catena-Poly[[[pyridinecopper(II)]-(μ-2-oxidonaphthalene-1-carbaldehyde pico­linoylhydrazonato)-[pyridinecopper(II)]-μ-sulfato] diethyl ether hemisolvate]

Wang, Q.; Li, D.; Wang, D.

doi:10.1107/S1600536809012653

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m520

doi:10.1107/S1600536809012653

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catena-Poly[[[pyridinecopper(II)]-(μ-2-oxidonaphthalene-1-carbaldehyde picolinoylhydrazonato)-[pyridinecopper(II)]-μ-sulfato] diethyl ether hemisolvate]

Quanchang Wang,^a Dacheng Li ^a ^* and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@lcu.edu.cn

(Received 18 February 2009; accepted 3 April 2009; online 18 April 2009)

The title compound, {[Cu₂(C₁₇H₁₁N₃O)(SO₄)(C₅H₅N)₂]·0.5C₄H₁₀O}_n, was synthesized by the reaction of 2-hydroxy-1-naphthylaldehyde-2-pyridinecarboxylhydrazone with copper sulfonate. A one-dimensional polymer was obtained via self-assembly. Each Cu ion is located in a distorted square-pyramidal coordination environment, with one Cu ion coordinated by two N and three O atoms, while the other links to two O and three N atoms. In the crystal, weak intermolecular C—H⋯O interactions connect the chains into a two-dimensional network.

Related literature

For the biological activity of aroylhydrazones, see Armstrong et al. (2003 ). For the crystal structure of a copper complex with a related picolinoylhydrazone derivative, see: Bai et al. (2006 ).

Experimental

Crystal data

[Cu₂(C₁₇H₁₁N₃O)(SO₄)(C₅H₅N)₂]·0.5C₄H₁₀O
M_r = 707.69
Monoclinic, C 2/c
a = 26.484 (2) Å
b = 14.0374 (15) Å
c = 16.8083 (17) Å
β = 108.404 (2)°
V = 5929.2 (10) Å³
Z = 8
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 298 K
0.38 × 0.32 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.589, T_max = 0.789
14633 measured reflections
5215 independent reflections
3268 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.01
5215 reflections
394 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.888 (3)
Cu1—N2	1.957 (4)
Cu1—O1	1.964 (3)
Cu1—N4	2.008 (4)
Cu1—O5ⁱ	2.389 (3)
Cu2—O3	2.011 (3)
Cu2—N3	2.015 (4)
Cu2—N1	2.016 (4)
Cu2—O4	2.036 (3)
Cu2—N5	2.189 (4)
Symmetry code: (i) $[x, -y+2, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O2ⁱ	0.93	2.46	3.386 (7)	174
C5—H5⋯O3ⁱⁱ	0.93	2.43	3.340 (7)	165
C19—H19⋯O7ⁱⁱⁱ	0.93	2.46	3.266 (7)	145
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012653/ez2166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012653/ez2166Isup2.hkl

checkCIF report

Comment top

Hydrazone complexes play an important role in the fields of photoelectric materials and medicines due to their biological and pharmacological activities (Armstrong et al., 2003). The molecular structure of the related salicylaldehyde-2-pyridinecarboxyl-hydrazone has been reported (Bai et al., 2006). To throw further light on the coordination characteristics of 2-pyridinecarboxyl-hydrazone and to explore the properties of their complexes, we report the structure of the title complex (I).

The structure of repeating unit of complex I is shown in Fig. 1 and the one-dimensional polymeric chain structure of the complex is shown in Fig. 2. In the complex, each Cu ion is located in a distorted square pyramidal coordination environment. Cu1 is coordinated to two N and three O atoms, while Cu2 links to two O and three N atoms. The Cu—O (2-naphthol) distance [1.888 (3) Å] is slightly shorter than the previously reported Cu—O (phenol) distance [1.954 (3) Å] (Bai et al., 2006), whereas the Cu—O (carbozone) distance [1.964 (3) Å] is longer than the related Cu—O (carbozone) distance of 1.942 (3) Å in the related complex (Bai et al., 2006). In the crystal, weak intermolecular C—H···O interactions connect the chains into a two-dimensional net structure.

Related literature top

For the biological activity of aroylhydrazones, see Armstrong et al. (2003). For the crystal structure of a copper complex with a related picolinoylhydrazone derivative, see: Bai et al. (2006).

Experimental top

The title compound was synthesizd by mixing 2-hydroxy-1-naphthylaldehyde-2-pyridinecarboxyl-hydrazone (0.0291 g, 0.1 mmol) and copper sulfonate (0.0319 g, 0.2 mmol) and stirring in 10 ml of pyridine for 6 h. The product was filtered and then layered with ether. 2 weeks later brown single crystals were obtained. Anal. Calcd (%) for 2(C27 H21 Cu2 N5 O6 S), C4 H10 O (Mr = 1415.44): C:49.22; H:3.70; N:9.90; Found (%): C: 49.30; H: 3.52; N: 9.76

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

Figures top

	Fig. 1. The molecular structure of the compound, showing 30% probability displacement ellipsoids. Unlabelled atoms are related to the labelled ones by symmetry operation (+x, 2 - y, -1/2 + z). H atoms have been omitted for clarity.
	Fig. 2. The one-dimensional polymeric structure of the title complex.

catena-Poly[[[pyridinecopper(II)]-(µ-2-oxidonaphthalene-1-carbaldehyde picolinoylhydrazonato)-[pyridinecopper(II)]-µ-sulfonato] diethyl ether hemisolvate] top

Crystal data top

[Cu₂(C₁₇H₁₁N₃O)(SO₄)(C₅H₅N)₂]·0.5C₄H₁₀O	F(000) = 2888
M_r = 707.69	D_x = 1.586 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2858 reflections
a = 26.484 (2) Å	θ = 2.3–25.3°
b = 14.0374 (15) Å	µ = 1.56 mm⁻¹
c = 16.8083 (17) Å	T = 298 K
β = 108.404 (2)°	Block, brown
V = 5929.2 (10) Å³	0.38 × 0.32 × 0.16 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5215 independent reflections
Radiation source: fine-focus sealed tube	3268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
phi and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
T_min = 0.589, T_max = 0.789	k = −16→16
14633 measured reflections	l = −12→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.052P)² + 19.1978P] where P = (F_o² + 2F_c²)/3
5215 reflections	(Δ/σ)_max = 0.001
394 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Cu₂(C₁₇H₁₁N₃O)(SO₄)(C₅H₅N)₂]·0.5C₄H₁₀O	V = 5929.2 (10) Å³
M_r = 707.69	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.484 (2) Å	µ = 1.56 mm⁻¹
b = 14.0374 (15) Å	T = 298 K
c = 16.8083 (17) Å	0.38 × 0.32 × 0.16 mm
β = 108.404 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5215 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3268 reflections with I > 2σ(I)
T_min = 0.589, T_max = 0.789	R_int = 0.055
14633 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.052P)² + 19.1978P] where P = (F_o² + 2F_c²)/3
5215 reflections	Δρ_max = 0.85 e Å⁻³
394 parameters	Δρ_min = −0.49 e Å⁻³

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
Cu1	0.19607 (2)	0.78202 (4)	0.14330 (4)	0.0327 (2)
Cu2	0.14395 (2)	1.00409 (4)	−0.08707 (4)	0.03123 (19)
N1	0.16100 (16)	0.9077 (3)	0.0066 (2)	0.0299 (10)
N2	0.20801 (16)	0.8671 (3)	0.0587 (3)	0.0297 (10)
N3	0.06961 (16)	0.9731 (3)	−0.0874 (3)	0.0331 (11)
N4	0.17578 (17)	0.6701 (3)	0.2012 (3)	0.0347 (11)
N5	0.16690 (18)	1.1384 (3)	−0.0190 (3)	0.0368 (11)
O1	0.12165 (13)	0.8167 (3)	0.0856 (2)	0.0366 (9)
O2	0.26870 (13)	0.7475 (3)	0.1794 (2)	0.0374 (9)
O3	0.12067 (13)	1.0678 (2)	−0.2000 (2)	0.0355 (9)
O4	0.20303 (13)	0.9942 (2)	−0.1402 (2)	0.0352 (9)
O5	0.19783 (14)	1.1264 (3)	−0.2360 (2)	0.0406 (9)
O6	0.15828 (16)	0.9758 (3)	−0.2900 (2)	0.0449 (10)
O7	1.0000	0.6854 (6)	0.2500	0.092 (3)
S1	0.17080 (5)	1.04166 (9)	−0.22080 (8)	0.0293 (3)
C1	0.1195 (2)	0.8746 (4)	0.0264 (3)	0.0307 (12)
C2	0.0669 (2)	0.9078 (4)	−0.0292 (3)	0.0326 (12)
C3	0.0197 (2)	0.8731 (4)	−0.0246 (4)	0.0456 (15)
H3	0.0191	0.8286	0.0161	0.055*
C4	−0.0273 (2)	0.9056 (5)	−0.0820 (4)	0.0550 (17)
H4	−0.0600	0.8828	−0.0808	0.066*
C5	−0.0247 (2)	0.9719 (5)	−0.1405 (4)	0.0532 (17)
H5	−0.0557	0.9948	−0.1794	0.064*
C6	0.0243 (2)	1.0040 (4)	−0.1408 (4)	0.0442 (15)
H6	0.0257	1.0494	−0.1803	0.053*
C7	0.2514 (2)	0.8798 (3)	0.0399 (3)	0.0313 (12)
H7	0.2495	0.9184	−0.0059	0.038*
C8	0.3020 (2)	0.8388 (3)	0.0846 (3)	0.0297 (12)
C9	0.3072 (2)	0.7729 (4)	0.1518 (3)	0.0321 (12)
C10	0.3584 (2)	0.7317 (4)	0.1922 (4)	0.0411 (14)
H10	0.3616	0.6859	0.2335	0.049*
C11	0.4018 (2)	0.7567 (4)	0.1727 (4)	0.0439 (15)
H11	0.4345	0.7299	0.2024	0.053*
C12	0.3994 (2)	0.8238 (4)	0.1071 (4)	0.0396 (14)
C13	0.3491 (2)	0.8645 (4)	0.0621 (3)	0.0332 (13)
C14	0.3484 (2)	0.9312 (4)	−0.0009 (4)	0.0464 (15)
H14	0.3162	0.9585	−0.0319	0.056*
C15	0.3939 (3)	0.9568 (5)	−0.0177 (4)	0.0624 (19)
H15	0.3920	1.0009	−0.0598	0.075*
C16	0.4427 (3)	0.9177 (5)	0.0272 (5)	0.067 (2)
H16	0.4734	0.9358	0.0156	0.080*
C17	0.4451 (2)	0.8525 (5)	0.0886 (4)	0.0556 (18)
H17	0.4779	0.8265	0.1188	0.067*
C18	0.1284 (2)	0.6663 (4)	0.2132 (4)	0.0499 (16)
H18	0.1068	0.7200	0.2012	0.060*
C19	0.1099 (3)	0.5857 (5)	0.2430 (4)	0.0609 (19)
H19	0.0768	0.5859	0.2512	0.073*
C20	0.1414 (3)	0.5058 (5)	0.2601 (4)	0.0580 (18)
H20	0.1294	0.4502	0.2785	0.070*
C21	0.1905 (3)	0.5093 (4)	0.2498 (4)	0.0531 (17)
H21	0.2129	0.4567	0.2628	0.064*
C22	0.2066 (2)	0.5922 (4)	0.2198 (3)	0.0404 (14)
H22	0.2399	0.5938	0.2124	0.048*
C23	0.1707 (2)	1.2197 (4)	−0.0595 (4)	0.0447 (15)
H23	0.1622	1.2175	−0.1176	0.054*
C24	0.1862 (3)	1.3053 (4)	−0.0203 (4)	0.0517 (17)
H24	0.1877	1.3598	−0.0510	0.062*
C25	0.1995 (3)	1.3085 (5)	0.0656 (4)	0.0590 (18)
H25	0.2109	1.3654	0.0939	0.071*
C26	0.1959 (3)	1.2281 (5)	0.1093 (4)	0.0578 (18)
H26	0.2042	1.2295	0.1673	0.069*
C27	0.1797 (2)	1.1443 (4)	0.0646 (4)	0.0473 (16)
H27	0.1776	1.0894	0.0943	0.057*
C28	0.9808 (4)	0.7425 (7)	0.1773 (8)	0.109 (4)
H28A	1.0083	0.7862	0.1733	0.131*
H28B	0.9504	0.7795	0.1798	0.131*
C29	0.9644 (4)	0.6756 (9)	0.1002 (7)	0.136 (4)
H29A	0.9954	0.6439	0.0952	0.204*
H29B	0.9481	0.7122	0.0505	0.204*
H29C	0.9396	0.6291	0.1072	0.204*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0341 (4)	0.0334 (4)	0.0307 (4)	0.0030 (3)	0.0104 (3)	0.0091 (3)
Cu2	0.0336 (4)	0.0347 (4)	0.0247 (3)	0.0023 (3)	0.0083 (3)	0.0051 (3)
N1	0.028 (2)	0.034 (2)	0.024 (2)	0.005 (2)	0.002 (2)	0.007 (2)
N2	0.032 (2)	0.028 (2)	0.026 (2)	0.002 (2)	0.004 (2)	0.0031 (19)
N3	0.029 (2)	0.038 (3)	0.029 (2)	0.004 (2)	0.004 (2)	0.001 (2)
N4	0.036 (3)	0.036 (3)	0.033 (3)	0.008 (2)	0.012 (2)	0.005 (2)
N5	0.049 (3)	0.037 (3)	0.025 (2)	−0.004 (2)	0.012 (2)	−0.002 (2)
O1	0.033 (2)	0.044 (2)	0.033 (2)	0.0032 (17)	0.0119 (18)	0.0116 (18)
O2	0.036 (2)	0.043 (2)	0.034 (2)	0.0059 (18)	0.0127 (18)	0.0159 (18)
O3	0.034 (2)	0.044 (2)	0.0280 (19)	0.0051 (17)	0.0087 (17)	0.0052 (17)
O4	0.034 (2)	0.045 (2)	0.0258 (19)	0.0071 (17)	0.0084 (17)	0.0092 (17)
O5	0.050 (2)	0.039 (2)	0.033 (2)	−0.0119 (19)	0.0138 (19)	0.0061 (18)
O6	0.061 (3)	0.044 (2)	0.034 (2)	−0.006 (2)	0.020 (2)	−0.0134 (18)
O7	0.071 (5)	0.065 (5)	0.150 (8)	0.000	0.047 (6)	0.000
S1	0.0337 (7)	0.0319 (7)	0.0224 (7)	−0.0006 (6)	0.0089 (6)	0.0004 (6)
C1	0.033 (3)	0.033 (3)	0.026 (3)	0.000 (2)	0.008 (2)	−0.002 (2)
C2	0.030 (3)	0.037 (3)	0.030 (3)	0.000 (2)	0.009 (2)	0.002 (2)
C3	0.039 (3)	0.053 (4)	0.046 (4)	0.004 (3)	0.016 (3)	0.011 (3)
C4	0.030 (3)	0.071 (5)	0.064 (4)	−0.004 (3)	0.016 (3)	0.006 (4)
C5	0.033 (3)	0.079 (5)	0.044 (4)	0.009 (3)	0.007 (3)	0.010 (4)
C6	0.040 (4)	0.053 (4)	0.036 (3)	0.008 (3)	0.007 (3)	0.010 (3)
C7	0.038 (3)	0.028 (3)	0.029 (3)	−0.003 (2)	0.011 (3)	0.000 (2)
C8	0.032 (3)	0.027 (3)	0.029 (3)	0.000 (2)	0.009 (2)	−0.002 (2)
C9	0.036 (3)	0.029 (3)	0.032 (3)	0.003 (2)	0.012 (3)	−0.002 (2)
C10	0.034 (3)	0.040 (3)	0.045 (3)	0.006 (3)	0.006 (3)	0.008 (3)
C11	0.031 (3)	0.041 (3)	0.055 (4)	0.008 (3)	0.006 (3)	0.004 (3)
C12	0.032 (3)	0.035 (3)	0.054 (4)	0.003 (3)	0.016 (3)	−0.007 (3)
C13	0.031 (3)	0.034 (3)	0.037 (3)	−0.004 (2)	0.015 (3)	−0.007 (3)
C14	0.043 (4)	0.053 (4)	0.047 (4)	−0.005 (3)	0.019 (3)	0.006 (3)
C15	0.065 (5)	0.069 (5)	0.063 (5)	−0.011 (4)	0.034 (4)	0.010 (4)
C16	0.054 (5)	0.071 (5)	0.085 (6)	−0.009 (4)	0.037 (4)	0.003 (4)
C17	0.043 (4)	0.057 (4)	0.070 (5)	0.003 (3)	0.022 (4)	−0.002 (4)
C18	0.050 (4)	0.047 (4)	0.060 (4)	0.021 (3)	0.028 (3)	0.021 (3)
C19	0.052 (4)	0.064 (5)	0.080 (5)	0.008 (4)	0.040 (4)	0.027 (4)
C20	0.059 (4)	0.055 (4)	0.067 (5)	0.004 (4)	0.028 (4)	0.032 (4)
C21	0.057 (4)	0.041 (4)	0.066 (4)	0.011 (3)	0.024 (4)	0.023 (3)
C22	0.043 (3)	0.038 (3)	0.044 (4)	0.007 (3)	0.018 (3)	0.008 (3)
C23	0.060 (4)	0.044 (4)	0.027 (3)	−0.003 (3)	0.010 (3)	0.000 (3)
C24	0.066 (4)	0.036 (3)	0.048 (4)	−0.004 (3)	0.011 (3)	−0.002 (3)
C25	0.068 (5)	0.047 (4)	0.055 (4)	−0.004 (3)	0.010 (4)	−0.016 (3)
C26	0.072 (5)	0.066 (5)	0.030 (3)	−0.006 (4)	0.009 (3)	−0.016 (3)
C27	0.064 (4)	0.047 (4)	0.033 (3)	−0.002 (3)	0.017 (3)	0.007 (3)
C28	0.076 (6)	0.081 (7)	0.184 (12)	0.020 (5)	0.058 (7)	0.039 (7)
C29	0.115 (9)	0.170 (12)	0.139 (10)	0.002 (8)	0.063 (8)	0.014 (10)

Geometric parameters (Å, º) top

Cu1—O2	1.888 (3)	C8—C13	1.459 (7)
Cu1—N2	1.957 (4)	C9—C10	1.432 (7)
Cu1—O1	1.964 (3)	C10—C11	1.339 (7)
Cu1—N4	2.008 (4)	C10—H10	0.9300
Cu1—O5ⁱ	2.389 (3)	C11—C12	1.436 (8)
Cu2—O3	2.011 (3)	C11—H11	0.9300
Cu2—N3	2.015 (4)	C12—C17	1.402 (8)
Cu2—N1	2.016 (4)	C12—C13	1.426 (7)
Cu2—O4	2.036 (3)	C13—C14	1.409 (8)
Cu2—N5	2.189 (4)	C14—C15	1.368 (8)
N1—C1	1.328 (6)	C14—H14	0.9300
N1—N2	1.398 (5)	C15—C16	1.388 (9)
N2—C7	1.296 (6)	C15—H15	0.9300
N3—C6	1.325 (6)	C16—C17	1.365 (9)
N3—C2	1.359 (6)	C16—H16	0.9300
N4—C18	1.333 (7)	C17—H17	0.9300
N4—C22	1.341 (6)	C18—C19	1.387 (8)
N5—C27	1.340 (7)	C18—H18	0.9300
N5—C23	1.349 (7)	C19—C20	1.372 (8)
O1—C1	1.273 (6)	C19—H19	0.9300
O2—C9	1.297 (6)	C20—C21	1.367 (8)
O3—S1	1.520 (4)	C20—H20	0.9300
O4—S1	1.510 (3)	C21—C22	1.387 (7)
O5—S1	1.452 (4)	C21—H21	0.9300
O5—Cu1ⁱⁱ	2.389 (3)	C22—H22	0.9300
O6—S1	1.440 (4)	C23—C24	1.371 (8)
O7—C28ⁱⁱⁱ	1.416 (10)	C23—H23	0.9300
O7—C28	1.416 (10)	C24—C25	1.374 (9)
C1—C2	1.486 (7)	C24—H24	0.9300
C2—C3	1.366 (7)	C25—C26	1.366 (9)
C3—C4	1.391 (8)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.389 (8)
C4—C5	1.371 (8)	C26—H26	0.9300
C4—H4	0.9300	C27—H27	0.9300
C5—C6	1.376 (8)	C28—C29	1.547 (13)
C5—H5	0.9300	C28—H28A	0.9700
C6—H6	0.9300	C28—H28B	0.9700
C7—C8	1.434 (7)	C29—H29A	0.9600
C7—H7	0.9300	C29—H29B	0.9600
C8—C9	1.433 (7)	C29—H29C	0.9600

O2—Cu1—N2	90.44 (16)	C7—C8—C13	120.0 (5)
O2—Cu1—O1	169.76 (15)	O2—C9—C10	117.0 (5)
N2—Cu1—O1	81.79 (16)	O2—C9—C8	124.6 (5)
O2—Cu1—N4	92.59 (16)	C10—C9—C8	118.5 (5)
N2—Cu1—N4	163.41 (17)	C11—C10—C9	122.4 (5)
O1—Cu1—N4	93.03 (16)	C11—C10—H10	118.8
O2—Cu1—O5ⁱ	96.92 (14)	C9—C10—H10	118.8
N2—Cu1—O5ⁱ	108.92 (15)	C10—C11—C12	121.8 (5)
O1—Cu1—O5ⁱ	91.92 (14)	C10—C11—H11	119.1
N4—Cu1—O5ⁱ	86.91 (16)	C12—C11—H11	119.1
O3—Cu2—N3	94.91 (16)	C17—C12—C13	119.7 (6)
O3—Cu2—N1	164.13 (16)	C17—C12—C11	121.7 (5)
N3—Cu2—N1	80.49 (17)	C13—C12—C11	118.6 (5)
O3—Cu2—O4	70.46 (13)	C14—C13—C12	117.0 (5)
N3—Cu2—O4	150.44 (16)	C14—C13—C8	123.3 (5)
N1—Cu2—O4	106.43 (15)	C12—C13—C8	119.7 (5)
O3—Cu2—N5	93.57 (15)	C15—C14—C13	121.7 (6)
N3—Cu2—N5	107.27 (17)	C15—C14—H14	119.1
N1—Cu2—N5	102.30 (16)	C13—C14—H14	119.1
O4—Cu2—N5	99.37 (16)	C14—C15—C16	120.9 (6)
C1—N1—N2	110.1 (4)	C14—C15—H15	119.6
C1—N1—Cu2	115.5 (3)	C16—C15—H15	119.6
N2—N1—Cu2	134.3 (3)	C17—C16—C15	119.3 (6)
C7—N2—N1	118.2 (4)	C17—C16—H16	120.3
C7—N2—Cu1	128.3 (4)	C15—C16—H16	120.3
N1—N2—Cu1	112.8 (3)	C16—C17—C12	121.4 (6)
C6—N3—C2	117.8 (5)	C16—C17—H17	119.3
C6—N3—Cu2	127.3 (4)	C12—C17—H17	119.3
C2—N3—Cu2	114.7 (3)	N4—C18—C19	123.0 (5)
C18—N4—C22	117.6 (5)	N4—C18—H18	118.5
C18—N4—Cu1	120.9 (4)	C19—C18—H18	118.5
C22—N4—Cu1	121.0 (4)	C20—C19—C18	118.8 (6)
C27—N5—C23	116.2 (5)	C20—C19—H19	120.6
C27—N5—Cu2	122.6 (4)	C18—C19—H19	120.6
C23—N5—Cu2	121.1 (3)	C21—C20—C19	118.8 (6)
C1—O1—Cu1	109.5 (3)	C21—C20—H20	120.6
C9—O2—Cu1	130.7 (3)	C19—C20—H20	120.6
S1—O3—Cu2	94.59 (17)	C20—C21—C22	119.4 (6)
S1—O4—Cu2	93.93 (17)	C20—C21—H21	120.3
S1—O5—Cu1ⁱⁱ	135.4 (2)	C22—C21—H21	120.3
C28ⁱⁱⁱ—O7—C28	110.9 (11)	N4—C22—C21	122.3 (5)
O6—S1—O5	112.6 (2)	N4—C22—H22	118.8
O6—S1—O4	111.3 (2)	C21—C22—H22	118.8
O5—S1—O4	110.4 (2)	N5—C23—C24	123.9 (5)
O6—S1—O3	110.2 (2)	N5—C23—H23	118.0
O5—S1—O3	111.0 (2)	C24—C23—H23	118.0
O4—S1—O3	100.8 (2)	C23—C24—C25	118.2 (6)
O1—C1—N1	125.7 (5)	C23—C24—H24	120.9
O1—C1—C2	119.5 (5)	C25—C24—H24	120.9
N1—C1—C2	114.8 (5)	C26—C25—C24	120.0 (6)
N3—C2—C3	122.6 (5)	C26—C25—H25	120.0
N3—C2—C1	114.3 (4)	C24—C25—H25	120.0
C3—C2—C1	123.1 (5)	C25—C26—C27	118.1 (6)
C2—C3—C4	118.6 (6)	C25—C26—H26	121.0
C2—C3—H3	120.7	C27—C26—H26	121.0
C4—C3—H3	120.7	N5—C27—C26	123.6 (6)
C5—C4—C3	118.9 (6)	N5—C27—H27	118.2
C5—C4—H4	120.5	C26—C27—H27	118.2
C3—C4—H4	120.5	O7—C28—C29	107.9 (8)
C4—C5—C6	119.1 (6)	O7—C28—H28A	110.1
C4—C5—H5	120.5	C29—C28—H28A	110.1
C6—C5—H5	120.5	O7—C28—H28B	110.1
N3—C6—C5	123.0 (6)	C29—C28—H28B	110.1
N3—C6—H6	118.5	H28A—C28—H28B	108.4
C5—C6—H6	118.5	C28—C29—H29A	109.5
N2—C7—C8	124.8 (5)	C28—C29—H29B	109.5
N2—C7—H7	117.6	H29A—C29—H29B	109.5
C8—C7—H7	117.6	C28—C29—H29C	109.5
C9—C8—C7	120.9 (5)	H29A—C29—H29C	109.5
C9—C8—C13	119.1 (5)	H29B—C29—H29C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2^iv	0.93	2.46	3.386 (7)	174
C5—H5···O3^v	0.93	2.43	3.340 (7)	165
C19—H19···O7^vi	0.93	2.46	3.266 (7)	145

Symmetry codes: (iv) −x+1/2, y+1/2, −z+1/2; (v) −x, y, −z−1/2; (vi) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₇H₁₁N₃O)(SO₄)(C₅H₅N)₂]·0.5C₄H₁₀O
M_r	707.69
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	26.484 (2), 14.0374 (15), 16.8083 (17)
β (°)	108.404 (2)
V (Å³)	5929.2 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.38 × 0.32 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.589, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	14633, 5215, 3268
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.01
No. of reflections	5215
No. of parameters	394
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.052P)² + 19.1978P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.49

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O2	1.888 (3)	Cu2—O3	2.011 (3)
Cu1—N2	1.957 (4)	Cu2—N3	2.015 (4)
Cu1—O1	1.964 (3)	Cu2—N1	2.016 (4)
Cu1—N4	2.008 (4)	Cu2—O4	2.036 (3)
Cu1—O5ⁱ	2.389 (3)	Cu2—N5	2.189 (4)

Symmetry code: (i) x, −y+2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2ⁱⁱ	0.93	2.46	3.386 (7)	174.2
C5—H5···O3ⁱⁱⁱ	0.93	2.43	3.340 (7)	165.2
C19—H19···O7^iv	0.93	2.46	3.266 (7)	144.7

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

Acknowledgements

We acknowledge the financial support of the National Natural Science Foundation of China (grant No. 20671048).

References

Armstrong, C. M., Bernhardt, P. V., Chin, P. & Richardson, D. R. (2003). Eur. J. Inorg. Chem. pp. 1145–1156. CSD CrossRef Google Scholar
Bai, Y., Dang, D. B., Cao, X., Duan, C. Y. & Meng, Q. J. (2006). Inorg. Chem. Commun. pp. 86–89. Web of Science CSD CrossRef 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

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Volume 65| Part 5| May 2009| Page m520

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

catena-Poly[[[pyridinecopper(II)]-(μ-2-oxido­naphthalene-1-carbaldehyde pico­linoylhydrazonato)-[pyridinecopper(II)]-μ-sulfato] di­ethyl ether hemisolvate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[pyridinecopper(II)]-(μ-2-oxidonaphthalene-1-carbaldehyde picolinoylhydrazonato)-[pyridinecopper(II)]-μ-sulfato] diethyl ether hemisolvate]