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Volume 69 
Part 9 
Page o1376  
September 2013  

Received 30 June 2013
Accepted 12 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.074
Data-to-parameter ratio = 15.1
Details
Open access

Ethyl 5-amino-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carboxylate

aChemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt,bFaculty of Education, Ain Shams University, Abbassia, Cairo, Egypt, and cInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
Correspondence e-mail: elgawy@sci.asu.edu.eg

In the title molecule, C13H15N3O4S, the benzene and pyrazole rings are inclined to each other at 77.48 (3)°. Two amino H atoms are involved in bifurcated hydrogen bonds, viz. intramolecular N-H...O and intermolecular N-H...O(N). The intermolecular hydrogen bonds link the molecules related by translation in [100] into chains. A short distance of 3.680 (3) Å between the centroids of benzene and pyrazole rings from neighbouring molecules shows the presence of [pi]-[pi] interactions, which link the hydrogen-bonded chains into layers parallel to the ab plane.

Related literature

For background details and information on the synthesis, see: Elgazwy, Ismail et al. (2012[Elgazwy, A.-S. S. H., Ismail, N. S. M., Atta-Allah, S. R., Sarg, M. T., Soliman, D. H. S., Zaki, M. Y. & Elgamas, M. A. (2012). Curr. Med. Chem. 19, 3967-3981.]); Elgazwy, Soliman et al. (2012[Elgazwy, A.-S. S. H., Soliman, D. H. S., Atta-Allah, S. R. & Ibrahim, D. A. (2012). Chem. Cent. J. 6, 1-18.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15N3O4S

  • Mr = 309.34

  • Monoclinic, P 21 /n

  • a = 6.27869 (7) Å

  • b = 15.43607 (12) Å

  • c = 15.27141 (13) Å

  • [beta] = 96.2633 (9)°

  • V = 1471.24 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.14 mm-1

  • T = 100 K

  • 0.25 × 0.12 × 0.10 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.800, Tmax = 1.000

  • 51079 measured reflections

  • 3043 independent reflections

  • 3035 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.074

  • S = 1.05

  • 3043 reflections

  • 201 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H01...O1i 0.852 (18) 2.554 (17) 3.0631 (13) 119.3 (13)
N3-H01...O2 0.852 (18) 2.237 (17) 2.8624 (13) 130.3 (14)
N3-H02...O3 0.865 (18) 2.456 (17) 2.9775 (13) 119.4 (13)
N3-H02...N2i 0.865 (18) 2.206 (18) 3.0216 (14) 157.1 (15)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, 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: XP (Siemens, 1994[Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5421 ).


Acknowledgements

The authors acknowledge the financial support of the Ain Shams University, established and supported under the Egyptian Government Cooperative Research Centers Program.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Elgazwy, A.-S. S. H., Ismail, N. S. M., Atta-Allah, S. R., Sarg, M. T., Soliman, D. H. S., Zaki, M. Y. & Elgamas, M. A. (2012). Curr. Med. Chem. 19, 3967-3981.  [ISI] [ChemPort] [PubMed]
Elgazwy, A.-S. S. H., Soliman, D. H. S., Atta-Allah, S. R. & Ibrahim, D. A. (2012). Chem. Cent. J. 6, 1-18.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.


Acta Cryst (2013). E69, o1376  [ doi:10.1107/S1600536813019326 ]

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