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Volume 69 
Part 12 
Page o1847  
December 2013  

Received 12 November 2013
Accepted 25 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.120
Data-to-parameter ratio = 16.4
Details
Open access

N-(1-Allyl-1H-indazol-5-yl)-4-methyl­benzene­sulfonamide

aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
Correspondence e-mail: h_abderrafia@yahoo.fr

The asymmetric unit of the title compound, C17H17N3O2S, contains two independent mol­ecules linked by an N-H...O hydrogen bond. The mol­ecules show different conformations. In the first mol­ecule, the fused five- and six-membered ring system is almost perpendicular to the plane through the atoms forming the allyl group, as indicated by the dihedral angle of 85.1 (4)°. The dihedral angle with the methyl­benzene­sulfonamide group is 78.8 (1)°. On the other hand, in the second mol­ecule, the dihedral angles between the indazole plane and the allyl and methyl­benzene­sulfonamide groups are 80.3 (3) and 41.5 (1)°, respectively. In the crystal, mol­ecules are further linked by N-H...N and C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Léonce, S., Pfeiffer, B., Rakib, E. M., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]); El-Sayed et al. (2011[El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.]); Mustafa et al. (2012[Mustafa, G., Khan, I. U., Ashraf, M., Afzal, I., Shahzad, S. A. & Shafiq, M. (2012). Bioorg. Med. Chem. 20, 2535-2539.]). For similar compounds, see: Abbassi et al. (2012[Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240-249.], 2013[Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.]); Chicha et al. (2013[Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17N3O2S

  • Mr = 327.40

  • Triclinic, [P \overline 1]

  • a = 8.8200 (4) Å

  • b = 10.4769 (5) Å

  • c = 19.7407 (10) Å

  • [alpha] = 80.211 (1)°

  • [beta] = 78.984 (1)°

  • [gamma] = 69.784 (1)°

  • V = 1669.51 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 296 K

  • 0.42 × 0.35 × 0.28 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.693, Tmax = 0.747

  • 31703 measured reflections

  • 6791 independent reflections

  • 5368 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.120

  • S = 1.02

  • 6791 reflections

  • 415 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N6-H6N...O1 0.79 2.11 2.900 (2) 176
N3-H3N...N5i 0.80 2.19 2.983 (2) 175
C21-H21...O4ii 0.93 2.49 3.245 (2) 138
C7-H7...O2iii 0.93 2.48 3.358 (2) 158
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) -x, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: IM2445 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240-249.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190-o191.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bouissane, L., El Kazzouli, S., Léonce, S., Pfeiffer, B., Rakib, E. M., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353.  [CSD] [CrossRef] [IUCr Journals]
El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.  [Web of Science] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mustafa, G., Khan, I. U., Ashraf, M., Afzal, I., Shahzad, S. A. & Shafiq, M. (2012). Bioorg. Med. Chem. 20, 2535-2539.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1847  [ doi:10.1107/S1600536813032091 ]

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