5-Amino-2,4,6-triiodo­isophthalic acid–4,4′-bipyridine N,N′-dioxide–water (1/1/1)

Kou-Lin Zhang; Jin-Bo Zhang; Seik Weng Ng

doi:10.1107/S1600536811007276

. 2011 Mar 5;67(Pt 4):o793. doi: 10.1107/S1600536811007276

5-Amino-2,4,6-triiodoisophthalic acid–4,4′-bipyridine N,N′-dioxide–water (1/1/1)

Kou-Lin Zhang ^a, Jin-Bo Zhang ^a, Seik Weng Ng ^b,^*

PMCID: PMC3099751 PMID: 21754083

Abstract

The aromatic rings of the N,N′-dioxide molecule in the title compound, C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O, are twisted by 14.0 (2)°. The –CO₂H substituents of the 5-amino-2,4,6-triiodoisophthalic acid are twisted by 83.0 (2) and 86.5 (2)° out of the plane of the aromatic ring. In the crystal, the three components are linked by O—H⋯O hydrogen bonds into a three-dimensional network. An N—H⋯O interaction also occurs. One of the amino H atom is not involved in hydrogen bonding.

Related literature

For the structure of the monohydrated carboxylic acid, see: Beck & Sheldrick (2008 ▶). For the 4,4′-bipyridinium 5-amino-2,4,6-triiodoisophthalate co-crystal of carboxylic acid, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O
M _r = 765.02
Monoclinic,
a = 7.5000 (2) Å
b = 17.0808 (4) Å
c = 16.523 (3) Å
β = 94.349 (2)°
V = 2110.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 4.49 mm⁻¹
T = 100 K
0.20 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.467, T _max = 0.807
10861 measured reflections
4660 independent reflections
4112 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.068
S = 1.04
4660 reflections
304 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007276/bt5482sup1.cif

e-67-0o793-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007276/bt5482Isup2.hkl

e-67-0o793-Isup2.hkl^{(228.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.84 (3)	1.64 (3)	2.478 (4)	174 (6)
O3—H3⋯O6ⁱⁱ	0.84 (3)	1.63 (3)	2.465 (4)	170 (7)
O1W—H1w1⋯O2	0.84 (3)	2.30 (3)	3.073 (4)	154 (4)
O1W—H1w2⋯O5ⁱⁱⁱ	0.84 (3)	2.12 (3)	2.945 (4)	167 (5)
N1—H11⋯O1w^iv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, Yangzhou University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The attempt at synthesizing the 4,4'-bipyridine adduct of cadmium 5-amino-2,4,6-triiodoisophthalate gave instead a co-crystal having a monoprotonated 4,4'-bipyridinium 5-amino-2,4,6-triiodoisophthalate as one component and a carboxylic acid as the other (Zhang et al., 2010). Replacing the metal ion by a zinc ion, and with 4,4'-bipyridine N,N'-dioxide in place of 4,4'-bipyridine, gave instead the title monohydrated neutral co-crystal, C₁₀H₈N₂O₂^.C₈H₄NI₂O₄^.H₂O (Scheme I, Fig. 1). In the N-heterocycle, the rings are twisted by 14.0 (2) °. In the carboxylic acid, the –CO₂H substituents are nearly perpendicular to the aromatic ring. The three components are linked by O–H···O hydrogen bonds into a layer structure (Table 1).

Experimental

Zinc nitrate hexahydrate (58 mg, 0.2 mmol), 5-amino-2,4,6-triiodoisophthalic acid (59 mg, 0.1 mmol), 4,4'-bipyridine N,N'-dioxide (56 mg, 0.1 mmol), sodium hydroxide (4 mg, 0.1 mmol) and water (6 ml) were heated ain a 16-ml, Teflon-lined Parr bomb. The bomb was heated at 343 K for 3 days. Greenish-yellow crystals were isolated from the cool mixture.