10-Ethyl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-10H-phenothia-zine.

In the title compound, C(17)H(15)N(3)OS, the phenothia-zine ring system is slightly bent, with a dihedral angle of 13.68 (7)° between the benzene rings. The dihedral angle between the oxadiazole ring and the adjacent benzene ring is 7.72 (7)°. In the crystal, a π-π inter-action with a centroid-centroid distance of 3.752 (2) Å is observed between the benzene rings of neighbouring mol-ecules.

Related literature

For general background to phenothia­zine derivatives, see: Kim et al. (2011 ▶); Hagfeldt et al. (2010 ▶). For related structures, see: Chu & Van der Helm (1975 ▶); Hdii et al. (1998 ▶); Li, Hu et al. (2009 ▶); Li, Lv et al. (2009 ▶); Yu et al. (2011 ▶).

Experimental

Crystal data

C17H15N3OS

M = 309.38

Triclinic,

a = 7.6752 (4) Å

b = 8.2913 (4) Å

c = 12.9469 (8) Å

α = 84.870 (4)°

β = 82.569 (4)°

γ = 63.696 (3)°

V = 731.92 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.15 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.968, T max = 0.979

5348 measured reflections

2554 independent reflections

2217 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.05

2554 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ▶) and SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200462X/is5065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200462X/is5065Isup3.hkl

Supplementary material file. DOI: 10.1107/S160053681200462X/is5065Isup3.cml

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

C17H15N3OS	Z = 2
Mr = 309.38	F(000) = 324
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6752 (4) Å	Cell parameters from 2708 reflections
b = 8.2913 (4) Å	θ = 3.0–31.6°
c = 12.9469 (8) Å	µ = 0.23 mm−1
α = 84.870 (4)°	T = 293 K
β = 82.569 (4)°	Block, yellow
γ = 63.696 (3)°	0.15 × 0.15 × 0.10 mm
V = 731.92 (7) Å3

Bruker SMART APEX diffractometer	2554 independent reflections
Radiation source: fine-focus sealed tube	2217 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.968, Tmax = 0.979	k = −9→9
5348 measured reflections	l = −15→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2148P] where P = (Fo2 + 2Fc2)/3
2554 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.28 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	0.37243 (8)	0.17365 (6)	0.11098 (4)	0.05078 (19)
O1	0.39396 (19)	0.69128 (15)	−0.27750 (9)	0.0430 (3)
C12	0.2887 (2)	0.3831 (2)	0.04285 (13)	0.0353 (4)
N1	0.0965 (2)	0.54971 (18)	0.19818 (11)	0.0410 (4)
C10	0.3234 (3)	0.5423 (2)	−0.11819 (13)	0.0388 (4)
C6	0.0893 (3)	0.3994 (2)	0.25572 (13)	0.0376 (4)
C7	0.1642 (2)	0.5454 (2)	0.09210 (13)	0.0371 (4)
C1	0.2039 (3)	0.2227 (2)	0.22245 (13)	0.0377 (4)
N2	0.5266 (2)	0.3956 (2)	−0.27726 (12)	0.0460 (4)
C13	0.4168 (3)	0.5350 (2)	−0.22376 (13)	0.0388 (4)
C11	0.3653 (3)	0.3829 (2)	−0.05932 (13)	0.0382 (4)
H11	0.4470	0.2736	−0.0898	0.046*
C9	0.1961 (3)	0.7029 (2)	−0.07199 (14)	0.0452 (5)
H9	0.1633	0.8110	−0.1103	0.054*
C5	−0.0285 (3)	0.4198 (2)	0.34965 (14)	0.0450 (4)
H5	−0.1070	0.5351	0.3734	0.054*
C15	0.0098 (3)	0.7238 (2)	0.24919 (15)	0.0454 (5)
H15A	0.0783	0.7936	0.2189	0.054*
H15B	0.0307	0.7016	0.3224	0.054*
N3	0.5841 (2)	0.4600 (2)	−0.37384 (12)	0.0477 (4)
C8	0.1174 (3)	0.7040 (2)	0.03038 (14)	0.0453 (5)
H8	0.0307	0.8133	0.0592	0.054*
C2	0.1976 (3)	0.0770 (2)	0.28143 (15)	0.0462 (5)
H2	0.2731	−0.0388	0.2577	0.055*
C14	0.5034 (3)	0.6320 (2)	−0.36985 (13)	0.0424 (4)
C4	−0.0320 (3)	0.2730 (3)	0.40882 (15)	0.0498 (5)
H4	−0.1109	0.2908	0.4716	0.060*
C16	−0.2063 (3)	0.8351 (3)	0.24062 (18)	0.0573 (6)
H16A	−0.2300	0.8537	0.1685	0.086*
H16B	−0.2488	0.9493	0.2713	0.086*
H16C	−0.2773	0.7728	0.2766	0.086*
C3	0.0812 (3)	0.1007 (3)	0.37469 (16)	0.0521 (5)
H3	0.0790	0.0020	0.4140	0.063*
C17	0.5164 (4)	0.7672 (3)	−0.44929 (15)	0.0558 (5)
H17A	0.5952	0.8184	−0.4272	0.084*
H17B	0.3878	0.8606	−0.4578	0.084*
H17C	0.5748	0.7102	−0.5145	0.084*

	U11	U22	U33	U12	U13	U23
S1	0.0589 (3)	0.0257 (3)	0.0468 (3)	−0.0033 (2)	0.0067 (2)	0.00176 (18)
O1	0.0540 (8)	0.0336 (6)	0.0387 (7)	−0.0177 (6)	−0.0011 (6)	0.0001 (5)
C12	0.0363 (9)	0.0266 (8)	0.0403 (9)	−0.0112 (7)	−0.0049 (7)	0.0004 (7)
N1	0.0469 (9)	0.0259 (7)	0.0425 (8)	−0.0103 (6)	0.0023 (7)	−0.0035 (6)
C10	0.0405 (10)	0.0356 (9)	0.0403 (9)	−0.0169 (8)	−0.0050 (8)	0.0008 (7)
C6	0.0380 (9)	0.0298 (9)	0.0413 (9)	−0.0111 (7)	−0.0060 (7)	−0.0005 (7)
C7	0.0352 (9)	0.0287 (8)	0.0438 (9)	−0.0110 (7)	−0.0022 (7)	−0.0016 (7)
C1	0.0412 (10)	0.0304 (9)	0.0393 (9)	−0.0134 (7)	−0.0066 (7)	0.0008 (7)
N2	0.0514 (10)	0.0370 (8)	0.0437 (8)	−0.0154 (7)	−0.0002 (7)	0.0004 (7)
C13	0.0407 (10)	0.0325 (9)	0.0427 (9)	−0.0156 (8)	−0.0067 (8)	0.0023 (7)
C11	0.0393 (10)	0.0281 (8)	0.0430 (9)	−0.0103 (7)	−0.0039 (8)	−0.0048 (7)
C9	0.0492 (11)	0.0290 (9)	0.0492 (10)	−0.0119 (8)	−0.0024 (9)	0.0070 (8)
C5	0.0437 (10)	0.0377 (10)	0.0460 (10)	−0.0118 (8)	0.0002 (8)	−0.0035 (8)
C15	0.0516 (11)	0.0325 (9)	0.0502 (10)	−0.0170 (8)	−0.0002 (9)	−0.0068 (8)
N3	0.0526 (10)	0.0434 (9)	0.0423 (8)	−0.0181 (8)	0.0011 (7)	−0.0023 (7)
C8	0.0472 (11)	0.0268 (9)	0.0505 (11)	−0.0078 (8)	0.0020 (9)	−0.0011 (7)
C2	0.0545 (12)	0.0309 (9)	0.0496 (10)	−0.0158 (8)	−0.0053 (9)	0.0009 (8)
C14	0.0471 (11)	0.0425 (10)	0.0374 (9)	−0.0197 (8)	−0.0031 (8)	−0.0014 (7)
C4	0.0507 (12)	0.0497 (11)	0.0452 (10)	−0.0212 (10)	0.0014 (9)	0.0039 (9)
C16	0.0530 (12)	0.0355 (10)	0.0696 (13)	−0.0089 (9)	0.0043 (10)	−0.0056 (9)
C3	0.0612 (13)	0.0424 (10)	0.0523 (11)	−0.0249 (10)	−0.0033 (10)	0.0093 (9)
C17	0.0736 (15)	0.0516 (12)	0.0451 (11)	−0.0321 (11)	−0.0024 (10)	0.0049 (9)

S1—C1	1.7541 (17)	C9—H9	0.9300
S1—C12	1.7583 (17)	C5—C4	1.388 (3)
O1—C14	1.362 (2)	C5—H5	0.9300
O1—C13	1.365 (2)	C15—C16	1.512 (3)
C12—C11	1.376 (2)	C15—H15A	0.9700
C12—C7	1.409 (2)	C15—H15B	0.9700
N1—C7	1.402 (2)	N3—C14	1.282 (2)
N1—C6	1.413 (2)	C8—H8	0.9300
N1—C15	1.472 (2)	C2—C3	1.379 (3)
C10—C9	1.387 (2)	C2—H2	0.9300
C10—C11	1.392 (2)	C14—C17	1.480 (2)
C10—C13	1.452 (2)	C4—C3	1.380 (3)
C6—C5	1.394 (2)	C4—H4	0.9300
C6—C1	1.407 (2)	C16—H16A	0.9600
C7—C8	1.402 (2)	C16—H16B	0.9600
C1—C2	1.387 (2)	C16—H16C	0.9600
N2—C13	1.287 (2)	C3—H3	0.9300
N2—N3	1.411 (2)	C17—H17A	0.9600
C11—H11	0.9300	C17—H17B	0.9600
C9—C8	1.383 (2)	C17—H17C	0.9600
C1—S1—C12	101.74 (8)	N1—C15—H15A	108.5
C14—O1—C13	102.81 (13)	C16—C15—H15A	108.5
C11—C12—C7	121.19 (15)	N1—C15—H15B	108.5
C11—C12—S1	116.40 (12)	C16—C15—H15B	108.5
C7—C12—S1	122.15 (13)	H15A—C15—H15B	107.5
C7—N1—C6	123.14 (14)	C14—N3—N2	106.14 (14)
C7—N1—C15	118.30 (14)	C9—C8—C7	122.01 (16)
C6—N1—C15	118.23 (14)	C9—C8—H8	119.0
C9—C10—C11	118.04 (16)	C7—C8—H8	119.0
C9—C10—C13	122.68 (16)	C3—C2—C1	121.15 (17)
C11—C10—C13	119.26 (15)	C3—C2—H2	119.4
C5—C6—C1	117.04 (16)	C1—C2—H2	119.4
C5—C6—N1	121.22 (15)	N3—C14—O1	112.57 (15)
C1—C6—N1	121.73 (15)	N3—C14—C17	129.09 (17)
C8—C7—N1	121.38 (15)	O1—C14—C17	118.33 (16)
C8—C7—C12	116.46 (15)	C3—C4—C5	120.19 (17)
N1—C7—C12	122.11 (15)	C3—C4—H4	119.9
C2—C1—C6	120.68 (16)	C5—C4—H4	119.9
C2—C1—S1	116.70 (13)	C15—C16—H16A	109.5
C6—C1—S1	122.48 (13)	C15—C16—H16B	109.5
C13—N2—N3	106.45 (14)	H16A—C16—H16B	109.5
N2—C13—O1	112.02 (15)	C15—C16—H16C	109.5
N2—C13—C10	128.50 (16)	H16A—C16—H16C	109.5
O1—C13—C10	119.47 (15)	H16B—C16—H16C	109.5
C12—C11—C10	121.51 (15)	C2—C3—C4	119.06 (17)
C12—C11—H11	119.2	C2—C3—H3	120.5
C10—C11—H11	119.2	C4—C3—H3	120.5
C8—C9—C10	120.70 (16)	C14—C17—H17A	109.5
C8—C9—H9	119.6	C14—C17—H17B	109.5
C10—C9—H9	119.6	H17A—C17—H17B	109.5
C4—C5—C6	121.87 (17)	C14—C17—H17C	109.5
C4—C5—H5	119.1	H17A—C17—H17C	109.5
C6—C5—H5	119.1	H17B—C17—H17C	109.5
N1—C15—C16	114.91 (16)