Bis[2,4-penta-nedionato(1-)]bis-[4,4,5,5-tetra-methyl--2-(4-pyrid-yl)-imidazoline-1-oxyl 3-oxide]manganese(II).

In the title compound, [Mn(C(5)H(7)O(2))(2)(C(12)H(16)N(3)O(2))], the manganese(II) cation (site symmetry ) is hexa-coordinated by four O and two N atoms in a distorted trans-MnN(2)O(4) octa-hedral geometry. The four O atoms belonging to two 2,4-penta-nedionate anions lie in the equatorial plane and the two N atoms occupy the axial coordination sites.

Related literature

For related structures, see: Caruso et al. (2005 ▶); Iskander et al. (2001 ▶); Rajak et al. (2000 ▶); Sangeetha et al. (2000 ▶); Sutradhar et al. (2006 ▶).

Experimental

Crystal data

[Mn(C5H7O2)2(C12H16N3O2)]

M = 721.71

Triclinic,

a = 7.277 (3) Å

b = 9.7167 (15) Å

c = 13.2643 (15) Å

α = 97.978 (10)°

β = 103.342 (10)°

γ = 92.869 (10)°

V = 900.4 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.42 mm−1

T = 293 (2) K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.951, T max = 0.970

6210 measured reflections

3264 independent reflections

2511 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.00

3264 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.58 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/S1600536808038440/hb2842sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038440/hb2842Isup2.hkl

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

[Mn(C5H7O2)2(C12H16N3O2)]	Z = 1
Mr = 721.71	F000 = 381
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.277 (3) Å	Cell parameters from 3264 reflections
b = 9.7167 (15) Å	θ = 2.9–25.5º
c = 13.2643 (15) Å	µ = 0.42 mm−1
α = 97.978 (10)º	T = 293 (2) K
β = 103.342 (10)º	Block, brown
γ = 92.869 (10)º	0.12 × 0.10 × 0.08 mm
V = 900.4 (4) Å3

Bruker APEXII CCD area-detector diffractometer	3264 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 293(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −6→8
Tmin = 0.951, Tmax = 0.970	k = −11→11
6210 measured reflections	l = −11→16

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.007
3264 reflections	Δρmax = 0.58 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
Mn1	0.0000	0.0000	0.0000	0.0236 (6)
C1	−0.0486 (4)	0.2828 (3)	0.0582 (2)	0.0237 (6)
C2	0.2048 (4)	0.2371 (3)	−0.0432 (2)	0.0249 (6)
C3	0.3726 (4)	0.2936 (3)	−0.0812 (2)	0.0343 (7)
H3A	0.4838	0.2496	−0.0522	0.052*
H3B	0.3946	0.3926	−0.0589	0.052*
H3C	0.3449	0.2741	−0.1564	0.052*
C4	0.1139 (4)	0.3210 (3)	0.0232 (2)	0.0264 (6)
H4	0.1672	0.4122	0.0467	0.032*
C5	−0.1320 (4)	0.3856 (3)	0.1294 (2)	0.0319 (7)
H5A	−0.2665	0.3830	0.1019	0.048*
H5B	−0.0754	0.4781	0.1327	0.048*
H5C	−0.1066	0.3607	0.1985	0.048*
C6	0.1703 (4)	0.1166 (3)	0.2387 (2)	0.0220 (6)
H6	0.0417	0.1238	0.2338	0.026*
C7	0.4138 (4)	0.0539 (3)	0.1578 (2)	0.0232 (6)
H7	0.4539	0.0187	0.0984	0.028*
C8	0.5526 (4)	0.0956 (3)	0.2535 (2)	0.0246 (6)
H8	0.6802	0.0871	0.2560	0.030*
C9	0.2971 (4)	0.1612 (3)	0.3371 (2)	0.0222 (6)
H9	0.2526	0.1967	0.3950	0.027*
C10	0.4944 (4)	0.1510 (3)	0.3461 (2)	0.0222 (6)
C11	0.6315 (4)	0.1986 (3)	0.4507 (2)	0.0222 (6)
C12	0.9181 (3)	0.2690 (3)	0.58642 (19)	0.0210 (6)
C13	0.7430 (4)	0.2984 (3)	0.6343 (2)	0.0232 (6)
C14	0.7504 (4)	0.2549 (3)	0.7443 (2)	0.0307 (7)
H14A	0.6361	0.2770	0.7652	0.046*
H14B	0.8576	0.3046	0.7948	0.046*
H14C	0.7620	0.1564	0.7404	0.046*
C15	0.6888 (4)	0.4434 (3)	0.6352 (2)	0.0328 (7)
H15A	0.6878	0.4715	0.5685	0.049*
H15B	0.7786	0.5045	0.6894	0.049*
H15C	0.5648	0.4483	0.6483	0.049*
C16	1.0020 (4)	0.1369 (3)	0.6128 (2)	0.0254 (6)
H16A	0.9033	0.0623	0.5969	0.038*
H16B	1.0634	0.1492	0.6861	0.038*
H16C	1.0930	0.1147	0.5722	0.038*
C17	1.0770 (4)	0.3830 (3)	0.6102 (2)	0.0260 (6)
H17A	1.1689	0.3565	0.5711	0.039*
H17B	1.1363	0.3975	0.6838	0.039*
H17C	1.0271	0.4677	0.5908	0.039*
N1	0.2243 (3)	0.0629 (2)	0.14911 (16)	0.0214 (5)
N2	0.5856 (3)	0.2134 (2)	0.54863 (17)	0.0250 (5)
N3	0.8188 (3)	0.2417 (2)	0.46660 (17)	0.0221 (5)
O1	−0.1368 (2)	0.16513 (17)	0.03794 (14)	0.0254 (4)
O2	0.9120 (3)	0.25072 (19)	0.39302 (14)	0.0277 (4)
O3	0.1567 (2)	0.11183 (18)	−0.07693 (14)	0.0259 (4)
O4	0.4265 (3)	0.1723 (2)	0.56899 (15)	0.0351 (5)

	U11	U22	U33	U12	U13	U23
Mn1	0.0270 (15)	0.0192 (14)	0.0214 (15)	0.0067 (11)	0.0002 (11)	0.0001 (11)
C1	0.0267 (14)	0.0198 (13)	0.0197 (14)	0.0041 (10)	−0.0057 (11)	0.0045 (10)
C2	0.0244 (14)	0.0214 (13)	0.0246 (15)	0.0003 (10)	−0.0055 (11)	0.0087 (11)
C3	0.0301 (16)	0.0276 (15)	0.0445 (19)	−0.0007 (12)	0.0041 (14)	0.0122 (13)
C4	0.0316 (15)	0.0180 (13)	0.0256 (15)	0.0005 (11)	−0.0013 (12)	0.0040 (11)
C5	0.0373 (17)	0.0220 (14)	0.0327 (17)	0.0074 (12)	0.0012 (13)	0.0017 (12)
C6	0.0193 (13)	0.0234 (13)	0.0245 (15)	0.0035 (10)	0.0056 (11)	0.0061 (11)
C7	0.0246 (14)	0.0242 (13)	0.0212 (15)	0.0045 (10)	0.0052 (11)	0.0045 (11)
C8	0.0208 (14)	0.0270 (14)	0.0258 (16)	0.0026 (10)	0.0051 (11)	0.0044 (11)
C9	0.0238 (14)	0.0234 (13)	0.0199 (14)	0.0033 (10)	0.0055 (11)	0.0038 (10)
C10	0.0233 (14)	0.0217 (13)	0.0209 (15)	0.0006 (10)	0.0035 (11)	0.0045 (10)
C11	0.0230 (14)	0.0260 (13)	0.0178 (14)	0.0022 (10)	0.0051 (11)	0.0030 (11)
C12	0.0201 (13)	0.0256 (14)	0.0151 (14)	0.0009 (10)	0.0007 (10)	0.0026 (10)
C13	0.0224 (14)	0.0268 (14)	0.0185 (14)	0.0038 (11)	0.0009 (11)	0.0029 (11)
C14	0.0270 (15)	0.0405 (17)	0.0236 (16)	0.0033 (12)	0.0035 (12)	0.0060 (12)
C15	0.0292 (16)	0.0346 (16)	0.0330 (18)	0.0106 (12)	0.0046 (13)	0.0017 (13)
C16	0.0225 (14)	0.0250 (14)	0.0284 (16)	0.0034 (10)	0.0040 (12)	0.0058 (11)
C17	0.0254 (14)	0.0254 (14)	0.0254 (16)	0.0013 (11)	0.0031 (12)	0.0034 (11)
N1	0.0236 (12)	0.0185 (11)	0.0221 (13)	0.0025 (8)	0.0051 (10)	0.0039 (9)
N2	0.0175 (12)	0.0340 (13)	0.0225 (13)	0.0003 (9)	0.0038 (9)	0.0040 (10)
N3	0.0192 (11)	0.0260 (11)	0.0206 (12)	0.0014 (9)	0.0038 (10)	0.0041 (9)
O1	0.0261 (10)	0.0207 (9)	0.0268 (11)	0.0038 (7)	0.0006 (8)	0.0039 (8)
O2	0.0235 (10)	0.0367 (11)	0.0239 (11)	0.0013 (8)	0.0087 (8)	0.0033 (8)
O3	0.0280 (10)	0.0210 (9)	0.0258 (11)	−0.0002 (7)	0.0011 (8)	0.0031 (8)
O4	0.0205 (10)	0.0555 (14)	0.0309 (12)	−0.0011 (9)	0.0076 (9)	0.0113 (10)

Mn1—O1i	1.9964 (17)	C9—C10	1.422 (4)
Mn1—O1	1.9964 (17)	C9—H9	0.9300
Mn1—O3	2.0597 (17)	C10—C11	1.508 (4)
Mn1—O3i	2.0597 (17)	C11—N3	1.365 (3)
Mn1—N1	2.242 (2)	C11—N2	1.405 (3)
Mn1—N1i	2.242 (2)	C12—C16	1.498 (3)
C1—O1	1.246 (3)	C12—C17	1.507 (3)
C1—C4	1.417 (4)	C12—N3	1.566 (3)
C1—C5	1.524 (4)	C12—C13	1.571 (4)
C2—O3	1.241 (3)	C13—C15	1.482 (4)
C2—C4	1.415 (4)	C13—N2	1.527 (3)
C2—C3	1.530 (4)	C13—C14	1.564 (4)
C3—H3A	0.9600	C14—H14A	0.9600
C3—H3B	0.9600	C14—H14B	0.9600
C3—H3C	0.9600	C14—H14C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C5—H5A	0.9600	C15—H15B	0.9600
C5—H5B	0.9600	C15—H15C	0.9600
C5—H5C	0.9600	C16—H16A	0.9600
C6—N1	1.379 (3)	C16—H16B	0.9600
C6—C9	1.412 (4)	C16—H16C	0.9600
C6—H6	0.9300	C17—H17A	0.9600
C7—N1	1.364 (3)	C17—H17B	0.9600
C7—C8	1.421 (4)	C17—H17C	0.9600
C7—H7	0.9300	N2—O4	1.304 (3)
C8—C10	1.434 (4)	N3—O2	1.320 (3)
C8—H8	0.9300
O1i—Mn1—O1	180.0	N3—C11—N2	108.1 (2)
O1i—Mn1—O3	87.80 (7)	N3—C11—C10	126.2 (2)
O1—Mn1—O3	92.20 (7)	N2—C11—C10	125.6 (2)
O1i—Mn1—O3i	92.20 (7)	C16—C12—C17	108.1 (2)
O1—Mn1—O3i	87.80 (7)	C16—C12—N3	106.9 (2)
O3—Mn1—O3i	180.0	C17—C12—N3	110.9 (2)
O1i—Mn1—N1	90.40 (7)	C16—C12—C13	112.5 (2)
O1—Mn1—N1	89.60 (7)	C17—C12—C13	117.4 (2)
O3—Mn1—N1	89.56 (7)	N3—C12—C13	100.45 (18)
O3i—Mn1—N1	90.44 (7)	C15—C13—N2	103.7 (2)
O1i—Mn1—N1i	89.60 (7)	C15—C13—C14	109.2 (2)
O1—Mn1—N1i	90.40 (7)	N2—C13—C14	112.0 (2)
O3—Mn1—N1i	90.44 (7)	C15—C13—C12	114.0 (2)
O3i—Mn1—N1i	89.56 (7)	N2—C13—C12	100.01 (19)
N1—Mn1—N1i	180.0	C14—C13—C12	116.9 (2)
O1—C1—C4	125.9 (2)	C13—C14—H14A	109.5
O1—C1—C5	112.3 (2)	C13—C14—H14B	109.5
C4—C1—C5	121.8 (2)	H14A—C14—H14B	109.5
O3—C2—C4	123.9 (2)	C13—C14—H14C	109.5
O3—C2—C3	113.3 (2)	H14A—C14—H14C	109.5
C4—C2—C3	122.8 (2)	H14B—C14—H14C	109.5
C2—C3—H3A	109.5	C13—C15—H15A	109.5
C2—C3—H3B	109.5	C13—C15—H15B	109.5
H3A—C3—H3B	109.5	H15A—C15—H15B	109.5
C2—C3—H3C	109.5	C13—C15—H15C	109.5
H3A—C3—H3C	109.5	H15A—C15—H15C	109.5
H3B—C3—H3C	109.5	H15B—C15—H15C	109.5
C2—C4—C1	127.8 (2)	C12—C16—H16A	109.5
C2—C4—H4	116.1	C12—C16—H16B	109.5
C1—C4—H4	116.1	H16A—C16—H16B	109.5
C1—C5—H5A	109.5	C12—C16—H16C	109.5
C1—C5—H5B	109.5	H16A—C16—H16C	109.5
H5A—C5—H5B	109.5	H16B—C16—H16C	109.5
C1—C5—H5C	109.5	C12—C17—H17A	109.5
H5A—C5—H5C	109.5	C12—C17—H17B	109.5
H5B—C5—H5C	109.5	H17A—C17—H17B	109.5
N1—C6—C9	124.4 (2)	C12—C17—H17C	109.5
N1—C6—H6	117.8	H17A—C17—H17C	109.5
C9—C6—H6	117.8	H17B—C17—H17C	109.5
N1—C7—C8	123.1 (2)	C7—N1—C6	116.8 (2)
N1—C7—H7	118.5	C7—N1—Mn1	124.50 (17)
C8—C7—H7	118.5	C6—N1—Mn1	118.67 (16)
C7—C8—C10	119.5 (2)	O4—N2—C11	127.6 (2)
C7—C8—H8	120.2	O4—N2—C13	120.6 (2)
C10—C8—H8	120.2	C11—N2—C13	111.6 (2)
C6—C9—C10	118.6 (2)	O2—N3—C11	126.1 (2)
C6—C9—H9	120.7	O2—N3—C12	122.78 (18)
C10—C9—H9	120.7	C11—N3—C12	110.91 (19)
C9—C10—C8	117.6 (2)	C1—O1—Mn1	118.40 (17)
C9—C10—C11	119.2 (2)	C2—O3—Mn1	119.22 (17)
C8—C10—C11	123.2 (2)

Table 1

Selected bond lengths (Å)

Mn1—O1	1.9964 (17)
Mn1—O3	2.0597 (17)
Mn1—N1	2.242 (2)