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

Fun, H.-K.; Yeap, C.S.; Manjunath, K.; Prasad, D.J.; Poojary, B.

doi:10.1107/S1600536811025773

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1943

doi:10.1107/S1600536811025773

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

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § K. Manjunath,^b D. Jagadeesh Prasad ^b and Boja Poojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 27 June 2011; accepted 29 June 2011; online 9 July 2011)

In the title compound, C₂₀H₂₃N₃S, the central 1,2,4-triazole ring makes dihedral angles of 69.76 (9) and 81.69 (8)°, respectively, with the phenyl and benzene rings. In the crystal, molecules are linked into a centrosymmetric dimer by a pair of intermolecular N—H⋯S hydrogen bonds, generating an R₂²(8) ring motif.

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Holla et al. (1998 , 2003 ); Maxwell et al. (1994 ); Turan-Zitouni et al. (1999 ); Demirbas & Demirbas (2002 ); Kritsanida et al. (2002 ); Burch & Smith (1966 ); Kalyoncuoglu et al. (1992 ); Mir et al. (1970 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₃N₃S
M_r = 337.47
Triclinic, $[P \overline 1]$
a = 6.3249 (2) Å
b = 12.4958 (5) Å
c = 12.9125 (4) Å
α = 77.649 (1)°
β = 78.133 (1)°
γ = 76.551 (1)°
V = 956.44 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 297 K
0.57 × 0.29 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.907, T_max = 0.973
30772 measured reflections
8473 independent reflections
5131 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.190
S = 1.05
8473 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.90	2.43	3.2982 (11)	161
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025773/is2744sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025773/is2744Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025773/is2744Isup3.cml

checkCIF report

Comment top

1,2,4-Triazole derivatives possess comprehensive bioactivities such as antimicrobial (Holla et al., 1998), anti-inflammatory (Maxwell et al., 1994), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas & Demirbas, 2002) and antiviral activities (Kritsanida et al., 2002). Among the 1,2,4-triazoles, the mercapto-thione-substituted 1,2,4-triazole ring systems have been well studied and so far, a variety of biological activities have been reported for a large number of their derivatives, such as antibacterial (Burch & Smith, 1966), antifungal (Kalyoncuoglu et al., 1992), antitubercular (Mir et al., 1970) and anticancer properties (Holla et al., 2003).

The central 1,2,4-triazole ring makes dihedral angles of 69.76 (9) and 81.69 (8)°, respectively, with the phenyl C1–C6 ring and the benzene C10–C15 rings (Fig. 1). In the crystal structure, the molecules are linked into a centrosymmetric dimer by intermolecular N2—H1N2···S1 hydrogen bonds (Table 1 and Fig. 2) generating an R₂²(8) ring motif (Bernstein et al., 1995).

Related literature top

For general background to and applications of 1,2,4-triazole derivatives, see: Holla et al. (1998, 2003); Maxwell et al. (1994); Turan-Zitouni et al. (1999); Demirbas & Demirbas (2002); Kritsanida et al. (2002); Burch & Smith (1966); Kalyoncuoglu et al. (1992); Mir et al. (1970). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 2-{2-[4-isobutylphenyl] propanoyl}-N-phenylhydrazinecarbothioamide (0.1 mol) and 5% sodium hydroxide (100 ml) was refluxed for 6 h. The reaction mixture was then poured into ice cold water and acidified with dilute hydrochloric acid. The precipitate thus obtained was filtered, dried and re-crystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, showing the molecules linked into dimers stacked along the a axis. Hydrogen bonds (dashed lines) are shown.

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

Crystal data top

C₂₀H₂₃N₃S	Z = 2
M_r = 337.47	F(000) = 360
Triclinic, P1	D_x = 1.172 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3249 (2) Å	Cell parameters from 7323 reflections
b = 12.4958 (5) Å	θ = 3.4–33.2°
c = 12.9125 (4) Å	µ = 0.18 mm⁻¹
α = 77.649 (1)°	T = 297 K
β = 78.133 (1)°	Block, yellow
γ = 76.551 (1)°	0.57 × 0.29 × 0.16 mm
V = 956.44 (6) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	8473 independent reflections
Radiation source: fine-focus sealed tube	5131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 35.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.907, T_max = 0.973	k = −20→20
30772 measured reflections	l = −20→20

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0928P)² + 0.0747P] where P = (F_o² + 2F_c²)/3
8473 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₂₃N₃S	γ = 76.551 (1)°
M_r = 337.47	V = 956.44 (6) Å³
Triclinic, P1	Z = 2
a = 6.3249 (2) Å	Mo Kα radiation
b = 12.4958 (5) Å	µ = 0.18 mm⁻¹
c = 12.9125 (4) Å	T = 297 K
α = 77.649 (1)°	0.57 × 0.29 × 0.16 mm
β = 78.133 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	8473 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5131 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.973	R_int = 0.029
30772 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
8473 reflections	Δρ_min = −0.27 e Å⁻³
220 parameters

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	−0.08075 (6)	−0.01849 (3)	0.18539 (3)	0.05785 (12)
N1	0.20563 (16)	0.11866 (8)	0.18008 (7)	0.04246 (19)
N2	0.20973 (18)	0.07739 (9)	0.02809 (8)	0.0521 (2)
H1N2	0.1912	0.0441	−0.0240	0.062*
N3	0.35825 (18)	0.14653 (10)	0.00916 (9)	0.0543 (2)
C1	0.2972 (3)	0.08271 (16)	0.35969 (12)	0.0758 (5)
H1A	0.4358	0.0431	0.3351	0.091*
C2	0.2366 (4)	0.0957 (2)	0.46651 (14)	0.0993 (8)
H2A	0.3370	0.0649	0.5135	0.119*
C3	0.0349 (3)	0.15220 (18)	0.50391 (13)	0.0847 (6)
H3A	−0.0044	0.1580	0.5763	0.102*
C4	−0.1105 (3)	0.2006 (2)	0.43437 (14)	0.0882 (6)
H4A	−0.2477	0.2416	0.4589	0.106*
C5	−0.0538 (2)	0.18870 (16)	0.32681 (12)	0.0683 (4)
H5A	−0.1532	0.2210	0.2795	0.082*
C6	0.14823 (19)	0.12949 (9)	0.29125 (9)	0.0447 (2)
C7	0.1115 (2)	0.05877 (9)	0.13045 (9)	0.0444 (2)
C8	0.35300 (19)	0.17053 (10)	0.10269 (9)	0.0465 (2)
C9	0.4782 (2)	0.24956 (11)	0.12384 (12)	0.0538 (3)
H9A	0.5611	0.2109	0.1820	0.065*
C10	0.3240 (2)	0.35217 (11)	0.15951 (11)	0.0514 (3)
C11	0.3736 (3)	0.40631 (16)	0.23145 (16)	0.0768 (5)
H11A	0.4992	0.3759	0.2628	0.092*
C12	0.2420 (3)	0.50401 (16)	0.25793 (18)	0.0815 (5)
H12A	0.2810	0.5382	0.3065	0.098*
C13	0.0531 (2)	0.55268 (11)	0.21409 (13)	0.0621 (3)
C14	−0.0013 (3)	0.49653 (14)	0.14492 (14)	0.0685 (4)
H14A	−0.1302	0.5254	0.1160	0.082*
C15	0.1316 (3)	0.39832 (13)	0.11773 (12)	0.0628 (3)
H15A	0.0909	0.3629	0.0706	0.075*
C16	−0.0877 (3)	0.66265 (13)	0.23725 (17)	0.0775 (5)
H16A	−0.0122	0.6946	0.2777	0.093*
H16B	−0.1012	0.7132	0.1695	0.093*
C17	−0.3145 (3)	0.65684 (16)	0.29847 (17)	0.0830 (5)
H17A	−0.3827	0.6169	0.2609	0.100*
C18	−0.3071 (7)	0.5916 (2)	0.4111 (2)	0.1563 (16)
H18A	−0.4547	0.5920	0.4490	0.234*
H18B	−0.2301	0.6254	0.4481	0.234*
H18C	−0.2319	0.5159	0.4077	0.234*
C19	−0.4555 (4)	0.7724 (2)	0.2994 (2)	0.1071 (8)
H19A	−0.4593	0.8111	0.2268	0.161*
H19B	−0.3944	0.8132	0.3371	0.161*
H19C	−0.6025	0.7664	0.3347	0.161*
C20	0.6445 (3)	0.28229 (17)	0.02293 (16)	0.0785 (5)
H20A	0.7416	0.2161	0.0025	0.118*
H20B	0.7290	0.3299	0.0384	0.118*
H20C	0.5664	0.3212	−0.0348	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0759 (2)	0.0634 (2)	0.04339 (17)	−0.03438 (17)	−0.00472 (14)	−0.01132 (13)
N1	0.0465 (5)	0.0467 (5)	0.0371 (4)	−0.0112 (4)	−0.0079 (3)	−0.0105 (3)
N2	0.0607 (6)	0.0613 (6)	0.0401 (5)	−0.0211 (5)	−0.0017 (4)	−0.0180 (4)
N3	0.0545 (6)	0.0665 (6)	0.0446 (5)	−0.0202 (5)	0.0000 (4)	−0.0140 (5)
C1	0.0783 (10)	0.0904 (11)	0.0531 (8)	0.0225 (8)	−0.0283 (7)	−0.0263 (7)
C2	0.1055 (14)	0.1307 (17)	0.0557 (9)	0.0281 (13)	−0.0401 (10)	−0.0338 (10)
C3	0.0979 (13)	0.1126 (14)	0.0452 (7)	−0.0087 (11)	−0.0106 (8)	−0.0313 (9)
C4	0.0690 (10)	0.1325 (17)	0.0594 (9)	0.0050 (10)	−0.0025 (8)	−0.0440 (10)
C5	0.0541 (7)	0.0994 (11)	0.0485 (7)	0.0027 (7)	−0.0115 (6)	−0.0237 (7)
C6	0.0515 (6)	0.0486 (5)	0.0372 (5)	−0.0106 (4)	−0.0097 (4)	−0.0112 (4)
C7	0.0522 (6)	0.0451 (5)	0.0386 (5)	−0.0112 (4)	−0.0075 (4)	−0.0118 (4)
C8	0.0440 (6)	0.0524 (6)	0.0442 (5)	−0.0114 (4)	−0.0063 (4)	−0.0098 (4)
C9	0.0451 (6)	0.0584 (7)	0.0622 (7)	−0.0169 (5)	−0.0124 (5)	−0.0093 (5)
C10	0.0509 (6)	0.0551 (6)	0.0541 (7)	−0.0213 (5)	−0.0118 (5)	−0.0074 (5)
C11	0.0578 (8)	0.0883 (11)	0.1032 (13)	−0.0129 (7)	−0.0314 (9)	−0.0415 (10)
C12	0.0699 (10)	0.0860 (11)	0.1100 (14)	−0.0250 (8)	−0.0201 (9)	−0.0476 (11)
C13	0.0638 (8)	0.0529 (7)	0.0696 (8)	−0.0249 (6)	0.0022 (6)	−0.0089 (6)
C14	0.0738 (9)	0.0646 (8)	0.0661 (9)	−0.0039 (7)	−0.0249 (8)	−0.0072 (7)
C15	0.0684 (8)	0.0658 (8)	0.0600 (8)	−0.0090 (7)	−0.0266 (7)	−0.0126 (6)
C16	0.0772 (10)	0.0588 (8)	0.0919 (12)	−0.0259 (7)	0.0129 (9)	−0.0153 (8)
C17	0.0817 (11)	0.0830 (11)	0.0885 (13)	−0.0356 (9)	0.0170 (9)	−0.0327 (9)
C18	0.206 (4)	0.110 (2)	0.105 (2)	−0.033 (2)	0.059 (2)	0.0048 (16)
C19	0.0893 (14)	0.1154 (17)	0.1069 (17)	−0.0089 (13)	0.0160 (13)	−0.0416 (14)
C20	0.0566 (8)	0.0913 (11)	0.0899 (12)	−0.0339 (8)	0.0087 (8)	−0.0195 (9)

Geometric parameters (Å, º) top

S1—C7	1.6766 (12)	C11—C12	1.374 (2)
N1—C7	1.3766 (13)	C11—H11A	0.9300
N1—C8	1.3815 (15)	C12—C13	1.382 (2)
N1—C6	1.4341 (14)	C12—H12A	0.9300
N2—C7	1.3361 (15)	C13—C14	1.384 (2)
N2—N3	1.3716 (15)	C13—C16	1.506 (2)
N2—H1N2	0.9023	C14—C15	1.385 (2)
N3—C8	1.2975 (15)	C14—H14A	0.9300
C1—C6	1.3695 (17)	C15—H15A	0.9300
C1—C2	1.388 (2)	C16—C17	1.498 (2)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.354 (3)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.511 (4)
C3—C4	1.366 (3)	C17—C19	1.512 (3)
C3—H3A	0.9300	C17—H17A	0.9800
C4—C5	1.392 (2)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.3620 (19)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C8—C9	1.4982 (17)	C19—H19B	0.9600
C9—C10	1.5145 (19)	C19—H19C	0.9600
C9—C20	1.543 (2)	C20—H20A	0.9600
C9—H9A	0.9800	C20—H20B	0.9600
C10—C11	1.3808 (19)	C20—H20C	0.9600
C10—C15	1.3836 (18)

C7—N1—C8	107.80 (9)	C11—C12—C13	121.61 (15)
C7—N1—C6	125.16 (10)	C11—C12—H12A	119.2
C8—N1—C6	126.94 (10)	C13—C12—H12A	119.2
C7—N2—N3	113.85 (10)	C12—C13—C14	116.87 (14)
C7—N2—H1N2	124.5	C12—C13—C16	122.73 (16)
N3—N2—H1N2	121.5	C14—C13—C16	120.39 (15)
C8—N3—N2	104.11 (10)	C13—C14—C15	121.57 (14)
C6—C1—C2	118.49 (15)	C13—C14—H14A	119.2
C6—C1—H1A	120.8	C15—C14—H14A	119.2
C2—C1—H1A	120.8	C10—C15—C14	121.04 (14)
C3—C2—C1	121.58 (15)	C10—C15—H15A	119.5
C3—C2—H2A	119.2	C14—C15—H15A	119.5
C1—C2—H2A	119.2	C17—C16—C13	115.34 (13)
C2—C3—C4	119.39 (15)	C17—C16—H16A	108.4
C2—C3—H3A	120.3	C13—C16—H16A	108.4
C4—C3—H3A	120.3	C17—C16—H16B	108.4
C3—C4—C5	120.11 (16)	C13—C16—H16B	108.4
C3—C4—H4A	119.9	H16A—C16—H16B	107.5
C5—C4—H4A	119.9	C16—C17—C18	111.5 (2)
C6—C5—C4	119.58 (14)	C16—C17—C19	111.03 (16)
C6—C5—H5A	120.2	C18—C17—C19	111.5 (2)
C4—C5—H5A	120.2	C16—C17—H17A	107.5
C5—C6—C1	120.81 (12)	C18—C17—H17A	107.5
C5—C6—N1	119.09 (10)	C19—C17—H17A	107.5
C1—C6—N1	120.09 (11)	C17—C18—H18A	109.5
N2—C7—N1	103.26 (10)	C17—C18—H18B	109.5
N2—C7—S1	128.48 (9)	H18A—C18—H18B	109.5
N1—C7—S1	128.26 (9)	C17—C18—H18C	109.5
N3—C8—N1	110.98 (10)	H18A—C18—H18C	109.5
N3—C8—C9	124.99 (12)	H18B—C18—H18C	109.5
N1—C8—C9	123.92 (11)	C17—C19—H19A	109.5
C8—C9—C10	111.30 (10)	C17—C19—H19B	109.5
C8—C9—C20	110.08 (12)	H19A—C19—H19B	109.5
C10—C9—C20	110.99 (12)	C17—C19—H19C	109.5
C8—C9—H9A	108.1	H19A—C19—H19C	109.5
C10—C9—H9A	108.1	H19B—C19—H19C	109.5
C20—C9—H9A	108.1	C9—C20—H20A	109.5
C11—C10—C15	117.19 (14)	C9—C20—H20B	109.5
C11—C10—C9	121.54 (12)	H20A—C20—H20B	109.5
C15—C10—C9	121.21 (12)	C9—C20—H20C	109.5
C12—C11—C10	121.64 (14)	H20A—C20—H20C	109.5
C12—C11—H11A	119.2	H20B—C20—H20C	109.5
C10—C11—H11A	119.2

C7—N2—N3—C8	0.55 (15)	C6—N1—C8—C9	−0.56 (18)
C6—C1—C2—C3	0.6 (4)	N3—C8—C9—C10	113.63 (14)
C1—C2—C3—C4	−2.1 (4)	N1—C8—C9—C10	−62.26 (15)
C2—C3—C4—C5	2.1 (4)	N3—C8—C9—C20	−9.86 (18)
C3—C4—C5—C6	−0.7 (3)	N1—C8—C9—C20	174.25 (13)
C4—C5—C6—C1	−0.8 (3)	C8—C9—C10—C11	147.05 (15)
C4—C5—C6—N1	−179.42 (17)	C20—C9—C10—C11	−89.98 (18)
C2—C1—C6—C5	0.8 (3)	C8—C9—C10—C15	−35.72 (18)
C2—C1—C6—N1	179.43 (18)	C20—C9—C10—C15	87.25 (16)
C7—N1—C6—C5	−68.30 (17)	C15—C10—C11—C12	−2.2 (3)
C8—N1—C6—C5	107.57 (15)	C9—C10—C11—C12	175.17 (16)
C7—N1—C6—C1	113.07 (16)	C10—C11—C12—C13	0.2 (3)
C8—N1—C6—C1	−71.06 (18)	C11—C12—C13—C14	2.0 (3)
N3—N2—C7—N1	−0.83 (14)	C11—C12—C13—C16	−176.77 (17)
N3—N2—C7—S1	178.99 (9)	C12—C13—C14—C15	−2.3 (2)
C8—N1—C7—N2	0.77 (12)	C16—C13—C14—C15	176.50 (15)
C6—N1—C7—N2	177.31 (10)	C11—C10—C15—C14	1.8 (2)
C8—N1—C7—S1	−179.06 (9)	C9—C10—C15—C14	−175.50 (14)
C6—N1—C7—S1	−2.52 (17)	C13—C14—C15—C10	0.4 (3)
N2—N3—C8—N1	−0.02 (13)	C12—C13—C16—C17	−114.2 (2)
N2—N3—C8—C9	−176.36 (12)	C14—C13—C16—C17	67.1 (2)
C7—N1—C8—N3	−0.49 (13)	C13—C16—C17—C18	65.7 (3)
C6—N1—C8—N3	−176.95 (11)	C13—C16—C17—C19	−169.34 (19)
C7—N1—C8—C9	175.90 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.90	2.43	3.2982 (11)	161

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃N₃S
M_r	337.47
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	6.3249 (2), 12.4958 (5), 12.9125 (4)
α, β, γ (°)	77.649 (1), 78.133 (1), 76.551 (1)
V (Å³)	956.44 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.57 × 0.29 × 0.16

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.907, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	30772, 8473, 5131
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.813

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.190, 1.05
No. of reflections	8473
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.90	2.43	3.2982 (11)	161

Symmetry code: (i) −x, −y, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160.

References

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Volume 67| Part 8| August 2011| Page o1943

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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