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

The mol-ecule of the title compound, [Mn(NCS)(2)(C(16)H(18)N(4))], has crystallographic twofold rotation symmetry, with the Mn(II) atom lying on the rotation axis. The Mn(II) atom is six-coordinated by four N atoms of the Schiff base ligand and by two N atoms of two thio-cyanate ligands, forming a distorted octa-hedral geometry.

Related literature

For background to Schiff base compounds, see: Ruck & Jacobsen (2002 ▶); Mukhopadhyay et al. (2003 ▶); Polt et al. (2003 ▶); Mukherjee et al. (2001 ▶). For complexes derived from N,N′-bis­(1-(pyridin-2-yl)ethyl­idene)ethane-1,2-diamine, see: Gourbatsis et al. (1998 ▶); Louloudi et al. (1999 ▶); Karmakar et al. (2002 ▶); Banerjee et al. (2004 ▶). For related n class="Chemical">MnII 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(C16H18N4)]

M = 437.44

Monoclinic,

a = 12.570 (4) Å

b = 16.341 (5) Å

c = 9.962 (3) Å

β = 90.857 (4)°

V = 2045.9 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.867, T max = 0.881

4479 measured reflections

2173 independent reflections

1590 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.093

S = 1.02

2173 reflections

124 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.35 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/S1600536810021550/ci5097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021550/ci5097Isup2.hkl

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

[Mn(NCS)2(C16H18N4)]	F(000) = 900
Mr = 437.44	Dx = 1.420 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1222 reflections
a = 12.570 (4) Å	θ = 2.6–25.3°
b = 16.341 (5) Å	µ = 0.86 mm−1
c = 9.962 (3) Å	T = 298 K
β = 90.857 (4)°	Block, brown
V = 2045.9 (10) Å3	0.17 × 0.15 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2173 independent reflections
Radiation source: fine-focus sealed tube	1590 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scan	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→12
Tmin = 0.867, Tmax = 0.881	k = −20→20
4479 measured reflections	l = −12→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0354P)2 + 1.1621P] where P = (Fo2 + 2Fc2)/3
2173 reflections	(Δ/σ)max = 0.001
124 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.35 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	0.5000	0.28864 (3)	0.2500	0.04525 (18)
N1	0.42596 (16)	0.32743 (14)	0.03855 (19)	0.0533 (5)
N2	0.44344 (15)	0.17790 (12)	0.13277 (18)	0.0471 (5)
N3	0.63772 (18)	0.34541 (15)	0.1706 (2)	0.0648 (6)
S1	0.82249 (6)	0.38624 (6)	0.04009 (8)	0.0872 (3)
C1	0.4168 (2)	0.40396 (19)	−0.0058 (3)	0.0700 (8)
H1	0.4354	0.4463	0.0523	0.084*
C2	0.3812 (2)	0.4238 (2)	−0.1337 (3)	0.0770 (9)
H2	0.3750	0.4781	−0.1605	0.092*
C3	0.3554 (2)	0.3616 (2)	−0.2193 (3)	0.0774 (9)
H3	0.3325	0.3729	−0.3065	0.093*
C4	0.3636 (2)	0.28185 (19)	−0.1753 (3)	0.0658 (8)
H4	0.3455	0.2388	−0.2323	0.079*
C5	0.39910 (18)	0.26645 (16)	−0.0454 (2)	0.0492 (6)
C6	0.40708 (18)	0.18264 (16)	0.0130 (2)	0.0482 (6)
C7	0.3715 (2)	0.11213 (18)	−0.0729 (3)	0.0731 (8)
H7A	0.4227	0.1028	−0.1418	0.110*
H7B	0.3036	0.1246	−0.1134	0.110*
H7C	0.3654	0.0639	−0.0184	0.110*
C8	0.4512 (2)	0.10020 (15)	0.2047 (2)	0.0563 (7)
H8A	0.4556	0.0555	0.1410	0.068*
H8B	0.3881	0.0922	0.2580	0.068*
C9	0.7137 (2)	0.36210 (16)	0.1152 (2)	0.0515 (6)

	U11	U22	U33	U12	U13	U23
Mn1	0.0431 (3)	0.0515 (3)	0.0411 (3)	0.000	0.0002 (2)	0.000
N1	0.0524 (12)	0.0574 (14)	0.0500 (12)	0.0008 (10)	−0.0029 (9)	0.0033 (10)
N2	0.0468 (11)	0.0525 (13)	0.0418 (11)	0.0001 (9)	−0.0008 (9)	−0.0012 (9)
N3	0.0507 (13)	0.0863 (17)	0.0575 (13)	−0.0072 (12)	0.0016 (10)	0.0114 (12)
S1	0.0612 (5)	0.1388 (9)	0.0619 (5)	−0.0238 (5)	0.0102 (4)	0.0159 (5)
C1	0.081 (2)	0.0640 (19)	0.0650 (17)	0.0042 (16)	−0.0056 (15)	0.0044 (15)
C2	0.080 (2)	0.078 (2)	0.0727 (19)	0.0090 (17)	−0.0060 (17)	0.0206 (17)
C3	0.069 (2)	0.104 (3)	0.0589 (17)	−0.0006 (18)	−0.0151 (15)	0.0212 (18)
C4	0.0610 (17)	0.084 (2)	0.0523 (15)	−0.0075 (15)	−0.0149 (12)	0.0052 (15)
C5	0.0352 (12)	0.0679 (17)	0.0444 (13)	−0.0030 (11)	−0.0011 (10)	0.0014 (12)
C6	0.0387 (13)	0.0629 (16)	0.0430 (13)	−0.0037 (11)	0.0018 (10)	−0.0049 (11)
C7	0.086 (2)	0.077 (2)	0.0553 (16)	−0.0141 (17)	−0.0139 (15)	−0.0073 (14)
C8	0.0657 (17)	0.0558 (16)	0.0475 (14)	−0.0064 (13)	−0.0019 (11)	0.0004 (11)
C9	0.0520 (15)	0.0619 (17)	0.0405 (12)	−0.0004 (13)	−0.0061 (11)	0.0071 (11)

Mn1—N3	2.127 (2)	C2—C3	1.363 (4)
Mn1—N3i	2.127 (2)	C2—H2	0.93
Mn1—N2	2.263 (2)	C3—C4	1.378 (4)
Mn1—N2i	2.263 (2)	C3—H3	0.93
Mn1—N1i	2.376 (2)	C4—C5	1.386 (3)
Mn1—N1	2.376 (2)	C4—H4	0.93
N1—C1	1.331 (3)	C5—C6	1.491 (4)
N1—C5	1.341 (3)	C6—C7	1.500 (3)
N2—C6	1.273 (3)	C7—H7A	0.96
N2—C8	1.461 (3)	C7—H7B	0.96
N3—C9	1.144 (3)	C7—H7C	0.96
S1—C9	1.617 (3)	C8—C8i	1.512 (5)
C1—C2	1.382 (4)	C8—H8A	0.97
C1—H1	0.93	C8—H8B	0.97
N3—Mn1—N3i	128.28 (13)	C1—C2—H2	120.9
N3—Mn1—N2	114.09 (8)	C2—C3—C4	119.4 (3)
N3i—Mn1—N2	106.83 (8)	C2—C3—H3	120.3
N3—Mn1—N2i	106.83 (8)	C4—C3—H3	120.3
N3i—Mn1—N2i	114.09 (8)	C3—C4—C5	119.3 (3)
N2—Mn1—N2i	73.78 (10)	C3—C4—H4	120.3
N3—Mn1—N1i	84.43 (8)	C5—C4—H4	120.3
N3i—Mn1—N1i	82.20 (8)	N1—C5—C4	121.5 (2)
N2—Mn1—N1i	141.89 (7)	N1—C5—C6	115.1 (2)
N2i—Mn1—N1i	68.89 (7)	C4—C5—C6	123.4 (2)
N3—Mn1—N1	82.20 (8)	N2—C6—C5	116.3 (2)
N3i—Mn1—N1	84.43 (8)	N2—C6—C7	126.0 (2)
N2—Mn1—N1	68.89 (7)	C5—C6—C7	117.7 (2)
N2i—Mn1—N1	141.89 (7)	C6—C7—H7A	109.5
N1i—Mn1—N1	149.06 (11)	C6—C7—H7B	109.5
C1—N1—C5	118.1 (2)	H7A—C7—H7B	109.5
C1—N1—Mn1	125.15 (18)	C6—C7—H7C	109.5
C5—N1—Mn1	116.51 (16)	H7A—C7—H7C	109.5
C6—N2—C8	122.2 (2)	H7B—C7—H7C	109.5
C6—N2—Mn1	122.72 (17)	N2—C8—C8i	109.89 (15)
C8—N2—Mn1	115.07 (14)	N2—C8—H8A	109.7
C9—N3—Mn1	166.9 (2)	C8i—C8—H8A	109.7
N1—C1—C2	123.5 (3)	N2—C8—H8B	109.7
N1—C1—H1	118.3	C8i—C8—H8B	109.7
C2—C1—H1	118.3	H8A—C8—H8B	108.2
C3—C2—C1	118.2 (3)	N3—C9—S1	178.7 (2)
C3—C2—H2	120.9

Table 1

Selected bond lengths (Å)

Mn1—N3	2.127 (2)
Mn1—N2	2.263 (2)
Mn1—N1	2.376 (2)