{2,2'-[(2,2-Dimethylpropane-1,3-diyl-dinitrilo)bis(phenylmethylidyne)]di-phenolato}copper(II).

The complete mol-ecule of the title complex, [Cu(C(31)H(28)N(2)O(2))], is generated by the application of twofold symmetry; the Cu and CMe(2) atoms lie on the axis. The geometry around the Cu(II) atom is distorted square-planar. The dihedral angle between the two phenyl rings is 76.0 (3) °. The crystal packing is stabilized by inter-molecular C-H⋯π inter-actions.

Related literature

For background to tetra­dentate Schiff bases and their complexes, see, for example: Kargar et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

[Cu(C31H28N2O2)]

M = 524.09

Tetragonal,

a = 9.7435 (14) Å

c = 25.717 (6) Å

V = 2441.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 291 K

0.21 × 0.11 × 0.08 mm

Data collection

STOE IPDS 2T Image Plate diffractometer

Absorption correction: multi-scan [MULABS (Blessing, 1995 ▶) in PLATON (Spek, 2009 ▶)] T min = 0.995, T max = 1.000

5595 measured reflections

2376 independent reflections

1380 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.064

S = 0.84

2376 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 918 Friedel pairs

Flack parameter: 0.00 (3)

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 datablock(s) global, I. DOI: 10.1107/S1600536811028844/tk2765sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028844/tk2765Isup2.hkl

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

[Cu(C31H28N2O2)]	Dx = 1.426 Mg m−3
Mr = 524.09	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 374 reflections
Hall symbol: P 4abw 2nw	θ = 2.2–24.9°
a = 9.7435 (14) Å	µ = 0.93 mm−1
c = 25.717 (6) Å	T = 291 K
V = 2441.5 (8) Å3	Block, dark-green
Z = 4	0.21 × 0.11 × 0.08 mm
F(000) = 1092

STOE IPDS 2T Image Plate diffractometer	2376 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
graphite	Rint = 0.088
Detector resolution: 0.15 mm pixels mm-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −10→3
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]'	k = −11→12
Tmin = 0.995, Tmax = 1.000	l = −27→31
5595 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0005P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max < 0.001
2376 reflections	Δρmax = 0.83 e Å−3
165 parameters	Δρmin = −0.47 e Å−3
0 restraints	Absolute structure: Flack (1983), 918 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (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	−0.17381 (7)	0.17381 (7)	0.7500	0.0303 (2)
O1	−0.1851 (4)	0.3469 (4)	0.71702 (12)	0.0358 (9)
N1	−0.0615 (4)	0.0946 (4)	0.69403 (16)	0.0277 (11)
C1	−0.1327 (5)	0.3836 (5)	0.6724 (2)	0.0241 (14)
C2	−0.1492 (6)	0.5209 (6)	0.6563 (2)	0.0368 (16)
H2	−0.1866	0.5835	0.6797	0.044*
C3	−0.1129 (5)	0.5662 (6)	0.6081 (3)	0.0409 (17)
H3	−0.1289	0.6570	0.5987	0.049*
C4	−0.0523 (6)	0.4770 (6)	0.5734 (2)	0.0442 (18)
H4	−0.0287	0.5068	0.5402	0.053*
C5	−0.0271 (6)	0.3441 (7)	0.5881 (2)	0.0359 (16)
H5	0.0148	0.2852	0.5644	0.043*
C6	−0.0622 (5)	0.2935 (5)	0.6374 (2)	0.0253 (13)
C7	−0.0273 (5)	0.1505 (6)	0.6502 (2)	0.0255 (13)
C8	0.0569 (6)	0.0710 (6)	0.61152 (19)	0.0285 (13)
C9	0.0001 (6)	−0.0316 (6)	0.5810 (2)	0.0365 (17)
H9	−0.0939	−0.0476	0.5828	0.044*
C10	0.0788 (7)	−0.1105 (7)	0.5483 (2)	0.0459 (19)
H10	0.0380	−0.1793	0.5286	0.055*
C11	0.2187 (7)	−0.0879 (7)	0.5445 (3)	0.0479 (19)
H11	0.2731	−0.1408	0.5226	0.058*
C12	0.2746 (6)	0.0156 (7)	0.5742 (2)	0.048 (2)
H12A	0.3684	0.0325	0.5720	0.058*
C13	0.1964 (5)	0.0942 (5)	0.6069 (2)	0.0352 (16)
H13	0.2374	0.1639	0.6261	0.042*
C14	−0.0324 (6)	−0.0503 (5)	0.70648 (18)	0.0356 (15)
H14A	0.0016	−0.0953	0.6754	0.043*
H14B	−0.1176	−0.0948	0.7162	0.043*
C15	0.0712 (6)	−0.0712 (6)	0.7500	0.046 (2)
C16	0.2175 (5)	−0.0535 (7)	0.7303 (2)	0.069 (2)
H16A	0.2807	−0.0680	0.7584	0.104*
H16B	0.2289	0.0377	0.7169	0.104*
H16C	0.2351	−0.1190	0.7033	0.104*

	U11	U22	U33	U12	U13	U23
Cu1	0.0317 (3)	0.0317 (3)	0.0277 (5)	0.0088 (6)	0.0062 (4)	0.0062 (4)
O1	0.044 (2)	0.034 (2)	0.029 (2)	0.013 (3)	0.012 (2)	0.005 (2)
N1	0.030 (3)	0.026 (3)	0.027 (3)	0.001 (2)	−0.001 (2)	0.005 (2)
C1	0.016 (3)	0.028 (3)	0.028 (3)	0.002 (3)	0.000 (3)	0.006 (3)
C2	0.027 (4)	0.033 (4)	0.050 (4)	0.002 (3)	0.000 (4)	0.007 (3)
C3	0.030 (4)	0.033 (4)	0.060 (5)	0.002 (3)	0.003 (4)	0.021 (4)
C4	0.043 (4)	0.047 (4)	0.042 (4)	0.006 (4)	0.005 (4)	0.021 (4)
C5	0.033 (4)	0.043 (4)	0.032 (4)	−0.005 (4)	0.005 (3)	0.008 (4)
C6	0.021 (3)	0.028 (4)	0.027 (3)	−0.001 (3)	−0.002 (3)	0.009 (3)
C7	0.020 (3)	0.036 (4)	0.021 (3)	−0.001 (3)	−0.006 (3)	0.001 (3)
C8	0.034 (4)	0.032 (4)	0.019 (3)	0.000 (3)	−0.007 (3)	0.010 (3)
C9	0.032 (4)	0.037 (4)	0.041 (4)	0.002 (3)	0.000 (3)	−0.006 (3)
C10	0.061 (5)	0.044 (5)	0.032 (4)	0.008 (4)	0.002 (4)	−0.007 (3)
C11	0.050 (5)	0.058 (5)	0.035 (4)	0.022 (4)	0.010 (4)	−0.008 (4)
C12	0.024 (4)	0.076 (5)	0.044 (5)	0.010 (4)	0.014 (3)	0.020 (4)
C13	0.024 (4)	0.040 (4)	0.042 (4)	−0.011 (3)	0.000 (3)	0.004 (3)
C14	0.044 (4)	0.024 (3)	0.038 (4)	0.005 (3)	0.019 (3)	0.000 (3)
C15	0.048 (3)	0.048 (3)	0.040 (5)	0.018 (5)	0.023 (4)	0.023 (4)
C16	0.048 (5)	0.113 (6)	0.047 (5)	0.037 (4)	0.020 (3)	0.028 (4)

Cu1—O1i	1.891 (3)	C8—C9	1.386 (7)
Cu1—O1	1.891 (3)	C9—C10	1.373 (7)
Cu1—N1i	1.966 (4)	C9—H9	0.9300
Cu1—N1	1.966 (4)	C10—C11	1.384 (7)
O1—C1	1.305 (5)	C10—H10	0.9300
N1—C7	1.295 (6)	C11—C12	1.377 (8)
N1—C14	1.475 (6)	C11—H11	0.9300
C1—C2	1.410 (7)	C12—C13	1.369 (7)
C1—C6	1.433 (7)	C12—H12A	0.9300
C2—C3	1.362 (7)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.521 (6)
C3—C4	1.380 (8)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.371 (8)	C15—C14i	1.521 (6)
C4—H4	0.9300	C15—C16i	1.522 (6)
C5—C6	1.405 (6)	C15—C16	1.522 (6)
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.471 (7)	C16—H16B	0.9600
C7—C8	1.504 (7)	C16—H16C	0.9600
C8—C13	1.383 (7)
O1—Cu1—N1	93.11 (16)	C10—C9—C8	121.8 (6)
O1i—Cu1—O1	95.6 (2)	C10—C9—H9	119.1
O1i—Cu1—N1i	93.11 (16)	C8—C9—H9	119.1
O1—Cu1—N1i	147.96 (16)	C9—C10—C11	120.3 (7)
O1i—Cu1—N1	147.96 (16)	C9—C10—H10	119.9
N1i—Cu1—N1	95.7 (2)	C11—C10—H10	119.9
C1—O1—Cu1	128.0 (3)	C12—C11—C10	117.8 (6)
C7—N1—C14	122.8 (4)	C12—C11—H11	121.1
C7—N1—Cu1	127.9 (4)	C10—C11—H11	121.1
C14—N1—Cu1	108.9 (3)	C13—C12—C11	122.0 (6)
O1—C1—C2	118.3 (5)	C13—C12—H12A	119.0
O1—C1—C6	124.9 (5)	C11—C12—H12A	119.0
C2—C1—C6	116.8 (5)	C12—C13—C8	120.6 (6)
C3—C2—C1	123.1 (6)	C12—C13—H13	119.7
C3—C2—H2	118.5	C8—C13—H13	119.7
C1—C2—H2	118.5	N1—C14—C15	114.6 (4)
C2—C3—C4	119.8 (6)	N1—C14—H14A	108.6
C2—C3—H3	120.1	C15—C14—H14A	108.6
C4—C3—H3	120.1	N1—C14—H14B	108.6
C5—C4—C3	119.6 (6)	C15—C14—H14B	108.6
C5—C4—H4	120.2	H14A—C14—H14B	107.6
C3—C4—H4	120.2	C14—C15—C14i	111.3 (7)
C4—C5—C6	122.5 (6)	C14—C15—C16i	107.1 (3)
C4—C5—H5	118.8	C14i—C15—C16i	111.2 (3)
C6—C5—H5	118.8	C14—C15—C16	111.2 (3)
C5—C6—C1	118.0 (5)	C14i—C15—C16	107.1 (3)
C5—C6—C7	118.6 (5)	C16i—C15—C16	108.9 (7)
C1—C6—C7	123.4 (5)	C15—C16—H16A	109.5
N1—C7—C6	122.2 (5)	C15—C16—H16B	109.5
N1—C7—C8	119.9 (5)	H16A—C16—H16B	109.5
C6—C7—C8	117.8 (5)	C15—C16—H16C	109.5
C13—C8—C9	117.4 (5)	H16A—C16—H16C	109.5
C13—C8—C7	120.6 (5)	H16B—C16—H16C	109.5
C9—C8—C7	121.9 (5)
O1i—Cu1—O1—C1	−148.3 (5)	C14—N1—C7—C8	−5.7 (8)
N1i—Cu1—O1—C1	106.7 (5)	Cu1—N1—C7—C8	−178.3 (3)
N1—Cu1—O1—C1	0.9 (5)	C5—C6—C7—N1	−176.9 (5)
O1i—Cu1—N1—C7	100.2 (5)	C1—C6—C7—N1	1.7 (8)
O1—Cu1—N1—C7	−5.5 (5)	C5—C6—C7—C8	6.1 (7)
N1i—Cu1—N1—C7	−154.7 (5)	C1—C6—C7—C8	−175.2 (4)
O1i—Cu1—N1—C14	−73.3 (5)	N1—C7—C8—C13	−101.0 (6)
O1—Cu1—N1—C14	−178.9 (3)	C6—C7—C8—C13	76.0 (6)
N1i—Cu1—N1—C14	31.9 (3)	N1—C7—C8—C9	76.0 (7)
Cu1—O1—C1—C2	−177.3 (4)	C6—C7—C8—C9	−107.0 (6)
Cu1—O1—C1—C6	4.5 (8)	C13—C8—C9—C10	1.7 (8)
O1—C1—C2—C3	−172.2 (5)	C7—C8—C9—C10	−175.5 (6)
C6—C1—C2—C3	6.2 (9)	C8—C9—C10—C11	−0.7 (10)
C1—C2—C3—C4	−2.5 (9)	C9—C10—C11—C12	−0.3 (10)
C2—C3—C4—C5	−1.1 (9)	C10—C11—C12—C13	0.3 (10)
C3—C4—C5—C6	0.8 (9)	C11—C12—C13—C8	0.7 (9)
C4—C5—C6—C1	3.0 (8)	C9—C8—C13—C12	−1.7 (8)
C4—C5—C6—C7	−178.2 (5)	C7—C8—C13—C12	175.5 (5)
O1—C1—C6—C5	172.0 (5)	C7—N1—C14—C15	113.2 (5)
C2—C1—C6—C5	−6.2 (7)	Cu1—N1—C14—C15	−73.0 (5)
O1—C1—C6—C7	−6.7 (8)	N1—C14—C15—C14i	39.7 (3)
C2—C1—C6—C7	175.1 (5)	N1—C14—C15—C16i	161.4 (5)
C14—N1—C7—C6	177.4 (4)	N1—C14—C15—C16	−79.7 (7)
Cu1—N1—C7—C6	4.8 (8)

Cg1, Cg2 and Cg3 are the centroids of the Cu/O1/C1/C6/C7/N1, Cu/O1'/C1'/C6'/C7'/N1' and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ii	0.93	2.85	3.415 (6)	120
C3—H3···Cg2iii	0.93	2.85	3.415 (6)	120
C12—H12A···Cg3iv	0.93	2.76	3.458 (6)	132

Cu1—O1	1.891 (3)
Cu1—N1	1.966 (4)

O1—Cu1—N1	93.11 (16)
O1i—Cu1—O1	95.6 (2)
N1i—Cu1—N1	95.7 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the Cu/O1/C1/C6/C7/N1, Cu/O1′/C1′/C6′/C7′/N1′ and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ii	0.93	2.85	3.415 (6)	120
C3—H3⋯Cg2iii	0.93	2.85	3.415 (6)	120
C12—H12A⋯Cg3iv	0.93	2.76	3.458 (6)	132

Symmetry codes: (ii) ; (iii) ; (iv) .