Dichlorido[2,2'-(oxydimethyl-ene)dipyridine]copper(II).

In the title complex, [CuCl(2)(C(12)H(12)N(2)O)], the Cu(II) ion is coordinated in a distorted trigonal-bipyramidal environment. In the crystal structure, there is a weak π-π stacking inter-action between symmetry-related pyridine rings, with a centroid-to-centroid distance of 3.8134 (17) Å. In addition, there is relatively close contact between the pyridine ring π-system and a symmetry-related Cu(II) ion (Cu⋯centroid distance of 3.868 Å).

Related literature

For the isotypic Cd and Zn analogs of the title compound, see: Li (2007 ▶) and Li (2008 ▶), respectively.

Experimental

Crystal data

[CuCl2(C12H12N2O)]

M = 334.68

Monoclinic,

a = 8.1599 (10) Å

b = 12.5534 (15) Å

c = 15.3846 (14) Å

β = 123.574 (9)°

V = 1313.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.06 mm−1

T = 298 (2) K

0.46 × 0.40 × 0.34 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.451, T max = 0.541 (expected range = 0.414–0.497)

5381 measured reflections

2323 independent reflections

2152 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.066

S = 1.09

2323 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034612/lh2712sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034612/lh2712Isup2.hkl

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

[CuCl2(C12H12N2O)]	F(000) = 676
Mr = 334.68	Dx = 1.693 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4907 reflections
a = 8.1599 (10) Å	θ = 2.3–28.3°
b = 12.5534 (15) Å	µ = 2.06 mm−1
c = 15.3846 (14) Å	T = 298 K
β = 123.574 (9)°	Block, green
V = 1313.0 (3) Å3	0.46 × 0.40 × 0.34 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2323 independent reflections
Radiation source: fine-focus sealed tube	2152 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.451, Tmax = 0.541	k = −11→14
5381 measured reflections	l = −18→13

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.5176P] where P = (Fo2 + 2Fc2)/3
2323 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.27 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	−0.0360 (3)	0.76246 (18)	−0.10853 (17)	0.0407 (5)
H1A	−0.1499	0.7554	−0.1795	0.049*
H1B	0.0687	0.7967	−0.1103	0.049*
C2	−0.0341 (4)	0.8555 (2)	0.1167 (2)	0.0481 (6)
H2	0.0297	0.8372	0.1868	0.058*
C3	−0.1666 (4)	0.9378 (2)	0.0794 (2)	0.0576 (7)
H3	−0.1909	0.9750	0.1235	0.069*
C4	−0.2628 (4)	0.9644 (2)	−0.0242 (2)	0.0604 (7)
H4	−0.3532	1.0200	−0.0516	0.072*
C5	−0.2232 (4)	0.9072 (2)	−0.0868 (2)	0.0507 (6)
H5	−0.2882	0.9231	−0.1574	0.061*
C6	−0.0864 (3)	0.82611 (17)	−0.04415 (17)	0.0357 (5)
C7	0.1210 (3)	0.59462 (18)	−0.09417 (16)	0.0369 (5)
H7A	0.2093	0.6368	−0.1039	0.044*
H7B	0.0243	0.5614	−0.1601	0.044*
C8	0.2343 (3)	0.51119 (17)	−0.01249 (15)	0.0320 (4)
C9	0.3812 (3)	0.46002 (18)	0.15917 (17)	0.0368 (5)
H9	0.4090	0.4735	0.2255	0.044*
C10	0.4063 (3)	0.34591 (18)	0.0442 (2)	0.0427 (5)
H10	0.4507	0.2836	0.0311	0.051*
C11	0.2964 (3)	0.41864 (18)	−0.03445 (18)	0.0405 (5)
H11	0.2645	0.4055	−0.1016	0.049*
C12	0.4491 (3)	0.36715 (19)	0.14218 (19)	0.0420 (5)
H12	0.5231	0.3193	0.1965	0.050*
Cl1	0.46540 (8)	0.76638 (5)	0.12142 (4)	0.04202 (15)
Cl2	0.20944 (9)	0.63873 (5)	0.25169 (4)	0.04202 (15)
Cu1	0.18810 (4)	0.673873 (19)	0.102078 (18)	0.03121 (10)
N1	0.0076 (3)	0.80023 (14)	0.05709 (14)	0.0359 (4)
N2	0.2764 (2)	0.53190 (13)	0.08332 (13)	0.0310 (4)
O1	0.0261 (2)	0.66050 (11)	−0.05971 (11)	0.0324 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0432 (12)	0.0411 (13)	0.0352 (11)	0.0067 (10)	0.0201 (10)	0.0108 (10)
C2	0.0580 (15)	0.0417 (13)	0.0490 (14)	0.0070 (12)	0.0323 (12)	−0.0021 (11)
C3	0.0632 (17)	0.0426 (14)	0.0748 (19)	0.0087 (13)	0.0430 (16)	−0.0074 (13)
C4	0.0536 (15)	0.0377 (14)	0.086 (2)	0.0142 (12)	0.0366 (15)	0.0069 (14)
C5	0.0452 (13)	0.0427 (14)	0.0552 (15)	0.0097 (11)	0.0221 (12)	0.0123 (12)
C6	0.0320 (11)	0.0316 (11)	0.0395 (12)	0.0005 (8)	0.0173 (10)	0.0059 (9)
C7	0.0425 (12)	0.0396 (12)	0.0326 (11)	−0.0007 (10)	0.0232 (10)	−0.0024 (9)
C8	0.0300 (10)	0.0321 (11)	0.0352 (10)	−0.0050 (8)	0.0189 (9)	−0.0044 (9)
C9	0.0341 (11)	0.0374 (12)	0.0345 (11)	0.0015 (9)	0.0162 (9)	0.0023 (9)
C10	0.0391 (12)	0.0308 (11)	0.0646 (16)	0.0000 (9)	0.0327 (12)	−0.0045 (11)
C11	0.0420 (12)	0.0394 (13)	0.0470 (13)	−0.0066 (10)	0.0290 (11)	−0.0112 (10)
C12	0.0355 (11)	0.0354 (12)	0.0523 (14)	0.0047 (10)	0.0225 (11)	0.0072 (10)
Cl1	0.0417 (3)	0.0411 (3)	0.0482 (3)	−0.0068 (2)	0.0279 (3)	−0.0045 (2)
Cl2	0.0550 (3)	0.0420 (3)	0.0353 (3)	−0.0009 (3)	0.0289 (3)	0.0015 (2)
Cu1	0.03650 (16)	0.02880 (16)	0.02902 (15)	0.00285 (10)	0.01855 (12)	0.00079 (9)
N1	0.0363 (10)	0.0307 (9)	0.0402 (10)	0.0028 (8)	0.0209 (8)	0.0014 (8)
N2	0.0314 (8)	0.0288 (9)	0.0325 (9)	−0.0017 (7)	0.0175 (7)	−0.0023 (7)
O1	0.0341 (8)	0.0336 (8)	0.0286 (7)	0.0023 (6)	0.0168 (6)	0.0025 (6)

C1—O1	1.428 (3)	C7—H7B	0.9700
C1—C6	1.496 (3)	C8—N2	1.341 (3)
C1—H1A	0.9700	C8—C11	1.382 (3)
C1—H1B	0.9700	C9—N2	1.343 (3)
C2—N1	1.336 (3)	C9—C12	1.376 (3)
C2—C3	1.372 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C12	1.372 (4)
C3—C4	1.373 (4)	C10—C11	1.379 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.375 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.379 (3)	Cl1—Cu1	2.4109 (6)
C5—H5	0.9300	Cl2—Cu1	2.2538 (6)
C6—N1	1.341 (3)	Cu1—N2	2.0021 (17)
C7—O1	1.421 (3)	Cu1—N1	2.0092 (18)
C7—C8	1.499 (3)	Cu1—O1	2.0813 (14)
C7—H7A	0.9700
O1—C1—C6	106.14 (17)	N2—C9—H9	118.9
O1—C1—H1A	110.5	C12—C9—H9	118.9
C6—C1—H1A	110.5	C12—C10—C11	118.8 (2)
O1—C1—H1B	110.5	C12—C10—H10	120.6
C6—C1—H1B	110.5	C11—C10—H10	120.6
H1A—C1—H1B	108.7	C10—C11—C8	119.4 (2)
N1—C2—C3	123.0 (2)	C10—C11—H11	120.3
N1—C2—H2	118.5	C8—C11—H11	120.3
C3—C2—H2	118.5	C10—C12—C9	119.3 (2)
C2—C3—C4	118.8 (3)	C10—C12—H12	120.4
C2—C3—H3	120.6	C9—C12—H12	120.4
C4—C3—H3	120.6	N2—Cu1—N1	155.06 (7)
C3—C4—C5	118.8 (2)	N2—Cu1—O1	78.29 (6)
C3—C4—H4	120.6	N1—Cu1—O1	77.99 (7)
C5—C4—H4	120.6	N2—Cu1—Cl2	98.17 (5)
C4—C5—C6	119.6 (2)	N1—Cu1—Cl2	97.71 (6)
C4—C5—H5	120.2	O1—Cu1—Cl2	147.65 (4)
C6—C5—H5	120.2	N2—Cu1—Cl1	93.36 (5)
N1—C6—C5	121.6 (2)	N1—Cu1—Cl1	96.97 (6)
N1—C6—C1	116.70 (18)	O1—Cu1—Cl1	96.81 (4)
C5—C6—C1	121.7 (2)	Cl2—Cu1—Cl1	115.53 (2)
O1—C7—C8	107.73 (16)	C2—N1—C6	118.2 (2)
O1—C7—H7A	110.2	C2—N1—Cu1	126.14 (16)
C8—C7—H7A	110.2	C6—N1—Cu1	115.53 (15)
O1—C7—H7B	110.2	C8—N2—C9	118.52 (18)
C8—C7—H7B	110.2	C8—N2—Cu1	115.92 (14)
H7A—C7—H7B	108.5	C9—N2—Cu1	125.45 (14)
N2—C8—C11	121.7 (2)	C7—O1—C1	115.70 (16)
N2—C8—C7	116.77 (18)	C7—O1—Cu1	112.11 (12)
C11—C8—C7	121.47 (19)	C1—O1—Cu1	111.27 (12)
N2—C9—C12	122.3 (2)
N1—C2—C3—C4	0.7 (4)	Cl1—Cu1—N1—C6	81.62 (15)
C2—C3—C4—C5	0.2 (4)	C11—C8—N2—C9	−0.2 (3)
C3—C4—C5—C6	−1.0 (4)	C7—C8—N2—C9	−178.63 (18)
C4—C5—C6—N1	1.0 (4)	C11—C8—N2—Cu1	176.38 (15)
C4—C5—C6—C1	−179.2 (2)	C7—C8—N2—Cu1	−2.1 (2)
O1—C1—C6—N1	27.4 (3)	C12—C9—N2—C8	1.0 (3)
O1—C1—C6—C5	−152.4 (2)	C12—C9—N2—Cu1	−175.19 (16)
O1—C7—C8—N2	−20.0 (2)	N1—Cu1—N2—C8	33.8 (2)
O1—C7—C8—C11	161.56 (18)	O1—Cu1—N2—C8	15.52 (14)
C12—C10—C11—C8	0.7 (3)	Cl2—Cu1—N2—C8	162.86 (13)
N2—C8—C11—C10	−0.7 (3)	Cl1—Cu1—N2—C8	−80.74 (14)
C7—C8—C11—C10	177.7 (2)	N1—Cu1—N2—C9	−149.93 (18)
C11—C10—C12—C9	0.1 (3)	O1—Cu1—N2—C9	−168.19 (18)
N2—C9—C12—C10	−1.0 (3)	Cl2—Cu1—N2—C9	−20.85 (17)
C3—C2—N1—C6	−0.7 (4)	Cl1—Cu1—N2—C9	95.55 (17)
C3—C2—N1—Cu1	−176.6 (2)	C8—C7—O1—C1	160.80 (17)
C5—C6—N1—C2	−0.1 (3)	C8—C7—O1—Cu1	31.76 (19)
C1—C6—N1—C2	−180.0 (2)	C6—C1—O1—C7	−166.95 (17)
C5—C6—N1—Cu1	176.21 (18)	C6—C1—O1—Cu1	−37.49 (19)
C1—C6—N1—Cu1	−3.6 (2)	N2—Cu1—O1—C7	−26.88 (13)
N2—Cu1—N1—C2	143.8 (2)	N1—Cu1—O1—C7	160.88 (14)
O1—Cu1—N1—C2	162.1 (2)	Cl2—Cu1—O1—C7	−113.67 (13)
Cl2—Cu1—N1—C2	14.7 (2)	Cl1—Cu1—O1—C7	65.17 (13)
Cl1—Cu1—N1—C2	−102.4 (2)	N2—Cu1—O1—C1	−158.20 (14)
N2—Cu1—N1—C6	−32.2 (3)	N1—Cu1—O1—C1	29.56 (14)
O1—Cu1—N1—C6	−13.90 (15)	Cl2—Cu1—O1—C1	115.01 (13)
Cl2—Cu1—N1—C6	−161.33 (15)	Cl1—Cu1—O1—C1	−66.16 (13)

Cl1—Cu1	2.4109 (6)
Cl2—Cu1	2.2538 (6)
Cu1—N2	2.0021 (17)
Cu1—N1	2.0092 (18)
Cu1—O1	2.0813 (14)

N2—Cu1—N1	155.06 (7)
N2—Cu1—O1	78.29 (6)
N1—Cu1—O1	77.99 (7)
N2—Cu1—Cl2	98.17 (5)
N1—Cu1—Cl2	97.71 (6)
O1—Cu1—Cl2	147.65 (4)
N2—Cu1—Cl1	93.36 (5)
N1—Cu1—Cl1	96.97 (6)
O1—Cu1—Cl1	96.81 (4)
Cl2—Cu1—Cl1	115.53 (2)