Dimethyl 1-(3-hy­droxy-2-iodo-1-phenyl­prop­yl)-1H-1,2,3-triazole-4,5-dicarboxyl­ate

Hoong-Kun Fun; Tze Shyang Chia; Sivasubramanian Archana; Murugan Dinesh; Alagusundaram Ponnuswamy

doi:10.1107/S1600536812018193

. 2012 Apr 28;68(Pt 5):o1559. doi: 10.1107/S1600536812018193

Dimethyl 1-(3-hydroxy-2-iodo-1-phenylpropyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Sivasubramanian Archana ^b, Murugan Dinesh ^b, Alagusundaram Ponnuswamy ^b

PMCID: PMC3344657 PMID: 22590419

Abstract

In the title compound, C₁₅H₁₆IN₃O₅, the central triazole ring is essentially planar (r.m.s deviation = 0.0034 Å) and makes a dihedral angle of 70.14 (5)° with the pendant benzene ring. The mean planes of the two methoxycarbonyl groups make dihedral angles of 22.52 (7) and 40.93 (4)° with the triazole ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R ₂ ²(18) loops. The dimers are linked by C—H⋯O and C—H⋯N interactions into sheets lying parallel to the ac plane.

Related literature

For background to the industrial applications of 1,2,3-triazoles, see: Wamhoff (1984 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₆IN₃O₅
M _r = 445.21
Triclinic,
a = 8.0504 (3) Å
b = 9.6941 (4) Å
c = 11.1893 (4) Å
α = 106.426 (1)°
β = 91.798 (1)°
γ = 98.606 (1)°
V = 825.65 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 100 K
0.31 × 0.24 × 0.14 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.579, T _max = 0.763
21676 measured reflections
5934 independent reflections
5827 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.015
wR(F ²) = 0.038
S = 1.10
5934 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018193/hb6752sup1.cif

e-68-o1559-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018193/hb6752Isup2.hkl

e-68-o1559-Isup2.hkl^{(290.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018193/hb6752Isup3.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
O5—H1O5⋯O3ⁱ	0.74 (2)	2.22 (2)	2.9213 (11)	159 (2)
C9—H9A⋯O1ⁱⁱ	0.97	2.57	3.3595 (13)	139
C13—H13B⋯O3ⁱⁱⁱ	0.96	2.48	3.4375 (14)	174
C13—H13C⋯O5ⁱ	0.96	2.58	3.4247 (14)	147
C15—H15C⋯N2^iv	0.96	2.62	3.4903 (14)	151

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

supplementary crystallographic information

Comment

1,2,3-Triazoles are important in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners as well as biologically active agents (Wamhoff et al., 1984). As part of our sudies in this area, we now describe the synthesis and structure of the title compound, (I) (Fig. 1).

The central triazole ring (N1–N3/C10/C11) is essentially planar [r.m.s deviation = 0.0034 Å] and makes a dihedral angle of 70.14 (5)° with the terminal benzene ring (C1–C6). The mean planes of the two methyl carboxylate groups (O1/O2/C14/C15 with maximum deviation = 0.0199 (6) Å at atom C14 and O3/O4/C12/C13 with maximum deviation = 0.0060 (6) Å at atom C12) make dihedral angles of 22.52 (7) and 40.93 (4)°, respectively with the triazole ring.

In the crystal (Fig. 2), the molecules are linked by O5—H1O5···O3, C9—H9A···O1, C13—H13B···O3, C13—H13C···O5 and C15—H15C···N2 hydrogen bonds (Table 1) into sheets parallel to ac plane.

Experimental

A mixture of 3-azido-2-iodo-3-phenylpropan-1-ol (0.3 g, 0.99 mmol) and dimethyl but-2-ynedioate (0.14 g, 0.99 mmol) was heated to reflux in toluene for 3 h. The solvent was evaporated under reduced pressure to afford the crude reaction mass which was then subjected to column chromatography using silica gel (60–120 mesh) as the stationary phase and petroleum ether:ethyl acetate (80:20) as the mobile phase to give colourless blocks of (I) by slow recrystallization from the eluant. Yield: 0.35 g (81%); M.p.: 129–130 °C.