1-[5-Methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazol-4-yl]ethanone

N Vinutha; S Madan Kumar; Nithinchandra; Kalluraya Balakrishna; N K Lokanath; D Revannasiddaiah

doi:10.1107/S1600536813029425

. 2013 Oct 31;69(Pt 11):o1724. doi: 10.1107/S1600536813029425

1-[5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]ethanone

N Vinutha ^a, S Madan Kumar ^a, Nithinchandra ^b, Kalluraya Balakrishna ^b, N K Lokanath ^a, D Revannasiddaiah ^a,^*

PMCID: PMC3884370 PMID: 24454146

Abstract

The asymmetric unit of the title compound, C₁₁H₁₀N₄O₃, contains two independent molecules in which the benzene rings make dihedral angles of 38.3 (2) and 87.1 (2)° with respect to the triazole rings. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds, forming chains along [021]. Further, weak C—O⋯π [3.865 (5) Å, 83.8 (3)°] and N—O⋯π [3.275 (5) and 3.240 (6) Å, 141.8 (4) and 102.8 (3)°] interactions are observed.

Related literature

For chemical and biological properties and pharmocological applications of 1,2,3-triazole derivative, see: Nithinchandra et al. (2012 ▶, 2013 ▶); Biagi et al. (2004 ▶); Manfredini et al. (2000 ▶); Sherement et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-69-o1724-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₀N₄O₃
M _r = 246.23
Orthorhombic,
a = 7.2786 (10) Å
b = 11.5055 (16) Å
c = 27.220 (4) Å
V = 2279.5 (6) Å³
Z = 8
Cu Kα radiation
μ = 0.91 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.818, T _max = 0.831
8697 measured reflections
1910 independent reflections
1617 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.138
S = 1.08
1910 reflections
329 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Mercury.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029425/is5313sup1.cif

e-69-o1724-sup1.cif^{(31.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029425/is5313Isup2.hkl

e-69-o1724-Isup2.hkl^{(92.1KB, 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
C5B—H5B1⋯O3A ⁱ	0.96	2.51	3.306 (8)	141
C10B—H10B⋯O1A	0.93	2.58	3.197 (7)	124

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

supplementary crystallographic information

1. Comment

1,2,3-Triazoles are attractive constructs, because of their unique chemical properties and they find many applications in organic and medicinal chemistry (Nithinchandra et al., 2013). They are found to be potent antimicrobial (Sherement et al., 2004)and antiviral agents. Some of them have exhibited antiproliferative and anti-inflammatory property (Nithinchandra et al., 2012). Also, 1,2,3-triazoles are used as DNA cleaving agents (Manfredini et al., 2000) and potassium channel activators (Biagi et al., 2004).

The asymmetric unit of of the title compound consists of two molecules A and B (Fig. 1). They show conformational difference, as evident from dihedral angles. The dihedral angle between benzene ring and triazole moiety is 38.2 (3)° in A and 87.6 (4)° in B. The values of the bond lengths are similar to the reported literature (Allen et al., 1987).

In the crystal, the molecules are linked to one another with the C—H···O hydrogen bonds (Table 1). Also, short contacts of the type C3A—O1A···Cg4(x + 1/2, y - 1, z) with a distance 3.865 (5) Å [angle 83.8 (3)°], N4A—O2A···Cg3(x - 1, y - 1, z + 1/2) with a distance 3.275 (5) Å [angle 141.8 (4)°] and N4B—O3B···Cg1(x - 1/2, y - 1, z) with a distance 3.240 (6) Å [angle 102.8 (3)°] help in crystal stabilization. These interactions form a three dimensional architecture (Fig. 2), where Cg1, Cg3 and Cg4 are the centroids of the N1A/N2A/N3A/C1A/C2A, N1B/N2B/N3B/C1B/C2B and C6B–C11B rings, respectively.

2. Experimental

1-Azido-4-nitrobenzene (0.01 mol) was treated with acetyl acetone (0.01 mol) in methanol (10 ml) and the mixture was cooled to 0 °C. Sodium methoxide (0.01 mol) was added under inert atmosphere to the above mixture and stirred at ambient temperature for 8 h. Progress of the reaction was monitored by TLC (ethyl acetate/petroleum ether, 2:3, v/v). After completion of the reaction, the mixture was poured onto ice cold water. The precipitated solid was filtered, washed with water and recrystallized from ethanol. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.