{N-Methyl-N'-[1-(pyridin-2-yl)ethyl-idene]ethane-1,2-diamine-κN,N',N''}-bis(thio-cyanato-κN)zinc(II).

In the title compound, [Zn(NCS)(2)(C(10)H(15)N(3))], the Zn atom is five-coordinated by the three N-donor atoms of the Schiff base ligand and by two N atoms from two thio-cyanate anions, forming a distorted ZnN(5) trigonal-bipyramidal coordination geometry for the metal ion. The side chain of the ligand is disordered over two sets of sites in a 0.655 (12):0.345 (12) ratio. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, generating [100] chains.

Related literature

For the biological activity of Schiff base compounds, see: Panneerselvam et al. (2005 ▶); Shi et al. (2007 ▶); Singh et al. (2006 ▶, 2007 ▶); Zhong et al. (2006 ▶). For the Schiff base complexes we reported previously, see: Li & Qiu (2008a ▶,b ▶).

Experimental

Crystal data

[Zn(NCS)2(C10H15N3)]

M = 358.78

Monoclinic,

a = 7.6674 (3) Å

b = 14.8062 (5) Å

c = 14.3766 (6) Å

β = 101.853 (2)°

V = 1597.30 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.80 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.715, T max = 0.738

9004 measured reflections

3352 independent reflections

2095 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.02

3352 reflections

201 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811019945/hb5892sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019945/hb5892Isup2.hkl

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

[Zn(NCS)2(C10H15N3)]	F(000) = 736
Mr = 358.78	Dx = 1.492 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2372 reflections
a = 7.6674 (3) Å	θ = 2.6–25.1°
b = 14.8062 (5) Å	µ = 1.80 mm−1
c = 14.3766 (6) Å	T = 298 K
β = 101.853 (2)°	Block, colorless
V = 1597.30 (11) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	2095 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 26.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.715, Tmax = 0.738	k = −17→18
9004 measured reflections	l = −18→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0323P)2 + 1.952P] where P = (Fo2 + 2Fc2)/3
3352 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.46 e Å−3
12 restraints	Δρmin = −0.46 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	Occ. (<1)
Zn1	0.72087 (6)	−0.07353 (3)	0.71636 (3)	0.05504 (17)
S1	1.28221 (17)	−0.15205 (10)	0.89256 (10)	0.0835 (4)
S2	0.3366 (2)	−0.32564 (11)	0.66375 (10)	0.1063 (6)
N1	0.7424 (4)	−0.0555 (2)	0.5676 (2)	0.0524 (8)
N2	0.6777 (4)	0.0641 (2)	0.6890 (2)	0.0559 (8)
N4	0.9697 (5)	−0.1140 (3)	0.7651 (3)	0.0760 (11)
N5	0.5583 (5)	−0.1782 (2)	0.6923 (2)	0.0684 (10)
C1	0.7390 (5)	0.0309 (3)	0.5392 (3)	0.0515 (9)
C2	0.7683 (5)	0.0539 (3)	0.4504 (3)	0.0628 (11)
H2	0.7670	0.1142	0.4319	0.075*
C3	0.7993 (6)	−0.0131 (4)	0.3901 (3)	0.0708 (13)
H3	0.8193	0.0015	0.3303	0.085*
C4	0.8009 (6)	−0.1007 (4)	0.4174 (3)	0.0706 (13)
H4	0.8207	−0.1469	0.3770	0.085*
C5	0.7719 (6)	−0.1192 (3)	0.5074 (3)	0.0629 (11)
H5	0.7731	−0.1792	0.5268	0.075*
C6	0.7014 (5)	0.0970 (3)	0.6107 (3)	0.0577 (10)
C7	0.6971 (7)	0.1958 (3)	0.5876 (4)	0.0877 (15)
H7A	0.6442	0.2284	0.6325	0.132*
H7B	0.6279	0.2052	0.5247	0.132*
H7C	0.8164	0.2172	0.5907	0.132*
C11	1.1008 (6)	−0.1300 (3)	0.8180 (3)	0.0573 (10)
C12	0.4653 (6)	−0.2395 (3)	0.6815 (3)	0.0586 (10)
C8	0.6362 (7)	0.1164 (3)	0.7662 (3)	0.0810 (14)	0.655 (12)
H8A	0.5502	0.1631	0.7417	0.097*	0.655 (12)
H8B	0.7431	0.1451	0.8016	0.097*	0.655 (12)
C9	0.5577 (12)	0.0508 (5)	0.8318 (5)	0.074 (3)	0.655 (12)
H9A	0.5582	0.0803	0.8921	0.089*	0.655 (12)
H9B	0.4349	0.0371	0.8026	0.089*	0.655 (12)
C10	0.7978 (14)	−0.0366 (8)	0.9293 (6)	0.089 (3)	0.655 (12)
H10A	0.7586	−0.0160	0.9849	0.133*	0.655 (12)
H10B	0.8964	−0.0004	0.9196	0.133*	0.655 (12)
H10C	0.8346	−0.0986	0.9377	0.133*	0.655 (12)
N3	0.6540 (6)	−0.0290 (3)	0.8480 (2)	0.0814 (12)	0.655 (12)
H3A	0.5729	−0.0703	0.8591	0.098*	0.655 (12)
C8'	0.6362 (7)	0.1164 (3)	0.7662 (3)	0.0810 (14)	0.345 (12)
H8'A	0.5082	0.1233	0.7582	0.097*	0.345 (12)
H8'B	0.6893	0.1760	0.7673	0.097*	0.345 (12)
C9'	0.709 (2)	0.0678 (7)	0.8562 (7)	0.097 (7)	0.345 (12)
H9'A	0.6658	0.0959	0.9081	0.116*	0.345 (12)
H9'B	0.8382	0.0719	0.8702	0.116*	0.345 (12)
C10'	0.723 (2)	−0.0647 (13)	0.9393 (8)	0.066 (5)	0.345 (12)
H10D	0.6699	−0.0338	0.9854	0.099*	0.345 (12)
H10E	0.8497	−0.0565	0.9546	0.099*	0.345 (12)
H10F	0.6955	−0.1279	0.9400	0.099*	0.345 (12)
N3'	0.6540 (6)	−0.0290 (3)	0.8480 (2)	0.0814 (12)	0.345 (12)
H3'A	0.5331	−0.0302	0.8394	0.098*	0.345 (12)

	U11	U22	U33	U12	U13	U23
Zn1	0.0644 (3)	0.0492 (3)	0.0518 (3)	0.0000 (2)	0.0128 (2)	0.0037 (2)
S1	0.0678 (8)	0.0948 (10)	0.0845 (9)	0.0061 (7)	0.0077 (6)	−0.0070 (7)
S2	0.1434 (14)	0.0975 (11)	0.0869 (9)	−0.0621 (10)	0.0447 (9)	−0.0190 (8)
N1	0.062 (2)	0.0456 (19)	0.0502 (18)	−0.0062 (15)	0.0126 (15)	−0.0006 (15)
N2	0.061 (2)	0.0461 (18)	0.061 (2)	0.0029 (16)	0.0128 (16)	−0.0033 (16)
N4	0.074 (3)	0.082 (3)	0.073 (3)	0.008 (2)	0.018 (2)	0.021 (2)
N5	0.082 (3)	0.055 (2)	0.069 (2)	−0.007 (2)	0.017 (2)	0.0074 (18)
C1	0.042 (2)	0.057 (2)	0.053 (2)	−0.0039 (18)	0.0023 (17)	0.0080 (19)
C2	0.055 (3)	0.071 (3)	0.059 (3)	−0.008 (2)	0.003 (2)	0.020 (2)
C3	0.064 (3)	0.100 (4)	0.048 (2)	−0.015 (3)	0.010 (2)	0.009 (3)
C4	0.068 (3)	0.092 (4)	0.054 (3)	−0.010 (3)	0.018 (2)	−0.012 (2)
C5	0.072 (3)	0.056 (3)	0.064 (3)	−0.005 (2)	0.022 (2)	−0.002 (2)
C6	0.054 (2)	0.044 (2)	0.070 (3)	−0.0030 (18)	0.002 (2)	0.004 (2)
C7	0.114 (4)	0.048 (3)	0.099 (4)	−0.001 (3)	0.015 (3)	0.008 (3)
C11	0.065 (3)	0.051 (2)	0.060 (3)	−0.005 (2)	0.024 (2)	0.003 (2)
C12	0.075 (3)	0.059 (3)	0.045 (2)	−0.002 (2)	0.022 (2)	0.007 (2)
C8	0.097 (4)	0.060 (3)	0.089 (4)	−0.004 (3)	0.025 (3)	−0.019 (3)
C9	0.081 (6)	0.080 (6)	0.062 (4)	0.033 (4)	0.018 (4)	−0.005 (4)
C10	0.111 (7)	0.092 (7)	0.059 (5)	0.030 (5)	0.010 (5)	−0.003 (4)
N3	0.092 (3)	0.097 (3)	0.057 (2)	−0.012 (3)	0.020 (2)	−0.009 (2)
C8'	0.097 (4)	0.060 (3)	0.089 (4)	−0.004 (3)	0.025 (3)	−0.019 (3)
C9'	0.096 (14)	0.151 (18)	0.044 (8)	−0.025 (12)	0.015 (8)	−0.013 (9)
C10'	0.090 (12)	0.066 (10)	0.046 (7)	0.005 (9)	0.025 (8)	0.016 (7)
N3'	0.092 (3)	0.097 (3)	0.057 (2)	−0.012 (3)	0.020 (2)	−0.009 (2)

Zn1—N5	1.974 (4)	C5—H5	0.9300
Zn1—N4	1.986 (4)	C6—C7	1.499 (6)
Zn1—N2	2.088 (3)	C7—H7A	0.9600
Zn1—N3	2.163 (4)	C7—H7B	0.9600
Zn1—N1	2.195 (3)	C7—H7C	0.9600
S1—C11	1.605 (5)	C8—C9	1.559 (7)
S2—C12	1.601 (5)	C8—H8A	0.9700
N1—C5	1.330 (5)	C8—H8B	0.9700
N1—C1	1.342 (5)	C9—N3	1.388 (6)
N2—C6	1.273 (5)	C9—H9A	0.9700
N2—C8	1.441 (5)	C9—H9B	0.9700
N4—C11	1.154 (5)	C10—N3	1.437 (7)
N5—C12	1.145 (5)	C10—H10A	0.9600
C1—C2	1.383 (5)	C10—H10B	0.9600
C1—C6	1.490 (6)	C10—H10C	0.9600
C2—C3	1.371 (6)	N3—H3A	0.9100
C2—H2	0.9300	C9'—H9'A	0.9700
C3—C4	1.354 (6)	C9'—H9'B	0.9700
C3—H3	0.9300	C10'—H10D	0.9600
C4—C5	1.385 (6)	C10'—H10E	0.9600
C4—H4	0.9300	C10'—H10F	0.9600
N5—Zn1—N4	110.56 (16)	C6—C7—H7A	109.5
N5—Zn1—N2	131.51 (14)	C6—C7—H7B	109.5
N4—Zn1—N2	117.70 (15)	H7A—C7—H7B	109.5
N5—Zn1—N3	97.92 (16)	C6—C7—H7C	109.5
N4—Zn1—N3	99.59 (16)	H7A—C7—H7C	109.5
N2—Zn1—N3	79.09 (15)	H7B—C7—H7C	109.5
N5—Zn1—N1	95.51 (13)	N4—C11—S1	179.4 (4)
N4—Zn1—N1	96.97 (14)	N5—C12—S2	178.5 (4)
N2—Zn1—N1	74.85 (12)	N2—C8—C9	107.8 (4)
N3—Zn1—N1	153.44 (15)	N2—C8—H8A	110.2
C5—N1—C1	118.3 (3)	C9—C8—H8A	110.2
C5—N1—Zn1	127.2 (3)	N2—C8—H8B	110.2
C1—N1—Zn1	114.3 (3)	C9—C8—H8B	110.2
C6—N2—C8	124.6 (4)	H8A—C8—H8B	108.5
C6—N2—Zn1	119.6 (3)	N3—C9—C8	111.9 (5)
C8—N2—Zn1	115.5 (3)	N3—C9—H9A	109.2
C11—N4—Zn1	159.8 (4)	C8—C9—H9A	109.2
C12—N5—Zn1	177.7 (4)	N3—C9—H9B	109.2
N1—C1—C2	121.3 (4)	C8—C9—H9B	109.2
N1—C1—C6	114.3 (3)	H9A—C9—H9B	107.9
C2—C1—C6	124.4 (4)	N3—C10—H10A	109.5
C3—C2—C1	119.2 (4)	N3—C10—H10B	109.5
C3—C2—H2	120.4	H10A—C10—H10B	109.5
C1—C2—H2	120.4	N3—C10—H10C	109.5
C4—C3—C2	120.2 (4)	H10A—C10—H10C	109.5
C4—C3—H3	119.9	H10B—C10—H10C	109.5
C2—C3—H3	119.9	C9—N3—C10	119.7 (7)
C3—C4—C5	117.8 (4)	C9—N3—Zn1	109.1 (3)
C3—C4—H4	121.1	C10—N3—Zn1	114.1 (5)
C5—C4—H4	121.1	C9—N3—H3A	104.0
N1—C5—C4	123.3 (4)	C10—N3—H3A	104.0
N1—C5—H5	118.4	Zn1—N3—H3A	104.0
C4—C5—H5	118.4	H9'A—C9'—H9'B	108.1
N2—C6—C1	116.2 (3)	H10D—C10'—H10E	109.5
N2—C6—C7	124.7 (4)	H10D—C10'—H10F	109.5
C1—C6—C7	119.1 (4)	H10E—C10'—H10F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···S1i	0.91	2.66	3.551 (5)	165

Table 1

Selected bond lengths (Å)

Zn1—N5	1.974 (4)
Zn1—N4	1.986 (4)
Zn1—N2	2.088 (3)
Zn1—N3	2.163 (4)
Zn1—N1	2.195 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯S1i	0.91	2.66	3.551 (5)	165

Symmetry code: (i) .