3-[1-(4-Isobutyl­phen­yl)eth­yl]-4-[(E)-4-methyl­benzyl­ideneamino]-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Jebas, S.R.; Sujith, K.V.; Kalluraya, B.

doi:10.1107/S1600536808036350

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages o2313-o2314

doi:10.1107/S1600536808036350

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3-[1-(4-Isobutylphenyl)ethyl]-4-[(E)-4-methylbenzylideneamino]-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ K. V. Sujith ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 November 2008; accepted 6 November 2008; online 13 November 2008)

In the title compound, C₂₂H₂₆N₄S, the dihedral angles formed by the triazole ring with the two benzene rings are 87.51 (3) and 20.98 (3)°. The benzene rings are inclined at 71.88 (2)°. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. The crystal packing is strengthened by intermolecular N—H⋯S hydrogen bonding and π–π stacking interactions between the triazole and benzene rings, with a centroid–centroid distance of 3.6618 (5) Å, together with N⋯N [2.1299 (9)–2.2121 (9) Å] short contacts and C—H⋯π interactions. In the crystal packing, molecules are stacked along the a axis.

Related literature

For related literature on componds containing a triazole ring, see: Clemons et al. (2004 ); Demirbas & Ugurluoglu (2004 ); Demirbas et al. (2002 ); Johnston et al. (2002 ); Shujuan et al. (2004 ); For bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₆N₄S
M_r = 378.53
Triclinic, $[P \overline 1]$
a = 7.7614 (2) Å
b = 10.7649 (2) Å
c = 12.9552 (2) Å
α = 85.900 (1)°
β = 78.575 (1)°
γ = 72.542 (1)°
V = 1012.01 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100.0 (1) K
0.61 × 0.40 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.902, T_max = 0.971
27492 measured reflections
8863 independent reflections
7661 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.110
S = 1.05
8863 reflections
260 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.859 (9)	2.411 (9)	3.2619 (7)	171.0 (13)
C10—H10A⋯S1	0.93	2.55	3.1834 (8)	126
C12—H12A⋯Cg2ⁱⁱ	0.93	2.70	3.5531 (9)	152
C21—H21B⋯Cg2ⁱⁱⁱ	0.96	2.99	3.8326 (9)	148
Symmetry codes: (i) -x+2, -y-1, -z+2; (ii) -x+1, -y, -z+2; (iii) -x+2, -y, -z+1. Cg2 is the centroid of the C1–C6 ring.

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/S1600536808036350/ng2513sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036350/ng2513Isup2.hkl

checkCIF report

Comment top

Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, Fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), while Vorozole, Letrozole and Anastrozole are non-steroidal drugs used for the treatment of cancer (Clemons et al., 2004) and Loreclezole is used as an anticonvulsant (Johnston et al., 2002). Some Schiff base derivatives of acetic acid hydrazides containing 1,2,4-triazole-5-one ring have displayed anti-tumor activity against breast cancer, while 2-phenyl ethylideneamino and 2-phenyl ethylamino derivatives of 4-amino-1,2,4-triazol-5-ones have been found to be effective towards lung cell cancer and breast cancer (Demirbas et al., 2004, 2002). Due to the progress that occurs in dealing with the chemistry of substituted 4-amino-1,2,4-triazole-3-thiones and their derivatives as well as their biological activity, we synthesized and here report the crystal structure of 1,2,4-triazole Schiff base.

Bond lengths and angles in (I) (Fig. 1) are found to have normal values (Allen et al., 1987). The two benzene rings are essentially planar with the maximum deviation from planarity being 0.017 (1)Å for atom C6 and 0.013 (1)Å for atom C14 respectively. The dihedral angle formed by the triazole (N1/N2/C9/N3/C8) ring with the two benzene rings (C1—C6; C11—C16) are 87.51 (3)° and 20.98 (3)° respectively. The benzene rings (C1—C6; C11—C16) form dihedral angle of 71.88 (2)°, indicating that they are inclined to each other. An intramolecular C—H···S hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995).

The crystal packing is consolidated by intermolecular N—H···S hydrogen bonding (Table.1). Furthermore the packing is strengthened by π—π stacking interactions involving the triazole (N1/N2/C9/N3/C8) (Cg1) ring and the symmetry related (C11—C16) ring (Cg3) [Cg1···Cg3ⁱ = 3.6618 (5) Å; symmetry code: (i) 2-X,-Y,2-Z] together with N···N = 2.1299 (9)–2.2121 (9)Å short contacts and C—H···π interactions. In the crystal packing, the molecules are stacked along the a axis (Fig. 2).

Related literature top

For related literature on componds containing a triazole ring, see: Clemons et al. (2004); Demirbas & Ugurluoglu (2004); Demirbas et al. (2002); Johnston et al. (2002); Shujuan et al. (2004); For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). Cg2 is the centroid of the C1–C6 ring.

Experimental top

The title Schiff-base compound was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]- 4H-1,2,4-triazole-3-thiol (0.01 mol) and 4-methylbenzaldehyde (0.01 mol) in ethanol (50 ml) by adding 3 drops of concentrated Sulfuric acid for 3 h. The solid product obtained was collected by filtration, washed with ethanol and dried. The product obtained was then recrystallized using ethanol. Crystals suitable for X-ray analysis were obtained from acetone–N,N-dimethylformamide (DMF) (1:3) solution by slow evaporation. (Yield 63%; m.p. 415 K, M.F C₂₂H₂₆N₄S)

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.
	Fig. 2. The crystal packing of the title compound,viewed down the a axis.

3-[1-(4-Isobutylphenyl)ethyl]-4-[(E)-4-methylbenzylideneamino]- 1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₂H₂₆N₄S	Z = 2
M_r = 378.53	F(000) = 404
Triclinic, P1	D_x = 1.242 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7614 (2) Å	Cell parameters from 9961 reflections
b = 10.7649 (2) Å	θ = 2.6–26.3°
c = 12.9552 (2) Å	µ = 0.17 mm⁻¹
α = 85.900 (1)°	T = 100 K
β = 78.575 (1)°	Block, colourless
γ = 72.542 (1)°	0.61 × 0.40 × 0.17 mm
V = 1012.01 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8863 independent reflections
Radiation source: fine-focus sealed tube	7661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.902, T_max = 0.971	k = −17→16
27492 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.059P)² + 0.2347P] where P = (F_o² + 2F_c²)/3
8863 reflections	(Δ/σ)_max < 0.001
260 parameters	Δρ_max = 0.62 e Å⁻³
3 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₂H₂₆N₄S	γ = 72.542 (1)°
M_r = 378.53	V = 1012.01 (4) Å³
Triclinic, P1	Z = 2
a = 7.7614 (2) Å	Mo Kα radiation
b = 10.7649 (2) Å	µ = 0.17 mm⁻¹
c = 12.9552 (2) Å	T = 100 K
α = 85.900 (1)°	0.61 × 0.40 × 0.17 mm
β = 78.575 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8863 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7661 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.971	R_int = 0.021
27492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.62 e Å⁻³
8863 reflections	Δρ_min = −0.33 e Å⁻³
260 parameters

Special details top

Experimental. The 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
S1	0.83244 (3)	−0.312534 (18)	1.075041 (15)	0.01912 (5)
N1	1.05221 (9)	−0.33177 (6)	0.77577 (5)	0.01633 (12)
N2	0.98892 (9)	−0.37998 (6)	0.87246 (5)	0.01608 (11)
N3	0.91368 (8)	−0.17456 (6)	0.89131 (5)	0.01308 (10)
N4	0.86457 (9)	−0.04642 (6)	0.92483 (5)	0.01403 (11)
C1	0.77565 (11)	0.10391 (8)	0.71426 (6)	0.01826 (13)
H1A	0.8435	0.1436	0.7453	0.022*
C2	0.59831 (11)	0.17417 (8)	0.70084 (7)	0.01935 (14)
H2A	0.5499	0.2600	0.7231	0.023*
C3	0.49225 (10)	0.11785 (7)	0.65462 (6)	0.01578 (12)
C4	0.57282 (11)	−0.00989 (8)	0.61889 (6)	0.01597 (12)
H4A	0.5068	−0.0488	0.5857	0.019*
C5	0.75003 (10)	−0.07996 (7)	0.63202 (6)	0.01550 (12)
H5A	0.8006	−0.1646	0.6072	0.019*
C6	0.85251 (10)	−0.02490 (7)	0.68188 (5)	0.01447 (12)
C7	1.03785 (10)	−0.10614 (7)	0.70691 (6)	0.01530 (12)
H7A	1.0913	−0.0483	0.7367	0.018*
C8	1.00579 (10)	−0.20638 (7)	0.78940 (5)	0.01400 (12)
C9	0.90821 (10)	−0.28846 (7)	0.94628 (6)	0.01424 (12)
C10	0.72862 (10)	−0.01464 (7)	1.00254 (6)	0.01398 (12)
H10A	0.6706	−0.0763	1.0322	0.017*
C11	0.66417 (9)	0.11699 (7)	1.04473 (5)	0.01333 (11)
C12	0.52948 (11)	0.14034 (7)	1.13612 (6)	0.01629 (13)
H12A	0.4819	0.0738	1.1664	0.020*
C13	0.46617 (11)	0.26249 (8)	1.18207 (6)	0.01813 (13)
H13A	0.3773	0.2766	1.2432	0.022*
C14	0.53423 (10)	0.36416 (7)	1.13763 (6)	0.01632 (13)
C15	0.66461 (11)	0.34123 (7)	1.04410 (6)	0.01662 (13)
H15A	0.7078	0.4090	1.0120	0.020*
C16	0.73062 (10)	0.21915 (7)	0.99839 (6)	0.01555 (12)
H16A	0.8190	0.2052	0.9370	0.019*
C17	0.29282 (11)	0.18675 (8)	0.64939 (6)	0.01881 (14)
C18	0.23940 (11)	0.33496 (8)	0.63355 (7)	0.02000 (14)
H18A	0.2704	0.3726	0.6916	0.024*
C19	0.34375 (14)	0.37502 (10)	0.53048 (8)	0.02956 (19)
H19A	0.3082	0.4683	0.5242	0.044*
H19B	0.3153	0.3391	0.4724	0.044*
H19C	0.4735	0.3429	0.5299	0.044*
C20	0.03200 (13)	0.38811 (10)	0.63867 (9)	0.0304 (2)
H20A	−0.0020	0.4813	0.6320	0.046*
H20B	−0.0308	0.3638	0.7049	0.046*
H20C	−0.0015	0.3526	0.5823	0.046*
C22	0.47296 (13)	0.49376 (9)	1.19093 (8)	0.02463 (17)
H22A	0.3411	0.5236	1.2070	0.037*
H22B	0.5180	0.5557	1.1449	0.037*
H22C	0.5206	0.4848	1.2549	0.037*
C21	1.17512 (11)	−0.17176 (9)	0.61034 (6)	0.02119 (15)
H21A	1.2908	−0.2167	0.6304	0.032*
H21B	1.1919	−0.1069	0.5577	0.032*
H21C	1.1287	−0.2329	0.5824	0.032*
H17A	0.2165 (17)	0.1675 (13)	0.7137 (8)	0.027 (3)*
H17B	0.2573 (18)	0.1510 (13)	0.5935 (9)	0.027 (3)*
H1N2	1.0236 (18)	−0.4620 (8)	0.8863 (11)	0.026 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02447 (10)	0.01202 (8)	0.01508 (8)	−0.00159 (7)	0.00310 (6)	0.00220 (6)
N1	0.0200 (3)	0.0127 (3)	0.0138 (2)	−0.0021 (2)	−0.0016 (2)	0.0001 (2)
N2	0.0210 (3)	0.0098 (2)	0.0149 (2)	−0.0019 (2)	−0.0014 (2)	−0.00002 (19)
N3	0.0153 (2)	0.0094 (2)	0.0127 (2)	−0.00191 (19)	−0.00099 (18)	0.00014 (18)
N4	0.0164 (2)	0.0096 (2)	0.0144 (2)	−0.0017 (2)	−0.00228 (19)	−0.00062 (19)
C1	0.0216 (3)	0.0136 (3)	0.0202 (3)	−0.0035 (3)	−0.0077 (3)	−0.0007 (2)
C2	0.0223 (3)	0.0130 (3)	0.0222 (3)	−0.0010 (3)	−0.0081 (3)	−0.0031 (3)
C3	0.0184 (3)	0.0140 (3)	0.0139 (3)	−0.0027 (2)	−0.0038 (2)	−0.0002 (2)
C4	0.0193 (3)	0.0145 (3)	0.0142 (3)	−0.0047 (2)	−0.0037 (2)	−0.0001 (2)
C5	0.0195 (3)	0.0121 (3)	0.0136 (3)	−0.0033 (2)	−0.0022 (2)	−0.0002 (2)
C6	0.0172 (3)	0.0123 (3)	0.0124 (3)	−0.0030 (2)	−0.0022 (2)	0.0017 (2)
C7	0.0158 (3)	0.0144 (3)	0.0141 (3)	−0.0033 (2)	−0.0014 (2)	0.0019 (2)
C8	0.0149 (3)	0.0126 (3)	0.0125 (3)	−0.0016 (2)	−0.0017 (2)	0.0001 (2)
C9	0.0160 (3)	0.0103 (3)	0.0145 (3)	−0.0022 (2)	−0.0013 (2)	0.0009 (2)
C10	0.0149 (3)	0.0109 (3)	0.0152 (3)	−0.0027 (2)	−0.0025 (2)	0.0000 (2)
C11	0.0138 (3)	0.0112 (3)	0.0139 (3)	−0.0021 (2)	−0.0025 (2)	−0.0004 (2)
C12	0.0187 (3)	0.0133 (3)	0.0156 (3)	−0.0047 (2)	0.0001 (2)	−0.0011 (2)
C13	0.0195 (3)	0.0156 (3)	0.0172 (3)	−0.0042 (3)	0.0011 (2)	−0.0034 (2)
C14	0.0168 (3)	0.0122 (3)	0.0189 (3)	−0.0023 (2)	−0.0031 (2)	−0.0027 (2)
C15	0.0179 (3)	0.0122 (3)	0.0191 (3)	−0.0043 (2)	−0.0019 (2)	−0.0007 (2)
C16	0.0161 (3)	0.0128 (3)	0.0165 (3)	−0.0038 (2)	−0.0008 (2)	−0.0007 (2)
C17	0.0179 (3)	0.0180 (3)	0.0196 (3)	−0.0027 (3)	−0.0049 (2)	−0.0013 (3)
C18	0.0183 (3)	0.0173 (3)	0.0218 (3)	−0.0004 (3)	−0.0048 (3)	−0.0015 (3)
C19	0.0284 (4)	0.0265 (4)	0.0291 (4)	−0.0038 (3)	−0.0043 (3)	0.0082 (3)
C20	0.0196 (4)	0.0248 (4)	0.0423 (5)	0.0017 (3)	−0.0076 (3)	−0.0024 (4)
C22	0.0285 (4)	0.0154 (3)	0.0273 (4)	−0.0048 (3)	0.0010 (3)	−0.0070 (3)
C21	0.0191 (3)	0.0231 (4)	0.0175 (3)	−0.0038 (3)	0.0017 (2)	0.0005 (3)

Geometric parameters (Å, º) top

S1—C9	1.6843 (7)	C12—C13	1.3904 (11)
N1—C8	1.3039 (10)	C12—H12A	0.9300
N1—N2	1.3769 (9)	C13—C14	1.3945 (11)
N2—C9	1.3434 (9)	C13—H13A	0.9300
N2—H1N2	0.859 (8)	C14—C15	1.4001 (11)
N3—C9	1.3809 (9)	C14—C22	1.5030 (11)
N3—C8	1.3839 (9)	C15—C16	1.3883 (10)
N3—N4	1.3932 (9)	C15—H15A	0.9300
N4—C10	1.2868 (9)	C16—H16A	0.9300
C1—C6	1.3937 (11)	C17—C18	1.5328 (12)
C1—C2	1.3957 (11)	C17—H17A	0.970 (8)
C1—H1A	0.9300	C17—H17B	0.965 (8)
C2—C3	1.3966 (11)	C18—C19	1.5243 (13)
C2—H2A	0.9300	C18—C20	1.5276 (12)
C3—C4	1.3988 (11)	C18—H18A	0.9800
C3—C17	1.5153 (11)	C19—H19A	0.9600
C4—C5	1.3933 (11)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.3937 (11)	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C6—C7	1.5260 (10)	C20—H20C	0.9600
C7—C8	1.5031 (10)	C22—H22A	0.9600
C7—C21	1.5317 (11)	C22—H22B	0.9600
C7—H7A	0.9800	C22—H22C	0.9600
C10—C11	1.4607 (10)	C21—H21A	0.9600
C10—H10A	0.9300	C21—H21B	0.9600
C11—C12	1.3973 (10)	C21—H21C	0.9600
C11—C16	1.3997 (11)

C8—N1—N2	104.10 (6)	C12—C13—H13A	119.6
C9—N2—N1	113.95 (6)	C14—C13—H13A	119.6
C9—N2—H1N2	123.7 (9)	C13—C14—C15	118.39 (7)
N1—N2—H1N2	120.6 (9)	C13—C14—C22	120.58 (7)
C9—N3—C8	108.26 (6)	C15—C14—C22	121.01 (7)
C9—N3—N4	131.25 (6)	C16—C15—C14	121.17 (7)
C8—N3—N4	119.96 (6)	C16—C15—H15A	119.4
C10—N4—N3	115.74 (6)	C14—C15—H15A	119.4
C6—C1—C2	120.96 (7)	C15—C16—C11	119.99 (7)
C6—C1—H1A	119.5	C15—C16—H16A	120.0
C2—C1—H1A	119.5	C11—C16—H16A	120.0
C1—C2—C3	121.17 (7)	C3—C17—C18	117.04 (7)
C1—C2—H2A	119.4	C3—C17—H17A	108.6 (8)
C3—C2—H2A	119.4	C18—C17—H17A	108.0 (8)
C2—C3—C4	117.51 (7)	C3—C17—H17B	109.9 (8)
C2—C3—C17	122.25 (7)	C18—C17—H17B	107.4 (8)
C4—C3—C17	120.10 (7)	H17A—C17—H17B	105.3 (11)
C5—C4—C3	121.31 (7)	C19—C18—C20	110.91 (8)
C5—C4—H4A	119.3	C19—C18—C17	112.08 (7)
C3—C4—H4A	119.3	C20—C18—C17	109.57 (8)
C4—C5—C6	120.88 (7)	C19—C18—H18A	108.0
C4—C5—H5A	119.6	C20—C18—H18A	108.0
C6—C5—H5A	119.6	C17—C18—H18A	108.0
C1—C6—C5	118.09 (7)	C18—C19—H19A	109.5
C1—C6—C7	120.91 (7)	C18—C19—H19B	109.5
C5—C6—C7	120.86 (7)	H19A—C19—H19B	109.5
C8—C7—C6	108.52 (6)	C18—C19—H19C	109.5
C8—C7—C21	110.40 (6)	H19A—C19—H19C	109.5
C6—C7—C21	113.55 (6)	H19B—C19—H19C	109.5
C8—C7—H7A	108.1	C18—C20—H20A	109.5
C6—C7—H7A	108.1	C18—C20—H20B	109.5
C21—C7—H7A	108.1	H20A—C20—H20B	109.5
N1—C8—N3	110.74 (6)	C18—C20—H20C	109.5
N1—C8—C7	126.21 (7)	H20A—C20—H20C	109.5
N3—C8—C7	123.00 (6)	H20B—C20—H20C	109.5
N2—C9—N3	102.85 (6)	C14—C22—H22A	109.5
N2—C9—S1	127.09 (6)	C14—C22—H22B	109.5
N3—C9—S1	129.97 (6)	H22A—C22—H22B	109.5
N4—C10—C11	120.87 (7)	C14—C22—H22C	109.5
N4—C10—H10A	119.6	H22A—C22—H22C	109.5
C11—C10—H10A	119.6	H22B—C22—H22C	109.5
C12—C11—C16	119.12 (7)	C7—C21—H21A	109.5
C12—C11—C10	117.53 (7)	C7—C21—H21B	109.5
C16—C11—C10	123.35 (6)	H21A—C21—H21B	109.5
C13—C12—C11	120.40 (7)	C7—C21—H21C	109.5
C13—C12—H12A	119.8	H21A—C21—H21C	109.5
C11—C12—H12A	119.8	H21B—C21—H21C	109.5
C12—C13—C14	120.87 (7)

C8—N1—N2—C9	−1.39 (9)	C6—C7—C8—N3	−66.34 (9)
C9—N3—N4—C10	−33.22 (11)	C21—C7—C8—N3	168.62 (7)
C8—N3—N4—C10	156.15 (7)	N1—N2—C9—N3	2.75 (9)
C6—C1—C2—C3	0.00 (13)	N1—N2—C9—S1	−174.08 (6)
C1—C2—C3—C4	−2.26 (12)	C8—N3—C9—N2	−2.97 (8)
C1—C2—C3—C17	173.47 (8)	N4—N3—C9—N2	−174.43 (7)
C2—C3—C4—C5	2.09 (11)	C8—N3—C9—S1	173.73 (6)
C17—C3—C4—C5	−173.73 (7)	N4—N3—C9—S1	2.27 (12)
C3—C4—C5—C6	0.34 (11)	N3—N4—C10—C11	−179.96 (6)
C2—C1—C6—C5	2.44 (12)	N4—C10—C11—C12	−173.19 (7)
C2—C1—C6—C7	−173.48 (7)	N4—C10—C11—C16	6.71 (11)
C4—C5—C6—C1	−2.61 (11)	C16—C11—C12—C13	−1.82 (11)
C4—C5—C6—C7	173.32 (7)	C10—C11—C12—C13	178.09 (7)
C1—C6—C7—C8	108.52 (8)	C11—C12—C13—C14	0.56 (12)
C5—C6—C7—C8	−67.29 (9)	C12—C13—C14—C15	1.58 (12)
C1—C6—C7—C21	−128.32 (8)	C12—C13—C14—C22	−176.58 (8)
C5—C6—C7—C21	55.87 (9)	C13—C14—C15—C16	−2.50 (12)
N2—N1—C8—N3	−0.65 (8)	C22—C14—C15—C16	175.66 (8)
N2—N1—C8—C7	−178.19 (7)	C14—C15—C16—C11	1.26 (12)
C9—N3—C8—N1	2.37 (9)	C12—C11—C16—C15	0.92 (11)
N4—N3—C8—N1	174.96 (6)	C10—C11—C16—C15	−178.99 (7)
C9—N3—C8—C7	180.00 (7)	C2—C3—C17—C18	35.20 (11)
N4—N3—C8—C7	−7.40 (10)	C4—C3—C17—C18	−149.19 (7)
C6—C7—C8—N1	110.92 (8)	C3—C17—C18—C19	60.72 (10)
C21—C7—C8—N1	−14.12 (11)	C3—C17—C18—C20	−175.71 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.86 (1)	2.41 (1)	3.2619 (7)	171 (1)
C10—H10A···S1	0.93	2.55	3.1834 (8)	126
C12—H12A···Cg2ⁱⁱ	0.93	2.70	3.5531 (9)	152
C21—H21B···Cg2ⁱⁱⁱ	0.96	2.99	3.8326 (9)	148

Symmetry codes: (i) −x+2, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₄S
M_r	378.53
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.7614 (2), 10.7649 (2), 12.9552 (2)
α, β, γ (°)	85.900 (1), 78.575 (1), 72.542 (1)
V (Å³)	1012.01 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.61 × 0.40 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.902, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	27492, 8863, 7661
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.110, 1.05
No. of reflections	8863
No. of parameters	260
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.33

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
N2—H1N2···S1ⁱ	0.859 (9)	2.411 (9)	3.2619 (7)	171.0 (13)
C10—H10A···S1	0.93	2.55	3.1834 (8)	126
C12—H12A···Cg2ⁱⁱ	0.93	2.70	3.5531 (9)	152
C21—H21B···Cg2ⁱⁱⁱ	0.96	2.99	3.8326 (9)	148

Symmetry codes: (i) −x+2, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+2, −y, −z+1.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship.

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
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Clemons, M., Coleman, R. E. & Verma, S. (2004). Cancer Treat. Rev. 30, 325–332. Web of Science CrossRef PubMed CAS Google Scholar
Demirbas, N. & Ugurluoglu, R. (2004). Turk. J. Chem. 28, 679–690. CAS Google Scholar
Demirbas, N., Ugurluoglu, R. & Demirbasx, A. (2002). Bioorg. Med. Chem. 10, 3717–3723. Web of Science CrossRef PubMed CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shujuan, S., Hongxiang, L., Gao, Y., Fan, P., Ma, B., Ge, W. & Wang, X. (2004). J. Pharm. Biomed. Anal. 34, 1117–1124. Web of Science PubMed Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Pages o2313-o2314

doi:10.1107/S1600536808036350

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

3-[1-(4-Iso­butyl­phen­yl)eth­yl]-4-[(E)-4-methyl­benzyl­­idene­amino]-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-[1-(4-Isobutylphenyl)ethyl]-4-[(E)-4-methylbenzylideneamino]-1H-1,2,4-triazole-5(4H)-thione