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Volume 68 
Part 11 
Pages o3204-o3205  
November 2012  

Received 10 October 2012
Accepted 18 October 2012
Online 24 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.051
wR = 0.146
Data-to-parameter ratio = 14.4
Details
Open access

2-Cyano-3-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate

aDepartment of Chemistry, Pennsylvania State University, University Park, PA 16802, USA
Correspondence e-mail: hpy1@psu.edu

In dimethyl sulfoxide solvated 9-(2-carboxy-2-cyanovinyl)julolidine, C16H16N2O2·C2H6OS, the essentially planar -CH=(CN)-CO2H substituent (r.m.s. deviation = 0.014 Å) is almost coplanar with respect to the benzene ring, the dihedral angle between the two planes being 0.48 (2)°. The conformations of the fused, non-aromatic rings were found to be half-chair. In the crystal, the acid molecule forms a hydrogen bond to the O atom of the solvent molecule. The acid molecule is disordered over two positions with respect to the methylene C atoms in a 1:1 ratio. The crystal studied was found to be a racemic twin.

Related literature

For the synthesis of 9-(2-carboxy-2-cyanovinyl)julolidine, commonly known as CCVJ, see: Rumble et al. (2012[Rumble, C., Rich, K., He, G. & Maroncelli, M. (2012). J. Phys. Chem. A, doi: 10.1021/jp309019g.]). For a related molecule, see: Liang et al. (2009[Liang, M., Yennawar, H. & Maroncelli, M. (2009). Acta Cryst. E65, o1687.]). For fluorescent-rotor probe studies of CCVJ, see: Sawada et al. (1992[Sawada, S., Iio, T., Hayashi, Y. & Takahashi, S. (1992). Anal. Biochem. 204, 110-117.]); Haidekker et al. (2001[Haidekker, M. A., Ling, T., Anglo, M., Stevens, H. Y., Frangos, J. A. & Theodorakis, E. A. (2001). Chem. Biol. 8, 123-131.]). For other applications, see: Iwaki et al. (1993[Iwaki, T., Torigoe, C., Noji, M. & Nakanishi, M. (1993). Biochemistry, 32, 7589-7592.]); Haidekker et al. (2002[Haidekker, M. A., Tsai, A. G., Brady, T., Stevens, H. Y., Frangos, J. A., Theodorakis, E. & Intaglietta, M. (2002). Am. J. Physiol. Heart Circ. Physiol. 282, H1609-H1614.]); Tanaka et al. (2008[Tanaka, K., Inafuku, K. & Chujo, Y. (2008). Bioorg. Med. Chem. 16, 10029-10033.]); Hawe et al. (2010[Hawe, A., Filipe, V. & Jiskoot, W. (2010). Pharm. Res. 27, 314-326.]); Levitt et al. (2011[Levitt, J. A., Chung, P.-H., Kuimova, M. K., Yahioglu, G., Wang, Y., Qu, J.-L. & Suhling, K. (2011). ChemPhysChem, 12, 662-672.]), Dishari & Hickner (2012[Dishari, S. K. & Hickner, M. A. (2012). ACS Macro Lett. 1, 291-295.]); Howell et al. (2012[Howell, S., Dakanali, M., Theodorakis, E. A. & Haidekker, M. A. (2012). J. Fluoresc. 22, 457-465.]). For a mechanismic study, see: Rumble et al. (2012[Rumble, C., Rich, K., He, G. & Maroncelli, M. (2012). J. Phys. Chem. A, doi: 10.1021/jp309019g.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O2·C2H6OS

  • Mr = 346.44

  • Monoclinic, P 21

  • a = 10.215 (3) Å

  • b = 7.4588 (19) Å

  • c = 11.819 (3) Å

  • [beta] = 100.170 (5)°

  • V = 886.4 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 298 K

  • 0.20 × 0.16 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.971

  • 5962 measured reflections

  • 3443 independent reflections

  • 2520 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.146

  • S = 1.02

  • 3443 reflections

  • 239 parameters

  • 45 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1096 Friedel pairs

  • Flack parameter: 0.51 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3 0.85 (3) 1.83 (3) 2.609 (2) 153 (4)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5301 ).


Acknowledgements

This work was supported by the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences of the US Department of Energy through grant DE-FG02-09ER16118. We also acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dishari, S. K. & Hickner, M. A. (2012). ACS Macro Lett. 1, 291-295.  [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Haidekker, M. A., Ling, T., Anglo, M., Stevens, H. Y., Frangos, J. A. & Theodorakis, E. A. (2001). Chem. Biol. 8, 123-131.  [CrossRef] [PubMed] [ChemPort]
Haidekker, M. A., Tsai, A. G., Brady, T., Stevens, H. Y., Frangos, J. A., Theodorakis, E. & Intaglietta, M. (2002). Am. J. Physiol. Heart Circ. Physiol. 282, H1609-H1614.  [PubMed] [ChemPort]
Hawe, A., Filipe, V. & Jiskoot, W. (2010). Pharm. Res. 27, 314-326.  [ISI] [CrossRef] [ChemPort] [PubMed]
Howell, S., Dakanali, M., Theodorakis, E. A. & Haidekker, M. A. (2012). J. Fluoresc. 22, 457-465.  [CrossRef] [ChemPort] [PubMed]
Iwaki, T., Torigoe, C., Noji, M. & Nakanishi, M. (1993). Biochemistry, 32, 7589-7592.  [CrossRef] [ChemPort] [PubMed] [ISI]
Levitt, J. A., Chung, P.-H., Kuimova, M. K., Yahioglu, G., Wang, Y., Qu, J.-L. & Suhling, K. (2011). ChemPhysChem, 12, 662-672.  [ISI] [CrossRef] [ChemPort] [PubMed]
Liang, M., Yennawar, H. & Maroncelli, M. (2009). Acta Cryst. E65, o1687.  [CSD] [CrossRef] [details]
Rumble, C., Rich, K., He, G. & Maroncelli, M. (2012). J. Phys. Chem. A, doi: 10.1021/jp309019g.
Sawada, S., Iio, T., Hayashi, Y. & Takahashi, S. (1992). Anal. Biochem. 204, 110-117.  [CrossRef] [PubMed] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tanaka, K., Inafuku, K. & Chujo, Y. (2008). Bioorg. Med. Chem. 16, 10029-10033.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3204-o3205   [ doi:10.1107/S1600536812043383 ]

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