5-[(Z)-2,3-Dimeth­oxy­benzyl­idene]-1,2,4-triazolo[3,2-b][1,3]thia­zol-6(5H)-one

Guo, L.; Lin, G.-T.; Wang, J.; Ni, L.; Ge, R.-S.

doi:10.1107/S1600536812042559

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3139

doi:10.1107/S1600536812042559

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5-[(Z)-2,3-Dimethoxybenzylidene]-1,2,4-triazolo[3,2-b][1,3]thiazol-6(5H)-one

Lu Guo,^a Gao-Tong Lin,^a Jia Wang,^a Li Ni ^a and Ren-Shan Ge ^a ^*

^aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
^*Correspondence e-mail: profgrs@163.com

(Received 2 September 2012; accepted 11 October 2012; online 20 October 2012)

The title compound, C₁₃H₁₁N₃O₃S, was synthesized from 1H-1,2,4-triazole-5-thiol in a one pot reaction. The fused thiazolo[3,2-b][1,2,4]triazole system is essentially coplanar with the benzene ring: they enclose an interplanar angle of 1.37 (13)°. The olefinic double bond is in a Z conformation. In the crystal, C—H⋯N hydrogen bonds link the molecules 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_r = 289.31
Monoclinic, C 2
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.135
S = 1.07
2096 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ), 724 Friedel pairs
Flack parameter: 0.00 (10)

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) $[x+{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ ; (ii) -x, y-1, -z; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042559/fy2070sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812042559/fy2070Isup3.cml

checkCIF report

Comment top

Darbufelone, a 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)thiazol-4-one derivative, is a new non-steroidal anti-inflammatory drug (NSAID), acting as a COX-2 and LOX-5 dual inhibitor (Martin et al., 1999). It is made and developed by the Warner-Lambert Company of the USA. The title compound, 5(Z)-(2,3-dimethoxybenzylidene)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one, is structurally related to Darbufelone and other compounds bearing fused thiazole and triazole rings, which have attracted our interest in a search for better anti-inflammatory agents.

The thiazole and 1,2,4-triazole moieties are present in various molecules having biological activity, especially in antiinflammatory agents (Karthikeyan, 2009; Tozkoparan et al., 2002, 2007). Compounds which contain fused thiazole and triazole rings, thiazolo-triazoles, also show significant biological and pharmacological properties: antiinflammatory, antitumoral, analgesic, antipyretic, antimicrobial (Tozkoparan et al., 2000; Lesyk et al., 2007; El-Sherif et al., 2006). Thus, in the present work, with the aim of further clarifying the molecular structure of this type of compounds, the single-crystal X-ray analysis of 5(Z)-(2,3-dimethoxybenzylidene)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one(I), has been carried out.

The title compound consists of a fused thiazolo[3,2-b]-l,2,4-triazole system and a phenyl group which bears 2,3-dimethoxy substituents (Fig. 1). The thiazolo[3,2-b][1,2,4]triazole system is essentially planar and the two rings nearly share a common plane with interplanar angle of 0.89 (18)°. The r.m.s. deviation of heavy atoms from the triazole and thiazolo ring mean planes are 0.0034 and 0.0020 Å, respectively. The benzene ring at the C5 position is in the cis (Z) configuration. The C4—C5 bond is a double bond [1.343 (4) Å]. The C3—C4 [1.489 (4), Å,] and C5—C6 [1.439 (4) Å] bonds are found to have normal single-bond lengths. A similar lengthening of the S1—C2 bond relative to the S1—C4 bond has been observed in the structure of a similar compound (Özbey et al., 1999; Köysal et al., 2004). The crystal of the title compound is stabilized by C—H···N intermolecular contacts. There are three intermolecular hydrogen-bond interactions: C9—H9···N2, C8—H8···N3 and C1—H1···N3 (Table 1).

Related literature top

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 top

4 ml of 90% formic acid contained in a round-bottomed flask was heated at 100°C for 15 minutes, and then 1.82 g (20 mmol) thiosemicarbazide was added. The heating was continued for 30 minutes, during which time crystalline 2-formylhydrazinecarbothioamide separated. The reaction mixture was cooled to 0 °C to give a white solid. Then a solution of 10 mmol 2-formylhydrazinecarbothioamide and 2 ml 20% NaOH was heated for 1 h. The reaction mixture was cooled, poured onto crushed ice, and neutralized with conc. HCl. The resulting solid 1H-1,2,4-triazole-5-thiol was filtered, dried, and recrystallized from ethanol.

To 1 mmol of 1H-1,2,4-triazole-5-thiol, 1.5 mmol of monochloroacetic acid, 0.01 mol of 2,3-dimethoxy benzaldehyde, 1 ml acetic anhydride, 0.01 mol of anhydrous sodium acetate, and 2 ml glacial acetic acid were added and refluxed for 3 h. The reaction mixture was cooled, and poured onto crushed ice. The mixture was then allowed to reach room temperature, then filtered and washed with water to obtain a crude product. The resulting solid was collected and crystallized from acetic acid. Single crystals were grown from acetic acid by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A crystal-packing diagram the title compound. Hydrogen bonds are shown as dashed lines.

5-[(Z)-2,3-Dimethoxybenzylidene]-1,2,4- triazolo[3,2-b][1,3]thiazol-6(5H)-one top

Crystal data top

C₁₃H₁₁N₃O₃S	F(000) = 600
M_r = 289.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.102P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.135	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.30 e Å⁻³
2096 reflections	Δρ_min = −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	Absolute structure parameter: 0.00 (10)

Crystal data top

C₁₃H₁₁N₃O₃S	V = 1283.8 (2) Å³
M_r = 289.31	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 11.5904 (13) Å	µ = 0.26 mm⁻¹
b = 7.0570 (8) Å	T = 293 K
c = 16.4519 (18) Å	0.32 × 0.22 × 0.20 mm
β = 107.445 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2096 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2022 reflections with I > 2σ(I)
T_min = 0.314, T_max = 1.000	R_int = 0.074
3567 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.135	Δρ_max = 0.30 e Å⁻³
S = 1.07	Δρ_min = −0.40 e Å⁻³
2096 reflections	Absolute structure: Flack (1983), 724 Friedel pairs
184 parameters	Absolute structure parameter: 0.00 (10)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y−3/2, z; (ii) −x, y−1, −z; (iii) −x−1/2, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₃S
M_r	289.31
Crystal system, space group	Monoclinic, C2
Temperature (K)	293
a, b, c (Å)	11.5904 (13), 7.0570 (8), 16.4519 (18)
β (°)	107.445 (2)
V (Å³)	1283.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.32 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.314, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3567, 2096, 2022
R_int	0.074

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.135, 1.07
No. of reflections	2096
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.40
Absolute structure	Flack (1983), 724 Friedel pairs
Absolute structure parameter	0.00 (10)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2ⁱ	0.93	2.46	3.375 (4)	166.6
C8—H8···N3ⁱⁱ	0.93	2.60	3.529 (4)	173.3
C1—H1···N3ⁱⁱⁱ	0.93	2.65	3.556 (4)	164.0

Symmetry codes: (i) x+1/2, y−3/2, z; (ii) −x, y−1, −z; (iii) −x−1/2, y+1/2, −z.

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grant Nos. LY12H16003 and Y4110197) and the Project of Wenzhou Sci & Tech Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences is gratefully acknowledged for the data collection.

References

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Volume 68| Part 11| November 2012| Page o3139

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-[(Z)-2,3-Dimeth­­oxy­benzyl­­idene]-1,2,4-triazolo[3,2-b][1,3]thia­zol-6(5H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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5-[(Z)-2,3-Dimethoxybenzylidene]-1,2,4-triazolo[3,2-b][1,3]thiazol-6(5H)-one