9-(2,5-Dimethyl-phen-oxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

In the title compound, C(23)H(20)NO(2) (+)·CF(3)SO(3) (-), 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 inter-actions 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 = 491.48

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.185

S = 1.01

4000 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.23 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045090/xu5358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045090/xu5358Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045090/xu5358Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H20NO2+·CF3SO3−	F(000) = 2032
Mr = 491.48	Dx = 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

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	Rint = 0.106
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.5°
ω scans	h = −14→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −20→20
Tmin = 0.960, Tmax = 0.985	l = −23→25
32535 measured 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0901P)2 + 0.2728P] where P = (Fo2 + 2Fc2)/3
4000 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.23 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	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .