Literature DB >> 21580656

9-(2-Ethyl-phenoxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

Damian Trzybiński¹, Karol Krzymiński, Artur Sikorski, Piotr Malecha, Jerzy Błażejowski.

Abstract

In the crystal structure of the title compound, C(23)H(20)NO(2) (+)·CF(3)SO(3) (-), the cations form inversion dimers through π-π inter-actions between the acridine ring systems. These dimers are further linked by C-H⋯π inter-actions. The cations and anions are connected by C-H⋯O and C-F⋯π inter-actions. The acridine and benzene ring systems are oriented at a dihedral angle of 20.8 (1)°. The carboxyl group is twisted at an angle of 66.2 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel in the lattice.

Entities: CellLine Chemical Disease Species

Year: 2010 PMID： 21580656 PMCID： PMC2984008 DOI： 10.1107/S1600536810008950

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to 9-(phenoxycarbonyl)-10-alkylacridinium salts, see: Brown et al. (2009 ▶); Rak et al. (1999 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2005a ▶,b ▶). For intermolecular interactions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Steiner (1999 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Niziołek et al. (2008 ▶); Sato (1996 ▶).

Experimental

Crystal data

C23H20NO2 +·CF3O3S− M = 491.47 Triclinic, a = 9.8519 (4) Å b = 10.9533 (4) Å c = 11.7805 (4) Å α = 104.379 (3)° β = 101.475 (3)° γ = 109.983 (3)° V = 1099.61 (7) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 295 K 0.40 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer 21109 measured reflections 3914 independent reflections 2956 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.116 S = 1.10 3914 reflections 309 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.30 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008950/ng2739sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008950/ng2739Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₃H₂₀NO₂⁺·CF₃O₃S⁻	Z = 2
M_r = 491.47	F(000) = 508
Triclinic, P1	D_x = 1.484 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8519 (4) Å	Cell parameters from 10425 reflections
b = 10.9533 (4) Å	θ = 3.1–29.2°
c = 11.7805 (4) Å	µ = 0.21 mm⁻¹
α = 104.379 (3)°	T = 295 K
β = 101.475 (3)°	Block, yellow
γ = 109.983 (3)°	0.40 × 0.35 × 0.20 mm
V = 1099.61 (7) Å³

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2956 reflections with I > 2σ(I)
Radiation source: Enhanced (Mo) X-ray Source	R_int = 0.039
graphite	θ_max = 25.1°, θ_min = 3.1°
Detector resolution: 10.4002 pixels mm^-1	h = −11→11
ω scans	k = −13→13
21109 measured reflections	l = −14→14
3914 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0737P)²] where P = (F_o² + 2F_c²)/3
3914 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
C8	0.4629 (2)	0.70220 (17)	0.44477 (16)	0.0468 (4)
H8	0.3781	0.7136	0.4600	0.056*
C7	0.4857 (2)	0.69994 (19)	0.33477 (18)	0.0561 (5)
H7	0.4164	0.7087	0.2745	0.067*
C6	0.6146 (3)	0.68432 (19)	0.31214 (18)	0.0573 (5)
H6	0.6298	0.6842	0.2367	0.069*
C5	0.7175 (2)	0.66940 (17)	0.39617 (17)	0.0508 (5)
H5	0.8014	0.6591	0.3780	0.061*
C4	0.8753 (2)	0.62222 (19)	0.79550 (18)	0.0535 (5)
H4	0.9549	0.6038	0.7759	0.064*
C3	0.8550 (2)	0.6234 (2)	0.90569 (19)	0.0583 (5)
H3	0.9214	0.6064	0.9612	0.070*
C2	0.7358 (2)	0.64984 (19)	0.93822 (18)	0.0559 (5)
H2	0.7247	0.6518	1.0151	0.067*
C1	0.6372 (2)	0.67241 (18)	0.85755 (16)	0.0499 (5)
H1	0.5573	0.6881	0.8792	0.060*
C9	0.55076 (18)	0.69321 (15)	0.65368 (15)	0.0374 (4)
N10	0.79811 (15)	0.65304 (13)	0.59893 (13)	0.0419 (3)
C13	0.56732 (19)	0.68738 (15)	0.53759 (15)	0.0381 (4)
C14	0.69716 (19)	0.66950 (15)	0.51165 (15)	0.0403 (4)
C11	0.65277 (19)	0.67276 (16)	0.74035 (15)	0.0394 (4)
C12	0.77656 (19)	0.64875 (15)	0.70957 (15)	0.0404 (4)
C15	0.4184 (2)	0.71774 (16)	0.68401 (15)	0.0389 (4)
O16	0.46656 (13)	0.83893 (11)	0.77566 (10)	0.0435 (3)
O17	0.28868 (14)	0.63985 (12)	0.63199 (12)	0.0554 (4)
C18	0.3528 (2)	0.88341 (16)	0.80457 (16)	0.0439 (4)
C19	0.3118 (2)	0.86926 (16)	0.90748 (17)	0.0478 (4)
C20	0.2093 (2)	0.92574 (19)	0.9350 (2)	0.0615 (6)
H20	0.1775	0.9189	1.0032	0.074*
C21	0.1550 (3)	0.9905 (2)	0.8641 (2)	0.0690 (6)
H21	0.0875	1.0273	0.8851	0.083*
C22	0.1986 (3)	1.0024 (2)	0.7621 (2)	0.0671 (6)
H22	0.1602	1.0460	0.7140	0.080*
C23	0.3001 (2)	0.94881 (18)	0.73174 (19)	0.0552 (5)
H23	0.3321	0.9567	0.6637	0.066*
C24	0.3714 (2)	0.79938 (18)	0.98693 (17)	0.0554 (5)
H24A	0.3664	0.8357	1.0692	0.067*
H24B	0.4774	0.8221	0.9933	0.067*
C25	0.2850 (3)	0.6427 (2)	0.9388 (2)	0.0644 (5)
H25A	0.3346	0.6040	0.9891	0.097*
H25B	0.2832	0.6063	0.8552	0.097*
H25C	0.1828	0.6189	0.9416	0.097*
C26	0.9362 (2)	0.6389 (2)	0.5764 (2)	0.0623 (5)
H26A	0.9481	0.6594	0.5034	0.093*
H26B	0.9257	0.5459	0.5655	0.093*
H26C	1.0239	0.7022	0.6456	0.093*
S27	0.07676 (5)	0.73990 (4)	0.26699 (4)	0.04742 (17)
O28	−0.07260 (15)	0.73377 (15)	0.22221 (13)	0.0649 (4)
O29	0.09669 (19)	0.68219 (15)	0.36225 (14)	0.0740 (4)
O30	0.14440 (18)	0.70502 (16)	0.17469 (13)	0.0743 (4)
C31	0.1906 (3)	0.9229 (2)	0.3455 (2)	0.0740 (6)
F32	0.1421 (2)	0.97409 (17)	0.43606 (15)	0.1282 (7)
F33	0.1861 (2)	0.99425 (14)	0.27126 (17)	0.1192 (6)
F34	0.33510 (19)	0.95023 (16)	0.39672 (18)	0.1263 (7)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0487 (11)	0.0493 (10)	0.0471 (10)	0.0242 (9)	0.0164 (9)	0.0174 (8)
C7	0.0650 (14)	0.0608 (11)	0.0476 (11)	0.0298 (10)	0.0164 (10)	0.0226 (9)
C6	0.0724 (14)	0.0590 (11)	0.0465 (11)	0.0259 (10)	0.0281 (10)	0.0219 (9)
C5	0.0521 (12)	0.0501 (10)	0.0548 (11)	0.0202 (9)	0.0292 (10)	0.0168 (8)
C4	0.0414 (11)	0.0578 (11)	0.0627 (12)	0.0277 (9)	0.0110 (9)	0.0169 (9)
C3	0.0565 (13)	0.0641 (12)	0.0565 (12)	0.0317 (10)	0.0074 (10)	0.0226 (9)
C2	0.0645 (13)	0.0650 (12)	0.0485 (11)	0.0358 (11)	0.0167 (10)	0.0240 (9)
C1	0.0541 (12)	0.0592 (11)	0.0501 (10)	0.0328 (9)	0.0219 (9)	0.0233 (9)
C9	0.0346 (9)	0.0342 (8)	0.0447 (9)	0.0151 (7)	0.0147 (7)	0.0123 (7)
N10	0.0325 (8)	0.0425 (7)	0.0491 (8)	0.0162 (6)	0.0158 (7)	0.0096 (6)
C13	0.0388 (9)	0.0344 (8)	0.0409 (9)	0.0157 (7)	0.0134 (7)	0.0109 (7)
C14	0.0402 (10)	0.0351 (8)	0.0429 (9)	0.0134 (7)	0.0168 (8)	0.0090 (7)
C11	0.0379 (10)	0.0372 (8)	0.0438 (9)	0.0171 (7)	0.0133 (8)	0.0125 (7)
C12	0.0354 (9)	0.0366 (8)	0.0447 (10)	0.0145 (7)	0.0107 (8)	0.0086 (7)
C15	0.0401 (11)	0.0419 (9)	0.0410 (9)	0.0212 (8)	0.0151 (8)	0.0166 (7)
O16	0.0375 (7)	0.0442 (6)	0.0504 (7)	0.0205 (5)	0.0174 (6)	0.0106 (5)
O17	0.0375 (8)	0.0531 (7)	0.0640 (8)	0.0168 (6)	0.0143 (6)	0.0053 (6)
C18	0.0367 (10)	0.0373 (8)	0.0559 (11)	0.0181 (7)	0.0156 (8)	0.0079 (8)
C19	0.0435 (10)	0.0404 (9)	0.0545 (11)	0.0151 (8)	0.0194 (9)	0.0082 (8)
C20	0.0549 (13)	0.0570 (11)	0.0730 (13)	0.0250 (10)	0.0312 (11)	0.0116 (10)
C21	0.0579 (14)	0.0588 (12)	0.0956 (17)	0.0356 (11)	0.0316 (13)	0.0131 (12)
C22	0.0613 (14)	0.0552 (11)	0.0932 (16)	0.0354 (11)	0.0211 (12)	0.0257 (11)
C23	0.0530 (12)	0.0502 (10)	0.0668 (12)	0.0251 (9)	0.0205 (10)	0.0203 (9)
C24	0.0553 (12)	0.0599 (11)	0.0536 (11)	0.0243 (10)	0.0252 (10)	0.0163 (9)
C25	0.0621 (14)	0.0642 (12)	0.0767 (14)	0.0260 (10)	0.0307 (11)	0.0335 (11)
C26	0.0382 (11)	0.0780 (13)	0.0666 (13)	0.0265 (10)	0.0203 (10)	0.0117 (11)
S27	0.0507 (3)	0.0533 (3)	0.0460 (3)	0.0255 (2)	0.0210 (2)	0.0191 (2)
O28	0.0476 (9)	0.0797 (9)	0.0687 (9)	0.0282 (7)	0.0186 (7)	0.0245 (7)
O29	0.0943 (12)	0.0861 (10)	0.0733 (10)	0.0504 (9)	0.0386 (9)	0.0506 (8)
O30	0.0806 (11)	0.1006 (11)	0.0617 (9)	0.0510 (9)	0.0407 (8)	0.0266 (8)
C31	0.0712 (17)	0.0610 (13)	0.0783 (15)	0.0277 (12)	0.0042 (13)	0.0196 (12)
F32	0.1628 (18)	0.1019 (12)	0.0962 (11)	0.0735 (12)	0.0201 (12)	−0.0158 (9)
F33	0.1130 (13)	0.0720 (9)	0.1535 (15)	0.0184 (9)	0.0082 (11)	0.0619 (10)
F34	0.0701 (11)	0.0882 (10)	0.1607 (16)	0.0141 (9)	−0.0251 (11)	0.0193 (10)

C8—C7	1.354 (3)	O16—C18	1.432 (2)
C8—C13	1.427 (2)	C18—C23	1.379 (2)
C8—H8	0.9300	C18—C19	1.380 (3)
C7—C6	1.405 (3)	C19—C20	1.401 (3)
C7—H7	0.9300	C19—C24	1.500 (3)
C6—C5	1.352 (3)	C20—C21	1.365 (3)
C6—H6	0.9300	C20—H20	0.9300
C5—C14	1.414 (2)	C21—C22	1.375 (3)
C5—H5	0.9300	C21—H21	0.9300
C4—C3	1.350 (3)	C22—C23	1.382 (3)
C4—C12	1.416 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C3—C2	1.402 (3)	C24—C25	1.523 (3)
C3—H3	0.9300	C24—H24A	0.9700
C2—C1	1.349 (3)	C24—H24B	0.9700
C2—H2	0.9300	C25—H25A	0.9600
C1—C11	1.420 (2)	C25—H25B	0.9600
C1—H1	0.9300	C25—H25C	0.9600
C9—C13	1.398 (2)	C26—H26A	0.9600
C9—C11	1.401 (2)	C26—H26B	0.9600
C9—C15	1.509 (2)	C26—H26C	0.9600
N10—C12	1.371 (2)	S27—O30	1.4242 (14)
N10—C14	1.374 (2)	S27—O29	1.4307 (14)
N10—C26	1.488 (2)	S27—O28	1.4331 (15)
C13—C14	1.437 (2)	S27—C31	1.806 (2)
C11—C12	1.427 (2)	C31—F33	1.314 (3)
C15—O17	1.192 (2)	C31—F34	1.326 (3)
C15—O16	1.3442 (19)	C31—F32	1.330 (3)

C7—C8—C13	120.82 (17)	C23—C18—O16	116.69 (16)
C7—C8—H8	119.6	C19—C18—O16	119.15 (16)
C13—C8—H8	119.6	C18—C19—C20	115.51 (18)
C8—C7—C6	119.67 (19)	C18—C19—C24	123.48 (16)
C8—C7—H7	120.2	C20—C19—C24	121.01 (18)
C6—C7—H7	120.2	C21—C20—C19	121.7 (2)
C5—C6—C7	122.33 (18)	C21—C20—H20	119.1
C5—C6—H6	118.8	C19—C20—H20	119.1
C7—C6—H6	118.8	C20—C21—C22	120.97 (19)
C6—C5—C14	119.89 (18)	C20—C21—H21	119.5
C6—C5—H5	120.1	C22—C21—H21	119.5
C14—C5—H5	120.1	C21—C22—C23	119.4 (2)
C3—C4—C12	120.51 (18)	C21—C22—H22	120.3
C3—C4—H4	119.7	C23—C22—H22	120.3
C12—C4—H4	119.7	C18—C23—C22	118.5 (2)
C4—C3—C2	121.39 (18)	C18—C23—H23	120.8
C4—C3—H3	119.3	C22—C23—H23	120.8
C2—C3—H3	119.3	C19—C24—C25	113.77 (17)
C1—C2—C3	119.77 (19)	C19—C24—H24A	108.8
C1—C2—H2	120.1	C25—C24—H24A	108.8
C3—C2—H2	120.1	C19—C24—H24B	108.8
C2—C1—C11	121.50 (18)	C25—C24—H24B	108.8
C2—C1—H1	119.2	H24A—C24—H24B	107.7
C11—C1—H1	119.2	C24—C25—H25A	109.5
C13—C9—C11	120.83 (15)	C24—C25—H25B	109.5
C13—C9—C15	119.28 (15)	H25A—C25—H25B	109.5
C11—C9—C15	119.87 (15)	C24—C25—H25C	109.5
C12—N10—C14	121.94 (14)	H25A—C25—H25C	109.5
C12—N10—C26	117.26 (16)	H25B—C25—H25C	109.5
C14—N10—C26	120.80 (15)	N10—C26—H26A	109.5
C9—C13—C8	122.77 (15)	N10—C26—H26B	109.5
C9—C13—C14	118.70 (16)	H26A—C26—H26B	109.5
C8—C13—C14	118.51 (15)	N10—C26—H26C	109.5
N10—C14—C5	121.66 (16)	H26A—C26—H26C	109.5
N10—C14—C13	119.56 (15)	H26B—C26—H26C	109.5
C5—C14—C13	118.77 (17)	O30—S27—O29	114.62 (9)
C9—C11—C1	122.87 (16)	O30—S27—O28	115.38 (9)
C9—C11—C12	119.01 (15)	O29—S27—O28	115.01 (9)
C1—C11—C12	118.12 (16)	O30—S27—C31	103.15 (11)
N10—C12—C4	121.62 (16)	O29—S27—C31	103.45 (10)
N10—C12—C11	119.71 (15)	O28—S27—C31	102.78 (10)
C4—C12—C11	118.67 (16)	F33—C31—F34	107.8 (2)
O17—C15—O16	125.00 (15)	F33—C31—F32	106.5 (2)
O17—C15—C9	123.94 (15)	F34—C31—F32	106.5 (2)
O16—C15—C9	111.05 (14)	F33—C31—S27	112.23 (16)
C15—O16—C18	117.14 (13)	F34—C31—S27	112.05 (16)
C23—C18—C19	123.94 (16)	F32—C31—S27	111.42 (18)

C13—C8—C7—C6	−0.7 (3)	C9—C11—C12—N10	3.3 (2)
C8—C7—C6—C5	0.9 (3)	C1—C11—C12—N10	−177.78 (14)
C7—C6—C5—C14	−0.1 (3)	C9—C11—C12—C4	−177.29 (15)
C12—C4—C3—C2	0.4 (3)	C1—C11—C12—C4	1.6 (2)
C4—C3—C2—C1	1.1 (3)	C13—C9—C15—O17	63.9 (2)
C3—C2—C1—C11	−1.2 (3)	C11—C9—C15—O17	−114.36 (19)
C11—C9—C13—C8	177.50 (15)	C13—C9—C15—O16	−115.39 (16)
C15—C9—C13—C8	−0.7 (2)	C11—C9—C15—O16	66.40 (18)
C11—C9—C13—C14	−4.3 (2)	O17—C15—O16—C18	−6.3 (2)
C15—C9—C13—C14	177.54 (13)	C9—C15—O16—C18	172.96 (13)
C7—C8—C13—C9	178.04 (16)	C15—O16—C18—C23	−82.25 (18)
C7—C8—C13—C14	−0.2 (2)	C15—O16—C18—C19	102.93 (18)
C12—N10—C14—C5	−177.94 (14)	C23—C18—C19—C20	0.5 (3)
C26—N10—C14—C5	2.0 (2)	O16—C18—C19—C20	174.87 (14)
C12—N10—C14—C13	2.1 (2)	C23—C18—C19—C24	−179.24 (17)
C26—N10—C14—C13	−178.01 (14)	O16—C18—C19—C24	−4.8 (2)
C6—C5—C14—N10	179.25 (16)	C18—C19—C20—C21	−0.2 (3)
C6—C5—C14—C13	−0.8 (2)	C24—C19—C20—C21	179.50 (18)
C9—C13—C14—N10	2.6 (2)	C19—C20—C21—C22	0.3 (3)
C8—C13—C14—N10	−179.08 (14)	C20—C21—C22—C23	−0.6 (3)
C9—C13—C14—C5	−177.38 (14)	C19—C18—C23—C22	−0.8 (3)
C8—C13—C14—C5	0.9 (2)	O16—C18—C23—C22	−175.31 (16)
C13—C9—C11—C1	−177.50 (15)	C21—C22—C23—C18	0.8 (3)
C15—C9—C11—C1	0.7 (2)	C18—C19—C24—C25	−83.8 (2)
C13—C9—C11—C12	1.4 (2)	C20—C19—C24—C25	96.5 (2)
C15—C9—C11—C12	179.56 (13)	O30—S27—C31—F33	60.3 (2)
C2—C1—C11—C9	178.74 (17)	O29—S27—C31—F33	−179.97 (18)
C2—C1—C11—C12	−0.1 (3)	O28—S27—C31—F33	−60.0 (2)
C14—N10—C12—C4	175.56 (15)	O30—S27—C31—F34	−61.1 (2)
C26—N10—C12—C4	−4.4 (2)	O29—S27—C31—F34	58.6 (2)
C14—N10—C12—C11	−5.0 (2)	O28—S27—C31—F34	178.62 (18)
C26—N10—C12—C11	175.04 (14)	O30—S27—C31—F32	179.70 (16)
C3—C4—C12—N10	177.62 (16)	O29—S27—C31—F32	−60.58 (18)
C3—C4—C12—C11	−1.8 (3)	O28—S27—C31—F32	59.41 (18)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O28ⁱ	0.93	2.55	3.221 (2)	130
C5—H5···O28ⁱⁱ	0.93	2.56	3.222 (3)	129
C24—H24B···Cg4ⁱⁱⁱ	0.96	2.92	3.603 (2)	129
C26—H26A···O29ⁱⁱ	0.96	2.43	3.280 (3)	148
C26—H26C···Cg4ⁱⁱ	0.96	2.80	3.741 (2)	165

X—I···J	I···J	X···J	X—I···J
C31—F32···Cg3^iv	3.474 (2)	4.003 (2)	103.67 (14)
C31—F33···Cg1^iv	3.241 (2)	4.087 (2)	121.73 (14)
C31—F34···Cg3^iv	3.762 (2)	4.003 (2)	90.62 (13)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	1^v	4.022 (2)	0.00	3.571 (2)	1.850 (2)
1	3^v	3.702 (2)	1.80	3.532 (2)	1.109 (2)
2	3^v	3.965 (2)	4.29	3.451 (2)	1.960 (2)
3	1^v	3.702 (2)	1.80	3.544 (2)	1.070 (2)
3	2^v	3.965 (2)	4.29	3.566 (2)	1.733 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O28ⁱ	0.93	2.55	3.221 (2)	130
C5—H5⋯O28ⁱⁱ	0.93	2.56	3.222 (3)	129
C24—H24B⋯Cg4ⁱⁱⁱ	0.96	2.92	3.603 (2)	129
C26—H26A⋯O29ⁱⁱ	0.96	2.43	3.280 (3)	148
C26—H26C⋯Cg4ⁱⁱ	0.96	2.80	3.741 (2)	165

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

C—F⋯π 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
C31—F32⋯Cg3^iv	3.474 (2)	4.003 (2)	103.67 (14)
C31—F33⋯Cg1^iv	3.241 (2)	4.087 (2)	121.73 (14)
C31—F34⋯Cg3^iv	3.762 (2)	4.003 (2)	90.62 (13)

Symmetry code: (iv) −x + 1, −y + 2, −z + 1.

Table 3

π–π interactions (Å,°)

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 is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	1^v	4.022 (2)	0.00	3.571 (2)	1.850 (2)
1	3^v	3.702 (2)	1.80	3.532 (2)	1.109 (2)
2	3^v	3.965 (2)	4.29	3.451 (2)	1.960 (2)
3	1^v	3.702 (2)	1.80	3.544 (2)	1.070 (2)
3	2^v	3.965 (2)	4.29	3.566 (2)	1.733 (2)

Symmetry code: (v) −x + 1, −y + 1, −z + 1.

7 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 9-(2,6-Difluorophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate and its precursor 2,6-difluorophenyl acridine-9-carboxylate: C-H...O, C-F...pi, S-O...pi and pi-pi stacking interactions.

Authors: Artur Sikorski; Karol Krzymiński; Agnieszka Niziołek; Jerzy Błazejowski
Journal: Acta Crystallogr C Date: 2005-11-11 Impact factor: 1.172

3. Toward an Understanding of the Chemiluminescence Accompanying the Reaction of 9-Carboxy-10-methylacridinium Phenyl Ester with Hydrogen Peroxide.

Authors: Janusz Rak; Piotr Skurski; Jerzy Blazejowski
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

4. 2-Ethylphenyl acridine-9-carboxylate and 2,5-dimethylphenyl acridine-9-carboxylate.

Authors: Artur Sikorski; Karol Krzymiński; Antoni Konitz; Jerzy Błazejowski
Journal: Acta Crystallogr C Date: 2004-12-18 Impact factor: 1.172

5. Development and application of a novel acridinium ester for use as a chemiluminescent emitter in nucleic acid hybridisation assays using chemiluminescence quenching.

Authors: Richard C Brown; Zhaoqiang Li; Andrew J Rutter; Xiaojing Mu; Owen H Weeks; Keith Smith; Ian Weeks
Journal: Org Biomol Chem Date: 2008-11-24 Impact factor: 3.876

6. Experimental electron density study of the supramolecular aggregation between 4,4'-dipyridyl-N,N'-dioxide and 1,4-diiodotetrafluorobenzene at 90 K.

Authors: Riccardo Bianchi; Alessandra Forni; Tullio Pilati
Journal: Acta Crystallogr B Date: 2004-09-15

7. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20