10-Acetyl-10H-phenothia-zine 5-oxide.

In the title compound, C(14)H(11)NO(2)S, the sulfoxide O atom is disordered over two sites with occupancies of 0.886 (4) and 0.114 (4), reflecting a partial inversion of the lone pair at the tetra-hedral S-atom site. In the crystal, a supra-molecular arrangement arises from weak inter-molecular C-H⋯O hydrogen bonds. π-π contacts between the aromatic rings of symmetry-related mol-ecules [centroid-centroid distances = 3.7547 (15) and 3.9577 (15) Å] in parallel accumulation further stabilize the crystal structure.

Related literature

For synthetic details, see: Gilman & Nelson (1953 ▶); Chan et al. (1998 ▶). For a general background to phenothia­zine-based mol­ecules, see: Miller et al. (1999 ▶); Lam et al. (2001 ▶); Wermuth (2003 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

C14H11NO2S

M = 257.30

Monoclinic,

a = 8.1244 (1) Å

b = 14.1787 (2) Å

c = 10.7576 (1) Å

β = 100.963 (1)°

V = 1216.59 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.20 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.950, T max = 0.967

11538 measured reflections

3067 independent reflections

2404 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.09

3067 reflections

174 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S1600536809028487/bh2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028487/bh2235Isup2.hkl

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

C14H11NO2S	F(000) = 536
Mr = 257.30	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Melting point: 443 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.1244 (1) Å	Cell parameters from 4917 reflections
b = 14.1787 (2) Å	θ = 2.4–27.7°
c = 10.7576 (1) Å	µ = 0.26 mm−1
β = 100.963 (1)°	T = 296 K
V = 1216.59 (3) Å3	Block, orange
Z = 4	0.20 × 0.14 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	3067 independent reflections
Radiation source: fine-focus sealed tube	2404 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 28.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.950, Tmax = 0.967	k = −18→18
11538 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.5122P] where P = (Fo2 + 2Fc2)/3
3067 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.24 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2768 (2)	1.03984 (14)	0.34599 (17)	0.0419 (4)
C2	0.4325 (3)	1.08344 (17)	0.3653 (2)	0.0552 (6)
H2A	0.4440	1.1461	0.3911	0.066*
C3	0.5687 (3)	1.0329 (2)	0.3456 (2)	0.0679 (7)
H3A	0.6736	1.0614	0.3585	0.081*
C4	0.5520 (3)	0.9400 (2)	0.3069 (2)	0.0603 (6)
H4A	0.6461	0.9059	0.2960	0.072*
C5	0.3958 (2)	0.89724 (16)	0.28427 (19)	0.0482 (5)
H5A	0.3845	0.8353	0.2554	0.058*
C6	0.2563 (2)	0.94696 (13)	0.30478 (16)	0.0372 (4)
C7	−0.0305 (2)	0.97033 (13)	0.19798 (17)	0.0383 (4)
C8	−0.0329 (2)	1.06443 (13)	0.23222 (18)	0.0415 (4)
C9	−0.1414 (3)	1.12817 (16)	0.1596 (2)	0.0552 (5)
H9A	−0.1414	1.1914	0.1824	0.066*
C10	−0.2486 (3)	1.09580 (18)	0.0533 (2)	0.0600 (6)
H10A	−0.3219	1.1375	0.0040	0.072*
C11	−0.2480 (3)	1.00256 (18)	0.0197 (2)	0.0580 (6)
H11A	−0.3223	0.9815	−0.0515	0.070*
C12	−0.1381 (2)	0.93909 (15)	0.09038 (19)	0.0467 (5)
H12A	−0.1369	0.8763	0.0657	0.056*
C13	0.0405 (3)	0.82363 (14)	0.3156 (2)	0.0479 (5)
C14	0.1638 (3)	0.76880 (16)	0.4099 (2)	0.0602 (6)
H14A	0.1048	0.7321	0.4622	0.090*
H14B	0.2386	0.8116	0.4619	0.090*
H14C	0.2271	0.7276	0.3659	0.090*
N1	0.09014 (18)	0.90973 (10)	0.27386 (15)	0.0388 (3)
O2	−0.1007 (2)	0.79521 (12)	0.2791 (2)	0.0756 (6)
S1	0.09806 (7)	1.10145 (4)	0.37655 (5)	0.05019 (17)
O1A	0.1306 (3)	1.20324 (11)	0.37154 (19)	0.0716 (7)	0.886 (4)
O1B	0.0214 (17)	1.0640 (10)	0.4755 (10)	0.068 (5)	0.114 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0440 (10)	0.0426 (10)	0.0387 (9)	−0.0069 (8)	0.0070 (7)	0.0010 (8)
C2	0.0588 (13)	0.0576 (13)	0.0471 (11)	−0.0228 (11)	0.0047 (9)	0.0040 (9)
C3	0.0425 (11)	0.100 (2)	0.0595 (14)	−0.0217 (13)	0.0069 (10)	0.0140 (14)
C4	0.0384 (10)	0.0930 (19)	0.0505 (12)	0.0062 (11)	0.0108 (9)	0.0122 (12)
C5	0.0444 (10)	0.0558 (12)	0.0440 (10)	0.0094 (9)	0.0074 (8)	0.0036 (9)
C6	0.0354 (9)	0.0394 (10)	0.0362 (9)	−0.0009 (7)	0.0050 (7)	0.0030 (7)
C7	0.0326 (8)	0.0359 (9)	0.0469 (10)	0.0023 (7)	0.0090 (7)	0.0043 (7)
C8	0.0413 (10)	0.0369 (9)	0.0491 (10)	0.0044 (8)	0.0153 (8)	0.0038 (8)
C9	0.0607 (13)	0.0416 (11)	0.0674 (14)	0.0151 (10)	0.0230 (11)	0.0118 (10)
C10	0.0512 (12)	0.0671 (15)	0.0618 (13)	0.0193 (11)	0.0109 (10)	0.0222 (11)
C11	0.0445 (11)	0.0760 (16)	0.0510 (12)	0.0027 (11)	0.0028 (9)	0.0102 (11)
C12	0.0416 (10)	0.0466 (11)	0.0512 (11)	−0.0019 (9)	0.0072 (8)	0.0018 (9)
C13	0.0452 (11)	0.0334 (10)	0.0637 (13)	0.0001 (8)	0.0065 (9)	0.0048 (9)
C14	0.0633 (14)	0.0438 (12)	0.0713 (14)	0.0045 (10)	0.0071 (11)	0.0160 (10)
N1	0.0348 (7)	0.0305 (7)	0.0496 (9)	0.0005 (6)	0.0040 (6)	0.0027 (6)
O2	0.0546 (10)	0.0521 (10)	0.1130 (15)	−0.0162 (8)	−0.0019 (9)	0.0240 (9)
S1	0.0644 (3)	0.0362 (3)	0.0524 (3)	−0.0005 (2)	0.0175 (2)	−0.0066 (2)
O1A	0.1022 (16)	0.0319 (9)	0.0786 (14)	−0.0026 (9)	0.0119 (11)	−0.0088 (8)
O1B	0.084 (11)	0.080 (11)	0.045 (8)	0.017 (8)	0.020 (7)	−0.003 (7)

C1—C2	1.387 (3)	C8—S1	1.786 (2)
C1—C6	1.389 (3)	C9—C10	1.377 (3)
C1—S1	1.778 (2)	C9—H9A	0.9300
C2—C3	1.369 (4)	C10—C11	1.371 (3)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.380 (4)	C11—C12	1.388 (3)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.385 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—O2	1.209 (2)
C5—C6	1.388 (3)	C13—N1	1.387 (2)
C5—H5A	0.9300	C13—C14	1.500 (3)
C6—N1	1.428 (2)	C14—H14A	0.9600
C7—C12	1.384 (3)	C14—H14B	0.9600
C7—C8	1.385 (3)	C14—H14C	0.9600
C7—N1	1.436 (2)	S1—O1B	1.433 (5)
C8—C9	1.394 (3)	S1—O1A	1.4700 (17)
C2—C1—C6	121.40 (19)	C11—C10—C9	120.4 (2)
C2—C1—S1	120.45 (17)	C11—C10—H10A	119.8
C6—C1—S1	118.14 (14)	C9—C10—H10A	119.8
C3—C2—C1	119.0 (2)	C10—C11—C12	121.0 (2)
C3—C2—H2A	120.5	C10—C11—H11A	119.5
C1—C2—H2A	120.5	C12—C11—H11A	119.5
C2—C3—C4	120.7 (2)	C7—C12—C11	119.3 (2)
C2—C3—H3A	119.6	C7—C12—H12A	120.4
C4—C3—H3A	119.6	C11—C12—H12A	120.4
C3—C4—C5	120.3 (2)	O2—C13—N1	120.32 (18)
C3—C4—H4A	119.9	O2—C13—C14	121.16 (19)
C5—C4—H4A	119.9	N1—C13—C14	118.48 (18)
C4—C5—C6	119.9 (2)	C13—C14—H14A	109.5
C4—C5—H5A	120.0	C13—C14—H14B	109.5
C6—C5—H5A	120.0	H14A—C14—H14B	109.5
C5—C6—C1	118.67 (17)	C13—C14—H14C	109.5
C5—C6—N1	122.65 (17)	H14A—C14—H14C	109.5
C1—C6—N1	118.40 (16)	H14B—C14—H14C	109.5
C12—C7—C8	119.46 (17)	C13—N1—C6	124.75 (15)
C12—C7—N1	122.58 (17)	C13—N1—C7	120.12 (15)
C8—C7—N1	117.90 (16)	C6—N1—C7	115.08 (14)
C7—C8—C9	121.0 (2)	O1B—S1—O1A	119.8 (6)
C7—C8—S1	118.55 (14)	O1B—S1—C1	116.2 (6)
C9—C8—S1	120.37 (16)	O1A—S1—C1	108.47 (11)
C10—C9—C8	118.8 (2)	O1B—S1—C8	105.4 (6)
C10—C9—H9A	120.6	O1A—S1—C8	109.77 (10)
C8—C9—H9A	120.6	C1—S1—C8	93.87 (9)
C6—C1—C2—C3	−1.4 (3)	C14—C13—N1—C6	6.2 (3)
S1—C1—C2—C3	177.45 (17)	O2—C13—N1—C7	6.8 (3)
C1—C2—C3—C4	0.2 (3)	C14—C13—N1—C7	−171.17 (19)
C2—C3—C4—C5	1.7 (3)	C5—C6—N1—C13	54.0 (3)
C3—C4—C5—C6	−2.3 (3)	C1—C6—N1—C13	−132.1 (2)
C4—C5—C6—C1	1.1 (3)	C5—C6—N1—C7	−128.52 (19)
C4—C5—C6—N1	174.92 (18)	C1—C6—N1—C7	45.4 (2)
C2—C1—C6—C5	0.8 (3)	C12—C7—N1—C13	−51.1 (3)
S1—C1—C6—C5	−178.09 (14)	C8—C7—N1—C13	131.6 (2)
C2—C1—C6—N1	−173.37 (17)	C12—C7—N1—C6	131.29 (19)
S1—C1—C6—N1	7.8 (2)	C8—C7—N1—C6	−46.0 (2)
C12—C7—C8—C9	−0.4 (3)	C2—C1—S1—O1B	−116.3 (7)
N1—C7—C8—C9	177.03 (17)	C6—C1—S1—O1B	62.6 (7)
C12—C7—C8—S1	176.25 (15)	C2—C1—S1—O1A	22.1 (2)
N1—C7—C8—S1	−6.3 (2)	C6—C1—S1—O1A	−159.03 (15)
C7—C8—C9—C10	0.9 (3)	C2—C1—S1—C8	134.44 (17)
S1—C8—C9—C10	−175.71 (16)	C6—C1—S1—C8	−46.70 (16)
C8—C9—C10—C11	−0.2 (3)	C7—C8—S1—O1B	−72.4 (6)
C9—C10—C11—C12	−1.0 (3)	C9—C8—S1—O1B	104.2 (6)
C8—C7—C12—C11	−0.8 (3)	C7—C8—S1—O1A	157.27 (16)
N1—C7—C12—C11	−178.08 (18)	C9—C8—S1—O1A	−26.1 (2)
C10—C11—C12—C7	1.5 (3)	C7—C8—S1—C1	46.07 (16)
O2—C13—N1—C6	−175.9 (2)	C9—C8—S1—C1	−137.28 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1Ai	0.93	2.31	3.207 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1Ai	0.93	2.31	3.207 (3)	163

Symmetry code: (i) .