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Volume 69 
Part 9 
Page o1447  
September 2013  

Received 10 August 2013
Accepted 13 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.003 Å
R = 0.061
wR = 0.159
Data-to-parameter ratio = 15.1
Details
Open access

2-Aminobenzoic acid-4,4'-bipyridine (2/1)

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The asymmetric unit of title co-crystal, C10H8N2·2C7H7NO2, comprises a centrosymmetric 4,4'-bipyridine molecule, and a 2-aminobenzoic acid molecule in a general position. The latter is effectively planar [C-C-C-O torsion angle = 5.0 (3)°] owing to an intramolecular N-H...O(carbonyl) hydrogen bond. Three-molecule aggregates are formed via O-H...N(pyridyl) hydrogen bonds and these are connected into supramolecular layers in the bc plane by N-H...O(carbonyl) hydrogen bonds and [pi]-[pi] interactions between pyridyl and benzene rings [inter-centroid distance = 3.634 (2) Å]. Layers are connected along the a axis by weak [pi]-[pi] interactions between benzene rings [3.964 (2) Å].

Related literature

For co-crystals of 2-aminobenzoic acid with pyridyl derivatives, see: Arman, Kaulgud et al. (2012[Arman, H. D., Kaulgud, T., Miller, T. & Tiekink, E. R. T. (2012). Z. Kristallogr. Cryst. Mat. 227, 227-232.]); Arman, Miller & Tiekink (2012[Arman, H. D., Miller, T. & Tiekink, E. R. T. (2012). Z. Kristallogr. Cryst. Mat. 227, 825-830.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N2·2C7H7NO2

  • Mr = 430.46

  • Monoclinic, P 21 /c

  • a = 10.782 (5) Å

  • b = 10.998 (5) Å

  • c = 8.951 (4) Å

  • [beta] = 107.215 (7)°

  • V = 1013.9 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 98 K

  • 0.46 × 0.11 × 0.09 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.723, Tmax = 1.000

  • 7849 measured reflections

  • 2320 independent reflections

  • 1932 reflections with I > 2[sigma](I)

  • Rint = 0.049

  • Standard reflections: 0

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.159

  • S = 1.11

  • 2320 reflections

  • 154 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1n...O2 0.88 (1) 2.02 (2) 2.697 (2) 132 (2)
O1-H1o...N2i 0.85 (1) 1.81 (1) 2.655 (2) 174 (2)
N1-H2n...O2ii 0.88 (2) 2.14 (2) 3.002 (3) 170 (2)
Symmetry codes: (i) x, y, z+1; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2276 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Arman, H. D., Kaulgud, T., Miller, T. & Tiekink, E. R. T. (2012). Z. Kristallogr. Cryst. Mat. 227, 227-232.  [CrossRef] [ChemPort]
Arman, H. D., Miller, T. & Tiekink, E. R. T. (2012). Z. Kristallogr. Cryst. Mat. 227, 825-830.  [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1447  [ doi:10.1107/S160053681302271X ]

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