1-(10H-Phenothia-zin-2-yl)ethanone.

In the title compound, C(14)H(11)NOS, the thia-zine ring adopts a slightly distorted boat conformation. The dihedral angle between the mean planes of the two benzene rings is 20.2 (9)°. An inter-molecular N-H⋯O hydrogen bond and a weak C-H⋯π inter-action occur in the crystal, creating a two-dimensional network parallel to the bc plane.

Related literature

For applications of phenothia­zines in drugs and medicine, see: Miller et al. (1999 ▶); Wermuth (2003 ▶); Wang et al. (2008 ▶); Lam et al. (2001 ▶); Kojilo et al. (2001 ▶). For related structures, see: Bell et al. (1968 ▶); McDowell (1969 ▶, 1970 ▶, 1975 ▶, 1976 ▶, 1978 ▶, 1980 ▶); Chu & Van der Helm (1974 ▶, 1975 ▶, 1977) ▶); Phelps & Cordes (1974 ▶, 1975 ▶); Harrison et al. (2007 ▶); Wang et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H11NOS

M = 241.30

Monoclinic,

a = 14.3445 (18) Å

b = 5.5425 (7) Å

c = 15.694 (2) Å

β = 114.494 (2)°

V = 1135.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.55 × 0.55 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.868, T max = 0.974

8194 measured reflections

3331 independent reflections

2828 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.04

3331 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001851/is2662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001851/is2662Isup2.hkl

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

C14H11NOS	F(000) = 504
Mr = 241.30	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2781 reflections
a = 14.3445 (18) Å	θ = 2.6–30.6°
b = 5.5425 (7) Å	µ = 0.27 mm−1
c = 15.694 (2) Å	T = 100 K
β = 114.494 (2)°	Plate, orange
V = 1135.4 (2) Å3	0.55 × 0.55 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	3331 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 31.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→18
Tmin = 0.868, Tmax = 0.974	k = −8→7
8194 measured reflections	l = −21→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.4353P] where P = (Fo2 + 2Fc2)/3
3331 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.29 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
S1	0.26560 (3)	0.41617 (6)	0.15897 (2)	0.01761 (10)
O1	0.65447 (8)	0.81327 (19)	0.54988 (7)	0.0213 (2)
N1	0.30331 (9)	0.8588 (2)	0.28579 (8)	0.0165 (2)
C11	0.55267 (10)	0.5672 (2)	0.42245 (9)	0.0140 (2)
C8	0.37282 (10)	0.4732 (2)	0.26461 (9)	0.0139 (2)
C12	0.47152 (10)	0.7316 (2)	0.39393 (9)	0.0143 (2)
H11	0.4778	0.8723	0.4282	0.017*
C13	0.64777 (10)	0.6258 (2)	0.50679 (9)	0.0158 (3)
C5	0.17254 (10)	0.5996 (2)	0.17352 (9)	0.0158 (3)
C7	0.38142 (10)	0.6876 (2)	0.31481 (9)	0.0137 (2)
C10	0.54264 (10)	0.3531 (2)	0.37268 (9)	0.0148 (2)
H9	0.5960	0.2420	0.3918	0.018*
C6	0.20076 (10)	0.8030 (2)	0.23161 (9)	0.0154 (2)
C14	0.73624 (11)	0.4520 (3)	0.53624 (10)	0.0212 (3)
H13A	0.7645	0.4522	0.4905	0.032*
H13B	0.7127	0.2927	0.5412	0.032*
H13C	0.7879	0.5003	0.5959	0.032*
C2	0.02171 (11)	0.9054 (3)	0.17891 (11)	0.0228 (3)
H2	−0.0286	1.0098	0.1799	0.027*
C4	0.06974 (11)	0.5477 (3)	0.12089 (10)	0.0201 (3)
H4	0.0514	0.4087	0.0845	0.024*
C1	0.12425 (11)	0.9539 (3)	0.23424 (10)	0.0199 (3)
H1	0.1420	1.0881	0.2733	0.024*
C3	−0.00598 (11)	0.7028 (3)	0.12236 (10)	0.0231 (3)
H3	−0.0747	0.6703	0.0856	0.028*
C9	0.45264 (10)	0.3070 (2)	0.29454 (9)	0.0150 (2)
H14	0.4456	0.1634	0.2618	0.018*
H15	0.3129 (13)	0.971 (3)	0.3234 (12)	0.018 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01602 (18)	0.01739 (18)	0.01652 (17)	−0.00026 (12)	0.00384 (13)	−0.00450 (11)
O1	0.0212 (5)	0.0192 (5)	0.0192 (5)	−0.0004 (4)	0.0041 (4)	−0.0037 (4)
N1	0.0149 (5)	0.0108 (5)	0.0202 (5)	0.0003 (4)	0.0036 (4)	−0.0024 (4)
C11	0.0145 (6)	0.0128 (6)	0.0148 (5)	−0.0002 (4)	0.0061 (5)	0.0008 (4)
C8	0.0137 (6)	0.0131 (6)	0.0150 (5)	−0.0022 (4)	0.0059 (5)	−0.0003 (4)
C12	0.0162 (6)	0.0112 (6)	0.0156 (6)	−0.0004 (4)	0.0067 (5)	−0.0008 (4)
C13	0.0159 (6)	0.0159 (6)	0.0160 (6)	−0.0009 (5)	0.0070 (5)	0.0015 (5)
C5	0.0155 (6)	0.0153 (6)	0.0150 (6)	0.0007 (5)	0.0045 (5)	0.0019 (4)
C7	0.0147 (6)	0.0113 (6)	0.0155 (6)	−0.0003 (5)	0.0065 (5)	0.0012 (4)
C10	0.0150 (6)	0.0124 (6)	0.0177 (6)	0.0014 (5)	0.0074 (5)	0.0012 (5)
C6	0.0147 (6)	0.0142 (6)	0.0154 (6)	−0.0003 (5)	0.0042 (5)	0.0018 (4)
C14	0.0158 (7)	0.0205 (7)	0.0233 (7)	0.0024 (5)	0.0041 (6)	0.0005 (5)
C2	0.0164 (7)	0.0238 (7)	0.0252 (7)	0.0043 (5)	0.0055 (6)	−0.0004 (5)
C4	0.0189 (7)	0.0203 (7)	0.0177 (6)	−0.0022 (5)	0.0043 (5)	−0.0019 (5)
C1	0.0181 (7)	0.0179 (7)	0.0219 (6)	0.0019 (5)	0.0063 (6)	−0.0020 (5)
C3	0.0141 (6)	0.0273 (8)	0.0225 (7)	−0.0005 (5)	0.0022 (5)	−0.0011 (6)
C9	0.0175 (6)	0.0104 (6)	0.0190 (6)	−0.0007 (5)	0.0096 (5)	−0.0015 (4)

S1—C8	1.7606 (13)	C5—C6	1.4003 (18)
S1—C5	1.7664 (14)	C10—C9	1.3868 (18)
O1—C13	1.2216 (16)	C10—H9	0.9300
N1—C7	1.3930 (16)	C6—C1	1.3939 (18)
N1—C6	1.3948 (17)	C14—H13A	0.9600
N1—H15	0.829 (18)	C14—H13B	0.9600
C11—C10	1.3946 (18)	C14—H13C	0.9600
C11—C12	1.3980 (18)	C2—C3	1.384 (2)
C11—C13	1.4903 (18)	C2—C1	1.390 (2)
C8—C9	1.3908 (18)	C2—H2	0.9300
C8—C7	1.4026 (18)	C4—C3	1.393 (2)
C12—C7	1.3932 (18)	C4—H4	0.9300
C12—H11	0.9300	C1—H1	0.9300
C13—C14	1.5051 (19)	C3—H3	0.9300
C5—C4	1.3891 (19)	C9—H14	0.9300
C8—S1—C5	100.77 (6)	C1—C6—N1	119.56 (12)
C7—N1—C6	123.39 (11)	C1—C6—C5	118.93 (12)
C7—N1—H15	113.9 (12)	N1—C6—C5	121.51 (12)
C6—N1—H15	115.0 (12)	C13—C14—H13A	109.5
C10—C11—C12	119.76 (12)	C13—C14—H13B	109.5
C10—C11—C13	121.79 (12)	H13A—C14—H13B	109.5
C12—C11—C13	118.44 (11)	C13—C14—H13C	109.5
C9—C8—C7	120.20 (12)	H13A—C14—H13C	109.5
C9—C8—S1	118.33 (10)	H13B—C14—H13C	109.5
C7—C8—S1	121.34 (10)	C3—C2—C1	120.39 (13)
C7—C12—C11	120.84 (12)	C3—C2—H2	119.8
C7—C12—H11	119.6	C1—C2—H2	119.8
C11—C12—H11	119.6	C5—C4—C3	120.36 (13)
O1—C13—C11	120.67 (12)	C5—C4—H4	119.8
O1—C13—C14	120.76 (12)	C3—C4—H4	119.8
C11—C13—C14	118.55 (12)	C2—C1—C6	120.52 (13)
C4—C5—C6	120.19 (12)	C2—C1—H1	119.7
C4—C5—S1	118.48 (10)	C6—C1—H1	119.7
C6—C5—S1	121.18 (10)	C2—C3—C4	119.54 (13)
N1—C7—C12	119.68 (11)	C2—C3—H3	120.2
N1—C7—C8	121.47 (12)	C4—C3—H3	120.2
C12—C7—C8	118.83 (12)	C10—C9—C8	120.71 (12)
C9—C10—C11	119.62 (12)	C10—C9—H14	119.6
C9—C10—H9	120.2	C8—C9—H14	119.6
C11—C10—H9	120.2
C5—S1—C8—C9	159.37 (10)	C12—C11—C10—C9	0.86 (18)
C5—S1—C8—C7	−24.72 (12)	C13—C11—C10—C9	−179.90 (11)
C10—C11—C12—C7	−1.68 (18)	C7—N1—C6—C1	156.10 (12)
C13—C11—C12—C7	179.06 (11)	C7—N1—C6—C5	−24.60 (19)
C10—C11—C13—O1	−179.23 (12)	C4—C5—C6—C1	−1.17 (19)
C12—C11—C13—O1	0.02 (18)	S1—C5—C6—C1	174.31 (10)
C10—C11—C13—C14	2.26 (18)	C4—C5—C6—N1	179.53 (13)
C12—C11—C13—C14	−178.50 (12)	S1—C5—C6—N1	−5.00 (18)
C8—S1—C5—C4	−158.90 (11)	C6—C5—C4—C3	2.7 (2)
C8—S1—C5—C6	25.55 (12)	S1—C5—C4—C3	−172.88 (11)
C6—N1—C7—C12	−156.23 (12)	C3—C2—C1—C6	1.8 (2)
C6—N1—C7—C8	25.55 (19)	N1—C6—C1—C2	178.23 (13)
C11—C12—C7—N1	−177.47 (11)	C5—C6—C1—C2	−1.1 (2)
C11—C12—C7—C8	0.80 (18)	C1—C2—C3—C4	−0.3 (2)
C9—C8—C7—N1	179.12 (11)	C5—C4—C3—C2	−2.0 (2)
S1—C8—C7—N1	3.28 (17)	C11—C10—C9—C8	0.82 (19)
C9—C8—C7—C12	0.89 (18)	C7—C8—C9—C10	−1.71 (19)
S1—C8—C7—C12	−174.95 (9)	S1—C8—C9—C10	174.25 (10)

Cg3 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H15···O1i	0.829 (18)	2.198 (18)	3.0042 (15)	164.3 (17)
C9—H14···Cg3ii	0.93	2.64	3.306 (7)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H15⋯O1i	0.829 (18)	2.198 (18)	3.0042 (15)	164.3 (17)
C9—H14⋯Cg3ii	0.93	2.64	3.306 (7)	130

Symmetry codes: (i) ; (ii) .