[Journal logo]

Volume 65 
Part 6 
Pages o1242-o1243  
June 2009  

Received 25 April 2009
Accepted 2 May 2009
Online 14 May 2009


[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.046
wR = 0.139
Data-to-parameter ratio = 17.2
Details

4-{[(E)-(4-Chlorophenyl)methylidene]amino}-3-{2-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,a*+ Samuel Robinson Jebas,a++ K. V Sujithb and Balakrishna Kallurayab

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent molecules, labelled A to I. The orientation of the 2-[4-(2-methylpropyl)phenyl]ethyl unit with respect to the rest of the molecule is significantly different in molecules E, F, H and I compared to the other independent molecules. The isobutyl group of molecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chlorophenyl and methylpropylphenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in molecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent molecule, a C-H...S hydrogen bond is observed. The crystal packing is stabilized by N-H...S and C-H...S hydrogen bonds, and by C-H...[pi] interactions involving the methylpropylphenyl ring.

Related literature

For the activity of ibuprofen, see: Amir & Kumar (2007[Amir, M. & Kumar, S. (2007). Acta Pharm. 57, 31-45.]). For the activity of 1,2,4-triazol-5-one compounds, see: Demirbas et al. (2002[Demirbas, N., Ugurluoglu, R. & Demirbasx, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.], 2004[Demirbas, N., Alpay-Karaoglu, S., Demirbas, A. & Sancak, K. (2004). Eur. J. Med. Chem. 39, 793-804.]). 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-S19.]). For related structures, see: Fun et al. (2008a[Fun, H.-K., Jebas, S. R., Razak, I. A., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008a). Acta Cryst. E64, o1076-o1077.],b[Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008b). Acta Cryst. E64, o1001-o1002.]). 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 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

  • C21H23ClN4S

  • Mr = 398.94

  • Triclinic, [P \overline 1]

  • a = 13.1781 (2) Å

  • b = 23.7731 (4) Å

  • c = 30.8550 (5) Å

  • [alpha] = 92.861 (1)°

  • [beta] = 101.520 (1)°

  • [gamma] = 92.254 (1)°

  • V = 9447.8 (3) Å3

  • Z = 18

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 100 K

  • 0.55 × 0.34 × 0.13 mm
Data collection

  • Bruker SMART 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 = 0.855, Tmax = 0.962

  • 157626 measured reflections

  • 38430 independent reflections

  • 27090 reflections with I > 2[sigma](I)

  • Rint = 0.044
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.139

  • S = 1.01

  • 38430 reflections

  • 2230 parameters

  • 71 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.84 e Å-3

  • [Delta][rho]min = -0.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AB...S1Fi 0.86 2.52 3.373 (2) 170
N1B-H1BB...S1Cii 0.86 2.47 3.3072 (19) 163
N1C-H1CB...S1Biii 0.86 2.45 3.285 (2) 165
N1D-H1DB...S1Eiv 0.86 2.48 3.3289 (19) 171
N1E-H1EB...S1Dv 0.86 2.41 3.253 (2) 168
N1F-H1FB...S1Ai 0.86 2.41 3.256 (2) 167
N1G-H1GB...S1Hiv 0.86 2.43 3.287 (2) 174
N1H-H1HB...S1Gv 0.86 2.45 3.3047 (19) 170
N1I-H1IB...S1Ivi 0.86 2.45 3.301 (2) 172
C10D-H10D...S1Civ 0.98 2.87 3.769 (2) 152
C10G-H10G...S1Fiv 0.98 2.82 3.662 (2) 144
C7A-H7AA...S1A 0.93 2.58 3.174 (2) 122
C7B-H7BA...S1B 0.93 2.57 3.240 (2) 130
C7C-H7CA...S1C 0.93 2.58 3.254 (2) 130
C7D-H7DA...S1D 0.93 2.59 3.174 (2) 121
C7E-H7EA...S1E 0.93 2.56 3.223 (2) 129
C7F-H7FA...S1F 0.93 2.56 3.229 (2) 130
C7G-H7GA...S1G 0.93 2.61 3.178 (2) 120
C7H-H7HA...S1H 0.93 2.55 3.187 (2) 126
C7I-H7IA...S1I 0.93 2.61 3.179 (2) 120
C4D-H4DA...Cg1 0.93 2.72 3.588 (2) 156
C4E-H4EA...Cg2 0.93 2.84 3.566 (3) 136
C4G-H4GA...Cg3 0.93 2.86 3.701 (2) 152
C4H-H4HA...Cg4 0.93 2.51 3.338 (2) 148
C4A-H4AA...Cg5vi 0.93 2.72 3.606 (2) 159
C4C-H4CA...Cg6vii 0.93 2.96 3.670 (2) 134
C4F-H4FA...Cg7vi 0.93 2.78 3.524 (3) 137
C4I-H4IA...Cg8viii 0.93 2.88 3.719 (2) 151
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y+1, z; (iii) x-1, y-1, z; (iv) x+1, y, z; (v) x-1, y, z; (vi) -x+1, -y+1, -z+1; (vii) x, y-1, z; (viii) -x+2, -y+1, -z+1. Cg1 is the centroid of the N1/C2-C5 ring.

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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2794 ).

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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-S19.
Amir, M. & Kumar, S. (2007). Acta Pharm. 57, 31-45.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [details]
Demirbas, N., Alpay-Karaoglu, S., Demirbas, A. & Sancak, K. (2004). Eur. J. Med. Chem. 39, 793-804.  [CrossRef] [PubMed] [ChemPort]
Demirbas, N., Ugurluoglu, R. & Demirbasx, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.  [CrossRef] [PubMed] [ChemPort]
Fun, H.-K., Jebas, S. R., Razak, I. A., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008a). Acta Cryst. E64, o1076-o1077.  [CrossRef] [details]
Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008b). Acta Cryst. E64, o1001-o1002.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [CrossRef] [details]

Acta Cryst (2009). E65, o1242-o1243   [ doi:10.1107/S160053680901650X ]

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.