Bis(nitrato-κO)bis-[4,4,5,5-tetra-methyl-2-(5-methyl-1H-imidazol-4-yl-κN)-2-imidazoline-1-oxyl 3-oxide-κO]nickel(II).

In the centrosymmetric mononuclear title complex, [Ni(NO(3))(2)(C(11)H(17)N(4)O(2))(2)], the Ni(II) atom displays a distorted octa-hedral coordination geometry and is six-coordinated by two N,O-bidentate nitronyl nitroxide radical ligands and two monodentate nitrate anions.

Related literature

For general background to mol­ecular magnetic materials, see: Li et al. (2004 ▶); Wang et al. (2008 ▶); Yamamoto et al. (2001 ▶). For the synthesis, see: Ullman et al. (1970 ▶, 1972 ▶). For the related isomorphous Co complex, see: Gao et al. (2010 ▶).

Experimental

Crystal data

[Ni(NO3)2(C11H17N4O2)2]

M = 657.30

Monoclinic,

a = 7.8313 (5) Å

b = 10.7772 (8) Å

c = 17.3009 (12) Å

β = 101.464 (1)°

V = 1431.07 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 295 K

0.43 × 0.17 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.741, T max = 0.939

12170 measured reflections

3280 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.084

S = 1.03

3280 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040402/bg2419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040402/bg2419Isup2.hkl

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

[Ni(NO3)2(C11H17N4O2)2]	F(000) = 688
Mr = 657.30	Dx = 1.525 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4292 reflections
a = 7.8313 (5) Å	θ = 2.7–28.3°
b = 10.7772 (8) Å	µ = 0.75 mm−1
c = 17.3009 (12) Å	T = 295 K
β = 101.464 (1)°	Block, dark blue
V = 1431.07 (17) Å3	0.43 × 0.17 × 0.09 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.741, Tmax = 0.939	k = −13→14
12170 measured reflections	l = −22→22

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.047P)2 + 0.4906P] where P = (Fo2 + 2Fc2)/3
3280 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.0000	0.0000	0.02551 (9)
O1	0.00030 (13)	0.87872 (10)	0.09062 (7)	0.0356 (3)
O2	0.56556 (16)	0.72951 (13)	0.14208 (11)	0.0628 (4)
O3	−0.11891 (17)	1.14165 (13)	0.06167 (9)	0.0535 (4)
O4	0.0728 (2)	1.27774 (17)	0.11237 (13)	0.0793 (5)
O5	−0.1945 (2)	1.29491 (15)	0.12542 (11)	0.0695 (5)
N1	0.13496 (15)	0.80628 (12)	0.11228 (7)	0.0293 (3)
N2	0.40216 (17)	0.73607 (13)	0.13945 (9)	0.0389 (3)
N3	0.25299 (15)	1.03606 (12)	0.04597 (7)	0.0288 (3)
N4	0.50665 (16)	1.12494 (12)	0.08397 (8)	0.0341 (3)
H4D	0.5873	1.1801	0.0877	0.041*
N5	−0.07686 (18)	1.23919 (14)	0.10055 (9)	0.0409 (3)
C1	0.30161 (18)	0.83775 (14)	0.11699 (9)	0.0293 (3)
C2	0.1134 (2)	0.68040 (14)	0.14566 (10)	0.0335 (3)
C3	0.2948 (2)	0.62185 (15)	0.14399 (10)	0.0378 (4)
C4	0.0799 (3)	0.70293 (19)	0.22840 (12)	0.0527 (5)
H4A	−0.0233	0.7523	0.2252	0.079*
H4B	0.1775	0.7459	0.2593	0.079*
H4C	0.0644	0.6248	0.2528	0.079*
C5	−0.0410 (2)	0.61400 (18)	0.09556 (13)	0.0506 (5)
H5A	−0.1470	0.6545	0.1013	0.076*
H5B	−0.0432	0.5293	0.1125	0.076*
H5C	−0.0305	0.6162	0.0412	0.076*
C6	0.3723 (3)	0.5458 (2)	0.21666 (14)	0.0598 (6)
H6A	0.4829	0.5128	0.2109	0.090*
H6B	0.2949	0.4789	0.2224	0.090*
H6C	0.3880	0.5979	0.2626	0.090*
C7	0.3019 (3)	0.5479 (2)	0.06956 (14)	0.0571 (5)
H7A	0.4210	0.5298	0.0677	0.086*
H7B	0.2505	0.5957	0.0240	0.086*
H7C	0.2386	0.4717	0.0701	0.086*
C8	0.36190 (18)	0.95783 (14)	0.09802 (9)	0.0276 (3)
C9	0.52150 (19)	1.01413 (14)	0.12285 (9)	0.0299 (3)
C10	0.34633 (19)	1.13445 (15)	0.03893 (10)	0.0337 (3)
H10A	0.3070	1.2021	0.0070	0.040*
C11	0.6814 (2)	0.98292 (17)	0.18240 (11)	0.0404 (4)
H11C	0.7305	1.0575	0.2080	0.061*
H11D	0.7650	0.9439	0.1566	0.061*
H11A	0.6515	0.9273	0.2210	0.061*

	U11	U22	U33	U12	U13	U23
Ni1	0.01760 (14)	0.02601 (15)	0.03174 (15)	−0.00258 (9)	0.00206 (10)	0.00404 (10)
O1	0.0231 (5)	0.0370 (6)	0.0476 (6)	0.0047 (4)	0.0095 (5)	0.0158 (5)
O2	0.0250 (6)	0.0460 (8)	0.1147 (13)	0.0068 (5)	0.0077 (7)	0.0061 (8)
O3	0.0379 (7)	0.0565 (8)	0.0675 (9)	−0.0097 (6)	0.0138 (6)	−0.0187 (7)
O4	0.0414 (8)	0.0697 (11)	0.1226 (15)	−0.0215 (8)	0.0061 (9)	−0.0141 (10)
O5	0.0641 (10)	0.0521 (9)	0.0981 (13)	−0.0120 (7)	0.0301 (9)	−0.0232 (8)
N1	0.0246 (6)	0.0287 (6)	0.0341 (6)	0.0005 (5)	0.0043 (5)	0.0069 (5)
N2	0.0255 (6)	0.0314 (7)	0.0570 (9)	0.0015 (5)	0.0010 (6)	0.0022 (6)
N3	0.0213 (6)	0.0293 (6)	0.0349 (7)	−0.0026 (5)	0.0038 (5)	0.0022 (5)
N4	0.0240 (6)	0.0355 (7)	0.0426 (7)	−0.0093 (5)	0.0065 (5)	0.0005 (6)
N5	0.0339 (7)	0.0410 (8)	0.0465 (8)	−0.0070 (6)	0.0048 (6)	0.0088 (6)
C1	0.0228 (7)	0.0301 (7)	0.0335 (7)	−0.0003 (5)	0.0022 (5)	0.0008 (6)
C2	0.0318 (8)	0.0281 (7)	0.0389 (8)	−0.0039 (6)	0.0026 (6)	0.0081 (6)
C3	0.0334 (8)	0.0277 (7)	0.0481 (9)	0.0001 (6)	−0.0021 (7)	0.0029 (7)
C4	0.0653 (13)	0.0497 (11)	0.0470 (10)	0.0018 (9)	0.0204 (9)	0.0140 (8)
C5	0.0362 (9)	0.0387 (9)	0.0703 (13)	−0.0094 (7)	−0.0052 (8)	0.0032 (9)
C6	0.0520 (12)	0.0473 (11)	0.0704 (14)	0.0064 (9)	−0.0113 (10)	0.0195 (10)
C7	0.0538 (12)	0.0469 (11)	0.0690 (14)	0.0022 (9)	0.0082 (10)	−0.0133 (10)
C8	0.0219 (7)	0.0289 (7)	0.0319 (7)	0.0002 (5)	0.0048 (5)	−0.0008 (6)
C9	0.0226 (7)	0.0356 (8)	0.0320 (7)	−0.0013 (6)	0.0064 (6)	−0.0031 (6)
C10	0.0265 (7)	0.0334 (8)	0.0408 (8)	−0.0039 (6)	0.0060 (6)	0.0049 (6)
C11	0.0240 (8)	0.0500 (10)	0.0443 (9)	−0.0005 (7)	−0.0004 (7)	−0.0003 (7)

Ni1—N3i	2.0206 (12)	C2—C4	1.525 (3)
Ni1—N3	2.0206 (12)	C2—C3	1.560 (2)
Ni1—O1i	2.0408 (10)	C3—C7	1.525 (3)
Ni1—O1	2.0408 (10)	C3—C6	1.522 (3)
Ni1—O3	2.1751 (13)	C4—H4A	0.9600
Ni1—O3i	2.1751 (13)	C4—H4B	0.9600
O1—N1	1.3057 (16)	C4—H4C	0.9600
O2—N2	1.2733 (18)	C5—H5A	0.9600
O3—N5	1.256 (2)	C5—H5B	0.9600
O4—N5	1.221 (2)	C5—H5C	0.9600
O5—N5	1.246 (2)	C6—H6A	0.9600
N1—C1	1.3351 (18)	C6—H6B	0.9600
N1—C2	1.4971 (19)	C6—H6C	0.9600
N2—C1	1.3603 (19)	C7—H7A	0.9600
N2—C3	1.501 (2)	C7—H7B	0.9600
N3—C10	1.3073 (19)	C7—H7C	0.9600
N3—C8	1.3942 (19)	C8—C9	1.379 (2)
N4—C10	1.344 (2)	C9—C11	1.493 (2)
N4—C9	1.364 (2)	C10—H10A	0.9300
N4—H4D	0.8600	C11—H11C	0.9600
C1—C8	1.438 (2)	C11—H11D	0.9600
C2—C5	1.520 (2)	C11—H11A	0.9600
N3i—Ni1—N3	180.0	C7—C3—C6	109.94 (17)
N3i—Ni1—O1i	88.25 (5)	N2—C3—C2	101.00 (12)
N3—Ni1—O1i	91.75 (5)	C7—C3—C2	114.39 (14)
N3i—Ni1—O1	91.75 (5)	C6—C3—C2	114.66 (16)
N3—Ni1—O1	88.25 (5)	C2—C4—H4A	109.5
O1i—Ni1—O1	180.00 (4)	C2—C4—H4B	109.5
N3i—Ni1—O3	81.15 (5)	H4A—C4—H4B	109.5
N3—Ni1—O3	98.85 (5)	C2—C4—H4C	109.5
O1i—Ni1—O3	89.55 (5)	H4A—C4—H4C	109.5
O1—Ni1—O3	90.45 (5)	H4B—C4—H4C	109.5
N3i—Ni1—O3i	98.85 (5)	C2—C5—H5A	109.5
N3—Ni1—O3i	81.15 (5)	C2—C5—H5B	109.5
O1i—Ni1—O3i	90.45 (5)	H5A—C5—H5B	109.5
O1—Ni1—O3i	89.55 (5)	C2—C5—H5C	109.5
O3—Ni1—O3i	180.00 (6)	H5A—C5—H5C	109.5
N1—O1—Ni1	118.74 (8)	H5B—C5—H5C	109.5
N5—O3—Ni1	139.27 (11)	C3—C6—H6A	109.5
O1—N1—C1	126.13 (13)	C3—C6—H6B	109.5
O1—N1—C2	120.40 (11)	H6A—C6—H6B	109.5
C1—N1—C2	112.98 (12)	C3—C6—H6C	109.5
O2—N2—C1	125.14 (14)	H6A—C6—H6C	109.5
O2—N2—C3	121.44 (13)	H6B—C6—H6C	109.5
C1—N2—C3	112.16 (12)	C3—C7—H7A	109.5
C10—N3—C8	105.61 (12)	C3—C7—H7B	109.5
C10—N3—Ni1	129.94 (11)	H7A—C7—H7B	109.5
C8—N3—Ni1	124.33 (10)	C3—C7—H7C	109.5
C10—N4—C9	109.33 (13)	H7A—C7—H7C	109.5
C10—N4—H4D	125.3	H7B—C7—H7C	109.5
C9—N4—H4D	125.3	C9—C8—N3	109.59 (13)
O4—N5—O5	121.93 (17)	C9—C8—C1	130.05 (14)
O4—N5—O3	120.99 (17)	N3—C8—C1	120.35 (13)
O5—N5—O3	117.07 (15)	N4—C9—C8	104.39 (13)
N1—C1—N2	108.43 (13)	N4—C9—C11	121.00 (14)
N1—C1—C8	125.18 (13)	C8—C9—C11	134.40 (15)
N2—C1—C8	126.34 (13)	N3—C10—N4	111.07 (14)
N1—C2—C5	110.16 (13)	N3—C10—H10A	124.5
N1—C2—C4	105.75 (14)	N4—C10—H10A	124.5
C5—C2—C4	110.14 (16)	C9—C11—H11C	109.5
N1—C2—C3	100.75 (12)	C9—C11—H11D	109.5
C5—C2—C3	115.06 (15)	H11C—C11—H11D	109.5
C4—C2—C3	114.15 (14)	C9—C11—H11A	109.5
N2—C3—C7	105.64 (15)	H11C—C11—H11A	109.5
N2—C3—C6	110.44 (15)	H11D—C11—H11A	109.5