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Volume 66 
Part 7 
Page o1749  
July 2010  

Received 13 June 2010
Accepted 17 June 2010
Online 23 June 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.043
wR = 0.113
Data-to-parameter ratio = 11.1
Details
Open access

1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4-(trifluoromethyl)phenyl]thiosemicarbazide

Humayun Pervez,a Mohammad S. Iqbal,b Naveeda Saira,a Muhammad Yaquba and M. Nawaz Tahirc*

aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan,bDepartment of Chemistry, Government College University, Lahore, Pakistan, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C17H10F6N4O2S, an intramolecular N-H...N hydrogen bonds forms an S(5) ring whereas N-H...O and C-H...S interactions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the molecules are dimerized due to N-H...O interactions. [pi]-[pi] interactions are present between the benzene rings [centroid-centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoromethyl)phenyl ring [centroids-centroid distance = 3.7827 (16) Å]. One of the trifluoromethoxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoromethyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).

Related literature

For background to the synthesis, see: Pervez et al. (2009[Pervez, H., Yaqub, M., Manzoor, N., Tahir, M. N. & Iqbal, M. S. (2009). Acta Cryst. E65, o2858.], 2010b[Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010b). Lett. Drug Des. Discov. 7, 102-108.],c[Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010c). Acta Cryst. E66, o1609.]). For a related structure, see: Pervez et al. (2010a[Pervez, H., Iqbal, M. S., Saira, N., Yaqub, M. & Tahir, M. N. (2010a). Acta Cryst. E66, o1169-o1170.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C17H10F6N4O2S

  • Mr = 448.35

  • Triclinic, [P \overline 1]

  • a = 7.5452 (11) Å

  • b = 8.3177 (13) Å

  • c = 16.048 (2) Å

  • [alpha] = 104.452 (6)°

  • [beta] = 94.752 (7)°

  • [gamma] = 103.606 (7)°

  • V = 937.1 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 296 K

  • 0.32 × 0.24 × 0.22 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.952

  • 13964 measured reflections

  • 3351 independent reflections

  • 2191 reflections with I > 2[sigma](I)

  • Rint = 0.045
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.113

  • S = 1.02

  • 3351 reflections

  • 302 parameters

  • 11 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 1.98 2.829 (3) 168
N3-H3A...O1 0.86 2.01 2.716 (3) 138
N4-H4A...N2 0.86 2.19 2.627 (3) 111
C12-H12...S1 0.93 2.56 3.210 (3) 128
Symmetry code: (i) -x+2, -y+3, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2270 ).

Acknowledgements

This work was supported by the Higher Education Commission (HEC), Pakistan (project No. 20-873/R&D/07/452).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Pervez, H., Iqbal, M. S., Saira, N., Yaqub, M. & Tahir, M. N. (2010a). Acta Cryst. E66, o1169-o1170.  [CrossRef] [details]
Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010b). Lett. Drug Des. Discov. 7, 102-108.  [CrossRef] [ChemPort]
Pervez, H., Yaqub, M., Manzoor, N., Tahir, M. N. & Iqbal, M. S. (2009). Acta Cryst. E65, o2858.  [CrossRef] [details]
Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010c). Acta Cryst. E66, o1609.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1749  [ doi:10.1107/S1600536810023494 ]

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