Aqua­(2,4-dihydroxy­benzoato-κO¹)bis­(1,10-phenanthroline-κ²N,N′)nickel(II) 2,4-dihydroxy­benzoate monohydrate

The crystal structure of the title compound, [Ni(C₇H₅O₄)(C₁₂H₈N₂)₂(H₂O)](C₇H₅O₄)·H₂O, consists of Ni^II complex cations, 2,4-dihydroxy­benzoate (dHBA) anions and solvent water mol­ecules. The Ni^II complex cation assumes a distorted octa­hedral coordination geometry formed by two 1,10-phenanthroline (phen) ligands, one dHBA ion and a water mol­ecule. π–π Stacking is observed between partially overlapped, parallel phen ligands and between a nearly parallel phen ligand and benzene ring of dHBA.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Aqua(2,4-dihydroxybenzoato-κO¹)bis(1,10-phenanthroline-κ²N,N')nickel(II) 2,4-dihydroxybenzoate monohydrate

Crystal data

[Ni(C7H5O4)(C12H8N2)2(H2O)](C7H5O4)·H2O	Z = 2
Mr = 761.37	F(000) = 788
Triclinic, P1	Dx = 1.490 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.347 (4) Å	Cell parameters from 3600 reflections
b = 13.408 (6) Å	θ = 3.0–23.0°
c = 13.578 (6) Å	µ = 0.64 mm^−1
α = 118.829 (14)°	T = 295 K
β = 90.106 (14)°	Prism, green
γ = 116.327 (13)°	0.35 × 0.19 × 0.13 mm
V = 1697.1 (13) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	7612 independent reflections
Radiation source: fine-focus sealed tube	5990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −16→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
Tmin = 0.785, Tmax = 0.920	l = −17→17
16731 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.1081P] where P = (Fo^2 + 2Fc^2)/3
7612 reflections	(Δ/σ)max = 0.001
482 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ni	0.311102 (19)	0.56630 (2)	0.756762 (19)	0.03817 (8)
O1	0.25627 (12)	0.39229 (12)	0.59853 (11)	0.0489 (3)
O2	0.15371 (14)	0.23226 (13)	0.63157 (12)	0.0607 (4)
O9	0.24175 (16)	0.45999 (15)	0.83154 (13)	0.0703 (4)
H9A	0.1971	0.3665	0.7709	0.114 (10)*
H9B	0.2378	0.4765	0.9084	0.093 (9)*
O3	0.27797 (14)	0.34334 (13)	0.39826 (13)	0.0608 (4)
H3	0.2801	0.3856	0.4817	0.091*
O1W	0.97228 (17)	0.33608 (15)	0.97300 (14)	0.0766 (5)
H1A	0.9310	0.3408	0.9142	0.092 (9)*
H1B	1.0556	0.3943	0.9896	0.087 (9)*
O4	0.09673 (16)	−0.09748 (15)	0.08634 (12)	0.0712 (4)
H4	0.0701	−0.1802	0.0714	0.107*
O5	0.78510 (16)	0.47694 (17)	0.95945 (13)	0.0817 (5)
O6	0.80850 (16)	0.31543 (19)	0.82086 (15)	0.0831 (5)
O7	0.62476 (17)	0.11133 (17)	0.65295 (13)	0.0766 (5)
H7	0.7092	0.1768	0.7026	0.115*
O8	0.22723 (16)	0.06702 (17)	0.62990 (16)	0.0855 (6)
H8	0.1958	0.1252	0.6537	0.128*
N1	0.49046 (14)	0.60144 (16)	0.80208 (14)	0.0457 (4)
N2	0.38624 (13)	0.74551 (14)	0.91946 (12)	0.0423 (3)
N3	0.35782 (13)	0.65592 (14)	0.65969 (12)	0.0390 (3)
N4	0.14685 (13)	0.56518 (14)	0.72147 (13)	0.0415 (3)
C1	0.5383 (2)	0.5259 (2)	0.7444 (2)	0.0559 (5)
H1	0.4883	0.4469	0.6734	0.067*
C2	0.6604 (2)	0.5603 (3)	0.7859 (3)	0.0692 (7)
H2	0.6904	0.5041	0.7436	0.083*
C3	0.7353 (2)	0.6756 (3)	0.8880 (2)	0.0707 (7)
H11	0.8173	0.6993	0.9157	0.085*
C4	0.68908 (18)	0.7600 (2)	0.9527 (2)	0.0591 (6)
C5	0.7600 (2)	0.8847 (3)	1.0610 (2)	0.0777 (8)
H5	0.8438	0.9160	1.0916	0.093*
C6	0.7080 (2)	0.9575 (3)	1.1193 (2)	0.0766 (7)
H6	0.7566	1.0381	1.1893	0.092*
C7	0.5794 (2)	0.9137 (2)	1.07594 (18)	0.0562 (5)
C8	0.5176 (2)	0.9812 (2)	1.13518 (18)	0.0663 (6)
H12	0.5609	1.0603	1.2074	0.080*
C9	0.3953 (2)	0.9318 (2)	1.08791 (18)	0.0631 (6)
H9	0.3539	0.9763	1.1271	0.076*
C10	0.33197 (19)	0.81267 (19)	0.97901 (17)	0.0512 (5)
H10	0.2479	0.7792	0.9471	0.061*
C11	0.50849 (17)	0.79412 (18)	0.96779 (16)	0.0449 (4)
C12	0.56382 (17)	0.7168 (2)	0.90551 (17)	0.0463 (4)
C13	0.46180 (18)	0.69756 (19)	0.62733 (18)	0.0498 (4)
H13	0.5263	0.6879	0.6491	0.060*
C14	0.4787 (2)	0.7551 (2)	0.5622 (2)	0.0599 (5)
H14	0.5531	0.7829	0.5410	0.072*
C15	0.3857 (2)	0.7703 (2)	0.52973 (19)	0.0592 (5)
H15	0.3956	0.8078	0.4855	0.071*
C16	0.27425 (19)	0.72908 (19)	0.56359 (16)	0.0494 (4)
C17	0.1727 (2)	0.7466 (2)	0.5388 (2)	0.0617 (6)
H17	0.1782	0.7855	0.4965	0.074*
C18	0.0699 (2)	0.7074 (2)	0.5763 (2)	0.0632 (6)
H18	0.0065	0.7217	0.5606	0.076*
C19	0.05575 (18)	0.6448 (2)	0.63923 (18)	0.0521 (5)
C20	−0.04936 (19)	0.6005 (2)	0.6801 (2)	0.0648 (6)
H20	−0.1154	0.6128	0.6676	0.078*
C21	−0.05433 (19)	0.5402 (2)	0.7374 (2)	0.0651 (6)
H21	−0.1239	0.5104	0.7640	0.078*
C22	0.04490 (17)	0.5227 (2)	0.75640 (18)	0.0522 (5)
H22	0.0396	0.4798	0.7949	0.063*
C23	0.15280 (16)	0.62518 (17)	0.66384 (15)	0.0418 (4)
C24	0.26448 (16)	0.67114 (16)	0.62751 (14)	0.0398 (4)
C25	0.19293 (16)	0.26995 (17)	0.56450 (16)	0.0421 (4)
C26	0.16917 (15)	0.17379 (17)	0.43909 (15)	0.0400 (4)
C27	0.21037 (17)	0.21327 (18)	0.36149 (16)	0.0435 (4)
C28	0.1854 (2)	0.1216 (2)	0.24484 (17)	0.0539 (5)
H28	0.2134	0.1499	0.1945	0.065*
C29	0.11879 (19)	−0.0125 (2)	0.20187 (16)	0.0503 (5)
C30	0.07776 (19)	−0.05419 (19)	0.27731 (17)	0.0562 (5)
H30	0.0337	−0.1438	0.2495	0.067*
C31	0.10259 (18)	0.03776 (19)	0.39345 (17)	0.0522 (5)
H31	0.0743	0.0088	0.4433	0.063*
C32	0.7415 (2)	0.3645 (2)	0.86803 (18)	0.0636 (6)
C33	0.6048 (2)	0.2867 (2)	0.80770 (17)	0.0561 (5)
C34	0.5529 (2)	0.1638 (2)	0.70197 (17)	0.0587 (5)
C35	0.4276 (2)	0.0949 (2)	0.64385 (19)	0.0640 (6)
H35	0.3949	0.0146	0.5727	0.077*
C36	0.3508 (2)	0.1435 (2)	0.6898 (2)	0.0629 (6)
C37	0.3993 (2)	0.2650 (2)	0.7951 (2)	0.0663 (6)
H37	0.3478	0.2991	0.8262	0.080*
C38	0.5251 (2)	0.3337 (2)	0.85224 (18)	0.0623 (6)
H38	0.5576	0.4144	0.9230	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.04080 (13)	0.03646 (13)	0.03941 (13)	0.02207 (10)	0.01396 (9)	0.01963 (10)
O1	0.0615 (8)	0.0363 (7)	0.0449 (7)	0.0231 (6)	0.0202 (6)	0.0206 (6)
O2	0.0806 (10)	0.0437 (7)	0.0495 (8)	0.0239 (7)	0.0264 (7)	0.0264 (7)
O9	0.1140 (13)	0.0475 (8)	0.0504 (8)	0.0381 (9)	0.0375 (8)	0.0296 (7)
O3	0.0845 (10)	0.0423 (7)	0.0550 (8)	0.0268 (7)	0.0269 (7)	0.0306 (7)
O1W	0.0793 (12)	0.0515 (9)	0.0688 (10)	0.0200 (9)	0.0058 (9)	0.0243 (8)
O4	0.1009 (12)	0.0551 (9)	0.0419 (7)	0.0346 (9)	0.0205 (8)	0.0203 (7)
O5	0.0835 (11)	0.0640 (10)	0.0480 (8)	0.0115 (9)	0.0114 (8)	0.0208 (8)
O6	0.0732 (11)	0.0832 (12)	0.0692 (11)	0.0314 (10)	0.0145 (9)	0.0329 (10)
O7	0.0854 (12)	0.0745 (11)	0.0532 (9)	0.0428 (10)	0.0159 (8)	0.0215 (8)
O8	0.0795 (12)	0.0614 (10)	0.0946 (13)	0.0317 (9)	−0.0037 (10)	0.0319 (10)
N1	0.0487 (9)	0.0541 (9)	0.0514 (9)	0.0334 (8)	0.0206 (7)	0.0331 (8)
N2	0.0456 (8)	0.0401 (8)	0.0402 (8)	0.0231 (7)	0.0119 (7)	0.0196 (7)
N3	0.0392 (7)	0.0353 (7)	0.0415 (7)	0.0199 (6)	0.0131 (6)	0.0191 (6)
N4	0.0376 (7)	0.0406 (8)	0.0417 (8)	0.0191 (6)	0.0121 (6)	0.0198 (7)
C1	0.0620 (12)	0.0649 (13)	0.0703 (13)	0.0438 (11)	0.0326 (11)	0.0455 (11)
C2	0.0663 (14)	0.0905 (18)	0.107 (2)	0.0577 (14)	0.0495 (14)	0.0738 (17)
C3	0.0491 (12)	0.103 (2)	0.106 (2)	0.0454 (14)	0.0333 (13)	0.0804 (18)
C4	0.0462 (11)	0.0791 (15)	0.0746 (14)	0.0285 (11)	0.0188 (10)	0.0591 (13)
C5	0.0453 (13)	0.0905 (19)	0.0836 (17)	0.0151 (13)	0.0016 (12)	0.0553 (16)
C6	0.0608 (15)	0.0672 (15)	0.0639 (14)	0.0060 (12)	−0.0070 (12)	0.0342 (13)
C7	0.0576 (12)	0.0474 (11)	0.0475 (10)	0.0130 (9)	0.0057 (9)	0.0273 (9)
C8	0.0832 (17)	0.0417 (11)	0.0441 (11)	0.0198 (11)	0.0110 (11)	0.0142 (9)
C9	0.0822 (16)	0.0480 (11)	0.0511 (11)	0.0362 (12)	0.0257 (11)	0.0186 (10)
C10	0.0582 (11)	0.0470 (11)	0.0457 (10)	0.0302 (9)	0.0182 (9)	0.0200 (9)
C11	0.0465 (10)	0.0444 (10)	0.0438 (9)	0.0187 (8)	0.0105 (8)	0.0275 (8)
C12	0.0445 (10)	0.0560 (11)	0.0536 (11)	0.0254 (9)	0.0170 (9)	0.0395 (10)
C13	0.0483 (10)	0.0485 (11)	0.0580 (11)	0.0263 (9)	0.0230 (9)	0.0307 (9)
C14	0.0648 (13)	0.0595 (13)	0.0677 (13)	0.0330 (11)	0.0366 (11)	0.0408 (11)
C15	0.0795 (14)	0.0534 (12)	0.0560 (12)	0.0332 (11)	0.0261 (11)	0.0375 (10)
C16	0.0585 (11)	0.0405 (10)	0.0430 (10)	0.0223 (9)	0.0084 (9)	0.0211 (8)
C17	0.0740 (15)	0.0575 (13)	0.0608 (13)	0.0338 (11)	0.0069 (11)	0.0362 (11)
C18	0.0598 (13)	0.0658 (14)	0.0677 (14)	0.0368 (12)	0.0045 (11)	0.0340 (12)
C19	0.0444 (10)	0.0492 (11)	0.0523 (11)	0.0244 (9)	0.0042 (9)	0.0200 (9)
C20	0.0426 (11)	0.0751 (15)	0.0725 (14)	0.0342 (11)	0.0133 (10)	0.0332 (13)
C21	0.0436 (11)	0.0820 (16)	0.0739 (15)	0.0335 (11)	0.0268 (11)	0.0433 (13)
C22	0.0423 (10)	0.0572 (12)	0.0554 (11)	0.0233 (9)	0.0180 (9)	0.0310 (10)
C23	0.0375 (9)	0.0363 (9)	0.0385 (9)	0.0177 (7)	0.0050 (7)	0.0125 (7)
C24	0.0427 (9)	0.0336 (8)	0.0358 (8)	0.0184 (7)	0.0081 (7)	0.0148 (7)
C25	0.0419 (9)	0.0395 (9)	0.0457 (9)	0.0214 (8)	0.0162 (8)	0.0228 (8)
C26	0.0387 (9)	0.0379 (9)	0.0429 (9)	0.0193 (7)	0.0149 (7)	0.0214 (8)
C27	0.0463 (10)	0.0390 (9)	0.0495 (10)	0.0231 (8)	0.0165 (8)	0.0255 (8)
C28	0.0696 (13)	0.0520 (11)	0.0471 (10)	0.0300 (10)	0.0232 (10)	0.0319 (9)
C29	0.0576 (11)	0.0486 (11)	0.0402 (9)	0.0275 (9)	0.0143 (9)	0.0206 (8)
C30	0.0642 (12)	0.0348 (9)	0.0503 (11)	0.0155 (9)	0.0173 (10)	0.0188 (9)
C31	0.0593 (11)	0.0416 (10)	0.0482 (10)	0.0187 (9)	0.0227 (9)	0.0254 (9)
C32	0.0718 (14)	0.0587 (13)	0.0423 (11)	0.0167 (11)	0.0131 (10)	0.0301 (10)
C33	0.0726 (14)	0.0478 (11)	0.0414 (10)	0.0218 (10)	0.0148 (10)	0.0276 (9)
C34	0.0772 (15)	0.0516 (12)	0.0427 (10)	0.0279 (11)	0.0147 (10)	0.0267 (9)
C35	0.0797 (16)	0.0485 (12)	0.0477 (11)	0.0269 (12)	0.0048 (11)	0.0204 (10)
C36	0.0753 (15)	0.0496 (12)	0.0608 (13)	0.0270 (11)	0.0077 (12)	0.0320 (11)
C37	0.0842 (16)	0.0567 (13)	0.0648 (13)	0.0386 (13)	0.0240 (12)	0.0346 (11)
C38	0.0850 (16)	0.0440 (11)	0.0469 (11)	0.0263 (11)	0.0172 (11)	0.0231 (9)

Geometric parameters (Å, º)

Ni—O1	2.0681 (15)	C8—H12	0.9300
Ni—O9	2.0279 (16)	C9—C10	1.400 (3)
Ni—N1	2.0723 (16)	C9—H9	0.9300
Ni—N2	2.1002 (17)	C10—H10	0.9300
Ni—N3	2.1047 (17)	C11—C12	1.428 (3)
Ni—N4	2.0748 (15)	C13—C14	1.392 (3)
O1—C25	1.283 (2)	C13—H13	0.9300
O2—C25	1.244 (2)	C14—C15	1.359 (3)
O9—H9A	0.9711	C14—H14	0.9300
O9—H9B	0.9625	C15—C16	1.408 (3)
O3—C27	1.362 (2)	C15—H15	0.9300
O3—H3	0.9866	C16—C24	1.393 (3)
O1W—H1A	0.9879	C16—C17	1.441 (3)
O1W—H1B	0.9137	C17—C18	1.347 (3)
O4—C29	1.354 (2)	C17—H17	0.9300
O4—H4	0.9158	C18—C19	1.425 (3)
O5—C32	1.255 (3)	C18—H18	0.9300
O6—C32	1.268 (3)	C19—C23	1.407 (2)
O7—C34	1.352 (3)	C19—C20	1.407 (3)
O7—H7	0.9630	C20—C21	1.352 (3)
O8—C36	1.358 (3)	C20—H20	0.9300
O8—H8	0.9429	C21—C22	1.391 (3)
N1—C1	1.325 (2)	C21—H21	0.9300
N1—C12	1.358 (3)	C22—H22	0.9300
N2—C10	1.322 (2)	C23—C24	1.437 (3)
N2—C11	1.358 (2)	C25—C26	1.481 (3)
N3—C13	1.325 (2)	C26—C27	1.397 (3)
N3—C24	1.361 (2)	C26—C31	1.402 (3)
N4—C22	1.327 (2)	C27—C28	1.378 (3)
N4—C23	1.349 (2)	C28—C29	1.388 (3)
C1—C2	1.390 (3)	C28—H28	0.9300
C1—H1	0.9300	C29—C30	1.386 (3)
C2—C3	1.352 (4)	C30—C31	1.374 (3)
C2—H2	0.9300	C30—H30	0.9300
C3—C4	1.413 (3)	C31—H31	0.9300
C3—H11	0.9300	C32—C33	1.489 (3)
C4—C12	1.408 (3)	C33—C38	1.384 (3)
C4—C5	1.431 (4)	C33—C34	1.402 (3)
C5—C6	1.342 (4)	C34—C35	1.376 (3)
C5—H5	0.9300	C35—C36	1.368 (3)
C6—C7	1.431 (3)	C35—H35	0.9300
C6—H6	0.9300	C36—C37	1.394 (3)
C7—C8	1.400 (3)	C37—C38	1.378 (3)
C7—C11	1.405 (3)	C37—H37	0.9300
C8—C9	1.353 (3)	C38—H38	0.9300
O9—Ni—O1	89.00 (7)	C15—C14—C13	119.5 (2)
O9—Ni—N1	92.39 (7)	C15—C14—H14	120.3
O1—Ni—N1	93.98 (6)	C13—C14—H14	120.3
O9—Ni—N4	94.57 (7)	C14—C15—C16	119.6 (2)
O1—Ni—N4	93.06 (6)	C14—C15—H15	120.2
N1—Ni—N4	170.18 (6)	C16—C15—H15	120.2
O9—Ni—N2	91.80 (7)	C24—C16—C15	117.23 (18)
O1—Ni—N2	173.81 (5)	C24—C16—C17	118.76 (19)
N1—Ni—N2	79.85 (6)	C15—C16—C17	124.0 (2)
N4—Ni—N2	93.00 (6)	C18—C17—C16	120.8 (2)
O9—Ni—N3	171.54 (6)	C18—C17—H17	119.6
O1—Ni—N3	85.28 (7)	C16—C17—H17	119.6
N1—Ni—N3	94.21 (6)	C17—C18—C19	121.75 (19)
N4—Ni—N3	79.55 (6)	C17—C18—H18	119.1
N2—Ni—N3	94.55 (7)	C19—C18—H18	119.1
C25—O1—Ni	133.46 (12)	C23—C19—C20	116.5 (2)
Ni—O9—H9A	109.1	C23—C19—C18	118.8 (2)
Ni—O9—H9B	137.9	C20—C19—C18	124.69 (19)
H9A—O9—H9B	112.9	C21—C20—C19	119.95 (19)
C27—O3—H3	100.9	C21—C20—H20	120.0
H1A—O1W—H1B	103.6	C19—C20—H20	120.0
C29—O4—H4	109.8	C20—C21—C22	119.8 (2)
C34—O7—H7	105.5	C20—C21—H21	120.1
C36—O8—H8	105.7	C22—C21—H21	120.1
C1—N1—C12	118.61 (17)	N4—C22—C21	122.2 (2)
C1—N1—Ni	128.26 (14)	N4—C22—H22	118.9
C12—N1—Ni	113.12 (12)	C21—C22—H22	118.9
C10—N2—C11	118.01 (16)	N4—C23—C19	122.90 (18)
C10—N2—Ni	129.79 (13)	N4—C23—C24	117.55 (15)
C11—N2—Ni	112.19 (12)	C19—C23—C24	119.55 (18)
C13—N3—C24	117.88 (17)	N3—C24—C16	122.99 (17)
C13—N3—Ni	129.57 (13)	N3—C24—C23	116.70 (16)
C24—N3—Ni	112.55 (12)	C16—C24—C23	120.31 (16)
C22—N4—C23	118.52 (16)	O2—C25—O1	122.94 (17)
C22—N4—Ni	127.76 (14)	O2—C25—C26	121.02 (17)
C23—N4—Ni	113.49 (11)	O1—C25—C26	116.03 (17)
N1—C1—C2	122.5 (2)	C27—C26—C31	117.24 (17)
N1—C1—H1	118.8	C27—C26—C25	122.22 (17)
C2—C1—H1	118.8	C31—C26—C25	120.54 (17)
C3—C2—C1	119.8 (2)	O3—C27—C28	117.52 (18)
C3—C2—H2	120.1	O3—C27—C26	121.44 (16)
C1—C2—H2	120.1	C28—C27—C26	121.04 (18)
C2—C3—C4	120.0 (2)	C27—C28—C29	120.53 (19)
C2—C3—H11	120.0	C27—C28—H28	119.7
C4—C3—H11	120.0	C29—C28—H28	119.7
C12—C4—C3	116.6 (2)	O4—C29—C30	122.79 (19)
C12—C4—C5	118.4 (2)	O4—C29—C28	117.66 (19)
C3—C4—C5	124.9 (2)	C30—C29—C28	119.55 (18)
C6—C5—C4	121.4 (2)	C31—C30—C29	119.60 (19)
C6—C5—H5	119.3	C31—C30—H30	120.2
C4—C5—H5	119.3	C29—C30—H30	120.2
C5—C6—C7	121.5 (2)	C30—C31—C26	122.05 (19)
C5—C6—H6	119.3	C30—C31—H31	119.0
C7—C6—H6	119.3	C26—C31—H31	119.0
C8—C7—C11	117.02 (19)	O5—C32—O6	123.5 (2)
C8—C7—C6	124.4 (2)	O5—C32—C33	118.7 (2)
C11—C7—C6	118.6 (2)	O6—C32—C33	117.7 (2)
C9—C8—C7	120.35 (19)	C38—C33—C34	117.7 (2)
C9—C8—H12	119.8	C38—C33—C32	121.5 (2)
C7—C8—H12	119.8	C34—C33—C32	120.8 (2)
C8—C9—C10	118.9 (2)	O7—C34—C35	118.2 (2)
C8—C9—H9	120.5	O7—C34—C33	121.2 (2)
C10—C9—H9	120.5	C35—C34—C33	120.6 (2)
N2—C10—C9	123.02 (19)	C36—C35—C34	120.5 (2)
N2—C10—H10	118.5	C36—C35—H35	119.7
C9—C10—H10	118.5	C34—C35—H35	119.7
N2—C11—C7	122.66 (18)	O8—C36—C35	117.1 (2)
N2—C11—C12	117.38 (16)	O8—C36—C37	122.7 (2)
C7—C11—C12	119.94 (18)	C35—C36—C37	120.3 (2)
N1—C12—C4	122.51 (19)	C38—C37—C36	118.8 (2)
N1—C12—C11	117.40 (16)	C38—C37—H37	120.6
C4—C12—C11	120.07 (19)	C36—C37—H37	120.6
N3—C13—C14	122.86 (18)	C37—C38—C33	122.1 (2)
N3—C13—H13	118.6	C37—C38—H38	118.9
C14—C13—H13	118.6	C33—C38—H38	118.9
O9—Ni—O1—C25	6.44 (17)	C24—N3—C13—C14	−0.2 (3)
N1—Ni—O1—C25	98.76 (17)	Ni—N3—C13—C14	179.77 (14)
N4—Ni—O1—C25	−88.09 (17)	N3—C13—C14—C15	0.2 (3)
N3—Ni—O1—C25	−167.33 (17)	C13—C14—C15—C16	0.7 (3)
O9—Ni—N1—C1	85.77 (18)	C14—C15—C16—C24	−1.4 (3)
O1—Ni—N1—C1	−3.39 (18)	C14—C15—C16—C17	176.8 (2)
N2—Ni—N1—C1	177.17 (18)	C24—C16—C17—C18	−0.2 (3)
N3—Ni—N1—C1	−88.95 (18)	C15—C16—C17—C18	−178.4 (2)
O9—Ni—N1—C12	−93.22 (14)	C16—C17—C18—C19	−1.4 (3)
O1—Ni—N1—C12	177.63 (13)	C17—C18—C19—C23	0.8 (3)
N2—Ni—N1—C12	−1.81 (12)	C17—C18—C19—C20	−179.5 (2)
N3—Ni—N1—C12	92.07 (14)	C23—C19—C20—C21	−1.4 (3)
O9—Ni—N2—C10	−84.40 (18)	C18—C19—C20—C21	178.9 (2)
N1—Ni—N2—C10	−176.50 (18)	C19—C20—C21—C22	0.4 (4)
N4—Ni—N2—C10	10.28 (18)	C23—N4—C22—C21	−1.2 (3)
N3—Ni—N2—C10	90.02 (18)	Ni—N4—C22—C21	172.95 (16)
O9—Ni—N2—C11	94.28 (13)	C20—C21—C22—N4	1.0 (3)
N1—Ni—N2—C11	2.18 (12)	C22—N4—C23—C19	0.0 (3)
N4—Ni—N2—C11	−171.04 (13)	Ni—N4—C23—C19	−174.89 (14)
N3—Ni—N2—C11	−91.30 (13)	C22—N4—C23—C24	179.60 (16)
O1—Ni—N3—C13	−84.19 (16)	Ni—N4—C23—C24	4.67 (19)
N1—Ni—N3—C13	9.47 (16)	C20—C19—C23—N4	1.2 (3)
N4—Ni—N3—C13	−178.18 (17)	C18—C19—C23—N4	−179.07 (17)
N2—Ni—N3—C13	89.60 (16)	C20—C19—C23—C24	−178.33 (17)
O1—Ni—N3—C24	95.81 (12)	C18—C19—C23—C24	1.4 (3)
N1—Ni—N3—C24	−170.53 (11)	C13—N3—C24—C16	−0.6 (2)
N4—Ni—N3—C24	1.82 (11)	Ni—N3—C24—C16	179.43 (13)
N2—Ni—N3—C24	−90.40 (12)	C13—N3—C24—C23	−179.96 (15)
O9—Ni—N4—C22	8.27 (17)	Ni—N3—C24—C23	0.04 (18)
O1—Ni—N4—C22	97.51 (17)	C15—C16—C24—N3	1.4 (3)
N2—Ni—N4—C22	−83.78 (17)	C17—C16—C24—N3	−176.94 (17)
N3—Ni—N4—C22	−177.86 (17)	C15—C16—C24—C23	−179.25 (17)
O9—Ni—N4—C23	−177.36 (12)	C17—C16—C24—C23	2.4 (3)
O1—Ni—N4—C23	−88.13 (12)	N4—C23—C24—N3	−3.2 (2)
N2—Ni—N4—C23	90.59 (13)	C19—C23—C24—N3	176.39 (15)
N3—Ni—N4—C23	−3.49 (11)	N4—C23—C24—C16	177.41 (15)
C12—N1—C1—C2	0.2 (3)	C19—C23—C24—C16	−3.0 (3)
Ni—N1—C1—C2	−178.76 (16)	Ni—O1—C25—O2	−3.4 (3)
N1—C1—C2—C3	−1.0 (3)	Ni—O1—C25—C26	177.12 (11)
C1—C2—C3—C4	0.7 (4)	O2—C25—C26—C27	178.97 (17)
C2—C3—C4—C12	0.4 (3)	O1—C25—C26—C27	−1.5 (2)
C2—C3—C4—C5	−179.3 (2)	O2—C25—C26—C31	−0.5 (3)
C12—C4—C5—C6	2.5 (4)	O1—C25—C26—C31	178.98 (17)
C3—C4—C5—C6	−177.8 (2)	C31—C26—C27—O3	−178.65 (17)
C4—C5—C6—C7	0.0 (4)	C25—C26—C27—O3	1.8 (3)
C5—C6—C7—C8	176.5 (2)	C31—C26—C27—C28	0.5 (3)
C5—C6—C7—C11	−2.4 (4)	C25—C26—C27—C28	−179.04 (17)
C11—C7—C8—C9	−0.6 (3)	O3—C27—C28—C29	178.93 (18)
C6—C7—C8—C9	−179.5 (2)	C26—C27—C28—C29	−0.2 (3)
C7—C8—C9—C10	−0.1 (4)	C27—C28—C29—O4	179.65 (18)
C11—N2—C10—C9	1.1 (3)	C27—C28—C29—C30	−0.3 (3)
Ni—N2—C10—C9	179.71 (16)	O4—C29—C30—C31	−179.4 (2)
C8—C9—C10—N2	−0.1 (3)	C28—C29—C30—C31	0.6 (3)
C10—N2—C11—C7	−1.9 (3)	C29—C30—C31—C26	−0.3 (3)
Ni—N2—C11—C7	179.27 (15)	C27—C26—C31—C30	−0.2 (3)
C10—N2—C11—C12	176.61 (17)	C25—C26—C31—C30	179.31 (18)
Ni—N2—C11—C12	−2.2 (2)	O5—C32—C33—C38	−2.1 (3)
C8—C7—C11—N2	1.6 (3)	O6—C32—C33—C38	−179.1 (2)
C6—C7—C11—N2	−179.43 (19)	O5—C32—C33—C34	176.5 (2)
C8—C7—C11—C12	−176.82 (19)	O6—C32—C33—C34	−0.5 (3)
C6—C7—C11—C12	2.1 (3)	C38—C33—C34—O7	180.0 (2)
C1—N1—C12—C4	1.0 (3)	C32—C33—C34—O7	1.3 (3)
Ni—N1—C12—C4	−179.95 (15)	C38—C33—C34—C35	1.6 (3)
C1—N1—C12—C11	−177.89 (18)	C32—C33—C34—C35	−177.1 (2)
Ni—N1—C12—C11	1.2 (2)	O7—C34—C35—C36	179.8 (2)
C3—C4—C12—N1	−1.2 (3)	C33—C34—C35—C36	−1.7 (3)
C5—C4—C12—N1	178.49 (19)	C34—C35—C36—O8	−177.2 (2)
C3—C4—C12—C11	177.60 (18)	C34—C35—C36—C37	1.4 (4)
C5—C4—C12—C11	−2.7 (3)	O8—C36—C37—C38	177.6 (2)
N2—C11—C12—N1	0.7 (3)	C35—C36—C37—C38	−0.9 (4)
C7—C11—C12—N1	179.27 (17)	C36—C37—C38—C33	0.8 (4)
N2—C11—C12—C4	−178.14 (17)	C34—C33—C38—C37	−1.1 (3)
C7—C11—C12—C4	0.4 (3)	C32—C33—C38—C37	177.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O6	0.99	1.77	2.715 (3)	159
O1W—H1B···O5^i	0.91	1.78	2.685 (3)	172
O3—H3···O1	0.99	1.58	2.517 (2)	157
O4—H4···O1W^ii	0.92	1.68	2.589 (3)	172
O7—H7···O6	0.96	1.62	2.508 (3)	151
O8—H8···O2	0.94	1.87	2.733 (3)	151
O9—H9A···O2	0.97	1.72	2.632 (3)	155
O9—H9B···O5^iii	0.96	1.66	2.611 (3)	167
C20—H20···O3^iv	0.93	2.59	3.509 (4)	168

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