Aqua­(benzene-1,3-dioxy­acetato-κO)­tetrakis(1H-imidazole-κN³)­nickel(II) monohydrate

In the title complex {systematic name: aqua­[p-phenyl­enebis­(dioxy­acetato)-κO]­tetrakis(1H-imidazole-κN³)­nickel(II) mono­hydrate}, [Ni(C₁₀H₈O₆)(C₃H₄N₂)₄(H₂O)]·H₂O, the Ni^II atom shows a distorted octahedral configuration, defined by one carboxyl O atom of the benzene-1,3-dioxy­acetate group, four N atoms from four imidazole ligands and one water mol­ecule. A three-dimensional supramolecular network is constructed by hydrogen-bonding and π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.112
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

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.

aqua[p-phenylenebis(dioxyacetato)-κO]tetrakis(1H-imidazole-κN³)nickel(II) monohydrate

Crystal data

[Ni(C10H8O6)(C3H4N2)4(H2O)]·H2O	Z = 2
Mr = 591.21	F(000) = 616
Triclinic, P1	Dx = 1.494 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3099 (17) Å	Cell parameters from 12270 reflections
b = 9.896 (2) Å	θ = 3.2–27.5°
c = 16.986 (3) Å	µ = 0.80 mm^−1
α = 75.95 (3)°	T = 293 K
β = 75.93 (3)°	Prism, green
γ = 87.62 (3)°	0.38 × 0.27 × 0.19 mm
V = 1314.2 (5) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5980 independent reflections
Radiation source: fine-focus sealed tube	4469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.751, Tmax = 0.863	l = −22→21
12870 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.4263P] where P = (Fo^2 + 2Fc^2)/3
5980 reflections	(Δ/σ)max = 0.001
364 parameters	Δρmax = 0.60 e Å^−3
6 restraints	Δρmin = −0.32 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ni1	0.59626 (4)	0.59054 (4)	0.218253 (18)	0.0287 (1)
N1	0.4526 (3)	0.7454 (2)	0.16209 (13)	0.0373 (5)
N2	0.2720 (3)	0.9163 (3)	0.15821 (17)	0.0511 (6)
N3	0.8003 (3)	0.6357 (2)	0.11502 (13)	0.0361 (5)
N4	0.9456 (3)	0.6640 (3)	−0.01503 (14)	0.0471 (6)
N5	0.5243 (3)	0.4307 (2)	0.17245 (13)	0.0358 (5)
N6	0.5322 (3)	0.2232 (3)	0.14655 (15)	0.0444 (6)
N7	0.3959 (3)	0.5335 (2)	0.32312 (12)	0.0331 (5)
N8	0.2507 (3)	0.4467 (2)	0.45168 (13)	0.0388 (5)
O1	0.6737 (2)	0.7510 (2)	0.26680 (10)	0.0365 (4)
O2	0.7643 (2)	0.6333 (2)	0.37733 (11)	0.0406 (5)
O3	0.7282 (3)	0.8444 (2)	0.44665 (11)	0.0493 (5)
O4	0.8743 (3)	0.9737 (2)	0.67201 (11)	0.0420 (5)
O5	0.9852 (3)	0.9095 (2)	0.81121 (12)	0.0446 (5)
O6	1.0163 (2)	0.6874 (2)	0.80822 (11)	0.0402 (4)
O1W	0.7461 (2)	0.4500 (2)	0.28594 (11)	0.0369 (4)
O2W	0.7404 (3)	1.0025 (2)	0.13848 (16)	0.0569 (6)
C1	0.3517 (4)	0.8261 (3)	0.20569 (19)	0.0496 (7)
C2	0.3236 (5)	0.8980 (4)	0.0782 (2)	0.0620 (9)
C3	0.4340 (4)	0.7925 (4)	0.08350 (19)	0.0561 (9)
C4	0.8085 (4)	0.6116 (3)	0.04066 (16)	0.0394 (6)
C5	1.0350 (5)	0.7233 (4)	0.0252 (2)	0.0658 (10)
C6	0.9448 (4)	0.7042 (4)	0.1050 (2)	0.0574 (9)
C7	0.5994 (4)	0.3112 (4)	0.1782 (2)	0.0521 (8)
C8	0.4014 (4)	0.2890 (3)	0.11986 (18)	0.0445 (7)
C9	0.3984 (4)	0.4162 (3)	0.13546 (18)	0.0433 (7)
C10	0.4001 (3)	0.4839 (3)	0.40183 (16)	0.0386 (6)
C11	0.1396 (4)	0.4725 (3)	0.40270 (17)	0.0418 (6)
C12	0.2293 (3)	0.5261 (3)	0.32388 (16)	0.0394 (6)
C13	0.7148 (3)	0.7415 (3)	0.33531 (15)	0.0316 (5)
C14	0.7020 (4)	0.8748 (3)	0.36465 (15)	0.0378 (6)
C15	0.7425 (3)	0.9517 (3)	0.48274 (15)	0.0346 (6)
C16	0.7107 (4)	1.0887 (3)	0.45203 (16)	0.0386 (6)
C17	0.7368 (4)	1.1854 (3)	0.49523 (17)	0.0421 (7)
C18	0.7923 (4)	1.1466 (3)	0.56780 (16)	0.0405 (6)
C19	0.8196 (3)	1.0065 (3)	0.59923 (15)	0.0349 (6)
C20	0.7937 (4)	0.9090 (3)	0.55745 (15)	0.0365 (6)
C21	0.9106 (3)	0.8310 (3)	0.70149 (15)	0.0344 (6)
C22	0.9761 (3)	0.8099 (3)	0.77990 (15)	0.0322 (6)
H1	0.3397	0.8190	0.2624	0.059*
H2	0.2904	0.9470	0.0309	0.074*
H3	0.4896	0.7573	0.0384	0.067*
H4	0.7270	0.5633	0.0290	0.047*
H5	1.1379	0.7682	0.0024	0.079*
H6	0.9771	0.7337	0.1470	0.069*
H7	0.6900	0.2900	0.2018	0.062*
H8	0.3288	0.2533	0.0957	0.053*
H9	0.3219	0.4845	0.1230	0.052*
H10	0.4971	0.4757	0.4206	0.046*
H11	0.0255	0.4564	0.4199	0.050*
H12	0.1856	0.5539	0.2771	0.047*
H14A	0.7847	0.9421	0.3271	0.045*
H14B	0.5932	0.9143	0.3648	0.045*
H16	0.6726	1.1165	0.4035	0.046*
H17	0.7163	1.2788	0.4747	0.051*
H18	0.8112	1.2131	0.5951	0.049*
H20	0.8103	0.8151	0.5789	0.044*
H21B	0.9928	0.8009	0.6582	0.041*
H21A	0.8109	0.7745	0.7138	0.041*
H22	0.2008	0.9756	0.1744	0.061*
H23	0.9728	0.6611	−0.0668	0.056*
H24	0.5652	0.1407	0.1436	0.053*
H25	0.2284	0.4128	0.5049	0.047*
H1W1	0.777 (3)	0.492 (3)	0.3177 (16)	0.055*
H1W2	0.829 (2)	0.418 (3)	0.2563 (16)	0.055*
H2W1	0.829 (3)	1.033 (4)	0.145 (2)	0.085*
H2W2	0.707 (4)	0.928 (3)	0.1750 (19)	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.03290 (18)	0.03324 (19)	0.02119 (15)	0.00179 (13)	−0.00785 (13)	−0.00789 (12)
N1	0.0426 (13)	0.0380 (13)	0.0313 (11)	0.0054 (10)	−0.0147 (10)	−0.0032 (9)
N2	0.0511 (15)	0.0396 (15)	0.0648 (17)	0.0163 (12)	−0.0159 (14)	−0.0175 (13)
N3	0.0367 (12)	0.0436 (14)	0.0281 (10)	0.0030 (10)	−0.0079 (10)	−0.0090 (10)
N4	0.0521 (15)	0.0589 (17)	0.0252 (11)	0.0085 (12)	−0.0029 (11)	−0.0083 (11)
N5	0.0348 (12)	0.0411 (14)	0.0370 (12)	0.0035 (10)	−0.0109 (10)	−0.0176 (10)
N6	0.0490 (14)	0.0376 (14)	0.0533 (14)	0.0044 (11)	−0.0179 (12)	−0.0185 (11)
N7	0.0362 (12)	0.0361 (12)	0.0267 (10)	0.0051 (9)	−0.0081 (9)	−0.0070 (9)
N8	0.0453 (13)	0.0419 (14)	0.0258 (10)	0.0000 (11)	−0.0058 (10)	−0.0043 (9)
O1	0.0526 (11)	0.0368 (11)	0.0249 (8)	−0.0010 (9)	−0.0182 (9)	−0.0074 (7)
O2	0.0569 (12)	0.0422 (11)	0.0288 (9)	0.0088 (9)	−0.0208 (9)	−0.0106 (8)
O3	0.0903 (16)	0.0364 (11)	0.0323 (10)	0.0006 (11)	−0.0328 (11)	−0.0107 (8)
O4	0.0694 (13)	0.0352 (11)	0.0309 (9)	0.0082 (9)	−0.0257 (10)	−0.0131 (8)
O5	0.0580 (13)	0.0451 (12)	0.0436 (10)	0.0128 (10)	−0.0287 (10)	−0.0205 (9)
O6	0.0448 (11)	0.0434 (12)	0.0335 (9)	0.0143 (9)	−0.0120 (9)	−0.0111 (8)
O1W	0.0391 (10)	0.0439 (12)	0.0320 (9)	0.0101 (9)	−0.0118 (9)	−0.0156 (8)
O2W	0.0636 (15)	0.0411 (13)	0.0683 (15)	0.0012 (11)	−0.0298 (13)	−0.0033 (11)
C1	0.062 (2)	0.0472 (18)	0.0405 (15)	0.0139 (15)	−0.0119 (15)	−0.0147 (13)
C2	0.076 (2)	0.064 (2)	0.0522 (18)	0.0180 (19)	−0.0318 (19)	−0.0112 (17)
C3	0.069 (2)	0.064 (2)	0.0372 (15)	0.0241 (18)	−0.0152 (16)	−0.0164 (15)
C4	0.0418 (15)	0.0481 (17)	0.0281 (12)	0.0057 (13)	−0.0073 (12)	−0.0106 (12)
C5	0.056 (2)	0.081 (3)	0.053 (2)	−0.0202 (19)	0.0081 (17)	−0.0185 (19)
C6	0.0525 (19)	0.078 (3)	0.0431 (16)	−0.0166 (18)	−0.0017 (15)	−0.0232 (16)
C7	0.0520 (18)	0.053 (2)	0.067 (2)	0.0077 (15)	−0.0329 (17)	−0.0262 (16)
C8	0.0450 (16)	0.0528 (19)	0.0422 (15)	−0.0019 (14)	−0.0164 (14)	−0.0172 (14)
C9	0.0447 (16)	0.0479 (18)	0.0451 (15)	0.0075 (13)	−0.0207 (14)	−0.0172 (13)
C10	0.0383 (15)	0.0448 (17)	0.0309 (13)	0.0024 (12)	−0.0101 (12)	−0.0045 (12)
C11	0.0353 (14)	0.0499 (18)	0.0392 (14)	0.0009 (13)	−0.0046 (13)	−0.0133 (13)
C12	0.0387 (15)	0.0510 (18)	0.0300 (13)	0.0053 (13)	−0.0112 (12)	−0.0105 (12)
C13	0.0322 (13)	0.0402 (15)	0.0239 (11)	−0.0025 (11)	−0.0081 (11)	−0.0087 (10)
C14	0.0539 (17)	0.0374 (15)	0.0279 (12)	−0.0023 (13)	−0.0182 (12)	−0.0098 (11)
C15	0.0443 (15)	0.0365 (15)	0.0276 (12)	0.0008 (12)	−0.0127 (12)	−0.0121 (11)
C16	0.0489 (16)	0.0416 (16)	0.0284 (12)	0.0051 (13)	−0.0170 (12)	−0.0071 (11)
C17	0.0605 (18)	0.0301 (15)	0.0368 (14)	0.0073 (13)	−0.0154 (14)	−0.0075 (11)
C18	0.0594 (18)	0.0326 (15)	0.0344 (13)	0.0064 (13)	−0.0147 (13)	−0.0149 (11)
C19	0.0443 (15)	0.0370 (15)	0.0268 (12)	0.0042 (12)	−0.0115 (12)	−0.0116 (11)
C20	0.0526 (17)	0.0302 (14)	0.0290 (12)	0.0021 (12)	−0.0138 (12)	−0.0078 (10)
C21	0.0465 (15)	0.0324 (14)	0.0274 (12)	0.0044 (12)	−0.0117 (12)	−0.0110 (10)
C22	0.0274 (12)	0.0424 (16)	0.0272 (12)	0.0049 (11)	−0.0054 (11)	−0.0111 (11)

Geometric parameters (Å, º)

Ni1—N1	2.092 (2)	O1W—H1W1	0.85 (3)
Ni1—N3	2.094 (2)	O1W—H1W2	0.85 (3)
Ni1—N5	2.090 (2)	O2W—H2W1	0.85 (3)
Ni1—N7	2.101 (2)	O2W—H2W2	0.85 (3)
Ni1—O1	2.143 (2)	C1—H1	0.9300
Ni1—O1W	2.140 (2)	C2—C3	1.362 (5)
O1—C13	1.272 (3)	C2—H2	0.9300
O2—C13	1.249 (3)	C3—H3	0.9300
O5—C22	1.241 (3)	C4—H4	0.9300
O6—C22	1.255 (3)	C5—C6	1.352 (5)
N1—C1	1.348 (4)	C5—H5	0.9300
N1—C3	1.348 (4)	C6—H6	0.9300
N2—C1	1.322 (4)	C7—H7	0.9300
N2—C2	1.375 (4)	C8—C9	1.346 (4)
N2—H22	0.8600	C8—H8	0.9300
N3—C4	1.327 (3)	C9—H9	0.9300
N3—C6	1.358 (4)	C10—H10	0.9300
N4—C4	1.323 (4)	C11—C12	1.354 (4)
N4—C5	1.357 (4)	C11—H11	0.9300
N4—H23	0.8600	C12—H12	0.9300
N5—C7	1.307 (4)	C13—C14	1.511 (4)
N5—C9	1.374 (3)	C14—H14A	0.9700
N6—C7	1.331 (4)	C14—H14B	0.9700
N6—C8	1.359 (4)	C15—C16	1.369 (4)
N6—H24	0.8600	C15—C20	1.399 (3)
N7—C10	1.316 (3)	C16—C17	1.391 (4)
N7—C12	1.385 (3)	C16—H16	0.9300
N8—C10	1.330 (4)	C17—C18	1.383 (4)
N8—C11	1.364 (4)	C17—H17	0.9300
N8—H25	0.8600	C18—C19	1.390 (4)
O3—C15	1.371 (3)	C18—H18	0.9300
O3—C14	1.420 (3)	C19—C20	1.380 (4)
O4—C19	1.381 (3)	C20—H20	0.9300
O4—C21	1.425 (3)	C21—C22	1.524 (3)
O5—C22	1.241 (3)	C21—H21B	0.9700
O6—C22	1.255 (3)	C21—H21A	0.9700
N1—Ni1—N3	92.89 (9)	C3—C2—N2	104.9 (3)
N1—Ni1—N7	89.90 (9)	C3—C2—H2	127.5
N1—Ni1—O1	84.99 (8)	C4—N3—Ni1	125.7 (2)
N1—Ni1—O1W	172.46 (8)	C4—N4—C5	106.8 (2)
N3—Ni1—N7	176.75 (9)	C4—N3—C6	104.3 (2)
N3—Ni1—O1	90.55 (8)	C4—N4—H23	126.6
N3—Ni1—O1W	89.25 (8)	C5—N4—H23	126.6
N5—Ni1—N1	96.40 (9)	C5—C6—N3	110.1 (3)
N5—Ni1—N3	89.41 (9)	C5—C6—H6	124.9
N5—Ni1—N7	88.63 (9)	C6—N3—Ni1	129.7 (2)
N5—Ni1—O1	178.62 (8)	C6—C5—N4	106.4 (3)
N5—Ni1—O1W	90.85 (8)	C6—C5—H5	126.8
N7—Ni1—O1	91.35 (8)	C7—N5—Ni1	122.4 (2)
N7—Ni1—O1W	88.19 (8)	C7—N5—C9	104.2 (2)
O1W—Ni1—O1	87.77 (7)	C7—N6—C8	106.8 (3)
Ni1—O1W—H1W1	107 (2)	C7—N6—H24	126.6
Ni1—O1W—H1W2	116 (2)	C8—N6—H24	126.6
N1—C1—H1	124.0	C8—C9—N5	110.2 (3)
N1—C3—C2	111.6 (3)	C8—C9—H9	124.9
N1—C3—H3	124.2	C9—N5—Ni1	133.4 (2)
N2—C1—N1	112.0 (3)	C9—C8—N6	106.0 (2)
N2—C1—H1	124.0	C9—C8—H8	127.0
N2—C2—H2	127.5	C10—N7—Ni1	128.3 (2)
N3—C4—H4	123.8	C10—N7—C12	104.0 (2)
N3—C6—H6	124.9	C10—N8—C11	107.2 (2)
N4—C4—N3	112.4 (3)	C10—N8—H25	126.4
N4—C4—H4	123.8	C11—N8—H25	126.4
N4—C5—H5	126.8	C11—C12—N7	110.0 (2)
N5—C7—N6	112.8 (3)	C11—C12—H12	125.0
N5—C7—H7	123.6	C12—N7—Ni1	127.4 (2)
N5—C9—H9	124.9	C12—C11—N8	106.0 (2)
N6—C7—H7	123.6	C12—C11—H11	127.0
N6—C8—H8	127.0	C13—O1—Ni1	129.4 (2)
N7—C10—N8	112.8 (2)	C13—C14—H14A	109.9
N7—C10—H10	123.6	C13—C14—H14B	109.9
N7—C12—H12	125.0	C15—O3—C14	119.4 (2)
N8—C10—H10	123.6	C15—C16—C17	118.3 (2)
N8—C11—H11	127.0	C15—C16—H16	120.8
O1—C13—C14	115.0 (2)	C15—C20—H20	120.1
O2—C13—O1	125.0 (2)	C16—C15—O3	125.7 (2)
O2—C13—C14	120.0 (2)	C16—C15—C20	120.9 (2)
O3—C14—C13	108.7 (2)	C16—C17—H17	119.0
O3—C14—H14A	109.9	C17—C16—H16	120.8
O3—C14—H14B	109.9	C17—C18—C19	118.8 (2)
O3—C15—C20	113.4 (2)	C17—C18—H18	120.6
O4—C19—C18	116.4 (2)	C18—C17—C16	121.9 (3)
O4—C21—C22	110.9 (2)	C18—C17—H17	119.0
O4—C21—H21A	109.5	C19—O4—C21	116.2 (2)
O4—C21—H21B	109.5	C19—C18—H18	120.6
O5—C22—O6	125.0 (2)	C19—C20—C15	119.9 (3)
O5—C22—C21	120.2 (2)	C19—C20—H20	120.1
O6—C22—C21	114.8 (2)	C20—C19—O4	123.6 (2)
C1—N1—Ni1	122.0 (2)	C20—C19—C18	120.1 (2)
C1—N2—C2	107.5 (3)	C22—C21—H21A	109.5
C1—N2—H22	126.3	C22—C21—H21B	109.5
C2—N2—H22	126.3	H1W1—O1W—H1W2	110 (2)
C2—C3—H3	124.2	H2W1—O2W—H2W2	111 (2)
C3—N1—Ni1	134.0 (2)	H14A—C14—H14B	108.3
C3—N1—C1	104.0 (2)	H21B—C21—H21A	108.0
Ni1—N1—C1—N2	−179.6 (2)	O1—C13—C14—O3	171.7 (2)
Ni1—N1—C3—C2	−179.7 (2)	O2—C13—C14—O3	−8.9 (4)
Ni1—N3—C4—N4	173.31 (19)	O3—C15—C16—C17	−177.9 (3)
Ni1—N3—C6—C5	−173.4 (3)	O3—C15—C20—C19	177.6 (3)
Ni1—N5—C7—N6	178.8 (2)	O4—C19—C20—C15	−178.2 (3)
Ni1—N5—C9—C8	−177.7 (2)	O4—C21—C22—O5	2.8 (4)
Ni1—N7—C10—N8	−174.32 (18)	O4—C21—C22—O6	−177.8 (2)
Ni1—N7—C12—C11	174.1 (2)	O1W—Ni1—N3—C4	117.9 (2)
Ni1—O1—C13—O2	22.1 (4)	O1W—Ni1—N3—C6	−68.2 (3)
Ni1—O1—C13—C14	−158.57 (18)	O1W—Ni1—N5—C7	−13.3 (3)
N1—Ni1—N3—C4	−69.4 (2)	O1W—Ni1—N5—C9	163.9 (3)
N1—Ni1—N3—C6	104.5 (3)	O1W—Ni1—N7—C10	24.9 (2)
N1—Ni1—N5—C7	168.8 (3)	O1W—Ni1—N7—C12	−147.9 (2)
N1—Ni1—N5—C9	−14.0 (3)	O1W—Ni1—O1—C13	−29.4 (2)
N1—Ni1—N7—C10	−147.9 (2)	C1—N1—C3—C2	−0.7 (4)
N1—Ni1—N7—C12	39.4 (2)	C1—N2—C2—C3	0.8 (4)
N1—Ni1—O1—C13	148.5 (2)	C2—N2—C1—N1	−1.3 (4)
N2—C2—C3—N1	0.0 (4)	C3—N1—C1—N2	1.2 (4)
N3—Ni1—N1—C1	−140.4 (2)	C4—N4—C5—C6	−0.4 (4)
N3—Ni1—N1—C3	38.4 (3)	C4—N3—C6—C5	1.5 (4)
N3—Ni1—N5—C7	76.0 (3)	C5—N4—C4—N3	1.5 (4)
N3—Ni1—N5—C9	−106.9 (3)	C6—N3—C4—N4	−1.9 (3)
N3—Ni1—O1—C13	−118.7 (2)	C7—N5—C9—C8	−0.1 (4)
N4—C5—C6—N3	−0.7 (5)	C7—N6—C8—C9	1.2 (3)
N5—Ni1—N1—C1	129.8 (2)	C8—N6—C7—N5	−1.4 (4)
N5—Ni1—N1—C3	−51.3 (3)	C9—N5—C7—N6	0.9 (4)
N5—Ni1—N3—C4	27.0 (2)	C10—N7—C12—C11	−0.1 (3)
N5—Ni1—N3—C6	−159.1 (3)	C10—N8—C11—C12	−0.4 (3)
N5—Ni1—N7—C10	115.7 (2)	C11—N8—C10—N7	0.4 (3)
N5—Ni1—N7—C12	−57.0 (2)	C12—N7—C10—N8	−0.2 (3)
N6—C8—C9—N5	−0.7 (3)	C14—O3—C15—C16	9.9 (4)
N7—Ni1—N1—C1	41.2 (2)	C14—O3—C15—C20	−170.5 (2)
N7—Ni1—N1—C3	−139.9 (3)	C15—O3—C14—C13	172.2 (2)
N7—Ni1—N5—C7	−101.5 (3)	C15—C16—C17—C18	−0.4 (5)
N7—Ni1—N5—C9	75.7 (3)	C16—C15—C20—C19	−2.8 (4)
O1—Ni1—N7—C10	−62.9 (2)	C16—C17—C18—C19	−1.3 (5)
N7—Ni1—O1—C13	58.7 (2)	C17—C18—C19—O4	−179.7 (3)
N8—C11—C12—N7	0.3 (3)	C17—C18—C19—C20	1.0 (4)
O1—Ni1—N1—C1	−50.1 (2)	C18—C19—C20—C15	1.0 (4)
O1—Ni1—N1—C3	128.7 (3)	C19—O4—C21—C22	177.7 (2)
O1—Ni1—N3—C4	−154.4 (2)	C20—C15—C16—C17	2.5 (4)
O1—Ni1—N3—C6	19.5 (3)	C21—O4—C19—C18	−176.7 (2)
O1—Ni1—N7—C12	124.4 (2)	C21—O4—C19—C20	2.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O5^i	0.86	1.88	2.720 (3)	164
N4—H23···O6^ii	0.86	2.02	2.869 (3)	170
N6—H24···O2W^iii	0.86	1.96	2.739 (4)	151
N8—H25···O2^iv	0.86	1.96	2.792 (3)	163
N8—H25···O3^iv	0.86	2.52	3.001 (3)	116
O1W—H1W1···O2	0.85 (3)	1.90 (3)	2.688 (3)	154 (3)
O1W—H1W2···O6^v	0.85 (3)	1.92 (3)	2.758 (3)	167 (3)
O2W—H2W1···O5^vi	0.85 (3)	2.02 (3)	2.857 (3)	167 (4)
O2W—H2W2···O1	0.85 (3)	2.02 (3)	2.854 (3)	168 (3)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y+2, −z+1.