Crystal structure of 2-{[1-(4-bromo­benz­yl)-1H-1,2,3-triazol-4-yl]meth­oxy}naph­thalene-1,4-dione

Rajamani Raja; Subramani Kandhasamy; Paramasivam T Perumal; A SubbiahPandi

doi:10.1107/S2056989015004429

. 2015 Mar 11;71(Pt 4):o231–o232. doi: 10.1107/S2056989015004429

Crystal structure of 2-{[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}naphthalene-1,4-dione

Rajamani Raja ^a, Subramani Kandhasamy ^b, Paramasivam T Perumal ^b, A SubbiahPandi ^a,^*

PMCID: PMC4438838 PMID: 26029429

Abstract

In the title compound, C₂₀H₁₄BrN₃O₃, the benzene ring makes dihedral angles of 71.30 (11) and 68.95 (14)° with the naphthalene ring system and the triazole ring, respectively. The latter two ring systems are coplanar, with a dihedral angle of 2.92 (12)°. The O atoms deviate from the naphthalene ring system by 0.029 (2) and −0.051 (2) Å. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds, forming ribbons parallel to (10-1). The ribbons are linked via C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.4451 (14) Å], forming slabs parallel to the bc plane.

Keywords: crystal structure, triazole, naphthalene, hydrogen bonds

Related literature

For some general background and examples of the pharmacological and biological activity of triazole and its derivatives, see, for example: Abu-Orabi et al. (1989 ▸); Demirbaş et al. (2002 ▸); Kritsanida et al. (2002 ▸). For the biological activity of naphthalene compounds, see, for example: Upadhayaya et al. (2010 ▸); Rokade & Sayyed (2009 ▸). graphic file with name e-71-0o231-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₄BrN₃O₃
M _r = 424.25
Monoclinic,
a = 16.4383 (5) Å
b = 13.1684 (4) Å
c = 8.2255 (2) Å
β = 90.827 (1)°
V = 1780.36 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T _min = 0.593, T _max = 0.652
17010 measured reflections
4415 independent reflections
2887 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.119
S = 1.01
4415 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015004429/su5090sup1.cif

e-71-0o231-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004429/su5090Isup2.hkl

e-71-0o231-Isup2.hkl^{(216.3KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015004429/su5090Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015004429/su5090fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.^{(1.6MB, tif)}

c . DOI: 10.1107/S2056989015004429/su5090fig2.tif

A partial view along the c axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Click here for additional data file.^{(3.7MB, tif)}

c . DOI: 10.1107/S2056989015004429/su5090fig3.tif

A perspective view along the c axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).

CCDC reference: 1052111

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C1H1N1ⁱ	0.93	2.57	3.251(3)	131
C13H13O2ⁱ	0.93	2.53	3.277(3)	138
C11H11AO2ⁱⁱ	0.97	2.46	3.425(3)	175

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

Acknowledgments

The authors thank Dr Jagan, Department of Chemistry, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

S1. Comment

Triazoles and triazole derivatives play an important role in pharmaceuticals, agrochemicals, dyes, photographic materials, and in corrosion inhibition and have many biological applications (Abu-Orabi et al., 1989; Demirbaş et al., 2002; Kritsanida et al., 2002. Naphthalene derivatives has been identified as new range of potent antimicrobials effective against wide range of human pathogens and have diverse and interesting antibiotic properties with minimum toxicity (Rokade & Sayyed, 2009; Upadhayaya et al. 2010).

The molecular structure of the title compound is shown in Fig. 1. The benzene ring (C15-C20) makes dihedral angles of 71.30 (11) and 68.95 (14) ° with the naphthalene ring system and the triazole ring, respectively. The latter two rings are coplanar with a dihedral angle of 2.92 (12) °. Atoms O1 and O2 deviate from the naphthalene ring by 0.029 (2) and -0.051 (2) Å, respectively. Atom Br1 deviates from the benzene ring to which it is attached by -0.028 (1) Å

In the crystal, molecules are linked by C-H···O and C-H···N hydrogen bonds forming ribbons parallel to (101); see Table 1 and Fig. 2. The ribbons are linked by C-H···O hydrogen bonds and π–π stacking interactions [Cg2···Cg3ⁱ = 3.4451 (14) Å; Cg2 and Cg3 are the centroids of rings naphthalene rings C1-C5/C10 and C5-C10, respectively; symmetry code: (i) x, -y+1/2, z-1/2], forming slabs parallel to the bc plane (Table 1 and Fig. 3).

S2. Experimental

The triazole appended lawsone was synthesized in a two step procedure. To a solution of lawsone (0.87 g, 5 mmol) in DMF (20 ml) was added potassium carbonate (1.04 g, 7.5 mmol) and the solution was stirred at room temperature. Propargyl bromide (0.7 mL, 7.5 mmol) was added drop wise and the resulting mixture was allowed to stir overnight. After completion of the reaction, in the mixture was partitioned between DCM and water, and the DCM layer was collected. The aqueous layer was extracted three times with DCM. The combined organic extracts were dried over anhydrous Na₂SO₄, and concentrated under vacuum to obtain the desired propargyllated lawsone that was later converted to a triazole using click chemistry. Propargyllated lawsone (0.636 g, 3 mmol) was dissolved in 1:1 THF / H₂O mixture and triethyl amine (0.7 ml, 5 mmol), sodium azide (0.26 g, 4 mmol), 4-bromobenzyl bromide (0.68 mL, 4 mmol) and cuprous iodide (catalytic amount) were added to this solution. The resulting mixture was allowed to stir overnight at room temperature. Upon completion of the reaction, the mixture was filtered, extract with ethyl acetate, concentrated under vacuum and then subjected to column chromatography to obtain the desired product. The overall yield was 0.61 g (60%). Colourless block-like crystals were obtained on slow evaporation of the solvent.