10-Methyl-9-(2-nitro­phenoxy­carbon­yl)acridinium trifluoro­methane­sulfonate

Sikorski, A.; Niziołek, A.; Krzymiński, K.; Lis, T.; Błażejowski, J.

doi:10.1107/S1600536807068109

Volume 64
Part 2
Pages o372-o373
February 2008

Received 18 November 2007
Accepted 21 December 2007
Online 4 January 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.064
wR = 0.130
Data-to-parameter ratio = 10.0
Details

10-Methyl-9-(2-nitrophenoxycarbonyl)acridinium trifluoromethanesulfonate

Artur Sikorski,^a Agnieszka Niziolek,^a Karol Krzyminski,^a Tadeusz Lis ^b and Jerzy Blazejowski ^a ^*

^aFaculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk, Poland, and ^bFaculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland
Correspondence e-mail: bla@chem.univ.gda.pl

The crystal structure of the title compound, C₂₁H₁₅N₂O₄⁺·CF₃O₃S^-, is stabilized by C-HO and C-HF hydrogen bonds, by C-F [pi] , N-O [pi] and S-O [pi] interactions, and by OO [2.70 (4) Å] and OF [2.85 (1) or 2.92 (1) Å] contacts; [pi] - [pi] interactions are also present. In the packing of the molecules, acridine units are either parallel or inclined at an angle of 12.5 (1)°. The nitrophenoxycarbonyl unit is disordered over two position; the site occupancy factors are 0.89 and 0.11.

Related literature

For general background, see: Adamczyk et al. (2004); Becker et al. (1999); Rak et al. (1999); Razavi & McCapra (2000a,b); Roda et al. (2003); Zomer & Jacquemijns (2001). For related structures, see: Bianchi et al. (2004); Butcher et al. (2004); Dorn et al. (2005); Hunter & Sanders (1990); Kaafarani et al. (2003); Lyssenko & Antipin (2004); Sato (1996); Sikorski et al. (2007); Sridhar et al. (2006); Steiner (1999). For analysis of intermolecular interactions, see: Spek (2003).

Experimental

Crystal data

C₂₁H₁₅N₂O₄⁺·CF₃O₃S^-
M_r = 508.42
Monoclinic, P 2₁ /c
a = 12.459 (4) Å
b = 21.361 (6) Å
c = 8.123 (3) Å
= 108.42 (3)°
V = 2051.1 (12) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 100 (2) K
0.40 × 0.10 × 0.02 mm

Data collection

Kuma KM-4 CCD -geometry diffractometer
Absorption correction: none
22835 measured reflections
3671 independent reflections
2959 reflections with I > 2(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.130
S = 1.20
3671 reflections
366 parameters
21 restraints
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O30ⁱ	0.95	2.39	3.111 (4)	132
C3-H3O25ⁱ	0.95	2.59	3.268 (10)	129
C5-H5F34ⁱⁱ	0.95	2.55	3.339 (4)	141
C6-H6O31	0.95	2.44	3.196 (4)	136
C20-H20O29ⁱ	0.95	2.59	3.273 (9)	129
C27-H27AO29ⁱⁱⁱ	0.98	2.57	3.246 (4)	126
C27-H27CO30ⁱⁱ	0.98	2.56	3.508 (4)	162
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
C-F [pi] , N-O [pi] and S-O [pi] interactions (Å,°)

X	I	J	IJ	XJ	X-IJ
C32	F33	Cg4^iv	3.690 (4)	4.002 (5)	93.6 (2)
C32	F33	Cg4A^iv	3.949 (18)	4.31 (2)	96.6 (3)
C32	F34	Cg4^iv	3.356 (4)	4.002 (5)	109.3 (2)
C32	F34	Cg4A^iv	3.663 (18)	4.31 (2)	110.3 (3)
N24	O25	Cg4ⁱⁱ	3.443 (9)	3.710 (5)	92.7 (5)
N24	O25	Cg4Aⁱⁱ	3.13 (2)	3.45 (2)	94.8 (6)
N24A	O25A	Cg4ⁱⁱ	3.41 (4)	4.19 (3)	126 (3)
N24A	O25A	Cg4Aⁱⁱ	3.10 (4)	3.91 (3)	128 (3)
S28	O30	Cg1ⁱⁱ	3.810 (3)	3.707 (2)	74.9 (1)
S28	O31	Cg1ⁱⁱ	3.529 (3)	3.707 (2)	85.6 (1)
S28	O31	Cg3ⁱⁱ	3.205 (3)	4.221 (2)	126.7 (1)
Symmetry codes: (ii) $[x, -y+{3\over 2}, z-{1\over 2}]$ ; (iv) $[x-1, -y+{3\over 2}, z-{1\over 2}]$ . Notes: Cg represents the centroid of each ring, as follows: Cg1 ring C9/C11/C12/N10/C14/C13, Cg3 ring C5-C8/C13/C14, Cg4 ring C18-C23 and Cg4A ring C18A-C23A.

Table 3
[pi] - [pi] interactions (Å,°)

CgI	CgJ	CgCg	Dihedral angle	Interplanar distance	Offset
1	2^v	3.547 (2)	3.4	3.504 (3)	0.556 (3)
2	2^v	3.981 (2)	0.0	3.504 (3)	1.891 (3)
Symmetry codes: (v) -x+1, -y+1, -z+1. Notes: Cg represents the centroid of each ring, as follows: Cg1 ring C9/C11/C12/N10/C14/C13 and Cg2 ring C1-C4/C12/C11. CgCg is the distance between ring centroids. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Version 1.171. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Version 1.171. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2382 ).

Acknowledgements

This study was financed by the State Funds for Scientific Research (grant No. N204 123 32/3143, contract No. 3143/H03/2007/32) for the period 2007-2010.

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organic compounds