Bis{μ-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}dicopper(II) N,N′-dimethyl­formamide disolvate

Yu, G.; Ding, Y.; Wang, L.; Fu, Z.; Hu, X.

doi:10.1107/S1600536808005394

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m504

doi:10.1107/S1600536808005394

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Bis{μ-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}dicopper(II) N,N′-dimethylformamide disolvate

Guofeng Yu,^a ^* Yu Ding,^a Li Wang,^a Zhengbing Fu ^a and Xinliang Hu ^a

^aDepartment of Chemistry, Xiaogan University, Xiaogan, Hubei 432000, People's Republic of China
^*Correspondence e-mail: dy9802@126.com

(Received 8 December 2007; accepted 26 February 2008; online 29 February 2008)

The title compound, [Cu₂(C₂₀H₁₄N₂O₂)₂]·2C₃H₇NO, consists of a centrosymmetric dimer composed of two copper(II) ions and two tetradentate salphen ligands {H₂salphen is 2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenol}, and two dimethylformamide solvent molecules. The Cu^II atom is bonded to two N imino atoms and three phenolate O atoms of salphen. One deprotonated phenol group of each ligand bridges two Cu atoms, forming the dimer. The geometry about the five-coordinate Cu atom can best be described as slightly distorted rectangular pyramidal. The crystal structure is stabilized by π–π interactions [centroid-centroid distance 3.779 (2) Å] and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Suzuki et al. (1997 ).

Experimental

Crystal data

[Cu₂(C₂₀H₁₄N₂O₂)₂]·2C₃H₇NO
M_r = 901.94
Monoclinic, P 2₁ /n
a = 8.1864 (5) Å
b = 14.792 (1) Å
c = 16.9584 (11) Å
β = 93.252 (1)°
V = 2050.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 294 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.811, T_max = 0.898
13976 measured reflections
4468 independent reflections
3126 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.129
S = 0.98
4468 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.907 (2)
Cu1—O2	1.909 (2)
Cu1—N1	1.946 (2)
Cu1—N2	1.950 (2)
Cu1—O1ⁱ	2.783 (11).
Symmetry code: (i) -x-3, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3	0.93	2.44	3.244 (4)	145
C5—H5⋯O3	0.93	2.54	3.333 (4)	144
C23—H23⋯O2ⁱⁱ	0.93	2.58	3.457 (5)	158
C7—H7⋯O3ⁱⁱⁱ	0.93	2.41	3.333 (4)	170
C2—H2⋯O3ⁱⁱⁱ	0.93	2.47	3.389 (4)	172
C21—H21A⋯O3	0.96	2.36	2.756 (5)	104
Symmetry codes: (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global, New_Global_Publ_Block_1. DOI: 10.1107/S1600536808005394/br2066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005394/br2066Isup2.hkl

checkCIF report

Comment top

The stucture of the title compound, [Cu(salphen)]₂˙2DMF, (DMF= N,N'-dimethylformamide), (I), is shown in Fig.1.

The salphen derivatives and their manganese complexes have been synthesized and characterized(Suzuki et al.,1997).

Herein, we report the crystal structure of such a compound. As shown in Fig.1, the molecular structure of the title compound is constructed of a centrosymmetric dimer in which the copper(II) atoms are linked by µ-phenoxo bridges from one of the phenolic oxygen atoms of each salphen ligand to the opposite metal center. The distance of Cu1···Cu1(2 - x,-y,-z) separation and the angles of Cu1–O1–Cu1(2 - x,-y,-z)are 3.436 Å, and 92.19°, respectively. Two nitrogen atoms and two oxygen atoms from salphen ligands occupy the coordination sites about each copper. The apical Cu–O (phenoxo) and Cu–N (imine) (see Table 2) bond distances are somewhat shorter than the long equatorial Cu1—O1 distance. The basal atoms about the two copper atoms are coplanar; consequently, the environment around each copper atom can be described as a distorted triangular pyramid.

The centroid-centroid distance between the C8—C13 benzene ring (centroid Cg1) belonging to one salicylaldehyde ring system in one dimer and the C15—C20 benzene ring (centroid Cg2) of the salicylaldehyde ring system from the neighboring dimer at (2 - x, -y, -z) is 3.779 (2), and the dihedral angles (between planes Cg1 and Cg2) and (between planes Cg1- Cg2 vector and the normal to the C8—C13 ring) are 10.82 and 16.52°, respectively; these values indicate the existence of significant π-π stacking interactions between adjacent rings, as shown in Fig.2, which stabilizes the crystal structure together with the hydrogen bonds.

Related literature top

For related literature, see: Suzuki et al. (1997).

Experimental top

[Cu(C₂₀H₁₄N₂O₂)]₂.2DMF was prepared as followings: to a solution of H₂salphen 0.158 mg(0.5 mmol) in methanol (20 mL) and DMF(20 mL) was added Cu(OAc)₂˙2H₂O(0.113 g, 0.5 mmol). After the mixture was stirred for half an hour, the solution was filtered. The filtrate was kept for several days at ambient temperature, and green-black block crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level.
	Fig. 2. The molecular packing diagram of (I).

Bis{µ-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolato}dicopper(II) N,N'-dimethylformamide disolvate top

Crystal data top

[Cu₂(C₂₀H₁₄N₂O₂)₂]·2C₃H₇NO	F(000) = 932
M_r = 901.94	D_x = 1.461 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3178 reflections
a = 8.1864 (5) Å	θ = 2.8–23.0°
b = 14.792 (1) Å	µ = 1.10 mm⁻¹
c = 16.9584 (11) Å	T = 294 K
β = 93.252 (1)°	Block, black
V = 2050.2 (2) Å³	0.20 × 0.10 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4468 independent reflections
Radiation source: fine-focus sealed tube	3126 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.811, T_max = 0.898	k = −14→18
13976 measured reflections	l = −20→21

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0609P)²] where P = (F_o² + 2F_c²)/3
4468 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu₂(C₂₀H₁₄N₂O₂)₂]·2C₃H₇NO	V = 2050.2 (2) Å³
M_r = 901.94	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1864 (5) Å	µ = 1.10 mm⁻¹
b = 14.792 (1) Å	T = 294 K
c = 16.9584 (11) Å	0.20 × 0.10 × 0.10 mm
β = 93.252 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4468 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3126 reflections with I > 2σ(I)
T_min = 0.811, T_max = 0.898	R_int = 0.083
13976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	Δρ_max = 0.52 e Å⁻³
4468 reflections	Δρ_min = −0.36 e Å⁻³
273 parameters

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	0.87999 (4)	0.02801 (2)	0.07623 (2)	0.03962 (15)
C1	0.7432 (3)	0.2022 (2)	0.05569 (18)	0.0394 (7)
C2	0.6560 (4)	0.2775 (2)	0.0271 (2)	0.0506 (8)
H2	0.5941	0.2742	−0.0205	0.061*
C3	0.6622 (5)	0.3569 (2)	0.0699 (2)	0.0614 (10)
H3	0.6053	0.4075	0.0508	0.074*
C4	0.7528 (5)	0.3612 (2)	0.1410 (3)	0.0688 (11)
H4	0.7547	0.4146	0.1700	0.083*
C5	0.8397 (4)	0.2880 (2)	0.1695 (2)	0.0546 (9)
H5	0.9014	0.2921	0.2171	0.065*
C6	0.8359 (3)	0.2075 (2)	0.12719 (18)	0.0392 (7)
C7	0.6479 (4)	0.0977 (2)	−0.04292 (18)	0.0399 (7)
H7	0.5858	0.1452	−0.0647	0.048*
C8	0.6304 (4)	0.0124 (2)	−0.08095 (17)	0.0412 (7)
C9	0.7215 (4)	−0.0655 (2)	−0.05630 (19)	0.0419 (7)
C10	0.6853 (4)	−0.1464 (2)	−0.0970 (2)	0.0509 (8)
H10	0.7399	−0.1991	−0.0812	0.061*
C11	0.5710 (4)	−0.1499 (3)	−0.1597 (2)	0.0585 (10)
H11	0.5500	−0.2046	−0.1853	0.070*
C12	0.4865 (4)	−0.0729 (3)	−0.1852 (2)	0.0566 (9)
H12	0.4112	−0.0753	−0.2283	0.068*
C13	0.5161 (4)	0.0058 (2)	−0.1460 (2)	0.0495 (9)
H13	0.4588	0.0573	−0.1627	0.059*
C14	0.9997 (4)	0.1198 (2)	0.21836 (19)	0.0473 (8)
H14	1.0089	0.1718	0.2492	0.057*
C15	1.0785 (4)	0.0411 (2)	0.2491 (2)	0.0478 (8)
C16	1.0733 (4)	−0.0430 (2)	0.2097 (2)	0.0483 (9)
C17	1.1600 (5)	−0.1157 (3)	0.2469 (2)	0.0654 (11)
H17	1.1591	−0.1720	0.2226	0.078*
C18	1.2455 (5)	−0.1043 (3)	0.3184 (3)	0.0746 (12)
H18	1.3026	−0.1529	0.3411	0.090*
C19	1.2486 (5)	−0.0225 (3)	0.3570 (2)	0.0787 (14)
H19	1.3061	−0.0159	0.4055	0.094*
C20	1.1659 (5)	0.0486 (3)	0.3230 (2)	0.0652 (11)
H20	1.1671	0.1038	0.3493	0.078*
C21	0.7335 (6)	0.1052 (3)	0.4145 (3)	0.0950 (15)
H21A	0.8299	0.0998	0.3852	0.142*
H21B	0.6512	0.0643	0.3932	0.142*
H21C	0.7597	0.0905	0.4689	0.142*
C22	0.5134 (5)	0.2143 (3)	0.4363 (3)	0.0993 (17)
H22A	0.4918	0.2780	0.4326	0.149*
H22B	0.5093	0.1953	0.4902	0.149*
H22C	0.4325	0.1820	0.4042	0.149*
C23	0.7679 (5)	0.2604 (3)	0.3829 (2)	0.0601 (10)
H23	0.7243	0.3184	0.3800	0.072*
N1	0.7417 (3)	0.11587 (16)	0.01899 (14)	0.0367 (6)
N2	0.9162 (3)	0.12659 (17)	0.15158 (14)	0.0384 (6)
N3	0.6731 (4)	0.1958 (2)	0.40887 (18)	0.0592 (8)
O1	0.8363 (3)	−0.06591 (14)	0.00094 (13)	0.0492 (6)
O2	0.9963 (3)	−0.05820 (15)	0.14172 (14)	0.0524 (6)
O3	0.9070 (3)	0.25103 (17)	0.36246 (15)	0.0639 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0424 (2)	0.0340 (2)	0.0420 (2)	0.00078 (17)	−0.00157 (16)	0.00026 (17)
C1	0.0368 (16)	0.0327 (17)	0.0494 (18)	−0.0021 (13)	0.0080 (13)	0.0017 (14)
C2	0.052 (2)	0.0390 (19)	0.060 (2)	−0.0029 (16)	−0.0039 (16)	0.0066 (17)
C3	0.069 (2)	0.035 (2)	0.080 (3)	0.0043 (17)	−0.001 (2)	0.0036 (19)
C4	0.094 (3)	0.033 (2)	0.080 (3)	−0.002 (2)	0.004 (2)	−0.011 (2)
C5	0.067 (2)	0.044 (2)	0.052 (2)	−0.0055 (17)	−0.0006 (17)	−0.0067 (17)
C6	0.0384 (16)	0.0331 (18)	0.0468 (18)	−0.0044 (13)	0.0090 (13)	−0.0004 (14)
C7	0.0396 (16)	0.0368 (18)	0.0431 (17)	0.0010 (14)	0.0015 (13)	0.0054 (14)
C8	0.0402 (17)	0.0428 (19)	0.0410 (18)	−0.0072 (14)	0.0065 (13)	−0.0002 (15)
C9	0.0402 (17)	0.0417 (19)	0.0445 (18)	−0.0069 (15)	0.0090 (14)	−0.0039 (15)
C10	0.054 (2)	0.043 (2)	0.057 (2)	−0.0049 (16)	0.0113 (17)	−0.0072 (17)
C11	0.059 (2)	0.060 (3)	0.058 (2)	−0.0212 (19)	0.0127 (18)	−0.0195 (19)
C12	0.048 (2)	0.072 (3)	0.049 (2)	−0.0140 (19)	0.0005 (16)	−0.012 (2)
C13	0.0421 (19)	0.057 (2)	0.049 (2)	−0.0032 (16)	0.0006 (15)	0.0002 (17)
C14	0.0434 (18)	0.054 (2)	0.0449 (19)	−0.0027 (16)	0.0038 (15)	−0.0066 (16)
C15	0.0367 (17)	0.060 (2)	0.0468 (19)	−0.0023 (15)	0.0010 (14)	0.0082 (17)
C16	0.0377 (17)	0.056 (2)	0.051 (2)	−0.0013 (15)	0.0059 (15)	0.0180 (17)
C17	0.067 (2)	0.060 (3)	0.068 (3)	0.004 (2)	0.001 (2)	0.024 (2)
C18	0.068 (3)	0.080 (3)	0.075 (3)	0.003 (2)	−0.006 (2)	0.039 (3)
C19	0.071 (3)	0.108 (4)	0.055 (2)	−0.005 (3)	−0.016 (2)	0.026 (3)
C20	0.062 (2)	0.083 (3)	0.049 (2)	−0.005 (2)	−0.0043 (18)	0.007 (2)
C21	0.113 (4)	0.057 (3)	0.119 (4)	0.005 (3)	0.038 (3)	0.011 (3)
C22	0.066 (3)	0.095 (4)	0.140 (5)	−0.001 (3)	0.032 (3)	−0.015 (3)
C23	0.073 (3)	0.047 (2)	0.060 (2)	0.001 (2)	0.002 (2)	−0.0103 (19)
N1	0.0376 (13)	0.0332 (14)	0.0393 (14)	−0.0014 (11)	0.0030 (11)	0.0017 (11)
N2	0.0356 (13)	0.0390 (15)	0.0405 (14)	−0.0020 (11)	0.0026 (11)	−0.0006 (12)
N3	0.0649 (19)	0.0447 (19)	0.070 (2)	0.0021 (15)	0.0183 (16)	−0.0075 (16)
O1	0.0563 (14)	0.0337 (12)	0.0564 (14)	0.0036 (11)	−0.0077 (11)	−0.0049 (11)
O2	0.0599 (15)	0.0405 (13)	0.0557 (14)	0.0052 (11)	−0.0063 (11)	0.0072 (11)
O3	0.0575 (16)	0.0729 (18)	0.0617 (16)	−0.0080 (14)	0.0076 (13)	−0.0121 (14)

Geometric parameters (Å, º) top

Cu1—O1	1.907 (2)	C12—C13	1.355 (5)
Cu1—O2	1.909 (2)	C12—H12	0.9300
Cu1—N1	1.946 (2)	C13—H13	0.9300
Cu1—N2	1.950 (2)	C14—N2	1.293 (4)
Cu1—O1ⁱ	2.783 (11)	C14—C15	1.416 (4)
C1—C2	1.395 (4)	C14—H14	0.9300
C1—C6	1.396 (4)	C15—C20	1.411 (5)
C1—N1	1.420 (4)	C15—C16	1.412 (5)
C2—C3	1.380 (5)	C16—O2	1.302 (4)
C2—H2	0.9300	C16—C17	1.416 (4)
C3—C4	1.381 (6)	C17—C18	1.375 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.369 (5)	C18—C19	1.375 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.389 (4)	C19—C20	1.360 (6)
C5—H5	0.9300	C19—H19	0.9300
C6—N2	1.416 (4)	C20—H20	0.9300
C7—N1	1.294 (4)	C21—N3	1.431 (5)
C7—C8	1.421 (4)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C13	1.409 (4)	C21—H21C	0.9600
C8—C9	1.423 (5)	C22—N3	1.438 (5)
C9—O1	1.312 (4)	C22—H22A	0.9600
C9—C10	1.405 (4)	C22—H22B	0.9600
C10—C11	1.376 (5)	C22—H22C	0.9600
C10—H10	0.9300	C23—O3	1.216 (4)
C11—C12	1.389 (5)	C23—N3	1.321 (5)
C11—H11	0.9300	C23—H23	0.9300

O1—Cu1—O2	88.35 (10)	N2—C14—H14	116.8
O1—Cu1—N1	94.06 (10)	C15—C14—H14	116.8
O2—Cu1—N1	173.09 (10)	C20—C15—C16	119.3 (3)
O1—Cu1—N2	177.59 (9)	C20—C15—C14	117.4 (4)
O2—Cu1—N2	93.78 (10)	C16—C15—C14	123.3 (3)
N1—Cu1—N2	83.69 (10)	O2—C16—C15	124.8 (3)
C2—C1—C6	119.9 (3)	O2—C16—C17	118.0 (3)
C2—C1—N1	125.1 (3)	C15—C16—C17	117.2 (3)
C6—C1—N1	115.0 (3)	C18—C17—C16	121.1 (4)
C3—C2—C1	119.6 (3)	C18—C17—H17	119.4
C3—C2—H2	120.2	C16—C17—H17	119.4
C1—C2—H2	120.2	C17—C18—C19	121.5 (4)
C2—C3—C4	120.0 (3)	C17—C18—H18	119.3
C2—C3—H3	120.0	C19—C18—H18	119.3
C4—C3—H3	120.0	C20—C19—C18	118.8 (4)
C5—C4—C3	120.9 (4)	C20—C19—H19	120.6
C5—C4—H4	119.5	C18—C19—H19	120.6
C3—C4—H4	119.5	C19—C20—C15	122.1 (4)
C4—C5—C6	120.0 (3)	C19—C20—H20	119.0
C4—C5—H5	120.0	C15—C20—H20	119.0
C6—C5—H5	120.0	N3—C21—H21A	109.5
C5—C6—C1	119.5 (3)	N3—C21—H21B	109.5
C5—C6—N2	125.2 (3)	H21A—C21—H21B	109.5
C1—C6—N2	115.2 (3)	N3—C21—H21C	109.5
N1—C7—C8	126.3 (3)	H21A—C21—H21C	109.5
N1—C7—H7	116.8	H21B—C21—H21C	109.5
C8—C7—H7	116.8	N3—C22—H22A	109.5
C13—C8—C7	117.5 (3)	N3—C22—H22B	109.5
C13—C8—C9	119.2 (3)	H22A—C22—H22B	109.5
C7—C8—C9	123.3 (3)	N3—C22—H22C	109.5
O1—C9—C10	118.9 (3)	H22A—C22—H22C	109.5
O1—C9—C8	124.2 (3)	H22B—C22—H22C	109.5
C10—C9—C8	116.9 (3)	O3—C23—N3	126.1 (4)
C11—C10—C9	121.8 (3)	O3—C23—H23	116.9
C11—C10—H10	119.1	N3—C23—H23	116.9
C9—C10—H10	119.1	C7—N1—C1	122.1 (3)
C10—C11—C12	121.0 (3)	C7—N1—Cu1	124.6 (2)
C10—C11—H11	119.5	C1—N1—Cu1	113.06 (19)
C12—C11—H11	119.5	C14—N2—C6	122.3 (3)
C13—C12—C11	118.6 (3)	C14—N2—Cu1	124.7 (2)
C13—C12—H12	120.7	C6—N2—Cu1	112.94 (19)
C11—C12—H12	120.7	C23—N3—C21	119.5 (3)
C12—C13—C8	122.4 (4)	C23—N3—C22	122.2 (3)
C12—C13—H13	118.8	C21—N3—C22	118.3 (3)
C8—C13—H13	118.8	C9—O1—Cu1	126.3 (2)
N2—C14—C15	126.4 (3)	C16—O2—Cu1	126.9 (2)

Symmetry code: (i) −x−3, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.44	3.244 (4)	145
C5—H5···O3	0.93	2.54	3.333 (4)	144
C23—H23···O2ⁱⁱ	0.93	2.58	3.457 (5)	158
C7—H7···O3ⁱⁱⁱ	0.93	2.41	3.333 (4)	170
C2—H2···O3ⁱⁱⁱ	0.93	2.47	3.389 (4)	172
C21—H21A···O3	0.96	2.36	2.756 (5)	104

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂₀H₁₄N₂O₂)₂]·2C₃H₇NO
M_r	901.94
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	8.1864 (5), 14.792 (1), 16.9584 (11)
β (°)	93.252 (1)
V (Å³)	2050.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.811, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	13976, 4468, 3126
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.129, 0.98
No. of reflections	4468
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.36

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.907 (2)	Cu1—N2	1.950 (2)
Cu1—O2	1.909 (2)	Cu1—O1ⁱ	2.783 (11)
Cu1—N1	1.946 (2)

Symmetry code: (i) −x−3, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.44	3.244 (4)	145.1
C5—H5···O3	0.93	2.54	3.333 (4)	143.9
C23—H23···O2ⁱⁱ	0.93	2.58	3.457 (5)	157.6
C7—H7···O3ⁱⁱⁱ	0.93	2.41	3.333 (4)	170.0
C2—H2···O3ⁱⁱⁱ	0.93	2.47	3.389 (4)	171.8
C21—H21A···O3	0.96	2.36	2.756 (5)	104.0

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

Acknowledgements

This work was supported by the Natural Science Foundation of Xiaogan University (Z2008012).

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (20081). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suzuki, M., Ishikawa, T., Harada, A., Ohba, S., Sakamoto, M. & Nishida, Y. (1997). Polyhedron, 16, 2553–2561. CSD CrossRef CAS Web of Science Google Scholar

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

Bis{μ-2,2′-[o-phenyl­enebis(nitrilo­methyl­­idyne)]diphenolato}dicopper(II) N,N′-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}dicopper(II) N,N′-dimethylformamide disolvate