supplementary materials
6-(4-Methylphenyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole
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-HN interaction also occurs.
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.
H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for
aromatic and methyl H, respectively, and constrained to ride on their parent
atoms with Uiso(H) = xUeq(C), where x = 1.5 for
methyl H and x = 1.2 for aromatic H atoms.
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).
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 |
| Mr = 382.43 | Dx = 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 | Rint = 0.030 |
| ω scans | θmax = 27.9°, θmin = 2.2° |
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005) | h = −9→9 |
| Tmin = 0.959, Tmax = 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(Fo2) + (0.0558P)2 + 0.2342P]
where P = (Fo2 + 2Fc2)/3 |
| 4184 reflections | (Δ/σ)max = 0.003 |
| 248 parameters | Δρmax = 0.34 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
| C19H18N4O3S | V = 1760.2 (6) Å3 |
| Mr = 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 | 3593 reflections with I > 2σ(I) |
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005) | Rint = 0.030 |
| Tmin = 0.959, Tmax = 0.975 | θmax = 27.9° |
| 12668 measured reflections | Standard reflections: 0 |
| 4184 independent reflections | |
Refinement top
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.094 | Δρmax = 0.34 e Å−3 |
| S = 1.06 | Δρmin = −0.26 e Å−3 |
| 4184 reflections | Absolute structure: ? |
| 248 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | Uiso*/Ueq | |
| 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, °) 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, °) 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 codes: (i) x+1/2, −y+3/2, z+1/2. |
Table 1
Hydrogen-bond geometry (Å, °) 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 codes: (i) x+1/2, −y+3/2, z+1/2. |
The authors thank Guiyang College for financial support.
Karabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521–529.
Mathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823–840.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
![[Figure 1]](./bx2183fig1thm.gif)
![[Figure 2]](./bx2183fig2thm.gif)
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.