1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

Yu-Guang Wang; Guo-Bo Huang; Bing-Chun Zhu

doi:10.1107/S160053680901263X

. 2009 Apr 10;65(Pt 5):o1015–o1016. doi: 10.1107/S160053680901263X

1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

Yu-Guang Wang ^a,^*, Guo-Bo Huang ^b, Bing-Chun Zhu ^c,^d

PMCID: PMC2977702 PMID: 21583838

Abstract

In the molecule of the title compound, C₁₈H₁₆F₂N₄O₂, the 1,2,4-triazole ring forms dihedral angles of 3.6 (2) and 14.9 (6)° with the 4-difluoromethoxy-substituted benzene ring and the 2,3-dimethyl-substituted benzene ring, respectively. The OCHF₂ group is twisted away from the plane of the benzene ring, as shown by the C—O—C—C torsion angle of 145.8 (2)°. The conformation is stabilized by an intermolecular N—H⋯N hydrogen bond. In the crystal, short C—H⋯O interactions lead to chains of molecules.

Related literature

For general background regarding the biological and pharmacological activities of 1,2,4-triazoles and their derivatives, see: Wahbi et al. (1995 ▶); Chai et al. (2003 ▶); Hashimoto et al. (1990 ▶); Kalluraya et al. (1996 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Kanazawa et al. (1988 ▶); Vlasova et al. (1971 ▶); Labanauskas et al. (2004 ▶); Tozkoparan et al. (2007 ▶). For a related synthesis, see: Drutkowski et al. (2002 ▶); Frohberg et al. (2002 ▶).

Experimental

Crystal data

C₁₈H₁₆F₂N₄O₂
M _r = 358.35
Triclinic,
a = 7.5543 (10) Å
b = 7.8132 (10) Å
c = 14.8190 (19) Å
α = 95.974 (2)°
β = 98.593 (1)°
γ = 101.523 (1)°
V = 839.28 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.49 × 0.31 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.948, T _max = 0.990
6446 measured reflections
3115 independent reflections
2366 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.123
S = 1.06
3115 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks wyg, I. DOI: 10.1107/S160053680901263X/ez2162sup1.cif

e-65-o1015-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901263X/ez2162Isup2.hkl

e-65-o1015-Isup2.hkl^{(152.8KB, 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—H4D⋯N3	0.86	2.27	2.717 (2)	113
C6—H6⋯O2ⁱ	0.93	2.43	3.344 (2)	169
C8—H8⋯O2ⁱ	0.93	2.26	3.159 (2)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful for the financial support of the Education Office Foundation of Zhejiang Province (project No. Y200803795).

supplementary crystallographic information

Comment

1,2,4-Triazoles and their derivatives have long been known to exhibit diverse biological and pharmacological activities, such as antitubercular, anticancer (Vlasova et al., 1971; Kalluraya et al., 1996), anticonvulsant (Almasirad et al., 2004; Kanazawa et al., 1988; Chai et al., 2003; Hashimoto et al., 1990), anti-inflammatory (Labanauskas et al. ,2004), herbicidal, and analgesic properties (Tozkoparan et al., 2007; Amir & Shikha, 2004). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring has been reported (Wahbi et al., 1995). Herein, we report the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The planar 1,2,4-triazole ring is oriented at dihedral angles of 3.6 (2)° and 14.9 (6)° with respect to the 4-difluoromethoxy-substituted benzene ring and 2,3-dimethyl-substituted benzene ring, respectively. The CHF₂ group is twisted away from the plane of the benzene ring, as shown by the C1—O1—C2—C3 torsion angle [145.8 (2)°].

Experimental

The general procedure to synthesize the title compound: 2-amine-N-(2,3-dimethyl-phenyl)-2-[(4-difluoromethoxy- phenyl)hydrazono]acetamide (10 mmol), 1.5 mL of a 37%-solution of formaldehyde (20 mmol) and 0.1 g p-toluene sulfonic acid were refluxed in approximately 50 mL ethanol. The reaction was complete after 10 h. The mixture was cooled to room temperature and the solvent was evaporated. The solid product was collected and recrystallized from 2-propanol (Drutkowski et al., 2002; Frohberg et al., 2002).