{6,6'-Dieth-oxy-2,2'-[4,5-dimethyl-o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}copper(II).

In the title complex, [Cu(C(26)H(26)N(2)O(4))], the Cu(II) ion lies on a crystallographic twofold rotation axis and is coordinated in a slightly distorted square-planar environment. The dihedral angle between the central benzene ring and each of the two symmetry-related outer benzene rings is 5.1 (2)°. The crystal structure is stabilized by inter-molecular π-π inter-actions with centroid-centroid distances in the range 3.466 (2)-3.6431 (16) Å.

Related literature

For background to Schiff base–metal complexes, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶); Elmali et al. (2000 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Cu(C26H26N2O4)]

M = 494.03

Monoclinic,

a = 14.9755 (7) Å

b = 15.8803 (7) Å

c = 12.2264 (6) Å

β = 119.285 (2)°

V = 2536.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 296 K

0.27 × 0.21 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.992

31403 measured reflections

3157 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.147

S = 1.05

3157 reflections

152 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042789/lh5150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042789/lh5150Isup2.hkl

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

[Cu(C26H26N2O4)]	F(000) = 1028
Mr = 494.03	Dx = 1.294 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2273 reflections
a = 14.9755 (7) Å	θ = 2.5–27.5°
b = 15.8803 (7) Å	µ = 0.89 mm−1
c = 12.2264 (6) Å	T = 296 K
β = 119.285 (2)°	Block, green
V = 2536.0 (2) Å3	0.27 × 0.21 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→20
Tmin = 0.982, Tmax = 0.992	k = 0→21
3157 measured reflections	l = −16→0

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0549P)2 + 4.1197P] where P = (Fo2 + 2Fc2)/3
3157 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.46 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 > 2sigma(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	0.51186 (3)	0.2500	0.0401 (2)
O1	0.06365 (19)	0.42620 (14)	0.2039 (2)	0.0464 (6)
N1	0.0519 (2)	0.60241 (16)	0.1905 (3)	0.0401 (7)
O2	0.1286 (2)	0.28916 (14)	0.1524 (3)	0.0591 (8)
C1	0.1134 (3)	0.4353 (2)	0.1421 (3)	0.0395 (8)
C2	0.1501 (3)	0.3619 (2)	0.1111 (3)	0.0444 (9)
C3	0.2022 (3)	0.3667 (3)	0.0445 (4)	0.0548 (10)
H3A	0.2271	0.3177	0.0272	0.066*
C4	0.2178 (3)	0.4435 (3)	0.0029 (4)	0.0590 (11)
H4A	0.2514	0.4457	−0.0440	0.071*
C5	0.1843 (3)	0.5156 (3)	0.0305 (4)	0.0531 (10)
H5A	0.1958	0.5670	0.0028	0.064*
C6	0.1315 (3)	0.5138 (2)	0.1013 (3)	0.0411 (8)
C7	0.0998 (3)	0.5921 (2)	0.1269 (3)	0.0449 (9)
H7A	0.1145	0.6403	0.0954	0.054*
C8	0.0270 (3)	0.6835 (2)	0.2165 (3)	0.0436 (9)
C9	0.0525 (3)	0.7599 (2)	0.1837 (4)	0.0544 (10)
H9A	0.0881	0.7601	0.1392	0.065*
C10	0.0264 (3)	0.8356 (2)	0.2158 (4)	0.0621 (13)
C11	0.0545 (4)	0.9164 (3)	0.1760 (5)	0.0899 (18)
H11A	0.0925	0.9516	0.2481	0.135*
H11B	−0.0067	0.9451	0.1169	0.135*
H11C	0.0957	0.9041	0.1376	0.135*
C12	0.1611 (3)	0.2112 (2)	0.1270 (4)	0.0537 (10)
H12A	0.2352	0.2095	0.1671	0.064*
H12B	0.1336	0.2044	0.0373	0.064*
C13	0.1234 (4)	0.1426 (3)	0.1764 (5)	0.0774 (14)
H13A	0.1490	0.0896	0.1659	0.116*
H13B	0.0499	0.1419	0.1313	0.116*
H13C	0.1469	0.1521	0.2638	0.116*

	U11	U22	U33	U12	U13	U23
Cu1	0.0526 (4)	0.0263 (3)	0.0492 (4)	0.000	0.0309 (3)	0.000
O1	0.0652 (17)	0.0318 (12)	0.0572 (16)	0.0001 (11)	0.0415 (15)	0.0021 (11)
N1	0.0440 (18)	0.0284 (15)	0.0416 (17)	0.0005 (12)	0.0161 (15)	0.0026 (12)
O2	0.084 (2)	0.0334 (14)	0.084 (2)	0.0090 (13)	0.0601 (18)	0.0010 (13)
C1	0.041 (2)	0.0384 (19)	0.042 (2)	−0.0003 (15)	0.0224 (18)	0.0007 (15)
C2	0.050 (2)	0.045 (2)	0.044 (2)	0.0025 (17)	0.0278 (19)	−0.0011 (16)
C3	0.056 (3)	0.057 (2)	0.061 (3)	0.002 (2)	0.037 (2)	−0.006 (2)
C4	0.058 (3)	0.071 (3)	0.066 (3)	−0.005 (2)	0.045 (2)	−0.002 (2)
C5	0.057 (2)	0.053 (2)	0.052 (2)	−0.0105 (19)	0.029 (2)	0.0052 (19)
C6	0.0423 (19)	0.0403 (18)	0.0402 (19)	−0.0024 (16)	0.0199 (16)	0.0006 (16)
C7	0.049 (2)	0.040 (2)	0.042 (2)	−0.0098 (16)	0.0197 (19)	0.0053 (16)
C8	0.048 (2)	0.0262 (17)	0.042 (2)	−0.0007 (15)	0.0111 (17)	0.0014 (15)
C9	0.060 (3)	0.0328 (19)	0.054 (2)	−0.0060 (18)	0.015 (2)	0.0081 (17)
C10	0.069 (3)	0.0271 (19)	0.053 (3)	−0.0036 (18)	0.001 (2)	0.0032 (16)
C11	0.116 (4)	0.032 (2)	0.083 (4)	−0.015 (2)	0.019 (3)	0.010 (2)
C12	0.055 (2)	0.044 (2)	0.064 (3)	0.0131 (18)	0.031 (2)	−0.0042 (18)
C13	0.101 (4)	0.039 (2)	0.103 (4)	0.011 (2)	0.058 (3)	0.000 (2)

Cu1—O1i	1.898 (2)	C6—C7	1.419 (5)
Cu1—O1	1.898 (2)	C7—H7A	0.9300
Cu1—N1i	1.938 (3)	C8—C9	1.389 (5)
Cu1—N1	1.938 (3)	C8—C8i	1.406 (7)
O1—C1	1.303 (4)	C9—C10	1.379 (5)
N1—C7	1.301 (5)	C9—H9A	0.9300
N1—C8	1.419 (4)	C10—C10i	1.404 (9)
O2—C2	1.361 (4)	C10—C11	1.504 (5)
O2—C12	1.419 (4)	C11—H11A	0.9600
C1—C2	1.417 (5)	C11—H11B	0.9600
C1—C6	1.417 (5)	C11—H11C	0.9600
C2—C3	1.378 (5)	C12—C13	1.484 (6)
C3—C4	1.385 (5)	C12—H12A	0.9700
C3—H3A	0.9300	C12—H12B	0.9700
C4—C5	1.358 (5)	C13—H13A	0.9600
C4—H4A	0.9300	C13—H13B	0.9600
C5—C6	1.430 (5)	C13—H13C	0.9600
C5—H5A	0.9300
O1i—Cu1—O1	88.42 (14)	N1—C7—H7A	117.2
O1i—Cu1—N1i	93.93 (11)	C6—C7—H7A	117.2
O1—Cu1—N1i	174.47 (11)	C9—C8—C8i	119.1 (2)
O1i—Cu1—N1	174.47 (11)	C9—C8—N1	126.1 (4)
O1—Cu1—N1	93.93 (11)	C8i—C8—N1	114.82 (19)
N1i—Cu1—N1	84.17 (17)	C10—C9—C8	121.6 (4)
C1—O1—Cu1	127.2 (2)	C10—C9—H9A	119.2
C7—N1—C8	122.0 (3)	C8—C9—H9A	119.2
C7—N1—Cu1	124.8 (2)	C9—C10—C10i	119.4 (3)
C8—N1—Cu1	113.1 (2)	C9—C10—C11	119.2 (4)
C2—O2—C12	119.4 (3)	C10i—C10—C11	121.4 (3)
O1—C1—C2	118.0 (3)	C10—C11—H11A	109.5
O1—C1—C6	124.3 (3)	C10—C11—H11B	109.5
C2—C1—C6	117.6 (3)	H11A—C11—H11B	109.5
O2—C2—C3	124.8 (3)	C10—C11—H11C	109.5
O2—C2—C1	114.0 (3)	H11A—C11—H11C	109.5
C3—C2—C1	121.2 (3)	H11B—C11—H11C	109.5
C2—C3—C4	120.7 (4)	O2—C12—C13	108.2 (3)
C2—C3—H3A	119.6	O2—C12—H12A	110.1
C4—C3—H3A	119.6	C13—C12—H12A	110.1
C5—C4—C3	120.2 (4)	O2—C12—H12B	110.1
C5—C4—H4A	119.9	C13—C12—H12B	110.1
C3—C4—H4A	119.9	H12A—C12—H12B	108.4
C4—C5—C6	121.0 (4)	C12—C13—H13A	109.5
C4—C5—H5A	119.5	C12—C13—H13B	109.5
C6—C5—H5A	119.5	H13A—C13—H13B	109.5
C1—C6—C7	123.4 (3)	C12—C13—H13C	109.5
C1—C6—C5	119.2 (3)	H13A—C13—H13C	109.5
C7—C6—C5	117.3 (3)	H13B—C13—H13C	109.5
N1—C7—C6	125.7 (3)
O1i—Cu1—O1—C1	169.0 (3)	C2—C1—C6—C7	−179.4 (3)
N1—Cu1—O1—C1	−6.0 (3)	O1—C1—C6—C5	−177.9 (3)
O1—Cu1—N1—C7	8.1 (3)	C2—C1—C6—C5	0.7 (5)
N1i—Cu1—N1—C7	−177.1 (4)	C4—C5—C6—C1	−0.6 (6)
O1—Cu1—N1—C8	−175.5 (2)	C4—C5—C6—C7	179.5 (3)
N1i—Cu1—N1—C8	−0.69 (17)	C8—N1—C7—C6	177.1 (3)
Cu1—O1—C1—C2	−176.4 (2)	Cu1—N1—C7—C6	−6.9 (5)
Cu1—O1—C1—C6	2.2 (5)	C1—C6—C7—N1	0.7 (6)
C12—O2—C2—C3	0.1 (6)	C5—C6—C7—N1	−179.4 (3)
C12—O2—C2—C1	179.8 (3)	C7—N1—C8—C9	−2.6 (6)
O1—C1—C2—O2	−0.6 (5)	Cu1—N1—C8—C9	−179.1 (3)
C6—C1—C2—O2	−179.3 (3)	C7—N1—C8—C8i	178.5 (4)
O1—C1—C2—C3	179.1 (3)	Cu1—N1—C8—C8i	2.0 (5)
C6—C1—C2—C3	0.5 (5)	C8i—C8—C9—C10	0.2 (6)
O2—C2—C3—C4	178.0 (4)	N1—C8—C9—C10	−178.7 (3)
C1—C2—C3—C4	−1.7 (6)	C8—C9—C10—C10i	0.7 (7)
C2—C3—C4—C5	1.8 (7)	C8—C9—C10—C11	−179.0 (4)
C3—C4—C5—C6	−0.6 (6)	C2—O2—C12—C13	−177.2 (4)
O1—C1—C6—C7	2.0 (6)