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Volume 69 
Part 7 
Pages o1016-o1017  
July 2013  

Received 10 May 2013
Accepted 23 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.098
Data-to-parameter ratio = 16.3
Details
Open access

N-[(3-Ethylphenyl)carbamothioyl]-2,2-diphenylacetamide

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

In the title molecule, C23H22N2OS, the diphenylacetyl and ethylbenzene groups adopt a trans-cis conformation, respectively, with respect to the S atom across the (S=)C-N bonds. This conformation is stabilized by an intramolecular N-H...O hydrogen bond and a weak C-H...S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N-H...O hydrogen bonds link molecules into chains along [100]. A weak C-H...[pi] interaction is also observed.

Related literature

For the biological activity of carbonylthiourea derivatives, see: Zhong et al. (2008[Zhong, Z., Xing, R., Liu, S., Wang, L., Cai, S. & Li, P. (2008). Carbohydr. Res. 343, 566-570.]); Saeed et al. (2010[Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.]). For related structures, see: Yusof et al. (2012a[Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o982.],b[Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012b). Acta Cryst. E68, o2670.]). 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 for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For standard bond lenths, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C23H22N2OS

  • Mr = 374.49

  • Orthorhombic, P n a 21

  • a = 10.0608 (2) Å

  • b = 17.9092 (5) Å

  • c = 10.8495 (3) Å

  • V = 1954.87 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 100 K

  • 0.26 × 0.23 × 0.09 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 = 0.955, Tmax = 0.983

  • 11560 measured reflections

  • 4121 independent reflections

  • 2885 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.098

  • S = 0.99

  • 4121 reflections

  • 253 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1761 Friedel pairs

  • Flack parameter: 0.17 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O1 0.90 (3) 1.82 (3) 2.630 (3) 148 (3)
C21-H21A...S1 0.95 2.61 3.255 (3) 126
N1-H1N1...O1i 0.82 (3) 2.25 (3) 3.023 (3) 157 (3)
C7-H7A...Cgii 1.00 2.87 3.844 (3) 166
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (ii) [-x-{\script{1\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}].

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: LH5616 ).


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]
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
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]
Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012b). Acta Cryst. E68, o2670.  [CSD] [CrossRef] [IUCr Journals]
Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o982.  [CSD] [CrossRef] [IUCr Journals]
Zhong, Z., Xing, R., Liu, S., Wang, L., Cai, S. & Li, P. (2008). Carbohydr. Res. 343, 566-570.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1016-o1017   [ doi:10.1107/S1600536813014268 ]

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