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Volume 69 
Part 6 
Pages o977-o978  
June 2013  

Received 27 March 2013
Accepted 20 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.140
Data-to-parameter ratio = 12.7
Details
Open access

Ethyl 7-oxo-7H-benzo[de]imidazo[5,1-a]isoquinoline-11-carboxylate-trifluoroacetic acid (1/1)

aDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA
Correspondence e-mail: dzsquared@aol.com

The structure of the title trifluoroacetic acid adduct, C17H12N2O3·C2HF3O2, contains a trifluoroacetic acid molecule hydrogen bonded to the imine N atom of the imidazole ring of a nearly planar four-fused-ring system (r.m.s. deviatiation = 0.013 Å). The carboxylic acid group of the triflouroacetic acid molecule is twisted with respect to the mean plane of the four-fused-ring sytem by 75.9 (2)°. A short intramolecular C-H...O hydrogen bond occurs. In the crystal, the adduct molecules are arranged into stacks along the b axis via [pi]-[pi] interactions between imidazole rings and between imidazole and one of the benzene rings [centroid-centroid distances 3.352 (2) and 3.485 (2) Å, respectively]. Molecules are linked via C-H...O hydrogen bonds, forming an alternating polymeric head-to-head/tail-to-tail stepped chain approximately along the a-axis direction and tilted on an axis bisecting the b and c axes.

Related literature

For 19F NMR studies of related compounds, see: Stibrany (2003[Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure 19F NMR Catalyst Probe, ACS Symp. Series 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210-221. Washington, DC: ACS Press.]). For polymerization studies, see: Stibrany et al. (2003[Stibrany, R. T., Schulz, D. N., Kacker, S., Patil, A. O., Baugh, L. S., Rucker, S. P., Zushma, S., Berluche, E. & Sissano, J. A. (2003). Macromolecules, 36, 8584-8586.]). For their use as agents to study electron transfer, see: Knapp et al. (1990[Knapp, S., Keenan, T. P., Zhang, X., Fikar, R., Potenza, J. A. & Schugar, H. J. (1990). J. Am. Chem. Soc. 112, 3452-3464.]). For related structures, see: Baugh et al. (2006[Baugh, L. S., Sissano, J. A., Kacker, S., Berluche, E., Stibrany, R. T., Schulz, D. N. & Rucker, S. P. (2006). J. Polym. Sci. Part A Polym. Chem. 44, 1817-1840.]); Stibrany (2003[Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure 19F NMR Catalyst Probe, ACS Symp. Series 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210-221. Washington, DC: ACS Press.]); Stibrany et al. (2002[Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.], 2004[Stibrany, R. T., Lobanov, M. V., Schugar, H. J. & Potenza, J. A. (2004). Inorg. Chem. 43, 1472-1480.]); Stibrany & Potenza (2008[Stibrany, R. T. & Potenza, J. A. (2008). Acta Cryst. C64, m213-m216.], 2009[Stibrany, R. T. & Potenza, J. A. (2009). Acta Cryst. C65, o406-o409.]); Gorun et al. (1996[Gorun, S. M., Stibrany, R. T., Katritzky, A. R., Slawinski, J. J., Faid-Allah, H. & Brunner, F. (1996). Inorg. Chem. 35, 3-4.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12N2O3·C2HF3O2

  • Mr = 406.31

  • Triclinic, [P \overline 1]

  • a = 7.642 (3) Å

  • b = 8.111 (4) Å

  • c = 14.043 (6) Å

  • [alpha] = 97.539 (8)°

  • [beta] = 98.055 (8)°

  • [gamma] = 92.695 (8)°

  • V = 852.6 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 100 K

  • 0.48 × 0.10 × 0.07 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.711, Tmax = 1.00

  • 7689 measured reflections

  • 3380 independent reflections

  • 2642 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.140

  • S = 1.00

  • 3380 reflections

  • 267 parameters

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22...O11 0.93 2.15 2.981 (3) 148
O2-H2O...N13 1.03 (3) 1.58 (3) 2.597 (2) 170 (3)
C13-H13...O30i 0.93 2.28 3.143 (3) 154
C23-H23...O11ii 0.93 2.46 3.320 (3) 155
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT, SMART 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: GK2567 ).


References

Baugh, L. S., Sissano, J. A., Kacker, S., Berluche, E., Stibrany, R. T., Schulz, D. N. & Rucker, S. P. (2006). J. Polym. Sci. Part A Polym. Chem. 44, 1817-1840.  [CrossRef] [ChemPort]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gorun, S. M., Stibrany, R. T., Katritzky, A. R., Slawinski, J. J., Faid-Allah, H. & Brunner, F. (1996). Inorg. Chem. 35, 3-4.  [CrossRef] [PubMed] [ChemPort] [ISI]
Knapp, S., Keenan, T. P., Zhang, X., Fikar, R., Potenza, J. A. & Schugar, H. J. (1990). J. Am. Chem. Soc. 112, 3452-3464.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure 19F NMR Catalyst Probe, ACS Symp. Series 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210-221. Washington, DC: ACS Press.
Stibrany, R. T., Lobanov, M. V., Schugar, H. J. & Potenza, J. A. (2004). Inorg. Chem. 43, 1472-1480.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Stibrany, R. T. & Potenza, J. A. (2008). Acta Cryst. C64, m213-m216.  [CSD] [CrossRef] [ChemPort] [details]
Stibrany, R. T. & Potenza, J. A. (2009). Acta Cryst. C65, o406-o409.  [CrossRef] [ChemPort] [details]
Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.  [CSD] [CrossRef] [ChemPort] [details]
Stibrany, R. T., Schulz, D. N., Kacker, S., Patil, A. O., Baugh, L. S., Rucker, S. P., Zushma, S., Berluche, E. & Sissano, J. A. (2003). Macromolecules, 36, 8584-8586.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o977-o978   [ doi:10.1107/S1600536813013834 ]

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