1-(5,5-Dioxido-10H-phenothia-zin-10-yl)ethanone.

In the title compound, C(14)H(11)NO(3)S, the six-membered thia-zine 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 inter-molecular C-H⋯O inter-actions.

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 = 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

Δρmax = 0.26 e Å−3

Δρmin = −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.

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

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

Supplementary material file. DOI: 10.1107/S1600536811021854/yk2011Isup3.cml

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

C14H11NO3S	F(000) = 568
Mr = 273.30	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3700 reflections
a = 12.5715 (6) Å	θ = 3.3–32.3°
b = 8.7648 (4) Å	µ = 0.26 mm−1
c = 11.5828 (5) Å	T = 173 K
β = 92.142 (4)°	Block, colorless
V = 1275.38 (10) Å3	0.35 × 0.15 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2597 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2263 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 16.1500 pixels mm-1	θmax = 26.4°, θmin = 3.3°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −10→10
Tmin = 0.916, Tmax = 0.963	l = −14→13
5342 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.3216P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.27860 (3)	0.53431 (4)	0.88913 (3)	0.03458 (15)
O1	0.18673 (10)	0.57759 (15)	0.95043 (10)	0.0481 (3)
O2	0.34587 (11)	0.41839 (15)	0.93886 (12)	0.0552 (4)
O3	0.14803 (10)	0.98466 (14)	0.75069 (12)	0.0492 (3)
N1	0.22033 (10)	0.75636 (14)	0.71011 (11)	0.0301 (3)
C1	0.35385 (12)	0.69784 (18)	0.86054 (13)	0.0330 (3)
C2	0.44865 (13)	0.7260 (2)	0.92270 (15)	0.0441 (4)
H2B	0.4745	0.6564	0.9801	0.053*
C3	0.50395 (14)	0.8569 (2)	0.89904 (17)	0.0521 (5)
H3A	0.5685	0.8793	0.9410	0.063*
C4	0.46595 (15)	0.9559 (2)	0.81450 (18)	0.0523 (5)
H4A	0.5045	1.0467	0.7999	0.063*
C5	0.37288 (14)	0.9262 (2)	0.75021 (15)	0.0415 (4)
H5A	0.3487	0.9941	0.6909	0.050*
C6	0.31596 (11)	0.79526 (17)	0.77439 (13)	0.0307 (3)
C7	0.21083 (11)	0.60193 (17)	0.67173 (13)	0.0303 (3)
C8	0.18008 (14)	0.5650 (2)	0.55873 (15)	0.0413 (4)
H8A	0.1651	0.6434	0.5038	0.050*
C9	0.17142 (16)	0.4131 (2)	0.52666 (16)	0.0486 (5)
H9A	0.1488	0.3881	0.4498	0.058*
C10	0.19506 (15)	0.2974 (2)	0.60424 (16)	0.0470 (4)
H10A	0.1866	0.1939	0.5814	0.056*
C11	0.23104 (13)	0.33228 (18)	0.71510 (15)	0.0388 (4)
H11A	0.2510	0.2536	0.7680	0.047*
C12	0.23754 (12)	0.48386 (17)	0.74801 (13)	0.0301 (3)
C13	0.13555 (12)	0.85896 (18)	0.70914 (14)	0.0355 (4)
C14	0.03011 (14)	0.8073 (2)	0.65925 (19)	0.0527 (5)
H14A	−0.0254	0.8789	0.6816	0.079*
H14B	0.0140	0.7054	0.6886	0.079*
H14C	0.0326	0.8039	0.5748	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0430 (2)	0.0320 (2)	0.0286 (2)	0.00086 (16)	−0.00171 (16)	0.00387 (15)
O1	0.0580 (8)	0.0502 (7)	0.0371 (6)	−0.0057 (6)	0.0143 (6)	−0.0048 (6)
O2	0.0673 (9)	0.0431 (7)	0.0538 (8)	0.0057 (6)	−0.0169 (7)	0.0151 (6)
O3	0.0556 (8)	0.0313 (6)	0.0604 (8)	0.0070 (5)	−0.0022 (6)	−0.0060 (6)
N1	0.0334 (6)	0.0253 (6)	0.0311 (6)	−0.0007 (5)	−0.0050 (5)	0.0007 (5)
C1	0.0332 (7)	0.0339 (8)	0.0319 (8)	0.0001 (6)	−0.0005 (6)	−0.0033 (6)
C2	0.0391 (8)	0.0518 (10)	0.0406 (9)	0.0034 (8)	−0.0086 (7)	−0.0069 (8)
C3	0.0363 (9)	0.0687 (13)	0.0509 (11)	−0.0097 (9)	−0.0056 (8)	−0.0147 (10)
C4	0.0475 (10)	0.0565 (12)	0.0532 (11)	−0.0216 (9)	0.0068 (9)	−0.0083 (9)
C5	0.0473 (9)	0.0389 (9)	0.0385 (9)	−0.0100 (7)	0.0036 (7)	0.0000 (7)
C6	0.0322 (7)	0.0300 (7)	0.0299 (7)	−0.0021 (6)	0.0011 (6)	−0.0044 (6)
C7	0.0310 (7)	0.0268 (7)	0.0330 (8)	−0.0024 (6)	−0.0006 (6)	−0.0009 (6)
C8	0.0534 (10)	0.0380 (9)	0.0321 (8)	−0.0081 (8)	−0.0040 (7)	0.0014 (7)
C9	0.0667 (12)	0.0443 (10)	0.0346 (9)	−0.0121 (9)	−0.0004 (8)	−0.0097 (8)
C10	0.0620 (11)	0.0310 (9)	0.0485 (10)	−0.0071 (8)	0.0104 (9)	−0.0115 (8)
C11	0.0467 (9)	0.0269 (8)	0.0432 (9)	0.0013 (7)	0.0080 (7)	−0.0001 (7)
C12	0.0326 (7)	0.0280 (7)	0.0297 (7)	0.0006 (6)	0.0031 (6)	−0.0008 (6)
C13	0.0401 (8)	0.0311 (8)	0.0351 (8)	0.0023 (6)	0.0018 (6)	0.0060 (7)
C14	0.0363 (9)	0.0519 (11)	0.0697 (13)	0.0035 (8)	−0.0019 (9)	0.0010 (10)

S1—O2	1.4292 (13)	C5—C6	1.387 (2)
S1—O1	1.4294 (13)	C5—H5A	0.9500
S1—C12	1.7524 (16)	C7—C8	1.389 (2)
S1—C1	1.7557 (16)	C7—C12	1.394 (2)
O3—C13	1.210 (2)	C8—C9	1.386 (2)
N1—C13	1.394 (2)	C8—H8A	0.9500
N1—C7	1.4283 (19)	C9—C10	1.380 (3)
N1—C6	1.4314 (19)	C9—H9A	0.9500
C1—C6	1.384 (2)	C10—C11	1.380 (2)
C1—C2	1.391 (2)	C10—H10A	0.9500
C2—C3	1.374 (3)	C11—C12	1.384 (2)
C2—H2B	0.9500	C11—H11A	0.9500
C3—C4	1.380 (3)	C13—C14	1.496 (2)
C3—H3A	0.9500	C14—H14A	0.9800
C4—C5	1.388 (3)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800
O2—S1—O1	117.73 (8)	C8—C7—C12	118.45 (14)
O2—S1—C12	110.23 (8)	C8—C7—N1	122.08 (14)
O1—S1—C12	108.36 (7)	C12—C7—N1	119.41 (13)
O2—S1—C1	109.97 (8)	C9—C8—C7	119.52 (16)
O1—S1—C1	109.16 (7)	C9—C8—H8A	120.2
C12—S1—C1	99.91 (7)	C7—C8—H8A	120.2
C13—N1—C7	123.62 (12)	C10—C9—C8	121.26 (16)
C13—N1—C6	118.52 (13)	C10—C9—H9A	119.4
C7—N1—C6	116.52 (12)	C8—C9—H9A	119.4
C6—C1—C2	121.92 (15)	C11—C10—C9	119.88 (16)
C6—C1—S1	117.79 (11)	C11—C10—H10A	120.1
C2—C1—S1	120.29 (13)	C9—C10—H10A	120.1
C3—C2—C1	118.35 (17)	C10—C11—C12	118.89 (16)
C3—C2—H2B	120.8	C10—C11—H11A	120.6
C1—C2—H2B	120.8	C12—C11—H11A	120.6
C2—C3—C4	120.13 (17)	C11—C12—C7	121.87 (15)
C2—C3—H3A	119.9	C11—C12—S1	120.77 (12)
C4—C3—H3A	119.9	C7—C12—S1	117.36 (11)
C3—C4—C5	121.69 (17)	O3—C13—N1	119.75 (15)
C3—C4—H4A	119.2	O3—C13—C14	121.93 (15)
C5—C4—H4A	119.2	N1—C13—C14	118.29 (14)
C6—C5—C4	118.54 (17)	C13—C14—H14A	109.5
C6—C5—H5A	120.7	C13—C14—H14B	109.5
C4—C5—H5A	120.7	H14A—C14—H14B	109.5
C1—C6—C5	119.33 (14)	C13—C14—H14C	109.5
C1—C6—N1	119.19 (13)	H14A—C14—H14C	109.5
C5—C6—N1	121.45 (14)	H14B—C14—H14C	109.5
O2—S1—C1—C6	154.78 (12)	C13—N1—C7—C12	−121.42 (16)
O1—S1—C1—C6	−74.65 (14)	C6—N1—C7—C12	45.13 (19)
C12—S1—C1—C6	38.88 (13)	C12—C7—C8—C9	3.4 (2)
O2—S1—C1—C2	−24.71 (16)	N1—C7—C8—C9	−179.49 (16)
O1—S1—C1—C2	105.85 (14)	C7—C8—C9—C10	−1.5 (3)
C12—S1—C1—C2	−140.62 (14)	C8—C9—C10—C11	−1.9 (3)
C6—C1—C2—C3	1.8 (3)	C9—C10—C11—C12	3.3 (3)
S1—C1—C2—C3	−178.75 (14)	C10—C11—C12—C7	−1.3 (2)
C1—C2—C3—C4	−0.8 (3)	C10—C11—C12—S1	177.93 (13)
C2—C3—C4—C5	−1.0 (3)	C8—C7—C12—C11	−2.0 (2)
C3—C4—C5—C6	1.7 (3)	N1—C7—C12—C11	−179.24 (14)
C2—C1—C6—C5	−1.1 (2)	C8—C7—C12—S1	178.73 (12)
S1—C1—C6—C5	179.43 (12)	N1—C7—C12—S1	1.50 (18)
C2—C1—C6—N1	177.23 (14)	O2—S1—C12—C11	26.68 (16)
S1—C1—C6—N1	−2.26 (19)	O1—S1—C12—C11	−103.47 (14)
C4—C5—C6—C1	−0.6 (2)	C1—S1—C12—C11	142.39 (13)
C4—C5—C6—N1	−178.90 (15)	O2—S1—C12—C7	−154.06 (12)
C13—N1—C6—C1	122.59 (15)	O1—S1—C12—C7	75.79 (13)
C7—N1—C6—C1	−44.68 (19)	C1—S1—C12—C7	−38.35 (13)
C13—N1—C6—C5	−59.1 (2)	C7—N1—C13—O3	174.72 (15)
C7—N1—C6—C5	133.59 (15)	C6—N1—C13—O3	8.4 (2)
C13—N1—C7—C8	61.5 (2)	C7—N1—C13—C14	−3.5 (2)
C6—N1—C7—C8	−131.99 (15)	C6—N1—C13—C14	−169.76 (14)

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

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

Symmetry codes: (i) ; (ii) .