Bis{μ-4-chloro-2-[(2-pyridyleth-yl)imino-meth-yl]phenolato}bis-[chloridocopper(II)].

The title compound, [Cu(2)(C(14)H(12)ClN(2)O)(2)Cl(2)], is a copper(II) dimer where the metal centres are bridged by O atoms from a 5-chloro-salicylaldehyde group. The coordination geometry of each copper(II) centre is distorted square-pyramidal, with two N atoms from a 2-ethyl-amino-pyridine group and two O atoms from a 5-chloro-salicylaldehyde group occupying the basal positions, and with a Cl atom at the apical position. The dimer is centrosymmetric, with a crystallographic inversion centre midway between the two Cu atoms [Cu⋯Cu = 3.103 (9) Å].

Related literature

For related literature, see: Du et al. (2003 ▶); Rojas et al. (2004 ▶); Yamada (1999 ▶).

Experimental

Crystal data

[Cu2(C14H12ClN2O)2Cl2]

M = 717.39

Monoclinic,

a = 9.9703 (10) Å

b = 9.0119 (11) Å

c = 16.5018 (16) Å

β = 96.0390 (10)°

V = 1474.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.84 mm−1

T = 298 (2) K

0.50 × 0.42 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.460, T max = 0.957

7139 measured reflections

2587 independent reflections

2101 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.05

2587 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536808022162/gw2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022162/gw2043Isup2.hkl

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

[Cu2(C14H12Cl1N2O)2Cl2]	F000 = 724
Mr = 717.39	Dx = 1.616 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 9.9703 (10) Å	Cell parameters from 3383 reflections
b = 9.0119 (11) Å	θ = 2.3–28.1º
c = 16.5018 (16) Å	µ = 1.84 mm−1
β = 96.0390 (10)º	T = 298 (2) K
V = 1474.5 (3) Å3	Block, brown
Z = 2	0.50 × 0.42 × 0.02 mm

Bruker SMART CCD area-detector diffractometer	2587 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.460, Tmax = 0.957	k = −10→10
7139 measured reflections	l = −14→19

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0359P)2 + 0.6685P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2587 reflections	Δρmax = 0.38 e Å−3
181 parameters	Δρmin = −0.32 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	0.40654 (3)	0.92113 (4)	0.05596 (2)	0.03066 (13)
Cl1	1.06351 (9)	0.91583 (13)	0.29917 (6)	0.0704 (3)
Cl2	0.29315 (9)	1.11255 (9)	0.11335 (5)	0.0489 (2)
N1	0.3451 (2)	0.7177 (2)	0.01064 (14)	0.0326 (5)
N2	0.4538 (2)	0.8209 (2)	0.16031 (13)	0.0328 (5)
O1	0.60250 (18)	0.9870 (2)	0.05178 (11)	0.0332 (5)
C1	0.3444 (3)	0.7399 (4)	0.19511 (18)	0.0451 (8)
H1A	0.3116	0.7990	0.2380	0.054*
H1B	0.3796	0.6477	0.2191	0.054*
C2	0.2278 (3)	0.7060 (3)	0.13033 (19)	0.0431 (8)
H2A	0.1642	0.6415	0.1538	0.052*
H2B	0.1814	0.7979	0.1147	0.052*
C3	0.2706 (3)	0.6337 (3)	0.05563 (18)	0.0378 (7)
C4	0.2375 (4)	0.4895 (4)	0.0332 (2)	0.0553 (9)
H4	0.1859	0.4316	0.0648	0.066*
C5	0.2823 (5)	0.4327 (4)	−0.0368 (3)	0.0684 (12)
H5	0.2613	0.3357	−0.0526	0.082*
C6	0.3568 (4)	0.5184 (4)	−0.0824 (2)	0.0557 (10)
H6	0.3866	0.4812	−0.1300	0.067*
C7	0.3882 (3)	0.6617 (3)	−0.05733 (18)	0.0423 (8)
H7	0.4401	0.7205	−0.0882	0.051*
C8	0.5714 (3)	0.8170 (3)	0.19992 (16)	0.0346 (7)
H8	0.5789	0.7624	0.2480	0.042*
C9	0.6936 (3)	0.8864 (3)	0.17933 (16)	0.0304 (6)
C10	0.7074 (3)	0.9662 (3)	0.10664 (16)	0.0304 (6)
C11	0.8341 (3)	1.0216 (3)	0.09434 (18)	0.0392 (7)
H11	0.8453	1.0702	0.0458	0.047*
C12	0.9435 (3)	1.0062 (4)	0.15249 (19)	0.0429 (8)
H12	1.0267	1.0463	0.1439	0.051*
C13	0.9277 (3)	0.9303 (3)	0.22358 (19)	0.0418 (8)
C14	0.8076 (3)	0.8687 (3)	0.23679 (18)	0.0387 (7)
H14	0.8005	0.8144	0.2841	0.046*

	U11	U22	U33	U12	U13	U23
Cu1	0.0349 (2)	0.0311 (2)	0.02574 (19)	−0.00498 (15)	0.00216 (14)	0.00274 (14)
Cl1	0.0410 (5)	0.1083 (9)	0.0574 (6)	0.0051 (5)	−0.0164 (4)	0.0100 (5)
Cl2	0.0554 (5)	0.0391 (5)	0.0541 (5)	0.0034 (4)	0.0150 (4)	−0.0099 (4)
N1	0.0365 (14)	0.0285 (13)	0.0315 (13)	−0.0010 (11)	−0.0028 (10)	0.0010 (10)
N2	0.0392 (14)	0.0313 (13)	0.0285 (12)	−0.0062 (11)	0.0061 (10)	0.0022 (10)
O1	0.0299 (11)	0.0400 (11)	0.0286 (10)	−0.0046 (9)	−0.0018 (8)	0.0094 (9)
C1	0.048 (2)	0.053 (2)	0.0358 (17)	−0.0115 (16)	0.0077 (14)	0.0078 (15)
C2	0.0405 (18)	0.0408 (18)	0.0485 (19)	−0.0105 (15)	0.0071 (14)	0.0110 (15)
C3	0.0378 (18)	0.0288 (16)	0.0441 (18)	−0.0024 (13)	−0.0078 (14)	0.0052 (13)
C4	0.067 (2)	0.0361 (19)	0.059 (2)	−0.0146 (17)	−0.0094 (18)	0.0057 (17)
C5	0.090 (3)	0.032 (2)	0.077 (3)	−0.001 (2)	−0.022 (2)	−0.0097 (19)
C6	0.073 (3)	0.042 (2)	0.050 (2)	0.0119 (19)	−0.0068 (18)	−0.0130 (17)
C7	0.0445 (19)	0.0434 (19)	0.0376 (17)	0.0064 (15)	−0.0026 (14)	−0.0032 (14)
C8	0.0470 (19)	0.0328 (16)	0.0236 (14)	0.0004 (14)	0.0017 (12)	0.0027 (12)
C9	0.0344 (16)	0.0293 (15)	0.0270 (15)	−0.0006 (12)	0.0009 (12)	−0.0026 (11)
C10	0.0345 (16)	0.0268 (15)	0.0293 (15)	−0.0010 (12)	0.0006 (12)	−0.0015 (11)
C11	0.0358 (18)	0.0423 (18)	0.0393 (17)	−0.0025 (14)	0.0028 (13)	0.0081 (14)
C12	0.0275 (16)	0.0469 (19)	0.053 (2)	−0.0012 (14)	−0.0005 (14)	0.0035 (16)
C13	0.0336 (18)	0.0494 (19)	0.0402 (18)	0.0040 (15)	−0.0070 (13)	−0.0002 (15)
C14	0.0416 (19)	0.0407 (17)	0.0321 (16)	0.0058 (14)	−0.0031 (13)	0.0030 (13)

Cu1—O1i	1.9547 (18)	C4—C5	1.381 (5)
Cu1—N2	1.958 (2)	C4—H4	0.9300
Cu1—N1	2.049 (2)	C5—C6	1.353 (6)
Cu1—O1	2.0500 (19)	C5—H5	0.9300
Cu1—Cl2	2.3187 (9)	C6—C7	1.382 (5)
Cl1—C13	1.747 (3)	C6—H6	0.9300
N1—C3	1.339 (4)	C7—H7	0.9300
N1—C7	1.341 (4)	C8—C9	1.441 (4)
N2—C8	1.282 (4)	C8—H8	0.9300
N2—C1	1.478 (4)	C9—C14	1.411 (4)
O1—C10	1.323 (3)	C9—C10	1.417 (4)
O1—Cu1i	1.9547 (18)	C10—C11	1.392 (4)
C1—C2	1.525 (4)	C11—C12	1.382 (4)
C1—H1A	0.9700	C11—H11	0.9300
C1—H1B	0.9700	C12—C13	1.381 (4)
C2—C3	1.495 (4)	C12—H12	0.9300
C2—H2A	0.9700	C13—C14	1.358 (4)
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.382 (4)
O1i—Cu1—N2	168.33 (9)	C5—C4—C3	118.9 (4)
O1i—Cu1—N1	93.65 (9)	C5—C4—H4	120.5
N2—Cu1—N1	86.74 (9)	C3—C4—H4	120.5
O1i—Cu1—O1	78.44 (8)	C6—C5—C4	119.9 (3)
N2—Cu1—O1	91.22 (8)	C6—C5—H5	120.0
N1—Cu1—O1	119.75 (9)	C4—C5—H5	120.0
O1i—Cu1—Cl2	94.50 (6)	C5—C6—C7	119.1 (3)
N2—Cu1—Cl2	93.82 (7)	C5—C6—H6	120.4
N1—Cu1—Cl2	132.43 (7)	C7—C6—H6	120.4
O1—Cu1—Cl2	107.80 (6)	N1—C7—C6	121.3 (3)
C3—N1—C7	119.7 (3)	N1—C7—H7	119.3
C3—N1—Cu1	117.75 (19)	C6—C7—H7	119.3
C7—N1—Cu1	122.2 (2)	N2—C8—C9	128.2 (3)
C8—N2—C1	117.5 (2)	N2—C8—H8	115.9
C8—N2—Cu1	125.7 (2)	C9—C8—H8	115.9
C1—N2—Cu1	116.79 (18)	C14—C9—C10	118.9 (3)
C10—O1—Cu1i	129.79 (18)	C14—C9—C8	115.7 (3)
C10—O1—Cu1	128.60 (17)	C10—C9—C8	125.4 (2)
Cu1i—O1—Cu1	101.56 (8)	O1—C10—C11	120.9 (3)
N2—C1—C2	111.4 (2)	O1—C10—C9	120.7 (3)
N2—C1—H1A	109.3	C11—C10—C9	118.4 (3)
C2—C1—H1A	109.3	C12—C11—C10	121.6 (3)
N2—C1—H1B	109.3	C12—C11—H11	119.2
C2—C1—H1B	109.3	C10—C11—H11	119.2
H1A—C1—H1B	108.0	C13—C12—C11	119.2 (3)
C3—C2—C1	113.7 (3)	C13—C12—H12	120.4
C3—C2—H2A	108.8	C11—C12—H12	120.4
C1—C2—H2A	108.8	C14—C13—C12	121.3 (3)
C3—C2—H2B	108.8	C14—C13—Cl1	119.0 (2)
C1—C2—H2B	108.8	C12—C13—Cl1	119.6 (3)
H2A—C2—H2B	107.7	C13—C14—C9	120.5 (3)
N1—C3—C4	121.0 (3)	C13—C14—H14	119.7
N1—C3—C2	115.7 (3)	C9—C14—H14	119.7
C4—C3—C2	123.3 (3)
O1i—Cu1—N1—C3	−146.8 (2)	C1—C2—C3—N1	−66.8 (3)
N2—Cu1—N1—C3	44.9 (2)	C1—C2—C3—C4	112.9 (3)
O1—Cu1—N1—C3	134.4 (2)	N1—C3—C4—C5	−0.2 (5)
Cl2—Cu1—N1—C3	−47.3 (2)	C2—C3—C4—C5	−179.8 (3)
O1i—Cu1—N1—C7	40.0 (2)	C3—C4—C5—C6	−0.3 (6)
N2—Cu1—N1—C7	−128.3 (2)	C4—C5—C6—C7	0.7 (6)
O1—Cu1—N1—C7	−38.7 (2)	C3—N1—C7—C6	0.2 (4)
Cl2—Cu1—N1—C7	139.5 (2)	Cu1—N1—C7—C6	173.2 (2)
O1i—Cu1—N2—C8	28.7 (6)	C5—C6—C7—N1	−0.7 (5)
N1—Cu1—N2—C8	121.0 (2)	C1—N2—C8—C9	−179.8 (3)
O1—Cu1—N2—C8	1.2 (2)	Cu1—N2—C8—C9	1.8 (4)
Cl2—Cu1—N2—C8	−106.7 (2)	N2—C8—C9—C14	177.1 (3)
O1i—Cu1—N2—C1	−149.7 (4)	N2—C8—C9—C10	−4.4 (5)
N1—Cu1—N2—C1	−57.5 (2)	Cu1i—O1—C10—C11	4.6 (4)
O1—Cu1—N2—C1	−177.2 (2)	Cu1—O1—C10—C11	−178.7 (2)
Cl2—Cu1—N2—C1	74.8 (2)	Cu1i—O1—C10—C9	−175.26 (18)
O1i—Cu1—O1—C10	−177.4 (3)	Cu1—O1—C10—C9	1.4 (4)
N2—Cu1—O1—C10	−2.9 (2)	C14—C9—C10—O1	−179.1 (3)
N1—Cu1—O1—C10	−89.8 (2)	C8—C9—C10—O1	2.5 (4)
Cl2—Cu1—O1—C10	91.5 (2)	C14—C9—C10—C11	1.1 (4)
O1i—Cu1—O1—Cu1i	0.0	C8—C9—C10—C11	−177.4 (3)
N2—Cu1—O1—Cu1i	174.53 (10)	O1—C10—C11—C12	177.3 (3)
N1—Cu1—O1—Cu1i	87.59 (11)	C9—C10—C11—C12	−2.9 (4)
Cl2—Cu1—O1—Cu1i	−91.06 (8)	C10—C11—C12—C13	1.8 (5)
C8—N2—C1—C2	−159.3 (3)	C11—C12—C13—C14	1.1 (5)
Cu1—N2—C1—C2	19.3 (3)	C11—C12—C13—Cl1	−177.7 (2)
N2—C1—C2—C3	50.8 (4)	C12—C13—C14—C9	−2.9 (5)
C7—N1—C3—C4	0.2 (4)	Cl1—C13—C14—C9	175.9 (2)
Cu1—N1—C3—C4	−173.1 (2)	C10—C9—C14—C13	1.7 (4)
C7—N1—C3—C2	179.8 (3)	C8—C9—C14—C13	−179.7 (3)
Cu1—N1—C3—C2	6.5 (3)

Table 1

Selected bond lengths (Å)

Cu1—O1i	1.9547 (18)
Cu1—N2	1.958 (2)
Cu1—Cl2	2.3187 (9)

Symmetry code: (i) .