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

In the mol-ecule of the title compound, C(17)H(22)N(4)S, the triazolothia-diazole ring system is essentially planar and forms a dihedral angle of 74.34 (6)° with the benzene ring. In the crystal structure, mol-ecules are linked into chains running along the b axis by C-H⋯π inter-actions; adjacent chains are cross-linked via C-H⋯N hydrogen bonds and short S⋯N contacts [3.2694 (14) and 3.2953 (14) Å].

Related literature

For a related structure, see: Fun et al. (2008 ▶). For biological activities of triazole and 1,3,4-thia­diazo­les, see: Al-Soud et al. (2004 ▶); Labanauskas et al. (2004 ▶); Mathew et al. (2006 ▶); Ragenovic et al. (2001 ▶). For pharmacological activities of thia­diazo­les, see: Karegoudar et al. (2008 ▶); Swamy et al. (2006 ▶); Wang et al. (1996 ▶). For the preparation, see: Bhalerao et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H22N4S

M = 314.45

Orthorhombic,

a = 11.4341 (5) Å

b = 9.1939 (4) Å

c = 30.9870 (13) Å

V = 3257.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 100.0 (1) K

0.44 × 0.09 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.917, T max = 0.990

40117 measured reflections

5793 independent reflections

4079 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.04

5793 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.49 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/S1600536808027086/ci2662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027086/ci2662Isup2.hkl

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

C17H22N4S	F000 = 1344
Mr = 314.45	Dx = 1.282 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8453 reflections
a = 11.4341 (5) Å	θ = 2.2–29.2º
b = 9.1939 (4) Å	µ = 0.20 mm−1
c = 30.9870 (13) Å	T = 100.0 (1) K
V = 3257.5 (2) Å3	Needle, colourless
Z = 8	0.44 × 0.09 × 0.05 mm

Bruker SMART APEXII CCD area-detector diffractometer	5793 independent reflections
Radiation source: fine-focus sealed tube	4079 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
T = 100.0(1) K	θmax = 32.4º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.917, Tmax = 0.990	k = −13→13
40117 measured reflections	l = −40→46

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0517P)2 + 2.0837P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
5793 reflections	Δρmax = 0.60 e Å−3
203 parameters	Δρmin = −0.49 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	0.53939 (3)	0.06763 (4)	0.266708 (12)	0.01935 (10)
N1	0.62584 (12)	0.31200 (15)	0.16919 (4)	0.0209 (3)
N2	0.53144 (12)	0.24935 (15)	0.19196 (4)	0.0213 (3)
N3	0.69861 (12)	0.18920 (14)	0.22283 (4)	0.0175 (3)
N4	0.76251 (12)	0.11936 (15)	0.25470 (4)	0.0193 (3)
C1	0.57968 (14)	0.17716 (17)	0.22372 (5)	0.0186 (3)
C2	0.72430 (14)	0.27501 (17)	0.18787 (5)	0.0186 (3)
C3	0.68928 (14)	0.05296 (16)	0.27988 (5)	0.0179 (3)
C4	0.72469 (14)	−0.03276 (17)	0.31922 (5)	0.0178 (3)
H4A	0.6795	−0.1233	0.3192	0.021*
C5	0.69098 (14)	0.05277 (16)	0.35984 (5)	0.0182 (3)
C6	0.76816 (15)	0.14778 (18)	0.38014 (5)	0.0206 (3)
H6A	0.8439	0.1579	0.3696	0.025*
C7	0.73313 (15)	0.22797 (18)	0.41606 (5)	0.0208 (3)
H7A	0.7861	0.2906	0.4292	0.025*
C8	0.62023 (15)	0.21602 (17)	0.43254 (5)	0.0194 (3)
C9	0.54403 (15)	0.12017 (18)	0.41213 (5)	0.0204 (3)
H9A	0.4683	0.1099	0.4226	0.025*
C10	0.57850 (15)	0.03957 (17)	0.37645 (5)	0.0201 (3)
H10A	0.5258	−0.0240	0.3635	0.024*
C11	0.58366 (16)	0.29969 (18)	0.47213 (5)	0.0222 (3)
H11A	0.5067	0.3408	0.4671	0.027*
H11B	0.6377	0.3798	0.4763	0.027*
C12	0.57973 (16)	0.20868 (18)	0.51362 (5)	0.0225 (3)
H12A	0.5174	0.1363	0.5105	0.027*
C13	0.69373 (19)	0.1279 (2)	0.52134 (6)	0.0376 (5)
H13A	0.6888	0.0747	0.5479	0.056*
H13B	0.7569	0.1964	0.5230	0.056*
H13C	0.7075	0.0614	0.4980	0.056*
C14	0.54985 (18)	0.3048 (2)	0.55214 (5)	0.0309 (4)
H14A	0.5453	0.2462	0.5777	0.046*
H14B	0.4759	0.3515	0.5473	0.046*
H14C	0.6095	0.3773	0.5557	0.046*
C15	0.85352 (14)	−0.07336 (18)	0.31744 (5)	0.0214 (3)
H15A	0.8690	−0.1260	0.2913	0.032*
H15B	0.8727	−0.1331	0.3418	0.032*
H15C	0.9002	0.0134	0.3181	0.032*
C16	0.84512 (15)	0.31316 (19)	0.17390 (5)	0.0223 (3)
H16A	0.8872	0.2247	0.1669	0.027*
H16B	0.8856	0.3602	0.1976	0.027*
C17	0.84575 (17)	0.4136 (2)	0.13488 (6)	0.0279 (4)
H17A	0.9250	0.4364	0.1272	0.042*
H17B	0.8046	0.5016	0.1417	0.042*
H17C	0.8080	0.3662	0.1110	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.01693 (19)	0.02416 (19)	0.01697 (18)	0.00140 (16)	−0.00137 (14)	0.00051 (14)
N1	0.0194 (7)	0.0226 (6)	0.0208 (6)	0.0010 (6)	−0.0020 (5)	0.0008 (5)
N2	0.0206 (7)	0.0228 (6)	0.0204 (6)	0.0003 (6)	−0.0035 (5)	0.0018 (5)
N3	0.0152 (6)	0.0223 (6)	0.0150 (6)	0.0028 (5)	−0.0032 (5)	−0.0016 (5)
N4	0.0180 (7)	0.0236 (6)	0.0162 (6)	0.0037 (5)	−0.0028 (5)	0.0004 (5)
C1	0.0173 (7)	0.0207 (7)	0.0179 (7)	0.0010 (6)	−0.0022 (6)	−0.0016 (5)
C2	0.0201 (8)	0.0202 (7)	0.0156 (7)	0.0018 (6)	−0.0018 (6)	−0.0014 (5)
C3	0.0170 (7)	0.0216 (7)	0.0152 (6)	0.0025 (6)	−0.0012 (5)	−0.0031 (6)
C4	0.0157 (7)	0.0203 (7)	0.0174 (7)	−0.0008 (6)	−0.0005 (6)	0.0007 (5)
C5	0.0177 (8)	0.0213 (7)	0.0156 (7)	0.0016 (6)	−0.0016 (6)	0.0029 (6)
C6	0.0160 (8)	0.0273 (8)	0.0187 (7)	−0.0008 (6)	0.0009 (6)	0.0040 (6)
C7	0.0206 (8)	0.0243 (7)	0.0176 (7)	−0.0033 (6)	−0.0021 (6)	0.0005 (6)
C8	0.0213 (8)	0.0211 (7)	0.0159 (7)	0.0011 (6)	−0.0011 (6)	0.0009 (6)
C9	0.0169 (8)	0.0261 (7)	0.0183 (7)	−0.0009 (6)	0.0000 (6)	0.0000 (6)
C10	0.0199 (8)	0.0231 (7)	0.0173 (7)	−0.0015 (6)	−0.0019 (6)	−0.0001 (6)
C11	0.0229 (8)	0.0220 (7)	0.0216 (7)	0.0004 (7)	−0.0003 (6)	−0.0025 (6)
C12	0.0250 (8)	0.0251 (7)	0.0173 (7)	−0.0009 (7)	0.0011 (6)	−0.0027 (6)
C13	0.0396 (12)	0.0501 (12)	0.0232 (9)	0.0150 (10)	−0.0006 (8)	0.0033 (8)
C14	0.0390 (11)	0.0327 (9)	0.0209 (8)	−0.0027 (8)	0.0081 (7)	−0.0058 (7)
C15	0.0191 (8)	0.0254 (7)	0.0197 (7)	0.0004 (7)	−0.0011 (6)	0.0021 (6)
C16	0.0197 (8)	0.0283 (8)	0.0190 (7)	−0.0001 (7)	−0.0025 (6)	0.0018 (6)
C17	0.0250 (9)	0.0339 (9)	0.0250 (8)	−0.0023 (8)	−0.0005 (7)	0.0058 (7)

S1—C1	1.7323 (16)	C9—H9A	0.93
S1—C3	1.7669 (16)	C10—H10A	0.93
N1—C2	1.311 (2)	C11—C12	1.535 (2)
N1—N2	1.412 (2)	C11—H11A	0.97
N2—C1	1.309 (2)	C11—H11B	0.97
N3—C1	1.365 (2)	C12—C13	1.519 (3)
N3—C2	1.372 (2)	C12—C14	1.524 (2)
N3—N4	1.3861 (17)	C12—H12A	0.98
N4—C3	1.297 (2)	C13—H13A	0.96
C2—C16	1.490 (2)	C13—H13B	0.96
C3—C4	1.507 (2)	C13—H13C	0.96
C4—C15	1.521 (2)	C14—H14A	0.96
C4—C5	1.533 (2)	C14—H14B	0.96
C4—H4A	0.98	C14—H14C	0.96
C5—C10	1.391 (2)	C15—H15A	0.96
C5—C6	1.392 (2)	C15—H15B	0.96
C6—C7	1.394 (2)	C15—H15C	0.96
C6—H6A	0.93	C16—C17	1.522 (2)
C7—C8	1.393 (2)	C16—H16A	0.97
C7—H7A	0.93	C16—H16B	0.97
C8—C9	1.391 (2)	C17—H17A	0.96
C8—C11	1.507 (2)	C17—H17B	0.96
C9—C10	1.388 (2)	C17—H17C	0.96
C1—S1—C3	87.95 (8)	C8—C11—H11A	108.7
C2—N1—N2	109.27 (13)	C12—C11—H11A	108.7
C1—N2—N1	105.09 (13)	C8—C11—H11B	108.7
C1—N3—C2	106.02 (13)	C12—C11—H11B	108.7
C1—N3—N4	118.26 (13)	H11A—C11—H11B	107.6
C2—N3—N4	135.73 (14)	C13—C12—C14	110.66 (15)
C3—N4—N3	107.84 (13)	C13—C12—C11	111.92 (15)
N2—C1—N3	111.33 (14)	C14—C12—C11	110.27 (14)
N2—C1—S1	139.54 (14)	C13—C12—H12A	108.0
N3—C1—S1	109.12 (11)	C14—C12—H12A	108.0
N1—C2—N3	108.30 (14)	C11—C12—H12A	108.0
N1—C2—C16	127.38 (14)	C12—C13—H13A	109.5
N3—C2—C16	124.30 (14)	C12—C13—H13B	109.5
N4—C3—C4	124.01 (14)	H13A—C13—H13B	109.5
N4—C3—S1	116.82 (12)	C12—C13—H13C	109.5
C4—C3—S1	119.17 (12)	H13A—C13—H13C	109.5
C3—C4—C15	111.06 (13)	H13B—C13—H13C	109.5
C3—C4—C5	109.16 (12)	C12—C14—H14A	109.5
C15—C4—C5	113.52 (13)	C12—C14—H14B	109.5
C3—C4—H4A	107.6	H14A—C14—H14B	109.5
C15—C4—H4A	107.6	C12—C14—H14C	109.5
C5—C4—H4A	107.6	H14A—C14—H14C	109.5
C10—C5—C6	118.29 (14)	H14B—C14—H14C	109.5
C10—C5—C4	119.44 (14)	C4—C15—H15A	109.5
C6—C5—C4	122.23 (14)	C4—C15—H15B	109.5
C5—C6—C7	120.70 (15)	H15A—C15—H15B	109.5
C5—C6—H6A	119.6	C4—C15—H15C	109.5
C7—C6—H6A	119.6	H15A—C15—H15C	109.5
C8—C7—C6	121.16 (15)	H15B—C15—H15C	109.5
C8—C7—H7A	119.4	C2—C16—C17	112.23 (14)
C6—C7—H7A	119.4	C2—C16—H16A	109.2
C9—C8—C7	117.63 (14)	C17—C16—H16A	109.2
C9—C8—C11	121.30 (15)	C2—C16—H16B	109.2
C7—C8—C11	121.02 (15)	C17—C16—H16B	109.2
C10—C9—C8	121.49 (15)	H16A—C16—H16B	107.9
C10—C9—H9A	119.3	C16—C17—H17A	109.5
C8—C9—H9A	119.3	C16—C17—H17B	109.5
C9—C10—C5	120.72 (15)	H17A—C17—H17B	109.5
C9—C10—H10A	119.6	C16—C17—H17C	109.5
C5—C10—H10A	119.6	H17A—C17—H17C	109.5
C8—C11—C12	114.32 (13)	H17B—C17—H17C	109.5
C2—N1—N2—C1	0.16 (17)	N4—C3—C4—C5	107.16 (17)
C1—N3—N4—C3	0.31 (18)	S1—C3—C4—C5	−72.12 (15)
C2—N3—N4—C3	179.77 (16)	C3—C4—C5—C10	85.48 (17)
N1—N2—C1—N3	−0.05 (17)	C15—C4—C5—C10	−150.03 (14)
N1—N2—C1—S1	−178.90 (15)	C3—C4—C5—C6	−92.33 (17)
C2—N3—C1—N2	−0.07 (17)	C15—C4—C5—C6	32.2 (2)
N4—N3—C1—N2	179.54 (13)	C10—C5—C6—C7	−0.3 (2)
C2—N3—C1—S1	179.14 (10)	C4—C5—C6—C7	177.54 (14)
N4—N3—C1—S1	−1.25 (17)	C5—C6—C7—C8	−0.3 (2)
C3—S1—C1—N2	−179.82 (19)	C6—C7—C8—C9	0.6 (2)
C3—S1—C1—N3	1.31 (11)	C6—C7—C8—C11	178.26 (15)
N2—N1—C2—N3	−0.20 (17)	C7—C8—C9—C10	−0.4 (2)
N2—N1—C2—C16	178.03 (15)	C11—C8—C9—C10	−178.00 (15)
C1—N3—C2—N1	0.17 (17)	C8—C9—C10—C5	−0.2 (2)
N4—N3—C2—N1	−179.34 (15)	C6—C5—C10—C9	0.6 (2)
C1—N3—C2—C16	−178.13 (15)	C4—C5—C10—C9	−177.35 (14)
N4—N3—C2—C16	2.4 (3)	C9—C8—C11—C12	75.4 (2)
N3—N4—C3—C4	−178.48 (13)	C7—C8—C11—C12	−102.21 (18)
N3—N4—C3—S1	0.82 (16)	C8—C11—C12—C13	52.6 (2)
C1—S1—C3—N4	−1.30 (13)	C8—C11—C12—C14	176.26 (15)
C1—S1—C3—C4	178.03 (12)	N1—C2—C16—C17	3.7 (2)
N4—C3—C4—C15	−18.7 (2)	N3—C2—C16—C17	−178.28 (14)
S1—C3—C4—C15	161.97 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N1i	0.93	2.51	3.440 (2)	177
C15—H15A···Cg1ii	0.96	2.67	3.5090 (17)	146
C16—H16B···Cg1iii	0.97	2.93	3.6772 (18)	135
C17—H17B···Cg2iii	0.96	2.92	3.614 (2)	130
C15—H15B···Cg3ii	0.96	2.74	3.6335 (17)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N1i	0.93	2.51	3.440 (2)	177
C15—H15A⋯Cg1ii	0.96	2.67	3.5090 (17)	146
C16—H16B⋯Cg1iii	0.97	2.93	3.6772 (18)	135
C17—H17B⋯Cg2iii	0.96	2.92	3.614 (2)	130
C15—H15B⋯Cg3ii	0.96	2.74	3.6335 (17)	155

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids of the S1/C1/N3/N4/C3, N1/N2/C1/N3/C2 and C5–C10 rings, respectively.