2-[(2-Amino­phen­yl)sulfan­yl]-N-(4-meth­oxy­phen­yl)acetamide

Shahzad Murtaza; M Nawaz Tahir; Javaria Tariq; Aadil Abbas; Naghmana Kausar

doi:10.1107/S1600536812024178

. 2012 May 31;68(Pt 6):o1968. doi: 10.1107/S1600536812024178

2-[(2-Aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide

Shahzad Murtaza ^a, M Nawaz Tahir ^b,^*, Javaria Tariq ^a, Aadil Abbas ^a, Naghmana Kausar ^a

PMCID: PMC3379516 PMID: 22719714

Abstract

In the title compound, C₁₅H₁₆N₂O₂S, the dihedral angle between the 4-methoxyaniline and 2-aminobenzenethiole fragments is 35.60 (9)°. A short intramolecular N—H⋯S contact leads to an S(5) ring. In the crystal, molecules are consolidated in the form of polymeric chains along [010] as a result of N—H⋯O hydrogen bonds, which generate R ₃ ²(18) and R ₄ ³(22) loops. The polymeric chains are interlinked through C—H⋯O interaction and complete R ₂ ²(8) ring motifs.

Related literature

For a related structure, see: Haisa et al. (1980 ▶). For hydrogen-bond motif notation, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1968-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₆N₂O₂S
M _r = 288.36
Monoclinic,
a = 12.9935 (16) Å
b = 4.7990 (4) Å
c = 23.433 (3) Å
β = 95.506 (7)°
V = 1454.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.25 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.965, T _max = 0.975
11532 measured reflections
2845 independent reflections
1525 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.121
S = 1.01
2845 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 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/S1600536812024178/hb6821sup1.cif

e-68-o1968-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024178/hb6821Isup2.hkl

e-68-o1968-Isup2.hkl^{(136.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024178/hb6821Isup3.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—H2B⋯S1	0.86	2.60	3.004 (3)	110
N1—H1⋯O2ⁱ	0.86	2.00	2.848 (3)	170
N2—H2A⋯O2ⁱⁱ	0.86	2.38	3.200 (3)	161
C3—H3⋯O1ⁱⁱⁱ	0.93	2.47	3.393 (5)	170

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the 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) has been synthesized to check its biological application as antimicrobial agent owing to the concept that amide moiety is an important part of different drugs.

The crystal structure of N-(4-methoxyphenyl)acetamide (Haisa et al., 1980) has been published which is related to the title compound (I, Fig. 1).

In (I), the 4-methoxyanilinic and 2-aminobenzenethiolic groups A (C1–C7/N1/O1) and B (C10—C15/N2/S1) are almost planar with r. m. s. deviation of 0.0150 Å and 0.0134 Å, respectively. The dihedral angle between A/B is 35.60 (9)°. The central acetamide moiety C (C8/C9/O2) is of course planar. The dihedral angle between A/C and B/C is 48.43 (10)° and 78.07 (8)°, respectively. There exist S(5) ring motif (Bernstein et al., 1995) due to H-bonding of N—H···S type (Table 1, Fig. 2). The molecules are stabilized in the form of one-dimensional polymeric network due to H-bondings (Table 1, Fig. 2) of N—H···O type. There exist R₃²(18) and R₄³(22) ring motifs in the polymeric network when three and four molecules respectively, are connected with each other.

Experimental

2-Aminobenzothiol (0.125 g, 0.5 mmol) was dissolved in anhydrous diethylether (10 ml) and NaH (0.024 g, 1 mmol) was added to it at temperature 273–278 K. A separately prepared solution of 2-chloro-N-(4-methoxyphenyl)acetamide (0.1 g, 0.5 mmol) in anhydrous diethylether (10 ml) was added drop wise to above mixture. The mixture was stirred for 4 h and solvent was evaporated to get greyish crystals of (I). m.p. 400 K