3-Ethyl-4-[3-(1H-imidazol-1-yl)prop­yl]-5-phenyl-4H-1,2,4-triazole dihydrate

Anuradha Gurumoorthy; Vasuki Gopalsamy; Dilek Ünlüer; Esra Düğdü; Babu Varghesee

doi:10.1107/S160053681003936X

. 2010 Oct 9;66(Pt 11):o2777–o2778. doi: 10.1107/S160053681003936X

3-Ethyl-4-[3-(1H-imidazol-1-yl)propyl]-5-phenyl-4H-1,2,4-triazole dihydrate

Anuradha Gurumoorthy ^a, Vasuki Gopalsamy ^b,^*, Dilek Ünlüer ^c, Esra Düğdü ^c, Babu Varghesee ^d

PMCID: PMC3008975 PMID: 21588976

Abstract

In the title compound, C₁₆H₁₉N₅·2H₂O, the triazole ring makes dihedral angles of 70.61 (6) and 41.89 (8)°, respectively, with the imidazole and benzene rings. The water molecules are involved in intermolecular O—H⋯N and O—H⋯O hydrogen bonds, which stabilize the crystal packing.

Related literature

For a related structure, see: Rizzoli et al. (2009 ▶); Kalkan et al. (2007 ▶). For bond lengths and angles in triazole rings, see: Thenmozhi et al. (2010 ▶); Rizzoli et al. (2009 ▶); Dolzhenko et al. (2010 ▶); Ocak Ískeleli et al. (2005 ▶); Ünver et al. (2010 ▶). For the biological activity of triazole Schiff bases, see: Thenmozhi et al. (2010 ▶) and of 1,2,4-triazole derivatives, see: Ünver et al. (2010 ▶). For the search for and synthesis of new antibiotics, see: Köysal et al. (2006 ▶). For the synthesis, see: Ünver et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₉N₅·2H₂O
M _r = 317.39
Monoclinic,
a = 11.0787 (16) Å
b = 9.8428 (8) Å
c = 16.3289 (18) Å
β = 105.602 (9)°
V = 1715.0 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan North et al. (1968 ▶) T _min = 0.821, T _max = 0.876
3030 measured reflections
2868 independent reflections
2166 reflections with I > 2σ(I)
R _int = 0.029
2 standard reflections every 60 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.123
S = 1.08
2868 reflections
226 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ZORTEP (Zsolnai, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003936X/jh2213sup1.cif

e-66-o2777-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003936X/jh2213Isup2.hkl

e-66-o2777-Isup2.hkl^{(140.8KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

C7—N1	1.308 (2)
C7—N3	1.373 (2)
C8—N2	1.312 (2)
C8—N3	1.363 (2)
N1—N2	1.387 (2)

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C8—N3—C7	105.09 (14)
C8—N3—C11	126.52 (14)
C7—N3—C11	128.05 (14)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.91 (1)	1.98 (1)	2.882 (3)	172 (3)
O1—H1B⋯N2ⁱ	0.90 (1)	2.02 (1)	2.913 (2)	170 (3)
O2—H2A⋯N5ⁱⁱ	0.91 (1)	1.95 (1)	2.859 (3)	176 (2)
O2—H2B⋯O1ⁱⁱⁱ	0.91 (1)	2.08 (2)	2.949 (3)	160 (3)

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

Acknowledgments

DÜ and ED thank the Research Fund of Karadeniz Technical University for its support of this work.

supplementary crystallographic information

Comment

The biological importance of imidazoles and triazoles has stimulated much work on these heterocycles. 1,2,4-Triazole is a basic aromatic ring and possesses good coordination ability due to the presence of nitrogen atoms (Thenmozhi et al.,2010). 1,2,4-Triazole compounds posses important pharmacology activities such as antifungal and antiviral activities. Examples of such compounds bearing the 1,2,4-Triazole residues are fluconazole, the powerful azole antifungal agent as well as the potent antiviral N-nucleoside ribavirin. Furthermore various 1,2,4-Triazole derivatives have been reported as fungicidal, insecticidal, antimicrobial as well as anticonvulsants, antidepressants and plant growth regulator anticoagulants (Ünver et al., 2010). 1,2,4-Triazole derivatives are also used to build polymetallic complexes. Compounds derived from triazole possess antimicrobial, analgesic, anti-inflammatory, local anesthetic, antineoplastic and antimalarial properties. Some triazole Schiff bases also exhibit antiproliferative and anticancer activities (Thenmozhi et al., 2010). 1,2,4-Triazole moieties interact strongly with heme iron and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, it was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatese inhibitors very useful for preventing breast cancer (Ünver et al., 2010). Some of the azole derivatives used as common antibiotics, such as amphotericin B, exhibit toxic effects on humans along with antimicrobial effects. Although different antimicrobial agents are used in the treatment of microbial infections, an increasing resistance to these drugs is observed. Therefore, the search for and synthesis of new antibiotics different from commonly used ones is of current importance (Köysal et al., 2006). In a search for new triazole compounds with better biological activity, the title compound (I), was synthesized. We report here the crystal structure of the title compound, (I) (Fig.1), a new 1,2,4-triazole derivative. The compound (I) crystallizes as a dihydrate, the bond lengths and angles (Table 1) are generally normal in the triazole ring (Thenmozhi et al., 2010; Rizzoli et al., 2009; Dolzhenko et al., 2010; Ocak Ískeleli et al., 2005; Ünver et al., 2010). Atom N3 has a trigonal configuration, the sum of the three bond angles around them being 360° (Kalkan et al., 2007). The dihedral angles between the planes A(N1/N2/C7/N3/C8), B(N4/C14/N5/C15/C16) and C(C1/C2/C3/C4/C5/C6) are A/B = 70.61 (6)°, A/C = 41.89 (8)° and B/C = 68.16 (7)°. The triazole ring is essentially planar with r.m.s deviation of 0.0046Å (Dolzhenko et al., 2010). The C—N bond lengths in the triazole ring of all molecules lie in the range of 1.260 (3)–1.349 (4) Å. These are longer than a typical double C═ N bond [1.269 (2) Å], but shorter than a C—N single bond [1.443 (4) Å], (Thenmozhi et al., 2010) indicating the possibility of electron delocalization. The N3–C11–C12–C13 torsion angle of 172.00 (15)° indicates that the triazole ring and the imidazole moiety has an E-configuration across the C11–C12 bond. This configuration is stabilized by an intramolecular C11–H11···N4 hydrogen bond with H11···N4 distance of 2.54 Å. The uncoordinated water molecules are involved in intermolecular O–H···O and O–H···N hydrogen bonds (Table 2), which stabilize the crystal packing.

Experimental

The compound was synthesized by published method (Ünver et al., 2009).