2-(5-Bromo-thio-phen-2-yl)-5-[5-(10-ethyl-phenothia-zin-3-yl)thio-phen-2-yl]-1,3,4-oxadiazole.

The mol-ecule of the title compound, C(24)H(16)BrN(3)OS(3), contains three approximately planar fragments, viz. an oxadiazole ring plus two adjacent thio-phene groups, and two phenothia-zine benzene rings, with largest deviations from the least-squares planes of 0.051 (3), 0.019 (4) and 0.014 (3) Å, respectively. The phenothia-zine unit adopts a butterfly conformation, with a dihedral angle of 38.06 (15)° between the terminal benzene rings. The dihedral angle between the 2,5-bis-(thio-phen-2-yl)oxadiazole unit and the attached benzene ring is 15.35 (11)°. In the crystal, mol-ecules form stacks along the b-axis direction; neighboring mol-ecules within the stack are related by inversion centers, with shortest inter-centroid separations of 3.741 (2) and 3.767 (2) Å.

Related literature

For electro-optical properties of phenothia­zine derivatives, see: Lai et al. (2001 ▶, 2003 ▶); Han et al. (2008 ▶); Meng et al. (2010 ▶); Zhang et al. (2005 ▶); Park et al. (2011 ▶); Kim et al. (2011 ▶); Hagfeldt et al. (2010 ▶); Wu et al. (2010 ▶). For related structures, see: Chu & Van der Helm (1975 ▶); Hdii et al. (1998 ▶); Li et al. (2009a ▶,b ▶); Yu et al. (2011 ▶); Pan et al. (2012 ▶).

Experimental

Crystal data

C24H16BrN3OS3

M = 538.49

Triclinic,

a = 7.4300 (5) Å

b = 7.6019 (5) Å

c = 22.1933 (14) Å

α = 89.315 (4)°

β = 89.170 (4)°

γ = 64.891 (4)°

V = 1134.93 (13) Å3

Z = 2

Mo Kα radiation

μ = 2.11 mm−1

T = 296 K

0.10 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.812, T max = 0.860

11444 measured reflections

3972 independent reflections

3138 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.06

3972 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004 ▶) and SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201361X/yk2050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201361X/yk2050Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201361X/yk2050Isup3.cml

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

C24H16BrN3OS3	Z = 2
Mr = 538.49	F(000) = 544
Triclinic, P1	Dx = 1.576 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4300 (5) Å	Cell parameters from 4410 reflections
b = 7.6019 (5) Å	θ = 2.8–25.6°
c = 22.1933 (14) Å	µ = 2.11 mm−1
α = 89.315 (4)°	T = 296 K
β = 89.170 (4)°	Block, yellow
γ = 64.891 (4)°	0.10 × 0.08 × 0.07 mm
V = 1134.93 (13) Å3

Bruker APEXII CCD area-detector diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
phi and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.812, Tmax = 0.860	k = −8→9
11444 measured reflections	l = −26→26

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0813P)2 + 0.0555P] where P = (Fo2 + 2Fc2)/3
3972 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	−0.64760 (7)	0.55973 (6)	0.18906 (2)	0.0835 (2)
C1	0.3622 (6)	0.2273 (5)	0.96143 (15)	0.0594 (9)
H1	0.2281	0.2762	0.9718	0.071*
C2	0.4887 (7)	0.2710 (5)	0.99607 (17)	0.0673 (10)
H2	0.4416	0.3463	1.0304	0.081*
C3	0.6867 (7)	0.2023 (5)	0.97957 (17)	0.0682 (11)
H3	0.7731	0.2313	1.0031	0.082*
C4	0.7577 (5)	0.0905 (5)	0.92832 (16)	0.0587 (9)
H4	0.8904	0.0489	0.9170	0.070*
C5	0.6325 (5)	0.0397 (4)	0.89353 (14)	0.0456 (7)
C6	0.4320 (5)	0.1113 (4)	0.91116 (13)	0.0465 (7)
C7	0.9127 (5)	−0.2003 (6)	0.83409 (18)	0.0666 (10)
H7A	0.9822	−0.1174	0.8320	0.080*
H7B	0.9341	−0.2683	0.7961	0.080*
C8	0.9994 (6)	−0.3473 (6)	0.8843 (2)	0.0839 (13)
H8A	0.9828	−0.2808	0.9219	0.126*
H8B	1.1383	−0.4238	0.8765	0.126*
H8C	0.9320	−0.4307	0.8863	0.126*
C9	0.5786 (5)	−0.0232 (4)	0.79035 (14)	0.0437 (7)
C10	0.6538 (5)	−0.0294 (5)	0.73245 (15)	0.0522 (8)
H10	0.7888	−0.0638	0.7269	0.063*
C11	0.5316 (5)	0.0147 (4)	0.68302 (15)	0.0501 (8)
H11	0.5870	0.0038	0.6446	0.060*
C12	0.3283 (5)	0.0748 (4)	0.68915 (13)	0.0450 (7)
C13	0.2503 (5)	0.0895 (4)	0.74764 (14)	0.0465 (7)
H13	0.1138	0.1335	0.7532	0.056*
C14	0.3721 (5)	0.0401 (4)	0.79706 (14)	0.0452 (7)
C15	0.1960 (5)	0.1204 (4)	0.63696 (14)	0.0468 (7)
C16	0.0059 (5)	0.1390 (4)	0.63392 (15)	0.0508 (8)
H16	−0.0620	0.1199	0.6671	0.061*
C17	−0.0786 (5)	0.1891 (4)	0.57703 (14)	0.0516 (8)
H17	−0.2075	0.2072	0.5685	0.062*
C18	0.0480 (5)	0.2087 (4)	0.53520 (15)	0.0488 (7)
C19	0.0111 (5)	0.2606 (4)	0.47247 (14)	0.0469 (7)
C20	−0.1542 (5)	0.3449 (4)	0.39177 (14)	0.0448 (7)
C21	−0.3225 (5)	0.3959 (4)	0.35297 (14)	0.0449 (7)
C22	−0.5041 (5)	0.4019 (4)	0.36531 (16)	0.0546 (8)
H22	−0.5420	0.3753	0.4032	0.065*
C23	−0.6299 (5)	0.4525 (4)	0.31502 (17)	0.0570 (8)
H23	−0.7589	0.4620	0.3157	0.068*
C24	−0.5401 (5)	0.4854 (4)	0.26594 (14)	0.0515 (8)
N1	0.6991 (4)	−0.0788 (4)	0.84232 (12)	0.0492 (6)
N2	0.1313 (4)	0.2746 (4)	0.43185 (12)	0.0563 (7)
N3	0.0218 (4)	0.3301 (4)	0.37835 (12)	0.0554 (7)
O1	−0.1732 (3)	0.3035 (3)	0.45107 (9)	0.0466 (5)
S1	0.27273 (13)	0.04182 (14)	0.86988 (4)	0.0583 (3)
S2	0.27462 (13)	0.16405 (12)	0.56662 (4)	0.0537 (2)
S3	−0.30112 (13)	0.45375 (12)	0.27857 (4)	0.0536 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.1064 (4)	0.0847 (3)	0.0675 (3)	−0.0479 (3)	−0.0321 (3)	0.0175 (2)
C1	0.070 (2)	0.0534 (17)	0.0436 (19)	−0.0159 (16)	0.0046 (17)	0.0046 (15)
C2	0.101 (3)	0.0543 (18)	0.046 (2)	−0.032 (2)	−0.005 (2)	−0.0026 (15)
C3	0.102 (3)	0.066 (2)	0.052 (2)	−0.051 (2)	−0.014 (2)	0.0023 (17)
C4	0.065 (2)	0.0672 (19)	0.056 (2)	−0.0394 (17)	−0.0077 (17)	0.0088 (17)
C5	0.0504 (18)	0.0507 (15)	0.0412 (17)	−0.0270 (14)	−0.0026 (14)	0.0072 (13)
C6	0.0567 (19)	0.0486 (15)	0.0362 (17)	−0.0243 (14)	−0.0032 (14)	0.0072 (13)
C7	0.047 (2)	0.078 (2)	0.068 (3)	−0.0199 (17)	0.0001 (18)	−0.0067 (19)
C8	0.071 (3)	0.077 (2)	0.083 (3)	−0.011 (2)	−0.022 (2)	0.000 (2)
C9	0.0466 (17)	0.0477 (15)	0.0412 (17)	−0.0242 (13)	0.0027 (14)	−0.0011 (13)
C10	0.0461 (18)	0.0637 (18)	0.050 (2)	−0.0267 (15)	0.0068 (15)	−0.0067 (15)
C11	0.054 (2)	0.0569 (17)	0.0405 (18)	−0.0245 (15)	0.0095 (15)	−0.0066 (14)
C12	0.0524 (19)	0.0425 (14)	0.0420 (18)	−0.0219 (13)	0.0056 (14)	−0.0029 (13)
C13	0.0435 (17)	0.0532 (16)	0.0441 (18)	−0.0219 (13)	0.0037 (14)	−0.0011 (13)
C14	0.0495 (18)	0.0504 (15)	0.0415 (17)	−0.0267 (14)	0.0020 (14)	−0.0004 (13)
C15	0.059 (2)	0.0415 (14)	0.0412 (17)	−0.0224 (14)	0.0048 (15)	−0.0023 (12)
C16	0.056 (2)	0.0576 (17)	0.0407 (18)	−0.0262 (15)	0.0045 (15)	0.0028 (14)
C17	0.0516 (19)	0.0571 (17)	0.0462 (19)	−0.0231 (15)	0.0030 (15)	−0.0027 (14)
C18	0.0534 (19)	0.0445 (14)	0.0458 (18)	−0.0184 (13)	0.0029 (15)	−0.0016 (13)
C19	0.0511 (19)	0.0452 (15)	0.0428 (18)	−0.0189 (13)	0.0016 (15)	−0.0026 (13)
C20	0.0490 (18)	0.0435 (14)	0.0403 (17)	−0.0183 (13)	0.0085 (14)	−0.0030 (12)
C21	0.0519 (18)	0.0408 (14)	0.0429 (17)	−0.0208 (13)	0.0075 (14)	−0.0007 (12)
C22	0.057 (2)	0.0539 (17)	0.052 (2)	−0.0230 (15)	0.0095 (17)	0.0028 (15)
C23	0.0512 (19)	0.0544 (17)	0.066 (2)	−0.0227 (15)	0.0007 (17)	0.0030 (16)
C24	0.063 (2)	0.0463 (15)	0.0466 (19)	−0.0247 (15)	−0.0021 (16)	0.0022 (14)
N1	0.0415 (14)	0.0610 (14)	0.0447 (16)	−0.0214 (12)	−0.0002 (12)	−0.0031 (12)
N2	0.0556 (17)	0.0717 (16)	0.0431 (16)	−0.0287 (14)	0.0030 (13)	0.0036 (13)
N3	0.0538 (17)	0.0719 (16)	0.0417 (16)	−0.0282 (13)	0.0047 (13)	0.0035 (13)
O1	0.0484 (13)	0.0497 (11)	0.0405 (12)	−0.0197 (9)	0.0060 (10)	0.0007 (9)
S1	0.0539 (5)	0.0906 (6)	0.0417 (5)	−0.0418 (4)	0.0041 (4)	0.0022 (4)
S2	0.0562 (5)	0.0677 (5)	0.0411 (5)	−0.0300 (4)	0.0038 (4)	0.0003 (4)
S3	0.0612 (5)	0.0636 (5)	0.0419 (5)	−0.0326 (4)	0.0042 (4)	0.0040 (4)

Br1—C24	1.871 (3)	C12—C13	1.400 (4)
C1—C2	1.370 (5)	C12—C15	1.471 (4)
C1—C6	1.382 (4)	C13—C14	1.376 (4)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.381 (6)	C14—S1	1.765 (3)
C2—H2	0.9300	C15—C16	1.361 (5)
C3—C4	1.385 (5)	C15—S2	1.736 (3)
C3—H3	0.9300	C16—C17	1.394 (5)
C4—C5	1.394 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.363 (4)
C5—C6	1.403 (4)	C17—H17	0.9300
C5—N1	1.406 (4)	C18—C19	1.441 (4)
C6—S1	1.758 (3)	C18—S2	1.726 (3)
C7—N1	1.469 (4)	C19—N2	1.295 (4)
C7—C8	1.511 (6)	C19—O1	1.358 (4)
C7—H7A	0.9700	C20—N3	1.295 (4)
C7—H7B	0.9700	C20—O1	1.369 (4)
C8—H8A	0.9600	C20—C21	1.438 (5)
C8—H8B	0.9600	C21—C22	1.355 (5)
C8—H8C	0.9600	C21—S3	1.726 (3)
C9—C10	1.387 (4)	C22—C23	1.407 (5)
C9—C14	1.406 (4)	C22—H22	0.9300
C9—N1	1.417 (4)	C23—C24	1.344 (5)
C10—C11	1.379 (5)	C23—H23	0.9300
C10—H10	0.9300	C24—S3	1.715 (4)
C11—C12	1.385 (4)	N2—N3	1.405 (4)
C11—H11	0.9300
C2—C1—C6	120.6 (4)	C12—C13—H13	119.4
C2—C1—H1	119.7	C13—C14—C9	120.9 (3)
C6—C1—H1	119.7	C13—C14—S1	120.3 (2)
C1—C2—C3	119.5 (3)	C9—C14—S1	118.7 (2)
C1—C2—H2	120.2	C16—C15—C12	129.4 (3)
C3—C2—H2	120.2	C16—C15—S2	110.0 (2)
C2—C3—C4	120.6 (4)	C12—C15—S2	120.6 (2)
C2—C3—H3	119.7	C15—C16—C17	114.4 (3)
C4—C3—H3	119.7	C15—C16—H16	122.8
C3—C4—C5	120.7 (3)	C17—C16—H16	122.8
C3—C4—H4	119.6	C18—C17—C16	112.8 (3)
C5—C4—H4	119.6	C18—C17—H17	123.6
C4—C5—C6	117.6 (3)	C16—C17—H17	123.6
C4—C5—N1	122.9 (3)	C17—C18—C19	128.1 (3)
C6—C5—N1	119.5 (3)	C17—C18—S2	111.1 (3)
C1—C6—C5	120.9 (3)	C19—C18—S2	120.8 (2)
C1—C6—S1	120.4 (3)	N2—C19—O1	113.1 (3)
C5—C6—S1	118.6 (2)	N2—C19—C18	128.8 (3)
N1—C7—C8	112.8 (3)	O1—C19—C18	118.0 (3)
N1—C7—H7A	109.0	N3—C20—O1	112.7 (3)
C8—C7—H7A	109.0	N3—C20—C21	128.5 (3)
N1—C7—H7B	109.0	O1—C20—C21	118.8 (3)
C8—C7—H7B	109.0	C22—C21—C20	129.4 (3)
H7A—C7—H7B	107.8	C22—C21—S3	111.6 (3)
C7—C8—H8A	109.5	C20—C21—S3	119.0 (2)
C7—C8—H8B	109.5	C21—C22—C23	113.3 (3)
H8A—C8—H8B	109.5	C21—C22—H22	123.4
C7—C8—H8C	109.5	C23—C22—H22	123.4
H8A—C8—H8C	109.5	C24—C23—C22	111.5 (3)
H8B—C8—H8C	109.5	C24—C23—H23	124.2
C10—C9—C14	117.6 (3)	C22—C23—H23	124.2
C10—C9—N1	123.4 (3)	C23—C24—S3	113.5 (3)
C14—C9—N1	119.0 (3)	C23—C24—Br1	127.3 (3)
C11—C10—C9	121.1 (3)	S3—C24—Br1	119.19 (18)
C11—C10—H10	119.4	C5—N1—C9	117.9 (2)
C9—C10—H10	119.4	C5—N1—C7	119.3 (3)
C10—C11—C12	121.6 (3)	C9—N1—C7	118.0 (3)
C10—C11—H11	119.2	C19—N2—N3	106.0 (3)
C12—C11—H11	119.2	C20—N3—N2	106.1 (3)
C11—C12—C13	117.6 (3)	C19—O1—C20	102.1 (2)
C11—C12—C15	122.4 (3)	C6—S1—C14	98.95 (15)
C13—C12—C15	120.1 (3)	C18—S2—C15	91.68 (16)
C14—C13—C12	121.1 (3)	C24—S3—C21	90.13 (16)
C14—C13—H13	119.4