N-[(E)-(5-Methyl-thio-phen-2-yl)methyl-idene]-1H-1,2,4-triazol-3-amine.

In the title Schiff base, C(8)H(8)N(4)S, a condensation product of 5-methyl-thio-phene-2-carboxaldehyde and 3-amino-1,2,4-triazole, the dihedral angle between the triazolyl and thienyl rings is 6.44 (14)°. The compound exists as a polymeric chain arising from inter-molecular N-H⋯N bonding.

Related literature

For a related comound, see: Chohan et al. (2009 ▶). For the biological properties of such compounds, see: Foroumadi et al. (2003 ▶); Manfredini et al. (2000 ▶).

Experimental

Crystal data

C8H8N4S

M = 192.24

Orthorhombic,

a = 7.2570 (7) Å

b = 8.9522 (8) Å

c = 14.2930 (15) Å

V = 928.56 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 (2) K

0.24 × 0.16 × 0.14 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.928, T max = 0.956

5793 measured reflections

2206 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.05

2206 reflections

134 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 854 Friedel pairs

Flack parameter: −0.02 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808041494/ng2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041494/ng2524Isup2.hkl

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

C8H8N4S	F(000) = 400
Mr = 192.24	Dx = 1.375 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2206 reflections
a = 7.2570 (7) Å	θ = 2.7–28.3°
b = 8.9522 (8) Å	µ = 0.31 mm−1
c = 14.2930 (15) Å	T = 296 K
V = 928.56 (16) Å3	Prismatic, light brown
Z = 4	0.24 × 0.16 × 0.14 mm

Bruker KAPPA APEXII CCD diffractometer	2206 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 7.4 pixels mm-1	θmax = 28.3°, θmin = 2.7°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.928, Tmax = 0.956	l = −17→19
5793 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.0383P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2206 reflections	Δρmax = 0.20 e Å−3
134 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 854 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (10)

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 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	0.48892 (7)	−0.18020 (5)	0.00175 (3)	0.0512 (2)
N1	0.5269 (2)	0.13362 (16)	0.09627 (10)	0.0456 (4)
N2	0.4898 (2)	0.29617 (16)	0.22417 (10)	0.0498 (5)
N3	0.5397 (2)	0.43946 (17)	0.23930 (11)	0.0502 (5)
N4	0.6332 (3)	0.39225 (19)	0.09806 (13)	0.0659 (7)
C1	0.5665 (3)	−0.0136 (2)	−0.04286 (12)	0.0460 (5)
C2	0.6222 (3)	−0.0303 (3)	−0.13344 (14)	0.0565 (7)
C3	0.6008 (3)	−0.1767 (3)	−0.16735 (14)	0.0562 (7)
C4	0.5306 (3)	−0.2720 (2)	−0.10199 (12)	0.0497 (5)
C5	0.4937 (4)	−0.4350 (3)	−0.11161 (16)	0.0737 (9)
C6	0.5724 (3)	0.1226 (2)	0.00957 (13)	0.0473 (5)
C7	0.5491 (3)	0.27297 (19)	0.13780 (12)	0.0432 (5)
C8	0.6228 (3)	0.4940 (3)	0.16478 (17)	0.0654 (8)
H2	0.663 (3)	0.048 (2)	−0.1784 (19)	0.0678*
H3	0.629 (3)	−0.210 (3)	−0.2327 (18)	0.0675*
H3N	0.515 (3)	0.488 (3)	0.2891 (17)	0.0602*
H5A	0.52067	−0.48427	−0.05354	0.1103*
H5B	0.57023	−0.47560	−0.16015	0.1103*
H5C	0.36648	−0.45026	−0.12734	0.1103*
H6	0.621 (3)	0.209 (2)	−0.0237 (15)	0.0567*
H8	0.671 (4)	0.595 (2)	0.1599 (17)	0.0785*

	U11	U22	U33	U12	U13	U23
S1	0.0642 (3)	0.0540 (3)	0.0354 (2)	−0.0070 (2)	0.0078 (2)	−0.0047 (2)
N1	0.0516 (8)	0.0465 (7)	0.0386 (7)	0.0015 (7)	−0.0023 (7)	−0.0011 (6)
N2	0.0668 (10)	0.0434 (7)	0.0392 (7)	0.0024 (7)	0.0000 (8)	0.0002 (5)
N3	0.0644 (10)	0.0439 (8)	0.0422 (8)	0.0024 (7)	−0.0020 (8)	−0.0053 (6)
N4	0.0895 (14)	0.0554 (10)	0.0529 (10)	−0.0181 (9)	0.0184 (10)	−0.0072 (8)
C1	0.0475 (9)	0.0518 (10)	0.0388 (8)	−0.0018 (7)	0.0027 (8)	−0.0017 (7)
C2	0.0641 (13)	0.0637 (13)	0.0418 (10)	−0.0064 (9)	0.0110 (9)	0.0012 (9)
C3	0.0605 (12)	0.0706 (13)	0.0376 (9)	0.0014 (10)	0.0098 (9)	−0.0096 (9)
C4	0.0515 (10)	0.0573 (10)	0.0404 (8)	−0.0008 (8)	0.0011 (8)	−0.0092 (7)
C5	0.100 (2)	0.0629 (12)	0.0582 (12)	−0.0099 (13)	0.0055 (13)	−0.0160 (10)
C6	0.0521 (9)	0.0499 (9)	0.0398 (8)	−0.0004 (8)	−0.0003 (8)	0.0008 (7)
C7	0.0475 (9)	0.0431 (8)	0.0391 (8)	0.0031 (7)	−0.0022 (8)	0.0003 (7)
C8	0.0827 (16)	0.0504 (11)	0.0630 (13)	−0.0152 (11)	0.0126 (12)	−0.0079 (10)

S1—C1	1.7169 (19)	C1—C6	1.432 (3)
S1—C4	1.7220 (18)	C2—C3	1.406 (4)
N1—C6	1.286 (2)	C3—C4	1.364 (3)
N1—C7	1.391 (2)	C4—C5	1.490 (3)
N2—N3	1.350 (2)	C2—H2	1.00 (2)
N2—C7	1.324 (2)	C3—H3	1.00 (3)
N3—C8	1.318 (3)	C5—H5A	0.9600
N4—C7	1.355 (3)	C5—H5B	0.9600
N4—C8	1.321 (3)	C5—H5C	0.9600
N3—H3N	0.85 (3)	C6—H6	0.974 (19)
C1—C2	1.365 (3)	C8—H8	0.97 (2)
S1···N1	3.1295 (15)	N4···H5Avii	2.5700
S1···C4i	3.647 (2)	N4···H6	2.39 (2)
N1···S1	3.1295 (15)	C1···N4v	3.419 (3)
N1···N3ii	2.963 (2)	C4···S1viii	3.647 (2)
N2···N4	2.252 (2)	C8···N2iii	3.241 (3)
N2···C8ii	3.241 (3)	C7···H3vi	3.03 (2)
N2···N3ii	3.243 (2)	C7···H3Nii	2.80 (3)
N3···N1iii	2.963 (2)	H2···N2iv	2.83 (2)
N3···N4	2.171 (2)	H2···N3iv	2.87 (2)
N3···N2iii	3.243 (2)	H3···N2ix	2.94 (2)
N4···C1iv	3.419 (3)	H3···C7ix	3.03 (2)
N4···N3	2.171 (2)	H3N···N1iii	2.12 (3)
N1···H3Nii	2.12 (3)	H3N···N2iii	2.77 (3)
N2···H8ii	2.71 (2)	H3N···C7iii	2.80 (3)
N2···H2v	2.83 (2)	H5A···N4x	2.5700
N2···H3vi	2.94 (2)	H6···N4	2.39 (2)
N2···H3Nii	2.77 (3)	H8···N2iii	2.71 (2)
N3···H2v	2.87 (2)
C1—S1—C4	92.13 (9)	N1—C7—N4	125.46 (16)
C6—N1—C7	116.76 (15)	N2—C7—N4	114.44 (16)
N3—N2—C7	102.19 (14)	N3—C8—N4	110.7 (2)
N2—N3—C8	110.20 (17)	C1—C2—H2	128.6 (14)
C7—N4—C8	102.42 (18)	C3—C2—H2	117.8 (14)
C8—N3—H3N	125.6 (17)	C2—C3—H3	125.2 (15)
N2—N3—H3N	124.1 (17)	C4—C3—H3	121.9 (15)
S1—C1—C6	123.72 (14)	C4—C5—H5A	109.00
C2—C1—C6	125.52 (19)	C4—C5—H5B	109.00
S1—C1—C2	110.75 (16)	C4—C5—H5C	110.00
C1—C2—C3	113.4 (2)	H5A—C5—H5B	109.00
C2—C3—C4	112.85 (18)	H5A—C5—H5C	109.00
S1—C4—C3	110.91 (15)	H5B—C5—H5C	109.00
C3—C4—C5	128.07 (19)	N1—C6—H6	120.2 (12)
S1—C4—C5	121.02 (15)	C1—C6—H6	115.6 (12)
N1—C6—C1	124.19 (17)	N3—C8—H8	124.6 (15)
N1—C7—N2	120.07 (16)	N4—C8—H8	124.7 (15)
C1—S1—C4—C3	−0.12 (18)	C8—N4—C7—N2	−0.4 (3)
C4—S1—C1—C2	−0.28 (18)	C7—N4—C8—N3	0.4 (2)
C4—S1—C1—C6	−179.69 (19)	C8—N4—C7—N1	−178.6 (2)
C1—S1—C4—C5	178.8 (2)	C2—C1—C6—N1	−176.6 (2)
C6—N1—C7—N4	−7.9 (3)	S1—C1—C2—C3	0.6 (2)
C7—N1—C6—C1	177.03 (19)	C6—C1—C2—C3	−180.0 (2)
C6—N1—C7—N2	173.91 (18)	S1—C1—C6—N1	2.7 (3)
C7—N2—N3—C8	0.1 (2)	C1—C2—C3—C4	−0.7 (3)
N3—N2—C7—N1	178.54 (17)	C2—C3—C4—S1	0.5 (2)
N3—N2—C7—N4	0.2 (2)	C2—C3—C4—C5	−178.4 (2)
N2—N3—C8—N4	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···N1iii	0.85 (3)	2.12 (3)	2.963 (2)	172 (2)
C6—H6···N4	0.974 (19)	2.39 (2)	2.761 (3)	101.7 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯N1i	0.85 (3)	2.12 (3)	2.963 (2)	172 (2)

Symmetry code: (i) .