3-(2-Amino­phenyl­sulfanyl)-1,3-diphenyl­propan-1-one

Marzieh Yaeghoobi; Hamid Khaledi; Zanariah Abdullah; Noorsaadah AbdRahman

doi:10.1107/S1600536811022112

. 2011 Jun 18;67(Pt 7):o1693. doi: 10.1107/S1600536811022112

3-(2-Aminophenylsulfanyl)-1,3-diphenylpropan-1-one

Marzieh Yaeghoobi ^a, Hamid Khaledi ^a,^*, Zanariah Abdullah ^a, Noorsaadah AbdRahman ^a

PMCID: PMC3152142 PMID: 21837090

Abstract

In the title compound, C₂₁H₁₉NOS, the three aromatic rings are not coplanar, the dihedral angles between them being 84.75 (7), 88.01 (8) and 8.36 (16)°. In the crystal, two types of C—H⋯ π interactions, one of which is weak, and N—H⋯π interactions link the molecules into layers parallel to the ab plane.

Related literature

For a similar structure, see: Morgant et al. (1996 ▶).

Experimental

Crystal data

C₂₁H₁₉NOS
M _r = 333.43
Monoclinic,
a = 11.1741 (16) Å
b = 5.6788 (8) Å
c = 27.308 (4) Å
β = 95.266 (2)°
V = 1725.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.18 × 0.07 × 0.02 mm

Data collection

Bruker APEX-II CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.996
7303 measured reflections
3195 independent reflections
1784 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.101
S = 0.95
3195 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811022112/go2015sup1.cif

e-67-o1693-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022112/go2015Isup2.hkl

e-67-o1693-Isup2.hkl^{(156.8KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C10–C15 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cg1ⁱ	0.91 (3)	2.55 (3)	3.400 (3)	155 (2)
C12—H12⋯Cg1ⁱⁱ	0.93	2.86	3.581 (4)	135
C14—H14⋯Cg2ⁱ	0.93	2.93	3.587 (3)	128

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

Acknowledgments

The authors would like to thank the Ministry of Science, Technology and Innovation (MOSTI) for funding this study (Science fund grant No. 53–02-03–1059).

supplementary crystallographic information

Comment

The title compound (Fig. 1) was obtained during the synthesis of benzothiazepines II in an ionic liquid media (Fig. 2) and is suggested to be the intermediate compound which upon subsequent cyclization would form the seven-membered thiazepine ring. The three aromatic rings of the molecule are non-planar as are in the structure of a related compound (Morgant et al., 1996). The dihedral angles between the phenyl rings plane are 84.75 (7)° (between C1/C6 and C10/C15), 88.01 (8) ° (between C1/C6 and C16/C21) and 8.36 (16) ° (between C10/C15 and C16/C21). The amino hydrogen, H1B, is involved in an N—H··· π interaction (Table 1). In the crystal, the N—H···π interactions connect the adjacent molecules into infinite chains along the b axis. The one-dimensional link is supplemented by weak C14—H14··· π interactions. The chains are connected into two-dimensional-arrays parallel to the ab plane via C12—H12··· π interactions (Table 1).

Experimental

The title compound was synthesized as illustrated in Fig. 2. A mixture of the chalcone (0.208 g, 1 mmol), o-aminothiophenol (0.088 ml, 1.1 mmol) and ionic liquid, IL, (0.1 g) was heated at 80°C for 80 min. The two products, I & II, were extracted with diethyether and separated by column chromatography (hexane: ethylacatate, 8:2). The second fraction, containing (I), was evaporated and the resulting solid was recrystallized from ethanol at room temperature to give the colorless crystals of the title compound.