Crystal structure of ethyl 2-(1H-benzimidazol-2-yl)-2-[2-(4-nitro­phen­yl)hydrazinyl­idene]acetate

Mohamed Loughzail; Abdesselam Baouid; Lahcen El Ammari; Mohamed Saadi; Moha Berraho

doi:10.1107/S2056989015004818

. 2015 Mar 14;71(Pt 4):o236–o237. doi: 10.1107/S2056989015004818

Crystal structure of ethyl 2-(1H-benzimidazol-2-yl)-2-[2-(4-nitrophenyl)hydrazinylidene]acetate

Mohamed Loughzail ^a, Abdesselam Baouid ^a, Lahcen El Ammari ^b, Mohamed Saadi ^b, Moha Berraho ^c,^*

PMCID: PMC4438822 PMID: 26029432

Abstract

The title compound, C₁₇H₁₅N₅O₄, was obtained via the condensation of 3-ethoxy-2-[2-(4-nitrophenyl)hydrazono]-3-oxopropanoic acid with 1,2-diaminobenzene. In the molecule, the dihedral angles between the acetate group and the two aromatic subunits (benzimidazole and nitrophenylhydrazone) are 7.35 (9) and 18.23 (9)°, respectively. Intramolecular N—H⋯O and N—H⋯N contacts occur. In the crystal, C—H⋯O and N—H⋯O hydrogen bonds link the molecules into chains along the b-axis direction.

Keywords: crystal structure, benzimidazole, nitrophenylhydrazone, hydrogen bonding

Related literature

For the pharmacological activity of benzimidazole derivatives, see: Luo et al. (2011 ▸); Ouattara et al. (2011 ▸); Bhrigu et al. (2012 ▸); Singh et al. (2012 ▸); Parajuli et al. (2014 ▸). For their agrochemical activity, see: Attrassi et al. (2007 ▸).

Experimental

Crystal data

C₁₇H₁₅N₅O₄
M _r = 353.34
Monoclinic,
a = 12.877 (5) Å
b = 5.874 (5) Å
c = 21.988 (5) Å
β = 99.060 (5)°
V = 1642.4 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.33 × 0.17 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
24995 measured reflections
3362 independent reflections
2562 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.108
S = 1.03
3362 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick,2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick,2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015004818/im2461sup1.cif

e-71-0o236-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004818/im2461Isup2.hkl

e-71-0o236-Isup2.hkl^{(161.6KB, hkl)}

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

Supporting information file. DOI: 10.1107/S2056989015004818/im2461Isup3.cml

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

. DOI: 10.1107/S2056989015004818/im2461fig1.tif

Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

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

b . DOI: 10.1107/S2056989015004818/im2461fig2.tif

Partial packing view showing the C—H⋯O and N—H⋯O interactions (dashed lines) and the formation of a chain parallel to the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1052904

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2O4ⁱ	0.86	2.50	3.161(3)	134
C8H8O4ⁱ	0.93	2.54	3.258(3)	134
N2H2O4	0.86	2.21	2.750(3)	121
N4H4N1	0.86	2.02	2.679(3)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

S1. Comment

The development of an efficient synthesis of bioactive compounds is a major challenge in modern chemistry. The high therapeutic properties of benzimidazole derivatives related drugs have encouraged the medicinal chemists to synthesize a large number of new chemotherapeutic agents. The benzimidazole motif is an integral part in numerous fields, as pharmaceuticals (Luo et al., 2011; Ouattara et al., 2011; Bhrigu et al., 2012; Singh et al., 2012; Parajuli et al., 2014), and agrochemicals (Attrassi et al., 2007). The structure of this new product was determined by its single-crystal X-ray structure. The dihedral angles between the acetate chain and the two aromatic subunits (benzimidazole and nitrophenylhydrazone) are 7.35 (9)° and 18.23 (9)°, respectively. In the crystal structure, the molecules are linked by C—H···O and N—H···O intermolecular hydrogen bonds into chains along the b axis (Fig.2). In addition an intramolecular N—H···O hydrogen bond is also observed.

S2. Experimental

1,2-diaminobenzene (0.5 g, 4.6 mmol) and 3-ethoxy-2-[2-(4-nitrophenyl)hydrazono]-3-oxopropanoic acid (1.19 g, 4.6 mmol) were heated in xylene (15 ml) for 12 h. The solvent was evaporated. The title compound was isolated by column chromatography on silica gel using hexane/ethyl acetate as eluent. The solid product was recrystallized in dichloromethane at 15°C to give yellow crystals (yield: 45%) of the title compound.