Bis(acetyl-acetonato-κ(2)O,O')bis-(pyridine-κN)nickel(II) dihydrate.

The title compound, [Ni(C(5)H(7)O(2))(2)(C(5)H(5)N)(2)]·2H(2)O, crystallizes with two half-mol-ecules in the asymmetric unit. The Ni(II) ion of each unique complex mol-ecule lies on an inversion centre and has an octa-hedral coordination geometry. The crystal structure features weak O-H⋯O hydrogen bonds, which form chains running parallel to the a axis.

Related literature

For the structures of octa­hedral complexes of the type [M(acac)2(L)2]2 (M = Ni; acac = acetyl­acetonate, 1,3-diphenyl-1,3 propane­dianato; L = pyridine, 3-cyano­pyridine, 4-cyano­pyridine, 3-methyl­pyridine, 2-methyl­pyridine, 4-pyridyl­tetra­thia­fulvalene), see: Elder (1968 ▶); Zukerman-Schpector et al. (2000 ▶, 2007 ▶); Wang et al. (2006 ▶); Soldatov et al. (2001 ▶).

Experimental

Crystal data

[Ni(C5H7O2)2(C5H5N)2]·2H2O

M = 451.13

Monoclinic,

a = 16.362 (5) Å

b = 14.476 (5) Å

c = 9.543 (5) Å

β = 91.510 (5)°

V = 2259.5 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 296 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

55078 measured reflections

5587 independent reflections

4298 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.103

S = 1.05

5587 reflections

269 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002699/kj2219sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002699/kj2219Isup2.hkl

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

[Ni(C5H7O2)2(C5H5N)2]·2H2O	F(000) = 952
Mr = 451.13	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9929 reflections
a = 16.362 (5) Å	θ = 2.6–28.3°
b = 14.476 (5) Å	µ = 0.89 mm−1
c = 9.543 (5) Å	T = 296 K
β = 91.510 (5)°	Block, blue
V = 2259.5 (16) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	4298 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.018
Graphite monochromator	θmax = 28.3°, θmin = 1.2°
Detector resolution: 18.4 pixels mm-1	h = −21→21
φ and ω scans	k = −18→19
55078 measured reflections	l = −12→12
5587 independent reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.9372P] where P = (Fo2 + 2Fc2)/3
5587 reflections	(Δ/σ)max < 0.001
269 parameters	Δρmax = 0.22 e Å−3
6 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.50000	0.50000	0.50000	0.0388 (1)
O1	0.59123 (8)	0.40479 (9)	0.52664 (13)	0.0504 (4)
O2	0.47500 (7)	0.45218 (9)	0.30232 (12)	0.0478 (4)
N1	0.41637 (9)	0.40607 (11)	0.58429 (15)	0.0458 (4)
C1	0.43286 (13)	0.36179 (16)	0.7042 (2)	0.0623 (7)
C2	0.38029 (16)	0.29902 (19)	0.7614 (3)	0.0771 (9)
C3	0.30771 (15)	0.27972 (18)	0.6921 (3)	0.0771 (9)
C4	0.29001 (13)	0.32532 (18)	0.5691 (2)	0.0703 (8)
C5	0.34512 (11)	0.38751 (15)	0.5184 (2)	0.0549 (6)
C6	0.68575 (14)	0.28756 (18)	0.4746 (3)	0.0733 (8)
C7	0.61380 (11)	0.34840 (14)	0.43447 (19)	0.0502 (6)
C8	0.57898 (14)	0.33964 (17)	0.3012 (2)	0.0663 (8)
C9	0.51543 (12)	0.39087 (14)	0.24124 (18)	0.0509 (6)
C10	0.49162 (19)	0.3735 (2)	0.0893 (2)	0.0821 (9)
Ni2	0.00000	0.50000	0.50000	0.0454 (1)
O3	0.05752 (8)	0.38202 (8)	0.44348 (15)	0.0548 (4)
O4	−0.07630 (8)	0.43023 (9)	0.62668 (15)	0.0553 (4)
N2	0.08437 (10)	0.51694 (10)	0.67131 (18)	0.0518 (5)
C11	0.16473 (15)	0.51415 (17)	0.6544 (3)	0.0696 (8)
C12	0.22079 (17)	0.5225 (2)	0.7630 (3)	0.0834 (10)
C13	0.19364 (18)	0.53429 (18)	0.8970 (3)	0.0774 (9)
C14	0.11092 (17)	0.53708 (17)	0.9161 (3)	0.0722 (9)
C15	0.05890 (14)	0.52919 (14)	0.8021 (2)	0.0602 (7)
C16	0.08741 (14)	0.22314 (14)	0.4275 (3)	0.0663 (8)
C17	0.03892 (11)	0.30288 (11)	0.48564 (19)	0.0464 (5)
C18	−0.02264 (13)	0.28323 (12)	0.5796 (2)	0.0552 (6)
C19	−0.07502 (11)	0.34409 (12)	0.64369 (18)	0.0449 (5)
C20	−0.13618 (13)	0.30541 (16)	0.7449 (2)	0.0629 (7)
O1W	0.33029 (12)	0.55261 (16)	0.2056 (2)	0.0998 (8)
O2W	0.18999 (13)	0.41332 (17)	0.2490 (2)	0.1108 (9)
H1	0.48220	0.37390	0.75120	0.0750*
H2	0.39370	0.27000	0.84590	0.0930*
H3	0.27140	0.23680	0.72780	0.0930*
H4	0.24100	0.31420	0.52040	0.0840*
H5	0.33240	0.41800	0.43490	0.0660*
H6A	0.68450	0.27370	0.57290	0.1100*
H6B	0.73570	0.31920	0.45470	0.1100*
H6C	0.68270	0.23120	0.42180	0.1100*
H8	0.60090	0.29390	0.24500	0.0800*
H10A	0.43520	0.38940	0.07350	0.1230*
H10B	0.49960	0.30950	0.06770	0.1230*
H10C	0.52500	0.41070	0.03030	0.1230*
H11	0.18390	0.50610	0.56430	0.0840*
H12	0.27650	0.52020	0.74620	0.1000*
H13	0.23040	0.54020	0.97250	0.0930*
H14	0.09040	0.54420	1.00550	0.0870*
H15	0.00300	0.53250	0.81620	0.0720*
H16A	0.12230	0.24540	0.35560	0.0990*
H16B	0.05050	0.17770	0.38880	0.0990*
H16C	0.12020	0.19580	0.50150	0.0990*
H18	−0.02930	0.22120	0.60200	0.0660*
H20A	−0.18290	0.34540	0.74740	0.0940*
H20B	−0.11120	0.30130	0.83690	0.0940*
H20C	−0.15310	0.24500	0.71440	0.0940*
H11W	0.35400	0.50780	0.17200	0.1500*
H22W	0.35500	0.57180	0.27800	0.1500*
H1W	0.15010	0.41390	0.30310	0.1660*
H2W	0.20310	0.47070	0.25810	0.1660*

	U11	U22	U33	U12	U13	U23
Ni1	0.0400 (2)	0.0425 (2)	0.0336 (2)	0.0005 (1)	−0.0026 (1)	−0.0044 (1)
O1	0.0492 (7)	0.0560 (7)	0.0456 (6)	0.0076 (6)	−0.0067 (5)	−0.0061 (6)
O2	0.0511 (7)	0.0537 (7)	0.0383 (6)	0.0006 (6)	−0.0061 (5)	−0.0068 (5)
N1	0.0468 (8)	0.0504 (8)	0.0402 (7)	−0.0042 (6)	−0.0011 (6)	−0.0032 (6)
C1	0.0618 (12)	0.0696 (13)	0.0550 (11)	−0.0134 (10)	−0.0092 (9)	0.0098 (10)
C2	0.0854 (17)	0.0819 (17)	0.0640 (13)	−0.0222 (13)	0.0003 (12)	0.0185 (12)
C3	0.0743 (15)	0.0784 (16)	0.0795 (15)	−0.0278 (13)	0.0189 (12)	0.0000 (13)
C4	0.0523 (11)	0.0885 (16)	0.0700 (13)	−0.0208 (11)	0.0018 (10)	−0.0099 (12)
C5	0.0479 (10)	0.0685 (12)	0.0480 (9)	−0.0059 (9)	−0.0016 (8)	−0.0052 (9)
C6	0.0612 (13)	0.0821 (16)	0.0767 (14)	0.0246 (12)	0.0031 (11)	0.0002 (12)
C7	0.0452 (9)	0.0539 (10)	0.0517 (10)	0.0038 (8)	0.0076 (7)	−0.0003 (8)
C8	0.0707 (13)	0.0781 (15)	0.0503 (11)	0.0186 (11)	0.0041 (9)	−0.0187 (10)
C9	0.0597 (11)	0.0565 (11)	0.0366 (8)	−0.0056 (9)	0.0031 (7)	−0.0058 (8)
C10	0.117 (2)	0.0896 (17)	0.0392 (10)	0.0126 (15)	−0.0071 (11)	−0.0138 (11)
Ni2	0.0479 (2)	0.0291 (2)	0.0602 (2)	0.0021 (1)	0.0166 (2)	0.0029 (1)
O3	0.0569 (8)	0.0353 (6)	0.0730 (9)	0.0058 (5)	0.0172 (6)	−0.0004 (6)
O4	0.0558 (7)	0.0408 (7)	0.0703 (8)	−0.0018 (6)	0.0198 (6)	0.0068 (6)
N2	0.0554 (9)	0.0389 (7)	0.0615 (9)	0.0026 (6)	0.0120 (7)	0.0016 (7)
C11	0.0579 (13)	0.0834 (16)	0.0680 (14)	0.0098 (11)	0.0090 (10)	−0.0047 (11)
C12	0.0616 (14)	0.102 (2)	0.0864 (18)	0.0118 (14)	−0.0030 (13)	−0.0064 (15)
C13	0.0899 (18)	0.0682 (15)	0.0734 (15)	0.0006 (13)	−0.0124 (13)	−0.0001 (12)
C14	0.0941 (18)	0.0618 (13)	0.0613 (13)	−0.0074 (13)	0.0111 (12)	−0.0023 (11)
C15	0.0655 (13)	0.0493 (10)	0.0667 (13)	−0.0038 (9)	0.0165 (10)	−0.0018 (9)
C16	0.0661 (13)	0.0401 (10)	0.0920 (16)	0.0103 (9)	−0.0103 (11)	−0.0159 (10)
C17	0.0490 (9)	0.0346 (8)	0.0549 (10)	0.0015 (7)	−0.0133 (7)	−0.0053 (7)
C18	0.0684 (12)	0.0327 (8)	0.0644 (11)	−0.0072 (8)	−0.0026 (9)	0.0044 (8)
C19	0.0475 (9)	0.0425 (9)	0.0442 (9)	−0.0102 (7)	−0.0103 (7)	0.0058 (7)
C20	0.0660 (12)	0.0641 (13)	0.0586 (11)	−0.0177 (10)	0.0023 (9)	0.0164 (10)
O1W	0.0906 (13)	0.1176 (17)	0.0896 (13)	0.0192 (12)	−0.0296 (10)	−0.0028 (12)
O2W	0.1004 (15)	0.1241 (18)	0.1093 (16)	0.0189 (13)	0.0298 (12)	−0.0021 (13)

Ni1—O1	2.0427 (17)	C1—H1	0.9300
Ni1—O2	2.0407 (16)	C2—H2	0.9300
Ni1—N1	2.1039 (19)	C3—H3	0.9300
Ni1—O1i	2.0427 (17)	C4—H4	0.9300
Ni1—O2i	2.0407 (16)	C5—H5	0.9300
Ni1—N1i	2.1039 (19)	C6—H6A	0.9600
Ni2—N2ii	2.126 (2)	C6—H6C	0.9600
Ni2—N2	2.126 (2)	C6—H6B	0.9600
Ni2—O3	2.0299 (16)	C8—H8	0.9300
Ni2—O4	2.0297 (17)	C10—H10B	0.9600
Ni2—O3ii	2.0298 (16)	C10—H10A	0.9600
Ni2—O4ii	2.0297 (17)	C10—H10C	0.9600
O1—C7	1.262 (2)	C11—C12	1.371 (4)
O2—C9	1.259 (2)	C12—C13	1.375 (4)
O3—C17	1.254 (2)	C13—C14	1.371 (4)
O4—C19	1.258 (2)	C14—C15	1.368 (4)
O1W—H22W	0.8400	C16—C17	1.514 (3)
O1W—H11W	0.8300	C17—C18	1.395 (3)
O2W—H2W	0.8600	C18—C19	1.383 (3)
O2W—H1W	0.8400	C19—C20	1.516 (3)
N1—C5	1.337 (2)	C11—H11	0.9300
N1—C1	1.333 (3)	C12—H12	0.9300
N2—C11	1.330 (3)	C13—H13	0.9300
N2—C15	1.338 (3)	C14—H14	0.9300
C1—C2	1.374 (4)	C15—H15	0.9300
C2—C3	1.373 (4)	C16—H16A	0.9600
C3—C4	1.371 (4)	C16—H16B	0.9600
C4—C5	1.371 (3)	C16—H16C	0.9600
C6—C7	1.511 (3)	C18—H18	0.9300
C7—C8	1.386 (3)	C20—H20B	0.9600
C8—C9	1.388 (3)	C20—H20C	0.9600
C9—C10	1.513 (3)	C20—H20A	0.9600
Ni1···O1W	3.972 (3)	N2···O4ii	2.944 (3)
Ni1···O1Wi	3.972 (3)	N2···O3	2.947 (3)
Ni1···H22W	3.3100	N2···O3ii	2.932 (3)
Ni1···H22Wi	3.3100	C2···C10vi	3.523 (4)
Ni2···H1Wii	3.3700	C2···C9vi	3.536 (4)
Ni2···H1W	3.3700	C4···C11	3.525 (4)
O1···N1	2.928 (2)	C9···C2v	3.536 (4)
O1···O2	2.908 (2)	C10···C2v	3.523 (4)
O1···N1i	2.937 (3)	C11···C4	3.525 (4)
O1···O1Wi	2.896 (3)	C1···H10Bvi	3.0200
O1···O2i	2.867 (2)	C4···H2v	3.0800
O1···C9	2.970 (3)	C5···H2v	2.9300
O1···C5i	3.215 (3)	C7···H22Wi	3.0100
O1···C1	3.195 (3)	C10···H11W	3.0900
O1W···Ni1	3.972 (3)	C14···H18vii	2.9800
O1W···O2	2.908 (3)	C15···H18vii	2.9700
O1W···O2W	3.092 (4)	C16···H4	2.9500
O1W···Ni1	3.972 (3)	C17···H1W	3.0200
O1W···O1i	2.896 (3)	C18···H20Bv	2.9600
O2···O1W	2.908 (3)	C19···H16Bvi	3.0900
O2···C7	2.976 (3)	H1···O2i	2.6700
O2···O1	2.908 (2)	H1···O1	2.8600
O2···C1i	3.088 (3)	H1W···O3	2.1000
O2···N1	2.957 (2)	H1W···C17	3.0200
O2···C5	3.143 (3)	H1W···Ni2	3.3700
O2···O1i	2.867 (2)	H1W···O4ii	2.6500
O2···N1i	2.905 (2)	H1W···H16A	2.5300
O2W···O1W	3.092 (4)	H1W···Ni2	3.3700
O2W···O4ii	3.180 (3)	H2···C4vi	3.0800
O2W···O3	2.926 (3)	H2···C5vi	2.9300
O3···N2ii	2.932 (3)	H2W···O4ii	2.7700
O3···O4	2.922 (2)	H2W···O1W	2.4600
O3···C19	2.979 (3)	H3···O2Wvi	2.5600
O3···O2W	2.926 (3)	H4···C16	2.9500
O3···C11	3.256 (3)	H5···O2W	2.8900
O3···O4ii	2.818 (2)	H5···O1i	2.8700
O3···N2	2.947 (3)	H5···O2	2.7300
O3···C15ii	3.246 (3)	H6A···H8vi	2.3800
O4···N2	2.934 (3)	H6C···O1Wviii	2.8600
O4···O3ii	2.818 (2)	H6C···H8	2.3100
O4···C17	2.983 (3)	H8···H10B	2.3500
O4···C15	3.091 (3)	H8···H6Av	2.3800
O4···O2Wii	3.180 (3)	H8···H6C	2.3100
O4···N2ii	2.944 (3)	H10A···H11W	2.3800
O4···O3	2.922 (2)	H10B···C1v	3.0200
O4···C11ii	3.120 (4)	H10B···H8	2.3500
O1···H22Wi	2.0700	H11···O4ii	2.6600
O1···H5i	2.8700	H11W···O2	2.4500
O1···H1	2.8600	H11W···C10	3.0900
O1W···H6Ciii	2.8600	H11W···H10A	2.3800
O1W···H20Aii	2.8700	H13···O1Wix	2.7300
O1W···H13iv	2.7300	H14···H15x	2.5700
O1W···H2W	2.4600	H15···H14x	2.5700
O2···H1i	2.6700	H15···O4	2.6500
O2···H22W	2.6200	H15···O3ii	2.9200
O2···H11W	2.4500	H16A···O2W	2.8700
O2···H5	2.7300	H16A···H1W	2.5300
O2W···H5	2.8900	H16B···C19v	3.0900
O2W···H3v	2.5600	H16B···H18	2.5300
O2W···H16A	2.8700	H18···C15xi	2.9700
O3···H1W	2.1000	H18···C14xi	2.9800
O3···H15ii	2.9200	H18···H16B	2.5300
O4···H15	2.6500	H18···H20C	2.3400
O4···H1Wii	2.6500	H20A···O1Wii	2.8700
O4···H11ii	2.6600	H20B···C18vi	2.9600
O4···H2Wii	2.7700	H20C···H18	2.3400
N1···O1	2.928 (2)	H22W···C7i	3.0100
N1···O2	2.957 (2)	H22W···Ni1	3.3100
N1···O1i	2.937 (3)	H22W···O2	2.6200
N1···O2i	2.905 (2)	H22W···Ni1	3.3100
N2···O4	2.934 (3)	H22W···O1i	2.0700
O1—Ni1—O2	90.81 (5)	C3—C2—H2	120.00
O1—Ni1—N1	89.82 (6)	C4—C3—H3	121.00
O1—Ni1—O1i	180.00	C2—C3—H3	121.00
O1—Ni1—O2i	89.19 (5)	C3—C4—H4	120.00
O1—Ni1—N1i	90.18 (6)	C5—C4—H4	120.00
O2—Ni1—N1	91.01 (5)	C4—C5—H5	119.00
O1i—Ni1—O2	89.19 (5)	N1—C5—H5	119.00
O2—Ni1—O2i	180.00	H6A—C6—H6B	109.00
O2—Ni1—N1i	88.99 (5)	H6A—C6—H6C	109.00
O1i—Ni1—N1	90.18 (6)	C7—C6—H6A	109.00
O2i—Ni1—N1	88.99 (5)	C7—C6—H6B	109.00
N1—Ni1—N1i	180.00	H6B—C6—H6C	110.00
O1i—Ni1—O2i	90.81 (5)	C7—C6—H6C	109.00
O1i—Ni1—N1i	89.82 (6)	C7—C8—H8	116.00
O2i—Ni1—N1i	91.01 (5)	C9—C8—H8	116.00
O4—Ni2—N2	89.80 (6)	H10A—C10—H10C	109.00
O3ii—Ni2—O4	87.92 (5)	H10B—C10—H10C	109.00
O4—Ni2—O4ii	180.00	C9—C10—H10C	109.00
O4—Ni2—N2ii	90.20 (6)	H10A—C10—H10B	110.00
O3ii—Ni2—N2	89.70 (6)	C9—C10—H10A	109.00
O4ii—Ni2—N2	90.20 (6)	C9—C10—H10B	109.00
N2—Ni2—N2ii	180.00	N2—C11—C12	123.3 (3)
O3ii—Ni2—O4ii	92.08 (5)	C11—C12—C13	119.2 (3)
O3ii—Ni2—N2ii	90.30 (6)	C12—C13—C14	118.1 (3)
O4ii—Ni2—N2ii	89.80 (6)	C13—C14—C15	119.2 (3)
O3—Ni2—O4	92.08 (5)	N2—C15—C14	123.4 (2)
O3—Ni2—N2	90.30 (6)	C16—C17—C18	118.30 (16)
O3—Ni2—O3ii	180.00	O3—C17—C18	125.29 (16)
O3—Ni2—O4ii	87.92 (5)	O3—C17—C16	116.41 (17)
O3—Ni2—N2ii	89.70 (6)	C17—C18—C19	128.36 (16)
Ni1—O1—C7	125.16 (12)	O4—C19—C20	116.07 (16)
Ni1—O2—C9	124.90 (11)	O4—C19—C18	125.66 (17)
Ni2—O3—C17	124.41 (12)	C18—C19—C20	118.27 (17)
Ni2—O4—C19	124.19 (12)	C12—C11—H11	118.00
H11W—O1W—H22W	111.00	N2—C11—H11	118.00
H1W—O2W—H2W	97.00	C13—C12—H12	120.00
Ni1—N1—C1	121.33 (13)	C11—C12—H12	120.00
Ni1—N1—C5	121.19 (13)	C14—C13—H13	121.00
C1—N1—C5	117.47 (17)	C12—C13—H13	121.00
Ni2—N2—C15	121.38 (14)	C13—C14—H14	120.00
C11—N2—C15	116.8 (2)	C15—C14—H14	120.00
Ni2—N2—C11	121.83 (16)	N2—C15—H15	118.00
N1—C1—C2	123.0 (2)	C14—C15—H15	118.00
C1—C2—C3	119.1 (2)	C17—C16—H16C	109.00
C2—C3—C4	118.4 (2)	H16A—C16—H16B	110.00
C3—C4—C5	119.5 (2)	C17—C16—H16B	109.00
N1—C5—C4	122.63 (18)	H16B—C16—H16C	110.00
C6—C7—C8	118.55 (19)	H16A—C16—H16C	109.00
O1—C7—C8	125.31 (18)	C17—C16—H16A	109.00
O1—C7—C6	116.13 (18)	C17—C18—H18	116.00
C7—C8—C9	127.9 (2)	C19—C18—H18	116.00
O2—C9—C10	115.84 (18)	C19—C20—H20B	109.00
O2—C9—C8	125.64 (17)	C19—C20—H20C	109.00
C8—C9—C10	118.52 (19)	H20A—C20—H20C	109.00
N1—C1—H1	118.00	H20B—C20—H20C	109.00
C2—C1—H1	119.00	H20A—C20—H20B	110.00
C1—C2—H2	120.00	C19—C20—H20A	109.00
O2—Ni1—O1—C7	2.88 (15)	Ni1—O1—C7—C6	176.78 (14)
N1—Ni1—O1—C7	93.89 (15)	Ni1—O1—C7—C8	−2.0 (3)
O2i—Ni1—O1—C7	−177.12 (15)	Ni1—O2—C9—C8	6.1 (3)
N1i—Ni1—O1—C7	−86.11 (15)	Ni1—O2—C9—C10	−173.57 (15)
O1—Ni1—O2—C9	−4.80 (15)	Ni2—O3—C17—C18	−1.4 (3)
N1—Ni1—O2—C9	−94.64 (15)	Ni2—O3—C17—C16	178.01 (14)
O1i—Ni1—O2—C9	175.20 (15)	Ni2—O4—C19—C20	178.97 (12)
N1i—Ni1—O2—C9	85.37 (15)	Ni2—O4—C19—C18	−0.4 (3)
O1—Ni1—N1—C1	49.00 (15)	C1—N1—C5—C4	−0.3 (3)
O2—Ni1—N1—C1	139.81 (15)	Ni1—N1—C1—C2	−179.04 (18)
O1i—Ni1—N1—C1	−131.00 (15)	Ni1—N1—C5—C4	178.68 (16)
O2i—Ni1—N1—C1	−40.19 (15)	C5—N1—C1—C2	0.0 (3)
O1—Ni1—N1—C5	−129.99 (15)	Ni2—N2—C11—C12	−178.3 (2)
O2—Ni1—N1—C5	−39.18 (15)	C15—N2—C11—C12	0.4 (3)
O1i—Ni1—N1—C5	50.01 (15)	C11—N2—C15—C14	−1.2 (3)
O2i—Ni1—N1—C5	140.82 (15)	Ni2—N2—C15—C14	177.59 (17)
O4ii—Ni2—N2—C15	145.01 (15)	N1—C1—C2—C3	0.7 (4)
O4—Ni2—O3—C17	1.15 (15)	C1—C2—C3—C4	−1.1 (4)
N2—Ni2—O3—C17	90.97 (15)	C2—C3—C4—C5	0.7 (4)
O4ii—Ni2—O3—C17	−178.85 (15)	C3—C4—C5—N1	0.0 (3)
N2ii—Ni2—O3—C17	−89.04 (15)	O1—C7—C8—C9	1.8 (4)
O3—Ni2—O4—C19	−0.32 (15)	C6—C7—C8—C9	−177.0 (2)
N2—Ni2—O4—C19	−90.61 (15)	C7—C8—C9—C10	175.5 (2)
O3ii—Ni2—O4—C19	179.68 (15)	C7—C8—C9—O2	−4.1 (4)
N2ii—Ni2—O4—C19	89.39 (15)	N2—C11—C12—C13	0.1 (4)
O3—Ni2—N2—C11	51.62 (16)	C11—C12—C13—C14	0.1 (4)
O4—Ni2—N2—C11	143.71 (16)	C12—C13—C14—C15	−0.8 (4)
O3ii—Ni2—N2—C11	−128.38 (16)	C13—C14—C15—N2	1.4 (4)
O4ii—Ni2—N2—C11	−36.29 (16)	O3—C17—C18—C19	0.5 (3)
O3—Ni2—N2—C15	−127.07 (15)	C16—C17—C18—C19	−178.9 (2)
O4—Ni2—N2—C15	−34.99 (15)	C17—C18—C19—C20	−178.79 (19)
O3ii—Ni2—N2—C15	52.93 (15)	C17—C18—C19—O4	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H1W···O3	0.84	2.10	2.926 (3)	166
O2W—H2W···O1W	0.86	2.46	3.092 (4)	131
O1W—H11W···O2	0.83	2.45	2.908 (3)	116
O1W—H22W···O1i	0.84	2.07	2.896 (3)	169
C3—H3···O2Wvi	0.93	2.56	3.445 (4)	159

Table 1

Selected bond lengths (Å)

Ni1—O1	2.0427 (17)
Ni1—O2	2.0407 (16)
Ni1—N1	2.1039 (19)
Ni2—N2	2.126 (2)
Ni2—O3	2.0299 (16)
Ni2—O4	2.0297 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H1W⋯O3	0.84	2.10	2.926 (3)	166
O2W—H2W⋯O1W	0.86	2.46	3.092 (4)	131
O1W—H11W⋯O2	0.83	2.45	2.908 (3)	116
O1W—H22W⋯O1i	0.84	2.07	2.896 (3)	169

Symmetry code: (i) .