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Volume 69 
Part 11 
Page o1616  
November 2013  

Received 30 September 2013
Accepted 2 October 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.112
Data-to-parameter ratio = 15.6
Details
Open access

2-Amino­benzoic acid-4-[2-(pyridin-4-yl)eth­yl]pyridine (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 the title co-crystal, C12H12N2·2C7H7NO2, comprises a centrosymmetric 4-[2-(pyridin-4-yl)eth­yl]pyridine mol­ecule and a 2-amino­benzoic acid mol­ecule in a general position. The acid has a small twist between the carb­oxy­lic acid residue and the ring [dihedral angle = 7.13 (6)°] despite the presence of 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 pyridine and benzene rings [inter-centroid distance = 3.6332 (9) Å]. Layers are connected along the a axis by weak [pi]-[pi] inter­actions between benzene rings [3.9577 (10) 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 et al. (2012[Arman, H. D., Miller, T. & Tiekink, E. R. T. (2012). Z. Kristallogr. Cryst. Mat. 227, 825-830.]). For the isostructural 4,4'-bipyridyl analogue, see: Arman & Tiekink (2013[Arman, H. D. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o1447.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2·2C7H7NO2

  • Mr = 458.51

  • Monoclinic, P 21 /c

  • a = 11.305 (2) Å

  • b = 11.102 (2) Å

  • c = 8.8737 (16) Å

  • [beta] = 94.565 (5)°

  • V = 1110.2 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 98 K

  • 0.34 × 0.10 × 0.07 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.864, Tmax = 1.000

  • 8527 measured reflections

  • 2545 independent reflections

  • 2386 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.112

  • S = 1.08

  • 2545 reflections

  • 163 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.36 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
N1-H1n...O2 0.86 (1) 2.03 (1) 2.6961 (15) 134 (2)
O1-H1o...N2 0.86 (1) 1.78 (1) 2.6290 (14) 172 (2)
N1-H2n...O2i 0.85 (1) 2.19 (1) 3.0106 (15) 163 (1)
Symmetry code: (i) [x, -y-{\script{1\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: XU5744 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) and the University of Malaya (UM) 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]
Arman, H. D. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o1447.  [CSD] [CrossRef] [IUCr Journals]
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] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1616  [ doi:10.1107/S1600536813027128 ]

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