Crystal structure of 2-nitro-N-(2-nitro­phen­yl)benzamide

Rodolfo Moreno-Fuquen; Alexis Azcárate; Alan R Kennedy

doi:10.1107/S2056989015008695

. 2015 May 9;71(Pt 6):o389–o390. doi: 10.1107/S2056989015008695

Crystal structure of 2-nitro-N-(2-nitrophenyl)benzamide

Rodolfo Moreno-Fuquen ^a,^*, Alexis Azcárate ^a, Alan R Kennedy ^b

PMCID: PMC4459296 PMID: 26090182

Abstract

In the title compound, C₁₃H₉N₃O₅, the mean plane of the non-H atoms of the central amide fragment C—N—C(=O)—C [r.m.s. deviation = 0.0442 Å] forms dihedral angles of 71.76 (6) and 24.29 (10)° with the C-bonded and N-bonded benzene rings, respectively. In the crystal, molecules are linked by N—H⋯O hydrogen bonds forming C(4) chains along [100]. Weak C—H⋯O contacts link the molecules into (100) sheets containing edge-fused R ₄ ⁴(30) rings. Together, the N—H⋯O and C—H⋯O hydrogen bonds generate a three-dimensional network.

Keywords: crystal structure, benzamide, anticonvulsant properties, antimicrobial properties, inhibitors of diverse enzymes, hydrogen bonding

Related literature

For anticonvulsant and antimicrobial properties of benzanilide compounds, see: Leander (1992 ▸); Ahles et al. (2004 ▸). For studies as selective inhibitors of diverse enzymes, see: Goldman et al. (2003 ▸); Weisberg et al. (2006 ▸). For related structures, see: Sun et al. (2009 ▸); Saeed & Simpson (2009 ▸); Moreno-Fuquen et al. (2014 ▸). graphic file with name e-71-0o389-scheme1.jpg

Experimental

Crystal data

C₁₃H₉N₃O₅
M _r = 287.23
Orthorhombic,
a = 7.7564 (2) Å
b = 12.1142 (4) Å
c = 12.9355 (4) Å
V = 1215.45 (6) Å³
Z = 4
Cu Kα radiation
μ = 1.06 mm⁻¹
T = 123 K
0.35 × 0.05 × 0.02 mm

Data collection

Oxford Diffraction Gemini S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T _min = 0.657, T _max = 1.000
4952 measured reflections
2367 independent reflections
2259 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.088
S = 1.06
2367 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015008695/hb7415sup1.cif

e-71-0o389-sup1.cif^{(187.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008695/hb7415Isup2.hkl

e-71-0o389-Isup2.hkl^{(130.2KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008695/hb7415Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015008695/hb7415fig1.tif

The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Click here for additional data file.^{(1.2MB, tif)}

C x y z . DOI: 10.1107/S2056989015008695/hb7415fig2.tif

Part of the crystal structure of (I), showing the formation of C(4) chains along [100] [symmetry code: (i) x − Inline graphic , −y + , −z + 1].

Click here for additional data file.^{(1.3MB, tif)}

x y z x y z . DOI: 10.1107/S2056989015008695/hb7415fig3.tif

Part of the crystal structure of (I), showing the formation of Inline graphic (30) rings within a 2-D hydrogen-bonded network (dashed lines) running parallel to (100) [Symmetry codes: (ii) −x + , −y + 2, z − ; (iii) −x + , −y + 1, z − ].

CCDC reference: 1063243

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1NO1ⁱ	0.93(3)	2.00(3)	2.859(2)	154(2)
C5H5O5ⁱⁱ	0.95	2.57	3.427(3)	150
C10H10O1ⁱⁱⁱ	0.95	2.46	3.271(3)	144

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

Acknowledgments

RMF is grateful to the Universidad del Valle, Colombia, for partial financial support.

supplementary crystallographic information

S1. Comment

The crystal structure determination of 2-nitro-N-(2-nitrophenyl)benzamide (I), is part of a study on phenylbenzamides carried out in our research group, and it was synthesized from the reaction between of 2-nitrobenzoic acid and 2-nitroaniline mediated by the presence of thionyl chloride. Benzanilides are versatile intermediate towards a diversity of heterocyclic compounds. Benzanilide systems as ameltolid, very similar to the molecule under study, have different properties ranging from anticonvulsant (Leander, 1992); antimicrobial drug (suramin) or as treatment in patients with prostate carcinoma (Alhes et al., 2004); as inhibitor of tyrosine-kinase, (imatinib) (Goldman et al., 2003) or a selective inhibitor of BCR-ABL, (nilotinib) (Weisberg et al., 2006). Similar compounds to (I) have been reported in the literature: N-(2,4-Dinitrophenyl)-4-nitrobenzamide (II) (Sun et al., 2009), N-(2-Nitrophenyl)benzamide (III) (Saed & Simpson, 2009) and 4-Bromo-N-(2-nitrophenyl)benzamide (IV) (Moreno-Fuquen et al., 2014). The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(═O1)—C1, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0442 Å) and it forms dihedral angles of 71.76 (6)° with the C1-C6 and 24.29 (10)° with the C8-C13 rings respectively. Bond lengths and bond angles in the molecule are in a good agreement with those found in the related compounds (II), (III) and (IV). A small lengthening of C7-N1 bond in (III) is observed [N1-C7= 1.3742 (11)Å], possibly caused by the formation of intramolecular S rings (6) in that structure. In the crystal structure (Fig. 2), molecules are linked by N-H···O hydrogen bonds of medium-strength and weak C-H···O intermolecular contacts (see Table 1). The N1-H1···O1 hydrogen bond interactions are responsible for crystal growth in [100]. In this interaction, the N-H in the molecule at (x,y,z) acts as a hydrogen-bond donor to O1 atom of the carbonyl group at (x-1/2,-y+3/2,-z+1). These interactions generate C(4) chains of molecules along [100]. Two C-H···O weak intermolecular contacts are further observed that run parallel to the bc plane in this structure (see Fig. 3). The group C5-H5 in the molecule at (x,y,z) acts as hydrogen bond donor to O5 atom of the nitro group in the molecule at (-x+3/2,-y+2,+z-1/2) and the C10-H10 group in the molecule at (x,y,z) acts as a hydrogen bond donor to O1 atom of the carbonyl group in the molecule at (-x+3/2,-y+1,+z-1/2). The combination of these interactions generate edge-fused R₄⁴(30) rings.

S2. Experimental

A mass of 0.200 g (1.197 mmol) of 2-nitrobenzoic acid was refluxed with 2 ml of thionyl chloride for one hour. Then an equimolar amount of 2-nitroaniline was added and dissolved in 10 ml of acetonitrile and it was placed under reflux and constant stirring for 3 hours. Subsequently, the final solvent was slowly evaporated to obtain yellow needles of the title compound. [m.p. 431 (1)K].