Bis{2-meth-oxy-6-[(3-methoxy-prop-yl)imino-meth-yl]phenolato-κN,O}copper(II).

The title complex, [Cu(C(12)H(16)NO(3))(2)], adopts a distorted square-planar coordination geometry with the Cu(II) ion situated on a crystallographic inversion center. The two Schiff base ligands are coordinated in a trans fashion. In the crystal structure, non-classical inter-molecular C-H⋯O hydrogen bonds involving the ether O atoms link the Schiff base mol-ecules into a two-dimensional network parallel to (101).

Related literature

For similar copper(II) structures with Schiff base ligands: see: Akitsu & Einaga (2004 ▶); Bluhm et al. (2003 ▶); Castiñeiras et al. (1990 ▶); Costamagna et al. (1998 ▶); King et al. (1973 ▶); Lacroix et al. (2004 ▶); Zhang et al. (2001 ▶).

Experimental

Crystal data

[Cu(C12H16NO3)2]

M = 508.06

Monoclinic,

a = 11.2189 (9) Å

b = 10.7004 (8) Å

c = 9.5002 (7) Å

β = 96.912 (1)°

V = 1132.18 (15) Å3

Z = 2

Mo Kα radiation

μ = 1.01 mm−1

T = 100 (2) K

0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.614, T max = 0.668

6343 measured reflections

2298 independent reflections

2065 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.079

S = 1.09

2298 reflections

153 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035289/lh2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035289/lh2719Isup2.hkl

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

[Cu(C12H16N1O3)2]	F000 = 534
Mr = 508.06	Dx = 1.490 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3703 reflections
a = 11.2189 (9) Å	θ = 2.6–26.4º
b = 10.7004 (8) Å	µ = 1.01 mm−1
c = 9.5002 (7) Å	T = 100 (2) K
β = 96.9120 (10)º	Block, black
V = 1132.18 (15) Å3	0.50 × 0.50 × 0.40 mm
Z = 2

Bruker SMART APEXII diffractometer	2065 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 100(2) K	θmax = 26.4º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→7
Tmin = 0.614, Tmax = 0.668	k = −13→12
6343 measured reflections	l = −11→11
2298 independent reflections

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.0531P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2298 reflections	Δρmax = 0.31 e Å−3
153 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	0.5000	0.01161 (11)
N1	0.06486 (12)	0.67268 (12)	0.54175 (13)	0.0124 (3)
O1	−0.10464 (10)	0.55690 (11)	0.34077 (12)	0.0157 (3)
O2	−0.26520 (10)	0.57869 (11)	0.11946 (12)	0.0168 (3)
O3	0.38383 (10)	0.83717 (11)	0.73181 (13)	0.0203 (3)
C1	−0.12843 (14)	0.67057 (15)	0.29658 (16)	0.0123 (3)
C2	−0.21677 (14)	0.68788 (15)	0.17655 (16)	0.0133 (3)
C3	−0.24800 (15)	0.80571 (16)	0.12650 (17)	0.0146 (3)
H3	−0.3084	0.8153	0.0481	0.018*
C4	−0.19103 (15)	0.91184 (16)	0.19081 (17)	0.0160 (4)
H4	−0.2131	0.9930	0.1564	0.019*
C5	−0.10354 (15)	0.89779 (15)	0.30333 (17)	0.0146 (3)
H5	−0.0639	0.9695	0.3453	0.018*
C6	−0.07147 (15)	0.77820 (15)	0.35771 (16)	0.0128 (3)
C7	0.02158 (15)	0.77112 (16)	0.47516 (16)	0.0134 (3)
H7	0.0557	0.8486	0.5081	0.016*
C8	−0.35395 (15)	0.59005 (17)	−0.00057 (17)	0.0185 (4)
H8A	−0.4248	0.6325	0.0275	0.028*
H8B	−0.3767	0.5067	−0.0372	0.028*
H8C	−0.3214	0.6388	−0.0744	0.028*
C9	0.16306 (14)	0.69566 (15)	0.65644 (16)	0.0136 (3)
H9A	0.1512	0.6429	0.7392	0.016*
H9B	0.1613	0.7842	0.6862	0.016*
C10	0.28466 (15)	0.66641 (16)	0.60836 (17)	0.0166 (4)
H10A	0.2902	0.5756	0.5904	0.020*
H10B	0.2919	0.7107	0.5183	0.020*
C11	0.38687 (15)	0.70517 (15)	0.71811 (18)	0.0161 (4)
H11A	0.3781	0.6652	0.8103	0.019*
H11B	0.4645	0.6787	0.6881	0.019*
C12	0.47976 (15)	0.88352 (17)	0.82805 (18)	0.0214 (4)
H12A	0.4776	0.8444	0.9210	0.032*
H12B	0.4719	0.9743	0.8369	0.032*
H12C	0.5562	0.8639	0.7929	0.032*

	U11	U22	U33	U12	U13	U23
Cu1	0.01075 (17)	0.01035 (17)	0.01270 (16)	−0.00026 (10)	−0.00282 (11)	0.00036 (10)
N1	0.0102 (7)	0.0140 (7)	0.0128 (6)	−0.0004 (6)	0.0000 (6)	−0.0016 (6)
O1	0.0166 (6)	0.0117 (6)	0.0170 (6)	0.0001 (5)	−0.0057 (5)	0.0011 (5)
O2	0.0164 (6)	0.0158 (6)	0.0163 (6)	−0.0019 (5)	−0.0061 (5)	−0.0006 (5)
O3	0.0167 (6)	0.0128 (6)	0.0286 (7)	−0.0022 (5)	−0.0085 (5)	0.0003 (5)
C1	0.0108 (8)	0.0133 (8)	0.0133 (7)	0.0012 (7)	0.0033 (6)	0.0004 (6)
C2	0.0116 (8)	0.0149 (8)	0.0138 (7)	−0.0009 (7)	0.0027 (7)	−0.0009 (6)
C3	0.0114 (8)	0.0191 (9)	0.0130 (7)	0.0020 (7)	0.0002 (6)	0.0032 (7)
C4	0.0171 (9)	0.0135 (8)	0.0176 (8)	0.0024 (7)	0.0029 (7)	0.0030 (7)
C5	0.0165 (9)	0.0108 (8)	0.0169 (8)	−0.0004 (7)	0.0032 (7)	−0.0011 (7)
C6	0.0115 (8)	0.0141 (8)	0.0132 (8)	0.0013 (7)	0.0029 (7)	0.0003 (6)
C7	0.0136 (8)	0.0120 (8)	0.0149 (8)	−0.0014 (6)	0.0024 (7)	−0.0026 (6)
C8	0.0157 (9)	0.0219 (9)	0.0166 (8)	−0.0013 (7)	−0.0039 (7)	0.0006 (7)
C9	0.0115 (8)	0.0143 (8)	0.0140 (8)	−0.0008 (7)	−0.0025 (6)	−0.0021 (6)
C10	0.0146 (9)	0.0172 (8)	0.0176 (8)	−0.0001 (7)	0.0000 (7)	−0.0027 (7)
C11	0.0136 (8)	0.0145 (8)	0.0198 (8)	0.0005 (7)	0.0002 (7)	−0.0012 (7)
C12	0.0175 (9)	0.0200 (9)	0.0256 (9)	−0.0055 (7)	−0.0022 (8)	−0.0030 (8)

Cu1—O1i	1.9000 (11)	C5—C6	1.410 (2)
Cu1—O1	1.9000 (11)	C5—H5	0.9500
Cu1—N1i	2.0079 (13)	C6—C7	1.435 (2)
Cu1—N1	2.0079 (13)	C7—H7	0.9500
N1—C7	1.293 (2)	C8—H8A	0.9800
N1—C9	1.474 (2)	C8—H8B	0.9800
O1—C1	1.3038 (19)	C8—H8C	0.9800
O2—C2	1.3724 (19)	C9—C10	1.522 (2)
O2—C8	1.4258 (19)	C9—H9A	0.9900
O3—C12	1.415 (2)	C9—H9B	0.9900
O3—C11	1.419 (2)	C10—C11	1.512 (2)
C1—C6	1.408 (2)	C10—H10A	0.9900
C1—C2	1.430 (2)	C10—H10B	0.9900
C2—C3	1.378 (2)	C11—H11A	0.9900
C3—C4	1.406 (2)	C11—H11B	0.9900
C3—H3	0.9500	C12—H12A	0.9800
C4—C5	1.370 (2)	C12—H12B	0.9800
C4—H4	0.9500	C12—H12C	0.9800
O1i—Cu1—O1	180.0	C6—C7—H7	115.9
O1i—Cu1—N1i	92.11 (5)	O2—C8—H8A	109.5
O1—Cu1—N1i	87.89 (5)	O2—C8—H8B	109.5
O1i—Cu1—N1	87.89 (5)	H8A—C8—H8B	109.5
O1—Cu1—N1	92.11 (5)	O2—C8—H8C	109.5
N1i—Cu1—N1	180.00 (7)	H8A—C8—H8C	109.5
C7—N1—C9	115.41 (14)	H8B—C8—H8C	109.5
C7—N1—Cu1	123.18 (11)	N1—C9—C10	111.16 (12)
C9—N1—Cu1	121.36 (10)	N1—C9—H9A	109.4
C1—O1—Cu1	129.66 (11)	C10—C9—H9A	109.4
C2—O2—C8	116.66 (13)	N1—C9—H9B	109.4
C12—O3—C11	112.53 (13)	C10—C9—H9B	109.4
O1—C1—C6	124.41 (15)	H9A—C9—H9B	108.0
O1—C1—C2	118.23 (14)	C11—C10—C9	111.67 (13)
C6—C1—C2	117.35 (14)	C11—C10—H10A	109.3
O2—C2—C3	124.78 (15)	C9—C10—H10A	109.3
O2—C2—C1	114.10 (14)	C11—C10—H10B	109.3
C3—C2—C1	121.12 (15)	C9—C10—H10B	109.3
C2—C3—C4	120.37 (15)	H10A—C10—H10B	107.9
C2—C3—H3	119.8	O3—C11—C10	108.16 (14)
C4—C3—H3	119.8	O3—C11—H11A	110.1
C5—C4—C3	119.73 (16)	C10—C11—H11A	110.1
C5—C4—H4	120.1	O3—C11—H11B	110.1
C3—C4—H4	120.1	C10—C11—H11B	110.1
C4—C5—C6	120.85 (16)	H11A—C11—H11B	108.4
C4—C5—H5	119.6	O3—C12—H12A	109.5
C6—C5—H5	119.6	O3—C12—H12B	109.5
C1—C6—C5	120.53 (15)	H12A—C12—H12B	109.5
C1—C6—C7	121.93 (15)	O3—C12—H12C	109.5
C5—C6—C7	117.53 (15)	H12A—C12—H12C	109.5
N1—C7—C6	128.21 (16)	H12B—C12—H12C	109.5
N1—C7—H7	115.9
O1i—Cu1—N1—C7	−173.21 (13)	C3—C4—C5—C6	−1.4 (2)
O1—Cu1—N1—C7	6.79 (13)	O1—C1—C6—C5	−179.61 (15)
O1i—Cu1—N1—C9	4.07 (11)	C2—C1—C6—C5	1.5 (2)
O1—Cu1—N1—C9	−175.93 (11)	O1—C1—C6—C7	1.2 (3)
N1i—Cu1—O1—C1	172.75 (14)	C2—C1—C6—C7	−177.67 (14)
N1—Cu1—O1—C1	−7.25 (14)	C4—C5—C6—C1	0.4 (2)
Cu1—O1—C1—C6	4.5 (2)	C4—C5—C6—C7	179.60 (14)
Cu1—O1—C1—C2	−176.60 (10)	C9—N1—C7—C6	178.39 (15)
C8—O2—C2—C3	0.2 (2)	Cu1—N1—C7—C6	−4.2 (2)
C8—O2—C2—C1	179.96 (13)	C1—C6—C7—N1	−1.1 (3)
O1—C1—C2—O2	−1.3 (2)	C5—C6—C7—N1	179.74 (16)
C6—C1—C2—O2	177.71 (13)	C7—N1—C9—C10	−101.17 (16)
O1—C1—C2—C3	178.53 (14)	Cu1—N1—C9—C10	81.35 (15)
C6—C1—C2—C3	−2.5 (2)	N1—C9—C10—C11	172.66 (13)
O2—C2—C3—C4	−178.62 (14)	C12—O3—C11—C10	−177.34 (13)
C1—C2—C3—C4	1.6 (2)	C9—C10—C11—O3	−64.55 (18)
C2—C3—C4—C5	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O3ii	0.98	2.58	3.476 (2)	151
C9—H9A···O1i	0.99	2.31	2.782 (2)	108
C9—H9B···O3	0.99	2.55	2.918 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O3i	0.98	2.58	3.476 (2)	151
C9—H9A⋯O1ii	0.99	2.31	2.782 (2)	108
C9—H9B⋯O3	0.99	2.55	2.918 (2)	102

Symmetry codes: (i) ; (ii) .