9-Phenyl-10H-acridinium trifluoro­methane­sulfonate

Trzybiński, D.; Zadykowicz, B.; Krzymiński, K.; Sikorski, A.; Błażejowski, J.

doi:10.1107/S1600536810040900

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 (C-C) = 0.006 Å
Disorder in solvent or counterion
R = 0.059
wR = 0.184
Data-to-parameter ratio = 11.7
Details

9-Phenyl-10H-acridinium trifluoromethanesulfonate

Damian Trzybinski,^a Beata Zadykowicz,^a Karol Krzyminski,^a Artur Sikorski ^a and Jerzy Blazejowski ^a ^*

^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-HO, C-HO 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); Wróblewska et al. (2004); Zomer & Jacquemijns (2001). For related structures, see: Huta et al. (2002); Magnussen et al. (2007); Stowell et al. (1991); Toma et al. (1994); Trzybinski et al. (2010); Zadykowicz et al. (2009a,b). For intermolecular interactions, see: Aakeröy et al. (1992); Dorn et al. (2005); Novoa et al. (2006); Takahashi et al. (2001). For the synthesis, see: Tsuge et al. (1965); Zadykowicz et al. (2009b). For the treatment of the disorder, see: Müller et al. (2006).

Experimental

Crystal data

C₁₉H₁₄N⁺·CF₃SO₃^-
M_r = 405.39
Monoclinic, P 2₁ /n
a = 9.7064 (5) Å
b = 8.9220 (3) Å
c = 21.8665 (9) Å
= 100.902 (4)°
V = 1859.47 (14) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.895, T_max = 1.000
35783 measured reflections
3296 independent reflections
1565 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(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
_max = 0.31 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C3-H3O24Aⁱ	0.93	2.44	3.333 (9)	160
C4-H4O22A	0.93	2.59	3.348 (8)	139
C5-H5O23A	0.93	2.28	3.154 (9)	157
N10-H10O22A	0.83 (4)	2.43 (4)	3.198 (9)	154 (3)
C17-H17Cg2ⁱⁱ	0.93	2.99	3.632 (7)	127
C20-H20O24Aⁱⁱⁱ	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	IJ	XJ	X-IJ
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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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organic compounds