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Volume 68 
Part 1 
Page o201  
January 2012  

Received 5 December 2011
Accepted 13 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 15.5
Details
Open access

N-(Pyrrolidin-1-ylcarbothioyl)benzamide

aSchool of Chemical Sciences & Food Technology, Faculty of Science & Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia,bDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia, and cFuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia
Correspondence e-mail: mbkassim@ukm.my

In the title compound, C12H14N2OS, the pyrrolidine ring adopts an envelope conformation with the C atom at the 3-position as the flap and makes a dihedral angle of 65.80 (9)° with the benzene ring. In the crystal, N-H...O hydrogen bonds join c-glide related molecules into chains extended along [001] that are further connected into (100) layers via C-H...O interactions.

Related literature

For related compounds, their structural parameters and chemical properties, see: Al-abbasi et al. (2010[Al-abbasi, A. A., Yarmo, M. A. & Kassim, M. B. (2010). Acta Cryst. E66, o2896.], 2011[Al-abbasi, A. A., Yamin, B. M. & Kassim, M. B. (2011). Acta Cryst. E67, o1891.]); Al-abbasi & Kassim (2011[Al-abbasi, A. A. & Kassim, M. B. (2011). Acta Cryst. E67, o611.]); Ngah et al. (2006[Ngah, N., Kassim, M. B. & Yamin, B. M. (2006). Acta Cryst. E62, o4501-o4502.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N2OS

  • Mr = 234.31

  • Monoclinic, P 21 /c

  • a = 10.3666 (4) Å

  • b = 14.6008 (5) Å

  • c = 7.8240 (3) Å

  • [beta] = 98.446 (4)°

  • V = 1171.40 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.29 mm-1

  • T = 150 K

  • 0.13 × 0.06 × 0.03 mm

Data collection
  • Oxford Diffraction Gemini area-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]) Tmin = 0.870, Tmax = 0.934

  • 8077 measured reflections

  • 2245 independent reflections

  • 1958 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.098

  • S = 1.03

  • 2245 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.27 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 2.05 2.8637 (17) 157
C11-H11A...O1ii 0.97 2.52 3.339 (2) 142
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); data reduction: CrysAlis RED; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2440 ).


Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (UKM-OUP-TK-16-73/2011 and UKM-PTS-016-2010) and the Libyan Government for providing a scholarship to AAA.

References

Al-abbasi, A. A. & Kassim, M. B. (2011). Acta Cryst. E67, o611.  [CSD] [CrossRef] [details]
Al-abbasi, A. A., Yamin, B. M. & Kassim, M. B. (2011). Acta Cryst. E67, o1891.  [CSD] [CrossRef] [details]
Al-abbasi, A. A., Yarmo, M. A. & Kassim, M. B. (2010). Acta Cryst. E66, o2896.  [CSD] [CrossRef] [details]
Ngah, N., Kassim, M. B. & Yamin, B. M. (2006). Acta Cryst. E62, o4501-o4502.  [CSD] [CrossRef] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o201  [ doi:10.1107/S1600536811053694 ]

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