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Volume 69 
Part 4 
Pages o464-o465  
April 2013  

Received 19 February 2013
Accepted 25 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 13.6
Details
Open access

3-(4-Chlorophenyl)-5-(4-ethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide ethanol monosolvate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and dFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent molecule. In the molecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the ethoxyphenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22 (7)°. The ethoxy group is coplanar with the attached benzene ring [C-O-C-Cmethyl = 175.50 (11)° and r.m.s. deviation = 0.0459 (1) Å for the nine non-H atoms]. In the crystal, the pyrazoline molecules are linked by N-H...Oethoxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol molecules by N-H...Oethanol and Oethanol-H...S hydrogen bonds. 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 ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Chantrapromma et al. (2012[Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830-o831.]); Nonthason et al. (2011[Nonthason, P., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3501-o3502.]). For background to and applications of pyrazoline derivatives, see: Bilgin et al. (1992[Bilgin, A. A., Palaska, E. & Sunal, R. (1992). Arzneim. Forschung. Drug Res. 42, 1271-1273.], 1993[Bilgin, A. A., Palaska, E. & Sunal, R. (1993). Arzneim. Forschung. Drug Res. 43, 1041-1044.], 1994[Bilgin, A. A., Palaska, E., Sunal, R. & Gumuxsel, B. (1994). Pharmazie, 49, 67-69.]); Gokhan et al. (2003[Gokhan, N., Yesilada, A., Ucar, G., Erol, K. & Bilgin, A. A. (2003). Arch. Pharm. Med. Chem. 336, 362-371.]); Ruhoglu et al. (2005[Ruhoglu, O., Ozdemir, Z., Calis, U., Gumusel, B. & Bilgin, A. A. (2005). Arzneim. Forschung. Drug Res. 55, 431-436.]); Zhang et al. (2000[Zhang, X. H., Wu, S. K., Gao, Z. Q., Lee, C. S., Lee, S. T. & Kwong, H. L. (2000). Thin Solid Films, 371, 40-46.]). For the fluorescent properties and antioxidant activity of pyrazoline derivatives by DPPH scavenging, see: Molyneux (2004[Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18ClN3OS·C2H6O

  • Mr = 405.94

  • Monoclinic, P 21 /c

  • a = 9.3145 (4) Å

  • b = 25.3673 (12) Å

  • c = 9.5565 (5) Å

  • [beta] = 115.082 (1)°

  • V = 2045.12 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 100 K

  • 0.49 × 0.24 × 0.24 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.864, Tmax = 0.929

  • 17996 measured reflections

  • 3514 independent reflections

  • 3228 reflections with I > 2[sigma](I)

  • Rint = 0.023

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

  • wR(F2) = 0.071

  • S = 1.06

  • 3514 reflections

  • 258 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C10-C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N3-H2N3...O1i 0.879 (18) 2.225 (18) 3.0531 (16) 157.1 (17)
N3-H1N3...O2i 0.857 (19) 2.019 (19) 2.8324 (18) 158.0 (16)
O2-H1O2...S2ii 0.85 (2) 2.43 (2) 3.2340 (12) 159.1 (16)
C5-H5A...Cg2iii 0.95 2.96 3.5701 (15) 123
C8-H8A...Cg1iv 0.99 2.89 3.8543 (17) 165
Symmetry codes: (i) x, y, z-1; (ii) -x+2, -y, -z+1; (iii) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: RZ5045 ).


Acknowledgements

This work was supported by the Thailand Research Fund (TRF) through the Royal Golden Jubilee Ph.D. Program (PHD/0257/2553). The authors extend their appreciation to Prince of Songkla University and the Malaysian Government and Universiti Sains Malaysia for APEX DE2012 grant (No. 1002/PFIZIK/910323) and RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins From S.typhi By X-ray Protein Crystallography, No. 1001/PSKBP/8630013).

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.
Bilgin, A. A., Palaska, E. & Sunal, R. (1992). Arzneim. Forschung. Drug Res. 42, 1271-1273.  [ChemPort]
Bilgin, A. A., Palaska, E. & Sunal, R. (1993). Arzneim. Forschung. Drug Res. 43, 1041-1044.  [ChemPort]
Bilgin, A. A., Palaska, E., Sunal, R. & Gumuxsel, B. (1994). Pharmazie, 49, 67-69.  [ChemPort] [PubMed]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830-o831.  [CSD] [CrossRef] [details]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Gokhan, N., Yesilada, A., Ucar, G., Erol, K. & Bilgin, A. A. (2003). Arch. Pharm. Med. Chem. 336, 362-371.
Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.  [ChemPort]
Nonthason, P., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3501-o3502.  [CSD] [CrossRef] [details]
Ruhoglu, O., Ozdemir, Z., Calis, U., Gumusel, B. & Bilgin, A. A. (2005). Arzneim. Forschung. Drug Res. 55, 431-436.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, X. H., Wu, S. K., Gao, Z. Q., Lee, C. S., Lee, S. T. & Kwong, H. L. (2000). Thin Solid Films, 371, 40-46.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o464-o465   [ doi:10.1107/S1600536813005369 ]

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