3-[1-(4-Isobutyl-phen-yl)eth-yl]-4-[(E)-4-methyl-benzyl-ideneamino]-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(22)H(26)N(4)S, 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 intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. The crystal packing is strengthened by inter-molecular N-H⋯S hydrogen bonding and π-π stacking inter-actions 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 inter-actions. In the crystal packing, mol-ecules 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 = 378.53

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.05

8863 reflections

260 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.33 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036350/ng2513sup1.cif

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

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

C22H26N4S	Z = 2
Mr = 378.53	F000 = 404
Triclinic, P1	Dx = 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 = 2.6–26.3º
c = 12.9552 (2) Å	µ = 0.17 mm−1
α = 85.900 (1)º	T = 100.0 (1) K
β = 78.575 (1)º	Block, colourless
γ = 72.542 (1)º	0.61 × 0.40 × 0.17 mm
V = 1012.01 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8863 independent reflections
Radiation source: fine-focus sealed tube	7661 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 100.0(1) K	θmax = 35.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.902, Tmax = 0.971	k = −17→16
27492 measured reflections	l = −20→20

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.059P)2 + 0.2347P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
8863 reflections	Δρmax = 0.62 e Å−3
260 parameters	Δρmin = −0.33 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) . Cg2 is the centroid of the C1–C6 ring.