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

In the mol-ecule of the title compound, C(19)H(18)N(4)O(3)S, the planar central heterocylic ring system is oriented with respect to the trimethoxy-phenyl and 2-methyl-phenyl 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, inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. These dimers are connected via a C-H⋯π contact between the 2-methyl-phenyl and trimethoxy-phenyl rings, and a π-π contact between the thia-diazole and trimethoxy-phenyl 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 = 382.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.07

3984 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802062X/hk2487Isup2.hkl

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

C19H18N4O3S	F000 = 800
Mr = 382.43	Dx = 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 = 1.9–27.9º
c = 14.096 (3) Å	µ = 0.22 mm−1
β = 91.88 (3)º	T = 113 (2) K
V = 1687.7 (6) Å3	Prism, colorless
Z = 4	0.24 × 0.20 × 0.16 mm

Rigaku Saturn CCD area-detector diffractometer	3984 independent reflections
Radiation source: rotating anode	3408 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.031
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 1.9º
ω and φ scans	h = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −20→20
Tmin = 0.923, Tmax = 0.965	l = −17→18
11990 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.1888P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
3984 reflections	Δρmax = 0.39 e Å−3
248 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) . CgA is the centroid of the trimethoxyphenyl ring.