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

Du, H.; Du, H.; An, Y.; Li, S.

doi:10.1107/S160053680802062X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1481

doi:10.1107/S160053680802062X

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

Haitang Du,^a,^b ^* Haijun Du,^c Ying An ^a and Shengnan Li ^a

^aDepartment of Chemistry, College of Science, Tianjin University, Tianjin 300072, People's Republic of China, ^bDepartment of Biology and Environment alTechnology, Guiyang College, Guiyang 550005, People's Republic of China, and ^cSchool of Chemistry and Environmental Sciences, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 2 July 2008; accepted 4 July 2008; online 12 July 2008)

In the molecule of the title compound, C₁₉H₁₈N₄O₃S, the planar central heterocylic ring system is oriented with respect to the trimethoxyphenyl and 2-methylphenyl rings at dihedral angles of 4.43 (3) and 4.32 (3)°, respectively. The dihedral angle between the two benzene rings is 7.65 (4)°. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules into centrosymmetric R₂²(18) dimers. These dimers are connected via a C—H⋯π contact between the 2-methylphenyl and trimethoxyphenyl rings, and a π–π contact between the thiadiazole and trimethoxyphenyl rings [interplanar distance 3.51 Å, dihedral angles 4.17(4)°]. An intramolecular C—H⋯N hydrogen bond is also present.

Related literature

For general background, see: Karabasanagouda et al. (2007 ); Mathew et al. (2007 ). For ring motif details, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₈N₄O₃S
M_r = 382.43
Monoclinic, P 2₁ /c
a = 7.5108 (15) Å
b = 15.950 (3) Å
c = 14.096 (3) Å
β = 91.88 (3)°
V = 1687.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 113 (2) K
0.24 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.923, T_max = 0.965
11990 measured reflections
3984 independent reflections
3408 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.108
S = 1.07
3984 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.95	2.45	3.127 (3)	128
C7—H7C⋯N2ⁱ	0.98	2.62	3.524 (3)	154
C19—H19B⋯CgAⁱⁱ	0.98	2.90	3.808 (3)	155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y, -z. CgA is the centroid of the trimethoxyphenyl ring.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (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) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802062X/hk2487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802062X/hk2487Isup2.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 = 4.63 (4)°, A/C = 4.08 (3)°, A/D = 7.65 (4)°, B/C = 0.94 (3)°, B/D = 4.59 (4)° and C/D = 4.25 (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 4.43 (3)° and 4.32 (3)°, respectively. The intra- molecular C-H···N hydrogen bond (Table 1) results in the formation of a planar six-membered ring E (N3/N4/C1/C2/C10/H2), in which it is oriented with respect to the other rings at dihedral angles of A/E = 3.24 (4)°, B/E = 1.39 (3)°, C/E = 1.03 (3)° and D/E = 5.25 (4)°. So, rings A, B, C and E are also nearly coplanar.

In the crystal structure, intermolecular weak C-H···N hydrogen bonds (Table 1) link the molecules to form a R²₂(18) ring motif (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The C—H···π contact (Table 1) between the 2-methylphenyl and trimethoxyphenyl rings and a π—π contact between the thiadiazole and trimethoxyphenyl rings CgC···CgAⁱ [symmetry code: (i) 1 - x, 1 - y, 1 - z] further stabilize the structure, with centroid-centroid distance of 3.506 (1) Å.

Related literature top

For general background, see: Karabasanagouda et al. (2007); Mathew et al. (2007). For ring motif details, see: Bernstein et al. (1995). CgA is the centroid of the C1–C6 ring.

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 2-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-dimethyl- formamide/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: CrystalStructure (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) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

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 [symmetry code: (') -x, -y, -z]. Hydrogen bonds are shown as dashed lines.

6-(2-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 = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 435 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5108 (15) Å	Cell parameters from 4684 reflections
b = 15.950 (3) Å	θ = 1.9–27.9°
c = 14.096 (3) Å	µ = 0.22 mm⁻¹
β = 91.88 (3)°	T = 113 K
V = 1687.7 (6) Å³	Prism, colorless
Z = 4	0.24 × 0.20 × 0.16 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3984 independent reflections
Radiation source: rotating anode	3408 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.031
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −20→20
T_min = 0.923, T_max = 0.965	l = −17→18
11990 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0664P)² + 0.1888P] where P = (F_o² + 2F_c²)/3
3984 reflections	(Δ/σ)_max = 0.002
248 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₈N₄O₃S	V = 1687.7 (6) Å³
M_r = 382.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5108 (15) Å	µ = 0.22 mm⁻¹
b = 15.950 (3) Å	T = 113 K
c = 14.096 (3) Å	0.24 × 0.20 × 0.16 mm
β = 91.88 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3984 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3408 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.965	R_int = 0.031
11990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
3984 reflections	Δρ_min = −0.35 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 > 2sigma(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	0.45611 (5)	0.68554 (2)	0.69693 (2)	0.02005 (12)
O1	0.04396 (14)	0.40664 (6)	0.30838 (7)	0.0227 (2)
O2	0.03955 (14)	0.24866 (6)	0.34593 (7)	0.0223 (2)
O3	0.17803 (14)	0.18588 (6)	0.51532 (7)	0.0209 (2)
N1	0.43365 (17)	0.44321 (7)	0.69492 (9)	0.0208 (3)
N2	0.48819 (18)	0.51377 (8)	0.74703 (9)	0.0226 (3)
N3	0.36258 (15)	0.55345 (7)	0.61030 (8)	0.0156 (2)
N4	0.31020 (15)	0.61420 (7)	0.54614 (8)	0.0164 (2)
C1	0.27851 (18)	0.41101 (8)	0.54193 (10)	0.0162 (3)
C2	0.20134 (19)	0.44117 (8)	0.45750 (10)	0.0176 (3)
H2	0.2018	0.4995	0.4439	0.021*
C3	0.12374 (18)	0.38475 (9)	0.39346 (10)	0.0173 (3)
C4	0.12199 (18)	0.29857 (8)	0.41238 (10)	0.0170 (3)
C5	0.19617 (18)	0.26966 (8)	0.49906 (10)	0.0169 (3)
C6	0.27654 (18)	0.32539 (8)	0.56254 (10)	0.0174 (3)
H6	0.3303	0.3053	0.6201	0.021*
C7	0.0480 (2)	0.49299 (9)	0.28278 (11)	0.0232 (3)
H7A	−0.0099	0.5263	0.3314	0.035*
H7B	−0.0152	0.5009	0.2215	0.035*
H7C	0.1720	0.5112	0.2778	0.035*
C8	0.1222 (2)	0.17048 (9)	0.32363 (12)	0.0276 (4)
H8A	0.2513	0.1750	0.3349	0.041*
H8B	0.0968	0.1568	0.2568	0.041*
H8C	0.0751	0.1262	0.3639	0.041*
C9	0.2468 (2)	0.15402 (9)	0.60340 (11)	0.0247 (3)
H9A	0.3756	0.1639	0.6083	0.037*
H9B	0.2232	0.0937	0.6069	0.037*
H9C	0.1890	0.1826	0.6557	0.037*
C10	0.35879 (18)	0.46709 (8)	0.61313 (10)	0.0164 (3)
C11	0.44294 (18)	0.57788 (9)	0.69380 (10)	0.0182 (3)
C12	0.35200 (18)	0.68710 (8)	0.58207 (9)	0.0159 (3)
C13	0.32100 (18)	0.76838 (8)	0.53561 (10)	0.0167 (3)
C14	0.3639 (2)	0.84107 (9)	0.58780 (11)	0.0212 (3)
H14	0.4101	0.8357	0.6510	0.025*
C15	0.3405 (2)	0.92022 (9)	0.54955 (11)	0.0240 (3)
H15	0.3724	0.9686	0.5855	0.029*
C16	0.2700 (2)	0.92787 (9)	0.45800 (11)	0.0245 (3)
H16	0.2521	0.9819	0.4309	0.029*
C17	0.22563 (19)	0.85687 (9)	0.40588 (11)	0.0210 (3)
H17	0.1762	0.8634	0.3434	0.025*
C18	0.25090 (18)	0.77609 (9)	0.44191 (10)	0.0174 (3)
C19	0.2042 (2)	0.70232 (9)	0.37935 (10)	0.0206 (3)
H19A	0.1633	0.7224	0.3166	0.031*
H19B	0.1093	0.6697	0.4079	0.031*
H19C	0.3096	0.6669	0.3727	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0259 (2)	0.01750 (18)	0.01647 (19)	−0.00076 (13)	−0.00384 (14)	−0.00149 (12)
O1	0.0347 (6)	0.0148 (5)	0.0181 (5)	0.0021 (4)	−0.0071 (4)	0.0011 (4)
O2	0.0258 (6)	0.0165 (5)	0.0242 (6)	0.0014 (4)	−0.0056 (4)	−0.0036 (4)
O3	0.0278 (6)	0.0142 (5)	0.0203 (5)	−0.0019 (4)	−0.0035 (4)	0.0032 (4)
N1	0.0244 (7)	0.0189 (6)	0.0190 (6)	0.0012 (5)	−0.0023 (5)	−0.0002 (5)
N2	0.0287 (7)	0.0196 (6)	0.0193 (6)	0.0012 (5)	−0.0038 (5)	−0.0006 (5)
N3	0.0173 (6)	0.0158 (5)	0.0136 (5)	0.0000 (4)	−0.0010 (4)	0.0005 (4)
N4	0.0182 (6)	0.0149 (5)	0.0160 (6)	0.0005 (4)	−0.0002 (4)	0.0024 (4)
C1	0.0154 (6)	0.0170 (6)	0.0164 (7)	0.0007 (5)	0.0026 (5)	−0.0006 (5)
C2	0.0202 (7)	0.0150 (6)	0.0177 (7)	0.0015 (5)	0.0012 (5)	−0.0004 (5)
C3	0.0200 (7)	0.0179 (7)	0.0140 (6)	0.0031 (5)	0.0005 (5)	0.0003 (5)
C4	0.0171 (7)	0.0155 (6)	0.0184 (7)	−0.0001 (5)	0.0003 (5)	−0.0022 (5)
C5	0.0167 (7)	0.0142 (6)	0.0199 (7)	0.0010 (5)	0.0034 (5)	0.0014 (5)
C6	0.0168 (7)	0.0190 (7)	0.0165 (7)	0.0019 (5)	0.0005 (5)	0.0020 (5)
C7	0.0316 (8)	0.0161 (7)	0.0217 (7)	0.0028 (6)	−0.0042 (6)	0.0037 (5)
C8	0.0387 (9)	0.0170 (7)	0.0265 (8)	0.0034 (6)	−0.0065 (7)	−0.0061 (6)
C9	0.0335 (9)	0.0177 (7)	0.0227 (8)	−0.0002 (6)	−0.0037 (6)	0.0058 (6)
C10	0.0169 (7)	0.0146 (6)	0.0177 (7)	0.0008 (5)	0.0016 (5)	0.0014 (5)
C11	0.0196 (7)	0.0196 (6)	0.0154 (7)	−0.0006 (5)	−0.0010 (5)	−0.0013 (5)
C12	0.0147 (6)	0.0180 (7)	0.0149 (7)	−0.0003 (5)	0.0002 (5)	−0.0013 (5)
C13	0.0161 (7)	0.0163 (6)	0.0176 (7)	0.0005 (5)	0.0006 (5)	0.0000 (5)
C14	0.0233 (7)	0.0198 (7)	0.0204 (7)	0.0001 (6)	−0.0018 (6)	−0.0023 (6)
C15	0.0287 (8)	0.0161 (6)	0.0271 (8)	−0.0007 (6)	−0.0012 (6)	−0.0030 (6)
C16	0.0297 (8)	0.0168 (7)	0.0270 (8)	0.0013 (6)	0.0005 (6)	0.0025 (6)
C17	0.0218 (7)	0.0216 (7)	0.0198 (7)	0.0011 (6)	0.0004 (5)	0.0019 (5)
C18	0.0163 (7)	0.0190 (7)	0.0169 (7)	0.0004 (5)	0.0015 (5)	0.0003 (5)
C19	0.0245 (8)	0.0200 (7)	0.0172 (7)	−0.0012 (6)	−0.0015 (5)	−0.0009 (5)

Geometric parameters (Å, º) top

S1—C11	1.7205 (15)	C7—H7A	0.9800
S1—C12	1.7749 (15)	C7—H7B	0.9800
O1—C3	1.3682 (17)	C7—H7C	0.9800
O1—C7	1.4244 (16)	C8—H8A	0.9800
O2—C4	1.3625 (16)	C8—H8B	0.9800
O2—C8	1.4325 (17)	C8—H8C	0.9800
O3—C5	1.3633 (16)	C9—H9A	0.9800
O3—C9	1.4229 (17)	C9—H9B	0.9800
N1—C10	1.3221 (18)	C9—H9C	0.9800
N1—N2	1.3978 (17)	C12—C13	1.4677 (19)
N2—C11	1.3067 (18)	C13—C14	1.4048 (19)
N3—C11	1.3619 (18)	C13—C18	1.411 (2)
N3—N4	1.3742 (16)	C14—C15	1.382 (2)
N3—C10	1.3783 (17)	C14—H14	0.9500
N4—C12	1.3026 (17)	C15—C16	1.384 (2)
C1—C2	1.392 (2)	C15—H15	0.9500
C1—C6	1.3964 (19)	C16—C17	1.385 (2)
C1—C10	1.4600 (19)	C16—H16	0.9500
C2—C3	1.3893 (19)	C17—C18	1.3956 (19)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.4003 (19)	C18—C19	1.5050 (19)
C4—C5	1.404 (2)	C19—H19A	0.9800
C5—C6	1.3855 (19)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800

C11—S1—C12	88.13 (6)	O3—C9—H9A	109.5
C3—O1—C7	117.15 (11)	O3—C9—H9B	109.5
C4—O2—C8	117.97 (11)	H9A—C9—H9B	109.5
C5—O3—C9	117.47 (11)	O3—C9—H9C	109.5
C10—N1—N2	109.59 (11)	H9A—C9—H9C	109.5
C11—N2—N1	105.19 (12)	H9B—C9—H9C	109.5
C11—N3—N4	118.44 (11)	N1—C10—N3	107.73 (12)
C11—N3—C10	105.66 (11)	N1—C10—C1	125.26 (12)
N4—N3—C10	135.89 (12)	N3—C10—C1	126.93 (12)
C12—N4—N3	108.26 (11)	N2—C11—N3	111.83 (13)
C2—C1—C6	120.59 (13)	N2—C11—S1	138.82 (11)
C2—C1—C10	121.79 (12)	N3—C11—S1	109.35 (10)
C6—C1—C10	117.59 (12)	N4—C12—C13	125.61 (13)
C3—C2—C1	119.05 (13)	N4—C12—S1	115.82 (10)
C3—C2—H2	120.5	C13—C12—S1	118.57 (10)
C1—C2—H2	120.5	C14—C13—C18	119.37 (13)
O1—C3—C2	124.52 (12)	C14—C13—C12	117.71 (13)
O1—C3—C4	114.26 (12)	C18—C13—C12	122.93 (12)
C2—C3—C4	121.23 (13)	C15—C14—C13	121.71 (14)
O2—C4—C3	116.72 (12)	C15—C14—H14	119.1
O2—C4—C5	124.38 (12)	C13—C14—H14	119.1
C3—C4—C5	118.83 (12)	C14—C15—C16	118.96 (14)
O3—C5—C6	124.34 (13)	C14—C15—H15	120.5
O3—C5—C4	115.42 (12)	C16—C15—H15	120.5
C6—C5—C4	120.22 (12)	C15—C16—C17	120.04 (14)
C5—C6—C1	120.03 (13)	C15—C16—H16	120.0
C5—C6—H6	120.0	C17—C16—H16	120.0
C1—C6—H6	120.0	C16—C17—C18	122.30 (14)
O1—C7—H7A	109.5	C16—C17—H17	118.8
O1—C7—H7B	109.5	C18—C17—H17	118.8
H7A—C7—H7B	109.5	C17—C18—C13	117.60 (13)
O1—C7—H7C	109.5	C17—C18—C19	118.83 (13)
H7A—C7—H7C	109.5	C13—C18—C19	123.57 (12)
H7B—C7—H7C	109.5	C18—C19—H19A	109.5
O2—C8—H8A	109.5	C18—C19—H19B	109.5
O2—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8B	109.5	C18—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	0.13 (16)	C2—C1—C10—N1	179.68 (13)
C11—N3—N4—C12	−0.04 (16)	C6—C1—C10—N1	1.6 (2)
C10—N3—N4—C12	−178.51 (15)	C2—C1—C10—N3	3.3 (2)
C6—C1—C2—C3	−0.6 (2)	C6—C1—C10—N3	−174.73 (13)
C10—C1—C2—C3	−178.64 (13)	N1—N2—C11—N3	−0.07 (16)
C7—O1—C3—C2	2.7 (2)	N1—N2—C11—S1	−179.34 (13)
C7—O1—C3—C4	−177.29 (12)	N4—N3—C11—N2	−178.90 (12)
C1—C2—C3—O1	−179.99 (13)	C10—N3—C11—N2	−0.01 (16)
C1—C2—C3—C4	0.0 (2)	N4—N3—C11—S1	0.58 (15)
C8—O2—C4—C3	138.95 (14)	C10—N3—C11—S1	179.48 (9)
C8—O2—C4—C5	−44.2 (2)	C12—S1—C11—N2	178.60 (18)
O1—C3—C4—O2	−1.28 (18)	C12—S1—C11—N3	−0.68 (10)
C2—C3—C4—O2	178.74 (12)	N3—N4—C12—C13	179.15 (12)
O1—C3—C4—C5	−178.28 (12)	N3—N4—C12—S1	−0.53 (14)
C2—C3—C4—C5	1.7 (2)	C11—S1—C12—N4	0.74 (11)
C9—O3—C5—C6	−0.1 (2)	C11—S1—C12—C13	−178.97 (11)
C9—O3—C5—C4	−178.32 (12)	N4—C12—C13—C14	175.74 (13)
O2—C4—C5—O3	−1.3 (2)	S1—C12—C13—C14	−4.59 (17)
C3—C4—C5—O3	175.43 (12)	N4—C12—C13—C18	−4.3 (2)
O2—C4—C5—C6	−179.60 (13)	S1—C12—C13—C18	175.39 (11)
C3—C4—C5—C6	−2.9 (2)	C18—C13—C14—C15	−0.5 (2)
O3—C5—C6—C1	−175.88 (13)	C12—C13—C14—C15	179.46 (13)
C4—C5—C6—C1	2.2 (2)	C13—C14—C15—C16	1.2 (2)
C2—C1—C6—C5	−0.5 (2)	C14—C15—C16—C17	−0.6 (2)
C10—C1—C6—C5	177.61 (12)	C15—C16—C17—C18	−0.7 (2)
N2—N1—C10—N3	−0.13 (15)	C16—C17—C18—C13	1.3 (2)
N2—N1—C10—C1	−177.07 (12)	C16—C17—C18—C19	−178.14 (14)
C11—N3—C10—N1	0.09 (15)	C14—C13—C18—C17	−0.7 (2)
N4—N3—C10—N1	178.69 (14)	C12—C13—C18—C17	179.32 (13)
C11—N3—C10—C1	176.96 (13)	C14—C13—C18—C19	178.70 (13)
N4—N3—C10—C1	−4.4 (3)	C12—C13—C18—C19	−1.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.95	2.45	3.127 (3)	128
C7—H7C···N2ⁱ	0.98	2.62	3.524 (3)	154
C19—H19B···CgAⁱⁱ	0.98	2.90	3.808 (3)	155

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₃S
M_r	382.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	7.5108 (15), 15.950 (3), 14.096 (3)
β (°)	91.88 (3)
V (Å³)	1687.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.923, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	11990, 3984, 3408
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 1.07
No. of reflections	3984
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.35

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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
C2—H2···N4	0.95	2.45	3.127 (3)	128.00
C7—H7C···N2ⁱ	0.98	2.62	3.524 (3)	154.00
C19—H19B···CgAⁱⁱ	0.98	2.896	3.808 (3)	155.30

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z.

Acknowledgements

The authors thank Guiyang College (grant No. 2008012) for financial support.

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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 and CrystalStructure. 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1481

doi:10.1107/S160053680802062X

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

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