6-(4-Methyl­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Du, H.-T.; Du, H.-J.; Zhou, W.

doi:10.1107/S1600536808030936

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2040

doi:10.1107/S1600536808030936

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6-(4-Methylphenyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Hai-Tang Du,^a ^* Hai-Jun Du ^b and Weiyi Zhou ^c

^aInstitute of Natural Products, Research Center for Eco-Environmental Sciences, Guiyang College, Guiyang 550005, People's Republic of China, ^bSchool of Chemistry and Environment Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China, and ^cAnalytical Center, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 24 September 2008; accepted 25 September 2008; online 30 September 2008)

In the molecule of the title compound, C₁₉H₁₈N₄O₃S, the central heterocylic ring system is oriented with respect to the trimethoxyphenyl and 4-methylphenyl rings at dihedral angles of 1.1 (5) and 15.1 (5)°, respectively. The dihedral angle between the two benzene rings is 16.1 (4)°. In the crystal structure, molecules are linked by intermolecular C—H⋯O hydrogen bonds, and an intramolecular C—H⋯N interaction also occurs.

Related literature

For general background, see: Karabasanagouda et al. (2007 ); Mathew et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₈N₄O₃S
M_r = 382.43
Monoclinic, P 2₁ /n
a = 7.2613 (15) Å
b = 18.519 (4) Å
c = 13.314 (3) Å
β = 100.52 (3)°
V = 1760.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 113 (2) K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.959, T_max = 0.975
12668 measured reflections
4184 independent reflections
3593 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.06
4184 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.93	2.37	3.059 (2)	131
C7—H7B⋯O3ⁱ	0.96	2.45	3.202 (2)	135
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030936/bx2183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030936/bx2183Isup2.hkl

checkCIF report

Comment top

1,2,4-Triazole and 1,3,4-thiadiazole represent one of the most biologically active classes of compounds, possessing a wide spectrum of activities. Various substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles are associated with diverse pharmacological activities such as antimicrobial (Karabasanagouda et al., 2007) and anti-inflammatory activity (Mathew et al., 2007). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C1—C6), B (N1—N3/C10/C11), C (S1/N3/N4/C11/C12) and D (C13—C18) are, of course, planar, and the dihedral angles between them are A/B = 0.61 (3)°, A/C = 1.57 (3)°, A/D = 16.09 (4)°, B/C = 0.96 (4)°, B/D = 15.53 (4)° and C/D = 14.60 (4)°. So, rings B and C are nearly coplanar. The coplanar ring system is oriented with respect to rings A and D at dihedral angles of 1.36 (3)° and 14.77 (4)°.

In the crystal structure, intramolecular C—H···N hydrogen bond results in the formation of a six-membered ring, intermolecular C—H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Karabasanagouda et al. (2007); Mathew et al. (2007).

Experimental top

For the preparation of the title compound, 4-amino-5-(3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole-3-thiol (0.01 M) and 4-methylbenzoic acid (0.01 M) were dissolved in dry phosphorous oxychloride (10 ml). The resulted solution was further heated under reflux for 7 h. The reaction mixture was cooled to room temperature and the mixture was gradually poured onto crushed ice with stirring. Finally, powdered potassium carbonate and the required amount of solid potassium hydroxide were added until the pH of the mixture was raised to 8, to remove the excess of phosphorous oxychloride. The mixture was allowed to stand overnight and the solid was separated. It was filtered, washed with cold water, and then dried. Crystals suitable for X-ray analysis were obtained by the recrystallization of the solid residue from a mixture of N,N-dimethylformamide/ ethanol (1:1) by slow evaporation at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. [Symmetry code: O3 (x+1/2, -y+3/2, z+1/2)].

6-(4-Methylphenyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4- triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₁₉H₁₈N₄O₃S	F(000) = 800
M_r = 382.43	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 461 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.2613 (15) Å	Cell parameters from 4938 reflections
b = 18.519 (4) Å	θ = 2.2–27.9°
c = 13.314 (3) Å	µ = 0.21 mm⁻¹
β = 100.52 (3)°	T = 113 K
V = 1760.2 (6) Å³	Prism, colourless
Z = 4	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn diffractometer	4184 independent reflections
Radiation source: rotating anode	3593 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.030
ω scans	θ_max = 27.9°, θ_min = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −9→9
T_min = 0.959, T_max = 0.975	k = −21→24
12668 measured reflections	l = −14→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0558P)² + 0.2342P] where P = (F_o² + 2F_c²)/3
4184 reflections	(Δ/σ)_max = 0.003
248 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₁₈N₄O₃S	V = 1760.2 (6) Å³
M_r = 382.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2613 (15) Å	µ = 0.21 mm⁻¹
b = 18.519 (4) Å	T = 113 K
c = 13.314 (3) Å	0.20 × 0.18 × 0.12 mm
β = 100.52 (3)°

Data collection top

Rigaku Saturn diffractometer	4184 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3593 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.975	R_int = 0.030
12668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
4184 reflections	Δρ_min = −0.26 e Å⁻³
248 parameters

Special details top

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	0.94253 (4)	1.187575 (15)	0.09160 (2)	0.01899 (10)
O1	0.66918 (12)	0.79479 (4)	0.06276 (7)	0.02001 (19)
O2	0.48496 (12)	0.74823 (4)	−0.11902 (7)	0.01879 (19)
O3	0.40808 (13)	0.83645 (5)	−0.27867 (7)	0.0217 (2)
N1	0.68396 (15)	1.08768 (5)	−0.14953 (8)	0.0197 (2)
N2	0.75719 (15)	1.15421 (5)	−0.11050 (8)	0.0215 (2)
N3	0.80820 (13)	1.07072 (5)	0.01101 (8)	0.0154 (2)
N4	0.87889 (13)	1.04929 (5)	0.10918 (8)	0.0161 (2)
C1	0.65260 (15)	0.96291 (6)	−0.08603 (9)	0.0147 (2)
C2	0.69065 (16)	0.91670 (6)	−0.00221 (9)	0.0157 (2)
H2	0.7524	0.9338	0.0607	0.019*
C3	0.63518 (16)	0.84455 (6)	−0.01355 (9)	0.0154 (2)
C4	0.54233 (16)	0.81924 (6)	−0.10783 (9)	0.0156 (2)
C5	0.50224 (16)	0.86673 (6)	−0.19093 (9)	0.0161 (2)
C6	0.55682 (16)	0.93877 (6)	−0.18036 (9)	0.0163 (2)
H6	0.5298	0.9703	−0.2354	0.020*
C7	0.74671 (19)	0.82186 (7)	0.16222 (10)	0.0222 (3)
H7A	0.8675	0.8426	0.1612	0.033*
H7B	0.7594	0.7830	0.2107	0.033*
H7C	0.6652	0.8581	0.1814	0.033*
C8	0.62703 (18)	0.70088 (7)	−0.14319 (11)	0.0233 (3)
H8A	0.6576	0.7145	−0.2077	0.035*
H8B	0.5816	0.6521	−0.1470	0.035*
H8C	0.7369	0.7043	−0.0910	0.035*
C9	0.36549 (19)	0.88121 (7)	−0.36669 (10)	0.0235 (3)
H9A	0.2894	0.9210	−0.3527	0.035*
H9B	0.2987	0.8536	−0.4228	0.035*
H9C	0.4796	0.8992	−0.3840	0.035*
C10	0.71354 (16)	1.03844 (6)	−0.07648 (9)	0.0158 (2)
C11	0.82850 (17)	1.14151 (6)	−0.01460 (10)	0.0175 (2)
C12	0.95402 (16)	1.10531 (6)	0.15977 (10)	0.0166 (2)
C13	1.04249 (16)	1.10151 (6)	0.26740 (9)	0.0165 (2)
C14	1.08199 (17)	1.16412 (7)	0.32607 (10)	0.0205 (3)
H14	1.0555	1.2091	0.2959	0.025*
C15	1.15986 (18)	1.15957 (7)	0.42833 (10)	0.0221 (3)
H15	1.1834	1.2018	0.4663	0.026*
C16	1.20416 (18)	1.09329 (7)	0.47618 (10)	0.0213 (3)
C17	1.16536 (18)	1.03064 (7)	0.41664 (10)	0.0221 (3)
H17	1.1934	0.9857	0.4469	0.026*
C18	1.08647 (17)	1.03423 (6)	0.31419 (10)	0.0200 (3)
H18	1.0625	0.9920	0.2762	0.024*
C19	1.2948 (2)	1.08960 (8)	0.58656 (11)	0.0297 (3)
H19A	1.4187	1.0700	0.5923	0.044*
H19B	1.2217	1.0592	0.6226	0.044*
H19C	1.3021	1.1372	0.6154	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02085 (17)	0.01264 (15)	0.02384 (17)	−0.00229 (10)	0.00504 (12)	−0.00188 (11)
O1	0.0277 (5)	0.0151 (4)	0.0155 (4)	−0.0007 (3)	−0.0008 (4)	0.0016 (3)
O2	0.0206 (4)	0.0136 (4)	0.0223 (5)	−0.0038 (3)	0.0040 (4)	−0.0029 (3)
O3	0.0277 (5)	0.0203 (4)	0.0149 (4)	−0.0055 (4)	−0.0020 (4)	−0.0003 (3)
N1	0.0231 (5)	0.0157 (5)	0.0206 (5)	−0.0005 (4)	0.0047 (4)	0.0002 (4)
N2	0.0271 (6)	0.0150 (5)	0.0233 (6)	−0.0019 (4)	0.0068 (5)	−0.0005 (4)
N3	0.0157 (5)	0.0125 (4)	0.0183 (5)	−0.0004 (4)	0.0042 (4)	0.0001 (4)
N4	0.0158 (5)	0.0161 (5)	0.0164 (5)	0.0004 (4)	0.0030 (4)	−0.0008 (4)
C1	0.0130 (5)	0.0144 (5)	0.0175 (6)	0.0004 (4)	0.0049 (4)	−0.0013 (4)
C2	0.0155 (5)	0.0155 (5)	0.0158 (6)	0.0000 (4)	0.0020 (4)	−0.0020 (4)
C3	0.0154 (5)	0.0148 (5)	0.0160 (6)	0.0016 (4)	0.0030 (4)	0.0009 (4)
C4	0.0150 (5)	0.0137 (5)	0.0186 (6)	−0.0021 (4)	0.0040 (5)	−0.0022 (4)
C5	0.0139 (5)	0.0196 (5)	0.0149 (6)	−0.0012 (4)	0.0028 (4)	−0.0019 (4)
C6	0.0154 (5)	0.0176 (5)	0.0161 (6)	0.0002 (4)	0.0038 (4)	0.0015 (4)
C7	0.0280 (7)	0.0206 (6)	0.0152 (6)	0.0018 (5)	−0.0034 (5)	0.0011 (5)
C8	0.0247 (6)	0.0166 (6)	0.0274 (7)	0.0015 (5)	0.0011 (5)	−0.0029 (5)
C9	0.0249 (6)	0.0302 (7)	0.0146 (6)	−0.0042 (5)	0.0016 (5)	0.0024 (5)
C10	0.0158 (5)	0.0159 (5)	0.0163 (6)	0.0012 (4)	0.0047 (4)	−0.0013 (4)
C11	0.0183 (6)	0.0124 (5)	0.0231 (6)	−0.0007 (4)	0.0069 (5)	0.0001 (4)
C12	0.0151 (5)	0.0138 (5)	0.0223 (6)	−0.0002 (4)	0.0065 (5)	−0.0015 (4)
C13	0.0139 (5)	0.0176 (5)	0.0188 (6)	−0.0012 (4)	0.0052 (5)	−0.0037 (4)
C14	0.0208 (6)	0.0159 (5)	0.0250 (7)	0.0001 (5)	0.0048 (5)	−0.0036 (5)
C15	0.0236 (6)	0.0194 (6)	0.0234 (7)	−0.0032 (5)	0.0047 (5)	−0.0080 (5)
C16	0.0206 (6)	0.0240 (6)	0.0202 (6)	−0.0031 (5)	0.0062 (5)	−0.0042 (5)
C17	0.0266 (6)	0.0177 (6)	0.0227 (7)	−0.0017 (5)	0.0064 (5)	0.0004 (5)
C18	0.0229 (6)	0.0166 (6)	0.0211 (6)	−0.0029 (5)	0.0059 (5)	−0.0038 (4)
C19	0.0365 (8)	0.0299 (7)	0.0217 (7)	−0.0041 (6)	0.0029 (6)	−0.0034 (5)

Geometric parameters (Å, º) top

S1—C11	1.7276 (13)	C7—H7A	0.9600
S1—C12	1.7675 (13)	C7—H7B	0.9600
O1—C3	1.3604 (14)	C7—H7C	0.9600
O1—C7	1.4315 (15)	C8—H8A	0.9600
O2—C4	1.3792 (13)	C8—H8B	0.9600
O2—C8	1.4346 (15)	C8—H8C	0.9600
O3—C5	1.3619 (14)	C9—H9A	0.9600
O3—C9	1.4225 (15)	C9—H9B	0.9600
N1—C10	1.3218 (15)	C9—H9C	0.9600
N1—N2	1.4035 (14)	C12—C13	1.4611 (18)
N2—C11	1.3085 (17)	C13—C14	1.3983 (16)
N3—C11	1.3693 (15)	C13—C18	1.4034 (17)
N3—N4	1.3727 (14)	C14—C15	1.3781 (19)
N3—C10	1.3763 (15)	C14—H14	0.9300
N4—C12	1.3012 (15)	C15—C16	1.3931 (18)
C1—C2	1.3934 (16)	C15—H15	0.9300
C1—C6	1.3935 (17)	C16—C17	1.4044 (17)
C1—C10	1.4655 (16)	C16—C19	1.4981 (19)
C2—C3	1.3959 (16)	C17—C18	1.3812 (18)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.3931 (17)	C18—H18	0.9300
C4—C5	1.4017 (16)	C19—H19A	0.9600
C5—C6	1.3915 (16)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600

C11—S1—C12	88.01 (6)	O3—C9—H9A	109.5
C3—O1—C7	116.15 (9)	O3—C9—H9B	109.5
C4—O2—C8	113.06 (9)	H9A—C9—H9B	109.5
C5—O3—C9	117.79 (10)	O3—C9—H9C	109.5
C10—N1—N2	109.48 (10)	H9A—C9—H9C	109.5
C11—N2—N1	105.02 (10)	H9B—C9—H9C	109.5
C11—N3—N4	118.38 (10)	N1—C10—N3	108.18 (10)
C11—N3—C10	105.37 (10)	N1—C10—C1	126.06 (11)
N4—N3—C10	136.25 (10)	N3—C10—C1	125.75 (11)
C12—N4—N3	108.12 (10)	N2—C11—N3	111.94 (10)
C2—C1—C6	121.21 (11)	N2—C11—S1	139.02 (9)
C2—C1—C10	120.27 (11)	N3—C11—S1	109.04 (9)
C6—C1—C10	118.52 (11)	N4—C12—C13	122.48 (11)
C1—C2—C3	119.35 (11)	N4—C12—S1	116.44 (10)
C1—C2—H2	120.3	C13—C12—S1	121.08 (9)
C3—C2—H2	120.3	C14—C13—C18	118.77 (11)
O1—C3—C4	115.91 (10)	C14—C13—C12	121.10 (11)
O1—C3—C2	123.93 (11)	C18—C13—C12	120.12 (10)
C4—C3—C2	120.15 (11)	C15—C14—C13	120.43 (12)
O2—C4—C3	120.33 (10)	C15—C14—H14	119.8
O2—C4—C5	119.86 (10)	C13—C14—H14	119.8
C3—C4—C5	119.78 (10)	C14—C15—C16	121.63 (11)
O3—C5—C6	124.79 (11)	C14—C15—H15	119.2
O3—C5—C4	114.71 (10)	C16—C15—H15	119.2
C6—C5—C4	120.50 (11)	C15—C16—C17	117.64 (12)
C5—C6—C1	118.99 (11)	C15—C16—C19	120.81 (11)
C5—C6—H6	120.5	C17—C16—C19	121.52 (12)
C1—C6—H6	120.5	C18—C17—C16	121.46 (12)
O1—C7—H7A	109.5	C18—C17—H17	119.3
O1—C7—H7B	109.5	C16—C17—H17	119.3
H7A—C7—H7B	109.5	C17—C18—C13	120.06 (11)
O1—C7—H7C	109.5	C17—C18—H18	120.0
H7A—C7—H7C	109.5	C13—C18—H18	120.0
H7B—C7—H7C	109.5	C16—C19—H19A	109.5
O2—C8—H8A	109.5	C16—C19—H19B	109.5
O2—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8B	109.5	C16—C19—H19C	109.5
O2—C8—H8C	109.5	H19A—C19—H19C	109.5
H8A—C8—H8C	109.5	H19B—C19—H19C	109.5
H8B—C8—H8C	109.5

C10—N1—N2—C11	0.10 (13)	C2—C1—C10—N1	−179.02 (11)
C11—N3—N4—C12	0.36 (14)	C6—C1—C10—N1	1.10 (18)
C10—N3—N4—C12	−179.17 (12)	C2—C1—C10—N3	−0.50 (18)
C6—C1—C2—C3	1.35 (17)	C6—C1—C10—N3	179.61 (10)
C10—C1—C2—C3	−178.53 (10)	N1—N2—C11—N3	0.69 (13)
C7—O1—C3—C4	−173.70 (10)	N1—N2—C11—S1	−179.31 (11)
C7—O1—C3—C2	7.59 (16)	N4—N3—C11—N2	179.15 (9)
C1—C2—C3—O1	178.51 (10)	C10—N3—C11—N2	−1.19 (13)
C1—C2—C3—C4	−0.15 (17)	N4—N3—C11—S1	−0.85 (13)
C8—O2—C4—C3	−87.14 (13)	C10—N3—C11—S1	178.81 (7)
C8—O2—C4—C5	94.73 (13)	C12—S1—C11—N2	−179.22 (15)
O1—C3—C4—O2	2.14 (16)	C12—S1—C11—N3	0.79 (9)
C2—C3—C4—O2	−179.09 (10)	N3—N4—C12—C13	179.87 (10)
O1—C3—C4—C5	−179.73 (10)	N3—N4—C12—S1	0.32 (12)
C2—C3—C4—C5	−0.96 (17)	C11—S1—C12—N4	−0.68 (10)
C9—O3—C5—C6	1.35 (17)	C11—S1—C12—C13	179.76 (10)
C9—O3—C5—C4	−178.93 (10)	N4—C12—C13—C14	−164.70 (11)
O2—C4—C5—O3	−0.68 (16)	S1—C12—C13—C14	14.83 (16)
C3—C4—C5—O3	−178.82 (10)	N4—C12—C13—C18	14.20 (17)
O2—C4—C5—C6	179.05 (10)	S1—C12—C13—C18	−166.27 (9)
C3—C4—C5—C6	0.91 (17)	C18—C13—C14—C15	−1.05 (18)
O3—C5—C6—C1	179.96 (11)	C12—C13—C14—C15	177.87 (11)
C4—C5—C6—C1	0.26 (17)	C13—C14—C15—C16	0.95 (19)
C2—C1—C6—C5	−1.40 (17)	C14—C15—C16—C17	−0.48 (19)
C10—C1—C6—C5	178.49 (10)	C14—C15—C16—C19	177.87 (12)
N2—N1—C10—N3	−0.83 (13)	C15—C16—C17—C18	0.14 (19)
N2—N1—C10—C1	177.90 (11)	C19—C16—C17—C18	−178.20 (12)
C11—N3—C10—N1	1.20 (13)	C16—C17—C18—C13	−0.27 (19)
N4—N3—C10—N1	−179.23 (11)	C14—C13—C18—C17	0.71 (17)
C11—N3—C10—C1	−177.54 (11)	C12—C13—C18—C17	−178.21 (11)
N4—N3—C10—C1	2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.93	2.37	3.059 (2)	131
C6—H6···N1	0.93	2.61	2.913 (2)	100
C14—H14···S1	0.93	2.72	3.131 (2)	108
C7—H7B···O3ⁱ	0.96	2.45	3.202 (2)	135

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₃S
M_r	382.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	7.2613 (15), 18.519 (4), 13.314 (3)
β (°)	100.52 (3)
V (Å³)	1760.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.959, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	12668, 4184, 3593
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.06
No. of reflections	4184
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.93	2.37	3.059 (2)	131
C6—H6···N1	0.93	2.61	2.913 (2)	100
C14—H14···S1	0.93	2.72	3.131 (2)	108
C7—H7B···O3ⁱ	0.96	2.45	3.202 (2)	135

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Acknowledgements

The authors thank Guiyang College for financial support.

References

Karabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521–529. Web of Science CrossRef PubMed 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
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o2040

doi:10.1107/S1600536808030936

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

6-(4-Methyl­phen­yl)-3-(3,4,5-tri­meth­oxy­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-(4-Methylphenyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole