catena-Poly[[aqua­(2,2′-bipyridine-κ2N,N′)copper(II)]-μ-5-nitro­isophthalato-κ3O1,O1′:O3]

Hao, L.; Liu, X.

doi:10.1107/S1600536808035150

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1500

doi:10.1107/S1600536808035150

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: catena-Poly[[aqua(2,2′-bipyridine-κ²N,N′)copper(II)]-μ-5-nitroisophthalato-κ³O¹,O^1′:O³]

Lujiang Hao ^a ^* and Xia Liu ^b

^aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and ^bMaize Research Insitute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 28 September 2008; accepted 28 October 2008; online 8 November 2008)

In the asymmetric unit of the title compound, [Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]_n, there are two symmetry-independent one-dimensional coordination polymers related by a non-crystallographic inversion center. Within the polymers, the Cu^IIatoms, coordinated by the water molecule and the chelating 2,2′-bipyridine ligands, are bridged by 5-nitrobenzene-1,3-dicarboxylate dianions which act as tridentate ligands; the carboxylate groups exhibit monodentate and symmetric bidentate coordination modes. The Cu^II atoms show a strongly distorted octahedral coordination geometry. In the crystal structure, the two symmetry-independent coordination polymers form another one-dimensional polymeric structure via O—H⋯O hydrogen bonds between coordinated water molecules and carboxylate groups.

Related literature

For the uses of carboxylic acids in materials science, see: Church & Halvorson (1959 ), and in biological systems, see: Okabe & Oya (2000 ); Kim et al. (2001 ).

Experimental

Crystal data

[Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]
M_r = 446.85
Monoclinic, P 2₁ /n
a = 10.1326 (10) Å
b = 23.263 (3) Å
c = 15.6087 (15) Å
β = 97.28 (2)°
V = 3649.6 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.865, T_max = 0.907
18862 measured reflections
6694 independent reflections
5089 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.123
S = 1.00
6694 reflections
535 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H1W⋯O2ⁱ	0.83 (4)	1.98 (2)	2.742 (3)	153 (4)
O1—H4W⋯O10ⁱⁱ	0.82 (3)	1.95 (2)	2.724 (3)	158 (4)
O12—H2W⋯O5	0.82 (4)	2.07 (3)	2.760 (3)	141 (4)
O1—H3W⋯O13	0.83 (3)	2.13 (3)	2.778 (3)	135 (4)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536808035150/gk2170sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035150/gk2170Isup2.hkl

checkCIF report

Comment top

In recent years, carboxylic acids have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959) and in biological systems (Okabe & Oya, 2000). For example, Kim et al. (2001) focused on the syntheses of transition metal complexes containing benzene carboxylate and rigid aromatic pyridine ligands in order to study their electronic conductivity and magnetic properties. The importance of transition metal dicarboxylate complexes motivated us to pursue synthetic strategies for these compounds, using 5-nitroisophthalic acid as a polydentate ligand. Here we report the synthesis and X-ray crystal structure analysis of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The title compound, [Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]_n is a one-dimensional coordination polymer (Fig. 2). There are two symmetry independent 1D polymers in the crystal. The Cu(II) atom shows a strongly disordered coordination geometry. It is coordinated by two carboxylate groups from two different 5-nitroisophthalate ligands, 2,2'-bipyridyl and water molecule. The carboxylate groups act in a monodentate and bidentate coordination modes.The symmetry independent polymeric chains are linked via O-H···O hydrogen bonds (Table 1).

Related literature top

For the uses of carboxylic acids in materials science, see: Church & Halvorson (1959), and in biological systems, see: Okabe & Oya (2000); Kim et al. (2001).

Experimental top

A mixture of copper dichloride (0.5 mmol), 2,2'-bipyridine (0.5 mmol), and 5-nitroisophthalic acid (0.5 mmol) in H₂O (8 ml) and ethanol (8 ml) was sealed in a 25 ml Teflon-lined stainless steel autoclave and kept at 413 K for three days. Blue crystals were obtained after cooling to room temperature (yield 27%). Anal. Calc. for C₁₈H₁₃CuN₃O₇: C 48.34, H 2.91, N 10.74%; Found: C 48.30, H 2.84, N 10.69%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. A view of the title structure showing the atomic numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. One of the symmetry-independent coordination polymers

catena-Poly[[aqua(2,2'-bipyridine-κ²N,N')copper(II)]- µ-5-nitroisophthalato-κ³O¹,O^1':O³] top

Crystal data top

[Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]	F(000) = 1816
M_r = 446.85	D_x = 1.627 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6694 reflections
a = 10.1326 (10) Å	θ = 1.8–25.5°
b = 23.263 (3) Å	µ = 1.25 mm⁻¹
c = 15.6087 (15) Å	T = 293 K
β = 97.28 (2)°	Block, blue
V = 3649.6 (7) Å³	0.12 × 0.10 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	6694 independent reflections
Radiation source: fine-focus sealed tube	5089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
T_min = 0.865, T_max = 0.907	k = −28→22
18862 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.075P)² + 2.4671P] where P = (F_o² + 2F_c²)/3
6694 reflections	(Δ/σ)_max = 0.003
535 parameters	Δρ_max = 0.83 e Å⁻³
6 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]	V = 3649.6 (7) Å³
M_r = 446.85	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1326 (10) Å	µ = 1.25 mm⁻¹
b = 23.263 (3) Å	T = 293 K
c = 15.6087 (15) Å	0.12 × 0.10 × 0.08 mm
β = 97.28 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6694 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5089 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.907	R_int = 0.025
18862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	6 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.83 e Å⁻³
6694 reflections	Δρ_min = −0.40 e Å⁻³
535 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
Cu1	1.16168 (4)	0.154431 (15)	0.85573 (3)	0.02711 (13)
Cu2	0.12372 (4)	0.354405 (16)	0.93350 (3)	0.03053 (13)
C1	1.1959 (4)	0.07213 (16)	1.0079 (2)	0.0457 (9)
H1	1.2145	0.1048	1.0416	0.055*
C2	1.2039 (5)	0.0193 (2)	1.0471 (3)	0.0635 (13)
H2	1.2268	0.0161	1.1065	0.076*
C3	1.1773 (5)	−0.02890 (18)	0.9970 (3)	0.0634 (13)
H3	1.1810	−0.0651	1.0224	0.076*
C4	1.1452 (4)	−0.02334 (16)	0.9089 (3)	0.0481 (10)
H4	1.1282	−0.0556	0.8741	0.058*
C5	1.1388 (3)	0.03117 (13)	0.8732 (2)	0.0291 (7)
C6	1.1072 (3)	0.04138 (13)	0.7785 (2)	0.0266 (7)
C7	1.0796 (3)	−0.00183 (15)	0.7180 (2)	0.0376 (8)
H7	1.0788	−0.0401	0.7354	0.045*
C8	1.0527 (4)	0.01249 (16)	0.6306 (2)	0.0408 (9)
H8	1.0328	−0.0160	0.5891	0.049*
C9	1.0562 (4)	0.06932 (16)	0.6068 (2)	0.0415 (9)
H9	1.0383	0.0800	0.5491	0.050*
C10	1.0866 (3)	0.11017 (14)	0.6700 (2)	0.0337 (8)
H10	1.0889	0.1486	0.6536	0.040*
C11	0.3761 (3)	0.19406 (14)	0.8105 (2)	0.0284 (7)
C12	0.8756 (3)	0.17568 (14)	0.8380 (2)	0.0286 (7)
C13	0.7500 (3)	0.20954 (13)	0.80617 (19)	0.0232 (6)
C14	0.6258 (3)	0.18759 (13)	0.8202 (2)	0.0252 (6)
H14	0.6213	0.1526	0.8484	0.030*
C15	0.5081 (3)	0.21767 (13)	0.79223 (19)	0.0228 (6)
C16	0.5143 (3)	0.27058 (14)	0.7520 (2)	0.0287 (7)
H16	0.4375	0.2912	0.7332	0.034*
C17	0.6391 (3)	0.29176 (14)	0.7409 (2)	0.0300 (7)
C18	0.7573 (3)	0.26273 (13)	0.7665 (2)	0.0268 (7)
H18	0.8388	0.2784	0.7574	0.032*
C19	0.0858 (4)	0.43908 (16)	0.7844 (3)	0.0419 (9)
H19	0.0717	0.4066	0.7497	0.050*
C20	0.0710 (4)	0.49282 (18)	0.7464 (3)	0.0506 (10)
H20	0.0493	0.4965	0.6869	0.061*
C21	0.0891 (4)	0.54045 (17)	0.7982 (3)	0.0530 (11)
H21	0.0801	0.5770	0.7741	0.064*
C22	0.1206 (3)	0.53393 (15)	0.8859 (3)	0.0437 (9)
H22	0.1312	0.5660	0.9217	0.052*
C23	0.1365 (3)	0.47885 (13)	0.9207 (2)	0.0331 (8)
C24	0.1701 (3)	0.46692 (14)	1.0141 (2)	0.0312 (7)
C25	0.1994 (4)	0.50930 (15)	1.0773 (3)	0.0450 (10)
H25	0.1976	0.5480	1.0620	0.054*
C26	0.2313 (4)	0.49311 (18)	1.1632 (3)	0.0505 (10)
H26	0.2502	0.5209	1.2059	0.061*
C27	0.2346 (4)	0.43618 (19)	1.1844 (3)	0.0502 (10)
H27	0.2573	0.4245	1.2414	0.060*
C28	0.2036 (4)	0.39641 (17)	1.1200 (2)	0.0423 (9)
H28	0.2048	0.3577	1.1348	0.051*
C29	0.4118 (3)	0.33262 (14)	0.9445 (2)	0.0276 (7)
C30	0.5355 (3)	0.29913 (13)	0.9800 (2)	0.0245 (7)
C31	0.6609 (3)	0.31950 (13)	0.9659 (2)	0.0247 (6)
H31	0.6668	0.3529	0.9339	0.030*
C32	0.7773 (3)	0.29078 (12)	0.9988 (2)	0.0230 (6)
C33	0.7701 (3)	0.24090 (13)	1.0462 (2)	0.0281 (7)
H33	0.8466	0.2213	1.0687	0.034*
C34	0.6445 (3)	0.22111 (13)	1.0589 (2)	0.0274 (7)
C35	0.5281 (3)	0.24928 (14)	1.0278 (2)	0.0273 (7)
H35	0.4461	0.2350	1.0387	0.033*
C36	0.9110 (3)	0.31370 (13)	0.9804 (2)	0.0265 (7)
N1	1.1618 (3)	0.07821 (11)	0.92194 (18)	0.0308 (6)
N2	1.1133 (2)	0.09711 (10)	0.75448 (17)	0.0256 (6)
N3	0.1197 (3)	0.43222 (12)	0.86995 (18)	0.0310 (6)
N4	0.1716 (3)	0.41090 (11)	1.03653 (19)	0.0315 (6)
N5	0.6350 (3)	0.16771 (13)	1.1080 (2)	0.0421 (8)
N6	0.6481 (4)	0.34942 (14)	0.7038 (2)	0.0526 (9)
O1	0.0918 (2)	0.30549 (9)	0.81941 (17)	0.0320 (5)
O2	0.3006 (2)	0.31188 (9)	0.96166 (16)	0.0358 (6)
O3	0.4241 (3)	0.37683 (12)	0.90419 (19)	0.0532 (7)
O4	0.9139 (2)	0.35925 (10)	0.93797 (18)	0.0392 (6)
O5	1.0167 (2)	0.28721 (10)	1.00723 (16)	0.0360 (6)
O6	0.5265 (3)	0.14511 (15)	1.1064 (3)	0.0852 (13)
O7	0.7369 (3)	0.14842 (12)	1.1487 (2)	0.0579 (8)
O8	0.5457 (3)	0.37104 (19)	0.6687 (4)	0.128 (2)
O9	0.7554 (3)	0.37294 (13)	0.7091 (2)	0.0734 (10)
O10	0.9862 (2)	0.19817 (9)	0.82626 (16)	0.0328 (5)
O11	0.8637 (3)	0.12791 (13)	0.8686 (2)	0.0653 (9)
O12	1.1948 (2)	0.20384 (9)	0.97015 (16)	0.0319 (5)
O13	0.2693 (2)	0.22031 (10)	0.78406 (16)	0.0369 (6)
O14	0.3736 (2)	0.14837 (10)	0.85273 (17)	0.0390 (6)
H1W	1.245 (4)	0.2303 (13)	0.960 (3)	0.080*
H2W	1.132 (3)	0.2151 (17)	0.994 (3)	0.080*
H3W	0.157 (3)	0.2969 (18)	0.795 (3)	0.080*
H4W	0.042 (4)	0.2781 (13)	0.824 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0215 (2)	0.0234 (2)	0.0363 (2)	0.00148 (15)	0.00314 (16)	0.00163 (15)
Cu2	0.0210 (2)	0.0245 (2)	0.0466 (3)	0.00113 (15)	0.00654 (18)	0.00113 (16)
C1	0.065 (3)	0.041 (2)	0.031 (2)	0.0004 (19)	0.0076 (18)	0.0047 (16)
C2	0.096 (4)	0.060 (3)	0.033 (2)	0.006 (3)	0.007 (2)	0.014 (2)
C3	0.092 (4)	0.040 (2)	0.059 (3)	0.004 (2)	0.012 (3)	0.031 (2)
C4	0.063 (3)	0.0273 (18)	0.053 (3)	−0.0023 (17)	0.005 (2)	0.0101 (16)
C5	0.0230 (16)	0.0246 (16)	0.0396 (19)	−0.0009 (12)	0.0039 (14)	0.0044 (13)
C6	0.0201 (15)	0.0235 (15)	0.0361 (18)	−0.0006 (12)	0.0037 (13)	0.0017 (13)
C7	0.0313 (18)	0.0270 (17)	0.054 (2)	−0.0024 (14)	0.0052 (16)	−0.0048 (16)
C8	0.036 (2)	0.043 (2)	0.042 (2)	−0.0019 (16)	0.0012 (16)	−0.0122 (16)
C9	0.041 (2)	0.048 (2)	0.034 (2)	0.0023 (17)	−0.0006 (16)	−0.0037 (16)
C10	0.0362 (19)	0.0319 (17)	0.0323 (19)	0.0054 (14)	0.0015 (15)	0.0049 (14)
C11	0.0197 (16)	0.0332 (17)	0.0332 (18)	−0.0034 (13)	0.0071 (13)	−0.0116 (14)
C12	0.0172 (16)	0.0347 (18)	0.0332 (18)	0.0028 (13)	0.0008 (13)	0.0056 (14)
C13	0.0147 (14)	0.0287 (16)	0.0257 (16)	0.0017 (12)	0.0008 (12)	0.0000 (12)
C14	0.0219 (16)	0.0261 (15)	0.0283 (16)	−0.0010 (12)	0.0054 (13)	−0.0006 (13)
C15	0.0156 (14)	0.0280 (15)	0.0252 (16)	−0.0013 (12)	0.0041 (12)	−0.0061 (12)
C16	0.0173 (15)	0.0372 (18)	0.0314 (18)	0.0093 (13)	0.0027 (13)	0.0019 (14)
C17	0.0269 (17)	0.0298 (16)	0.0343 (18)	0.0035 (13)	0.0078 (14)	0.0110 (13)
C18	0.0156 (14)	0.0337 (17)	0.0314 (18)	−0.0016 (12)	0.0039 (12)	0.0049 (13)
C19	0.040 (2)	0.040 (2)	0.049 (2)	0.0029 (16)	0.0137 (17)	0.0071 (17)
C20	0.043 (2)	0.058 (3)	0.052 (2)	0.0069 (19)	0.0135 (19)	0.024 (2)
C21	0.040 (2)	0.034 (2)	0.088 (3)	0.0026 (17)	0.021 (2)	0.027 (2)
C22	0.031 (2)	0.0237 (17)	0.078 (3)	0.0018 (14)	0.0160 (19)	0.0050 (18)
C23	0.0160 (15)	0.0232 (16)	0.062 (2)	0.0000 (12)	0.0137 (15)	0.0010 (15)
C24	0.0149 (15)	0.0292 (17)	0.051 (2)	−0.0005 (12)	0.0090 (14)	−0.0043 (15)
C25	0.032 (2)	0.0279 (18)	0.077 (3)	−0.0019 (15)	0.0121 (19)	−0.0106 (18)
C26	0.034 (2)	0.059 (3)	0.058 (3)	−0.0019 (18)	0.0037 (19)	−0.021 (2)
C27	0.039 (2)	0.064 (3)	0.048 (2)	0.0050 (19)	0.0075 (18)	−0.006 (2)
C28	0.037 (2)	0.043 (2)	0.047 (2)	0.0056 (17)	0.0058 (17)	−0.0007 (17)
C29	0.0166 (15)	0.0327 (17)	0.0326 (18)	0.0031 (13)	−0.0002 (13)	−0.0046 (14)
C30	0.0155 (15)	0.0300 (16)	0.0279 (17)	0.0005 (12)	0.0024 (12)	−0.0048 (12)
C31	0.0192 (15)	0.0241 (15)	0.0312 (17)	−0.0012 (12)	0.0053 (12)	−0.0004 (12)
C32	0.0156 (15)	0.0266 (15)	0.0276 (16)	−0.0004 (11)	0.0059 (12)	−0.0043 (12)
C33	0.0187 (15)	0.0345 (17)	0.0305 (18)	0.0020 (13)	0.0017 (13)	0.0005 (13)
C34	0.0216 (16)	0.0316 (16)	0.0288 (17)	−0.0020 (13)	0.0027 (13)	0.0043 (13)
C35	0.0175 (15)	0.0342 (17)	0.0307 (18)	−0.0059 (13)	0.0050 (13)	0.0015 (13)
C36	0.0140 (15)	0.0294 (16)	0.0370 (18)	0.0009 (12)	0.0073 (13)	−0.0085 (14)
N1	0.0305 (15)	0.0280 (14)	0.0347 (16)	−0.0011 (11)	0.0068 (12)	0.0048 (11)
N2	0.0213 (13)	0.0233 (13)	0.0320 (15)	0.0026 (10)	0.0030 (11)	−0.0005 (11)
N3	0.0216 (14)	0.0277 (14)	0.0446 (18)	0.0022 (11)	0.0075 (12)	0.0052 (12)
N4	0.0239 (14)	0.0268 (14)	0.0445 (18)	0.0028 (11)	0.0071 (12)	−0.0015 (12)
N5	0.0325 (17)	0.0448 (18)	0.0488 (19)	−0.0039 (14)	0.0042 (14)	0.0181 (14)
N6	0.044 (2)	0.049 (2)	0.068 (2)	0.0143 (16)	0.0185 (17)	0.0321 (17)
O1	0.0243 (12)	0.0261 (12)	0.0455 (14)	0.0024 (9)	0.0044 (10)	−0.0001 (10)
O2	0.0148 (11)	0.0301 (12)	0.0621 (16)	0.0023 (9)	0.0033 (10)	−0.0029 (11)
O3	0.0327 (14)	0.0511 (17)	0.075 (2)	0.0086 (12)	0.0035 (13)	0.0290 (15)
O4	0.0241 (12)	0.0291 (12)	0.0669 (17)	−0.0021 (9)	0.0153 (12)	0.0085 (11)
O5	0.0157 (11)	0.0366 (12)	0.0564 (16)	0.0029 (9)	0.0072 (10)	−0.0003 (11)
O6	0.0464 (19)	0.086 (2)	0.116 (3)	−0.0290 (17)	−0.0150 (19)	0.065 (2)
O7	0.0401 (16)	0.0511 (17)	0.083 (2)	0.0105 (13)	0.0080 (15)	0.0336 (15)
O8	0.046 (2)	0.117 (3)	0.226 (5)	0.037 (2)	0.036 (3)	0.131 (4)
O9	0.061 (2)	0.0534 (18)	0.102 (3)	−0.0163 (16)	−0.0027 (19)	0.0388 (18)
O10	0.0121 (10)	0.0274 (11)	0.0583 (15)	0.0017 (8)	0.0015 (10)	−0.0021 (10)
O11	0.0313 (15)	0.0648 (19)	0.101 (2)	0.0135 (13)	0.0130 (15)	0.0564 (18)
O12	0.0267 (12)	0.0261 (11)	0.0415 (14)	0.0039 (9)	−0.0003 (10)	−0.0027 (10)
O13	0.0157 (11)	0.0404 (13)	0.0550 (16)	0.0031 (10)	0.0066 (10)	−0.0012 (11)
O14	0.0223 (12)	0.0378 (14)	0.0583 (16)	−0.0027 (10)	0.0103 (11)	0.0048 (11)

Geometric parameters (Å, º) top

Cu1—O10	2.049 (2)	C19—N3	1.345 (5)
Cu1—N1	2.052 (3)	C19—C20	1.384 (5)
Cu1—N2	2.078 (3)	C19—H19	0.9300
Cu1—O12	2.115 (2)	C20—C21	1.371 (6)
Cu1—O14ⁱ	2.158 (2)	C20—H20	0.9300
Cu1—O13ⁱ	2.258 (2)	C21—C22	1.374 (6)
Cu2—O2	2.046 (2)	C21—H21	0.9300
Cu2—N3	2.062 (3)	C22—C23	1.393 (5)
Cu2—N4	2.086 (3)	C22—H22	0.9300
Cu2—O1	2.104 (2)	C23—N3	1.341 (4)
Cu2—O4ⁱⁱ	2.139 (2)	C23—C24	1.481 (5)
Cu2—O5ⁱⁱ	2.294 (2)	C24—N4	1.349 (4)
C1—N1	1.350 (5)	C24—C25	1.400 (5)
C1—C2	1.372 (6)	C25—C26	1.391 (6)
C1—H1	0.9300	C25—H25	0.9300
C2—C3	1.373 (6)	C26—C27	1.364 (6)
C2—H2	0.9300	C26—H26	0.9300
C3—C4	1.379 (6)	C27—C28	1.373 (6)
C3—H3	0.9300	C27—H27	0.9300
C4—C5	1.383 (5)	C28—N4	1.346 (5)
C4—H4	0.9300	C28—H28	0.9300
C5—N1	1.337 (4)	C29—O3	1.220 (4)
C5—C6	1.491 (5)	C29—O2	1.284 (4)
C6—N2	1.353 (4)	C29—C30	1.520 (4)
C6—C7	1.383 (5)	C30—C35	1.386 (4)
C7—C8	1.398 (5)	C30—C31	1.400 (4)
C7—H7	0.9300	C31—C32	1.395 (4)
C8—C9	1.375 (5)	C31—H31	0.9300
C8—H8	0.9300	C32—C33	1.382 (4)
C9—C10	1.375 (5)	C32—C36	1.518 (4)
C9—H9	0.9300	C33—C34	1.391 (4)
C10—N2	1.347 (4)	C33—H33	0.9300
C10—H10	0.9300	C34—C35	1.383 (4)
C11—O14	1.253 (4)	C34—N5	1.470 (4)
C11—O13	1.265 (4)	C35—H35	0.9300
C11—C15	1.506 (4)	C36—O4	1.252 (4)
C12—O11	1.222 (4)	C36—O5	1.260 (4)
C12—O10	1.271 (4)	N5—O6	1.216 (4)
C12—C13	1.525 (4)	N5—O7	1.226 (4)
C13—C18	1.390 (4)	N6—O9	1.211 (4)
C13—C14	1.401 (4)	N6—O8	1.218 (4)
C14—C15	1.404 (4)	O1—H3W	0.83 (3)
C14—H14	0.9300	O1—H4W	0.82 (3)
C15—C16	1.387 (4)	O4—Cu2ⁱ	2.139 (2)
C16—C17	1.388 (5)	O5—Cu2ⁱ	2.294 (2)
C16—H16	0.9300	O12—H1W	0.82 (4)
C17—C18	1.389 (4)	O12—H2W	0.82 (4)
C17—N6	1.468 (4)	O13—Cu1ⁱⁱ	2.258 (2)
C18—H18	0.9300	O14—Cu1ⁱⁱ	2.158 (2)

O10—Cu1—N1	119.16 (10)	N3—C19—C20	122.2 (4)
O10—Cu1—N2	91.92 (10)	N3—C19—H19	118.9
N1—Cu1—N2	79.26 (10)	C20—C19—H19	118.9
O10—Cu1—O12	87.71 (9)	C21—C20—C19	118.5 (4)
N1—Cu1—O12	93.12 (10)	C21—C20—H20	120.7
N2—Cu1—O12	171.06 (10)	C19—C20—H20	120.7
O10—Cu1—O14ⁱ	149.84 (9)	C20—C21—C22	119.7 (3)
N1—Cu1—O14ⁱ	90.99 (10)	C20—C21—H21	120.1
N2—Cu1—O14ⁱ	94.65 (10)	C22—C21—H21	120.1
O12—Cu1—O14ⁱ	90.11 (10)	C21—C22—C23	119.4 (4)
O10—Cu1—O13ⁱ	90.66 (9)	C21—C22—H22	120.3
N1—Cu1—O13ⁱ	150.04 (10)	C23—C22—H22	120.3
N2—Cu1—O13ⁱ	98.11 (10)	N3—C23—C22	120.9 (4)
O12—Cu1—O13ⁱ	90.83 (9)	N3—C23—C24	115.2 (3)
O14ⁱ—Cu1—O13ⁱ	59.29 (8)	C22—C23—C24	123.8 (3)
O2—Cu2—N3	119.41 (10)	N4—C24—C25	120.2 (3)
O2—Cu2—N4	91.57 (10)	N4—C24—C23	115.5 (3)
N3—Cu2—N4	78.83 (11)	C25—C24—C23	124.3 (3)
O2—Cu2—O1	87.52 (9)	C26—C25—C24	119.4 (4)
N3—Cu2—O1	94.37 (10)	C26—C25—H25	120.3
N4—Cu2—O1	171.62 (10)	C24—C25—H25	120.3
O2—Cu2—O4ⁱⁱ	149.99 (9)	C27—C26—C25	119.5 (4)
N3—Cu2—O4ⁱⁱ	90.60 (9)	C27—C26—H26	120.3
N4—Cu2—O4ⁱⁱ	94.38 (10)	C25—C26—H26	120.3
O1—Cu2—O4ⁱⁱ	90.54 (10)	C26—C27—C28	118.7 (4)
O2—Cu2—O5ⁱⁱ	91.14 (9)	C26—C27—H27	120.6
N3—Cu2—O5ⁱⁱ	149.09 (9)	C28—C27—H27	120.6
N4—Cu2—O5ⁱⁱ	96.95 (10)	N4—C28—C27	123.0 (4)
O1—Cu2—O5ⁱⁱ	91.40 (9)	N4—C28—H28	118.5
O4ⁱⁱ—Cu2—O5ⁱⁱ	58.96 (8)	C27—C28—H28	118.5
N1—C1—C2	122.1 (4)	O3—C29—O2	125.0 (3)
N1—C1—H1	119.0	O3—C29—C30	119.1 (3)
C2—C1—H1	119.0	O2—C29—C30	115.9 (3)
C1—C2—C3	118.7 (4)	C35—C30—C31	118.7 (3)
C1—C2—H2	120.6	C35—C30—C29	121.8 (3)
C3—C2—H2	120.6	C31—C30—C29	119.5 (3)
C2—C3—C4	119.7 (4)	C32—C31—C30	121.5 (3)
C2—C3—H3	120.1	C32—C31—H31	119.3
C4—C3—H3	120.1	C30—C31—H31	119.3
C3—C4—C5	118.8 (4)	C33—C32—C31	120.0 (3)
C3—C4—H4	120.6	C33—C32—C36	120.3 (3)
C5—C4—H4	120.6	C31—C32—C36	119.7 (3)
N1—C5—C4	121.7 (3)	C32—C33—C34	117.7 (3)
N1—C5—C6	115.7 (3)	C32—C33—H33	121.1
C4—C5—C6	122.6 (3)	C34—C33—H33	121.1
N2—C6—C7	121.3 (3)	C35—C34—C33	123.2 (3)
N2—C6—C5	114.6 (3)	C35—C34—N5	118.3 (3)
C7—C6—C5	124.1 (3)	C33—C34—N5	118.4 (3)
C6—C7—C8	119.4 (3)	C34—C35—C30	118.9 (3)
C6—C7—H7	120.3	C34—C35—H35	120.5
C8—C7—H7	120.3	C30—C35—H35	120.5
C9—C8—C7	118.9 (3)	O4—C36—O5	121.0 (3)
C9—C8—H8	120.5	O4—C36—C32	118.6 (3)
C7—C8—H8	120.5	O5—C36—C32	120.4 (3)
C8—C9—C10	118.8 (3)	O4—C36—Cu2ⁱ	57.03 (16)
C8—C9—H9	120.6	O5—C36—Cu2ⁱ	64.09 (16)
C10—C9—H9	120.6	C32—C36—Cu2ⁱ	174.0 (2)
N2—C10—C9	123.0 (3)	C5—N1—C1	119.0 (3)
N2—C10—H10	118.5	C5—N1—Cu1	115.6 (2)
C9—C10—H10	118.5	C1—N1—Cu1	125.1 (2)
O14—C11—O13	120.5 (3)	C10—N2—C6	118.5 (3)
O14—C11—C15	119.1 (3)	C10—N2—Cu1	126.8 (2)
O13—C11—C15	120.4 (3)	C6—N2—Cu1	114.8 (2)
O14—C11—Cu1ⁱⁱ	58.05 (16)	C23—N3—C19	119.2 (3)
O13—C11—Cu1ⁱⁱ	62.60 (17)	C23—N3—Cu2	115.6 (2)
C15—C11—Cu1ⁱⁱ	174.8 (2)	C19—N3—Cu2	124.6 (2)
O11—C12—O10	124.3 (3)	C28—N4—C24	119.1 (3)
O11—C12—C13	118.5 (3)	C28—N4—Cu2	126.4 (2)
O10—C12—C13	117.1 (3)	C24—N4—Cu2	114.5 (2)
C18—C13—C14	119.6 (3)	O6—N5—O7	123.5 (3)
C18—C13—C12	121.0 (3)	O6—N5—C34	118.3 (3)
C14—C13—C12	119.4 (3)	O7—N5—C34	118.2 (3)
C13—C14—C15	121.0 (3)	O9—N6—O8	123.4 (3)
C13—C14—H14	119.5	O9—N6—C17	119.1 (3)
C15—C14—H14	119.5	O8—N6—C17	117.6 (4)
C16—C15—C14	119.8 (3)	Cu2—O1—H3W	118 (3)
C16—C15—C11	120.1 (3)	Cu2—O1—H4W	112 (3)
C14—C15—C11	120.0 (3)	H3W—O1—H4W	113 (4)
C15—C16—C17	117.8 (3)	C29—O2—Cu2	122.8 (2)
C15—C16—H16	121.1	C36—O4—Cu2ⁱ	93.58 (18)
C17—C16—H16	121.1	C36—O5—Cu2ⁱ	86.30 (19)
C16—C17—C18	123.9 (3)	C12—O10—Cu1	121.3 (2)
C16—C17—N6	118.4 (3)	Cu1—O12—H1W	106 (3)
C18—C17—N6	117.6 (3)	Cu1—O12—H2W	121 (3)
C13—C18—C17	117.9 (3)	H1W—O12—H2W	112 (4)
C13—C18—H18	121.0	C11—O13—Cu1ⁱⁱ	87.6 (2)
C17—C18—H18	121.0	C11—O14—Cu1ⁱⁱ	92.45 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H1W···O2ⁱ	0.83 (4)	1.98 (2)	2.742 (3)	153 (4)
O1—H4W···O10ⁱⁱ	0.82 (3)	1.95 (2)	2.724 (3)	158 (4)
O12—H2W···O5	0.82 (4)	2.07 (3)	2.760 (3)	141 (4)
O1—H3W···O13	0.83 (3)	2.13 (3)	2.778 (3)	135 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]
M_r	446.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.1326 (10), 23.263 (3), 15.6087 (15)
β (°)	97.28 (2)
V (Å³)	3649.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.865, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	18862, 6694, 5089
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.124, 1.00
No. of reflections	6694
No. of parameters	535
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.40

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H1W···O2ⁱ	0.83 (4)	1.98 (2)	2.742 (3)	153 (4)
O1—H4W···O10ⁱⁱ	0.82 (3)	1.95 (2)	2.724 (3)	158 (4)
O12—H2W···O5	0.82 (4)	2.07 (3)	2.760 (3)	141 (4)
O1—H3W···O13	0.83 (3)	2.13 (3)	2.778 (3)	135 (4)

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

Acknowledgements

This work was supported by the Natural Science Foundation of Shandong Province (grant No. Y2007D39).

References

Bruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Church, B. S. & Halvorson, H. (1959). Nature (London), 183, 124–125. CrossRef PubMed CAS Web of Science Google Scholar
Kim, Y., Lee, E. & Jung, D. Y. (2001). Chem. Mater. 13, 2684–2690. Web of Science CSD CrossRef CAS Google Scholar
Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416–1417. Web of Science CSD CrossRef CAS IUCr Journals 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 64| Part 12| December 2008| Page m1500

doi:10.1107/S1600536808035150

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

Retracted: catena-Poly[[aqua­(2,2′-bi­pyridine-κ2N,N′)copper(II)]-μ-5-nitro­isophthalato-κ3O1,O1′:O3]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: catena-Poly[[aqua(2,2′-bipyridine-κ²N,N′)copper(II)]-μ-5-nitroisophthalato-κ³O¹,O^1′:O³]