9-(Biphenyl-4-yl­oxycarbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate

Trzybiński, D.; Skupień, M.; Krzymiński, K.; Sikorski, A.; Błażejowski, J.

doi:10.1107/S1600536809007569

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o770-o771

doi:10.1107/S1600536809007569

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9-(Biphenyl-4-yloxycarbonyl)-10-methylacridinium trifluoromethanesulfonate

Damian Trzybiński,^a Magdalena Skupień,^a Karol Krzymiński,^a Artur Sikorski ^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 24 February 2009; accepted 2 March 2009; online 14 March 2009)

In the crystal structure of the title compound, C₂₇H₂₀NO₂⁺·CF₃SO₃⁻, the cations form inversion dimers through π–π interactions between the acridine ring systems [centroid-centroid distances = 3.668 (2)–3.994 (2) Å]. These dimers are further linked by C—H⋯O and C—H⋯π interactions. The cation and the anion are connected by C—H⋯O interactions. The mean plane of the acridine ring system makes dihedral angles of 10.6 (1) and 82.5 (1)°, respectively, with the adjacent phenyl ring and the carboxy group. The two phenyl rings of the biphenyl group are oriented at 42.9 (1)°.

Related literature

For general background, see: Adamczyk et al. (2004 ); Becker et al. (1999 ); Dodeigne et al. (2000 ); Rak et al. (1999 ); Zomer & Jacquemijns (2001 ). For related structures, see: Sikorski et al. (2007 , 2008 ). For molecular interactions, see: Bianchi et al. (2004 ); Hunter & Sanders (1990 ); Steiner (1999 ); Takahashi et al. (2001 ). For the synthesis, see: Sato (1996 ); Sikorski et al. (2007).

Experimental

Crystal data

C₂₇H₂₀NO₂⁺·CF₃SO₃⁻
M_r = 539.52
Monoclinic, P 2₁ /c
a = 9.4619 (2) Å
b = 12.4558 (5) Å
c = 20.7903 (7) Å
β = 94.559 (3)°
V = 2442.50 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.6 × 0.12 × 0.1 mm

Data collection

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.887, T_max = 0.977
42490 measured reflections
4408 independent reflections
3454 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.05
4408 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O33ⁱ	0.93	2.58	3.228 (3)	127
C7—H7⋯O34	0.93	2.59	3.431 (3)	151
C8—H8⋯O32	0.93	2.52	3.335 (2)	147
C22—H22⋯O33ⁱⁱ	0.93	2.51	3.271 (3)	140
C28—H28⋯O34ⁱⁱⁱ	0.93	2.52	3.429 (3)	166
C30—H30A⋯O17ⁱ	0.96	2.55	3.125 (2)	118
C29—H29⋯Cg2^iv	0.93	2.81	3.417 (2)	123
C30—H30A⋯Cg4ⁱ	0.96	2.83	3.683 (2)	148
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x+1, y, z. Cg2 and Cg4 are the centroids of the C1–C4/C11/C12 and C18–C23 rings, respectively.

Table 2
π–π Interactions (Å,°)

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgJ_Perp	CgI_Offset	CgJ_Offset
1	1^v	3.993 (2)	0	3.609 (2)	3.609 (2)	1.709 (2)	1.709 (2)
1	3^v	3.668 (2)	2.0	3.583 (2)	3.578 (2)	0.785 (2)	0.807 (2)
2	3^v	3.944 (2)	2.4	3.507 (2)	3.577 (2)	1.804 (2)	1.661 (2)
Symmetry codes: (v) -x, -y+2, -z+1. Notes: Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp and CgJ_Perp are the perpendicular distances of CgI from ring J and of CgJ from ring I, respectively. CgI_Offset and CgJ_Offset are the distances between CgI and the perpendicular projection of CgJ on ring I, and between CgJ and the perpendicular projection of CgI on ring J, respectively.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: 10.1107/S1600536809007569/is2396sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007569/is2396Isup2.hkl

checkCIF report

Comment top

There has long been interest in phenyl 10-methylacridinium-9-carboxylates, owing to their distinctive chemiluminogenic features (Rak et al., 1999; Dodeigne et al., 2000; Zomer & Jacquemijns, 2001). Compounds of this kind are oxidized by hydrogen peroxide or other peroxides in alkaline media: the phenoxycarbonyl fragments are removed and the rest of the molecules are converted to electronically excited, light-emitting 10-methyl-9-acridinones. The above-mentioned chemiluminescence is the basis for using of phenyl 10-methylacridinium-9-carboxylates as chemiluminescent indicators, or as chemiluminogenic fragments of the chemiluminescent labels (Dodeigne et al., 2000; Zomer & Jacquemijns, 2001) applied in assays of biologically and environmentally important entities such as antigens, antibodies, enzymes and DNA fragments (Becker et al., 1999; Adamczyk et al., 2004). As the structure of the phenyl fragment affects the efficiency of chemiluminescence (Zomer & Jacquemijns, 2001), we undertook investigations to enrich our knowledge of this effect. Here, we discuss the crystal structure of phenyl 10-methylacridinium-9-carboxylate substituted by phenyl in the phenyl fragment. The phenyl group, which enlarges the phenoxycarbonyl fragment removed during oxidation, may influence the stability and chemiluminescent efficiency of the compound investigated.

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 (Sikorski et al., 2007, 2008). With respective average deviations from planarity of 0.026 (2) Å and 0.006 (2) Å, the acridine and benzene (C18—C23) ring systems in the cation are oriented at 10.6 (1)°. The C18—C23 and C24—C29 benzene ring systems, with respective average deviations from planarity of 0.006 (2) Å and 0.007 (2) Å, are mutually oriented at a dihedral angle of 42.9 (1)°. The carboxy group is twisted at an angle of 82.5 (1)° relative to the acridine skeleton. The mean planes of the acridine moieties are either parallel or are inclined at an angle of 21.1 (1)°.

In the crystal structure, the inversely oriented cations form dimers through multidirectional π–π interactions involving acridine moieties (Table 2, Fig. 2). These dimers are linked by C–H···O (Table 1, Fig. 2) and C–H···π (Table 1, Fig. 2) interactions to neighboring cations, and by C–H···O (Table 1, Fig. 2) interactions to neighboring anions. The C–H···O interactions are of the hydrogen-bond type (Steiner, 1999; Bianchi et al., 2004). The C–H···π interactions should be of an attractive nature (Takahashi et al., 2001), like the π–π interactions (Hunter & Sanders, 1990). The crystal structure is stabilized by a network of these short-range specific interactions and by long-range electrostatic interactions between ions.

Related literature top

For general background, see: Adamczyk et al. (2004); Becker et al. (1999); Dodeigne et al. (2000); Rak et al. (1999); Zomer & Jacquemijns (2001). For related structures, see: Sikorski et al. (2007, 2008). For molecular interactions, see: Bianchi et al. (2004); Hunter & Sanders (1990); Steiner (1999); Takahashi et al. (2001). For the synthesis, see: Sato (1996); Sikorski et al. (2007). Cg2 and Cg4 are the centroids of the C1–C4/C11/C12 and C18–C23 rings, respectively.

Experimental top

The compound was synthesized in three steps (Sikorski et al., 2007). First, 9-(chlorocarbonyl)-acridine was produced by treating acridine-9-carboxylic acid with a tenfold molar excess of thionyl chloride. Then, esterification with biphenyl-4-ol was carried out 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). The crude product was purified chromatographically (SiO₂, cyclohexane/ethyl acetate, 3/2 v/v). The biphenyl-4-yl acridine-9-carboxylate thus obtained was quaternalized with a fivefold molar excess of methyl trifluoromethanesulfonate dissolved in anhydrous dichloromethane. The crude 9-[(biphenyl-4-yloxy)carbonyl]-10-methylacridinium salt was dissolved in a small amount of ethanol, filtered and precipitated with a 25 v/v excess of diethyl ether (yield 50%). Yellow crystals suitable for X-ray investigations were grown from absolute ethanol solution (m.p. 241–243 K).

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) and 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. Cg1, Cg2, Cg3 and Cg4 denote the ring centroids.
	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 and π–π interactions by dotted lines. H atoms not involved in interactions have been omitted. [Symmetry codes: (i) x - 1, y, z; (ii) x, -y + 3/2, z + 1/2; (iii) x + 1, -y + 3/2, z + 1/2; (iv) x + 1, y, z; (v) -x, -y+2, -z + 1.]

9-(Biphenyl-4-yloxycarbonyl)-10-methylacridinium trifluoromethanesulfonate top

Crystal data top

C₂₇H₂₀NO₂⁺·CF₃SO₃⁻	F(000) = 1112
M_r = 539.52	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1909 reflections
a = 9.4619 (2) Å	θ = 3.0–29.2°
b = 12.4558 (5) Å	µ = 0.20 mm⁻¹
c = 20.7903 (7) Å	T = 295 K
β = 94.559 (3)°	Needle, yellow
V = 2442.50 (14) Å³	0.6 × 0.12 × 0.1 mm
Z = 4

Data collection top

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer	4408 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→14
T_min = 0.887, T_max = 0.977	l = −24→24
42490 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0642P)² + 0.3778P] where P = (F_o² + 2F_c²)/3
4408 reflections	(Δ/σ)_max = 0.001
344 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₇H₂₀NO₂⁺·CF₃SO₃⁻	V = 2442.50 (14) Å³
M_r = 539.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4619 (2) Å	µ = 0.20 mm⁻¹
b = 12.4558 (5) Å	T = 295 K
c = 20.7903 (7) Å	0.6 × 0.12 × 0.1 mm
β = 94.559 (3)°

Data collection top

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer	4408 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3454 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.977	R_int = 0.033
42490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
4408 reflections	Δρ_min = −0.39 e Å⁻³
344 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
C1	0.0826 (2)	0.85546 (17)	0.66803 (10)	0.0559 (5)
H1	0.1794	0.8419	0.6743	0.067*
C2	0.0070 (2)	0.8721 (2)	0.71966 (11)	0.0666 (6)
H2	0.0516	0.8705	0.7612	0.080*
C3	−0.1399 (2)	0.8920 (2)	0.71009 (11)	0.0661 (6)
H3	−0.1913	0.9025	0.7459	0.079*
C4	−0.2082 (2)	0.89610 (17)	0.65079 (10)	0.0556 (5)
H4	−0.3052	0.9097	0.6462	0.067*
C5	−0.1940 (2)	0.87413 (17)	0.41735 (10)	0.0533 (5)
H5	−0.2913	0.8854	0.4114	0.064*
C6	−0.1171 (2)	0.86205 (18)	0.36536 (11)	0.0608 (6)
H6	−0.1632	0.8652	0.3242	0.073*
C7	0.0303 (2)	0.84498 (17)	0.37199 (11)	0.0589 (5)
H7	0.0807	0.8385	0.3356	0.071*
C8	0.0983 (2)	0.83809 (16)	0.43131 (10)	0.0506 (5)
H8	0.1956	0.8261	0.4355	0.061*
C9	0.08977 (17)	0.84149 (13)	0.54978 (9)	0.0411 (4)
N10	−0.19839 (14)	0.88388 (11)	0.53452 (7)	0.0409 (4)
C11	0.01625 (17)	0.85832 (14)	0.60431 (9)	0.0426 (4)
C12	−0.13276 (18)	0.87986 (14)	0.59538 (9)	0.0432 (4)
C13	0.02305 (17)	0.84892 (13)	0.48766 (9)	0.0407 (4)
C14	−0.12638 (17)	0.86960 (13)	0.48029 (9)	0.0405 (4)
C15	0.24609 (17)	0.81633 (15)	0.55824 (9)	0.0442 (4)
O16	0.26663 (11)	0.71126 (10)	0.55470 (6)	0.0468 (3)
O17	0.33626 (14)	0.88239 (12)	0.56714 (9)	0.0750 (5)
C18	0.40924 (17)	0.67406 (14)	0.56630 (9)	0.0397 (4)
C19	0.48541 (18)	0.65153 (15)	0.51460 (9)	0.0453 (4)
H19	0.4465	0.6623	0.4726	0.054*
C20	0.62226 (18)	0.61225 (15)	0.52661 (8)	0.0443 (4)
H20	0.6754	0.5962	0.4921	0.053*
C21	0.68130 (17)	0.59638 (14)	0.58923 (8)	0.0378 (4)
C22	0.59895 (19)	0.61933 (16)	0.63985 (9)	0.0472 (4)
H22	0.6366	0.6088	0.6821	0.057*
C23	0.46215 (19)	0.65756 (16)	0.62865 (9)	0.0493 (5)
H23	0.4072	0.6718	0.6628	0.059*
C24	0.82954 (17)	0.55657 (14)	0.60215 (8)	0.0385 (4)
C25	0.88247 (19)	0.47452 (16)	0.56618 (9)	0.0497 (5)
H25	0.8243	0.4422	0.5336	0.060*
C26	1.0212 (2)	0.44002 (18)	0.57816 (11)	0.0587 (5)
H26	1.0549	0.3842	0.5539	0.070*
C27	1.1092 (2)	0.48737 (19)	0.62543 (11)	0.0603 (6)
H27	1.2029	0.4649	0.6327	0.072*
C28	1.0580 (2)	0.56810 (19)	0.66193 (11)	0.0607 (6)
H28	1.1171	0.6003	0.6943	0.073*
C29	0.91906 (19)	0.60188 (16)	0.65086 (9)	0.0505 (5)
H29	0.8850	0.6558	0.6765	0.061*
C30	−0.35306 (18)	0.90607 (18)	0.52817 (11)	0.0586 (5)
H30A	−0.4013	0.8538	0.5524	0.088*
H30B	−0.3875	0.9021	0.4835	0.088*
H30C	−0.3703	0.9766	0.5445	0.088*
S31	0.43886 (5)	0.83310 (5)	0.31913 (2)	0.05338 (17)
O32	0.42879 (16)	0.85116 (15)	0.38681 (7)	0.0738 (5)
O33	0.56626 (19)	0.87108 (17)	0.29520 (8)	0.0896 (6)
O34	0.31337 (17)	0.85327 (16)	0.27869 (8)	0.0865 (6)
C35	0.4565 (3)	0.6904 (2)	0.31430 (13)	0.0827 (8)
F36	0.3429 (3)	0.64219 (17)	0.33492 (13)	0.1497 (9)
F37	0.5652 (2)	0.65377 (17)	0.35025 (10)	0.1352 (8)
F38	0.4689 (3)	0.65853 (16)	0.25421 (10)	0.1447 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0429 (10)	0.0619 (13)	0.0621 (13)	0.0029 (9)	−0.0010 (9)	−0.0086 (10)
C2	0.0657 (14)	0.0780 (16)	0.0557 (13)	0.0022 (12)	0.0015 (11)	−0.0135 (11)
C3	0.0630 (13)	0.0762 (16)	0.0614 (14)	0.0035 (11)	0.0188 (11)	−0.0153 (11)
C4	0.0403 (10)	0.0604 (13)	0.0681 (14)	0.0041 (9)	0.0168 (10)	−0.0122 (10)
C5	0.0399 (10)	0.0544 (12)	0.0645 (13)	0.0030 (9)	−0.0023 (9)	−0.0015 (10)
C6	0.0603 (13)	0.0672 (15)	0.0542 (12)	0.0026 (11)	−0.0006 (10)	−0.0018 (10)
C7	0.0614 (13)	0.0612 (13)	0.0559 (13)	−0.0003 (10)	0.0170 (10)	−0.0024 (10)
C8	0.0394 (9)	0.0508 (12)	0.0631 (13)	0.0009 (8)	0.0135 (9)	−0.0019 (9)
C9	0.0294 (8)	0.0343 (10)	0.0597 (11)	−0.0011 (7)	0.0052 (8)	−0.0027 (8)
N10	0.0263 (7)	0.0368 (8)	0.0598 (10)	0.0017 (6)	0.0048 (6)	−0.0044 (7)
C11	0.0323 (8)	0.0389 (10)	0.0568 (11)	0.0007 (7)	0.0045 (8)	−0.0047 (8)
C12	0.0357 (9)	0.0346 (10)	0.0600 (12)	−0.0001 (7)	0.0095 (8)	−0.0063 (8)
C13	0.0317 (8)	0.0333 (9)	0.0577 (11)	−0.0008 (7)	0.0079 (8)	−0.0023 (8)
C14	0.0328 (8)	0.0312 (9)	0.0575 (11)	−0.0004 (7)	0.0048 (8)	−0.0028 (7)
C15	0.0292 (9)	0.0450 (11)	0.0588 (12)	0.0014 (8)	0.0070 (8)	−0.0039 (8)
O16	0.0289 (6)	0.0435 (7)	0.0673 (8)	0.0036 (5)	−0.0001 (5)	−0.0044 (6)
O17	0.0305 (7)	0.0491 (9)	0.1453 (16)	−0.0025 (6)	0.0065 (8)	−0.0091 (9)
C18	0.0279 (8)	0.0392 (10)	0.0518 (11)	0.0032 (7)	0.0021 (7)	−0.0023 (7)
C19	0.0388 (9)	0.0560 (12)	0.0401 (10)	0.0052 (8)	−0.0025 (8)	0.0003 (8)
C20	0.0368 (9)	0.0562 (12)	0.0403 (10)	0.0056 (8)	0.0063 (8)	−0.0029 (8)
C21	0.0356 (9)	0.0363 (9)	0.0413 (9)	0.0008 (7)	0.0020 (7)	−0.0009 (7)
C22	0.0426 (10)	0.0601 (12)	0.0383 (10)	0.0084 (9)	−0.0003 (8)	0.0004 (8)
C23	0.0426 (10)	0.0609 (12)	0.0456 (11)	0.0071 (9)	0.0108 (8)	−0.0043 (9)
C24	0.0335 (8)	0.0389 (10)	0.0429 (10)	0.0022 (7)	0.0016 (7)	0.0068 (7)
C25	0.0396 (9)	0.0508 (12)	0.0589 (12)	0.0032 (8)	0.0044 (8)	−0.0043 (9)
C26	0.0483 (11)	0.0570 (13)	0.0730 (14)	0.0149 (10)	0.0175 (10)	0.0068 (10)
C27	0.0351 (10)	0.0697 (15)	0.0759 (14)	0.0100 (10)	0.0028 (10)	0.0266 (12)
C28	0.0449 (11)	0.0656 (14)	0.0683 (14)	−0.0025 (10)	−0.0171 (10)	0.0106 (11)
C29	0.0460 (10)	0.0477 (11)	0.0562 (12)	0.0035 (9)	−0.0062 (9)	0.0011 (9)
C30	0.0273 (9)	0.0701 (14)	0.0787 (15)	0.0081 (9)	0.0060 (9)	−0.0022 (11)
S31	0.0446 (3)	0.0750 (4)	0.0403 (3)	0.0105 (2)	0.0021 (2)	0.0059 (2)
O32	0.0688 (10)	0.1071 (13)	0.0460 (9)	0.0136 (9)	0.0071 (7)	−0.0074 (8)
O33	0.0748 (11)	0.1331 (16)	0.0616 (10)	−0.0285 (11)	0.0099 (8)	0.0162 (10)
O34	0.0632 (10)	0.1304 (16)	0.0636 (10)	0.0386 (10)	−0.0095 (8)	0.0109 (10)
C35	0.094 (2)	0.0887 (19)	0.0651 (16)	0.0174 (16)	0.0063 (14)	0.0031 (14)
F36	0.160 (2)	0.1052 (16)	0.185 (2)	−0.0438 (14)	0.0162 (17)	0.0355 (14)
F37	0.1460 (17)	0.1334 (16)	0.1238 (16)	0.0835 (14)	−0.0050 (13)	0.0290 (12)
F38	0.231 (3)	0.1055 (14)	0.0970 (14)	0.0430 (15)	0.0084 (15)	−0.0326 (11)

Geometric parameters (Å, º) top

C1—C2	1.352 (3)	C19—C20	1.388 (2)
C1—C11	1.421 (3)	C19—H19	0.9300
C1—H1	0.9300	C20—C21	1.389 (2)
C2—C3	1.411 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.388 (2)
C3—C4	1.347 (3)	C21—C24	1.492 (2)
C3—H3	0.9300	C22—C23	1.382 (3)
C4—C12	1.418 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.358 (3)	C24—C25	1.384 (3)
C5—C14	1.411 (3)	C24—C29	1.388 (3)
C5—H5	0.9300	C25—C26	1.385 (3)
C6—C7	1.407 (3)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.370 (3)
C7—C8	1.347 (3)	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.371 (3)
C8—C13	1.425 (3)	C27—H27	0.9300
C8—H8	0.9300	C28—C29	1.383 (3)
C9—C11	1.392 (3)	C28—H28	0.9300
C9—C13	1.395 (3)	C29—H29	0.9300
C9—C15	1.508 (2)	C30—H30A	0.9600
N10—C12	1.365 (2)	C30—H30B	0.9600
N10—C14	1.374 (2)	C30—H30C	0.9600
N10—C30	1.485 (2)	S31—O33	1.4212 (17)
C11—C12	1.433 (2)	S31—O34	1.4216 (16)
C13—C14	1.433 (2)	S31—O32	1.4356 (15)
C15—O17	1.189 (2)	S31—C35	1.788 (3)
C15—O16	1.326 (2)	C35—F37	1.305 (3)
O16—C18	1.4289 (19)	C35—F38	1.325 (3)
C18—C23	1.368 (3)	C35—F36	1.332 (3)
C18—C19	1.370 (3)

C2—C1—C11	120.93 (19)	C18—C19—H19	120.9
C2—C1—H1	119.5	C20—C19—H19	120.9
C11—C1—H1	119.5	C19—C20—C21	121.24 (16)
C1—C2—C3	119.5 (2)	C19—C20—H20	119.4
C1—C2—H2	120.3	C21—C20—H20	119.4
C3—C2—H2	120.3	C22—C21—C20	118.23 (15)
C4—C3—C2	122.1 (2)	C22—C21—C24	120.56 (15)
C4—C3—H3	118.9	C20—C21—C24	121.21 (15)
C2—C3—H3	118.9	C23—C22—C21	121.20 (17)
C3—C4—C12	120.16 (18)	C23—C22—H22	119.4
C3—C4—H4	119.9	C21—C22—H22	119.4
C12—C4—H4	119.9	C18—C23—C22	118.63 (17)
C6—C5—C14	120.09 (18)	C18—C23—H23	120.7
C6—C5—H5	120.0	C22—C23—H23	120.7
C14—C5—H5	120.0	C25—C24—C29	117.95 (16)
C5—C6—C7	121.9 (2)	C25—C24—C21	121.59 (16)
C5—C6—H6	119.0	C29—C24—C21	120.46 (16)
C7—C6—H6	119.0	C24—C25—C26	120.71 (19)
C8—C7—C6	119.76 (19)	C24—C25—H25	119.6
C8—C7—H7	120.1	C26—C25—H25	119.6
C6—C7—H7	120.1	C27—C26—C25	120.6 (2)
C7—C8—C13	120.91 (18)	C27—C26—H26	119.7
C7—C8—H8	119.5	C25—C26—H26	119.7
C13—C8—H8	119.5	C26—C27—C28	119.42 (18)
C11—C9—C13	121.68 (16)	C26—C27—H27	120.3
C11—C9—C15	119.01 (17)	C28—C27—H27	120.3
C13—C9—C15	119.29 (16)	C27—C28—C29	120.3 (2)
C12—N10—C14	122.46 (14)	C27—C28—H28	119.9
C12—N10—C30	117.50 (15)	C29—C28—H28	119.9
C14—N10—C30	120.04 (16)	C28—C29—C24	121.01 (19)
C9—C11—C1	122.90 (17)	C28—C29—H29	119.5
C9—C11—C12	118.22 (17)	C24—C29—H29	119.5
C1—C11—C12	118.87 (17)	N10—C30—H30A	109.5
N10—C12—C4	121.77 (16)	N10—C30—H30B	109.5
N10—C12—C11	119.83 (15)	H30A—C30—H30B	109.5
C4—C12—C11	118.40 (18)	N10—C30—H30C	109.5
C9—C13—C8	122.43 (16)	H30A—C30—H30C	109.5
C9—C13—C14	118.75 (16)	H30B—C30—H30C	109.5
C8—C13—C14	118.82 (17)	O33—S31—O34	115.21 (11)
N10—C14—C5	122.53 (16)	O33—S31—O32	114.53 (10)
N10—C14—C13	118.99 (16)	O34—S31—O32	115.76 (10)
C5—C14—C13	118.47 (16)	O33—S31—C35	103.03 (14)
O17—C15—O16	125.81 (16)	O34—S31—C35	102.70 (13)
O17—C15—C9	123.99 (17)	O32—S31—C35	102.97 (12)
O16—C15—C9	110.20 (15)	F37—C35—F38	108.1 (2)
C15—O16—C18	116.83 (13)	F37—C35—F36	106.1 (2)
C23—C18—C19	122.49 (16)	F38—C35—F36	107.6 (3)
C23—C18—O16	118.58 (15)	F37—C35—S31	112.9 (2)
C19—C18—O16	118.86 (16)	F38—C35—S31	111.5 (2)
C18—C19—C20	118.19 (17)	F36—C35—S31	110.4 (2)

C11—C1—C2—C3	0.4 (3)	C13—C9—C15—O17	97.2 (2)
C1—C2—C3—C4	−0.7 (4)	C11—C9—C15—O16	97.79 (19)
C2—C3—C4—C12	0.3 (3)	C13—C9—C15—O16	−83.2 (2)
C14—C5—C6—C7	−0.1 (3)	O17—C15—O16—C18	3.8 (3)
C5—C6—C7—C8	1.4 (3)	C9—C15—O16—C18	−175.79 (14)
C6—C7—C8—C13	−0.6 (3)	C15—O16—C18—C23	84.4 (2)
C13—C9—C11—C1	−177.44 (17)	C15—O16—C18—C19	−98.6 (2)
C15—C9—C11—C1	1.6 (3)	C23—C18—C19—C20	−1.1 (3)
C13—C9—C11—C12	2.3 (3)	O16—C18—C19—C20	−178.00 (16)
C15—C9—C11—C12	−178.69 (16)	C18—C19—C20—C21	−0.2 (3)
C2—C1—C11—C9	−179.9 (2)	C19—C20—C21—C22	1.0 (3)
C2—C1—C11—C12	0.4 (3)	C19—C20—C21—C24	−178.56 (17)
C14—N10—C12—C4	179.19 (17)	C20—C21—C22—C23	−0.4 (3)
C30—N10—C12—C4	0.0 (2)	C24—C21—C22—C23	179.15 (18)
C14—N10—C12—C11	−1.1 (2)	C19—C18—C23—C22	1.7 (3)
C30—N10—C12—C11	179.76 (16)	O16—C18—C23—C22	178.58 (17)
C3—C4—C12—N10	−179.76 (19)	C21—C22—C23—C18	−0.9 (3)
C3—C4—C12—C11	0.5 (3)	C22—C21—C24—C25	137.96 (19)
C9—C11—C12—N10	−0.3 (2)	C20—C21—C24—C25	−42.5 (3)
C1—C11—C12—N10	179.44 (16)	C22—C21—C24—C29	−42.4 (3)
C9—C11—C12—C4	179.45 (17)	C20—C21—C24—C29	137.10 (19)
C1—C11—C12—C4	−0.8 (3)	C29—C24—C25—C26	−0.8 (3)
C11—C9—C13—C8	176.29 (17)	C21—C24—C25—C26	178.82 (17)
C15—C9—C13—C8	−2.7 (3)	C24—C25—C26—C27	−0.7 (3)
C11—C9—C13—C14	−2.9 (2)	C25—C26—C27—C28	1.4 (3)
C15—C9—C13—C14	178.10 (15)	C26—C27—C28—C29	−0.4 (3)
C7—C8—C13—C9	179.55 (18)	C27—C28—C29—C24	−1.2 (3)
C7—C8—C13—C14	−1.3 (3)	C25—C24—C29—C28	1.8 (3)
C12—N10—C14—C5	−179.76 (16)	C21—C24—C29—C28	−177.87 (17)
C30—N10—C14—C5	−0.6 (3)	O33—S31—C35—F37	61.9 (2)
C12—N10—C14—C13	0.5 (2)	O34—S31—C35—F37	−178.0 (2)
C30—N10—C14—C13	179.62 (16)	O32—S31—C35—F37	−57.4 (2)
C6—C5—C14—N10	178.39 (19)	O33—S31—C35—F38	−60.0 (2)
C6—C5—C14—C13	−1.8 (3)	O34—S31—C35—F38	60.1 (2)
C9—C13—C14—N10	1.5 (2)	O32—S31—C35—F38	−179.3 (2)
C8—C13—C14—N10	−177.72 (16)	O33—S31—C35—F36	−179.51 (19)
C9—C13—C14—C5	−178.30 (16)	O34—S31—C35—F36	−59.5 (2)
C8—C13—C14—C5	2.5 (2)	O32—S31—C35—F36	61.1 (2)
C11—C9—C15—O17	−81.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O33ⁱ	0.93	2.58	3.228 (3)	127
C7—H7···O34	0.93	2.59	3.431 (3)	151
C8—H8···O32	0.93	2.52	3.335 (2)	147
C22—H22···O33ⁱⁱ	0.93	2.51	3.271 (3)	140
C28—H28···O34ⁱⁱⁱ	0.93	2.52	3.429 (3)	166
C30—H30A···O17ⁱ	0.96	2.55	3.125 (2)	118
C29—H29···Cg2^iv	0.93	2.81	3.417 (2)	123
C30—H30A···Cg4ⁱ	0.96	2.83	3.683 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₀NO₂⁺·CF₃SO₃⁻
M_r	539.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.4619 (2), 12.4558 (5), 20.7903 (7)
β (°)	94.559 (3)
V (Å³)	2442.50 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.6 × 0.12 × 0.1

Data collection
Diffractometer	Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.887, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	42490, 4408, 3454
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.05
No. of reflections	4408
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.39

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O33ⁱ	0.93	2.58	3.228 (3)	127
C7—H7···O34	0.93	2.59	3.431 (3)	151
C8—H8···O32	0.93	2.52	3.335 (2)	147
C22—H22···O33ⁱⁱ	0.93	2.51	3.271 (3)	140
C28—H28···O34ⁱⁱⁱ	0.93	2.52	3.429 (3)	166
C30—H30A···O17ⁱ	0.96	2.55	3.125 (2)	118
C29—H29···Cg2^iv	0.93	2.81	3.417 (2)	123
C30—H30A···Cg4ⁱ	0.96	2.83	3.683 (2)	148

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

π–π Interactions (Å,°) top

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgJ_Perp	CgI_Offset	CgJ_Offset
1	1^v	3.993 (2)	0	3.609 (2)	3.609 (2)	1.709 (2)	1.709 (2)
1	3^v	3.668 (2)	2.0	3.583 (2)	3.578 (2)	0.785 (2)	0.807 (2)
2	3^v	3.944 (2)	2.4	3.507 (2)	3.577 (2)	1.804 (2)	1.661 (2)

Symmetry codes: (v) -x, -y+2, -z+1.

Notes: Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 rings, respectively. CgI···CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp and CgJ_Perp are the perpendicular distances of CgI from ring J and of CgJ from ring I, respectively. CgI_Offset and CgJ_Offset are the distances between CgI and the perpendicular projection of CgJ on ring I, and between CgJ and the perpendicular projection of CgI on ring J, respectively.

Acknowledgements

The financing of this work by State Funds for Scientific Research (grant No. N204 123 32/3143, contract No. 3143/H03/2007/32 of the Polish Ministry of Research and Higher Education) for the period 2007–2010 is acknowledged.

References

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

9-(Bi­phenyl-4-yl­oxycarbon­yl)-10-methyl­acridinium tri­fluoro­methane­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(Biphenyl-4-yloxycarbonyl)-10-methylacridinium trifluoromethanesulfonate