Di­thio­cyanatobis­[4,4,5,5-tetra­methyl-2-(4-pyridyl-[kappa]N)-1H-imidazoline-1-oxyl]­zinc(II)

In the title compound, [Zn(NCS)₂(C₁₂H₁₆N₃O)₂], the Zn^II ion has a distorted tetrahedral coordination. It is bonded to two thio­cyanate and two pyridyl N atoms. The metal ion and the two thio­cyanate ligands lie on a mirror plane with the Zn-N_py and average Zn-N_NCS bond distances being 2.036 (2) and 1.931 (4) Å, respectively

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Bis(2-(4-pyridyl)-4,4,5,5- tetramethylimidazoline-1-oxyl)Zinc(II) dithiocyanate.

Crystal data

[Zn(C12H16N3O)2(NCS)2]	F(000) = 644
Mr = 618.09	Dx = 1.383 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 6.1103 (2) Å	Cell parameters from 12252 reflections
b = 20.699 (1) Å	θ = 1.0–27.9°
c = 11.7877 (5) Å	µ = 1.01 mm^−1
β = 95.302 (3)°	T = 293 K
V = 1484.50 (11) Å^3	Prism, orange
Z = 2	0.12 × 0.05 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer	2469 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 27.9°, θmin = 1.7°
φ and ω scans	h = −8→8
13554 measured reflections	k = −23→27
3614 independent reflections	l = −14→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters not refined
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 0.2948P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3614 reflections	Δρmax = 0.23 e Å^−3
199 parameters	Δρmin = −0.35 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0098 (15)

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	Occ. (<1)
Zn	0.37830 (6)	0.2500	0.24657 (4)	0.04977 (17)
S1	0.8360 (2)	0.2500	0.58850 (10)	0.0763 (3)
S2	0.87002 (18)	0.2500	−0.03294 (10)	0.0718 (3)
O1	−0.1486 (4)	0.54916 (12)	0.09311 (18)	0.0668 (7)	0.848 (3)
O1'	−0.503 (2)	0.4513 (6)	0.3517 (11)	0.069 (4)	0.152 (3)
N1	0.5387 (6)	0.2500	0.3965 (3)	0.0656 (9)
N2	0.5555 (6)	0.2500	0.1203 (3)	0.0709 (9)
N3	0.1723 (3)	0.32744 (10)	0.24257 (16)	0.0460 (5)
N4	−0.2534 (3)	0.54195 (10)	0.17640 (16)	0.0491 (5)
N5	−0.3909 (4)	0.49661 (11)	0.32605 (19)	0.0602 (6)
C1	0.6628 (6)	0.2500	0.4774 (3)	0.0522 (8)
C2	0.6876 (6)	0.2500	0.0565 (3)	0.0519 (8)
C3	0.0542 (4)	0.33986 (13)	0.3306 (2)	0.0558 (6)
H3	0.0712	0.3127	0.3936	0.067*
C4	−0.0898 (4)	0.39033 (13)	0.3324 (2)	0.0556 (6)
H4	−0.1703	0.3965	0.3947	0.067*
C5	−0.1145 (3)	0.43227 (11)	0.24017 (18)	0.0422 (5)
C6	0.0033 (4)	0.41927 (13)	0.1484 (2)	0.0508 (6)
H6	−0.0113	0.4456	0.0842	0.061*
C7	0.1430 (4)	0.36680 (12)	0.1531 (2)	0.0521 (6)
H7	0.2207	0.3585	0.0905	0.062*
C8	−0.2567 (3)	0.48945 (11)	0.2472 (2)	0.0450 (5)
C9	−0.4264 (4)	0.58903 (12)	0.2024 (2)	0.0525 (6)
C10	−0.4780 (4)	0.56359 (13)	0.3210 (2)	0.0531 (6)
C11	−0.6128 (5)	0.57937 (18)	0.1075 (3)	0.0807 (9)
H11A	−0.6679	0.5360	0.1105	0.121*
H11B	−0.5579	0.5867	0.0348	0.121*
H11C	−0.7292	0.6094	0.1176	0.121*
C12	−0.3382 (5)	0.65732 (14)	0.1980 (3)	0.0758 (9)
H12A	−0.3119	0.6677	0.1211	0.114*
H12B	−0.2031	0.6605	0.2462	0.114*
H12C	−0.4437	0.6869	0.2240	0.114*
C13	−0.3517 (5)	0.59922 (16)	0.4198 (2)	0.0707 (8)
H13A	−0.1986	0.6008	0.4076	0.106*
H13B	−0.3693	0.5769	0.4897	0.106*
H13C	−0.4077	0.6424	0.4242	0.106*
C14	−0.7202 (4)	0.56226 (16)	0.3416 (3)	0.0760 (9)
H14A	−0.7356	0.5461	0.4168	0.114*
H14B	−0.7984	0.5346	0.2864	0.114*
H14C	−0.7794	0.6052	0.3346	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0491 (2)	0.0412 (2)	0.0600 (3)	0.000	0.01041 (18)	0.000
S1	0.0858 (7)	0.0726 (8)	0.0669 (7)	0.000	−0.0122 (6)	0.000
S2	0.0629 (6)	0.0732 (7)	0.0829 (8)	0.000	0.0248 (5)	0.000
O1	0.0751 (15)	0.0643 (15)	0.0658 (14)	0.0148 (11)	0.0320 (12)	0.0198 (11)
O1'	0.071 (8)	0.054 (8)	0.088 (9)	0.002 (6)	0.039 (7)	0.021 (7)
N1	0.0636 (19)	0.061 (2)	0.071 (2)	0.000	−0.0005 (17)	0.000
N2	0.067 (2)	0.075 (3)	0.074 (2)	0.000	0.0219 (18)	0.000
N3	0.0516 (11)	0.0403 (11)	0.0466 (11)	−0.0021 (8)	0.0066 (9)	−0.0012 (9)
N4	0.0509 (11)	0.0476 (12)	0.0487 (11)	−0.0023 (9)	0.0038 (9)	0.0073 (9)
N5	0.0632 (13)	0.0483 (13)	0.0733 (15)	0.0081 (10)	0.0288 (11)	0.0059 (11)
C1	0.056 (2)	0.044 (2)	0.058 (2)	0.000	0.0122 (17)	0.000
C2	0.0523 (19)	0.043 (2)	0.061 (2)	0.000	0.0049 (17)	0.000
C3	0.0731 (16)	0.0462 (15)	0.0496 (14)	0.0098 (12)	0.0140 (12)	0.0105 (11)
C4	0.0679 (16)	0.0483 (15)	0.0533 (15)	0.0083 (12)	0.0208 (12)	0.0087 (12)
C5	0.0427 (11)	0.0394 (12)	0.0445 (12)	−0.0031 (9)	0.0046 (9)	0.0003 (10)
C6	0.0610 (15)	0.0484 (15)	0.0440 (13)	0.0047 (11)	0.0109 (11)	0.0054 (11)
C7	0.0622 (15)	0.0463 (14)	0.0500 (14)	0.0028 (11)	0.0174 (11)	−0.0006 (11)
C8	0.0419 (12)	0.0390 (13)	0.0538 (14)	−0.0015 (9)	0.0031 (10)	0.0017 (10)
C9	0.0451 (12)	0.0414 (14)	0.0692 (16)	0.0026 (10)	−0.0041 (11)	0.0050 (12)
C10	0.0445 (12)	0.0473 (14)	0.0684 (16)	0.0034 (10)	0.0110 (11)	−0.0030 (12)
C11	0.0685 (18)	0.083 (2)	0.085 (2)	0.0015 (16)	−0.0203 (16)	0.0129 (18)
C12	0.089 (2)	0.0431 (16)	0.096 (2)	−0.0062 (14)	0.0072 (18)	0.0054 (15)
C13	0.0689 (18)	0.075 (2)	0.0673 (19)	0.0064 (15)	0.0028 (14)	−0.0097 (15)
C14	0.0515 (15)	0.074 (2)	0.105 (2)	0.0016 (14)	0.0234 (16)	−0.0111 (18)

Geometric parameters (Å, º)

Zn—N2	1.919 (3)	C5—C8	1.475 (3)
Zn—N1	1.940 (4)	C6—C7	1.379 (3)
Zn—N3^i	2.036 (2)	C6—H6	0.9300
Zn—N3	2.036 (2)	C7—H7	0.9300
S1—C1	1.605 (4)	C9—C12	1.515 (4)
S2—C2	1.603 (4)	C9—C11	1.534 (4)
O1—N4	1.230 (3)	C9—C10	1.553 (4)
O1'—N5	1.216 (12)	C10—C14	1.522 (3)
N1—C1	1.163 (5)	C10—C13	1.526 (4)
N2—C2	1.153 (5)	C11—H11A	0.9600
N3—C7	1.332 (3)	C11—H11B	0.9600
N3—C3	1.342 (3)	C11—H11C	0.9600
N4—C8	1.372 (3)	C12—H12A	0.9600
N4—C9	1.491 (3)	C12—H12B	0.9600
N5—C8	1.303 (3)	C12—H12C	0.9600
N5—C10	1.484 (3)	C13—H13A	0.9600
C3—C4	1.367 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.389 (3)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.380 (3)	C14—H14C	0.9600
N2—Zn—N1	115.64 (15)	N4—C9—C12	110.0 (2)
N2—Zn—N3^i	111.95 (8)	N4—C9—C11	104.9 (2)
N1—Zn—N3^i	106.27 (8)	C12—C9—C11	109.8 (2)
N2—Zn—N3	111.95 (8)	N4—C9—C10	99.81 (18)
N1—Zn—N3	106.27 (8)	C12—C9—C10	116.7 (2)
N3^i—Zn—N3	103.87 (11)	C11—C9—C10	114.4 (2)
C1—N1—Zn	169.7 (3)	N5—C10—C14	109.1 (2)
C2—N2—Zn	170.0 (3)	N5—C10—C13	105.5 (2)
C7—N3—C3	116.9 (2)	C14—C10—C13	108.5 (2)
C7—N3—Zn	122.52 (15)	N5—C10—C9	104.53 (19)
C3—N3—Zn	120.54 (16)	C14—C10—C9	115.5 (2)
O1—N4—C8	128.3 (2)	C13—C10—C9	113.1 (2)
O1—N4—C9	121.1 (2)	C9—C11—H11A	109.5
C8—N4—C9	110.02 (19)	C9—C11—H11B	109.5
O1'—N5—C8	119.7 (7)	H11A—C11—H11B	109.5
O1'—N5—C10	121.4 (6)	C9—C11—H11C	109.5
C8—N5—C10	108.9 (2)	H11A—C11—H11C	109.5
N1—C1—S1	179.5 (3)	H11B—C11—H11C	109.5
N2—C2—S2	179.6 (4)	C9—C12—H12A	109.5
N3—C3—C4	123.4 (2)	C9—C12—H12B	109.5
N3—C3—H3	118.3	H12A—C12—H12B	109.5
C4—C3—H3	118.3	C9—C12—H12C	109.5
C3—C4—C5	119.3 (2)	H12A—C12—H12C	109.5
C3—C4—H4	120.4	H12B—C12—H12C	109.5
C5—C4—H4	120.4	C10—C13—H13A	109.5
C6—C5—C4	117.7 (2)	C10—C13—H13B	109.5
C6—C5—C8	123.6 (2)	H13A—C13—H13B	109.5
C4—C5—C8	118.7 (2)	C10—C13—H13C	109.5
C7—C6—C5	119.2 (2)	H13A—C13—H13C	109.5
C7—C6—H6	120.4	H13B—C13—H13C	109.5
C5—C6—H6	120.4	C10—C14—H14A	109.5
N3—C7—C6	123.4 (2)	C10—C14—H14B	109.5
N3—C7—H7	118.3	H14A—C14—H14B	109.5
C6—C7—H7	118.3	C10—C14—H14C	109.5
N5—C8—N4	112.9 (2)	H14A—C14—H14C	109.5
N5—C8—C5	123.0 (2)	H14B—C14—H14C	109.5
N4—C8—C5	124.0 (2)
N2—Zn—N1—C1	0.000 (5)	C9—N4—C8—N5	−6.8 (3)
N3^i—Zn—N1—C1	124.90 (6)	O1—N4—C8—C5	5.4 (4)
N3—Zn—N1—C1	−124.90 (6)	C9—N4—C8—C5	176.7 (2)
N1—Zn—N2—C2	0.000 (1)	C6—C5—C8—N5	169.9 (2)
N3^i—Zn—N2—C2	−121.91 (7)	C4—C5—C8—N5	−12.8 (3)
N3—Zn—N2—C2	121.91 (7)	C6—C5—C8—N4	−13.9 (4)
N2—Zn—N3—C7	9.7 (2)	C4—C5—C8—N4	163.4 (2)
N1—Zn—N3—C7	136.9 (2)	O1—N4—C9—C12	−48.8 (3)
N3^i—Zn—N3—C7	−111.25 (19)	C8—N4—C9—C12	139.2 (2)
N2—Zn—N3—C3	−172.2 (2)	O1—N4—C9—C11	69.2 (3)
N1—Zn—N3—C3	−45.0 (2)	C8—N4—C9—C11	−102.8 (2)
N3^i—Zn—N3—C3	66.9 (2)	O1—N4—C9—C10	−172.0 (2)
Zn—N1—C1—S1	0.00 (9)	C8—N4—C9—C10	15.9 (2)
Zn—N2—C2—S2	180.00 (3)	O1'—N5—C10—C14	−4.9 (8)
C7—N3—C3—C4	−0.6 (4)	C8—N5—C10—C14	140.6 (2)
Zn—N3—C3—C4	−178.8 (2)	O1'—N5—C10—C13	111.5 (8)
N3—C3—C4—C5	−1.3 (4)	C8—N5—C10—C13	−103.0 (2)
C3—C4—C5—C6	2.4 (4)	O1'—N5—C10—C9	−129.0 (8)
C3—C4—C5—C8	−175.1 (2)	C8—N5—C10—C9	16.5 (3)
C4—C5—C6—C7	−1.6 (4)	N4—C9—C10—N5	−18.6 (2)
C8—C5—C6—C7	175.8 (2)	C12—C9—C10—N5	−137.0 (2)
C3—N3—C7—C6	1.4 (4)	C11—C9—C10—N5	92.8 (3)
Zn—N3—C7—C6	179.61 (19)	N4—C9—C10—C14	−138.5 (2)
C5—C6—C7—N3	−0.3 (4)	C12—C9—C10—C14	103.1 (3)
O1'—N5—C8—N4	139.6 (8)	C11—C9—C10—C14	−27.1 (3)
C10—N5—C8—N4	−6.6 (3)	N4—C9—C10—C13	95.5 (2)
O1'—N5—C8—C5	−43.9 (8)	C12—C9—C10—C13	−22.8 (3)
C10—N5—C8—C5	170.0 (2)	C11—C9—C10—C13	−153.0 (2)
O1—N4—C8—N5	−178.1 (2)

Symmetry code: (i) x, −y+1/2, z.