3-Ethyl-6-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

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

doi:10.1107/S1600536808027086

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1838-o1839

doi:10.1107/S1600536808027086

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3-Ethyl-6-{1-[4-(2-methylpropyl)phenyl]ethyl}-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

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

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574199, India, and ^cDepartment of Physics, K.L.E. Society's K.L.E. Institute of Technology, Gokul Road, Hubli 590030, India
^*Correspondence e-mail: hkfun@usm.my

(Received 22 August 2008; accepted 22 August 2008; online 30 August 2008)

In the molecule of the title compound, C₁₇H₂₂N₄S, the triazolothiadiazole ring system is essentially planar and forms a dihedral angle of 74.34 (6)° with the benzene ring. In the crystal structure, molecules are linked into chains running along the b axis by C—H⋯π interactions; 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_r = 314.45
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.04
5793 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.49 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1, Cg2 and Cg3 are the centroids of the S1/C1/N3/N4/C3, N1/N2/C1/N3/C2 and C5–C10 rings, respectively.

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/S1600536808027086/ci2662sup1.cif

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

checkCIF report

Comment top

1,2,4-Triazole and 1,3,4-thiadiazoles represent one of the most biologically active classes of compounds, possessing a wide spectrum of activities (Ragenovic et al., 2001; Al-Soud et al., 2004; Labanauskas et al., 2004). Various substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their analogues are associated with diverse pharmacological activities such as antimicrobial (Swamy et al., 2006), antibacterial (Wang et al., 1996), antitubercular, anti-inflammatory and antifungal (Karegoudar et al., 2008). A triazolo-thiadiazole system may be viewed as a cyclic analogue of two very important components viz. thiosemicarbazide and biguanide, which often display diverse biological activities (Mathew et al., 2006). The required 4-amino-3-mercapto-5-ethyl-1,2,4-triazole was prepared in good yield through multi step reaction by using the method of Reid and Heindel (Bhalerao et al., 1994). Phosphorous oxychloride was necessary for this condensation, which activate the carbonyl group of aromatic acids and increases its electrophilicity to enhance the addition of triazole to it. Previously, we have reported the crystal structure of a triazolo-thiadiazole system carrying ibuprofen moiety (Fun et al., 2008). In continuation of our work, we report here the crystal structure of the title compound.

Bond lengths in the title molecule have normal values (Allen et al., 1987). The triazolothiadiazole (S1/C1/N2/N1/C2/N3/N4/C3) ring system is essentially planar, with a maximium deviation of 0.013 (1) Å for atom S1. The dihedral angle between the triazolothiadiazole ring system and the benzene ring (C5–C10) is 74.34 (6)°.

The crystal packing is consolidated by weak C—H···π interactions (Table 1) involving the thiadiazole (S1/C1/N3/N4/C3, centroid Cg1), triazole (N1/N2/C1/N3/C2, centroid Cg2) and benzene (C5–C10, centroid Cg3) rings, and C—H···N hydrogen bonds. The C—H···π interactions link the molecules into chains running along the b axis. The adjacent chains are cross-linked via C—H···N hydrogen bonds (Table 1) and short S···N contacts [3.2694 (14) Å or 3.2953 (14) Å] (Fig. 2).

Related literature top

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). Cg1, Cg2 and Cg3 are the centroids of the S1/C1/N3/N4/C3, N1/N2/C1/N3/C2 and C5–C10 rings, respectively.

Experimental top

A mixture of 4-amino-3-mercapto-5-ethyl-1,2,4-triazole (0.01 mol), 2-(4-isobutylphenyl)propanoic acid (0.01 mol) and POCl₃ (10 ml) was refluxed in a water bath for 16 h. Excess POCl₃ was removed under reduced pressure. The reaction mixture was cooled, poured into crushed ice, and neutralized with sodium bicarbonate solution. The resulting solid product was filtered off, washed with water, dried, and recrystallized from ethanol-dimethylformamide (1/1, v/v) (yield 49%; m.p. 369–371 K). Analysis (%) for C₁₇H₂₂N₄S found (calculated): C 64.89 (64.96), H 6.97 (7.006), N 17.78 (17.83) S 10.11 (10.19).

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 along the a axis. Short S···N contacts are shown as dashed lines.

(I) top

Crystal data top

C₁₇H₂₂N₄S	F(000) = 1344
M_r = 314.45	D_x = 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 = 2.2–29.2°
b = 9.1939 (4) Å	µ = 0.20 mm⁻¹
c = 30.9870 (13) Å	T = 100 K
V = 3257.5 (2) Å³	Needle, colourless
Z = 8	0.44 × 0.09 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5793 independent reflections
Radiation source: fine-focus sealed tube	4079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 32.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.917, T_max = 0.990	k = −13→13
40117 measured reflections	l = −40→46

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 2.0837P] where P = (F_o² + 2F_c²)/3
5793 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₇H₂₂N₄S	V = 3257.5 (2) Å³
M_r = 314.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.4341 (5) Å	µ = 0.20 mm⁻¹
b = 9.1939 (4) Å	T = 100 K
c = 30.9870 (13) Å	0.44 × 0.09 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5793 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4079 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.990	R_int = 0.048
40117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.60 e Å⁻³
5793 reflections	Δρ_min = −0.49 e Å⁻³
203 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	0.53939 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x+1, −y−3/2, z−1/2; (iii) x+1, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₂N₄S
M_r	314.45
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	11.4341 (5), 9.1939 (4), 30.9870 (13)
V (Å³)	3257.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.44 × 0.09 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.917, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	40117, 5793, 4079
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.753

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.04
No. of reflections	5793
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.49

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
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) −x+1, y−1/2, −z+1/2; (ii) x+1, −y−3/2, z−1/2; (iii) x+1, −y−1/2, z−1/2.

Footnotes

‡Permanent address,: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641114, India.

§Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. SKV and BK are grateful to Kerala State Council for Science, Technology and the Environment, Thiruvananthapuram, for financial assistance.

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–S19. CrossRef Web of Science Google Scholar
Al-Soud, Y. A., Al-Dweri, M. N. & Al-Masoudi, N. A. (2004). Farmaco, 59, 775–783. CrossRef PubMed CAS Google Scholar
Bhalerao, U. T., Muralikrishna, C. & Rani, B. R. (1994). Tetrahedron, 50, 4019–4024. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Jebas, S. R., Razak, I. A., Sujith, K. V., Patil, P. S., Kalluraya, B. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1076–o1077. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karegoudar, P., Prasad, D. J., Ashok, M., Mahalinga, M., Poojary, B. & Holla, B. S. (2008). Eur. J. Med. Chem. 43, 808–815. Web of Science CrossRef PubMed CAS Google Scholar
Labanauskas, L., Udrenaite, E., Gaidelis, P. & Bruktus, A. (2004). Farmaco, 59, 255–259. CrossRef PubMed CAS Google Scholar
Mathew, V., Keshavayya, J. & Vaidya, V. P. (2006). Eur. J. Med. Chem. 41, 1048–1058. Web of Science CrossRef PubMed CAS Google Scholar
Ragenovic, K. C., Dimova, V., Kakurinov, V., Labor, D. & Molnar, A. B. (2001). Molecules, 6, 815–824. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swamy, S. N., Basappa, B. S., Prabhuswamy, P. B., Doreswamy, B. H., Prasad, J. S. & Rangappa, K. S. (2006). Eur. J. Med. Chem. 41, 531–538. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wang, Z., You, T., Xu, Y., Haijian, S. & Haoxin, S. (1996). Molecules, 1, 68–71. CrossRef CAS Google Scholar

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Volume 64| Part 9| September 2008| Pages o1838-o1839

doi:10.1107/S1600536808027086

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

3-Ethyl-6-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-Ethyl-6-{1-[4-(2-methylpropyl)phenyl]ethyl}-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole