N-(2-Nitro­phenyl­carbamothio­yl)acetamide

Durre Shahwar; M Nawaz Tahir; Muhammad Mansha Chohan; Muhammad Akmal Khan; Nadeem Ahmad

doi:10.1107/S1600536812016947

. 2012 Apr 28;68(Pt 5):o1578. doi: 10.1107/S1600536812016947

N-(2-Nitrophenylcarbamothioyl)acetamide

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, Muhammad Mansha Chohan ^a, Muhammad Akmal Khan ^a, Nadeem Ahmad ^c

PMCID: PMC3344673 PMID: 22590435

Abstract

In the title compound, C₉H₉N₃O₃S, the benzene ring and the N-carbamothioylacetamide unit are oriented at a dihedral angle of 54.82 (4)°. The dihedral angle between the ring and its attached nitro group is 28.54 (12)°. An intramolecular, bifurcated N—H⋯(O,O) hydrogen bond generates two S(6) rings. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R ₂ ²(8) loops. Weak C—H⋯O interactions link the dimers.

Related literature

For related structures, see: Shahwar et al. (2012a ▶,b ▶,c ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₉H₉N₃O₃S
M _r = 239.25
Monoclinic,
a = 4.1992 (1) Å
b = 11.6081 (3) Å
c = 22.1035 (6) Å
β = 94.815 (1)°
V = 1073.63 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.945, T _max = 0.965
10065 measured reflections
2711 independent reflections
1969 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.105
S = 1.01
2711 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.22 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016947/hb6744sup1.cif

e-68-o1578-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016947/hb6744Isup2.hkl

e-68-o1578-Isup2.hkl^{(130.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016947/hb6744Isup3.cml

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	2.23	2.661 (2)	111
N2—H2⋯O3	0.86	1.93	2.630 (2)	137
N3—H3A⋯S1ⁱ	0.86	2.59	3.4371 (14)	168
C9—H9C⋯O2ⁱⁱ	0.96	2.51	3.428 (3)	161

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound I (Fig. 1) is in continuation to synthesize different derivatives of N-carbamothioylacetamide.

We have reported the crystal structures of N-(2-methylphenylcarbamothioyl)acetamide (Shahwar et al., 2012a), N-(3-chlorophenylcarbamothioyl)acetamide (Shahwar et al., 2012b) and N-(phenylcarbamothioyl)acetamide (Shahwar et al., 2012c) which are related to the (I).

In (I), the phenyl ring A (C1–C6) and the N-carbamothioylacetamide moiety B (N2/C7/S1/N3/C8/O3/C9) are planar with r. m. s. deviation of 0.0028 Å and 0.0181 Å, respectively. The dihedral angle between A/B is 54.82 (4)°. The nitro group C (O1/N1/O2) is of course planar. The dihedral angle between A/C and B/C are 28.68 (18) and 66.59 (12)°, respectively. There exist intramolecular H–bonding of N—H···O type (Table 1, Fig. 1) with two S(6) ring motifs (Bernstein et al., 1995). The molecules are dimerized due to N—H···S type of hydrogen bonds with R₂²(8) ring motifs (Table 1, Fig. 2). The dimers are interlinked from CH₃ groups due to C—H···O H–bondings (Table 1, Fig. 2) with nitro groups.

Experimental

Acetylchloride (0.1 mol, 7.13 ml) was added dropwise to a stirred solution of KSCN (0.11 mol) in dry acetone (50 ml), followed by slow addition of 2-nitroaniline (0.1 mol) in dry acetone (25 ml). The mixture was refluxed for 5–10 min, then poured on ice cooled water, which resulted in crude precipitate. Recrystallization of the precipitate from ethylacetate yielded colourless needles.