[Journal logo]

Volume 69 
Part 8 
Pages o1227-o1228  
August 2013  

Received 19 June 2013
Accepted 1 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.104
Data-to-parameter ratio = 20.3
Details
Open access

3-(4-Aminophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: suchada.c@psu.ac.th

In the molecule of title pyrazoline derivative, C17H18N4OS, the pyrazole ring adopts an envelope conformation with the flap atom, which bears the methoxyphenyl substituent, displaced by 0.0750 (12) Å from the plane through the other ring atoms. The two substituted benzene rings make a dihedral angle of 70.59 (6)°. The methoxy group is twisted slightly with respect to the attached benzene ring [Cmethyl-O-C-C torsion angle = -8.84 (15)°]. An intramolecular N-H...N hydrogen bond occurs. In the crystal, the pyrazoline molecules are linked by N-H...O and N-H...S hydrogen bonds into zigzag layers parallel to the bc plane and stacked along the a axis by [pi]-[pi] interactions with centroid-centroid distances of 3.4690 (7) and 3.5792 (7) Å. C-H...[pi] interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Fun et al. (2011[Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o701-o702.]); Quah et al. (2013[Quah, C. K., Fun, H.-K., Suwunwong, T., Boonnak, N. & Chantrapromma, S. (2013). Acta Cryst. E69, o464-o465.]). For background to and applications of pyrazoline derivatives, see: Gong et al. (2010[Gong, Z.-L., Zheng, L.-W., Zhao, B.-X., Yang, D.-Z., Lv, H.-S., Liu, W.-Y. & Lian, S. (2010). J. Photochem. Photobiol. A Chem. 209, 49-55.]); Husain et al. (2008[Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393-403.]); Khode et al. (2009[Khode, S., Maddi, V., Aragade, P., Palkar, M., Ronad, P. K., Mamledesai, S., Thippeswamy, A. H. M. & Satyanarayana, D. (2009). Eur J. Med. Chem. 44, 1682-1688.]); Lv et al. (2011[Lv, P.-C., Li, D.-D., Li, Q.-S., Lu, X., Xiao, Z.-P. & Zhu, H.-L. (2011). Bioorg. Med. Chem. Lett. 21, 5374-5377.]); Sakthinathan et al. (2012[Sakthinathan, S. P., Vanangamudi, G. & Thirunarayanan, G. (2012). Spectrochim. Acta A. 95, 693-700.]); Shaharyar et al. (2010[Shaharyar, M., Abdullah, M. M., Bakht, M. A. & Majeed, J. (2010). Eur J. Med. Chem. 45, 114-119.]); Shoman et al. (2009[Shoman, M. E., Abdel-Aziz, M., Aly, O. M., Farag, H. H. & Morsy, M. A. (2009). Eur J. Med. Chem. 44, 3068-3076.]). For the stability of the temperature controller, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N4OS

  • Mr = 326.42

  • Monoclinic, P 21 /c

  • a = 8.0052 (2) Å

  • b = 17.3439 (5) Å

  • c = 12.4588 (3) Å

  • [beta] = 114.789 (1)°

  • V = 1570.41 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 100 K

  • 0.57 × 0.39 × 0.29 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.886, Tmax = 0.940

  • 23819 measured reflections

  • 4571 independent reflections

  • 4045 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.104

  • S = 1.05

  • 4571 reflections

  • 225 parameters

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N3-H1N3...S1i 0.866 (17) 2.664 (17) 3.4559 (12) 152.5 (15)
N3-H2N3...S1ii 0.84 (2) 2.60 (2) 3.4142 (12) 164.2 (18)
N4-H2N4...N1 0.881 (17) 2.209 (16) 2.6093 (15) 107.2 (13)
N4-H2N4...O1ii 0.881 (17) 2.567 (17) 3.3022 (14) 141.5 (13)
C8-H8A...Cg2i 0.99 2.66 3.4159 (13) 133
Symmetry codes: (i) -x+1, -y+2, -z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, 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: RZ5075 ).


Acknowledgements

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) is gratefully acknowledge. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. The authors extend their appreciation to Prince of Songkla University and Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o701-o702.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Gong, Z.-L., Zheng, L.-W., Zhao, B.-X., Yang, D.-Z., Lv, H.-S., Liu, W.-Y. & Lian, S. (2010). J. Photochem. Photobiol. A Chem. 209, 49-55.  [CSD] [CrossRef] [ChemPort]
Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393-403.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Khode, S., Maddi, V., Aragade, P., Palkar, M., Ronad, P. K., Mamledesai, S., Thippeswamy, A. H. M. & Satyanarayana, D. (2009). Eur J. Med. Chem. 44, 1682-1688.  [CrossRef] [PubMed] [ChemPort]
Lv, P.-C., Li, D.-D., Li, Q.-S., Lu, X., Xiao, Z.-P. & Zhu, H.-L. (2011). Bioorg. Med. Chem. Lett. 21, 5374-5377.  [CrossRef] [ChemPort] [PubMed]
Quah, C. K., Fun, H.-K., Suwunwong, T., Boonnak, N. & Chantrapromma, S. (2013). Acta Cryst. E69, o464-o465.  [CrossRef] [ChemPort] [IUCr Journals]
Sakthinathan, S. P., Vanangamudi, G. & Thirunarayanan, G. (2012). Spectrochim. Acta A. 95, 693-700.  [ChemPort]
Shaharyar, M., Abdullah, M. M., Bakht, M. A. & Majeed, J. (2010). Eur J. Med. Chem. 45, 114-119.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shoman, M. E., Abdel-Aziz, M., Aly, O. M., Farag, H. H. & Morsy, M. A. (2009). Eur J. Med. Chem. 44, 3068-3076.  [CrossRef] [PubMed] [ChemPort]
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, o1227-o1228   [ doi:10.1107/S1600536813018096 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.