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Volume 69 
Part 3 
Page o457  
March 2013  

Received 6 February 2013
Accepted 22 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.138
Data-to-parameter ratio = 12.0
Details
Open access

N,N-Bis(4-nitrophenyl)acetamide

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

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[Kim, S. Y., An, G. & Rhee, H. (2003). Synlett, pp. 112-114.]); Krigbaum et al. (1968[Krigbaum, W. R., Roe, R.-J. & Woods, J. D. (1968). Acta Cryst. B24, 1304-1312.]); Yamasaki et al. (2003[Yamasaki, R., Tanatani, A., Azumaya, I., Saito, S., Yamaguchi, K. & Kagechika, H. (2003). Org. Lett. 5, 1265-1267.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O5

  • Mr = 301.26

  • Triclinic, [P \overline 1]

  • a = 7.454 (3) Å

  • b = 8.070 (4) Å

  • c = 12.078 (5) Å

  • [alpha] = 81.449 (10)°

  • [beta] = 74.676 (10)°

  • [gamma] = 88.062 (13)°

  • V = 692.9 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.984, Tmax = 0.991

  • 4684 measured reflections

  • 2397 independent reflections

  • 2038 reflections with F2 > 2[sigma](F2)

  • Rint = 0.096

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.138

  • S = 1.06

  • 2397 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

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
Symmetry codes: (i) -x-1, -y, -z+1; (ii) -x, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider, et al., 2002[Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2098 ).


Acknowledgements

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

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kim, S. Y., An, G. & Rhee, H. (2003). Synlett, pp. 112-114.
Krigbaum, W. R., Roe, R.-J. & Woods, J. D. (1968). Acta Cryst. B24, 1304-1312.  [CrossRef] [ChemPort] [details] [ISI]
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.  [ISI] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yamasaki, R., Tanatani, A., Azumaya, I., Saito, S., Yamaguchi, K. & Kagechika, H. (2003). Org. Lett. 5, 1265-1267.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o457  [ doi:10.1107/S1600536813005175 ]

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