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Volume 69 
Part 12 
Page o1801  
December 2013  

Received 12 November 2013
Accepted 15 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.167
Data-to-parameter ratio = 16.3
Details
Open access

1-Octylindoline-2,3-dione

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,bLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat, Morocco,cInstitute of Physical and Theoretical Chemistry, University of Regensburg, D-93040 Regensburg, Germany, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: fatimazahrae_qachchachi@yahoo.fr

In the title compound, C16H21NO2, the indoline ring and the two ketone O atoms are approximately coplanar, the largest deviation from the mean plane being 0.063 (2) Å. The mean plane through the fused ring system is nearly perpendicular to the mean plane passing through the 1-octyl chain [dihedral angle = 77.53 (17)°]. In the crystal, mol­ecules are linked by C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010[Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M. S. & Ahsan, W. (2010). Int. J. Pharm. Sci. Drug Res. 2, 229-235.]); Malhotra et al. (2011[Malhotra, S., Balwani, S., Dhawan, A., Singh, B. K., Kumar, S., Thimmulappa, R., Biswal, S., Olsen, C. E., Van der Eycken, E., Prasad, A. K., Ghosh, B. & Parmar, V. S. (2011). Med. Chem. Commun. 2, 743-751.]); Da Silva et al. (2001[Da Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]); Ramachandran (2011[Ramachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289-294.]); Smitha et al. (2008[Smitha, S., Pandeya, S. N., Stables, J. P. & Ganapathy, S. (2008). Sci. Pharm. 76, 621-636.]). For the structure of a related compound, see: Mamari et al. (2010[Mamari, K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1410.]).

[Scheme 1]

Experimental

Crystal data
  • C16H21NO2

  • Mr = 259.34

  • Monoclinic, P 21 /c

  • a = 20.266 (4) Å

  • b = 4.6925 (1) Å

  • c = 15.7807 (11) Å

  • [beta] = 108.941 (18)°

  • V = 1419.5 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.63 mm-1

  • T = 123 K

  • 0.31 × 0.07 × 0.04 mm

Data collection
  • Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.899, Tmax = 0.979

  • 13541 measured reflections

  • 2811 independent reflections

  • 2462 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.167

  • S = 1.18

  • 2811 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.49 3.156 (3) 129
C6-H6...O2ii 0.93 2.57 3.260 (3) 131
C4-H4...O2iii 0.93 2.55 3.470 (3) 170
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+3, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5095 ).


References

Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M. S. & Ahsan, W. (2010). Int. J. Pharm. Sci. Drug Res. 2, 229-235.  [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [IUCr Journals]
Da Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Malhotra, S., Balwani, S., Dhawan, A., Singh, B. K., Kumar, S., Thimmulappa, R., Biswal, S., Olsen, C. E., Van der Eycken, E., Prasad, A. K., Ghosh, B. & Parmar, V. S. (2011). Med. Chem. Commun. 2, 743-751.  [CrossRef] [ChemPort]
Mamari, K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1410.  [CSD] [CrossRef] [IUCr Journals]
Oxford Diffraction (2012). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Ramachandran, S. (2011). Int. J. Res. Pharm. Chem. 1, 289-294.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smitha, S., Pandeya, S. N., Stables, J. P. & Ganapathy, S. (2008). Sci. Pharm. 76, 621-636.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1801  [ doi:10.1107/S1600536813031383 ]

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