4-Chloro-7-methoxy­methyl-2-phenyl-7H-pyrrolo[2,3-b]pyridine

Selig, R.; Schollmeyer, D.; Albrecht, W.; Laufer, S.

doi:10.1107/S1600536810008822

Volume 66
Part 4
Page o822
April 2010

Received 8 March 2010
Accepted 8 March 2010
Online 13 March 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.079
Data-to-parameter ratio = 17.8
Details

4-Chloro-7-methoxymethyl-2-phenyl-7H-pyrrolo[2,3-b]pyridine

Roland Selig,^a Dieter Schollmeyer,^b Wolfgang Albrecht ^c and Stefan Laufer ^a ^*

^aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany,^bUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany, and ^cc-a-i-r biosciences GmbH, Paul-Ehrlich-Strasse 15, 72076 Tübingen, Germany
Correspondence e-mail: stefan.laufer@uni-tuebingen.de

In the title compound, C₁₅H₁₃ClN₂O, the phenyl group makes a dihedral angle of 7.91 (8)° with the pyrrole ring. The crystal structure forms a three-dimensional network stabilized by [pi] - [pi] interactions [centroid-centroid distances = 3.807 (1) Å] between the pyridine and phenyl rings and via intermolecular C-HO hydrogen bonds.

Related literature

Chlorination of 2-phenyl-1H-pyrrolo[2,3-b]pyridine was performed by an analogous procedure, see: Layek et al. (2009).

Experimental

Crystal data

C₁₅H₁₃ClN₂O
M_r = 272.72
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4785 (8) Å
b = 9.6576 (10) Å
c = 15.8560 (16) Å
V = 1298.3 (2) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 173 K
0.32 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEXII diffractometer
5977 measured reflections
3084 independent reflections
2667 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.079
S = 1.03
3084 reflections
173 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1299 Friedel pairs
Flack parameter: 0.02 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O15ⁱ	0.95	2.32	3.237 (2)	162
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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: BT5211 ).

Acknowledgements

The authors would like to thank the Federal Ministry of Education and Research, Germany, Merckle GmbH, Ulm, Germany, and the Fonds der Chemischen Industrie, Germany, for their generous support of this work.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Bruker (2006). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Layek, M., Gajare, V., Kalita, D., Islam, A., Mukkanti, K. & Pal, M. (2009). Tetrahedron, 65, 4814-4819
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds