catena-Poly[[aqua­(2,2′-bipyridyl)cobalt(II)]-μ-5-nitro­isophthalato]

Liu, Y.; He, Q.; Zhang, X.; Xue, Z.; Lv, C.

doi:10.1107/S1600536808038178

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1605-m1606

doi:10.1107/S1600536808038178

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RETRACTED ARTICLE

This article has been retracted.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

Retracted: catena-Poly[[aqua(2,2′-bipyridyl)cobalt(II)]-μ-5-nitroisophthalato]

Ying Liu,^a ^* Qingpeng He,^a Xianxi Zhang,^a Zechun Xue ^a and Chunyan Lv ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: yllctu@yahoo.com.cn

(Received 13 November 2008; accepted 17 November 2008; online 22 November 2008)

In the crystal structure of the title compound, [Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]_n, there are two symmetry-independent one-dimensional coordination polymers, which are approximately related by noncrystallographic inversion symmetry. Each zigzag chain is constructed from one Co^II ion, one O-monodentate 5-nitroisophthalate (ndc) dianion, one N,N′-bidentate 2,2′-bipyridyl ligand and one water molecule. A symmetry-generated O,O′-bidentate ndc dianion completes the cobalt coordination environment, which could be described as very distorted cis-CoN₂O₄ octahedral. The bridging ndc ligands result in parallel chains running along the a direction, and O—H⋯O hydrogen bonds arising from the water molecules complete the structure.

Related literature

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

Experimental

Crystal data

[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]
M_r = 442.24
Monoclinic, P 2₁ /n
a = 10.0125 (10) Å
b = 23.575 (2) Å
c = 15.403 (2) Å
β = 97.28 (1)°
V = 3606.3 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 (2) K
0.43 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.673, T_max = 0.825
18893 measured reflections
6672 independent reflections
5103 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.106
S = 1.01
6672 reflections
535 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N2	2.065 (2)
Co1—N1	2.075 (2)
Co1—O2	2.0369 (19)
Co1—O1W	2.102 (2)
Co1—O5ⁱ	2.131 (2)
Co1—O6ⁱ	2.257 (2)
Co2—N3	2.073 (2)
Co2—N4	2.078 (3)
Co2—O12	2.031 (2)
Co2—O2W	2.089 (2)
Co2—O10ⁱⁱ	2.116 (2)
Co2—O9ⁱⁱ	2.294 (2)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O12ⁱ	0.830 (10)	2.01 (2)	2.771 (3)	153 (3)
O2W—H4W⋯O2ⁱⁱ	0.831 (10)	1.957 (17)	2.747 (3)	159 (3)
O1W—H2W⋯O9	0.830 (10)	2.05 (2)	2.763 (3)	143 (3)
O2W—H3W⋯O6	0.835 (10)	2.10 (3)	2.781 (3)	138 (3)
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/S1600536808038178/hb2844sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038178/hb2844Isup2.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). 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, (I), (Fig. 1).

Compound (I) is constructed from two zigzag chains, each containing one Co^II atom, one O-monodentate 5-nitroisophthalato (ndc) dianion, one N,N-bidentate 2,2'-bipyridyl ligand and one water molecule. A symmetry-generated, O,O-bidentate ndc dianion completes the cobalt coordination, which could be described as very distorted cis-CoN₂O₄ octahedral (Table 1). The bridging ndc ligands result in parallel chains running along the a direction (Fig. 2) and O—H···O hydrogen bonds arising from the water molecules (Table 2) complete the structure (Fig. 3).

Related literature top

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

Experimental top

A mixture of cobalt 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) sealed in a 25 ml Teflon-lined stainless steel autoclave was kept at 413 K for three days. Red blocks of (I) were obtained after cooling to room temperature with a yield of 27%. Anal. Calc. for C₁₈H₁₃CoN₃O₇: 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. The asymmetric unit of (I), extended to show the Co coordination spheres, showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms). Symmetry codes: O5A, O6A; A = (1+x, y, z), O9A, O10A, A = (x-1, y, z).
	Fig. 2. Part of a one-dimensional polymeric chain in (I)
	Fig. 3. The packing diagram of (I) formed with the hydrogen bonds.

catena-Poly[[aqua(2,2'-bipyridyl)cobalt(II)]-µ-5-nitroisophthalato] top

Crystal data top

[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]	F(000) = 1800
M_r = 442.24	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6672 reflections
a = 10.0125 (10) Å	θ = 1.7–25.5°
b = 23.575 (2) Å	µ = 1.00 mm⁻¹
c = 15.403 (2) Å	T = 293 K
β = 97.28 (1)°	Block, red
V = 3606.3 (7) Å³	0.43 × 0.28 × 0.20 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	6672 independent reflections
Radiation source: fine-focus sealed tube	5103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
T_min = 0.673, T_max = 0.825	k = −28→22
18893 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0548P)² + 2.8058P] where P = (F_o² + 2F_c²)/3
6672 reflections	(Δ/σ)_max = 0.032
535 parameters	Δρ_max = 0.95 e Å⁻³
6 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]	V = 3606.3 (7) Å³
M_r = 442.24	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0125 (10) Å	µ = 1.00 mm⁻¹
b = 23.575 (2) Å	T = 293 K
c = 15.403 (2) Å	0.43 × 0.28 × 0.20 mm
β = 97.28 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6672 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5103 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.825	R_int = 0.025
18893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.95 e Å⁻³
6672 reflections	Δρ_min = −0.29 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
Co1	1.16169 (4)	0.154445 (14)	0.85573 (2)	0.02466 (11)
Co2	0.12374 (4)	0.354444 (15)	0.93350 (3)	0.02797 (12)
C1	0.0858 (3)	0.43912 (15)	0.7845 (2)	0.0469 (8)
H1	0.0715	0.4073	0.7489	0.056*
C2	0.0708 (4)	0.49272 (17)	0.7466 (3)	0.0555 (10)
H2	0.0482	0.4963	0.6864	0.067*
C3	0.0893 (4)	0.54031 (16)	0.7979 (3)	0.0570 (10)
H3	0.0810	0.5763	0.7731	0.068*
C4	0.1204 (3)	0.53368 (14)	0.8864 (3)	0.0474 (9)
H4	0.1307	0.5651	0.9231	0.057*
C5	0.1365 (3)	0.47893 (12)	0.9205 (2)	0.0363 (7)
C6	0.1704 (3)	0.46688 (12)	1.0143 (2)	0.0361 (7)
C7	0.1997 (3)	0.50925 (14)	1.0774 (3)	0.0490 (9)
H7	0.1978	0.5474	1.0616	0.059*
C8	0.2313 (3)	0.49307 (17)	1.1631 (3)	0.0557 (10)
H8	0.2506	0.5203	1.2067	0.067*
C9	0.2341 (4)	0.43613 (17)	1.1843 (3)	0.0559 (10)
H9	0.2569	0.4248	1.2421	0.067*
C10	0.2034 (3)	0.39623 (15)	1.1200 (2)	0.0468 (8)
H10	0.2049	0.3580	1.1351	0.056*
C11	0.5280 (3)	0.24937 (12)	1.02748 (19)	0.0320 (6)
H11	0.4449	0.2352	1.0380	0.038*
C12	0.6449 (3)	0.22104 (12)	1.05893 (19)	0.0321 (6)
C13	0.7703 (3)	0.24074 (12)	1.04616 (19)	0.0327 (7)
H13	0.8479	0.2213	1.0685	0.039*
C14	0.7776 (3)	0.29080 (11)	0.99863 (18)	0.0271 (6)
C15	0.9110 (3)	0.31378 (12)	0.9803 (2)	0.0312 (6)
C16	0.6606 (3)	0.31947 (12)	0.96577 (18)	0.0286 (6)
H16	0.6666	0.3527	0.9339	0.034*
C17	0.5354 (3)	0.29914 (12)	0.98002 (18)	0.0288 (6)
C18	0.4121 (3)	0.33266 (13)	0.9446 (2)	0.0325 (7)
C19	1.1953 (4)	0.07221 (15)	1.0079 (2)	0.0512 (9)
H19	1.2137	0.1044	1.0424	0.061*
C20	1.2036 (5)	0.01944 (18)	1.0474 (3)	0.0684 (12)
H20	1.2268	0.0164	1.1076	0.082*
C21	1.1774 (5)	−0.02879 (17)	0.9971 (3)	0.0688 (12)
H21	1.1813	−0.0645	1.0230	0.083*
C22	1.1455 (4)	−0.02303 (14)	0.9087 (2)	0.0526 (9)
H22	1.1289	−0.0547	0.8731	0.063*
C23	1.1386 (3)	0.03108 (12)	0.8732 (2)	0.0327 (7)
C24	1.1073 (3)	0.04138 (12)	0.7783 (2)	0.0314 (6)
C25	1.0794 (3)	−0.00192 (13)	0.7180 (2)	0.0411 (8)
H25	1.0787	−0.0396	0.7357	0.049*
C26	1.0526 (3)	0.01263 (15)	0.6307 (2)	0.0456 (8)
H26	1.0329	−0.0152	0.5883	0.055*
C27	1.0556 (3)	0.06936 (15)	0.6071 (2)	0.0459 (8)
H27	1.0365	0.0798	0.5486	0.055*
C28	1.0866 (3)	0.11017 (13)	0.6701 (2)	0.0381 (7)
H28	1.0889	0.1480	0.6532	0.046*
C29	0.8750 (3)	0.17566 (13)	0.8380 (2)	0.0336 (7)
C30	0.7500 (3)	0.20949 (12)	0.80607 (18)	0.0274 (6)
C31	0.7569 (3)	0.26263 (12)	0.76643 (19)	0.0314 (6)
H31	0.8396	0.2780	0.7575	0.038*
C32	0.6258 (3)	0.18764 (12)	0.81981 (19)	0.0297 (6)
H32	0.6210	0.1529	0.8477	0.036*
C33	0.6392 (3)	0.29172 (12)	0.7409 (2)	0.0347 (7)
C34	0.5084 (3)	0.21757 (12)	0.79203 (18)	0.0273 (6)
C35	0.5143 (3)	0.27061 (13)	0.75206 (19)	0.0332 (7)
H35	0.4363	0.2910	0.7336	0.040*
C36	0.3756 (3)	0.19401 (13)	0.8104 (2)	0.0331 (7)
H1W	1.243 (3)	0.2304 (11)	0.958 (3)	0.080*
H2W	1.126 (2)	0.2153 (14)	0.989 (3)	0.080*
H3W	0.164 (2)	0.2956 (15)	0.803 (3)	0.080*
H4W	0.042 (3)	0.2778 (10)	0.823 (3)	0.080*
N1	1.1134 (2)	0.09709 (10)	0.75443 (15)	0.0302 (5)
N2	1.1617 (3)	0.07823 (10)	0.92182 (16)	0.0349 (6)
N3	0.1199 (2)	0.43207 (10)	0.87001 (17)	0.0349 (6)
N4	0.1713 (2)	0.41090 (10)	1.03641 (17)	0.0361 (6)
N5	0.6352 (3)	0.16753 (12)	1.10790 (19)	0.0477 (7)
N6	0.6479 (3)	0.34937 (13)	0.7036 (2)	0.0578 (9)
O1	0.8634 (2)	0.12806 (12)	0.8691 (2)	0.0705 (9)
O2	0.98644 (19)	0.19824 (8)	0.82627 (15)	0.0379 (5)
O3	0.7556 (3)	0.37273 (12)	0.7088 (2)	0.0801 (10)
O4	0.5459 (3)	0.37066 (17)	0.6681 (3)	0.1342 (19)
O5	0.3733 (2)	0.14822 (9)	0.85254 (16)	0.0440 (6)
O6	0.26919 (19)	0.22039 (9)	0.78407 (15)	0.0422 (5)
O7	0.5264 (3)	0.14506 (14)	1.1063 (2)	0.0932 (12)
O8	0.7366 (3)	0.14819 (11)	1.14856 (19)	0.0642 (8)
O9	1.0167 (2)	0.28717 (9)	1.00726 (15)	0.0411 (5)
O10	0.9137 (2)	0.35927 (9)	0.93795 (16)	0.0442 (6)
O11	0.4241 (2)	0.37689 (11)	0.90426 (18)	0.0586 (7)
O12	0.30031 (19)	0.31194 (9)	0.96161 (15)	0.0409 (5)
O1W	1.1948 (2)	0.20370 (8)	0.97017 (15)	0.0371 (5)
O2W	0.0917 (2)	0.30554 (8)	0.81966 (16)	0.0374 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01864 (19)	0.02268 (19)	0.0325 (2)	0.00142 (14)	0.00270 (15)	0.00151 (15)
Co2	0.01822 (19)	0.0237 (2)	0.0425 (2)	0.00121 (14)	0.00602 (16)	0.00113 (16)
C1	0.0428 (19)	0.048 (2)	0.052 (2)	0.0030 (15)	0.0148 (16)	0.0066 (16)
C2	0.046 (2)	0.065 (3)	0.057 (2)	0.0082 (18)	0.0139 (18)	0.024 (2)
C3	0.043 (2)	0.042 (2)	0.090 (3)	0.0027 (16)	0.020 (2)	0.026 (2)
C4	0.0326 (18)	0.0322 (17)	0.080 (3)	0.0017 (14)	0.0173 (17)	0.0057 (17)
C5	0.0193 (14)	0.0299 (15)	0.062 (2)	−0.0004 (12)	0.0141 (14)	0.0001 (14)
C6	0.0188 (14)	0.0342 (16)	0.057 (2)	−0.0007 (12)	0.0101 (13)	−0.0045 (14)
C7	0.0352 (18)	0.0352 (18)	0.078 (3)	−0.0024 (14)	0.0127 (18)	−0.0098 (17)
C8	0.038 (2)	0.067 (3)	0.062 (3)	−0.0018 (17)	0.0042 (18)	−0.022 (2)
C9	0.043 (2)	0.073 (3)	0.052 (2)	0.0057 (18)	0.0078 (17)	−0.0072 (19)
C10	0.0398 (19)	0.051 (2)	0.050 (2)	0.0067 (16)	0.0065 (16)	0.0001 (17)
C11	0.0204 (14)	0.0411 (16)	0.0348 (17)	−0.0058 (12)	0.0051 (12)	0.0010 (13)
C12	0.0267 (15)	0.0373 (16)	0.0323 (16)	−0.0020 (12)	0.0039 (12)	0.0048 (12)
C13	0.0210 (14)	0.0419 (17)	0.0347 (17)	0.0023 (12)	0.0012 (12)	0.0005 (13)
C14	0.0194 (14)	0.0317 (14)	0.0313 (15)	−0.0005 (11)	0.0069 (11)	−0.0043 (12)
C15	0.0185 (14)	0.0359 (16)	0.0403 (17)	0.0013 (12)	0.0077 (12)	−0.0087 (13)
C16	0.0228 (14)	0.0299 (14)	0.0336 (16)	−0.0011 (11)	0.0054 (12)	−0.0007 (12)
C17	0.0194 (14)	0.0358 (16)	0.0310 (16)	0.0001 (11)	0.0023 (11)	−0.0047 (12)
C18	0.0209 (15)	0.0387 (17)	0.0373 (17)	0.0023 (12)	0.0010 (12)	−0.0054 (13)
C19	0.070 (3)	0.048 (2)	0.0355 (19)	0.0013 (18)	0.0076 (17)	0.0048 (15)
C20	0.102 (4)	0.065 (3)	0.038 (2)	0.005 (2)	0.009 (2)	0.0146 (19)
C21	0.096 (3)	0.046 (2)	0.063 (3)	0.002 (2)	0.008 (2)	0.030 (2)
C22	0.068 (3)	0.0338 (18)	0.056 (2)	−0.0038 (17)	0.0053 (19)	0.0100 (16)
C23	0.0258 (15)	0.0308 (15)	0.0415 (18)	−0.0007 (12)	0.0043 (12)	0.0044 (13)
C24	0.0230 (14)	0.0304 (15)	0.0408 (17)	−0.0015 (12)	0.0042 (12)	0.0016 (13)
C25	0.0343 (17)	0.0329 (16)	0.056 (2)	−0.0028 (13)	0.0052 (15)	−0.0044 (15)
C26	0.0389 (19)	0.051 (2)	0.046 (2)	−0.0031 (15)	0.0035 (15)	−0.0147 (16)
C27	0.045 (2)	0.055 (2)	0.0367 (18)	0.0019 (16)	−0.0003 (15)	−0.0041 (15)
C28	0.0405 (18)	0.0378 (17)	0.0353 (17)	0.0061 (14)	0.0027 (14)	0.0054 (13)
C29	0.0221 (15)	0.0413 (17)	0.0369 (17)	0.0018 (13)	0.0017 (12)	0.0045 (13)
C30	0.0185 (14)	0.0351 (15)	0.0285 (15)	0.0014 (11)	0.0021 (11)	−0.0006 (12)
C31	0.0192 (14)	0.0402 (16)	0.0351 (16)	−0.0014 (12)	0.0045 (12)	0.0051 (13)
C32	0.0256 (15)	0.0311 (15)	0.0328 (15)	−0.0014 (12)	0.0060 (12)	−0.0004 (12)
C33	0.0303 (16)	0.0368 (16)	0.0379 (17)	0.0033 (13)	0.0078 (13)	0.0108 (13)
C34	0.0193 (13)	0.0346 (15)	0.0284 (15)	−0.0007 (11)	0.0047 (11)	−0.0063 (12)
C35	0.0215 (14)	0.0439 (17)	0.0340 (16)	0.0086 (12)	0.0030 (12)	0.0023 (13)
C36	0.0240 (15)	0.0401 (17)	0.0361 (17)	−0.0022 (13)	0.0070 (12)	−0.0110 (13)
N1	0.0251 (12)	0.0298 (12)	0.0358 (14)	0.0034 (10)	0.0039 (10)	0.0004 (10)
N2	0.0335 (14)	0.0349 (14)	0.0369 (15)	−0.0008 (11)	0.0067 (11)	0.0042 (11)
N3	0.0247 (13)	0.0352 (14)	0.0458 (17)	0.0018 (10)	0.0085 (11)	0.0055 (11)
N4	0.0264 (13)	0.0343 (14)	0.0483 (16)	0.0041 (10)	0.0079 (11)	−0.0007 (11)
N5	0.0348 (16)	0.0546 (17)	0.0532 (18)	−0.0040 (14)	0.0034 (13)	0.0203 (14)
N6	0.0458 (19)	0.0573 (19)	0.073 (2)	0.0145 (16)	0.0191 (16)	0.0331 (16)
O1	0.0359 (14)	0.0722 (18)	0.105 (2)	0.0136 (13)	0.0152 (14)	0.0578 (17)
O2	0.0161 (10)	0.0346 (11)	0.0623 (14)	0.0004 (8)	0.0022 (9)	−0.0024 (10)
O3	0.065 (2)	0.0644 (18)	0.108 (2)	−0.0176 (15)	−0.0012 (17)	0.0410 (17)
O4	0.0504 (19)	0.129 (3)	0.228 (5)	0.039 (2)	0.036 (2)	0.134 (3)
O5	0.0274 (12)	0.0441 (13)	0.0621 (15)	−0.0034 (9)	0.0117 (10)	0.0051 (11)
O6	0.0187 (10)	0.0491 (13)	0.0594 (15)	0.0039 (9)	0.0073 (10)	−0.0021 (11)
O7	0.0504 (18)	0.100 (2)	0.123 (3)	−0.0321 (16)	−0.0136 (18)	0.068 (2)
O8	0.0439 (15)	0.0619 (17)	0.087 (2)	0.0111 (12)	0.0070 (14)	0.0357 (14)
O9	0.0185 (10)	0.0453 (12)	0.0603 (14)	0.0035 (9)	0.0079 (10)	−0.0007 (10)
O10	0.0276 (11)	0.0363 (12)	0.0711 (16)	−0.0028 (9)	0.0161 (11)	0.0094 (11)
O11	0.0374 (14)	0.0576 (16)	0.0799 (18)	0.0077 (11)	0.0040 (13)	0.0303 (14)
O12	0.0190 (10)	0.0378 (12)	0.0658 (15)	0.0009 (9)	0.0052 (10)	−0.0032 (10)
O1W	0.0303 (12)	0.0335 (11)	0.0465 (13)	0.0030 (9)	0.0009 (10)	−0.0036 (9)
O2W	0.0287 (11)	0.0335 (11)	0.0502 (13)	0.0025 (9)	0.0050 (10)	0.0004 (10)

Geometric parameters (Å, º) top

Co1—N2	2.065 (2)	C19—C20	1.382 (5)
Co1—N1	2.075 (2)	C19—H19	0.9300
Co1—O2	2.0369 (19)	C20—C21	1.382 (6)
Co1—O1W	2.102 (2)	C20—H20	0.9300
Co1—O5ⁱ	2.131 (2)	C21—C22	1.365 (5)
Co1—O6ⁱ	2.257 (2)	C21—H21	0.9300
Co2—N3	2.073 (2)	C22—C23	1.386 (4)
Co2—N4	2.078 (3)	C22—H22	0.9300
Co2—O12	2.031 (2)	C23—N2	1.344 (4)
Co2—O2W	2.089 (2)	C23—C24	1.475 (4)
Co2—O10ⁱⁱ	2.116 (2)	C24—N1	1.367 (4)
Co2—O9ⁱⁱ	2.294 (2)	C24—C25	1.385 (4)
C1—N3	1.329 (4)	C25—C26	1.380 (5)
C1—C2	1.392 (5)	C25—H25	0.9300
C1—H1	0.9300	C26—C27	1.387 (5)
C2—C3	1.372 (6)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.374 (4)
C3—C4	1.367 (6)	C27—H27	0.9300
C3—H3	0.9300	C28—N1	1.329 (4)
C4—C5	1.395 (4)	C28—H28	0.9300
C4—H4	0.9300	C29—O1	1.231 (4)
C5—N3	1.349 (4)	C29—O2	1.270 (3)
C5—C6	1.470 (5)	C29—C30	1.513 (4)
C6—N4	1.362 (4)	C30—C32	1.386 (4)
C6—C7	1.398 (5)	C30—C31	1.399 (4)
C7—C8	1.373 (5)	C31—C33	1.377 (4)
C7—H7	0.9300	C31—H31	0.9300
C8—C9	1.381 (5)	C32—C34	1.391 (4)
C8—H8	0.9300	C32—H32	0.9300
C9—C10	1.372 (5)	C33—C35	1.377 (4)
C9—H9	0.9300	C33—N6	1.482 (4)
C10—N4	1.332 (4)	C34—C35	1.398 (4)
C10—H10	0.9300	C34—C36	1.500 (4)
C11—C12	1.381 (4)	C35—H35	0.9300
C11—C17	1.389 (4)	C36—O6	1.256 (3)
C11—H11	0.9300	C36—O5	1.261 (4)
C12—C13	1.376 (4)	C36—Co1ⁱⁱ	2.515 (3)
C12—N5	1.479 (4)	N5—O7	1.209 (4)
C13—C14	1.396 (4)	N5—O8	1.212 (3)
C13—H13	0.9300	N6—O3	1.204 (4)
C14—C16	1.390 (4)	N6—O4	1.205 (4)
C14—C15	1.501 (4)	O5—Co1ⁱⁱ	2.131 (2)
C15—O9	1.255 (3)	O6—Co1ⁱⁱ	2.257 (2)
C15—O10	1.257 (4)	O9—Co2ⁱ	2.294 (2)
C16—C17	1.386 (4)	O10—Co2ⁱ	2.116 (2)
C16—H16	0.9300	O1W—H1W	0.830 (10)
C17—C18	1.508 (4)	O1W—H2W	0.830 (10)
C18—O11	1.228 (4)	O2W—H3W	0.835 (10)
C18—O12	1.278 (3)	O2W—H4W	0.831 (10)
C19—N2	1.334 (4)

O2—Co1—N2	119.80 (9)	C20—C19—H19	119.1
O2—Co1—N1	92.92 (9)	C19—C20—C21	119.9 (4)
N2—Co1—N1	77.83 (9)	C19—C20—H20	120.1
O2—Co1—O1W	86.94 (8)	C21—C20—H20	120.1
N2—Co1—O1W	94.42 (9)	C22—C21—C20	118.7 (3)
N1—Co1—O1W	171.00 (9)	C22—C21—H21	120.6
O2—Co1—O5ⁱ	149.41 (9)	C20—C21—H21	120.6
N2—Co1—O5ⁱ	90.78 (9)	C21—C22—C23	118.6 (3)
N1—Co1—O5ⁱ	94.31 (9)	C21—C22—H22	120.7
O1W—Co1—O5ⁱ	90.33 (9)	C23—C22—H22	120.7
O2—Co1—O6ⁱ	89.58 (8)	N2—C23—C22	123.0 (3)
N2—Co1—O6ⁱ	150.47 (9)	N2—C23—C24	114.6 (2)
N1—Co1—O6ⁱ	99.27 (9)	C22—C23—C24	122.4 (3)
O1W—Co1—O6ⁱ	89.73 (8)	N1—C24—C25	122.7 (3)
O5ⁱ—Co1—O6ⁱ	59.93 (8)	N1—C24—C23	114.4 (2)
O12—Co2—N3	119.99 (9)	C25—C24—C23	122.9 (3)
O12—Co2—N4	92.54 (9)	C26—C25—C24	117.9 (3)
N3—Co2—N4	77.48 (10)	C26—C25—H25	121.0
O12—Co2—O2W	86.76 (9)	C24—C25—H25	121.0
N3—Co2—O2W	95.71 (9)	C25—C26—C27	119.2 (3)
N4—Co2—O2W	171.71 (10)	C25—C26—H26	120.4
O12—Co2—O10ⁱⁱ	149.51 (9)	C27—C26—H26	120.4
N3—Co2—O10ⁱⁱ	90.50 (9)	C28—C27—C26	120.0 (3)
N4—Co2—O10ⁱⁱ	94.22 (9)	C28—C27—H27	120.0
O2W—Co2—O10ⁱⁱ	90.54 (9)	C26—C27—H27	120.0
O12—Co2—O9ⁱⁱ	90.11 (8)	N1—C28—C27	121.8 (3)
N3—Co2—O9ⁱⁱ	149.55 (8)	N1—C28—H28	119.1
N4—Co2—O9ⁱⁱ	98.13 (9)	C27—C28—H28	119.1
O2W—Co2—O9ⁱⁱ	90.14 (8)	O1—C29—O2	124.4 (3)
O10ⁱⁱ—Co2—O9ⁱⁱ	59.50 (8)	O1—C29—C30	119.5 (3)
N3—C1—C2	122.0 (4)	O2—C29—C30	116.0 (3)
N3—C1—H1	119.0	C32—C30—C31	119.6 (2)
C2—C1—H1	119.0	C32—C30—C29	118.4 (3)
C3—C2—C1	120.1 (4)	C31—C30—C29	121.9 (2)
C3—C2—H2	120.0	C33—C31—C30	118.9 (3)
C1—C2—H2	120.0	C33—C31—H31	120.6
C4—C3—C2	118.6 (3)	C30—C31—H31	120.6
C4—C3—H3	120.7	C30—C32—C34	120.3 (3)
C2—C3—H3	120.7	C30—C32—H32	119.9
C3—C4—C5	118.8 (3)	C34—C32—H32	119.9
C3—C4—H4	120.6	C35—C33—C31	122.8 (3)
C5—C4—H4	120.6	C35—C33—N6	118.6 (3)
N3—C5—C4	122.7 (3)	C31—C33—N6	118.5 (3)
N3—C5—C6	113.9 (3)	C32—C34—C35	120.5 (3)
C4—C5—C6	123.4 (3)	C32—C34—C36	119.2 (3)
N4—C6—C7	121.6 (3)	C35—C34—C36	120.2 (2)
N4—C6—C5	115.2 (3)	C33—C35—C34	117.9 (3)
C7—C6—C5	123.2 (3)	C33—C35—H35	121.0
C8—C7—C6	118.2 (3)	C34—C35—H35	121.0
C8—C7—H7	120.9	O6—C36—O5	121.3 (3)
C6—C7—H7	120.9	O6—C36—C34	119.4 (3)
C7—C8—C9	119.5 (3)	O5—C36—C34	119.3 (3)
C7—C8—H8	120.2	O6—C36—Co1ⁱⁱ	63.61 (16)
C9—C8—H8	120.3	O5—C36—Co1ⁱⁱ	57.85 (15)
C10—C9—C8	120.0 (4)	C34—C36—Co1ⁱⁱ	174.8 (2)
C10—C9—H9	120.0	C28—N1—C24	118.4 (3)
C8—C9—H9	120.0	C28—N1—Co1	125.6 (2)
N4—C10—C9	121.6 (3)	C24—N1—Co1	115.95 (19)
N4—C10—H10	119.2	C19—N2—C23	118.0 (3)
C9—C10—H10	119.2	C19—N2—Co1	124.5 (2)
C12—C11—C17	119.6 (3)	C23—N2—Co1	117.12 (19)
C12—C11—H11	120.2	C1—N3—C5	117.8 (3)
C17—C11—H11	120.2	C1—N3—Co2	124.4 (2)
C13—C12—C11	122.3 (3)	C5—N3—Co2	117.2 (2)
C13—C12—N5	118.7 (3)	C10—N4—C6	119.1 (3)
C11—C12—N5	119.0 (3)	C10—N4—Co2	125.1 (2)
C12—C13—C14	118.0 (3)	C6—N4—Co2	115.9 (2)
C12—C13—H13	121.0	O7—N5—O8	122.6 (3)
C14—C13—H13	121.0	O7—N5—C12	118.7 (3)
C16—C14—C13	120.3 (3)	O8—N5—C12	118.7 (3)
C16—C14—C15	119.0 (3)	O3—N6—O4	122.7 (3)
C13—C14—C15	120.7 (2)	O3—N6—C33	119.3 (3)
O9—C15—O10	121.7 (3)	O4—N6—C33	118.0 (3)
O9—C15—C14	119.4 (3)	C29—O2—Co1	120.23 (19)
O10—C15—C14	118.9 (2)	C36—O5—Co1ⁱⁱ	92.08 (17)
C17—C16—C14	120.8 (3)	C36—O6—Co1ⁱⁱ	86.49 (18)
C17—C16—H16	119.6	C15—O9—Co2ⁱ	85.29 (18)
C14—C16—H16	119.6	C15—O10—Co2ⁱ	93.31 (17)
C16—C17—C11	119.0 (3)	C18—O12—Co2	121.93 (19)
C16—C17—C18	118.5 (3)	Co1—O1W—H1W	105 (3)
C11—C17—C18	122.5 (3)	Co1—O1W—H2W	115 (3)
O11—C18—O12	124.9 (3)	H1W—O1W—H2W	111.4 (18)
O11—C18—C17	120.0 (3)	Co2—O2W—H3W	111 (3)
O12—C18—C17	115.1 (3)	Co2—O2W—H4W	114 (3)
N2—C19—C20	121.7 (3)	H3W—O2W—H4W	111.0 (17)
N2—C19—H19	119.1

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
O1W—H1W···O12ⁱ	0.83 (1)	2.01 (2)	2.771 (3)	153 (3)
O2W—H4W···O2ⁱⁱ	0.83 (1)	1.96 (2)	2.747 (3)	159 (3)
O1W—H2W···O9	0.83 (1)	2.05 (2)	2.763 (3)	143 (3)
O2W—H3W···O6	0.84 (1)	2.10 (3)	2.781 (3)	138 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]
M_r	442.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.0125 (10), 23.575 (2), 15.403 (2)
β (°)	97.28 (1)
V (Å³)	3606.3 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.43 × 0.28 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.673, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	18893, 6672, 5103
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.106, 1.01
No. of reflections	6672
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)	0.95, −0.29

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

Selected bond lengths (Å) top

Co1—N2	2.065 (2)	Co2—N3	2.073 (2)
Co1—N1	2.075 (2)	Co2—N4	2.078 (3)
Co1—O2	2.0369 (19)	Co2—O12	2.031 (2)
Co1—O1W	2.102 (2)	Co2—O2W	2.089 (2)
Co1—O5ⁱ	2.131 (2)	Co2—O10ⁱⁱ	2.116 (2)
Co1—O6ⁱ	2.257 (2)	Co2—O9ⁱⁱ	2.294 (2)

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
O1W—H1W···O12ⁱ	0.830 (10)	2.01 (2)	2.771 (3)	153 (3)
O2W—H4W···O2ⁱⁱ	0.831 (10)	1.957 (17)	2.747 (3)	159 (3)
O1W—H2W···O9	0.830 (10)	2.05 (2)	2.763 (3)	143 (3)
O2W—H3W···O6	0.835 (10)	2.10 (3)	2.781 (3)	138 (3)

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

Acknowledgements

The authors thank the Natural Science Foundation of China (grant No. 20501011) and are grateful for financial support from Liaocheng University (grant No. X071011).

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
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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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1605-m1606

doi:10.1107/S1600536808038178

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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′-bi­pyridyl)cobalt(II)]-μ-5-nitro­isophthalato]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: catena-Poly[[aqua(2,2′-bipyridyl)cobalt(II)]-μ-5-nitroisophthalato]