{2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}copper(II)

Dong, W.-K.; Wu, J.-C.; Yao, J.; Gong, S.-S.; Tong, J.-F.

doi:10.1107/S1600536809023010

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m802

doi:10.1107/S1600536809023010

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{2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}copper(II)

Wen-Kui Dong,^a ^* Jian-Chao Wu,^a Jian Yao,^a Shang-Sheng Gong ^a and Jun-Feng Tong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 12 June 2009; accepted 15 June 2009; online 20 June 2009)

The title complex, [Cu(C₂₆H₂₂N₂O₄)], is isostructural with its Ni analogue. All intramolecular distances and angles are very similar for the two structures, whereas the packing of the molecules, including C—H⋯O and C—H⋯π interactions, are slightly different.

Related literature

For transition metal complexes with multidentate salen-type ligands, see: Akine et al. (2005 ); Dong et al. (2009a ,b ); Katsuki (1995 ); Ray et al. (2003 ); Sun et al. (2008 ). For the isostructural Ni complex, see: Dong et al. (2009c ).

Experimental

Crystal data

[Cu(C₂₆H₂₂N₂O₄)]
M_r = 490.00
Monoclinic, P 2₁ /n
a = 13.0288 (17) Å
b = 7.8934 (12) Å
c = 21.292 (2) Å
β = 103.217 (2)°
V = 2131.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 298 K
0.41 × 0.17 × 0.07 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.670, T_max = 0.929
10698 measured reflections
3753 independent reflections
2278 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.108
S = 1.03
3753 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O3ⁱ	0.96	2.64	3.375 (5)	134
C23—H23⋯O2ⁱⁱ	0.93	2.43	3.261 (5)	149
C4—H4C⋯Cg8ⁱ	0.96	2.68	3.564 (6)	153
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg8 is the centroid of the C21–C26 ring.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023010/at2815sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023010/at2815Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with multidentate salen-type ligands are very interesting in modern coordination chemistry because they have mono-, di- or tri-nuclear metal complexes with important stereochemistry (Katsuki et al., 1995; Akine et al., 2005; Dong et al., 2009b). Metal derivatives of salen-type compounds have been investigated extensively, and copper(II) complexes play a major role in both synthetic and structural research (Ray et al., 2003; Dong et al., 2009a).

In this paper, a new mononuclear copper(II) complex with salen-type bisoxime chelating ligand, 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol, has been synthesized (Sun et al., 2008). The X-ray crystallography of the title complex (Fig. 1) reveals the complex crystallizes in the monoclinic system, with P2₁/c space group. There is a crystallographic twofold screw axis (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z). The dihedral angle between the coordination plane of O3—Cu1—N1 and that of O4—Cu1—N2 is 26.53°, indicating slight distortion toward tetrahedral geometry from the square planar structure [Cu1—O3: 1.876 (3) Å; Cu1—O4: 1.895 (3) Å; Cu1—N1: 1.976 (3) Å; Cu1—N2: 1.947 (3) Å]), with a mean deviation of 0.016 Å from the N₂O₂ plane. The crystal structure is further stabilized by intermolecular C16—H16A···O3, C23—H23···O2 hydrogen bonds and C4—H4C···π interactions (Table 1), which link neighbouring molecules into extended chains along the c axis.

Related literature top

For transition metal complexes with multidentate salen-type ligands, see: Akine et al. (2005); Dong et al. (2009a,b); Katsuki (1995); Ray et al. (2003); Sun et al. (2008). For the isostructural Ni complex, see: Dong et al. (2009c). Cg8 is the centroid of the C21–C26 ring.

Experimental top

A solution of Cu(II) acetate monohydrate (1.7 mg, 0.0085 mmol) in ethanol (5 ml) was added dropwise to a solution of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol (3.4 mg, 0.0079 mmol) in dichloromethane (5 ml). The colour of the mixing solution turns to brown, immediately, and was allowed to stand at room temperature for about one week, the solvent was partially evaporated and obtained dark-brown needle-like single crystals suitable for X-ray crystallographic analysis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecule structure of the title complex possessing a crystallographic twofold screw axis passing through the middle point of (–O)–H₂C—CH₂–(O–) unit (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z). Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

{2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}copper(II) top

Crystal data top

[Cu(C₂₆H₂₂N₂O₄)]	F(000) = 1012
M_r = 490.00	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2535 reflections
a = 13.0288 (17) Å	θ = 3.0–25.3°
b = 7.8934 (12) Å	µ = 1.06 mm⁻¹
c = 21.292 (2) Å	T = 298 K
β = 103.217 (2)°	Needle, dark-brown
V = 2131.7 (5) Å³	0.41 × 0.17 × 0.07 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	2278 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
T_min = 0.670, T_max = 0.929	k = −9→9
10698 measured reflections	l = −25→23

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0328P)² + 2.0905P] where P = (F_o² + 2F_c²)/3
3753 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Cu(C₂₆H₂₂N₂O₄)]	V = 2131.7 (5) Å³
M_r = 490.00	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.0288 (17) Å	µ = 1.06 mm⁻¹
b = 7.8934 (12) Å	T = 298 K
c = 21.292 (2) Å	0.41 × 0.17 × 0.07 mm
β = 103.217 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3753 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2278 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.929	R_int = 0.051
10698 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
3753 reflections	Δρ_min = −0.41 e Å⁻³
298 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	0.73155 (4)	0.18038 (7)	0.77719 (2)	0.04608 (19)
N1	0.7004 (3)	0.1798 (4)	0.86373 (14)	0.0465 (9)
N2	0.8811 (2)	0.2362 (4)	0.79867 (15)	0.0452 (9)
O1	0.7720 (2)	0.1113 (4)	0.91807 (14)	0.0680 (9)
O2	0.9266 (2)	0.2769 (4)	0.86424 (13)	0.0512 (8)
O3	0.5864 (2)	0.1927 (4)	0.74053 (12)	0.0555 (8)
O4	0.7494 (2)	0.0995 (4)	0.69654 (13)	0.0562 (8)
C1	0.8537 (4)	0.0179 (6)	0.9005 (2)	0.0689 (14)
H1A	0.8289	−0.0266	0.8572	0.083*
H1B	0.8730	−0.0772	0.9297	0.083*
C2	0.9486 (3)	0.1269 (6)	0.9028 (2)	0.0637 (13)
H2A	0.9779	0.1594	0.9472	0.076*
H2B	1.0015	0.0610	0.8882	0.076*
C3	0.6172 (3)	0.2413 (5)	0.87978 (19)	0.0465 (11)
C4	0.6114 (4)	0.2381 (7)	0.94956 (19)	0.0661 (14)
H4A	0.6453	0.1376	0.9697	0.099*
H4B	0.5389	0.2384	0.9523	0.099*
H4C	0.6463	0.3362	0.9711	0.099*
C5	0.5175 (3)	0.2722 (5)	0.76545 (19)	0.0435 (10)
C6	0.5294 (3)	0.3069 (5)	0.83128 (19)	0.0447 (10)
C7	0.4498 (4)	0.4048 (6)	0.8504 (2)	0.0572 (12)
H7	0.4581	0.4316	0.8938	0.069*
C8	0.3623 (4)	0.4603 (6)	0.8078 (2)	0.0622 (13)
H8	0.3129	0.5248	0.8225	0.075*
C9	0.3450 (3)	0.4223 (6)	0.7418 (2)	0.0532 (12)
C10	0.4212 (3)	0.3260 (5)	0.7203 (2)	0.0466 (10)
C11	0.4048 (3)	0.2850 (6)	0.6547 (2)	0.0553 (12)
H11	0.4546	0.2203	0.6404	0.066*
C12	0.3158 (4)	0.3395 (7)	0.6113 (2)	0.0737 (15)
H12	0.3054	0.3109	0.5679	0.088*
C13	0.2418 (4)	0.4369 (7)	0.6322 (3)	0.0781 (16)
H13	0.1819	0.4739	0.6027	0.094*
C14	0.2557 (4)	0.4787 (6)	0.6952 (3)	0.0694 (14)
H14	0.2057	0.5458	0.7082	0.083*
C15	0.9430 (3)	0.2702 (5)	0.7603 (2)	0.0441 (10)
C16	1.0539 (3)	0.3300 (6)	0.7877 (2)	0.0596 (12)
H16A	1.0532	0.4490	0.7969	0.089*
H16B	1.0961	0.3103	0.7569	0.089*
H16C	1.0831	0.2690	0.8266	0.089*
C17	0.8113 (3)	0.1659 (5)	0.66393 (18)	0.0388 (10)
C18	0.9056 (3)	0.2506 (5)	0.69117 (19)	0.0418 (10)
C19	0.9665 (3)	0.3161 (6)	0.6492 (2)	0.0530 (11)
H19	1.0285	0.3736	0.6672	0.064*
C20	0.9390 (3)	0.2994 (6)	0.5845 (2)	0.0564 (12)
H20	0.9819	0.3440	0.5592	0.068*
C21	0.8443 (3)	0.2135 (5)	0.5550 (2)	0.0485 (11)
C22	0.7806 (3)	0.1459 (5)	0.59432 (19)	0.0427 (10)
C23	0.6864 (3)	0.0651 (5)	0.5649 (2)	0.0502 (11)
H23	0.6435	0.0213	0.5904	0.060*
C24	0.6560 (4)	0.0493 (6)	0.4991 (2)	0.0613 (13)
H24	0.5929	−0.0043	0.4802	0.074*
C25	0.7202 (4)	0.1138 (7)	0.4606 (2)	0.0712 (15)
H25	0.7005	0.1010	0.4160	0.085*
C26	0.8112 (4)	0.1952 (7)	0.4879 (2)	0.0641 (13)
H26	0.8524	0.2398	0.4615	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0401 (3)	0.0603 (4)	0.0372 (3)	−0.0043 (3)	0.0077 (2)	−0.0032 (3)
N1	0.046 (2)	0.056 (2)	0.0345 (19)	−0.0113 (19)	0.0022 (16)	0.0057 (18)
N2	0.043 (2)	0.050 (2)	0.039 (2)	−0.0019 (17)	0.0021 (16)	−0.0126 (17)
O1	0.060 (2)	0.093 (3)	0.0447 (19)	−0.0031 (19)	−0.0005 (16)	0.0194 (18)
O2	0.0535 (18)	0.051 (2)	0.0445 (17)	−0.0028 (15)	0.0010 (13)	−0.0102 (15)
O3	0.0415 (16)	0.087 (2)	0.0368 (16)	−0.0011 (17)	0.0062 (13)	−0.0113 (16)
O4	0.0506 (18)	0.077 (2)	0.0449 (17)	−0.0232 (16)	0.0196 (14)	−0.0171 (16)
C1	0.068 (3)	0.055 (3)	0.070 (3)	0.002 (3)	−0.012 (3)	0.018 (3)
C2	0.056 (3)	0.064 (3)	0.062 (3)	0.013 (3)	−0.005 (2)	0.002 (3)
C3	0.052 (3)	0.051 (3)	0.037 (2)	−0.019 (2)	0.011 (2)	0.000 (2)
C4	0.068 (3)	0.093 (4)	0.039 (3)	−0.018 (3)	0.015 (2)	0.002 (3)
C5	0.041 (2)	0.046 (3)	0.044 (2)	−0.015 (2)	0.011 (2)	−0.001 (2)
C6	0.047 (2)	0.048 (3)	0.041 (2)	−0.010 (2)	0.015 (2)	−0.005 (2)
C7	0.066 (3)	0.060 (3)	0.051 (3)	−0.016 (3)	0.025 (3)	−0.005 (2)
C8	0.058 (3)	0.051 (3)	0.085 (4)	−0.007 (3)	0.032 (3)	−0.006 (3)
C9	0.045 (3)	0.043 (3)	0.073 (3)	−0.011 (2)	0.017 (2)	0.007 (3)
C10	0.041 (2)	0.047 (3)	0.051 (3)	−0.013 (2)	0.008 (2)	0.004 (2)
C11	0.044 (3)	0.060 (3)	0.059 (3)	−0.012 (2)	0.005 (2)	0.006 (2)
C12	0.058 (3)	0.090 (4)	0.063 (3)	−0.021 (3)	−0.008 (3)	0.018 (3)
C13	0.048 (3)	0.075 (4)	0.100 (5)	−0.006 (3)	−0.006 (3)	0.028 (4)
C14	0.045 (3)	0.057 (3)	0.106 (4)	−0.003 (2)	0.016 (3)	0.011 (3)
C15	0.039 (2)	0.037 (3)	0.056 (3)	0.0032 (19)	0.008 (2)	−0.009 (2)
C16	0.043 (3)	0.062 (3)	0.070 (3)	−0.004 (2)	0.006 (2)	−0.008 (3)
C17	0.033 (2)	0.040 (3)	0.045 (2)	0.0005 (19)	0.0113 (18)	−0.006 (2)
C18	0.039 (2)	0.042 (3)	0.045 (2)	0.002 (2)	0.0125 (19)	−0.003 (2)
C19	0.043 (2)	0.052 (3)	0.066 (3)	−0.004 (2)	0.017 (2)	−0.001 (3)
C20	0.057 (3)	0.062 (3)	0.057 (3)	−0.001 (3)	0.026 (2)	0.004 (3)
C21	0.051 (3)	0.051 (3)	0.046 (3)	0.009 (2)	0.013 (2)	0.006 (2)
C22	0.044 (2)	0.044 (3)	0.041 (2)	0.006 (2)	0.0108 (19)	−0.001 (2)
C23	0.049 (3)	0.050 (3)	0.050 (3)	0.001 (2)	0.010 (2)	−0.002 (2)
C24	0.055 (3)	0.077 (4)	0.045 (3)	0.004 (3)	−0.004 (2)	−0.008 (3)
C25	0.072 (4)	0.094 (4)	0.044 (3)	0.010 (3)	0.005 (3)	0.009 (3)
C26	0.066 (3)	0.078 (4)	0.051 (3)	0.008 (3)	0.019 (2)	0.016 (3)

Geometric parameters (Å, º) top

Cu1—O3	1.876 (3)	C10—C11	1.402 (6)
Cu1—O4	1.895 (3)	C11—C12	1.376 (6)
Cu1—N2	1.947 (3)	C11—H11	0.9300
Cu1—N1	1.976 (3)	C12—C13	1.385 (7)
N1—C3	1.302 (5)	C12—H12	0.9300
N1—O1	1.417 (4)	C13—C14	1.352 (7)
N2—C15	1.301 (5)	C13—H13	0.9300
N2—O2	1.423 (4)	C14—H14	0.9300
O1—C1	1.414 (5)	C15—C18	1.449 (5)
O2—C2	1.432 (5)	C15—C16	1.504 (5)
O3—C5	1.304 (5)	C16—H16A	0.9600
O4—C17	1.290 (4)	C16—H16B	0.9600
C1—C2	1.497 (6)	C16—H16C	0.9600
C1—H1A	0.9700	C17—C18	1.403 (5)
C1—H1B	0.9700	C17—C22	1.453 (5)
C2—H2A	0.9700	C18—C19	1.422 (5)
C2—H2B	0.9700	C19—C20	1.346 (6)
C3—C6	1.450 (6)	C19—H19	0.9300
C3—C4	1.505 (5)	C20—C21	1.421 (6)
C4—H4A	0.9600	C20—H20	0.9300
C4—H4B	0.9600	C21—C26	1.404 (6)
C4—H4C	0.9600	C21—C22	1.411 (5)
C5—C6	1.401 (5)	C22—C23	1.398 (5)
C5—C10	1.458 (5)	C23—C24	1.372 (5)
C6—C7	1.426 (6)	C23—H23	0.9300
C7—C8	1.357 (6)	C24—C25	1.394 (6)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.402 (6)	C25—C26	1.357 (6)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.407 (6)	C26—H26	0.9300
C9—C14	1.417 (6)

O3—Cu1—O4	87.76 (11)	C11—C10—C5	120.1 (4)
O3—Cu1—N2	160.95 (14)	C9—C10—C5	120.5 (4)
O4—Cu1—N2	88.05 (12)	C12—C11—C10	120.7 (5)
O3—Cu1—N1	89.17 (12)	C12—C11—H11	119.7
O4—Cu1—N1	159.73 (14)	C10—C11—H11	119.7
N2—Cu1—N1	100.93 (13)	C11—C12—C13	120.0 (5)
C3—N1—O1	111.1 (3)	C11—C12—H12	120.0
C3—N1—Cu1	127.2 (3)	C13—C12—H12	120.0
O1—N1—Cu1	121.7 (3)	C14—C13—C12	120.6 (5)
C15—N2—O2	113.0 (3)	C14—C13—H13	119.7
C15—N2—Cu1	129.1 (3)	C12—C13—H13	119.7
O2—N2—Cu1	116.9 (2)	C13—C14—C9	121.4 (5)
C1—O1—N1	112.2 (3)	C13—C14—H14	119.3
N2—O2—C2	111.0 (3)	C9—C14—H14	119.3
C5—O3—Cu1	125.3 (2)	N2—C15—C18	120.2 (4)
C17—O4—Cu1	124.9 (3)	N2—C15—C16	120.0 (4)
O1—C1—C2	110.9 (4)	C18—C15—C16	119.8 (4)
O1—C1—H1A	109.5	C15—C16—H16A	109.5
C2—C1—H1A	109.5	C15—C16—H16B	109.5
O1—C1—H1B	109.5	H16A—C16—H16B	109.5
C2—C1—H1B	109.5	C15—C16—H16C	109.5
H1A—C1—H1B	108.0	H16A—C16—H16C	109.5
O2—C2—C1	113.6 (3)	H16B—C16—H16C	109.5
O2—C2—H2A	108.8	O4—C17—C18	124.6 (4)
C1—C2—H2A	108.8	O4—C17—C22	116.4 (3)
O2—C2—H2B	108.8	C18—C17—C22	118.9 (4)
C1—C2—H2B	108.8	C17—C18—C19	118.4 (4)
H2A—C2—H2B	107.7	C17—C18—C15	122.0 (4)
N1—C3—C6	121.0 (4)	C19—C18—C15	119.6 (4)
N1—C3—C4	119.0 (4)	C20—C19—C18	123.4 (4)
C6—C3—C4	120.0 (4)	C20—C19—H19	118.3
C3—C4—H4A	109.5	C18—C19—H19	118.3
C3—C4—H4B	109.5	C19—C20—C21	120.0 (4)
H4A—C4—H4B	109.5	C19—C20—H20	120.0
C3—C4—H4C	109.5	C21—C20—H20	120.0
H4A—C4—H4C	109.5	C26—C21—C22	118.7 (4)
H4B—C4—H4C	109.5	C26—C21—C20	122.2 (4)
O3—C5—C6	124.9 (4)	C22—C21—C20	119.1 (4)
O3—C5—C10	116.2 (4)	C23—C22—C21	118.8 (4)
C6—C5—C10	119.0 (4)	C23—C22—C17	121.0 (4)
C5—C6—C7	118.0 (4)	C21—C22—C17	120.1 (4)
C5—C6—C3	122.1 (4)	C24—C23—C22	121.2 (4)
C7—C6—C3	119.8 (4)	C24—C23—H23	119.4
C8—C7—C6	122.6 (4)	C22—C23—H23	119.4
C8—C7—H7	118.7	C23—C24—C25	119.7 (4)
C6—C7—H7	118.7	C23—C24—H24	120.1
C7—C8—C9	121.2 (4)	C25—C24—H24	120.1
C7—C8—H8	119.4	C26—C25—C24	120.3 (4)
C9—C8—H8	119.4	C26—C25—H25	119.9
C8—C9—C10	118.5 (4)	C24—C25—H25	119.9
C8—C9—C14	123.5 (5)	C25—C26—C21	121.3 (4)
C10—C9—C14	118.0 (5)	C25—C26—H26	119.3
C11—C10—C9	119.4 (4)	C21—C26—H26	119.3

O3—Cu1—N1—C3	−25.1 (4)	C14—C9—C10—C5	176.7 (4)
O4—Cu1—N1—C3	−106.3 (5)	O3—C5—C10—C11	2.8 (6)
N2—Cu1—N1—C3	138.7 (3)	C6—C5—C10—C11	−176.6 (4)
O3—Cu1—N1—O1	156.5 (3)	O3—C5—C10—C9	−175.8 (4)
O4—Cu1—N1—O1	75.2 (5)	C6—C5—C10—C9	4.7 (6)
N2—Cu1—N1—O1	−39.8 (3)	C9—C10—C11—C12	0.7 (6)
O3—Cu1—N2—C15	−51.8 (6)	C5—C10—C11—C12	−178.0 (4)
O4—Cu1—N2—C15	25.6 (4)	C10—C11—C12—C13	0.5 (7)
N1—Cu1—N2—C15	−172.7 (4)	C11—C12—C13—C14	−0.3 (8)
O3—Cu1—N2—O2	115.2 (4)	C12—C13—C14—C9	−1.1 (8)
O4—Cu1—N2—O2	−167.5 (3)	C8—C9—C14—C13	−179.1 (5)
N1—Cu1—N2—O2	−5.8 (3)	C10—C9—C14—C13	2.2 (7)
C3—N1—O1—C1	169.7 (4)	O2—N2—C15—C18	−174.5 (3)
Cu1—N1—O1—C1	−11.6 (4)	Cu1—N2—C15—C18	−7.2 (6)
C15—N2—O2—C2	−111.8 (4)	O2—N2—C15—C16	5.5 (5)
Cu1—N2—O2—C2	79.2 (3)	Cu1—N2—C15—C16	172.9 (3)
O4—Cu1—O3—C5	−166.2 (3)	Cu1—O4—C17—C18	30.4 (5)
N2—Cu1—O3—C5	−88.8 (5)	Cu1—O4—C17—C22	−151.3 (3)
N1—Cu1—O3—C5	33.8 (3)	O4—C17—C18—C19	179.4 (4)
O3—Cu1—O4—C17	125.2 (3)	C22—C17—C18—C19	1.2 (6)
N2—Cu1—O4—C17	−36.2 (3)	O4—C17—C18—C15	0.4 (6)
N1—Cu1—O4—C17	−153.3 (4)	C22—C17—C18—C15	−177.8 (3)
N1—O1—C1—C2	93.8 (4)	N2—C15—C18—C17	−12.2 (6)
N2—O2—C2—C1	−57.3 (5)	C16—C15—C18—C17	167.8 (4)
O1—C1—C2—O2	−55.4 (5)	N2—C15—C18—C19	168.8 (4)
O1—N1—C3—C6	−175.4 (3)	C16—C15—C18—C19	−11.2 (6)
Cu1—N1—C3—C6	6.0 (6)	C17—C18—C19—C20	−0.9 (6)
O1—N1—C3—C4	2.4 (5)	C15—C18—C19—C20	178.1 (4)
Cu1—N1—C3—C4	−176.1 (3)	C18—C19—C20—C21	0.5 (7)
Cu1—O3—C5—C6	−24.8 (6)	C19—C20—C21—C26	178.9 (4)
Cu1—O3—C5—C10	155.8 (3)	C19—C20—C21—C22	−0.4 (6)
O3—C5—C6—C7	176.0 (4)	C26—C21—C22—C23	−0.8 (6)
C10—C5—C6—C7	−4.6 (6)	C20—C21—C22—C23	178.5 (4)
O3—C5—C6—C3	−6.4 (6)	C26—C21—C22—C17	−178.6 (4)
C10—C5—C6—C3	173.0 (4)	C20—C21—C22—C17	0.7 (6)
N1—C3—C6—C5	15.5 (6)	O4—C17—C22—C23	2.8 (6)
C4—C3—C6—C5	−162.4 (4)	C18—C17—C22—C23	−178.9 (4)
N1—C3—C6—C7	−167.0 (4)	O4—C17—C22—C21	−179.5 (4)
C4—C3—C6—C7	15.2 (6)	C18—C17—C22—C21	−1.1 (6)
C5—C6—C7—C8	2.0 (6)	C21—C22—C23—C24	0.7 (6)
C3—C6—C7—C8	−175.6 (4)	C17—C22—C23—C24	178.5 (4)
C6—C7—C8—C9	0.6 (7)	C22—C23—C24—C25	0.3 (7)
C7—C8—C9—C10	−0.6 (6)	C23—C24—C25—C26	−1.4 (7)
C7—C8—C9—C14	−179.3 (4)	C24—C25—C26—C21	1.4 (8)
C8—C9—C10—C11	179.2 (4)	C22—C21—C26—C25	−0.3 (7)
C14—C9—C10—C11	−2.0 (6)	C20—C21—C26—C25	−179.5 (5)
C8—C9—C10—C5	−2.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3ⁱ	0.96	2.64	3.375 (5)	134
C23—H23···O2ⁱⁱ	0.93	2.43	3.261 (5)	149
C4—H4C···Cg8ⁱ	0.96	2.68	3.564 (6)	153

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂₆H₂₂N₂O₄)]
M_r	490.00
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.0288 (17), 7.8934 (12), 21.292 (2)
β (°)	103.217 (2)
V (Å³)	2131.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.41 × 0.17 × 0.07

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.670, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	10698, 3753, 2278
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.108, 1.03
No. of reflections	3753
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.41

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3ⁱ	0.96	2.64	3.375 (5)	133.5
C23—H23···O2ⁱⁱ	0.93	2.43	3.261 (5)	149.2
C4—H4C···Cg8ⁱ	0.96	2.68	3.564 (6)	153

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

Acknowledgements

The authors acknowledge finanical support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University.

References

Akine, S., Takanori, T., Taniguchi, T. & Nabeshima, T. (2005). Inorg. Chem. 44, 3270–3274. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Dong, W. K., Sun, Y. X., Zhang, Y. P., Li, L., He, X. N. & Tang, X. L. (2009b). Inorg. Chim. Acta, 362, 117–124. Web of Science CSD CrossRef CAS Google Scholar
Dong, W.-K., Wu, J.-C., Yao, J., Gong, S.-S. & Tong, J.-F. (2009c). Acta Cryst. E65, m803. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katsuki, T. (1995). Coord. Chem. Rev. 140, 189–214. CrossRef CAS Web of Science Google Scholar
Ray, M. S., Mukhopadhyay, G. M., Drew, M. G. B., Lu, T. H., Chaudhuri, S. & Ghosh, A. (2003). Inorg. Chem. Commun. 6, 961–965. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 65| Part 7| July 2009| Page m802

doi:10.1107/S1600536809023010

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

{2,2′-[1,1′-(Ethyl­ene­dioxy­di­nitrilo)di­ethyl­­idyne]di-1-naphtholato}copper(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}copper(II)