Di-μ-chlorido-bis-(chlorido{2-[(4-ethyl-phen-yl)imino-meth-yl]pyridine-κN,N'}copper(II)).

The binuclear title complex, [Cu(2)Cl(4)(C(14)H(14)N(2))(2)], is located on a crystallographic inversion centre. The Cu(II) ion is in a distorted square-pyramid coordination environment formed by the bichelating N-heterocyclic ligand, two bridging Cl atoms and one terminal Cl atom. One of the bridging Cu-Cl bonds is significantly longer than the other.

Related literature

For the synthesis of the ligand, see: Dehghanpour et al. (2009 ▶). For background to diimine complexes and related structures, see: Mahmoudi et al. (2009 ▶); Salehzadeh et al. (2011 ▶).

Experimental

Crystal data

[Cu2Cl4(C14H14N2)2]

M = 689.42

Monoclinic,

a = 10.1254 (3) Å

b = 8.8384 (3) Å

c = 16.2117 (4) Å

β = 100.8830 (18)°

V = 1424.73 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.89 mm−1

T = 150 K

0.18 × 0.18 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.672, T max = 0.795

13286 measured reflections

3246 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.11

3246 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.59 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032053/kj2183sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032053/kj2183Isup2.hkl

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

[Cu2Cl4(C14H14N2)2]	F(000) = 700
Mr = 689.42	Dx = 1.607 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5841 reflections
a = 10.1254 (3) Å	θ = 2.6–27.5°
b = 8.8384 (3) Å	µ = 1.89 mm−1
c = 16.2117 (4) Å	T = 150 K
β = 100.8830 (18)°	Block, green
V = 1424.73 (7) Å3	0.18 × 0.18 × 0.12 mm
Z = 2

Nonius KappaCCD diffractometer	3246 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −13→10
Absorption correction: multi-scan (SORTAV (Blessing, 1995)	k = −11→11
Tmin = 0.672, Tmax = 0.795	l = −20→21
13286 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0322P)2 + 1.7627P] where P = (Fo2 + 2Fc2)/3
3246 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

Experimental. multi-scan from symmetry-related measurements SORTAV (Blessing, 1995)

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	0.49287 (3)	0.40798 (4)	0.59239 (2)	0.01724 (11)
Cl1	0.65548 (6)	0.56294 (8)	0.55534 (4)	0.01911 (16)
Cl2	0.41609 (7)	0.59028 (8)	0.66720 (4)	0.02404 (17)
N1	0.5981 (2)	0.2194 (3)	0.57146 (14)	0.0185 (5)
N2	0.3756 (2)	0.2450 (3)	0.63198 (13)	0.0178 (5)
C1	0.7060 (3)	0.2085 (3)	0.53486 (17)	0.0222 (6)
H1A	0.7364	0.2955	0.5095	0.027*
C2	0.7742 (3)	0.0725 (3)	0.53322 (18)	0.0240 (6)
H2A	0.8512	0.0678	0.5076	0.029*
C3	0.7307 (3)	−0.0556 (3)	0.56855 (18)	0.0243 (6)
H3A	0.7777	−0.1486	0.5685	0.029*
C4	0.6167 (3)	−0.0455 (3)	0.60428 (18)	0.0224 (6)
H4A	0.5825	−0.1322	0.6279	0.027*
C5	0.5544 (3)	0.0924 (3)	0.60479 (16)	0.0173 (6)
C6	0.4297 (3)	0.1137 (3)	0.63732 (17)	0.0197 (6)
H6A	0.3902	0.0318	0.6618	0.024*
C7	0.2512 (3)	0.2625 (3)	0.66176 (17)	0.0193 (6)
C8	0.2360 (3)	0.1939 (3)	0.73601 (17)	0.0226 (6)
H8A	0.3085	0.1399	0.7688	0.027*
C9	0.1134 (3)	0.2047 (3)	0.76209 (17)	0.0225 (6)
H9A	0.1029	0.1566	0.8129	0.027*
C10	0.0059 (3)	0.2836 (3)	0.71632 (18)	0.0228 (6)
C11	0.0253 (3)	0.3551 (4)	0.64241 (18)	0.0250 (6)
H11A	−0.0465	0.4107	0.6100	0.030*
C12	0.1477 (3)	0.3464 (3)	0.61556 (17)	0.0233 (6)
H12A	0.1600	0.3974	0.5660	0.028*
C13	−0.1281 (3)	0.2884 (4)	0.74484 (18)	0.0270 (7)
H13A	−0.1718	0.1881	0.7348	0.032*
H13B	−0.1868	0.3633	0.7103	0.032*
C14	−0.1168 (3)	0.3292 (4)	0.83719 (19)	0.0332 (7)
H14A	−0.2069	0.3336	0.8510	0.050*
H14B	−0.0731	0.4280	0.8479	0.050*
H14C	−0.0633	0.2523	0.8721	0.050*

	U11	U22	U33	U12	U13	U23
Cu1	0.01785 (18)	0.0172 (2)	0.01712 (18)	−0.00025 (13)	0.00446 (13)	0.00089 (13)
Cl1	0.0199 (3)	0.0202 (4)	0.0171 (3)	−0.0028 (3)	0.0029 (2)	0.0011 (3)
Cl2	0.0224 (3)	0.0254 (4)	0.0252 (4)	0.0003 (3)	0.0070 (3)	−0.0061 (3)
N1	0.0169 (11)	0.0186 (12)	0.0195 (12)	0.0009 (9)	0.0022 (9)	0.0004 (9)
N2	0.0186 (11)	0.0191 (12)	0.0158 (11)	−0.0023 (9)	0.0037 (9)	−0.0004 (9)
C1	0.0219 (14)	0.0231 (16)	0.0222 (14)	−0.0025 (12)	0.0053 (11)	0.0021 (12)
C2	0.0212 (14)	0.0249 (16)	0.0269 (16)	0.0016 (12)	0.0065 (12)	−0.0005 (12)
C3	0.0254 (15)	0.0213 (16)	0.0259 (16)	0.0030 (12)	0.0044 (12)	−0.0015 (12)
C4	0.0245 (15)	0.0173 (14)	0.0245 (15)	0.0002 (12)	0.0021 (12)	0.0013 (12)
C5	0.0182 (13)	0.0201 (15)	0.0128 (13)	−0.0013 (11)	0.0008 (10)	0.0013 (11)
C6	0.0222 (14)	0.0201 (15)	0.0168 (14)	−0.0042 (11)	0.0036 (11)	0.0022 (11)
C7	0.0182 (13)	0.0203 (15)	0.0194 (14)	−0.0024 (11)	0.0038 (11)	−0.0011 (11)
C8	0.0225 (14)	0.0237 (15)	0.0211 (14)	0.0015 (12)	0.0032 (11)	0.0017 (12)
C9	0.0238 (14)	0.0254 (16)	0.0190 (14)	−0.0008 (12)	0.0057 (11)	0.0012 (12)
C10	0.0207 (14)	0.0230 (16)	0.0253 (15)	−0.0046 (12)	0.0062 (12)	−0.0042 (12)
C11	0.0192 (14)	0.0306 (17)	0.0246 (15)	0.0020 (12)	0.0024 (11)	0.0027 (13)
C12	0.0252 (15)	0.0265 (16)	0.0181 (14)	0.0014 (12)	0.0037 (11)	0.0045 (12)
C13	0.0208 (14)	0.0346 (18)	0.0262 (15)	−0.0013 (13)	0.0061 (12)	0.0001 (13)
C14	0.0292 (16)	0.043 (2)	0.0295 (17)	0.0026 (15)	0.0116 (14)	−0.0006 (15)

Cu1—N1	2.040 (2)	C6—H6A	0.9500
Cu1—N2	2.046 (2)	C7—C8	1.382 (4)
Cu1—Cl2	2.2423 (7)	C7—C12	1.383 (4)
Cu1—Cl1	2.3067 (7)	C8—C9	1.388 (4)
Cu1—Cl1i	2.5883 (7)	C8—H8A	0.9500
Cl1—Cu1i	2.5883 (7)	C9—C10	1.384 (4)
N1—C1	1.342 (3)	C9—H9A	0.9500
N1—C5	1.356 (3)	C10—C11	1.401 (4)
N2—C6	1.280 (3)	C10—C13	1.514 (4)
N2—C7	1.439 (3)	C11—C12	1.390 (4)
C1—C2	1.388 (4)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.378 (4)	C13—C14	1.523 (4)
C2—H2A	0.9500	C13—H13A	0.9900
C3—C4	1.389 (4)	C13—H13B	0.9900
C3—H3A	0.9500	C14—H14A	0.9800
C4—C5	1.373 (4)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800
C5—C6	1.469 (4)
N1—Cu1—N2	80.19 (9)	N2—C6—H6A	120.7
N1—Cu1—Cl2	157.23 (7)	C5—C6—H6A	120.7
N2—Cu1—Cl2	93.15 (7)	C8—C7—C12	120.6 (2)
N1—Cu1—Cl1	91.19 (6)	C8—C7—N2	119.6 (2)
N2—Cu1—Cl1	170.06 (7)	C12—C7—N2	119.8 (2)
Cl2—Cu1—Cl1	92.96 (3)	C7—C8—C9	119.2 (3)
N1—Cu1—Cl1i	99.05 (6)	C7—C8—H8A	120.4
N2—Cu1—Cl1i	95.18 (6)	C9—C8—H8A	120.4
Cl2—Cu1—Cl1i	103.25 (3)	C10—C9—C8	122.0 (3)
Cl1—Cu1—Cl1i	91.04 (2)	C10—C9—H9A	119.0
Cu1—Cl1—Cu1i	88.96 (2)	C8—C9—H9A	119.0
C1—N1—C5	118.1 (2)	C9—C10—C11	117.5 (3)
C1—N1—Cu1	128.83 (19)	C9—C10—C13	120.6 (3)
C5—N1—Cu1	112.96 (17)	C11—C10—C13	121.8 (3)
C6—N2—C7	117.7 (2)	C12—C11—C10	121.3 (3)
C6—N2—Cu1	113.14 (18)	C12—C11—H11A	119.3
C7—N2—Cu1	128.77 (18)	C10—C11—H11A	119.3
N1—C1—C2	121.4 (3)	C7—C12—C11	119.3 (3)
N1—C1—H1A	119.3	C7—C12—H12A	120.3
C2—C1—H1A	119.3	C11—C12—H12A	120.3
C3—C2—C1	120.2 (3)	C10—C13—C14	113.7 (2)
C3—C2—H2A	119.9	C10—C13—H13A	108.8
C1—C2—H2A	119.9	C14—C13—H13A	108.8
C2—C3—C4	118.5 (3)	C10—C13—H13B	108.8
C2—C3—H3A	120.8	C14—C13—H13B	108.8
C4—C3—H3A	120.8	H13A—C13—H13B	107.7
C5—C4—C3	118.6 (3)	C13—C14—H14A	109.5
C5—C4—H4A	120.7	C13—C14—H14B	109.5
C3—C4—H4A	120.7	H14A—C14—H14B	109.5
N1—C5—C4	123.2 (2)	C13—C14—H14C	109.5
N1—C5—C6	113.8 (2)	H14A—C14—H14C	109.5
C4—C5—C6	122.9 (2)	H14B—C14—H14C	109.5
N2—C6—C5	118.6 (2)
N1—Cu1—Cl1—Cu1i	99.07 (6)	Cu1—N1—C5—C6	8.5 (3)
Cl2—Cu1—Cl1—Cu1i	−103.33 (3)	C3—C4—C5—N1	0.5 (4)
Cl1i—Cu1—Cl1—Cu1i	0.0	C3—C4—C5—C6	177.0 (3)
N2—Cu1—N1—C1	174.6 (2)	C7—N2—C6—C5	178.1 (2)
Cl2—Cu1—N1—C1	−110.9 (2)	Cu1—N2—C6—C5	−8.1 (3)
Cl1—Cu1—N1—C1	−10.3 (2)	N1—C5—C6—N2	−0.3 (4)
Cl1i—Cu1—N1—C1	80.9 (2)	C4—C5—C6—N2	−177.0 (3)
N2—Cu1—N1—C5	−9.83 (18)	C6—N2—C7—C8	42.2 (4)
Cl2—Cu1—N1—C5	64.6 (3)	Cu1—N2—C7—C8	−130.5 (2)
Cl1—Cu1—N1—C5	165.18 (17)	C6—N2—C7—C12	−137.1 (3)
Cl1i—Cu1—N1—C5	−103.57 (17)	Cu1—N2—C7—C12	50.2 (3)
N1—Cu1—N2—C6	9.73 (19)	C12—C7—C8—C9	2.6 (4)
Cl2—Cu1—N2—C6	−148.34 (18)	N2—C7—C8—C9	−176.7 (2)
N1—Cu1—N2—C7	−177.3 (2)	C7—C8—C9—C10	−0.6 (4)
Cl2—Cu1—N2—C7	24.6 (2)	C8—C9—C10—C11	−0.9 (4)
C5—N1—C1—C2	−2.0 (4)	C8—C9—C10—C13	177.7 (3)
Cu1—N1—C1—C2	173.3 (2)	C9—C10—C11—C12	0.5 (4)
N1—C1—C2—C3	0.9 (4)	C13—C10—C11—C12	−178.1 (3)
C1—C2—C3—C4	1.0 (4)	C8—C7—C12—C11	−3.0 (4)
C2—C3—C4—C5	−1.7 (4)	N2—C7—C12—C11	176.3 (3)
C1—N1—C5—C4	1.3 (4)	C10—C11—C12—C7	1.5 (4)
Cu1—N1—C5—C4	−174.7 (2)	C9—C10—C13—C14	49.0 (4)
C1—N1—C5—C6	−175.4 (2)	C11—C10—C13—C14	−132.5 (3)

Table 1

Selected bond lengths (Å)

Cu1—N1	2.040 (2)
Cu1—N2	2.046 (2)
Cu1—Cl2	2.2423 (7)
Cu1—Cl1	2.3067 (7)
Cu1—Cl1i	2.5883 (7)

Symmetry code: (i) .