3-[(Z)-Benzyl­idene]-2,3-dihydro-1,5-benzothia­zepin-4(5H)-one

V Sabari; G Jagadeesan; Raman Selvakumar; Mannickam Bakthadoss; S Aravindhan

doi:10.1107/S1600536811042991

. 2011 Oct 29;67(Pt 11):o3061. doi: 10.1107/S1600536811042991

3-[(Z)-Benzylidene]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

V Sabari ^a, G Jagadeesan ^a, Raman Selvakumar ^b, Mannickam Bakthadoss ^b, S Aravindhan ^a,^*

PMCID: PMC3247452 PMID: 22220070

Abstract

In the title compound, C₁₆H₁₃NOS, the seven-membered ring adopts a distorted half-chair conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains running along the b axis. The crystal packing is further stabilized by C—H⋯O interactions.

Related literature

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000 ▶); Rajsner et al. (1971 ▶); Metys et al. (1965 ▶). For the conformation of thiazepin derivatives, see: Sridevi et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₃NOS
M _r = 267.33
Orthorhombic,
a = 10.7711 (9) Å
b = 7.8736 (7) Å
c = 31.610 (3) Å
V = 2680.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker KappaCCD APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.980, T _max = 0.990
13085 measured reflections
3306 independent reflections
2643 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.112
S = 1.04
3306 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042991/bt5678sup1.cif

e-67-o3061-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042991/bt5678Isup2.hkl

e-67-o3061-Isup2.hkl^{(159KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042991/bt5678Isup3.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
N—H⋯Oⁱ	0.872 (18)	1.996 (18)	2.8480 (16)	165.4 (16)
C14—H14⋯Oⁱⁱ	0.93	2.57	3.485 (2)	167
C16—H16⋯O	0.93	2.60	3.397 (2)	144

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

Acknowledgments

SA thanks the UGC, India, for financial support.

supplementary crystallographic information

Comment

The title compound is used as an intermediate for the synthesis of dosulepin, which is an antidepressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thiazepin-5,5-dioxide derivatives possess antihistaminic and antiallergenic activities (Rajsner et al., 1971). Benzene thiazepin derivatives are identified as a new type of effective antihistaminic compounds (Metys et al., 1965). Considering the wide range of biological activities of the thiazepin derivatives, we determined the crystal structure of the title compound. The seven membered thiazepin ring adopts a distorted half-chair conformation (Sridevi et al., 2011). Crystal structure and crystal packing of the molecule were stabilized by intra (C16—H16···O) and Inter (N—H···O, C14—H14···O) molecular interaction.

Experimental

A mixture of (z)-methyl2-(bromomethyl)-3-phenylacrylate (2 mmol) and O-aminothiophenol(2 mmol) in the presence of potassium tert-butoxide (2,4 mmol) in dry THF (10 ml) was stirred at room temperature for 1 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3X20ml). The organic layer was washed with brine (2X20ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which provided a crude mass (Z)-methyl 2-((2-aminnophyenylthio)methyl)-3-phenylacrylate.The crude product was treated with a catalytic amount of p-toluene sulphonic acid (0.4 mmol),in p-xylene(10 ml), under reflux conditions for 12 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure and worked up as mentioned previously, which successfully provide the crude final product. The final product was purified by column chromatography on silica gel to afford the title compound in good yield(71%).