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

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

doi:10.1107/S1600536808009513

. 2008 Apr 10;64(Pt 5):o833. doi: 10.1107/S1600536808009513

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

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

PMCID: PMC2961265 PMID: 21202322

Abstract

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—H⋯N intramolecular hydrogen bond is also present. Molecules are linked by intermolecular N—H⋯O and C—H⋯S 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,
a = 7.955 (3) Å
b = 7.811 (3) Å
c = 23.414 (8) Å
β = 90.827 (6)°
V = 1454.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.112
S = 1.02
2710 reflections
191 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009513/sg2229sup1.cif

e-64-0o833-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009513/sg2229Isup2.hkl

e-64-0o833-Isup2.hkl^{(133.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (2)	2.04 (2)	2.697 (2)	132.2 (18)
C15—H15A⋯N2	0.96	2.56	2.961	105
N2—H2⋯O1ⁱ	0.86 (2)	2.30 (2)	3.021 (2)	142 (2)
C13—H13⋯S1ⁱⁱ	0.93	2.85	3.700	154

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

The title compound, (I), is analogous to N-(3-iodophenyl)-N'-(2-methylbenzoyl) thiourea (II), (Yusof et al., 2007) except that the iodophenyl group is replaced by the 3-methylpyridine group (Fig.1). The bond lengths and angles are in normal range (Allen et al., 1987). The central thiourea moiety, S1/N1/N2/C9, pyridine, N3/(C10—C14), and benzene,(C1—C6) rings are each planar with maximum deviation of 0.033 (2)Å for N2 atom from the least square plane. The central thiourea moiety makes dihedral angle with the pyridine and benzene rings of 64.58 (8) and 62.03 (8)° respectively. The dihedral angle between the pyridine and benzene rings (4.03 (10)°) is smaller compared to that in (II) of 31.88 (9)°. The molecule maintains the trans-cis geometry of the thiourea moiety which is stabilized by the intrahydrogen bond between the carbonyl oxygen atom O1 and the thioamide hydrogen atom, H15A. In the crystal structure, the molecules are linked by the N2—H2···O1 and C13—H13···S1 intermolecular hydrogen bonds (symmtery codes as in Table 2).

Experimental

The mixture of 2-methylbenzoyl chloride (9.720 g, 0.025mole) with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2-amino-3-methyl pyridine,(2.703 g, 0.025 mol) in 40 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The colourless crystals obtained after a few days, was found suitable for X-ray investigations. The yield was 85% and the melting point is 412.3–413.8 K.