7-Bromo-3,3-dibutyl-8-meth­oxy-2,3-di­hydro-1,5-benzothia­zepin-4(5H)-one

C V Deepu; M Manjula; K J Pampa; D G Bhadregowda; N K Lokanath

doi:10.1107/S1600536813013238

. 2013 Jun 19;69(Pt 7):o1129. doi: 10.1107/S1600536813013238

7-Bromo-3,3-dibutyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

C V Deepu ^a, M Manjula ^b, K J Pampa ^c, D G Bhadregowda ^a,^*, N K Lokanath ^b

PMCID: PMC3770397 PMID: 24046682

Abstract

In the title compound C₁₈H₂₆BrNO₂S, the thiazepine ring adopts a boat conformation. The dihedral angle between the mean planes through the benzene ring and the four C atoms making up the basal plane of the boat is 35.8 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For reference bond lengths, see: Allen et al. (1987 ▶). For background to the uses of this class of compounds, see: Fedi et al. (2008 ▶); Ganesh et al. (2011 ▶); Riedel et al. (2007 ▶). graphic file with name e-69-o1129-scheme1.jpg

Experimental

Crystal data

C₁₈H₂₆BrNO₂S
M _r = 400.30
Monoclinic,
a = 7.7844 (18) Å
b = 11.251 (2) Å
c = 22.039 (6) Å
β = 98.199 (8)°
V = 1910.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.32 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
16056 measured reflections
4662 independent reflections
2750 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.141
S = 1.03
4662 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013238/hb7081sup1.cif

e-69-o1129-sup1.cif^{(27KB, cif)}

Structure factors: contains datablock(s) mm. DOI: 10.1107/S1600536813013238/hb7081Isup2.hkl

e-69-o1129-Isup2.hkl^{(228.4KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813013238/hb7081Isup3.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
N14—H14⋯O15ⁱ	0.86	2.13	2.985 (3)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

MM thanks the IOE and the University of Mysore for the award of a fellowship and research grants. The data collection was performed at the Solid Sate and Structural Chemistry Unit, IISC.

supplementary crystallographic information

Comment

The title compound C₁₈H₂₅Br_NO₂S, was synthesized from 3,3-dibutyl-2,3- dihydro-8-methoxybenzo[b][1,4]thiazepin-4(5H)-one. The molecule is a bicyclic structure with one aromatic ring fused to a seven membered ring, on which two heteroatoms are present. The derivatives of this molecule able to provide high affinity ligands for more than one type of the receptor (Fedi et al., 2008). The compound is mainly used to treat schizophrenia and also find applications as neuroleptics, antidepressants, antihistaminic (Ganesh et al., 2011; Riedel et al., 2007). The N14—C13 bond is shorter than an usual N—C single bond [1.356 Å compared to 1.416 Å (Allen et al. 1987)]. The atoms C5, C6, C11 and C12 present in the central thiazepine ring forms a basal plane and the S10 atom as the bow, representing the boat conformation of thiazepine ring.

Experimental

3,3-dibutyl-2,3-dihydro-8-methoxybenzo[b][1,4]thiazepin-4(5H)-one in dichloromethane, acetonitrile, cooled to 5°C and added N-bromosuccinimide over a period of 15 min. Then reaction mixture was brought to room temperature, stirred for 2 h and again cooled to 5°C, then N-bromosuccinimide is added at 5°C, cooled to -5°C for 1 h, filtered, washed with cold acetonitrile and then dried in vacuum and product was recrystallized from acetonitrile solution to yield light brown blocks.