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Volume 66 
Part 11 
Pages o2845-o2846  
November 2010  

Received 17 September 2010
Accepted 12 October 2010
Online 20 October 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.006 Å
Disorder in solvent or counterion
R = 0.059
wR = 0.184
Data-to-parameter ratio = 11.7
Details
Open access

9-Phenyl-10H-acridinium trifluoromethanesulfonate

aFaculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk, Poland
Correspondence e-mail: bla@chem.univ.gda.pl

In the crystal structure of the title compound, C19H14N+·CF3SO3-, the cations are linked to each other by very weak C-H...[pi] interactions, while the cations and anions are connected by N-H...O, C-H...O and S-O...[pi] interactions. The acridine ring system and the phenyl ring are oriented at an angle of 80.1 (1)° with respect to each other. The mean planes of adjacent acridine units are either parallel or inclined at an angle of 35.6 (1)°. The trifluoromethanesulfonate anions are disordered over two positions; the site occupancy factors are 0.591 (8) and 0.409 (8).

Related literature

For general background to chemiluminescence, see: Sato (1996[Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.]); Wróblewska et al. (2004[Wróblewska, A., Huta, O. M., Midyanyj, S. V., Patsay, I. O., Rak, J. & Blazejowski, J. (2004). J. Org. Chem. 69, 1607-1614.]); Zomer & Jacquemijns (2001[Zomer, G. & Jacquemijns, M. (2001). Chemiluminescence in Analytical Chemistry, edited by A. M. Garcia-Campana & W. R. G. Baeyens, pp. 529-549. New York: Marcel Dekker.]). For related structures, see: Huta et al. (2002[Huta, O. M., Patsaj, I. O., Konitz, A., Meszko, J. & Blazejowski, J. (2002). Acta Cryst. C58, o295-o297.]); Magnussen et al. (2007[Magnussen, M., Brock-Nannestad, T. & Bendix, J. (2007). Acta Cryst. C63, m51-m53.]); Stowell et al. (1991[Stowell, J. G., Toma, P. H. & Byrn, S. R. (1991). Acta Cryst. C47, 1637-1640.]); Toma et al. (1994[Toma, P. H., Kelley, M. P., Borchardt, T. B., Byrn, S. R. & Kahr, B. (1994). Chem. Mater. 6, 1317-1324.]); Trzybinski et al. (2010[Trzybinski, D., Zadykowicz, B., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o1548-o1549.]); Zadykowicz et al. (2009a[Zadykowicz, B., Trzybinski, D., Sikorski, A. & Blazejowski, J. (2009a). Acta Cryst. E65, o566-o567.],b[Zadykowicz, B., Krzyminski, K., Trzybinski, D., Sikorski, A. & Blazejowski, J. (2009b). Acta Cryst. E65, o768-o769.]). For intermolecular interactions, see: Aakeröy et al. (1992[Aakeröy, C. B., Seddon, K. R. & Leslie, M. (1992). Struct. Chem. 3, 63-65.]); Dorn et al. (2005[Dorn, T., Janiak, C. & Abu-Shandi, K. (2005). CrystEngComm, 7, 633-641.]); Novoa et al. (2006[Novoa, J. J., Mota, F. & D'Oria, E. (2006). Hydrogen Bonding - New Insights, edited by S. Grabowski, pp. 193-244. The Netherlands: Springer.]); Takahashi et al. (2001[Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.]). For the synthesis, see: Tsuge et al. (1965[Tsuge, O., Nishinohara, M. & Sadano, K. (1965). Bull. Chem. Soc. Jpn, 38, 2037-2041.]); Zadykowicz et al. (2009b[Zadykowicz, B., Krzyminski, K., Trzybinski, D., Sikorski, A. & Blazejowski, J. (2009b). Acta Cryst. E65, o768-o769.]). For the treatment of the disorder, see: Müller et al. (2006[Müller, P., Herbst-Imer, R., Spek, A. L., Schneider, T. R. & Sawaya, M. R. (2006). Crystal Structure Refinement: A Crystallographer's Guide to SHELXL, edited by P. Müller, pp. 57-91. Oxford, New York: Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N+·CF3SO3-

  • Mr = 405.39

  • Monoclinic, P 21 /n

  • a = 9.7064 (5) Å

  • b = 8.9220 (3) Å

  • c = 21.8665 (9) Å

  • [beta] = 100.902 (4)°

  • V = 1859.47 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 295 K

  • 0.40 × 0.15 × 0.04 mm

Data collection
  • Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.895, Tmax = 1.000

  • 35783 measured reflections

  • 3296 independent reflections

  • 1565 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.184

  • S = 1.03

  • 3296 reflections

  • 281 parameters

  • 18 restraints

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C4/C11/C12 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...O24Ai 0.93 2.44 3.333 (9) 160
C4-H4...O22A 0.93 2.59 3.348 (8) 139
C5-H5...O23A 0.93 2.28 3.154 (9) 157
N10-H10...O22A 0.83 (4) 2.43 (4) 3.198 (9) 154 (3)
C17-H17...Cg2ii 0.93 2.99 3.632 (7) 127
C20-H20...O24Aiii 0.93 2.56 3.461 (9) 162
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1.

Table 2
S-O...[pi] interactions (Å, °)

Cg1 and Cg3 are the centroids of the C9/N10/C11-C14 and C5-C8/C13/C14 rings, respectively.

X I J I...J X...J X-I...J
S21 O23A Cg1iii 3.125 (11) 3.923 (2) 114.7 (5)
S21 O22B Cg3iii 3.387 (7) 3.990 (2) 104.7 (3)
S21 O23B Cg1iii 3.159 (9) 3.923 (2) 111.8 (4)
Symmetry code: (iii) -x+1, -y+1, z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 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: VM2046 ).


Acknowledgements

This study was financed by the State Funds for Scientific Research (grant DS/ 8820-4-0087-9).

References

Aakeröy, C. B., Seddon, K. R. & Leslie, M. (1992). Struct. Chem. 3, 63-65.
Dorn, T., Janiak, C. & Abu-Shandi, K. (2005). CrystEngComm, 7, 633-641.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Huta, O. M., Patsaj, I. O., Konitz, A., Meszko, J. & Blazejowski, J. (2002). Acta Cryst. C58, o295-o297.  [CSD] [CrossRef] [details]
Magnussen, M., Brock-Nannestad, T. & Bendix, J. (2007). Acta Cryst. C63, m51-m53.  [CSD] [CrossRef] [details]
Müller, P., Herbst-Imer, R., Spek, A. L., Schneider, T. R. & Sawaya, M. R. (2006). Crystal Structure Refinement: A Crystallographer's Guide to SHELXL, edited by P. Müller, pp. 57-91. Oxford, New York: Oxford University Press.
Novoa, J. J., Mota, F. & D'Oria, E. (2006). Hydrogen Bonding - New Insights, edited by S. Grabowski, pp. 193-244. The Netherlands: Springer.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stowell, J. G., Toma, P. H. & Byrn, S. R. (1991). Acta Cryst. C47, 1637-1640.  [CrossRef] [details]
Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.  [ISI] [CrossRef] [ChemPort]
Toma, P. H., Kelley, M. P., Borchardt, T. B., Byrn, S. R. & Kahr, B. (1994). Chem. Mater. 6, 1317-1324.  [CrossRef] [ChemPort] [ISI]
Trzybinski, D., Zadykowicz, B., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o1548-o1549.  [CrossRef] [details]
Tsuge, O., Nishinohara, M. & Sadano, K. (1965). Bull. Chem. Soc. Jpn, 38, 2037-2041.  [CrossRef] [ChemPort] [ISI]
Wróblewska, A., Huta, O. M., Midyanyj, S. V., Patsay, I. O., Rak, J. & Blazejowski, J. (2004). J. Org. Chem. 69, 1607-1614.  [CrossRef] [PubMed] [ChemPort]
Zadykowicz, B., Krzyminski, K., Trzybinski, D., Sikorski, A. & Blazejowski, J. (2009b). Acta Cryst. E65, o768-o769.  [CSD] [CrossRef] [details]
Zadykowicz, B., Trzybinski, D., Sikorski, A. & Blazejowski, J. (2009a). Acta Cryst. E65, o566-o567.  [CSD] [CrossRef] [details]
Zomer, G. & Jacquemijns, M. (2001). Chemiluminescence in Analytical Chemistry, edited by A. M. Garcia-Campana & W. R. G. Baeyens, pp. 529-549. New York: Marcel Dekker.


Acta Cryst (2010). E66, o2845-o2846   [ doi:10.1107/S1600536810040900 ]

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