{N,N'-Bis[1-(2-pyrid-yl)ethyl-idene]propane-1,2-diamine-κN,N',N'',N'''}bis-(thio-cyanato-κN)manganese(II).

In the title compound, [Mn(NCS)(2)(C(17)H(20)N(4))], the Mn(II) atom is six-coordinated by the N,N',N'',N'''-tetra-dentate Schiff base ligand and by two trans-N atoms from two thio-cyanate anions, forming a distorted octa-hedral geometry. The dihedral angle between the aromatic rings of the Schiff base is 9.5 (3)°.

Related literature

For another complex containing 1,2-bis­(2′-pyridyl­methyl­ene­amino)­propane, see: Ouyang et al. (2002 ▶). For related manganese(II) complexes with Schiff bases, see: Louloudi et al. (1999 ▶); Sra et al. (2000 ▶); Karmakar et al. (2005 ▶); Deoghoria et al. (2005 ▶). For the synthesis of the Schiff base, see: Gourbatsis et al. (1990 ▶).

Experimental

Crystal data

[Mn(NCS)2(C17H20N4)]

M = 451.47

Triclinic,

a = 8.647 (3) Å

b = 9.135 (2) Å

c = 14.608 (3) Å

α = 84.701 (3)°

β = 79.407 (3)°

γ = 70.509 (3)°

V = 1068.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 298 K

0.33 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.771, T max = 0.789

11100 measured reflections

4608 independent reflections

2211 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.224

S = 0.99

4608 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021549/hb5486sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021549/hb5486Isup2.hkl

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

[Mn(NCS)2(C17H20N4)]	Z = 2
Mr = 451.47	F(000) = 466
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.647 (3) Å	Cell parameters from 1307 reflections
b = 9.135 (2) Å	θ = 2.3–24.5°
c = 14.608 (3) Å	µ = 0.83 mm−1
α = 84.701 (3)°	T = 298 K
β = 79.407 (3)°	Block, brown
γ = 70.509 (3)°	0.33 × 0.30 × 0.30 mm
V = 1068.6 (5) Å3

Bruker SMART CCD diffractometer	4608 independent reflections
Radiation source: fine-focus sealed tube	2211 reflections with I > 2σ(I)
graphite	Rint = 0.078
ω scan	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.771, Tmax = 0.789	k = −11→11
11100 measured reflections	l = −18→18

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1044P)2] where P = (Fo2 + 2Fc2)/3
4608 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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	1.02210 (10)	0.54382 (9)	0.27241 (5)	0.0601 (3)
N1	1.2061 (6)	0.6565 (5)	0.3134 (3)	0.0644 (12)
N2	1.0220 (6)	0.7580 (5)	0.1819 (3)	0.0673 (12)
N3	0.8157 (6)	0.5912 (5)	0.1875 (3)	0.0701 (13)
N4	0.9013 (5)	0.3471 (5)	0.3008 (3)	0.0665 (12)
N5	0.8737 (7)	0.6394 (7)	0.3994 (4)	0.0906 (17)
N6	1.2282 (6)	0.3744 (6)	0.1940 (4)	0.0772 (15)
S1	0.6757 (2)	0.8093 (2)	0.54416 (16)	0.1097 (7)
S2	1.4735 (2)	0.1575 (2)	0.08162 (12)	0.0855 (5)
C1	1.2937 (8)	0.6060 (8)	0.3826 (5)	0.089 (2)
H1	1.2883	0.5148	0.4151	0.107*
C2	1.3917 (9)	0.6811 (8)	0.4088 (5)	0.096 (2)
H2	1.4508	0.6422	0.4578	0.116*
C3	1.3997 (8)	0.8144 (8)	0.3608 (5)	0.088 (2)
H3	1.4654	0.8677	0.3765	0.106*
C4	1.3109 (7)	0.8693 (6)	0.2897 (5)	0.0750 (17)
H4	1.3155	0.9601	0.2565	0.090*
C5	1.2135 (6)	0.7880 (6)	0.2674 (4)	0.0574 (13)
C6	1.1124 (7)	0.8394 (7)	0.1905 (4)	0.0631 (14)
C7	1.1270 (9)	0.9785 (7)	0.1307 (5)	0.095 (2)
H7A	1.2372	0.9548	0.0956	0.142*
H7B	1.1054	1.0646	0.1696	0.142*
H7C	1.0477	1.0050	0.0888	0.142*
C8	0.9234 (8)	0.7889 (8)	0.1062 (4)	0.087 (2)
H8	0.8913	0.8996	0.0880	0.104*
C9	1.0322 (10)	0.6917 (9)	0.0230 (5)	0.106 (2)
H9A	1.1312	0.7198	0.0042	0.159*
H9B	0.9712	0.7114	−0.0281	0.159*
H9C	1.0619	0.5833	0.0409	0.159*
C10	0.7743 (8)	0.7434 (8)	0.1372 (5)	0.098 (2)
H10A	0.7250	0.7379	0.0837	0.118*
H10B	0.6935	0.8213	0.1779	0.118*
C11	0.7315 (7)	0.4988 (6)	0.1900 (4)	0.0617 (14)
C12	0.5892 (7)	0.5241 (7)	0.1393 (5)	0.0843 (19)
H12A	0.5809	0.6123	0.0970	0.126*
H12B	0.4880	0.5428	0.1833	0.126*
H12C	0.6072	0.4335	0.1050	0.126*
C13	0.7763 (6)	0.3606 (6)	0.2541 (4)	0.0613 (14)
C14	0.6956 (7)	0.2485 (8)	0.2671 (5)	0.0826 (18)
H14	0.6105	0.2573	0.2340	0.099*
C15	0.7432 (8)	0.1242 (8)	0.3297 (5)	0.094 (2)
H15	0.6899	0.0495	0.3389	0.112*
C16	0.8672 (9)	0.1124 (8)	0.3771 (5)	0.094 (2)
H16	0.9006	0.0303	0.4195	0.112*
C17	0.9429 (8)	0.2251 (7)	0.3610 (4)	0.0808 (18)
H17	1.0283	0.2165	0.3937	0.097*
C18	0.7938 (7)	0.7096 (6)	0.4577 (4)	0.0589 (14)
C19	1.3320 (7)	0.2828 (7)	0.1471 (4)	0.0631 (15)

	U11	U22	U33	U12	U13	U23
Mn1	0.0670 (6)	0.0649 (6)	0.0607 (5)	−0.0367 (5)	−0.0173 (4)	0.0090 (4)
N1	0.082 (3)	0.060 (3)	0.064 (3)	−0.036 (2)	−0.024 (2)	0.011 (2)
N2	0.078 (3)	0.075 (3)	0.066 (3)	−0.041 (3)	−0.030 (2)	0.012 (2)
N3	0.075 (3)	0.072 (3)	0.077 (3)	−0.039 (3)	−0.026 (3)	0.017 (3)
N4	0.063 (3)	0.077 (3)	0.071 (3)	−0.036 (2)	−0.018 (2)	0.009 (3)
N5	0.089 (4)	0.110 (5)	0.082 (4)	−0.051 (4)	−0.001 (3)	−0.006 (3)
N6	0.079 (4)	0.077 (4)	0.086 (4)	−0.040 (3)	−0.016 (3)	0.003 (3)
S1	0.0955 (14)	0.1071 (16)	0.1234 (16)	−0.0214 (12)	−0.0135 (12)	−0.0410 (13)
S2	0.0850 (12)	0.0822 (12)	0.0928 (12)	−0.0285 (10)	−0.0153 (9)	−0.0139 (9)
C1	0.116 (5)	0.088 (5)	0.091 (5)	−0.060 (4)	−0.049 (4)	0.026 (4)
C2	0.114 (5)	0.099 (5)	0.102 (5)	−0.051 (5)	−0.063 (4)	0.019 (4)
C3	0.096 (5)	0.078 (5)	0.115 (5)	−0.047 (4)	−0.047 (4)	0.001 (4)
C4	0.080 (4)	0.052 (3)	0.103 (5)	−0.029 (3)	−0.030 (4)	0.003 (3)
C5	0.055 (3)	0.060 (3)	0.062 (3)	−0.025 (3)	−0.010 (3)	−0.006 (3)
C6	0.065 (3)	0.067 (4)	0.064 (3)	−0.030 (3)	−0.015 (3)	0.008 (3)
C7	0.121 (6)	0.080 (5)	0.103 (5)	−0.061 (4)	−0.037 (4)	0.039 (4)
C8	0.113 (5)	0.080 (5)	0.085 (4)	−0.049 (4)	−0.042 (4)	0.027 (4)
C9	0.143 (7)	0.102 (6)	0.083 (5)	−0.051 (5)	−0.026 (5)	0.003 (4)
C10	0.108 (5)	0.110 (6)	0.110 (5)	−0.070 (5)	−0.060 (4)	0.042 (4)
C11	0.057 (3)	0.059 (3)	0.075 (4)	−0.026 (3)	−0.011 (3)	−0.005 (3)
C12	0.065 (4)	0.088 (5)	0.112 (5)	−0.032 (3)	−0.037 (4)	0.006 (4)
C13	0.056 (3)	0.064 (4)	0.069 (3)	−0.032 (3)	0.002 (3)	−0.004 (3)
C14	0.067 (4)	0.086 (5)	0.113 (5)	−0.046 (4)	−0.021 (4)	0.000 (4)
C15	0.094 (5)	0.090 (5)	0.113 (6)	−0.059 (4)	−0.015 (4)	0.022 (4)
C16	0.099 (5)	0.089 (5)	0.106 (5)	−0.054 (4)	−0.022 (4)	0.034 (4)
C17	0.087 (4)	0.086 (5)	0.088 (4)	−0.047 (4)	−0.034 (4)	0.022 (4)
C18	0.057 (4)	0.052 (4)	0.075 (4)	−0.026 (3)	−0.022 (3)	0.013 (3)
C19	0.063 (4)	0.061 (4)	0.075 (4)	−0.030 (3)	−0.024 (3)	0.013 (3)

Mn1—N5	2.127 (6)	C5—C6	1.495 (7)
Mn1—N6	2.149 (6)	C6—C7	1.501 (8)
Mn1—N2	2.258 (5)	C7—H7A	0.9600
Mn1—N3	2.260 (4)	C7—H7B	0.9600
Mn1—N4	2.334 (4)	C7—H7C	0.9600
Mn1—N1	2.346 (4)	C8—C10	1.465 (8)
N1—C1	1.331 (7)	C8—C9	1.540 (9)
N1—C5	1.336 (6)	C8—H8	0.9800
N2—C6	1.274 (6)	C9—H9A	0.9600
N2—C8	1.470 (7)	C9—H9B	0.9600
N3—C11	1.281 (6)	C9—H9C	0.9600
N3—C10	1.476 (7)	C10—H10A	0.9700
N4—C17	1.345 (7)	C10—H10B	0.9700
N4—C13	1.348 (6)	C11—C13	1.486 (8)
N5—C18	1.097 (7)	C11—C12	1.493 (7)
N6—C19	1.164 (7)	C12—H12A	0.9600
S1—C18	1.608 (7)	C12—H12B	0.9600
S2—C19	1.600 (7)	C12—H12C	0.9600
C1—C2	1.376 (8)	C13—C14	1.402 (7)
C1—H1	0.9300	C14—C15	1.389 (8)
C2—C3	1.364 (9)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.351 (8)
C3—C4	1.364 (8)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.376 (8)
C4—C5	1.389 (7)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
N5—Mn1—N6	152.6 (2)	H7A—C7—H7B	109.5
N5—Mn1—N2	102.5 (2)	C6—C7—H7C	109.5
N6—Mn1—N2	99.53 (18)	H7A—C7—H7C	109.5
N5—Mn1—N3	98.1 (2)	H7B—C7—H7C	109.5
N6—Mn1—N3	103.71 (18)	C10—C8—N2	109.6 (5)
N2—Mn1—N3	73.15 (16)	C10—C8—C9	109.9 (6)
N5—Mn1—N4	86.78 (19)	N2—C8—C9	107.8 (5)
N6—Mn1—N4	85.41 (17)	C10—C8—H8	109.8
N2—Mn1—N4	142.80 (16)	N2—C8—H8	109.8
N3—Mn1—N4	69.88 (16)	C9—C8—H8	109.8
N5—Mn1—N1	82.92 (18)	C8—C9—H9A	109.5
N6—Mn1—N1	89.82 (17)	C8—C9—H9B	109.5
N2—Mn1—N1	69.50 (15)	H9A—C9—H9B	109.5
N3—Mn1—N1	141.88 (17)	C8—C9—H9C	109.5
N4—Mn1—N1	147.69 (16)	H9A—C9—H9C	109.5
C1—N1—C5	117.9 (5)	H9B—C9—H9C	109.5
C1—N1—Mn1	125.2 (4)	C8—C10—N3	110.8 (5)
C5—N1—Mn1	116.7 (3)	C8—C10—H10A	109.5
C6—N2—C8	121.8 (5)	N3—C10—H10A	109.5
C6—N2—Mn1	122.4 (4)	C8—C10—H10B	109.5
C8—N2—Mn1	115.5 (3)	N3—C10—H10B	109.5
C11—N3—C10	122.6 (5)	H10A—C10—H10B	108.1
C11—N3—Mn1	122.1 (4)	N3—C11—C13	115.4 (5)
C10—N3—Mn1	114.9 (3)	N3—C11—C12	125.6 (5)
C17—N4—C13	117.9 (5)	C13—C11—C12	118.9 (5)
C17—N4—Mn1	125.7 (4)	C11—C12—H12A	109.5
C13—N4—Mn1	116.3 (3)	C11—C12—H12B	109.5
C18—N5—Mn1	169.2 (6)	H12A—C12—H12B	109.5
C19—N6—Mn1	174.9 (5)	C11—C12—H12C	109.5
N1—C1—C2	123.6 (6)	H12A—C12—H12C	109.5
N1—C1—H1	118.2	H12B—C12—H12C	109.5
C2—C1—H1	118.2	N4—C13—C14	120.4 (5)
C3—C2—C1	118.0 (6)	N4—C13—C11	116.3 (5)
C3—C2—H2	121.0	C14—C13—C11	123.3 (5)
C1—C2—H2	121.0	C15—C14—C13	119.7 (6)
C2—C3—C4	119.7 (6)	C15—C14—H14	120.2
C2—C3—H3	120.1	C13—C14—H14	120.2
C4—C3—H3	120.1	C16—C15—C14	119.6 (6)
C3—C4—C5	119.2 (6)	C16—C15—H15	120.2
C3—C4—H4	120.4	C14—C15—H15	120.2
C5—C4—H4	120.4	C15—C16—C17	118.2 (6)
N1—C5—C4	121.6 (5)	C15—C16—H16	120.9
N1—C5—C6	115.6 (4)	C17—C16—H16	120.9
C4—C5—C6	122.8 (5)	N4—C17—C16	124.2 (6)
N2—C6—C5	115.6 (5)	N4—C17—H17	117.9
N2—C6—C7	126.2 (5)	C16—C17—H17	117.9
C5—C6—C7	118.2 (5)	N5—C18—S1	178.7 (6)
C6—C7—H7A	109.5	N6—C19—S2	179.4 (6)
C6—C7—H7B	109.5

Table 1

Selected bond lengths (Å)

Mn1—N5	2.127 (6)
Mn1—N6	2.149 (6)
Mn1—N2	2.258 (5)
Mn1—N3	2.260 (4)
Mn1—N4	2.334 (4)
Mn1—N1	2.346 (4)