catena-Poly[[[(pyridine-κN)copper(II)]-μ-3-{1-[(2-amino-eth-yl)imino]-eth-yl}-6-methyl-2-oxo-2H-pyran-4-olato-κN,N,O:O] perchlorate].

In the title compound, {[Cu(C(10)H(13)N(2)O(3))(C(5)H(5)N)]ClO(4)}(n), the Cu(II) atom has an N(3)O(2) coordination sphere. The complex contains two different ligands, viz. a pyridine mol-ecule and a Schiff base mol-ecule, resulting from the condensation of ethyl-enodiamine with dehydro-acetic acid. The Cu(II) atom exhibits a square-pyramidal geometry: three of the four donors of the pyramid base belong to the Schiff base ligand (an N atom from the amine group, a second N atom from the imine group and the O atom of the pyran-one residue) and the fourth donor is the pyridine N atom. The coordination around the metal ion is completed by a longer axial bond to the pyran-one O atom of an adjacent Schiff base, so forming a one-dimensional polymer. The complex has a +1 charge that is compensated by a perchlorate ion. The crystal packing, which can be described as alternating chains of cations and tetra-hedral perchlorate anions along the a axis, is stabilized by inter-molecular N-H⋯O, C-H⋯O and C-H⋯N hydrogen-bonding interactions.

Related literature

For the synthesis of similar compounds: El-Abbassi et al. (1987 ▶); Fettouhi et al. (1996 ▶); El-Kihel et al. (1999 ▶); Tan & Kok-Peng Ang (1988 ▶); Djerrari et al. (2002 ▶); El-Kubaisi & Ismail (1994 ▶); Danilova et al. (2003 ▶); Munde et al. (2010 ▶). For their applications, see: Maiti et al. (1988 ▶); Mohan et al. (1981 ▶); Das & Livingstoone (1976 ▶); Moutet & Ali Ourari (1997 ▶); Ourari et al. (2008 ▶).

Experimental

Crystal data

[Cu(C10H13N2O3)(C5H5N)]ClO4

M = 451.32

Orthorhombic,

a = 8.8090 (2) Å

b = 19.9017 (4) Å

c = 20.9053 (5) Å

V = 3664.99 (14) Å3

Z = 8

Mo Kα radiation

μ = 1.38 mm−1

T = 295 K

0.12 × 0.11 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

7008 measured reflections

3731 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.03

3731 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.49 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046411/go2033sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046411/go2033Isup2.hkl

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

[Cu(C10H13N2O3)(C5H5N)]ClO4	Dx = 1.636 Mg m−3
Mr = 451.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pcab	Cell parameters from 4212 reflections
a = 8.8090 (2) Å	θ = 1.0–26.4°
b = 19.9017 (4) Å	µ = 1.38 mm−1
c = 20.9053 (5) Å	T = 295 K
V = 3664.99 (14) Å3	Plate, black
Z = 8	0.12 × 0.11 × 0.05 mm
F(000) = 1848

Nonius KappaCCD diffractometer	2619 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.022
graphite	θmax = 26.4°, θmin = 3.1°
Detector resolution: 9 pixels mm-1	h = 0→10
CCD rotation images, thick slices scans	k = 0→24
7008 measured reflections	l = 0→26
3731 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.807P] where P = (Fo2 + 2Fc2)/3
3731 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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
C1	0.2273 (4)	0.02862 (16)	0.45790 (16)	0.0517 (8)
H1	0.1798	0.0658	0.4399	0.062*
C2	0.3060 (4)	−0.01413 (18)	0.41827 (18)	0.0600 (9)
H2	0.311	−0.0058	0.3746	0.072*
C3	0.3770 (4)	−0.06940 (19)	0.4441 (2)	0.0600 (9)
H3	0.4319	−0.0988	0.4183	0.072*
C4	0.3652 (4)	−0.08009 (18)	0.5081 (2)	0.0630 (10)
H4	0.4119	−0.1171	0.5268	0.076*
C5	0.2830 (4)	−0.03545 (16)	0.54523 (18)	0.0560 (8)
H5	0.2742	−0.0439	0.5888	0.067*
C6	0.1257 (4)	0.09736 (17)	0.71225 (16)	0.0559 (9)
H6A	0.1883	0.137	0.7179	0.067*
H6B	0.1258	0.0722	0.752	0.067*
C7	−0.0333 (4)	0.11746 (18)	0.69521 (16)	0.0567 (9)
H7A	−0.1003	0.0789	0.6975	0.068*
H7B	−0.0699	0.1514	0.7247	0.068*
C8	−0.2344 (4)	0.22163 (17)	0.65805 (17)	0.0576 (9)
H8A	−0.2762	0.1859	0.6834	0.086*
H8B	−0.3139	0.2426	0.6338	0.086*
H8C	−0.1879	0.2543	0.6856	0.086*
C9	−0.1166 (3)	0.19342 (14)	0.61287 (14)	0.0398 (6)
C10	−0.1085 (3)	0.21966 (14)	0.54728 (14)	0.0380 (6)
C11	−0.1603 (3)	0.28666 (15)	0.53460 (15)	0.0430 (7)
C12	−0.1244 (4)	0.26748 (18)	0.42205 (14)	0.0508 (8)
C13	−0.1460 (6)	0.3012 (2)	0.3588 (2)	0.0908 (15)
H13A	−0.0797	0.3394	0.3559	0.136*
H13B	−0.2495	0.3158	0.3549	0.136*
H13C	−0.1228	0.2702	0.3251	0.136*
C14	−0.0700 (4)	0.20627 (18)	0.43217 (15)	0.0562 (9)
H14	−0.0417	0.1798	0.3975	0.067*
C15	−0.0541 (3)	0.18023 (15)	0.49603 (14)	0.0423 (7)
N1	0.2158 (3)	0.01933 (12)	0.52137 (12)	0.0432 (6)
N2	0.1869 (3)	0.05540 (13)	0.65998 (12)	0.0532 (7)
H2A	0.1582	0.0124	0.6655	0.064*
H2B	0.289	0.057	0.6602	0.064*
N3	−0.0300 (3)	0.14435 (12)	0.62977 (12)	0.0429 (6)
O1	0.0066 (2)	0.12212 (10)	0.50150 (10)	0.0491 (5)
O2	−0.1684 (3)	0.30769 (10)	0.47159 (11)	0.0541 (6)
O3	−0.1950 (3)	0.33001 (10)	0.57362 (11)	0.0519 (6)
O11	−0.1778 (3)	0.09728 (16)	0.29504 (16)	0.0869 (9)
O21	0.0241 (4)	0.16739 (14)	0.26635 (16)	0.0868 (9)
O31	−0.0210 (4)	0.06891 (19)	0.21098 (16)	0.1067 (11)
O41	0.0701 (4)	0.06507 (16)	0.31535 (17)	0.0910 (10)
Cl1	−0.02517 (10)	0.09943 (4)	0.27165 (4)	0.0553 (2)
Cu1	0.10791 (4)	0.089862 (17)	0.576431 (17)	0.03931 (14)

	U11	U22	U33	U12	U13	U23
C1	0.057 (2)	0.0475 (18)	0.0504 (19)	0.0085 (15)	0.0026 (16)	−0.0018 (15)
C2	0.065 (2)	0.062 (2)	0.053 (2)	0.0106 (18)	0.0082 (17)	−0.0093 (16)
C3	0.054 (2)	0.057 (2)	0.069 (2)	0.0124 (16)	0.0062 (17)	−0.0149 (19)
C4	0.063 (2)	0.0489 (19)	0.078 (3)	0.0197 (16)	−0.0030 (19)	−0.0071 (18)
C5	0.064 (2)	0.0480 (18)	0.056 (2)	0.0109 (16)	−0.0041 (17)	−0.0006 (16)
C6	0.075 (2)	0.0528 (19)	0.0397 (18)	0.0080 (17)	−0.0046 (16)	0.0028 (14)
C7	0.070 (2)	0.062 (2)	0.0386 (18)	0.0066 (17)	0.0109 (16)	0.0073 (16)
C8	0.065 (2)	0.0550 (19)	0.053 (2)	0.0112 (17)	0.0181 (17)	0.0024 (16)
C9	0.0388 (15)	0.0399 (15)	0.0406 (16)	−0.0040 (12)	0.0029 (12)	−0.0041 (12)
C10	0.0381 (15)	0.0365 (14)	0.0392 (15)	0.0007 (12)	−0.0003 (12)	0.0003 (12)
C11	0.0422 (16)	0.0434 (16)	0.0434 (17)	−0.0011 (13)	0.0003 (13)	0.0008 (13)
C12	0.062 (2)	0.0546 (19)	0.0354 (17)	0.0125 (15)	0.0016 (14)	0.0023 (14)
C13	0.123 (4)	0.094 (3)	0.055 (3)	0.040 (3)	0.002 (2)	0.021 (2)
C14	0.073 (2)	0.061 (2)	0.0352 (17)	0.0186 (17)	−0.0016 (15)	−0.0023 (14)
C15	0.0423 (16)	0.0458 (16)	0.0387 (16)	0.0055 (13)	−0.0009 (12)	−0.0036 (13)
N1	0.0465 (14)	0.0377 (12)	0.0456 (15)	0.0032 (10)	−0.0024 (11)	−0.0017 (11)
N2	0.0679 (18)	0.0489 (15)	0.0428 (15)	0.0100 (13)	−0.0001 (13)	0.0044 (12)
N3	0.0466 (15)	0.0428 (13)	0.0394 (14)	0.0003 (11)	0.0031 (11)	0.0037 (11)
O1	0.0591 (13)	0.0467 (12)	0.0415 (12)	0.0163 (10)	−0.0048 (10)	−0.0058 (9)
O2	0.0671 (14)	0.0458 (12)	0.0494 (13)	0.0110 (11)	0.0009 (11)	0.0060 (10)
O3	0.0640 (14)	0.0388 (11)	0.0528 (13)	0.0068 (10)	0.0018 (11)	−0.0062 (10)
O11	0.0555 (15)	0.116 (2)	0.089 (2)	−0.0077 (16)	0.0063 (16)	0.0173 (18)
O21	0.093 (2)	0.0626 (17)	0.105 (2)	−0.0126 (16)	−0.0017 (18)	0.0161 (16)
O31	0.109 (3)	0.145 (3)	0.067 (2)	−0.022 (2)	−0.0035 (19)	−0.038 (2)
O41	0.088 (2)	0.091 (2)	0.094 (2)	0.0057 (18)	−0.0299 (18)	0.0290 (18)
Cl1	0.0575 (5)	0.0638 (5)	0.0447 (5)	−0.0077 (4)	−0.0079 (4)	0.0055 (4)
Cu1	0.0458 (2)	0.0370 (2)	0.0352 (2)	0.00416 (15)	0.00067 (15)	0.00081 (14)

C1—N1	1.344 (4)	C10—C11	1.434 (4)
C1—C2	1.375 (4)	C11—O3	1.226 (4)
C1—H1	0.93	C11—O2	1.384 (4)
C2—C3	1.376 (5)	C12—C14	1.326 (5)
C2—H2	0.93	C12—O2	1.365 (4)
C3—C4	1.358 (6)	C12—C13	1.495 (5)
C3—H3	0.93	C13—H13A	0.96
C4—C5	1.385 (5)	C13—H13B	0.96
C4—H4	0.93	C13—H13C	0.96
C5—N1	1.337 (4)	C14—C15	1.439 (4)
C5—H5	0.93	C14—H14	0.93
C6—N2	1.477 (4)	C15—O1	1.279 (4)
C6—C7	1.499 (5)	N1—Cu1	2.049 (2)
C6—H6A	0.97	N2—Cu1	2.001 (3)
C6—H6B	0.97	N2—H2A	0.9
C7—N3	1.469 (4)	N2—H2B	0.9
C7—H7A	0.97	N3—Cu1	1.974 (2)
C7—H7B	0.97	O1—Cu1	1.914 (2)
C8—C9	1.512 (4)	O3—Cu1i	2.358 (2)
C8—H8A	0.96	O11—Cl1	1.431 (3)
C8—H8B	0.96	O21—Cl1	1.425 (3)
C8—H8C	0.96	O31—Cl1	1.407 (3)
C9—N3	1.288 (4)	O41—Cl1	1.417 (3)
C9—C10	1.469 (4)	Cu1—O3ii	2.358 (2)
C10—C15	1.412 (4)
N1—C1—C2	123.2 (3)	O2—C12—C13	111.8 (3)
N1—C1—H1	118.4	C12—C13—H13A	109.5
C2—C1—H1	118.4	C12—C13—H13B	109.5
C1—C2—C3	119.2 (4)	H13A—C13—H13B	109.5
C1—C2—H2	120.4	C12—C13—H13C	109.5
C3—C2—H2	120.4	H13A—C13—H13C	109.5
C4—C3—C2	118.5 (3)	H13B—C13—H13C	109.5
C4—C3—H3	120.8	C12—C14—C15	120.9 (3)
C2—C3—H3	120.8	C12—C14—H14	119.5
C3—C4—C5	119.5 (3)	C15—C14—H14	119.5
C3—C4—H4	120.3	O1—C15—C10	125.2 (3)
C5—C4—H4	120.3	O1—C15—C14	116.7 (3)
N1—C5—C4	123.1 (3)	C10—C15—C14	118.1 (3)
N1—C5—H5	118.5	C5—N1—C1	116.6 (3)
C4—C5—H5	118.5	C5—N1—Cu1	123.7 (2)
N2—C6—C7	108.4 (3)	C1—N1—Cu1	119.7 (2)
N2—C6—H6A	110	C6—N2—Cu1	108.96 (19)
C7—C6—H6A	110	C6—N2—H2A	109.9
N2—C6—H6B	110	Cu1—N2—H2A	109.9
C7—C6—H6B	110	C6—N2—H2B	109.9
H6A—C6—H6B	108.4	Cu1—N2—H2B	109.9
N3—C7—C6	107.5 (3)	H2A—N2—H2B	108.3
N3—C7—H7A	110.2	C9—N3—C7	121.3 (3)
C6—C7—H7A	110.2	C9—N3—Cu1	128.7 (2)
N3—C7—H7B	110.2	C7—N3—Cu1	109.75 (19)
C6—C7—H7B	110.2	C15—O1—Cu1	124.85 (19)
H7A—C7—H7B	108.5	C12—O2—C11	122.0 (2)
C9—C8—H8A	109.5	C11—O3—Cu1i	132.6 (2)
C9—C8—H8B	109.5	O31—Cl1—O41	110.9 (2)
H8A—C8—H8B	109.5	O31—Cl1—O21	109.4 (2)
C9—C8—H8C	109.5	O41—Cl1—O21	109.14 (19)
H8A—C8—H8C	109.5	O31—Cl1—O11	108.7 (2)
H8B—C8—H8C	109.5	O41—Cl1—O11	108.8 (2)
N3—C9—C10	119.8 (3)	O21—Cl1—O11	109.94 (19)
N3—C9—C8	121.1 (3)	O1—Cu1—N3	89.50 (9)
C10—C9—C8	119.0 (3)	O1—Cu1—N2	172.52 (11)
C15—C10—C11	119.0 (3)	N3—Cu1—N2	84.80 (10)
C15—C10—C9	121.8 (3)	O1—Cu1—N1	89.20 (9)
C11—C10—C9	119.2 (3)	N3—Cu1—N1	168.32 (10)
O3—C11—O2	114.0 (3)	N2—Cu1—N1	95.41 (10)
O3—C11—C10	127.6 (3)	O1—Cu1—O3ii	95.50 (9)
O2—C11—C10	118.3 (3)	N3—Cu1—O3ii	95.48 (9)
C14—C12—O2	121.4 (3)	N2—Cu1—O3ii	89.86 (10)
C14—C12—C13	126.9 (3)	N1—Cu1—O3ii	96.20 (9)
N1—C1—C2—C3	0.0 (5)	C6—C7—N3—Cu1	39.9 (3)
C1—C2—C3—C4	0.8 (6)	C10—C15—O1—Cu1	−25.3 (4)
C2—C3—C4—C5	−0.1 (6)	C14—C15—O1—Cu1	155.8 (2)
C3—C4—C5—N1	−1.3 (6)	C14—C12—O2—C11	−0.7 (5)
N2—C6—C7—N3	−49.7 (4)	C13—C12—O2—C11	179.3 (3)
N3—C9—C10—C15	23.6 (4)	O3—C11—O2—C12	175.7 (3)
C8—C9—C10—C15	−152.3 (3)	C10—C11—O2—C12	−2.1 (4)
N3—C9—C10—C11	−157.8 (3)	O2—C11—O3—Cu1i	42.7 (4)
C8—C9—C10—C11	26.3 (4)	C10—C11—O3—Cu1i	−139.8 (3)
C15—C10—C11—O3	−171.4 (3)	C15—O1—Cu1—N3	31.6 (3)
C9—C10—C11—O3	10.0 (5)	C15—O1—Cu1—N1	−160.0 (3)
C15—C10—C11—O2	6.1 (4)	C15—O1—Cu1—O3ii	−63.8 (3)
C9—C10—C11—O2	−172.5 (2)	C9—N3—Cu1—O1	−16.1 (3)
O2—C12—C14—C15	−0.6 (6)	C7—N3—Cu1—O1	158.9 (2)
C13—C12—C14—C15	179.5 (4)	C9—N3—Cu1—N2	168.7 (3)
C11—C10—C15—O1	173.9 (3)	C7—N3—Cu1—N2	−16.2 (2)
C9—C10—C15—O1	−7.5 (5)	C9—N3—Cu1—N1	−99.8 (5)
C11—C10—C15—C14	−7.2 (4)	C7—N3—Cu1—N1	75.3 (6)
C9—C10—C15—C14	171.3 (3)	C9—N3—Cu1—O3ii	79.4 (3)
C12—C14—C15—O1	−176.5 (3)	C7—N3—Cu1—O3ii	−105.6 (2)
C12—C14—C15—C10	4.6 (5)	C6—N2—Cu1—N3	−11.2 (2)
C4—C5—N1—C1	2.0 (5)	C6—N2—Cu1—N1	−179.5 (2)
C4—C5—N1—Cu1	−175.0 (3)	C6—N2—Cu1—O3ii	84.3 (2)
C2—C1—N1—C5	−1.3 (5)	C5—N1—Cu1—O1	−162.4 (3)
C2—C1—N1—Cu1	175.8 (3)	C1—N1—Cu1—O1	20.7 (2)
C7—C6—N2—Cu1	36.0 (3)	C5—N1—Cu1—N3	−78.7 (6)
C10—C9—N3—C7	179.1 (3)	C1—N1—Cu1—N3	104.4 (5)
C8—C9—N3—C7	−5.1 (4)	C5—N1—Cu1—N2	11.7 (3)
C10—C9—N3—Cu1	−6.4 (4)	C1—N1—Cu1—N2	−165.2 (2)
C8—C9—N3—Cu1	169.4 (2)	C5—N1—Cu1—O3ii	102.2 (3)
C6—C7—N3—C9	−144.6 (3)	C1—N1—Cu1—O3ii	−74.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11iii	0.90	2.34	3.182 (4)	156.
N2—H2A···O41iii	0.90	2.57	3.338 (4)	144.
N2—H2B···O31iv	0.90	2.31	3.142 (4)	153.
C1—H1···O1	0.93	2.29	2.842 (4)	118.
C5—H5···N2	0.93	2.59	3.121 (4)	117.
C8—H8B···O3	0.96	2.39	2.809 (4)	106.

Table 1

Selected bond lengths (Å)

N1—Cu1	2.049 (2)
N2—Cu1	2.001 (3)
N3—Cu1	1.974 (2)
O1—Cu1	1.914 (2)
O3—Cu1i	2.358 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O11ii	0.90	2.34	3.182 (4)	156
N2—H2A⋯O41ii	0.90	2.57	3.338 (4)	144
N2—H2B⋯O31iii	0.90	2.31	3.142 (4)	153
C1—H1⋯O1	0.93	2.29	2.842 (4)	118
C5—H5⋯N2	0.93	2.59	3.121 (4)	117
C8—H8B⋯O3	0.96	2.39	2.809 (4)	106

Symmetry codes: (ii) ; (iii) .