N-(Pyrrolidin-1-ylcarbothio­yl)benzamide

Al-abbasi, A.A.; Mohamed Tahir, M.I.; Kassim, M.B.

doi:10.1107/S1600536811053694

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 15.5
Details

N-(Pyrrolidin-1-ylcarbothioyl)benzamide

Aisha A. Al-abbasi,^a Mohamed Ibrahim Mohamed Tahir ^b and Mohammad B. Kassim ^a,^c ^*

^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-HO hydrogen bonds join c-glide related molecules into chains extended along [001] that are further connected into (100) layers via C-HO interactions.

Related literature

For related compounds, their structural parameters and chemical properties, see: Al-abbasi et al. (2010, 2011); Al-abbasi & Kassim (2011); Ngah et al. (2006).

Experimental

Crystal data

C₁₂H₁₄N₂OS
M_r = 234.31
Monoclinic, P 2₁ /c
a = 10.3666 (4) Å
b = 14.6008 (5) Å
c = 7.8240 (3) Å
= 98.446 (4)°
V = 1171.40 (8) Å³
Z = 4
Cu K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ) T_min = 0.870, T_max = 0.934
8077 measured reflections
2245 independent reflections
1958 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.098
S = 1.03
2245 reflections
145 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.05	2.8637 (17)	157
C11-H11AO1ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

organic compounds