Bis(2-{[2-(isopropyl-aza-nium-yl)eth-yl]imino-meth-yl}-6-meth-oxy-phenolato)copper(II) bis-(thio-cyanate).

The asymmetric unit of the title compound, [Cu(C(13)H(20)N(2)O(2))(2)](NCS)(2), contains one half-dication, located on an inversion center, and one thio-cyanate anion. Each Cu(II) atom is four-coordinated by two phenolate O and two imine N atoms from two symmetry-related Schiff base 2-{[2-(isopropyl-aza-nium-yl)eth-yl]imino-meth-yl}-6-meth-oxy-phenolate (L) ligands in a distorted square-planar geometry. The ammonium groups are involved in the formation of N-H⋯O and N-H⋯N hydrogen bonds, which link one dication and two anions into an electroneutral cluster. When very weak Cu-N interactions with a distance of 2.910 (5) Å between the metal and the thiocyanate anions in apical positions are considered, the secondary coordination polyhedron is a very elongated CuN(4)O(2) octahedron.

Related literature

For background to copper(II) complexes with Schiff base ligands, see: Fernandez et al. (2010 ▶); Biswas et al. (2010 ▶); Chakraborty et al. (2010 ▶). For related complexes, see: Ji & Lu (2010 ▶); Cai (2009 ▶); Xia et al. (2008 ▶); Suleiman Gwaram et al. (2010 ▶); Ma (2008 ▶).

Experimental

Crystal data

[Cu(C13H20N2O2)2](NCS)2

M = 652.32

Orthorhombic,

a = 13.5307 (12) Å

b = 9.7992 (9) Å

c = 24.114 (2) Å

V = 3197.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 298 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.848, T max = 0.882

13234 measured reflections

2406 independent reflections

1666 reflections with I > 2σ(I)

R int = 0.063

θmax = 23.8°

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.143

S = 1.15

2406 reflections

190 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.36 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001322/cv5037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001322/cv5037Isup2.hkl

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

[Cu(C13H20N2O2)2](NCS)2	Dx = 1.355 Mg m−3
Mr = 652.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1594 reflections
a = 13.5307 (12) Å	θ = 2.3–24.5°
b = 9.7992 (9) Å	µ = 0.86 mm−1
c = 24.114 (2) Å	T = 298 K
V = 3197.3 (5) Å3	Block, blue
Z = 4	0.20 × 0.18 × 0.15 mm
F(000) = 1372

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 23.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.848, Tmax = 0.882	k = −11→8
13234 measured reflections	l = −27→27

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + 13.3941P] where P = (Fo2 + 2Fc2)/3
2406 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.38 e Å−3
6 restraints	Δρmin = −0.36 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
Cu1	0.0000	0.5000	1.0000	0.0565 (4)
N1	0.1018 (4)	0.3629 (5)	0.97413 (19)	0.0449 (13)
N2	0.0401 (4)	0.4022 (5)	0.85934 (19)	0.0496 (14)
H2A	0.0758	0.4746	0.8706	0.059*
H2B	−0.0187	0.4064	0.8767	0.059*
N3	0.0998 (7)	0.6598 (8)	0.9151 (4)	0.112 (3)
O1	0.0858 (3)	0.5576 (5)	1.05728 (17)	0.0600 (13)
O2	0.1714 (4)	0.7103 (5)	1.12935 (19)	0.0683 (14)
S1	0.1299 (2)	0.8802 (4)	0.84850 (14)	0.1397 (13)
C1	0.2387 (5)	0.4671 (7)	1.0238 (2)	0.0493 (17)
C2	0.1830 (5)	0.5544 (7)	1.0579 (2)	0.0484 (16)
C3	0.2338 (5)	0.6371 (7)	1.0960 (3)	0.0539 (17)
C4	0.3351 (5)	0.6389 (8)	1.0981 (3)	0.063 (2)
H4	0.3672	0.6978	1.1224	0.075*
C5	0.3903 (5)	0.5527 (8)	1.0640 (3)	0.066 (2)
H5	0.4590	0.5537	1.0657	0.079*
C6	0.3431 (5)	0.4669 (7)	1.0282 (3)	0.0589 (19)
H6	0.3800	0.4075	1.0063	0.071*
C7	0.1925 (5)	0.3692 (7)	0.9874 (2)	0.0525 (17)
H7	0.2338	0.3034	0.9720	0.063*
C8	0.0748 (5)	0.2484 (6)	0.9380 (2)	0.0536 (17)
H8A	0.0056	0.2269	0.9436	0.064*
H8B	0.1131	0.1690	0.9487	0.064*
C9	0.0919 (5)	0.2770 (6)	0.8775 (3)	0.0560 (18)
H9A	0.1622	0.2872	0.8708	0.067*
H9B	0.0687	0.2002	0.8557	0.067*
C10	0.0230 (6)	0.4153 (7)	0.7987 (3)	0.064 (2)
H10	−0.0103	0.3324	0.7857	0.077*
C11	0.1193 (7)	0.4276 (10)	0.7687 (3)	0.114 (4)
H11A	0.1546	0.3429	0.7713	0.172*
H11B	0.1579	0.4991	0.7851	0.172*
H11C	0.1072	0.4487	0.7304	0.172*
C12	−0.0447 (7)	0.5355 (8)	0.7880 (3)	0.098 (3)
H12A	−0.1033	0.5264	0.8101	0.147*
H12B	−0.0624	0.5378	0.7495	0.147*
H12C	−0.0112	0.6186	0.7977	0.147*
C13	0.2134 (6)	0.8058 (8)	1.1669 (3)	0.084 (3)
H13A	0.2598	0.7600	1.1906	0.127*
H13B	0.1621	0.8459	1.1890	0.127*
H13C	0.2468	0.8761	1.1464	0.127*
C14	0.1133 (7)	0.7473 (10)	0.8862 (4)	0.097 (3)

	U11	U22	U33	U12	U13	U23
Cu1	0.0503 (6)	0.0653 (7)	0.0539 (6)	0.0066 (7)	−0.0009 (6)	−0.0144 (7)
N1	0.047 (3)	0.046 (3)	0.041 (3)	−0.004 (3)	0.005 (3)	0.002 (3)
N2	0.058 (3)	0.050 (3)	0.041 (3)	0.013 (3)	0.009 (3)	−0.001 (3)
N3	0.137 (6)	0.072 (5)	0.127 (6)	0.006 (5)	−0.054 (5)	0.004 (5)
O1	0.049 (3)	0.080 (3)	0.051 (3)	0.004 (2)	0.001 (2)	−0.016 (2)
O2	0.069 (3)	0.072 (3)	0.064 (3)	0.003 (3)	−0.011 (3)	−0.018 (3)
S1	0.120 (2)	0.160 (3)	0.139 (3)	0.040 (2)	0.023 (2)	0.056 (2)
C1	0.050 (4)	0.057 (4)	0.041 (3)	0.008 (3)	0.005 (3)	0.007 (3)
C2	0.050 (4)	0.057 (4)	0.039 (4)	−0.001 (3)	−0.004 (3)	0.008 (3)
C3	0.065 (5)	0.051 (4)	0.047 (4)	0.001 (4)	0.001 (4)	0.006 (3)
C4	0.066 (5)	0.063 (5)	0.060 (5)	−0.017 (4)	−0.014 (4)	0.017 (4)
C5	0.050 (5)	0.077 (5)	0.071 (5)	−0.006 (4)	−0.004 (4)	0.015 (4)
C6	0.054 (4)	0.065 (5)	0.058 (4)	0.003 (4)	0.009 (4)	0.013 (4)
C7	0.066 (5)	0.053 (4)	0.039 (4)	0.007 (4)	0.015 (3)	0.004 (3)
C8	0.066 (5)	0.045 (4)	0.050 (4)	0.007 (4)	0.005 (3)	0.001 (3)
C9	0.073 (5)	0.050 (4)	0.046 (4)	0.014 (4)	−0.006 (4)	−0.005 (3)
C10	0.092 (6)	0.061 (5)	0.040 (4)	0.006 (4)	0.001 (4)	−0.001 (4)
C11	0.152 (9)	0.138 (9)	0.053 (5)	0.033 (7)	0.045 (6)	0.019 (5)
C12	0.152 (9)	0.084 (6)	0.058 (5)	0.033 (6)	−0.032 (5)	0.008 (4)
C13	0.109 (7)	0.072 (5)	0.071 (5)	0.003 (5)	−0.020 (5)	−0.019 (4)
C14	0.102 (7)	0.076 (6)	0.114 (8)	0.008 (6)	−0.041 (7)	−0.021 (6)

Cu1—O1i	1.891 (4)	C5—C6	1.364 (9)
Cu1—O1	1.891 (4)	C5—H5	0.9300
Cu1—N1i	2.023 (5)	C6—H6	0.9300
Cu1—N1	2.023 (5)	C7—H7	0.9300
N1—C7	1.271 (8)	C8—C9	1.504 (8)
N1—C8	1.466 (7)	C8—H8A	0.9700
N2—C9	1.480 (7)	C8—H8B	0.9700
N2—C10	1.486 (7)	C9—H9A	0.9700
N2—H2A	0.9001	C9—H9B	0.9700
N2—H2B	0.9000	C10—C11	1.496 (10)
N3—C14	1.120 (11)	C10—C12	1.513 (9)
O1—C2	1.316 (7)	C10—H10	0.9800
O2—C3	1.370 (7)	C11—H11A	0.9600
O2—C13	1.421 (8)	C11—H11B	0.9600
S1—C14	1.603 (11)	C11—H11C	0.9600
C1—C2	1.404 (8)	C12—H12A	0.9600
C1—C6	1.417 (9)	C12—H12B	0.9600
C1—C7	1.443 (9)	C12—H12C	0.9600
C2—C3	1.405 (9)	C13—H13A	0.9600
C3—C4	1.372 (9)	C13—H13B	0.9600
C4—C5	1.396 (10)	C13—H13C	0.9600
C4—H4	0.9300
O1i—Cu1—O1	180	N1—C8—C9	113.3 (5)
O1i—Cu1—N1i	90.3 (2)	N1—C8—H8A	108.9
O1—Cu1—N1i	89.7 (2)	C9—C8—H8A	108.9
O1i—Cu1—N1	89.7 (2)	N1—C8—H8B	108.9
O1—Cu1—N1	90.3 (2)	C9—C8—H8B	108.9
N1i—Cu1—N1	180.0 (3)	H8A—C8—H8B	107.7
C7—N1—C8	115.3 (6)	N2—C9—C8	111.6 (5)
C7—N1—Cu1	123.2 (5)	N2—C9—H9A	109.3
C8—N1—Cu1	121.4 (4)	C8—C9—H9A	109.3
C9—N2—C10	115.9 (5)	N2—C9—H9B	109.3
C9—N2—H2A	108.1	C8—C9—H9B	109.3
C10—N2—H2A	108.2	H9A—C9—H9B	108.0
C9—N2—H2B	108.6	N2—C10—C11	110.3 (6)
C10—N2—H2B	108.5	N2—C10—C12	109.2 (6)
H2A—N2—H2B	107.4	C11—C10—C12	112.5 (7)
C2—O1—Cu1	127.9 (4)	N2—C10—H10	108.3
C3—O2—C13	118.2 (6)	C11—C10—H10	108.3
C2—C1—C6	119.6 (6)	C12—C10—H10	108.3
C2—C1—C7	121.9 (6)	C10—C11—H11A	109.5
C6—C1—C7	118.4 (6)	C10—C11—H11B	109.5
O1—C2—C1	123.0 (6)	H11A—C11—H11B	109.5
O1—C2—C3	118.8 (6)	C10—C11—H11C	109.5
C1—C2—C3	118.1 (6)	H11A—C11—H11C	109.5
O2—C3—C4	126.0 (7)	H11B—C11—H11C	109.5
O2—C3—C2	112.7 (6)	C10—C12—H12A	109.5
C4—C3—C2	121.3 (7)	C10—C12—H12B	109.5
C3—C4—C5	120.3 (7)	H12A—C12—H12B	109.5
C3—C4—H4	119.8	C10—C12—H12C	109.5
C5—C4—H4	119.8	H12A—C12—H12C	109.5
C6—C5—C4	119.8 (7)	H12B—C12—H12C	109.5
C6—C5—H5	120.1	O2—C13—H13A	109.5
C4—C5—H5	120.1	O2—C13—H13B	109.5
C5—C6—C1	120.8 (7)	H13A—C13—H13B	109.5
C5—C6—H6	119.6	O2—C13—H13C	109.5
C1—C6—H6	119.6	H13A—C13—H13C	109.5
N1—C7—C1	127.2 (6)	H13B—C13—H13C	109.5
N1—C7—H7	116.4	N3—C14—S1	175.6 (11)
C1—C7—H7	116.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.90	2.13	2.972 (10)	155
N2—H2B···O1i	0.90	1.87	2.665 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.90	2.13	2.972 (10)	155
N2—H2B⋯O1i	0.90	1.87	2.665 (6)	147

Symmetry code: (i) .