Chlorido(pyridine-2-carbaldehyde oximato-κN,N')(pyridine-2-carbaldehyde oxime-κN,N')copper(II).

In the title compound, [Cu(C(6)H(5)N(2)O)Cl(C(6)H(6)N(2)O)], the Cu atom is coordinated by one neutral and one deprotonated pyridine-2-carboxaldehyde oxime (pco) ligand, resulting in the formation of two five-membered CuN(2)C(2) rings. Together with the additional coordinating chloride anion, the coordination polyhedron of copper is best described as a distorted square-pyramid, the distortion parameter being 0.288. The two organic ligands are linked by an intramolecular O-H⋯O hydrogen bond.

Related literature

For related literature, see: Addison et al. (1984 ▶); Afrati et al. (2005 ▶); Korpi et al. (2005 ▶); Pearse et al. (1989 ▶); Stamatatos et al. (2006 ▶).

Experimental

Crystal data

[Cu(C6H5N2O)Cl(C6H6N2O)]

M = 342.24

Monoclinic,

a = 16.686 (2) Å

b = 12.064 (2) Å

c = 13.805 (1) Å

β = 109.02 (1)°

V = 2627.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 1.87 mm−1

T = 293 (2) K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008 ▶) T min = 0.488, T max = 0.594 (expected range = 0.620–0.755)

6487 measured reflections

2318 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.110

S = 1.01

2318 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536808014748/im2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014748/im2064Isup2.hkl

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

[Cu(C6H5N2O)Cl(C6H6N2O)]	F000 = 1384
Mr = 342.24	Dx = 1.730 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2343 reflections
a = 16.686 (2) Å	θ = 2.4–26.6º
b = 12.064 (2) Å	µ = 1.87 mm−1
c = 13.805 (1) Å	T = 293 (2) K
β = 109.02 (1)º	Block, dark green
V = 2627.3 (5) Å3	0.22 × 0.18 × 0.15 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2318 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SHELXTL; Sheldrick, 2008)	h = −14→19
Tmin = 0.488, Tmax = 0.594	k = −14→13
6487 measured reflections	l = −16→16

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.065P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2318 reflections	Δρmax = 0.40 e Å−3
181 parameters	Δρmin = −0.39 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	0.45583 (2)	0.75857 (3)	0.08754 (3)	0.03490 (18)
Cl1	0.39133 (6)	0.74459 (6)	−0.09737 (7)	0.0452 (3)
N2	0.39301 (17)	0.8985 (2)	0.1014 (2)	0.0365 (6)
N3	0.53622 (18)	0.6345 (2)	0.0978 (2)	0.0432 (7)
N4	0.39418 (17)	0.6311 (2)	0.1352 (2)	0.0386 (7)
O2	0.60997 (16)	0.6484 (2)	0.0801 (2)	0.0594 (7)
C1	0.3107 (2)	0.9115 (3)	0.0892 (3)	0.0445 (9)
H1A	0.2761	0.8491	0.0764	0.053*
N1	0.54953 (17)	0.8713 (2)	0.1156 (2)	0.0431 (7)
C11	0.4316 (2)	0.5328 (3)	0.1314 (3)	0.0427 (9)
C5	0.4419 (2)	0.9892 (3)	0.1166 (3)	0.0433 (8)
O1	0.63020 (15)	0.8491 (3)	0.1224 (2)	0.0666 (8)
H1B	0.6346	0.7834	0.1100	0.100*
C2	0.2750 (3)	1.0126 (4)	0.0946 (3)	0.0585 (11)
H2A	0.2177	1.0187	0.0866	0.070*
C9	0.3236 (3)	0.4362 (4)	0.1762 (3)	0.0647 (12)
H9A	0.3002	0.3707	0.1903	0.078*
C7	0.3232 (2)	0.6295 (3)	0.1599 (3)	0.0457 (9)
H7A	0.2973	0.6968	0.1638	0.055*
C12	0.5115 (2)	0.5390 (3)	0.1109 (3)	0.0463 (9)
H12A	0.5426	0.4760	0.1076	0.056*
C6	0.5299 (2)	0.9703 (3)	0.1257 (3)	0.0483 (9)
H6A	0.5692	1.0276	0.1381	0.058*
C10	0.3975 (3)	0.4349 (3)	0.1509 (3)	0.0579 (11)
H10A	0.4239	0.3680	0.1471	0.069*
C8	0.2865 (3)	0.5352 (4)	0.1798 (3)	0.0593 (11)
H8A	0.2365	0.5388	0.1957	0.071*
C4	0.4094 (3)	1.0927 (3)	0.1215 (3)	0.0636 (12)
H4A	0.4440	1.1550	0.1313	0.076*
C3	0.3253 (3)	1.1034 (3)	0.1118 (4)	0.0718 (13)
H3A	0.3029	1.1729	0.1171	0.086*

	U11	U22	U33	U12	U13	U23
Cu1	0.0277 (3)	0.0340 (3)	0.0441 (3)	0.00547 (15)	0.0132 (2)	−0.00158 (17)
Cl1	0.0482 (6)	0.0432 (5)	0.0407 (5)	0.0035 (4)	0.0094 (4)	−0.0023 (4)
N2	0.0355 (16)	0.0317 (15)	0.0418 (16)	0.0041 (12)	0.0118 (13)	−0.0026 (12)
N3	0.0398 (17)	0.0480 (19)	0.0432 (17)	0.0156 (14)	0.0152 (14)	0.0003 (14)
N4	0.0385 (16)	0.0366 (16)	0.0392 (16)	0.0031 (12)	0.0107 (13)	0.0023 (12)
O2	0.0440 (16)	0.0712 (19)	0.0731 (19)	0.0207 (14)	0.0327 (14)	0.0047 (15)
C1	0.040 (2)	0.044 (2)	0.049 (2)	0.0096 (16)	0.0142 (17)	0.0009 (16)
N1	0.0286 (16)	0.0516 (19)	0.0505 (18)	−0.0040 (13)	0.0147 (14)	−0.0005 (14)
C11	0.052 (2)	0.0372 (19)	0.032 (2)	0.0057 (16)	0.0044 (17)	−0.0001 (15)
C5	0.052 (2)	0.038 (2)	0.040 (2)	0.0022 (16)	0.0157 (18)	−0.0024 (16)
O1	0.0326 (15)	0.077 (2)	0.092 (2)	−0.0025 (13)	0.0241 (15)	−0.0042 (17)
C2	0.051 (2)	0.066 (3)	0.059 (3)	0.029 (2)	0.019 (2)	0.002 (2)
C9	0.069 (3)	0.058 (3)	0.058 (3)	−0.024 (2)	0.009 (2)	0.009 (2)
C7	0.041 (2)	0.051 (2)	0.047 (2)	−0.0006 (17)	0.0166 (17)	0.0022 (17)
C12	0.052 (2)	0.044 (2)	0.040 (2)	0.0195 (18)	0.0113 (18)	−0.0006 (17)
C6	0.045 (2)	0.045 (2)	0.056 (2)	−0.0115 (17)	0.0177 (18)	−0.0050 (18)
C10	0.071 (3)	0.036 (2)	0.053 (2)	−0.0020 (19)	0.002 (2)	0.0001 (18)
C8	0.052 (3)	0.067 (3)	0.057 (3)	−0.014 (2)	0.016 (2)	0.006 (2)
C4	0.080 (3)	0.031 (2)	0.079 (3)	0.0027 (19)	0.025 (3)	−0.0044 (19)
C3	0.088 (4)	0.044 (3)	0.084 (3)	0.033 (2)	0.029 (3)	−0.004 (2)

Cu1—N3	1.984 (3)	C5—C4	1.371 (5)
Cu1—N1	2.012 (3)	C5—C6	1.451 (5)
Cu1—N2	2.029 (3)	O1—H1B	0.8200
Cu1—N4	2.072 (3)	C2—C3	1.352 (6)
Cu1—Cl1	2.4316 (10)	C2—H2A	0.9300
N2—C1	1.338 (4)	C9—C8	1.354 (6)
N2—C5	1.340 (4)	C9—C10	1.385 (6)
N3—C12	1.256 (5)	C9—H9A	0.9300
N3—O2	1.341 (3)	C7—C8	1.361 (5)
N4—C7	1.335 (4)	C7—H7A	0.9300
N4—C11	1.350 (4)	C12—H12A	0.9300
C1—C2	1.370 (5)	C6—H6A	0.9300
C1—H1A	0.9300	C10—H10A	0.9300
N1—C6	1.258 (4)	C8—H8A	0.9300
N1—O1	1.345 (3)	C4—C3	1.371 (6)
C11—C10	1.375 (5)	C4—H4A	0.9300
C11—C12	1.453 (5)	C3—H3A	0.9300
N3—Cu1—N1	91.79 (14)	C4—C5—C6	123.0 (4)
N3—Cu1—N2	168.29 (12)	N1—O1—H1B	109.5
N1—Cu1—N2	79.19 (11)	C3—C2—C1	118.4 (4)
N3—Cu1—N4	79.15 (12)	C3—C2—H2A	120.8
N1—Cu1—N4	151.07 (12)	C1—C2—H2A	120.8
N2—Cu1—N4	105.21 (11)	C8—C9—C10	118.3 (4)
N3—Cu1—Cl1	94.60 (9)	C8—C9—H9A	120.9
N1—Cu1—Cl1	107.40 (9)	C10—C9—H9A	120.9
N2—Cu1—Cl1	95.22 (8)	N4—C7—C8	124.0 (4)
N4—Cu1—Cl1	100.71 (8)	N4—C7—H7A	118.0
C1—N2—C5	118.1 (3)	C8—C7—H7A	118.0
C1—N2—Cu1	128.8 (2)	N3—C12—C11	116.1 (3)
C5—N2—Cu1	112.8 (2)	N3—C12—H12A	121.9
C12—N3—O2	120.3 (3)	C11—C12—H12A	121.9
C12—N3—Cu1	117.1 (2)	N1—C6—C5	115.7 (3)
O2—N3—Cu1	122.1 (2)	N1—C6—H6A	122.2
C7—N4—C11	117.2 (3)	C5—C6—H6A	122.2
C7—N4—Cu1	131.7 (2)	C11—C10—C9	119.9 (4)
C11—N4—Cu1	110.9 (2)	C11—C10—H10A	120.0
N2—C1—C2	122.9 (4)	C9—C10—H10A	120.0
N2—C1—H1A	118.5	C9—C8—C7	119.2 (4)
C2—C1—H1A	118.5	C9—C8—H8A	120.4
C6—N1—O1	118.2 (3)	C7—C8—H8A	120.4
C6—N1—Cu1	116.6 (2)	C5—C4—C3	119.3 (4)
O1—N1—Cu1	125.2 (2)	C5—C4—H4A	120.4
N4—C11—C10	121.4 (4)	C3—C4—H4A	120.4
N4—C11—C12	115.3 (3)	C2—C3—C4	119.8 (4)
C10—C11—C12	123.2 (3)	C2—C3—H3A	120.1
N2—C5—C4	121.4 (4)	C4—C3—H3A	120.1
N2—C5—C6	115.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2	0.82	1.70	2.488 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2	0.82	1.70	2.488 (5)	162