{4-[(2,4-Dichloro­benzo­yloxy)meth­yl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichloro­benzoate

Dilmurot Ismatov; Umarkhon Azizov; Samat Talipov; Jamshid Ashurov

doi:10.1107/S1600536811035550

. 2011 Sep 14;67(Pt 10):o2590. doi: 10.1107/S1600536811035550

{4-[(2,4-Dichlorobenzoyloxy)methyl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate

Dilmurot Ismatov ^a,^*, Umarkhon Azizov ^b, Samat Talipov ^c, Jamshid Ashurov ^c

PMCID: PMC3201422 PMID: 22065713

Abstract

In the title molecule, C₂₄H₁₅Cl₄N₃O₄, the triazole ring makes dihedral angles of 72.02 (12), 81.60 (12) and 73.82 (11)°, respectively, with the adjacent phenyl ring and the two dichlorobenzene rings. In the crystal, a weak C—H⋯N interaction, a short Cl⋯Cl contact [3.307 (2) Å] and a π–π stacking interaction [centroid–centroid distance = 3.568 (4) Å] are observed. An intramolecular C—H⋯O interaction is also present.

Related literature

For the pharmacological activities of 1,2,3-triazole derivatives, see: Dzhuraev et al. (1990 ▶); Karimkulov et al. (1991 ▶); Zakirov et al. (2001 ▶). For a related structure, see: Jin et al. (2004 ▶).

Experimental

Crystal data

C₂₄H₁₅Cl₄N₃O₄
M _r = 551.19
Monoclinic,
a = 8.908 (5) Å
b = 19.567 (5) Å
c = 13.908 (5) Å
β = 104.010 (5)°
V = 2352.1 (17) Å³
Z = 4
Cu Kα radiation
μ = 4.91 mm⁻¹
T = 293 K
0.6 × 0.4 × 0.3 mm

Data collection

Oxford Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.050, T _max = 0.229
20081 measured reflections
4196 independent reflections
3370 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.107
S = 1.02
4196 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035550/is2762sup1.cif

e-67-o2590-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035550/is2762Isup2.hkl

e-67-o2590-Isup2.hkl^{(209.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035550/is2762Isup3.cml

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
C6—H6B⋯O4	0.97	2.49	3.280 (3)	139
C9—H9⋯N2ⁱ	0.93	2.58	3.288 (3)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (grant No. FA-F3-T-141).

supplementary crystallographic information

Comment

In last few decades, much attention has been paid to the synthesis of 1,2,3-triazole systems mainly due to their broad spectrum of pharmacological properties. 1,2,3-Triazole derivatives possess variety of pharmacological activities such as anti inflammatory, antiviral and antibacterial (Dzhuraev et al., 1990; Karimkulov et al., 1991; Zakirov et al., 2001).

In the title compound, {4-[(2,4-dichlorobenzoyloxy)methyl]-1-phenyl-1H-1,2,3-triazol-5-yl}methyl 2,4-dichlorobenzoate, C₂₄H₁₅N₃O₄Cl₄, the triazole ring (N1/N2/N3/C4/C5) is ideal planar with a greatest deviation of 0.0037 (12) Å (atom N3) from the mean plane and the benzyl rings of dichlorobenzoyloxy substituents (C8–C13 and C16–C21) are tilted out of this plane at 81.60 (12) and 73.82 (11)°, respectively. The dihedral angles between these benzyl rings and corresponding carboxylic fragments (O1/C7/O2 and O3/C15/O4) are 5.9 (4) and 26.9 (3)°, respectively. The dihedral angle between the triazole and phenyl (C22–C27) rings is 72.02 (12)°. The C5—N1 and C4—N2 bond lengths in the triazole ring are 1.352 (3) and 1.361 (3) Å, respectively. The values of these distances are shorter than the pertinent single bond length of 1.443 Å and are longer than the double bond length of 1.269 Å (Jin et al., 2004).

An intermolecular Cl1···Cl1 (-x, 1 - y, 2 - z) contact and a π–π stacking interaction with a Cg1···Cg2 (x - 1/2, 1/2 - y, z + 1/2) distance of 3.568 (4) Å stabilize the crystal structure; Cg1 and Cg2 are the centroids of the C8–C13 and C16–C21 rings, respectively.

Experimental

As a result of etherification 24.6 g (0.13 mole) of 2,4-dichlorbenzoic acid with 5.54 g (0.07 mole) of 2-butendiole-1, 4 refluxing for 2 h in benzene containing sulfuric acid as catalyst was got of 1,4-bis-(2,4-dichlorbenzoyloxy)-butene-2 [yield 22.55 g (82.2%), m.p. 364–365 K]. The reaction of obtaining bis-ester with 6.8 g (0.57 mole) phenylazide in 100 ml of toluene was carrying out within 7 h. Then the reaction mixture was cooled. The precipitate [1-phenyl-4,5-bis-(dichlorobenzoyloxymethyl)-1,2,3-triazole, yield 27.84 g (96.8%)] was collected by filtration and purified by recrystallization from ethanol (m.p. 383–384 K).