4-Amino-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Chantrapromma, S.

doi:10.1107/S1600536808022794

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1590-o1591

doi:10.1107/S1600536808022794

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4-Amino-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* K. V. Sujith,^b P. S. Patil,^c B. Kalluraya ^b and Suchada Chantrapromma ^d ‡

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 13 July 2008; accepted 20 July 2008; online 26 July 2008)

In the title triazole compound, C₁₄H₂₀N₄S, 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 molecules 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_r = 276.41
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.07
3612 reflections
199 parameters
29 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ), 1293 Friedel pairs
Flack parameter: 0.05 (9)

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

Data collection: APEX2 (Bruker, 2005); cell refinement: 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 ).

Supporting information

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

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

checkCIF report

Comment top

In recent decades, a large number of reports concerning 4-amino-1,2,4-triazol-3-thiones have appeared owing to a wide variety of their biological activity. The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting drug candidates, including H1/H2 histamine receptor blockers, cholinesterase-active agents, CNS stimulants, antianxiety agents, and sedatives (Bhat et al., 2004). The amino and thione groups are ready-made nucleophilic centers for the synthesis of condensed nitrogen and sulfur heterocyclic rings, e.g., triazolothiadiazoles, triazolothiadiazines and triazolothiadiazepines (Raafat et al., 2006). Substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antitumorial, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). The broad biological activities that the 1,2,4-triazoles shown may be due to the presence of the >N—C—S moiety (Holla et al., 2002). Due to the progress that occurs in dealing with the chemistry of substituted 4-amino-1,2,4-triazole-3-thiones as well as their biological activity, we report here the crystal structure of the title triazole compound.

The bond distances and angles in the title molecule (Fig .1) have normal values (Allen et al., 1987) and are comparable with those observed in related structures (Fun et al., 2008a,b,c). The triazole ring (C1/C2/N1-N3) is planar to within ±0.004 Å. The chiral carbon atom C3 is in a distorted tetrahedral configuration. The dihedral angle between the triazole and benzene (C4-C9) rings is 83.29 (11)°. The 2-methylpropyl group is disordered over two sites. The orientation of this group with respect to the benzene ring can be indicated by the torsion angles C7–C10–C11–C12 = 167.1 (4)° and C7–C10–C11–C13 = -53.8 (5)° [C7–C10–C11–C12A = -162.4 (5)° and C7–C10–C11–C13A = 58.6 (10)° for the minor component].

In the crystal packing, the molecules are linked into chains along the b axis by N—H···S hydrogen bonds (Fig. 2). These chains are cross-linked into a two dimensional network parallel to the ab plane by C—H···S hydrogen bonds (Table 1).

Related literature top

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 top

The title compound was prepared by following the literature procedure (Karthikeyan et al., 2007). The solid product obtained was collected by filtration, washed with ethanol and dried. Colourless single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation (yield 61%; m.p. 423–424 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Both disorder components are shown.
	Fig. 2. The packing diagram of the title compound, viewed along the c axis. Only the major disorder component is shown. Hydrogen bonds are shown as dashed lines.

4-Amino-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole- 5(4H)-thione top

Crystal data top

C₁₄H₂₀N₄S	F(000) = 296
M_r = 276.41	D_x = 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 = 2.8–30.0°
c = 14.8271 (6) Å	µ = 0.21 mm⁻¹
β = 97.223 (3)°	T = 100 K
V = 748.03 (7) Å³	Block, colourless
Z = 2	0.58 × 0.39 × 0.13 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3612 independent reflections
Radiation source: fine-focus sealed tube	3295 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.888, T_max = 0.974	l = −20→20
10373 measured reflections

Refinement top

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0623P)² + 0.2342P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3612 reflections	Δρ_max = 0.74 e Å⁻³
199 parameters	Δρ_min = −0.54 e Å⁻³
29 restraints	Absolute structure: Flack (1983), 1293 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (9)

Crystal data top

C₁₄H₂₀N₄S	V = 748.03 (7) Å³
M_r = 276.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.9720 (3) Å	µ = 0.21 mm⁻¹
b = 8.5153 (5) Å	T = 100 K
c = 14.8271 (6) Å	0.58 × 0.39 × 0.13 mm
β = 97.223 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3612 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3295 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.974	R_int = 0.029
10373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	Δρ_max = 0.74 e Å⁻³
S = 1.07	Δρ_min = −0.54 e Å⁻³
3612 reflections	Absolute structure: Flack (1983), 1293 Friedel pairs
199 parameters	Absolute structure parameter: 0.05 (9)
29 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₄S
M_r	276.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	5.9720 (3), 8.5153 (5), 14.8271 (6)
β (°)	97.223 (3)
V (Å³)	748.03 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.58 × 0.39 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.888, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	10373, 3612, 3295
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.07
No. of reflections	3612
No. of parameters	199
No. of restraints	29
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.54
Absolute structure	Flack (1983), 1293 Friedel pairs
Absolute structure parameter	0.05 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

KVS and BK are grateful to the Kerala State Council for Science Technology and the Environment, Thiruvananthapuram, for financial assistance. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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. CrossRef Web of Science Google Scholar
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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 64| Part 8| August 2008| Pages o1590-o1591

doi:10.1107/S1600536808022794

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

4-Amino-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-Amino-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione