3-Methyl-4-{(E)-[4-(methyl­sulfan­yl)benzyl­idene]amino}-1H-1,2,4-triazole-5(4H)-thione

Sarojini, B.K.; Manjula, P.S.; Hegde, G.; Kour, D.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536813009690

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages o718-o719

https://doi.org/10.1107/S1600536813009690

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3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione

B. K. Sarojini,^a P. S. Manjula,^a Gurumurthy Hegde,^b Dalbir Kour,^c Vivek K. Gupta ^c and Rajni Kant ^c ^*

^aDepartment of Chemistry, PA College of Engineering, Nadupadavu 574 153, D.K. Mangalore, India, ^bFaculty of Industrial Science and Technology, University Malaysia Pahang, LebuhrayaTunRazak, 2630 0Gambang, Kuantan, Pahang Darul Makmur, Malaysia, and ^cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 3 April 2013; accepted 9 April 2013; online 13 April 2013)

In the title molecule, C₁₁H₁₂N₄S₂, the dihedral angle between the triazole and benzene rings is 21.31 (5)°. A weak intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the crystal, pairs of N—H⋯S hydrogen bonds form inversion dimers. In addition, π–π interactions are observed between the benzene rings, with a centroid–centroid separation of 3.7599 (11) Å.

Related literature

For background to Schiff base compounds, see: Dubey & Vaid (1991 ); Yadav et al. (1994 ); Galic et al. (2001 ). For biological applications of sulfur- and nitrogen-containing compounds, see: Wei et al. (1981 , 1982 ); Thieme et al. (1973a ,b ); Dornow et al. (1964 ); Barrera et al. (1985 ); Malik et al., (2011 ). For related structures, see: Devarajegowda et al. (2012 ); Fun et al. (2008 ); Wang et al. (2008 ). For standard bond-length data, see: Allen et al. (1987 ). For hydrogen-bond graph-set motifs, see: Bernstein et al.(1995 ).

Experimental

Crystal data

C₁₁H₁₂N₄S₂
M_r = 264.37
Triclinic, $[P \overline 1]$
a = 7.7873 (2) Å
b = 9.5982 (2) Å
c = 9.6041 (2) Å
α = 76.608 (2)°
β = 70.602 (2)°
γ = 68.570 (2)°
V = 625.30 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.866, T_max = 1.000
30316 measured reflections
2449 independent reflections
2121 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.03
2449 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯S1	0.93	2.57	3.212 (2)	126
N2—H2⋯S1ⁱ	0.86	2.48	3.328 (2)	169
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009690/lh5604sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009690/lh5604Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009690/lh5604Isup3.cml

checkCIF report

Comment top

During the last few decades, there has been a considerable interest in the chemistry of Schiff base compounds (Dubey & Vaid, 1991; Yadav et al.,1994). Schiff bases, containing different donor atoms, also find use in analytical applications and metal coordination (Galic et al., 2001). Since many compounds containing sulfur and nitrogen atoms are antihypertensive (Wei et al., 1981, 1982), analgesic (Thieme et al., 1973a,b), anti-inflammatory (Dornow et al., 1964), sedative (Barrera et al., 1985), or fungicidal (Malik et al., 2011), synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity.

In the title compound (Fig. 1), the bond lengths and angles have values in the normal ranges (Allen et al., 1987) and are comparable with closely related structures (Devarajegowda et al., 2012; Fun et al., 2008; Wang et al., 2008). The dihedral angle between the triazole ring (N1/N2/C3/N4/C5) and the benzene ring (C9—C14) is 21.31 (5)°. The molecule exists in the thione tautomeric form, with an S═C distance of 1.681 (3) Å, which indicates substantial double-bond character for this bond [1.671 (24) Å](Allen et al., 1987). The methylidene amino linkage (N7/C8) is slightly twisted from the mean plane of the 1,2,4 triazole ring as indicated by the torsion angle C3–N4–N7–C8 of -30.8 (2)°. A weak intramolecular C—H···S hydrogen bond generates an S(6) ring motif (Bernstein et al.,1995). The packing of molecules within the unit cell is shown in Fig. 2. In the crystal, pairs of N—H···S hydrogen bonds form inversion dimers. In addition, π–π interactions are observed between the benzene rings with Cg···Cg(-x,-y,1-z) = 3.7599 (11) Å, where Cg is the centroid of the C9—C14 ring.

Related literature top

For background to Schiff base compounds, see: Dubey & Vaid (1991); Yadav et al. (1994); Galic et al. (2001). For biological applications of sulfur- and nitrogen-containing compounds, see: Wei et al. (1981, 1982); Thieme et al. (1973a,b); Dornow et al. (1964); Barrera et al. (1985); Malik et al., (2011). For related structures, see: Devarajegowda et al. (2012); Fun et al. (2008); Wang et al. (2008). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond graph-set motifs, see: Bernstein et al.(1995).

Experimental top

To a suspension of 4-(methylthio)benzaldehyde (1.52 g, 0.01 mol) in methanol (15 ml), 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.01 mol, 1.65 g) was added and heated to form a clear solution. To this a few drops of conc.H₂SO₄ was added as a catalyst and refluxed for 5 h on a water bath. The precipitate formed was filtered and recrystallized from mixture of methanol and dioxane (2:1) to yield the titled compound. The single crystals were grown from a solution of the titlr compound of methanol (mp. 355–357 K).

Structure description top

For background to Schiff base compounds, see: Dubey & Vaid (1991); Yadav et al. (1994); Galic et al. (2001). For biological applications of sulfur- and nitrogen-containing compounds, see: Wei et al. (1981, 1982); Thieme et al. (1973a,b); Dornow et al. (1964); Barrera et al. (1985); Malik et al., (2011). For related structures, see: Devarajegowda et al. (2012); Fun et al. (2008); Wang et al. (2008). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond graph-set motifs, see: Bernstein et al.(1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed along the a axis. Hydrogen bonds are shown as dashed lines.

3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₁H₁₂N₄S₂	Z = 2
M_r = 264.37	F(000) = 276
Triclinic, P1	D_x = 1.404 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7873 (2) Å	Cell parameters from 15170 reflections
b = 9.5982 (2) Å	θ = 3.4–29.1°
c = 9.6041 (2) Å	µ = 0.41 mm⁻¹
α = 76.608 (2)°	T = 293 K
β = 70.602 (2)°	Block, white
γ = 68.570 (2)°	0.3 × 0.2 × 0.1 mm
V = 625.30 (2) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2449 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.4°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
T_min = 0.866, T_max = 1.000	l = −11→11
30316 measured reflections

Refinement top

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0446P)² + 0.2502P] where P = (F_o² + 2F_c²)/3
2449 reflections	(Δ/σ)_max = 0.001
156 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₂N₄S₂	γ = 68.570 (2)°
M_r = 264.37	V = 625.30 (2) Å³
Triclinic, P1	Z = 2
a = 7.7873 (2) Å	Mo Kα radiation
b = 9.5982 (2) Å	µ = 0.41 mm⁻¹
c = 9.6041 (2) Å	T = 293 K
α = 76.608 (2)°	0.3 × 0.2 × 0.1 mm
β = 70.602 (2)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2449 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2121 reflections with I > 2σ(I)
T_min = 0.866, T_max = 1.000	R_int = 0.041
30316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
2449 reflections	Δρ_min = −0.17 e Å⁻³
156 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.15017 (7)	0.32917 (5)	0.84285 (5)	0.04691 (16)
S2	0.40556 (6)	−0.40134 (5)	0.33254 (5)	0.03932 (14)
N1	−0.3639 (2)	0.35160 (17)	1.09693 (16)	0.0409 (4)
N2	−0.2053 (2)	0.39804 (16)	1.03276 (16)	0.0389 (3)
H2	−0.1954	0.4764	1.0542	0.047*
N4	−0.14673 (19)	0.20528 (14)	0.93293 (14)	0.0308 (3)
N7	−0.0745 (2)	0.07943 (15)	0.85714 (15)	0.0356 (3)
C3	−0.0676 (2)	0.31151 (18)	0.93426 (18)	0.0322 (3)
C5	−0.3237 (2)	0.23338 (19)	1.03460 (18)	0.0351 (4)
C6	−0.4492 (3)	0.1392 (2)	1.0656 (2)	0.0530 (5)
H6A	−0.5573	0.1702	1.1492	0.079*
H6B	−0.3784	0.0353	1.0876	0.079*
H6C	−0.4932	0.1511	0.9800	0.079*
C8	0.0461 (2)	0.08739 (18)	0.73055 (19)	0.0359 (4)
H8	0.0818	0.1743	0.6941	0.043*
C9	0.1295 (2)	−0.03748 (18)	0.64155 (18)	0.0332 (3)
C10	0.2741 (3)	−0.0280 (2)	0.5103 (2)	0.0411 (4)
H10	0.3162	0.0561	0.4831	0.049*
C11	0.3554 (3)	−0.1409 (2)	0.4205 (2)	0.0413 (4)
H11	0.4527	−0.1331	0.3339	0.050*
C12	0.2930 (2)	−0.26694 (18)	0.45838 (18)	0.0324 (3)
C13	0.1500 (2)	−0.27788 (19)	0.58982 (18)	0.0367 (4)
H13	0.1084	−0.3622	0.6172	0.044*
C14	0.0695 (2)	−0.16417 (19)	0.67990 (18)	0.0364 (4)
H14	−0.0262	−0.1727	0.7674	0.044*
C15	0.2776 (3)	−0.5350 (2)	0.4030 (2)	0.0513 (5)
H15A	0.2824	−0.5749	0.5035	0.077*
H15B	0.3350	−0.6157	0.3423	0.077*
H15C	0.1464	−0.4864	0.4011	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0418 (3)	0.0503 (3)	0.0534 (3)	−0.0245 (2)	0.0056 (2)	−0.0266 (2)
S2	0.0395 (2)	0.0369 (2)	0.0370 (2)	−0.00991 (18)	0.00102 (18)	−0.01659 (18)
N1	0.0374 (8)	0.0447 (8)	0.0427 (8)	−0.0163 (7)	−0.0004 (6)	−0.0192 (7)
N2	0.0401 (8)	0.0359 (7)	0.0437 (8)	−0.0157 (6)	−0.0011 (6)	−0.0196 (6)
N4	0.0360 (7)	0.0278 (6)	0.0321 (7)	−0.0115 (5)	−0.0071 (6)	−0.0110 (5)
N7	0.0419 (8)	0.0298 (7)	0.0387 (8)	−0.0102 (6)	−0.0094 (6)	−0.0152 (6)
C3	0.0369 (8)	0.0293 (8)	0.0321 (8)	−0.0110 (7)	−0.0065 (7)	−0.0102 (6)
C5	0.0363 (8)	0.0378 (9)	0.0333 (8)	−0.0134 (7)	−0.0062 (7)	−0.0106 (7)
C6	0.0496 (11)	0.0582 (12)	0.0599 (12)	−0.0311 (10)	−0.0024 (9)	−0.0191 (10)
C8	0.0431 (9)	0.0310 (8)	0.0377 (9)	−0.0113 (7)	−0.0117 (7)	−0.0114 (7)
C9	0.0353 (8)	0.0314 (8)	0.0344 (8)	−0.0057 (7)	−0.0112 (7)	−0.0121 (7)
C10	0.0419 (9)	0.0377 (9)	0.0456 (10)	−0.0163 (8)	−0.0056 (8)	−0.0123 (8)
C11	0.0386 (9)	0.0414 (9)	0.0398 (9)	−0.0139 (8)	0.0018 (7)	−0.0135 (7)
C12	0.0310 (8)	0.0312 (8)	0.0331 (8)	−0.0038 (6)	−0.0087 (7)	−0.0103 (6)
C13	0.0414 (9)	0.0304 (8)	0.0369 (9)	−0.0112 (7)	−0.0049 (7)	−0.0104 (7)
C14	0.0389 (9)	0.0356 (9)	0.0316 (8)	−0.0098 (7)	−0.0034 (7)	−0.0107 (7)
C15	0.0498 (11)	0.0516 (11)	0.0546 (12)	−0.0224 (9)	0.0052 (9)	−0.0285 (9)

Geometric parameters (Å, º) top

S1—C3	1.6818 (17)	C8—C9	1.458 (2)
S2—C12	1.7565 (16)	C8—H8	0.9300
S2—C15	1.7837 (19)	C9—C14	1.388 (2)
N1—C5	1.294 (2)	C9—C10	1.395 (2)
N1—N2	1.3688 (19)	C10—C11	1.374 (2)
N2—C3	1.332 (2)	C10—H10	0.9300
N2—H2	0.8600	C11—C12	1.393 (2)
N4—C5	1.372 (2)	C11—H11	0.9300
N4—C3	1.3744 (19)	C12—C13	1.391 (2)
N4—N7	1.3944 (18)	C13—C14	1.382 (2)
N7—C8	1.272 (2)	C13—H13	0.9300
C5—C6	1.479 (2)	C14—H14	0.9300
C6—H6A	0.9600	C15—H15A	0.9600
C6—H6B	0.9600	C15—H15B	0.9600
C6—H6C	0.9600	C15—H15C	0.9600

C12—S2—C15	104.35 (8)	C14—C9—C10	118.42 (15)
C5—N1—N2	103.74 (13)	C14—C9—C8	123.14 (15)
C3—N2—N1	114.29 (13)	C10—C9—C8	118.44 (15)
C3—N2—H2	122.9	C11—C10—C9	121.01 (16)
N1—N2—H2	122.9	C11—C10—H10	119.5
C5—N4—C3	108.19 (13)	C9—C10—H10	119.5
C5—N4—N7	119.83 (13)	C10—C11—C12	120.40 (16)
C3—N4—N7	131.85 (13)	C10—C11—H11	119.8
C8—N7—N4	116.65 (13)	C12—C11—H11	119.8
N2—C3—N4	102.66 (14)	C13—C12—C11	118.93 (15)
N2—C3—S1	126.93 (12)	C13—C12—S2	125.20 (13)
N4—C3—S1	130.36 (12)	C11—C12—S2	115.88 (13)
N1—C5—N4	111.08 (14)	C14—C13—C12	120.34 (16)
N1—C5—C6	125.65 (16)	C14—C13—H13	119.8
N4—C5—C6	123.27 (15)	C12—C13—H13	119.8
C5—C6—H6A	109.5	C13—C14—C9	120.90 (16)
C5—C6—H6B	109.5	C13—C14—H14	119.6
H6A—C6—H6B	109.5	C9—C14—H14	119.6
C5—C6—H6C	109.5	S2—C15—H15A	109.5
H6A—C6—H6C	109.5	S2—C15—H15B	109.5
H6B—C6—H6C	109.5	H15A—C15—H15B	109.5
N7—C8—C9	121.10 (15)	S2—C15—H15C	109.5
N7—C8—H8	119.4	H15A—C15—H15C	109.5
C9—C8—H8	119.5	H15B—C15—H15C	109.5

C5—N1—N2—C3	−0.8 (2)	N4—N7—C8—C9	−179.55 (14)
C5—N4—N7—C8	153.95 (16)	N7—C8—C9—C14	7.1 (3)
C3—N4—N7—C8	−30.8 (2)	N7—C8—C9—C10	−174.05 (16)
N1—N2—C3—N4	1.71 (19)	C14—C9—C10—C11	0.1 (3)
N1—N2—C3—S1	−176.03 (13)	C8—C9—C10—C11	−178.77 (17)
C5—N4—C3—N2	−1.95 (17)	C9—C10—C11—C12	0.7 (3)
N7—N4—C3—N2	−177.60 (15)	C10—C11—C12—C13	−1.3 (3)
C5—N4—C3—S1	175.68 (14)	C10—C11—C12—S2	178.86 (14)
N7—N4—C3—S1	0.0 (3)	C15—S2—C12—C13	5.91 (18)
N2—N1—C5—N4	−0.59 (19)	C15—S2—C12—C11	−174.23 (14)
N2—N1—C5—C6	179.81 (18)	C11—C12—C13—C14	1.0 (3)
C3—N4—C5—N1	1.67 (19)	S2—C12—C13—C14	−179.17 (13)
N7—N4—C5—N1	177.93 (14)	C12—C13—C14—C9	−0.1 (3)
C3—N4—C5—C6	−178.72 (16)	C10—C9—C14—C13	−0.4 (3)
N7—N4—C5—C6	−2.5 (2)	C8—C9—C14—C13	178.42 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S1	0.93	2.57	3.212 (2)	126
N2—H2···S1ⁱ	0.86	2.48	3.328 (2)	169

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₄S₂
M_r	264.37
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7873 (2), 9.5982 (2), 9.6041 (2)
α, β, γ (°)	76.608 (2), 70.602 (2), 68.570 (2)
V (Å³)	625.30 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.866, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	30316, 2449, 2121
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.03
No. of reflections	2449
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S1	0.93	2.57	3.212 (2)	126
N2—H2···S1ⁱ	0.86	2.479	3.328 (2)	169

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

RK acknowledges the Department of Science & Technology for the sanction of the single-crystal X-ray diffractometer as a National Facility under mega research project No. SR/S2/ CMP-47/2003.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027–2030. CSD CrossRef CAS Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607. CSD CrossRef IUCr Journals Google Scholar
Dornow, A., Menzel, H. & Marx, P. (1964). Chem. Ber. 97, 2173–2178. CrossRef CAS Web of Science Google Scholar
Dubey, S. N. & Vaid, B. K. (1991). Synth. React. Inorg. Met. Org. Chem. 21, 1299–1311. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B., Muralidharan, A. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1509. Web of Science CSD CrossRef IUCr Journals Google Scholar
Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187–194. CAS Google Scholar
Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387–1394. Web of Science CrossRef CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thieme, P., König, H. & Amann, A. (1973a). BASF, German Patent 2228259. Google Scholar
Thieme, P., König, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q. Google Scholar
Wang, M., Cao, M., Hu, B., Cheng, C. X. & Song, X. G. (2008). Acta Cryst. E64, o374. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, P. H. L. & Bell, C. S. (1981). Chem. Abstr. 96, 104227. Google Scholar
Wei, P. H. L. & Bell, C. S. (1982). American Home Products Corporation, US Patent No. 4302585. Google Scholar
Yadav, S., Srivastava, S. & Pandey, O. P. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 925–939. CrossRef CAS Web of Science Google Scholar

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Volume 69| Part 5| May 2013| Pages o718-o719

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

3-Methyl-4-{(E)-[4-(methyl­sulfan­yl)benzyl­­idene]amino}-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione