Chlorido[2,2′-(oxydimethyl­ene)­dipyridine]copper(II) perchlorate–aqua­chlorido[2,2′-(oxydimethyl­ene)­dipyridine]copper(II) perchlorate (1/1)

Li, H.; Xie, L.M.; Zhang, S.G.

doi:10.1107/S1600536809027123

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m933

doi:10.1107/S1600536809027123

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Chlorido[2,2′-(oxydimethylene)dipyridine]copper(II) perchlorate–aquachlorido[2,2′-(oxydimethylene)dipyridine]copper(II) perchlorate (1/1)

Hong Li,^a ^* Long Miao Xie ^b and Shi Guo Zhang ^a

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: honglizhang1968@yahoo.cn

(Received 5 July 2009; accepted 10 July 2009; online 18 July 2009)

The asymmetric unit of the title compound, [CuCl(C₁₂H₁₂N₂O)][CuCl(C₁₂H₁₂N₂O)(H₂O)](ClO₄)₂, contains two different discrete cations. In one cation, the Cu^II ion is coordinated in a slightly distorted square-planar geometry, while in the other the Cu^II ion is in a slightly distorted square-pyramidal environment. In the crystal structure, there are O—H⋯O hydrogen bonds between coordinated water molecules and perchlorate anions. Both types of cations are linked into one-dimensional chains along the b axis by weak electrostatic Cu⋯Cl interactions, with Cu⋯Cl distances of 2.8088 (16) and 3.2074 (17) Å.

Related literature

For related structures, see: Li (2007 , 2008a ,b ).

Experimental

Crystal data

[CuCl(C₁₂H₁₂N₂O)][CuCl(C₁₂H₁₂N₂O)(H₂O)](ClO₄)₂
M_r = 815.37
Triclinic, $[P \overline 1]$
a = 10.997 (2) Å
b = 12.882 (3) Å
c = 12.913 (3) Å
α = 97.174 (3)°
β = 112.031 (3)°
γ = 106.851 (3)°
V = 1565.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.76 mm⁻¹
T = 298 K
0.42 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.525, T_max = 0.709
8530 measured reflections
6009 independent reflections
4063 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.185
S = 1.05
6009 reflections
411 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cl3—Cu2	2.2511 (15)
Cl4—Cu1	2.2067 (14)
Cu1—N3	1.968 (4)
Cu1—O1	1.970 (3)
Cu1—N4	1.973 (4)
Cu2—N2	1.970 (4)
Cu2—N1	1.972 (4)
Cu2—O2	2.005 (4)
Cu2—O11	2.298 (4)

N3—Cu1—O1	80.97 (17)
N3—Cu1—N4	161.79 (19)
O1—Cu1—N4	81.04 (17)
N3—Cu1—Cl4	98.72 (13)
O1—Cu1—Cl4	173.09 (12)
N4—Cu1—Cl4	98.80 (14)
N2—Cu2—N1	159.85 (19)
N2—Cu2—O2	80.78 (17)
N1—Cu2—O2	80.45 (16)
N2—Cu2—Cl3	98.32 (14)
N1—Cu2—Cl3	98.09 (13)
O2—Cu2—Cl3	165.86 (13)
N2—Cu2—O11	93.89 (17)
N1—Cu2—O11	92.93 (17)
O2—Cu2—O11	88.68 (16)
Cl3—Cu2—O11	105.46 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11A⋯O5ⁱ	0.90	2.05	2.725 (8)	131
O11—H11B⋯O9ⁱⁱ	0.90	1.92	2.787 (10)	163
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027123/lh2860sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027123/lh2860Isup2.hkl

checkCIF report

Comment top

Derivatives of pyridine play an important role in modern coordination chemistry and some complexes using 2,2'-(oxydimethylene)dipyridine as a ligand have already been reported (Li, 2007, 2008a,b). Herein we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. Atom Cu1 is in a slightly distorted square-planar coordination environment and atom Cu2 is coordinated in a slightly distorted square-pyramidal environment with the O atom of the coordinated H₂O ligand in the apical site. 2,2'-(oxydimethylene)dipyridine acts as a tridentate ligand as in the related Cu^II, Zn^II and Cd^II complexes (Li, 2007, 2008a,b). In the crystal structure, there are O—H···O hydrogen bonds between coordinated water molecule and perchlorate ions and both types of cation are linked into one-dimensional chains along the b axis by weak electrostatic Cu···Cl interactions with Cu···Cl distances of 2.8088 (16) and 3.2074 (17) Å (see Fig. 2).

Related literature top

For related structures, see: Li (2007, 2008a,b).

Experimental top

An 8ml methanol solution of 2,2'-(oxydimetheylene)dipyridine (0.0386 g, 0.193 mmol) was added to an 8 ml H₂O solution containing Cu(ClO₄)₂.6H₂O (0.0730 g, 0.197 mmol), and the mixture was stirred for a few minutes. Then, diluted HCl solution was added into the mixed solution in drops until the pH = 4.0. Blue single crystals were obtained after the solution had been allowed to stand at room temperature for three weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Chlorido[2,2'-(oxydimethylene)dipyridine]copper(II) perchlorate– aquachlorido[2,2'-(oxydimethylene)dipyridine]copper(II) perchlorate (1/1) top

Crystal data top

[CuCl(C₁₂H₁₂N₂O)][CuCl(C₁₂H₁₂N₂O)(H₂O)](ClO₄)₂	Z = 2
M_r = 815.37	F(000) = 824
Triclinic, P1	D_x = 1.730 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.997 (2) Å	Cell parameters from 2082 reflections
b = 12.882 (3) Å	θ = 2.2–23.8°
c = 12.913 (3) Å	µ = 1.76 mm⁻¹
α = 97.174 (3)°	T = 298 K
β = 112.031 (3)°	Block, blue
γ = 106.851 (3)°	0.42 × 0.23 × 0.21 mm
V = 1565.7 (5) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	6009 independent reflections
Radiation source: fine-focus sealed tube	4063 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.525, T_max = 0.709	k = −15→15
8530 measured reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1088P)²] where P = (F_o² + 2F_c²)/3
6009 reflections	(Δ/σ)_max < 0.001
411 parameters	Δρ_max = 1.01 e Å⁻³
3 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[CuCl(C₁₂H₁₂N₂O)][CuCl(C₁₂H₁₂N₂O)(H₂O)](ClO₄)₂	γ = 106.851 (3)°
M_r = 815.37	V = 1565.7 (5) Å³
Triclinic, P1	Z = 2
a = 10.997 (2) Å	Mo Kα radiation
b = 12.882 (3) Å	µ = 1.76 mm⁻¹
c = 12.913 (3) Å	T = 298 K
α = 97.174 (3)°	0.42 × 0.23 × 0.21 mm
β = 112.031 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	6009 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4063 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.709	R_int = 0.024
8530 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	3 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.05	Δρ_max = 1.01 e Å⁻³
6009 reflections	Δρ_min = −0.60 e Å⁻³
411 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.6320 (7)	0.2031 (5)	1.2505 (5)	0.0595 (16)
H1	0.7080	0.2218	1.2317	0.071*
C2	0.6551 (8)	0.2240 (6)	1.3637 (6)	0.078 (2)
H2	0.7464	0.2573	1.4224	0.093*
C3	0.5399 (10)	0.1947 (7)	1.3902 (6)	0.085 (2)
H3	0.5543	0.2069	1.4671	0.102*
C4	0.4070 (9)	0.1483 (6)	1.3042 (6)	0.073 (2)
H4	0.3296	0.1303	1.3211	0.088*
C5	0.3891 (7)	0.1283 (5)	1.1908 (5)	0.0507 (14)
C6	0.2451 (6)	0.0723 (5)	1.0915 (5)	0.0567 (15)
H6A	0.2091	−0.0075	1.0855	0.068*
H6B	0.1803	0.1047	1.1031	0.068*
C7	0.1462 (6)	0.0206 (5)	0.8805 (5)	0.0583 (15)
H7A	0.0685	0.0471	0.8607	0.070*
H7B	0.1126	−0.0563	0.8852	0.070*
C8	0.2003 (6)	0.0257 (5)	0.7912 (5)	0.0499 (13)
C9	0.1103 (7)	−0.0147 (6)	0.6740 (6)	0.0661 (17)
H9	0.0131	−0.0438	0.6492	0.079*
C10	0.1668 (8)	−0.0112 (7)	0.5942 (6)	0.074 (2)
H10	0.1084	−0.0395	0.5153	0.089*
C11	0.3108 (8)	0.0351 (6)	0.6341 (5)	0.0664 (17)
H11	0.3509	0.0395	0.5821	0.080*
C12	0.3942 (6)	0.0742 (5)	0.7500 (5)	0.0514 (14)
H12	0.4914	0.1050	0.7763	0.062*
C13	0.1523 (7)	0.3151 (6)	0.6299 (5)	0.0659 (17)
H13	0.1544	0.2623	0.5751	0.079*
C14	0.2190 (6)	0.3236 (5)	0.7442 (5)	0.0572 (15)
H14	0.2672	0.2757	0.7668	0.069*
C15	0.0808 (7)	0.3866 (6)	0.5959 (5)	0.073 (2)
H15	0.0355	0.3836	0.5180	0.088*
C16	0.0780 (7)	0.4616 (6)	0.6790 (5)	0.0682 (18)
H16	0.0288	0.5091	0.6576	0.082*
C17	0.1485 (6)	0.4672 (5)	0.7953 (5)	0.0500 (13)
C18	0.1488 (7)	0.5490 (5)	0.8875 (5)	0.0558 (14)
H18A	0.2063	0.6247	0.8940	0.067*
H18B	0.0536	0.5460	0.8689	0.067*
C19	0.2582 (7)	0.6040 (5)	1.0978 (5)	0.0579 (15)
H19A	0.1815	0.6096	1.1152	0.069*
H19B	0.3072	0.6762	1.0898	0.069*
C20	0.3576 (6)	0.5727 (5)	1.1929 (5)	0.0489 (13)
C21	0.4126 (7)	0.6304 (6)	1.3080 (5)	0.0646 (17)
H21	0.3854	0.6890	1.3279	0.077*
C22	0.5060 (7)	0.6021 (6)	1.3923 (6)	0.0704 (18)
H22	0.5467	0.6431	1.4693	0.084*
C23	0.5389 (7)	0.5114 (6)	1.3611 (5)	0.0645 (17)
H23	0.5995	0.4882	1.4172	0.077*
C24	0.4815 (6)	0.4558 (5)	1.2464 (5)	0.0555 (15)
H24	0.5037	0.3944	1.2257	0.067*
Cl1	0.19499 (15)	0.84371 (14)	0.29265 (13)	0.0570 (4)
Cl2	0.89001 (17)	0.69411 (16)	0.70403 (14)	0.0648 (4)
Cl3	0.47655 (15)	0.34451 (11)	0.99732 (12)	0.0504 (4)
Cl4	0.65816 (14)	0.13410 (12)	1.00771 (12)	0.0496 (3)
Cu1	0.44927 (6)	0.12094 (6)	0.99775 (5)	0.0443 (2)
Cu2	0.31420 (7)	0.41888 (6)	0.99518 (5)	0.0482 (2)
N1	0.3943 (5)	0.4871 (4)	1.1630 (4)	0.0453 (10)
N2	0.2185 (5)	0.3987 (4)	0.8269 (4)	0.0483 (11)
N3	0.3399 (5)	0.0696 (4)	0.8284 (4)	0.0455 (10)
N4	0.4983 (5)	0.1550 (4)	1.1649 (4)	0.0492 (11)
O1	0.2589 (4)	0.0900 (3)	0.9887 (3)	0.0487 (9)
O2	0.2049 (4)	0.5195 (3)	0.9940 (3)	0.0533 (10)
O3	1.0211 (5)	0.7169 (5)	0.6997 (5)	0.0934 (16)
O4	0.8206 (10)	0.7530 (10)	0.6406 (10)	0.221 (5)
O5	0.9105 (10)	0.7257 (15)	0.8086 (7)	0.335 (10)
O6	0.8156 (9)	0.5888 (7)	0.6593 (12)	0.253 (7)
O7	0.1715 (12)	0.7738 (12)	0.3473 (14)	0.304 (9)
O8	0.3380 (7)	0.8819 (6)	0.3202 (8)	0.157 (3)
O9	0.1338 (12)	0.7967 (16)	0.1870 (8)	0.356 (12)
O10	0.1404 (10)	0.9200 (9)	0.3042 (11)	0.218 (5)
O11	0.1331 (5)	0.2760 (4)	0.9973 (4)	0.0675 (11)
H11A	0.1292	0.3169	1.0566	0.101*
H11B	0.0516	0.2676	0.9381	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.065 (4)	0.061 (4)	0.047 (3)	0.026 (3)	0.018 (3)	0.009 (3)
C2	0.082 (5)	0.078 (5)	0.053 (4)	0.030 (4)	0.012 (4)	0.004 (3)
C3	0.125 (7)	0.099 (6)	0.048 (4)	0.060 (6)	0.042 (5)	0.017 (4)
C4	0.102 (6)	0.080 (5)	0.072 (5)	0.050 (5)	0.057 (5)	0.031 (4)
C5	0.071 (4)	0.045 (3)	0.057 (3)	0.033 (3)	0.039 (3)	0.019 (3)
C6	0.065 (4)	0.056 (4)	0.072 (4)	0.030 (3)	0.046 (3)	0.023 (3)
C7	0.042 (3)	0.061 (4)	0.070 (4)	0.021 (3)	0.019 (3)	0.018 (3)
C8	0.047 (3)	0.048 (3)	0.056 (3)	0.024 (3)	0.018 (3)	0.018 (3)
C9	0.045 (3)	0.071 (4)	0.064 (4)	0.023 (3)	0.005 (3)	0.016 (3)
C10	0.077 (5)	0.088 (5)	0.049 (4)	0.039 (4)	0.012 (3)	0.017 (4)
C11	0.083 (5)	0.072 (5)	0.052 (4)	0.033 (4)	0.032 (3)	0.018 (3)
C12	0.054 (3)	0.060 (4)	0.046 (3)	0.024 (3)	0.024 (3)	0.020 (3)
C13	0.079 (5)	0.060 (4)	0.053 (4)	0.015 (4)	0.033 (3)	0.008 (3)
C14	0.066 (4)	0.052 (4)	0.047 (3)	0.016 (3)	0.024 (3)	0.008 (3)
C15	0.078 (5)	0.085 (5)	0.041 (4)	0.016 (4)	0.021 (3)	0.014 (3)
C16	0.073 (4)	0.078 (5)	0.048 (4)	0.030 (4)	0.017 (3)	0.025 (3)
C17	0.047 (3)	0.052 (4)	0.047 (3)	0.013 (3)	0.020 (3)	0.017 (3)
C18	0.061 (4)	0.054 (4)	0.054 (3)	0.027 (3)	0.022 (3)	0.018 (3)
C19	0.080 (4)	0.053 (4)	0.056 (4)	0.037 (3)	0.037 (3)	0.015 (3)
C20	0.055 (3)	0.046 (3)	0.050 (3)	0.017 (3)	0.029 (3)	0.009 (3)
C21	0.086 (5)	0.062 (4)	0.049 (4)	0.032 (4)	0.031 (3)	0.009 (3)
C22	0.081 (5)	0.076 (5)	0.049 (4)	0.022 (4)	0.032 (3)	0.002 (3)
C23	0.063 (4)	0.072 (5)	0.046 (3)	0.021 (3)	0.013 (3)	0.016 (3)
C24	0.070 (4)	0.048 (3)	0.051 (3)	0.023 (3)	0.027 (3)	0.016 (3)
Cl1	0.0530 (9)	0.0720 (11)	0.0519 (9)	0.0266 (8)	0.0252 (7)	0.0185 (8)
Cl2	0.0521 (9)	0.0780 (12)	0.0550 (9)	0.0191 (8)	0.0207 (7)	0.0063 (8)
Cl3	0.0574 (8)	0.0420 (8)	0.0598 (8)	0.0232 (6)	0.0293 (7)	0.0150 (6)
Cl4	0.0424 (7)	0.0506 (8)	0.0599 (8)	0.0209 (6)	0.0233 (6)	0.0149 (6)
Cu1	0.0410 (4)	0.0507 (4)	0.0428 (4)	0.0176 (3)	0.0196 (3)	0.0103 (3)
Cu2	0.0602 (5)	0.0470 (4)	0.0409 (4)	0.0263 (3)	0.0209 (3)	0.0102 (3)
N1	0.054 (3)	0.041 (3)	0.041 (2)	0.016 (2)	0.021 (2)	0.010 (2)
N2	0.057 (3)	0.041 (3)	0.043 (3)	0.014 (2)	0.021 (2)	0.010 (2)
N3	0.046 (3)	0.045 (3)	0.043 (3)	0.017 (2)	0.017 (2)	0.010 (2)
N4	0.063 (3)	0.048 (3)	0.047 (3)	0.027 (2)	0.030 (2)	0.016 (2)
O1	0.049 (2)	0.051 (2)	0.057 (2)	0.0208 (18)	0.0314 (19)	0.0182 (19)
O2	0.066 (3)	0.054 (2)	0.045 (2)	0.033 (2)	0.0210 (18)	0.0109 (18)
O3	0.061 (3)	0.107 (4)	0.113 (4)	0.026 (3)	0.042 (3)	0.029 (3)
O4	0.147 (8)	0.260 (12)	0.351 (15)	0.151 (9)	0.128 (9)	0.141 (11)
O5	0.136 (8)	0.70 (3)	0.089 (6)	0.059 (12)	0.076 (6)	−0.015 (10)
O6	0.111 (6)	0.093 (6)	0.52 (2)	−0.001 (5)	0.152 (10)	0.014 (9)
O7	0.200 (10)	0.398 (19)	0.52 (2)	0.167 (12)	0.248 (14)	0.384 (19)
O8	0.078 (4)	0.124 (6)	0.285 (10)	0.039 (4)	0.084 (5)	0.091 (6)
O9	0.201 (11)	0.66 (3)	0.104 (7)	0.225 (16)	−0.020 (7)	−0.122 (12)
O10	0.153 (7)	0.171 (9)	0.366 (14)	0.118 (7)	0.112 (8)	0.048 (9)
O11	0.071 (3)	0.066 (3)	0.066 (3)	0.019 (2)	0.035 (2)	0.019 (2)

Geometric parameters (Å, º) top

C1—N4	1.360 (7)	C17—C18	1.486 (8)
C1—C2	1.364 (8)	C18—O2	1.430 (6)
C1—H1	0.9300	C18—H18A	0.9700
C2—C3	1.394 (11)	C18—H18B	0.9700
C2—H2	0.9300	C19—O2	1.415 (6)
C3—C4	1.356 (10)	C19—C20	1.496 (8)
C3—H3	0.9300	C19—H19A	0.9700
C4—C5	1.381 (8)	C19—H19B	0.9700
C4—H4	0.9300	C20—N1	1.340 (7)
C5—N4	1.328 (7)	C20—C21	1.385 (8)
C5—C6	1.502 (9)	C21—C22	1.360 (9)
C6—O1	1.430 (6)	C21—H21	0.9300
C6—H6A	0.9700	C22—C23	1.377 (9)
C6—H6B	0.9700	C22—H22	0.9300
C7—O1	1.426 (7)	C23—C24	1.370 (8)
C7—C8	1.483 (8)	C23—H23	0.9300
C7—H7A	0.9700	C24—N1	1.342 (7)
C7—H7B	0.9700	C24—H24	0.9300
C8—N3	1.335 (7)	Cl1—O7	1.239 (8)
C8—C9	1.386 (8)	Cl1—O9	1.244 (8)
C9—C10	1.388 (10)	Cl1—O10	1.313 (7)
C9—H9	0.9300	Cl1—O8	1.389 (6)
C10—C11	1.376 (9)	Cl2—O5	1.273 (7)
C10—H10	0.9300	Cl2—O6	1.285 (8)
C11—C12	1.360 (8)	Cl2—O4	1.360 (8)
C11—H11	0.9300	Cl2—O3	1.409 (5)
C12—N3	1.353 (7)	Cl3—Cu2	2.2511 (15)
C12—H12	0.9300	Cl4—Cu1	2.2067 (14)
C13—C14	1.353 (8)	Cu1—N3	1.968 (4)
C13—C15	1.386 (9)	Cu1—O1	1.970 (3)
C13—H13	0.9300	Cu1—N4	1.973 (4)
C14—N2	1.352 (7)	Cu2—N2	1.970 (4)
C14—H14	0.9300	Cu2—N1	1.972 (4)
C15—C16	1.367 (9)	Cu2—O2	2.005 (4)
C15—H15	0.9300	Cu2—O11	2.298 (4)
C16—C17	1.389 (8)	O11—H11A	0.8969
C16—H16	0.9300	O11—H11B	0.8995
C17—N2	1.336 (7)

N4—C1—C2	120.2 (6)	C20—C19—H19B	110.1
N4—C1—H1	119.9	H19A—C19—H19B	108.4
C2—C1—H1	119.9	N1—C20—C21	120.4 (5)
C1—C2—C3	119.1 (7)	N1—C20—C19	117.7 (5)
C1—C2—H2	120.5	C21—C20—C19	121.9 (5)
C3—C2—H2	120.5	C22—C21—C20	120.6 (6)
C4—C3—C2	120.2 (6)	C22—C21—H21	119.7
C4—C3—H3	119.9	C20—C21—H21	119.7
C2—C3—H3	119.9	C21—C22—C23	118.5 (6)
C3—C4—C5	118.6 (7)	C21—C22—H22	120.8
C3—C4—H4	120.7	C23—C22—H22	120.8
C5—C4—H4	120.7	C24—C23—C22	119.2 (6)
N4—C5—C4	121.6 (6)	C24—C23—H23	120.4
N4—C5—C6	117.1 (5)	C22—C23—H23	120.4
C4—C5—C6	121.3 (6)	N1—C24—C23	122.1 (6)
O1—C6—C5	107.2 (5)	N1—C24—H24	119.0
O1—C6—H6A	110.3	C23—C24—H24	119.0
C5—C6—H6A	110.3	O7—Cl1—O9	109.6 (11)
O1—C6—H6B	110.3	O7—Cl1—O10	111.8 (7)
C5—C6—H6B	110.3	O9—Cl1—O10	104.2 (8)
H6A—C6—H6B	108.5	O7—Cl1—O8	108.2 (6)
O1—C7—C8	108.0 (5)	O9—Cl1—O8	105.6 (7)
O1—C7—H7A	110.1	O10—Cl1—O8	117.1 (6)
C8—C7—H7A	110.1	O5—Cl2—O6	111.9 (9)
O1—C7—H7B	110.1	O5—Cl2—O4	108.8 (9)
C8—C7—H7B	110.1	O6—Cl2—O4	108.4 (7)
H7A—C7—H7B	108.4	O5—Cl2—O3	109.3 (5)
N3—C8—C9	121.3 (5)	O6—Cl2—O3	109.4 (5)
N3—C8—C7	117.1 (5)	O4—Cl2—O3	108.9 (5)
C9—C8—C7	121.6 (6)	N3—Cu1—O1	80.97 (17)
C8—C9—C10	119.2 (6)	N3—Cu1—N4	161.79 (19)
C8—C9—H9	120.4	O1—Cu1—N4	81.04 (17)
C10—C9—H9	120.4	N3—Cu1—Cl4	98.72 (13)
C11—C10—C9	118.8 (6)	O1—Cu1—Cl4	173.09 (12)
C11—C10—H10	120.6	N4—Cu1—Cl4	98.80 (14)
C9—C10—H10	120.6	N2—Cu2—N1	159.85 (19)
C12—C11—C10	119.5 (6)	N2—Cu2—O2	80.78 (17)
C12—C11—H11	120.2	N1—Cu2—O2	80.45 (16)
C10—C11—H11	120.2	N2—Cu2—Cl3	98.32 (14)
N3—C12—C11	122.0 (6)	N1—Cu2—Cl3	98.09 (13)
N3—C12—H12	119.0	O2—Cu2—Cl3	165.86 (13)
C11—C12—H12	119.0	N2—Cu2—O11	93.89 (17)
C14—C13—C15	118.8 (6)	N1—Cu2—O11	92.93 (17)
C14—C13—H13	120.6	O2—Cu2—O11	88.68 (16)
C15—C13—H13	120.6	Cl3—Cu2—O11	105.46 (12)
N2—C14—C13	122.7 (6)	C20—N1—C24	119.1 (5)
N2—C14—H14	118.6	C20—N1—Cu2	115.3 (4)
C13—C14—H14	118.6	C24—N1—Cu2	125.5 (4)
C16—C15—C13	118.8 (6)	C17—N2—C14	119.1 (5)
C16—C15—H15	120.6	C17—N2—Cu2	115.1 (4)
C13—C15—H15	120.6	C14—N2—Cu2	125.8 (4)
C15—C16—C17	120.2 (6)	C8—N3—C12	119.2 (5)
C15—C16—H16	119.9	C8—N3—Cu1	115.0 (4)
C17—C16—H16	119.9	C12—N3—Cu1	125.8 (4)
N2—C17—C16	120.4 (6)	C5—N4—C1	120.3 (5)
N2—C17—C18	118.3 (5)	C5—N4—Cu1	115.0 (4)
C16—C17—C18	121.3 (6)	C1—N4—Cu1	124.6 (4)
O2—C18—C17	107.8 (5)	C7—O1—C6	117.4 (5)
O2—C18—H18A	110.2	C7—O1—Cu1	115.1 (3)
C17—C18—H18A	110.2	C6—O1—Cu1	115.1 (3)
O2—C18—H18B	110.2	C19—O2—C18	117.2 (4)
C17—C18—H18B	110.2	C19—O2—Cu2	115.9 (3)
H18A—C18—H18B	108.5	C18—O2—Cu2	115.2 (3)
O2—C19—C20	107.9 (4)	Cu2—O11—H11A	94.6
O2—C19—H19A	110.1	Cu2—O11—H11B	109.4
C20—C19—H19A	110.1	H11A—O11—H11B	101.6
O2—C19—H19B	110.1

N4—C1—C2—C3	0.5 (10)	O11—Cu2—N2—C17	96.4 (4)
C1—C2—C3—C4	−1.4 (11)	N1—Cu2—N2—C14	166.6 (5)
C2—C3—C4—C5	1.7 (11)	O2—Cu2—N2—C14	−171.9 (5)
C3—C4—C5—N4	−1.1 (10)	Cl3—Cu2—N2—C14	22.4 (5)
C3—C4—C5—C6	177.2 (6)	O11—Cu2—N2—C14	−83.8 (5)
N4—C5—C6—O1	−16.3 (7)	C9—C8—N3—C12	−0.3 (8)
C4—C5—C6—O1	165.4 (5)	C7—C8—N3—C12	178.8 (5)
O1—C7—C8—N3	13.7 (7)	C9—C8—N3—Cu1	−179.5 (4)
O1—C7—C8—C9	−167.1 (5)	C7—C8—N3—Cu1	−0.3 (6)
N3—C8—C9—C10	1.2 (9)	C11—C12—N3—C8	−0.2 (8)
C7—C8—C9—C10	−177.9 (6)	C11—C12—N3—Cu1	178.9 (4)
C8—C9—C10—C11	−1.6 (10)	O1—Cu1—N3—C8	−9.1 (4)
C9—C10—C11—C12	1.2 (10)	N4—Cu1—N3—C8	−0.1 (8)
C10—C11—C12—N3	−0.3 (10)	Cl4—Cu1—N3—C8	163.9 (4)
C15—C13—C14—N2	0.2 (10)	O1—Cu1—N3—C12	171.7 (5)
C14—C13—C15—C16	−1.2 (10)	N4—Cu1—N3—C12	−179.2 (5)
C13—C15—C16—C17	1.4 (10)	Cl4—Cu1—N3—C12	−15.2 (5)
C15—C16—C17—N2	−0.6 (9)	C4—C5—N4—C1	0.1 (8)
C15—C16—C17—C18	179.2 (6)	C6—C5—N4—C1	−178.2 (5)
N2—C17—C18—O2	−11.5 (7)	C4—C5—N4—Cu1	−179.3 (5)
C16—C17—C18—O2	168.8 (5)	C6—C5—N4—Cu1	2.3 (6)
O2—C19—C20—N1	10.1 (7)	C2—C1—N4—C5	0.1 (9)
O2—C19—C20—C21	−171.0 (5)	C2—C1—N4—Cu1	179.6 (5)
N1—C20—C21—C22	0.8 (9)	N3—Cu1—N4—C5	−0.5 (8)
C19—C20—C21—C22	−178.0 (6)	O1—Cu1—N4—C5	8.5 (4)
C20—C21—C22—C23	−3.2 (10)	Cl4—Cu1—N4—C5	−164.5 (4)
C21—C22—C23—C24	2.7 (10)	N3—Cu1—N4—C1	−180.0 (5)
C22—C23—C24—N1	0.3 (10)	O1—Cu1—N4—C1	−170.9 (5)
C21—C20—N1—C24	2.1 (8)	Cl4—Cu1—N4—C1	16.1 (5)
C19—C20—N1—C24	−179.0 (5)	C8—C7—O1—C6	−161.6 (4)
C21—C20—N1—Cu2	−177.1 (4)	C8—C7—O1—Cu1	−21.1 (6)
C19—C20—N1—Cu2	1.8 (6)	C5—C6—O1—C7	163.5 (4)
C23—C24—N1—C20	−2.7 (8)	C5—C6—O1—Cu1	23.1 (5)
C23—C24—N1—Cu2	176.4 (4)	N3—Cu1—O1—C7	17.4 (4)
N2—Cu2—N1—C20	12.5 (8)	N4—Cu1—O1—C7	−159.8 (4)
O2—Cu2—N1—C20	−9.0 (4)	Cl4—Cu1—O1—C7	−70.6 (10)
Cl3—Cu2—N1—C20	156.7 (4)	N3—Cu1—O1—C6	158.8 (4)
O11—Cu2—N1—C20	−97.2 (4)	N4—Cu1—O1—C6	−18.4 (4)
N2—Cu2—N1—C24	−166.6 (5)	Cl4—Cu1—O1—C6	70.8 (11)
O2—Cu2—N1—C24	171.8 (5)	C20—C19—O2—C18	−158.7 (5)
Cl3—Cu2—N1—C24	−22.4 (5)	C20—C19—O2—Cu2	−17.4 (6)
O11—Cu2—N1—C24	83.7 (5)	C17—C18—O2—C19	159.6 (5)
C16—C17—N2—C14	−0.5 (8)	C17—C18—O2—Cu2	18.0 (6)
C18—C17—N2—C14	179.8 (5)	N2—Cu2—O2—C19	−157.4 (4)
C16—C17—N2—Cu2	179.3 (4)	N1—Cu2—O2—C19	15.3 (4)
C18—C17—N2—Cu2	−0.4 (7)	Cl3—Cu2—O2—C19	−69.9 (6)
C13—C14—N2—C17	0.6 (9)	O11—Cu2—O2—C19	108.5 (4)
C13—C14—N2—Cu2	−179.1 (5)	N2—Cu2—O2—C18	−15.2 (4)
N1—Cu2—N2—C17	−13.2 (8)	N1—Cu2—O2—C18	157.4 (4)
O2—Cu2—N2—C17	8.4 (4)	Cl3—Cu2—O2—C18	72.2 (6)
Cl3—Cu2—N2—C17	−157.4 (4)	O11—Cu2—O2—C18	−109.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11A···O5ⁱ	0.90	2.05	2.725 (8)	131
O11—H11B···O9ⁱⁱ	0.90	1.92	2.787 (10)	163

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[CuCl(C₁₂H₁₂N₂O)][CuCl(C₁₂H₁₂N₂O)(H₂O)](ClO₄)₂
M_r	815.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.997 (2), 12.882 (3), 12.913 (3)
α, β, γ (°)	97.174 (3), 112.031 (3), 106.851 (3)
V (Å³)	1565.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.42 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.525, 0.709
No. of measured, independent and observed [I > 2σ(I)] reflections	8530, 6009, 4063
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.185, 1.05
No. of reflections	6009
No. of parameters	411
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.60

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Cl3—Cu2	2.2511 (15)	Cu2—N2	1.970 (4)
Cl4—Cu1	2.2067 (14)	Cu2—N1	1.972 (4)
Cu1—N3	1.968 (4)	Cu2—O2	2.005 (4)
Cu1—O1	1.970 (3)	Cu2—O11	2.298 (4)
Cu1—N4	1.973 (4)

N3—Cu1—O1	80.97 (17)	N1—Cu2—O2	80.45 (16)
N3—Cu1—N4	161.79 (19)	N2—Cu2—Cl3	98.32 (14)
O1—Cu1—N4	81.04 (17)	N1—Cu2—Cl3	98.09 (13)
N3—Cu1—Cl4	98.72 (13)	O2—Cu2—Cl3	165.86 (13)
O1—Cu1—Cl4	173.09 (12)	N2—Cu2—O11	93.89 (17)
N4—Cu1—Cl4	98.80 (14)	N1—Cu2—O11	92.93 (17)
N2—Cu2—N1	159.85 (19)	O2—Cu2—O11	88.68 (16)
N2—Cu2—O2	80.78 (17)	Cl3—Cu2—O11	105.46 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11A···O5ⁱ	0.90	2.05	2.725 (8)	131.4
O11—H11B···O9ⁱⁱ	0.90	1.92	2.787 (10)	162.7

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1.

Acknowledgements

The authors thank the Project of Scientific Studies Development of Shandong Provincial Education Department (grant No. J08LC51) and the Natural Science Foundation of Shandong Province (grant No. Y2007B26).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. M. (2007). Acta Cryst. E63, m2241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, J. M. (2008a). Acta Cryst. E64, m1467. Web of Science CrossRef IUCr Journals Google Scholar
Li, J. (2008b). Acta Cryst. E64, m1468. Web of Science 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page m933

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

Chlorido[2,2′-(oxydi­methyl­ene)­di­pyridine]copper(II) perchlorate–aqua­chlorido[2,2′-(oxydi­methyl­ene)­di­pyridine]copper(II) perchlorate (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Chlorido[2,2′-(oxydimethylene)dipyridine]copper(II) perchlorate–aquachlorido[2,2′-(oxydimethylene)dipyridine]copper(II) perchlorate (1/1)