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

Costa, D.P. da; Nobre, S.M.; Lisboa, B.G.; Vicenti, J.R. de M.; Back, D.F.

doi:10.1107/S1600536812051963

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 (C-C) = 0.003 Å
R = 0.049
wR = 0.143
Data-to-parameter ratio = 15.4
Details

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

Daniel Pereira da Costa,^a Sabrina Madruga Nobre,^a ^* Bruna Gonçalves Lisboa,^a Juliano Rosa de Menezes Vicenti ^a and Davi Fernando Back ^b

^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-HO hydrogen bond forms an S(6) ring motif. In the crystal, molecules are connected via N-HO hydrogen bonds, generating infinite chains along [1-10].

Related literature

For the synthesis of bisamides, see: Apurba et al. (2002); Fry et al. (2010). For similar bisamide crystal structures, see: Booysen et al. (2009). For applications of bisamides as catalysts, see: Maurya et al. (2003); Liu et al. (2011).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M_r = 300.31
Triclinic, $[P \overline 1]$
a = 4.6311 (3) Å
b = 5.0435 (3) Å
c = 15.2957 (9) Å
= 89.091 (4)°
= 83.315 (4)°
= 85.956 (4)°
V = 353.94 (4) Å³
Z = 1
Mo K radiation
= 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) T_min = 0.966, T_max = 0.989
9142 measured reflections
1535 independent reflections
924 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.143
S = 1.01
1535 reflections
100 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.82	1.76	2.495 (2)	148
N-H0O1ⁱ	0.86	2.21	2.993 (2)	151
Symmetry code: (i) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Booysen, I., Gerber, T. I. A., Hosten, E. & Mayer, P. (2009). Acta Cryst. E65, o850.
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.
Liu, H. Y., Wang, K., Fu, H. Y., Yuan, M. L. & Chen, H. (2011). Chin. Chem. Lett. 22, 738-740.
Maurya, M. R., Titinchi, S. J. J. & Chand, S. (2003). Catal. Lett. 89, 219-227.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds