176 (7)	0.0198 (7)	0.0218 (7)	−0.0027 (6)	0.0049 (6)	0.0102 (6)
O6	0.0224 (8)	0.0343 (9)	0.0252 (8)	0.0001 (7)	0.0080 (6)	0.0192 (7)
O7	0.0233 (7)	0.0179 (7)	0.0152 (6)	−0.0015 (6)	0.0052 (6)	0.0055 (6)
O8	0.0325 (9)	0.0242 (8)	0.0258 (8)	−0.0073 (7)	0.0148 (7)	0.0085 (7)
O9	0.0155 (7)	0.0219 (8)	0.0323 (8)	−0.0004 (6)	0.0055 (6)	0.0165 (7)
O10	0.0278 (8)	0.0280 (9)	0.0395 (9)	0.0097 (7)	0.0165 (7)	0.0225 (8)
O11	0.0183 (8)	0.0322 (9)	0.0500 (11)	0.0004 (7)	0.0011 (7)	0.0273 (9)
O12	0.100 (3)	0.080 (2)	0.0591 (18)	0.031 (2)	0.0050 (18)	0.0261 (17)
N1	0.0170 (8)	0.0145 (8)	0.0168 (8)	0.0001 (6)	0.0054 (6)	0.0068 (6)
N2	0.0131 (7)	0.0141 (8)	0.0160 (7)	0.0005 (6)	0.0044 (6)	0.0056 (6)
N3	0.0151 (8)	0.0147 (8)	0.0161 (7)	−0.0007 (6)	0.0035 (6)	0.0063 (6)
N4	0.0177 (8)	0.0189 (8)	0.0175 (8)	0.0005 (7)	0.0057 (6)	0.0063 (7)
C1	0.0195 (9)	0.0204 (10)	0.0169 (9)	0.0033 (8)	0.0048 (7)	0.0092 (8)
C2	0.0170 (9)	0.0193 (10)	0.0150 (9)	−0.0006 (8)	0.0042 (7)	0.0064 (8)
C3	0.0223 (10)	0.0287 (12)	0.0183 (10)	−0.0041 (9)	0.0029 (8)	0.0067 (9)
C4	0.0319 (12)	0.0228 (11)	0.0173 (10)	−0.0079 (9)	0.0059 (9)	0.0022 (8)
C5	0.0382 (13)	0.0139 (9)	0.0206 (10)	0.0002 (9)	0.0139 (9)	0.0053 (8)
C6	0.0221 (10)	0.0154 (9)	0.0179 (9)	0.0014 (8)	0.0097 (7)	0.0078 (8)
C7	0.0232 (10)	0.0202 (10)	0.0239 (10)	0.0060 (8)	0.0114 (8)	0.0123 (8)
C8	0.0143 (9)	0.0201 (10)	0.0220 (9)	0.0024 (7)	0.0052 (7)	0.0124 (8)
C9	0.0141 (8)	0.0174 (9)	0.0174 (9)	0.0022 (7)	0.0045 (7)	0.0095 (7)
C10	0.0204 (9)	0.0204 (10)	0.0158 (9)	0.0040 (8)	0.0059 (7)	0.0080 (8)
C11	0.0224 (10)	0.0193 (10)	0.0168 (9)	−0.0014 (8)	0.0032 (8)	0.0031 (8)
C12	0.0204 (10)	0.0183 (10)	0.0219 (10)	−0.0055 (8)	0.0050 (8)	0.0054 (8)
C13	0.0173 (9)	0.0153 (9)	0.0177 (9)	0.0007 (7)	0.0068 (7)	0.0067 (7)
C14	0.0215 (10)	0.0169 (9)	0.0193 (9)	0.0012 (8)	0.0092 (8)	0.0066 (8)
C15	0.0148 (9)	0.0247 (10)	0.0211 (10)	0.0003 (8)	0.0039 (7)	0.0098 (8)
C16	0.0145 (9)	0.0200 (9)	0.0128 (8)	−0.0026 (7)	0.0022 (7)	0.0053 (7)
C17	0.0221 (10)	0.0209 (10)	0.0189 (9)	−0.0035 (8)	0.0053 (8)	0.0090 (8)
C18	0.0255 (11)	0.0192 (10)	0.0212 (10)	0.0001 (8)	0.0044 (8)	0.0113 (8)
C19	0.0189 (9)	0.0171 (9)	0.0164 (9)	−0.0006 (8)	0.0029 (7)	0.0069 (7)
C20	0.0243 (10)	0.0202 (10)	0.0233 (10)	0.0044 (8)	0.0043 (8)	0.0101 (8)
C21	0.0182 (10)	0.0247 (11)	0.0254 (10)	0.0050 (8)	0.0045 (8)	0.0098 (9)
C22	0.0165 (9)	0.0227 (10)	0.0240 (10)	0.0003 (8)	0.0046 (8)	0.0099 (8)
C23	0.0167 (9)	0.0169 (9)	0.0167 (9)	−0.0009 (7)	0.0025 (7)	0.0067 (7)
C24	0.0160 (9)	0.0165 (9)	0.0138 (8)	−0.0010 (7)	0.0018 (7)	0.0050 (7)
C25	0.0181 (10)	0.0263 (12)	0.0396 (13)	0.0032 (9)	0.0066 (9)	0.0067 (10)
C26	0.0198 (10)	0.0194 (10)	0.0190 (9)	0.0024 (8)	0.0029 (8)	0.0026 (8)
C27	0.0255 (11)	0.0199 (10)	0.0220 (10)	0.0053 (8)	0.0009 (8)	0.0065 (8)
C28	0.0294 (11)	0.0194 (10)	0.0181 (9)	0.0003 (8)	0.0036 (8)	0.0088 (8)
C29	0.0214 (10)	0.0198 (10)	0.0135 (8)	−0.0004 (8)	0.0041 (7)	0.0056 (7)
C30	0.0243 (11)	0.0264 (11)	0.0235 (10)	−0.0025 (9)	0.0100 (8)	0.0103 (9)
C31	0.0178 (10)	0.0286 (12)	0.0270 (11)	0.0013 (9)	0.0099 (8)	0.0076 (9)
C32	0.0205 (10)	0.0235 (11)	0.0242 (10)	0.0058 (8)	0.0070 (8)	0.0081 (9)
C33	0.0208 (10)	0.0197 (10)	0.0187 (9)	0.0020 (8)	0.0051 (8)	0.0083 (8)
C34	0.0165 (9)	0.0190 (9)	0.0138 (8)	0.0015 (7)	0.0050 (7)	0.0057 (7)
C35	0.0280 (12)	0.0318 (13)	0.0547 (17)	−0.0047 (10)	−0.0021 (11)	0.0284 (13)

Ni1—N2	1.969 (2)	C11—C12	1.392 (3)
Ni1—N1	1.970 (2)	C11—H11	0.9300
Ni1—O7	2.1247 (16)	C12—C13	1.386 (3)
Ni1—O5	2.1298 (16)	C12—H12	0.9300
Ni1—O1	2.1343 (16)	C13—C14	1.521 (3)
Ni1—O3	2.1449 (16)	C15—C16	1.495 (3)
O1—C1	1.258 (3)	C15—H15A	0.9600
O2—C1	1.250 (3)	C15—H15B	0.9600
O3—C7	1.280 (3)	C15—H15C	0.9600
O4—C7	1.229 (3)	C16—C17	1.410 (3)
O5—C8	1.286 (3)	C17—C18	1.369 (3)
O6—C8	1.232 (3)	C17—H17	0.9300
O7—C14	1.269 (3)	C18—C19	1.409 (3)
O8—C14	1.243 (3)	C18—H18	0.9300
O9—C23	1.342 (3)	C19—C20	1.413 (3)
O9—H9A	0.8200	C19—C24	1.417 (3)
O10—C33	1.341 (3)	C20—C21	1.373 (3)
O10—H10A	0.8200	C20—H20	0.9300
O11—C35	1.411 (3)	C21—C22	1.413 (3)
O11—H11A	0.87 (4)	C21—H21	0.9300
O12—H12A	0.82 (2)	C22—C23	1.384 (3)
O12—H12B	0.82 (2)	C22—H22	0.9300
N1—C2	1.332 (3)	C23—C24	1.419 (3)
N1—C6	1.334 (3)	C25—C26	1.495 (3)
N2—C13	1.329 (3)	C25—H25A	0.9600
N2—C9	1.340 (3)	C25—H25B	0.9600
N3—C16	1.337 (3)	C25—H25C	0.9600
N3—C24	1.374 (3)	C26—C27	1.400 (3)
N3—H3A	0.82 (3)	C27—C28	1.376 (3)
N4—C26	1.333 (3)	C27—H27	0.9300
N4—C34	1.374 (3)	C28—C29	1.410 (3)
N4—H4A	0.86 (3)	C28—H28	0.9300
C1—C2	1.518 (3)	C29—C30	1.412 (3)
C2—C3	1.389 (3)	C29—C34	1.416 (3)
C3—C4	1.389 (4)	C30—C31	1.368 (4)
C3—H3	0.9300	C30—H30	0.9300
C4—C5	1.384 (4)	C31—C32	1.405 (3)
C4—H4	0.9300	C31—H31	0.9300
C5—C6	1.388 (3)	C32—C33	1.389 (3)
C5—H5	0.9300	C32—H32	0.9300
C6—C7	1.519 (3)	C33—C34	1.413 (3)
C8—C9	1.513 (3)	C35—H35A	0.9600
C9—C10	1.383 (3)	C35—H35B	0.9600
C10—C11	1.394 (3)	C35—H35C	0.9600
C10—H10	0.9300
N2—Ni1—N1	173.76 (7)	O8—C14—C13	117.26 (19)
N2—Ni1—O7	78.07 (7)	O7—C14—C13	115.06 (18)
N1—Ni1—O7	107.32 (7)	C16—C15—H15A	109.5
N2—Ni1—O5	77.35 (7)	C16—C15—H15B	109.5
N1—Ni1—O5	97.45 (7)	H15A—C15—H15B	109.5
O7—Ni1—O5	155.11 (6)	C16—C15—H15C	109.5
N2—Ni1—O1	105.25 (7)	H15A—C15—H15C	109.5
N1—Ni1—O1	77.98 (7)	H15B—C15—H15C	109.5
O7—Ni1—O1	92.46 (6)	N3—C16—C17	119.24 (19)
O5—Ni1—O1	90.26 (6)	N3—C16—C15	119.15 (19)
N2—Ni1—O3	99.28 (7)	C17—C16—C15	121.58 (19)
N1—Ni1—O3	77.43 (7)	C18—C17—C16	119.7 (2)
O7—Ni1—O3	94.27 (6)	C18—C17—H17	120.1
O5—Ni1—O3	93.46 (6)	C16—C17—H17	120.1
O1—Ni1—O3	155.41 (6)	C17—C18—C19	121.2 (2)
C1—O1—Ni1	114.11 (14)	C17—C18—H18	119.4
C7—O3—Ni1	115.21 (13)	C19—C18—H18	119.4
C8—O5—Ni1	115.57 (13)	C18—C19—C20	123.2 (2)
C14—O7—Ni1	114.82 (13)	C18—C19—C24	117.50 (19)
C23—O9—H9A	109.5	C20—C19—C24	119.32 (19)
C33—O10—H10A	109.5	C21—C20—C19	119.7 (2)
C35—O11—H11A	111 (3)	C21—C20—H20	120.2
H12A—O12—H12B	134 (4)	C19—C20—H20	120.2
C2—N1—C6	121.35 (19)	C20—C21—C22	121.0 (2)
C2—N1—Ni1	119.01 (14)	C20—C21—H21	119.5
C6—N1—Ni1	119.57 (14)	C22—C21—H21	119.5
C13—N2—C9	121.36 (18)	C23—C22—C21	120.9 (2)
C13—N2—Ni1	118.90 (14)	C23—C22—H22	119.5
C9—N2—Ni1	119.74 (14)	C21—C22—H22	119.5
C16—N3—C24	122.90 (18)	O9—C23—C22	124.84 (19)
C16—N3—H3A	113 (2)	O9—C23—C24	116.69 (18)
C24—N3—H3A	124 (2)	C22—C23—C24	118.46 (19)
C26—N4—C34	123.3 (2)	N3—C24—C19	119.42 (18)
C26—N4—H4A	113 (2)	N3—C24—C23	119.95 (19)
C34—N4—H4A	123 (2)	C19—C24—C23	120.62 (19)
O2—C1—O1	126.9 (2)	C26—C25—H25A	109.5
O2—C1—C2	116.94 (19)	C26—C25—H25B	109.5
O1—C1—C2	116.19 (18)	H25A—C25—H25B	109.5
N1—C2—C3	121.0 (2)	C26—C25—H25C	109.5
N1—C2—C1	112.51 (18)	H25A—C25—H25C	109.5
C3—C2—C1	126.51 (19)	H25B—C25—H25C	109.5
C2—C3—C4	118.4 (2)	N4—C26—C27	119.0 (2)
C2—C3—H3	120.8	N4—C26—C25	117.8 (2)
C4—C3—H3	120.8	C27—C26—C25	123.2 (2)
C5—C4—C3	119.9 (2)	C28—C27—C26	120.4 (2)
C5—C4—H4	120.1	C28—C27—H27	119.8
C3—C4—H4	120.1	C26—C27—H27	119.8
C4—C5—C6	118.6 (2)	C27—C28—C29	120.4 (2)
C4—C5—H5	120.7	C27—C28—H28	119.8
C6—C5—H5	120.7	C29—C28—H28	119.8
N1—C6—C5	120.8 (2)	C28—C29—C30	123.9 (2)
N1—C6—C7	113.46 (18)	C28—C29—C34	117.7 (2)
C5—C6—C7	125.7 (2)	C30—C29—C34	118.4 (2)
O4—C7—O3	126.7 (2)	C31—C30—C29	119.6 (2)
O4—C7—C6	119.0 (2)	C31—C30—H30	120.2
O3—C7—C6	114.29 (18)	C29—C30—H30	120.2
O6—C8—O5	126.6 (2)	C30—C31—C32	122.0 (2)
O6—C8—C9	119.24 (19)	C30—C31—H31	119.0
O5—C8—C9	114.17 (18)	C32—C31—H31	119.0
N2—C9—C10	121.21 (19)	C33—C32—C31	120.2 (2)
N2—C9—C8	112.99 (18)	C33—C32—H32	119.9
C10—C9—C8	125.79 (18)	C31—C32—H32	119.9
C9—C10—C11	118.25 (19)	O10—C33—C32	125.2 (2)
C9—C10—H10	120.9	O10—C33—C34	116.59 (19)
C11—C10—H10	120.9	C32—C33—C34	118.2 (2)
C12—C11—C10	119.6 (2)	N4—C34—C33	119.24 (19)
C12—C11—H11	120.2	N4—C34—C29	119.19 (19)
C10—C11—H11	120.2	C33—C34—C29	121.57 (19)
C13—C12—C11	118.8 (2)	O11—C35—H35A	109.5
C13—C12—H12	120.6	O11—C35—H35B	109.5
C11—C12—H12	120.6	H35A—C35—H35B	109.5
N2—C13—C12	120.76 (19)	O11—C35—H35C	109.5
N2—C13—C14	113.11 (18)	H35A—C35—H35C	109.5
C12—C13—C14	126.12 (19)	H35B—C35—H35C	109.5
O8—C14—O7	127.7 (2)
N2—Ni1—O1—C1	−170.54 (14)	Ni1—N2—C9—C8	−1.5 (2)
N1—Ni1—O1—C1	3.97 (15)	O6—C8—C9—N2	178.34 (18)
O7—Ni1—O1—C1	111.16 (15)	O5—C8—C9—N2	−2.0 (2)
O5—Ni1—O1—C1	−93.59 (15)	O6—C8—C9—C10	−2.9 (3)
O3—Ni1—O1—C1	5.3 (2)	O5—C8—C9—C10	176.70 (19)
N2—Ni1—O3—C7	173.19 (15)	N2—C9—C10—C11	−0.9 (3)
N1—Ni1—O3—C7	−1.41 (15)	C8—C9—C10—C11	−179.59 (19)
O7—Ni1—O3—C7	−108.22 (15)	C9—C10—C11—C12	0.7 (3)
O5—Ni1—O3—C7	95.46 (15)	C10—C11—C12—C13	0.1 (3)
O1—Ni1—O3—C7	−2.7 (2)	C9—N2—C13—C12	0.5 (3)
N2—Ni1—O5—C8	−4.03 (14)	Ni1—N2—C13—C12	−178.84 (16)
N1—Ni1—O5—C8	172.48 (14)	C9—N2—C13—C14	−178.75 (17)
O7—Ni1—O5—C8	−13.2 (2)	Ni1—N2—C13—C14	1.9 (2)
O1—Ni1—O5—C8	−109.61 (15)	C11—C12—C13—N2	−0.7 (3)
O3—Ni1—O5—C8	94.72 (15)	C11—C12—C13—C14	178.5 (2)
N2—Ni1—O7—C14	1.19 (15)	Ni1—O7—C14—O8	−179.45 (19)
N1—Ni1—O7—C14	−175.57 (14)	Ni1—O7—C14—C13	−0.5 (2)
O5—Ni1—O7—C14	10.3 (2)	N2—C13—C14—O8	178.21 (19)
O1—Ni1—O7—C14	106.26 (15)	C12—C13—C14—O8	−1.0 (3)
O3—Ni1—O7—C14	−97.41 (15)	N2—C13—C14—O7	−0.8 (3)
O7—Ni1—N1—C2	−90.88 (16)	C12—C13—C14—O7	180.0 (2)
O5—Ni1—N1—C2	86.61 (16)	C24—N3—C16—C17	−1.1 (3)
O1—Ni1—N1—C2	−2.05 (15)	C24—N3—C16—C15	177.27 (18)
O3—Ni1—N1—C2	178.52 (16)	N3—C16—C17—C18	1.7 (3)
O7—Ni1—N1—C6	92.11 (16)	C15—C16—C17—C18	−176.62 (19)
O5—Ni1—N1—C6	−90.39 (16)	C16—C17—C18—C19	−1.1 (3)
O1—Ni1—N1—C6	−179.06 (16)	C17—C18—C19—C20	−179.5 (2)
O3—Ni1—N1—C6	1.51 (15)	C17—C18—C19—C24	−0.2 (3)
O7—Ni1—N2—C13	−1.72 (15)	C18—C19—C20—C21	178.8 (2)
O5—Ni1—N2—C13	−177.78 (16)	C24—C19—C20—C21	−0.6 (3)
O1—Ni1—N2—C13	−91.02 (15)	C19—C20—C21—C22	−0.1 (3)
O3—Ni1—N2—C13	90.73 (15)	C20—C21—C22—C23	0.4 (3)
O7—Ni1—N2—C9	178.94 (16)	C21—C22—C23—O9	179.8 (2)
O5—Ni1—N2—C9	2.87 (14)	C21—C22—C23—C24	0.0 (3)
O1—Ni1—N2—C9	89.63 (15)	C16—N3—C24—C19	−0.2 (3)
O3—Ni1—N2—C9	−88.62 (15)	C16—N3—C24—C23	179.11 (18)
Ni1—O1—C1—O2	173.66 (18)	C18—C19—C24—N3	0.8 (3)
Ni1—O1—C1—C2	−5.0 (2)	C20—C19—C24—N3	−179.81 (18)
C6—N1—C2—C3	−1.1 (3)	C18—C19—C24—C23	−178.48 (18)
Ni1—N1—C2—C3	−178.01 (16)	C20—C19—C24—C23	0.9 (3)
C6—N1—C2—C1	177.15 (17)	O9—C23—C24—N3	0.3 (3)
Ni1—N1—C2—C1	0.2 (2)	C22—C23—C24—N3	−179.88 (19)
O2—C1—C2—N1	−175.41 (18)	O9—C23—C24—C19	179.56 (18)
O1—C1—C2—N1	3.4 (3)	C22—C23—C24—C19	−0.6 (3)
O2—C1—C2—C3	2.7 (3)	C34—N4—C26—C27	1.9 (3)
O1—C1—C2—C3	−178.5 (2)	C34—N4—C26—C25	−177.4 (2)
N1—C2—C3—C4	0.4 (3)	N4—C26—C27—C28	−0.8 (3)
C1—C2—C3—C4	−177.5 (2)	C25—C26—C27—C28	178.4 (2)
C2—C3—C4—C5	0.0 (3)	C26—C27—C28—C29	−0.9 (3)
C3—C4—C5—C6	0.2 (3)	C27—C28—C29—C30	−178.3 (2)
C2—N1—C6—C5	1.2 (3)	C27—C28—C29—C34	1.4 (3)
Ni1—N1—C6—C5	178.16 (15)	C28—C29—C30—C31	179.9 (2)
C2—N1—C6—C7	−178.34 (18)	C34—C29—C30—C31	0.1 (3)
Ni1—N1—C6—C7	−1.4 (2)	C29—C30—C31—C32	0.1 (4)
C4—C5—C6—N1	−0.8 (3)	C30—C31—C32—C33	−0.4 (4)
C4—C5—C6—C7	178.7 (2)	C31—C32—C33—O10	−178.7 (2)
Ni1—O3—C7—O4	−177.46 (19)	C31—C32—C33—C34	0.6 (3)
Ni1—O3—C7—C6	1.1 (2)	C26—N4—C34—C33	178.0 (2)
N1—C6—C7—O4	178.78 (19)	C26—N4—C34—C29	−1.3 (3)
C5—C6—C7—O4	−0.8 (3)	O10—C33—C34—N4	−0.4 (3)
N1—C6—C7—O3	0.1 (3)	C32—C33—C34—N4	−179.72 (19)
C5—C6—C7—O3	−179.4 (2)	O10—C33—C34—C29	178.94 (19)
Ni1—O5—C8—O6	−176.08 (17)	C32—C33—C34—C29	−0.4 (3)
Ni1—O5—C8—C9	4.3 (2)	C28—C29—C34—N4	−0.4 (3)
C13—N2—C9—C10	0.3 (3)	C30—C29—C34—N4	179.36 (19)
Ni1—N2—C9—C10	179.66 (14)	C28—C29—C34—C33	−179.72 (19)
C13—N2—C9—C8	179.14 (17)	C30—C29—C34—C33	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O7i	0.93	2.54	3.164 (3)	124.
C11—H11···O1ii	0.93	2.52	3.154 (3)	126.
C15—H15A···O4iii	0.96	2.47	3.398 (3)	162.
C17—H17···O6iv	0.93	2.27	3.155 (3)	158.
C21—H21···O6	0.93	2.58	3.344 (3)	139.
C25—H25A···O8ii	0.96	2.50	3.169 (3)	127.
C27—H27···O4v	0.93	2.42	3.298 (3)	158.
N3—H3A···O11iii	0.82 (3)	1.92 (3)	2.732 (3)	171 (3)
N4—H4A···O8ii	0.86 (3)	1.89 (3)	2.706 (3)	157 (3)
O9—H9A···O5v	0.82	1.75	2.574 (2)	178.
O10—H10A···O2vi	0.82	1.76	2.562 (2)	166.
O11—H11A···O3	0.87 (4)	1.83 (4)	2.699 (2)	171 (4)
O12—H12A···O7	0.82 (2)	2.05 (2)	2.852 (4)	167 (5)
O12—H12B···O4i	0.82 (2)	2.32 (3)	3.049 (4)	149 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O7i	0.93	2.54	3.164 (3)	124
C11—H11⋯O1ii	0.93	2.52	3.154 (3)	126
C15—H15A⋯O4iii	0.96	2.47	3.398 (3)	162
C17—H17⋯O6iv	0.93	2.27	3.155 (3)	158
C21—H21⋯O6	0.93	2.58	3.344 (3)	139
C25—H25A⋯O8ii	0.96	2.50	3.169 (3)	127
C27—H27⋯O4v	0.93	2.42	3.298 (3)	158
N3—H3A⋯O11iii	0.82 (3)	1.92 (3)	2.732 (3)	171 (3)
N4—H4A⋯O8ii	0.86 (3)	1.89 (3)	2.706 (3)	157 (3)
O9—H9A⋯O5v	0.82	1.75	2.574 (2)	178
O10—H10A⋯O2vi	0.82	1.76	2.562 (2)	166
O11—H11A⋯O3	0.87 (4)	1.83 (4)	2.699 (2)	171 (4)
O12—H12A⋯O7	0.82 (2)	2.05 (2)	2.852 (4)	167 (5)
O12—H12B⋯O4i	0.82 (2)	2.32 (3)	3.049 (4)	149 (4)

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