Propane-1,3-diyl bis­(pyridine-4-carboxyl­ate)

Brito, I.; Vallejos, J.; Bolte, M.; López-Rodríguez, M.; Cárdenas, A.

doi:10.1107/S1600536810011700

Volume 66
Part 5
Page o1015
May 2010

Received 16 March 2010
Accepted 28 March 2010
Online 2 April 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.094
Data-to-parameter ratio = 13.0
Details

Propane-1,3-diyl bis(pyridine-4-carboxylate)

Iván Brito,^a ^* Javier Vallejos,^a Michael Bolte,^b Matías López-Rodríguez ^c and Alejandro Cárdenas ^d

^aDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile,^bInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany,^cInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain, and ^dDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
Correspondence e-mail: ivanbritob@yahoo.com

The title compound. C₁₅H₁₄N₂O₄, (I), has a gauche-gauche (O/C/C/C-O/C/C/C or GG) conformation and is a positional isomer of propane-1,3-diyl bis(pyridine-3-carboxylate), (II). The molecule of (I) lies on a twofold rotation axis, which passes through the central C atom of the aliphatic chain, giving one half-molecule per asymmetric unit. There is excellent agreement of the geometric parameters of (I) and (II). The most obvious differences between them are the O/C/C/C-O/C/C/C torsion angles [56.6 (2)° in (I) and 174.0 (3)/70.2 (3)° in (II) for GG and TG conformations, respectively] and the dihedral angle between the planes of the aromatic rings [80.3 (10)° in (I) and 76.5 (3)° in (II)]. The crystal structure is stabilized by weak C-H N and C-H O hydrogen bonding.

Related literature

The title compound can be used as a nucleophilic tecton in self-assembly reactions with metal centres of varying lability. For conformation definitions see: Carlucci et al. (2002). For related structures, see: Brito et al. (2010); Chatterjee et al. (2004).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Monoclinic, C 2/c
a = 23.022 (4) Å
b = 4.9336 (5) Å
c = 11.9604 (18) Å
= 98.118 (13)°
V = 1344.9 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 173 K
0.18 × 0.15 × 0.09 mm

Data collection

Stoe IPDS II two-circle diffractometer
4231 measured reflections
1251 independent reflections
799 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.094
S = 0.87
1251 reflections
96 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13N14ⁱ	0.95	2.65	3.505 (3)	151
C15-H15N14ⁱⁱ	0.95	2.72	3.496 (3)	139
C3-H3AO1ⁱⁱⁱ	0.99	2.98	3.516 (3)	115
C3-H3BO1^iv	0.99	2.62	3.521 (3)	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2297 ).

Acknowledgements

We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system. JV thanks the Universidad de Antofagasta for PhD fellowships.

References

Brito, I., Vallejos, J., Bolte, M. & López-Rodríguez, M. (2010). Acta Cryst. E66, o792.
Carlucci, L., Ciani, G., Proserpio, D. M. & Rizzato, S. (2002). CrystEngComm, 22, 121-129.
Chatterjee, B., Noveron, J. C., Resendiz, M., Liu, J., Yamamoto, T., Parker, D., Cinke, M., Nguyen, C., Arif, A. & Stang, P. (2004). J. Am. Chem. Soc. 126, 10645-10656.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.

organic compounds