5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

Younes Ouzidan; Youssef Kandri Rodi; Hafid Zouihri; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536812013177

. 2012 Mar 31;68(Pt 4):o1240. doi: 10.1107/S1600536812013177

5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

Younes Ouzidan ^a, Youssef Kandri Rodi ^b, Hafid Zouihri ^c, El Mokhtar Essassi ^d, Seik Weng Ng ^e,^f,^*

PMCID: PMC3344170 PMID: 22606173

Abstract

In the two independent molecules of the title compound, C₁₀H₇N₃O₃, the nitro substitutent is twisted slightly with respect to the benzodiazol fused-ring system [dihedral angles = 4.9 (3) and 8.5 (1)°]. The two independent molecules are disposed about a pseudo inversion center and are held together by N—H⋯O hydrogen bonds. The supramolecular dimer is essentially planar [dihedral angle between the fused rings = 2.0 (1)°]. Adjacent dimers are linked by acetylene–nitro C—H⋯O interactions, generating a ribbon motif along (110).

Related literature

For related structures, see: Ouzidan et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₀H₇N₃O₃
M _r = 217.19
Triclinic,
a = 7.2541 (2) Å
b = 10.0362 (2) Å
c = 14.6793 (3) Å
α = 100.978 (1)°
β = 92.047 (1)°
γ = 109.043 (1)°
V = 986.20 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.27 × 0.22 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer
20686 measured reflections
4506 independent reflections
2855 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.158
S = 1.05
4506 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013177/bt5859sup1.cif

e-68-o1240-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013177/bt5859Isup2.hkl

e-68-o1240-Isup2.hkl^{(220.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013177/bt5859Isup3.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
N1—H1⋯O4	0.96 (2)	1.81 (3)	2.766 (2)	173 (2)
N4—H4⋯O1	0.92 (2)	1.91 (2)	2.823 (2)	172 (2)
C4—H41⋯O3ⁱ	0.92 (4)	2.39 (4)	3.231 (4)	153 (3)
C14—H141⋯O6ⁱⁱ	0.88 (3)	2.51 (3)	3.383 (4)	169 (3)

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

Acknowledgments

We thank Université Mohammed V-Agdal and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study

supplementary crystallographic information

Comment

Benzodiazoles are of interest owing to their pharmacological properties. When the parent compound, benzodiazol-2-one, reacts with propargyl bromide, both amino groups are alkylated to give 1,3-bis(prop-2-ynyl)-benziodiazol-2-one (Ouzidan et al., 2011b). The presence of an electron-withdrawing nitro group allows only one amino group to be alklylated, as noted from the reactions of 5-nitrobenzodiazol-2-onezol with n-octyl bromide and n-nonyl bromide (Ouzidan et al., 2011b, 2011c). In the two independent molecules of C₁₀H₇N₃O₃(Scheme I), the nitro substitutent is slightly bent with respect to the benzodiazol fused-ring (Fig. 2). The two are disposed about a false inversion center, and are held together by N–H···O hydrogen bonds. Adjacent dimers are linked by C–H_acetylene···O_nitro interactions to generate a ribbon motif (Fig. 2).

Experimental

To a mixture of 5-nitro-1H-benzodiazol-2(3H)-one (0.25 g, 1.5 mmol), potassium carbonate (0.35 g, 2.5 mmol), tetra-n-butylammonium bromide (0.1 g,0.2 mmol) in DMF (15 ml) was added propargyl bromide (0.14 ml, 1.6 mmol). Stirring was continued at room temperature for 6 hours. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethylacetate/hexane; yellow crystals were obtained upon evaporation of the solvent.