{2,2′-[(2,2-Dimethylpropane-1,3-diyl­dinitrilo)bis(phenylmethylidyne)]di­phenolato}copper(II)

Kargar, H.; Kia, R.; Moghadam, M.; Froozandeh, F.; Tahir, M.N.

doi:10.1107/S1600536811028844

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1145

doi:10.1107/S1600536811028844

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{2,2′-[(2,2-Dimethylpropane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenolato}copper(II)

Hadi Kargar,^a ^* Reza Kia,^b,^c Majid Moghadam,^d Fatemeh Froozandeh ^a and Muhammad Nawaz Tahir ^e ^*

^aChemistry Department, Payame Noor University, Tehran 19395-4697, Iran, ^bX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^dCatalysis Division, Department of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 14 July 2011; accepted 18 July 2011; online 23 July 2011)

The complete molecule of the title complex, [Cu(C₃₁H₂₈N₂O₂)], is generated by the application of twofold symmetry; the Cu and CMe₂ 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 intermolecular C—H⋯π interactions.

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_r = 524.09
Tetragonal, P 4₁ 2₁ 2
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.064
S = 0.84
2376 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 918 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Selected geometric parameters (Å, °)

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) $[-y, -x, -z+{\script{3\over 2}}]$ .

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⋯Cg3^iv	0.93	2.76	3.458 (6)	132
Symmetry codes: (ii) $[-y-{\script{1\over 2}}, x+{\script{1\over 2}}, z+{\script{5\over 4}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{3\over 4}}]$ ; (iv) $[-y+{\script{1\over 2}}, x-{\script{1\over 2}}, z+{\script{5\over 4}}]$ .

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028844/tk2765sup1.cif

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

checkCIF report

Comment top

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of potentially tetradentate Schiff bases and their complexes (Kargar et al., 2009; Kargar et al., 2010), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises half of the Schiff base complex as the molecule has crystallographically imposed 2-fold symmetry . The geometry around the Cu^II atom is distorted square planar, Table 1. The dihedral angle between the two phenyl rings is 76.0 (3)°. The crystal packing is stabilized by the intermolecular C—H···π interactions, Table 2.

Related literature top

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

Experimental top

The title compound was synthesized by adding an methanolic solution (25 ml) of bis(2-hydroxybenzophenone)-2,2'-dimethyl propanediimine (2 mmol) to a solution of CuCl₂.4H₂O (2 mmol in 25 ml ethanol). The mixture was refluxed with stirring for half an hour. The resultant green solution was filtered. Dark-green single crystals for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

{2,2'-[(2,2-Dimethylpropane-1,3- diyldinitrilo)bis(phenylmethylidyne)]diphenolato}copper(II) top

Crystal data top

[Cu(C₃₁H₂₈N₂O₂)]	D_x = 1.426 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0005P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
2376 reflections	Δρ_max = 0.83 e Å⁻³
165 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 918 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

[Cu(C₃₁H₂₈N₂O₂)]	Z = 4
M_r = 524.09	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.93 mm⁻¹
a = 9.7435 (14) Å	T = 291 K
c = 25.717 (6) Å	0.21 × 0.11 × 0.08 mm
V = 2441.5 (8) Å³

Data collection top

STOE IPDS 2T Image Plate diffractometer	2376 independent reflections
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]'	1380 reflections with I > 2σ(I)
T_min = 0.995, T_max = 1.000	R_int = 0.088
5595 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.064	Δρ_max = 0.83 e Å⁻³
S = 0.84	Δρ_min = −0.47 e Å⁻³
2376 reflections	Absolute structure: Flack (1983), 918 Friedel pairs
165 parameters	Absolute structure parameter: 0.00 (3)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −y, −x, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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···Cg3^iv	0.93	2.76	3.458 (6)	132

Symmetry codes: (ii) −y−1/2, x+1/2, z+5/4; (iii) −x−1/2, y+1/2, −z−3/4; (iv) −y+1/2, x−1/2, z+5/4.

Experimental details

Crystal data
Chemical formula	[Cu(C₃₁H₂₈N₂O₂)]
M_r	524.09
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	291
a, c (Å)	9.7435 (14), 25.717 (6)
V (Å³)	2441.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.21 × 0.11 × 0.08

Data collection
Diffractometer	STOE IPDS 2T Image Plate diffractometer
Absorption correction	Multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]'
T_min, T_max	0.995, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5595, 2376, 1380
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.064, 0.84
No. of reflections	2376
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.47
Absolute structure	Flack (1983), 918 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Cu1—O1ⁱ	1.891 (3)	Cu1—N1	1.966 (4)
Cu1—N1ⁱ	1.966 (4)	O1—C1	1.305 (5)

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

Symmetry code: (i) −y, −x, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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···Cg3^iv	0.93	2.76	3.458 (6)	132

Symmetry codes: (ii) −y−1/2, x+1/2, z+5/4; (iii) −x−1/2, y+1/2, −z−3/4; (iv) −y+1/2, x−1/2, z+5/4.

Acknowledgements

HK and FF thank PNU for financial support. RK thanks the Science and Research Branch, Islamic Azad University, Tehran for support. MNT thanks Sargodha University for the research facilities.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776–o777. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2009). X-AREA Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 67| Part 8| August 2011| Page m1145

doi:10.1107/S1600536811028844

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{2,2′-[(2,2-Di­methylpropane-1,3-diyl­di­nitrilo)bis­(phenylmethyl­idyne)]di­phenolato}copper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[(2,2-Dimethylpropane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenolato}copper(II)