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Volume 69 
Part 5 
Pages o736-o737  
May 2013  

Received 10 April 2013
Accepted 10 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.136
Data-to-parameter ratio = 16.1
Details
Open access

4-(2H-1,3-Benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine

aP.S. Science and H.D. Patel Arts College, S.V. Campus, Kadi, Gujarat 382 715, India,bDepartment of Physics, Bhavan's Sheth R.A. College of Science, Ahmedabad, Gujarat 380 001, India, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C17H15N3O2, two independent molecules (A and B) comprise the asymmetric unit. The major conformational difference arises in the relative orientation of the pyrazole ring amine and dioxole substituents which are anti in A and syn in B. The five-membered dioxole ring in each molecule has an envelope conformation with the methylene C atom as the flap. The mean plane through the benzodioxole and benzene groups make dihedral angles of 31.67 (8) and 68.22 (9)°, respectively, with the pyrazole ring in A; the equivalent values for B are 47.18 (7) and 49.08 (9)°. In the crystal, supramolecular zigzag chains along the b-axis direction arise as a result of N-H...N hydrogen bonding. These are consolidated into supramolecular double chains via C-H...O and C-H...[pi] interactions.

Related literature

For background to the biological activity of amino substituted pyrazole derivatives, see: Tanitame et al. (2004[Tanitame, A., Oyamada, Y., Ofuji, K., Fujimoto, M., Iwai, N., Hiyama, Y., Suzuki, K., Ito, H., Terauchi, H., Kawasaki, M., Nagai, K., Wachi, M. & Yamagishi, J. (2004). J. Med. Chem. 47, 3693-3696.]); Chimenti et al. (2006[Chimenti, F., Bolasco, A., Manna, F., Secci, D., Chimenti, P., Granese, A., Befani, O., Turini, P., Cirilli, R., La Torre, F., Alcaro, S., Ortuso, F. & Langer, T. (2006). Curr. Med. Chem. 13, 1411-1428.]); Ding et al. (2009[Ding, X.-L., Zhang, H.-Y., Qi, L., Zhao, B.-X., Lian, S., Lv, H.-S. & Miao, J.-Y. (2009). Bioorg. Med. Chem. Lett. 19, 5325-5328.]); Shen et al. (2011[Shen, D.-M., Brady, E. J., Candelore, M. R., Dallas-Yang, Q., Ding, V. D.-H., Feeney, W. P., Jiang, G., McCann, M. E., Mock, S., Qureshi, S. A., Saperstein, R., Shen, X., Tong, X., Tota, L. M., Wright, M. J., Yang, X., Zheng, S., Chapman, K. T., Zhang, B. B., Tata, J. R. & Parmee, E. R. (2011). Bioorg. Med. Chem. Lett. 21, 76-81.]); Deng et al. (2012[Deng, H., Yu, Z., Shi, G., Chen, M., Tao, K. & Hou, T. (2012). Chem. Biol. Drug Des. 79, 279-289.]). For a related structure, see: Muruganantham et al. (2007[Muruganantham, R., Mobin, S. M. & Namboothiri, I. N. N. (2007). Org. Lett. 9, 1125-1128.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15N3O2

  • Mr = 293.32

  • Triclinic, [P \overline 1]

  • a = 9.7690 (7) Å

  • b = 10.4250 (7) Å

  • c = 14.283 (1) Å

  • [alpha] = 96.626 (2)°

  • [beta] = 91.903 (2)°

  • [gamma] = 91.164 (2)°

  • V = 1443.67 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.40 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.982

  • 29089 measured reflections

  • 6620 independent reflections

  • 4674 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.136

  • S = 1.02

  • 6620 reflections

  • 412 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1-Cg3 are the centroids of the C28-C33, C19-C24 and C2-C7 rings, respectviely.

D-H...A D-H H...A D...A D-H...A
N3-H1N...N5i 0.89 (2) 2.20 (2) 3.059 (2) 161 (2)
N6-H3N...N2ii 0.89 (1) 2.11 (1) 2.9914 (19) 170 (2)
C1-H1C...O3ii 0.96 2.54 3.479 (2) 164
C3-H3...Cg1iii 0.93 2.83 3.5365 (19) 133
C10-H10...Cg2ii 0.93 2.88 3.6055 (17) 135
C27-H27...Cg3i 0.93 2.94 3.5903 (18) 128
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SADABS and SAINT, 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.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: SU2585 ).


Acknowledgements

The authors are grateful to the Department of Science and Technology (DST), and SAIF, IIT Madras, Chennai, India, for the X-ray data collection. MCP is thankful to the University Grant Commission, New Delhi, India, for research funding under research project No. 39-715/2010(SR). We also thank the Ministry of Higher Education, Malaysia, for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.
Chimenti, F., Bolasco, A., Manna, F., Secci, D., Chimenti, P., Granese, A., Befani, O., Turini, P., Cirilli, R., La Torre, F., Alcaro, S., Ortuso, F. & Langer, T. (2006). Curr. Med. Chem. 13, 1411-1428.  [ISI] [CrossRef] [PubMed] [ChemPort]
Deng, H., Yu, Z., Shi, G., Chen, M., Tao, K. & Hou, T. (2012). Chem. Biol. Drug Des. 79, 279-289.  [CrossRef] [ChemPort] [PubMed]
Ding, X.-L., Zhang, H.-Y., Qi, L., Zhao, B.-X., Lian, S., Lv, H.-S. & Miao, J.-Y. (2009). Bioorg. Med. Chem. Lett. 19, 5325-5328.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.  [CrossRef] [PubMed] [ChemPort]
Muruganantham, R., Mobin, S. M. & Namboothiri, I. N. N. (2007). Org. Lett. 9, 1125-1128.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shen, D.-M., Brady, E. J., Candelore, M. R., Dallas-Yang, Q., Ding, V. D.-H., Feeney, W. P., Jiang, G., McCann, M. E., Mock, S., Qureshi, S. A., Saperstein, R., Shen, X., Tong, X., Tota, L. M., Wright, M. J., Yang, X., Zheng, S., Chapman, K. T., Zhang, B. B., Tata, J. R. & Parmee, E. R. (2011). Bioorg. Med. Chem. Lett. 21, 76-81.  [CrossRef] [ChemPort] [PubMed]
Tanitame, A., Oyamada, Y., Ofuji, K., Fujimoto, M., Iwai, N., Hiyama, Y., Suzuki, K., Ito, H., Terauchi, H., Kawasaki, M., Nagai, K., Wachi, M. & Yamagishi, J. (2004). J. Med. Chem. 47, 3693-3696.  [ISI] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o736-o737   [ doi:10.1107/S1600536813009914 ]

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