(Acetato-κO)(2-{[2-(dimethyl-amino)-ethyl-imino](phen-yl)meth-yl}-5-methoxy-phenolato-κN,N',O)copper(II).

The Cu(II) atom in the title complex, [Cu(C(18)H(21)N(2)O(2))(C(2)H(3)O(2))], is tetra-coordinated 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 intra-molecular inter-action 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 inter-molecular inter-actions, 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 = 419.96

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.02

3822 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033114/rk2108sup1.cif

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

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

[Cu(C18H21N2O2)(C2H3O2)]	F(000) = 876
Mr = 419.96	Dx = 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

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

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(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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