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

In the title compound, C(20)H(23)N(3)S, 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, mol-ecules are linked into a centrosymmetric dimer by a pair of inter-molecular N-H⋯S hydrogen bonds, generating an R(2) (2)(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 = 337.47

Triclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.190

S = 1.05

8473 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025773/is2744sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811025773/is2744Isup3.cml

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

C20H23N3S	Z = 2
Mr = 337.47	F(000) = 360
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0928P)2 + 0.0747P] where P = (Fo2 + 2Fc2)/3
8473 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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
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*

	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)

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)

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

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) .