3-[1-(4-Isobutyl-phen-yl)eth-yl]-6-(4-methyl-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the title compound, C(22)H(24)N(4)S, the methylphenyl and isobutylphenyl rings are inclined at an angle of 79.98 (1)° and they form dihedral angles of 4.59 (1) and 75.47 (1)°, respectively, with the triazolothia-diazole unit. An intra-molecular C-H⋯S hydrogen bond generates an S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯N hydrogen bonds and weak C-H⋯π and π-π inter-actions [centroid-centroid distances between the thia-diazole ring and a symmetry-related phenyl ring and between the triazole ring and the phenyl ring range from 3.5680 (8) to 3.7313 (8) Å].

Related literature

For information on the biological activity of triazole derivatives, thia­diazo­les and triazolothia­diazole compounds, see: Holla et al. (2003 ▶); Bekircan & Bektas (2006 ▶); Zhou et al. (2007 ▶); Bhat et al. (2004 ▶); Mathew et al. (2007 ▶); Karthikeyan et al. (2007 ▶); Chaturvedi et al. (1988 ▶); Shawali & Sayed (2006 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Tayseer et al. (2002 ▶).

Experimental

Crystal data

C22H24N4S

M = 376.51

Triclinic,

a = 7.2545 (1) Å

b = 8.1764 (1) Å

c = 17.6556 (3) Å

α = 97.390 (1)°

β = 96.120 (1)°

γ = 106.240 (1)°

V = 984.90 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 100.0 (1) K

0.46 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.922, T max = 0.969

15868 measured reflections

5687 independent reflections

4391 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.141

S = 1.08

5687 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.39 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/S1600536808013883/sj2495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013883/sj2495Isup2.hkl

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

C22H24N4S	Z = 2
Mr = 376.51	F000 = 400
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.2545 (1) Å	Cell parameters from 5597 reflections
b = 8.1764 (1) Å	θ = 2.6–32.0º
c = 17.6556 (3) Å	µ = 0.18 mm−1
α = 97.539 (1)º	T = 100.0 (1) K
β = 96.712 (1)º	Block, colourless
γ = 106.024 (1)º	0.46 × 0.20 × 0.18 mm
V = 984.90 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5687 independent reflections
Radiation source: fine-focus sealed tube	4391 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −10→8
Tmin = 0.922, Tmax = 0.969	k = −11→11
15868 measured reflections	l = −24→24

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0792P)2 + 0.0947P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
5687 reflections	Δρmax = 0.45 e Å−3
248 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.65630 (5)	0.70616 (5)	0.50456 (2)	0.02030 (11)
N1	0.77613 (18)	0.91957 (15)	0.40935 (7)	0.0187 (3)
N2	0.73966 (17)	0.75288 (15)	0.37235 (7)	0.0177 (3)
N3	0.6927 (2)	0.50811 (16)	0.29652 (7)	0.0237 (3)
N4	0.6461 (2)	0.47006 (16)	0.36878 (7)	0.0236 (3)
C1	0.8328 (2)	1.23186 (19)	0.51493 (8)	0.0197 (3)
H1A	0.8673	1.2404	0.4662	0.024*
C2	0.8563 (2)	1.3798 (2)	0.56768 (9)	0.0218 (3)
H2A	0.9089	1.4871	0.5541	0.026*
C3	0.8029 (2)	1.3718 (2)	0.64094 (8)	0.0212 (3)
C4	0.7242 (2)	1.2089 (2)	0.65980 (9)	0.0237 (3)
H4A	0.6859	1.2004	0.7080	0.028*
C5	0.7022 (2)	1.0597 (2)	0.60774 (8)	0.0222 (3)
H5A	0.6505	0.9524	0.6214	0.027*
C6	0.7572 (2)	1.06958 (18)	0.53493 (8)	0.0174 (3)
C7	0.7360 (2)	0.91381 (18)	0.47910 (8)	0.0172 (3)
C8	0.6765 (2)	0.62112 (18)	0.41226 (8)	0.0193 (3)
C9	0.7476 (2)	0.67599 (19)	0.29953 (8)	0.0202 (3)
C10	0.8042 (2)	0.7724 (2)	0.23493 (9)	0.0233 (3)
H10A	0.9227	0.8674	0.2557	0.028*
C11	0.6460 (2)	0.85129 (19)	0.20767 (8)	0.0220 (3)
C12	0.4859 (2)	0.75782 (19)	0.15229 (8)	0.0228 (3)
H12A	0.4751	0.6447	0.1309	0.027*
C13	0.3422 (2)	0.8308 (2)	0.12848 (9)	0.0245 (3)
H13A	0.2379	0.7664	0.0907	0.029*
C14	0.3510 (2)	0.99849 (19)	0.15996 (9)	0.0251 (3)
C15	0.5107 (3)	1.0916 (2)	0.21594 (9)	0.0289 (4)
H15A	0.5197	1.2035	0.2384	0.035*
C16	0.6563 (3)	1.0200 (2)	0.23864 (9)	0.0274 (4)
H16A	0.7628	1.0857	0.2752	0.033*
C17	0.8301 (3)	1.5347 (2)	0.69710 (9)	0.0274 (3)
H17A	0.7632	1.5074	0.7397	0.041*
H17B	0.7783	1.6128	0.6715	0.041*
H17C	0.9661	1.5879	0.7160	0.041*
C18	0.8520 (3)	0.6536 (2)	0.17039 (9)	0.0289 (4)
H18A	0.9693	0.6281	0.1885	0.043*
H18B	0.8694	0.7101	0.1263	0.043*
H18C	0.7472	0.5481	0.1560	0.043*
C19	0.1932 (3)	1.0768 (2)	0.13430 (10)	0.0296 (4)
H19A	0.1290	1.0994	0.1780	0.036*
H19B	0.0973	0.9928	0.0947	0.036*
C20	0.2641 (3)	1.2447 (2)	0.10233 (10)	0.0312 (4)
H20A	0.3529	1.3316	0.1440	0.037*
C21	0.3738 (3)	1.2215 (3)	0.03589 (11)	0.0437 (5)
H21A	0.4838	1.1846	0.0532	0.066*
H21B	0.4176	1.3293	0.0178	0.066*
H21C	0.2897	1.1360	−0.0055	0.066*
C22	0.0920 (3)	1.3099 (2)	0.07796 (11)	0.0419 (5)
H22A	0.1372	1.4156	0.0584	0.063*
H22B	0.0298	1.3303	0.1219	0.063*
H22C	0.0008	1.2249	0.0383	0.063*

	U11	U22	U33	U12	U13	U23
S1	0.0225 (2)	0.02041 (19)	0.01790 (18)	0.00448 (15)	0.00473 (14)	0.00591 (13)
N1	0.0200 (6)	0.0182 (6)	0.0187 (6)	0.0067 (5)	0.0031 (5)	0.0038 (5)
N2	0.0192 (6)	0.0172 (6)	0.0168 (6)	0.0051 (5)	0.0027 (5)	0.0044 (4)
N3	0.0277 (7)	0.0225 (6)	0.0202 (6)	0.0061 (6)	0.0036 (5)	0.0041 (5)
N4	0.0282 (7)	0.0208 (6)	0.0214 (6)	0.0052 (5)	0.0053 (5)	0.0059 (5)
C1	0.0205 (7)	0.0228 (7)	0.0177 (7)	0.0083 (6)	0.0047 (6)	0.0045 (6)
C2	0.0218 (7)	0.0214 (7)	0.0231 (7)	0.0077 (6)	0.0035 (6)	0.0047 (6)
C3	0.0189 (7)	0.0263 (7)	0.0194 (7)	0.0101 (6)	0.0011 (6)	0.0018 (6)
C4	0.0258 (8)	0.0294 (8)	0.0172 (7)	0.0096 (7)	0.0051 (6)	0.0039 (6)
C5	0.0250 (8)	0.0234 (7)	0.0194 (7)	0.0071 (6)	0.0051 (6)	0.0061 (6)
C6	0.0153 (7)	0.0208 (7)	0.0169 (6)	0.0073 (6)	0.0012 (5)	0.0031 (5)
C7	0.0146 (6)	0.0197 (7)	0.0180 (7)	0.0052 (5)	0.0019 (5)	0.0056 (5)
C8	0.0185 (7)	0.0195 (7)	0.0201 (7)	0.0043 (6)	0.0035 (6)	0.0064 (5)
C9	0.0219 (7)	0.0204 (7)	0.0177 (7)	0.0067 (6)	0.0016 (6)	0.0020 (5)
C10	0.0273 (8)	0.0236 (7)	0.0187 (7)	0.0064 (6)	0.0051 (6)	0.0040 (6)
C11	0.0302 (8)	0.0198 (7)	0.0163 (6)	0.0055 (6)	0.0069 (6)	0.0057 (5)
C12	0.0314 (8)	0.0183 (7)	0.0189 (7)	0.0062 (6)	0.0071 (6)	0.0032 (5)
C13	0.0310 (8)	0.0214 (7)	0.0189 (7)	0.0045 (6)	0.0039 (6)	0.0031 (6)
C14	0.0357 (9)	0.0217 (7)	0.0201 (7)	0.0095 (7)	0.0065 (7)	0.0072 (6)
C15	0.0447 (10)	0.0174 (7)	0.0231 (8)	0.0091 (7)	0.0002 (7)	0.0030 (6)
C16	0.0370 (9)	0.0202 (7)	0.0205 (7)	0.0032 (7)	−0.0003 (7)	0.0028 (6)
C17	0.0321 (9)	0.0292 (8)	0.0207 (7)	0.0132 (7)	0.0005 (7)	−0.0020 (6)
C18	0.0312 (9)	0.0353 (9)	0.0238 (8)	0.0140 (7)	0.0078 (7)	0.0060 (7)
C19	0.0377 (9)	0.0277 (8)	0.0259 (8)	0.0134 (7)	0.0049 (7)	0.0053 (6)
C20	0.0482 (11)	0.0217 (7)	0.0235 (8)	0.0140 (8)	−0.0024 (7)	0.0024 (6)
C21	0.0660 (14)	0.0411 (11)	0.0307 (9)	0.0211 (10)	0.0107 (9)	0.0158 (8)
C22	0.0616 (13)	0.0302 (9)	0.0340 (10)	0.0234 (9)	−0.0081 (9)	−0.0010 (7)

S1—C8	1.7248 (15)	C12—C13	1.388 (2)
S1—C7	1.7714 (14)	C12—H12A	0.9300
N1—C7	1.3018 (18)	C13—C14	1.391 (2)
N1—N2	1.3716 (17)	C13—H13A	0.9300
N2—C8	1.3672 (18)	C14—C15	1.395 (2)
N2—C9	1.3699 (18)	C14—C19	1.511 (2)
N3—C9	1.3113 (19)	C15—C16	1.387 (2)
N3—N4	1.4092 (18)	C15—H15A	0.9300
N4—C8	1.3133 (19)	C16—H16A	0.9300
C1—C2	1.383 (2)	C17—H17A	0.9600
C1—C6	1.397 (2)	C17—H17B	0.9600
C1—H1A	0.9300	C17—H17C	0.9600
C2—C3	1.397 (2)	C18—H18A	0.9600
C2—H2A	0.9300	C18—H18B	0.9600
C3—C4	1.397 (2)	C18—H18C	0.9600
C3—C17	1.503 (2)	C19—C20	1.533 (2)
C4—C5	1.386 (2)	C19—H19A	0.9700
C4—H4A	0.9300	C19—H19B	0.9700
C5—C6	1.395 (2)	C20—C21	1.513 (3)
C5—H5A	0.9300	C20—C22	1.527 (3)
C6—C7	1.464 (2)	C20—H20A	0.9800
C9—C10	1.503 (2)	C21—H21A	0.9600
C10—C11	1.525 (2)	C21—H21B	0.9600
C10—C18	1.533 (2)	C21—H21C	0.9600
C10—H10A	0.9800	C22—H22A	0.9600
C11—C12	1.392 (2)	C22—H22B	0.9600
C11—C16	1.394 (2)	C22—H22C	0.9600
C8—S1—C7	87.77 (7)	C12—C13—H13A	119.3
C7—N1—N2	107.74 (12)	C14—C13—H13A	119.3
C8—N2—C9	105.94 (12)	C13—C14—C15	117.59 (15)
C8—N2—N1	118.63 (12)	C13—C14—C19	121.14 (15)
C9—N2—N1	135.41 (12)	C15—C14—C19	121.27 (14)
C9—N3—N4	109.48 (12)	C16—C15—C14	121.08 (14)
C8—N4—N3	104.93 (12)	C16—C15—H15A	119.5
C2—C1—C6	119.97 (13)	C14—C15—H15A	119.5
C2—C1—H1A	120.0	C15—C16—C11	121.19 (15)
C6—C1—H1A	120.0	C15—C16—H16A	119.4
C1—C2—C3	121.54 (14)	C11—C16—H16A	119.4
C1—C2—H2A	119.2	C3—C17—H17A	109.5
C3—C2—H2A	119.2	C3—C17—H17B	109.5
C4—C3—C2	118.01 (14)	H17A—C17—H17B	109.5
C4—C3—C17	121.60 (14)	C3—C17—H17C	109.5
C2—C3—C17	120.39 (14)	H17A—C17—H17C	109.5
C5—C4—C3	120.94 (14)	H17B—C17—H17C	109.5
C5—C4—H4A	119.5	C10—C18—H18A	109.5
C3—C4—H4A	119.5	C10—C18—H18B	109.5
C4—C5—C6	120.46 (14)	H18A—C18—H18B	109.5
C4—C5—H5A	119.8	C10—C18—H18C	109.5
C6—C5—H5A	119.8	H18A—C18—H18C	109.5
C5—C6—C1	119.07 (13)	H18B—C18—H18C	109.5
C5—C6—C7	121.42 (13)	C14—C19—C20	114.77 (15)
C1—C6—C7	119.50 (12)	C14—C19—H19A	108.6
N1—C7—C6	122.53 (13)	C20—C19—H19A	108.6
N1—C7—S1	116.63 (11)	C14—C19—H19B	108.6
C6—C7—S1	120.84 (10)	C20—C19—H19B	108.6
N4—C8—N2	111.28 (13)	H19A—C19—H19B	107.6
N4—C8—S1	139.48 (11)	C21—C20—C22	111.13 (15)
N2—C8—S1	109.21 (10)	C21—C20—C19	111.68 (14)
N3—C9—N2	108.36 (13)	C22—C20—C19	109.77 (16)
N3—C9—C10	127.27 (13)	C21—C20—H20A	108.0
N2—C9—C10	124.35 (13)	C22—C20—H20A	108.0
C9—C10—C11	109.88 (13)	C19—C20—H20A	108.0
C9—C10—C18	109.90 (13)	C20—C21—H21A	109.5
C11—C10—C18	113.81 (13)	C20—C21—H21B	109.5
C9—C10—H10A	107.7	H21A—C21—H21B	109.5
C11—C10—H10A	107.7	C20—C21—H21C	109.5
C18—C10—H10A	107.7	H21A—C21—H21C	109.5
C12—C11—C16	117.76 (15)	H21B—C21—H21C	109.5
C12—C11—C10	121.62 (13)	C20—C22—H22A	109.5
C16—C11—C10	120.61 (14)	C20—C22—H22B	109.5
C13—C12—C11	120.99 (14)	H22A—C22—H22B	109.5
C13—C12—H12A	119.5	C20—C22—H22C	109.5
C11—C12—H12A	119.5	H22A—C22—H22C	109.5
C12—C13—C14	121.37 (15)	H22B—C22—H22C	109.5
C7—N1—N2—C8	−1.13 (17)	N4—N3—C9—N2	0.11 (17)
C7—N1—N2—C9	177.66 (15)	N4—N3—C9—C10	−178.01 (14)
C9—N3—N4—C8	−0.02 (17)	C8—N2—C9—N3	−0.16 (16)
C6—C1—C2—C3	−1.1 (2)	N1—N2—C9—N3	−179.05 (14)
C1—C2—C3—C4	−0.1 (2)	C8—N2—C9—C10	178.03 (14)
C1—C2—C3—C17	−179.98 (13)	N1—N2—C9—C10	−0.9 (3)
C2—C3—C4—C5	0.9 (2)	N3—C9—C10—C11	108.16 (17)
C17—C3—C4—C5	−179.20 (14)	N2—C9—C10—C11	−69.68 (18)
C3—C4—C5—C6	−0.5 (2)	N3—C9—C10—C18	−17.8 (2)
C4—C5—C6—C1	−0.6 (2)	N2—C9—C10—C18	164.34 (14)
C4—C5—C6—C7	179.78 (13)	C9—C10—C11—C12	−85.94 (17)
C2—C1—C6—C5	1.4 (2)	C18—C10—C11—C12	37.8 (2)
C2—C1—C6—C7	−178.96 (13)	C9—C10—C11—C16	93.15 (17)
N2—N1—C7—C6	−179.59 (12)	C18—C10—C11—C16	−143.13 (15)
N2—N1—C7—S1	1.19 (15)	C16—C11—C12—C13	0.4 (2)
C5—C6—C7—N1	176.10 (14)	C10—C11—C12—C13	179.48 (13)
C1—C6—C7—N1	−3.5 (2)	C11—C12—C13—C14	−1.2 (2)
C5—C6—C7—S1	−4.72 (19)	C12—C13—C14—C15	0.6 (2)
C1—C6—C7—S1	175.70 (11)	C12—C13—C14—C19	−179.48 (14)
C8—S1—C7—N1	−0.81 (12)	C13—C14—C15—C16	0.7 (2)
C8—S1—C7—C6	179.96 (12)	C19—C14—C15—C16	−179.20 (15)
N3—N4—C8—N2	−0.09 (16)	C14—C15—C16—C11	−1.5 (3)
N3—N4—C8—S1	178.05 (14)	C12—C11—C16—C15	0.9 (2)
C9—N2—C8—N4	0.15 (17)	C10—C11—C16—C15	−178.18 (14)
N1—N2—C8—N4	179.27 (12)	C13—C14—C19—C20	−122.58 (16)
C9—N2—C8—S1	−178.56 (10)	C15—C14—C19—C20	57.3 (2)
N1—N2—C8—S1	0.55 (16)	C14—C19—C20—C21	55.9 (2)
C7—S1—C8—N4	−178.04 (19)	C14—C19—C20—C22	179.58 (14)
C7—S1—C8—N2	0.12 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···S1	0.93	2.70	3.1194 (16)	108
C15—H15A···N3i	0.93	2.48	3.343 (2)	155
C4—H4A···Cg1ii	0.93	2.62	3.5063	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯S1	0.93	2.70	3.1194 (16)	108
C15—H15A⋯N3i	0.93	2.48	3.343 (2)	155
C4—H4A⋯Cg1ii	0.93	2.62	3.5063	160

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C11–C16 ring.