Tris(2,2'-bi-1H-imidazole-κN,N)-nickel(II) dinitrate N,N-dimethyl-formamide monosolvate.

The reaction of nickel salts and 4,4'-bipyridine with 2,2'-bi-imidazole (H(2)biim) yielded the title complex, [Ni(C(6)H(6)N(4))(3)](NO(3))(2)·C(3)H(7)NO. The Ni(II) atom is chelated by three H(2)biim ligands in a distorted octa-hedral coordination geometry. The two nitrate anions and one dimethyl-formamide (DMF) mol-ecule are not coordinated. The compound has a three-dimensional structure, formed by extensive hydrogen bonding between [Ni(H(2)biim)(3)](2+) cations and nitrate anions, each nitrate anion forming hydrogen bonds with an R(1) (2)(4) motif. The DMF molecule is disordered over three sets of sites, with occupancy ratios of 0.341 (16):0.350 (17):0.309 (19).

Related literature

For related literature on the 2,2′-biimidazole ligand, see: Ding et al. (2005 ▶); Gruia et al. (2007 ▶); Martinez Lorente et al. (1995 ▶). For related structures, see: Dai et al. (2010 ▶); Jin et al. (2010 ▶); Yang et al. (2005 ▶).

Experimental

Crystal data

[Ni(C6H6N4)3](NO3)2·C3H7NO

M = 658.27

Monoclinic,

a = 12.2150 (11) Å

b = 20.864 (2) Å

c = 12.1080 (12) Å

β = 90.528 (1)°

V = 3085.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 298 K

0.36 × 0.19 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.788, T max = 0.921

7496 measured reflections

4289 independent reflections

1969 reflections with I > 2σ(I)

R int = 0.131

Refinement

R[F 2 > 2σ(F 2)] = 0.109

wR(F 2) = 0.276

S = 1.06

4289 reflections

437 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.61 e Å−3

Absolute structure: Flack (1983 ▶), 2702 Friedel pairs

Flack parameter: 0.00 (6)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043030/zk2032sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043030/zk2032Isup2.hkl

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

[Ni(C6H6N4)3](NO3)2·C3H7NO	F(000) = 1360
Mr = 658.27	Dx = 1.417 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2150 (11) Å	Cell parameters from 1160 reflections
b = 20.864 (2) Å	θ = 2.5–17.3°
c = 12.1080 (12) Å	µ = 0.69 mm−1
β = 90.528 (1)°	T = 298 K
V = 3085.6 (5) Å3	Block, purple
Z = 4	0.36 × 0.19 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	4289 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
graphite	Rint = 0.131
phi and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
Tmin = 0.788, Tmax = 0.921	k = −23→24
7496 measured reflections	l = −14→13

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)] = 0.109	H-atom parameters constrained
wR(F2) = 0.276	w = 1/[σ2(Fo2) + (0.117P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4289 reflections	Δρmax = 0.54 e Å−3
437 parameters	Δρmin = −0.61 e Å−3
3 restraints	Absolute structure: Flack (1983), 1549 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

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	Occ. (<1)
Ni1	0.6556 (2)	0.33319 (8)	0.3945 (2)	0.0423 (5)
N1	0.7111 (15)	0.2490 (8)	0.3170 (16)	0.065 (5)
N2	0.6946 (14)	0.1433 (8)	0.3119 (16)	0.075 (5)
H2	0.6816	0.1045	0.3317	0.090*
N3	0.6035 (15)	0.2688 (8)	0.5051 (14)	0.062 (5)
N4	0.5823 (19)	0.1662 (7)	0.5541 (19)	0.072 (6)
H4	0.5800	0.1251	0.5481	0.086*
N5	0.5220 (19)	0.3337 (7)	0.2926 (18)	0.068 (6)
N6	0.3559 (17)	0.3726 (9)	0.2553 (18)	0.085 (6)
H6	0.2946	0.3922	0.2640	0.102*
N7	0.5692 (17)	0.4055 (8)	0.4700 (15)	0.067 (5)
N8	0.4052 (15)	0.4534 (8)	0.4806 (16)	0.079 (6)
H8	0.3384	0.4638	0.4666	0.095*
N9	0.7373 (16)	0.3892 (8)	0.2801 (16)	0.065 (5)
N10	0.8848 (15)	0.4446 (7)	0.2328 (16)	0.067 (5)
H10	0.9503	0.4596	0.2342	0.081*
N11	0.7983 (16)	0.3544 (8)	0.4856 (16)	0.064 (5)
N12	0.9522 (14)	0.4110 (8)	0.4904 (17)	0.076 (5)
H12	1.0047	0.4360	0.4712	0.091*
N13	0.161 (2)	0.4854 (9)	0.0305 (15)	0.072 (5)
N14	0.154 (2)	0.4795 (11)	0.2929 (17)	0.081 (6)
N15	0.102 (8)	0.110 (4)	0.383 (5)	0.103 (14)	0.341 (16)
N16	0.103 (6)	0.237 (4)	0.409 (5)	0.103 (14)	0.350 (17)
N17	0.266 (9)	0.186 (4)	0.395 (7)	0.103 (14)	0.309 (19)
O1	0.0657 (16)	0.4662 (7)	0.0412 (16)	0.102 (5)
O2	0.1804 (15)	0.5453 (8)	0.0304 (14)	0.093 (5)
O3	0.2365 (15)	0.4472 (8)	0.0272 (12)	0.098 (5)
O4	0.2461 (15)	0.5046 (7)	0.2861 (11)	0.081 (4)
O5	0.0835 (15)	0.5192 (7)	0.2951 (14)	0.091 (5)
O6	0.1376 (15)	0.4256 (8)	0.2796 (14)	0.097 (5)
O7	0.266 (6)	0.077 (3)	0.364 (4)	0.104 (11)	0.341 (16)
O8	−0.002 (5)	0.155 (3)	0.400 (4)	0.104 (11)	0.350 (17)
O9	0.358 (5)	0.104 (3)	0.352 (5)	0.104 (11)	0.309 (19)
C1	0.6771 (18)	0.1972 (8)	0.3734 (19)	0.066 (6)
C2	0.737 (3)	0.1628 (11)	0.212 (3)	0.089 (9)
H2B	0.7517	0.1368	0.1521	0.107*
C3	0.7530 (18)	0.2277 (10)	0.219 (2)	0.071 (6)
H3	0.7867	0.2530	0.1663	0.086*
C4	0.6245 (18)	0.2077 (10)	0.4790 (18)	0.068 (6)
C5	0.5439 (16)	0.2016 (10)	0.6411 (19)	0.074 (6)
H5	0.5196	0.1846	0.7075	0.089*
C6	0.5468 (17)	0.2652 (10)	0.6160 (18)	0.074 (6)
H6A	0.5199	0.2991	0.6577	0.089*
C7	0.446 (2)	0.3781 (10)	0.321 (2)	0.075 (7)
C8	0.380 (2)	0.3300 (10)	0.173 (2)	0.088 (7)
H8A	0.3379	0.3212	0.1104	0.106*
C9	0.479 (2)	0.3029 (11)	0.2000 (19)	0.083 (7)
H9	0.5120	0.2692	0.1626	0.099*
C10	0.469 (2)	0.4126 (10)	0.422 (2)	0.073 (7)
C11	0.469 (2)	0.4745 (10)	0.567 (2)	0.080 (7)
H11	0.4484	0.5041	0.6199	0.096*
C12	0.5682 (19)	0.4447 (9)	0.5607 (19)	0.071 (6)
H12A	0.6259	0.4501	0.6105	0.085*
C13	0.833 (2)	0.4131 (9)	0.317 (2)	0.064 (6)
C14	0.8125 (19)	0.4477 (10)	0.147 (2)	0.082 (6)
H14	0.8234	0.4689	0.0801	0.099*
C15	0.7209 (19)	0.4138 (9)	0.1757 (19)	0.073 (6)
H15	0.6584	0.4085	0.1324	0.088*
C16	0.8647 (18)	0.3931 (10)	0.427 (2)	0.062 (6)
C17	0.9403 (19)	0.3817 (11)	0.591 (2)	0.077 (7)
H17	0.9886	0.3849	0.6504	0.092*
C18	0.8452 (18)	0.3468 (9)	0.5885 (19)	0.071 (6)
H18	0.8174	0.3224	0.6461	0.086*
C19	0.176 (8)	0.065 (3)	0.405 (7)	0.097 (15)	0.341 (16)
H19	0.1619	0.0286	0.4466	0.117*	0.341 (16)
C20	0.126 (11)	0.178 (6)	0.403 (10)	0.10 (2)	0.341 (16)
H20A	0.1347	0.1849	0.4811	0.143*	0.341 (16)
H20B	0.0657	0.2034	0.3760	0.143*	0.341 (16)
H20C	0.1914	0.1899	0.3657	0.143*	0.341 (16)
C21	−0.015 (7)	0.094 (4)	0.373 (6)	0.100 (14)	0.341 (16)
H21A	−0.0309	0.0804	0.2988	0.150*	0.341 (16)
H21B	−0.0573	0.1315	0.3897	0.150*	0.341 (16)
H21C	−0.0325	0.0604	0.4236	0.150*	0.341 (16)
C22	0.001 (7)	0.214 (4)	0.413 (6)	0.097 (15)	0.350 (17)
H22	−0.0604	0.2396	0.4246	0.117*	0.350 (17)
C23	0.195 (11)	0.192 (7)	0.390 (9)	0.10 (2)	0.350 (17)
H23A	0.1675	0.1534	0.3550	0.143*	0.350 (17)
H23B	0.2286	0.1809	0.4591	0.143*	0.350 (17)
H23C	0.2477	0.2116	0.3427	0.143*	0.350 (17)
C24	0.135 (6)	0.296 (3)	0.467 (6)	0.100 (14)	0.350 (17)
H24A	0.0830	0.3288	0.4518	0.150*	0.350 (17)
H24B	0.2063	0.3088	0.4425	0.150*	0.350 (17)
H24C	0.1380	0.2875	0.5452	0.150*	0.350 (17)
C25	0.364 (9)	0.159 (5)	0.392 (7)	0.097 (15)	0.309 (19)
H25	0.4286	0.1781	0.4163	0.117*	0.309 (19)
C26	0.166 (12)	0.147 (6)	0.386 (12)	0.10 (2)	0.309 (19)
H26A	0.1795	0.1111	0.3375	0.143*	0.309 (19)
H26B	0.1077	0.1725	0.3559	0.143*	0.309 (19)
H26C	0.1463	0.1313	0.4574	0.143*	0.309 (19)
C27	0.251 (8)	0.256 (4)	0.397 (6)	0.100 (14)	0.309 (19)
H27A	0.2538	0.2709	0.4717	0.150*	0.309 (19)
H27B	0.1813	0.2663	0.3645	0.150*	0.309 (19)
H27C	0.3081	0.2760	0.3552	0.150*	0.309 (19)

	U11	U22	U33	U12	U13	U23
Ni1	0.0549 (11)	0.0431 (10)	0.0289 (10)	0.0010 (13)	−0.0019 (7)	−0.0009 (13)
N1	0.083 (13)	0.054 (10)	0.059 (13)	−0.001 (9)	0.002 (9)	−0.003 (10)
N2	0.113 (15)	0.051 (9)	0.061 (12)	0.011 (8)	0.017 (10)	−0.010 (9)
N3	0.084 (12)	0.052 (10)	0.051 (12)	−0.004 (8)	0.005 (9)	−0.002 (8)
N4	0.108 (18)	0.052 (11)	0.055 (14)	−0.008 (10)	0.012 (12)	0.015 (10)
N5	0.084 (13)	0.059 (10)	0.061 (13)	0.010 (10)	−0.014 (10)	−0.009 (9)
N6	0.096 (15)	0.088 (14)	0.072 (15)	0.023 (12)	−0.014 (13)	−0.004 (11)
N7	0.084 (15)	0.058 (10)	0.058 (13)	0.007 (9)	0.001 (10)	−0.002 (9)
N8	0.094 (14)	0.077 (11)	0.067 (14)	0.039 (10)	0.001 (11)	−0.012 (10)
N9	0.073 (13)	0.056 (10)	0.066 (14)	−0.003 (8)	−0.001 (10)	0.004 (9)
N10	0.069 (13)	0.062 (10)	0.071 (14)	−0.014 (9)	0.005 (10)	0.006 (10)
N11	0.076 (14)	0.053 (9)	0.061 (13)	−0.004 (9)	−0.014 (11)	0.000 (9)
N12	0.070 (12)	0.075 (12)	0.084 (15)	−0.018 (9)	−0.011 (10)	−0.008 (11)
N13	0.096 (17)	0.057 (12)	0.064 (13)	−0.004 (12)	0.018 (11)	0.023 (9)
N14	0.101 (18)	0.073 (15)	0.071 (15)	−0.011 (15)	−0.015 (12)	−0.006 (12)
N15	0.14 (4)	0.11 (3)	0.05 (2)	0.01 (3)	−0.01 (3)	0.03 (2)
N16	0.14 (4)	0.11 (3)	0.05 (2)	0.01 (3)	−0.01 (3)	0.03 (2)
N17	0.14 (4)	0.11 (3)	0.05 (2)	0.01 (3)	−0.01 (3)	0.03 (2)
O1	0.114 (15)	0.084 (11)	0.107 (15)	0.007 (10)	0.011 (11)	0.028 (10)
O2	0.121 (14)	0.074 (10)	0.085 (12)	−0.001 (9)	−0.003 (10)	0.013 (9)
O3	0.131 (14)	0.097 (11)	0.065 (11)	0.043 (11)	−0.005 (9)	0.027 (8)
O4	0.107 (13)	0.083 (10)	0.054 (10)	0.006 (10)	−0.009 (9)	0.011 (8)
O5	0.111 (13)	0.066 (9)	0.094 (14)	0.036 (9)	0.010 (10)	−0.012 (8)
O6	0.124 (14)	0.088 (11)	0.080 (13)	−0.002 (11)	−0.006 (10)	0.015 (10)
O7	0.14 (4)	0.11 (3)	0.056 (18)	0.00 (2)	−0.01 (2)	0.032 (18)
O8	0.14 (4)	0.11 (3)	0.056 (18)	0.00 (2)	−0.01 (2)	0.032 (18)
O9	0.14 (4)	0.11 (3)	0.056 (18)	0.00 (2)	−0.01 (2)	0.032 (18)
C1	0.092 (19)	0.050 (10)	0.057 (18)	0.008 (11)	0.004 (13)	−0.002 (11)
C2	0.12 (3)	0.072 (18)	0.07 (2)	0.011 (13)	0.013 (17)	−0.006 (14)
C3	0.100 (17)	0.058 (14)	0.056 (16)	0.010 (11)	0.008 (12)	−0.006 (11)
C4	0.089 (16)	0.061 (14)	0.054 (16)	−0.002 (11)	0.002 (12)	0.004 (12)
C5	0.101 (17)	0.061 (13)	0.060 (15)	0.004 (11)	0.030 (12)	0.008 (11)
C6	0.101 (17)	0.063 (13)	0.058 (15)	0.001 (11)	0.019 (12)	0.000 (10)
C7	0.084 (19)	0.069 (14)	0.071 (18)	0.011 (13)	−0.008 (14)	−0.014 (12)
C8	0.101 (19)	0.083 (15)	0.081 (17)	0.022 (15)	−0.014 (14)	−0.007 (15)
C9	0.096 (18)	0.078 (15)	0.074 (18)	0.017 (13)	−0.009 (14)	−0.005 (13)
C10	0.086 (18)	0.067 (13)	0.066 (17)	0.026 (12)	0.008 (13)	−0.006 (12)
C11	0.10 (2)	0.072 (14)	0.066 (17)	0.024 (13)	0.008 (14)	−0.010 (12)
C12	0.098 (17)	0.056 (12)	0.059 (15)	0.027 (12)	0.004 (12)	−0.010 (11)
C13	0.073 (16)	0.053 (11)	0.066 (17)	−0.004 (11)	0.004 (13)	−0.004 (11)
C14	0.088 (17)	0.082 (15)	0.077 (18)	−0.022 (13)	0.007 (14)	0.004 (13)
C15	0.090 (16)	0.064 (13)	0.066 (16)	−0.015 (11)	0.001 (12)	0.000 (11)
C16	0.067 (15)	0.056 (13)	0.064 (16)	−0.012 (10)	−0.002 (12)	−0.006 (11)
C17	0.073 (16)	0.075 (14)	0.083 (19)	−0.012 (12)	−0.018 (13)	−0.011 (14)
C18	0.078 (16)	0.063 (12)	0.073 (16)	0.001 (11)	−0.017 (12)	−0.002 (11)
C19	0.14 (5)	0.10 (3)	0.05 (3)	0.01 (3)	−0.01 (3)	0.03 (3)
C20	0.14 (7)	0.11 (6)	0.04 (3)	0.01 (5)	−0.02 (4)	0.04 (4)
C21	0.14 (4)	0.11 (3)	0.05 (3)	0.01 (3)	−0.01 (2)	0.03 (3)
C22	0.14 (5)	0.10 (3)	0.05 (3)	0.01 (3)	−0.01 (3)	0.03 (3)
C23	0.14 (7)	0.11 (6)	0.04 (3)	0.01 (5)	−0.02 (4)	0.04 (4)
C24	0.14 (4)	0.11 (3)	0.05 (3)	0.01 (3)	−0.01 (2)	0.03 (3)
C25	0.14 (5)	0.10 (3)	0.05 (3)	0.01 (3)	−0.01 (3)	0.03 (3)
C26	0.14 (7)	0.11 (6)	0.04 (3)	0.01 (5)	−0.02 (4)	0.04 (4)
C27	0.14 (4)	0.11 (3)	0.05 (3)	0.01 (3)	−0.01 (2)	0.03 (3)

Ni1—N3	2.005 (18)	N17—C25	1.32 (11)
Ni1—N5	2.04 (2)	N17—C27	1.47 (11)
Ni1—N7	2.060 (19)	N17—C26	1.48 (16)
Ni1—N9	2.075 (19)	O7—C19	1.24 (10)
Ni1—N11	2.101 (18)	O8—C22	1.25 (8)
Ni1—N1	2.106 (18)	O9—C25	1.24 (9)
N1—C1	1.35 (2)	C1—C4	1.45 (3)
N1—C3	1.37 (3)	C2—C3	1.37 (3)
N2—C1	1.37 (2)	C2—H2B	0.9300
N2—C2	1.38 (4)	C3—H3	0.9300
N2—H2	0.8600	C5—C6	1.36 (3)
N3—C4	1.34 (2)	C5—H5	0.9300
N3—C6	1.52 (3)	C6—H6A	0.9300
N4—C4	1.36 (3)	C7—C10	1.44 (3)
N4—C5	1.37 (3)	C8—C9	1.37 (3)
N4—H4	0.8600	C8—H8A	0.9300
N5—C7	1.35 (3)	C9—H9	0.9300
N5—C9	1.39 (3)	C11—C12	1.36 (3)
N6—C7	1.36 (3)	C11—H11	0.9300
N6—C8	1.37 (3)	C12—H12A	0.9300
N6—H6	0.8600	C13—C16	1.45 (3)
N7—C10	1.36 (3)	C14—C15	1.37 (3)
N7—C12	1.37 (3)	C14—H14	0.9300
N8—C10	1.36 (3)	C15—H15	0.9300
N8—C11	1.37 (3)	C17—C18	1.37 (3)
N8—H8	0.8600	C17—H17	0.9300
N9—C13	1.35 (3)	C18—H18	0.9300
N9—C15	1.38 (3)	C19—H19	0.9300
N10—C14	1.36 (3)	C20—H20A	0.9600
N10—C13	1.37 (3)	C20—H20B	0.9600
N10—H10	0.8600	C20—H20C	0.9600
N11—C16	1.35 (3)	C21—H21A	0.9600
N11—C18	1.38 (3)	C21—H21B	0.9600
N12—C16	1.36 (2)	C21—H21C	0.9600
N12—C17	1.37 (3)	C22—H22	0.9300
N12—H12	0.8600	C23—H23A	0.9600
N13—O3	1.22 (2)	C23—H23B	0.9600
N13—O1	1.23 (2)	C23—H23C	0.9600
N13—O2	1.27 (2)	C24—H24A	0.9600
N14—O6	1.15 (2)	C24—H24B	0.9600
N14—O5	1.20 (2)	C24—H24C	0.9600
N14—O4	1.24 (3)	C25—H25	0.9300
N15—C19	1.32 (8)	C26—H26A	0.9600
N15—C21	1.47 (11)	C26—H26B	0.9600
N15—C20	1.48 (12)	C26—H26C	0.9600
N16—C22	1.33 (9)	C27—H27A	0.9600
N16—C24	1.47 (9)	C27—H27B	0.9600
N16—C23	1.48 (13)	C27—H27C	0.9600
N3—Ni1—N5	98.6 (8)	N2—C2—H2B	126.5
N3—Ni1—N7	91.5 (8)	N1—C3—C2	109 (3)
N5—Ni1—N7	81.6 (8)	N1—C3—H3	125.7
N3—Ni1—N9	168.8 (8)	C2—C3—H3	125.7
N5—Ni1—N9	88.9 (8)	N3—C4—N4	112 (2)
N7—Ni1—N9	97.8 (6)	N3—C4—C1	116.0 (19)
N3—Ni1—N11	93.3 (7)	N4—C4—C1	132 (2)
N5—Ni1—N11	166.6 (7)	C6—C5—N4	110 (2)
N7—Ni1—N11	92.2 (8)	C6—C5—H5	125.0
N9—Ni1—N11	80.2 (8)	N4—C5—H5	125.0
N3—Ni1—N1	81.1 (7)	C5—C6—N3	105.0 (18)
N5—Ni1—N1	89.7 (7)	C5—C6—H6A	127.5
N7—Ni1—N1	167.6 (8)	N3—C6—H6A	127.5
N9—Ni1—N1	90.8 (7)	N5—C7—N6	110 (2)
N11—Ni1—N1	98.1 (7)	N5—C7—C10	115 (2)
C1—N1—C3	107.2 (17)	N6—C7—C10	133 (3)
C1—N1—Ni1	110.0 (15)	C9—C8—N6	107 (2)
C3—N1—Ni1	141.4 (15)	C9—C8—H8A	126.6
C1—N2—C2	107.2 (17)	N6—C8—H8A	126.6
C1—N2—H2	126.4	C8—C9—N5	109 (2)
C2—N2—H2	126.4	C8—C9—H9	125.4
C4—N3—C6	104.5 (18)	N5—C9—H9	125.4
C4—N3—Ni1	114.7 (15)	N7—C10—N8	111 (2)
C6—N3—Ni1	140.7 (13)	N7—C10—C7	118 (2)
C4—N4—C5	107.7 (16)	N8—C10—C7	130 (2)
C4—N4—H4	126.1	C12—C11—N8	108 (2)
C5—N4—H4	126.1	C12—C11—H11	125.8
C7—N5—C9	105 (2)	N8—C11—H11	125.8
C7—N5—Ni1	113.4 (16)	C11—C12—N7	109 (2)
C9—N5—Ni1	141.2 (17)	C11—C12—H12A	125.4
C7—N6—C8	107 (2)	N7—C12—H12A	125.4
C7—N6—H6	126.3	N9—C13—N10	110 (2)
C8—N6—H6	126.3	N9—C13—C16	115 (2)
C10—N7—C12	105.4 (19)	N10—C13—C16	135 (2)
C10—N7—Ni1	110.6 (15)	N10—C14—C15	108 (2)
C12—N7—Ni1	143.3 (16)	N10—C14—H14	126.2
C10—N8—C11	106 (2)	C15—C14—H14	126.2
C10—N8—H8	127.1	C14—C15—N9	108 (2)
C11—N8—H8	127.1	C14—C15—H15	125.8
C13—N9—C15	106.4 (19)	N9—C15—H15	125.8
C13—N9—Ni1	114.3 (16)	N11—C16—N12	110 (2)
C15—N9—Ni1	139.1 (16)	N11—C16—C13	120 (2)
C14—N10—C13	107.1 (19)	N12—C16—C13	130 (2)
C14—N10—H10	126.5	N12—C17—C18	108 (2)
C13—N10—H10	126.5	N12—C17—H17	125.8
C16—N11—C18	107.3 (19)	C18—C17—H17	125.8
C16—N11—Ni1	110.4 (15)	C17—C18—N11	108 (2)
C18—N11—Ni1	142.0 (17)	C17—C18—H18	126.2
C16—N12—C17	107 (2)	N11—C18—H18	126.2
C16—N12—H12	126.6	O7—C19—N15	113 (8)
C17—N12—H12	126.6	O7—C19—H19	123.6
O3—N13—O1	120.2 (19)	N15—C19—H19	123.6
O3—N13—O2	120 (2)	O8—C22—N16	112 (8)
O1—N13—O2	120 (2)	O8—C22—H22	124.0
O6—N14—O5	124 (3)	N16—C22—H22	124.0
O6—N14—O4	124 (3)	N16—C23—H23A	109.5
O5—N14—O4	111 (2)	N16—C23—H23B	109.5
C19—N15—C21	122 (8)	H23A—C23—H23B	109.5
C19—N15—C20	121 (9)	N16—C23—H23C	109.5
C21—N15—C20	114 (8)	H23A—C23—H23C	109.5
C22—N16—C24	122 (8)	H23B—C23—H23C	109.5
C22—N16—C23	120 (9)	N16—C24—H24A	109.5
C24—N16—C23	114 (8)	N16—C24—H24B	109.5
C25—N17—C27	123 (10)	H24A—C24—H24B	109.5
C25—N17—C26	120 (10)	N16—C24—H24C	109.5
C27—N17—C26	116 (10)	H24A—C24—H24C	109.5
N1—C1—N2	109.6 (18)	H24B—C24—H24C	109.5
N1—C1—C4	117.7 (18)	O9—C25—N17	111 (10)
N2—C1—C4	132.5 (18)	O9—C25—H25	124.5
C3—C2—N2	107 (3)	N17—C25—H25	124.5
C3—C2—H2B	126.5
N3—Ni1—N1—C1	4.9 (14)	N2—C2—C3—N1	−6(3)
N5—Ni1—N1—C1	−93.9 (15)	C6—N3—C4—N4	4(2)
N7—Ni1—N1—C1	−49 (4)	Ni1—N3—C4—N4	−176.8 (15)
N9—Ni1—N1—C1	177.2 (14)	C6—N3—C4—C1	178.6 (17)
N11—Ni1—N1—C1	97.0 (14)	Ni1—N3—C4—C1	−3(2)
N3—Ni1—N1—C3	169 (2)	C5—N4—C4—N3	−8(3)
N5—Ni1—N1—C3	70 (2)	C5—N4—C4—C1	179 (2)
N7—Ni1—N1—C3	115 (4)	N1—C1—C4—N3	7(3)
N9—Ni1—N1—C3	−19 (2)	N2—C1—C4—N3	−168 (2)
N11—Ni1—N1—C3	−99 (2)	N1—C1—C4—N4	−180 (2)
N5—Ni1—N3—C4	87.1 (16)	N2—C1—C4—N4	5(4)
N7—Ni1—N3—C4	168.8 (15)	C4—N4—C5—C6	9(3)
N9—Ni1—N3—C4	−45 (5)	N4—C5—C6—N3	−6(2)
N11—Ni1—N3—C4	−98.9 (15)	C4—N3—C6—C5	1(2)
N1—Ni1—N3—C4	−1.2 (15)	Ni1—N3—C6—C5	−177.4 (17)
N5—Ni1—N3—C6	−95 (2)	C9—N5—C7—N6	5(3)
N7—Ni1—N3—C6	−13 (2)	Ni1—N5—C7—N6	−175.1 (16)
N9—Ni1—N3—C6	134 (4)	C9—N5—C7—C10	175 (2)
N11—Ni1—N3—C6	79 (2)	Ni1—N5—C7—C10	−5(3)
N1—Ni1—N3—C6	177 (2)	C8—N6—C7—N5	−9(3)
N3—Ni1—N5—C7	90.6 (18)	C8—N6—C7—C10	−176 (3)
N7—Ni1—N5—C7	0.3 (18)	C7—N6—C8—C9	9(3)
N9—Ni1—N5—C7	−97.8 (18)	N6—C8—C9—N5	−7(3)
N11—Ni1—N5—C7	−63 (6)	C7—N5—C9—C8	1(3)
N1—Ni1—N5—C7	171.5 (19)	Ni1—N5—C9—C8	−179 (2)
N3—Ni1—N5—C9	−89 (3)	C12—N7—C10—N8	−2(2)
N7—Ni1—N5—C9	−179 (3)	Ni1—N7—C10—N8	171.0 (15)
N9—Ni1—N5—C9	83 (3)	C12—N7—C10—C7	178 (2)
N11—Ni1—N5—C9	118 (4)	Ni1—N7—C10—C7	−9(3)
N1—Ni1—N5—C9	−8(3)	C11—N8—C10—N7	2(3)
N3—Ni1—N7—C10	−93.7 (15)	C11—N8—C10—C7	−177 (2)
N5—Ni1—N7—C10	4.8 (15)	N5—C7—C10—N7	10 (3)
N9—Ni1—N7—C10	92.5 (16)	N6—C7—C10—N7	177 (2)
N11—Ni1—N7—C10	172.9 (16)	N5—C7—C10—N8	−170 (2)
N1—Ni1—N7—C10	−41 (4)	N6—C7—C10—N8	−3(5)
N3—Ni1—N7—C12	74 (3)	C10—N8—C11—C12	−2(3)
N5—Ni1—N7—C12	173 (3)	N8—C11—C12—N7	1(3)
N9—Ni1—N7—C12	−100 (2)	C10—N7—C12—C11	0(2)
N11—Ni1—N7—C12	−19 (3)	Ni1—N7—C12—C11	−168 (2)
N1—Ni1—N7—C12	127 (4)	C15—N9—C13—N10	−8(2)
N3—Ni1—N9—C13	−58 (4)	Ni1—N9—C13—N10	175.0 (13)
N5—Ni1—N9—C13	169.8 (15)	C15—N9—C13—C16	179.3 (18)
N7—Ni1—N9—C13	88.5 (16)	Ni1—N9—C13—C16	3(2)
N11—Ni1—N9—C13	−2.4 (14)	C14—N10—C13—N9	8(2)
N1—Ni1—N9—C13	−100.5 (14)	C14—N10—C13—C16	178 (2)
N3—Ni1—N9—C15	127 (4)	C13—N10—C14—C15	−4(2)
N5—Ni1—N9—C15	−5(2)	N10—C14—C15—N9	−1(2)
N7—Ni1—N9—C15	−87 (2)	C13—N9—C15—C14	6(2)
N11—Ni1—N9—C15	−177 (2)	Ni1—N9—C15—C14	−179.2 (16)
N1—Ni1—N9—C15	84 (2)	C18—N11—C16—N12	−1(2)
N3—Ni1—N11—C16	172.5 (15)	Ni1—N11—C16—N12	174.7 (13)
N5—Ni1—N11—C16	−34 (6)	C18—N11—C16—C13	−176.3 (19)
N7—Ni1—N11—C16	−95.9 (15)	Ni1—N11—C16—C13	−1(2)
N9—Ni1—N11—C16	1.7 (14)	C17—N12—C16—N11	1(2)
N1—Ni1—N11—C16	91.0 (15)	C17—N12—C16—C13	176 (2)
N3—Ni1—N11—C18	−15 (2)	N9—C13—C16—N11	−1(3)
N5—Ni1—N11—C18	139 (4)	N10—C13—C16—N11	−171 (2)
N7—Ni1—N11—C18	77 (2)	N9—C13—C16—N12	−176 (2)
N9—Ni1—N11—C18	175 (2)	N10—C13—C16—N12	15 (4)
N1—Ni1—N11—C18	−96 (2)	C16—N12—C17—C18	−1(2)
C3—N1—C1—N2	−1(2)	N12—C17—C18—N11	0(3)
Ni1—N1—C1—N2	168.2 (14)	C16—N11—C18—C17	0(2)
C3—N1—C1—C4	−177.3 (19)	Ni1—N11—C18—C17	−172.9 (18)
Ni1—N1—C1—C4	−8(2)	C21—N15—C19—O7	150 (7)
C2—N2—C1—N1	−2(3)	C20—N15—C19—O7	−51 (11)
C2—N2—C1—C4	173 (3)	C24—N16—C22—O8	−153 (6)
C1—N2—C2—C3	5(3)	C23—N16—C22—O8	0(10)
C1—N1—C3—C2	5(3)	C27—N17—C25—O9	−156 (8)
Ni1—N1—C3—C2	−160 (2)	C26—N17—C25—O9	18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5i	0.86	2.19	2.93 (2)	144.
N2—H2···O4i	0.86	2.30	2.98 (2)	136.
N4—H4···O1ii	0.86	1.91	2.77 (2)	176.
N4—H4···O3ii	0.86	2.45	3.04 (3)	127.
N6—H6···O6	0.86	2.05	2.90 (3)	171.
N6—H6···O4	0.86	2.43	3.09 (2)	133.
N8—H8···O2iii	0.86	2.09	2.82 (3)	141.
N8—H8···O3iii	0.86	2.36	2.98 (2)	130.
N10—H10···O5iv	0.86	2.17	2.98 (3)	156.
N10—H10···O6iv	0.86	2.45	3.16 (2)	140.
N12—H12···O2v	0.86	2.29	2.97 (2)	136.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5i	0.86	2.19	2.93 (2)	144
N2—H2⋯O4i	0.86	2.30	2.98 (2)	136
N4—H4⋯O1ii	0.86	1.91	2.77 (2)	176
N4—H4⋯O3ii	0.86	2.45	3.04 (3)	127
N6—H6⋯O6	0.86	2.05	2.90 (3)	171
N6—H6⋯O4	0.86	2.43	3.09 (2)	133
N8—H8⋯O2iii	0.86	2.09	2.82 (3)	141
N8—H8⋯O3iii	0.86	2.36	2.98 (2)	130
N10—H10⋯O5iv	0.86	2.17	2.98 (3)	156
N10—H10⋯O6iv	0.86	2.45	3.16 (2)	140
N12—H12⋯O2v	0.86	2.29	2.97 (2)	136

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