Hexakis(1H-imidazole-κN³)­nickel(II) benzene-1,3-dioxy­acetate

In the title complex, [Ni(C₃H₄N₂)₆](C₁₀H₈O₆), the Ni^II atom shows an octahedral coordination geometry, defined by six N atoms from different imidazole ligands. The cations and anions are linked by hydrogen bonds into a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.118
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C6      ..       5.37 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34    ..  O1      ..       2.62 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

hexakis(1H-imidazole-κN³)nickel(II) (m-phenylenedioxy)diacetate

Crystal data

[Ni(C3H4N2)6](C10H8O6)	Z = 2
Mr = 691.35	F(000) = 720
Triclinic, P1	Dx = 1.465 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.998 (2) Å	Cell parameters from 6147 reflections
b = 11.741 (2) Å	θ = 3.1–26.0°
c = 15.836 (3) Å	µ = 0.68 mm^−1
α = 102.28 (3)°	T = 293 K
β = 106.11 (3)°	Prism, green
γ = 90.14 (3)°	0.38 × 0.25 × 0.18 mm
V = 1567.2 (6) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5968 independent reflections
Radiation source: fine-focus sealed tube	4368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10 pixels mm^-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→14
Tmin = 0.781, Tmax = 0.887	l = −19→19
12850 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0704P)^2] where P = (Fo^2 + 2Fc^2)/3
5968 reflections	(Δ/σ)max < 0.001
424 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.48959 (4)	0.49556 (3)	0.23731 (2)	0.0299 (1)
N1	0.3041 (3)	0.4042 (2)	0.2603 (2)	0.0354 (5)
N2	0.1771 (3)	0.3090 (2)	0.3260 (2)	0.0496 (7)
N3	0.4887 (3)	0.6290 (2)	0.3500 (2)	0.0370 (5)
N4	0.5670 (3)	0.7777 (2)	0.4651 (2)	0.0522 (7)
N5	0.3277 (2)	0.5855 (2)	0.1527 (2)	0.0320 (5)
N6	0.1705 (3)	0.7189 (2)	0.1083 (2)	0.0386 (6)
N7	0.6734 (2)	0.5906 (2)	0.2164 (2)	0.0353 (5)
N8	0.8002 (3)	0.7069 (2)	0.1647 (2)	0.0483 (7)
N9	0.4923 (2)	0.3587 (2)	0.1274 (2)	0.0331 (5)
N10	0.4379 (3)	0.1941 (2)	0.0246 (2)	0.0398 (6)
N11	0.6531 (3)	0.4060 (2)	0.3229 (2)	0.0374 (5)
N12	0.7930 (3)	0.2647 (2)	0.3690 (2)	0.0475 (7)
O1	0.1228 (2)	0.1647 (2)	0.4328 (1)	0.0465 (5)
O2	−0.0946 (2)	0.0507 (2)	0.3817 (2)	0.0575 (6)
O3	0.2993 (2)	−0.0213 (2)	0.4142 (1)	0.0452 (5)
O4	0.1529 (2)	0.0318 (2)	0.1071 (1)	0.0489 (6)
O5	−0.2495 (2)	−0.0089 (2)	0.0926 (2)	0.0542 (6)
O6	−0.0710 (2)	−0.1391 (2)	0.0895 (2)	0.0431 (5)
C1	0.3148 (4)	0.3382 (3)	0.3195 (2)	0.0497 (8)
C2	0.1479 (3)	0.4155 (3)	0.2283 (2)	0.0426 (7)
C3	0.0701 (4)	0.3567 (3)	0.2687 (2)	0.0505 (8)
C4	0.5977 (3)	0.7133 (3)	0.3933 (2)	0.0443 (7)
C5	0.3834 (4)	0.6442 (3)	0.3986 (2)	0.0477 (8)
C6	0.4302 (4)	0.7353 (3)	0.4695 (2)	0.0537 (8)
C7	0.2836 (3)	0.6931 (2)	0.1746 (2)	0.0374 (7)
C8	0.2359 (3)	0.5427 (3)	0.0666 (2)	0.0418 (7)
C9	0.1382 (3)	0.6241 (3)	0.0391 (2)	0.0449 (7)
C10	0.6612 (3)	0.6596 (3)	0.1596 (2)	0.0449 (7)
C11	0.8289 (3)	0.5937 (3)	0.2583 (2)	0.0468 (8)
C12	0.9068 (4)	0.6664 (3)	0.2270 (2)	0.0521 (8)
C13	0.3895 (3)	0.2701 (2)	0.0852 (2)	0.0375 (7)
C14	0.6127 (3)	0.3361 (3)	0.0906 (2)	0.0424 (7)
C15	0.5817 (4)	0.2345 (3)	0.0277 (2)	0.0441 (7)
C16	0.6839 (3)	0.2950 (3)	0.3032 (2)	0.0420 (7)
C17	0.7502 (4)	0.4481 (3)	0.4079 (2)	0.0502 (8)
C18	0.8377 (4)	0.3613 (3)	0.4369 (2)	0.0554 (9)
C19	0.0492 (3)	0.0674 (3)	0.4075 (2)	0.0397 (7)
C20	0.1410 (3)	−0.0412 (3)	0.4105 (2)	0.0448 (7)
C21	0.3292 (3)	−0.0108 (2)	0.3358 (2)	0.0368 (6)
C22	0.4836 (3)	−0.0110 (3)	0.3363 (2)	0.0456 (8)
C23	0.5213 (3)	−0.0026 (2)	0.2592 (2)	0.0483 (8)
C24	0.4103 (3)	0.0101 (2)	0.1831 (2)	0.0436 (7)
C25	0.2564 (3)	0.0149 (2)	0.1843 (2)	0.0371 (6)
C26	0.2151 (3)	0.0022 (2)	0.2596 (2)	0.0360 (6)
C27	0.0015 (3)	0.0635 (2)	0.1095 (2)	0.0428 (7)
C28	−0.1143 (3)	−0.0363 (2)	0.0967 (2)	0.0360 (6)
H1	0.4078	0.3152	0.3525	0.060*
H2	0.1027	0.4576	0.1853	0.051*
H3	−0.0367	0.3504	0.2588	0.061*
H4	0.6854	0.7259	0.3755	0.053*
H5	0.2921	0.5979	0.3846	0.057*
H6	0.3791	0.7633	0.5127	0.064*
H7	0.3268	0.7444	0.2298	0.045*
H8	0.2399	0.4687	0.0319	0.050*
H9	0.0639	0.6162	−0.0163	0.054*
H10	0.5681	0.6738	0.1208	0.054*
H11	0.8742	0.5521	0.3018	0.056*
H12	1.0132	0.6846	0.2451	0.063*
H13	0.2944	0.2616	0.0964	0.045*
H14	0.7032	0.3839	0.1065	0.051*
H15	0.6453	0.1996	−0.0064	0.053*
H16	0.6345	0.2435	0.2491	0.050*
H17	0.7558	0.5244	0.4409	0.060*
H18	0.9125	0.3673	0.4919	0.066*
H20A	0.1368	−0.0699	0.4630	0.054*
H20B	0.0921	−0.1015	0.3575	0.054*
H22	0.5607	−0.0167	0.3880	0.055*
H23	0.6243	−0.0055	0.2587	0.058*
H24	0.4375	0.0153	0.1314	0.052*
H26	0.1116	0.0024	0.2593	0.043*
H27A	−0.0387	0.1065	0.0629	0.051*
H27B	0.0096	0.1161	0.1670	0.051*
H29	0.1593	0.2669	0.3609	0.060*
H30	0.6239	0.8361	0.5023	0.063*
H31	0.1263	0.7839	0.1094	0.046*
H32	0.8177	0.7546	0.1336	0.058*
H33	0.3876	0.1312	−0.0100	0.048*
H34	0.8285	0.1968	0.3687	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0253 (2)	0.0274 (2)	0.0367 (2)	0.0003 (1)	0.0073 (2)	0.0084 (1)
N1	0.032 (1)	0.032 (1)	0.044 (1)	0.000 (1)	0.012 (1)	0.010 (1)
N2	0.050 (2)	0.043 (1)	0.070 (2)	0.000 (1)	0.031 (2)	0.024 (1)
N3	0.036 (1)	0.034 (1)	0.038 (1)	0.001 (1)	0.006 (1)	0.005 (1)
N4	0.070 (2)	0.042 (1)	0.034 (2)	−0.007 (1)	0.005 (1)	−0.002 (1)
N5	0.028 (1)	0.031 (1)	0.038 (1)	0.0013 (9)	0.009 (1)	0.009 (1)
N6	0.035 (1)	0.035 (1)	0.051 (2)	0.008 (1)	0.014 (1)	0.017 (1)
N7	0.031 (1)	0.032 (1)	0.045 (2)	−0.001 (1)	0.010 (1)	0.012 (1)
N8	0.043 (2)	0.042 (1)	0.068 (2)	−0.003 (1)	0.020 (1)	0.024 (1)
N9	0.029 (1)	0.032 (1)	0.038 (1)	0.004 (1)	0.008 (1)	0.009 (1)
N10	0.040 (1)	0.032 (1)	0.043 (2)	0.000 (1)	0.007 (1)	0.004 (1)
N11	0.031 (1)	0.037 (1)	0.045 (2)	0.002 (1)	0.008 (1)	0.015 (1)
N12	0.039 (1)	0.050 (2)	0.062 (2)	0.012 (1)	0.015 (1)	0.030 (1)
O1	0.046 (1)	0.040 (1)	0.056 (1)	0.002 (1)	0.014 (1)	0.018 (1)
O2	0.037 (1)	0.060 (1)	0.074 (2)	0.002 (1)	0.006 (1)	0.025 (1)
O3	0.041 (1)	0.058 (1)	0.036 (1)	0.015 (1)	0.0067 (9)	0.014 (1)
O4	0.041 (1)	0.069 (1)	0.034 (1)	−0.011 (1)	0.0044 (9)	0.015 (1)
O5	0.037 (1)	0.044 (1)	0.074 (2)	0.006 (1)	0.013 (1)	0.001 (1)
O6	0.038 (1)	0.031 (1)	0.063 (1)	0.0037 (9)	0.013 (1)	0.0181 (9)
C1	0.041 (2)	0.050 (2)	0.066 (2)	0.004 (2)	0.016 (2)	0.028 (2)
C2	0.034 (2)	0.046 (2)	0.050 (2)	−0.002 (1)	0.010 (1)	0.017 (1)
C3	0.036 (2)	0.052 (2)	0.068 (2)	−0.003 (2)	0.019 (2)	0.018 (2)
C4	0.042 (2)	0.040 (2)	0.046 (2)	−0.002 (1)	0.007 (2)	0.008 (1)
C5	0.046 (2)	0.051 (2)	0.044 (2)	−0.003 (2)	0.015 (2)	0.004 (2)
C6	0.066 (2)	0.053 (2)	0.045 (2)	−0.003 (2)	0.023 (2)	0.006 (2)
C7	0.034 (2)	0.034 (1)	0.044 (2)	0.002 (1)	0.009 (1)	0.011 (1)
C8	0.040 (2)	0.036 (2)	0.044 (2)	0.003 (1)	0.008 (1)	0.004 (1)
C9	0.038 (2)	0.049 (2)	0.044 (2)	0.002 (1)	0.001 (1)	0.017 (2)
C10	0.033 (2)	0.047 (2)	0.057 (2)	0.001 (1)	0.010 (1)	0.021 (2)
C11	0.033 (2)	0.050 (2)	0.062 (2)	0.001 (1)	0.012 (2)	0.024 (2)
C12	0.032 (2)	0.058 (2)	0.070 (2)	−0.006 (2)	0.015 (2)	0.022 (2)
C13	0.032 (2)	0.033 (1)	0.048 (2)	0.001 (1)	0.011 (1)	0.010 (1)
C14	0.036 (2)	0.045 (2)	0.045 (2)	−0.002 (1)	0.013 (1)	0.004 (1)
C15	0.044 (2)	0.045 (2)	0.046 (2)	0.004 (1)	0.020 (2)	0.006 (1)
C16	0.032 (2)	0.043 (2)	0.054 (2)	0.005 (1)	0.011 (1)	0.018 (1)
C17	0.047 (2)	0.053 (2)	0.047 (2)	0.004 (2)	0.006 (2)	0.015 (2)
C18	0.046 (2)	0.070 (2)	0.052 (2)	0.005 (2)	0.005 (2)	0.029 (2)
C19	0.039 (2)	0.050 (2)	0.032 (2)	0.007 (1)	0.010 (1)	0.016 (1)
C20	0.051 (2)	0.045 (2)	0.044 (2)	0.008 (2)	0.015 (2)	0.020 (1)
C21	0.038 (2)	0.033 (1)	0.036 (2)	0.005 (1)	0.009 (1)	0.003 (1)
C22	0.035 (2)	0.042 (2)	0.051 (2)	0.007 (1)	0.001 (1)	0.006 (1)
C23	0.033 (2)	0.042 (2)	0.067 (2)	−0.002 (1)	0.017 (2)	0.003 (2)
C24	0.042 (2)	0.039 (2)	0.052 (2)	−0.007 (1)	0.021 (2)	0.005 (1)
C25	0.035 (2)	0.035 (1)	0.035 (2)	−0.008 (1)	0.003 (1)	0.002 (1)
C26	0.029 (1)	0.042 (2)	0.033 (2)	−0.001 (1)	0.007 (1)	0.002 (1)
C27	0.043 (2)	0.040 (2)	0.039 (2)	−0.003 (1)	−0.001 (1)	0.011 (1)
C28	0.035 (2)	0.037 (2)	0.032 (2)	0.001 (1)	0.003 (1)	0.009 (1)

Geometric parameters (Å, º)

Ni1—N1	2.136 (2)	O5—C28	1.247 (3)
Ni1—N3	2.111 (2)	O6—C28	1.261 (3)
Ni1—N5	2.135 (2)	C1—H1	0.9300
Ni1—N7	2.131 (2)	C2—C3	1.345 (4)
Ni1—N9	2.109 (2)	C2—H2	0.9300
Ni1—N11	2.148 (2)	C3—H3	0.9300
N1—C1	1.322 (4)	C4—H4	0.9300
N1—C2	1.373 (3)	C5—C6	1.344 (4)
N2—C1	1.322 (4)	C5—H5	0.9300
N2—C3	1.341 (4)	C6—H6	0.9300
N2—H29	0.8600	C7—H7	0.9300
N3—C4	1.321 (3)	C8—C9	1.358 (4)
N3—C5	1.368 (4)	C8—H8	0.9300
N4—C4	1.322 (4)	C9—H9	0.9300
N4—C6	1.352 (4)	C10—H10	0.9300
N4—H30	0.8600	C11—C12	1.356 (4)
N5—C7	1.329 (3)	C11—H11	0.9300
N5—C8	1.370 (4)	C12—H12	0.9300
N6—C7	1.331 (4)	C13—H13	0.9300
N6—C9	1.352 (4)	C14—C15	1.353 (4)
N6—H31	0.8600	C14—H14	0.9300
N7—C10	1.318 (4)	C15—H15	0.9300
N7—C11	1.369 (4)	C16—H16	0.9300
N8—C10	1.341 (4)	C17—C18	1.368 (4)
N8—C12	1.340 (4)	C17—H17	0.9300
N8—H32	0.8600	C18—H18	0.9300
N9—C13	1.320 (3)	C19—C20	1.523 (4)
N9—C14	1.368 (4)	C20—H20A	0.9700
N10—C13	1.332 (4)	C20—H20B	0.9700
N10—C15	1.361 (4)	C21—C26	1.387 (4)
N10—H33	0.8600	C21—C22	1.388 (4)
N11—C16	1.323 (4)	C22—C23	1.377 (4)
N11—C17	1.372 (4)	C22—H22	0.9300
N12—C16	1.329 (4)	C23—C24	1.371 (4)
N12—C18	1.358 (4)	C23—H23	0.9300
N12—H34	0.8600	C24—C25	1.391 (4)
O1—C19	1.248 (3)	C24—H24	0.9300
O2—C19	1.245 (3)	C25—C26	1.380 (4)
O3—C21	1.370 (3)	C26—H26	0.9300
O3—C20	1.426 (3)	C27—C28	1.509 (4)
O4—C25	1.369 (3)	C27—H27A	0.9700
O4—C27	1.422 (3)	C27—H27B	0.9700
N1—Ni1—N11	89.56 (9)	C2—C3—H3	126.8
N3—Ni1—N1	88.71 (9)	C3—N2—H29	126.0
N3—Ni1—N5	89.42 (9)	C3—C2—N1	109.8 (3)
N3—Ni1—N7	89.92 (9)	C3—C2—H2	125.1
N3—Ni1—N11	90.3 (1)	C4—N3—Ni1	126.9 (2)
N5—Ni1—N1	90.62 (9)	C4—N3—C5	104.1 (3)
N5—Ni1—N11	179.68 (9)	C4—N4—C6	107.9 (3)
N7—Ni1—N1	178.56 (9)	C4—N4—H30	126.1
N7—Ni1—N5	88.93 (8)	C5—N3—Ni1	128.9 (2)
N7—Ni1—N11	90.90 (9)	C5—C6—N4	105.6 (3)
N9—Ni1—N1	90.49 (9)	C5—C6—H6	127.2
N9—Ni1—N3	178.28 (8)	C6—N4—H30	126.1
N9—Ni1—N5	92.12 (9)	C6—C5—N3	110.6 (3)
N9—Ni1—N7	90.89 (9)	C6—C5—H5	124.7
N9—Ni1—N11	88.15 (9)	C7—N5—Ni1	127.5 (2)
N1—C1—N2	111.7 (3)	C7—N5—C8	104.1 (2)
N1—C1—H1	124.2	C7—N6—C9	107.2 (2)
N1—C2—H2	125.1	C7—N6—H31	126.4
N2—C1—H1	124.2	C8—N5—Ni1	128.1 (2)
N2—C3—C2	106.4 (3)	C8—C9—H9	126.8
N2—C3—H3	126.8	C9—N6—H31	126.4
N3—C4—N4	111.8 (3)	C9—C8—N5	110.1 (3)
N3—C4—H4	124.1	C9—C8—H8	125.0
N3—C5—H5	124.7	C10—N7—Ni1	127.1 (2)
N4—C4—H4	124.1	C10—N7—C11	104.9 (2)
N4—C6—H6	127.2	C10—N8—H32	126.2
N5—C7—N6	112.2 (3)	C11—N7—Ni1	128.1 (2)
N5—C7—H7	123.9	C11—C12—H12	126.8
N5—C8—H8	125.0	C12—N8—C10	107.6 (2)
N6—C7—H7	123.9	C12—N8—H32	126.2
N6—C9—C8	106.3 (3)	C12—C11—N7	109.7 (3)
N6—C9—H9	126.8	C12—C11—H11	125.1
N7—C10—N8	111.4 (3)	C13—N9—Ni1	129.1 (2)
N7—C10—H10	124.3	C13—N9—C14	104.4 (2)
N7—C11—H11	125.1	C13—N10—C15	107.4 (2)
N8—C10—H10	124.3	C13—N10—H33	126.3
N8—C12—C11	106.4 (3)	C14—N9—Ni1	126.2 (2)
N8—C12—H12	126.8	C14—C15—N10	105.6 (3)
N9—C13—N10	112.1 (2)	C14—C15—H15	127.2
N9—C13—H13	124.0	C15—N10—H33	126.3
N9—C14—H14	124.8	C15—C14—N9	110.5 (3)
N10—C13—H13	124.0	C15—C14—H14	124.8
N10—C15—H15	127.2	C16—N11—Ni1	126.5 (2)
N11—C16—N12	112.9 (3)	C16—N11—C17	104.1 (3)
N11—C16—H16	123.6	C16—N12—C18	107.1 (3)
N11—C17—H17	125.0	C16—N12—H34	126.4
N12—C16—H16	123.6	C17—N11—Ni1	129.4 (2)
N12—C18—C17	105.9 (3)	C17—C18—H18	127.0
N12—C18—H18	127.0	C18—N12—H34	126.4
O1—C19—C20	118.1 (3)	C18—C17—N11	110.0 (3)
O2—C19—O1	125.7 (3)	C18—C17—H17	125.0
O2—C19—C20	116.3 (3)	C19—C20—H20A	108.9
O3—C20—C19	113.5 (2)	C19—C20—H20B	108.9
O3—C20—H20A	108.9	C21—C22—H22	120.4
O3—C20—H20B	108.9	C21—C26—H26	120.3
O3—C21—C22	116.2 (3)	C22—C23—H23	119.3
O3—C21—C26	123.5 (3)	C23—C22—C21	119.1 (3)
O4—C25—C26	123.7 (3)	C23—C22—H22	120.4
O4—C25—C24	115.7 (3)	C23—C24—C25	119.0 (3)
O4—C27—C28	115.7 (2)	C23—C24—H24	120.5
O4—C27—H27A	108.3	C24—C23—C22	121.5 (3)
O4—C27—H27B	108.3	C24—C23—H23	119.3
O5—C28—O6	124.9 (3)	C25—C24—H24	120.5
O5—C28—C27	115.5 (3)	C26—C21—C22	120.3 (3)
O6—C28—C27	119.6 (3)	C26—C25—C24	120.5 (3)
C21—O3—C20	117.0 (2)	C25—C26—C21	119.5 (3)
C25—O4—C27	118.9 (2)	C25—C26—H26	120.3
C1—N1—Ni1	127.2 (2)	C28—C27—H27A	108.3
C1—N1—C2	104.2 (2)	C28—C27—H27B	108.3
C1—N2—C3	107.9 (3)	H20A—C20—H20B	107.7
C1—N2—H29	126.0	H27A—C27—H27B	107.4
C2—N1—Ni1	127.8 (2)
Ni1—N1—C1—N2	170.4 (2)	N9—Ni1—N11—C17	161.3 (3)
Ni1—N1—C2—C3	−170.5 (2)	N9—C14—C15—N10	0.8 (4)
Ni1—N3—C4—N4	−175.3 (2)	N11—Ni1—N1—C1	9.6 (3)
Ni1—N3—C5—C6	175.5 (2)	N11—Ni1—N1—C2	177.9 (2)
Ni1—N5—C7—N6	−174.4 (2)	N11—Ni1—N3—C4	75.7 (2)
Ni1—N5—C8—C9	174.2 (2)	N11—Ni1—N3—C5	−99.2 (3)
Ni1—N7—C10—N8	179.2 (2)	N11—Ni1—N7—C10	172.1 (3)
Ni1—N7—C11—C12	−178.9 (2)	N11—Ni1—N7—C11	−7.8 (3)
Ni1—N9—C13—N10	−173.5 (2)	N11—Ni1—N9—C13	102.0 (2)
Ni1—N9—C14—C15	173.2 (2)	N11—Ni1—N9—C14	−70.1 (2)
Ni1—N11—C16—N12	178.8 (2)	O1—C19—C20—O3	−19.2 (4)
Ni1—N11—C17—C18	−178.6 (2)	O2—C19—C20—O3	162.4 (3)
N11—C17—C18—N12	−0.3 (4)	O3—C21—C22—C23	179.0 (3)
N1—Ni1—N3—C4	165.3 (2)	O3—C21—C26—C25	178.5 (2)
N1—Ni1—N3—C5	−9.7 (3)	O4—C25—C26—C21	−177.9 (2)
N1—Ni1—N5—C7	99.3 (2)	O4—C27—C28—O5	−175.2 (3)
N1—Ni1—N5—C8	−74.5 (2)	O4—C27—C28—O6	3.6 (4)
N1—Ni1—N9—C13	12.4 (2)	C1—N1—C2—C3	0.0 (4)
N1—Ni1—N9—C14	−159.6 (2)	C1—N2—C3—C2	−0.3 (4)
N1—Ni1—N11—C16	73.1 (2)	C2—N1—C1—N2	−0.2 (4)
N1—Ni1—N11—C17	−108.2 (3)	C3—N2—C1—N1	0.3 (4)
N1—C2—C3—N2	0.2 (4)	C4—N3—C5—C6	−0.4 (4)
N3—Ni1—N1—C1	−80.8 (3)	C4—N4—C6—C5	0.4 (4)
N3—Ni1—N1—C2	87.6 (2)	C5—N3—C4—N4	0.6 (3)
N3—Ni1—N5—C7	10.5 (2)	C6—N4—C4—N3	−0.6 (4)
N3—Ni1—N7—C10	−97.6 (3)	C8—N5—C7—N6	0.5 (3)
N3—Ni1—N7—C11	82.5 (3)	C7—N5—C8—C9	−0.7 (3)
N3—Ni1—N11—C16	161.8 (2)	C7—N6—C9—C8	−0.3 (3)
N3—Ni1—N11—C17	−19.5 (3)	C9—N6—C7—N5	−0.1 (3)
N3—C5—C6—N4	0.0 (4)	C10—N7—C11—C12	1.2 (4)
N5—Ni1—N1—C1	−170.2 (3)	C10—N8—C12—C11	0.4 (4)
N5—Ni1—N1—C2	−1.8 (2)	C11—N7—C10—N8	−1.0 (4)
N5—Ni1—N3—C4	−104.1 (2)	C12—N8—C10—N7	0.4 (4)
N5—Ni1—N3—C5	81.0 (3)	C13—N9—C14—C15	−0.5 (3)
N5—Ni1—N7—C10	−8.2 (3)	C13—N10—C15—C14	−0.8 (3)
N5—Ni1—N7—C11	172.0 (3)	C14—N9—C13—N10	−0.1 (3)
N5—Ni1—N9—C13	−78.2 (2)	C15—N10—C13—N9	0.6 (3)
N5—Ni1—N9—C14	109.7 (2)	C16—N11—C17—C18	0.3 (3)
N5—C8—C9—N6	0.7 (3)	C16—N12—C18—C17	0.1 (3)
N7—Ni1—N3—C4	−15.2 (2)	C17—N11—C16—N12	−0.2 (3)
N7—Ni1—N3—C5	169.9 (3)	C18—N12—C16—N11	0.1 (3)
N7—Ni1—N5—C7	−79.4 (2)	C20—O3—C21—C22	−169.6 (2)
N7—Ni1—N5—C8	106.9 (2)	C20—O3—C21—C26	11.8 (4)
N7—Ni1—N9—C13	−167.1 (2)	C21—O3—C20—C19	−75.5 (3)
N7—Ni1—N9—C14	20.8 (2)	C21—C22—C23—C24	2.3 (5)
N7—Ni1—N11—C16	−108.3 (2)	C22—C21—C26—C25	0.0 (4)
N7—Ni1—N11—C17	70.5 (3)	C22—C23—C24—C25	0.3 (4)
N7—C11—C12—N8	−1.0 (4)	C23—C24—C25—O4	177.8 (3)
N9—Ni1—N1—C1	97.7 (3)	C23—C24—C25—C26	−2.8 (4)
N9—Ni1—N1—C2	−93.9 (2)	C24—C25—C26—C21	2.6 (4)
N9—Ni1—N5—C7	−170.2 (2)	C25—O4—C27—C28	−84.6 (3)
N9—Ni1—N5—C8	16.0 (2)	C26—C21—C22—C23	−2.4 (4)
N9—Ni1—N7—C10	83.9 (3)	C27—O4—C25—C24	−166.2 (2)
N9—Ni1—N7—C11	−95.9 (3)	C27—O4—C25—C26	14.4 (4)
N9—Ni1—N11—C16	−17.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H29···O1	0.86	1.91	2.765 (3)	176
N4—H30···O1^i	0.86	2.23	2.808 (4)	125
N4—H30···O3^i	0.86	2.28	3.109 (3)	161
N6—H31···O6^ii	0.86	1.97	2.731 (3)	147
N8—H32···O6^iii	0.86	1.95	2.775 (3)	160
N10—H33···O5^iv	0.86	1.90	2.751 (3)	170
N12—H34···O2^v	0.86	1.88	2.737 (3)	173
N12—H34···O1^v	0.86	2.62	3.172 (3)	123

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) −x, −y, −z; (v) x+1, y, z.