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

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)ethan-one oxime ligands and by the water O atom in a distorted square-pyramidal geometry. The two organic ligands are linked by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules and ions are linked by O-H⋯O hydrogen-bonding inter-actions, 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 = 470.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.00

2284 reflections

292 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 0.00 (2)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023872/aa2060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023872/aa2060Isup2.hkl

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

[Cu(C7H7N2O)(C7H8N2O)(H2O)]ClO4·H2O	F(000) = 482
Mr = 470.32	Dx = 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

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

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(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2284 reflections	Δρmax = 0.31 e Å−3
292 parameters	Δρmin = −0.36 e Å−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (2)

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .