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Volume 69 
Part 2 
Page o201  
February 2013  

Received 20 December 2012
Accepted 27 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.143
Data-to-parameter ratio = 15.4
Details
Open access

2,2'-Dihydroxy-N,N'-(ethane-1,2-diyl)dibenzamide

aEscola de Quimica e Alimentos, Universidade Federal do Rio Grande, Av. Italia, km 08, Campus Carreiros, 96203-900 Rio Grande-RS, Brazil, and bDepartamento de Quimica, Universidade Federal de Santa Maria, Av. Roraima Campus, 97105-900 Santa Maria-RS, Brazil
Correspondence e-mail: sabrinanobre@furg.br

The asymmetric unit of the title compound, C16H16N2O4, contains one half-molecule, the whole molecule being generated by an inversion center located at the mid-point of the C-C bond of the central ethane group. An intramolecular O-H...O hydrogen bond forms an S(6) ring motif. In the crystal, molecules are connected via N-H...O hydrogen bonds, generating infinite chains along [1-10].

Related literature

For the synthesis of bisamides, see: Apurba et al. (2002[Apurba, K., Patra, A. K., Olmstead, M. M. & Mascharak, P. K. (2002). Inorg. Chem. 41, 5403-5409.]); Fry et al. (2010[Fry, N. L., Rose, M. J., Rogow, D. L., Nyitray, C., Kaur, M. & Mascharak, P. K. (2010). Inorg. Chem. 49, 1487-1495.]). For similar bisamide crystal structures, see: Booysen et al. (2009[Booysen, I., Gerber, T. I. A., Hosten, E. & Mayer, P. (2009). Acta Cryst. E65, o850.]). For applications of bisamides as catalysts, see: Maurya et al. (2003[Maurya, M. R., Titinchi, S. J. J. & Chand, S. (2003). Catal. Lett. 89, 219-227.]); Liu et al. (2011[Liu, H. Y., Wang, K., Fu, H. Y., Yuan, M. L. & Chen, H. (2011). Chin. Chem. Lett. 22, 738-740.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O4

  • Mr = 300.31

  • Triclinic, [P \overline 1]

  • a = 4.6311 (3) Å

  • b = 5.0435 (3) Å

  • c = 15.2957 (9) Å

  • [alpha] = 89.091 (4)°

  • [beta] = 83.315 (4)°

  • [gamma] = 85.956 (4)°

  • V = 353.94 (4) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.34 × 0.24 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: gaussian (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.989

  • 9142 measured reflections

  • 1535 independent reflections

  • 924 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.143

  • S = 1.01

  • 1535 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.82 1.76 2.495 (2) 148
N-H0...O1i 0.86 2.21 2.993 (2) 151
Symmetry code: (i) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2096 ).


Acknowledgements

The authors gratefully acknowledge Professor Manfredo Hörner, Department of Chemistry, Universidade Federal de Santa Maria, Brazil, for his support and help with the X-ray measurements. They also thank PRONEX FAPERGS/CNPq 10/0009-2 and PRONEM FAPERGS/CNPq 11/2026-4 for funding this study.

References

Apurba, K., Patra, A. K., Olmstead, M. M. & Mascharak, P. K. (2002). Inorg. Chem. 41, 5403-5409.  [ISI] [PubMed]
Booysen, I., Gerber, T. I. A., Hosten, E. & Mayer, P. (2009). Acta Cryst. E65, o850.  [CSD] [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fry, N. L., Rose, M. J., Rogow, D. L., Nyitray, C., Kaur, M. & Mascharak, P. K. (2010). Inorg. Chem. 49, 1487-1495.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Liu, H. Y., Wang, K., Fu, H. Y., Yuan, M. L. & Chen, H. (2011). Chin. Chem. Lett. 22, 738-740.  [CrossRef] [ChemPort]
Maurya, M. R., Titinchi, S. J. J. & Chand, S. (2003). Catal. Lett. 89, 219-227.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o201  [ doi:10.1107/S1600536812051963 ]

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