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Volume 69 
Part 4 
Page o497  
April 2013  

Received 25 February 2013
Accepted 28 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.102
Data-to-parameter ratio = 17.7
Details
Open access

2-[(2-Azaniumylethyl)carbamoyl]phenolate-phenol (1/1)

aLaboratoire de Chimie Inorganiue et d'Environment, Université def Tlemcen, BP 119, Tlemcen 13 000, Algeria,bUnité de Recherche de Cimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 , Algeria,cLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria, and dCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title 1:1 adduct, C9H12N2O2·C6H6O, the dihedral angle between the benzene ring and the salicylic amide group is 6.68 (6)°. The conformation of the amide group is supported by two intramolecular N-H...O hydrogen bonds, which close S(6) and S(7) rings. In the crystal, the components are linked by O-H...O and N-H...O hydrogen bonds, generating (100) sheets.

Related literature

For background to salicylic amides as ligands, see: Koch (2001[Koch, K. R. (2001). Coord. Chem. Rev. 216, 473-488.]); Hancock & Martell (1989[Hancock, R. D. & Martell, A. E. (1989). Chem. Rev. 89, 1875-1914.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12N2O2·C6H6O

  • Mr = 274.31

  • Monoclinic, P 21 /c

  • a = 12.6494 (4) Å

  • b = 13.2145 (6) Å

  • c = 8.5445 (4) Å

  • [beta] = 100.637 (2)°

  • V = 1403.72 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.58 × 0.52 × 0.38 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.860, Tmax = 0.966

  • 12244 measured reflections

  • 3208 independent reflections

  • 2649 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.102

  • S = 1.03

  • 3208 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.82 1.87 2.6696 (13) 166
N1-H1N...O2 0.86 1.93 2.6490 (13) 140
N2-H2A...O1 0.89 2.21 2.8995 (14) 134
N2-H2A...O3 0.89 2.56 3.0547 (13) 116
N2-H2B...O2ii 0.89 1.93 2.7506 (13) 152
N2-H2C...O2iii 0.89 1.81 2.6939 (13) 174
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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 DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7050 ).


Acknowledgements

Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la direction générale de la recherche - Algeria) for financial support.

References

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hancock, R. D. & Martell, A. E. (1989). Chem. Rev. 89, 1875-1914.  [CrossRef] [ChemPort] [ISI]
Koch, K. R. (2001). Coord. Chem. Rev. 216, 473-488.  [ISI] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o497  [ doi:10.1107/S1600536813005849 ]

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