Chlorido{μ-2,6-bis­[(2-amino­eth­yl)imino­meth­yl]-4-chloro­phenolato}-μ-oxido-dicopper(II) trihydrate

Zhou, J.-J.; Xiao, W.; Mao, J.-W.; Zhou, H.

doi:10.1107/S160053681202301X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m794-m795

doi:10.1107/S160053681202301X

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Chlorido{μ-2,6-bis[(2-aminoethyl)iminomethyl]-4-chlorophenolato}-μ-oxido-dicopper(II) trihydrate

Jing-Jing Zhou,^a Wei Xiao,^b Jia-Wei Mao ^c and Hong Zhou ^a ^*

^aKey Laboratory for Green Chemical Processes of the Ministry of Education, Wuhan Institute of Technology, 430073 Wuhan, People's Republic of China, ^bInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, People's Republic of China, and ^cCollege of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, People's Republic of China
^*Correspondence e-mail: hzhouh@126.com

(Received 28 April 2012; accepted 20 May 2012; online 26 May 2012)

In the title dinuclear complex, [Cu₂(C₁₄H₂₀ClN₄O)ClO]·3H₂O, one Cu^II cation assumes a distorted square-planar coordination geometry and the other a distorted square-pyramidal coordination geometry. Both Cu^II cations are N,N′,O-chelated by one arm of the 2,6-bis[(2-aminoethyl)iminomethyl]-4-chlorophenolate anion, and one oxide anion bridges the two Cu^II cations, forming a dinuclear complex. One of the Cu^II cations is further coordinated by an Cl⁻ anion in the apical direction. In the crystal, lattice water molecules are linked with the complex molecule via O—H⋯Cl hydrogen bonds while O—H⋯O hydrogen bonding occurs between lattice water molecules , forming three-dimensional network structure.

Related literature

For the synthesis, see: Gagne et al. (1981 ). For a related oxygen anion-bridging complex, see: Olmstead et al. (2011 ). For the biological activity of Schiff bases, see: Raman et al. (2007 ); Hao et al. (2006 ). For the biological properties of binuclear complexes, see: Tian et al. (2007 ); Anbu et al. (2009 ). Several proteins in vivo contain transition metal atoms, especially, Cu^II, see: Dede et al. (2009 ); Veysel et al. (2003 ); Asokan et al. (1995 ).

Experimental

Crystal data

[Cu₂(C₁₄H₂₀ClN₄O)ClO]·3H₂O
M_r = 528.37
Monoclinic, P 2₁ /c
a = 11.201 (5) Å
b = 12.387 (7) Å
c = 16.718 (7) Å
β = 93.18 (4)°
V = 2316.0 (19) Å³
Z = 4
Mo Kα radiation
μ = 2.10 mm⁻¹
T = 291 K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.572, T_max = 0.633
12029 measured reflections
4087 independent reflections
3286 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.175
S = 1.02
4087 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WD⋯Cl1	0.85	1.90	2.583 (12)	136
O2W—H2WB⋯O3W	0.85	2.57	3.114 (13)	123
O3W—H3WD⋯Cl2	0.85	2.70	3.478 (10)	152

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681202301X/xu5529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202301X/xu5529Isup2.hkl

checkCIF report

Comment top

Schiff bases have received special attention of biochemists because of their biological activities (Raman et al., 2007; Hao et al., 2006). Researches show that binuclear complexes have good biological properties (Tian et al., 2007; Anbu et al., 2009). Several proteins in vivo contain transition metal centers, especially, the Cu(II) centers (Dede et al., 2009; Veysel et al., 2003). Thus, in this paper, we report on the synthesis and the crystal structure of a new binuclear copper complex. Although a similar complex has been reported in the literature (Asokan et al., 1995), however, the title complex has different substituent in the phenoxid group and counter anion with the reported complex. The crystal structure of the title complex is shown in Fig.1. The molecular unit contains a chloride anion and two copper ions. The coordination environment of the two copper ions are different. Cu2 has four coordinated atoms with quadrilateral configuration, all the atoms locate in an approximately plane with a mean plane derivation of 0.072 Å. While Cu1 has five coordinated atoms with a square pyramid configuration and the chloride anion occupies the apical position with Cu1-Cl2 distance of 2.484 Å. The basal plane is composed of two imino nitrogen atoms, one phenoxide atom and one oxygen anion derived from the solvent of H2O with a mean plane derivation of 0.016 Å. This oxygen anion bridged structure is also found in a dinuclear complex which was obtained by a similar experimental condition (Olmstead et al., 2011).

Related literature top

For the synthesis, see: Gagne et al. (1981). For a related oxygen anion-bridging complex, see: Olmstead et al. (2011). For the biological activity of Schiff bases, see: Raman et al. (2007); Hao et al. (2006). For the biological properties of binuclear complexes, see: Tian et al. (2007); Anbu et al. (2009). Several proteins in vivo contain transition metal atoms, especially, Cu^II, see: Dede et al. (2009); Veysel et al. (2003); Asokan et al. (1995).

Experimental top

2,6-Diformyl-4-chlorophenol was prepared according to the literature methods (Gagne et al., 1981). 2,6-Diformyl-4-chlorophenol (0.25 mmol, 0.046 g) in absolute methanol (10 ml) was added to a methanol solution (10 ml) containing 1,3-propanediamine (0.5 mmol, 0.037 g). The solution was stirred vigorously for 2 h at room temperature. Afterwards, a methanol solution (10 ml) of CuCl₂.2H₂O (0.5 mmol, 0.085 g) was added dropwise, the mixture was stirred for a further 6 h at ambient temperature. The dark-green block-shaped crystals suitable for X-ray structure analysis were obtained by evaporating the methanol solution of the complex over a period of one month.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I), showing the labeling of the non-H atoms and 30% probability ellipsoids. H atoms have been omitted for clarity.

Chlorido{µ-2,6-bis[(2-aminoethyl)iminomethyl]-4-chlorophenolato}-µ-oxido- dicopper(II) trihydrate top

Crystal data top

[Cu₂(C₁₄H₂₀ClN₄O)ClO]·3H₂O	F(000) = 1080
M_r = 528.37	D_x = 1.515 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4001 reflections
a = 11.201 (5) Å	θ = 2.4–26.6°
b = 12.387 (7) Å	µ = 2.10 mm⁻¹
c = 16.718 (7) Å	T = 291 K
β = 93.18 (4)°	Block, green
V = 2316.0 (19) Å³	0.30 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4087 independent reflections
Radiation source: sealed tube	3286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
T_min = 0.572, T_max = 0.633	k = −14→11
12029 measured reflections	l = −19→19

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.080P)² + 12.660P] where P = (F_o² + 2F_c²)/3
4087 reflections	(Δ/σ)_max = 0.076
244 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

[Cu₂(C₁₄H₂₀ClN₄O)ClO]·3H₂O	V = 2316.0 (19) Å³
M_r = 528.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.201 (5) Å	µ = 2.10 mm⁻¹
b = 12.387 (7) Å	T = 291 K
c = 16.718 (7) Å	0.30 × 0.26 × 0.24 mm
β = 93.18 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	4087 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3286 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.633	R_int = 0.024
12029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.080P)² + 12.660P] where P = (F_o² + 2F_c²)/3
4087 reflections	Δρ_max = 0.65 e Å⁻³
244 parameters	Δρ_min = −0.94 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.29197 (15)	0.09726 (13)	0.30847 (10)	0.0409 (4)
Cl2	0.31005 (15)	0.62287 (14)	0.44102 (10)	0.0435 (4)
Cu1	0.43928 (7)	0.66390 (6)	0.32886 (5)	0.0360 (2)
Cu2	0.22384 (7)	0.67193 (6)	0.21370 (5)	0.0360 (2)
C1	0.6375 (6)	0.7673 (6)	0.4411 (4)	0.0388 (15)
H1A	0.6233	0.8117	0.4874	0.047*
H1B	0.7089	0.7953	0.4180	0.047*
C2	0.6665 (7)	0.6538 (6)	0.4715 (4)	0.0451 (17)
H2A	0.6055	0.6302	0.5066	0.054*
H2B	0.7427	0.6541	0.5020	0.054*
C3	0.6721 (6)	0.5750 (5)	0.4003 (4)	0.0376 (15)
H3A	0.7219	0.6064	0.3607	0.045*
H3B	0.7101	0.5086	0.4191	0.045*
C4	0.5264 (6)	0.4435 (6)	0.3522 (4)	0.0395 (15)
H4	0.5824	0.3950	0.3744	0.047*
C5	0.3361 (6)	0.4596 (5)	0.2694 (4)	0.0360 (15)
C6	0.4249 (6)	0.3996 (6)	0.3141 (4)	0.0412 (16)
C7	0.4106 (6)	0.2905 (6)	0.3267 (4)	0.0358 (14)
H7	0.4677	0.2524	0.3577	0.043*
C8	0.3091 (7)	0.2369 (6)	0.2923 (4)	0.0460 (17)
C9	0.2214 (6)	0.2954 (5)	0.2455 (4)	0.0369 (14)
H9	0.1554	0.2602	0.2215	0.044*
C10	0.2354 (6)	0.4051 (5)	0.2363 (4)	0.0396 (15)
C11	0.1424 (6)	0.4496 (5)	0.1867 (4)	0.0409 (16)
H11	0.0913	0.3989	0.1621	0.049*
C12	0.0115 (6)	0.5819 (6)	0.1123 (5)	0.0472 (18)
H12A	−0.0533	0.6059	0.1440	0.057*
H12B	−0.0157	0.5176	0.0837	0.057*
C13	0.0339 (7)	0.6702 (6)	0.0498 (4)	0.0428 (16)
H13A	−0.0303	0.6710	0.0084	0.051*
H13B	0.1087	0.6570	0.0249	0.051*
C14	0.0392 (6)	0.7802 (5)	0.0960 (4)	0.0376 (15)
H14A	0.0569	0.8361	0.0578	0.045*
H14B	−0.0403	0.7947	0.1136	0.045*
N1	0.5352 (5)	0.7852 (5)	0.3811 (3)	0.0398 (13)
H1C	0.5640	0.8243	0.3411	0.048*
H1D	0.4827	0.8279	0.4050	0.048*
N2	0.5521 (5)	0.5481 (5)	0.3605 (3)	0.0417 (13)
N3	0.1152 (5)	0.5507 (5)	0.1690 (3)	0.0405 (13)
N4	0.1253 (5)	0.7929 (5)	0.1670 (3)	0.0437 (14)
H4A	0.0830	0.8191	0.2069	0.052*
H4B	0.1768	0.8452	0.1545	0.052*
O1	0.3458 (4)	0.5674 (4)	0.2586 (2)	0.0373 (10)
O2	0.3320 (4)	0.7525 (3)	0.2702 (3)	0.0360 (10)
O1W	0.2820 (9)	−0.0067 (9)	0.4419 (7)	0.144 (4)
H1WD	0.2653	0.0494	0.4142	0.173*
H1WC	0.2692	0.0055	0.4907	0.216*
O2W	0.1297 (9)	0.4729 (8)	0.3981 (7)	0.150 (4)
H2WD	0.1802	0.4946	0.3656	0.180*
H2WB	0.1094	0.5253	0.4272	0.224*
O3W	0.0267 (9)	0.7040 (8)	0.3693 (5)	0.120 (3)
H3WD	0.0988	0.6829	0.3681	0.144*
H3WA	−0.0136	0.6575	0.3937	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0444 (9)	0.0364 (9)	0.0429 (9)	−0.0072 (7)	0.0111 (7)	0.0118 (7)
Cl2	0.0412 (9)	0.0478 (10)	0.0426 (9)	−0.0115 (7)	0.0131 (7)	0.0021 (7)
Cu1	0.0350 (4)	0.0388 (5)	0.0352 (4)	−0.0085 (3)	0.0097 (3)	0.0019 (3)
Cu2	0.0359 (4)	0.0376 (5)	0.0352 (4)	0.0013 (3)	0.0082 (3)	0.0003 (3)
C1	0.038 (3)	0.045 (4)	0.034 (3)	0.009 (3)	0.007 (3)	0.010 (3)
C2	0.047 (4)	0.039 (4)	0.050 (4)	−0.003 (3)	0.014 (3)	0.014 (3)
C3	0.046 (4)	0.036 (3)	0.033 (3)	−0.005 (3)	0.015 (3)	0.016 (3)
C4	0.034 (3)	0.040 (4)	0.044 (4)	0.003 (3)	0.003 (3)	0.005 (3)
C5	0.040 (3)	0.039 (4)	0.030 (3)	0.017 (3)	0.009 (3)	−0.010 (3)
C6	0.038 (4)	0.042 (4)	0.044 (4)	0.012 (3)	0.012 (3)	−0.006 (3)
C7	0.038 (3)	0.043 (4)	0.026 (3)	0.002 (3)	0.006 (3)	0.003 (3)
C8	0.054 (4)	0.032 (4)	0.051 (4)	0.007 (3)	0.000 (3)	−0.008 (3)
C9	0.039 (4)	0.038 (3)	0.035 (3)	−0.007 (3)	0.006 (3)	−0.001 (3)
C10	0.047 (4)	0.028 (3)	0.044 (4)	0.016 (3)	0.000 (3)	0.007 (3)
C11	0.047 (4)	0.035 (4)	0.041 (4)	0.011 (3)	−0.002 (3)	−0.016 (3)
C12	0.038 (4)	0.031 (4)	0.073 (5)	0.002 (3)	−0.003 (3)	−0.008 (3)
C13	0.043 (4)	0.047 (4)	0.038 (4)	0.005 (3)	0.001 (3)	−0.005 (3)
C14	0.038 (3)	0.032 (3)	0.040 (4)	−0.011 (3)	−0.020 (3)	0.017 (3)
N1	0.036 (3)	0.040 (3)	0.044 (3)	0.009 (2)	0.008 (2)	−0.015 (3)
N2	0.047 (3)	0.042 (3)	0.037 (3)	0.007 (3)	0.016 (3)	−0.002 (2)
N3	0.046 (3)	0.039 (3)	0.038 (3)	0.002 (3)	0.014 (2)	−0.007 (2)
N4	0.044 (3)	0.045 (3)	0.040 (3)	−0.020 (3)	−0.014 (3)	0.010 (3)
O1	0.036 (2)	0.043 (3)	0.034 (2)	0.001 (2)	0.0127 (19)	−0.0118 (19)
O2	0.036 (2)	0.032 (2)	0.041 (2)	−0.0120 (19)	0.0114 (19)	0.0163 (19)
O1W	0.139 (9)	0.154 (9)	0.141 (9)	−0.022 (7)	0.014 (7)	−0.009 (7)
O2W	0.133 (8)	0.115 (8)	0.208 (12)	0.016 (6)	0.076 (8)	0.047 (8)
O3W	0.123 (7)	0.119 (7)	0.118 (7)	−0.016 (6)	0.000 (6)	0.015 (6)

Geometric parameters (Å, º) top

Cl1—C8	1.763 (7)	C7—C8	1.411 (10)
Cl2—Cu1	2.484 (2)	C7—H7	0.9300
Cu1—O2	1.865 (4)	C8—C9	1.420 (10)
Cu1—O1	1.941 (4)	C9—C10	1.377 (9)
Cu1—N2	1.965 (6)	C9—H9	0.9300
Cu1—N1	2.017 (6)	C10—C11	1.408 (9)
Cu1—Cu2	3.0040 (18)	C11—N3	1.319 (9)
Cu2—O2	1.797 (4)	C11—H11	0.9300
Cu2—N4	1.994 (6)	C12—N3	1.508 (9)
Cu2—O1	1.997 (5)	C12—C13	1.542 (10)
Cu2—N3	2.048 (6)	C12—H12A	0.9700
C1—N1	1.498 (8)	C12—H12B	0.9700
C1—C2	1.524 (9)	C13—C14	1.565 (9)
C1—H1A	0.9700	C13—H13A	0.9700
C1—H1B	0.9700	C13—H13B	0.9700
C2—C3	1.543 (10)	C14—N4	1.496 (7)
C2—H2A	0.9700	C14—H14A	0.9700
C2—H2B	0.9700	C14—H14B	0.9700
C3—N2	1.503 (9)	N1—H1C	0.9000
C3—H3A	0.9700	N1—H1D	0.9000
C3—H3B	0.9700	N4—H4A	0.9000
C4—N2	1.333 (9)	N4—H4B	0.9000
C4—C6	1.384 (10)	O1W—H1WD	0.8501
C4—H4	0.9300	O1W—H1WC	0.8499
C5—O1	1.353 (8)	O2W—H2WD	0.8496
C5—C10	1.401 (10)	O2W—H2WB	0.8500
C5—C6	1.420 (9)	O3W—H3WD	0.8500
C6—C7	1.378 (10)	O3W—H3WA	0.8501

O2—Cu1—O1	74.6 (2)	C7—C8—C9	120.1 (6)
O2—Cu1—N2	163.2 (2)	C7—C8—Cl1	119.4 (5)
O1—Cu1—N2	91.8 (2)	C9—C8—Cl1	120.5 (5)
O2—Cu1—N1	95.8 (2)	C10—C9—C8	119.0 (6)
O1—Cu1—N1	167.6 (2)	C10—C9—H9	120.5
N2—Cu1—N1	96.2 (2)	C8—C9—H9	120.5
O2—Cu1—Cl2	97.57 (13)	C9—C10—C5	121.7 (6)
O1—Cu1—Cl2	90.79 (13)	C9—C10—C11	111.5 (6)
N2—Cu1—Cl2	92.30 (16)	C5—C10—C11	126.7 (6)
N1—Cu1—Cl2	98.30 (17)	N3—C11—C10	131.2 (7)
O2—Cu1—Cu2	34.16 (13)	N3—C11—H11	114.4
O1—Cu1—Cu2	41.00 (14)	C10—C11—H11	114.4
N2—Cu1—Cu2	132.74 (18)	N3—C12—C13	117.3 (6)
N1—Cu1—Cu2	129.95 (17)	N3—C12—H12A	108.0
Cl2—Cu1—Cu2	90.55 (6)	C13—C12—H12A	108.0
O2—Cu2—N4	97.5 (2)	N3—C12—H12B	108.0
O2—Cu2—O1	74.66 (19)	C13—C12—H12B	108.0
N4—Cu2—O1	170.4 (2)	H12A—C12—H12B	107.2
O2—Cu2—N3	165.6 (2)	C12—C13—C14	106.7 (5)
N4—Cu2—N3	95.9 (2)	C12—C13—H13A	110.4
O1—Cu2—N3	92.4 (2)	C14—C13—H13A	110.4
O2—Cu2—Cu1	35.64 (14)	C12—C13—H13B	110.4
N4—Cu2—Cu1	133.09 (16)	C14—C13—H13B	110.4
O1—Cu2—Cu1	39.61 (13)	H13A—C13—H13B	108.6
N3—Cu2—Cu1	130.51 (17)	N4—C14—C13	119.2 (5)
N1—C1—C2	120.0 (6)	N4—C14—H14A	107.5
N1—C1—H1A	107.3	C13—C14—H14A	107.5
C2—C1—H1A	107.3	N4—C14—H14B	107.5
N1—C1—H1B	107.3	C13—C14—H14B	107.5
C2—C1—H1B	107.3	H14A—C14—H14B	107.0
H1A—C1—H1B	106.9	C1—N1—Cu1	123.3 (4)
C1—C2—C3	110.1 (6)	C1—N1—H1C	106.5
C1—C2—H2A	109.6	Cu1—N1—H1C	106.5
C3—C2—H2A	109.6	C1—N1—H1D	106.5
C1—C2—H2B	109.6	Cu1—N1—H1D	106.5
C3—C2—H2B	109.6	H1C—N1—H1D	106.5
H2A—C2—H2B	108.2	C4—N2—C3	116.4 (6)
N2—C3—C2	114.1 (5)	C4—N2—Cu1	123.3 (5)
N2—C3—H3A	108.7	C3—N2—Cu1	120.2 (4)
C2—C3—H3A	108.7	C11—N3—C12	123.0 (6)
N2—C3—H3B	108.7	C11—N3—Cu2	119.3 (5)
C2—C3—H3B	108.7	C12—N3—Cu2	117.5 (4)
H3A—C3—H3B	107.6	C14—N4—Cu2	123.4 (4)
N2—C4—C6	126.7 (6)	C14—N4—H4A	106.5
N2—C4—H4	116.7	Cu2—N4—H4A	106.5
C6—C4—H4	116.7	C14—N4—H4B	106.5
O1—C5—C10	119.5 (6)	Cu2—N4—H4B	106.5
O1—C5—C6	121.8 (6)	H4A—N4—H4B	106.5
C10—C5—C6	118.7 (6)	C5—O1—Cu1	124.8 (4)
C7—C6—C4	114.4 (6)	C5—O1—Cu2	129.2 (4)
C7—C6—C5	120.6 (7)	Cu1—O1—Cu2	99.4 (2)
C4—C6—C5	124.8 (7)	Cu2—O2—Cu1	110.2 (2)
C6—C7—C8	119.8 (6)	H1WD—O1W—H1WC	109.5
C6—C7—H7	120.1	H2WD—O2W—H2WB	109.5
C8—C7—H7	120.1	H3WD—O3W—H3WA	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WD···Cl1	0.85	1.90	2.583 (12)	136
O2W—H2WB···O3W	0.85	2.57	3.114 (13)	123
O3W—H3WD···Cl2	0.85	2.70	3.478 (10)	152

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₄H₂₀ClN₄O)ClO]·3H₂O
M_r	528.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	11.201 (5), 12.387 (7), 16.718 (7)
β (°)	93.18 (4)
V (Å³)	2316.0 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.10
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.572, 0.633
No. of measured, independent and observed [I > 2σ(I)] reflections	12029, 4087, 3286
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.175, 1.02
No. of reflections	4087
No. of parameters	244
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.080P)² + 12.660P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.94

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WD···Cl1	0.85	1.90	2.583 (12)	135.9
O2W—H2WB···O3W	0.85	2.57	3.114 (13)	123.0
O3W—H3WD···Cl2	0.85	2.70	3.478 (10)	151.9

Acknowledgements

The authors would like to thank the National Science Foundation of China (Nos. 21171135 and 20971102).

References

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Volume 68| Part 6| June 2012| Pages m794-m795

doi:10.1107/S160053681202301X

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

Chlorido{μ-2,6-bis­­[(2-amino­eth­yl)imino­meth­yl]-4-chloro­phenolato}-μ-oxido-dicopper(II) trihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Chlorido{μ-2,6-bis[(2-aminoethyl)iminomethyl]-4-chlorophenolato}-μ-oxido-dicopper(II) trihydrate