Dichlorido{2-[(3,4-dimethyl-phen-yl)imino-meth-yl]pyridine-κN,N'}copper(II).

In the title complex, [CuCl(2)(C(14)H(14)N(2))], the Cu(II) atom exhibits a very distorted tetra-hedral coordination geometry involving two chloride ions and two N-atom donors from the Schiff base ligand. The range for the six bond angles about the Cu(2+) cation is 81.49 (11)-145.95 (9)°. The chelate ring including the Cu(II) atom is approximately planar, with a maximum deviation of 0.039 (4) Å for one of the C atoms; this plane forms a dihedral angle of 46.69 (9)° with the CuCl(2) plane.

Related literature

For related structures, see: Mahmoudi et al. (2009 ▶); Wang & Zhong (2009 ▶). For background information on diimine complexes, see: Khalaj et al. (2010 ▶); Salehzadeh et al. (2011 ▶).

Experimental

Crystal data

[CuCl2(C14H14N2)]

M = 344.71

Triclinic,

a = 8.1171 (4) Å

b = 9.5784 (4) Å

c = 10.0609 (5) Å

α = 67.236 (2)°

β = 88.513 (2)°

γ = 81.336 (2)°

V = 712.61 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.89 mm−1

T = 150 K

0.18 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.725, T max = 0.830

6451 measured reflections

3189 independent reflections

2256 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.07

3189 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −0.62 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104390X/zs2154sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104390X/zs2154Isup2.hkl

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

[CuCl2(C14H14N2)]	Z = 2
Mr = 344.71	F(000) = 350
Triclinic, P1	Dx = 1.607 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1171 (4) Å	Cell parameters from 6451 reflections
b = 9.5784 (4) Å	θ = 3.2–27.4°
c = 10.0609 (5) Å	µ = 1.89 mm−1
α = 67.236 (2)°	T = 150 K
β = 88.513 (2)°	Block, green
γ = 81.336 (2)°	0.18 × 0.16 × 0.10 mm
V = 712.61 (6) Å3

Nonius KappaCCD diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 9 pixels mm-1	θmax = 27.4°, θmin = 3.2°
φ scans and ω scans with κ offsets	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→12
Tmin = 0.725, Tmax = 0.830	l = −12→13
6451 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.324P] where P = (Fo2 + 2Fc2)/3
3189 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.83 e Å−3
0 restraints	Δρmin = −0.62 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
Cu1	0.78165 (5)	0.20424 (5)	0.33299 (5)	0.02388 (17)
Cl1	1.03716 (11)	0.14201 (11)	0.26876 (12)	0.0344 (3)
Cl2	0.82609 (12)	0.35601 (10)	0.44190 (11)	0.0285 (2)
N1	0.7024 (4)	0.0099 (3)	0.3557 (3)	0.0214 (7)
N2	0.5411 (4)	0.2901 (3)	0.2659 (3)	0.0210 (7)
C1	0.7928 (5)	−0.1295 (4)	0.3991 (4)	0.0246 (8)
H1A	0.9088	−0.1414	0.4200	0.030*
C2	0.7211 (5)	−0.2577 (4)	0.4146 (4)	0.0268 (9)
H2A	0.7879	−0.3557	0.4440	0.032*
C3	0.5523 (5)	−0.2417 (4)	0.3868 (4)	0.0276 (9)
H3A	0.5013	−0.3282	0.3973	0.033*
C4	0.4583 (5)	−0.0967 (4)	0.3432 (4)	0.0242 (8)
H4A	0.3416	−0.0824	0.3242	0.029*
C5	0.5375 (4)	0.0264 (4)	0.3280 (4)	0.0199 (7)
C6	0.4535 (5)	0.1850 (4)	0.2758 (4)	0.0226 (8)
H6A	0.3379	0.2099	0.2500	0.027*
C7	0.4663 (5)	0.4479 (4)	0.2081 (4)	0.0221 (8)
C8	0.5689 (5)	0.5567 (4)	0.1391 (4)	0.0239 (8)
H8A	0.6856	0.5271	0.1362	0.029*
C9	0.4977 (5)	0.7090 (4)	0.0747 (4)	0.0267 (8)
H9A	0.5672	0.7830	0.0249	0.032*
C10	0.3303 (5)	0.7572 (4)	0.0800 (4)	0.0281 (9)
C11	0.2260 (5)	0.6473 (4)	0.1520 (4)	0.0250 (8)
C12	0.2963 (5)	0.4939 (4)	0.2149 (4)	0.0265 (8)
H12A	0.2271	0.4191	0.2634	0.032*
C13	0.2548 (5)	0.9237 (4)	0.0073 (4)	0.0321 (9)
H13A	0.3406	0.9834	−0.0456	0.048*
H13B	0.2103	0.9620	0.0803	0.048*
H13C	0.1645	0.9337	−0.0601	0.048*
C14	0.0420 (5)	0.6938 (4)	0.1616 (5)	0.0363 (10)
H14A	−0.0082	0.6034	0.2197	0.054*
H14B	−0.0102	0.7396	0.0644	0.054*
H14C	0.0245	0.7687	0.2068	0.054*

	U11	U22	U33	U12	U13	U23
Cu1	0.0176 (3)	0.0229 (3)	0.0336 (3)	−0.00222 (18)	0.0004 (2)	−0.0139 (2)
Cl1	0.0182 (5)	0.0407 (6)	0.0514 (7)	−0.0050 (4)	0.0058 (4)	−0.0255 (5)
Cl2	0.0269 (5)	0.0226 (4)	0.0390 (6)	−0.0013 (4)	−0.0050 (4)	−0.0156 (4)
N1	0.0205 (16)	0.0209 (15)	0.0232 (17)	−0.0002 (12)	−0.0008 (13)	−0.0100 (13)
N2	0.0222 (16)	0.0190 (15)	0.0228 (16)	−0.0036 (12)	0.0033 (13)	−0.0092 (13)
C1	0.023 (2)	0.0270 (19)	0.023 (2)	0.0004 (15)	0.0001 (16)	−0.0107 (17)
C2	0.033 (2)	0.0204 (18)	0.028 (2)	−0.0005 (16)	0.0044 (18)	−0.0118 (17)
C3	0.038 (2)	0.0225 (19)	0.027 (2)	−0.0094 (17)	0.0055 (18)	−0.0130 (17)
C4	0.024 (2)	0.030 (2)	0.023 (2)	−0.0081 (16)	0.0011 (16)	−0.0129 (17)
C5	0.0194 (18)	0.0211 (17)	0.0207 (19)	−0.0042 (14)	0.0025 (15)	−0.0095 (15)
C6	0.0180 (18)	0.0235 (18)	0.027 (2)	−0.0008 (14)	0.0016 (16)	−0.0114 (17)
C7	0.026 (2)	0.0196 (17)	0.0217 (19)	−0.0018 (15)	0.0007 (16)	−0.0092 (15)
C8	0.0213 (19)	0.0262 (19)	0.026 (2)	−0.0054 (15)	0.0013 (16)	−0.0110 (17)
C9	0.031 (2)	0.0251 (19)	0.023 (2)	−0.0063 (16)	−0.0010 (17)	−0.0079 (17)
C10	0.040 (2)	0.0171 (17)	0.023 (2)	0.0025 (16)	0.0032 (18)	−0.0054 (16)
C11	0.024 (2)	0.027 (2)	0.024 (2)	−0.0012 (16)	0.0016 (16)	−0.0096 (17)
C12	0.025 (2)	0.0255 (19)	0.027 (2)	−0.0038 (16)	0.0050 (17)	−0.0090 (17)
C13	0.043 (3)	0.0233 (19)	0.029 (2)	−0.0015 (17)	−0.0030 (19)	−0.0103 (18)
C14	0.030 (2)	0.029 (2)	0.039 (3)	0.0047 (17)	0.0020 (19)	−0.0039 (19)

Cu1—N1	1.988 (3)	C7—C8	1.391 (5)
Cu1—N2	2.025 (3)	C7—C12	1.392 (5)
Cu1—Cl2	2.2035 (10)	C8—C9	1.384 (5)
Cu1—Cl1	2.2204 (10)	C8—H8A	0.9500
N1—C1	1.335 (4)	C9—C10	1.374 (5)
N1—C5	1.348 (5)	C9—H9A	0.9500
N2—C6	1.290 (4)	C10—C11	1.413 (5)
N2—C7	1.433 (4)	C10—C13	1.510 (5)
C1—C2	1.391 (5)	C11—C12	1.390 (5)
C1—H1A	0.9500	C11—C14	1.505 (5)
C2—C3	1.379 (5)	C12—H12A	0.9500
C2—H2A	0.9500	C13—H13A	0.9800
C3—C4	1.390 (5)	C13—H13B	0.9800
C3—H3A	0.9500	C13—H13C	0.9800
C4—C5	1.383 (5)	C14—H14A	0.9800
C4—H4A	0.9500	C14—H14B	0.9800
C5—C6	1.462 (5)	C14—H14C	0.9800
C6—H6A	0.9500
N1—Cu1—N2	81.49 (11)	C8—C7—C12	119.9 (3)
N1—Cu1—Cl2	145.38 (9)	C8—C7—N2	117.6 (3)
N2—Cu1—Cl2	99.33 (8)	C12—C7—N2	122.5 (3)
N1—Cu1—Cl1	95.98 (9)	C9—C8—C7	118.7 (3)
N2—Cu1—Cl1	145.95 (9)	C9—C8—H8A	120.7
Cl2—Cu1—Cl1	101.41 (4)	C7—C8—H8A	120.7
C1—N1—C5	119.2 (3)	C10—C9—C8	122.5 (3)
C1—N1—Cu1	127.1 (3)	C10—C9—H9A	118.8
C5—N1—Cu1	113.6 (2)	C8—C9—H9A	118.8
C6—N2—C7	120.0 (3)	C9—C10—C11	119.0 (3)
C6—N2—Cu1	112.6 (2)	C9—C10—C13	121.6 (3)
C7—N2—Cu1	127.4 (2)	C11—C10—C13	119.4 (3)
N1—C1—C2	121.5 (3)	C12—C11—C10	118.8 (3)
N1—C1—H1A	119.2	C12—C11—C14	120.0 (3)
C2—C1—H1A	119.2	C10—C11—C14	121.2 (3)
C3—C2—C1	119.6 (3)	C11—C12—C7	121.1 (3)
C3—C2—H2A	120.2	C11—C12—H12A	119.4
C1—C2—H2A	120.2	C7—C12—H12A	119.4
C2—C3—C4	118.8 (3)	C10—C13—H13A	109.5
C2—C3—H3A	120.6	C10—C13—H13B	109.5
C4—C3—H3A	120.6	H13A—C13—H13B	109.5
C5—C4—C3	118.8 (3)	C10—C13—H13C	109.5
C5—C4—H4A	120.6	H13A—C13—H13C	109.5
C3—C4—H4A	120.6	H13B—C13—H13C	109.5
N1—C5—C4	122.1 (3)	C11—C14—H14A	109.5
N1—C5—C6	114.1 (3)	C11—C14—H14B	109.5
C4—C5—C6	123.7 (3)	H14A—C14—H14B	109.5
N2—C6—C5	118.0 (3)	C11—C14—H14C	109.5
N2—C6—H6A	121.0	H14A—C14—H14C	109.5
C5—C6—H6A	121.0	H14B—C14—H14C	109.5

Table 1

Selected bond lengths (Å)

Cu1—N1	1.988 (3)
Cu1—N2	2.025 (3)
Cu1—Cl2	2.2035 (10)
Cu1—Cl1	2.2204 (10)