catena-Poly[[[aqua­tripyridine­cobalt(II)]-μ-5-amino-2,4,6-triiodoisophthalato-κ2O1:O3] pyridine solvate]

Zhang, Y.; Zhao, J.; Tang, G.; Jiang, Z.

doi:10.1107/S1600536808032017

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1392-m1393

doi:10.1107/S1600536808032017

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catena-Poly[[[aquatripyridinecobalt(II)]-μ-5-amino-2,4,6-triiodoisophthalato-κ²O¹:O³] pyridine solvate]

Yu Zhang,^a ^* Jianying Zhao,^a Guodong Tang ^a and Zhengjing Jiang ^a

^aDepartment of Chemistry, Huaiyin Teachers College, Huai'an 223300, Jiangsu, People's Republic of China
^*Correspondence e-mail: yuzhang@hytc.edu.cn

(Received 20 September 2008; accepted 5 October 2008; online 15 October 2008)

The reaction of cobalt(II) nitrate with 5-amino-2,4,6-triiodoisophthalic acid (ATPA) in pyridine solution leads to the formation of the title compound, {[Co(C₈H₂I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N}_n. The Co²⁺ ion is six-coordinated by three N atoms, one water O atom and two O atoms from two ATPA ligands to form a distorted octahedral geometry. The two carboxylate groups of ATPA act as bridging ligands connecting the Co^II metal centers to form one-dimensional zigzag chains along the c axis, with Co—O distances in the range 2.104 (4)–2.135 (4) Å. The average Co—N distance is 2.171 Å. A classical O—H⋯N hydrogen bond is formed by the coordinating water molecule and the pyridine solvent molecule. The structure was refined from a racemically twinned crystal with a twin ratio of approximately 8:1.

Related literature

For the structure of a monohydrate of ATPA, see: Beck & Sheldrick (2008 ). For the Co coordination polymer of 1,3,5-benzenetricarboxylate, see: Livage et al. (2001 ). For the structure of diaquadiformatodipyridine Co^II, see: Zhu et al. (2004 ). For a reduction of the organic iodine contrast agents in wastewater load, see: Ziegler et al. (1997 ).

Experimental

Crystal data

[Co(C₈H₂I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N
M_r = 950.15
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.7759 (2) Å
b = 16.9083 (4) Å
c = 19.3380 (4) Å
V = 3196.45 (12) Å³
Z = 4
Mo Kα radiation
μ = 3.48 mm⁻¹
T = 296 (2) K
0.30 × 0.25 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.38, T_max = 0.75
16692 measured reflections
6038 independent reflections
4577 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.065
S = 1.04
6038 reflections
379 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.67 e Å⁻³
Absolute structure: Flack (1983 ), with 2515 Friedel pairs
Flack parameter: 0.13 (2)

Table 1
Selected geometric parameters (Å, °)

Co1—O1ⁱ	2.104 (4)
Co1—O5	2.106 (3)
Co1—O3	2.135 (4)
Co1—N2	2.161 (5)
Co1—N3	2.173 (5)
Co1—N4	2.180 (5)

O1ⁱ—Co1—O3	170.52 (16)
O1ⁱ—Co1—N3	102.93 (17)
O5—Co1—N3	172.68 (17)
N2—Co1—N4	178.48 (19)
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N5ⁱⁱ	0.85	1.94	2.748 (7)	159
Symmetry code: (ii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032017/si2113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032017/si2113Isup2.hkl

checkCIF report

Comment top

The crystal structure of ATPA (Beck & Sheldrick, 2008) is the precursor of the synthesis of a wide range of contrast agents with different amide-bound aliphatic side chains, which modulate their physical and physiological properties (Ziegler et al. 1997). However, to the best of our knowledge, there is no information about the structural characterization of its transition metal complexes.

The molecular structure of the title complex comprises of polymeric chains which extend along the c-axis. In the chain, each Co atom shows a distorted octahedron environment with a [3N+3O] coordination: three nitrogen atoms originate from pyridines, one oxygen from a water molecule and two oxygen atoms from two ATPA ligands. The two CO₂^- groups of the ATPA ligand coordinate to Co²⁺, bridging the Co metal centers. The bond lengths of the distorted octahedron are presented in Table 1. The average Co—N bond distance of the three pyridine ligands is 2.171 Å. The Co—O bond lengths in the title complex are slightly longer than those in the reported coordination polymers of cobalt and 1,3,5-benzenetricarboxylate (2.055 (2) Å) (Livage et al., 2001). The bond angles shown in Table 1 demonstrate the distorted octahedron in the Co coordination center. Compared with the data of the free ligand ATPA (Beck & Sheldrick, 2008), the C—O bond lengths are lengthened, the C—I and C—N bond distances are almost unchanged and the O—C—O bond angles are slightly expanded when the carboxylate groups are coordinated to central cations. The Co—N(py) and Co—O(H₂O) distances are in good agreement with those in diaqua-diformato-dipyridine-cobalt(II) (Zhu et al., 2004), where they are equal to 2.159 (4) Å and 2.143 (3) Å, respectively. A classic O—H···N hydrogen bond is formed by the coordinating water and the uncoordinated pyridine molecule (Table 2).

Related literature top

For the structure of a monohydrate of ATPA, see: Beck & Sheldrick (2008). For the Co coordination polymer of 1,3,5-benzenetricarboxylate, see: Livage et al. (2001). For the structure of diaquadiformatodipyridine Co^II, see: Zhu et al. (2004). For a reduction of the organic iodine contrast agents in wastewater load, see: Ziegler et al. (1997).

Experimental top

0.29 g (1 mmol) Co(NO₃)₂.6H₂O was dissolved in 10 ml ethanol, 0.54 g (1 mmol) 5-amino-2, 4, 6-triiodoisophthalic acid was dissolved in 10 ml pyridine. To mix two solutions gave a pale purple solution which was stirred at room temperature for 2 h, then filtered. After several days well formed light purple single crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Atoms labelled with an A belong to the symmetry-related ligand ATPA with symmetry code [A = -x + 3/2, -y, z + 1/2)].

catena-Poly[[[aquatripyridinecobalt(II)]-µ-5-amino-2,4,6- triiodoisophthalato-κ²O¹:O³] pyridine solvate] top

Crystal data top

[Co(C₈H2I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N	F(000) = 1812
M_r = 950.15	D_x = 1.974 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7120 reflections
a = 9.7759 (2) Å	θ = 4.7–43.0°
b = 16.9083 (4) Å	µ = 3.48 mm⁻¹
c = 19.3380 (4) Å	T = 296 K
V = 3196.45 (12) Å³	Sheet, light purple
Z = 4	0.30 × 0.25 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	6038 independent reflections
Radiation source: fine-focus sealed tube	4577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→9
T_min = 0.38, T_max = 0.75	k = −13→20
16692 measured reflections	l = −15→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0243P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
6038 reflections	Δρ_max = 0.68 e Å⁻³
379 parameters	Δρ_min = −0.67 e Å⁻³
3 restraints	Absolute structure: Flack (1983), with 2515 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (2)

Crystal data top

[Co(C₈H2I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N	V = 3196.45 (12) Å³
M_r = 950.15	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.7759 (2) Å	µ = 3.48 mm⁻¹
b = 16.9083 (4) Å	T = 296 K
c = 19.3380 (4) Å	0.30 × 0.25 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	6038 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4577 reflections with I > 2σ(I)
T_min = 0.38, T_max = 0.75	R_int = 0.027
16692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.68 e Å⁻³
S = 1.04	Δρ_min = −0.67 e Å⁻³
6038 reflections	Absolute structure: Flack (1983), with 2515 Friedel pairs
379 parameters	Absolute structure parameter: 0.13 (2)
3 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.8251 (6)	0.2139 (3)	0.8550 (3)	0.0319 (15)
C2	0.8423 (6)	0.2494 (3)	0.7900 (3)	0.0344 (16)
C3	0.7752 (6)	0.2152 (3)	0.7335 (3)	0.0299 (15)
C4	0.6949 (6)	0.1483 (3)	0.7390 (3)	0.0229 (14)
C5	0.6819 (6)	0.1159 (3)	0.8047 (3)	0.0286 (15)
C6	0.7445 (6)	0.1478 (3)	0.8629 (3)	0.0243 (14)
C7	0.6216 (7)	0.1144 (3)	0.6765 (3)	0.0276 (15)
C8	0.7222 (7)	0.1122 (3)	0.9341 (3)	0.0305 (15)
C9	0.9902 (7)	0.0943 (4)	1.1534 (4)	0.052 (2)
H9	1.0468	0.0501	1.1540	0.063*
C10	1.0171 (8)	0.1565 (5)	1.1968 (4)	0.067 (2)
H10	1.0909	0.1528	1.2270	0.080*
C11	0.9406 (10)	0.2230 (5)	1.1973 (4)	0.078 (3)
H11	0.9607	0.2651	1.2266	0.093*
C12	0.8332 (9)	0.2254 (5)	1.1531 (4)	0.078 (3)
H12	0.7768	0.2697	1.1520	0.093*
C13	0.8073 (7)	0.1626 (4)	1.1100 (4)	0.060 (2)
H13	0.7342	0.1661	1.0793	0.072*
C14	1.1101 (6)	−0.0851 (4)	1.0269 (3)	0.0397 (18)
H14	1.0619	−0.1279	1.0447	0.048*
C15	1.2437 (7)	−0.0963 (4)	1.0090 (3)	0.0488 (19)
H15	1.2859	−0.1451	1.0151	0.059*
C16	1.3142 (7)	−0.0329 (5)	0.9817 (3)	0.053 (2)
H16	1.4044	−0.0391	0.9674	0.064*
C17	1.2528 (6)	0.0377 (4)	0.9759 (3)	0.0471 (19)
H17	1.3000	0.0815	0.9592	0.057*
C18	1.1168 (7)	0.0434 (4)	0.9955 (3)	0.0448 (18)
H18	1.0733	0.0921	0.9911	0.054*
C19	0.6591 (7)	−0.1424 (4)	0.9923 (4)	0.0470 (19)
H19	0.6114	−0.1305	1.0326	0.056*
C20	0.6061 (7)	−0.1985 (4)	0.9494 (4)	0.057 (2)
H20	0.5249	−0.2240	0.9608	0.068*
C21	0.6717 (9)	−0.2166 (4)	0.8905 (4)	0.069 (2)
H21	0.6357	−0.2536	0.8599	0.082*
C22	0.7916 (9)	−0.1797 (4)	0.8766 (4)	0.063 (2)
H22	0.8416	−0.1925	0.8372	0.076*
C23	0.8384 (7)	−0.1222 (4)	0.9223 (4)	0.052 (2)
H23	0.9188	−0.0956	0.9113	0.062*
C24	−0.0436 (7)	0.0013 (4)	0.7430 (5)	0.062 (2)
H24	−0.1309	−0.0202	0.7465	0.074*
C25	0.0132 (9)	0.0325 (5)	0.8004 (4)	0.064 (2)
H25	−0.0337	0.0321	0.8422	0.076*
C26	0.1384 (11)	0.0640 (5)	0.7959 (5)	0.096 (3)
H26	0.1804	0.0855	0.8348	0.115*
C27	0.2020 (9)	0.0641 (6)	0.7351 (5)	0.101 (3)
H27	0.2884	0.0867	0.7309	0.121*
C28	0.1404 (9)	0.0313 (5)	0.6790 (4)	0.082 (3)
H28	0.1862	0.0311	0.6369	0.098*
Co1	0.83021 (7)	−0.00406 (5)	1.04654 (4)	0.0312 (2)
I1	0.92570 (5)	0.26385 (3)	0.94026 (2)	0.05269 (14)
I2	0.78262 (5)	0.27575 (3)	0.63848 (2)	0.05874 (16)
I3	0.56454 (5)	0.01146 (3)	0.81795 (2)	0.05039 (14)
N1	0.9245 (6)	0.3143 (3)	0.7821 (3)	0.0630 (17)
H1A	0.9357	0.3349	0.7418	0.076*
H1B	0.9649	0.3345	0.8174	0.076*
N2	0.8833 (5)	0.0964 (3)	1.1102 (2)	0.0393 (14)
N3	1.0452 (5)	−0.0175 (3)	1.0205 (2)	0.0348 (13)
N4	0.7763 (6)	−0.1033 (3)	0.9799 (3)	0.0379 (14)
N5	0.0172 (7)	−0.0004 (4)	0.6829 (3)	0.0660 (19)
O1	0.6899 (4)	0.0730 (2)	0.6366 (2)	0.0386 (11)
O2	0.5004 (5)	0.1311 (3)	0.6709 (2)	0.0555 (14)
O3	0.8147 (4)	0.0677 (2)	0.95601 (19)	0.0329 (10)
O4	0.6139 (4)	0.1298 (2)	0.9646 (2)	0.0460 (12)
O5	0.6191 (3)	0.0161 (2)	1.05937 (18)	0.0423 (11)
H5B	0.5951	0.0603	1.0423	0.051*
H5A	0.5963	0.0143	1.1018	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (4)	0.029 (4)	0.026 (4)	0.003 (3)	−0.003 (3)	−0.007 (3)
C2	0.043 (4)	0.029 (4)	0.032 (4)	−0.014 (3)	0.003 (3)	−0.004 (3)
C3	0.038 (3)	0.029 (4)	0.023 (3)	−0.005 (3)	−0.004 (3)	0.001 (3)
C4	0.026 (4)	0.022 (3)	0.020 (3)	0.004 (3)	−0.001 (3)	−0.007 (3)
C5	0.032 (3)	0.032 (4)	0.022 (4)	−0.002 (3)	0.003 (3)	−0.003 (3)
C6	0.033 (4)	0.022 (3)	0.017 (3)	0.006 (3)	−0.004 (3)	−0.002 (3)
C7	0.041 (4)	0.020 (4)	0.021 (4)	0.010 (3)	0.005 (3)	0.004 (3)
C8	0.045 (4)	0.027 (4)	0.019 (4)	−0.006 (3)	−0.005 (4)	−0.007 (3)
C9	0.050 (4)	0.053 (5)	0.053 (5)	−0.004 (4)	−0.023 (4)	0.006 (4)
C10	0.078 (6)	0.071 (6)	0.052 (5)	−0.045 (5)	−0.022 (5)	−0.004 (5)
C11	0.122 (8)	0.054 (6)	0.058 (5)	−0.033 (6)	0.009 (6)	−0.022 (5)
C12	0.103 (7)	0.056 (6)	0.075 (6)	0.004 (5)	−0.025 (5)	−0.024 (5)
C13	0.067 (5)	0.054 (5)	0.059 (5)	0.011 (5)	−0.006 (5)	−0.020 (4)
C14	0.042 (4)	0.043 (4)	0.035 (4)	0.004 (4)	0.001 (3)	0.000 (4)
C15	0.046 (5)	0.057 (5)	0.043 (5)	0.020 (4)	0.002 (4)	−0.008 (4)
C16	0.028 (4)	0.088 (6)	0.044 (5)	0.013 (4)	0.003 (3)	−0.009 (4)
C17	0.032 (4)	0.064 (6)	0.045 (4)	−0.008 (4)	−0.001 (3)	0.010 (4)
C18	0.046 (5)	0.041 (4)	0.048 (5)	0.001 (4)	0.003 (4)	0.004 (4)
C19	0.048 (5)	0.037 (4)	0.056 (5)	0.005 (4)	0.003 (4)	0.004 (4)
C20	0.047 (5)	0.043 (5)	0.080 (6)	−0.017 (4)	−0.010 (4)	0.001 (5)
C21	0.088 (7)	0.050 (5)	0.068 (5)	−0.009 (5)	−0.026 (5)	−0.008 (5)
C22	0.085 (6)	0.060 (6)	0.046 (5)	0.000 (5)	−0.004 (5)	−0.028 (4)
C23	0.055 (5)	0.051 (5)	0.049 (5)	−0.011 (4)	0.006 (4)	−0.005 (4)
C24	0.041 (5)	0.061 (5)	0.083 (6)	0.005 (4)	0.005 (5)	−0.002 (6)
C25	0.078 (6)	0.067 (6)	0.046 (5)	0.019 (5)	0.010 (5)	0.001 (5)
C26	0.115 (9)	0.122 (8)	0.050 (6)	−0.044 (7)	−0.034 (6)	0.010 (6)
C27	0.059 (6)	0.167 (10)	0.078 (7)	−0.047 (6)	−0.011 (6)	0.020 (8)
C28	0.063 (6)	0.131 (9)	0.051 (6)	−0.003 (6)	0.014 (5)	0.023 (6)
Co1	0.0333 (4)	0.0350 (5)	0.0254 (5)	−0.0001 (4)	−0.0013 (4)	0.0022 (5)
I1	0.0737 (3)	0.0481 (3)	0.0363 (3)	−0.0171 (3)	−0.0127 (3)	−0.0058 (2)
I2	0.0883 (4)	0.0569 (3)	0.0311 (3)	−0.0191 (3)	0.0001 (3)	0.0134 (3)
I3	0.0633 (3)	0.0495 (3)	0.0384 (3)	−0.0231 (3)	−0.0053 (2)	0.0067 (2)
N1	0.092 (4)	0.062 (4)	0.035 (3)	−0.045 (4)	−0.014 (4)	0.007 (3)
N2	0.048 (4)	0.042 (4)	0.027 (3)	−0.004 (3)	0.000 (3)	−0.001 (3)
N3	0.031 (3)	0.038 (3)	0.035 (3)	0.002 (3)	0.003 (2)	0.006 (3)
N4	0.043 (3)	0.039 (4)	0.031 (3)	0.003 (3)	0.002 (3)	−0.002 (3)
N5	0.063 (4)	0.089 (5)	0.047 (4)	0.014 (4)	−0.012 (4)	−0.011 (4)
O1	0.047 (3)	0.041 (3)	0.028 (2)	−0.001 (2)	0.002 (2)	−0.013 (2)
O2	0.048 (3)	0.075 (4)	0.044 (3)	0.015 (3)	−0.012 (3)	−0.020 (3)
O3	0.037 (3)	0.036 (3)	0.026 (2)	0.001 (2)	−0.005 (2)	0.007 (2)
O4	0.049 (3)	0.064 (3)	0.025 (3)	0.021 (2)	0.010 (2)	0.001 (2)
O5	0.045 (3)	0.048 (3)	0.034 (2)	0.007 (2)	0.006 (2)	0.010 (2)

Geometric parameters (Å, º) top

C1—C6	1.376 (7)	C18—N3	1.336 (7)
C1—C2	1.404 (7)	C18—H18	0.9300
C1—I1	2.097 (6)	C19—N4	1.344 (7)
C2—N1	1.368 (7)	C19—C20	1.363 (9)
C2—C3	1.400 (7)	C19—H19	0.9300
C3—C4	1.381 (7)	C20—C21	1.342 (9)
C3—I2	2.105 (5)	C20—H20	0.9300
C4—C5	1.389 (7)	C21—C22	1.355 (9)
C4—C7	1.517 (8)	C21—H21	0.9300
C5—C6	1.390 (7)	C22—C23	1.391 (8)
C5—I3	2.122 (6)	C22—H22	0.9300
C6—C8	1.519 (4)	C23—N4	1.309 (7)
C7—O2	1.223 (6)	C23—H23	0.9300
C7—O1	1.238 (6)	C24—N5	1.306 (8)
C8—O4	1.248 (6)	C24—C25	1.348 (9)
C8—O3	1.250 (6)	C24—H24	0.9300
C9—N2	1.337 (7)	C25—C26	1.338 (10)
C9—C10	1.372 (9)	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.331 (11)
C10—C11	1.350 (10)	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.359 (11)
C11—C12	1.355 (10)	C27—H27	0.9300
C11—H11	0.9300	C28—N5	1.321 (9)
C12—C13	1.373 (9)	C28—H28	0.9300
C12—H12	0.9300	Co1—O1ⁱ	2.104 (4)
C13—N2	1.345 (7)	Co1—O5	2.106 (3)
C13—H13	0.9300	Co1—O3	2.135 (4)
C14—N3	1.312 (7)	Co1—N2	2.161 (5)
C14—C15	1.365 (8)	Co1—N3	2.173 (5)
C14—H14	0.9300	Co1—N4	2.180 (5)
C15—C16	1.379 (9)	N1—H1A	0.8600
C15—H15	0.9300	N1—H1B	0.8600
C16—C17	1.342 (8)	O1—Co1ⁱⁱ	2.104 (4)
C16—H16	0.9300	O5—H5B	0.8500
C17—C18	1.386 (8)	O5—H5A	0.8499
C17—H17	0.9300

C6—C1—C2	121.0 (5)	C19—C20—H20	120.2
C6—C1—I1	120.6 (4)	C20—C21—C22	118.4 (8)
C2—C1—I1	118.4 (4)	C20—C21—H21	120.8
N1—C2—C3	121.3 (5)	C22—C21—H21	120.8
N1—C2—C1	120.9 (5)	C21—C22—C23	118.7 (8)
C3—C2—C1	117.8 (5)	C21—C22—H22	120.6
C4—C3—C2	123.0 (5)	C23—C22—H22	120.6
C4—C3—I2	119.1 (4)	N4—C23—C22	124.0 (7)
C2—C3—I2	117.7 (4)	N4—C23—H23	118.0
C3—C4—C5	116.5 (5)	C22—C23—H23	118.0
C3—C4—C7	121.1 (5)	N5—C24—C25	123.6 (7)
C5—C4—C7	122.5 (5)	N5—C24—H24	118.2
C4—C5—C6	123.2 (5)	C25—C24—H24	118.2
C4—C5—I3	119.2 (4)	C26—C25—C24	118.6 (8)
C6—C5—I3	117.6 (4)	C26—C25—H25	120.7
C1—C6—C5	118.5 (5)	C24—C25—H25	120.7
C1—C6—C8	120.3 (5)	C27—C26—C25	119.0 (9)
C5—C6—C8	121.1 (5)	C27—C26—H26	120.5
O2—C7—O1	126.7 (7)	C25—C26—H26	120.5
O2—C7—C4	116.2 (6)	C26—C27—C28	119.9 (8)
O1—C7—C4	117.2 (5)	C26—C27—H27	120.1
O4—C8—O3	126.7 (5)	C28—C27—H27	120.1
O4—C8—C6	117.0 (6)	N5—C28—C27	121.6 (8)
O3—C8—C6	116.2 (5)	N5—C28—H28	119.2
N2—C9—C10	120.7 (7)	C27—C28—H28	119.2
N2—C9—H9	119.6	O1ⁱ—Co1—O5	84.29 (15)
C10—C9—H9	119.6	O1ⁱ—Co1—O3	170.52 (16)
C11—C10—C9	122.5 (8)	O5—Co1—O3	86.29 (15)
C11—C10—H10	118.7	O1ⁱ—Co1—N2	89.21 (16)
C9—C10—H10	118.7	O5—Co1—N2	92.37 (17)
C10—C11—C12	116.7 (8)	O3—Co1—N2	92.18 (17)
C10—C11—H11	121.7	O1ⁱ—Co1—N3	102.93 (17)
C12—C11—H11	121.7	O5—Co1—N3	172.68 (17)
C11—C12—C13	120.2 (8)	O3—Co1—N3	86.47 (17)
C11—C12—H12	119.9	N2—Co1—N3	88.95 (19)
C13—C12—H12	119.9	O1ⁱ—Co1—N4	92.29 (17)
N2—C13—C12	122.7 (7)	O5—Co1—N4	87.53 (18)
N2—C13—H13	118.7	O3—Co1—N4	86.31 (16)
C12—C13—H13	118.7	N2—Co1—N4	178.48 (19)
N3—C14—C15	124.1 (6)	N3—Co1—N4	91.0 (2)
N3—C14—H14	118.0	C2—N1—H1A	120.0
C15—C14—H14	118.0	C2—N1—H1B	120.0
C14—C15—C16	117.8 (7)	H1A—N1—H1B	120.0
C14—C15—H15	121.1	C9—N2—C13	117.2 (6)
C16—C15—H15	121.1	C9—N2—Co1	121.5 (5)
C17—C16—C15	120.0 (6)	C13—N2—Co1	121.3 (5)
C17—C16—H16	120.0	C14—N3—C18	116.9 (5)
C15—C16—H16	120.0	C14—N3—Co1	122.5 (4)
C16—C17—C18	117.9 (7)	C18—N3—Co1	120.7 (4)
C16—C17—H17	121.0	C23—N4—C19	115.3 (6)
C18—C17—H17	121.0	C23—N4—Co1	125.4 (5)
N3—C18—C17	123.2 (6)	C19—N4—Co1	118.7 (5)
N3—C18—H18	118.4	C24—N5—C28	117.2 (7)
C17—C18—H18	118.4	C7—O1—Co1ⁱⁱ	141.2 (4)
N4—C19—C20	123.9 (7)	C8—O3—Co1	132.1 (4)
N4—C19—H19	118.0	Co1—O5—H5B	111.5
C20—C19—H19	118.0	Co1—O5—H5A	111.4
C21—C20—C19	119.6 (7)	H5B—O5—H5A	109.4
C21—C20—H20	120.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N5ⁱⁱⁱ	0.85	1.94	2.748 (7)	159

Symmetry code: (iii) −x+1/2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₈H2I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N
M_r	950.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.7759 (2), 16.9083 (4), 19.3380 (4)
V (Å³)	3196.45 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.48
Crystal size (mm)	0.30 × 0.25 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.38, 0.75
No. of measured, independent and observed [I > 2σ(I)] reflections	16692, 6038, 4577
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.065, 1.04
No. of reflections	6038
No. of parameters	379
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.67
Absolute structure	Flack (1983), with 2515 Friedel pairs
Absolute structure parameter	0.13 (2)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Co1—O1ⁱ	2.104 (4)	Co1—N2	2.161 (5)
Co1—O5	2.106 (3)	Co1—N3	2.173 (5)
Co1—O3	2.135 (4)	Co1—N4	2.180 (5)

O1ⁱ—Co1—O3	170.52 (16)	O5—Co1—N3	172.68 (17)
O1ⁱ—Co1—N3	102.93 (17)	N2—Co1—N4	178.48 (19)

Symmetry code: (i) −x+3/2, −y, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N5ⁱⁱ	0.85	1.94	2.748 (7)	159

Symmetry code: (ii) −x+1/2, −y, z+1/2.

Acknowledgements

This work was financially supported by the Natural Science Foundation of Jiangsu Province Education Office (grant No. 04KJB150015). We also thank Dr Zaichao Zhang for his support.

References

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