{μ-1,5-Bis[(E)-1-(2-pyrid­yl)ethyl­idene]carbonohydrazidato(1−)}bis­[chlorido­methano­lcopper(II)] perchlorate

Huang, W.

doi:10.1107/S1600536809040471

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1347

https://doi.org/10.1107/S1600536809040471

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{μ-1,5-Bis[(E)-1-(2-pyridyl)ethylidene]carbonohydrazidato(1−)}bis[chloridomethanolcopper(II)] perchlorate

Wei Huang ^a ^*

^aAnhui Key Laboratory of Functional Coordination Compounds, School of Chemistry and Chemical Engineering, Anqing Teachers College, Anqing, 246011 Anhui, People's Republic of China
^*Correspondence e-mail: whuang_nju@yahoo.cn

(Received 16 July 2009; accepted 5 October 2009; online 10 October 2009)

The title dinuclear copper complex, [Cu₂(C₁₅H₁₅N₆O)Cl₂(CH₃OH)₂]ClO₄, was prepared by the reaction of copper(II) chloride with bis[1-(2-pyridyl)ethylidene]carbonohydrazide in the presence of sodium perchlorate in a methanol solution. It features a mono-deprotonated bis-tridentate ligand, which coordinates to two independent Cu^II ions, one of which is coordinated by pyridyl N, hydrazyl N and carbonyl O atoms. The second Cu^II ion is coordinated by the pyridyl N and two hydrazyl N atoms from different hydrazyl groups. The coordination environments of both Cu^II ions are completed by a chloride ion and a methanol molecule. The dihedral angle between the pyridyl groups is 27.46 (10)°. The crystal packing is stabilized by O—H⋯O(perchlorate), O—H⋯Cl and N—H⋯Cl hydrogen bonding.

Related literature

For the definition of the distortion parameter, see: Addison et al. (1984 ).

Experimental

Crystal data

[Cu₂(C₁₅H₁₅N₆O)Cl₂(CH₄O)₂]ClO₄
M_r = 656.84
Orthorhombic, P b c a
a = 8.0319 (3) Å
b = 16.6784 (6) Å
c = 37.3492 (13) Å
V = 5003.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 2.07 mm⁻¹
T = 298 K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008 ) T_min = 0.675, T_max = 0.783
30236 measured reflections
5692 independent reflections
4016 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.142
S = 1.04
5692 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯Cl2ⁱ	0.86	2.91	3.766 (4)	176
O1W—H1W⋯Cl1ⁱⁱ	1.01	2.31	3.205 (4)	147
O2W—H2W⋯O7ⁱⁱⁱ	1.00	1.90	2.855 (6)	159
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) x+1, y, z.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809040471/fi2081sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040471/fi2081Isup2.hkl

checkCIF report

Comment top

Recent research has witnessed considerable interest in the development of new multidentate ligands. Polyamine tripod ligands containing appropriate binding sites and shape may be designed to form special topological structures. The molecular topology of the host molecule can be synthetically modulated to bind many different chemical species from transition metals to lanthanide ions. To this purpose, the title compound was synthesized and structurally characterized. It features a dinuclear copper(II) complex assembled from one mono-deprotonated, bis-tridentate ligand and two distinct copper(II) ions. The coordination of Cu1 is achieved by pyridyl-N, hydrazine-N (deprotonated hydrazine group) and carbonyl-O, Cu2 is coordinated by the second pyridyl-N, hydrazine-N and the second hydrazine-N of the first hydrazine group (Fig. 1 ).The coordination environments of both Cu^II ions are completed by one chloride ion and one methaol molecule. Both of the copper atoms adopt similar distorted 4 + 1 coordinated square-pyramid geometries with a distortion parameter 0.197 for Cu1 and 0.101 for Cu2 (Addison et al., 1984). The crystal packing is stabilised by O-H···O(perchlorate), O-H···Cl and N-H···Cl hydrogen bonding (Fig. 2) The dihedral angle between the pyridyl groups is 27.46 (10)°.

Related literature top

For the definition of distortion parameter, see: Addison et al. (1984).

Experimental top

A methanolic solution (15 ml) containing the ligand (0.1 mmol, 0.03 g) was added dropwise to a methanolic solution (10 ml) containing CuCl₂.2H₂O (0.1 mmol, 0.034 g). After stirring for 2 h, the solution was filtered. Dark-green block-shaped crystals suitable for single-crystal X-ray diffraction were obtained by evaporating the resulting filtration in air for several days (yield: 65.6% based on the ligand). Anal calc (%). for C₁₇H₂₃Cl₃Cu₂N₆O₇: H 3.53 C 31.09 N 12.79 Found: H 3.42, C 31.21, N 12.86.

Structure description top

For the definition of distortion parameter, see: Addison et al. (1984).

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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The dinuclear cation and the perchlorate anion in the structure of the title compound. Thermal ellipsoids are drawn at the 50% level.
	Fig. 2. The hydrogen bonding pattern in the title compound.

{µ-1,5-Bis[(E)-1-(2- pyridyl)ethylidene]carbonohydrazidato(1-)}bis[chloridomethanolcopper(II)] perchlorate top

Crystal data top

[Cu₂(C₁₅H₁₅N₆O)Cl₂(CH₄O)₂]ClO₄	F(000) = 2656
M_r = 656.84	D_x = 1.744 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15443 reflections
a = 8.0319 (3) Å	θ = 2.3–27.0°
b = 16.6784 (6) Å	µ = 2.07 mm⁻¹
c = 37.3492 (13) Å	T = 298 K
V = 5003.3 (3) Å³	Block, dark-green
Z = 8	0.18 × 0.16 × 0.12 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5692 independent reflections
Radiation source: fine-focus sealed tube	4016 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008)	h = −10→10
T_min = 0.675, T_max = 0.783	k = −21→21
30236 measured reflections	l = −48→39

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0713P)² + 3.3159P] where P = (F_o² + 2F_c²)/3
5692 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Cu₂(C₁₅H₁₅N₆O)Cl₂(CH₄O)₂]ClO₄	V = 5003.3 (3) Å³
M_r = 656.84	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.0319 (3) Å	µ = 2.07 mm⁻¹
b = 16.6784 (6) Å	T = 298 K
c = 37.3492 (13) Å	0.18 × 0.16 × 0.12 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5692 independent reflections
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008)	4016 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.783	R_int = 0.064
30236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.04	Δρ_max = 0.90 e Å⁻³
5692 reflections	Δρ_min = −0.67 e Å⁻³
318 parameters

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 > 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
Cu1	0.62011 (6)	0.28060 (3)	0.033586 (13)	0.03826 (15)
Cu2	0.81104 (6)	0.39647 (3)	0.143708 (12)	0.03630 (15)
C1	0.8701 (6)	0.4718 (3)	0.21601 (12)	0.0538 (11)
H1A	0.8464	0.5205	0.2050	0.065*
C1W	0.3072 (9)	0.2671 (5)	0.08697 (17)	0.112 (3)
H1WA	0.1939	0.2822	0.0916	0.167*
H1WB	0.3761	0.2840	0.1066	0.167*
H1WC	0.3143	0.2100	0.0844	0.167*
C2	0.9166 (7)	0.4715 (3)	0.25190 (13)	0.0610 (13)
H2A	0.9248	0.5191	0.2647	0.073*
C2W	1.2080 (7)	0.4315 (5)	0.1542 (2)	0.098 (2)
H2WA	1.3027	0.4607	0.1455	0.147*
H2WB	1.2250	0.3752	0.1504	0.147*
H2WC	1.1941	0.4417	0.1794	0.147*
C3	0.9502 (6)	0.3989 (3)	0.26802 (12)	0.0569 (12)
H3A	0.9802	0.3970	0.2921	0.068*
C4	0.9391 (5)	0.3293 (3)	0.24833 (11)	0.0486 (10)
H4A	0.9623	0.2799	0.2588	0.058*
C5	0.8929 (5)	0.3338 (3)	0.21264 (11)	0.0411 (9)
C6	0.8894 (7)	0.1789 (3)	0.20249 (13)	0.0591 (12)
H6A	0.8749	0.1424	0.1829	0.089*
H6B	0.8048	0.1694	0.2201	0.089*
H6C	0.9971	0.1708	0.2130	0.089*
C7	0.8762 (5)	0.2626 (3)	0.18923 (11)	0.0398 (9)
C8	0.7643 (5)	0.2622 (2)	0.09818 (10)	0.0368 (8)
C9	0.8716 (5)	0.4960 (3)	0.06034 (12)	0.0481 (10)
H9A	0.9033	0.4835	0.0845	0.072*
H9B	0.8118	0.5459	0.0600	0.072*
H9C	0.9695	0.5006	0.0457	0.072*
C10	0.7642 (4)	0.4315 (2)	0.04617 (10)	0.0346 (8)
C11	0.6971 (5)	0.4355 (2)	0.00899 (10)	0.0364 (8)
C12	0.7161 (5)	0.5001 (3)	−0.01319 (11)	0.0447 (10)
H12A	0.7704	0.5459	−0.0051	0.054*
C13	0.6538 (6)	0.4967 (3)	−0.04776 (13)	0.0543 (12)
H13A	0.6684	0.5398	−0.0633	0.065*
C14	0.5709 (6)	0.4299 (3)	−0.05879 (12)	0.0579 (12)
H14A	0.5266	0.4270	−0.0818	0.069*
C15	0.5539 (6)	0.3668 (3)	−0.03538 (11)	0.0491 (10)
H15A	0.4969	0.3213	−0.0429	0.059*
N1	0.8586 (4)	0.4049 (2)	0.19707 (9)	0.0411 (8)
N2	0.8459 (4)	0.28245 (19)	0.15635 (9)	0.0387 (7)
N3	0.8162 (5)	0.2289 (2)	0.12969 (9)	0.0424 (8)
H3B	0.8291	0.1781	0.1324	0.051*
N4	0.7825 (4)	0.34270 (19)	0.09563 (8)	0.0359 (7)
N5	0.7277 (4)	0.36484 (18)	0.06188 (8)	0.0340 (7)
N6	0.6157 (4)	0.3682 (2)	−0.00234 (9)	0.0392 (7)
O1	0.7099 (4)	0.21631 (15)	0.07431 (7)	0.0447 (7)
O1W	0.3611 (4)	0.3035 (2)	0.05585 (9)	0.0620 (9)
O2W	1.0641 (4)	0.45651 (19)	0.13568 (8)	0.0540 (8)
O4	0.2605 (8)	0.6862 (8)	0.1635 (3)	0.276 (6)
O5	0.1217 (13)	0.6334 (4)	0.20860 (15)	0.189 (4)
O6	0.0314 (10)	0.7448 (4)	0.17370 (16)	0.159 (3)
O7	0.0200 (11)	0.6230 (3)	0.15081 (16)	0.167 (3)
Cl1	0.54972 (14)	0.18014 (6)	−0.00266 (3)	0.0493 (3)
Cl2	0.64899 (14)	0.50485 (7)	0.13951 (3)	0.0529 (3)
Cl3	0.1126 (2)	0.66852 (9)	0.17526 (4)	0.0740 (4)
H1W	0.2879	0.2904	0.0347	0.089*
H2W	1.0197	0.5118	0.1398	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0495 (3)	0.0282 (3)	0.0371 (3)	−0.0014 (2)	−0.0063 (2)	−0.00165 (19)
Cu2	0.0432 (3)	0.0324 (3)	0.0332 (3)	0.0015 (2)	−0.00304 (19)	−0.00154 (19)
C1	0.063 (3)	0.047 (3)	0.051 (3)	−0.004 (2)	−0.004 (2)	−0.006 (2)
C1W	0.101 (5)	0.180 (8)	0.055 (4)	−0.031 (5)	0.007 (4)	0.014 (4)
C2	0.075 (3)	0.060 (3)	0.048 (3)	−0.006 (3)	−0.007 (2)	−0.013 (2)
C2W	0.051 (3)	0.128 (6)	0.115 (5)	0.007 (4)	−0.011 (3)	−0.010 (5)
C3	0.062 (3)	0.072 (4)	0.037 (2)	−0.005 (3)	−0.005 (2)	−0.004 (2)
C4	0.054 (2)	0.057 (3)	0.034 (2)	−0.004 (2)	−0.0024 (19)	0.0016 (19)
C5	0.038 (2)	0.048 (3)	0.037 (2)	−0.0022 (17)	0.0008 (16)	0.0019 (19)
C6	0.082 (3)	0.045 (3)	0.050 (3)	0.006 (2)	−0.002 (2)	0.007 (2)
C7	0.042 (2)	0.040 (2)	0.038 (2)	0.0016 (17)	0.0020 (17)	0.0037 (17)
C8	0.047 (2)	0.032 (2)	0.0311 (19)	−0.0011 (16)	0.0009 (16)	−0.0001 (16)
C9	0.055 (2)	0.040 (2)	0.050 (3)	−0.0123 (19)	−0.0035 (19)	0.0011 (19)
C10	0.0360 (19)	0.030 (2)	0.038 (2)	0.0001 (15)	0.0023 (16)	−0.0010 (16)
C11	0.0362 (19)	0.033 (2)	0.040 (2)	0.0052 (16)	0.0035 (16)	−0.0015 (16)
C12	0.051 (2)	0.037 (2)	0.046 (2)	0.0006 (18)	0.0006 (19)	0.0029 (18)
C13	0.067 (3)	0.049 (3)	0.047 (3)	0.013 (2)	0.002 (2)	0.015 (2)
C14	0.076 (3)	0.057 (3)	0.041 (2)	0.011 (3)	−0.013 (2)	0.002 (2)
C15	0.060 (3)	0.042 (2)	0.045 (2)	0.003 (2)	−0.015 (2)	0.0004 (19)
N1	0.0473 (19)	0.037 (2)	0.0389 (18)	−0.0001 (14)	−0.0046 (15)	−0.0018 (15)
N2	0.0471 (19)	0.0336 (18)	0.0355 (17)	−0.0011 (14)	−0.0040 (14)	−0.0013 (14)
N3	0.065 (2)	0.0291 (18)	0.0333 (17)	0.0030 (15)	−0.0065 (15)	0.0006 (14)
N4	0.0467 (18)	0.0319 (18)	0.0289 (16)	−0.0031 (14)	−0.0004 (13)	0.0008 (13)
N5	0.0393 (17)	0.0304 (17)	0.0322 (16)	0.0006 (13)	−0.0007 (13)	−0.0013 (13)
N6	0.0456 (18)	0.0320 (18)	0.0399 (18)	0.0011 (14)	−0.0058 (14)	−0.0006 (14)
O1	0.0696 (19)	0.0259 (14)	0.0386 (15)	−0.0030 (13)	−0.0103 (13)	−0.0012 (12)
O1W	0.060 (2)	0.069 (2)	0.057 (2)	0.0002 (16)	0.0050 (16)	0.0026 (17)
O2W	0.0486 (17)	0.055 (2)	0.0578 (19)	−0.0072 (15)	−0.0076 (14)	−0.0021 (15)
O4	0.077 (4)	0.488 (17)	0.263 (9)	−0.028 (7)	−0.029 (5)	0.232 (11)
O5	0.361 (11)	0.138 (5)	0.068 (3)	−0.100 (6)	−0.028 (5)	0.020 (3)
O6	0.242 (8)	0.129 (5)	0.108 (4)	0.047 (6)	−0.015 (5)	−0.033 (4)
O7	0.295 (9)	0.073 (3)	0.131 (5)	−0.026 (4)	−0.096 (5)	−0.015 (3)
Cl1	0.0617 (7)	0.0353 (6)	0.0509 (6)	−0.0058 (5)	−0.0110 (5)	−0.0075 (4)
Cl2	0.0561 (6)	0.0500 (7)	0.0526 (6)	0.0180 (5)	−0.0067 (5)	−0.0051 (5)
Cl3	0.0885 (10)	0.0661 (9)	0.0673 (9)	−0.0155 (7)	0.0015 (7)	−0.0110 (7)

Geometric parameters (Å, º) top

Cu1—N5	1.959 (3)	C6—H6B	0.9600
Cu1—N6	1.985 (3)	C6—H6C	0.9600
Cu1—O1	1.996 (3)	C7—N2	1.294 (5)
Cu1—Cl1	2.2270 (11)	C8—O1	1.253 (4)
Cu1—O1W	2.273 (3)	C8—N4	1.354 (5)
Cu2—N2	1.979 (3)	C8—N3	1.367 (5)
Cu2—N4	2.020 (3)	C9—C10	1.477 (5)
Cu2—N1	2.034 (3)	C9—H9A	0.9600
Cu2—Cl2	2.2330 (11)	C9—H9B	0.9600
Cu2—O2W	2.285 (3)	C9—H9C	0.9600
C1—N1	1.324 (6)	C10—N5	1.292 (5)
C1—C2	1.392 (6)	C10—C11	1.491 (5)
C1—H1A	0.9300	C11—N6	1.366 (5)
C1W—O1W	1.380 (7)	C11—C12	1.367 (6)
C1W—H1WA	0.9600	C12—C13	1.386 (6)
C1W—H1WB	0.9600	C12—H12A	0.9300
C1W—H1WC	0.9600	C13—C14	1.362 (7)
C2—C3	1.378 (7)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.375 (6)
C2W—O2W	1.411 (6)	C14—H14A	0.9300
C2W—H2WA	0.9600	C15—N6	1.330 (5)
C2W—H2WB	0.9600	C15—H15A	0.9300
C2W—H2WC	0.9600	N2—N3	1.358 (5)
C3—C4	1.378 (6)	N3—H3B	0.8600
C3—H3A	0.9300	N4—N5	1.386 (4)
C4—C5	1.386 (6)	O1W—H1W	1.0086
C4—H4A	0.9300	O2W—H2W	1.0003
C5—N1	1.349 (5)	O4—Cl3	1.301 (7)
C5—C7	1.481 (6)	O5—Cl3	1.378 (6)
C6—C7	1.486 (6)	O6—Cl3	1.430 (7)
C6—H6A	0.9600	O7—Cl3	1.401 (5)

N5—Cu1—N6	81.04 (13)	O1—C8—N3	118.1 (4)
N5—Cu1—O1	79.33 (12)	N4—C8—N3	115.5 (3)
N6—Cu1—O1	156.56 (13)	C10—C9—H9A	109.5
N5—Cu1—Cl1	168.39 (10)	C10—C9—H9B	109.5
N6—Cu1—Cl1	97.97 (10)	H9A—C9—H9B	109.5
O1—Cu1—Cl1	98.68 (8)	C10—C9—H9C	109.5
N5—Cu1—O1W	94.93 (13)	H9A—C9—H9C	109.5
N6—Cu1—O1W	96.16 (13)	H9B—C9—H9C	109.5
O1—Cu1—O1W	98.17 (13)	N5—C10—C9	126.7 (4)
Cl1—Cu1—O1W	96.68 (10)	N5—C10—C11	112.3 (3)
N2—Cu2—N4	78.56 (13)	C9—C10—C11	120.8 (3)
N2—Cu2—N1	78.81 (14)	N6—C11—C12	120.8 (4)
N4—Cu2—N1	157.34 (13)	N6—C11—C10	115.2 (3)
N2—Cu2—Cl2	151.28 (11)	C12—C11—C10	124.0 (4)
N4—Cu2—Cl2	103.35 (10)	C11—C12—C13	119.5 (4)
N1—Cu2—Cl2	97.03 (10)	C11—C12—H12A	120.2
N2—Cu2—O2W	109.06 (13)	C13—C12—H12A	120.2
N4—Cu2—O2W	100.30 (12)	C14—C13—C12	119.4 (4)
N1—Cu2—O2W	86.07 (13)	C14—C13—H13A	120.3
Cl2—Cu2—O2W	98.88 (9)	C12—C13—H13A	120.3
N1—C1—C2	122.0 (5)	C13—C14—C15	118.9 (4)
N1—C1—H1A	119.0	C13—C14—H14A	120.6
C2—C1—H1A	119.0	C15—C14—H14A	120.6
O1W—C1W—H1WA	109.5	N6—C15—C14	122.6 (4)
O1W—C1W—H1WB	109.5	N6—C15—H15A	118.7
H1WA—C1W—H1WB	109.5	C14—C15—H15A	118.7
O1W—C1W—H1WC	109.5	C1—N1—C5	119.7 (4)
H1WA—C1W—H1WC	109.5	C1—N1—Cu2	126.5 (3)
H1WB—C1W—H1WC	109.5	C5—N1—Cu2	113.6 (3)
C3—C2—C1	118.5 (5)	C7—N2—N3	124.1 (3)
C3—C2—H2A	120.8	C7—N2—Cu2	119.9 (3)
C1—C2—H2A	120.8	N3—N2—Cu2	115.6 (2)
O2W—C2W—H2WA	109.5	N2—N3—C8	114.7 (3)
O2W—C2W—H2WB	109.5	N2—N3—H3B	122.6
H2WA—C2W—H2WB	109.5	C8—N3—H3B	122.6
O2W—C2W—H2WC	109.5	C8—N4—N5	107.1 (3)
H2WA—C2W—H2WC	109.5	C8—N4—Cu2	113.0 (2)
H2WB—C2W—H2WC	109.5	N5—N4—Cu2	136.6 (2)
C4—C3—C2	119.6 (4)	C10—N5—N4	124.8 (3)
C4—C3—H3A	120.2	C10—N5—Cu1	118.2 (3)
C2—C3—H3A	120.2	N4—N5—Cu1	116.1 (2)
C3—C4—C5	119.0 (4)	C15—N6—C11	118.7 (4)
C3—C4—H4A	120.5	C15—N6—Cu1	128.4 (3)
C5—C4—H4A	120.5	C11—N6—Cu1	112.8 (2)
N1—C5—C4	121.2 (4)	C8—O1—Cu1	109.9 (2)
N1—C5—C7	115.5 (3)	C1W—O1W—Cu1	121.4 (4)
C4—C5—C7	123.3 (4)	C1W—O1W—H1W	112.5
C7—C6—H6A	109.5	Cu1—O1W—H1W	102.2
C7—C6—H6B	109.5	C2W—O2W—Cu2	122.3 (4)
H6A—C6—H6B	109.5	C2W—O2W—H2W	119.3
C7—C6—H6C	109.5	Cu2—O2W—H2W	93.8
H6A—C6—H6C	109.5	O4—Cl3—O5	110.7 (5)
H6B—C6—H6C	109.5	O4—Cl3—O7	112.7 (7)
N2—C7—C5	111.9 (4)	O5—Cl3—O7	112.7 (4)
N2—C7—C6	124.7 (4)	O4—Cl3—O6	101.6 (6)
C5—C7—C6	123.4 (4)	O5—Cl3—O6	116.0 (5)
O1—C8—N4	126.4 (3)	O7—Cl3—O6	102.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl2ⁱ	0.86	2.91	3.766 (4)	176
O1W—H1W···Cl1ⁱⁱ	1.01	2.31	3.205 (4)	147
O2W—H2W···O7ⁱⁱⁱ	1.00	1.90	2.855 (6)	159

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x−1/2, −y+1/2, −z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₅H₁₅N₆O)Cl₂(CH₄O)₂]ClO₄
M_r	656.84
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	8.0319 (3), 16.6784 (6), 37.3492 (13)
V (Å³)	5003.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.07
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SHELXTL; Sheldrick, 2008)
T_min, T_max	0.675, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	30236, 5692, 4016
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.142, 1.04
No. of reflections	5692
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.67

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl2ⁱ	0.86	2.91	3.766 (4)	176.2
O1W—H1W···Cl1ⁱⁱ	1.01	2.31	3.205 (4)	147.4
O2W—H2W···O7ⁱⁱⁱ	1.00	1.90	2.855 (6)	158.8

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x−1/2, −y+1/2, −z; (iii) x+1, y, z.

Acknowledgements

The author acknowledges financial support from Anqing Teachers' College.

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page m1347

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

{μ-1,5-Bis[(E)-1-(2-pyrid­yl)ethyl­­idene]carbonohydrazidato(1−)}bis­­[chlorido­methano­lcopper(II)] perchlorate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{μ-1,5-Bis[(E)-1-(2-pyridyl)ethylidene]carbonohydrazidato(1−)}bis[chloridomethanolcopper(II)] perchlorate