Dibenzyl 3,3′-diethyl-4,4′-dimethyl-2,2′-methylenebis(pyrrole-5-carboxylate)

Kim, H.-J.

doi:10.1107/S1600536810004459

Volume 66
Part 3
Page o566
March 2010

Received 21 January 2010
Accepted 4 February 2010
Online 10 February 2010

Key indicators
Single-crystal X-ray study
T = 162 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.136
Data-to-parameter ratio = 18.2
Details

Dibenzyl 3,3'-diethyl-4,4'-dimethyl-2,2'-methylenebis(pyrrole-5-carboxylate)

Hee-Joon Kim ^a ^*

^aDepartment of Applied Chemistry, Kumoh National Institute of Technology, 1 Yangho-dong, Gumi 730-701, Republic of Korea
Correspondence e-mail: hjk@kumoh.ac.kr

In the title compound, C₃₁H₃₄N₂O₄, the two pyrrole rings are bent around the central methylene C atom, making a dihedral angle of 64.83 (7)°. In the crystal, molecules are linked into dimers via N-HO=C hydrogen bonds. These dimers are packed through [pi] [pi] interactions between neighboring pyrrole rings with a separation between the mean planes of symmetry-related pyrrole rings of 3.61 (2) Å and a centroid-centroid distance of 4.33 Å. Parallel phenyl groups in neighboring dimers also exhibit efficient [pi] [pi] interactions, characterized by an interplane separation of 3.378 (8) Å and a centroid-centroid distance of 3.97 Å.

Related literature

For the preparation of the title compound, see: Twyman & Sanders (1999). For related structures, see: Bonnett et al. (1972); Senge (2005); Vega et al. (2003). For the use of dipyrrylmethanes in organic synthesis, see: Chen et al. (2000) and references cited therein; Jasat & Dolphin (1997); Shanmugathasan et al. (2000).

Experimental

Crystal data

C₃₁H₃₄N₂O₄
M_r = 498.60
Monoclinic, P 2/n
a = 14.2002 (9) Å
b = 7.9220 (5) Å
c = 25.0939 (16) Å
= 104.373 (3)°
V = 2734.6 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 162 K
0.35 × 0.32 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.972, T_max = 0.993
37570 measured reflections
6304 independent reflections
4371 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.136
S = 1.05
6304 reflections
346 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	0.87 (2)	2.09 (2)	2.9334 (18)	163.4 (18)
N2-H2O3ⁱ	0.89 (2)	2.00 (2)	2.8610 (17)	162.8 (17)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2271 ).

Acknowledgements

This work was supported by Kumoh National Institute of Technology.

References

Bonnett, R., Hursthouse, M. B. & Neidle, S. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 1335-1340.
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA.
Chen, J., Burghart, A., Derecskei-Kovacs, A. & Burgess, K. (2000). J. Org. Chem. 65, 2900-2906.
Jasat, A. & Dolphin, D. (1997). Chem. Rev. 97, 2267-2340.
Senge, M. O. (2005). Acta Cryst. E61, o506-o508.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shanmugathasan, S., Edwards, C. & Boyle, R. W. (2000). Tetrahedron, 56, 1025-1046.
Twyman, L. J. & Sanders, J. K. M. (1999). Tetrahedron Lett. 40, 6681-6684.
Vega, I. E. D., Camiolo, S., Gale, P. A., Hursthouse, M. B. & Light, M. E. (2003). Chem. Commun. pp. 1686-1687.

organic compounds