Literature DB >> 23723880

4-Amino-3-(3-meth-oxy-benz-yl)-1H-1,2,4-triazole-5(4H)-thione.

B K Sarojini¹, P S Manjula, Gurumurthy Hegde, Dalbir Kour, Sumati Anthal, Vivek K Gupta, Rajni Kant.

Abstract

In the title mol-ecule, C10H12N4SO, the triazole ring forms a dihedral angle of 73.0 (5)° with the benzene ring. The meth-oxy group is approximtely coplanar with the benzene ring with a C C-O-Cmeth-yl torsion angle of 4.7 (3)°. In the crystal, N-H⋯S hydrogen bonds connect pairs of inversion-related mol-ecules, which are in turn connected by N-H⋯N hydrogen bonds into chains of rings along [010]. Weak C-H⋯O hydrogen bonds connect these chains into a two-dimensional network parallel to (-102).

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 23723880 PMCID： PMC3648260 DOI： 10.1107/S1600536813009859

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the chemistry of triazoles, see: Holla et al. (2001 ▶, 2006 ▶). For the biological activity of 1,2,4-triazole derivatives, see: Cansiz et al. (2001 ▶); Jones et al. (1965 ▶); Kane et al. (1988 ▶); Mullican et al. (1993 ▶). For related structures, see: Chen et al. (2007 ▶); Gao et al. (2011 ▶); Karczmarzyk et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H12N4OS M = 236.30 Monoclinic, a = 7.4580 (3) Å b = 5.8006 (2) Å c = 25.2817 (10) Å β = 94.513 (4)° V = 1090.32 (7) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 293 K 0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.946, T max = 1.000 15190 measured reflections 2130 independent reflections 1748 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.088 S = 1.03 2130 reflections 154 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009859/lh5605sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009859/lh5605Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813009859/lh5605Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₁₂N₄OS	F(000) = 496
M_r = 236.30	D_x = 1.440 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7374 reflections
a = 7.4580 (3) Å	θ = 3.5–29.0°
b = 5.8006 (2) Å	µ = 0.28 mm⁻¹
c = 25.2817 (10) Å	T = 293 K
β = 94.513 (4)°	Plate, white
V = 1090.32 (7) Å³	0.3 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2130 independent reflections
Radiation source: fine-focus sealed tube	1748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
T_min = 0.946, T_max = 1.000	l = −31→31
15190 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0408P)² + 0.3289P] where P = (F_o² + 2F_c²)/3
2130 reflections	(Δ/σ)_max = 0.002
154 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	U_iso*/U_eq
S1	0.79363 (6)	1.26508 (8)	1.014843 (19)	0.03712 (16)
O1	0.4364 (2)	0.7659 (2)	0.66746 (5)	0.0467 (4)
N1	0.6715 (2)	0.7764 (2)	0.91172 (6)	0.0323 (4)
N2	0.77124 (19)	0.8746 (2)	0.95420 (6)	0.0319 (4)
H2	0.8621	0.8077	0.9707	0.038*
C3	0.7134 (2)	1.0833 (3)	0.96726 (6)	0.0254 (4)
N4	0.56824 (17)	1.1164 (2)	0.93177 (5)	0.0239 (3)
C5	0.5471 (2)	0.9287 (3)	0.89877 (6)	0.0246 (4)
N6	0.4558 (2)	1.3106 (3)	0.92853 (8)	0.0360 (4)
C7	0.4041 (2)	0.9044 (3)	0.85492 (6)	0.0284 (4)
H7A	0.2994	0.9908	0.8639	0.034*
H7B	0.3696	0.7434	0.8519	0.034*
C8	0.4584 (2)	0.9870 (3)	0.80138 (6)	0.0249 (4)
C9	0.5382 (2)	1.2018 (3)	0.79529 (7)	0.0322 (4)
H9	0.5617	1.2972	0.8246	0.039*
C10	0.5823 (2)	1.2730 (3)	0.74597 (8)	0.0339 (4)
H10	0.6347	1.4170	0.7423	0.041*
C11	0.5501 (2)	1.1344 (3)	0.70177 (7)	0.0328 (4)
H11	0.5805	1.1838	0.6686	0.039*
C12	0.4717 (2)	0.9206 (3)	0.70779 (7)	0.0290 (4)
C13	0.4246 (2)	0.8490 (3)	0.75726 (7)	0.0271 (4)
H13	0.3696	0.7064	0.7607	0.032*
C14	0.4954 (3)	0.8208 (4)	0.61719 (8)	0.0492 (5)
H14A	0.4348	0.9572	0.6037	0.074*
H14B	0.4686	0.6950	0.5932	0.074*
H14C	0.6228	0.8475	0.6205	0.074*
H62	0.524 (3)	1.436 (4)	0.9246 (8)	0.049 (6)*
H61	0.403 (3)	1.324 (4)	0.9573 (10)	0.065 (8)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0330 (3)	0.0444 (3)	0.0325 (3)	0.0079 (2)	−0.00694 (19)	−0.0124 (2)
O1	0.0607 (9)	0.0517 (8)	0.0284 (7)	−0.0206 (7)	0.0078 (6)	−0.0085 (6)
N1	0.0352 (8)	0.0312 (8)	0.0297 (9)	0.0065 (6)	−0.0034 (7)	−0.0030 (6)
N2	0.0317 (8)	0.0324 (8)	0.0303 (8)	0.0109 (6)	−0.0064 (7)	−0.0018 (6)
C3	0.0232 (8)	0.0305 (9)	0.0227 (9)	0.0032 (7)	0.0025 (7)	0.0025 (7)
N4	0.0223 (7)	0.0239 (7)	0.0250 (7)	0.0044 (5)	−0.0015 (6)	−0.0009 (6)
C5	0.0267 (8)	0.0244 (8)	0.0228 (9)	−0.0007 (7)	0.0033 (7)	0.0004 (6)
N6	0.0353 (9)	0.0290 (9)	0.0422 (11)	0.0141 (7)	−0.0073 (8)	−0.0061 (7)
C7	0.0264 (9)	0.0310 (9)	0.0273 (9)	−0.0015 (7)	−0.0010 (7)	−0.0032 (7)
C8	0.0204 (8)	0.0265 (8)	0.0272 (9)	0.0033 (6)	−0.0028 (7)	0.0003 (7)
C9	0.0355 (10)	0.0263 (9)	0.0341 (10)	−0.0017 (7)	−0.0023 (8)	−0.0043 (7)
C10	0.0326 (10)	0.0238 (9)	0.0450 (11)	−0.0031 (7)	0.0003 (8)	0.0055 (8)
C11	0.0311 (9)	0.0363 (10)	0.0310 (10)	−0.0006 (8)	0.0016 (8)	0.0079 (8)
C12	0.0261 (9)	0.0335 (9)	0.0267 (9)	−0.0010 (7)	−0.0012 (7)	−0.0008 (7)
C13	0.0256 (9)	0.0248 (8)	0.0304 (10)	−0.0024 (7)	−0.0004 (7)	0.0008 (7)
C14	0.0469 (13)	0.0726 (15)	0.0287 (11)	−0.0096 (11)	0.0073 (9)	−0.0059 (10)

S1—C3	1.6745 (17)	C7—H7B	0.9700
O1—C12	1.368 (2)	C8—C13	1.380 (2)
O1—C14	1.414 (2)	C8—C9	1.395 (2)
N1—C5	1.304 (2)	C9—C10	1.377 (3)
N1—N2	1.381 (2)	C9—H9	0.9300
N2—C3	1.335 (2)	C10—C11	1.382 (3)
N2—H2	0.8600	C10—H10	0.9300
C3—N4	1.364 (2)	C11—C12	1.384 (2)
N4—C5	1.373 (2)	C11—H11	0.9300
N4—N6	1.4029 (19)	C12—C13	1.389 (2)
C5—C7	1.483 (2)	C13—H13	0.9300
N6—H62	0.90 (2)	C14—H14A	0.9600
N6—H61	0.86 (3)	C14—H14B	0.9600
C7—C8	1.521 (2)	C14—H14C	0.9600
C7—H7A	0.9700

C12—O1—C14	117.84 (15)	C13—C8—C7	119.48 (15)
C5—N1—N2	104.16 (13)	C9—C8—C7	121.71 (15)
C3—N2—N1	113.69 (14)	C10—C9—C8	120.12 (16)
C3—N2—H2	123.2	C10—C9—H9	119.9
N1—N2—H2	123.2	C8—C9—H9	119.9
N2—C3—N4	102.72 (14)	C9—C10—C11	121.26 (16)
N2—C3—S1	130.12 (13)	C9—C10—H10	119.4
N4—C3—S1	127.17 (12)	C11—C10—H10	119.4
C3—N4—C5	109.59 (13)	C10—C11—C12	118.69 (17)
C3—N4—N6	126.24 (14)	C10—C11—H11	120.7
C5—N4—N6	124.17 (14)	C12—C11—H11	120.7
N1—C5—N4	109.83 (15)	O1—C12—C11	124.32 (16)
N1—C5—C7	125.34 (15)	O1—C12—C13	115.29 (15)
N4—C5—C7	124.83 (14)	C11—C12—C13	120.39 (16)
N4—N6—H62	108.4 (14)	C8—C13—C12	120.74 (15)
N4—N6—H61	109.5 (17)	C8—C13—H13	119.6
H62—N6—H61	109 (2)	C12—C13—H13	119.6
C5—C7—C8	114.15 (14)	O1—C14—H14A	109.5
C5—C7—H7A	108.7	O1—C14—H14B	109.5
C8—C7—H7A	108.7	H14A—C14—H14B	109.5
C5—C7—H7B	108.7	O1—C14—H14C	109.5
C8—C7—H7B	108.7	H14A—C14—H14C	109.5
H7A—C7—H7B	107.6	H14B—C14—H14C	109.5
C13—C8—C9	118.79 (16)

C5—N1—N2—C3	−0.81 (19)	C5—C7—C8—C13	132.14 (16)
N1—N2—C3—N4	1.00 (18)	C5—C7—C8—C9	−49.4 (2)
N1—N2—C3—S1	−179.11 (13)	C13—C8—C9—C10	−0.1 (3)
N2—C3—N4—C5	−0.80 (17)	C7—C8—C9—C10	−178.66 (16)
S1—C3—N4—C5	179.30 (13)	C8—C9—C10—C11	−0.4 (3)
N2—C3—N4—N6	179.29 (16)	C9—C10—C11—C12	0.1 (3)
S1—C3—N4—N6	−0.6 (3)	C14—O1—C12—C11	4.7 (3)
N2—N1—C5—N4	0.25 (18)	C14—O1—C12—C13	−174.70 (17)
N2—N1—C5—C7	−179.94 (15)	C10—C11—C12—O1	−178.59 (17)
C3—N4—C5—N1	0.36 (19)	C10—C11—C12—C13	0.8 (3)
N6—N4—C5—N1	−179.74 (16)	C9—C8—C13—C12	1.0 (2)
C3—N4—C5—C7	−179.46 (15)	C7—C8—C13—C12	179.59 (15)
N6—N4—C5—C7	0.4 (3)	O1—C12—C13—C8	178.05 (15)
N1—C5—C7—C8	−87.4 (2)	C11—C12—C13—C8	−1.4 (3)
N4—C5—C7—C8	92.39 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1ⁱ	0.97	2.46	3.308 (2)	146
N6—H62···N1ⁱⁱ	0.90 (2)	2.30 (2)	3.190 (2)	174
N2—H2···S1ⁱⁱⁱ	0.86	2.60	3.377 (1)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1ⁱ	0.97	2.46	3.308 (2)	146
N6—H62⋯N1ⁱⁱ	0.90 (2)	2.30 (2)	3.190 (2)	174
N2—H2⋯S1ⁱⁱⁱ	0.86	2.60	3.377 (1)	151

Symmetry codes: (i) ; (ii) ; (iii) .

8 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and studies on some new fluorine containing triazolothiadiazines as possible antibacterial, antifungal and anticancer agents.

Authors: B Shivarama Holla; B Sooryanarayana Rao; B K Sarojini; P M Akberali; N Suchetha Kumari
Journal: Eur J Med Chem Date: 2006-04-17 Impact factor: 6.514

3. Synthesis of some halogen-containing 1,2,4-triazolo-1,3,4-thiadiazines and their antibacterial and anticancer screening studies--part I.

Authors: B S Holla; B K Sarojini; B S Rao; P M Akberali; N S Kumari; V Shetty
Journal: Farmaco Date: 2001-08

4. 2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents.

Authors: J M Kane; M W Dudley; S M Sorensen; F P Miller
Journal: J Med Chem Date: 1988-06 Impact factor: 7.446

5. Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally-active, nonulcerogenic antiinflammatory agents.

Authors: M D Mullican; M W Wilson; D T Connor; C R Kostlan; D J Schrier; R D Dyer
Journal: J Med Chem Date: 1993-04-16 Impact factor: 7.446