10H-Phenothia-zine 5-oxide.

In the title compound, C(12)H(9)NOS, the sulfoxide O atom is disordered over two sites with occupancies of 0.907 (4) and 0.093 (4). The dihedral angle betweeen the two aromatic rings is 18.40 (14)°. Different types of supramolecular interactions including inter-molecular N-H⋯O hydrogen bonds and π-π contacts [centroid-centroid distances = 3.9096 (16) and 4.1423 (16) Å] between the aromatic rings of symmetry-related mol-ecules are observed in the crystal structure.

Related literature

For N-aryl­phenothia­zine structures, see: Chu & Van der Helm (1974 ▶, 1975 ▶, 1976 ▶) and for N-aryl­phenothia­zine oxide structures, see: Chu et al. (1985 ▶), Wang et al. (2009 ▶). For a dioxophenothia­zinium cation co-crystallized with terephthalate trihydrate, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C12H9NOS

M = 215.26

Monoclinic,

a = 6.4482 (4) Å

b = 7.6610 (5) Å

c = 22.0956 (14) Å

β = 110.466 (2)°

V = 1022.62 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 297 K

0.50 × 0.50 × 0.40 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.871, T max = 0.895

7632 measured reflections

2361 independent reflections

1962 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.175

S = 1.04

2361 reflections

146 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010) ▶; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047914/si2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047914/si2310Isup2.hkl

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

C12H9NOS	F(000) = 448
Mr = 215.26	Dx = 1.398 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3079 reflections
a = 6.4482 (4) Å	θ = 2.7–27.3°
b = 7.6610 (5) Å	µ = 0.28 mm−1
c = 22.0956 (14) Å	T = 297 K
β = 110.466 (2)°	Block, brown
V = 1022.62 (11) Å3	0.50 × 0.50 × 0.40 mm
Z = 4

Bruker APEX area-detector diffractometer	2361 independent reflections
Radiation source: fine-focus sealed tube	1962 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scan	θmax = 28.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.871, Tmax = 0.895	k = −9→9
7632 measured reflections	l = −28→29

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.098P)2 + 0.4384P] where P = (Fo2 + 2Fc2)/3
2361 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.44 e Å−3
6 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	Occ. (<1)
S5	0.42382 (10)	0.16598 (9)	0.58407 (3)	0.0511 (3)
O5	0.5476 (3)	0.3348 (3)	0.60011 (10)	0.0515 (6)	0.907 (4)
O5'	0.537 (2)	0.0431 (17)	0.5773 (6)	0.024 (4)	0.093 (4)
N10	−0.0212 (3)	0.2763 (3)	0.59516 (10)	0.0465 (5)
H10A	−0.1256	0.3363	0.6009	0.056*
C1	−0.1959 (5)	0.3230 (3)	0.48155 (14)	0.0563 (7)
H1A	−0.3197	0.3677	0.4885	0.068*
C2	−0.1951 (6)	0.3105 (4)	0.42027 (16)	0.0695 (9)
H2A	−0.3182	0.3472	0.3859	0.083*
C3	−0.0141 (7)	0.2438 (4)	0.40843 (15)	0.0746 (10)
H3A	−0.0169	0.2332	0.3662	0.090*
C4A	0.1721 (4)	0.2076 (3)	0.52193 (12)	0.0459 (6)
C4	0.1689 (6)	0.1936 (4)	0.45877 (15)	0.0624 (8)
H4A	0.2917	0.1500	0.4509	0.075*
C5A	0.3231 (4)	0.1236 (3)	0.64649 (12)	0.0458 (6)
C6	0.4605 (5)	0.0291 (4)	0.69942 (15)	0.0621 (8)
H6A	0.5904	−0.0202	0.6979	0.075*
C7	0.4058 (6)	0.0086 (4)	0.75312 (16)	0.0750 (9)
H7A	0.4974	−0.0554	0.7880	0.090*
C8	0.2155 (7)	0.0822 (4)	0.75575 (15)	0.0725 (9)
H8A	0.1807	0.0699	0.7930	0.087*
C9A	0.1255 (4)	0.1936 (3)	0.64756 (12)	0.0433 (5)
C9	0.0752 (5)	0.1739 (4)	0.70411 (15)	0.0592 (7)
H9A	−0.0533	0.2232	0.7067	0.071*
C10A	−0.0122 (4)	0.2694 (3)	0.53439 (12)	0.0429 (5)

	U11	U22	U33	U12	U13	U23
S5	0.0328 (4)	0.0552 (4)	0.0649 (5)	0.0046 (2)	0.0165 (3)	−0.0057 (3)
O5	0.0265 (9)	0.0631 (13)	0.0647 (13)	−0.0072 (8)	0.0156 (9)	−0.0056 (9)
O5'	0.024 (4)	0.025 (4)	0.025 (4)	0.0011 (10)	0.0089 (16)	−0.0008 (10)
N10	0.0303 (9)	0.0531 (12)	0.0573 (13)	0.0056 (9)	0.0166 (9)	0.0031 (10)
C1	0.0421 (14)	0.0503 (14)	0.0633 (17)	−0.0057 (11)	0.0018 (12)	0.0081 (12)
C2	0.067 (2)	0.0634 (18)	0.0589 (18)	−0.0144 (15)	−0.0016 (15)	0.0080 (14)
C3	0.096 (3)	0.073 (2)	0.0481 (17)	−0.026 (2)	0.0172 (17)	−0.0066 (15)
C4A	0.0401 (13)	0.0447 (12)	0.0511 (14)	−0.0055 (10)	0.0139 (11)	−0.0057 (10)
C4	0.0675 (19)	0.0626 (17)	0.0614 (17)	−0.0154 (14)	0.0279 (15)	−0.0152 (14)
C5A	0.0364 (12)	0.0416 (12)	0.0532 (14)	−0.0010 (10)	0.0077 (10)	−0.0025 (10)
C6	0.0524 (16)	0.0517 (15)	0.0674 (18)	0.0074 (12)	0.0024 (13)	0.0060 (13)
C7	0.080 (2)	0.0612 (19)	0.063 (2)	−0.0008 (17)	−0.0001 (17)	0.0118 (15)
C8	0.095 (3)	0.0701 (19)	0.0504 (17)	−0.0125 (18)	0.0227 (17)	0.0062 (14)
C9A	0.0352 (12)	0.0415 (12)	0.0502 (14)	−0.0050 (9)	0.0113 (10)	−0.0005 (10)
C9	0.0559 (17)	0.0644 (17)	0.0630 (17)	−0.0101 (13)	0.0278 (14)	−0.0038 (13)
C10A	0.0333 (11)	0.0391 (11)	0.0526 (14)	−0.0056 (9)	0.0101 (10)	0.0009 (10)

S5—O5'	1.233 (13)	C4A—C10A	1.393 (3)
S5—O5	1.496 (2)	C4A—C4	1.393 (4)
S5—C5A	1.748 (3)	C4—H4A	0.9300
S5—C4A	1.750 (3)	C5A—C9A	1.390 (3)
N10—C10A	1.365 (3)	C5A—C6	1.397 (4)
N10—C9A	1.368 (3)	C6—C7	1.360 (5)
N10—H10A	0.8600	C6—H6A	0.9300
C1—C2	1.359 (5)	C7—C8	1.370 (5)
C1—C10A	1.403 (3)	C7—H7A	0.9300
C1—H1A	0.9300	C8—C9	1.376 (5)
C2—C3	1.380 (5)	C8—H8A	0.9300
C2—H2A	0.9300	C9A—C9	1.404 (4)
C3—C4	1.364 (5)	C9—H9A	0.9300
C3—H3A	0.9300
O5'—S5—O5	113.5 (6)	C4A—C4—H4A	120.0
O5'—S5—C5A	110.7 (6)	C9A—C5A—C6	120.1 (3)
O5—S5—C5A	106.75 (12)	C9A—C5A—S5	122.5 (2)
O5'—S5—C4A	118.1 (6)	C6—C5A—S5	117.0 (2)
O5—S5—C4A	107.46 (12)	C7—C6—C5A	120.5 (3)
C5A—S5—C4A	98.86 (12)	C7—C6—H6A	119.7
C10A—N10—C9A	124.1 (2)	C5A—C6—H6A	119.7
C10A—N10—H10A	118.0	C6—C7—C8	119.9 (3)
C9A—N10—H10A	118.0	C6—C7—H7A	120.0
C2—C1—C10A	120.8 (3)	C8—C7—H7A	120.0
C2—C1—H1A	119.6	C7—C8—C9	120.9 (3)
C10A—C1—H1A	119.6	C7—C8—H8A	119.5
C1—C2—C3	120.8 (3)	C9—C8—H8A	119.5
C1—C2—H2A	119.6	N10—C9A—C5A	122.1 (2)
C3—C2—H2A	119.6	N10—C9A—C9	119.8 (2)
C4—C3—C2	119.9 (3)	C5A—C9A—C9	118.2 (2)
C4—C3—H3A	120.1	C8—C9—C9A	120.2 (3)
C2—C3—H3A	120.1	C8—C9—H9A	119.9
C10A—C4A—C4	120.6 (3)	C9A—C9—H9A	119.9
C10A—C4A—S5	121.9 (2)	N10—C10A—C4A	122.7 (2)
C4—C4A—S5	117.2 (2)	N10—C10A—C1	119.6 (2)
C3—C4—C4A	120.1 (3)	C4A—C10A—C1	117.7 (3)
C3—C4—H4A	120.0
C10A—C1—C2—C3	0.3 (4)	C5A—C6—C7—C8	−0.6 (5)
C1—C2—C3—C4	−1.6 (5)	C6—C7—C8—C9	1.5 (5)
O5'—S5—C4A—C10A	145.5 (7)	C10A—N10—C9A—C5A	13.3 (4)
O5—S5—C4A—C10A	−84.5 (2)	C10A—N10—C9A—C9	−165.2 (2)
C5A—S5—C4A—C10A	26.3 (2)	C6—C5A—C9A—N10	−175.3 (2)
O5'—S5—C4A—C4	−40.9 (7)	S5—C5A—C9A—N10	11.0 (3)
O5—S5—C4A—C4	89.1 (2)	C6—C5A—C9A—C9	3.2 (4)
C5A—S5—C4A—C4	−160.1 (2)	S5—C5A—C9A—C9	−170.48 (19)
C2—C3—C4—C4A	0.8 (5)	C7—C8—C9—C9A	0.0 (5)
C10A—C4A—C4—C3	1.3 (4)	N10—C9A—C9—C8	176.2 (3)
S5—C4A—C4—C3	−172.4 (2)	C5A—C9A—C9—C8	−2.3 (4)
O5'—S5—C5A—C9A	−151.4 (7)	C9A—N10—C10A—C4A	−13.6 (4)
O5—S5—C5A—C9A	84.6 (2)	C9A—N10—C10A—C1	165.2 (2)
C4A—S5—C5A—C9A	−26.7 (2)	C4—C4A—C10A—N10	176.3 (2)
O5'—S5—C5A—C6	34.7 (7)	S5—C4A—C10A—N10	−10.4 (3)
O5—S5—C5A—C6	−89.3 (2)	C4—C4A—C10A—C1	−2.5 (4)
C4A—S5—C5A—C6	159.4 (2)	S5—C4A—C10A—C1	170.87 (18)
C9A—C5A—C6—C7	−1.8 (4)	C2—C1—C10A—N10	−177.1 (2)
S5—C5A—C6—C7	172.2 (2)	C2—C1—C10A—C4A	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···O5i	0.86	2.10	2.856 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10A⋯O5i	0.86	2.10	2.856 (3)	146

Symmetry code: (i) .