5-Bromo-1<i>H</i>-indole-2,3-dione

Gurung, Sita; Golen, James A.; Manke, David R.

doi:10.1107/s2414314616001772

Cited by 4 publications

(2 citation statements)

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“…2). Despite the coordination of the carbonyl oxygen atoms to the sodium cations, the C O bonds and other metric parameters are data reports consistent with those in neutral 5-substituted isatins (Gurung et al, 2016). Pairs of sodium cations are linked by the isatin molecules to form a one-dimensional coordination polymer along the c axis.…”

Section: Structure Descriptionmentioning

confidence: 55%

Poly[diaqua(μ₃-2,3-dioxoindoline-5-sulfonato)sodium]

et al. 2017

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] n , is a one-dimensional coordination polymer extending along the c axis. It consist of isatin sulfonate molecules linking pairs of sodium cations with Na-O bonds to both carbonyl and sulfonate oxygen atoms whereby two oxygen atoms of symmetry-related carbonyl groups bridge two sodium cations. The sodium cation possesses an octahedral coordination environment, including one sulfonate and three carbonyl oxygen atoms bound in the equatorial plane, and two water molecules bound axially. The isatin moiety of the organic ligand is nearly planar, with a mean deviation from planarity of 0.038 Å . The chains of the coordination polymer are further linked into a three-dimensional network with eight distinct interactions, including one N-HÁ Á ÁO and four O-HÁ Á ÁO hydrogen bonds, two C-HÁ Á ÁO interactions and one -interaction. Structure descriptionAs part of our standing project to study the crystal structures of N-H isatins, we report the crystal structure of the title compound. The asymmetric unit comprises a sodium cation, a 2,3-dioxoindoline-5-sulfonate anion and two coordinating water molecules (Fig. 1). The isatin moiety of the anion is nearly planar. The sodium cation possesses an octahedral configuration, and is coordinated by three carbonyl oxygen atoms, two water molecules, and one sulfonate oxygen atom. Two symmetry-related O1 carbonyl oxygen atoms bridge two sodium cations, with the O2 carbonyl oxygen binding to only a single sodium cation. The O5 sulfonate oxygen atom and the two water oxygen atoms (O6, O7) complete the sodium coordination environment (Fig. 2). Despite the coordination of the carbonyl oxygen atoms to the sodium cations, the C O bonds and other metric parameters are

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Section: Structure Descriptionmentioning

confidence: 55%

Poly[diaqua(μ₃-2,3-dioxoindoline-5-sulfonato)sodium]

et al. 2017

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“…The structure of the title compound demonstrates intermolecular Br1Á Á ÁO2 close contacts of 3.085 (2) Å , which are also observed in the structures of 4-bromoisatin and 6-bromoisatin (Huang et al, 2016;Turbitt et al, 2016). No such halogen interactions were observed for 5-bromoisatin, 7-fluoroisatin or 7-chloroisatin (Gurung et al, 2016;Mohamed et al, 2007Mohamed et al, , 2008Shankland et al, 2007;Sun et al, 2010).…”

Section: Structure Descriptionmentioning

confidence: 57%

7-Bromo-1H-indole-2,3-dione

Golen

Manke

2016

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The title compound, C8H4BrNO2, has a single planar molecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.034 Å. The molecules dimerize in the solid state through N—H...O hydrogen bonds. These dimers are further linked by intermolecular Br...O close contacts of 3.085 (2) Å to yield infinite chains along [20-1]. The nine-membered rings of the isatins stack along theaaxis, with parallel slipped π–π interactions [intercentroid distance = 3.8320 (7) Å, interplanar distance = 3.341 (2) Å and slippage = 1.876 (4) Å].

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