4-(2-Methoxy-phenyl)-3-(3,4,5-tri-methoxy-phen-ethyl)-2H-1,2,4-triazole-5(4H)-thione.

The title compound, C(20)H(23)N(3)O(4)S, is an important biologically active heterocyclic compound. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 78.60 (3) (trimethoxyphenyl ring) and 71.57 (3)° (methoxyphenyl ring). In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains along the c axis.

Related literature

For general background, see: Holla et al. (1998 ▶); Turan-Zitouni et al. (1999 ▶); Demirbas et al. (2002 ▶); Paulvannan et al. (2000 ▶); Kritsanida et al. (2002 ▶); Omar et al. (1986 ▶). 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

C20H23N3O4S

M = 401.47

Triclinic,

a = 8.6368 (6) Å

b = 10.5422 (7) Å

c = 11.6944 (8) Å

α = 91.733 (1)°

β = 92.955 (1)°

γ = 104.075 (1)°

V = 1030.44 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 (2) K

0.55 × 0.35 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: integration (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.946

8266 measured reflections

4149 independent reflections

3689 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.07

4149 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066433/hk2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066433/hk2411Isup2.hkl

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

C20H23N3O4S	Z = 2
Mr = 401.47	F(000) = 424
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Melting point: 491(1) K
a = 8.6368 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5422 (7) Å	Cell parameters from 5348 reflections
c = 11.6944 (8) Å	θ = 2.4–26.4°
α = 91.733 (1)°	µ = 0.19 mm−1
β = 92.955 (1)°	T = 100 K
γ = 104.075 (1)°	Rectangular, colourless
V = 1030.44 (12) Å3	0.55 × 0.35 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	4149 independent reflections
Radiation source: fine-focus sealed tube	3689 reflections with I > 2σ(I)
graphite	Rint = 0.061
ω and φ scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: integration (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.926, Tmax = 0.946	k = −13→12
8266 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.3128P] where P = (Fo2 + 2Fc2)/3
4149 reflections	(Δ/σ)max = 0.001
261 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.25 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	1.22156 (4)	0.29397 (4)	1.24108 (3)	0.02234 (11)
O1	0.73558 (18)	0.35378 (12)	0.44984 (10)	0.0440 (3)
O2	0.73876 (11)	0.15824 (11)	0.30066 (8)	0.0224 (2)
O3	0.76675 (13)	−0.07402 (10)	0.37013 (8)	0.0262 (2)
O4	1.16300 (12)	0.44582 (10)	0.89915 (9)	0.0260 (2)
N1	0.87413 (14)	0.11839 (12)	1.02120 (9)	0.0201 (3)
N2	0.94616 (14)	0.15655 (12)	1.12957 (10)	0.0193 (2)
H2N	0.8869 (19)	0.1498 (17)	1.1889 (15)	0.022 (4)*
N3	1.12777 (13)	0.22471 (11)	1.01432 (9)	0.0177 (2)
C1	0.98802 (16)	0.16129 (14)	0.95339 (11)	0.0187 (3)
C2	1.09805 (17)	0.22420 (14)	1.12896 (11)	0.0185 (3)
C3	0.97520 (16)	0.15040 (14)	0.82582 (11)	0.0210 (3)
H3A	1.0517	0.1012	0.7992	0.025*
H3B	1.0058	0.2393	0.7958	0.025*
C4	0.80733 (17)	0.08197 (15)	0.77691 (11)	0.0213 (3)
H4A	0.7863	−0.0128	0.7904	0.026*
H4B	0.7277	0.1174	0.8169	0.026*
C5	0.78916 (16)	0.10143 (14)	0.64979 (11)	0.0198 (3)
C6	0.77190 (19)	0.22128 (15)	0.61242 (12)	0.0268 (3)
H6	0.7712	0.2900	0.6667	0.032*
C7	0.75566 (19)	0.24094 (16)	0.49577 (13)	0.0267 (3)
C8	0.75539 (16)	0.13938 (14)	0.41670 (11)	0.0201 (3)
C9	0.77218 (16)	0.01948 (14)	0.45455 (11)	0.0193 (3)
C10	0.79036 (16)	0.00040 (14)	0.57146 (12)	0.0199 (3)
H10	0.8035	−0.0812	0.5972	0.024*
C11	0.7409 (4)	0.4614 (2)	0.52929 (18)	0.0692 (8)
H11A	0.6571	0.4357	0.5834	0.104*
H11B	0.7236	0.5364	0.4873	0.104*
H11C	0.8457	0.4857	0.5714	0.104*
C12	0.57722 (19)	0.1091 (2)	0.25334 (14)	0.0394 (4)
H12A	0.5360	0.0190	0.2762	0.059*
H12B	0.5757	0.1105	0.1695	0.059*
H12C	0.5100	0.1642	0.2820	0.059*
C13	0.7628 (2)	−0.20286 (16)	0.40713 (14)	0.0354 (4)
H13A	0.8643	−0.2026	0.4488	0.053*
H13B	0.7465	−0.2639	0.3403	0.053*
H13C	0.6748	−0.2303	0.4577	0.053*
C14	1.27708 (16)	0.28093 (14)	0.96606 (11)	0.0185 (3)
C15	1.29400 (17)	0.39505 (14)	0.90645 (11)	0.0207 (3)
C16	1.43893 (18)	0.44820 (15)	0.85927 (12)	0.0258 (3)
H16	1.4522	0.5250	0.8167	0.031*
C17	1.56401 (18)	0.38788 (17)	0.87504 (13)	0.0302 (4)
H17	1.6636	0.4252	0.8440	0.036*
C18	1.54665 (18)	0.27456 (17)	0.93495 (13)	0.0294 (3)
H18	1.6336	0.2347	0.9453	0.035*
C19	1.40069 (17)	0.21988 (15)	0.97969 (12)	0.0237 (3)
H19	1.3861	0.1409	1.0194	0.028*
C20	1.1700 (2)	0.55440 (16)	0.82719 (16)	0.0380 (4)
H20A	1.2536	0.6296	0.8585	0.057*
H20B	1.0666	0.5774	0.8240	0.057*
H20C	1.1947	0.5305	0.7498	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.02592 (19)	0.0233 (2)	0.01559 (18)	0.00255 (14)	−0.00210 (13)	0.00064 (13)
O1	0.0882 (10)	0.0284 (7)	0.0253 (6)	0.0323 (7)	0.0050 (6)	0.0065 (5)
O2	0.0211 (5)	0.0317 (6)	0.0138 (5)	0.0047 (4)	0.0009 (4)	0.0054 (4)
O3	0.0389 (6)	0.0217 (6)	0.0171 (5)	0.0057 (5)	0.0037 (4)	−0.0024 (4)
O4	0.0298 (5)	0.0184 (5)	0.0309 (6)	0.0082 (4)	−0.0018 (4)	0.0057 (4)
N1	0.0227 (6)	0.0228 (6)	0.0144 (5)	0.0052 (5)	−0.0009 (4)	0.0003 (5)
N2	0.0222 (6)	0.0225 (6)	0.0127 (5)	0.0041 (5)	0.0015 (5)	0.0018 (5)
N3	0.0208 (6)	0.0175 (6)	0.0142 (5)	0.0037 (5)	0.0006 (4)	0.0023 (4)
C1	0.0221 (7)	0.0161 (7)	0.0176 (7)	0.0044 (5)	−0.0002 (5)	0.0017 (5)
C2	0.0246 (7)	0.0165 (7)	0.0161 (6)	0.0077 (5)	0.0013 (5)	0.0033 (5)
C3	0.0243 (7)	0.0221 (7)	0.0159 (6)	0.0042 (6)	0.0014 (5)	0.0018 (5)
C4	0.0248 (7)	0.0220 (7)	0.0160 (6)	0.0037 (6)	0.0008 (5)	0.0010 (5)
C5	0.0194 (7)	0.0230 (7)	0.0161 (6)	0.0037 (5)	0.0004 (5)	0.0012 (5)
C6	0.0397 (9)	0.0234 (8)	0.0189 (7)	0.0115 (7)	0.0018 (6)	−0.0031 (6)
C7	0.0382 (8)	0.0227 (8)	0.0226 (7)	0.0131 (6)	0.0026 (6)	0.0051 (6)
C8	0.0208 (7)	0.0267 (8)	0.0134 (6)	0.0068 (6)	0.0013 (5)	0.0031 (5)
C9	0.0193 (6)	0.0211 (7)	0.0165 (6)	0.0031 (5)	0.0023 (5)	−0.0021 (5)
C10	0.0225 (7)	0.0186 (7)	0.0183 (7)	0.0044 (5)	0.0008 (5)	0.0023 (5)
C11	0.152 (3)	0.0320 (11)	0.0399 (11)	0.0512 (15)	0.0137 (13)	0.0079 (9)
C12	0.0228 (8)	0.0672 (13)	0.0262 (8)	0.0064 (8)	−0.0028 (6)	0.0151 (8)
C13	0.0555 (11)	0.0198 (8)	0.0284 (8)	0.0029 (7)	0.0116 (7)	−0.0035 (6)
C14	0.0196 (6)	0.0197 (7)	0.0151 (6)	0.0027 (5)	0.0008 (5)	−0.0015 (5)
C15	0.0243 (7)	0.0188 (7)	0.0175 (6)	0.0032 (6)	−0.0008 (5)	−0.0016 (5)
C16	0.0319 (8)	0.0233 (8)	0.0178 (7)	−0.0023 (6)	0.0035 (6)	0.0003 (6)
C17	0.0237 (7)	0.0374 (9)	0.0245 (7)	−0.0022 (6)	0.0072 (6)	−0.0076 (7)
C18	0.0233 (7)	0.0361 (9)	0.0300 (8)	0.0113 (7)	0.0006 (6)	−0.0083 (7)
C19	0.0280 (7)	0.0219 (8)	0.0218 (7)	0.0084 (6)	−0.0006 (6)	−0.0015 (6)
C20	0.0477 (10)	0.0211 (8)	0.0438 (10)	0.0067 (7)	−0.0093 (8)	0.0116 (7)

S1—C2	1.6775 (14)	C7—C8	1.393 (2)
O1—C7	1.3650 (18)	C8—C9	1.390 (2)
O1—C11	1.435 (2)	C9—C10	1.3944 (19)
O2—C8	1.3826 (15)	C10—H10	0.9500
O2—C12	1.4397 (18)	C11—H11A	0.9800
O3—C9	1.3647 (17)	C11—H11B	0.9800
O3—C13	1.4309 (19)	C11—H11C	0.9800
O4—C15	1.3642 (17)	C12—H12A	0.9800
O4—C20	1.4324 (18)	C12—H12B	0.9800
N1—C1	1.2987 (19)	C12—H12C	0.9800
N1—N2	1.3861 (15)	C13—H13A	0.9800
N2—C2	1.3326 (19)	C13—H13B	0.9800
N2—H2N	0.878 (17)	C13—H13C	0.9800
N3—C2	1.3778 (17)	C14—C19	1.3792 (19)
N3—C1	1.3789 (18)	C14—C15	1.389 (2)
N3—C14	1.4340 (18)	C15—C16	1.391 (2)
C1—C3	1.4892 (18)	C16—C17	1.388 (2)
C3—C4	1.5266 (19)	C16—H16	0.9500
C3—H3A	0.9900	C17—C18	1.384 (2)
C3—H3B	0.9900	C17—H17	0.9500
C4—C5	1.5122 (18)	C18—C19	1.389 (2)
C4—H4A	0.9900	C18—H18	0.9500
C4—H4B	0.9900	C19—H19	0.9500
C5—C10	1.3859 (19)	C20—H20A	0.9800
C5—C6	1.389 (2)	C20—H20B	0.9800
C6—C7	1.391 (2)	C20—H20C	0.9800
C6—H6	0.9500
C7—O1—C11	116.44 (13)	C5—C10—H10	120.3
C8—O2—C12	113.01 (11)	C9—C10—H10	120.3
C9—O3—C13	116.17 (11)	O1—C11—H11A	109.5
C15—O4—C20	117.11 (12)	O1—C11—H11B	109.5
C1—N1—N2	103.56 (11)	H11A—C11—H11B	109.5
C2—N2—N1	113.78 (11)	O1—C11—H11C	109.5
C2—N2—H2N	125.4 (11)	H11A—C11—H11C	109.5
N1—N2—H2N	119.5 (11)	H11B—C11—H11C	109.5
C2—N3—C1	107.91 (12)	O2—C12—H12A	109.5
C2—N3—C14	126.41 (11)	O2—C12—H12B	109.5
C1—N3—C14	125.68 (11)	H12A—C12—H12B	109.5
N1—C1—N3	111.33 (12)	O2—C12—H12C	109.5
N1—C1—C3	126.51 (12)	H12A—C12—H12C	109.5
N3—C1—C3	122.13 (12)	H12B—C12—H12C	109.5
N2—C2—N3	103.34 (11)	O3—C13—H13A	109.5
N2—C2—S1	128.07 (11)	O3—C13—H13B	109.5
N3—C2—S1	128.58 (11)	H13A—C13—H13B	109.5
C1—C3—C4	112.98 (12)	O3—C13—H13C	109.5
C1—C3—H3A	109.0	H13A—C13—H13C	109.5
C4—C3—H3A	109.0	H13B—C13—H13C	109.5
C1—C3—H3B	109.0	C19—C14—C15	121.49 (13)
C4—C3—H3B	109.0	C19—C14—N3	119.04 (13)
H3A—C3—H3B	107.8	C15—C14—N3	119.47 (12)
C5—C4—C3	111.07 (12)	O4—C15—C14	115.78 (12)
C5—C4—H4A	109.4	O4—C15—C16	125.22 (13)
C3—C4—H4A	109.4	C14—C15—C16	118.99 (13)
C5—C4—H4B	109.4	C17—C16—C15	119.34 (14)
C3—C4—H4B	109.4	C17—C16—H16	120.3
H4A—C4—H4B	108.0	C15—C16—H16	120.3
C10—C5—C6	120.43 (13)	C18—C17—C16	121.38 (14)
C10—C5—C4	120.11 (13)	C18—C17—H17	119.3
C6—C5—C4	119.45 (12)	C16—C17—H17	119.3
C5—C6—C7	120.17 (13)	C17—C18—C19	119.21 (14)
C5—C6—H6	119.9	C17—C18—H18	120.4
C7—C6—H6	119.9	C19—C18—H18	120.4
O1—C7—C6	125.01 (14)	C14—C19—C18	119.55 (14)
O1—C7—C8	115.33 (13)	C14—C19—H19	120.2
C6—C7—C8	119.65 (14)	C18—C19—H19	120.2
O2—C8—C9	120.15 (12)	O4—C20—H20A	109.5
O2—C8—C7	119.89 (13)	O4—C20—H20B	109.5
C9—C8—C7	119.96 (12)	H20A—C20—H20B	109.5
O3—C9—C8	115.17 (12)	O4—C20—H20C	109.5
O3—C9—C10	124.48 (13)	H20A—C20—H20C	109.5
C8—C9—C10	120.34 (13)	H20B—C20—H20C	109.5
C5—C10—C9	119.45 (13)
C1—N1—N2—C2	1.85 (15)	C6—C7—C8—C9	−0.4 (2)
N2—N1—C1—N3	−0.12 (15)	C13—O3—C9—C8	−172.13 (13)
N2—N1—C1—C3	−178.15 (13)	C13—O3—C9—C10	6.8 (2)
C2—N3—C1—N1	−1.52 (16)	O2—C8—C9—O3	−1.54 (19)
C14—N3—C1—N1	178.47 (12)	C7—C8—C9—O3	178.61 (13)
C2—N3—C1—C3	176.61 (12)	O2—C8—C9—C10	179.45 (12)
C14—N3—C1—C3	−3.4 (2)	C7—C8—C9—C10	−0.4 (2)
N1—N2—C2—N3	−2.71 (15)	C6—C5—C10—C9	−0.7 (2)
N1—N2—C2—S1	176.30 (10)	C4—C5—C10—C9	179.49 (12)
C1—N3—C2—N2	2.48 (14)	O3—C9—C10—C5	−177.96 (13)
C14—N3—C2—N2	−177.52 (12)	C8—C9—C10—C5	1.0 (2)
C1—N3—C2—S1	−176.53 (11)	C2—N3—C14—C19	72.32 (18)
C14—N3—C2—S1	3.5 (2)	C1—N3—C14—C19	−107.68 (15)
N1—C1—C3—C4	0.6 (2)	C2—N3—C14—C15	−107.91 (15)
N3—C1—C3—C4	−177.23 (12)	C1—N3—C14—C15	72.09 (18)
C1—C3—C4—C5	166.39 (11)	C20—O4—C15—C14	−172.91 (13)
C3—C4—C5—C10	104.08 (15)	C20—O4—C15—C16	6.9 (2)
C3—C4—C5—C6	−75.69 (17)	C19—C14—C15—O4	−179.94 (12)
C10—C5—C6—C7	0.0 (2)	N3—C14—C15—O4	0.29 (18)
C4—C5—C6—C7	179.76 (14)	C19—C14—C15—C16	0.2 (2)
C11—O1—C7—C6	3.6 (3)	N3—C14—C15—C16	−179.52 (12)
C11—O1—C7—C8	−177.92 (19)	O4—C15—C16—C17	178.73 (13)
C5—C6—C7—O1	178.94 (15)	C14—C15—C16—C17	−1.5 (2)
C5—C6—C7—C8	0.6 (2)	C15—C16—C17—C18	1.2 (2)
C12—O2—C8—C9	82.37 (17)	C16—C17—C18—C19	0.3 (2)
C12—O2—C8—C7	−97.78 (17)	C15—C14—C19—C18	1.3 (2)
O1—C7—C8—O2	1.3 (2)	N3—C14—C19—C18	−178.96 (12)
C6—C7—C8—O2	179.79 (13)	C17—C18—C19—C14	−1.5 (2)
O1—C7—C8—C9	−178.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2i	0.878 (17)	1.890 (18)	2.7558 (15)	168.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O2i	0.878 (17)	1.890 (18)	2.7558 (15)	168.4 (15)

Symmetry code: (i) .