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Volume 69 
Part 5 
Page o673  
May 2013  

Received 28 January 2013
Accepted 1 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.124
Data-to-parameter ratio = 13.1
Details
Open access

N,N'-(Propane-1,3-diyl)bis(2-aminobenzamide)

The title compound, C17H20N4O2, was prepared by the reaction between 1,3-diaminopropane and isatoic anhydride in water. The carbonyl O atoms are involved in intramolecular hydrogen bonding with the amine group and intermolecular hydrogen bonding with an amide H atom of an adjacent molecule. In the crystal, pairs of N-H...O hydrogen bonds link molecules into inversion dimers and further N-H...O hydrogen bonds link the dimers into ladder-like chains along the a axis.

Related literature

For related molecules and syntheses, see: Clark & Wagner (1944[Clark, R. H. & Wagner, E. C. (1944). J. Org. Chem. 09, 55-67.]); Swamy & Kumar (1996[Swamy, S. J. & Kumar, B. K. (1996). Indian J. Chem. Sect. A, 35, 489-493.]); Swamy et al. (2003[Swamy, S. J., Veerapratap, B., Nagaraju, D., Suresh, K. & Someshwar, P. (2003). Tetrahedron, 59, 10093-10096.], 2004[Swamy, S. J., Suresh, K., Someshwar, P. & Nagaraju, D. (2004). Synth. Commun. 34, 1847-1853.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20N4O2

  • Mr = 312.37

  • Triclinic, [P \overline 1]

  • a = 5.6590 (7) Å

  • b = 9.8279 (12) Å

  • c = 14.6732 (18) Å

  • [alpha] = 95.258 (2)°

  • [beta] = 95.263 (2)°

  • [gamma] = 98.888 (2)°

  • V = 798.21 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.32 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.983

  • 6168 measured reflections

  • 3048 independent reflections

  • 2539 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.124

  • S = 1.06

  • 3048 reflections

  • 232 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H1N4...O2 0.87 (2) 2.10 (2) 2.711 (3) 126.6 (18)
N1-H2N1...O1 0.89 (2) 2.20 (2) 2.851 (2) 130.2 (19)
N3-H3N3...O1i 0.902 (19) 2.055 (19) 2.9286 (16) 162.8 (15)
N2-H2N2...O2ii 0.882 (17) 1.942 (18) 2.7872 (17) 160.3 (16)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2394 ).


Acknowledgements

SJ thanks the University Grants Commission, New Delhi, India, for financial assistance (No. MRP-359/11).

References

Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clark, R. H. & Wagner, E. C. (1944). J. Org. Chem. 09, 55-67.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Swamy, S. J. & Kumar, B. K. (1996). Indian J. Chem. Sect. A, 35, 489-493.
Swamy, S. J., Suresh, K., Someshwar, P. & Nagaraju, D. (2004). Synth. Commun. 34, 1847-1853.  [ISI] [CrossRef] [ChemPort]
Swamy, S. J., Veerapratap, B., Nagaraju, D., Suresh, K. & Someshwar, P. (2003). Tetrahedron, 59, 10093-10096.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o673  [ doi:10.1107/S160053681300888X ]

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