{N,N-Dimethyl-N'-[1-(2-pyrid-yl)ethyl-idene]propane-1,3-diamine}bis(thio-cyanato-κN)-copper(II).

In the title complex, [Cu(NCS)(2)(C(12)H(19)N(3))], the Cu(II) atom is five-coordinated in a square-pyramidal geometry defined by one pyridine N, one imine N, and one amine N atom of the tridentate Schiff base ligand and two N-bonded thio-cyanate ions (one of the latter occupying the apical site). The three bridging C atoms and the two terminal C atoms of the Schiff base are disordered over two sets of sites, with occupancies of 0.465 (2) and 0.535 (2).

Related literature

For a related structure and background to Schiff bases, see: Xue et al. (2010 ▶).

Experimental

Crystal data

[Cu(NCS)2(C12H19N3)]

M = 385.00

Monoclinic,

a = 13.723 (2) Å

b = 7.2380 (12) Å

c = 18.237 (3) Å

β = 103.559 (2)°

V = 1760.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.48 mm−1

T = 298 K

0.23 × 0.21 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.727, T max = 0.746

13886 measured reflections

3816 independent reflections

2698 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.04

3816 reflections

237 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.47 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/S1600536810036378/hb5636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036378/hb5636Isup2.hkl

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

[Cu(NCS)2(C12H19N3)]	F(000) = 796
Mr = 385.00	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2747 reflections
a = 13.723 (2) Å	θ = 2.3–24.5°
b = 7.2380 (12) Å	µ = 1.48 mm−1
c = 18.237 (3) Å	T = 298 K
β = 103.559 (2)°	Block, blue
V = 1760.9 (5) Å3	0.23 × 0.21 × 0.21 mm
Z = 4

Bruker SMART CCD diffractometer	3816 independent reflections
Radiation source: fine-focus sealed tube	2698 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→17
Tmin = 0.727, Tmax = 0.746	k = −9→9
13886 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.6842P] where P = (Fo2 + 2Fc2)/3
3816 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.57 e Å−3
16 restraints	Δρmin = −0.47 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)
Cu1	0.24814 (3)	0.82783 (5)	0.39009 (2)	0.04378 (15)
N1	0.3853 (2)	0.8651 (4)	0.36614 (15)	0.0459 (7)
N2	0.2846 (2)	1.0789 (4)	0.43585 (14)	0.0457 (6)
N4	0.2763 (2)	0.7053 (4)	0.50065 (18)	0.0594 (8)
N5	0.2289 (2)	0.5969 (5)	0.33292 (18)	0.0624 (8)
S1	0.2253 (2)	0.6298 (3)	0.63328 (10)	0.1725 (10)
S2	0.23557 (7)	0.28351 (14)	0.24673 (6)	0.0611 (3)
C1	0.4337 (3)	0.7542 (6)	0.3285 (2)	0.0647 (10)
H1	0.4028	0.6446	0.3090	0.078*
C2	0.5270 (3)	0.7936 (7)	0.3170 (2)	0.0752 (13)
H2	0.5584	0.7124	0.2904	0.090*
C3	0.5724 (3)	0.9539 (7)	0.3454 (2)	0.0716 (12)
H3	0.6358	0.9835	0.3388	0.086*
C4	0.5236 (3)	1.0714 (6)	0.3839 (2)	0.0601 (10)
H4	0.5533	1.1821	0.4032	0.072*
C5	0.4300 (2)	1.0238 (5)	0.39356 (17)	0.0443 (7)
C6	0.3702 (2)	1.1400 (4)	0.43399 (18)	0.0452 (8)
C7	0.4155 (3)	1.3171 (5)	0.4690 (2)	0.0701 (12)
H7A	0.4090	1.4104	0.4307	0.105*
H7B	0.4851	1.2979	0.4921	0.105*
H7C	0.3812	1.3563	0.5065	0.105*
N3	0.0939 (2)	0.8665 (4)	0.36804 (17)	0.0606 (8)	0.465 (11)
C8	0.2202 (3)	1.1843 (5)	0.4750 (2)	0.0684 (11)	0.465 (11)
H8A	0.2116	1.3077	0.4538	0.082*	0.465 (11)
H8B	0.2549	1.1961	0.5276	0.082*	0.465 (11)
C9	0.1197 (6)	1.1045 (16)	0.4713 (5)	0.062 (3)	0.465 (11)
H9A	0.0797	1.1912	0.4924	0.074*	0.465 (11)
H9B	0.1263	0.9918	0.5009	0.074*	0.465 (11)
C10	0.0677 (7)	1.0625 (13)	0.3896 (5)	0.056 (3)	0.465 (11)
H10A	0.0886	1.1517	0.3566	0.067*	0.465 (11)
H10B	−0.0043	1.0731	0.3830	0.067*	0.465 (11)
C11	0.053 (3)	0.696 (4)	0.396 (2)	0.092 (10)	0.465 (11)
H11A	−0.0185	0.7058	0.3873	0.138*	0.465 (11)
H11B	0.0812	0.6838	0.4496	0.138*	0.465 (11)
H11C	0.0705	0.5903	0.3705	0.138*	0.465 (11)
C12	0.066 (3)	0.888 (6)	0.2842 (6)	0.071 (8)	0.465 (11)
H12A	−0.0053	0.9054	0.2678	0.107*	0.465 (11)
H12B	0.0849	0.7789	0.2611	0.107*	0.465 (11)
H12C	0.0998	0.9931	0.2700	0.107*	0.465 (11)
N3'	0.0939 (2)	0.8665 (4)	0.36804 (17)	0.0606 (8)	0.535 (11)
C8'	0.2202 (3)	1.1843 (5)	0.4750 (2)	0.0684 (11)	0.535 (11)
H8'A	0.2415	1.3124	0.4803	0.082*	0.535 (11)
H8'B	0.2252	1.1336	0.5250	0.082*	0.535 (11)
C9'	0.1099 (5)	1.1713 (11)	0.4277 (7)	0.077 (3)	0.535 (11)
H9'A	0.0703	1.2595	0.4484	0.093*	0.535 (11)
H9'B	0.1091	1.2112	0.3768	0.093*	0.535 (11)
C10'	0.0573 (6)	0.9862 (12)	0.4224 (6)	0.069 (3)	0.535 (11)
H10C	0.0711	0.9278	0.4717	0.082*	0.535 (11)
H10D	−0.0145	1.0035	0.4055	0.082*	0.535 (11)
C11'	0.036 (2)	0.703 (3)	0.3837 (17)	0.071 (5)	0.535 (11)
H11D	−0.0346	0.7331	0.3720	0.106*	0.535 (11)
H11E	0.0569	0.6702	0.4360	0.106*	0.535 (11)
H11F	0.0467	0.6009	0.3531	0.106*	0.535 (11)
C12'	0.052 (3)	0.896 (5)	0.2860 (6)	0.071 (7)	0.535 (11)
H12D	−0.0197	0.9133	0.2770	0.106*	0.535 (11)
H12E	0.0653	0.7900	0.2584	0.106*	0.535 (11)
H12F	0.0815	1.0035	0.2697	0.106*	0.535 (11)
C13	0.2546 (3)	0.6730 (5)	0.5551 (2)	0.0572 (9)
C14	0.2316 (2)	0.4674 (5)	0.29685 (19)	0.0481 (8)

	U11	U22	U33	U12	U13	U23
Cu1	0.0369 (2)	0.0457 (2)	0.0496 (2)	−0.00511 (18)	0.01183 (16)	−0.00953 (18)
N1	0.0412 (15)	0.0515 (17)	0.0463 (15)	−0.0058 (12)	0.0131 (12)	−0.0059 (12)
N2	0.0448 (16)	0.0426 (16)	0.0496 (15)	0.0014 (13)	0.0109 (12)	−0.0037 (12)
N4	0.066 (2)	0.057 (2)	0.0533 (18)	−0.0049 (15)	0.0097 (15)	0.0003 (15)
N5	0.0559 (19)	0.0598 (19)	0.072 (2)	−0.0085 (16)	0.0162 (16)	−0.0233 (17)
S1	0.264 (3)	0.178 (2)	0.1026 (12)	−0.0650 (18)	0.0974 (15)	0.0160 (12)
S2	0.0560 (6)	0.0568 (6)	0.0762 (6)	−0.0069 (4)	0.0269 (5)	−0.0187 (5)
C1	0.055 (2)	0.078 (3)	0.064 (2)	−0.011 (2)	0.0212 (19)	−0.025 (2)
C2	0.051 (2)	0.107 (4)	0.075 (3)	−0.005 (2)	0.031 (2)	−0.023 (2)
C3	0.042 (2)	0.106 (4)	0.071 (3)	−0.012 (2)	0.0205 (19)	0.002 (2)
C4	0.045 (2)	0.069 (3)	0.064 (2)	−0.0139 (19)	0.0068 (17)	0.003 (2)
C5	0.0366 (17)	0.0494 (19)	0.0435 (17)	−0.0030 (15)	0.0024 (13)	0.0060 (15)
C6	0.0428 (19)	0.0389 (18)	0.0486 (18)	−0.0020 (14)	0.0004 (14)	0.0025 (14)
C7	0.062 (2)	0.046 (2)	0.093 (3)	−0.0065 (19)	−0.001 (2)	−0.012 (2)
N3	0.0378 (16)	0.073 (2)	0.069 (2)	−0.0027 (15)	0.0079 (14)	−0.0122 (17)
C8	0.069 (3)	0.059 (2)	0.079 (3)	0.009 (2)	0.023 (2)	−0.021 (2)
C9	0.062 (6)	0.061 (7)	0.078 (7)	0.003 (5)	0.047 (5)	−0.009 (5)
C10	0.034 (5)	0.066 (7)	0.072 (6)	0.017 (4)	0.019 (4)	0.007 (5)
C11	0.019 (8)	0.155 (18)	0.096 (19)	−0.026 (9)	0.003 (9)	0.037 (10)
C12	0.032 (9)	0.105 (17)	0.065 (12)	−0.007 (8)	−0.012 (8)	0.027 (10)
N3'	0.0378 (16)	0.073 (2)	0.069 (2)	−0.0027 (15)	0.0079 (14)	−0.0122 (17)
C8'	0.069 (3)	0.059 (2)	0.079 (3)	0.009 (2)	0.023 (2)	−0.021 (2)
C9'	0.067 (6)	0.058 (6)	0.126 (10)	0.003 (4)	0.061 (7)	−0.008 (6)
C10'	0.058 (5)	0.074 (6)	0.083 (7)	0.005 (4)	0.034 (5)	0.001 (5)
C11'	0.038 (12)	0.120 (12)	0.053 (6)	−0.007 (6)	0.007 (8)	0.019 (6)
C12'	0.050 (13)	0.061 (10)	0.100 (15)	−0.006 (7)	0.013 (8)	0.010 (9)
C13	0.066 (2)	0.043 (2)	0.061 (2)	−0.0099 (18)	0.0108 (19)	0.0024 (18)
C14	0.0348 (17)	0.054 (2)	0.0550 (19)	−0.0070 (15)	0.0103 (14)	−0.0051 (17)

Cu1—N5	1.955 (3)	N3—C11	1.494 (9)
Cu1—N2	2.013 (3)	N3—C10	1.537 (7)
Cu1—N1	2.047 (3)	C8—C9	1.483 (7)
Cu1—N3	2.078 (3)	C8—H8A	0.9700
Cu1—N4	2.153 (3)	C8—H8B	0.9700
N1—C1	1.331 (4)	C9—C10	1.525 (9)
N1—C5	1.343 (4)	C9—H9A	0.9700
N2—C6	1.264 (4)	C9—H9B	0.9700
N2—C8	1.472 (4)	C10—H10A	0.9700
N4—C13	1.126 (4)	C10—H10B	0.9700
N5—C14	1.151 (4)	C11—H11A	0.9600
S1—C13	1.600 (4)	C11—H11B	0.9600
S2—C14	1.622 (4)	C11—H11C	0.9600
C1—C2	1.375 (5)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C2—C3	1.361 (6)	C12—H12C	0.9600
C2—H2	0.9300	C9'—C10'	1.514 (9)
C3—C4	1.373 (5)	C9'—H9'A	0.9700
C3—H3	0.9300	C9'—H9'B	0.9700
C4—C5	1.380 (5)	C10'—H10C	0.9700
C4—H4	0.9300	C10'—H10D	0.9700
C5—C6	1.486 (5)	C11'—H11D	0.9600
C6—C7	1.500 (4)	C11'—H11E	0.9600
C7—H7A	0.9600	C11'—H11F	0.9600
C7—H7B	0.9600	C12'—H12D	0.9600
C7—H7C	0.9600	C12'—H12E	0.9600
N3—C12	1.494 (9)	C12'—H12F	0.9600
N5—Cu1—N2	169.17 (12)	C11—N3—Cu1	105.6 (16)
N5—Cu1—N1	90.84 (12)	C10—N3—Cu1	111.3 (4)
N2—Cu1—N1	79.51 (11)	N2—C8—C9	115.7 (4)
N5—Cu1—N3	90.46 (12)	N2—C8—H8A	108.3
N2—Cu1—N3	95.82 (11)	C9—C8—H8A	108.3
N1—Cu1—N3	152.40 (12)	N2—C8—H8B	108.3
N5—Cu1—N4	96.85 (13)	C9—C8—H8B	108.3
N2—Cu1—N4	90.64 (11)	H8A—C8—H8B	107.4
N1—Cu1—N4	106.39 (12)	C8—C9—C10	109.8 (7)
N3—Cu1—N4	100.82 (12)	C8—C9—H9A	109.7
C1—N1—C5	117.9 (3)	C10—C9—H9A	109.7
C1—N1—Cu1	128.7 (3)	C8—C9—H9B	109.7
C5—N1—Cu1	113.4 (2)	C10—C9—H9B	109.7
C6—N2—C8	119.9 (3)	H9A—C9—H9B	108.2
C6—N2—Cu1	116.6 (2)	C9—C10—N3	110.5 (7)
C8—N2—Cu1	123.3 (2)	C9—C10—H10A	109.5
C13—N4—Cu1	152.2 (3)	N3—C10—H10A	109.5
C14—N5—Cu1	169.4 (3)	C9—C10—H10B	109.5
N1—C1—C2	123.3 (4)	N3—C10—H10B	109.5
N1—C1—H1	118.4	H10A—C10—H10B	108.1
C2—C1—H1	118.4	N3—C11—H11A	109.5
C3—C2—C1	118.6 (4)	N3—C11—H11B	109.5
C3—C2—H2	120.7	H11A—C11—H11B	109.5
C1—C2—H2	120.7	N3—C11—H11C	109.5
C2—C3—C4	119.2 (4)	H11A—C11—H11C	109.5
C2—C3—H3	120.4	H11B—C11—H11C	109.5
C4—C3—H3	120.4	N3—C12—H12A	109.5
C3—C4—C5	119.4 (4)	N3—C12—H12B	109.5
C3—C4—H4	120.3	H12A—C12—H12B	109.5
C5—C4—H4	120.3	N3—C12—H12C	109.5
N1—C5—C4	121.6 (3)	H12A—C12—H12C	109.5
N1—C5—C6	114.3 (3)	H12B—C12—H12C	109.5
C4—C5—C6	124.1 (3)	C10'—C9'—H9'A	107.7
N2—C6—C5	116.1 (3)	C10'—C9'—H9'B	107.7
N2—C6—C7	125.6 (3)	H9'A—C9'—H9'B	107.1
C5—C6—C7	118.3 (3)	C9'—C10'—H10C	109.9
C6—C7—H7A	109.5	C9'—C10'—H10D	109.9
C6—C7—H7B	109.5	H10C—C10'—H10D	108.3
H7A—C7—H7B	109.5	H11D—C11'—H11E	109.5
C6—C7—H7C	109.5	H11D—C11'—H11F	109.5
H7A—C7—H7C	109.5	H11E—C11'—H11F	109.5
H7B—C7—H7C	109.5	H12D—C12'—H12E	109.5
C12—N3—C11	114 (2)	H12D—C12'—H12F	109.5
C12—N3—C10	98.4 (18)	H12E—C12'—H12F	109.5
C11—N3—C10	122.9 (19)	N4—C13—S1	178.9 (4)
C12—N3—Cu1	102.7 (18)	N5—C14—S2	179.4 (3)

Table 1

Selected bond lengths (Å)

Cu1—N5	1.955 (3)
Cu1—N2	2.013 (3)
Cu1—N1	2.047 (3)
Cu1—N3	2.078 (3)
Cu1—N4	2.153 (3)