4-(4-Methylphenyl)-3-phenyl-4<i>H</i>-1,2,4-triazole

Chinnakali, K.; Fun, Hoong‐Kun; Senthilvelan, Annamalai; Sriraghavan, K.; Ramakrishnan, V. T.

doi:10.1107/s0108270199002693

Cited by 3 publications

(4 citation statements)

References 2 publications

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“…The C=N bond distance in the title compound is comparable with those found in the 1,2,4-triazole units [8][9][10]. The bond value of N(3)-N(4) [1.381(2) Å] matches very well with the single bond lengths reported for the related structures [10][11][12][13][14][15] and is noticeably shorter than those observed in the 1,2,4-triazole rings [8,9,16]. Fig.…”

Section: Resultssupporting

confidence: 81%

Crystal and molecular structure of 3‐phenyl‐4‐(p‐chlorobenzylamino)‐4,5‐dihydro‐1‐H‐1,2,4‐triazol‐5‐on

Yılmaz¹,

Ağar

Güven

et al. 2004

Cryst. Res. Technol.

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The structure of the title compound, C 15 H 13 N 4 OCl was determined by single crystal X-ray diffraction technique. The structure consists of a p-chlorobenzylamino moiety and triazol and phenyl rings. The title compound crystallizes in the monoclinic space group P2 1 /c with a = 14.368(3), b = 6.255(3), c = 17.631(3) Å, β = 113.24 (3) o , Z = 4, V = 1455.8(8) Å 3 and D x = 1.372 gcm -3 . The structure was solved by direct methods and refined by full-matrix least-squares method (R=0.0477). The dihedral angle between the triazole moiety and the phenyl ring is 28.8 (3) o . The molecular packing is stabilized by N-H…N and N-H…O types of inter molecular hydrogen bonds.

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Section: Resultssupporting

confidence: 81%

Crystal and molecular structure of 3‐phenyl‐4‐(p‐chlorobenzylamino)‐4,5‐dihydro‐1‐H‐1,2,4‐triazol‐5‐on

Yılmaz¹,

Ağar

Güven

et al. 2004

Cryst. Res. Technol.

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“…Many workers reported on crystal structures showing the importance of CH/p bonds. Examples include (1,3-butadiynyl-C 1 )(g5-cyclopentadienyl)(triphenylphosphane-P)Ni, 135 2,3-dihydro-2-alkyl-3-hydroxybenzisothiazole 1,1-dioxides, 136 3-hydroxyphenyl-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid, 137 4-(p-methoxyphenyl)-3,5-bis(2-pyridyl)-4H-1,2,4triazole, 138 methyl (4-methylbenzyl)-3-oxoperhydronaphthalene-2-carboxylate, 139 4-(4-methylphenyl)-3-phenyl-4H-1,2,4-triazole, 140 5-bis[3-(4-methylphenyl)-3-oxopropyl]cyclopentan-1-one, a-methyltyrosinato-2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclododecane]cobalt, 141 binary hydrotris(indazol-1-yl)borato metal complexes, 142 RuCl 2 C 6 H 6 (CH 3 CN), 143 dithia[3.3.1]-metacyclophanes, 144 p-xylylenediammonium disorbate, 145 hexahelicenes 146 and so on. 147…”

Section: Interactions Involving Aromatic P-groupsmentioning

confidence: 99%

CH/? hydrogen bonds in crystals

Nishio¹

2004

CrystEngComm

1,375

781

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The nature and characteristics of the CH/p interaction are discussed by comparison with other weak molecular forces such as the CH/O and OH/p interaction. The CH/p interaction is a kind of hydrogen bond operating between a soft acid CH and a soft base p-system (double and triple bonds, C 6 and C 5 aromatic rings, heteroaromatics, convex surfaces of fullerenes and nanotubes). The consequences of CH/p hydrogen bonds in supramolecular chemistry are reviewed on grounds of recent crystallographic findings and database analyses. The topics include intramolecular interactions, crystal packing (organic and organometallic compounds), host/ guest complexes (cavity-type inclusion compounds of cyclodextrins and synthetic macrocyclic hosts such as calixarenes, catenanes, rotaxanes and pseudorotaxanes), lattice-inclusion type clathrates (including liquid crystals, porphyrin derivatives, cyclopentadienyl compounds and C 60 fullerenes), enantioselective clathrate formation, catalytic enantioface discriminating reactions and solid-state photoreaction. The implications of the CH/p concept for crystal engineering and drug design are evident.

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“…3,4-Diaryl-1,2,4-triazole derivatives have been reported by Mazur et al (2004a,b), Chinnakali et al (1999) and Rogers et al (1990). For pyridine C-HÁ Á ÁN interactions, see also Mootz & Wussow (1981).…”

Section: Related Literaturementioning

confidence: 89%

“…3,4-diaryl-1,2,4-triazole derivatives have been described in literature [refcodes: WAKBEQ, HAMSUK, GOLYUB, VEXPIX; Mazur et al (2004a;2004b), Chinnakali et al (1999) and Rogers et al (1990)].…”

Section: Data Collectionmentioning

confidence: 99%

4-(4-Methylphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole

Mazur

Kozioł

Modzelewska-Banachiewicz

2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 294 K; mean (C-C) = 0.005 Å; R factor = 0.053; wR factor = 0.164; data-to-parameter ratio = 15.7.The crystal structure of the title compound, C 14 H 12 N 4 , is built from two symmetry-independent molecules which are nearly related by translation by the vector a/2. The two molecules exhibit almost identical bond distances and angles but they show significantly different conformations. The relative orientations of the pyridyl and benzene rings about the triazole ring are different in the two molecules, and they pack differently in the crystal structure. Weak intermolecular C-HÁ Á ÁN, C-HÁ Á Á and Á Á Á interactions stabilize the crystal structure [the distance between the triazole ring centroids is 3.687 (4) Å ]. Related literature 3,4-Diaryl-1,2,4-triazole derivatives have been reported by Experimental Crystal data C 14 H 12 N 4 M r = 236.28 Triclinic, P1 a = 10.730 (2) Å b = 10.929 (3) Å c = 11.647 (3) Å = 105.21 (3) = 99.49 (2) = 108.34 (2) V = 1204.5 (6) Å 3 Z = 4 Cu K radiation = 0.65 mm À1 T = 294 (2) K 0.42 Â 0.28 Â 0.20 mm Data collection Kuma KM-4 four-circle diffractometer Absorption correction: none 5413 measured reflections 5153 independent reflections 1942 reflections with I > 2(I) R int = 0.039 3 standard reflections every 100 reflections intensity decay: 0.8%

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4-(4-Methylphenyl)-3-phenyl-4H-1,2,4-triazole

Cited by 3 publications

References 2 publications

Crystal and molecular structure of 3‐phenyl‐4‐(p‐chlorobenzylamino)‐4,5‐dihydro‐1‐H‐1,2,4‐triazol‐5‐on

Crystal and molecular structure of 3‐phenyl‐4‐(p‐chlorobenzylamino)‐4,5‐dihydro‐1‐H‐1,2,4‐triazol‐5‐on

CH/? hydrogen bonds in crystals

4-(4-Methylphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole

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