Bis(pentane-2,4-dionato)bis-[2-(4-pyrid-yl)-4,4,5,5-tetra-methyl-imidazoline-1-oxyl 3-oxide]nickel(II).

In the title compound, [Ni(C(5)H(7)O(2))(2)(C(12)H(16)N(3)O(2))], the Ni(II) cation is hexa-coordinated by four O and two N atoms, showing a slightly distorted octa-hedral geometry. The Ni(II) cation lies on an inversion centre, as a consequence of which the asymmetric unit comprises one half-mol-ecule. The four O atoms belonging to two pentane-2,4-dionate ligands lie in the equatorial plane and two pyridyl N atoms occupy the axial coordination sites.

Related literature

For related literature, see: Caneschi et al. (1989 ▶); Tsukuda et al. (2002 ▶); Vostrikova et al. (2000 ▶); Kuchar et al. (2003 ▶).

Experimental

Crystal data

[Ni(C5H7O2)2(C12H16N3O2)]

M = 725.48

Triclinic,

a = 6.9862 (10) Å

b = 10.121 (3) Å

c = 12.735 (3) Å

α = 98.20 (2)°

β = 103.21 (2)°

γ = 93.08 (2)°

V = 864.1 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.62 mm−1

T = 293 (2) K

0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.776, T max = 0.875

5805 measured reflections

2968 independent reflections

2356 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.00

2968 reflections

229 parameters

H-atom parameters not refined

Δρmax = 0.38 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536808018552/kp2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018552/kp2176Isup2.hkl

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

[Ni(C5H7O2)2(C12H16N3O2)]	Z = 1
Mr = 725.48	F000 = 384
Triclinic, P1	Dx = 1.394 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.9862 (10) Å	Cell parameters from 2968 reflections
b = 10.121 (3) Å	θ = 3.1–25.0º
c = 12.735 (3) Å	µ = 0.62 mm−1
α = 98.20 (2)º	T = 293 (2) K
β = 103.21 (2)º	Block, green
γ = 93.08 (2)º	0.43 × 0.28 × 0.22 mm
V = 864.1 (3) Å3

Bruker APEXII CCD area-detector diffractometer	2968 independent reflections
Radiation source: fine-focus sealed tube	2356 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −6→8
Tmin = 0.776, Tmax = 0.876	k = −12→12
5805 measured reflections	l = −11→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters not refined
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0577P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2968 reflections	Δρmax = 0.38 e Å−3
229 parameters	Δρmin = −0.51 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.0000	0.0000	0.0000	0.01842 (16)
C1	0.6315 (4)	0.1982 (3)	0.4503 (2)	0.0171 (5)
C2	0.4941 (4)	0.1511 (2)	0.3460 (2)	0.0157 (5)
C3	0.5524 (4)	0.0953 (3)	0.2533 (2)	0.0182 (5)
H3	0.6852	0.0863	0.2562	0.022*
C4	0.4134 (4)	0.0538 (2)	0.1578 (2)	0.0169 (5)
H4	0.4551	0.0175	0.0965	0.020*
C5	0.1699 (4)	0.1168 (2)	0.2385 (2)	0.0163 (5)
H5	0.0360	0.1243	0.2334	0.020*
C6	0.2972 (3)	0.1614 (2)	0.33692 (19)	0.0159 (5)
H6	0.2511	0.1980	0.3967	0.019*
C7	0.9190 (3)	0.2686 (2)	0.58605 (18)	0.0148 (5)
C8	0.7425 (4)	0.2983 (3)	0.6346 (2)	0.0181 (5)
C9	0.6895 (4)	0.4438 (3)	0.6355 (2)	0.0260 (6)
H9A	0.6955	0.4711	0.5671	0.039*
H9B	0.7816	0.5013	0.6938	0.039*
H9C	0.5585	0.4500	0.6462	0.039*
C10	0.7513 (4)	0.2543 (3)	0.7443 (2)	0.0232 (6)
H10A	0.6333	0.2747	0.7674	0.035*
H10B	0.8640	0.3008	0.7971	0.035*
H10C	0.7623	0.1595	0.7378	0.035*
C11	1.0773 (3)	0.3828 (3)	0.6102 (2)	0.0186 (6)
H11A	1.1758	0.3599	0.5708	0.028*
H11B	1.1372	0.3998	0.6872	0.028*
H11C	1.0201	0.4616	0.5882	0.028*
C12	1.0024 (4)	0.1370 (3)	0.6126 (2)	0.0186 (5)
H12A	0.8965	0.0672	0.5967	0.028*
H12B	1.0684	0.1480	0.6886	0.028*
H12C	1.0945	0.1133	0.5690	0.028*
C13	−0.1318 (4)	0.3856 (3)	0.1296 (2)	0.0236 (6)
H13A	−0.2720	0.3832	0.1017	0.035*
H13B	−0.0716	0.4731	0.1295	0.035*
H13C	−0.1042	0.3661	0.2028	0.035*
C14	−0.0496 (4)	0.2828 (2)	0.05844 (19)	0.0169 (5)
C15	0.1142 (4)	0.3210 (2)	0.0228 (2)	0.0193 (6)
H15	0.1681	0.4094	0.0447	0.023*
C16	0.2042 (4)	0.2369 (2)	−0.0434 (2)	0.0183 (6)
C17	0.3724 (4)	0.2937 (3)	−0.0815 (2)	0.0257 (6)
H17A	0.4877	0.2489	−0.0560	0.039*
H17B	0.3981	0.3877	−0.0531	0.039*
H17C	0.3400	0.2812	−0.1599	0.039*
N1	0.2240 (3)	0.06298 (19)	0.14880 (16)	0.0147 (4)
N2	0.5853 (3)	0.2130 (2)	0.54884 (17)	0.0188 (5)
N3	0.8188 (3)	0.2419 (2)	0.46714 (16)	0.0154 (5)
O1	0.4272 (2)	0.1725 (2)	0.56916 (14)	0.0276 (5)
O2	0.9117 (2)	0.25109 (18)	0.39294 (14)	0.0212 (4)
O3	−0.1365 (2)	0.16536 (16)	0.03800 (13)	0.0173 (4)
O4	0.1568 (2)	0.11205 (17)	−0.07687 (13)	0.0183 (4)

	U11	U22	U33	U12	U13	U23
Ni1	0.0180 (3)	0.0196 (3)	0.0157 (3)	0.00152 (18)	0.00049 (19)	0.00216 (19)
C1	0.0170 (13)	0.0237 (14)	0.0112 (13)	0.0031 (10)	0.0052 (10)	0.0011 (10)
C2	0.0157 (13)	0.0186 (13)	0.0127 (13)	0.0000 (10)	0.0026 (10)	0.0040 (10)
C3	0.0149 (13)	0.0234 (14)	0.0164 (14)	0.0020 (10)	0.0039 (11)	0.0028 (11)
C4	0.0173 (13)	0.0198 (13)	0.0143 (13)	0.0030 (10)	0.0041 (10)	0.0039 (10)
C5	0.0133 (12)	0.0192 (13)	0.0180 (14)	0.0022 (10)	0.0045 (10)	0.0069 (10)
C6	0.0166 (13)	0.0217 (13)	0.0100 (13)	0.0024 (10)	0.0039 (10)	0.0026 (10)
C7	0.0139 (12)	0.0242 (14)	0.0047 (12)	0.0012 (10)	0.0009 (10)	0.0000 (10)
C8	0.0134 (13)	0.0279 (15)	0.0114 (13)	0.0040 (10)	0.0003 (10)	0.0018 (11)
C9	0.0217 (14)	0.0332 (16)	0.0218 (15)	0.0111 (12)	0.0025 (11)	0.0012 (12)
C10	0.0186 (14)	0.0393 (17)	0.0112 (14)	0.0027 (11)	0.0023 (11)	0.0046 (12)
C11	0.0155 (13)	0.0246 (14)	0.0144 (14)	0.0020 (10)	0.0016 (10)	0.0017 (11)
C12	0.0148 (13)	0.0241 (14)	0.0170 (14)	0.0024 (10)	0.0039 (10)	0.0034 (11)
C13	0.0270 (15)	0.0192 (14)	0.0214 (15)	0.0067 (11)	0.0002 (11)	0.0001 (11)
C14	0.0179 (13)	0.0193 (14)	0.0094 (13)	0.0045 (10)	−0.0062 (10)	0.0029 (10)
C15	0.0221 (14)	0.0155 (13)	0.0168 (14)	0.0003 (10)	−0.0029 (11)	0.0035 (10)
C16	0.0165 (13)	0.0207 (14)	0.0144 (13)	−0.0002 (10)	−0.0061 (10)	0.0087 (10)
C17	0.0190 (14)	0.0257 (15)	0.0308 (16)	−0.0023 (11)	0.0009 (12)	0.0093 (12)
N1	0.0183 (11)	0.0148 (11)	0.0113 (11)	0.0021 (8)	0.0037 (9)	0.0019 (8)
N2	0.0099 (11)	0.0332 (13)	0.0128 (12)	0.0012 (9)	0.0023 (9)	0.0030 (9)
N3	0.0096 (10)	0.0243 (12)	0.0112 (11)	−0.0003 (8)	0.0012 (9)	0.0014 (8)
O1	0.0109 (9)	0.0545 (13)	0.0181 (10)	−0.0025 (8)	0.0046 (8)	0.0083 (9)
O2	0.0145 (9)	0.0369 (11)	0.0126 (9)	0.0002 (8)	0.0058 (7)	0.0010 (8)
O3	0.0157 (9)	0.0184 (9)	0.0159 (9)	0.0034 (7)	−0.0005 (7)	0.0022 (7)
O4	0.0172 (9)	0.0214 (10)	0.0140 (9)	−0.0006 (7)	−0.0002 (7)	0.0027 (7)

Ni1—O3i	2.0239 (17)	C9—H9B	0.9600
Ni1—O3	2.0239 (17)	C9—H9C	0.9600
Ni1—O4i	2.0292 (16)	C10—H10A	0.9600
Ni1—O4	2.0292 (16)	C10—H10B	0.9600
Ni1—N1	2.154 (2)	C10—H10C	0.9600
Ni1—N1i	2.154 (2)	C11—H11A	0.9600
C1—N3	1.318 (3)	C11—H11B	0.9600
C1—N2	1.355 (3)	C11—H11C	0.9600
C1—C2	1.450 (3)	C12—H12A	0.9600
C2—C6	1.364 (3)	C12—H12B	0.9600
C2—C3	1.390 (4)	C12—H12C	0.9600
C3—C4	1.366 (4)	C13—C14	1.506 (3)
C3—H3	0.9300	C13—H13A	0.9600
C4—N1	1.312 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—N1	1.337 (3)	C14—O3	1.269 (3)
C5—C6	1.361 (3)	C14—C15	1.380 (4)
C5—H5	0.9300	C15—C16	1.388 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—N3	1.495 (3)	C16—O4	1.275 (3)
C7—C11	1.503 (3)	C16—C17	1.488 (3)
C7—C8	1.526 (3)	C17—H17A	0.9600
C7—C12	1.533 (3)	C17—H17B	0.9600
C8—N2	1.491 (3)	C17—H17C	0.9600
C8—C10	1.515 (3)	N2—O1	1.252 (3)
C8—C9	1.537 (4)	N3—O2	1.273 (3)
C9—H9A	0.9600
O3i—Ni1—O3	180.00 (12)	C8—C10—H10A	109.5
O3i—Ni1—O4i	87.77 (7)	C8—C10—H10B	109.5
O3—Ni1—O4i	92.23 (7)	H10A—C10—H10B	109.5
O3i—Ni1—O4	92.23 (7)	C8—C10—H10C	109.5
O3—Ni1—O4	87.77 (7)	H10A—C10—H10C	109.5
O4i—Ni1—O4	180.00 (9)	H10B—C10—H10C	109.5
O3i—Ni1—N1	91.68 (7)	C7—C11—H11A	109.5
O3—Ni1—N1	88.33 (7)	C7—C11—H11B	109.5
O4i—Ni1—N1	91.41 (7)	H11A—C11—H11B	109.5
O4—Ni1—N1	88.59 (7)	C7—C11—H11C	109.5
O3i—Ni1—N1i	88.32 (7)	H11A—C11—H11C	109.5
O3—Ni1—N1i	91.67 (7)	H11B—C11—H11C	109.5
O4i—Ni1—N1i	88.59 (7)	C7—C12—H12A	109.5
O4—Ni1—N1i	91.41 (7)	C7—C12—H12B	109.5
N1—Ni1—N1i	180.00 (8)	H12A—C12—H12B	109.5
N3—C1—N2	107.4 (2)	C7—C12—H12C	109.5
N3—C1—C2	127.1 (2)	H12A—C12—H12C	109.5
N2—C1—C2	125.4 (2)	H12B—C12—H12C	109.5
C6—C2—C3	117.6 (2)	C14—C13—H13A	109.5
C6—C2—C1	119.1 (2)	C14—C13—H13B	109.5
C3—C2—C1	123.3 (2)	H13A—C13—H13B	109.5
C4—C3—C2	119.6 (2)	C14—C13—H13C	109.5
C4—C3—H3	120.2	H13A—C13—H13C	109.5
C2—C3—H3	120.2	H13B—C13—H13C	109.5
N1—C4—C3	123.0 (2)	O3—C14—C15	125.1 (2)
N1—C4—H4	118.5	O3—C14—C13	116.2 (2)
C3—C4—H4	118.5	C15—C14—C13	118.7 (2)
N1—C5—C6	124.5 (2)	C14—C15—C16	124.7 (2)
N1—C5—H5	117.8	C14—C15—H15	117.7
C6—C5—H5	117.8	C16—C15—H15	117.7
C5—C6—C2	118.5 (2)	O4—C16—C15	126.3 (2)
C5—C6—H6	120.7	O4—C16—C17	114.7 (2)
C2—C6—H6	120.7	C15—C16—C17	118.9 (2)
N3—C7—C11	110.84 (19)	C16—C17—H17A	109.5
N3—C7—C8	100.11 (18)	C16—C17—H17B	109.5
C11—C7—C8	114.5 (2)	H17A—C17—H17B	109.5
N3—C7—C12	105.69 (19)	C16—C17—H17C	109.5
C11—C7—C12	112.2 (2)	H17A—C17—H17C	109.5
C8—C7—C12	112.4 (2)	H17B—C17—H17C	109.5
N2—C8—C7	98.88 (19)	C4—N1—C5	116.8 (2)
N2—C8—C10	109.8 (2)	C4—N1—Ni1	124.33 (16)
C7—C8—C10	115.3 (2)	C5—N1—Ni1	118.92 (16)
N2—C8—C9	106.9 (2)	O1—N2—C1	127.2 (2)
C7—C8—C9	113.5 (2)	O1—N2—C8	121.2 (2)
C10—C8—C9	111.4 (2)	C1—N2—C8	111.4 (2)
C8—C9—H9A	109.5	O2—N3—C1	125.5 (2)
C8—C9—H9B	109.5	O2—N3—C7	122.47 (18)
H9A—C9—H9B	109.5	C1—N3—C7	111.82 (19)
C8—C9—H9C	109.5	C14—O3—Ni1	122.70 (15)
H9A—C9—H9C	109.5	C16—O4—Ni1	121.69 (15)
H9B—C9—H9C	109.5

Ni1—O3	2.0239 (17)
Ni1—O4	2.0292 (16)
Ni1—N1	2.154 (2)

O3i—Ni1—O3	180
O3—Ni1—O4	87.77 (7)
O4i—Ni1—O4	180
O3—Ni1—N1	88.32 (7)
O4—Ni1—N1	88.59 (7)
N1—Ni1—N1i	180

Symmetry code: (i) .