1-(5,5-Dioxido-10H-phenothia­zin-10-yl)ethanone

M S Siddegowda; Jerry P Jasinski; James A Golen; H S Yathirajan

doi:10.1107/S1600536811021854

. 2011 Jun 18;67(Pt 7):o1702. doi: 10.1107/S1600536811021854

1-(5,5-Dioxido-10H-phenothiazin-10-yl)ethanone

M S Siddegowda ^a, Jerry P Jasinski ^b,^*, James A Golen ^b, H S Yathirajan ^a

PMCID: PMC3151987 PMID: 21837098

Abstract

In the title compound, C₁₄H₁₁NO₃S, the six-membered thiazine ring fused to two benzene rings adopts a distorted boat conformation. The dihedral angle between the mean planes of the two benzene rings is 45.8 (1)°. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For synthetic dyes and electroluminescent materials containing phenothiazine, see: Miller et al. (1999 ▶). For antipsychotic drugs, see: Wermuth et al. (2003 ▶). For applications of phenothiazine derivatives in medicine, see: Wang et al. (2008 ▶). For their antitumor activity, see: Lam et al. (2001 ▶). For related structures, see: Harrison et al. (2007 ▶); Jasinski et al. (2011 ▶). For standard bond lengths, see Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₄H₁₁NO₃S
M _r = 273.30
Monoclinic,
a = 12.5715 (6) Å
b = 8.7648 (4) Å
c = 11.5828 (5) Å
β = 92.142 (4)°
V = 1275.38 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 K
0.35 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.916, T _max = 0.963
5342 measured reflections
2597 independent reflections
2263 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.02
2597 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811021854/yk2011sup1.cif

e-67-o1702-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021854/yk2011Isup2.hkl

e-67-o1702-Isup2.hkl^{(127.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811021854/yk2011Isup3.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
C2—H2B⋯O2ⁱ	0.95	2.50	3.246 (2)	135
C8—H8A⋯O1ⁱⁱ	0.95	2.54	3.376 (2)	147
C9—H9A⋯O3ⁱⁱ	0.95	2.56	3.322 (2)	137

Open in a new tab

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

Acknowledgments

MSS thanks the University of Mysore for the research facilities and R. L. Fine Chem, Bangalore, India, for the gift sample. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Phenothiazine is a well known heterocycle. The phenothiazine structure occurs in many synthetic dyes, electroluminescent materials (Miller et al., 1999) and drugs, especially various antipsychotic drugs, e.g. chlorpromazine and antihistaminic drugs, e.g. promethazine (Wermuth, 2003). Recently, researchers have found some new applications for phenothiazine derivatives in medicine related to antitubercular (Wang et al., 2008) and antitumor activities (Lam et al., 2001). The title compound has been used in the synthesis of oxomemazine, an antihistamine and anticholinergic drug of the phenothiazine chemical class used for the treatment of coughs. The crystal structures of dioxopromethazinium picrate (Harrison et al., 2007) and 1-(10H-phenothiazin-2-yl)ethanone (Jasinski et al., 2011) have been reported. In view of the importance of phenothiazines, this paper reports the crystal structure of the title compound, C₁₄H₁₁NO₃S.

In the title compound the six-membered thiazine ring fused to two benzene rings adopts a distorted boat conformation. (Cremer & Pople, 1975) with puckering parameters Q, θ and φ of 0.6257 (12) Å, 95.85 (13)° and 180.29 (15)°, respectively (Fig. 1). For an ideal boat θ and φ have values of 90.0° and 180°. The dihedral angle between the mean planes of the two benzene rings is 45.8 (1)°. The ethanone group extends away from corner of the boat crease with a -169.76 (14)° (C6/N1/C13/C14) torsion angle. The SO₂ group extends away from the opposite corner of the boat crease with a 105.8 (14)° (C2/C1/S1/O1) torsion angle. Bond lengths are in normal ranges (Allenet al., 1987). Crystal packing is stabiized by weak C—H···O (Table 1, Fig. 2) intermolecular interactions.

Experimental

The title compound was obtained as a gift sample from RL Fine Chem, Bangalore, India. X-ray quality crystals were obtained by slow evaporation of solution of a 1:1 mixture of acetone:ethanol (m.p.: 495 K).