[Journal logo]

Volume 69 
Part 6 
Page o967  
June 2013  

Received 7 May 2013
Accepted 15 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.087
Data-to-parameter ratio = 13.8
Details
Open access

N-[(2,6-Diethylphenyl)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 compound, C25H26N2OS, the diethyl-substituted benzene ring forms dihedral angles of 67.38 (9) and 55.32 (9)° with the terminal benzene rings. The molecule adopts a trans-cis conformation with respect to the orientations of the diphenylmethane and 1,3-diethylbenzene groups with respect to the S atom across the C-N bonds. This conformation is stabilized by an intramolecular N-H...O hydrogen bond, which generates an S(6) ring. In the crystal, pairs of N-H...S hydrogen bonds link the molecules into inversion dimers, forming R22(6) loops. The dimer linkage is reinforced by a pair of C-H...S hydrogen bonds, which generate R22(8) loops. Weak C-H...[pi] and [pi]-[pi] [centroid-centroid seperation = 3.8821 (10) Å] interactions also occur in the crystal structure.

Related literature

For related structures and backgroud to thiourea derivatives, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C25H26N2OS

  • Mr = 402.54

  • Triclinic, [P \overline 1]

  • a = 8.0091 (1) Å

  • b = 11.7289 (2) Å

  • c = 11.8923 (2) Å

  • [alpha] = 79.008 (1)°

  • [beta] = 80.628 (1)°

  • [gamma] = 83.936 (1)°

  • V = 1078.79 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 100 K

  • 0.41 × 0.17 × 0.08 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.934, Tmax = 0.987

  • 20294 measured reflections

  • 3767 independent reflections

  • 3123 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.087

  • S = 1.06

  • 3767 reflections

  • 272 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O1 0.86 (2) 1.96 (2) 2.6702 (19) 140 (2)
N1-H1N1...S1i 0.85 (2) 2.59 (2) 3.4225 (16) 167.4 (18)
C7-H7A...S1i 1.00 2.64 3.6172 (17) 165
C10-H10A...Cg1ii 0.95 2.56 3.3859 (19) 146
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, 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: HB7080 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811151 to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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] [ISI] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012b). Acta Cryst. E68, o2670.  [CSD] [CrossRef] [details]
Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o982.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o967  [ doi:10.1107/S1600536813013354 ]

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.