1-Do­decyl­indoline-2,3-dione

Fatima-Zahrae Qachchachi; Fouad Ouazzani Chahdi; Houria Misbahi; Michael Bodensteiner; Lahcen El Ammari

doi:10.1107/S1600536814001792

. 2014 Jan 31;70(Pt 2):o229. doi: 10.1107/S1600536814001792

1-Dodecylindoline-2,3-dione

Fatima-Zahrae Qachchachi ^a,^*, Fouad Ouazzani Chahdi ^a, Houria Misbahi ^b, Michael Bodensteiner ^c, Lahcen El Ammari ^d

PMCID: PMC3998367 PMID: 24764928

Abstract

The structure of the title compound, C₂₀H₂₉NO₂, is isotypic to that of its homologue 1-octylindoline-2,3-dione. The indoline ring and the two carbonyl-group O atoms are approximately coplanar, the largest deviation from the mean plane being 0.0760 (10) Å. The mean plane through the fused-ring system is nearly perpendicular to the mean plane passing through the 1-dodecyl chain [dihedral angle = 77.69 (5)°]. All C atoms of the dodecyl group are in an antiperiplanar arrangement. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For biological activity of indoline derivatives, see: Bhrigu et al. (2010 ▶); Malhotra et al. (2011 ▶); Da Silva et al. (2001 ▶); Ramachandran (2011 ▶); Smitha et al. (2008 ▶). For similar compounds see: Qachchachi et al. (2013 ▶). graphic file with name e-70-0o229-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₉NO₂
M _r = 315.44
Monoclinic,
a = 25.2013 (7) Å
b = 4.66818 (9) Å
c = 15.7013 (4) Å
β = 104.926 (3)°
V = 1784.84 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 123 K
0.12 × 0.11 × 0.04 mm

Data collection

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012 ▶); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995 ▶)] T _min = 0.942, T _max = 0.979
12640 measured reflections
3493 independent reflections
3039 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.100
S = 1.02
3493 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2012 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001792/rz5103sup1.cif

e-70-0o229-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001792/rz5103Isup2.hkl

e-70-0o229-Isup2.hkl^{(171.3KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814001792/rz5103Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=983507

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.95	2.47	3.1423 (14)	127
C6—H6⋯O2ⁱⁱ	0.95	2.55	3.2360 (13)	130
C8—H8⋯O2ⁱⁱⁱ	0.95	2.52	3.4598 (13)	169

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

supplementary crystallographic information

1. Comment

Isatin (1H-indoline-2,3-dione) and derivatives possess a broad range of biological and pharmacological properties and are widely used as starting materials for the synthesis of heterocyclic compounds and as substrates for drug synthesis relevant to application as insecticides and fungicides. These compounds find applications also in a broad range of therapies as anticancer drugs, antibiotics and antidepressants (Bhrigu et al., 2010; Malhotra et al., 2011; Da Silva et al., 2001; Ramachandran, 2011; Smitha et al., 2008). In our work, we are interested in developing a new isatin derivative with the addition of an alkyl halide to explore other potential applications.

The molecule of title compound is build up from a fused five- and six-membered ring system linked to a 1-dodecyl chain and to two ketone O atoms as shown in Fig. 1. The indoline ring and the two carbonyl-group O atoms are nearly coplanar, the largest deviation from the mean plane being 0.0760 (10) Å for atom O1. The plane of the fused ring system is nearly perpendicular to the mean plane passing through the 1-dodecyl chain as indicated by the dihedral angle of 77.69 (5)°. The dodecyl substituent has all carbon atoms in an antiperiplanar conformation. The structure of the title compound is similar to that of its homologue 1-octylindoline-2,3-dione (Qachchachi et al., 2013).

In the crystal, the molecules are linked by C6–H6···O1, C6–H6···O2 and C8–H8···O2 hydrogen bonds in the way to build a three-dimensional network as shown in Fig. 2 and Table 2.

2. Experimental

To a solution of isatin (0.5 g, 3.4 mmol) dissolved in DMF (30 ml) was added potassium carbonate (0.61 g, 4.4 mmol), a catalytic quantity of tetra-n-butylammonium bromide (0.1 g, 0.4 mmol) and 1-bromododecane (0.9 ml, 3.7 mmol). The mixture was stirred for 48 h and the reaction monitored by thin layer chromatography. The mixture was filtered and the solvent removed under vacuum. The solid obtained was recrystallized from ethanol to afford the title compound as orange crystals in 86% yield (m. p. 321 K).