Poly[aqua[μ(2)-1,2-bis-(imidazol-1-yl-methyl)benzene-κN:N](μ(2)-5-bromo-benzene-1,3-dicarboxyl-ato-κO,O:O)nickel(II)].

In the two-dimensional title coordination polymer, [Ni(C(8)H(3)BrO(4))(C(14)H(14)N(4))(H(2)O)](n), the Ni(II) atom adopts a distorted octa-hedral geometry, being ligated by three O atoms from two different 5-bromo-benzene-1,3-dicarboxyl-ate ligands, two N atoms from two 1,2-bis-(imidazol-1-ylmeth-yl)benzene ligands and one coordinated water mol-ecule. The Ni atoms are bridged by the 5-bromo-benzene-1,3-dicarboxyl-ate ligands, forming chains, which are further linked by 1,2-bis-(imidazol-1-ylmeth-yl)benzene, generating a layer structure parallel to (001).

Related literature

For general background to self-assembly coordination polymers with metal ions and bis­(imidazole) ligands inter­connected by flexible spacers, see: Qi et al. (2008 ▶); Liu et al. (2009 ▶). For the role played by different organic anions in directing the final structure and topology, see: Hu et al. (2008 ▶). For related structures, see: Liu et al. (2008 ▶).

Experimental

Crystal data

[Ni(C8H3BrO4)(C14H14N4)(H2O)]

M = 558.03

Triclinic,

a = 9.1374 (12) Å

b = 10.1394 (14) Å

c = 12.9642 (18) Å

α = 80.046 (2)°

β = 83.233 (2)°

γ = 70.004 (2)°

V = 1109.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.72 mm−1

T = 293 K

0.26 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS: Bruker, 1997 ▶) T min = 0.538, T max = 0.641

8172 measured reflections

4055 independent reflections

3029 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.085

S = 1.04

4055 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −1.12 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016286/at2774sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016286/at2774Isup2.hkl

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

[Ni(C8H3BrO4)(C14H14N4)(H2O)]	Z = 2
Mr = 558.03	F(000) = 564
Triclinic, P1	Dx = 1.670 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1374 (12) Å	Cell parameters from 2114 reflections
b = 10.1394 (14) Å	θ = 2.4–24.0°
c = 12.9642 (18) Å	µ = 2.72 mm−1
α = 80.046 (2)°	T = 293 K
β = 83.233 (2)°	Block, green
γ = 70.004 (2)°	0.26 × 0.20 × 0.18 mm
V = 1109.5 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	4055 independent reflections
Radiation source: sealed tube	3029 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS: Bruker, 1997)	h = −11→9
Tmin = 0.538, Tmax = 0.641	k = −12→11
8172 measured reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.029P)2 + 0.735P] where P = (Fo2 + 2Fc2)/3
4055 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −1.12 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	−0.11002 (5)	0.18147 (4)	0.34656 (3)	0.02475 (13)
N1	0.1280 (3)	0.0814 (3)	0.3229 (2)	0.0286 (7)
N2	0.3530 (3)	−0.0730 (3)	0.2776 (2)	0.0332 (7)
N3	0.4261 (3)	−0.5489 (3)	0.3554 (2)	0.0372 (8)
N4	0.6546 (3)	−0.7159 (3)	0.3708 (2)	0.0313 (7)
O1	−0.0886 (3)	0.3683 (2)	0.27370 (18)	0.0326 (6)
O2	−0.0881 (4)	0.4666 (3)	0.4146 (2)	0.0581 (9)
O3	−0.1442 (3)	0.9777 (2)	0.37521 (17)	0.0287 (5)
O4	−0.1529 (3)	1.0986 (2)	0.21699 (17)	0.0308 (6)
O1W	−0.0840 (3)	0.2116 (3)	0.4966 (2)	0.0341 (7)
Br1	−0.14928 (6)	0.76345 (5)	−0.06669 (3)	0.06060 (18)
C1	−0.0961 (4)	0.4705 (3)	0.3195 (3)	0.0282 (8)
C2	−0.1196 (4)	0.6114 (3)	0.2502 (3)	0.0251 (8)
C3	−0.1282 (4)	0.6229 (4)	0.1422 (3)	0.0291 (8)
H3	−0.1227	0.5444	0.1120	0.035*
C4	−0.1448 (4)	0.7516 (4)	0.0806 (3)	0.0306 (8)
C5	−0.1547 (4)	0.8709 (4)	0.1226 (3)	0.0309 (8)
H5	−0.1661	0.9569	0.0796	0.037*
C6	−0.1473 (4)	0.8599 (3)	0.2307 (3)	0.0239 (7)
C7	−0.1303 (4)	0.7308 (3)	0.2944 (3)	0.0242 (7)
H7	−0.1260	0.7240	0.3665	0.029*
C8	−0.1508 (4)	0.9869 (3)	0.2772 (3)	0.0247 (8)
C9	0.2459 (5)	0.1249 (4)	0.3411 (3)	0.0454 (11)
H9	0.2329	0.2076	0.3682	0.055*
C10	0.3845 (5)	0.0317 (4)	0.3144 (3)	0.0489 (11)
H10	0.4826	0.0376	0.3199	0.059*
C11	0.1973 (4)	−0.0380 (4)	0.2842 (3)	0.0342 (9)
H11	0.1444	−0.0919	0.2638	0.041*
C12	0.4673 (4)	−0.2047 (4)	0.2455 (3)	0.0468 (11)
H12A	0.4975	−0.2743	0.3074	0.056*
H12B	0.5601	−0.1848	0.2128	0.056*
C13	0.4039 (4)	−0.2660 (4)	0.1699 (3)	0.0388 (10)
C14	0.4232 (5)	−0.2198 (5)	0.0633 (4)	0.0578 (12)
H14	0.4746	−0.1540	0.0412	0.069*
C15	0.3664 (5)	−0.2713 (5)	−0.0108 (4)	0.060
H15	0.3765	−0.2380	−0.0819	0.072*
C16	0.2960 (4)	−0.3706 (3)	0.0223 (3)	0.060
H16	0.2594	−0.4069	−0.0267	0.072*
C17	0.2782 (4)	−0.4182 (3)	0.1269 (3)	0.0678 (15)
H17	0.2305	−0.4871	0.1477	0.081*
C18	0.3299 (4)	−0.3658 (4)	0.2031 (3)	0.0427 (10)
C19	0.3027 (5)	−0.4184 (4)	0.3173 (4)	0.0550 (12)
H19A	0.2961	−0.3452	0.3587	0.066*
H19B	0.2035	−0.4356	0.3275	0.066*
C20	0.5718 (4)	−0.6006 (4)	0.3131 (3)	0.0400 (10)
H20	0.6095	−0.5598	0.2505	0.048*
C21	0.5557 (5)	−0.7398 (4)	0.4541 (3)	0.0456 (10)
H21	0.5813	−0.8154	0.5082	0.055*
C22	0.4150 (5)	−0.6367 (5)	0.4458 (3)	0.0491 (11)
H22	0.3280	−0.6278	0.4926	0.059*
H1WA	−0.067 (5)	0.285 (5)	0.483 (3)	0.059 (16)*
H1WB	−0.008 (5)	0.158 (4)	0.529 (3)	0.047 (14)*

	U11	U22	U33	U12	U13	U23
Ni1	0.0333 (3)	0.0136 (2)	0.0266 (2)	−0.00590 (19)	−0.00584 (19)	−0.00212 (18)
N1	0.0322 (18)	0.0215 (16)	0.0319 (16)	−0.0074 (14)	−0.0049 (13)	−0.0040 (13)
N2	0.0253 (18)	0.0315 (18)	0.0413 (18)	−0.0055 (14)	−0.0041 (14)	−0.0079 (14)
N3	0.0277 (18)	0.0291 (18)	0.048 (2)	−0.0014 (14)	−0.0009 (15)	−0.0063 (15)
N4	0.0332 (18)	0.0224 (17)	0.0362 (17)	−0.0061 (14)	−0.0031 (14)	−0.0044 (14)
O1	0.0496 (16)	0.0163 (12)	0.0325 (13)	−0.0115 (12)	−0.0013 (12)	−0.0046 (10)
O2	0.118 (3)	0.0240 (15)	0.0365 (16)	−0.0248 (16)	−0.0304 (17)	0.0041 (12)
O3	0.0397 (15)	0.0172 (12)	0.0281 (13)	−0.0078 (11)	−0.0057 (11)	−0.0015 (10)
O4	0.0452 (16)	0.0179 (13)	0.0313 (13)	−0.0116 (12)	−0.0099 (11)	−0.0011 (10)
O1W	0.0465 (19)	0.0231 (16)	0.0311 (15)	−0.0087 (15)	−0.0100 (13)	−0.0006 (12)
Br1	0.1137 (5)	0.0440 (3)	0.0264 (2)	−0.0292 (3)	−0.0036 (2)	−0.00487 (19)
C1	0.035 (2)	0.0182 (19)	0.032 (2)	−0.0078 (16)	−0.0067 (16)	−0.0026 (15)
C2	0.0250 (19)	0.0179 (18)	0.0340 (19)	−0.0079 (15)	−0.0046 (15)	−0.0045 (15)
C3	0.036 (2)	0.0230 (19)	0.0308 (19)	−0.0107 (16)	−0.0016 (16)	−0.0076 (15)
C4	0.041 (2)	0.029 (2)	0.0225 (18)	−0.0123 (17)	−0.0039 (16)	−0.0030 (15)
C5	0.043 (2)	0.0176 (18)	0.0308 (19)	−0.0116 (17)	−0.0045 (17)	0.0044 (15)
C6	0.0235 (19)	0.0167 (17)	0.0319 (19)	−0.0069 (15)	−0.0033 (15)	−0.0031 (14)
C7	0.0260 (19)	0.0187 (18)	0.0283 (18)	−0.0070 (15)	−0.0077 (15)	−0.0016 (14)
C8	0.0231 (19)	0.0146 (18)	0.035 (2)	−0.0040 (14)	−0.0050 (15)	−0.0012 (15)
C9	0.047 (3)	0.037 (2)	0.062 (3)	−0.018 (2)	−0.005 (2)	−0.018 (2)
C10	0.038 (3)	0.050 (3)	0.067 (3)	−0.022 (2)	−0.004 (2)	−0.016 (2)
C11	0.030 (2)	0.029 (2)	0.046 (2)	−0.0084 (17)	−0.0084 (17)	−0.0067 (17)
C12	0.026 (2)	0.046 (3)	0.063 (3)	0.0006 (19)	−0.003 (2)	−0.018 (2)
C13	0.031 (2)	0.035 (2)	0.041 (2)	0.0059 (18)	−0.0073 (18)	−0.0122 (19)
C14	0.063 (3)	0.037 (3)	0.056 (3)	0.003 (2)	−0.004 (2)	−0.001 (2)
C15	0.059	0.050	0.054	0.015	−0.024	−0.016
C16	0.059	0.050	0.054	0.015	−0.024	−0.016
C17	0.038 (3)	0.050 (3)	0.115 (5)	−0.002 (2)	−0.015 (3)	−0.029 (3)
C18	0.025 (2)	0.034 (2)	0.061 (3)	0.0076 (18)	−0.0108 (19)	−0.013 (2)
C19	0.032 (2)	0.039 (3)	0.079 (3)	0.003 (2)	0.007 (2)	−0.003 (2)
C20	0.035 (2)	0.032 (2)	0.045 (2)	−0.0026 (19)	0.0000 (19)	−0.0001 (19)
C21	0.049 (3)	0.044 (3)	0.040 (2)	−0.015 (2)	−0.002 (2)	0.0038 (19)
C22	0.044 (3)	0.054 (3)	0.046 (3)	−0.016 (2)	0.005 (2)	−0.005 (2)

Ni1—O1	2.027 (2)	C4—C5	1.381 (5)
Ni1—N4i	2.057 (3)	C5—C6	1.395 (5)
Ni1—N1	2.072 (3)	C5—H5	0.9300
Ni1—O1W	2.073 (3)	C6—C7	1.392 (4)
Ni1—O4ii	2.133 (2)	C6—C8	1.503 (4)
Ni1—O3ii	2.157 (2)	C7—H7	0.9300
Ni1—C8ii	2.456 (3)	C8—Ni1iv	2.456 (3)
N1—C11	1.315 (4)	C9—C10	1.345 (5)
N1—C9	1.354 (4)	C9—H9	0.9300
N2—C11	1.339 (4)	C10—H10	0.9300
N2—C10	1.361 (5)	C11—H11	0.9300
N2—C12	1.478 (4)	C12—C13	1.508 (5)
N3—C20	1.341 (4)	C12—H12A	0.9700
N3—C22	1.360 (5)	C12—H12B	0.9700
N3—C19	1.466 (5)	C13—C18	1.383 (6)
N4—C20	1.314 (4)	C13—C14	1.392 (6)
N4—C21	1.368 (5)	C14—C15	1.393 (6)
N4—Ni1iii	2.057 (3)	C14—H14	0.9300
O1—C1	1.260 (4)	C15—C16	1.357 (6)
O2—C1	1.237 (4)	C15—H15	0.9300
O3—C8	1.264 (4)	C16—C17	1.368 (6)
O3—Ni1iv	2.157 (2)	C16—H16	0.9300
O4—C8	1.255 (4)	C17—C18	1.395 (5)
O4—Ni1iv	2.133 (2)	C17—H17	0.9300
O1W—H1WA	0.80 (5)	C18—C19	1.507 (6)
O1W—H1WB	0.82 (4)	C19—H19A	0.9700
Br1—C4	1.897 (3)	C19—H19B	0.9700
C1—C2	1.512 (5)	C20—H20	0.9300
C2—C3	1.394 (4)	C21—C22	1.353 (5)
C2—C7	1.396 (4)	C21—H21	0.9300
C3—C4	1.377 (5)	C22—H22	0.9300
C3—H3	0.9300
O1—Ni1—N4i	88.51 (11)	C6—C7—C2	120.1 (3)
O1—Ni1—N1	90.67 (10)	C6—C7—H7	119.9
N4i—Ni1—N1	178.90 (11)	C2—C7—H7	119.9
O1—Ni1—O1W	95.91 (11)	O4—C8—O3	121.2 (3)
N4i—Ni1—O1W	87.85 (12)	O4—C8—C6	118.9 (3)
N1—Ni1—O1W	91.50 (11)	O3—C8—C6	119.8 (3)
O1—Ni1—O4ii	100.66 (9)	O4—C8—Ni1iv	60.26 (16)
N4i—Ni1—O4ii	90.21 (10)	O3—C8—Ni1iv	61.33 (16)
N1—Ni1—O4ii	90.66 (10)	C6—C8—Ni1iv	170.6 (2)
O1W—Ni1—O4ii	163.26 (11)	C10—C9—N1	110.4 (3)
O1—Ni1—O3ii	162.21 (9)	C10—C9—H9	124.8
N4i—Ni1—O3ii	91.35 (10)	N1—C9—H9	124.8
N1—Ni1—O3ii	89.66 (10)	C9—C10—N2	106.4 (3)
O1W—Ni1—O3ii	101.87 (10)	C9—C10—H10	126.8
O4ii—Ni1—O3ii	61.55 (9)	N2—C10—H10	126.8
O1—Ni1—C8ii	131.29 (10)	N1—C11—N2	112.2 (3)
N4i—Ni1—C8ii	93.07 (11)	N1—C11—H11	123.9
N1—Ni1—C8ii	88.03 (11)	N2—C11—H11	123.9
O1W—Ni1—C8ii	132.80 (12)	N2—C12—C13	112.5 (3)
O4ii—Ni1—C8ii	30.73 (9)	N2—C12—H12A	109.1
O3ii—Ni1—C8ii	30.95 (9)	C13—C12—H12A	109.1
C11—N1—C9	104.8 (3)	N2—C12—H12B	109.1
C11—N1—Ni1	127.0 (2)	C13—C12—H12B	109.1
C9—N1—Ni1	128.2 (2)	H12A—C12—H12B	107.8
C11—N2—C10	106.2 (3)	C18—C13—C14	120.0 (4)
C11—N2—C12	126.8 (3)	C18—C13—C12	122.4 (4)
C10—N2—C12	126.9 (3)	C14—C13—C12	117.6 (4)
C20—N3—C22	106.9 (3)	C15—C14—C13	120.7 (5)
C20—N3—C19	127.8 (3)	C15—C14—H14	119.7
C22—N3—C19	125.2 (3)	C13—C14—H14	119.7
C20—N4—C21	105.2 (3)	C16—C15—C14	119.0 (4)
C20—N4—Ni1iii	125.5 (3)	C16—C15—H15	120.5
C21—N4—Ni1iii	128.8 (3)	C14—C15—H15	120.5
C1—O1—Ni1	124.9 (2)	C15—C16—C17	120.9 (3)
C8—O3—Ni1iv	87.72 (19)	C15—C16—H16	119.6
C8—O4—Ni1iv	89.01 (19)	C17—C16—H16	119.6
Ni1—O1W—H1WA	99 (3)	C16—C17—C18	121.5 (3)
Ni1—O1W—H1WB	120 (3)	C16—C17—H17	119.3
H1WA—O1W—H1WB	104 (4)	C18—C17—H17	119.2
O2—C1—O1	126.4 (3)	C13—C18—C17	118.0 (4)
O2—C1—C2	117.8 (3)	C13—C18—C19	122.7 (4)
O1—C1—C2	115.9 (3)	C17—C18—C19	119.3 (4)
C3—C2—C7	119.6 (3)	N3—C19—C18	112.9 (3)
C3—C2—C1	120.7 (3)	N3—C19—H19A	109.0
C7—C2—C1	119.8 (3)	C18—C19—H19A	109.0
C4—C3—C2	119.3 (3)	N3—C19—H19B	109.0
C4—C3—H3	120.3	C18—C19—H19B	109.0
C2—C3—H3	120.3	H19A—C19—H19B	107.8
C3—C4—C5	122.1 (3)	N4—C20—N3	111.8 (3)
C3—C4—Br1	118.7 (2)	N4—C20—H20	124.1
C5—C4—Br1	119.3 (3)	N3—C20—H20	124.1
C4—C5—C6	118.7 (3)	C22—C21—N4	109.7 (4)
C4—C5—H5	120.7	C22—C21—H21	125.1
C6—C5—H5	120.7	N4—C21—H21	125.1
C7—C6—C5	120.2 (3)	C21—C22—N3	106.4 (4)
C7—C6—C8	120.3 (3)	C21—C22—H22	126.8
C5—C6—C8	119.5 (3)	N3—C22—H22	126.8
O1—Ni1—N1—C11	−131.0 (3)	C7—C6—C8—O3	−2.7 (5)
N4i—Ni1—N1—C11	−173 (47)	C5—C6—C8—O3	179.9 (3)
O1W—Ni1—N1—C11	133.1 (3)	C7—C6—C8—Ni1iv	91.6 (15)
O4ii—Ni1—N1—C11	−30.3 (3)	C5—C6—C8—Ni1iv	−85.7 (15)
O3ii—Ni1—N1—C11	31.2 (3)	C11—N1—C9—C10	−0.5 (5)
C8ii—Ni1—N1—C11	0.3 (3)	Ni1—N1—C9—C10	−179.1 (3)
O1—Ni1—N1—C9	47.3 (3)	N1—C9—C10—N2	0.4 (5)
N4i—Ni1—N1—C9	5(6)	C11—N2—C10—C9	−0.1 (5)
O1W—Ni1—N1—C9	−48.6 (3)	C12—N2—C10—C9	−175.4 (4)
O4ii—Ni1—N1—C9	148.0 (3)	C9—N1—C11—N2	0.5 (4)
O3ii—Ni1—N1—C9	−150.5 (3)	Ni1—N1—C11—N2	179.1 (2)
C8ii—Ni1—N1—C9	178.6 (3)	C10—N2—C11—N1	−0.2 (4)
N4i—Ni1—O1—C1	73.7 (3)	C12—N2—C11—N1	175.1 (3)
N1—Ni1—O1—C1	−105.6 (3)	C11—N2—C12—C13	29.1 (5)
O1W—Ni1—O1—C1	−14.0 (3)	C10—N2—C12—C13	−156.5 (4)
O4ii—Ni1—O1—C1	163.6 (3)	N2—C12—C13—C18	−91.9 (4)
O3ii—Ni1—O1—C1	163.4 (3)	N2—C12—C13—C14	88.7 (4)
C8ii—Ni1—O1—C1	166.5 (3)	C18—C13—C14—C15	1.1 (6)
Ni1—O1—C1—O2	14.5 (5)	C12—C13—C14—C15	−179.5 (3)
Ni1—O1—C1—C2	−164.5 (2)	C13—C14—C15—C16	−2.1 (6)
O2—C1—C2—C3	179.4 (3)	C14—C15—C16—C17	1.2 (5)
O1—C1—C2—C3	−1.5 (5)	C15—C16—C17—C18	0.6 (3)
O2—C1—C2—C7	0.5 (5)	C14—C13—C18—C17	0.7 (5)
O1—C1—C2—C7	179.6 (3)	C12—C13—C18—C17	−178.7 (3)
C7—C2—C3—C4	0.9 (5)	C14—C13—C18—C19	−178.9 (3)
C1—C2—C3—C4	−178.0 (3)	C12—C13—C18—C19	1.7 (5)
C2—C3—C4—C5	−0.6 (5)	C16—C17—C18—C13	−1.6 (4)
C2—C3—C4—Br1	177.9 (3)	C16—C17—C18—C19	178.0 (2)
C3—C4—C5—C6	0.1 (6)	C20—N3—C19—C18	20.2 (6)
Br1—C4—C5—C6	−178.4 (3)	C22—N3—C19—C18	−163.9 (4)
C4—C5—C6—C7	0.0 (5)	C13—C18—C19—N3	−94.0 (5)
C4—C5—C6—C8	177.3 (3)	C17—C18—C19—N3	86.4 (4)
C5—C6—C7—C2	0.4 (5)	C21—N4—C20—N3	0.6 (4)
C8—C6—C7—C2	−177.0 (3)	Ni1iii—N4—C20—N3	−172.4 (2)
C3—C2—C7—C6	−0.8 (5)	C22—N3—C20—N4	−0.1 (4)
C1—C2—C7—C6	178.1 (3)	C19—N3—C20—N4	176.4 (4)
Ni1iv—O4—C8—O3	7.4 (3)	C20—N4—C21—C22	−0.9 (4)
Ni1iv—O4—C8—C6	−169.3 (3)	Ni1iii—N4—C21—C22	171.8 (3)
Ni1iv—O3—C8—O4	−7.4 (3)	N4—C21—C22—N3	0.8 (5)
Ni1iv—O3—C8—C6	169.3 (3)	C20—N3—C22—C21	−0.5 (4)
C7—C6—C8—O4	174.1 (3)	C19—N3—C22—C21	−177.1 (4)
C5—C6—C8—O4	−3.3 (5)