2-Methyl-N-[(3-methyl-2-pyrid­yl)carbamothio­yl]benzamide

Yamin, B.M.; Yousuf, S.; Yusof, M.S.M.; Jusoh, R.H.

doi:10.1107/S1600536808009513

Volume 64
Part 5
Page o833
May 2008

Received 25 March 2008
Accepted 7 April 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 14.2
Details

2-Methyl-N-[(3-methyl-2-pyridyl)carbamothioyl]benzamide

B. M. Yamin,^a S. Yousuf,^b ^* M. S. M. Yusof ^c and R. H. Jusoh ^c

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia,^bHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^cDepartment of Chemistry, Universiti Malaysia Terengganu, Manngabang Telipot, Terengganu, Malaysia
Correspondence e-mail: sammer_yousuf@yahoo.com

In the title compound, C₁₅H₁₅N₃OS, the thiourea group is stabilized by an intramolecular hydrogen bond between the carbonyl O atom and the thioamide group. A C-HN intramolecular hydrogen bond is also present. Molecules are linked by intermolecular N-HO and C-HS hydrogen bonds.

Related literature

For the crystal structure of N-(3-iodophenyl)-N'-(2-methylbenzoyl)thiourea, see: Yusof et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₅N₃OS
M_r = 285.36
Monoclinic, P 2₁ /n
a = 7.955 (3) Å
b = 7.811 (3) Å
c = 23.414 (8) Å
= 90.827 (6)°
V = 1454.6 (9) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 298 (2) K
0.49 × 0.46 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.899, T_max = 0.963
7524 measured reflections
2710 independent reflections
2099 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.112
S = 1.02
2710 reflections
191 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.86 (2)	2.04 (2)	2.697 (2)	132.2 (18)
C15-H15AN2	0.96	2.56	2.961	105
N2-H2O1ⁱ	0.86 (2)	2.30 (2)	3.021 (2)	142 (2)
C13-H13S1ⁱⁱ	0.93	2.85	3.700	154
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2229 ).

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia for Fundamental Research Grants UKM-ST-01-FRGS-0003-2006 and UMT-FRGS-59001, and Universiti Kebangsaan Malaysia and HEJ Research Institute of Chemistry, University of Karachi, for research facilities.

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.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Yusof, M. S. M., Ahmad Mushtari, N. & Yamin, B. M. (2007). Acta Cryst. E63, o4709.

organic compounds