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Volume 69 
Part 5 
Page o677  
May 2013  

Received 22 March 2013
Accepted 29 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.097
Data-to-parameter ratio = 13.5
Details
Open access

N,N'-[2,2'-(Phenylazanediyl)bis(ethane-2,1-diyl)]dipicolinamide

aCollege of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
Correspondence e-mail: ligaonan2008@163.com

The asymmetric unit of the title compound, C22H23N5O2, contains two independent molecules with similar conformations; the terminal pyridine rings are oriented at dihedral angles of 23.99 (8) and 18.07 (8)° with respect to the central benzene ring in one molecule and 28.99 (8) and 23.22 (8)° in the other. In the crystal, N-H...O and weak C-H...O hydrogen bonds link the molecules into a three-dimensional supramolecular structure. Weak intermolecular C-H...[pi] interactions are also observed in the crystal.

Related literature

For background to bis(pyridinecarboxamide) derivatives, see: Cornman et al. (1999[Cornman, C. R., Zovinka, E. P., Boyajian, Y. D., Olmstead, M. M. & Noll, B. C. (1999). Inorg. Chim. Acta, 285, 134-137.]); Song et al. (2010[Song, Y. J., Lee, J. H., Koo, H. G., Lee, T. G., Myoung, S.-H., Kim, C., Kim, S.-J. & Kim, Y. (2010). Inorg. Chem. Commun. 13, 753-756.]); Singh et al. (2008[Singh, A. K., Jacob, W., Boudalis, A. K., Tuchagues, J.-P. & Mukherjee, R. (2008). Eur. J. Inorg. Chem. pp. 2820-2829.]). For the synthesis, see: Jain et al. (2004[Jain, S. L., Bhattacharyya, P., Milton, H. L., Slawin, A. M. A., Crayston, J. A. & Woollins, J. D. (2004). Dalton Trans. pp. 862-871.]); Lee et al. (2006[Lee, S. J., Lee, S. S., Lee, J. Y. & Jung, J. H. (2006). Chem. Mater. 18, 4713-4715.]); Barnes et al. (1978[Barnes, D. J., Chapman, R. L., Vagg, R. S. & Watton, E. C. (1978). J. Chem. Eng. Data, 23, 349-350.]). For related structures, see: Adolph et al. (2012[Adolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92-98.]); Munro & Wilson (2010[Munro, O. Q. & Wilson, C. (2010). Acta Cryst. C66, o535-o539.]); Yan et al. (2012[Yan, Y., Zhao, W., Bhagavathy, G. V., Faurie, A., Mosey, N. J. & Petitjean, A. (2012). Chem. Commun. 48, 7829-7831.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23N5O2

  • Mr = 389.45

  • Monoclinic, P 21 /n

  • a = 8.64349 (7) Å

  • b = 24.8210 (3) Å

  • c = 18.40861 (18) Å

  • [beta] = 90.5648 (8)°

  • V = 3949.20 (7) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.70 mm-1

  • T = 100 K

  • 0.12 × 0.08 × 0.07 mm

Data collection
  • Agilent Xcalibur Atlas Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.886, Tmax = 0.950

  • 28468 measured reflections

  • 7050 independent reflections

  • 6128 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.097

  • S = 1.14

  • 7050 reflections

  • 523 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the C9-C14 benzene and C31-C36 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
N2-H2...O3 0.86 2.44 3.1099 (18) 135
N7-H7...O1i 0.86 2.42 3.0998 (18) 136
C24-H24...O2ii 0.93 2.48 3.311 (2) 149
C25-H25...O4iii 0.93 2.54 3.213 (2) 129
C8-H8A...Cg6iv 0.97 2.72 3.6468 (18) 161
C30-H30B...Cg5v 0.97 2.74 3.6584 (18) 159
Symmetry codes: (i) x-1, y, z; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5691 ).


Acknowledgements

This work was supported financially by the Natural Science Foundation of Hainan Province, China (grant 212014) and the Scientific Research Foundation of Hainan Normal University.

References

Adolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92-98.  [ISI] [CSD] [CrossRef] [ChemPort]
Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Barnes, D. J., Chapman, R. L., Vagg, R. S. & Watton, E. C. (1978). J. Chem. Eng. Data, 23, 349-350.  [CrossRef] [ChemPort]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cornman, C. R., Zovinka, E. P., Boyajian, Y. D., Olmstead, M. M. & Noll, B. C. (1999). Inorg. Chim. Acta, 285, 134-137.  [ISI] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Jain, S. L., Bhattacharyya, P., Milton, H. L., Slawin, A. M. A., Crayston, J. A. & Woollins, J. D. (2004). Dalton Trans. pp. 862-871.  [CSD] [CrossRef]
Lee, S. J., Lee, S. S., Lee, J. Y. & Jung, J. H. (2006). Chem. Mater. 18, 4713-4715.  [ISI] [CrossRef] [ChemPort]
Munro, O. Q. & Wilson, C. (2010). Acta Cryst. C66, o535-o539.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, A. K., Jacob, W., Boudalis, A. K., Tuchagues, J.-P. & Mukherjee, R. (2008). Eur. J. Inorg. Chem. pp. 2820-2829.  [ISI] [CSD] [CrossRef]
Song, Y. J., Lee, J. H., Koo, H. G., Lee, T. G., Myoung, S.-H., Kim, C., Kim, S.-J. & Kim, Y. (2010). Inorg. Chem. Commun. 13, 753-756.  [ISI] [CSD] [CrossRef] [ChemPort]
Yan, Y., Zhao, W., Bhagavathy, G. V., Faurie, A., Mosey, N. J. & Petitjean, A. (2012). Chem. Commun. 48, 7829-7831.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o677  [ doi:10.1107/S1600536813008696 ]

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