9-(2,5-Dimethyl­phen­oxy­carbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate

Trzybiński, D.; Krzymiński, K.; Błażejowski, J.

doi:10.1107/S1600536811045090

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3205-o3206

https://doi.org/10.1107/S1600536811045090

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9-(2,5-Dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate

Damian Trzybiński,^a Karol Krzymiński ^a and Jerzy Błażejowski ^a ^*

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

(Received 19 October 2011; accepted 27 October 2011; online 5 November 2011)

In the title compound, C₂₃H₂₀NO₂⁺·CF₃SO₃⁻, the acridine ring system is oriented at a dihedral angle of 23.1 (1)° with respect to the benzene ring and the carboxyl group is twisted at an angle of 74.1 (1)° relative to the acridine skeleton. In the crystal, adjacent cations are linked through C—H⋯π interactions and neighboring cations and anions via weak C—H⋯O hydrogen bonds. The mean planes of adjacent acridine units are either parallel or inclined at angles of 15.0 (1), 26.9 (1) and 48.1 (1)° in the crystal structure.

Related literature

For general background to the chemiluminogenic properties of 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulfonates, see: Brown et al. (2009 ); King et al. (2007 ); Krzymiński et al. (2011 ); Roda et al. (2003 ). For related structures, see: Krzymiński et al. (2009 ). For intermolecular interactions, see: Novoa et al. (2006 ); Takahashi et al. (2001 ). For the synthesis, see: Sato (1996 ); Krzymiński et al. (2011).

Experimental

Crystal data

C₂₃H₂₀NO₂⁺·CF₃SO₃⁻
M_r = 491.48
Orthorhombic, P b c a
a = 12.3604 (17) Å
b = 17.341 (3) Å
c = 21.101 (3) Å
V = 4522.8 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.60 × 0.15 × 0.10 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 = 0.960, T_max = 0.985
32535 measured reflections
4000 independent reflections
2050 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.185
S = 1.01
4000 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O29ⁱ	0.93	2.59	3.257 (5)	129
C5—H5⋯O30	0.93	2.58	3.466 (5)	160
C6—H6⋯O28	0.93	2.52	3.303 (5)	142
C7—H7⋯O29ⁱⁱ	0.93	2.39	3.188 (5)	144
C20—H20⋯Cg2ⁱⁱⁱ	0.93	2.81	3.439 (4)	126
C25—H25B⋯O28ⁱⁱ	0.96	2.49	3.289 (5)	141
C26—H26A⋯O30ⁱ	0.96	2.47	3.314 (5)	146
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811045090/xu5358sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045090/xu5358Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045090/xu5358Isup3.cml

checkCIF report

Comment top

Chemiluminescing 9-(phenoxycarbonyl)-10-methylacridinium cations are widely applied as indicators or fragments of labels in assays of biologically and environmentally important entities such as antigens, antibodies, enzymes or DNA fragments (Roda et al., 2003; King et al., 2007; Brown et al., 2009). The cations of these salts are oxidized by H₂O₂ in alkaline media, a reaction that is accompanied by the removal of the phenoxycarbonyl fragment and the conversion of the remaining part of the molecules to electronically excited, light-emitting 10-methyl-9-acridinone (Krzymiński et al., 2011). The efficiency of chemiluminescence – crucial to analytical applications – is affected by the constitution of the phenyl fragment. Here we present the crystal structure of 9-(2,5-dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate, whose chemiluminogenic features we have thoroughly investigated (Krzymiński et al., 2011).

In the cation of the title compound (Fig. 1), the bond lengths and angles characterizing the geometry of the acridinium moiety are typical of acridine-based derivatives (Krzymiński et al., 2009). With respective average deviations from planarity of 0.022 (3) Å and 0.006 (3) Å, the acridine and benzene ring systems are oriented at a dihedral angle of 23.1 (1)°. The carboxyl group is twisted at an angle of 74.1 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine moieties are parallel (at an angle 0.0 (1)°) or inclined at angles of 15.0 (1), 26.9 (1) and 48.1 (1)° in the crystal lattice.

In the crystal structure, the adjacent cations are linked by C–H···π (Table 1, Fig. 2) contacts and the neighboring cations and anions via C–H···O (Table 1, Figs. 1 and 2) interactions. The C–H···O interactions are of the hydrogen bond type (Novoa et al. 2006), while the C–H···π (Takahashi et al., 2001) contacts should be of an attractive nature. The crystal structure is stabilized by a network of these specific short-range interactions and by long-range electrostatic interactions between ions.

Related literature top

For general background to the chemiluminogenic properties of 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulfonates, see: Brown et al. (2009); King et al. (2007); Krzymiński et al. (2011); Roda et al. (2003). For related structures, see: Krzymiński et al. (2009). For intermolecular interactions, see: Novoa et al. (2006); Takahashi et al. (2001). For the synthesis, see: Sato (1996); Krzymiński et al. (2011).

Experimental top

2,5-Dimethylphenylacridine-9-carboxylate was synthesized by esterification of 9-(chlorocarbonyl)acridine (obtained in the reaction of acridine-9-carboxylic acid with a tenfold molar excess of thionyl chloride) with 2,5-dimethylphenol in anhydrous dichloromethane in the presence of N,N-diethylethanamine and a catalytic amount of N,N-dimethyl-4-pyridinamine (room temperature, 15 h) (Sato, 1996; Krzymiński et al., 2011). The product was purified chromatographically (SiO₂, cyclohexane/ethyl acetate, 1/1 v/v) and subsequently quaternarized with a fivefold molar excess of methyl trifluoromethanesulfonate dissolved in anhydrous dichloromethane. The crude 9-(2,5-dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate was dissolved in a small amount of ethanol, filtered and precipitated with a 20 v/v excess of diethyl ether. Yellow crystals suitable for X-ray investigations were grown from ethanol/water solution (1:1 v/v) (m.p. 509–511 K).

Structure description top

For general background to the chemiluminogenic properties of 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulfonates, see: Brown et al. (2009); King et al. (2007); Krzymiński et al. (2011); Roda et al. (2003). For related structures, see: Krzymiński et al. (2009). For intermolecular interactions, see: Novoa et al. (2006); Takahashi et al. (2001). For the synthesis, see: Sato (1996); Krzymiński et al. (2011).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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 (Sheldrick, 2008) PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 25% probability level and H atoms are shown as small spheres of arbitrary radius. Cg2 denotes the ring centroid. The C–H···O interactions are represented by dashed lines.
	Fig. 2. The arrangement of the ions in the crystal structure. The C–H···O interactions are represented by dashed lines, the C–H···π contacts by dotted lines. H atoms not involved in interactions have been omitted. [Symmetry codes: (i) –x + 1, –y + 1, –z + 1; (ii) –x + 1, y – 1/2, –z + 1/2; (iii) –x + 3/2, y – 1/2, z.]

9-(2,5-Dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate top

Crystal data top

C₂₃H₂₀NO₂⁺·CF₃SO₃⁻	F(000) = 2032
M_r = 491.48	D_x = 1.444 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4734 reflections
a = 12.3604 (17) Å	θ = 3.4–26.0°
b = 17.341 (3) Å	µ = 0.21 mm⁻¹
c = 21.101 (3) Å	T = 295 K
V = 4522.8 (12) Å³	Needle, yellow
Z = 8	0.60 × 0.15 × 0.10 mm

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	4000 independent reflections
Radiation source: enhanced (Mo) X-ray source	2050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.1°, θ_min = 3.5°
ω scans	h = −14→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −20→20
T_min = 0.960, T_max = 0.985	l = −23→25
32535 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0901P)² + 0.2728P] where P = (F_o² + 2F_c²)/3
4000 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₂₀NO₂⁺·CF₃SO₃⁻	V = 4522.8 (12) Å³
M_r = 491.48	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.3604 (17) Å	µ = 0.21 mm⁻¹
b = 17.341 (3) Å	T = 295 K
c = 21.101 (3) Å	0.60 × 0.15 × 0.10 mm

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	4000 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2050 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.985	R_int = 0.106
32535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.01	Δρ_max = 0.36 e Å⁻³
4000 reflections	Δρ_min = −0.23 e Å⁻³
310 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7203 (3)	0.1485 (2)	0.5953 (2)	0.0692 (11)
H1	0.7452	0.0981	0.5906	0.083*
C2	0.7290 (4)	0.1843 (3)	0.6520 (2)	0.0872 (14)
H2	0.7599	0.1587	0.6863	0.105*
C3	0.6911 (4)	0.2608 (3)	0.6593 (2)	0.0858 (14)
H3	0.6977	0.2849	0.6984	0.103*
C4	0.6455 (3)	0.2995 (2)	0.6105 (2)	0.0713 (12)
H4	0.6197	0.3493	0.6167	0.086*
C5	0.5462 (3)	0.3125 (2)	0.3893 (2)	0.0667 (11)
H5	0.5235	0.3633	0.3943	0.080*
C6	0.5383 (4)	0.2782 (2)	0.3321 (2)	0.0815 (13)
H6	0.5102	0.3061	0.2981	0.098*
C7	0.5711 (4)	0.2021 (2)	0.3224 (2)	0.0720 (12)
H7	0.5637	0.1796	0.2826	0.086*
C8	0.6132 (3)	0.1613 (2)	0.3704 (2)	0.0600 (10)
H8	0.6365	0.1111	0.3633	0.072*
C9	0.6641 (3)	0.15331 (18)	0.48358 (18)	0.0474 (9)
N10	0.5964 (2)	0.30431 (15)	0.50005 (16)	0.0503 (7)
C11	0.6738 (3)	0.18708 (19)	0.54298 (17)	0.0502 (9)
C12	0.6370 (3)	0.26519 (19)	0.55098 (19)	0.0503 (9)
C13	0.6231 (2)	0.19343 (17)	0.43212 (17)	0.0452 (9)
C14	0.5886 (3)	0.27166 (18)	0.44149 (19)	0.0493 (9)
C15	0.7004 (3)	0.07054 (19)	0.47513 (17)	0.0504 (9)
O16	0.61431 (18)	0.02474 (12)	0.47079 (13)	0.0576 (7)
O17	0.7921 (2)	0.05008 (14)	0.47341 (14)	0.0755 (9)
C18	0.6283 (3)	−0.05622 (18)	0.46459 (19)	0.0483 (9)
C19	0.6315 (3)	−0.09995 (19)	0.51964 (19)	0.0518 (9)
C20	0.6311 (2)	−0.1796 (2)	0.5100 (2)	0.0563 (10)
H20	0.6318	−0.2121	0.5451	0.068*
C21	0.6297 (3)	−0.2116 (2)	0.4508 (2)	0.0552 (10)
H21	0.6294	−0.2650	0.4468	0.066*
C22	0.6289 (3)	−0.16674 (19)	0.39689 (19)	0.0542 (10)
C23	0.6272 (3)	−0.08684 (19)	0.4050 (2)	0.0553 (10)
H23	0.6252	−0.0545	0.3699	0.066*
C24	0.6348 (3)	−0.0649 (2)	0.5843 (2)	0.0699 (11)
H24A	0.5841	−0.0231	0.5865	0.105*
H24B	0.7063	−0.0459	0.5927	0.105*
H24C	0.6161	−0.1032	0.6153	0.105*
C25	0.6290 (4)	−0.2022 (2)	0.3319 (2)	0.0846 (13)
H25A	0.7006	−0.1995	0.3143	0.127*
H25B	0.5796	−0.1746	0.3051	0.127*
H25C	0.6070	−0.2552	0.3348	0.127*
C26	0.5592 (3)	0.38590 (18)	0.5077 (2)	0.0727 (12)
H26A	0.5623	0.4000	0.5517	0.109*
H26B	0.4862	0.3906	0.4927	0.109*
H26C	0.6054	0.4194	0.4836	0.109*
S27	0.44245 (10)	0.50390 (5)	0.30301 (6)	0.0740 (4)
O28	0.4254 (3)	0.43431 (19)	0.2715 (2)	0.1310 (14)
O29	0.3900 (3)	0.57019 (19)	0.2803 (2)	0.1239 (13)
O30	0.4320 (3)	0.4936 (2)	0.37051 (17)	0.1162 (12)
C31	0.5832 (5)	0.5223 (4)	0.2920 (3)	0.1130 (19)
F32	0.6101 (4)	0.5876 (3)	0.3223 (3)	0.218 (3)
F33	0.6458 (3)	0.4707 (3)	0.3148 (2)	0.1741 (18)
F34	0.6094 (4)	0.5364 (4)	0.2353 (3)	0.221 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.084 (3)	0.060 (2)	0.064 (3)	0.000 (2)	−0.005 (2)	0.006 (2)
C2	0.113 (4)	0.092 (4)	0.056 (3)	0.000 (3)	−0.015 (3)	0.008 (3)
C3	0.103 (3)	0.097 (4)	0.058 (3)	−0.004 (3)	0.010 (3)	−0.017 (3)
C4	0.074 (3)	0.072 (3)	0.068 (3)	0.001 (2)	0.009 (2)	−0.011 (3)
C5	0.085 (3)	0.039 (2)	0.076 (3)	0.0017 (18)	−0.002 (2)	0.014 (2)
C6	0.115 (4)	0.061 (3)	0.069 (3)	0.000 (2)	−0.019 (3)	0.016 (3)
C7	0.107 (3)	0.059 (3)	0.050 (3)	−0.010 (2)	−0.005 (2)	0.002 (2)
C8	0.076 (3)	0.044 (2)	0.061 (3)	−0.0047 (17)	0.006 (2)	−0.002 (2)
C9	0.0457 (18)	0.0386 (18)	0.058 (3)	−0.0028 (14)	0.0055 (17)	0.0033 (18)
N10	0.0522 (16)	0.0377 (15)	0.061 (2)	−0.0010 (12)	0.0015 (15)	−0.0024 (16)
C11	0.057 (2)	0.045 (2)	0.049 (2)	−0.0060 (16)	0.0012 (18)	0.0022 (19)
C12	0.0508 (19)	0.049 (2)	0.051 (3)	−0.0053 (16)	0.0118 (17)	−0.005 (2)
C13	0.0497 (19)	0.0353 (18)	0.051 (2)	−0.0035 (14)	0.0058 (16)	0.0035 (18)
C14	0.052 (2)	0.0384 (18)	0.057 (3)	−0.0064 (15)	0.0017 (18)	0.0023 (19)
C15	0.054 (2)	0.0421 (19)	0.056 (3)	0.0008 (17)	0.0040 (18)	0.0039 (17)
O16	0.0504 (14)	0.0342 (12)	0.088 (2)	0.0021 (10)	0.0011 (13)	0.0011 (13)
O17	0.0518 (16)	0.0522 (15)	0.123 (3)	0.0057 (12)	0.0045 (16)	−0.0069 (16)
C18	0.0467 (19)	0.0346 (18)	0.064 (3)	0.0009 (14)	−0.0008 (18)	0.0045 (19)
C19	0.0448 (19)	0.048 (2)	0.062 (3)	−0.0001 (15)	−0.0006 (18)	0.005 (2)
C20	0.050 (2)	0.047 (2)	0.072 (3)	−0.0021 (16)	−0.0019 (19)	0.023 (2)
C21	0.051 (2)	0.0379 (19)	0.076 (3)	−0.0014 (15)	−0.0022 (19)	0.005 (2)
C22	0.058 (2)	0.044 (2)	0.061 (3)	0.0023 (16)	−0.0029 (19)	0.003 (2)
C23	0.061 (2)	0.042 (2)	0.062 (3)	0.0027 (16)	−0.0010 (19)	0.014 (2)
C24	0.075 (3)	0.071 (3)	0.064 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C25	0.117 (4)	0.064 (3)	0.073 (3)	0.004 (2)	−0.008 (3)	−0.004 (2)
C26	0.087 (3)	0.040 (2)	0.092 (3)	0.0105 (19)	0.001 (2)	−0.013 (2)
S27	0.1049 (9)	0.0443 (6)	0.0728 (9)	0.0084 (5)	−0.0034 (6)	−0.0028 (6)
O28	0.172 (4)	0.080 (2)	0.141 (4)	0.003 (2)	−0.026 (3)	−0.040 (2)
O29	0.140 (3)	0.080 (2)	0.152 (4)	0.027 (2)	−0.003 (3)	0.034 (2)
O30	0.166 (4)	0.112 (3)	0.071 (2)	0.007 (2)	0.020 (2)	0.007 (2)
C31	0.130 (5)	0.102 (4)	0.108 (5)	−0.007 (4)	0.007 (4)	0.029 (4)
F32	0.187 (4)	0.143 (4)	0.323 (8)	−0.075 (3)	−0.048 (4)	0.026 (4)
F33	0.110 (3)	0.186 (4)	0.227 (5)	0.038 (2)	0.005 (2)	0.091 (3)
F34	0.167 (4)	0.357 (7)	0.139 (4)	0.025 (4)	0.059 (3)	0.111 (5)

Geometric parameters (Å, º) top

C1—C2	1.354 (6)	O16—C18	1.421 (4)
C1—C11	1.413 (5)	C18—C23	1.364 (5)
C1—H1	0.9300	C18—C19	1.388 (5)
C2—C3	1.415 (6)	C19—C20	1.397 (5)
C2—H2	0.9300	C19—C24	1.495 (5)
C3—C4	1.352 (6)	C20—C21	1.367 (5)
C3—H3	0.9300	C20—H20	0.9300
C4—C12	1.394 (5)	C21—C22	1.378 (5)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.349 (6)	C22—C23	1.396 (5)
C5—C14	1.411 (5)	C22—C25	1.503 (6)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.397 (6)	C24—H24A	0.9600
C6—H6	0.9300	C24—H24B	0.9600
C7—C8	1.340 (5)	C24—H24C	0.9600
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.421 (5)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C13	1.386 (5)	C26—H26A	0.9600
C9—C11	1.389 (5)	C26—H26B	0.9600
C9—C15	1.514 (5)	C26—H26C	0.9600
N10—C14	1.363 (4)	S27—O28	1.394 (3)
N10—C12	1.366 (4)	S27—O29	1.404 (3)
N10—C26	1.496 (4)	S27—O30	1.441 (4)
C11—C12	1.439 (5)	S27—C31	1.784 (7)
C13—C14	1.436 (4)	C31—F34	1.264 (6)
C15—O17	1.188 (4)	C31—F33	1.276 (6)
C15—O16	1.331 (4)	C31—F32	1.343 (7)

C2—C1—C11	120.4 (4)	C23—C18—O16	117.9 (3)
C2—C1—H1	119.8	C19—C18—O16	117.8 (3)
C11—C1—H1	119.8	C18—C19—C20	114.7 (4)
C1—C2—C3	120.0 (4)	C18—C19—C24	122.9 (3)
C1—C2—H2	120.0	C20—C19—C24	122.4 (4)
C3—C2—H2	120.0	C21—C20—C19	122.3 (4)
C4—C3—C2	121.4 (4)	C21—C20—H20	118.8
C4—C3—H3	119.3	C19—C20—H20	118.8
C2—C3—H3	119.3	C20—C21—C22	121.7 (3)
C3—C4—C12	120.4 (4)	C20—C21—H21	119.2
C3—C4—H4	119.8	C22—C21—H21	119.2
C12—C4—H4	119.8	C21—C22—C23	117.3 (4)
C6—C5—C14	120.3 (4)	C21—C22—C25	121.4 (3)
C6—C5—H5	119.8	C23—C22—C25	121.2 (4)
C14—C5—H5	119.8	C18—C23—C22	120.0 (3)
C5—C6—C7	121.7 (4)	C18—C23—H23	120.0
C5—C6—H6	119.1	C22—C23—H23	120.0
C7—C6—H6	119.1	C19—C24—H24A	109.5
C8—C7—C6	120.1 (4)	C19—C24—H24B	109.5
C8—C7—H7	120.0	H24A—C24—H24B	109.5
C6—C7—H7	120.0	C19—C24—H24C	109.5
C7—C8—C13	121.3 (3)	H24A—C24—H24C	109.5
C7—C8—H8	119.3	H24B—C24—H24C	109.5
C13—C8—H8	119.3	C22—C25—H25A	109.5
C13—C9—C11	121.8 (3)	C22—C25—H25B	109.5
C13—C9—C15	119.5 (3)	H25A—C25—H25B	109.5
C11—C9—C15	118.7 (3)	C22—C25—H25C	109.5
C14—N10—C12	122.2 (3)	H25A—C25—H25C	109.5
C14—N10—C26	118.0 (3)	H25B—C25—H25C	109.5
C12—N10—C26	119.8 (3)	N10—C26—H26A	109.5
C9—C11—C1	122.7 (3)	N10—C26—H26B	109.5
C9—C11—C12	118.4 (3)	H26A—C26—H26B	109.5
C1—C11—C12	118.9 (3)	N10—C26—H26C	109.5
N10—C12—C4	121.6 (3)	H26A—C26—H26C	109.5
N10—C12—C11	119.4 (3)	H26B—C26—H26C	109.5
C4—C12—C11	118.9 (4)	O28—S27—O29	118.4 (3)
C9—C13—C8	123.5 (3)	O28—S27—O30	110.5 (2)
C9—C13—C14	118.4 (3)	O29—S27—O30	113.4 (2)
C8—C13—C14	118.1 (3)	O28—S27—C31	103.9 (3)
N10—C14—C5	121.7 (3)	O29—S27—C31	105.1 (3)
N10—C14—C13	119.8 (3)	O30—S27—C31	103.8 (3)
C5—C14—C13	118.5 (3)	F34—C31—F33	109.8 (6)
O17—C15—O16	125.6 (3)	F34—C31—F32	102.9 (6)
O17—C15—C9	124.7 (3)	F33—C31—F32	105.2 (6)
O16—C15—C9	109.7 (3)	F34—C31—S27	114.0 (5)
C15—O16—C18	119.9 (2)	F33—C31—S27	114.6 (5)
C23—C18—C19	124.0 (3)	F32—C31—S27	109.3 (5)

C11—C1—C2—C3	0.1 (6)	C9—C13—C14—N10	−0.3 (4)
C1—C2—C3—C4	0.2 (7)	C8—C13—C14—N10	179.7 (3)
C2—C3—C4—C12	−1.5 (7)	C9—C13—C14—C5	−179.6 (3)
C14—C5—C6—C7	0.1 (6)	C8—C13—C14—C5	0.4 (5)
C5—C6—C7—C8	−1.0 (7)	C13—C9—C15—O17	105.8 (4)
C6—C7—C8—C13	1.6 (6)	C11—C9—C15—O17	−73.8 (5)
C13—C9—C11—C1	−176.8 (3)	C13—C9—C15—O16	−74.9 (4)
C15—C9—C11—C1	2.8 (5)	C11—C9—C15—O16	105.5 (3)
C13—C9—C11—C12	1.7 (5)	O17—C15—O16—C18	1.2 (6)
C15—C9—C11—C12	−178.7 (3)	C9—C15—O16—C18	−178.1 (3)
C2—C1—C11—C9	179.2 (4)	C15—O16—C18—C23	−95.3 (4)
C2—C1—C11—C12	0.7 (5)	C15—O16—C18—C19	91.0 (4)
C14—N10—C12—C4	179.4 (3)	C23—C18—C19—C20	−1.3 (5)
C26—N10—C12—C4	−0.3 (5)	O16—C18—C19—C20	172.0 (3)
C14—N10—C12—C11	0.4 (5)	C23—C18—C19—C24	178.8 (3)
C26—N10—C12—C11	−179.2 (3)	O16—C18—C19—C24	−7.9 (5)
C3—C4—C12—N10	−176.6 (4)	C18—C19—C20—C21	1.1 (5)
C3—C4—C12—C11	2.3 (5)	C24—C19—C20—C21	−178.9 (3)
C9—C11—C12—N10	−1.5 (5)	C19—C20—C21—C22	0.2 (5)
C1—C11—C12—N10	177.0 (3)	C20—C21—C22—C23	−1.4 (5)
C9—C11—C12—C4	179.5 (3)	C20—C21—C22—C25	179.1 (3)
C1—C11—C12—C4	−1.9 (5)	C19—C18—C23—C22	0.1 (5)
C11—C9—C13—C8	179.1 (3)	O16—C18—C23—C22	−173.1 (3)
C15—C9—C13—C8	−0.4 (5)	C21—C22—C23—C18	1.2 (5)
C11—C9—C13—C14	−0.8 (5)	C25—C22—C23—C18	−179.3 (3)
C15—C9—C13—C14	179.6 (3)	O28—S27—C31—F34	67.3 (6)
C7—C8—C13—C9	178.7 (3)	O29—S27—C31—F34	−57.8 (6)
C7—C8—C13—C14	−1.3 (5)	O30—S27—C31—F34	−177.1 (6)
C12—N10—C14—C5	179.8 (3)	O28—S27—C31—F33	−60.5 (6)
C26—N10—C14—C5	−0.5 (5)	O29—S27—C31—F33	174.5 (5)
C12—N10—C14—C13	0.5 (4)	O30—S27—C31—F33	55.1 (6)
C26—N10—C14—C13	−179.8 (3)	O28—S27—C31—F32	−178.2 (5)
C6—C5—C14—N10	−179.2 (4)	O29—S27—C31—F32	56.7 (5)
C6—C5—C14—C13	0.2 (5)	O30—S27—C31—F32	−62.6 (5)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O29ⁱ	0.93	2.59	3.257 (5)	129
C5—H5···O30	0.93	2.58	3.466 (5)	160
C6—H6···O28	0.93	2.52	3.303 (5)	142
C7—H7···O29ⁱⁱ	0.93	2.39	3.188 (5)	144
C20—H20···Cg2ⁱⁱⁱ	0.93	2.81	3.439 (4)	126
C25—H25B···O28ⁱⁱ	0.96	2.49	3.289 (5)	141
C26—H26A···O30ⁱ	0.96	2.47	3.314 (5)	146

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀NO₂⁺·CF₃SO₃⁻
M_r	491.48
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	12.3604 (17), 17.341 (3), 21.101 (3)
V (Å³)	4522.8 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.60 × 0.15 × 0.10

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra Ruby CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.960, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	32535, 4000, 2050
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.185, 1.01
No. of reflections	4000
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O29ⁱ	0.93	2.59	3.257 (5)	129
C5—H5···O30	0.93	2.58	3.466 (5)	160
C6—H6···O28	0.93	2.52	3.303 (5)	142
C7—H7···O29ⁱⁱ	0.93	2.39	3.188 (5)	144
C20—H20···Cg2ⁱⁱⁱ	0.93	2.81	3.439 (4)	126
C25—H25B···O28ⁱⁱ	0.96	2.49	3.289 (5)	141
C26—H26A···O30ⁱ	0.96	2.47	3.314 (5)	146

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+3/2, y−1/2, z.

Acknowledgements

This study was financed by the State Funds for Scientific Research through National Center for Science grant No. N N204 375 740 (contract No. 3757/B/H03/2011/40). DT acknowledges financial support from the European Social Fund within the project "Educators for the elite – integrated training program for PhD students, post-docs and professors as academic teachers at the University of Gdansk" and the Human Capital Operational Program Action 4.1.1, Improving the quality on offer at tertiary educational institutions. This publication reflects the views only of the author: the sponsor cannot be held responsible for any use which may be made of the information contained therein.

References

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Volume 67| Part 12| December 2011| Pages o3205-o3206

https://doi.org/10.1107/S1600536811045090

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

9-(2,5-Di­methyl­phen­­oxy­carbon­yl)-10-methyl­acridinium tri­fluoro­methane­sulfonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(2,5-Dimethylphenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate