7-Chloro­indoline-2,3-dione

Jie Sun; Zai-Sheng Cai

doi:10.1107/S1600536809051526

. 2009 Dec 4;66(Pt 1):o25. doi: 10.1107/S1600536809051526

7-Chloroindoline-2,3-dione

Jie Sun ^a,^b, Zai-Sheng Cai ^b,^*

PMCID: PMC2980139 PMID: 21580131

Abstract

There are two molecules in the asymmetric unit of the title compound, C₈H₄ClNO₂. In the crystal, they are linked by N—H⋯O hydrogen bonds, generating centrosymmetric, tetrameric assemblies. A C—H⋯O interaction also occurs.

Related literature

For general background to oxyphenastatin derivatives and further synthetic details, see: Uddin et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₄ClNO₂
M _r = 181.57
Triclinic,
a = 7.2450 (14) Å
b = 8.6080 (17) Å
c = 12.470 (3) Å
α = 86.95 (3)°
β = 78.02 (3)°
γ = 84.89 (3)°
V = 757.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.876, T _max = 0.956
2988 measured reflections
2749 independent reflections
2051 reflections with I > 2σ(I)
R _int = 0.047
3 standard reflections every 200 reflections
intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.160
S = 1.01
2749 reflections
217 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051526/hb5233sup1.cif

e-66-00o25-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051526/hb5233Isup2.hkl

e-66-00o25-Isup2.hkl^{(134.9KB, 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
N1—H1A⋯O4ⁱ	0.86	2.12	2.961 (4)	165
N2—H2B⋯O4ⁱ	0.86	2.10	2.923 (3)	160
C14—H14A⋯O2ⁱⁱ	0.93	2.46	3.385 (4)	172

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

Acknowledgments

The authors thank the Center of Testing and Analysis of Nanjing University for support.

supplementary crystallographic information

Experimental

85 g (0.06 mol) Sodium sulfate and 300 ml water was added into a 1000 ml three mouthed flask, mixed till the sodium sulfate dissolved, then a saturated solution of 18 g (0.11 mol) chloral hydrate was added. While stirring, the mixture of 12.7 g (0.1 mol) p-chloroaniline, 12 ml hydrochloric acid and 100 ml water was dropped to the reaction mixture causing white precipitation. Then 22 g (0.32 mol) hydroxylamine hydrochloride was added and the mixture was heated to 348 K. After 5 h, light yellow precipitation appeared, filtered and washed with water, dried and then added the yellow precipitation into concentrated sulfuric acid (50 ml) in batches at 353 K. Heated to 363 K and stirred for 30 minutes and dumped the mixture into ice water (1000 ml), stirred for 40 minutes, filtered and washed with water to neutral, dried and Yellow blocks of (I) were obtained by slow evaporation of an acetone solution (yield; 90%, m.p. 463 K).