{6-[(2-Anilinoeth-yl)imino-meth-yl]-2-eth-oxyphenolato}(thio-cyanato-κN)-copper(II).

In the title complex, [Cu(C(17)H(19)N(2)O(2))(NCS)], the Cu(II) atom is chelated by the phenolate O atom, the imine N atom and the amine N atom of the N,N',O-tridentate 2-eth-oxy-6-[(2-anilino-ethyl)-iminometh-yl]phenolate ligand, and by the N atom of a thio-cyanate anion, forming a distorted CuON(3) square-planar geometry. The dihedral angle between the aromatic rings of the ligand is 67.9 (4)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, generating R(2) (2)(8) loops.

Related literature

For background to the structures and properties of copper complexes, see: Collinson & Fenton (1996 ▶); Hossain et al. (1996 ▶); Tarafder et al. (2002 ▶); Musie et al. (2003 ▶); García-Raso et al. (2003 ▶); Reddy et al. (2000 ▶); Ray et al. (2003 ▶); Arnold et al. (2003 ▶); Raptopoulou et al. (1998 ▶). For related structures, see: Wang et al. (2009a ▶,b ▶); Wang (2009 ▶); Hebbachi & Benali-Cherif (2005 ▶); Butcher et al. (2003 ▶); Elmali et al. (2000 ▶); Warda et al. (1997 ▶).

Experimental

Crystal data

[Cu(C17H19N2O2)(NCS)]

M = 404.96

Orthorhombic,

a = 13.6786 (5) Å

b = 10.4938 (4) Å

c = 25.2618 (10) Å

V = 3626.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.34 mm−1

T = 298 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.690, T max = 0.714

19741 measured reflections

3746 independent reflections

2041 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.182

S = 1.03

3746 reflections

229 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.25 e Å−3

Δρmin = −0.64 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; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010305/hb5365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010305/hb5365Isup2.hkl

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

[Cu(C17H19N2O2)(NCS)]	F(000) = 1672
Mr = 404.96	Dx = 1.484 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2506 reflections
a = 13.6786 (5) Å	θ = 2.4–24.9°
b = 10.4938 (4) Å	µ = 1.34 mm−1
c = 25.2618 (10) Å	T = 298 K
V = 3626.1 (2) Å3	Block, blue
Z = 8	0.30 × 0.27 × 0.27 mm

Bruker SMART CCD diffractometer	3746 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scan	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
Tmin = 0.690, Tmax = 0.714	k = −13→12
19741 measured reflections	l = −26→31

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0843P)2 + 3.6378P] where P = (Fo2 + 2Fc2)/3
3746 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 1.25 e Å−3
13 restraints	Δρmin = −0.64 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	0.88473 (4)	0.07765 (5)	0.49939 (2)	0.0424 (2)
O1	0.9189 (3)	0.0617 (3)	0.57256 (13)	0.0498 (9)
O2	0.9226 (4)	−0.0030 (7)	0.67464 (19)	0.0976 (17)
S1	0.82168 (12)	−0.35452 (14)	0.52360 (11)	0.1050 (8)
N1	0.9061 (3)	0.2590 (4)	0.50007 (17)	0.0454 (10)
N2	0.9049 (3)	0.0938 (4)	0.41821 (16)	0.0468 (10)
N3	0.8557 (4)	−0.1032 (4)	0.49588 (17)	0.0568 (12)
C1	0.9081 (4)	0.2849 (6)	0.5943 (2)	0.0625 (15)
C2	0.9123 (4)	0.1538 (6)	0.6078 (2)	0.0528 (14)
C3	0.9115 (5)	0.1206 (8)	0.6623 (2)	0.0731 (18)
C4	0.9057 (6)	0.2158 (12)	0.7003 (3)	0.108 (3)
H4	0.9043	0.1930	0.7358	0.130*
C5	0.9020 (7)	0.3417 (12)	0.6870 (4)	0.123 (4)
H5	0.8990	0.4034	0.7134	0.148*
C6	0.9027 (5)	0.3772 (8)	0.6348 (4)	0.094 (3)
H6	0.8995	0.4631	0.6260	0.113*
C7	0.9110 (4)	0.3275 (5)	0.5412 (3)	0.0585 (15)
H7	0.9172	0.4149	0.5360	0.070*
C8	0.9046 (4)	0.3177 (5)	0.4472 (2)	0.0597 (16)
H8A	0.9436	0.3948	0.4471	0.072*
H8B	0.8382	0.3397	0.4374	0.072*
C9	0.9458 (4)	0.2233 (5)	0.4086 (2)	0.0567 (14)
H9A	0.9303	0.2500	0.3728	0.068*
H9B	1.0163	0.2207	0.4121	0.068*
C10	0.8236 (4)	0.0581 (6)	0.3843 (2)	0.0529 (14)
C11	0.7402 (5)	0.1237 (8)	0.3838 (3)	0.110 (3)
H11	0.7344	0.1955	0.4052	0.132*
C12	0.6615 (6)	0.0878 (10)	0.3522 (5)	0.124 (3)
H12	0.6035	0.1339	0.3538	0.149*
C13	0.6683 (6)	−0.0091 (11)	0.3208 (3)	0.092 (3)
H13	0.6174	−0.0291	0.2978	0.110*
C14	0.7499 (7)	−0.0807 (10)	0.3217 (3)	0.117 (3)
H14	0.7538	−0.1532	0.3006	0.141*
C15	0.8299 (6)	−0.0466 (9)	0.3544 (3)	0.105 (3)
H15	0.8861	−0.0964	0.3551	0.126*
C16	0.8566 (12)	−0.0681 (15)	0.6821 (7)	0.215 (7)
H16A	0.8254	−0.0841	0.6483	0.258*
H16B	0.8102	−0.0210	0.7036	0.258*
C17	0.8735 (8)	−0.1978 (12)	0.7090 (4)	0.154 (4)
H17A	0.8550	−0.2650	0.6853	0.232*
H17B	0.8348	−0.2029	0.7406	0.232*
H17C	0.9414	−0.2065	0.7180	0.232*
C18	0.8418 (4)	−0.2070 (5)	0.5072 (2)	0.0523 (13)
H2	0.952 (3)	0.035 (4)	0.413 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.0542 (4)	0.0294 (3)	0.0437 (4)	−0.0002 (2)	−0.0047 (3)	0.0060 (3)
O1	0.058 (2)	0.048 (2)	0.0435 (19)	0.0116 (17)	−0.0025 (16)	0.0050 (16)
O2	0.076 (3)	0.147 (5)	0.069 (3)	0.005 (4)	0.018 (3)	0.042 (3)
S1	0.0524 (9)	0.0341 (8)	0.228 (2)	−0.0038 (7)	−0.0174 (12)	0.0304 (11)
N1	0.042 (2)	0.033 (2)	0.061 (3)	0.0013 (16)	0.000 (2)	0.006 (2)
N2	0.047 (3)	0.051 (3)	0.042 (2)	0.003 (2)	−0.0037 (19)	0.006 (2)
N3	0.074 (3)	0.034 (2)	0.063 (3)	−0.002 (2)	−0.006 (2)	0.004 (2)
C1	0.053 (4)	0.065 (4)	0.069 (4)	0.000 (3)	0.006 (3)	−0.018 (3)
C2	0.047 (3)	0.065 (4)	0.047 (3)	0.001 (3)	0.002 (2)	−0.005 (3)
C3	0.063 (4)	0.102 (5)	0.054 (4)	0.001 (4)	0.004 (3)	0.006 (4)
C4	0.087 (6)	0.182 (10)	0.056 (4)	−0.012 (7)	0.016 (4)	−0.040 (6)
C5	0.115 (8)	0.140 (9)	0.115 (8)	−0.022 (7)	0.028 (6)	−0.067 (8)
C6	0.092 (6)	0.083 (5)	0.106 (6)	−0.011 (4)	0.028 (5)	−0.049 (5)
C7	0.054 (3)	0.036 (3)	0.086 (5)	0.003 (2)	0.005 (3)	−0.007 (3)
C8	0.058 (4)	0.043 (3)	0.078 (4)	0.001 (3)	0.004 (3)	0.028 (3)
C9	0.045 (3)	0.064 (4)	0.061 (3)	0.000 (3)	0.003 (3)	0.022 (3)
C10	0.045 (3)	0.072 (4)	0.042 (3)	−0.003 (3)	−0.003 (2)	0.012 (3)
C11	0.062 (5)	0.122 (7)	0.146 (7)	0.022 (5)	−0.032 (5)	−0.036 (6)
C12	0.068 (6)	0.140 (9)	0.164 (9)	0.010 (5)	−0.048 (6)	−0.012 (7)
C13	0.068 (5)	0.152 (8)	0.056 (4)	−0.039 (6)	−0.019 (4)	0.032 (5)
C14	0.092 (6)	0.166 (9)	0.095 (6)	−0.021 (6)	−0.019 (5)	−0.057 (6)
C15	0.067 (5)	0.140 (8)	0.108 (6)	0.007 (5)	−0.015 (4)	−0.053 (6)
C16	0.199 (10)	0.184 (10)	0.261 (11)	0.002 (8)	0.075 (8)	−0.001 (8)
C17	0.148 (7)	0.157 (8)	0.158 (7)	−0.017 (6)	0.054 (6)	0.036 (6)
C18	0.046 (3)	0.034 (3)	0.077 (4)	0.001 (2)	−0.007 (3)	0.004 (3)

Cu1—O1	1.914 (3)	C7—H7	0.9300
Cu1—N1	1.926 (4)	C8—C9	1.499 (8)
Cu1—N3	1.941 (4)	C8—H8A	0.9700
Cu1—N2	2.076 (4)	C8—H8B	0.9700
O1—C2	1.316 (6)	C9—H9A	0.9700
O2—C16	1.148 (15)	C9—H9B	0.9700
O2—C3	1.342 (9)	C10—C11	1.332 (9)
S1—C18	1.627 (5)	C10—C15	1.336 (9)
N1—C7	1.265 (7)	C11—C12	1.392 (11)
N1—C8	1.470 (6)	C11—H11	0.9300
N2—C10	1.452 (7)	C12—C13	1.294 (12)
N2—C9	1.489 (7)	C12—H12	0.9300
N2—H2	0.901 (10)	C13—C14	1.346 (12)
N3—C18	1.142 (7)	C13—H13	0.9300
C1—C6	1.411 (9)	C14—C15	1.419 (10)
C1—C7	1.414 (8)	C14—H14	0.9300
C1—C2	1.419 (8)	C15—H15	0.9300
C2—C3	1.420 (8)	C16—C17	1.538 (17)
C3—C4	1.388 (11)	C16—H16A	0.9700
C4—C5	1.364 (13)	C16—H16B	0.9700
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.371 (13)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—H6	0.9300
O1—Cu1—N1	92.33 (17)	C9—C8—H8A	110.1
O1—Cu1—N3	90.50 (16)	N1—C8—H8B	110.1
N1—Cu1—N3	176.25 (19)	C9—C8—H8B	110.1
O1—Cu1—N2	158.24 (17)	H8A—C8—H8B	108.4
N1—Cu1—N2	84.73 (18)	N2—C9—C8	110.9 (4)
N3—Cu1—N2	93.54 (17)	N2—C9—H9A	109.5
C2—O1—Cu1	124.9 (3)	C8—C9—H9A	109.5
C16—O2—C3	121.6 (10)	N2—C9—H9B	109.5
C7—N1—C8	120.6 (5)	C8—C9—H9B	109.5
C7—N1—Cu1	125.2 (4)	H9A—C9—H9B	108.1
C8—N1—Cu1	113.8 (3)	C11—C10—C15	118.3 (6)
C10—N2—C9	115.3 (4)	C11—C10—N2	121.9 (6)
C10—N2—Cu1	117.4 (3)	C15—C10—N2	119.7 (6)
C9—N2—Cu1	106.5 (3)	C10—C11—C12	121.9 (8)
C10—N2—H2	107 (4)	C10—C11—H11	119.0
C9—N2—H2	109 (4)	C12—C11—H11	119.0
Cu1—N2—H2	100 (4)	C13—C12—C11	120.6 (9)
C18—N3—Cu1	162.8 (5)	C13—C12—H12	119.7
C6—C1—C7	118.2 (7)	C11—C12—H12	119.7
C6—C1—C2	119.6 (7)	C12—C13—C14	119.2 (7)
C7—C1—C2	122.2 (5)	C12—C13—H13	120.4
O1—C2—C1	123.5 (5)	C14—C13—H13	120.4
O1—C2—C3	118.4 (6)	C13—C14—C15	120.6 (8)
C1—C2—C3	118.1 (6)	C13—C14—H14	119.7
O2—C3—C4	122.7 (7)	C15—C14—H14	119.7
O2—C3—C2	117.5 (6)	C10—C15—C14	119.2 (8)
C4—C3—C2	119.6 (8)	C10—C15—H15	120.4
C5—C4—C3	122.0 (9)	C14—C15—H15	120.4
C5—C4—H4	119.0	O2—C16—C17	118.8 (15)
C3—C4—H4	119.0	O2—C16—H16A	107.6
C4—C5—C6	119.9 (9)	C17—C16—H16A	107.6
C4—C5—H5	120.0	O2—C16—H16B	107.6
C6—C5—H5	120.0	C17—C16—H16B	107.6
C5—C6—C1	120.8 (9)	H16A—C16—H16B	107.1
C5—C6—H6	119.6	C16—C17—H17A	109.5
C1—C6—H6	119.6	C16—C17—H17B	109.5
N1—C7—C1	126.7 (5)	H17A—C17—H17B	109.5
N1—C7—H7	116.7	C16—C17—H17C	109.5
C1—C7—H7	116.7	H17A—C17—H17C	109.5
N1—C8—C9	108.0 (4)	H17B—C17—H17C	109.5
N1—C8—H8A	110.1	N3—C18—S1	179.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.07 (3)	2.920 (6)	157 (5)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.914 (3)
Cu1—N1	1.926 (4)
Cu1—N3	1.941 (4)
Cu1—N2	2.076 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	2.07 (3)	2.920 (6)	157 (5)

Symmetry code: (i) .