2,2′-(4-Amino-4H-1,2,4-triazole-3,5-di­yl)diphenol

Sheng-Hui Chen; Gao-Yong Zhang; Jin-Feng Dong

doi:10.1107/S1600536809055536

. 2010 Jan 9;66(Pt 2):o330. doi: 10.1107/S1600536809055536

2,2′-(4-Amino-4H-1,2,4-triazole-3,5-diyl)diphenol

Sheng-Hui Chen ^a, Gao-Yong Zhang ^a, Jin-Feng Dong ^a,^*

PMCID: PMC2979808 PMID: 21579760

Abstract

The structure of the title compound, C₁₄H₁₂N₄O₂, was determined as part of a project on the coordination chemistry of 1,2,4-triazole derivatives. In the crystal structure, one of the two benzene rings is almost coplanar with the five-membered triazole ring (mean deviation = 0.019 Å), whereas the second benzene ring is rotated by 51.973 (2)°. The two N—C—N—N torsion angles [170.365 (2) and −170.942 (3)°] indicate that the amido group is slightly twisted away from the triazole plane. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonding is found.

Related literature

For background information on tthe coordination chemistry of 1,2,4-triazole derivatives, see: Lavrenova et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₂N₄O₂
M _r = 268.28
Orthorhombic,
a = 8.262 (2) Å
b = 9.384 (3) Å
c = 15.919 (4) Å
V = 1234.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.992
6343 measured reflections
1276 independent reflections
1143 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.112
S = 1.10
1276 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055536/nc2167sup1.cif

e-66-0o330-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055536/nc2167Isup2.hkl

e-66-0o330-Isup2.hkl^{(63.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.95 (5)	2.39 (6)	3.153 (4)	136 (4)
O1—H1⋯N1	0.82	1.87	2.598 (3)	148
O2—H2A⋯N2ⁱⁱ	0.82	1.91	2.705 (3)	162

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 20573079) for financial support.

supplementary crystallographic information

Experimental

2-hydroxy-N-(2-hydroxybenzoyl)benzohydrazide and hydrazine monohydrate were purchased from Acros and used without further purification. 2-hydroxy-N-(2-hydroxybenzoyl)benzohydrazide (4.08 g, 0.15 mmol) and hydrazine monohydrate(7.27 ml, 0.15 mol) were transfered into a 50 ml round-bottom flask. The mixture was stirred and refluxed for 3 h. After cooling, the solution was poured into ice water and the resulting light pink precipitate was collected by filtration, and recrystallized from ethanol. colorless crystal, 1.812 g (46.6 %), ¹H NMR (DMSO, 400 MHz, p.p.m.): 11.27 (s, 2H), 8.0 (q, 2H), 7.4 (m, 2H), 7.0 (q, 4H), 6.14 (s, 2H). m.p = 532.3–533.2 K. Anal. Calcd for C₁₄H₁₂O₂N₄: C, 62.69; H, 4.48; N, 20.90%, Found: C, 62.58; H, 4.42; N, 20.83 %. GC—MS(m/z): 268 (M⁺), 249, 221, 207, 117, 91, 77, 51, 32.