Crystal structure of 3-benzyl-sulfanyl-6-(5-methyl-1,2-oxazol-3-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the title compound, C14H11N5OS2, the triazolo-thia-diazole system is essentially planar (r.m.s. deviation = 0.002 Å) and makes dihedral angles of 6.33 (12) and 42.95 (14)° with the planes of the oxazole and phenyl rings, respectively. In the crystal, face-to-face π-π inter-actions are observed between the thia-diazole and oxazole rings [centroid-centroid distance = 3.4707 (18) Å], leading to columns along [010].

Related literature

For the pharmocological properties of isoxazole, see: Kuz’min et al. (2007 ▸); Yermolina et al. (2011 ▸); Lilienkampf et al. (2010 ▸); Kamal et al. (2011 ▸). For the bioactivity of 1,2,4-triazoles coupled with the thia­diazole heterocylic ring system, see: Singh & Singh (2009 ▸). For biological applications, such as anti­microbial, anti­cancer, anti­viral and anti­helmentic properties, see: Habib et al. (1997 ▸); Bhat et al. (2004 ▸); Farghaly et al. (2006 ▸); Khalil et al. (1999 ▸). For the synthesis, see: Vaarla & Rao (2014 ▸). For a similar structure, see: Dinçer et al. (2005 ▸).

Experimental

Crystal data

C14H11N5OS2

M = 329.40

Orthorhombic,

a = 16.271 (5) Å

b = 5.3804 (13) Å

c = 16.700 (4) Å

V = 1462.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.50 × 0.45 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▸) T min = 0.836, T max = 0.896

10433 measured reflections

3117 independent reflections

2905 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.08

3117 reflections

200 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▸)

Absolute structure parameter: 0.02 (2)

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015017351/tk5386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017351/tk5386Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017351/tk5386Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017351/tk5386fig1.tif

The title mol­ecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015017351/tk5386fig2.tif

View of the mol­ecular packing of the title compound down the b axis. All H atoms have been omitted for clarity.

CCDC reference: 1425251

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H11N5OS2	F(000) = 680
Mr = 329.40	Dx = 1.497 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5610 reflections
a = 16.271 (5) Å	θ = 5.0–55.6°
b = 5.3804 (13) Å	µ = 0.37 mm−1
c = 16.700 (4) Å	T = 296 K
V = 1462.0 (7) Å3	Block, colourless
Z = 4	0.50 × 0.45 × 0.30 mm

Bruker Kappa APEXII CCD diffractometer	3117 independent reflections
Radiation source: fine-focus sealed tube	2905 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −20→21
Tmin = 0.836, Tmax = 0.896	k = −6→7
10433 measured reflections	l = −16→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.1925P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.18 e Å−3
3117 reflections	Δρmin = −0.20 e Å−3
200 parameters	Absolute structure: Flack (1983)
1 restraint	Absolute structure parameter: 0.02 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.58876 (4)	0.55792 (12)	0.27749 (5)	0.0430 (2)
S2	0.56435 (4)	0.13539 (13)	0.56223 (5)	0.0480 (2)
O1	0.41434 (13)	1.1668 (4)	0.26095 (13)	0.0513 (7)
N1	0.47539 (15)	0.9833 (5)	0.26294 (16)	0.0500 (9)
N2	0.51832 (12)	0.5539 (4)	0.41898 (14)	0.0359 (6)
N3	0.57592 (12)	0.3670 (4)	0.41555 (14)	0.0348 (6)
N4	0.66919 (15)	0.1462 (4)	0.35159 (18)	0.0478 (8)
N5	0.65754 (15)	0.0517 (4)	0.42870 (17)	0.0464 (8)
C1	0.30250 (19)	1.3389 (5)	0.3361 (2)	0.0539 (10)
C2	0.37083 (16)	1.1579 (4)	0.32957 (17)	0.0396 (8)
C3	0.40056 (18)	0.9771 (5)	0.37679 (18)	0.0415 (8)
C4	0.46538 (15)	0.8755 (4)	0.33223 (17)	0.0350 (7)
C5	0.52042 (14)	0.6671 (4)	0.35064 (17)	0.0342 (7)
C6	0.61891 (16)	0.3354 (4)	0.34707 (18)	0.0381 (7)
C7	0.60185 (15)	0.1833 (5)	0.46600 (18)	0.0388 (8)
C8	0.61793 (19)	0.3882 (5)	0.6143 (2)	0.0488 (9)
C9	0.70934 (17)	0.3711 (4)	0.60716 (16)	0.0391 (8)
C10	0.7528 (2)	0.5388 (5)	0.5610 (2)	0.0523 (9)
C11	0.8368 (2)	0.5174 (7)	0.5528 (3)	0.0639 (11)
C12	0.8789 (2)	0.3276 (7)	0.5891 (2)	0.0603 (11)
C13	0.8372 (2)	0.1623 (6)	0.6353 (3)	0.0628 (11)
C14	0.7532 (2)	0.1828 (6)	0.6448 (2)	0.0556 (11)
H1A	0.32400	1.49870	0.35070	0.0810*
H1B	0.26440	1.28400	0.37630	0.0810*
H1C	0.27480	1.35110	0.28550	0.0810*
H3	0.38240	0.93020	0.42740	0.0500*
H8A	0.59980	0.54590	0.59240	0.0590*
H8B	0.60300	0.38470	0.67050	0.0590*
H10	0.72510	0.66720	0.53530	0.0630*
H11	0.86540	0.63330	0.52220	0.0770*
H12	0.93530	0.31210	0.58220	0.0730*
H13	0.86540	0.03440	0.66070	0.0750*
H14	0.72560	0.06900	0.67690	0.0670*

	U11	U22	U33	U12	U13	U23
S1	0.0443 (3)	0.0412 (3)	0.0434 (4)	0.0021 (3)	0.0010 (3)	−0.0021 (3)
S2	0.0399 (3)	0.0460 (3)	0.0582 (4)	−0.0038 (3)	0.0005 (4)	0.0125 (3)
O1	0.0461 (11)	0.0513 (11)	0.0566 (15)	0.0077 (8)	−0.0012 (9)	0.0149 (10)
N1	0.0457 (13)	0.0496 (13)	0.0546 (18)	0.0096 (10)	0.0017 (11)	0.0107 (12)
N2	0.0286 (10)	0.0314 (10)	0.0476 (13)	0.0009 (7)	−0.0017 (9)	−0.0029 (9)
N3	0.0276 (9)	0.0299 (10)	0.0470 (13)	0.0001 (7)	−0.0024 (9)	−0.0055 (9)
N4	0.0436 (13)	0.0434 (12)	0.0564 (15)	0.0092 (10)	−0.0002 (12)	−0.0080 (11)
N5	0.0415 (12)	0.0367 (12)	0.0611 (16)	0.0062 (9)	−0.0050 (12)	−0.0029 (11)
C1	0.0434 (15)	0.0392 (14)	0.079 (2)	0.0064 (11)	−0.0022 (16)	0.0071 (15)
C2	0.0334 (12)	0.0312 (12)	0.0543 (17)	−0.0041 (9)	−0.0055 (11)	−0.0018 (12)
C3	0.0426 (14)	0.0345 (12)	0.0474 (17)	0.0023 (10)	−0.0002 (12)	0.0018 (12)
C4	0.0322 (11)	0.0280 (10)	0.0449 (15)	−0.0040 (8)	−0.0077 (10)	−0.0004 (10)
C5	0.0303 (11)	0.0272 (11)	0.0450 (15)	−0.0033 (8)	−0.0048 (11)	−0.0058 (10)
C6	0.0332 (12)	0.0334 (11)	0.0478 (15)	−0.0024 (9)	−0.0036 (12)	−0.0068 (11)
C7	0.0312 (12)	0.0342 (12)	0.0509 (16)	−0.0024 (9)	−0.0054 (11)	−0.0011 (11)
C8	0.0520 (17)	0.0423 (14)	0.0522 (18)	0.0040 (12)	0.0088 (14)	−0.0035 (13)
C9	0.0451 (14)	0.0368 (12)	0.0354 (14)	−0.0027 (10)	0.0008 (11)	−0.0051 (11)
C10	0.0605 (17)	0.0420 (14)	0.0544 (17)	−0.0026 (12)	−0.0032 (17)	0.0069 (14)
C11	0.059 (2)	0.0688 (19)	0.064 (2)	−0.0199 (16)	0.0027 (18)	0.0050 (18)
C12	0.0470 (17)	0.072 (2)	0.062 (2)	−0.0033 (15)	−0.0081 (15)	−0.0165 (18)
C13	0.057 (2)	0.0575 (19)	0.074 (2)	0.0046 (15)	−0.0232 (18)	0.0005 (17)
C14	0.0602 (19)	0.0467 (16)	0.060 (2)	−0.0040 (13)	−0.0082 (15)	0.0126 (15)

S1—C5	1.753 (3)	C8—C9	1.495 (4)
S1—C6	1.739 (3)	C9—C10	1.382 (4)
S2—C7	1.738 (3)	C9—C14	1.390 (4)
S2—C8	1.835 (3)	C10—C11	1.378 (5)
O1—N1	1.401 (3)	C11—C12	1.371 (5)
O1—C2	1.348 (4)	C12—C13	1.359 (5)
N1—C4	1.305 (4)	C13—C14	1.380 (5)
N2—N3	1.376 (3)	C1—H1A	0.9600
N2—C5	1.294 (4)	C1—H1B	0.9600
N3—C6	1.351 (4)	C1—H1C	0.9600
N3—C7	1.366 (4)	C3—H3	0.9300
N4—N5	1.397 (4)	C8—H8A	0.9700
N4—C6	1.308 (3)	C8—H8B	0.9700
N5—C7	1.308 (4)	C10—H10	0.9300
C1—C2	1.482 (4)	C11—H11	0.9300
C2—C3	1.342 (4)	C12—H12	0.9300
C3—C4	1.402 (4)	C13—H13	0.9300
C4—C5	1.468 (3)	C14—H14	0.9300
C5—S1—C6	86.79 (13)	C10—C9—C14	117.8 (3)
C7—S2—C8	99.29 (14)	C9—C10—C11	120.6 (3)
N1—O1—C2	109.1 (2)	C10—C11—C12	120.9 (3)
O1—N1—C4	104.2 (2)	C11—C12—C13	119.3 (3)
N3—N2—C5	106.8 (2)	C12—C13—C14	120.5 (3)
N2—N3—C6	118.7 (2)	C9—C14—C13	121.0 (3)
N2—N3—C7	135.6 (2)	C2—C1—H1A	110.00
C6—N3—C7	105.7 (2)	C2—C1—H1B	109.00
N5—N4—C6	104.6 (2)	C2—C1—H1C	109.00
N4—N5—C7	109.6 (2)	H1A—C1—H1B	109.00
O1—C2—C1	115.7 (2)	H1A—C1—H1C	109.00
O1—C2—C3	109.6 (2)	H1B—C1—H1C	109.00
C1—C2—C3	134.7 (3)	C2—C3—H3	128.00
C2—C3—C4	104.0 (3)	C4—C3—H3	128.00
N1—C4—C3	113.0 (2)	S2—C8—H8A	109.00
N1—C4—C5	116.7 (2)	S2—C8—H8B	109.00
C3—C4—C5	130.2 (3)	C9—C8—H8A	109.00
S1—C5—N2	118.27 (17)	C9—C8—H8B	109.00
S1—C5—C4	119.8 (2)	H8A—C8—H8B	108.00
N2—C5—C4	121.9 (2)	C9—C10—H10	120.00
S1—C6—N3	109.44 (17)	C11—C10—H10	120.00
S1—C6—N4	138.7 (2)	C10—C11—H11	120.00
N3—C6—N4	111.9 (3)	C12—C11—H11	119.00
S2—C7—N3	124.7 (2)	C11—C12—H12	120.00
S2—C7—N5	127.1 (2)	C13—C12—H12	120.00
N3—C7—N5	108.2 (3)	C12—C13—H13	120.00
S2—C8—C9	112.91 (19)	C14—C13—H13	120.00
C8—C9—C10	120.9 (2)	C9—C14—H14	120.00
C8—C9—C14	121.3 (2)	C13—C14—H14	119.00
C5—S1—C6—N4	178.0 (3)	N5—N4—C6—N3	−0.3 (3)
C6—S1—C5—N2	−0.6 (2)	N5—N4—C6—S1	−178.5 (2)
C6—S1—C5—C4	−178.2 (2)	C6—N4—N5—C7	0.5 (3)
C5—S1—C6—N3	−0.21 (18)	N4—N5—C7—N3	−0.4 (3)
C8—S2—C7—N5	104.8 (3)	N4—N5—C7—S2	178.5 (2)
C8—S2—C7—N3	−76.5 (2)	C1—C2—C3—C4	178.8 (3)
C7—S2—C8—C9	−58.4 (2)	O1—C2—C3—C4	−0.1 (3)
N1—O1—C2—C1	−179.0 (2)	C2—C3—C4—C5	−178.1 (3)
C2—O1—N1—C4	−0.2 (3)	C2—C3—C4—N1	−0.1 (3)
N1—O1—C2—C3	0.1 (3)	C3—C4—C5—N2	−5.1 (4)
O1—N1—C4—C3	0.1 (3)	N1—C4—C5—S1	−5.5 (3)
O1—N1—C4—C5	178.5 (2)	N1—C4—C5—N2	176.9 (2)
C5—N2—N3—C6	−1.3 (3)	C3—C4—C5—S1	172.5 (2)
N3—N2—C5—C4	178.7 (2)	S2—C8—C9—C10	109.4 (3)
N3—N2—C5—S1	1.1 (3)	S2—C8—C9—C14	−68.8 (3)
C5—N2—N3—C7	−178.4 (3)	C8—C9—C10—C11	−178.1 (3)
N2—N3—C7—S2	−1.4 (4)	C14—C9—C10—C11	0.2 (5)
N2—N3—C6—N4	−177.8 (2)	C8—C9—C14—C13	177.4 (3)
C6—N3—C7—N5	0.2 (3)	C10—C9—C14—C13	−1.0 (5)
C7—N3—C6—N4	0.1 (3)	C9—C10—C11—C12	1.0 (6)
C7—N3—C6—S1	178.79 (17)	C10—C11—C12—C13	−1.6 (6)
N2—N3—C6—S1	0.9 (3)	C11—C12—C13—C14	0.9 (6)
N2—N3—C7—N5	177.6 (3)	C12—C13—C14—C9	0.4 (6)
C6—N3—C7—S2	−178.7 (2)