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Volume 69 
Part 6 
Page o991  
June 2013  

Received 15 May 2013
Accepted 19 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 8.9
Details
Open access

N,N'-Bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide dimethylformamide monosolvate

aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan,bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and cNESCOM, PO Box 2216 Islamabad, Pakistan
Correspondence e-mail: Humaira_siddiqi@yahoo.com

The molecular structure of the pyridine derivative, C19H15N3O4·C3H7NO, shows almost planar geometry with dihedral angles of 6.9 (1) and 13.4 (1)° between the pyridine ring and the two benzene rings. This conformation is stabilized by two intramolecular N-H...N(pyridine) bonds. In the crystal, strong O-H...O(carboxamide) and N-H...O(hydroxyphenyl) hydrogen bonds link the molecules, forming a three-dimensional structure. The dimethylformamide solvent molecules are not involved in the hydrogen bonding. The structure shows pseudosymmetry, but refinement in the space group Pbcn leads to significantly worse results and a disordered dimethylformamide molecule.

Related literature

For applications of aromatic polyamides, see: Hamciuc et al., (2001[Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287-293.]); Yang et al. (1998[Yang, G., Jikei, M. & Kakimoto, M.-A. (1998). Macromolecules, 31, 5964-5966.]); Diakoumakos & Mikroyannidis (1994[Diakoumakos, C. D. & Mikroyannidis, J. A. (1994). Polymer, 35, 1986-1990.]); Ebadi & Mehdipour-Ataei (2010[Ebadi, H. & Mehdipour-Ataei, S. (2010). Chin. J. Polym. Sci. 28, 29-37.]). For the structure of a related Co-complex, see: Ali et al. (2012[Ali, A., Hundal, G. & Gupta, R. (2012). Cryst. Growth Des. 12, 1308-1319.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O4·C3H7NO

  • Mr = 422.44

  • Orthorhombic, P c a 21

  • a = 16.8124 (12) Å

  • b = 10.9545 (8) Å

  • c = 10.9331 (7) Å

  • V = 2013.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 130 K

  • 0.47 × 0.41 × 0.39 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.962

  • 18386 measured reflections

  • 2536 independent reflections

  • 2434 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.099

  • S = 1.03

  • 2536 reflections

  • 284 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2B...N1 0.88 2.20 2.661 (2) 113
N3-H3A...N1 0.88 2.22 2.675 (2) 112
O2-H2...O1i 0.84 1.92 2.7572 (19) 179
O4-H4...O3ii 0.84 1.91 2.7464 (19) 172
N2-H2B...O2iii 0.88 2.44 3.125 (2) 135
N3-H3A...O4iv 0.88 2.41 3.043 (2) 130
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+1, z]; (ii) [x+{\script{1\over 2}}, -y+2, z]; (iii) [-x+1, -y+1, z+{\script{1\over 2}}]; (iv) [-x+1, -y+2, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6908 ).


Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for financial assistance and the Universität Paderborn, Germany, for carrying out XRD analysis.

References

Ali, A., Hundal, G. & Gupta, R. (2012). Cryst. Growth Des. 12, 1308-1319.  [CrossRef] [ChemPort]
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Diakoumakos, C. D. & Mikroyannidis, J. A. (1994). Polymer, 35, 1986-1990.  [CrossRef] [ChemPort]
Ebadi, H. & Mehdipour-Ataei, S. (2010). Chin. J. Polym. Sci. 28, 29-37.  [CrossRef] [ChemPort]
Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287-293.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yang, G., Jikei, M. & Kakimoto, M.-A. (1998). Macromolecules, 31, 5964-5966.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o991  [ doi:10.1107/S1600536813013810 ]

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