4-tert-Butyl-N-[(2,6-dimethyl­phen­yl)carbamothio­yl]benzamide

M Sukeri M Yusof; Suhana Arshad; Ibrahim Abdul Razak; Azhar Abdul Rahman

doi:10.1107/S1600536812034174

. 2012 Aug 11;68(Pt 9):o2670. doi: 10.1107/S1600536812034174

4-tert-Butyl-N-[(2,6-dimethylphenyl)carbamothioyl]benzamide

M Sukeri M Yusof ^a, Suhana Arshad ^b, Ibrahim Abdul Razak ^b,^*,^‡, Azhar Abdul Rahman ^b,^§

PMCID: PMC3435693 PMID: 22969564

Abstract

The asymmetric unit of the title compound, C₂₀H₂₄N₂OS, consists of two crystallographically independent molecules. In each molecule, an intramolecular N—H⋯O hydrogen bond forms an S(6) ring motif. The dihedral angles between the terminal benzene rings in the two molecules are 75.52 (7) and 42.80 (7)°. In the crystal, intermolecular N—H⋯S interactions link the molecules into a chain along the c axis.

Related literature

For related structures, see: Yusof, Mutalib et al. (2012 ▶); Yusof, Embong et al. (2012a ▶,b ▶); Usman et al. (2002 ▶); Al-abbasi et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₀H₂₄N₂OS
M _r = 340.47
Monoclinic,
a = 19.5893 (2) Å
b = 8.8118 (1) Å
c = 23.5034 (2) Å
β = 114.886 (1)°
V = 3680.37 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.41 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.929, T _max = 0.970
67130 measured reflections
10823 independent reflections
8234 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.120
S = 1.04
10823 reflections
459 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034174/is5176sup1.cif

e-68-o2670-sup1.cif^{(42.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034174/is5176Isup2.hkl

e-68-o2670-Isup2.hkl^{(529.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034174/is5176Isup3.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
N2A—H2NA⋯O1A	0.84 (2)	2.06 (2)	2.6972 (19)	133.1 (16)
N2B—H2NB⋯O1B	0.84 (2)	2.08 (2)	2.7183 (19)	132.4 (17)
N2A—H2NA⋯S1B	0.84 (2)	2.715 (17)	3.2598 (12)	124.3 (16)
N2B—H2NB⋯S1A ⁱ	0.84 (2)	2.780 (19)	3.3044 (12)	121.9 (16)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No.1001/PFIZIK/811151 and Universiti Malaysia Terengganu FRGS Research Grant 59166 to conduct this work.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of thiourea derivatives (Yusof, Mutalib et al., 2012; Yusof, Embong et al., 2012a,b) the title compound is prepared and its crystal structure is reported.

The asymmetric unit of the title compound consists of two crystallographically independent molecules A and B (Fig. 1). In both molecules, the intramolecular N2A—H2NA···O1A and N2B—H2NB···O1B hydrogen bonds (Table 1) generate S(6) ring motifs (Bernstein et al., 1995). The dihedral angles between the two terminal benzene rings in molecule A and B are 75.52 (7) and 42.80 (7)°, respectively. The bond lengths and angles are within normal ranges and comparable to the previously reported structures (Usman et al., 2002; Al-abbasi et al., 2010).

The crystal packing is shown in Fig. 2. The intermolecular N2A—H2NA···S1B and N2B—H2NB···S1A interactions (Table 1) link the molecules into a one-dimensional chain along the c axis.

Experimental

30 ml acetone solution of 2,4-dimethylaniline (0.93 g, 7.7 mmol) was added into 30 ml acetone containing 4-tert-butylbenzoyl chloride (1.50 g, 7.7 mmol) and ammonium thiocyanate (0.58 g, 9.5 mmol). The mixture was refluxed for 2.5 hours. The solution was filtered and left to evaporate at room temperature. The yellowish precipitate obtained after a few days was washed with water and cold ethanol. The crystals were obtained by recrystallization from DMF.