3-Amino­benzoic acid–1,2-bis­(4-pyrid­yl)ethane (1/1)

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536810014261

Volume 66
Part 5
Page o1138
May 2010

Received 25 March 2010
Accepted 19 April 2010
Online 24 April 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.108
Data-to-parameter ratio = 13.1
Details

3-Aminobenzoic acid-1,2-bis(4-pyridyl)ethane (1/1)

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, HsinChu, Taiwan 30015, People's Republic of China, and ^bDepartment of Medical Laboratory Science Biotechnology, Yuanpei University, HsinChu, Taiwan 30015, People's Republic of China
Correspondence e-mail: lush@mail.ypu.edu.tw

The asymmetric unit of the title compound, C₁₂H₁₂N₂·C₇H₇NO₂, contains two 3-aminobenzoic acid molecules and two 1,2-bis(4-pyridyl)ethane molecules. In the two 1,2-bis(4-pyridyl)ethane molecules, the dihedral angles between the pyridyl rings are 2.99 (9) and 46.78 (8)°. In the crystal, the molecules associate through amine and carboxyl group N-HO=C interactions between one of the 3-aminobenzoic acid molecules and one of the 1,2-bis(4-pyridyl)ethane molecules, generating R₂²(14) dimers, which are extended head-to-tail via amine and pyridine N-HN hydrogen bonds. Intermolecular O-HN, N-HO, N-HN and C-HO hydrogen bonding are observed in the crystal structure. C-H [pi] and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.9985 (10) Å] are also present.

Related literature

For applications of 3-aminobenzoic acid, see: Lynch & McClenaghan (2001); Smith (2005). For related structures, see: Smith et al. (1995); Lynch et al. (1998). For a similar dimeric R₂²(14) structure, see: Etter et al. (1990).

Experimental

Crystal data

C₁₂H₁₂N₂·C₇H₇NO₂
M_r = 321.37
Triclinic, $[P \overline 1]$
a = 9.0430 (3) Å
b = 13.0565 (5) Å
c = 14.6300 (5) Å
= 88.172 (3)°
= 79.366 (3)°
= 74.506 (3)°
V = 1635.72 (10) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.54 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.997, T_max = 1.000
12385 measured reflections
5971 independent reflections
4125 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.108
S = 0.99
5971 reflections
455 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.57 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C2-C7 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1CN2	0.84 (2)	1.79 (2)	2.6294 (19)	176 (2)
O3-H3AN6ⁱ	0.84 (1)	1.75 (1)	2.5790 (19)	171 (2)
N1-H1AO4ⁱⁱ	0.89 (2)	2.21 (2)	3.061 (2)	158.6 (17)
N1-H1BN3ⁱⁱⁱ	0.882 (19)	2.17 (2)	3.048 (2)	177.8 (19)
N4-H4AO2ⁱⁱ	0.89 (2)	2.19 (2)	3.035 (2)	157.6 (18)
N4-H4BN5^iv	0.89 (2)	2.13 (2)	3.017 (2)	171.9 (17)
C3-H3CO4ⁱⁱ	0.95	2.56	3.353 (2)	141
C22-H22AO2ⁱⁱ	0.95	2.54	3.327 (2)	141
C28-H28AO2^v	0.95	2.55	3.492 (2)	172
C38-H38AO4^vi	0.95	2.50	3.448 (2)	177
C12-H12ACg5^v	0.95	2.67	3.5510 (18)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x, y-1, z-1; (iv) -x+1, -y, -z; (v) -x+2, -y+1, -z; (vi) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2742 ).

Acknowledgements

This work was supported financially by Yuanpei University.

References

Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Lynch, D. E. & McClenaghan, I. (2001). Acta Cryst. C57, 830-832.
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1998). Aust. J. Chem. 51, 587-592.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. (2005). Acta Cryst. E61, o3398-o3400.
Smith, G., Gentner, J. M., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1995). Aust. J. Chem. 48, 1151-1166.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds