5-[(Z)-2,3-Dimeth-oxy-benzyl-idene]-1,2,4-triazolo[3,2-b][1,3]thia-zol-6(5H)-one.

The title compound, C(13)H(11)N(3)O(3)S, was synthesized from 1H-1,2,4-triazole-5-thiol in a one pot reaction. The fused thia-zolo[3,2-b][1,2,4]triazole system is essentially coplanar with the benzene ring: they enclose an inter-planar angle of 1.37 (13)°. The olefinic double bond is in a Z conformation. In the crystal, C-H⋯N hydrogen bonds link the mol-ecules into double layers parallel to the ab plane.

Related literature

For related structures, see: Özbey et al. (1999 ▶); Köysal et al. (2004 ▶). For background to the biological properties of fused thia­zolo[3,2-b][1,2,4]triazol derivatives, see: El-Sherif et al. (2006 ▶); Gilbertsen et al. (1999 ▶); Karthikeyan (2009 ▶); Lesyk et al. (2007 ▶); Martin et al. (1999 ▶); Tozkoparan et al. (2000 ▶, 2002 ▶, 2007 ▶).

Experimental

Crystal data

C13H11N3O3S

M = 289.31

Monoclinic,

a = 11.5904 (13) Å

b = 7.0570 (8) Å

c = 16.4519 (18) Å

β = 107.445 (2)°

V = 1283.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.32 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.314, T max = 1.000

3567 measured reflections

2096 independent reflections

2022 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.135

S = 1.07

2096 reflections

184 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 724 Friedel pairs

Flack parameter: 0.00 (10)

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042559/fy2070sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042559/fy2070Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042559/fy2070Isup3.cml

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

C13H11N3O3S	F(000) = 600
Mr = 289.31	Dx = 1.497 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 11.5904 (13) Å	Cell parameters from 2670 reflections
b = 7.0570 (8) Å	θ = 5.2–55.1°
c = 16.4519 (18) Å	µ = 0.26 mm−1
β = 107.445 (2)°	T = 293 K
V = 1283.8 (2) Å3	Prismatic, green
Z = 4	0.32 × 0.22 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→14
Tmin = 0.314, Tmax = 1.000	k = −6→8
3567 measured reflections	l = −20→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.30 e Å−3
2096 reflections	Δρmin = −0.40 e Å−3
184 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.004
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 724 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (10)

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	−0.01455 (7)	1.05191 (12)	0.10793 (4)	0.0509 (3)
N1	−0.0780 (2)	1.3372 (4)	0.18332 (14)	0.0416 (5)
N2	−0.1377 (2)	1.5049 (4)	0.17612 (17)	0.0508 (7)
N3	−0.1513 (3)	1.3773 (5)	0.04552 (16)	0.0590 (8)
O1	0.00045 (19)	1.2734 (4)	0.32636 (12)	0.0554 (6)
O2	0.21278 (18)	0.7058 (4)	0.40934 (11)	0.0527 (6)
O3	0.3203 (2)	0.3716 (4)	0.39185 (15)	0.0661 (7)
C1	−0.1790 (3)	1.5220 (5)	0.0926 (2)	0.0568 (9)
H1	−0.2245	1.6262	0.0669	0.068*
C2	−0.0877 (3)	1.2682 (5)	0.10527 (16)	0.0464 (7)
C3	−0.0130 (2)	1.2290 (4)	0.25439 (15)	0.0389 (6)
C4	0.0302 (2)	1.0558 (5)	0.22076 (14)	0.0380 (6)
C5	0.0954 (2)	0.9259 (4)	0.27501 (16)	0.0395 (6)
H5	0.1093	0.9551	0.3323	0.047*
C6	0.1475 (2)	0.7493 (5)	0.25979 (16)	0.0390 (6)
C7	0.1392 (3)	0.6801 (5)	0.17817 (17)	0.0441 (7)
H7	0.0975	0.7497	0.1304	0.053*
C8	0.1919 (3)	0.5107 (5)	0.16797 (18)	0.0468 (7)
H8	0.1847	0.4659	0.1135	0.056*
C9	0.2555 (3)	0.4070 (5)	0.23833 (19)	0.0464 (7)
H9	0.2930	0.2946	0.2308	0.056*
C10	0.2643 (2)	0.4684 (5)	0.32006 (18)	0.0455 (7)
C11	0.2112 (2)	0.6410 (5)	0.33035 (17)	0.0416 (6)
C12	0.3298 (3)	0.7237 (7)	0.47229 (19)	0.0620 (10)
H12A	0.3520	0.6048	0.5011	0.093*
H12B	0.3262	0.8195	0.5129	0.093*
H12C	0.3889	0.7585	0.4447	0.093*
C13	0.3783 (4)	0.1988 (7)	0.3845 (3)	0.0700 (10)
H13A	0.3209	0.1138	0.3482	0.105*
H13B	0.4105	0.1427	0.4399	0.105*
H13C	0.4429	0.2225	0.3606	0.105*

	U11	U22	U33	U12	U13	U23
S1	0.0663 (5)	0.0506 (5)	0.0329 (3)	0.0151 (4)	0.0104 (3)	−0.0014 (3)
N1	0.0420 (11)	0.0388 (14)	0.0433 (11)	0.0040 (10)	0.0117 (9)	−0.0009 (10)
N2	0.0488 (13)	0.0465 (18)	0.0533 (13)	0.0060 (12)	0.0095 (10)	0.0010 (12)
N3	0.0694 (16)	0.0561 (19)	0.0425 (13)	0.0161 (16)	0.0031 (12)	0.0062 (13)
O1	0.0653 (13)	0.0592 (16)	0.0403 (10)	0.0085 (12)	0.0136 (9)	−0.0072 (11)
O2	0.0555 (11)	0.0690 (17)	0.0331 (9)	0.0154 (11)	0.0126 (8)	0.0032 (10)
O3	0.0809 (15)	0.0590 (18)	0.0581 (13)	0.0246 (13)	0.0205 (11)	0.0176 (12)
C1	0.0598 (16)	0.047 (2)	0.0556 (16)	0.0153 (16)	0.0057 (14)	0.0117 (16)
C2	0.0492 (14)	0.0461 (17)	0.0409 (13)	0.0050 (14)	0.0090 (11)	−0.0015 (13)
C3	0.0373 (12)	0.0418 (17)	0.0376 (12)	−0.0009 (12)	0.0113 (10)	−0.0036 (12)
C4	0.0377 (11)	0.0444 (16)	0.0315 (10)	0.0002 (13)	0.0096 (9)	−0.0006 (13)
C5	0.0381 (11)	0.0444 (17)	0.0367 (12)	0.0002 (12)	0.0125 (10)	0.0006 (12)
C6	0.0366 (11)	0.0429 (16)	0.0376 (12)	−0.0013 (12)	0.0112 (10)	0.0020 (12)
C7	0.0462 (14)	0.0458 (17)	0.0387 (12)	0.0012 (13)	0.0102 (11)	0.0008 (13)
C8	0.0521 (14)	0.047 (2)	0.0433 (13)	−0.0039 (14)	0.0167 (11)	−0.0081 (13)
C9	0.0473 (14)	0.0385 (16)	0.0573 (16)	0.0006 (13)	0.0217 (12)	−0.0038 (14)
C10	0.0426 (13)	0.0462 (17)	0.0478 (15)	0.0039 (13)	0.0136 (12)	0.0076 (12)
C11	0.0395 (12)	0.0473 (17)	0.0395 (13)	0.0016 (13)	0.0139 (10)	0.0017 (12)
C12	0.0649 (19)	0.073 (3)	0.0406 (15)	0.0098 (19)	0.0047 (14)	−0.0010 (15)
C13	0.066 (2)	0.058 (2)	0.079 (2)	0.0158 (19)	0.0098 (18)	0.014 (2)

S1—C2	1.740 (3)	C5—H5	0.9300
S1—C4	1.772 (2)	C6—C11	1.401 (4)
N1—C2	1.346 (4)	C6—C7	1.405 (4)
N1—N2	1.358 (4)	C7—C8	1.375 (5)
N1—C3	1.411 (4)	C7—H7	0.9300
N2—C1	1.317 (4)	C8—C9	1.381 (4)
N3—C2	1.291 (4)	C8—H8	0.9300
N3—C1	1.377 (5)	C9—C10	1.387 (4)
O1—C3	1.189 (3)	C9—H9	0.9300
O2—C11	1.373 (3)	C10—C11	1.397 (5)
O2—C12	1.444 (4)	C12—H12A	0.9600
O3—C10	1.350 (4)	C12—H12B	0.9600
O3—C13	1.415 (5)	C12—H12C	0.9600
C1—H1	0.9300	C13—H13A	0.9600
C3—C4	1.489 (4)	C13—H13B	0.9600
C4—C5	1.343 (4)	C13—H13C	0.9600
C5—C6	1.439 (4)
C2—S1—C4	90.02 (15)	C8—C7—H7	119.6
C2—N1—N2	109.7 (2)	C6—C7—H7	119.6
C2—N1—C3	117.8 (3)	C7—C8—C9	120.2 (3)
N2—N1—C3	132.5 (2)	C7—C8—H8	119.9
C1—N2—N1	100.8 (3)	C9—C8—H8	119.9
C2—N3—C1	100.9 (3)	C8—C9—C10	120.8 (3)
C11—O2—C12	116.8 (2)	C8—C9—H9	119.6
C10—O3—C13	118.6 (3)	C10—C9—H9	119.6
N2—C1—N3	116.5 (3)	O3—C10—C9	124.5 (3)
N2—C1—H1	121.8	O3—C10—C11	116.7 (3)
N3—C1—H1	121.8	C9—C10—C11	118.9 (3)
N3—C2—N1	112.1 (3)	O2—C11—C10	121.6 (3)
N3—C2—S1	134.8 (2)	O2—C11—C6	117.2 (3)
N1—C2—S1	113.1 (2)	C10—C11—C6	121.1 (3)
O1—C3—N1	124.1 (3)	O2—C12—H12A	109.5
O1—C3—C4	128.9 (3)	O2—C12—H12B	109.5
N1—C3—C4	107.0 (2)	H12A—C12—H12B	109.5
C5—C4—C3	119.9 (2)	O2—C12—H12C	109.5
C5—C4—S1	128.0 (2)	H12A—C12—H12C	109.5
C3—C4—S1	112.1 (2)	H12B—C12—H12C	109.5
C4—C5—C6	131.1 (2)	O3—C13—H13A	109.5
C4—C5—H5	114.5	O3—C13—H13B	109.5
C6—C5—H5	114.5	H13A—C13—H13B	109.5
C11—C6—C7	118.0 (3)	O3—C13—H13C	109.5
C11—C6—C5	118.2 (2)	H13A—C13—H13C	109.5
C7—C6—C5	123.7 (3)	H13B—C13—H13C	109.5
C8—C7—C6	120.9 (3)
C2—N1—N2—C1	0.1 (3)	C3—C4—C5—C6	−179.9 (3)
C3—N1—N2—C1	−179.0 (3)	S1—C4—C5—C6	−0.1 (5)
N1—N2—C1—N3	0.5 (4)	C4—C5—C6—C11	−179.5 (3)
C2—N3—C1—N2	−0.9 (4)	C4—C5—C6—C7	1.2 (5)
C1—N3—C2—N1	0.9 (4)	C11—C6—C7—C8	0.1 (4)
C1—N3—C2—S1	179.5 (3)	C5—C6—C7—C8	179.4 (3)
N2—N1—C2—N3	−0.7 (4)	C6—C7—C8—C9	−0.9 (4)
C3—N1—C2—N3	178.5 (3)	C7—C8—C9—C10	1.9 (4)
N2—N1—C2—S1	−179.61 (19)	C13—O3—C10—C9	2.4 (5)
C3—N1—C2—S1	−0.4 (3)	C13—O3—C10—C11	−178.2 (3)
C4—S1—C2—N3	−178.2 (4)	C8—C9—C10—O3	177.1 (3)
C4—S1—C2—N1	0.4 (2)	C8—C9—C10—C11	−2.2 (4)
C2—N1—C3—O1	−178.9 (3)	C12—O2—C11—C10	55.9 (4)
N2—N1—C3—O1	0.1 (5)	C12—O2—C11—C6	−128.0 (3)
C2—N1—C3—C4	0.2 (3)	O3—C10—C11—O2	−1.9 (4)
N2—N1—C3—C4	179.1 (3)	C9—C10—C11—O2	177.5 (3)
O1—C3—C4—C5	−1.0 (5)	O3—C10—C11—C6	−177.9 (3)
N1—C3—C4—C5	180.0 (2)	C9—C10—C11—C6	1.5 (4)
O1—C3—C4—S1	179.2 (3)	C7—C6—C11—O2	−176.6 (3)
N1—C3—C4—S1	0.2 (3)	C5—C6—C11—O2	4.1 (4)
C2—S1—C4—C5	179.9 (3)	C7—C6—C11—C10	−0.5 (4)
C2—S1—C4—C3	−0.3 (2)	C5—C6—C11—C10	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2i	0.93	2.46	3.375 (4)	167
C8—H8···N3ii	0.93	2.60	3.529 (4)	173
C1—H1···N3iii	0.93	2.65	3.556 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N2i	0.93	2.46	3.375 (4)	167
C8—H8⋯N3ii	0.93	2.60	3.529 (4)	173
C1—H1⋯N3iii	0.93	2.65	3.556 (4)	164

Symmetry codes: (i) ; (ii) ; (iii) .