Diaqua-bis-(5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O)nickel(II) tetra-hydrate.

In the title complex, [Ni(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·4H(2)O, the Ni(II) ion is coordinated in a slightly distorted octa-hedral environment formed by two bis-chelating H(2)pimda (H(3)pimda is 2-propyl-1H-4,5-dicarb-oxy-lic acid) ligands and two coordinated water mol-ecules. In the crystal structure, a three-dimensional framework is formed by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds involving the solvent water mol-ecules, coordinated water mol-ecules, carboxyl-ate O atoms and the protonated N atoms of the H(2)pimda ligands. The propyl groups of each H(2)pimda ligand are disordered over two sets of sites with refined occupancies of 0.50 (2):0.50 (2) and 0.762 (11):0.238 (11). In one water solvent mol-ecule, one of the H atoms was refined as disordered over two sites of equal occupancy.

Related literature

For the potential uses and diverse structural types of imidazole-4,5-dicarb­oxy­lic acid complexes, see: Zou et al. (2006 ▶); Li et al. (2006 ▶); Liu et al. (2004 ▶); Sun et al. (2005 ▶).

Experimental

Crystal data

[Ni(C8H9N2O4)2(H2O)2]·4H2O

M = 561.15

Triclinic,

a = 10.466 (1) Å

b = 10.5829 (11) Å

c = 11.3011 (13) Å

α = 81.585 (1)°

β = 83.580 (1)°

γ = 86.869 (2)°

V = 1229.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.86 mm−1

T = 298 K

0.48 × 0.40 × 0.33 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.682, T max = 0.764

6402 measured reflections

4280 independent reflections

2986 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.208

S = 1.05

4280 reflections

358 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −1.16 e Å−3

Data collection: SMART (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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025237/lh5048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025237/lh5048Isup2.hkl

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

[Ni(C8H9N2O4)2(H2O)2]·4H2O	Z = 2
Mr = 561.15	F(000) = 588
Triclinic, P1	Dx = 1.516 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.466 (1) Å	Cell parameters from 2051 reflections
b = 10.5829 (11) Å	θ = 2.5–23.9°
c = 11.3011 (13) Å	µ = 0.86 mm−1
α = 81.585 (1)°	T = 298 K
β = 83.580 (1)°	Block, green
γ = 86.869 (2)°	0.48 × 0.40 × 0.33 mm
V = 1229.5 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	4280 independent reflections
Radiation source: fine-focus sealed tube	2986 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.682, Tmax = 0.764	k = −11→12
6402 measured reflections	l = −10→13

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0945P)2 + 3.581P] where P = (Fo2 + 2Fc2)/3
4280 reflections	(Δ/σ)max = 0.001
358 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −1.16 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	Occ. (<1)
Ni1	0.15302 (7)	0.21144 (7)	0.80787 (6)	0.0439 (3)
N1	0.3486 (4)	0.2176 (4)	0.8285 (4)	0.0403 (10)
N2	0.5487 (4)	0.2256 (4)	0.8689 (4)	0.0449 (11)
H2	0.6187	0.2557	0.8847	0.054*
N3	0.1723 (4)	0.2837 (4)	0.6268 (4)	0.0432 (11)
N4	0.1924 (5)	0.3537 (5)	0.4338 (4)	0.0520 (13)
H4	0.2055	0.3536	0.3573	0.062*
O1	0.2132 (4)	0.0190 (4)	0.7957 (4)	0.0502 (10)
O2	0.3797 (4)	−0.1188 (4)	0.8133 (4)	0.0621 (12)
O3	0.6045 (4)	−0.1139 (4)	0.8582 (4)	0.0596 (11)
H3	0.5301	−0.1123	0.8414	0.089*
O4	0.7386 (4)	0.0255 (4)	0.8992 (4)	0.0598 (12)
O5	0.1072 (4)	0.4049 (4)	0.8174 (3)	0.0493 (10)
O6	0.0993 (5)	0.5962 (4)	0.7061 (4)	0.0590 (11)
O7	0.1250 (5)	0.6826 (4)	0.4849 (4)	0.0625 (12)
H7	0.1167	0.6548	0.5568	0.094*
O8	0.1656 (4)	0.6062 (5)	0.3144 (4)	0.0671 (13)
O9	−0.0354 (4)	0.1738 (5)	0.7901 (5)	0.0746 (15)
H9C	−0.0961	0.1264	0.8235	0.090*
H9D	−0.0686	0.2430	0.7563	0.090*
O10	0.1162 (5)	0.1683 (5)	0.9898 (4)	0.0798 (17)
H10C	0.1598	0.1079	1.0266	0.096*
H10D	0.0495	0.1848	1.0361	0.096*
O11	0.9033 (5)	0.2266 (5)	0.1288 (5)	0.0849 (17)
H11C	0.8673	0.1570	0.1577	0.102*
H11D	0.8986	0.2744	0.1835	0.102*
O12	0.2218 (7)	0.3264 (7)	0.1953 (5)	0.110 (2)
H12C	0.1862	0.3693	0.1375	0.132*
H12D	0.2694	0.2670	0.1686	0.132*
O13	0.2630 (6)	0.6526 (7)	0.0459 (6)	0.112 (2)
H13C	0.2576	0.7035	−0.0191	0.135*
H13D	0.1980	0.6641	0.0960	0.135*
O14	0.1006 (8)	0.4916 (9)	0.0385 (7)	0.152 (3)
H14G	0.1650	0.5203	−0.0085	0.182*
H14F	0.0605	0.4436	0.0024	0.182*	0.50
H14H	0.0326	0.5153	0.0054	0.182*	0.50
C1	0.3287 (5)	−0.0078 (5)	0.8114 (5)	0.0436 (13)
C2	0.4061 (5)	0.0981 (5)	0.8310 (5)	0.0394 (12)
C3	0.5317 (5)	0.1013 (5)	0.8560 (5)	0.0417 (13)
C4	0.6338 (6)	−0.0005 (6)	0.8721 (5)	0.0466 (14)
C5	0.4375 (5)	0.2931 (5)	0.8528 (5)	0.0457 (14)
C6	0.4222 (7)	0.4317 (7)	0.8555 (8)	0.072 (2)
H6A	0.4286	0.4444	0.9379	0.086*	0.50 (2)
H6B	0.3345	0.4560	0.8394	0.086*	0.50 (2)
H6'A	0.4762	0.4594	0.9105	0.086*	0.50 (2)
H6'B	0.3334	0.4576	0.8773	0.086*	0.50 (2)
C7	0.5053 (15)	0.5269 (15)	0.7781 (18)	0.069 (6)	0.50 (2)
H7A	0.5949	0.5062	0.7896	0.082*	0.50 (2)
H7B	0.4838	0.6115	0.7996	0.082*	0.50 (2)
C8	0.484 (2)	0.525 (3)	0.645 (2)	0.093 (8)	0.50 (2)
H8A	0.4726	0.4389	0.6324	0.139*	0.50 (2)
H8B	0.5580	0.5582	0.5940	0.139*	0.50 (2)
H8C	0.4092	0.5771	0.6261	0.139*	0.50 (2)
C7'	0.4676 (19)	0.4840 (19)	0.718 (2)	0.068 (6)	0.50 (2)
H7'1	0.5570	0.4575	0.6994	0.082*	0.50 (2)
H7'2	0.4170	0.4455	0.6665	0.082*	0.50 (2)
C8'	0.4540 (19)	0.627 (2)	0.689 (2)	0.100 (8)	0.50 (2)
H8'1	0.3664	0.6540	0.7096	0.150*	0.50 (2)
H8'2	0.4775	0.6522	0.6047	0.150*	0.50 (2)
H8'3	0.5094	0.6655	0.7345	0.150*	0.50 (2)
C9	0.1183 (5)	0.4772 (6)	0.7179 (5)	0.0443 (13)
C10	0.1527 (5)	0.4136 (5)	0.6109 (5)	0.0380 (12)
C11	0.1660 (5)	0.4595 (6)	0.4900 (5)	0.0431 (13)
C12	0.1541 (5)	0.5891 (6)	0.4234 (5)	0.0470 (14)
C13	0.1946 (6)	0.2498 (6)	0.5181 (6)	0.0553 (16)
C14	0.2084 (10)	0.1182 (8)	0.4929 (7)	0.087 (3)
H14A	0.1637	0.1128	0.4232	0.104*	0.762 (11)
H14B	0.1647	0.0643	0.5605	0.104*	0.762 (11)
H14C	0.2409	0.0704	0.5641	0.104*	0.238 (11)
H14D	0.2791	0.1187	0.4296	0.104*	0.238 (11)
C15	0.3406 (12)	0.0638 (11)	0.4702 (11)	0.088 (4)	0.762 (11)
H15A	0.3896	0.0756	0.5354	0.106*	0.762 (11)
H15B	0.3823	0.1091	0.3964	0.106*	0.762 (11)
C16	0.3405 (16)	−0.0808 (12)	0.4595 (14)	0.128 (6)	0.762 (11)
H16A	0.2931	−0.1248	0.5296	0.192*	0.762 (11)
H16B	0.4275	−0.1150	0.4530	0.192*	0.762 (11)
H16C	0.3010	−0.0919	0.3892	0.192*	0.762 (11)
C15'	0.121 (4)	0.030 (4)	0.449 (3)	0.086 (11)	0.238 (11)
H15C	0.0543	0.0036	0.5125	0.103*	0.238 (11)
H15D	0.1707	−0.0455	0.4292	0.103*	0.238 (11)
C16'	0.058 (4)	0.093 (4)	0.338 (4)	0.110 (15)	0.238 (11)
H16D	0.0276	0.1778	0.3492	0.165*	0.238 (11)
H16E	−0.0124	0.0433	0.3268	0.165*	0.238 (11)
H16F	0.1205	0.0965	0.2684	0.165*	0.238 (11)

	U11	U22	U33	U12	U13	U23
Ni1	0.0360 (4)	0.0492 (5)	0.0421 (4)	0.0037 (3)	−0.0052 (3)	0.0065 (3)
N1	0.038 (2)	0.040 (2)	0.041 (2)	0.004 (2)	−0.0074 (19)	−0.0003 (19)
N2	0.036 (2)	0.047 (3)	0.050 (3)	−0.003 (2)	−0.011 (2)	0.004 (2)
N3	0.045 (3)	0.045 (3)	0.039 (3)	0.000 (2)	−0.007 (2)	0.000 (2)
N4	0.059 (3)	0.060 (3)	0.036 (3)	0.008 (3)	−0.008 (2)	−0.006 (2)
O1	0.049 (2)	0.046 (2)	0.054 (2)	−0.0064 (19)	−0.0120 (19)	0.0011 (18)
O2	0.061 (3)	0.042 (2)	0.084 (3)	0.004 (2)	−0.009 (2)	−0.012 (2)
O3	0.050 (3)	0.055 (3)	0.072 (3)	0.016 (2)	−0.007 (2)	−0.009 (2)
O4	0.039 (2)	0.067 (3)	0.067 (3)	0.010 (2)	−0.007 (2)	0.011 (2)
O5	0.052 (2)	0.058 (3)	0.035 (2)	0.0139 (19)	−0.0061 (17)	−0.0037 (18)
O6	0.078 (3)	0.050 (3)	0.049 (2)	0.011 (2)	−0.012 (2)	−0.0061 (19)
O7	0.075 (3)	0.050 (3)	0.059 (3)	0.003 (2)	−0.012 (2)	0.008 (2)
O8	0.060 (3)	0.084 (3)	0.047 (3)	0.009 (2)	−0.003 (2)	0.016 (2)
O9	0.041 (2)	0.081 (3)	0.089 (4)	−0.010 (2)	−0.015 (2)	0.039 (3)
O10	0.066 (3)	0.103 (4)	0.050 (3)	0.043 (3)	0.011 (2)	0.028 (3)
O11	0.076 (4)	0.083 (4)	0.098 (4)	−0.030 (3)	0.025 (3)	−0.040 (3)
O12	0.133 (6)	0.133 (6)	0.070 (4)	0.049 (4)	−0.022 (4)	−0.042 (4)
O13	0.094 (5)	0.138 (6)	0.122 (5)	0.009 (4)	−0.050 (4)	−0.049 (4)
O14	0.146 (7)	0.185 (9)	0.124 (7)	0.007 (6)	−0.015 (5)	−0.024 (6)
C1	0.040 (3)	0.046 (3)	0.043 (3)	0.000 (3)	−0.005 (2)	0.000 (2)
C2	0.038 (3)	0.040 (3)	0.037 (3)	0.004 (2)	−0.002 (2)	0.002 (2)
C3	0.039 (3)	0.042 (3)	0.040 (3)	0.003 (2)	−0.001 (2)	0.004 (2)
C4	0.041 (3)	0.053 (4)	0.039 (3)	0.008 (3)	0.002 (2)	0.004 (3)
C5	0.041 (3)	0.044 (3)	0.051 (3)	0.004 (3)	−0.012 (3)	0.000 (3)
C6	0.061 (4)	0.056 (4)	0.102 (6)	0.003 (3)	−0.032 (4)	−0.008 (4)
C7	0.054 (9)	0.052 (9)	0.103 (14)	−0.008 (7)	−0.022 (9)	−0.008 (8)
C8	0.067 (12)	0.12 (2)	0.096 (17)	−0.009 (12)	−0.022 (12)	−0.009 (14)
C7'	0.052 (10)	0.059 (11)	0.094 (15)	−0.008 (8)	−0.010 (11)	−0.008 (11)
C8'	0.091 (14)	0.084 (15)	0.119 (17)	0.010 (11)	−0.010 (12)	0.000 (12)
C9	0.041 (3)	0.048 (3)	0.043 (3)	0.006 (3)	−0.008 (2)	−0.001 (3)
C10	0.033 (3)	0.043 (3)	0.037 (3)	0.002 (2)	−0.007 (2)	0.000 (2)
C11	0.033 (3)	0.052 (3)	0.043 (3)	−0.001 (2)	−0.005 (2)	−0.001 (3)
C12	0.036 (3)	0.057 (4)	0.044 (3)	0.000 (3)	−0.007 (2)	0.007 (3)
C13	0.065 (4)	0.056 (4)	0.045 (3)	0.006 (3)	−0.010 (3)	−0.010 (3)
C14	0.123 (8)	0.074 (5)	0.061 (5)	0.017 (5)	−0.014 (5)	−0.007 (4)
C15	0.101 (9)	0.081 (8)	0.079 (7)	0.003 (7)	−0.002 (6)	−0.009 (6)
C16	0.162 (15)	0.080 (9)	0.133 (13)	0.006 (9)	0.028 (11)	−0.024 (8)
C15'	0.10 (3)	0.08 (2)	0.07 (2)	0.00 (2)	0.004 (19)	−0.006 (18)
C16'	0.12 (4)	0.10 (3)	0.10 (3)	0.01 (3)	0.02 (3)	0.00 (2)

Ni1—O10	2.038 (4)	C5—C6	1.472 (9)
Ni1—N3	2.069 (4)	C6—C7	1.485 (17)
Ni1—O9	2.071 (4)	C6—C7'	1.60 (2)
Ni1—N1	2.092 (4)	C6—H6A	0.9700
Ni1—O5	2.092 (4)	C6—H6B	0.9700
Ni1—O1	2.118 (4)	C6—H6'A	0.9700
N1—C5	1.334 (7)	C6—H6'B	0.9700
N1—C2	1.368 (7)	C7—C8	1.55 (3)
N2—C5	1.348 (7)	C7—H7A	0.9700
N2—C3	1.368 (7)	C7—H7B	0.9700
N2—H2	0.8600	C8—H8A	0.9600
N3—C13	1.322 (8)	C8—H8B	0.9600
N3—C10	1.366 (7)	C8—H8C	0.9600
N4—C13	1.347 (8)	C7'—C8'	1.50 (3)
N4—C11	1.367 (8)	C7'—H7'1	0.9700
N4—H4	0.8600	C7'—H7'2	0.9700
O1—C1	1.253 (7)	C8'—H8'1	0.9600
O2—C1	1.262 (7)	C8'—H8'2	0.9600
O3—C4	1.290 (7)	C8'—H8'3	0.9600
O3—H3	0.8200	C9—C10	1.469 (8)
O4—C4	1.227 (7)	C10—C11	1.376 (7)
O5—C9	1.262 (7)	C11—C12	1.471 (8)
O6—C9	1.255 (7)	C13—C14	1.459 (10)
O7—C12	1.294 (8)	C14—C15	1.479 (14)
O7—H7	0.8200	C14—C15'	1.51 (4)
O8—C12	1.212 (7)	C14—H14A	0.9700
O9—H9C	0.8500	C14—H14B	0.9700
O9—H9D	0.8501	C14—H14C	0.9700
O10—H10C	0.8500	C14—H14D	0.9700
O10—H10D	0.8500	C15—C16	1.552 (16)
O11—H11C	0.8500	C15—H15A	0.9700
O11—H11D	0.8500	C15—H15B	0.9700
O12—H12C	0.8500	C16—H16A	0.9600
O12—H12D	0.8500	C16—H16B	0.9600
O13—H13C	0.8500	C16—H16C	0.9600
O13—H13D	0.8500	C15'—C16'	1.52 (5)
O14—H14G	0.8500	C15'—H15C	0.9700
O14—H14F	0.8500	C15'—H15D	0.9700
O14—H14H	0.8500	C16'—H16D	0.9600
C1—C2	1.474 (8)	C16'—H16E	0.9600
C2—C3	1.378 (8)	C16'—H16F	0.9600
C3—C4	1.482 (8)
O10—Ni1—N3	170.23 (19)	C7—C6—H6'B	117.7
O10—Ni1—O9	89.5 (2)	C7'—C6—H6'B	111.2
N3—Ni1—O9	87.80 (18)	H6'A—C6—H6'B	109.4
O10—Ni1—N1	89.03 (19)	C6—C7—C8	109.0 (17)
N3—Ni1—N1	95.10 (18)	C6—C7—H7A	109.9
O9—Ni1—N1	170.79 (18)	C8—C7—H7A	109.9
O10—Ni1—O5	90.89 (18)	C6—C7—H7B	109.9
N3—Ni1—O5	79.85 (16)	C8—C7—H7B	109.9
O9—Ni1—O5	92.39 (19)	H7A—C7—H7B	108.3
N1—Ni1—O5	96.72 (17)	C8'—C7'—C6	113.1 (18)
O10—Ni1—O1	90.27 (18)	C8'—C7'—H7'1	109.0
N3—Ni1—O1	99.18 (17)	C6—C7'—H7'1	109.0
O9—Ni1—O1	91.48 (18)	C8'—C7'—H7'2	109.0
N1—Ni1—O1	79.43 (16)	C6—C7'—H7'2	109.0
O5—Ni1—O1	175.97 (16)	H7'1—C7'—H7'2	107.8
C5—N1—C2	106.1 (4)	C7'—C8'—H8'1	109.5
C5—N1—Ni1	143.1 (4)	C7'—C8'—H8'2	109.5
C2—N1—Ni1	110.3 (3)	H8'1—C8'—H8'2	109.5
C5—N2—C3	108.5 (5)	C7'—C8'—H8'3	109.5
C5—N2—H2	125.7	H8'1—C8'—H8'3	109.5
C3—N2—H2	125.7	H8'2—C8'—H8'3	109.5
C13—N3—C10	106.5 (5)	O6—C9—O5	124.3 (5)
C13—N3—Ni1	142.9 (4)	O6—C9—C10	119.7 (5)
C10—N3—Ni1	110.6 (3)	O5—C9—C10	116.0 (5)
C13—N4—C11	108.6 (5)	N3—C10—C11	109.6 (5)
C13—N4—H4	125.7	N3—C10—C9	118.3 (5)
C11—N4—H4	125.7	C11—C10—C9	132.1 (5)
C1—O1—Ni1	114.9 (4)	N4—C11—C10	105.0 (5)
C4—O3—H3	109.5	N4—C11—C12	122.5 (5)
C9—O5—Ni1	115.1 (4)	C10—C11—C12	132.4 (6)
C12—O7—H7	109.5	O8—C12—O7	121.5 (6)
Ni1—O9—H9C	141.0	O8—C12—C11	120.6 (6)
Ni1—O9—H9D	106.2	O7—C12—C11	117.8 (5)
H9C—O9—H9D	108.2	N3—C13—N4	110.2 (5)
Ni1—O10—H10C	118.9	N3—C13—C14	124.8 (6)
Ni1—O10—H10D	130.0	N4—C13—C14	124.8 (6)
H10C—O10—H10D	108.5	C13—C14—C15	117.4 (9)
H11C—O11—H11D	108.6	C13—C14—C15'	133.9 (16)
H12C—O12—H12D	108.7	C15—C14—C15'	106.0 (16)
H13C—O13—H13D	110.1	C13—C14—H14A	107.9
H14G—O14—H14F	108.6	C15—C14—H14A	107.9
H14G—O14—H14H	108.5	C13—C14—H14B	107.9
O1—C1—O2	123.8 (5)	C15—C14—H14B	107.9
O1—C1—C2	116.6 (5)	H14A—C14—H14B	107.2
O2—C1—C2	119.6 (5)	C13—C14—H14C	104.5
N1—C2—C3	109.8 (5)	C15'—C14—H14C	106.3
N1—C2—C1	118.5 (5)	C13—C14—H14D	104.7
C3—C2—C1	131.7 (5)	H14C—C14—H14D	105.7
N2—C3—C2	105.3 (5)	C14—C15—C16	111.6 (11)
N2—C3—C4	122.9 (5)	C14—C15—H15A	109.3
C2—C3—C4	131.8 (5)	C16—C15—H15A	109.3
O4—C4—O3	123.8 (5)	C14—C15—H15B	109.3
O4—C4—C3	119.7 (6)	C16—C15—H15B	109.3
O3—C4—C3	116.5 (5)	H15A—C15—H15B	108.0
N1—C5—N2	110.3 (5)	C14—C15'—C16'	113 (3)
N1—C5—C6	126.2 (5)	C14—C15'—H15C	109.0
N2—C5—C6	123.4 (5)	C16'—C15'—H15C	109.0
C5—C6—C7	123.6 (9)	C14—C15'—H15D	109.0
C5—C6—H6A	106.4	C16'—C15'—H15D	109.0
C7—C6—H6A	106.4	H15C—C15'—H15D	107.8
C5—C6—H6B	106.4	C15'—C16'—H16D	109.5
C7—C6—H6B	106.4	C15'—C16'—H16E	109.5
H6A—C6—H6B	106.5	H16D—C16'—H16E	109.5
C5—C6—H6'A	111.6	C15'—C16'—H16F	109.5
C7'—C6—H6'A	112.5	H16D—C16'—H16F	109.5
H6B—C6—H6'A	131.5	H16E—C16'—H16F	109.5
C5—C6—H6'B	111.7
O10—Ni1—N1—C5	−83.4 (6)	C2—N1—C5—C6	177.5 (6)
N3—Ni1—N1—C5	87.7 (6)	Ni1—N1—C5—C6	−12.2 (11)
O5—Ni1—N1—C5	7.4 (6)	C3—N2—C5—N1	−0.6 (6)
O1—Ni1—N1—C5	−173.9 (7)	C3—N2—C5—C6	−177.5 (6)
O10—Ni1—N1—C2	86.6 (4)	N1—C5—C6—C7	−121.2 (12)
N3—Ni1—N1—C2	−102.3 (4)	N2—C5—C6—C7	55.2 (13)
O5—Ni1—N1—C2	177.4 (3)	N1—C5—C6—C7'	−89.1 (10)
O1—Ni1—N1—C2	−3.8 (3)	N2—C5—C6—C7'	87.3 (10)
O9—Ni1—N3—C13	−82.1 (7)	C5—C6—C7—C8	64.8 (16)
N1—Ni1—N3—C13	89.1 (7)	C7'—C6—C7—C8	5.8 (18)
O5—Ni1—N3—C13	−174.9 (7)	C5—C6—C7'—C8'	176.0 (15)
O1—Ni1—N3—C13	9.1 (7)	C7—C6—C7'—C8'	−50.6 (17)
O9—Ni1—N3—C10	95.9 (4)	Ni1—O5—C9—O6	−177.5 (5)
N1—Ni1—N3—C10	−92.8 (4)	Ni1—O5—C9—C10	4.1 (6)
O5—Ni1—N3—C10	3.1 (3)	C13—N3—C10—C11	−1.3 (6)
O1—Ni1—N3—C10	−172.9 (3)	Ni1—N3—C10—C11	180.0 (3)
O10—Ni1—O1—C1	−85.5 (4)	C13—N3—C10—C9	176.6 (5)
N3—Ni1—O1—C1	97.0 (4)	Ni1—N3—C10—C9	−2.1 (6)
O9—Ni1—O1—C1	−175.0 (4)	O6—C9—C10—N3	−179.8 (5)
N1—Ni1—O1—C1	3.5 (4)	O5—C9—C10—N3	−1.3 (7)
O10—Ni1—O5—C9	179.0 (4)	O6—C9—C10—C11	−2.5 (9)
N3—Ni1—O5—C9	−4.1 (4)	O5—C9—C10—C11	176.0 (5)
O9—Ni1—O5—C9	−91.4 (4)	C13—N4—C11—C10	0.0 (7)
N1—Ni1—O5—C9	89.9 (4)	C13—N4—C11—C12	−178.7 (5)
Ni1—O1—C1—O2	176.4 (4)	N3—C10—C11—N4	0.8 (6)
Ni1—O1—C1—C2	−2.3 (6)	C9—C10—C11—N4	−176.7 (6)
C5—N1—C2—C3	−0.6 (6)	N3—C10—C11—C12	179.3 (6)
Ni1—N1—C2—C3	−174.4 (4)	C9—C10—C11—C12	1.8 (10)
C5—N1—C2—C1	177.9 (5)	N4—C11—C12—O8	1.2 (9)
Ni1—N1—C2—C1	4.1 (6)	C10—C11—C12—O8	−177.1 (6)
O1—C1—C2—N1	−1.3 (7)	N4—C11—C12—O7	178.0 (5)
O2—C1—C2—N1	179.9 (5)	C10—C11—C12—O7	−0.4 (9)
O1—C1—C2—C3	176.7 (5)	C10—N3—C13—N4	1.3 (7)
O2—C1—C2—C3	−2.1 (9)	Ni1—N3—C13—N4	179.3 (5)
C5—N2—C3—C2	0.2 (6)	C10—N3—C13—C14	−173.9 (7)
C5—N2—C3—C4	−177.9 (5)	Ni1—N3—C13—C14	4.2 (12)
N1—C2—C3—N2	0.2 (6)	C11—N4—C13—N3	−0.8 (7)
C1—C2—C3—N2	−177.9 (5)	C11—N4—C13—C14	174.3 (7)
N1—C2—C3—C4	178.1 (5)	N3—C13—C14—C15	−98.7 (10)
C1—C2—C3—C4	0.0 (10)	N4—C13—C14—C15	86.8 (10)
N2—C3—C4—O4	0.7 (8)	N3—C13—C14—C15'	103 (2)
C2—C3—C4—O4	−177.0 (6)	N4—C13—C14—C15'	−72 (2)
N2—C3—C4—O3	179.5 (5)	C13—C14—C15—C16	173.4 (9)
C2—C3—C4—O3	1.8 (9)	C15'—C14—C15—C16	−22.4 (18)
C2—N1—C5—N2	0.7 (6)	C13—C14—C15'—C16'	48 (4)
Ni1—N1—C5—N2	171.0 (4)	C15—C14—C15'—C16'	−112 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O13i	0.86	1.91	2.745 (7)	162
N4—H4···O12	0.86	1.88	2.734 (7)	171
O3—H3···O2	0.82	1.65	2.466 (6)	176
O7—H7···O6	0.82	1.70	2.523 (6)	180
O9—H9C···O4ii	0.85	2.11	2.960 (6)	174
O9—H9D···O8iii	0.85	1.96	2.807 (6)	173
O10—H10C···O4iv	0.85	1.87	2.724 (6)	177
O10—H10D···O11v	0.85	1.83	2.675 (7)	177
O11—H11C···O1vi	0.85	2.06	2.904 (6)	172
O11—H11C···O2vi	0.85	2.62	3.197 (7)	127
O11—H11D···O6i	0.85	1.99	2.830 (6)	172
O12—H12C···O14	0.85	1.84	2.676 (10)	166
O12—H12D···O3vi	0.85	2.07	2.904 (7)	167
O13—H13C···O11vii	0.85	2.23	2.889 (9)	134
O13—H13D···O8	0.85	2.44	3.068 (9)	131
O14—H14G···O13	0.85	1.99	2.488 (11)	117
O14—H14H···O14viii	0.85	1.54	2.355 (17)	160
O14—H14F···O5ix	0.85	2.19	2.778 (9)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O13i	0.86	1.91	2.745 (7)	162
N4—H4⋯O12	0.86	1.88	2.734 (7)	171
O3—H3⋯O2	0.82	1.65	2.466 (6)	176
O7—H7⋯O6	0.82	1.70	2.523 (6)	180
O9—H9C⋯O4ii	0.85	2.11	2.960 (6)	174
O9—H9D⋯O8iii	0.85	1.96	2.807 (6)	173
O10—H10C⋯O4iv	0.85	1.87	2.724 (6)	177
O10—H10D⋯O11v	0.85	1.83	2.675 (7)	177
O11—H11C⋯O1vi	0.85	2.06	2.904 (6)	172
O11—H11C⋯O2vi	0.85	2.62	3.197 (7)	127
O11—H11D⋯O6i	0.85	1.99	2.830 (6)	172
O12—H12C⋯O14	0.85	1.84	2.676 (10)	166
O12—H12D⋯O3vi	0.85	2.07	2.904 (7)	167
O13—H13C⋯O11vii	0.85	2.23	2.889 (9)	134
O13—H13D⋯O8	0.85	2.44	3.068 (9)	131
O14—H14G⋯O13	0.85	1.99	2.488 (11)	117
O14—H14H⋯O14viii	0.85	1.54	2.355 (17)	160
O14—H14F⋯O5ix	0.85	2.19	2.778 (9)	127

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