3-[1-(4-Isobutyl­phen­yl)eth­yl]-6-(4-methyl­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Fun, H.-K.; Jebas, S.R.; Razak, I.A.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Dharmaprakash, S.M.

doi:10.1107/S1600536808013883

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1076-o1077

doi:10.1107/S1600536808013883

Open

access

3-[1-(4-Isobutylphenyl)ethyl]-6-(4-methylphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

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

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

(Received 5 May 2008; accepted 9 May 2008; online 14 May 2008)

In the title compound, C₂₂H₂₄N₄S, 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 triazolothiadiazole unit. An intramolecular C—H⋯S hydrogen bond generates an S(5) ring motif. The crystal structure is stabilized by intermolecular C—H⋯N hydrogen bonds and weak C—H⋯π and π–π interactions [centroid–centroid distances between the thiadiazole 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_r = 376.51
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.141
S = 1.08
5687 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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) x, y+1, z; (ii) -x+1, -y, -z+1. Cg1 is the centroid of the C11–C16 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/S1600536808013883/sj2495sup1.cif

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

checkCIF report

Comment top

Triazoles and their heterocyclic derivatives represent an interesting class of compounds possessing a wide spectrum of biological activity, such as anticancer, anticonvulsant, analgesic, antibacterial, anthelmintic, antitubercular and anti-inflammatory activities (Holla et al., 2003; Bekircan & Bektas, 2006; Zhou et al., 2007). Similarly 1, 3,4-thiadiazoles were also found to possess antitumor, anti-inflammatory, antibacterial, antifungal, anticonvulsant and antitubercular properties (Bhat et al., 2004; Mathew et al., 2007). Thus triazolothiadiazole systems may be viewed as cyclic analogues of two very important components, which often display diverse pharmacological properties. Triazolothiadiazoles obtained by fusing the biolabile 1,2,4-triazole and 1,3,4-thiadiazole rings together have been reported to possess similar biological properties (Karthikeyan et al., 2007; Chaturvedi et al., 1988; Shawali & Sayed 2006) and the crystal structure of the title triazolothiadiazole compound is reported here.

Bond lengths and angles in the title compound (Fig 1) have normal values (Allen et al., 1987). The triazolothiadiazole ring is planar with the maximum deviation of 0.016 (2)Å for atom C7. The planes through the C1—C6 and C11—C16 rings form dihedral angles of 4.59 (1)° and 75.47 (1)° respectively, with the triazolothiadiazole unit. This is also planar with a dihedral angle of 1.34 (2) ° between the two five membered rings. A weak intramolecular C—H···S hydrogen bond generates an S(5) ring motif (Bernstein et al., (1995) and contributes to the planarity of the 4-methylphenyl-triazolothiadiazole portion of the molecule.

The crystal packing is stabilized by intermolecular C—H···N hydrogen bonds and a weak C—H···π interaction involving the C11—C16 ring (centroid Cg1, Table 1). π–π interactions are observed between the thiadiazole ring (S1/C7/N1—N2/C8) and the symmetry related phenyl rings (C1—C6) and between the triazole ring and the phenyl ring (C1—C6) with centroid to centroid distances ranging from 3.5680 (8)–3.7313 (8)Å [symmetry codes:1-X,-Y,1-Z;2-X, -Y,1-Z].

Related literature top

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). Cg1 is the centroid of the C11–C16 ring.

For related literature, see: Tayseer et al. (2002).

Experimental top

A mixture of 4-amino-3-mercapto-5-[1-(4-isobutylphenyl)ethyl]-1, 2,4-triazole (0.01 mol), p-toluic acid (0.01 mol) and 10 ml POCl₃ was refluxed on a water bath for about 9 h. Excess of POCl₃ was removed under reduced pressure. The reaction mixture was cooled, poured into crushed ice, and neutralized with aqueous ammonia. The resulting solid product was filtered off, washed with water, dried, and recrystallized from a mixture of ethanol and dimethylformamide, 1/1, v/v. (Yield 61%; m.p. 134–1360 C). Analysis (%) for C₂₂H₂₄N₄S found (calculated): C 70.16 (70.21), H 6.31 (6.38), N 14.78 (14.89).

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. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

3-[1-(4-Isobutylphenyl)ethyl]-6-(4-methylphenyl)-1,2,4- triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₂₂H₂₄N₄S	Z = 2
M_r = 376.51	F(000) = 400
Triclinic, P1	D_x = 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 = 2.6–32.0°
c = 17.6556 (3) Å	µ = 0.18 mm⁻¹
α = 97.539 (1)°	T = 100 K
β = 96.712 (1)°	Block, colourless
γ = 106.024 (1)°	0.46 × 0.20 × 0.18 mm
V = 984.90 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5687 independent reflections
Radiation source: fine-focus sealed tube	4391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→8
T_min = 0.922, T_max = 0.969	k = −11→11
15868 measured reflections	l = −24→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0792P)² + 0.0947P] where P = (F_o² + 2F_c²)/3
5687 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₂H₂₄N₄S	γ = 106.024 (1)°
M_r = 376.51	V = 984.90 (2) Å³
Triclinic, P1	Z = 2
a = 7.2545 (1) Å	Mo Kα radiation
b = 8.1764 (1) Å	µ = 0.18 mm⁻¹
c = 17.6556 (3) Å	T = 100 K
α = 97.539 (1)°	0.46 × 0.20 × 0.18 mm
β = 96.712 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5687 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4391 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.969	R_int = 0.029
15868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.08	Δρ_max = 0.45 e Å⁻³
5687 reflections	Δρ_min = −0.39 e Å⁻³
248 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	0.65630 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₄S
M_r	376.51
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.2545 (1), 8.1764 (1), 17.6556 (3)
α, β, γ (°)	97.539 (1), 96.712 (1), 106.024 (1)
V (Å³)	984.90 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.46 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.922, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	15868, 5687, 4391
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 1.08
No. of reflections	5687
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

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
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) x, y+1, z; (ii) −x+1, −y, −z+1.

Footnotes

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

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. FHK and IAR also thank the Malaysian Government and Universiti Sains Malaysia for the FRGS grant No. 203/PFIZIK/671064. 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–S19. CrossRef Web of Science Google Scholar
Bekircan, O. & Bektas, H. (2006). Molecules, 11, 469–477. Web of Science CrossRef PubMed CAS 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
Bhat, K. S., Prasad, D. J., Poojary, B. & Holla, B. S. (2004). Phosphorus, Sulfur Silicon, 179, 1595–1603. Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chaturvedi, B., Tiwari, N. and Nizamuddin. (1988). Agric. Biol. Chem. 52, 1229–1232. Google Scholar
Holla, B. S., Veerendra, B., Shivananda, M. K. & Poojary, B. (2003). Eur. J. Med. Chem. 38, 759–767. Web of Science CrossRef PubMed Google Scholar
Karthikeyan, M. S., Holla, B. S., Kalluraya, B. & Kumari, N. S. (2007). Monatsh. Chem. 138, 1309–1316. Web of Science CrossRef CAS Google Scholar
Mathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823–840. Web of Science CrossRef PubMed CAS Google Scholar
Shawali, A. S. & Sayed, A. R. (2006). J. Sulfur Chem. 27, 233–244. CrossRef CAS 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
Tayseer, A. A., Manal, A. D. & Hamdi, M. H. (2002). Molecules, 7, 494–500. Google Scholar
Zhou, S., Zhang, L., Jin, J., Zhang, A., Lei, X., Lin, J., He, J. & Zhang, H. (2007). Phosphorus, Sulfur Silicon, 182, 419–432. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1076-o1077

doi:10.1107/S1600536808013883

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

3-[1-(4-Iso­butyl­phen­yl)eth­yl]-6-(4-methyl­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-[1-(4-Isobutylphenyl)ethyl]-6-(4-methylphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole