[Journal logo]

Volume 69 
Part 9 
Page o1476  
September 2013  

Received 30 July 2013
Accepted 21 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.073
Data-to-parameter ratio = 37.1
Details
Open access

Dimethyl 6-iodo-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate

aDepartment of Chemistry, Çankiri Karatekin University, TR-18100 Çankiri, Turkey,bUniversität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C14H14INO4, the dihydropyridine ring adopts a twist conformation. In the crystal, pairs of N-H...O and C-H...O hydrogen bonds link the molecules into inversion R22(10) and R22(18) dimers, forming infinite double chains running along the c axis.

Related literature

For the conversion of 1,2-dihydroquinoline derivatives to the syntheses of quinolines, see: Dauphinee & Forrest (1978[Dauphinee, G. A. & Forrest, T. P. (1978). Can. J. Chem. 56, 632-634.]). For the conversion of 1,2-dihydroquinoline derivatives to the syntheses of 1,2,3,4-tetrahydroquinolines, see: Katritzky et al. (1996[Katritzky, A. R., Rachwal, S. & Rachwal, B. (1996). Tetrahedron, 52, 15031-15070.]). For literature methods for the preparation of 1,2-dihydroquinolines, see: Dauphinee & Forrest (1978[Dauphinee, G. A. & Forrest, T. P. (1978). Can. J. Chem. 56, 632-634.]); Durgadas et al. (2010[Durgadas, S., Chatare, V. K., Mukkanti, K. & Pal, S. (2010). Lett. Org. Chem. 7, 306-310.]); Gültekin & Frey (2012[Gültekin, Z. & Frey, W. (2012). Arkivoc, viii, 250-261.]); Makino et al. (2003[Makino, K., Hara, O., Takiguchi, Y., Katano, T., Asakawa, Y., Hatano, K. & Hamada, Y. (2003). Tetrahedron Lett. 44, 8925-8929.]); Yadav et al. (2007[Yadav, J. S., Reddy, B. V. S., Premalatha, K. & Murty, M. S. R. (2007). J. Mol. Catal. A, 271, 161-163.]); Waldmann et al. (2008[Waldmann, H., Karunakar, G. V. & Kumar, K. (2008). Org. Lett. 10, 2159-2162.]). For related structures, see: Gültekin et al. (2010[Gültekin, Z., Frey, W., Tercan, B. & Hökelek, T. (2010). Acta Cryst. E66, o2891-o2892.], 2011a[Gültekin, Z., Frey, W., Tercan, B. & Hökelek, T. (2011a). Acta Cryst. E67, o672-o673.],b[Gültekin, Z., Frey, W. & Hökelek, T. (2011b). Acta Cryst. E67, o576.], 2012a[Gültekin, Z., Bolte, M. & Hökelek, T. (2012a). Acta Cryst. E68, o606.],b[Gültekin, Z., Bolte, M. & Hökelek, T. (2012b). Acta Cryst. E68, o710-o711.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14INO4

  • Mr = 387.16

  • Triclinic, [P \overline 1]

  • a = 7.7994 (14) Å

  • b = 10.2797 (8) Å

  • c = 10.8056 (8) Å

  • [alpha] = 116.862 (3)°

  • [beta] = 103.956 (4)°

  • [gamma] = 96.780 (4)°

  • V = 723.80 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.22 mm-1

  • T = 100 K

  • 0.76 × 0.65 × 0.48 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: numerical (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.283, Tmax = 0.415

  • 43287 measured reflections

  • 7044 independent reflections

  • 6902 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.073

  • S = 1.24

  • 7044 reflections

  • 190 parameters

  • 1 restraint

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

  • [Delta][rho]max = 1.88 e Å-3

  • [Delta][rho]min = -1.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.82 (2) 2.17 (2) 2.9795 (19) 169 (2)
C5-H5...O1 0.95 2.22 2.866 (2) 125
C12-H12C...O1ii 0.98 2.46 3.132 (2) 126
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2137 ).


Acknowledgements

The title compound was synthesized at RWTH Aachen University, Germany. The authors thank Professor Magnus Rueping of RWTH Aachen University for helpful discussions.

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dauphinee, G. A. & Forrest, T. P. (1978). Can. J. Chem. 56, 632-634.  [CrossRef] [ChemPort] [ISI]
Durgadas, S., Chatare, V. K., Mukkanti, K. & Pal, S. (2010). Lett. Org. Chem. 7, 306-310.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gültekin, Z., Bolte, M. & Hökelek, T. (2012a). Acta Cryst. E68, o606.  [CrossRef] [details]
Gültekin, Z., Bolte, M. & Hökelek, T. (2012b). Acta Cryst. E68, o710-o711.  [CrossRef] [details]
Gültekin, Z. & Frey, W. (2012). Arkivoc, viii, 250-261.
Gültekin, Z., Frey, W. & Hökelek, T. (2011b). Acta Cryst. E67, o576.  [CSD] [CrossRef] [details]
Gültekin, Z., Frey, W., Tercan, B. & Hökelek, T. (2010). Acta Cryst. E66, o2891-o2892.  [CSD] [CrossRef] [details]
Gültekin, Z., Frey, W., Tercan, B. & Hökelek, T. (2011a). Acta Cryst. E67, o672-o673.  [CSD] [CrossRef] [details]
Katritzky, A. R., Rachwal, S. & Rachwal, B. (1996). Tetrahedron, 52, 15031-15070.  [CrossRef] [ChemPort] [ISI]
Makino, K., Hara, O., Takiguchi, Y., Katano, T., Asakawa, Y., Hatano, K. & Hamada, Y. (2003). Tetrahedron Lett. 44, 8925-8929.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Waldmann, H., Karunakar, G. V. & Kumar, K. (2008). Org. Lett. 10, 2159-2162.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yadav, J. S., Reddy, B. V. S., Premalatha, K. & Murty, M. S. R. (2007). J. Mol. Catal. A, 271, 161-163.  [ChemPort]


Acta Cryst (2013). E69, o1476  [ doi:10.1107/S1600536813023544 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.