6-(4-Methyl-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole.

In the mol-ecule of the title compound, C(19)H(18)N(4)O(3)S, the central heterocylic ring system is oriented with respect to the trimethoxy-phenyl and 4-methyl-phenyl 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, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, and an intra-molecular C-H⋯N inter-action also occurs.

Related literature

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

Experimental

Crystal data

C19H18N4O3S

M = 382.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.06

4184 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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

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.

	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*

	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)

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)

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

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) .