Aqua[1-(pyridin-2-yl)ethanone oximato][1-(2-pyridin-2-yl)ethanone oxime]­copper(II) perchlorate mono­hydrate

Zhong, B.; Li, S.; Chen, G.

doi:10.1107/S1600536812023872

metal-organic compounds

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Volume 68| Part 7| July 2012| Page m874

https://doi.org/10.1107/S1600536812023872

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Aqua[1-(pyridin-2-yl)ethanone oximato][1-(2-pyridin-2-yl)ethanone oxime]copper(II) perchlorate monohydrate

Baoyun Zhong,^a Shengli Li ^b and Guifang Chen ^b ^*

^aThe Third Middle School in Liaocheng, Shandong 252059, People's Republic of China, and ^bDepartment of Chemistry and Biology, Dongchang College Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@163.com

(Received 15 April 2012; accepted 25 May 2012; online 13 June 2012)

In the title compound, [Cu(C₇H₇N₂O)(C₇H₈N₂O)(H₂O)]ClO₄·H₂O, the Cu^II ion is five-coordinated by the N atoms from the 1-(pyridin-2-yl)ethanone oximate and 1-(pyridin-2-yl)ethanone oxime ligands and by the water O atom in a distorted square-pyramidal geometry. The two organic ligands are linked by an intramolecular O—H⋯O hydrogen bond. In the crystal, molecules and ions are linked by O—H⋯O hydrogen-bonding interactions, forming chains along the a axis. The perchlorate O atoms are disordered in a 0.58 (2):0.42 (2) ratio.

Related literature

For the coordination chemistry of oximes, see: Chaudhuri (2003 ); Pavlishchuk et al. (2003 ). For related structures, see: Qiu et al. (2011 ); Wu & Wu (2008 ); Zuo et al. (2007 ). For the properties of related complexes, see: Davidson et al. (2007 ); Clerac et al. (2002 ).

Experimental

Crystal data

[Cu(C₇H₇N₂O)(C₇H₈N₂O)(H₂O)]ClO₄·H₂O
M_r = 470.32
Monoclinic, P c
a = 6.3526 (7) Å
b = 15.7199 (14) Å
c = 9.8235 (9) Å
β = 101.235 (1)°
V = 962.20 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.39 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.587, T_max = 0.626
4732 measured reflections
2284 independent reflections
2062 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.00
2284 reflections
292 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 )
Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.63	2.421 (7)	163
O3—H3C⋯O2ⁱ	0.85	1.92	2.757 (6)	170
O3—H3D⋯O8ⁱ	0.85	1.82	2.658 (8)	170
O8—H8C⋯O6ⁱⁱ	0.85	1.86	2.660 (7)	157
O8—H8D⋯O4ⁱⁱⁱ	0.85	2.11	2.862 (7)	148
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x-1, y, z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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), Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812023872/aa2060sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812023872/aa2060Isup2.hkl

checkCIF report

Comment top

There is a new interest in the coordination chemistry of oximes (Davidson et al., 2007; Pavlishchuk et al., 2003; Chaudhuri, 2003). 2-pyridyl oximes are a subclass of oximes whose anions are versatile ligands for a variety of research objectives and have been key ligands in several areas of molecular magnetism, including single-molecule and single-chain magnets (Clerac et al., 2002).

In the title complex (Fig. 1) the Cu²⁺ center is five-coordinated by N atoms from two 1-(pyridin-2-yl)ethanone oxime ligands (one of them is deprotonated) and one water molecule. The two 1-(pyridin-2-yl)ethanone oxime ligands are coordinated to copper to form two five-membered CuC₂N₂ rings and a strong intramolecular hydrogen bond exists between the OH group and the negatively charged oxygen of the other ligand which is shorter than reported in the literature (Qiu et al., 2011; Wu et al. 2008). The copper atom adopts a distorted 4+1 square-pyramidal coordination mode with the distortion parameter being 0.005, which is smaller than the values reported in the literature (Qiu et al., 2011; Wu et al., 2008). Another water molecule and the perchlorate anion are not coordinated but they take part in the formation of H-bonds (Table 1). The perclorate O atoms are disordered between two orientations around the central Cl atom with the occupancies 0.42 (2) (O4/O7) and 0.58 (2) (O4A/O7A).

Related literature top

For the coordination chemistry of oximes, see: Chaudhuri (2003); Pavlishchuk et al. (2003). For related structures, see: Qiu et al. (2011); Wu & Wu (2008); Zuo et al. (2007). For the properties of related complexes, see: Davidson et al. (2007); Clerac et al. (2002). Scheme - water should coordinate via O atom, not H as shown

Experimental top

A solution of Cu(ClO₄)₂ (0.1311 g, 0.5 mmol) in H₂O (10 ml) was added to a solution of 1-(pyridin-2-yl)ethanone oxime (0.068 g, 0.5 mmol) in MeCN (10 ml). After 0.5 h stirring, solid NaOAc (0.082 g, 1 mmol) was added slowly, and the reaction mixture was kept under magnetic stirring for another 6h. A small quantity of undissolved material was removed by filtration and the solution was left to slowly evaporate, and after one month, green crystals suitable for X-ray diffraction were obtained. (20.5%, m.p. 310-315 K). FTIR (KBr) v (cm^-l): 3448 (O—H); 1597, (Cδb N); 2917, 1437, (C—H); 1157, 1177, 1260 (N—O).

Structure description top

For the coordination chemistry of oximes, see: Chaudhuri (2003); Pavlishchuk et al. (2003). For related structures, see: Qiu et al. (2011); Wu & Wu (2008); Zuo et al. (2007). For the properties of related complexes, see: Davidson et al. (2007); Clerac et al. (2002). Scheme - water should coordinate via O atom, not H as shown

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure with hydrogen bonds shown as dashed lines.

Aqua[1-(pyridin-2-yl)ethanone oximato][1-(pyridin-2-yl)ethanone oxime]copper(II) perchlorate monohydrate top

Crystal data top

[Cu(C₇H₇N₂O)(C₇H₈N₂O)(H₂O)]ClO₄·H₂O	F(000) = 482
M_r = 470.32	D_x = 1.623 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2353 reflections
a = 6.3526 (7) Å	θ = 2.5–24.1°
b = 15.7199 (14) Å	µ = 1.32 mm⁻¹
c = 9.8235 (9) Å	T = 298 K
β = 101.235 (1)°	Block, green
V = 962.20 (16) Å³	0.45 × 0.40 × 0.39 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	2284 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.587, T_max = 0.626	k = −18→18
4732 measured reflections	l = −9→11

Refinement top

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0657P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2284 reflections	Δρ_max = 0.31 e Å⁻³
292 parameters	Δρ_min = −0.36 e Å⁻³
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

[Cu(C₇H₇N₂O)(C₇H₈N₂O)(H₂O)]ClO₄·H₂O	V = 962.20 (16) Å³
M_r = 470.32	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 6.3526 (7) Å	µ = 1.32 mm⁻¹
b = 15.7199 (14) Å	T = 298 K
c = 9.8235 (9) Å	0.45 × 0.40 × 0.39 mm
β = 101.235 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2284 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2062 reflections with I > 2σ(I)
T_min = 0.587, T_max = 0.626	R_int = 0.031
4732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.096	Δρ_max = 0.31 e Å⁻³
S = 1.00	Δρ_min = −0.36 e Å⁻³
2284 reflections	Absolute structure: Flack (1983)
292 parameters	Absolute structure parameter: 0.00 (2)
2 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.90524 (7)	0.78796 (3)	0.51950 (6)	0.04434 (19)
N1	1.0620 (8)	0.8673 (3)	0.4096 (5)	0.0487 (11)
N2	0.7645 (8)	0.8981 (3)	0.5462 (5)	0.0529 (11)
N3	0.9979 (8)	0.6665 (3)	0.4862 (5)	0.0501 (11)
N4	0.7118 (8)	0.7233 (3)	0.6158 (5)	0.0559 (12)
O1	0.6121 (8)	0.9078 (3)	0.6241 (5)	0.0749 (13)
H1	0.5875	0.8617	0.6568	0.112*
O2	0.5748 (8)	0.7602 (3)	0.6854 (6)	0.0786 (14)
O3	1.1616 (7)	0.7948 (2)	0.7173 (4)	0.0574 (10)
H3C	1.2907	0.7810	0.7164	0.069*
H3D	1.1287	0.7759	0.7916	0.069*
O4	0.644 (5)	0.6788 (19)	0.031 (3)	0.173 (11)	0.42 (2)
O5	0.697 (5)	0.7657 (16)	0.225 (3)	0.113 (9)	0.42 (2)
O6	0.362 (4)	0.7125 (19)	0.129 (3)	0.156 (12)	0.42 (2)
O7	0.612 (4)	0.6234 (11)	0.239 (2)	0.133 (9)	0.42 (2)
O4A	0.616 (3)	0.7497 (16)	0.277 (2)	0.120 (7)	0.58 (2)
O5A	0.421 (4)	0.6442 (16)	0.159 (2)	0.183 (10)	0.58 (2)
O6A	0.776 (3)	0.6580 (10)	0.1461 (18)	0.140 (8)	0.58 (2)
O7A	0.530 (3)	0.7535 (10)	0.0400 (16)	0.146 (7)	0.58 (2)
O8	0.0118 (15)	0.7456 (7)	0.9393 (8)	0.149 (3)
H8C	0.1086	0.7216	0.9990	0.179*
H8D	−0.1035	0.7468	0.9708	0.179*
Cl1	0.5869 (3)	0.69941 (11)	0.15550 (19)	0.0719 (5)
C1	1.2136 (12)	0.8510 (4)	0.3400 (8)	0.073 (2)
H1A	1.2607	0.7951	0.3381	0.088*
C2	1.3084 (13)	0.9117 (4)	0.2689 (9)	0.077 (2)
H2	1.4162	0.8970	0.2213	0.093*
C3	1.2380 (11)	0.9941 (4)	0.2710 (7)	0.0660 (17)
H3	1.2958	1.0365	0.2234	0.079*
C4	1.0826 (10)	1.0129 (3)	0.3439 (6)	0.0552 (14)
H4	1.0358	1.0688	0.3478	0.066*
C5	0.9947 (9)	0.9500 (3)	0.4114 (5)	0.0426 (11)
C6	0.8256 (9)	0.9661 (3)	0.4914 (6)	0.0494 (13)
C7	0.7378 (12)	1.0516 (4)	0.5062 (8)	0.0723 (18)
H7A	0.7683	1.0679	0.6022	0.108*
H7B	0.5854	1.0509	0.4730	0.108*
H7C	0.8027	1.0916	0.4530	0.108*
C8	1.1394 (14)	0.6393 (5)	0.4171 (8)	0.070 (2)
H8	1.2088	0.6797	0.3724	0.084*
C9	1.1956 (15)	0.5537 (4)	0.4048 (9)	0.085 (2)
H9	1.2981	0.5373	0.3542	0.102*
C10	1.0912 (16)	0.4959 (4)	0.4713 (9)	0.088 (2)
H10	1.1217	0.4382	0.4666	0.106*
C11	0.9453 (15)	0.5222 (4)	0.5433 (9)	0.079 (2)
H11	0.8756	0.4826	0.5892	0.095*
C12	0.8964 (13)	0.6082 (3)	0.5501 (6)	0.0569 (17)
C13	0.7394 (12)	0.6412 (4)	0.6278 (8)	0.0603 (18)
C14	0.6098 (15)	0.5892 (6)	0.7110 (10)	0.094 (3)
H14A	0.4660	0.5828	0.6593	0.141*
H14B	0.6064	0.6176	0.7971	0.141*
H14C	0.6743	0.5341	0.7296	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0416 (3)	0.0393 (3)	0.0582 (3)	0.0006 (4)	0.0246 (2)	0.0052 (3)
N1	0.052 (3)	0.040 (2)	0.060 (3)	0.002 (2)	0.029 (2)	0.001 (2)
N2	0.053 (3)	0.050 (3)	0.065 (3)	0.010 (2)	0.033 (2)	0.000 (2)
N3	0.056 (3)	0.043 (2)	0.054 (3)	−0.001 (2)	0.017 (2)	0.002 (2)
N4	0.048 (3)	0.060 (3)	0.065 (3)	−0.003 (2)	0.023 (2)	0.008 (2)
O1	0.074 (3)	0.067 (3)	0.102 (3)	0.015 (2)	0.062 (3)	0.006 (2)
O2	0.059 (3)	0.080 (3)	0.111 (4)	0.003 (3)	0.051 (3)	0.021 (3)
O3	0.042 (2)	0.069 (2)	0.064 (3)	0.0020 (17)	0.0151 (19)	−0.0034 (18)
O4	0.19 (3)	0.19 (3)	0.14 (2)	0.02 (2)	0.04 (2)	−0.020 (19)
O5	0.115 (19)	0.083 (10)	0.13 (2)	−0.021 (12)	−0.001 (13)	0.023 (12)
O6	0.128 (18)	0.16 (2)	0.17 (2)	0.042 (17)	0.002 (16)	−0.028 (18)
O7	0.138 (18)	0.101 (12)	0.141 (16)	−0.011 (11)	−0.019 (13)	0.009 (10)
O4A	0.108 (14)	0.133 (15)	0.110 (13)	0.037 (11)	0.000 (8)	−0.033 (11)
O5A	0.18 (2)	0.172 (18)	0.198 (19)	−0.056 (18)	0.038 (16)	0.016 (16)
O6A	0.143 (13)	0.147 (13)	0.135 (14)	0.077 (11)	0.041 (10)	−0.022 (10)
O7A	0.187 (16)	0.123 (11)	0.120 (11)	0.013 (11)	0.006 (11)	0.038 (9)
O8	0.124 (6)	0.226 (9)	0.108 (5)	0.001 (7)	0.051 (5)	0.048 (6)
Cl1	0.0737 (12)	0.0706 (10)	0.0779 (11)	0.0041 (9)	0.0309 (9)	−0.0088 (8)
C1	0.085 (5)	0.049 (3)	0.102 (6)	0.009 (3)	0.057 (4)	0.009 (3)
C2	0.079 (5)	0.066 (4)	0.107 (5)	0.002 (4)	0.067 (4)	0.017 (4)
C3	0.069 (4)	0.062 (4)	0.075 (4)	−0.010 (3)	0.035 (3)	0.020 (3)
C4	0.059 (4)	0.039 (3)	0.069 (4)	−0.003 (2)	0.017 (3)	0.012 (2)
C5	0.045 (3)	0.037 (2)	0.047 (3)	0.000 (2)	0.015 (2)	0.002 (2)
C6	0.050 (3)	0.041 (3)	0.063 (3)	0.006 (2)	0.023 (3)	0.003 (2)
C7	0.080 (5)	0.058 (3)	0.086 (4)	0.025 (3)	0.033 (4)	−0.001 (3)
C8	0.090 (6)	0.048 (4)	0.082 (5)	0.001 (4)	0.040 (4)	0.005 (3)
C9	0.101 (6)	0.054 (4)	0.107 (6)	0.011 (4)	0.039 (5)	−0.006 (4)
C10	0.119 (7)	0.044 (3)	0.099 (5)	0.000 (4)	0.015 (5)	−0.005 (4)
C11	0.092 (6)	0.047 (3)	0.093 (6)	−0.019 (4)	0.004 (5)	0.009 (3)
C12	0.060 (3)	0.047 (3)	0.059 (4)	−0.010 (3)	0.000 (3)	0.006 (3)
C13	0.054 (4)	0.055 (4)	0.068 (4)	−0.012 (3)	0.003 (3)	0.018 (3)
C14	0.087 (5)	0.083 (5)	0.119 (7)	−0.025 (4)	0.035 (5)	0.035 (5)

Geometric parameters (Å, º) top

Cu1—N4	1.973 (5)	C1—C2	1.387 (8)
Cu1—N2	1.989 (4)	C1—H1A	0.9300
Cu1—N1	2.033 (5)	C2—C3	1.372 (9)
Cu1—N3	2.043 (5)	C2—H2	0.9300
Cu1—O3	2.282 (4)	C3—C4	1.360 (8)
N1—C1	1.311 (8)	C3—H3	0.9300
N1—C5	1.370 (7)	C4—C5	1.369 (7)
N2—C6	1.291 (7)	C4—H4	0.9300
N2—O1	1.355 (6)	C5—C6	1.472 (7)
N3—C8	1.300 (9)	C6—C7	1.472 (7)
N3—C12	1.345 (7)	C7—H7A	0.9600
N4—C13	1.305 (7)	C7—H7B	0.9600
N4—O2	1.340 (6)	C7—H7C	0.9600
O1—H1	0.8200	C8—C9	1.403 (10)
O3—H3C	0.8500	C8—H8	0.9300
O3—H3D	0.8500	C9—C10	1.364 (12)
O4—Cl1	1.38 (2)	C9—H9	0.9300
O5—Cl1	1.36 (3)	C10—C11	1.336 (13)
O6—Cl1	1.42 (3)	C10—H10	0.9300
O7—Cl1	1.438 (19)	C11—C12	1.392 (9)
O4A—Cl1	1.414 (18)	C11—H11	0.9300
O5A—Cl1	1.371 (18)	C12—C13	1.463 (11)
O6A—Cl1	1.385 (13)	C13—C14	1.509 (9)
O7A—Cl1	1.407 (13)	C14—H14A	0.9600
O8—H8C	0.8501	C14—H14B	0.9600
O8—H8D	0.8500	C14—H14C	0.9600

N4—Cu1—N2	92.72 (19)	C1—C2—H2	121.1
N4—Cu1—N1	170.52 (19)	C4—C3—C2	119.1 (5)
N2—Cu1—N1	79.4 (2)	C4—C3—H3	120.5
N4—Cu1—N3	79.7 (2)	C2—C3—H3	120.5
N2—Cu1—N3	170.2 (2)	C3—C4—C5	120.3 (5)
N1—Cu1—N3	107.58 (19)	C3—C4—H4	119.9
N4—Cu1—O3	91.35 (19)	C5—C4—H4	119.9
N2—Cu1—O3	96.39 (18)	C4—C5—N1	121.5 (5)
N1—Cu1—O3	94.67 (18)	C4—C5—C6	122.9 (5)
N3—Cu1—O3	90.01 (17)	N1—C5—C6	115.6 (4)
C1—N1—C5	117.1 (5)	N2—C6—C5	113.0 (4)
C1—N1—Cu1	130.0 (4)	N2—C6—C7	124.4 (5)
C5—N1—Cu1	112.9 (3)	C5—C6—C7	122.6 (5)
C6—N2—O1	116.6 (4)	C6—C7—H7A	109.5
C6—N2—Cu1	119.1 (4)	C6—C7—H7B	109.5
O1—N2—Cu1	124.2 (4)	H7A—C7—H7B	109.5
C8—N3—C12	117.6 (5)	C6—C7—H7C	109.5
C8—N3—Cu1	129.9 (4)	H7A—C7—H7C	109.5
C12—N3—Cu1	112.5 (4)	H7B—C7—H7C	109.5
C13—N4—O2	118.2 (5)	N3—C8—C9	125.0 (7)
C13—N4—Cu1	117.9 (5)	N3—C8—H8	117.5
O2—N4—Cu1	123.3 (4)	C9—C8—H8	117.5
N2—O1—H1	109.5	C10—C9—C8	116.3 (8)
Cu1—O3—H3C	120.6	C10—C9—H9	121.9
Cu1—O3—H3D	117.4	C8—C9—H9	121.9
H3C—O3—H3D	108.6	C11—C10—C9	119.9 (6)
H8C—O8—H8D	108.5	C11—C10—H10	120.0
O5—Cl1—O4	115.1 (18)	C9—C10—H10	120.0
O5A—Cl1—O6A	112.7 (14)	C10—C11—C12	120.7 (7)
O5A—Cl1—O7A	108.9 (13)	C10—C11—H11	119.7
O6A—Cl1—O7A	108.6 (11)	C12—C11—H11	119.6
O5A—Cl1—O4A	108.1 (14)	N3—C12—C11	120.5 (8)
O6A—Cl1—O4A	110.2 (10)	N3—C12—C13	116.1 (5)
O7A—Cl1—O4A	108.4 (11)	C11—C12—C13	123.4 (6)
O5—Cl1—O6	112.4 (16)	N4—C13—C12	113.4 (6)
O4—Cl1—O6	107.6 (18)	N4—C13—C14	120.4 (7)
O5—Cl1—O7	111.4 (13)	C12—C13—C14	126.2 (6)
O4—Cl1—O7	106.8 (16)	C13—C14—H14A	109.5
O6—Cl1—O7	102.6 (17)	C13—C14—H14B	109.5
N1—C1—C2	124.3 (6)	H14A—C14—H14B	109.5
N1—C1—H1A	117.9	C13—C14—H14C	109.5
C2—C1—H1A	117.9	H14A—C14—H14C	109.5
C3—C2—C1	117.8 (6)	H14B—C14—H14C	109.5
C3—C2—H2	121.1

N2—Cu1—N1—C1	−179.9 (7)	C1—N1—C5—C4	−0.2 (8)
N3—Cu1—N1—C1	−7.0 (7)	Cu1—N1—C5—C4	179.6 (4)
O3—Cu1—N1—C1	84.5 (6)	C1—N1—C5—C6	−179.5 (6)
N2—Cu1—N1—C5	0.3 (4)	Cu1—N1—C5—C6	0.3 (6)
N3—Cu1—N1—C5	173.2 (4)	O1—N2—C6—C5	178.7 (5)
O3—Cu1—N1—C5	−95.3 (4)	Cu1—N2—C6—C5	1.3 (7)
N4—Cu1—N2—C6	−175.7 (5)	O1—N2—C6—C7	−1.2 (9)
N1—Cu1—N2—C6	−1.0 (5)	Cu1—N2—C6—C7	−178.6 (5)
O3—Cu1—N2—C6	92.6 (5)	C4—C5—C6—N2	179.7 (5)
N4—Cu1—N2—O1	7.2 (5)	N1—C5—C6—N2	−1.0 (7)
N1—Cu1—N2—O1	−178.1 (5)	C4—C5—C6—C7	−0.4 (8)
O3—Cu1—N2—O1	−84.5 (5)	N1—C5—C6—C7	178.9 (6)
N4—Cu1—N3—C8	178.0 (7)	C12—N3—C8—C9	−0.4 (12)
N1—Cu1—N3—C8	4.3 (7)	Cu1—N3—C8—C9	177.8 (6)
O3—Cu1—N3—C8	−90.6 (7)	N3—C8—C9—C10	0.0 (13)
N4—Cu1—N3—C12	−3.7 (4)	C8—C9—C10—C11	−0.2 (13)
N1—Cu1—N3—C12	−177.5 (4)	C9—C10—C11—C12	0.7 (12)
O3—Cu1—N3—C12	87.6 (4)	C8—N3—C12—C11	0.9 (10)
N2—Cu1—N4—C13	−179.8 (5)	Cu1—N3—C12—C11	−177.6 (5)
N3—Cu1—N4—C13	6.4 (5)	C8—N3—C12—C13	179.5 (7)
O3—Cu1—N4—C13	−83.3 (5)	Cu1—N3—C12—C13	1.0 (7)
N2—Cu1—N4—O2	−9.3 (5)	C10—C11—C12—N3	−1.1 (11)
N3—Cu1—N4—O2	176.9 (5)	C10—C11—C12—C13	−179.6 (7)
O3—Cu1—N4—O2	87.2 (5)	O2—N4—C13—C12	−178.6 (5)
C5—N1—C1—C2	−0.1 (11)	Cu1—N4—C13—C12	−7.5 (8)
Cu1—N1—C1—C2	−179.9 (6)	O2—N4—C13—C14	3.6 (10)
N1—C1—C2—C3	−0.4 (13)	Cu1—N4—C13—C14	174.7 (6)
C1—C2—C3—C4	1.1 (12)	N3—C12—C13—N4	4.1 (9)
C2—C3—C4—C5	−1.4 (10)	C11—C12—C13—N4	−177.4 (6)
C3—C4—C5—N1	1.0 (8)	N3—C12—C13—C14	−178.3 (7)
C3—C4—C5—C6	−179.7 (6)	C11—C12—C13—C14	0.3 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.63	2.421 (7)	163
O3—H3C···O2ⁱ	0.85	1.92	2.757 (6)	170
O3—H3D···O8ⁱ	0.85	1.82	2.658 (8)	170
O8—H8C···O6ⁱⁱ	0.85	1.86	2.660 (7)	157
O8—H8D···O4ⁱⁱⁱ	0.85	2.11	2.862 (7)	148

Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x−1, y, z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₇N₂O)(C₇H₈N₂O)(H₂O)]ClO₄·H₂O
M_r	470.32
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	6.3526 (7), 15.7199 (14), 9.8235 (9)
β (°)	101.235 (1)
V (Å³)	962.20 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.45 × 0.40 × 0.39

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.587, 0.626
No. of measured, independent and observed [I > 2σ(I)] reflections	4732, 2284, 2062
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.00
No. of reflections	2284
No. of parameters	292
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36
Absolute structure	Flack (1983)
Absolute structure parameter	0.00 (2)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.63	2.421 (7)	162.8
O3—H3C···O2ⁱ	0.85	1.92	2.757 (6)	170.3
O3—H3D···O8ⁱ	0.85	1.82	2.658 (8)	169.5
O8—H8C···O6ⁱⁱ	0.85	1.86	2.660 (7)	157.3
O8—H8D···O4ⁱⁱⁱ	0.85	2.11	2.862 (7)	148.2

Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x−1, y, z+1.

References

Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143–190. Web of Science CrossRef CAS Google Scholar
Clerac, R., Miyasaka, H., Yamashita, M. & Coulon, C. (2002). J Am Chem Soc. 124, 12837–12844. Web of Science PubMed CAS Google Scholar
Davidson, M. G., Johnson, A. L., Jones, M. D., Lunn, M. D. & Mahon, M. F. (2007). Polyhedron. 26, 975–980. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pavlishchuk, V. V., Kolotilov, S. V., Addison, A. W., Prushan, M. J., Schollmeyer, D., Thompson, L. K., Weyhermuller, T. & Goreshnik, E. A. (2003). Dalton Trans. pp. 1587–1595. Web of Science CSD CrossRef Google Scholar
Qiu, X., Li, L. & Li, D. (2011). Acta Cryst. E67, m1810–m1811. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Google Scholar
Wu, G. & Wu, D. (2008). Acta Cryst. E64, m828. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zuo, J., Dou, J., Li, D., Wang, D. & Sun, Y. (2007). Acta Cryst. E63, m3183–m3184. Web of Science CSD CrossRef IUCr Journals Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Aqua[1-(pyridin-2-yl)ethanone oximato][1-(2-pyridin-2-yl)ethanone oxime]­copper(II) perchlorate mono­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Aqua[1-(pyridin-2-yl)ethanone oximato][1-(2-pyridin-2-yl)ethanone oxime]copper(II) perchlorate monohydrate