Crystal structure of N-carbamo­thioyl-2-methyl­benzamide

Farook Adam; Nadiah Ameram; Wai Mun Tan

doi:10.1107/S2056989015009585

. 2015 May 28;71(Pt 6):o425. doi: 10.1107/S2056989015009585

Crystal structure of N-carbamothioyl-2-methylbenzamide

Farook Adam ^a,^*, Nadiah Ameram ^a, Wai Mun Tan ^a

PMCID: PMC4459304 PMID: 26090205

Abstract

There are two molecules in the asymmetric unit of the title compound, C₉H₁₀N₂OS. In one, the dihedral angle between the aromatic ring and the carbamothioyl group is 52.31 (7)° and in the other it is 36.16 (6)°. Each molecule features an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring and the O and S atoms have an anti disposition. In the crystal, molecules are linked by N—H⋯S and N—H⋯O hydrogen bonds, generating separate [130] and [1-30] infinite chains. Weak C—H⋯O and C—H⋯S interactions are also observed.

Keywords: crystal structure, benzamide, thiourea, hydrogen bonding

Related literature

For related structures, see: Saeed & Flörke (2007 ▸); Shoukat et al. (2007 ▸); Hassan et al. (2008a ▸,b ▸,c ▸); Ameram et al. (2015 ▸). graphic file with name e-71-0o425-scheme1.jpg

Experimental

Crystal data

C₉H₁₀N₂OS
M _r = 194.25
Monoclinic,
a = 22.7886 (12) Å
b = 7.1133 (3) Å
c = 25.5388 (13) Å
β = 113.664 (3)°
V = 3791.8 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.46 × 0.33 × 0.10 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.814, T _max = 0.872
70711 measured reflections
5697 independent reflections
4862 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.110
S = 1.10
5697 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009585/hb7426sup1.cif

e-71-0o425-sup1.cif^{(1.1MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009585/hb7426Isup2.hkl

e-71-0o425-Isup2.hkl^{(453.5KB, hkl)}

Click here for additional data file.^{(3.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015009585/hb7426Isup3.cml

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015009585/hb7426fig1.tif

A view of the molecular structure of the title compound, showing the atom labellling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(1.9MB, tif)}

. DOI: 10.1107/S2056989015009585/hb7426fig2.tif

A view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1401733

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1AH1AS1A ⁱ	0.80(2)	2.60(2)	3.3227(16)	151.2(18)
N1BH1BS1B ⁱⁱ	0.84(2)	2.65(2)	3.4780(14)	172(2)
N2AH2AS1B ⁱⁱⁱ	0.85(2)	2.49(2)	3.2945(15)	157.8(19)
N2BH2BO1B	0.83(2)	1.98(2)	2.6404(18)	136(2)
N2AH3AO1A	0.83(2)	2.02(2)	2.6515(19)	133(2)
N2BH3BS1A ⁱⁱⁱ	0.89(2)	2.49(2)	3.3800(14)	177(2)
C5BH5BAO1A ^iv	0.95	2.45	3.3584(19)	160
C9BH9BAS1A ⁱ	0.98	2.80	3.6946(17)	152

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

Acknowledgments

The authors thank Universiti Sains Malaysia for research grants Nos. PKIMIA846017 and RU-1001/PKIMIA/811269 which partially supported this work.

supplementary crystallographic information

S1. Introduction

In the crystal, molecules are linked by pairs of C=O—H hydrogen bonds with the methyl group from molecule (B) is facing the group from the molecule (A) forming slabs which is parallel to the benzene ring plane (A) as the bond of C6–C7 (A and B) can free to rotate.

S2. Experimental

The title compound (Fig. 1) is a benzoyl thiourea intermediate to a compound recently reported by us (Ameram et al., 2015) and there is no substituent at the end of thioamide group.

S2.1. Synthesis and crystallization

Freshly prepared substituted o-benzoyl chloride (13 mmol) was added dropwise to a stirred acetone solution (30 ml) of ammonium thiocyanate (13 mmol). The mixture was stirred for 10 min. A white side product which is ammonium chloride was filtered off. The compound was left at room temperature to crystallize, to yield colourless plates of the title compound.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H-atoms on the N atoms were located in a difference-Fourier map and were freely refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and U_iso(H) = 1.2U_eq(aromatic C) or 1.5U_eq(methyl C).

S3. Results and discussion