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

Yennawar, H.; He, G.; Rumble, C.; Maroncelli, M.

doi:10.1107/S1600536812043383

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.051
wR = 0.146
Data-to-parameter ratio = 14.4
Details

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

Hemant Yennawar,^a ^* Gang He,^a Christopher Rumble ^a and Mark Maroncelli ^a

^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). For a related molecule, see: Liang et al. (2009). For fluorescent-rotor probe studies of CCVJ, see: Sawada et al. (1992); Haidekker et al. (2001). For other applications, see: Iwaki et al. (1993); Haidekker et al. (2002); Tanaka et al. (2008); Hawe et al. (2010); Levitt et al. (2011), Dishari & Hickner (2012); Howell et al. (2012). For a mechanismic study, see: Rumble et al. (2012).

Experimental

Crystal data

C₁₆H₁₆N₂O₂·C₂H₆OS
M_r = 346.44
Monoclinic, P 2₁
a = 10.215 (3) Å
b = 7.4588 (19) Å
c = 11.819 (3) Å
= 100.170 (5)°
V = 886.4 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.961, T_max = 0.971
5962 measured reflections
3443 independent reflections
2520 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), 1096 Friedel pairs
Flack parameter: 0.51 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3	0.85 (3)	1.83 (3)	2.609 (2)	153 (4)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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

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organic compounds