(2,2'-Bipyridine)(2-{1-[2-(dimethyl-amino)ethyl-imino]eth-yl}-4-methoxy-phenolato)copper(II) perchlorate.

The Cu atom of the title complex, [Cu(C(13)H(19)N(2)O(2))(C(10)H(8)N(2))]ClO(4), has a distorted square-pyramidal geometry with all three of the donor atoms from the N,N',O-tridentate Schiff base ligand in the equatorial positions and the bipyridine N atoms in an equatorial-axial binding mode. The Cu atom is 0.1801 (11) Å above the N(3)O mean basal plane.

Related literature

For the development of efficient catalytic systems for the coupling of CO2 with heterocycles into polycarbonates, see: Inoue et al. (1969 ▶). For the synthesis and catalytic studies of a series of bis­–(salicylaldiminato)zinc complexes, see: Darensbourg et al. (2001 ▶). For similar complexes, see: Dhar et al. (2006 ▶); Shen et al. (2003 ▶). For the synthesis, see: Hung & Lin (2009 ▶); Hung et al. (2008 ▶); For the chemical activity of complexes, see: Noh et al. (2007 ▶).

Experimental

Crystal data

[Cu(C13H19N2O2)(C10H8N2)]ClO4

M = 554.49

Monoclinic,

a = 10.1588 (10) Å

b = 18.2163 (17) Å

c = 13.3764 (13) Å

β = 92.610 (2)°

V = 2472.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 293 K

0.34 × 0.26 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.719, T max = 0.860

13946 measured reflections

4859 independent reflections

3488 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 0.98

4859 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 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/S1600536809014573/rk2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014573/rk2135Isup2.hkl

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

[Cu(C13H19N2O2)(C10H8N2)]ClO4	F(000) = 1148
Mr = 554.49	Dx = 1.489 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4710 reflections
a = 10.1588 (10) Å	θ = 2.3–25.6°
b = 18.2163 (17) Å	µ = 1.04 mm−1
c = 13.3764 (13) Å	T = 293 K
β = 92.610 (2)°	Parallelpiped, green
V = 2472.8 (4) Å3	0.34 × 0.26 × 0.15 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	4859 independent reflections
Radiation source: fine–focus sealed tube	3488 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.719, Tmax = 0.860	k = −22→16
13946 measured reflections	l = −16→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3
4859 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.30 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	0.62390 (3)	0.172001 (16)	0.82971 (2)	0.04095 (12)
O1	0.6832 (2)	0.15346 (10)	0.96441 (14)	0.0532 (5)
O2	0.9049 (3)	−0.10697 (14)	1.0997 (2)	0.1017 (10)
N1	0.5494 (2)	0.07290 (12)	0.81586 (16)	0.0457 (5)
N2	0.4979 (2)	0.19843 (13)	0.70841 (18)	0.0528 (6)
N3	0.8094 (2)	0.16361 (12)	0.75071 (17)	0.0469 (6)
N4	0.6989 (2)	0.27569 (11)	0.84447 (15)	0.0412 (5)
C1	0.7293 (3)	0.08881 (15)	0.9916 (2)	0.0455 (6)
C2	0.8227 (3)	0.08568 (17)	1.0724 (2)	0.0583 (8)
H2A	0.8483	0.1293	1.1039	0.070*
C3	0.8779 (4)	0.02114 (19)	1.1069 (2)	0.0681 (9)
H3A	0.9395	0.0215	1.1605	0.082*
C4	0.8411 (4)	−0.04469 (18)	1.0612 (2)	0.0665 (9)
C5	0.7497 (3)	−0.04455 (16)	0.9842 (2)	0.0576 (8)
H5A	0.7257	−0.0890	0.9544	0.069*
C6	0.6895 (3)	0.02080 (15)	0.94751 (19)	0.0439 (6)
C7	0.5849 (3)	0.01591 (15)	0.8687 (2)	0.0447 (7)
C8	0.5192 (3)	−0.05759 (16)	0.8497 (2)	0.0605 (8)
H8A	0.5193	−0.0850	0.9111	0.079 (10)*
H8B	0.5666	−0.0844	0.8011	0.102 (13)*
H8C	0.4300	−0.0500	0.8250	0.098 (13)*
C9	0.4456 (3)	0.06785 (18)	0.7363 (2)	0.0629 (8)
H9A	0.3599	0.0752	0.7639	0.075*
H9B	0.4469	0.0197	0.7054	0.075*
C10	0.4709 (3)	0.12658 (16)	0.6597 (2)	0.0603 (8)
H10A	0.5457	0.1125	0.6214	0.072*
H10B	0.3947	0.1309	0.6137	0.072*
C11	0.3779 (4)	0.2319 (2)	0.7440 (3)	0.0901 (13)
H11A	0.3197	0.2441	0.6879	0.135*
H11B	0.4002	0.2758	0.7809	0.135*
H11C	0.3349	0.1980	0.7867	0.135*
C12	0.5537 (4)	0.24885 (18)	0.6336 (2)	0.0728 (10)
H12A	0.4889	0.2579	0.5805	0.109*
H12B	0.6301	0.2267	0.6066	0.109*
H12C	0.5781	0.2944	0.6654	0.109*
C13	0.8909 (5)	−0.1720 (2)	1.0445 (3)	0.1034 (15)
H13A	0.9394	−0.2106	1.0783	0.155*
H13B	0.9244	−0.1648	0.9792	0.155*
H13C	0.7994	−0.1852	1.0380	0.155*
C14	0.8536 (3)	0.10711 (16)	0.6971 (2)	0.0578 (8)
H14A	0.8076	0.0630	0.6976	0.069*
C15	0.9634 (3)	0.11167 (19)	0.6418 (2)	0.0630 (9)
H15A	0.9903	0.0718	0.6045	0.076*
C16	1.0329 (3)	0.1763 (2)	0.6427 (3)	0.0689 (9)
H16A	1.1076	0.1809	0.6055	0.083*
C17	0.9908 (3)	0.23447 (17)	0.6995 (2)	0.0572 (8)
H17A	1.0379	0.2783	0.7021	0.069*
C18	0.8784 (3)	0.22671 (14)	0.75206 (19)	0.0415 (6)
C19	0.8210 (3)	0.28739 (14)	0.81221 (18)	0.0402 (6)
C20	0.8879 (3)	0.35225 (16)	0.8336 (2)	0.0531 (7)
H20A	0.9728	0.3592	0.8123	0.064*
C21	0.8265 (3)	0.40656 (17)	0.8872 (2)	0.0611 (8)
H21A	0.8702	0.4503	0.9025	0.073*
C22	0.7019 (3)	0.39554 (15)	0.9173 (2)	0.0546 (8)
H22A	0.6587	0.4319	0.9520	0.066*
C23	0.6409 (3)	0.32963 (14)	0.8954 (2)	0.0480 (7)
H23A	0.5561	0.3220	0.9166	0.058*
Cl	0.25347 (7)	0.09143 (4)	0.40216 (5)	0.05096 (19)
O3	0.2755 (3)	0.16261 (12)	0.4419 (2)	0.0957 (9)
O4	0.2085 (3)	0.09639 (16)	0.30025 (18)	0.0956 (9)
O5	0.1576 (3)	0.05517 (15)	0.4574 (2)	0.0958 (8)
O6	0.3729 (2)	0.05090 (16)	0.4085 (2)	0.0970 (9)

	U11	U22	U33	U12	U13	U23
Cu	0.0450 (2)	0.03477 (19)	0.04338 (19)	−0.00436 (14)	0.00530 (14)	−0.00633 (13)
O1	0.0719 (14)	0.0383 (11)	0.0488 (11)	−0.0068 (9)	−0.0037 (10)	−0.0082 (8)
O2	0.157 (3)	0.0660 (17)	0.0788 (17)	0.0307 (17)	−0.0360 (18)	0.0011 (13)
N1	0.0480 (14)	0.0429 (13)	0.0461 (12)	−0.0095 (11)	0.0028 (10)	−0.0070 (11)
N2	0.0570 (15)	0.0454 (14)	0.0554 (14)	0.0058 (12)	−0.0036 (12)	−0.0100 (11)
N3	0.0431 (13)	0.0430 (14)	0.0552 (14)	0.0014 (10)	0.0088 (11)	−0.0067 (10)
N4	0.0466 (13)	0.0356 (12)	0.0416 (12)	−0.0007 (10)	0.0033 (10)	−0.0018 (9)
C1	0.0533 (17)	0.0415 (16)	0.0424 (14)	−0.0072 (13)	0.0103 (12)	−0.0023 (12)
C2	0.071 (2)	0.0517 (19)	0.0519 (17)	−0.0082 (16)	−0.0031 (15)	−0.0078 (14)
C3	0.082 (2)	0.070 (2)	0.0515 (18)	−0.0007 (19)	−0.0059 (17)	−0.0052 (16)
C4	0.089 (3)	0.057 (2)	0.0532 (18)	0.0107 (18)	0.0023 (18)	−0.0003 (15)
C5	0.080 (2)	0.0413 (17)	0.0515 (17)	−0.0015 (15)	0.0065 (16)	−0.0040 (13)
C6	0.0526 (16)	0.0415 (15)	0.0383 (14)	−0.0049 (13)	0.0089 (12)	−0.0015 (11)
C7	0.0517 (16)	0.0389 (15)	0.0451 (15)	−0.0108 (13)	0.0191 (13)	−0.0092 (12)
C8	0.074 (2)	0.0480 (18)	0.0608 (19)	−0.0214 (16)	0.0146 (17)	−0.0062 (15)
C9	0.061 (2)	0.060 (2)	0.066 (2)	−0.0155 (16)	−0.0089 (16)	−0.0077 (16)
C10	0.070 (2)	0.0530 (19)	0.0569 (18)	0.0031 (16)	−0.0116 (16)	−0.0116 (14)
C11	0.063 (2)	0.103 (3)	0.103 (3)	0.028 (2)	−0.010 (2)	−0.035 (2)
C12	0.099 (3)	0.055 (2)	0.063 (2)	0.0052 (19)	−0.0126 (19)	0.0072 (16)
C13	0.149 (4)	0.068 (3)	0.092 (3)	0.037 (3)	−0.011 (3)	0.005 (2)
C14	0.0549 (18)	0.0486 (18)	0.070 (2)	0.0049 (14)	0.0082 (15)	−0.0145 (15)
C15	0.060 (2)	0.066 (2)	0.063 (2)	0.0147 (17)	0.0092 (16)	−0.0190 (16)
C16	0.0503 (19)	0.091 (3)	0.067 (2)	0.0089 (18)	0.0195 (16)	−0.0087 (18)
C17	0.0470 (17)	0.059 (2)	0.0658 (19)	−0.0041 (14)	0.0093 (15)	0.0006 (15)
C18	0.0399 (14)	0.0445 (15)	0.0398 (14)	0.0019 (12)	−0.0011 (11)	0.0024 (11)
C19	0.0429 (15)	0.0402 (15)	0.0371 (13)	−0.0018 (12)	−0.0026 (11)	0.0038 (11)
C20	0.0515 (18)	0.0513 (18)	0.0566 (17)	−0.0134 (14)	0.0023 (14)	−0.0014 (14)
C21	0.076 (2)	0.0430 (17)	0.0639 (19)	−0.0151 (16)	−0.0035 (17)	−0.0052 (14)
C22	0.077 (2)	0.0381 (16)	0.0488 (17)	0.0009 (15)	0.0025 (15)	−0.0054 (12)
C23	0.0541 (17)	0.0423 (16)	0.0480 (16)	0.0021 (13)	0.0060 (13)	−0.0046 (12)
Cl	0.0475 (4)	0.0508 (4)	0.0552 (4)	0.0010 (3)	0.0103 (3)	0.0000 (3)
O3	0.138 (3)	0.0527 (15)	0.097 (2)	−0.0073 (15)	0.0050 (18)	−0.0065 (13)
O4	0.0810 (17)	0.146 (3)	0.0593 (15)	0.0118 (17)	−0.0038 (13)	−0.0072 (15)
O5	0.0868 (18)	0.0864 (19)	0.118 (2)	−0.0077 (15)	0.0486 (16)	0.0223 (15)
O6	0.0599 (15)	0.113 (2)	0.118 (2)	0.0323 (15)	0.0115 (14)	0.0019 (17)

Cu—O1	1.9037 (19)	C9—H9B	0.9700
Cu—N1	1.963 (2)	C10—H10A	0.9700
Cu—N4	2.043 (2)	C10—H10B	0.9700
Cu—N2	2.077 (2)	C11—H11A	0.9600
Cu—N3	2.207 (2)	C11—H11B	0.9600
O1—C1	1.313 (3)	C11—H11C	0.9600
O2—C4	1.393 (4)	C12—H12A	0.9600
O2—C13	1.400 (4)	C12—H12B	0.9600
N1—C7	1.298 (3)	C12—H12C	0.9600
N1—C9	1.466 (3)	C13—H13A	0.9600
N2—C11	1.462 (4)	C13—H13B	0.9600
N2—C10	1.482 (4)	C13—H13C	0.9600
N2—C12	1.490 (4)	C14—C15	1.369 (4)
N3—C14	1.343 (3)	C14—H14A	0.9300
N3—C18	1.346 (3)	C15—C16	1.372 (4)
N4—C19	1.348 (3)	C15—H15A	0.9300
N4—C23	1.347 (3)	C16—C17	1.383 (4)
C1—C2	1.407 (4)	C16—H16A	0.9300
C1—C6	1.423 (4)	C17—C18	1.375 (4)
C2—C3	1.373 (4)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C19	1.501 (4)
C3—C4	1.389 (4)	C19—C20	1.386 (4)
C3—H3A	0.9300	C20—C21	1.387 (4)
C4—C5	1.355 (4)	C20—H20A	0.9300
C5—C6	1.416 (4)	C21—C22	1.360 (4)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.465 (4)	C22—C23	1.376 (4)
C7—C8	1.512 (4)	C22—H22A	0.9300
C8—H8A	0.9600	C23—H23A	0.9300
C8—H8B	0.9600	Cl—O5	1.413 (2)
C8—H8C	0.9600	Cl—O3	1.416 (2)
C9—C10	1.512 (4)	Cl—O6	1.419 (2)
C9—H9A	0.9700	Cl—O4	1.421 (2)
O1—Cu—N1	91.73 (9)	N2—C10—C9	111.1 (3)
O1—Cu—N4	88.40 (8)	N2—C10—H10A	109.4
N1—Cu—N4	179.21 (9)	C9—C10—H10A	109.4
O1—Cu—N2	159.65 (9)	N2—C10—H10B	109.4
N1—Cu—N2	85.30 (9)	C9—C10—H10B	109.4
N4—Cu—N2	94.31 (9)	H10A—C10—H10B	108.0
O1—Cu—N3	101.58 (9)	N2—C11—H11A	109.5
N1—Cu—N3	103.01 (9)	N2—C11—H11B	109.5
N4—Cu—N3	77.72 (8)	H11A—C11—H11B	109.5
N2—Cu—N3	98.71 (9)	N2—C11—H11C	109.5
C1—O1—Cu	121.01 (16)	H11A—C11—H11C	109.5
C4—O2—C13	117.4 (3)	H11B—C11—H11C	109.5
C7—N1—C9	121.2 (2)	N2—C12—H12A	109.5
C7—N1—Cu	125.99 (18)	N2—C12—H12B	109.5
C9—N1—Cu	112.81 (18)	H12A—C12—H12B	109.5
C11—N2—C10	111.8 (3)	N2—C12—H12C	109.5
C11—N2—C12	108.1 (3)	H12A—C12—H12C	109.5
C10—N2—C12	108.5 (2)	H12B—C12—H12C	109.5
C11—N2—Cu	109.6 (2)	O2—C13—H13A	109.5
C10—N2—Cu	103.51 (18)	O2—C13—H13B	109.5
C12—N2—Cu	115.31 (19)	H13A—C13—H13B	109.5
C14—N3—C18	118.4 (2)	O2—C13—H13C	109.5
C14—N3—Cu	128.5 (2)	H13A—C13—H13C	109.5
C18—N3—Cu	112.95 (17)	H13B—C13—H13C	109.5
C19—N4—C23	118.5 (2)	N3—C14—C15	122.8 (3)
C19—N4—Cu	117.37 (17)	N3—C14—H14A	118.6
C23—N4—Cu	123.61 (19)	C15—C14—H14A	118.6
O1—C1—C2	118.0 (2)	C14—C15—C16	118.6 (3)
O1—C1—C6	125.1 (3)	C14—C15—H15A	120.7
C2—C1—C6	116.9 (3)	C16—C15—H15A	120.7
C3—C2—C1	122.9 (3)	C15—C16—C17	119.3 (3)
C3—C2—H2A	118.5	C15—C16—H16A	120.3
C1—C2—H2A	118.5	C17—C16—H16A	120.3
C2—C3—C4	119.6 (3)	C18—C17—C16	119.1 (3)
C2—C3—H3A	120.2	C18—C17—H17A	120.4
C4—C3—H3A	120.2	C16—C17—H17A	120.4
C5—C4—C3	119.6 (3)	N3—C18—C17	121.7 (2)
C5—C4—O2	125.0 (3)	N3—C18—C19	114.9 (2)
C3—C4—O2	115.4 (3)	C17—C18—C19	123.4 (3)
C4—C5—C6	122.4 (3)	N4—C19—C20	121.2 (2)
C4—C5—H5A	118.8	N4—C19—C18	116.2 (2)
C6—C5—H5A	118.8	C20—C19—C18	122.6 (2)
C5—C6—C1	118.5 (3)	C21—C20—C19	119.1 (3)
C5—C6—C7	119.1 (2)	C21—C20—H20A	120.4
C1—C6—C7	122.3 (2)	C19—C20—H20A	120.4
N1—C7—C6	121.2 (2)	C22—C21—C20	119.6 (3)
N1—C7—C8	120.5 (3)	C22—C21—H21A	120.2
C6—C7—C8	118.3 (3)	C20—C21—H21A	120.2
C7—C8—H8A	109.5	C21—C22—C23	118.8 (3)
C7—C8—H8B	109.5	C21—C22—H22A	120.6
H8A—C8—H8B	109.5	C23—C22—H22A	120.6
C7—C8—H8C	109.5	N4—C23—C22	122.8 (3)
H8A—C8—H8C	109.5	N4—C23—H23A	118.6
H8B—C8—H8C	109.5	C22—C23—H23A	118.6
N1—C9—C10	108.0 (2)	O5—Cl—O3	109.42 (18)
N1—C9—H9A	110.1	O5—Cl—O6	109.47 (17)
C10—C9—H9A	110.1	O3—Cl—O6	109.50 (18)
N1—C9—H9B	110.1	O5—Cl—O4	109.41 (17)
C10—C9—H9B	110.1	O3—Cl—O4	109.93 (18)
H9A—C9—H9B	108.4	O6—Cl—O4	109.10 (17)