(Ethyl-enediamine-κ(2)N,N')bis-(perchlorato-κO)bis-(pyridine-κN)copper(II).

In the title compound, [Cu(ClO(4))(2)(C(2)H(8)N(2))(C(5)H(5)N)(2)], the Cu(II) cation is located on a twofold rotation axis and is coordinated by four N and two O atoms in a tetragonally distorted octahedral geometry. The crystal packing can be described as ClO(4) tetra-hedra and CuN(4)O(2) octa-hedra alternating in a zigzag fashion along the c axis. The structure is stabilized by intermolecular N-H⋯O and C-H⋯O hydrogen bonds, as well as π-π interactions [centroid-centroid distance = 3.7179 (15) Å].

Related literature

For synthesis and applications of similar compounds, see: De Stefano et al. (1999 ▶); Sing et al. (2004 ▶); Elliot & Herchenhart (1982 ▶); Moncol et al. (2008 ▶); Costes et al. (1998 ▶).

Experimental

Crystal data

[Cu(ClO4)2(C2H8N2)(C5H5N)2]

M = 480.74

Monoclinic,

a = 7.697 (1) Å

b = 17.238 (2) Å

c = 14.206 (1) Å

β = 100.551 (1)°

V = 1853.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.52 mm−1

T = 295 K

0.17 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

4657 measured reflections

2400 independent reflections

2117 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.08

2400 reflections

124 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.75 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); 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/S1600536812029868/zj2084sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029868/zj2084Isup2.hkl

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

[Cu(ClO4)2(C2H8N2)(C5H5N)2]	F(000) = 980
Mr = 480.74	Dx = 1.723 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.697 (1) Å	Cell parameters from 2471 reflections
b = 17.238 (2) Å	θ = 1.0–28.7°
c = 14.206 (1) Å	µ = 1.52 mm−1
β = 100.551 (1)°	T = 295 K
V = 1853.0 (3) Å3	Prism, colourless
Z = 4	0.17 × 0.15 × 0.13 mm

Nonius KappaCCD diffractometer	2117 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.026
Graphite monochromator	θmax = 28.7°, θmin = 2.9°
Detector resolution: 9 pixels mm-1	h = −10→10
CCD rotation images, thick slices scans	k = −21→23
4657 measured reflections	l = −19→19
2400 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0907P)2 + 1.252P] where P = (Fo2 + 2Fc2)/3
2400 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.75 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	1.0960 (4)	1.02744 (14)	0.77477 (19)	0.0420 (5)
H1A	1.1727	1.0316	0.7279	0.050*
H1B	1.1191	1.0711	0.8183	0.050*
C2	0.6763 (3)	0.78272 (14)	0.66706 (18)	0.0373 (5)
H2	0.6232	0.8232	0.6946	0.045*
C3	0.5711 (3)	0.72425 (15)	0.6214 (2)	0.0434 (5)
H3	0.4492	0.7256	0.6176	0.052*
C4	0.6494 (4)	0.66365 (15)	0.5815 (2)	0.0443 (6)
H4	0.5815	0.6230	0.5514	0.053*
C5	0.8304 (4)	0.66431 (15)	0.5869 (2)	0.0453 (6)
H5	0.8862	0.6242	0.5603	0.054*
C6	0.9274 (3)	0.72536 (15)	0.63244 (18)	0.0413 (5)
H6	1.0489	0.7261	0.6348	0.050*
N1	1.1296 (3)	0.95373 (12)	0.82833 (15)	0.0375 (4)
H1C	1.0923	0.9576	0.8846	0.045*
H1D	1.2463	0.9437	0.8405	0.045*
N2	0.8526 (3)	0.78360 (11)	0.67335 (14)	0.0331 (4)
O11	0.7648 (4)	0.86617 (14)	0.8613 (2)	0.0731 (8)
O12	0.8304 (3)	0.97537 (13)	0.95701 (16)	0.0552 (5)
O13	0.6922 (4)	0.86854 (17)	1.0120 (2)	0.0783 (9)
O14	0.5379 (3)	0.9459 (2)	0.8925 (3)	0.0996 (11)
Cl1	0.70478 (7)	0.91475 (3)	0.93029 (4)	0.0372 (2)
Cu1	1.0000	0.86690 (2)	0.7500	0.03224 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0521 (15)	0.0313 (11)	0.0429 (12)	−0.0063 (10)	0.0091 (11)	−0.0030 (9)
C2	0.0338 (11)	0.0349 (11)	0.0425 (12)	0.0019 (8)	0.0053 (9)	−0.0036 (9)
C3	0.0361 (12)	0.0412 (13)	0.0515 (14)	−0.0038 (9)	0.0043 (10)	−0.0029 (10)
C4	0.0472 (14)	0.0382 (13)	0.0462 (13)	−0.0093 (10)	0.0048 (11)	−0.0065 (10)
C5	0.0515 (15)	0.0365 (12)	0.0500 (14)	0.0010 (10)	0.0154 (11)	−0.0102 (10)
C6	0.0352 (12)	0.0423 (13)	0.0469 (13)	0.0015 (9)	0.0089 (10)	−0.0059 (10)
N1	0.0377 (10)	0.0357 (10)	0.0373 (9)	−0.0011 (8)	0.0022 (8)	−0.0035 (8)
N2	0.0334 (9)	0.0302 (9)	0.0347 (9)	−0.0003 (7)	0.0031 (7)	−0.0025 (7)
O11	0.0894 (19)	0.0654 (16)	0.0759 (16)	−0.0184 (12)	0.0450 (15)	−0.0287 (12)
O12	0.0490 (11)	0.0538 (12)	0.0612 (12)	−0.0194 (9)	0.0058 (9)	−0.0112 (10)
O13	0.085 (2)	0.091 (2)	0.0637 (16)	−0.0214 (14)	0.0274 (14)	0.0171 (13)
O14	0.0421 (13)	0.085 (2)	0.154 (3)	0.0104 (13)	−0.0286 (16)	−0.007 (2)
Cl1	0.0288 (3)	0.0418 (3)	0.0406 (3)	−0.00471 (19)	0.0051 (2)	−0.0045 (2)
Cu1	0.0302 (3)	0.0291 (3)	0.0357 (3)	0.000	0.00142 (16)	0.000

C1—N1	1.479 (3)	C6—N2	1.342 (3)
C1—C1i	1.517 (5)	C6—H6	0.9300
C1—H1A	0.9700	N1—H1C	0.9000
C1—H1B	0.9700	N1—H1D	0.9000
C2—N2	1.343 (3)	N1—Cu1	2.017 (2)
C2—C3	1.379 (3)	N2—Cu1	2.0206 (19)
C2—H2	0.9300	O11—Cu1	2.613 (3)
C3—C4	1.379 (4)	O11—Cl1	1.428 (2)
C3—H3	0.9300	O12—Cl1	1.427 (2)
C4—C5	1.381 (4)	O13—Cl1	1.425 (3)
C4—H4	0.9300	O14—Cl1	1.406 (2)
C5—C6	1.381 (4)	Cu1—N1i	2.017 (2)
C5—H5	0.9300	Cu1—N2i	2.0206 (19)
N1—C1—C1i	107.61 (17)	C1—N1—H1D	109.8
N1—C1—H1A	110.2	Cu1—N1—H1D	109.8
C1i—C1—H1A	110.2	H1C—N1—H1D	108.3
N1—C1—H1B	110.2	C6—N2—C2	118.1 (2)
C1i—C1—H1B	110.2	C6—N2—Cu1	121.47 (17)
H1A—C1—H1B	108.5	C2—N2—Cu1	120.30 (15)
N2—C2—C3	122.6 (2)	Cl1—O11—Cu1	139.39 (15)
N2—C2—H2	118.7	O14—Cl1—O13	109.3 (2)
C3—C2—H2	118.7	O14—Cl1—O12	110.42 (17)
C2—C3—C4	118.9 (2)	O13—Cl1—O12	109.67 (17)
C2—C3—H3	120.5	O14—Cl1—O11	110.5 (2)
C4—C3—H3	120.5	O13—Cl1—O11	108.03 (18)
C3—C4—C5	118.9 (2)	O12—Cl1—O11	108.87 (15)
C3—C4—H4	120.5	N1—Cu1—N1i	84.17 (12)
C5—C4—H4	120.5	N1—Cu1—N2i	93.31 (9)
C6—C5—C4	119.1 (2)	N1i—Cu1—N2i	175.59 (8)
C6—C5—H5	120.5	N1—Cu1—N2	175.59 (8)
C4—C5—H5	120.5	N1i—Cu1—N2	93.31 (9)
N2—C6—C5	122.4 (2)	N2i—Cu1—N2	89.42 (11)
N2—C6—H6	118.8	N1—Cu1—O11	89.85 (8)
C5—C6—H6	118.8	N1i—Cu1—O11	90.56 (10)
C1—N1—Cu1	109.36 (15)	N2i—Cu1—O11	93.06 (9)
C1—N1—H1C	109.8	N2—Cu1—O11	86.55 (8)
Cu1—N1—H1C	109.8
N2—C2—C3—C4	0.8 (4)	C1—N1—Cu1—N2	−69.6 (10)
C2—C3—C4—C5	−1.3 (4)	C1—N1—Cu1—O11	−104.80 (17)
C3—C4—C5—C6	0.3 (4)	C6—N2—Cu1—N1	−179 (100)
C4—C5—C6—N2	1.3 (4)	C2—N2—Cu1—N1	−3.5 (11)
C1i—C1—N1—Cu1	39.1 (3)	C6—N2—Cu1—N1i	125.50 (19)
C5—C6—N2—C2	−1.8 (4)	C2—N2—Cu1—N1i	−58.60 (19)
C5—C6—N2—Cu1	174.2 (2)	C6—N2—Cu1—N2i	−51.04 (17)
C3—C2—N2—C6	0.7 (4)	C2—N2—Cu1—N2i	124.9 (2)
C3—C2—N2—Cu1	−175.34 (19)	C6—N2—Cu1—O11	−144.1 (2)
Cu1—O11—Cl1—O14	107.9 (3)	C2—N2—Cu1—O11	31.77 (19)
Cu1—O11—Cl1—O13	−132.5 (3)	Cl1—O11—Cu1—N1	17.1 (3)
Cu1—O11—Cl1—O12	−13.5 (4)	Cl1—O11—Cu1—N1i	−67.1 (3)
C1—N1—Cu1—N1i	−14.22 (12)	Cl1—O11—Cu1—N2i	110.4 (3)
C1—N1—Cu1—N2i	162.14 (16)	Cl1—O11—Cu1—N2	−160.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O12	0.90	2.44	3.213 (3)	144
N1—H1C···O12ii	0.90	2.50	3.247 (3)	140
N1—H1D···O14iii	0.90	2.23	3.111 (4)	166
C2—H2···O11	0.93	2.53	3.076 (4)	118
C5—H5···O13iv	0.93	2.57	3.208 (4)	126

Table 1

Selected bond lengths (Å)

N1—Cu1	2.017 (2)
N2—Cu1	2.0206 (19)
O11—Cu1	2.613 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O12	0.90	2.44	3.213 (3)	144
N1—H1C⋯O12i	0.90	2.50	3.247 (3)	140
N1—H1D⋯O14ii	0.90	2.23	3.111 (4)	166
C2—H2⋯O11	0.93	2.53	3.076 (4)	118
C5—H5⋯O13iii	0.93	2.57	3.208 (4)	126

Symmetry codes: (i) ; (ii) ; (iii) .