3-(3-Methoxy­benz­yl)-4-(2-methoxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Hanif, M.; Qadeer, G.; Rama, N.H.; Ruzicka, A.

doi:10.1107/S1600536808037215

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages o2345-o2346

doi:10.1107/S1600536808037215

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3-(3-Methoxybenzyl)-4-(2-methoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione

Muhammad Hanif,^a Ghulam Qadeer,^a ^* Nasim Hasan Rama ^a and Ales Ruzicka ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nam. Cs. Legii' 565, 53210 Pardubice, Czech Republic
^*Correspondence e-mail: qadeerqau@yahoo.com

(Received 1 November 2008; accepted 10 November 2008; online 13 November 2008)

In the title compound, C₁₇H₁₇N₃O₂S, the five-membered ring forms dihedral angles of 53.02 (3) and 78.57 (3)° with the 3-methoxy-substituted and 2-methoxy-substituted benzene rings, respectively. In the crystal structure, molecules are linked into centrosymmetric dimers via intermolecular 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_r = 327.40
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.073
wR(F²) = 0.159
S = 1.10
3708 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) -x-1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Substituted triazole derivatives display significant biological activity including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to structure, possibly being due to the presence of the —N—C=S unit (Omar et al., 1986). We are interested in the synthesis and biological activity of substituted triazole derivatives and report here the synthesis and crystal structure of the title compound, (I) (Fig. 1).

In the molecluar structure of (I), the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in related structures (Öztürk et al., 2004a,b). The C7-S1 bond length [1.679 (3) A °] compares with 1.6773 (19) A ° in 4-(4-chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione (Ozturk et al., 2004a) and 1.668 (5) A ° in 4-amino-3-(1,2,3,4,5- pentahydroxypentyl)-1H-1,2,4-triazole-5(4H)-thione (Zhang et al., 2004). In the triazole ring, the N3-C8 bond [1.294 (4)] bond shows the expected double bond character.

The rings A (N1—N3/C7/C8), B (C1—C6) and C (C10—C15) are eesentially planar and dihedral angles between them are A/B = 78.57 (3)°, A/C = 53.02 (3)° and B/C = 16.23 (3)°. In the crystal structure, molecules are linked into centrosymmetric dimers via intermolecular N–H···S hydrogen bonds.

Related literature top

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 structure, see: Öztürk et al. (2004a,b); Zhang et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

The synthesis of the title compound was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(2-(3-methoxyphenyl)acetyl)thiosemicarbazide (3.45 g, 10 mmol) in 2 M NaOH for 5 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield: 75%; m.p. 469–470 K).

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).
	Fig. 2. Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.
	Fig. 3. The reaction scheme.

3-(3-Methoxybenzyl)-4-(2-methoxyphenyl)-1H-1,2,4-triazole-5(4H)- thione top

Crystal data top

C₁₇H₁₇N₃O₂S	Z = 2
M_r = 327.40	F(000) = 344
Triclinic, P1	D_x = 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

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	3708 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
ϕ and ω scans to fill the Ewald sphere	h = −9→9
Absorption correction: integration (Gaussian; Coppens, 1970)	k = −13→13
T_min = 0.946, T_max = 0.983	l = −15→15
10764 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0364P)² + 0.6393P] where P = (F_o² + 2F_c²)/3
3708 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₇N₃O₂S	γ = 75.187 (5)°
M_r = 327.40	V = 848.37 (8) Å³
Triclinic, P1	Z = 2
a = 7.3941 (3) Å	Mo Kα radiation
b = 10.6459 (5) Å	µ = 0.20 mm⁻¹
c = 12.1940 (8) Å	T = 293 K
α = 68.841 (5)°	0.40 × 0.24 × 0.15 mm
β = 74.317 (5)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	3708 independent reflections
Absorption correction: integration (Gaussian; Coppens, 1970)	2064 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.983	R_int = 0.079
10764 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.10	Δρ_max = 0.32 e Å⁻³
3708 reflections	Δρ_min = −0.24 e Å⁻³
208 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 > 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	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x−1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂S
M_r	327.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3941 (3), 10.6459 (5), 12.1940 (8)
α, β, γ (°)	68.841 (5), 74.317 (5), 75.187 (5)
V (Å³)	848.37 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.24 × 0.15

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration (Gaussian; Coppens, 1970)
T_min, T_max	0.946, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10764, 3708, 2064
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.159, 1.10
No. of reflections	3708
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), DIRAX/LSQ (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.86	2.42	3.277 (3)	171.8

Symmetry code: (i) −x−1, −y+1, −z+1.

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

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