Literature DB >> 24940299

4-[(E)-(4-Hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Balladka K Sarojini¹, Padmanabha S Manjula², B Narayana³, Jerry P Jasinski⁴.

Abstract

The title compound, C10H10N4OS, is nearly planar with the mean planes of the hy-droxy-benzyl and triazole rings inclined at an angle of only 3.2 (7)°. In the crystal, O-H⋯N hydrogen bonds between the hy-droxy group and the triazole ring in concert with weak N-H⋯S inter-molecular inter-actions between the triazole ring and thione group form chains along [-210] enclosing R 2 (2)(8) graph-set motifs. A weak intra-molecular C-H⋯S inter-action and inter-molecular π-π inter-actions [centroid-centroid distance = 3.5990 (15) Å] are also observed.

Entities: Chemical Disease Species

Year: 2014 PMID： 24940299 PMCID： PMC4051099 DOI： 10.1107/S1600536814012215

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

Related literature

For the chemistry of Schiff base compounds, see: Dubey & Vaid (1991 ▶); Yadav et al. (1994 ▶). For uses of Schiff bases in analytical applications and metal coordination, see: Galic et al. (2001 ▶); Wyrzykiewicz & Prukah (1998 ▶); Reddy & Lirgappa (1994 ▶). For the chemical and biological activity of Schiff base compounds, see: Barrera et al. (1985 ▶); Dornow et al. (1964 ▶); Malik et al. (2011 ▶); Thieme et al. (1973a ▶,b ▶); Wei & Bell (1982 ▶). For related structures see: Kant et al. (2012 ▶); Praveen et al. (2012 ▶); Kubicki et al. (2012 ▶); Jeyaseelan et al. (2012 ▶); Devarajegowda et al. (2012 ▶); Vinduvahini et al. (2011 ▶); Almutairi et al. (2012 ▶); Ding et al. (2009 ▶); Sarojini et al. (2007a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H10N4OS M = 234.28 Triclinic, a = 5.7677 (5) Å b = 7.7233 (8) Å c = 12.7269 (12) Å α = 84.104 (8)° β = 77.719 (8)° γ = 73.358 (9)° V = 530.23 (9) Å3 Z = 2 Cu Kα radiation μ = 2.59 mm−1 T = 173 K 0.28 × 0.16 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.723, T max = 1.000 3082 measured reflections 1987 independent reflections 1658 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.151 S = 1.05 1987 reflections 147 parameters H-atom parameters constrained Δρmax = 0.62 e Å−3 Δρmin = −0.40 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814012215/sj5405sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012215/sj5405Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814012215/sj5405Isup3.cml CCDC reference: 1005409 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₀H₁₀N₄OS	Z = 2
M_r = 234.28	F(000) = 244
Triclinic, P1	D_x = 1.467 Mg m⁻³
a = 5.7677 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.7233 (8) Å	Cell parameters from 1294 reflections
c = 12.7269 (12) Å	θ = 6.0–71.1°
α = 84.104 (8)°	µ = 2.59 mm⁻¹
β = 77.719 (8)°	T = 173 K
γ = 73.358 (9)°	Prism, colourless
V = 530.23 (9) Å³	0.28 × 0.16 × 0.12 mm

Agilent Eos Gemini diffractometer	1987 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1658 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.3°, θ_min = 3.6°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −8→9
T_min = 0.723, T_max = 1.000	l = −11→15
3082 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0895P)² + 0.0331P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
1987 reflections	Δρ_max = 0.62 e Å⁻³
147 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	U_iso*/U_eq
S1	1.11567 (12)	0.19885 (9)	0.52135 (5)	0.0379 (3)
O1	−0.1143 (3)	0.9783 (3)	0.86418 (16)	0.0377 (5)
H1	−0.2048	1.0077	0.8180	0.057*
N1	0.9248 (4)	0.4001 (3)	0.76560 (17)	0.0283 (5)
N2	1.1501 (4)	0.2819 (3)	0.72431 (16)	0.0256 (4)
N3	1.5264 (4)	0.1215 (3)	0.73740 (18)	0.0307 (5)
N4	1.4752 (4)	0.1066 (3)	0.63900 (17)	0.0300 (5)
H4	1.5835	0.0420	0.5881	0.036*
C1	1.2477 (4)	0.1981 (3)	0.6267 (2)	0.0265 (5)
C2	1.3255 (4)	0.2280 (3)	0.7878 (2)	0.0287 (5)
C3	0.7774 (5)	0.4764 (3)	0.7032 (2)	0.0318 (6)
H3	0.8179	0.4491	0.6293	0.038*
C4	0.5459 (4)	0.6061 (3)	0.7454 (2)	0.0276 (5)
C5	0.3644 (5)	0.6680 (4)	0.6829 (2)	0.0322 (6)
H5	0.3944	0.6250	0.6126	0.039*
C6	0.1427 (5)	0.7901 (3)	0.7209 (2)	0.0316 (6)
H6	0.0210	0.8298	0.6773	0.038*
C7	0.0976 (4)	0.8550 (3)	0.8236 (2)	0.0289 (5)
C8	0.2773 (5)	0.7967 (3)	0.8869 (2)	0.0327 (6)
H8	0.2482	0.8420	0.9566	0.039*
C9	0.4976 (5)	0.6732 (3)	0.8483 (2)	0.0324 (6)
H9	0.6186	0.6329	0.8923	0.039*
C10	1.2826 (5)	0.2836 (4)	0.9004 (2)	0.0384 (6)
H10A	1.1664	0.2240	0.9467	0.058*
H10B	1.2139	0.4151	0.9029	0.058*
H10C	1.4392	0.2481	0.9259	0.058*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0299 (4)	0.0437 (4)	0.0324 (4)	0.0105 (3)	−0.0096 (3)	−0.0190 (3)
O1	0.0277 (10)	0.0413 (11)	0.0346 (10)	0.0111 (8)	−0.0076 (8)	−0.0141 (8)
N1	0.0209 (10)	0.0271 (10)	0.0295 (11)	0.0057 (8)	−0.0011 (8)	−0.0113 (8)
N2	0.0212 (10)	0.0252 (9)	0.0255 (10)	0.0022 (8)	−0.0022 (8)	−0.0090 (8)
N3	0.0262 (11)	0.0329 (11)	0.0286 (11)	0.0026 (9)	−0.0061 (8)	−0.0104 (8)
N4	0.0229 (10)	0.0309 (10)	0.0295 (11)	0.0047 (8)	−0.0016 (8)	−0.0127 (8)
C1	0.0229 (11)	0.0252 (11)	0.0257 (11)	0.0025 (9)	−0.0016 (9)	−0.0085 (9)
C2	0.0223 (12)	0.0283 (12)	0.0314 (13)	0.0013 (9)	−0.0059 (10)	−0.0056 (10)
C3	0.0280 (13)	0.0294 (12)	0.0313 (13)	0.0013 (10)	−0.0011 (10)	−0.0077 (10)
C4	0.0224 (12)	0.0270 (11)	0.0280 (12)	0.0022 (9)	−0.0030 (9)	−0.0066 (9)
C5	0.0322 (13)	0.0355 (13)	0.0240 (12)	0.0016 (11)	−0.0048 (10)	−0.0121 (10)
C6	0.0265 (13)	0.0353 (13)	0.0291 (13)	0.0022 (10)	−0.0093 (10)	−0.0056 (10)
C7	0.0218 (12)	0.0258 (11)	0.0334 (13)	0.0021 (9)	−0.0024 (10)	−0.0063 (10)
C8	0.0293 (13)	0.0347 (13)	0.0300 (13)	0.0033 (11)	−0.0070 (10)	−0.0154 (11)
C9	0.0251 (13)	0.0350 (13)	0.0324 (13)	0.0060 (10)	−0.0099 (10)	−0.0118 (11)
C10	0.0342 (15)	0.0457 (15)	0.0285 (13)	0.0058 (12)	−0.0087 (11)	−0.0133 (12)

S1—C1	1.675 (2)	C4—C5	1.396 (4)
O1—H1	0.8400	C4—C9	1.401 (4)
O1—C7	1.354 (3)	C5—H5	0.9500
N1—N2	1.388 (3)	C5—C6	1.378 (4)
N1—C3	1.267 (3)	C6—H6	0.9500
N2—C1	1.392 (3)	C6—C7	1.394 (4)
N2—C2	1.374 (3)	C7—C8	1.393 (4)
N3—N4	1.369 (3)	C8—H8	0.9500
N3—C2	1.295 (3)	C8—C9	1.379 (3)
N4—H4	0.8800	C9—H9	0.9500
N4—C1	1.334 (3)	C10—H10A	0.9800
C2—C10	1.488 (4)	C10—H10B	0.9800
C3—H3	0.9500	C10—H10C	0.9800
C3—C4	1.454 (3)

C7—O1—H1	109.5	C4—C5—H5	119.3
C3—N1—N2	119.5 (2)	C6—C5—C4	121.4 (2)
N1—N2—C1	133.6 (2)	C6—C5—H5	119.3
C2—N2—N1	118.42 (19)	C5—C6—H6	120.1
C2—N2—C1	108.01 (19)	C5—C6—C7	119.7 (2)
C2—N3—N4	104.1 (2)	C7—C6—H6	120.1
N3—N4—H4	122.8	O1—C7—C6	122.3 (2)
C1—N4—N3	114.5 (2)	O1—C7—C8	117.8 (2)
C1—N4—H4	122.8	C8—C7—C6	119.8 (2)
N2—C1—S1	130.18 (18)	C7—C8—H8	120.1
N4—C1—S1	127.45 (18)	C9—C8—C7	119.9 (2)
N4—C1—N2	102.3 (2)	C9—C8—H8	120.1
N2—C2—C10	123.3 (2)	C4—C9—H9	119.5
N3—C2—N2	111.1 (2)	C8—C9—C4	121.1 (2)
N3—C2—C10	125.6 (2)	C8—C9—H9	119.5
N1—C3—H3	120.2	C2—C10—H10A	109.5
N1—C3—C4	119.6 (2)	C2—C10—H10B	109.5
C4—C3—H3	120.2	C2—C10—H10C	109.5
C5—C4—C3	120.1 (2)	H10A—C10—H10B	109.5
C5—C4—C9	118.0 (2)	H10A—C10—H10C	109.5
C9—C4—C3	121.9 (2)	H10B—C10—H10C	109.5

O1—C7—C8—C9	−179.1 (2)	C2—N2—C1—S1	175.0 (2)
N1—N2—C1—S1	−4.7 (4)	C2—N2—C1—N4	−2.0 (3)
N1—N2—C1—N4	178.3 (2)	C2—N3—N4—C1	−0.9 (3)
N1—N2—C2—N3	−178.6 (2)	C3—N1—N2—C1	−12.7 (4)
N1—N2—C2—C10	2.8 (4)	C3—N1—N2—C2	167.6 (2)
N1—C3—C4—C5	−169.2 (2)	C3—C4—C5—C6	179.6 (2)
N1—C3—C4—C9	11.1 (4)	C3—C4—C9—C8	179.7 (3)
N2—N1—C3—C4	−177.4 (2)	C4—C5—C6—C7	0.5 (4)
N3—N4—C1—S1	−175.24 (19)	C5—C4—C9—C8	0.0 (4)
N3—N4—C1—N2	1.9 (3)	C5—C6—C7—O1	178.4 (3)
N4—N3—C2—N2	−0.5 (3)	C5—C6—C7—C8	0.3 (4)
N4—N3—C2—C10	178.1 (3)	C6—C7—C8—C9	−0.9 (4)
C1—N2—C2—N3	1.6 (3)	C7—C8—C9—C4	0.7 (4)
C1—N2—C2—C10	−177.0 (2)	C9—C4—C5—C6	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.84	1.98	2.804 (3)	165
N4—H4···S1ⁱⁱ	0.88	2.46	3.324 (2)	166
C3—H3···S1	0.95	2.49	3.234 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3ⁱ	0.84	1.98	2.804 (3)	165
N4—H4⋯S1ⁱⁱ	0.88	2.46	3.324 (2)	166
C3—H3⋯S1	0.95	2.49	3.234 (3)	135

Symmetry codes: (i) ; (ii) .

7 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. 4-[(E)-(4-Fluoro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors: H C Devarajegowda; S Jeyaseelan; R Sathishkumar; Agnes Sylvia D'souza; Alphonsus D'souza
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-05-05

3. 3-Ethyl-4-[(E)-(4-fluoro-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

Authors: S Jeyaseelan; H C Devarajegowda; R Sathishkumar; Agnes Sylvia D'souza; Alphonsus D'souza
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-18

4. 3-(Adamantan-1-yl)-4-(prop-2-en-1-yl)-1H-1,2,4-triazole-5(4H)-thione.

Authors: Maha S Almutairi; Mona M Al-Shehri; Ali A El-Emam; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-02-10

5. 3-[2-(2,6-Dichloro-anilino)benz-yl]-4-[(4-meth-oxy-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

Authors: M Vinduvahini; K R Roopashree; Suman Bhattacharya; K Mohan Krishna; Venkatesh B Devaru
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-08-31

6. (E)-N'-(4-Meth-oxy-benzyl-idene)-2-m-tolyl-acetohydrazide.

Authors: A S Praveen; Jerry P Jasinski; Amanda C Keeley; H S Yathirajan; B Narayana
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-11-24

7. (1Z)-1-[(2E)-3-(4-Bromo-phen-yl)-1-(4-fluoro-phen-yl)prop-2-en-1-yl-idene]-2-(2,4-dinitro-phen-yl)hydrazine.

Authors: Rajni Kant; Vivek K Gupta; Kamini Kapoor; M Sapnakumari; B K Sarojini; B Narayana
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-06-23

7 in total

2 in total

1. The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thio-nes, including a second polymorph of 4-[(E)-(5-bromo-2-hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors: Padmanabha S Manjula; Balladka K Sarojini; Hemmige S Yathirajan; Mehmet Akkurt; Cem Cüneyt Ersanlı; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2015-08-06

2. Crystal structure of 4-[(E)-(4-chloro-benzyl-idene)amino]-3-(2-methyl-benz-yl)-1H-1,2,4-triazole-5(4H)-thione.

Authors: B K Sarojini; P S Manjula; B Narayana; Sumati Anthal; Rajni Kant
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2014-08-16

2 in total