N,N-Bis(4-nitro­phen­yl)acetamide

Kokichi Nanaura; Tsunehisa Okuno

doi:10.1107/S1600536813005175

. 2013 Feb 28;69(Pt 3):o457. doi: 10.1107/S1600536813005175

N,N-Bis(4-nitrophenyl)acetamide

Kokichi Nanaura ^a, Tsunehisa Okuno ^a,^*

PMCID: PMC3588481 PMID: 23476624

Abstract

In the title compound, C₁₄H₁₁N₃O₅, the dihedral angles between the amide group (r.m.s. deviation = 0.0429 Å) and the two benzene rings are 39.66 (6) and 63.04 (7)°. The dihedral angle between the benzene rings is 86.04 (7)°. The benzene rings form dihedral angles of 4.42 (5) and 8.91 (5)° with the adjacent nitro groups. In the crystal, molecules are linked via a pair of C—H⋯O hydrogen bonds, forming inversion dimers, which are linked via a second pair of C—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For the related structures of diphenylacetamide derivatives, see: Kim et al. (2003 ▶); Krigbaum et al. (1968 ▶); Yamasaki et al. (2003 ▶). graphic file with name e-69-0o457-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₁N₃O₅
M _r = 301.26
Triclinic,
a = 7.454 (3) Å
b = 8.070 (4) Å
c = 12.078 (5) Å
α = 81.449 (10)°
β = 74.676 (10)°
γ = 88.062 (13)°
V = 692.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 93 K
0.10 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T _min = 0.984, T _max = 0.991
4684 measured reflections
2397 independent reflections
2038 reflections with F ² > 2σ(F ²)
R _int = 0.096

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.138
S = 1.06
2397 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider, et al., 2002 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(24.6KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005175/ff2098sup1.cif

e-69-0o457-sup1.cif^{(24.6KB, cif)}

Click here for additional data file.^{(117.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005175/ff2098Isup2.hkl

e-69-0o457-Isup2.hkl^{(117.8KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005175/ff2098Isup3.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
C3—H3⋯O5ⁱ	0.95	2.39	3.183 (3)	141
C8—H8⋯O5ⁱⁱ	0.95	2.34	3.204 (3)	152

Open in a new tab

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

Acknowledgments

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

supplementary crystallographic information

Comment

The title compound, C₁₄H₁₁N₃O₅, is a derivative of diphenylacetamides, whose structures are paid attention because of relationship between their structures and molecular recognition functions (Yamasaki et al., 2003).

The structure of the C1/C7/N1/C13/O5/C14 amide group is almost planar (r.m.s. deviation = 0.0429 Å) The dihedral angles of the plane of the amide group with the C1—C6 phenyl ring and the C7—C12 phenyl ring are 39.66 (6)° and 63.04 (7)°, respectively. The dihedral angle between the two phenyl rings is 86.04 (7)°. In diphenylacetamide derivatives, electron deficient aromatic rings have a tendency to make a smaller dihedral angle to an amide part (Kim et al., 2003; Krigbaum et al., 1968; Yamasaki et al., 2003). The obtained geometry has a good agreement with the tendency.

The dihedral angle of the N2/O1/O2 nitro group with the C1—C6 phenyl ring are 8.91 (5)°. The dihedral angle of the N3/O3/O4 nitro group with the C7—C12 phenyl ring is 4.42 (5)°. The nitro groups have good conjugations with the corresponding phenyl groups. Intermolecular contacts are observed beween the nitro groups related by an inversion symmetry, where O4···N2ⁱ and N2···O4ⁱ are 2.948 (3) Å [Symmetry code: (i) -x, -y, -z].

Experimental

Single crystals with sufficient quality for X-ray crystallographical analysis were prepared by recrystallization from a mixed solution of dichloromethane and hexane.