Chlorido[N'-(2-oxidobenzil-idene)acetohydrazide-κO,N',O']copper(II) dihydrate.

In the title complex, [Cu(C(9)H(9)N(2)O(2))Cl]·2H(2)O, prepared from the Schiff base ligand N'-(2-hydroxy-benzil-idene)aceto-hydrazide and copper(II) chloride, the Cu(II) atom is coord-inated by two O atoms and one N atom from the ligand and by a Cl atom in a distorted square-planar geometry. The two donor O atoms of the tridentate Schiff base ligand are in a trans arrangement. In the crystal structure, there is an extensive inter-molecular hydrogen-bonding network; N-H⋯O, O-H⋯O and O-H⋯Cl inter-actions, involving the uncoordinated water mol-ecules, lead to the formation of a two-dimensional network parallel to the ab plane.

Related literature

For related structures, see: Ainscough et al. (1998 ▶); Chan et al. (1995 ▶); Koh et al. (1998 ▶). For similar square-planar copper(II) complexes, see: Li et al. (2008 ▶); Qiu & Wu (2004 ▶).

Experimental

Crystal data

[Cu(C9H9N2O2)Cl]·2H2O

M = 312.20

Triclinic,

a = 6.762 (2) Å

b = 8.987 (2) Å

c = 10.312 (3) Å

α = 76.940 (11)°

β = 84.645 (12)°

γ = 81.903 (13)°

V = 603.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.04 mm−1

T = 173 (2) K

0.16 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

5193 measured reflections

3520 independent reflections

3036 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.075

S = 1.06

3520 reflections

174 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.58 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000105/su2089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000105/su2089Isup2.hkl

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

[Cu(C9H9N2O2)Cl]·2H2O	Z = 2
Mr = 312.20	F(000) = 318
Triclinic, P1	Dx = 1.719 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.762 (2) Å	Cell parameters from 2138 reflections
b = 8.987 (2) Å	θ = 1.0–30.0°
c = 10.312 (3) Å	µ = 2.04 mm−1
α = 76.940 (11)°	T = 173 K
β = 84.645 (12)°	Prism, green
γ = 81.903 (13)°	0.16 × 0.12 × 0.10 mm
V = 603.1 (3) Å3

Nonius KappaCCD diffractometer	3036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 30.0°, θmin = 2.8°
π[Please check] scans	h = −9→8
5193 measured reflections	k = −12→12
3520 independent reflections	l = −13→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[s2(Fo2) + (0.0139P)2 + 0.4006P] where P = (Fo2 + 2Fc2)/3
3520 reflections	(Δ/σ)max = 0.036
174 parameters	Δρmax = 0.50 e Å−3
4 restraints	Δρmin = −0.58 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	0.70935 (3)	0.12114 (2)	0.20663 (2)	0.01876 (7)
Cl1	0.59285 (8)	0.32377 (5)	0.29307 (5)	0.02773 (12)
O1	0.6694 (2)	0.22971 (14)	0.02897 (14)	0.0247 (3)
O2	0.7955 (2)	−0.00478 (15)	0.37823 (14)	0.0238 (3)
O3	0.9689 (3)	−0.47969 (18)	0.23882 (18)	0.0330 (4)
O4	0.2576 (3)	0.44891 (19)	0.04512 (18)	0.0342 (4)
N1	0.8652 (2)	−0.18532 (18)	0.25675 (17)	0.0200 (3)
H1	0.899 (4)	−0.273 (3)	0.249 (3)	0.032 (7)*
N2	0.7995 (2)	−0.07024 (16)	0.15054 (15)	0.0169 (3)
C1	0.6714 (3)	0.1693 (2)	−0.07799 (19)	0.0195 (4)
C2	0.6135 (3)	0.2688 (2)	−0.1980 (2)	0.0229 (4)
H2	0.5741	0.3749	−0.1995	0.050*
C3	0.6125 (3)	0.2164 (2)	−0.3137 (2)	0.0251 (4)
H3	0.5735	0.2867	−0.3934	0.050*
C4	0.6682 (3)	0.0608 (2)	−0.3152 (2)	0.0263 (4)
H4	0.6668	0.0249	−0.3949	0.050*
C5	0.7249 (3)	−0.0390 (2)	−0.1993 (2)	0.0231 (4)
H5	0.7630	−0.1448	−0.1998	0.050*
C6	0.7283 (3)	0.0114 (2)	−0.07873 (19)	0.0189 (4)
C7	0.7920 (3)	−0.1029 (2)	0.03622 (19)	0.0193 (4)
H7	0.8299	−0.2062	0.0273	0.050*
C8	0.8581 (3)	−0.1417 (2)	0.37220 (19)	0.0210 (4)
C9	0.9213 (3)	−0.2590 (2)	0.4927 (2)	0.0286 (4)
H9A	0.9653	−0.3581	0.4679	0.050*
H9B	0.8083	−0.2698	0.5595	0.050*
H9C	1.0320	−0.2262	0.5298	0.050*
HW1	1.054 (4)	−0.504 (3)	0.180 (2)	0.050 (9)*
HW2	0.873 (4)	−0.529 (4)	0.240 (4)	0.089 (13)*
HW3	0.286 (5)	0.539 (2)	0.014 (3)	0.067 (10)*
HW4	0.367 (4)	0.398 (4)	0.067 (4)	0.076 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02308 (13)	0.01631 (12)	0.01686 (13)	−0.00064 (8)	−0.00474 (9)	−0.00321 (8)
Cl1	0.0375 (3)	0.0199 (2)	0.0257 (3)	0.00195 (19)	−0.0029 (2)	−0.00765 (18)
O1	0.0400 (8)	0.0171 (6)	0.0174 (7)	−0.0032 (6)	−0.0073 (6)	−0.0024 (5)
O2	0.0316 (8)	0.0215 (6)	0.0178 (7)	0.0027 (5)	−0.0065 (6)	−0.0049 (5)
O3	0.0398 (10)	0.0234 (7)	0.0359 (10)	−0.0038 (7)	−0.0016 (8)	−0.0069 (7)
O4	0.0302 (9)	0.0296 (8)	0.0425 (10)	−0.0032 (7)	−0.0075 (7)	−0.0052 (7)
N1	0.0234 (8)	0.0161 (7)	0.0192 (8)	−0.0002 (6)	−0.0047 (6)	−0.0013 (6)
N2	0.0173 (7)	0.0153 (7)	0.0173 (8)	−0.0008 (5)	−0.0048 (6)	−0.0008 (6)
C1	0.0191 (9)	0.0223 (9)	0.0176 (9)	−0.0052 (7)	−0.0017 (7)	−0.0034 (7)
C2	0.0249 (10)	0.0219 (9)	0.0208 (10)	−0.0048 (7)	−0.0042 (8)	−0.0002 (7)
C3	0.0233 (10)	0.0341 (10)	0.0167 (9)	−0.0066 (8)	−0.0031 (8)	−0.0003 (8)
C4	0.0268 (10)	0.0367 (11)	0.0179 (10)	−0.0075 (8)	−0.0012 (8)	−0.0088 (8)
C5	0.0223 (9)	0.0263 (9)	0.0223 (10)	−0.0042 (7)	−0.0001 (8)	−0.0087 (8)
C6	0.0188 (8)	0.0220 (9)	0.0169 (9)	−0.0050 (7)	−0.0023 (7)	−0.0042 (7)
C7	0.0190 (9)	0.0190 (8)	0.0204 (9)	−0.0028 (7)	−0.0018 (7)	−0.0049 (7)
C8	0.0197 (9)	0.0242 (9)	0.0178 (9)	−0.0011 (7)	−0.0030 (7)	−0.0022 (7)
C9	0.0357 (11)	0.0271 (10)	0.0198 (10)	0.0008 (8)	−0.0066 (9)	0.0009 (8)

Cu1—O1	1.8951 (13)	C1—C6	1.419 (3)
Cu1—N2	1.9373 (15)	C2—C3	1.380 (3)
Cu1—O2	1.9628 (13)	C2—H2	0.9500
Cu1—Cl1	2.2203 (5)	C3—C4	1.399 (3)
O1—C1	1.333 (2)	C3—H3	0.9500
O2—C8	1.257 (2)	C4—C5	1.373 (3)
O3—HW1	0.837 (17)	C4—H4	0.9500
O3—HW2	0.837 (18)	C5—C6	1.420 (3)
O4—HW3	0.840 (18)	C5—H5	0.9500
O4—HW4	0.835 (18)	C6—C7	1.438 (2)
N1—C8	1.330 (2)	C7—H7	0.9500
N1—N2	1.384 (2)	C8—C9	1.489 (3)
N1—H1	0.81 (3)	C9—H9A	0.9800
N2—C7	1.285 (2)	C9—H9B	0.9800
C1—C2	1.406 (3)	C9—H9C	0.9800
O1—Cu1—N2	92.17 (6)	C2—C3—H3	119.6
O1—Cu1—O2	170.21 (6)	C4—C3—H3	119.6
N2—Cu1—O2	81.39 (6)	C5—C4—C3	118.78 (18)
O1—Cu1—Cl1	93.63 (4)	C5—C4—H4	120.6
N2—Cu1—Cl1	173.31 (5)	C3—C4—H4	120.6
O2—Cu1—Cl1	93.27 (4)	C4—C5—C6	121.80 (18)
C1—O1—Cu1	126.91 (11)	C4—C5—H5	119.1
C8—O2—Cu1	112.67 (12)	C6—C5—H5	119.1
HW1—O3—HW2	107 (3)	C1—C6—C5	119.09 (17)
HW3—O4—HW4	104 (3)	C1—C6—C7	123.89 (17)
C8—N1—N2	114.80 (15)	C5—C6—C7	117.02 (17)
C8—N1—H1	123.0 (18)	N2—C7—C6	122.26 (16)
N2—N1—H1	122.1 (18)	N2—C7—H7	118.9
C7—N2—N1	119.37 (15)	C6—C7—H7	118.9
C7—N2—Cu1	129.28 (12)	O2—C8—N1	119.94 (16)
N1—N2—Cu1	111.15 (12)	O2—C8—C9	121.56 (18)
O1—C1—C2	117.80 (17)	N1—C8—C9	118.49 (17)
O1—C1—C6	124.33 (16)	C8—C9—H9A	109.5
C2—C1—C6	117.88 (17)	C8—C9—H9B	109.5
C3—C2—C1	121.67 (18)	H9A—C9—H9B	109.5
C3—C2—H2	119.2	C8—C9—H9C	109.5
C1—C2—H2	119.2	H9A—C9—H9C	109.5
C2—C3—C4	120.79 (18)	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.81 (3)	1.88 (3)	2.683 (2)	177 (3)
O3—HW1···O4i	0.84 (2)	1.94 (2)	2.777 (3)	177 (3)
O3—HW2···Cl1ii	0.84 (2)	2.41 (2)	3.2333 (18)	168 (4)
O4—HW3···O1iii	0.84 (2)	2.09 (2)	2.916 (2)	169 (3)
O4—HW4···O1	0.84 (2)	2.43 (2)	3.191 (2)	153 (3)
O4—HW4···Cl1	0.84 (2)	2.80 (3)	3.4648 (17)	137 (3)

Cu1—O1	1.8951 (13)
Cu1—N2	1.9373 (15)
Cu1—O2	1.9628 (13)
Cu1—Cl1	2.2203 (5)

O1—Cu1—N2	92.17 (6)
O1—Cu1—O2	170.21 (6)
N2—Cu1—O2	81.39 (6)
O1—Cu1—Cl1	93.63 (4)
N2—Cu1—Cl1	173.31 (5)
O2—Cu1—Cl1	93.27 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.81 (3)	1.88 (3)	2.683 (2)	177 (3)
O3—HW1⋯O4i	0.837 (17)	1.941 (18)	2.777 (3)	177 (3)
O3—HW2⋯Cl1ii	0.837 (18)	2.41 (2)	3.2333 (18)	168 (4)
O4—HW3⋯O1iii	0.840 (18)	2.087 (19)	2.916 (2)	169 (3)
O4—HW4⋯O1	0.835 (18)	2.43 (2)	3.191 (2)	153 (3)
O4—HW4⋯Cl1	0.835 (18)	2.80 (3)	3.4648 (17)	137 (3)

Symmetry codes: (i) ; (ii) ; (iii) .