3-(3-Methoxy-benz-yl)-4-(2-methoxy-phen-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(17)H(17)N(3)O(2)S, the five-membered ring forms dihedral angles of 53.02 (3) and 78.57 (3)° with the 3-meth-oxy-substituted and 2-meth-oxy-substituted benzene rings, respectively. In the crystal structure, mol-ecules are linked into centrosymmetric dimers via inter-molecular N-H⋯S hydrogen bonds.

Related literature

For background information on the biological activity of substituted triazole derivatives, see: Demirbas et al. (2002 ▶); Holla et al. (1998 ▶); Omar et al. (1986 ▶); Paulvannan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶); Kritsanida et al. (2002 ▶). For related structures, see: Öztürk et al. (2004a ▶,b ▶); Zhang et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H17N3O2S

M = 327.40

Triclinic,

a = 7.3941 (3) Å

b = 10.6459 (5) Å

c = 12.1940 (8) Å

α = 68.841 (5)°

β = 74.317 (5)°

γ = 75.187 (5)°

V = 848.37 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 (2) K

0.40 × 0.24 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: integration (Gaussian; Coppens, 1970 ▶) T min = 0.946, T max = 0.983

10764 measured reflections

3708 independent reflections

2064 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.159

S = 1.10

3708 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwin­owski & Minor, 1997 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037215/lh2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037215/lh2729Isup2.hkl

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

C17H17N3O2S	Z = 2
Mr = 327.40	F(000) = 344
Triclinic, P1	Dx = 1.282 Mg m−3
Hall symbol: -P 1	Melting point: 469(1) K
a = 7.3941 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6459 (5) Å	Cell parameters from 10808 reflections
c = 12.1940 (8) Å	θ = 1–27.5°
α = 68.841 (5)°	µ = 0.20 mm−1
β = 74.317 (5)°	T = 293 K
γ = 75.187 (5)°	Plate, colourless
V = 848.37 (8) Å3	0.40 × 0.24 × 0.15 mm

Bruker–Nonius KappaCCD area-detector diffractometer	3708 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans to fill the Ewald sphere	h = −9→9
Absorption correction: integration (Gaussian; Coppens, 1970)	k = −13→13
Tmin = 0.946, Tmax = 0.983	l = −15→15
10764 measured reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0364P)2 + 0.6393P] where P = (Fo2 + 2Fc2)/3
3708 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.24 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	−0.37112 (12)	0.55979 (11)	0.30006 (8)	0.0515 (3)
N2	−0.2330 (4)	0.4093 (3)	0.5026 (2)	0.0410 (7)
H2	−0.3425	0.4150	0.5499	0.049*
N1	−0.0166 (3)	0.4302 (3)	0.3462 (2)	0.0379 (6)
N3	−0.0666 (4)	0.3402 (3)	0.5425 (2)	0.0444 (7)
C7	−0.2087 (4)	0.4659 (3)	0.3847 (3)	0.0362 (7)
C10	0.3280 (4)	0.1679 (3)	0.4006 (3)	0.0416 (8)
C1	0.0831 (4)	0.4687 (4)	0.2239 (3)	0.0460 (9)
C8	0.0625 (4)	0.3535 (3)	0.4452 (3)	0.0374 (7)
C11	0.4677 (5)	0.1629 (4)	0.3017 (3)	0.0535 (9)
H11	0.5259	0.2385	0.2566	0.064*
O1	0.0235 (4)	0.2702 (3)	0.2152 (3)	0.0745 (8)
C14	0.2995 (6)	−0.0616 (4)	0.4330 (4)	0.0700 (12)
H14	0.2433	−0.1380	0.4789	0.084*
C9	0.2686 (4)	0.2945 (3)	0.4391 (3)	0.0446 (8)
H9A	0.2988	0.2723	0.5173	0.054*
H9B	0.3424	0.3630	0.3829	0.054*
C15	0.2434 (5)	0.0546 (4)	0.4662 (4)	0.0591 (11)
H15	0.1477	0.0574	0.5333	0.071*
C2	0.1052 (5)	0.3814 (5)	0.1581 (3)	0.0543 (10)
C3	0.2031 (6)	0.4167 (6)	0.0396 (4)	0.0767 (15)
H3	0.2209	0.3601	−0.0067	0.092*
C13	0.4385 (6)	−0.0674 (4)	0.3336 (4)	0.0634 (11)
H13	0.4743	−0.1460	0.3107	0.076*
C6	0.1539 (5)	0.5894 (4)	0.1775 (3)	0.0605 (11)
H6	0.1374	0.6459	0.2237	0.073*
C12	0.5230 (6)	0.0434 (4)	0.2686 (4)	0.0639 (11)
C5	0.2519 (6)	0.6227 (6)	0.0573 (4)	0.0808 (15)
H5	0.3011	0.7034	0.0217	0.097*
O2	0.6618 (5)	0.0512 (4)	0.1674 (3)	0.1103 (13)
C16	0.0674 (8)	0.1673 (6)	0.1580 (5)	0.106 (2)
H16A	0.0231	0.2046	0.0837	0.127*
H16B	0.0055	0.0915	0.2094	0.127*
H16C	0.2029	0.1366	0.1426	0.127*
C4	0.2727 (6)	0.5350 (7)	−0.0064 (4)	0.0838 (17)
H4	0.3387	0.5582	−0.0855	0.101*
C17	0.7351 (12)	−0.0684 (7)	0.1341 (7)	0.181 (4)
H17A	0.7803	−0.1401	0.2007	0.217*
H17B	0.8390	−0.0520	0.0666	0.217*
H17C	0.6375	−0.0952	0.1134	0.217*

	U11	U22	U33	U12	U13	U23
S1	0.0403 (5)	0.0619 (7)	0.0415 (5)	0.0027 (4)	−0.0018 (4)	−0.0162 (4)
N2	0.0386 (15)	0.0399 (17)	0.0390 (16)	−0.0030 (12)	0.0016 (12)	−0.0155 (13)
N1	0.0363 (14)	0.0392 (17)	0.0346 (15)	−0.0026 (12)	0.0005 (11)	−0.0154 (13)
N3	0.0486 (16)	0.0385 (17)	0.0425 (17)	−0.0052 (13)	−0.0046 (13)	−0.0135 (14)
C7	0.0415 (17)	0.0327 (19)	0.0339 (17)	−0.0070 (14)	0.0042 (13)	−0.0180 (15)
C10	0.0378 (17)	0.035 (2)	0.052 (2)	0.0009 (14)	−0.0134 (15)	−0.0141 (16)
C1	0.0340 (17)	0.059 (2)	0.0374 (18)	0.0044 (16)	−0.0034 (14)	−0.0182 (18)
C8	0.0442 (18)	0.0298 (18)	0.0399 (19)	−0.0055 (14)	−0.0060 (15)	−0.0152 (15)
C11	0.063 (2)	0.039 (2)	0.054 (2)	−0.0098 (17)	−0.0022 (18)	−0.0157 (18)
O1	0.086 (2)	0.076 (2)	0.076 (2)	−0.0040 (17)	−0.0174 (16)	−0.0474 (18)
C14	0.062 (2)	0.041 (2)	0.099 (3)	−0.0095 (19)	−0.010 (2)	−0.017 (2)
C9	0.0454 (19)	0.039 (2)	0.050 (2)	−0.0018 (15)	−0.0128 (16)	−0.0164 (17)
C15	0.046 (2)	0.044 (2)	0.077 (3)	−0.0036 (18)	0.0007 (19)	−0.020 (2)
C2	0.040 (2)	0.075 (3)	0.047 (2)	0.0079 (19)	−0.0101 (16)	−0.030 (2)
C3	0.049 (2)	0.124 (5)	0.050 (3)	0.015 (3)	−0.007 (2)	−0.041 (3)
C13	0.072 (3)	0.040 (2)	0.082 (3)	0.003 (2)	−0.022 (2)	−0.029 (2)
C6	0.041 (2)	0.068 (3)	0.053 (2)	−0.0121 (19)	−0.0062 (17)	0.003 (2)
C12	0.066 (3)	0.057 (3)	0.062 (3)	−0.002 (2)	0.000 (2)	−0.027 (2)
C5	0.052 (2)	0.102 (4)	0.061 (3)	−0.021 (2)	−0.005 (2)	0.007 (3)
O2	0.142 (3)	0.076 (2)	0.094 (3)	−0.024 (2)	0.042 (2)	−0.049 (2)
C16	0.129 (5)	0.094 (4)	0.130 (5)	0.021 (3)	−0.062 (4)	−0.077 (4)
C4	0.047 (2)	0.137 (5)	0.047 (3)	−0.002 (3)	0.000 (2)	−0.020 (3)
C17	0.222 (8)	0.116 (6)	0.175 (7)	−0.045 (5)	0.100 (6)	−0.102 (6)

S1—C7	1.679 (3)	C9—H9A	0.9700
N2—C7	1.324 (4)	C9—H9B	0.9700
N2—N3	1.377 (4)	C15—H15	0.9300
N2—H2	0.8600	C2—C3	1.390 (6)
N1—C7	1.369 (4)	C3—C4	1.353 (7)
N1—C8	1.375 (4)	C3—H3	0.9300
N1—C1	1.434 (4)	C13—C12	1.358 (6)
N3—C8	1.294 (4)	C13—H13	0.9300
C10—C11	1.367 (5)	C6—C5	1.407 (6)
C10—C15	1.380 (5)	C6—H6	0.9300
C10—C9	1.507 (5)	C12—O2	1.366 (5)
C1—C6	1.380 (5)	C5—C4	1.372 (7)
C1—C2	1.387 (5)	C5—H5	0.9300
C8—C9	1.485 (4)	O2—C17	1.407 (6)
C11—C12	1.402 (5)	C16—H16A	0.9599
C11—H11	0.9300	C16—H16B	0.9601
O1—C2	1.340 (5)	C16—H16C	0.9600
O1—C16	1.428 (5)	C4—H4	0.9300
C14—C15	1.370 (5)	C17—H17A	0.9600
C14—C13	1.370 (6)	C17—H17B	0.9600
C14—H14	0.9299	C17—H17C	0.9599
C7—N2—N3	113.7 (3)	O1—C2—C1	115.7 (3)
C7—N2—H2	123.2	O1—C2—C3	125.5 (4)
N3—N2—H2	123.1	C1—C2—C3	118.7 (5)
C7—N1—C8	108.1 (2)	C4—C3—C2	118.4 (5)
C7—N1—C1	125.4 (3)	C4—C3—H3	120.8
C8—N1—C1	126.5 (2)	C2—C3—H3	120.8
C8—N3—N2	103.9 (3)	C12—C13—C14	119.2 (4)
N2—C7—N1	103.5 (3)	C12—C13—H13	120.3
N2—C7—S1	129.2 (2)	C14—C13—H13	120.5
N1—C7—S1	127.3 (2)	C1—C6—C5	116.9 (5)
C11—C10—C15	119.2 (3)	C1—C6—H6	121.3
C11—C10—C9	120.7 (3)	C5—C6—H6	121.7
C15—C10—C9	120.1 (3)	C13—C12—O2	124.9 (4)
C6—C1—C2	123.1 (4)	C13—C12—C11	120.6 (4)
C6—C1—N1	118.8 (3)	O2—C12—C11	114.5 (4)
C2—C1—N1	118.1 (4)	C4—C5—C6	119.1 (5)
N3—C8—N1	110.8 (3)	C4—C5—H5	120.7
N3—C8—C9	125.4 (3)	C6—C5—H5	120.1
N1—C8—C9	123.8 (3)	C12—O2—C17	117.6 (4)
C10—C11—C12	119.8 (4)	O1—C16—H16A	109.5
C10—C11—H11	120.1	O1—C16—H16B	109.4
C12—C11—H11	120.1	H16A—C16—H16B	109.5
C2—O1—C16	117.5 (4)	O1—C16—H16C	109.5
C15—C14—C13	120.9 (4)	H16A—C16—H16C	109.5
C15—C14—H14	119.6	H16B—C16—H16C	109.5
C13—C14—H14	119.5	C3—C4—C5	123.7 (5)
C8—C9—C10	113.6 (3)	C3—C4—H4	118.3
C8—C9—H9A	108.9	C5—C4—H4	118.1
C10—C9—H9A	108.9	O2—C17—H17A	108.6
C8—C9—H9B	108.8	O2—C17—H17B	109.5
C10—C9—H9B	108.7	H17A—C17—H17B	109.5
H9A—C9—H9B	107.7	O2—C17—H17C	110.4
C14—C15—C10	120.4 (4)	H17A—C17—H17C	109.5
C14—C15—H15	119.9	H17B—C17—H17C	109.5
C10—C15—H15	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.42	3.277 (3)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.42	3.277 (3)	172

Symmetry code: (i) .