6-(3-Pyrid­yl)-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/S1600536808019855

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1402

doi:10.1107/S1600536808019855

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

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

^aDepartment of Biology and Environment Technology, 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 ^cDepartment of Chemistry, College of Science, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 26 June 2008; accepted 30 June 2008; online 5 July 2008)

In the molecule of the title compound, C₁₇H₁₅N₅O₃S, the planar central heterocylic ring system is oriented with respect to the benzene and pyridine rings at dihedral angles of 6.61 (3) and 19.22 (3)°, respectively. An intramolecular C—H⋯N hydrogen bond results in the formation of a six-membered ring, adopting a flattened boat conformation. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules.

Related literature

For general background, see: Karabasanagouda et al. (2007 ); Mathew et al. (2007 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₅N₅O₃S
M_r = 369.40
Monoclinic, P 2₁ /c
a = 7.4682 (15) Å
b = 14.128 (3) Å
c = 15.550 (3) Å
β = 90.46 (3)°
V = 1640.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 113 (2) K
0.20 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.956, T_max = 0.991
18716 measured reflections
3620 independent reflections
3121 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.108
S = 1.17
3620 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.41 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	2.40	3.0869 (19)	129
C9—H9A⋯N1ⁱ	0.98	2.60	3.576 (2)	171
C8—H8C⋯N5ⁱⁱ	0.98	2.63	3.573 (2)	161
C14—H14⋯N2ⁱⁱⁱ	0.95	2.57	3.410 (2)	148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019855/hk2481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019855/hk2481Isup2.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 (N5/C13–C17) are, of course, planar, and the dihedral angles between them are A/B = 6.28 (3)°, A/C = 6.97 (3)°, A/D = 25.30 (3)°, B/C = 0.95 (2)°, B/D = 19.38 (3)° and C/D = 19.06 (3)°. 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 6.61 (3)° and 19.22 (3)°. The intramolecular C—H···N hydrogen bond (Table 1) results in the formation of a six-membered ring E (N3/N4/C1/C2/C10/H2), in which it adopts flattened-boat [ϕ = -95.41 (2)° and θ = 21.96 (3)°] conformation, having total puckering amplitude, Q_T, of 1.463 (3) Å (Cremer & Pople, 1975).

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules, 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). For ring conformation puckering parameters, see: Cremer & Pople (1975).

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 nicotinic 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: 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); 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. Hydrogen bond is shown as dashed line.

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

Crystal data top

C₁₇H₁₅N₅O₃S	F(000) = 768
M_r = 369.40	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 448K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.4682 (15) Å	Cell parameters from 4807 reflections
b = 14.128 (3) Å	θ = 1.9–27.1°
c = 15.550 (3) Å	µ = 0.23 mm⁻¹
β = 90.46 (3)°	T = 113 K
V = 1640.6 (6) Å³	Prism, colourless
Z = 4	0.20 × 0.06 × 0.04 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3620 independent reflections
Radiation source: rotating anode	3121 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.2°, θ_min = 2.0°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
T_min = 0.956, T_max = 0.991	l = −19→19
18716 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0643P)² + 0.1727P] where P = (F_o² + 2F_c²)/3
3620 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₇H₁₅N₅O₃S	V = 1640.6 (6) Å³
M_r = 369.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4682 (15) Å	µ = 0.23 mm⁻¹
b = 14.128 (3) Å	T = 113 K
c = 15.550 (3) Å	0.20 × 0.06 × 0.04 mm
β = 90.46 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3620 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3121 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.991	R_int = 0.034
18716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.17	Δρ_max = 0.48 e Å⁻³
3620 reflections	Δρ_min = −0.41 e Å⁻³
238 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	0.47268 (5)	0.30203 (2)	0.32685 (2)	0.01906 (12)
O1	0.09766 (15)	0.49470 (8)	0.82026 (7)	0.0250 (3)
O2	−0.02336 (14)	0.65367 (8)	0.74798 (7)	0.0239 (3)
O3	0.02728 (14)	0.69219 (7)	0.58349 (7)	0.0236 (3)
N1	0.46168 (17)	0.25227 (9)	0.50417 (8)	0.0228 (3)
N2	0.39750 (17)	0.30533 (9)	0.57349 (8)	0.0217 (3)
N3	0.36415 (15)	0.39115 (8)	0.45790 (8)	0.0167 (3)
N4	0.32966 (15)	0.45519 (8)	0.39312 (7)	0.0167 (3)
N5	0.32739 (18)	0.61126 (9)	0.16139 (9)	0.0242 (3)
C1	0.24914 (18)	0.45989 (10)	0.59768 (9)	0.0178 (3)
C2	0.18824 (19)	0.54403 (10)	0.56074 (9)	0.0183 (3)
H2	0.2085	0.5569	0.5017	0.022*
C3	0.09733 (18)	0.60873 (10)	0.61183 (9)	0.0184 (3)
C4	0.07026 (18)	0.59006 (10)	0.69890 (9)	0.0186 (3)
C5	0.13206 (18)	0.50562 (11)	0.73504 (9)	0.0192 (3)
C6	0.22174 (18)	0.43975 (10)	0.68450 (9)	0.0189 (3)
H6	0.2636	0.3820	0.7087	0.023*
C7	0.1537 (2)	0.40859 (12)	0.85975 (10)	0.0285 (4)
H7A	0.0953	0.3551	0.8309	0.043*
H7B	0.1206	0.4092	0.9206	0.043*
H7C	0.2839	0.4023	0.8549	0.043*
C8	0.0881 (2)	0.72143 (13)	0.78883 (11)	0.0321 (4)
H8A	0.1680	0.6895	0.8298	0.048*
H8B	0.0139	0.7674	0.8194	0.048*
H8C	0.1596	0.7543	0.7455	0.048*
C9	0.0629 (2)	0.71792 (11)	0.49656 (10)	0.0240 (3)
H9A	0.1922	0.7258	0.4890	0.036*
H9B	0.0019	0.7776	0.4830	0.036*
H9C	0.0190	0.6681	0.4580	0.036*
C10	0.33868 (18)	0.38808 (10)	0.54526 (9)	0.0176 (3)
C11	0.43862 (19)	0.30623 (10)	0.43654 (10)	0.0183 (3)
C12	0.38009 (18)	0.41649 (10)	0.32131 (9)	0.0166 (3)
C13	0.36482 (18)	0.46502 (10)	0.23842 (9)	0.0171 (3)
C14	0.37053 (19)	0.41517 (10)	0.16155 (9)	0.0207 (3)
H14	0.3865	0.3485	0.1614	0.025*
C15	0.3526 (2)	0.46451 (11)	0.08527 (10)	0.0237 (3)
H15	0.3555	0.4322	0.0317	0.028*
C16	0.3304 (2)	0.56120 (11)	0.08802 (10)	0.0234 (3)
H16	0.3166	0.5943	0.0352	0.028*
C17	0.34453 (19)	0.56304 (10)	0.23455 (10)	0.0207 (3)
H17	0.3428	0.5973	0.2871	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0235 (2)	0.01467 (19)	0.0190 (2)	0.00266 (13)	0.00292 (15)	−0.00077 (12)
O1	0.0308 (6)	0.0273 (6)	0.0169 (5)	0.0015 (5)	0.0062 (4)	0.0028 (4)
O2	0.0222 (5)	0.0234 (6)	0.0262 (6)	0.0008 (4)	0.0076 (4)	−0.0053 (4)
O3	0.0308 (6)	0.0189 (5)	0.0211 (6)	0.0049 (4)	0.0035 (5)	0.0012 (4)
N1	0.0290 (7)	0.0187 (6)	0.0208 (7)	0.0034 (5)	0.0040 (5)	0.0011 (5)
N2	0.0263 (7)	0.0186 (6)	0.0202 (7)	0.0021 (5)	0.0023 (5)	0.0004 (5)
N3	0.0183 (6)	0.0140 (6)	0.0176 (6)	0.0004 (5)	0.0011 (5)	0.0001 (4)
N4	0.0173 (6)	0.0154 (6)	0.0172 (6)	−0.0005 (4)	−0.0001 (5)	0.0022 (4)
N5	0.0308 (7)	0.0171 (6)	0.0248 (7)	0.0010 (5)	0.0001 (6)	0.0014 (5)
C1	0.0158 (6)	0.0181 (7)	0.0194 (7)	−0.0026 (5)	0.0001 (6)	−0.0021 (5)
C2	0.0194 (7)	0.0192 (7)	0.0162 (7)	−0.0024 (5)	0.0011 (5)	−0.0001 (5)
C3	0.0167 (7)	0.0165 (7)	0.0218 (7)	−0.0020 (5)	−0.0009 (6)	−0.0013 (5)
C4	0.0161 (6)	0.0196 (7)	0.0202 (7)	−0.0029 (5)	0.0042 (6)	−0.0042 (6)
C5	0.0180 (7)	0.0230 (7)	0.0167 (7)	−0.0054 (6)	0.0021 (6)	−0.0008 (6)
C6	0.0176 (7)	0.0187 (7)	0.0206 (7)	−0.0019 (6)	−0.0003 (6)	−0.0001 (5)
C7	0.0331 (9)	0.0328 (9)	0.0195 (8)	0.0028 (7)	0.0024 (7)	0.0065 (7)
C8	0.0359 (9)	0.0312 (9)	0.0293 (9)	0.0037 (7)	−0.0016 (7)	−0.0147 (7)
C9	0.0274 (8)	0.0205 (7)	0.0240 (8)	0.0011 (6)	0.0009 (6)	0.0031 (6)
C10	0.0180 (7)	0.0184 (7)	0.0163 (7)	−0.0036 (5)	0.0005 (5)	0.0005 (5)
C11	0.0187 (7)	0.0148 (7)	0.0214 (7)	0.0004 (5)	0.0022 (6)	−0.0008 (5)
C12	0.0162 (6)	0.0135 (6)	0.0200 (7)	−0.0012 (5)	0.0007 (5)	−0.0013 (5)
C13	0.0150 (6)	0.0171 (7)	0.0192 (7)	−0.0009 (5)	0.0022 (5)	0.0003 (5)
C14	0.0238 (7)	0.0159 (7)	0.0225 (7)	−0.0009 (6)	0.0032 (6)	−0.0014 (5)
C15	0.0269 (8)	0.0243 (8)	0.0199 (7)	−0.0032 (6)	0.0035 (6)	−0.0020 (6)
C16	0.0249 (7)	0.0254 (8)	0.0200 (7)	−0.0010 (6)	0.0000 (6)	0.0048 (6)
C17	0.0247 (7)	0.0169 (7)	0.0205 (7)	0.0009 (6)	−0.0004 (6)	−0.0023 (5)

Geometric parameters (Å, º) top

S1—C11	1.7275 (15)	C3—C4	1.396 (2)
S1—C12	1.7606 (14)	C4—C5	1.396 (2)
O1—C5	1.3607 (17)	C5—C6	1.393 (2)
O1—C7	1.4242 (19)	C6—H6	0.9500
O2—C4	1.3739 (17)	C7—H7A	0.9800
O2—C8	1.416 (2)	C7—H7B	0.9800
O3—C3	1.3616 (17)	C7—H7C	0.9800
O3—C9	1.4269 (18)	C8—H8A	0.9800
N1—C11	1.3092 (19)	C8—H8B	0.9800
N1—N2	1.4007 (17)	C8—H8C	0.9800
N2—C10	1.3225 (19)	C9—H9A	0.9800
N3—C11	1.3645 (18)	C9—H9B	0.9800
N3—C10	1.3739 (18)	C9—H9C	0.9800
N3—N4	1.3767 (16)	C12—C13	1.4637 (19)
N4—C12	1.3016 (18)	C13—C14	1.388 (2)
N5—C17	1.331 (2)	C13—C17	1.394 (2)
N5—C16	1.343 (2)	C14—C15	1.381 (2)
C1—C2	1.395 (2)	C14—H14	0.9500
C1—C6	1.396 (2)	C15—C16	1.377 (2)
C1—C10	1.466 (2)	C15—H15	0.9500
C2—C3	1.392 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—H17	0.9500

C11—S1—C12	87.47 (7)	O2—C8—H8B	109.5
C5—O1—C7	117.36 (12)	H8A—C8—H8B	109.5
C4—O2—C8	113.05 (11)	O2—C8—H8C	109.5
C3—O3—C9	116.95 (11)	H8A—C8—H8C	109.5
C11—N1—N2	105.24 (12)	H8B—C8—H8C	109.5
C10—N2—N1	109.42 (12)	O3—C9—H9A	109.5
C11—N3—C10	105.84 (12)	O3—C9—H9B	109.5
C11—N3—N4	118.28 (12)	H9A—C9—H9B	109.5
C10—N3—N4	135.86 (12)	O3—C9—H9C	109.5
C12—N4—N3	107.34 (11)	H9A—C9—H9C	109.5
C17—N5—C16	117.03 (13)	H9B—C9—H9C	109.5
C2—C1—C6	121.46 (13)	N2—C10—N3	107.93 (12)
C2—C1—C10	120.62 (13)	N2—C10—C1	125.37 (13)
C6—C1—C10	117.88 (13)	N3—C10—C1	126.53 (13)
C3—C2—C1	118.93 (13)	N1—C11—N3	111.57 (13)
C3—C2—H2	120.5	N1—C11—S1	138.90 (12)
C1—C2—H2	120.5	N3—C11—S1	109.52 (10)
O3—C3—C2	124.89 (13)	N4—C12—C13	122.53 (13)
O3—C3—C4	114.79 (13)	N4—C12—S1	117.39 (11)
C2—C3—C4	120.32 (13)	C13—C12—S1	120.07 (10)
O2—C4—C5	120.23 (13)	C14—C13—C17	118.08 (14)
O2—C4—C3	119.58 (13)	C14—C13—C12	121.19 (13)
C5—C4—C3	120.15 (13)	C17—C13—C12	120.72 (13)
O1—C5—C6	124.69 (14)	C15—C14—C13	118.68 (14)
O1—C5—C4	115.13 (12)	C15—C14—H14	120.7
C6—C5—C4	120.18 (13)	C13—C14—H14	120.7
C5—C6—C1	118.96 (14)	C16—C15—C14	119.00 (14)
C5—C6—H6	120.5	C16—C15—H15	120.5
C1—C6—H6	120.5	C14—C15—H15	120.5
O1—C7—H7A	109.5	N5—C16—C15	123.50 (14)
O1—C7—H7B	109.5	N5—C16—H16	118.3
H7A—C7—H7B	109.5	C15—C16—H16	118.3
O1—C7—H7C	109.5	N5—C17—C13	123.69 (14)
H7A—C7—H7C	109.5	N5—C17—H17	118.2
H7B—C7—H7C	109.5	C13—C17—H17	118.2
O2—C8—H8A	109.5

C11—N1—N2—C10	0.12 (16)	N4—N3—C10—C1	3.5 (2)
C11—N3—N4—C12	0.04 (16)	C2—C1—C10—N2	−178.36 (14)
C10—N3—N4—C12	−178.10 (15)	C6—C1—C10—N2	−0.5 (2)
C6—C1—C2—C3	−0.4 (2)	C2—C1—C10—N3	−3.7 (2)
C10—C1—C2—C3	177.37 (13)	C6—C1—C10—N3	174.15 (13)
C9—O3—C3—C2	−5.2 (2)	N2—N1—C11—N3	0.27 (16)
C9—O3—C3—C4	175.44 (12)	N2—N1—C11—S1	−179.02 (14)
C1—C2—C3—O3	−178.33 (13)	C10—N3—C11—N1	−0.54 (16)
C1—C2—C3—C4	1.0 (2)	N4—N3—C11—N1	−179.19 (12)
C8—O2—C4—C5	90.63 (17)	C10—N3—C11—S1	178.96 (9)
C8—O2—C4—C3	−91.79 (17)	N4—N3—C11—S1	0.31 (15)
O3—C3—C4—O2	0.86 (19)	C12—S1—C11—N1	178.89 (18)
C2—C3—C4—O2	−178.51 (13)	C12—S1—C11—N3	−0.40 (10)
O3—C3—C4—C5	178.45 (13)	N3—N4—C12—C13	−179.41 (12)
C2—C3—C4—C5	−0.9 (2)	N3—N4—C12—S1	−0.38 (14)
C7—O1—C5—C6	−1.6 (2)	C11—S1—C12—N4	0.48 (11)
C7—O1—C5—C4	178.36 (13)	C11—S1—C12—C13	179.54 (12)
O2—C4—C5—O1	−2.16 (19)	N4—C12—C13—C14	−161.57 (13)
C3—C4—C5—O1	−179.73 (12)	S1—C12—C13—C14	19.42 (18)
O2—C4—C5—C6	177.85 (13)	N4—C12—C13—C17	18.6 (2)
C3—C4—C5—C6	0.3 (2)	S1—C12—C13—C17	−160.41 (11)
O1—C5—C6—C1	−179.70 (13)	C17—C13—C14—C15	−1.2 (2)
C4—C5—C6—C1	0.3 (2)	C12—C13—C14—C15	178.97 (13)
C2—C1—C6—C5	−0.2 (2)	C13—C14—C15—C16	0.3 (2)
C10—C1—C6—C5	−178.05 (13)	C17—N5—C16—C15	−0.9 (2)
N1—N2—C10—N3	−0.46 (16)	C14—C15—C16—N5	0.9 (2)
N1—N2—C10—C1	175.04 (13)	C16—N5—C17—C13	−0.1 (2)
C11—N3—C10—N2	0.60 (15)	C14—C13—C17—N5	1.1 (2)
N4—N3—C10—N2	178.89 (14)	C12—C13—C17—N5	−179.02 (13)
C11—N3—C10—C1	−174.83 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.95	2.40	3.0869 (19)	129
C9—H9A···N1ⁱ	0.98	2.60	3.576 (2)	171
C8—H8C···N5ⁱⁱ	0.98	2.63	3.573 (2)	161
C14—H14···N2ⁱⁱⁱ	0.95	2.57	3.410 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₅O₃S
M_r	369.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	7.4682 (15), 14.128 (3), 15.550 (3)
β (°)	90.46 (3)
V (Å³)	1640.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.06 × 0.04

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.956, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	18716, 3620, 3121
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.108, 1.17
No. of reflections	3620
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.41

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (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	0.95	2.40	3.0869 (19)	129.00
C9—H9A···N1ⁱ	0.98	2.60	3.576 (2)	171.00
C8—H8C···N5ⁱⁱ	0.98	2.63	3.573 (2)	161.00
C14—H14···N2ⁱⁱⁱ	0.95	2.57	3.410 (2)	148.00

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

Acknowledgements

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

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. 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

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Volume 64| Part 8| August 2008| Page o1402

doi:10.1107/S1600536808019855

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

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