(Acetato-κO)(2-{[2-(dimethyl­amino)­ethyl­imino](phen­yl)meth­yl}-5-methoxy­phenolato-κ3N,N′,O1)copper(II)

Lin, C.-S.; Lin, C.-H.; Huang, J.-H.; Ko, B.-T.

doi:10.1107/S1600536808033114

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1434

doi:10.1107/S1600536808033114

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(Acetato-κO)(2-{[2-(dimethylamino)ethylimino](phenyl)methyl}-5-methoxyphenolato-κ³N,N′,O¹)copper(II)

Chieh-Shen Lin,^a Chia-Her Lin,^b Jui-Hsien Huang ^a and Bao-Tsan Ko ^b ^*

^aDepartment of Chemistry, National Changhua University of Education, Changhua 500, Taiwan, and ^bDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
^*Correspondence e-mail: btko@cycu.edu.tw

(Received 27 August 2008; accepted 13 October 2008; online 18 October 2008)

The Cu^II atom in the title complex, [Cu(C₁₈H₂₁N₂O₂)(C₂H₃O₂)], is tetracoordinated by two N atoms and two O atoms, of which one O atom is attributed to the acetate group and the other atoms are from the tridentate salicylideneiminate ligand, forming a slight distorted square-planar environment. The other acetate O atom exhibits a very weak intramolecular interaction toward the Cu atom, the Cu—O distance of 2.771 (2) Å being shorter than the van der Waals radii for Cu and O atoms (2.92 Å). Furthermore, there are weak intermolecular interactions, in which the bonding O atom of the acetate group can bridge to the Cu atom of another complex, and the distance of 2.523 (2) Å is about 0.4 Å shorter than the van der Waals Cu—O distance in other crystal structures.

Related literature

For general background, see: Coates & Moore (2004 ); Darensbourg et al. (2001 ); Inoue et al. (1969 ); Shen et al. (2003 ). For related structures, see: Chen et al. (2006 ); Luo et al. (1998 , 1999 ).

Experimental

Crystal data

[Cu(C₁₈H₂₁N₂O₂)(C₂H₃O₂)]
M_r = 419.96
Monoclinic, P 2₁ /c
a = 11.9721 (16) Å
b = 15.674 (2) Å
c = 10.6346 (14) Å
β = 102.655 (3)°
V = 1947.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 293 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.656, T_max = 0.803
11008 measured reflections
3822 independent reflections
2673 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 1.02
3822 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); 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/S1600536808033114/rk2108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033114/rk2108Isup2.hkl

checkCIF report

Comment top

Carbon dioxide is the most abundant carbon resource in the atmosphere and is used by green plants and anaerobic bacteria for chemical production on a massive scale. In contrast, industrial and laboratory utilization of CO₂ as a chemical feedstock is rare. The reuse and recovery of CO₂ have received much attention from the viewpoint of carbon resources and environmental problems during the last two decades of the twentieth century. In particular, the catalytic coupling of CO₂ with heterocycles has been discovered and investigated over the past 35 years (Inoue et al., 1969). One of the major successes is the utilization of epoxides and CO₂ as starting materials to prepare the polycarbonates and/or cyclic carbonates in the presence of a transition metal catalyst. However, only a few metals, including Al, Cr, Co, Mg, Li, Zn, Cu, and Cd (Coates & Moore, 2004) are active for the coupling of epoxides and CO₂. Recently, Darensbourg et al., (2001) disclosed the synthesis, characterization and catalytic studies of a number of bis(salicylaldiminato)zinc complexes, in which the most active catalyst for co–polymerization of cyclohexene oxide and CO₂ giving poly(cyclohexene carbonate) (>99% carbonate linkages, Mn = 41000 g^.mol^-1, Mw/Mn = 10.3) with a turnover frequency of 6.9 h^-1. In addition, Shen et al. (2003) reported that binaphthyldiaminosalen–type Zn, Cu, and Co complexes efficiently catalyzed reactions of epoxides with CO₂ to achieve five–membered ring cyclic carbonates in the presence of various catalytic amounts of organic bases. Most recently, Chen et al., (2006) has synthesized a series of Schiff base zinc complexes which have shown high activity in the ring–opening poymerization of lactide (Chen et al., 2006). We report herein the synthesis and crystal structure study of a N,N,O–tridentate Schiff base Cu^II complex (I), a potential catalyst for CO₂/epoxide coupling copolymerization (Fig. 1).

The solid structure of I reveals a monomeric Cu^II complex (Fig. 1) containing a six–member and five–member ring coordinated from the tridentate salicylideneiminate ligand. The geometry around Cu atom is tetracoordinated with a slight distorted square planar environment in which two nitrogen atoms and two oxygen atoms are almost coplanar. The sums of bond angles around Cu center are 359.7 (1)°. The distances between the Cu atom and O1, O3, N1 and N2 are 1.908 (2), 1.968 (2), 2.073 (3), 1.969 (3)Å, respectively. These bond distances are similar to those found in other Schiff base Cu^II complexes (Luo et al., 1998). The other acetate's oxygen, O4 shows very weak intramolecular contact with Cu (Cu···O4 = 2.771 (2)Å) in comparison with Van der Waals contact (2.92Å) for Cu···O. In addition, there are weak intermolecular interactions, in which the bonding oxygen (O3) of acetate group can be bridged to the Cu atom of another complex and the distance (2.523 (2) Å) is about 0.4 Å shorter than Van der Waals contact of Cu···O in the other crystal structure.

Related literature top

Chen et al. (2006); Coates & Moore (2004); Darensbourg et al. (2001); Inoue et al. (1969); Luo et al. (1998, 1999); Shen et al. (2003). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that it said, for example, "For general background, see··· For related structures, see..; etc. Please revise this section as indicated.

Experimental top

The ligand, 5–methoxy–2–{1–[2–(dimethylamino)ethylimino]benzyl}phenol was prepared by the reaction in which 2–dimethylaminoethylamine (1.95 g, 22.1 mmol) and 5–methoxy–2–hydroxybenzophenone (4.60 g, 20.2 mmol) in refluxed ethanol (30 ml) for 24 h (Fig. 2). Volatile materials were removed under vacuum and the resulting solid was recrystallized from slowly cooling a hot hexane (40 ml) solution giving yellow powders (yield: 71%). The title complex was synthesized by the following procedures: 5–methoxy–2–{1–[2–(dimethylamino)ethylimino]benzyl}phenol (0.597 g, 2.0 mmol) and Cu(OAc)₂^.2H₂O (0.398 g, 2.0 mmol) was refluxed in EtOH (30 ml) for 3 h and the volatile materials were removed under vacuum giving green crystalline solid (Fig. 2). The resulting precipitate was crystallized from EtOH to yield green crystals.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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. A view of the molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The synthetic route of the title Cu complex.

(Acetato-κO)(2-{[2-(dimethylamino)ethylimino](phenyl)methyl}-5- methoxyphenolato-κ³N,N',O¹)copper(II) top

Crystal data top

[Cu(C₁₈H₂₁N₂O₂)(C₂H₃O₂)]	F(000) = 876
M_r = 419.96	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3118 reflections
a = 11.9721 (16) Å	θ = 2.2–25.4°
b = 15.674 (2) Å	µ = 1.15 mm⁻¹
c = 10.6346 (14) Å	T = 293 K
β = 102.655 (3)°	Prism, green
V = 1947.1 (4) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3822 independent reflections
Radiation source: Fine–focus sealed tube	2673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.656, T_max = 0.803	k = −18→19
11008 measured reflections	l = −8→13

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: Geom
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
3822 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cu(C₁₈H₂₁N₂O₂)(C₂H₃O₂)]	V = 1947.1 (4) Å³
M_r = 419.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9721 (16) Å	µ = 1.15 mm⁻¹
b = 15.674 (2) Å	T = 293 K
c = 10.6346 (14) Å	0.40 × 0.30 × 0.20 mm
β = 102.655 (3)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3822 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2673 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.803	R_int = 0.049
11008 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
3822 reflections	Δρ_min = −0.40 e Å⁻³
244 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Cu	0.93747 (3)	0.10053 (2)	0.02371 (4)	0.02773 (13)
O1	0.92068 (16)	0.06311 (14)	0.1893 (2)	0.0332 (5)
O2	0.7404 (2)	−0.04350 (17)	0.5113 (2)	0.0474 (6)
O3	1.09237 (16)	0.05131 (13)	0.0552 (2)	0.0303 (5)
O4	1.1426 (2)	0.17945 (16)	0.1343 (2)	0.0467 (6)
N1	0.7889 (2)	0.15948 (18)	−0.0052 (3)	0.0379 (7)
N2	0.9457 (2)	0.15348 (17)	−0.1526 (3)	0.0333 (6)
C1	0.8276 (2)	0.05790 (19)	0.2325 (3)	0.0268 (7)
C2	0.8331 (3)	0.0119 (2)	0.3478 (3)	0.0327 (7)
H2A	0.9021	−0.0132	0.3880	0.039*
C3	0.7400 (3)	0.0029 (2)	0.4025 (3)	0.0355 (8)
C4	0.6361 (3)	0.0424 (2)	0.3444 (3)	0.0434 (9)
H4A	0.5733	0.0386	0.3825	0.052*
C5	0.6277 (3)	0.0858 (2)	0.2337 (4)	0.0392 (8)
H5A	0.5581	0.1112	0.1967	0.047*
C6	0.7199 (2)	0.0949 (2)	0.1702 (3)	0.0290 (7)
C7	0.7052 (3)	0.1444 (2)	0.0533 (3)	0.0321 (7)
C8	0.5879 (2)	0.1779 (2)	−0.0065 (3)	0.0348 (8)
C9	0.5162 (3)	0.1296 (3)	−0.0985 (4)	0.0603 (12)
H9A	0.5396	0.0757	−0.1189	0.072*
C10	0.4106 (3)	0.1598 (3)	−0.1607 (4)	0.0675 (13)
H10A	0.3635	0.1267	−0.2232	0.081*
C11	0.3748 (3)	0.2386 (3)	−0.1307 (4)	0.0581 (11)
H11A	0.3038	0.2593	−0.1733	0.070*
C12	0.4432 (3)	0.2866 (3)	−0.0384 (4)	0.0635 (12)
H12A	0.4181	0.3397	−0.0169	0.076*
C13	0.5505 (3)	0.2568 (3)	0.0241 (4)	0.0527 (10)
H13A	0.5970	0.2902	0.0868	0.063*
C14	0.7695 (3)	0.2182 (3)	−0.1169 (4)	0.0592 (12)
H14A	0.7370	0.2715	−0.0952	0.071*
H14B	0.7167	0.1929	−0.1896	0.071*
C15	0.8852 (3)	0.2344 (2)	−0.1512 (4)	0.0535 (10)
H15A	0.8737	0.2613	−0.2352	0.064*
H15B	0.9306	0.2726	−0.0883	0.064*
C16	0.8860 (3)	0.0981 (3)	−0.2608 (4)	0.0561 (11)
H16A	0.8906	0.1237	−0.3415	0.084*
H16B	0.8071	0.0918	−0.2567	0.084*
H16C	0.9219	0.0430	−0.2539	0.084*
C17	1.0606 (3)	0.1696 (3)	−0.1764 (4)	0.0522 (10)
H17A	1.0535	0.1941	−0.2606	0.078*
H17B	1.1020	0.1169	−0.1717	0.078*
H17C	1.1011	0.2084	−0.1126	0.078*
C18	0.8349 (3)	−0.1007 (3)	0.5543 (4)	0.0537 (10)
H18A	0.8254	−0.1296	0.6309	0.081*
H18B	0.9050	−0.0688	0.5726	0.081*
H18C	0.8372	−0.1418	0.4881	0.081*
C19	1.1673 (3)	0.1069 (2)	0.1073 (3)	0.0329 (7)
C20	1.2906 (3)	0.0780 (3)	0.1325 (4)	0.0571 (12)
H20A	1.3396	0.1237	0.1713	0.086*
H20B	1.3096	0.0620	0.0525	0.086*
H20C	1.3008	0.0298	0.1896	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0244 (2)	0.0309 (2)	0.0274 (2)	0.00498 (16)	0.00454 (14)	0.00588 (17)
O1	0.0233 (11)	0.0480 (14)	0.0286 (13)	0.0067 (10)	0.0060 (9)	0.0079 (10)
O2	0.0479 (14)	0.0579 (18)	0.0401 (15)	−0.0047 (12)	0.0181 (11)	0.0103 (13)
O3	0.0234 (10)	0.0327 (13)	0.0332 (13)	−0.0008 (9)	0.0027 (9)	0.0013 (10)
O4	0.0470 (15)	0.0407 (16)	0.0502 (17)	0.0011 (12)	0.0061 (12)	−0.0130 (12)
N1	0.0352 (15)	0.0444 (19)	0.0333 (17)	0.0152 (13)	0.0055 (12)	0.0123 (13)
N2	0.0354 (15)	0.0289 (16)	0.0344 (17)	0.0033 (12)	0.0053 (12)	0.0072 (12)
C1	0.0257 (15)	0.0265 (17)	0.0271 (18)	−0.0019 (12)	0.0034 (13)	−0.0033 (13)
C2	0.0295 (16)	0.037 (2)	0.0309 (19)	0.0011 (14)	0.0042 (13)	0.0023 (14)
C3	0.0411 (19)	0.035 (2)	0.032 (2)	−0.0092 (15)	0.0106 (15)	−0.0030 (15)
C4	0.0347 (19)	0.050 (2)	0.052 (2)	0.0000 (16)	0.0217 (16)	0.0017 (19)
C5	0.0282 (17)	0.040 (2)	0.050 (2)	0.0031 (14)	0.0106 (15)	0.0002 (17)
C6	0.0242 (15)	0.0284 (18)	0.0334 (18)	0.0011 (13)	0.0039 (13)	−0.0032 (14)
C7	0.0293 (16)	0.0291 (19)	0.036 (2)	0.0068 (13)	0.0024 (14)	−0.0061 (15)
C8	0.0277 (17)	0.041 (2)	0.033 (2)	0.0092 (14)	0.0008 (14)	0.0031 (15)
C9	0.041 (2)	0.059 (3)	0.071 (3)	0.0148 (19)	−0.011 (2)	−0.026 (2)
C10	0.043 (2)	0.077 (3)	0.069 (3)	0.013 (2)	−0.017 (2)	−0.021 (2)
C11	0.0314 (19)	0.070 (3)	0.065 (3)	0.0144 (19)	−0.0067 (18)	0.011 (2)
C12	0.045 (2)	0.049 (3)	0.090 (3)	0.0256 (19)	0.002 (2)	−0.003 (2)
C13	0.038 (2)	0.047 (2)	0.065 (3)	0.0128 (17)	−0.0054 (18)	−0.011 (2)
C14	0.059 (2)	0.071 (3)	0.053 (3)	0.034 (2)	0.0219 (19)	0.034 (2)
C15	0.068 (3)	0.041 (2)	0.055 (3)	0.0165 (19)	0.022 (2)	0.0177 (19)
C16	0.070 (3)	0.053 (3)	0.041 (2)	−0.003 (2)	0.0019 (19)	0.0058 (19)
C17	0.048 (2)	0.062 (3)	0.051 (3)	0.0074 (19)	0.0203 (18)	0.021 (2)
C18	0.058 (2)	0.062 (3)	0.041 (2)	−0.005 (2)	0.0095 (18)	0.015 (2)
C19	0.0274 (16)	0.045 (2)	0.0265 (18)	−0.0012 (15)	0.0061 (13)	−0.0016 (16)
C20	0.0288 (19)	0.063 (3)	0.076 (3)	0.0009 (17)	0.0047 (18)	−0.011 (2)

Geometric parameters (Å, º) top

Cu—O1	1.908 (2)	C9—C10	1.377 (5)
Cu—N1	1.968 (3)	C9—H9A	0.9300
Cu—O3	1.968 (2)	C10—C11	1.368 (6)
Cu—N2	2.073 (3)	C10—H10A	0.9300
O1—C1	1.298 (3)	C11—C12	1.359 (5)
O2—C3	1.366 (4)	C11—H11A	0.9300
O2—C18	1.437 (4)	C12—C13	1.392 (5)
O3—C19	1.287 (4)	C12—H12A	0.9300
O4—C19	1.224 (4)	C13—H13A	0.9300
N1—C7	1.312 (4)	C14—C15	1.529 (5)
N1—C14	1.481 (4)	C14—H14A	0.9700
N2—C15	1.463 (4)	C14—H14B	0.9700
N2—C17	1.475 (4)	C15—H15A	0.9700
N2—C16	1.493 (4)	C15—H15B	0.9700
C1—C2	1.412 (4)	C16—H16A	0.9600
C1—C6	1.436 (4)	C16—H16B	0.9600
C2—C3	1.374 (4)	C16—H16C	0.9600
C2—H2A	0.9300	C17—H17A	0.9600
C3—C4	1.405 (5)	C17—H17B	0.9600
C4—C5	1.345 (5)	C17—H17C	0.9600
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.421 (4)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.443 (4)	C19—C20	1.510 (4)
C7—C8	1.505 (4)	C20—H20A	0.9600
C8—C13	1.378 (5)	C20—H20B	0.9600
C8—C9	1.378 (5)	C20—H20C	0.9600

O1—Cu—N1	90.82 (10)	C10—C11—C12	119.9 (3)
O1—Cu—O3	90.49 (8)	C10—C11—H11A	120.0
N1—Cu—O3	175.05 (11)	C12—C11—H11A	120.0
O1—Cu—N2	173.51 (10)	C13—C12—C11	120.4 (4)
N1—Cu—N2	83.74 (11)	C13—C12—H12A	119.8
O3—Cu—N2	94.64 (9)	C11—C12—H12A	119.8
C1—O1—Cu	128.17 (19)	C8—C13—C12	120.1 (3)
C3—O2—C18	117.2 (3)	C8—C13—H13A	119.9
C19—O3—Cu	110.5 (2)	C12—C13—H13A	119.9
C7—N1—C14	119.4 (3)	N1—C14—C15	107.7 (3)
C7—N1—Cu	126.8 (2)	N1—C14—H14A	110.2
C14—N1—Cu	113.3 (2)	C15—C14—H14A	110.2
C15—N2—C17	109.6 (3)	N1—C14—H14B	110.2
C15—N2—C16	111.0 (3)	C15—C14—H14B	110.2
C17—N2—C16	105.9 (3)	H14A—C14—H14B	108.5
C15—N2—Cu	102.5 (2)	N2—C15—C14	109.6 (3)
C17—N2—Cu	117.1 (2)	N2—C15—H15A	109.8
C16—N2—Cu	110.8 (2)	C14—C15—H15A	109.8
O1—C1—C2	117.3 (3)	N2—C15—H15B	109.8
O1—C1—C6	124.4 (3)	C14—C15—H15B	109.8
C2—C1—C6	118.3 (3)	H15A—C15—H15B	108.2
C3—C2—C1	122.2 (3)	N2—C16—H16A	109.5
C3—C2—H2A	118.9	N2—C16—H16B	109.5
C1—C2—H2A	118.9	H16A—C16—H16B	109.5
O2—C3—C2	124.1 (3)	N2—C16—H16C	109.5
O2—C3—C4	116.5 (3)	H16A—C16—H16C	109.5
C2—C3—C4	119.4 (3)	H16B—C16—H16C	109.5
C5—C4—C3	119.8 (3)	N2—C17—H17A	109.5
C5—C4—H4A	120.1	N2—C17—H17B	109.5
C3—C4—H4A	120.1	H17A—C17—H17B	109.5
C4—C5—C6	123.4 (3)	N2—C17—H17C	109.5
C4—C5—H5A	118.3	H17A—C17—H17C	109.5
C6—C5—H5A	118.3	H17B—C17—H17C	109.5
C7—C6—C5	120.2 (3)	O2—C18—H18A	109.5
C7—C6—C1	122.8 (3)	O2—C18—H18B	109.5
C5—C6—C1	116.9 (3)	H18A—C18—H18B	109.5
N1—C7—C6	123.0 (3)	O2—C18—H18C	109.5
N1—C7—C8	118.4 (3)	H18A—C18—H18C	109.5
C6—C7—C8	118.6 (3)	H18B—C18—H18C	109.5
C13—C8—C9	118.5 (3)	O4—C19—O3	123.3 (3)
C13—C8—C7	122.3 (3)	O4—C19—C20	120.9 (3)
C9—C8—C7	119.1 (3)	O3—C19—C20	115.8 (3)
C10—C9—C8	121.0 (4)	C19—C20—H20A	109.5
C10—C9—H9A	119.5	C19—C20—H20B	109.5
C8—C9—H9A	119.5	H20A—C20—H20B	109.5
C11—C10—C9	120.0 (4)	C19—C20—H20C	109.5
C11—C10—H10A	120.0	H20A—C20—H20C	109.5
C9—C10—H10A	120.0	H20B—C20—H20C	109.5

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₂₁N₂O₂)(C₂H₃O₂)]
M_r	419.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.9721 (16), 15.674 (2), 10.6346 (14)
β (°)	102.655 (3)
V (Å³)	1947.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.656, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	11008, 3822, 2673
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.02
No. of reflections	3822
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.40

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan, and in part from the project of specific research fields in Chung Yuan Christian University, Taiwan (No. CYCU-97-CR-CH).

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