[Journal logo]

Volume 69 
Part 8 
Pages o1255-o1256  
August 2013  

Received 12 June 2013
Accepted 5 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.081
Data-to-parameter ratio = 20.8
Details
Open access

2,2-Diphenyl-N-{[2-(trifluoromethyl)phenyl]carbamothioyl}acetamide

aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

The title molecule, C22H17F3N2OS, adopts a trans-cis conformation with respect to the positions of the carbonyl and trifluoromethylbenzene groups against the thiocarbonyl group across the C-N bonds. The molecular structure is stabilized by an intramolecular N-H...O hydrogen bond with an S(6) ring motif. The trifluoromethyl-substituted benzene ring forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings and is twisted from the O=C-N-(C=S)-N carbonylthiourea plane [maximum deviation = 0.0535 (12) Å], making a dihedral angle of 63.59 (8)°. In the crystal, N-H...O and C-H...F hydrogen bonds link the molecules into a layer parallel to the bc plane. A C-H...[pi] interaction is also observed.

Related literature

For the biological activity of thiourea derivatives, see: Vankatachalam et al. (2001[Vankatachalam, T. K., Sudbeck, E. A., Mao, C. & Uckun, F. M. (2001). Bioorg. Med. Chem. Lett. 11, 523-528.]). For related structures, see: Yusof, Arshad et al. (2012[Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012). Acta Cryst. E68, o2670.]); Yusof, Embong et al. (2012[Yusof, M. S. M., Embong, N. F., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1029.]); Yusof, Mutalib et al. (2012[Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o982.]). 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 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 the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17F3N2OS

  • Mr = 414.44

  • Orthorhombic, P c a 21

  • a = 20.0318 (4) Å

  • b = 10.2866 (2) Å

  • c = 9.5351 (2) Å

  • V = 1964.79 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 100 K

  • 0.56 × 0.18 × 0.06 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.892, Tmax = 0.987

  • 21265 measured reflections

  • 5618 independent reflections

  • 4608 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.081

  • S = 1.02

  • 5618 reflections

  • 270 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2568 Freidel pairs

  • Flack parameter: 0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1 0.96 (3) 1.93 (2) 2.6237 (19) 127 (2)
N2-H1N2...O1i 0.81 (2) 2.04 (2) 2.838 (2) 174 (2)
C9-H9A...F1ii 0.95 2.53 3.395 (2) 151
C7-H7A...Cg1iii 1.00 2.84 3.7826 (19) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y, z].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. 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: IS5283 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the USM Short Term Grant, No. 304/PFIZIK/6312078, to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

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). SADABS, APEX2 and SAINT. 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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vankatachalam, T. K., Sudbeck, E. A., Mao, C. & Uckun, F. M. (2001). Bioorg. Med. Chem. Lett. 11, 523-528.  [CSD] [CrossRef] [PubMed]
Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012). Acta Cryst. E68, o2670.  [CSD] [CrossRef] [IUCr Journals]
Yusof, M. S. M., Embong, N. F., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1029.  [CSD] [CrossRef] [IUCr Journals]
Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o982.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1255-o1256   [ doi:10.1107/S1600536813018680 ]

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.