{2-[2-(Ethyl-amino)ethyl-imino-meth-yl]-5-methoxy-phenolato}(thio-cyanato-κN)-copper(II).

In the title mononuclear copper(II) complex, [Cu(C(12)H(17)N(2)O(2))(NCS)], the Cu(II) atom is four-coordinated by an NNO-donor set of the tridentate Schiff base ligand and the N atom of a terminal thio-cyanate ligand in a slightly distorted square-planar geometry.

Related literature

For CuII complexes with n class="Chemical">Schiff base ligands, see: Dede et al. (2009 ▶); Rai (2010 ▶); Rajasekar et al. (2010 ▶); Roper et al. (1989 ▶). For related structures, see: Adams et al. (2003 ▶); Roy & Manassero (2010 ▶).

Experimental

Crystal data

[Cu(C12H17N2O2)(n class="Chemical">NCS)]

M = 342.90

Monoclinic,

a = 12.296 (6) Å

b = 10.582 (5) Å

c = 12.480 (6) Å

β = 113.810 (7)°

V = 1485.7 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.61 mm−1

T = 293 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.643, T max = 0.670

8523 measured reflections

3282 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.00

3282 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.61 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/S1600536810009402/ci5055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009402/ci5055Isup2.hkl

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

[Cu(C12H17N2O2)(NCS)]	F(000) = 708
Mr = 342.90	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2310 reflections
a = 12.296 (6) Å	θ = 2.6–25.0°
b = 10.582 (5) Å	µ = 1.61 mm−1
c = 12.480 (6) Å	T = 293 K
β = 113.810 (7)°	Block cut from needle, blue
V = 1485.7 (12) Å3	0.30 × 0.27 × 0.27 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3282 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scan	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.643, Tmax = 0.670	k = −13→13
8523 measured reflections	l = −16→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0551P)2 + 1.5145P] where P = (Fo2 + 2Fc2)/3
3282 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cu1	0.55890 (4)	0.38272 (4)	0.94272 (4)	0.04744 (18)
N1	0.6492 (3)	0.3114 (3)	1.0844 (3)	0.0465 (8)
N2	0.4301 (3)	0.2831 (3)	0.9449 (3)	0.0596 (9)
H2N	0.3686	0.3382	0.9287	0.072*
N3	0.4579 (3)	0.4525 (3)	0.7995 (3)	0.0488 (8)
O1	0.6770 (2)	0.4836 (3)	0.9392 (2)	0.0543 (7)
O2	1.0326 (3)	0.7210 (3)	1.0840 (3)	0.0718 (9)
S1	0.30391 (13)	0.57348 (14)	0.60132 (10)	0.0790 (4)
C1	0.7807 (3)	0.5063 (4)	1.0246 (3)	0.0460 (9)
C2	0.8513 (4)	0.5995 (4)	1.0075 (3)	0.0516 (10)
H2	0.8249	0.6414	0.9360	0.062*
C3	0.9598 (4)	0.6314 (4)	1.0944 (4)	0.0552 (10)
C4	0.9978 (5)	0.7842 (5)	0.9760 (4)	0.0858 (17)
H4A	0.9877	0.7240	0.9152	0.129*
H4B	1.0578	0.8443	0.9801	0.129*
H4C	0.9240	0.8276	0.9590	0.129*
C5	1.0006 (4)	0.5683 (5)	1.2010 (4)	0.0664 (12)
H5	1.0740	0.5885	1.2598	0.080*
C6	0.9326 (4)	0.4776 (4)	1.2183 (4)	0.0629 (12)
H6	0.9605	0.4365	1.2904	0.075*
C7	0.8217 (4)	0.4421 (4)	1.1327 (3)	0.0480 (9)
C8	0.7542 (4)	0.3458 (4)	1.1546 (3)	0.0510 (10)
H8	0.7884	0.3035	1.2258	0.061*
C9	0.5884 (4)	0.2097 (4)	1.1177 (4)	0.0597 (11)
H9A	0.6175	0.2042	1.2023	0.072*
H9B	0.6024	0.1293	1.0880	0.072*
C10	0.4593 (4)	0.2402 (4)	1.0658 (4)	0.0630 (12)
H10A	0.4129	0.1660	1.0658	0.076*
H10B	0.4421	0.3062	1.1106	0.076*
C11	0.3850 (5)	0.1848 (5)	0.8565 (4)	0.0792 (15)
H11A	0.4379	0.1126	0.8819	0.095*
H11B	0.3879	0.2159	0.7845	0.095*
C12	0.2620 (5)	0.1410 (5)	0.8301 (4)	0.0816 (16)
H12A	0.2569	0.1124	0.9009	0.122*
H12B	0.2422	0.0727	0.7748	0.122*
H12C	0.2074	0.2095	0.7976	0.122*
C13	0.3932 (4)	0.5018 (4)	0.7173 (3)	0.0459 (9)

	U11	U22	U33	U12	U13	U23
Cu1	0.0569 (3)	0.0430 (3)	0.0396 (3)	−0.0019 (2)	0.0166 (2)	0.00224 (19)
N1	0.063 (2)	0.0397 (17)	0.0379 (16)	0.0056 (15)	0.0213 (15)	0.0010 (13)
N2	0.077 (3)	0.0499 (19)	0.0485 (19)	−0.0137 (18)	0.0216 (18)	0.0024 (15)
N3	0.055 (2)	0.0471 (18)	0.0396 (17)	−0.0061 (16)	0.0142 (15)	0.0017 (14)
O1	0.0489 (16)	0.0666 (18)	0.0378 (14)	−0.0067 (14)	0.0073 (12)	0.0121 (12)
O2	0.0598 (19)	0.089 (2)	0.0557 (19)	−0.0252 (18)	0.0123 (15)	−0.0104 (16)
S1	0.0831 (9)	0.1010 (10)	0.0463 (6)	0.0400 (8)	0.0192 (6)	0.0180 (6)
C1	0.046 (2)	0.050 (2)	0.0409 (19)	0.0040 (18)	0.0167 (17)	−0.0023 (17)
C2	0.048 (2)	0.063 (3)	0.040 (2)	−0.002 (2)	0.0142 (17)	−0.0014 (18)
C3	0.052 (2)	0.060 (3)	0.051 (2)	−0.004 (2)	0.0181 (19)	−0.0141 (19)
C4	0.078 (4)	0.106 (4)	0.069 (3)	−0.044 (3)	0.024 (3)	−0.008 (3)
C5	0.051 (3)	0.078 (3)	0.054 (3)	0.002 (2)	0.004 (2)	−0.007 (2)
C6	0.063 (3)	0.068 (3)	0.045 (2)	0.010 (2)	0.008 (2)	0.003 (2)
C7	0.047 (2)	0.050 (2)	0.043 (2)	0.0092 (19)	0.0146 (17)	0.0009 (17)
C8	0.064 (3)	0.048 (2)	0.038 (2)	0.018 (2)	0.0180 (19)	0.0068 (17)
C9	0.087 (3)	0.044 (2)	0.047 (2)	0.001 (2)	0.025 (2)	0.0102 (18)
C10	0.086 (4)	0.052 (2)	0.052 (2)	−0.018 (2)	0.029 (2)	0.002 (2)
C11	0.103 (4)	0.073 (3)	0.065 (3)	−0.030 (3)	0.037 (3)	−0.011 (3)
C12	0.078 (3)	0.093 (4)	0.057 (3)	−0.029 (3)	0.009 (2)	−0.002 (3)
C13	0.054 (2)	0.046 (2)	0.038 (2)	−0.0007 (19)	0.0193 (18)	−0.0025 (17)

Cu1—O1	1.817 (3)	C4—H4B	0.96
Cu1—N1	1.828 (3)	C4—H4C	0.96
Cu1—N3	1.868 (3)	C5—C6	1.346 (6)
Cu1—N2	1.912 (4)	C5—H5	0.93
N1—C8	1.286 (5)	C6—C7	1.402 (6)
N1—C9	1.463 (5)	C6—H6	0.93
N2—C11	1.453 (6)	C7—C8	1.410 (6)
N2—C10	1.474 (5)	C8—H8	0.93
N2—H2N	0.91	C9—C10	1.488 (6)
N3—C13	1.139 (5)	C9—H9A	0.97
O1—C1	1.313 (4)	C9—H9B	0.97
O2—C3	1.346 (5)	C10—H10A	0.97
O2—C4	1.409 (6)	C10—H10B	0.97
S1—C13	1.610 (4)	C11—C12	1.487 (7)
C1—C2	1.386 (6)	C11—H11A	0.97
C1—C7	1.409 (5)	C11—H11B	0.97
C2—C3	1.379 (6)	C12—H12A	0.96
C2—H2	0.93	C12—H12B	0.96
C3—C5	1.389 (6)	C12—H12C	0.96
C4—H4A	0.96
O1—Cu1—N1	94.97 (13)	C3—C5—H5	120.4
O1—Cu1—N3	88.49 (13)	C5—C6—C7	122.9 (4)
N1—Cu1—N3	176.29 (15)	C5—C6—H6	118.5
O1—Cu1—N2	177.40 (14)	C7—C6—H6	118.5
N1—Cu1—N2	86.67 (15)	C6—C7—C1	117.6 (4)
N3—Cu1—N2	89.82 (15)	C6—C7—C8	120.9 (4)
C8—N1—C9	120.1 (3)	C1—C7—C8	121.6 (4)
C8—N1—Cu1	126.4 (3)	N1—C8—C7	125.5 (3)
C9—N1—Cu1	113.4 (3)	N1—C8—H8	117.3
C11—N2—C10	114.7 (3)	C7—C8—H8	117.3
C11—N2—Cu1	116.6 (3)	N1—C9—C10	107.1 (3)
C10—N2—Cu1	108.9 (3)	N1—C9—H9A	110.3
C11—N2—H2N	105.2	C10—C9—H9A	110.3
C10—N2—H2N	105.2	N1—C9—H9B	110.3
Cu1—N2—H2N	105.2	C10—C9—H9B	110.3
C13—N3—Cu1	174.4 (3)	H9A—C9—H9B	108.5
C1—O1—Cu1	127.7 (2)	N2—C10—C9	106.8 (4)
C3—O2—C4	118.0 (3)	N2—C10—H10A	110.4
O1—C1—C2	118.0 (3)	C9—C10—H10A	110.4
O1—C1—C7	122.9 (4)	N2—C10—H10B	110.4
C2—C1—C7	119.1 (4)	C9—C10—H10B	110.4
C3—C2—C1	121.3 (4)	H10A—C10—H10B	108.6
C3—C2—H2	119.3	N2—C11—C12	115.7 (4)
C1—C2—H2	119.3	N2—C11—H11A	108.4
O2—C3—C2	124.5 (4)	C12—C11—H11A	108.4
O2—C3—C5	115.7 (4)	N2—C11—H11B	108.4
C2—C3—C5	119.8 (4)	C12—C11—H11B	108.4
O2—C4—H4A	109.5	H11A—C11—H11B	107.4
O2—C4—H4B	109.5	C11—C12—H12A	109.5
H4A—C4—H4B	109.5	C11—C12—H12B	109.5
O2—C4—H4C	109.5	H12A—C12—H12B	109.5
H4A—C4—H4C	109.5	C11—C12—H12C	109.5
H4B—C4—H4C	109.5	H12A—C12—H12C	109.5
C6—C5—C3	119.3 (4)	H12B—C12—H12C	109.5
C6—C5—H5	120.4	N3—C13—S1	178.8 (4)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.817 (3)
Cu1—N1	1.828 (3)
Cu1—N3	1.868 (3)
Cu1—N2	1.912 (4)