4-Amino-3-{1-[4-(2-methyl-prop-yl)phen-yl]eth-yl}-1H-1,2,4-triazole-5(4H)-thione.

In the title triazole compound, C(14)H(20)N(4)S, the dihedral angle between the triazole and benzene rings is 83.29 (11)°. The methine H atom and two methyl groups of the isobutyl group are disordered over two sites with occupancies of 0.684 (9) and 0.316 (9). In the crystal structure, N-H⋯S hydrogen bonds link the mol-ecules into chains running along the b axis. These chains are cross-linked into a two-dimensional network parallel to the ab plane by C-H⋯S hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶,c ▶). For the activities and applications of 1,2,4-triazole derivatives, see: Bhat et al. (2004 ▶); Holla et al. (2002 ▶); Karthikeyan et al. (2007 ▶); Raafat et al. (2006 ▶); Wei et al. (2007 ▶).

Experimental

Crystal data

C14H20N4S

M = 276.41

Monoclinic,

a = 5.9720 (3) Å

b = 8.5153 (5) Å

c = 14.8271 (6) Å

β = 97.223 (3)°

V = 748.03 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 100.0 (1) K

0.58 × 0.39 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.888, T max = 0.974

10373 measured reflections

3612 independent reflections

3295 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.07

3612 reflections

199 parameters

29 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 1293 Friedel pairs

Flack parameter: 0.05 (9)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: n class="Gene">APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022794/ci2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022794/ci2633Isup2.hkl

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

C14H20N4S	F000 = 296
Mr = 276.41	Dx = 1.227 Mg m−3
Monoclinic, P21	Melting point = 423–424 K
Hall symbol: P 2yb	Mo Kα radiation λ = 0.71073 Å
a = 5.9720 (3) Å	Cell parameters from 3612 reflections
b = 8.5153 (5) Å	θ = 2.8–30.0º
c = 14.8271 (6) Å	µ = 0.21 mm−1
β = 97.223 (3)º	T = 100.0 (1) K
V = 748.03 (7) Å3	Block, colourless
Z = 2	0.58 × 0.39 × 0.13 mm

Bruker SMART APEXII CCD area-detector diffractometer	3612 independent reflections
Radiation source: fine-focus sealed tube	3295 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.8º
ω scans	h = −8→8
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.888, Tmax = 0.974	l = −20→20
10373 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.2342P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.74 e Å−3
3612 reflections	Δρmin = −0.54 e Å−3
199 parameters	Extinction correction: none
29 restraints	Absolute structure: Flack (1983), 1293 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (9)
Secondary atom site location: difference Fourier map

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
S1	0.52913 (8)	0.63928 (8)	0.56907 (3)	0.02823 (14)
N1	0.3013 (3)	0.7737 (3)	0.41731 (11)	0.0254 (4)
H1	0.3880	0.8576	0.4194	0.030*
N2	0.1200 (3)	0.7497 (3)	0.35093 (12)	0.0268 (4)
N3	0.1622 (3)	0.5540 (3)	0.44853 (12)	0.0255 (4)
N4	0.1075 (4)	0.4156 (3)	0.49036 (14)	0.0304 (5)
H4A	0.205 (5)	0.349 (4)	0.477 (2)	0.036 (8)*
H4B	0.120 (6)	0.435 (5)	0.551 (2)	0.050 (9)*
C1	0.3316 (3)	0.6572 (3)	0.47770 (12)	0.0236 (4)
C2	0.0397 (3)	0.6138 (3)	0.37174 (13)	0.0242 (5)
C3	−0.1391 (4)	0.5226 (3)	0.31435 (13)	0.0262 (5)
H3	−0.2464	0.4790	0.3546	0.031*
C4	−0.0251 (3)	0.3868 (3)	0.27194 (13)	0.0245 (4)
C5	−0.1039 (4)	0.2344 (3)	0.27769 (15)	0.0304 (5)
H5	−0.2342	0.2154	0.3068	0.037*
C6	0.0035 (4)	0.1101 (3)	0.24192 (15)	0.0299 (5)
H6	−0.0538	0.0068	0.2468	0.036*
C7	0.1950 (3)	0.1335 (4)	0.19865 (12)	0.0275 (4)
C8	0.2718 (4)	0.2844 (4)	0.19190 (16)	0.0324 (6)
H8	0.4009	0.3031	0.1620	0.039*
C9	0.1650 (4)	0.4104 (3)	0.22788 (15)	0.0291 (5)
H9	0.2220	0.5137	0.2224	0.035*
C10	0.3109 (4)	−0.0036 (4)	0.15975 (16)	0.0368 (6)
H10A	0.2910	−0.0980	0.1969	0.044*
H10B	0.4747	0.0186	0.1643	0.044*
C11	0.2221 (5)	−0.0394 (6)	0.0603 (2)	0.0730 (14)
H11A	0.2458	0.0624	0.0293	0.088*	0.685 (8)
H11B	0.0645	−0.0562	0.0639	0.088*	0.315 (8)
C12	0.3694 (11)	−0.1501 (9)	0.0159 (4)	0.0661 (18)	0.685 (8)
H12A	0.3053	−0.1668	−0.0475	0.099*	0.685 (8)
H12B	0.3782	−0.2507	0.0483	0.099*	0.685 (8)
H12C	0.5210	−0.1053	0.0179	0.099*	0.685 (8)
C13	−0.0227 (7)	−0.0626 (7)	0.0405 (3)	0.0514 (15)	0.685 (8)
H13A	−0.0626	−0.0822	−0.0247	0.077*	0.685 (8)
H13B	−0.1010	0.0318	0.0578	0.077*	0.685 (8)
H13C	−0.0679	−0.1528	0.0750	0.077*	0.685 (8)
C12A	0.309 (2)	−0.2128 (11)	0.0475 (8)	0.057 (3)	0.315 (8)
H12D	0.2612	−0.2475	−0.0149	0.085*	0.315 (8)
H12E	0.2456	−0.2831	0.0901	0.085*	0.315 (8)
H12F	0.4742	−0.2149	0.0595	0.085*	0.315 (8)
C13A	0.220 (3)	0.0688 (16)	−0.0169 (8)	0.096 (6)	0.315 (8)
H13D	0.1648	0.1717	−0.0002	0.144*	0.315 (8)
H13E	0.1214	0.0271	−0.0691	0.144*	0.315 (8)
H13F	0.3740	0.0797	−0.0329	0.144*	0.315 (8)
C14	−0.2708 (4)	0.6302 (4)	0.24338 (15)	0.0321 (5)
H14A	−0.3404	0.7156	0.2743	0.048*
H14B	−0.3886	0.5693	0.2069	0.048*
H14C	−0.1674	0.6742	0.2037	0.048*

	U11	U22	U33	U12	U13	U23
S1	0.0253 (2)	0.0327 (3)	0.0260 (2)	0.0030 (3)	0.00040 (16)	−0.0015 (2)
N1	0.0251 (8)	0.0242 (11)	0.0263 (8)	0.0010 (8)	0.0010 (6)	−0.0027 (7)
N2	0.0252 (9)	0.0283 (11)	0.0260 (8)	0.0019 (9)	0.0003 (6)	−0.0031 (7)
N3	0.0222 (8)	0.0301 (11)	0.0246 (8)	0.0005 (8)	0.0050 (6)	0.0010 (7)
N4	0.0269 (9)	0.0345 (12)	0.0308 (9)	−0.0024 (10)	0.0079 (7)	0.0085 (9)
C1	0.0222 (8)	0.0256 (13)	0.0239 (8)	0.0026 (10)	0.0068 (6)	−0.0016 (8)
C2	0.0227 (8)	0.0280 (14)	0.0224 (8)	0.0040 (10)	0.0045 (6)	0.0018 (8)
C3	0.0204 (9)	0.0301 (13)	0.0286 (9)	−0.0016 (10)	0.0044 (7)	0.0001 (9)
C4	0.0204 (9)	0.0295 (12)	0.0227 (8)	−0.0003 (10)	−0.0001 (7)	0.0000 (8)
C5	0.0283 (11)	0.0333 (14)	0.0312 (10)	−0.0001 (11)	0.0095 (8)	0.0065 (9)
C6	0.0326 (10)	0.0269 (14)	0.0302 (9)	−0.0007 (11)	0.0040 (8)	0.0039 (9)
C7	0.0235 (8)	0.0358 (12)	0.0220 (7)	0.0045 (13)	−0.0018 (6)	−0.0020 (11)
C8	0.0244 (10)	0.0444 (16)	0.0288 (10)	−0.0076 (11)	0.0054 (8)	−0.0084 (10)
C9	0.0263 (10)	0.0313 (13)	0.0304 (10)	−0.0074 (11)	0.0062 (8)	−0.0041 (9)
C10	0.0319 (12)	0.0444 (17)	0.0325 (11)	0.0092 (13)	−0.0017 (9)	−0.0107 (11)
C11	0.0469 (17)	0.120 (4)	0.0501 (17)	0.028 (2)	−0.0016 (13)	−0.044 (2)
C12	0.072 (4)	0.077 (4)	0.053 (3)	0.008 (3)	0.028 (3)	−0.029 (3)
C13	0.047 (2)	0.071 (4)	0.0333 (18)	−0.003 (2)	−0.0046 (16)	−0.018 (2)
C12A	0.040 (5)	0.092 (8)	0.040 (5)	−0.005 (5)	0.006 (4)	−0.021 (5)
C13A	0.086 (8)	0.107 (10)	0.090 (8)	0.008 (7)	−0.008 (6)	−0.040 (7)
C14	0.0249 (9)	0.0328 (13)	0.0368 (10)	−0.0003 (13)	−0.0027 (7)	0.0012 (11)

S1—C1	1.688 (2)	C10—C11	1.533 (4)
N1—C1	1.334 (3)	C10—H10A	0.99
N1—N2	1.384 (2)	C10—H10B	0.99
N1—H1	0.8800	C11—C13	1.468 (4)
N2—C2	1.304 (3)	C11—C13A	1.468 (7)
N3—C1	1.368 (3)	C11—C12	1.497 (5)
N3—C2	1.372 (3)	C11—C12A	1.584 (7)
N3—N4	1.390 (3)	C11—H11A	1.00
N4—H4A	0.85 (4)	C11—H11B	0.96
N4—H4B	0.91 (3)	C12—H12A	0.98
C2—C3	1.496 (3)	C12—H12B	0.98
C3—C4	1.518 (3)	C12—H12C	0.98
C3—C14	1.535 (3)	C13—H13A	0.98
C3—H3	1.00	C13—H13B	0.98
C4—C5	1.386 (4)	C13—H13C	0.98
C4—C9	1.394 (3)	C12A—H12D	0.98
C5—C6	1.378 (4)	C12A—H12E	0.98
C5—H5	0.95	C12A—H12F	0.98
C6—C7	1.394 (3)	C13A—H13D	0.98
C6—H6	0.95	C13A—H13E	0.98
C7—C8	1.372 (4)	C13A—H13F	0.98
C7—C10	1.508 (4)	C14—H14A	0.98
C8—C9	1.389 (4)	C14—H14B	0.98
C8—H8	0.95	C14—H14C	0.98
C9—H9	0.95
C1—N1—N2	113.3 (2)	C13—C11—C10	115.8 (3)
C1—N1—H1	123.4	C13A—C11—C10	126.3 (7)
N2—N1—H1	123.4	C12—C11—C10	113.4 (3)
C2—N2—N1	103.96 (18)	C13—C11—C12A	100.6 (5)
C1—N3—C2	108.67 (19)	C13A—C11—C12A	117.5 (8)
C1—N3—N4	127.56 (18)	C10—C11—C12A	102.8 (5)
C2—N3—N4	123.66 (19)	C13—C11—H11A	102.6
N3—N4—H4A	105 (2)	C12—C11—H11A	102.6
N3—N4—H4B	107 (3)	C10—C11—H11A	102.6
H4A—N4—H4B	112 (3)	C12A—C11—H11A	133.3
N1—C1—N3	103.48 (17)	C13A—C11—H11B	103.0
N1—C1—S1	128.94 (19)	C12—C11—H11B	124.4
N3—C1—S1	127.58 (18)	C10—C11—H11B	101.5
N2—C2—N3	110.60 (19)	C12A—C11—H11B	101.9
N2—C2—C3	125.67 (19)	H11A—C11—H11B	110.5
N3—C2—C3	123.2 (2)	C11—C12—H12A	109.5
C2—C3—C4	107.83 (17)	C11—C12—H12B	109.5
C2—C3—C14	110.3 (2)	H12A—C12—H12B	109.5
C4—C3—C14	112.86 (18)	C11—C12—H12C	109.5
C2—C3—H3	108.6	H12A—C12—H12C	109.5
C4—C3—H3	108.6	H12B—C12—H12C	109.5
C14—C3—H3	108.6	C11—C13—H13A	109.5
C5—C4—C9	117.8 (2)	H11B—C13—H13A	133.0
C5—C4—C3	120.96 (19)	C11—C13—H13B	109.5
C9—C4—C3	121.2 (2)	H11B—C13—H13B	100.7
C6—C5—C4	121.2 (2)	H13A—C13—H13B	109.5
C6—C5—H5	119.4	C11—C13—H13C	109.5
C4—C5—H5	119.4	H11B—C13—H13C	92.6
C5—C6—C7	121.0 (3)	H13A—C13—H13C	109.5
C5—C6—H6	119.5	H13B—C13—H13C	109.5
C7—C6—H6	119.5	C11—C12A—H12D	109.5
C8—C7—C6	117.9 (3)	C11—C12A—H12E	109.5
C8—C7—C10	121.6 (2)	H12D—C12A—H12E	109.5
C6—C7—C10	120.5 (3)	C11—C12A—H12F	109.5
C7—C8—C9	121.4 (2)	H12D—C12A—H12F	109.5
C7—C8—H8	119.3	H12E—C12A—H12F	109.5
C9—C8—H8	119.3	C11—C13A—H13D	109.5
C8—C9—C4	120.6 (2)	C11—C13A—H13E	109.5
C8—C9—H9	119.7	H13D—C13A—H13E	109.5
C4—C9—H9	119.7	C11—C13A—H13F	109.5
C7—C10—C11	113.7 (2)	H13D—C13A—H13F	109.5
C7—C10—H10A	108.8	H13E—C13A—H13F	109.5
C11—C10—H10A	108.8	C3—C14—H14A	109.5
C7—C10—H10B	108.8	C3—C14—H14B	109.5
C11—C10—H10B	108.8	H14A—C14—H14B	109.5
H10A—C10—H10B	107.7	C3—C14—H14C	109.5
C13—C11—C13A	91.1 (8)	H14A—C14—H14C	109.5
C13—C11—C12	116.9 (4)	H14B—C14—H14C	109.5
C13A—C11—C12	90.0 (8)
C1—N1—N2—C2	−0.4 (2)	C2—C3—C4—C9	−49.2 (3)
N2—N1—C1—N3	0.1 (2)	C14—C3—C4—C9	72.9 (3)
N2—N1—C1—S1	−179.58 (16)	C9—C4—C5—C6	0.7 (3)
C2—N3—C1—N1	0.3 (2)	C3—C4—C5—C6	−177.8 (2)
N4—N3—C1—N1	−175.8 (2)	C4—C5—C6—C7	−0.1 (3)
C2—N3—C1—S1	179.98 (16)	C5—C6—C7—C8	−0.7 (3)
N4—N3—C1—S1	3.8 (3)	C5—C6—C7—C10	−180.0 (2)
N1—N2—C2—N3	0.6 (2)	C6—C7—C8—C9	0.8 (3)
N1—N2—C2—C3	−171.3 (2)	C10—C7—C8—C9	−179.9 (2)
C1—N3—C2—N2	−0.6 (2)	C7—C8—C9—C4	−0.2 (4)
N4—N3—C2—N2	175.7 (2)	C5—C4—C9—C8	−0.6 (3)
C1—N3—C2—C3	171.53 (18)	C3—C4—C9—C8	177.9 (2)
N4—N3—C2—C3	−12.1 (3)	C8—C7—C10—C11	−88.8 (3)
N2—C2—C3—C4	105.2 (3)	C6—C7—C10—C11	90.4 (3)
N3—C2—C3—C4	−65.8 (2)	C7—C10—C11—C13	−53.8 (5)
N2—C2—C3—C14	−18.5 (3)	C7—C10—C11—C13A	58.6 (10)
N3—C2—C3—C14	170.53 (19)	C7—C10—C11—C12	167.1 (4)
C2—C3—C4—C5	129.3 (2)	C7—C10—C11—C12A	−162.4 (5)
C14—C3—C4—C5	−108.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.45	3.272 (3)	155
N4—H4A···S1ii	0.85 (3)	2.54 (3)	3.392 (3)	176 (3)
C5—H5···S1iii	0.95	2.78	3.704 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.45	3.272 (3)	155
N4—H4A⋯S1ii	0.85 (3)	2.54 (3)	3.392 (3)	176 (3)
C5—H5⋯S1iii	0.95	2.78	3.704 (2)	165

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