Dichlorido{N'-[(pyridin-2-yl)methyl-idene-κN]acetohydrazide-κN',O}copper(II).

In the title compound, [CuCl(2)(C(8)H(9)N(3)O)], the Cu(II) atom has a distorted square-pyramidal CuCl(2)N(2)O coordination geometry. The tridentate acetohydrazide ligand occupies three basal positions, the fourth basal position being defined by a chloride anion at a distance of 2.2116 (6) Å. The second chloride anion is in the apical position and forms a longer Cu-Cl distance of 2.4655 (7) Å. Inter-molecular N-H⋯Cl hydrogen bonds are present in the crystal, leading to the formation of chains along [10[Formula: see text]].

Related literature

For related copper(II) complexes with a similar tridentate ligand, see: Sen et al. (2005 ▶, 2007 ▶), Ray et al. (2008 ▶), Recio Despaigne et al. (2009 ▶); Datta et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

[CuCl2(C8H9N3O)]

M = 297.62

Monoclinic,

a = 6.8326 (12) Å

b = 15.137 (3) Å

c = 10.689 (3) Å

β = 95.664 (13)°

V = 1100.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.45 mm−1

T = 150 K

0.40 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.485, T max = 0.543

9791 measured reflections

2836 independent reflections

2378 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.070

S = 1.04

2836 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049671/wm2553sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049671/wm2553Isup2.hkl

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

[CuCl2(C8H9N3O)]	F(000) = 596
Mr = 297.62	Dx = 1.797 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4370 reflections
a = 6.8326 (12) Å	θ = 3.3–28.6°
b = 15.137 (3) Å	µ = 2.45 mm−1
c = 10.689 (3) Å	T = 150 K
β = 95.664 (13)°	Rectangular, green
V = 1100.0 (4) Å3	0.40 × 0.25 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
graphite	Rint = 0.024
phi and ω scans	θmax = 28.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.485, Tmax = 0.543	k = −19→20
9791 measured reflections	l = −14→6

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) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.2632P] where P = (Fo2 + 2Fc2)/3
2836 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.35 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	0.24493 (3)	0.323357 (14)	0.19561 (2)	0.03400 (8)
Cl2	0.47106 (7)	0.41980 (4)	0.26879 (5)	0.04816 (13)
Cl3	0.05430 (7)	0.30589 (3)	0.37823 (4)	0.04052 (12)
N1	0.4124 (2)	0.21177 (10)	0.19800 (14)	0.0346 (3)
C5	0.3171 (3)	0.14208 (12)	0.13949 (16)	0.0345 (4)
C4	0.4016 (3)	0.05932 (13)	0.13604 (19)	0.0443 (4)
H4	0.3316	0.0115	0.0952	0.053*
C1	0.5949 (3)	0.19982 (15)	0.25159 (19)	0.0427 (4)
H1	0.6633	0.2483	0.2918	0.051*
C2	0.6879 (3)	0.11807 (16)	0.2502 (2)	0.0517 (5)
H2	0.8185	0.1112	0.2885	0.062*
C3	0.5901 (3)	0.04753 (15)	0.1932 (2)	0.0524 (5)
H3	0.6511	−0.0088	0.1931	0.063*
C6	0.1226 (3)	0.16357 (13)	0.07736 (18)	0.0385 (4)
H6	0.0400	0.1212	0.0330	0.046*
N2	0.0738 (2)	0.24430 (10)	0.08798 (14)	0.0340 (3)
N3	−0.0947 (2)	0.28140 (11)	0.03418 (14)	0.0391 (3)
H3A	−0.1916	0.2506	−0.0048	0.047*
O1	0.0387 (2)	0.40997 (9)	0.10589 (13)	0.0437 (3)
C7	−0.0995 (3)	0.37105 (13)	0.04643 (16)	0.0377 (4)
C8	−0.2756 (3)	0.41705 (15)	−0.0143 (2)	0.0498 (5)
H8A	−0.3316	0.4550	0.0474	0.075*
H8B	−0.3737	0.3733	−0.0465	0.075*
H8C	−0.2380	0.4533	−0.0841	0.075*

	U11	U22	U33	U12	U13	U23
Cu1	0.02943 (13)	0.03512 (13)	0.03591 (13)	−0.00313 (9)	−0.00455 (8)	−0.00127 (8)
Cl2	0.0370 (2)	0.0471 (3)	0.0583 (3)	−0.0125 (2)	−0.0054 (2)	−0.0031 (2)
Cl3	0.0328 (2)	0.0516 (3)	0.0369 (2)	0.0043 (2)	0.00207 (16)	0.00244 (18)
N1	0.0301 (7)	0.0391 (8)	0.0342 (7)	−0.0002 (7)	0.0019 (6)	0.0013 (6)
C5	0.0336 (9)	0.0372 (9)	0.0327 (8)	−0.0003 (8)	0.0042 (7)	0.0003 (7)
C4	0.0477 (11)	0.0359 (10)	0.0504 (11)	0.0001 (9)	0.0104 (9)	0.0017 (8)
C1	0.0306 (9)	0.0526 (11)	0.0441 (10)	−0.0015 (9)	−0.0010 (7)	0.0026 (9)
C2	0.0347 (10)	0.0626 (14)	0.0573 (12)	0.0107 (10)	0.0017 (9)	0.0118 (11)
C3	0.0501 (12)	0.0462 (12)	0.0621 (13)	0.0136 (10)	0.0117 (10)	0.0111 (10)
C6	0.0375 (10)	0.0394 (10)	0.0380 (9)	−0.0045 (8)	0.0003 (7)	−0.0056 (7)
N2	0.0298 (7)	0.0398 (8)	0.0312 (7)	−0.0005 (6)	−0.0035 (5)	−0.0016 (6)
N3	0.0320 (8)	0.0430 (9)	0.0396 (8)	−0.0006 (7)	−0.0092 (6)	−0.0028 (6)
O1	0.0435 (7)	0.0380 (7)	0.0466 (7)	−0.0043 (6)	−0.0103 (6)	0.0044 (6)
C7	0.0365 (9)	0.0445 (10)	0.0313 (8)	0.0000 (8)	−0.0013 (7)	0.0054 (7)
C8	0.0432 (11)	0.0520 (12)	0.0516 (12)	0.0059 (10)	−0.0086 (9)	0.0072 (9)

Cu1—N2	1.9638 (15)	C2—C3	1.370 (3)
Cu1—N1	2.0390 (16)	C2—H2	0.9500
Cu1—O1	2.0872 (14)	C3—H3	0.9500
Cu1—Cl2	2.2116 (6)	C6—N2	1.275 (2)
Cu1—Cl3	2.4655 (7)	C6—H6	0.9500
N1—C1	1.332 (2)	N2—N3	1.357 (2)
N1—C5	1.359 (2)	N3—C7	1.364 (3)
C5—C4	1.381 (3)	N3—H3A	0.8800
C5—C6	1.462 (3)	O1—C7	1.235 (2)
C4—C3	1.381 (3)	C7—C8	1.484 (3)
C4—H4	0.9500	C8—H8A	0.9800
C1—C2	1.392 (3)	C8—H8B	0.9800
C1—H1	0.9500	C8—H8C	0.9800
N2—Cu1—N1	78.67 (6)	C1—C2—H2	120.2
N2—Cu1—O1	77.16 (6)	C2—C3—C4	119.2 (2)
N1—Cu1—O1	151.48 (6)	C2—C3—H3	120.4
N2—Cu1—Cl2	164.60 (5)	C4—C3—H3	120.4
N1—Cu1—Cl2	99.83 (5)	N2—C6—C5	114.00 (16)
O1—Cu1—Cl2	99.45 (4)	N2—C6—H6	123.0
N2—Cu1—Cl3	93.90 (5)	C5—C6—H6	123.0
N1—Cu1—Cl3	103.94 (4)	C6—N2—N3	125.27 (16)
O1—Cu1—Cl3	92.62 (5)	C6—N2—Cu1	119.37 (13)
Cl2—Cu1—Cl3	101.30 (2)	N3—N2—Cu1	115.30 (12)
C1—N1—C5	118.57 (17)	N2—N3—C7	113.47 (15)
C1—N1—Cu1	128.19 (14)	N2—N3—H3A	123.3
C5—N1—Cu1	113.21 (12)	C7—N3—H3A	123.3
N1—C5—C4	122.24 (18)	C7—O1—Cu1	112.58 (12)
N1—C5—C6	114.14 (16)	O1—C7—N3	119.99 (17)
C4—C5—C6	123.58 (18)	O1—C7—C8	123.20 (19)
C3—C4—C5	118.6 (2)	N3—C7—C8	116.80 (17)
C3—C4—H4	120.7	C7—C8—H8A	109.5
C5—C4—H4	120.7	C7—C8—H8B	109.5
N1—C1—C2	121.7 (2)	H8A—C8—H8B	109.5
N1—C1—H1	119.2	C7—C8—H8C	109.5
C2—C1—H1	119.2	H8A—C8—H8C	109.5
C3—C2—C1	119.7 (2)	H8B—C8—H8C	109.5
C3—C2—H2	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl3i	0.88	2.21	3.0799 (16)	170.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl3i	0.88	2.21	3.0799 (16)	170

Symmetry code: (i) .