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

In the crystal structure of the title compound, C(21)H(15)BrNO(2) (+)·CF(3)SO(3) (-), adjacent cations are linked through C-Br⋯π and π-π contacts [centroid-centroid distance = 3.744 (2) Å], and neighbouring cations and anions via C-H⋯O, C-F⋯π and S-O⋯π inter-actions. The acridine and benzene ring systems are oriented at a dihedral angle of 18.7 (1)°. The carb-oxy group is twisted at an angle of 69.3 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine moieties are either parallel or inclined at an angle of 27.8 (1)° in the lattice.

Related literature

For general background to the chemiluminescent properties of 9-phen­oxy­carbonyl-10-methyl­acridinium trifluoro­methane­sulfonates, see: King et al. (2007 ▶); Krzymiński et al. (2011 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Seo et al. (2009 ▶); Sikorski et al. (2005 ▶); Trzybiński et al. (2010 ▶). For similar C–Br⋯π, π–π, C–H⋯O, C–F⋯π and S–O⋯π inter­actions in related compounds, see: Sikorski et al. (2005 ▶); Trzybiński et al. (2010 ▶). For the synthesis, see: Sato (1996 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C21H15BrNO2 +·CF3O3S−

M = 542.32

Monoclinic,

a = 12.5718 (8) Å

b = 20.3617 (16) Å

c = 8.5162 (6) Å

β = 104.498 (7)°

V = 2110.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.11 mm−1

T = 295 K

0.46 × 0.25 × 0.02 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.668, T max = 1.000

16372 measured reflections

3735 independent reflections

2348 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 0.92

3735 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.40 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/S1600536812020892/fj2548sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020892/fj2548Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020892/fj2548Isup3.cml

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

C21H15BrNO2+·CF3O3S−	F(000) = 1088
Mr = 542.32	Dx = 1.707 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1539 reflections
a = 12.5718 (8) Å	θ = 3.0–29.2°
b = 20.3617 (16) Å	µ = 2.11 mm−1
c = 8.5162 (6) Å	T = 295 K
β = 104.498 (7)°	Plate, light-orange
V = 2110.6 (3) Å3	0.46 × 0.25 × 0.02 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3735 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	2348 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.2°
ω scans	h = −14→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −24→23
Tmin = 0.668, Tmax = 1.000	l = −10→10
16372 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0518P)2] where P = (Fo2 + 2Fc2)/3
3735 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.40 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	0.5650 (3)	0.70124 (15)	0.5969 (4)	0.0507 (8)
H1	0.5048	0.7209	0.6227	0.061*
C2	0.6310 (3)	0.73723 (16)	0.5286 (4)	0.0575 (9)
H2	0.6170	0.7818	0.5098	0.069*
C3	0.7204 (3)	0.70832 (18)	0.4856 (4)	0.0581 (9)
H3	0.7639	0.7337	0.4355	0.070*
C4	0.7451 (3)	0.64367 (16)	0.5157 (3)	0.0517 (8)
H4	0.8048	0.6252	0.4860	0.062*
C5	0.6664 (3)	0.43392 (15)	0.7299 (4)	0.0532 (8)
H5	0.7314	0.4166	0.7140	0.064*
C6	0.5970 (3)	0.39546 (15)	0.7872 (4)	0.0586 (9)
H6	0.6154	0.3516	0.8099	0.070*
C7	0.4988 (3)	0.41906 (15)	0.8135 (4)	0.0525 (8)
H7	0.4519	0.3910	0.8503	0.063*
C8	0.4724 (2)	0.48279 (14)	0.7851 (3)	0.0457 (7)
H8	0.4078	0.4988	0.8052	0.055*
C9	0.5181 (2)	0.59299 (13)	0.6949 (3)	0.0355 (7)
N10	0.70556 (19)	0.54005 (11)	0.6297 (2)	0.0397 (6)
C11	0.5865 (2)	0.63282 (13)	0.6305 (3)	0.0379 (7)
C12	0.6800 (2)	0.60492 (14)	0.5919 (3)	0.0405 (7)
C13	0.5419 (2)	0.52598 (13)	0.7246 (3)	0.0366 (7)
C14	0.6396 (2)	0.50086 (13)	0.6942 (3)	0.0380 (7)
C15	0.4213 (2)	0.62290 (13)	0.7426 (3)	0.0388 (7)
O16	0.32648 (15)	0.60104 (8)	0.6463 (2)	0.0410 (5)
O17	0.42777 (16)	0.66151 (10)	0.8497 (2)	0.0541 (6)
C18	0.2280 (2)	0.62507 (14)	0.6773 (3)	0.0417 (7)
C19	0.1815 (2)	0.68158 (14)	0.6025 (3)	0.0457 (8)
C20	0.0812 (3)	0.70147 (17)	0.6251 (4)	0.0596 (9)
H20	0.0476	0.7392	0.5743	0.072*
C21	0.0311 (3)	0.6654 (2)	0.7228 (4)	0.0664 (10)
H21	−0.0362	0.6791	0.7382	0.080*
C22	0.0792 (3)	0.60940 (19)	0.7976 (4)	0.0637 (10)
H22	0.0449	0.5855	0.8639	0.076*
C23	0.1787 (3)	0.58855 (15)	0.7748 (4)	0.0509 (8)
H23	0.2117	0.5505	0.8245	0.061*
Br24	0.25462 (3)	0.731793 (18)	0.47628 (4)	0.06770 (16)
C25	0.8105 (3)	0.51466 (16)	0.6062 (4)	0.0605 (9)
H25A	0.8261	0.4728	0.6587	0.091*
H25B	0.8685	0.5449	0.6522	0.091*
H25C	0.8050	0.5098	0.4923	0.091*
S26	0.17372 (8)	0.40673 (5)	0.95720 (10)	0.0608 (3)
O27	0.2606 (2)	0.41546 (17)	0.8843 (4)	0.1142 (11)
O28	0.1816 (3)	0.35388 (13)	1.0698 (3)	0.0968 (9)
O29	0.1332 (2)	0.46570 (12)	1.0126 (3)	0.0852 (8)
C30	0.0621 (3)	0.38096 (18)	0.7915 (4)	0.0625 (9)
F31	0.0855 (2)	0.32387 (11)	0.7309 (3)	0.0976 (7)
F32	0.0450 (2)	0.42450 (12)	0.6698 (2)	0.0985 (7)
F33	−0.03080 (19)	0.37394 (13)	0.8308 (3)	0.1006 (8)

	U11	U22	U33	U12	U13	U23
C1	0.044 (2)	0.0501 (19)	0.0606 (18)	0.0065 (16)	0.0176 (16)	0.0073 (15)
C2	0.056 (2)	0.0465 (18)	0.072 (2)	−0.0008 (17)	0.0180 (19)	0.0134 (16)
C3	0.053 (2)	0.063 (2)	0.061 (2)	−0.0112 (18)	0.0200 (17)	0.0060 (16)
C4	0.045 (2)	0.060 (2)	0.0563 (18)	−0.0036 (17)	0.0233 (16)	−0.0003 (15)
C5	0.053 (2)	0.0488 (19)	0.0603 (19)	0.0127 (17)	0.0193 (16)	−0.0009 (15)
C6	0.068 (3)	0.0403 (18)	0.068 (2)	0.0100 (18)	0.0181 (19)	0.0076 (15)
C7	0.051 (2)	0.050 (2)	0.0576 (19)	−0.0015 (17)	0.0163 (16)	0.0083 (15)
C8	0.0402 (19)	0.0512 (19)	0.0463 (16)	0.0000 (15)	0.0122 (14)	0.0017 (14)
C9	0.0288 (16)	0.0437 (17)	0.0319 (13)	0.0022 (13)	0.0035 (12)	−0.0038 (12)
N10	0.0327 (14)	0.0451 (14)	0.0426 (13)	0.0004 (12)	0.0120 (11)	−0.0088 (11)
C11	0.0318 (17)	0.0444 (17)	0.0365 (14)	−0.0006 (14)	0.0065 (13)	0.0004 (12)
C12	0.0351 (18)	0.0513 (19)	0.0350 (14)	−0.0040 (15)	0.0086 (13)	−0.0073 (13)
C13	0.0297 (17)	0.0463 (18)	0.0328 (14)	0.0000 (13)	0.0058 (12)	−0.0044 (12)
C14	0.0345 (18)	0.0438 (18)	0.0342 (14)	0.0004 (14)	0.0056 (13)	−0.0061 (12)
C15	0.0392 (19)	0.0388 (16)	0.0392 (16)	0.0002 (14)	0.0112 (14)	0.0036 (13)
O16	0.0297 (11)	0.0477 (11)	0.0461 (11)	0.0011 (9)	0.0102 (9)	−0.0073 (9)
O17	0.0409 (13)	0.0674 (14)	0.0534 (12)	−0.0011 (11)	0.0105 (10)	−0.0193 (11)
C18	0.0297 (17)	0.0493 (18)	0.0453 (15)	0.0000 (15)	0.0079 (13)	−0.0118 (14)
C19	0.0331 (19)	0.0549 (19)	0.0455 (16)	0.0011 (15)	0.0031 (14)	−0.0113 (14)
C20	0.045 (2)	0.065 (2)	0.062 (2)	0.0092 (19)	−0.0010 (17)	−0.0164 (18)
C21	0.032 (2)	0.091 (3)	0.076 (2)	−0.001 (2)	0.0114 (19)	−0.033 (2)
C22	0.048 (2)	0.085 (3)	0.062 (2)	−0.016 (2)	0.0208 (18)	−0.0191 (19)
C23	0.042 (2)	0.0555 (19)	0.0585 (19)	−0.0048 (16)	0.0189 (16)	−0.0061 (15)
Br24	0.0705 (3)	0.0676 (3)	0.0633 (2)	0.01066 (19)	0.01349 (18)	0.01921 (17)
C25	0.045 (2)	0.058 (2)	0.086 (2)	0.0032 (17)	0.0298 (18)	−0.0099 (18)
S26	0.0498 (6)	0.0710 (6)	0.0608 (5)	−0.0004 (4)	0.0121 (4)	−0.0092 (4)
O27	0.0577 (19)	0.157 (3)	0.143 (3)	−0.0291 (19)	0.0528 (18)	−0.044 (2)
O28	0.130 (3)	0.0818 (18)	0.0673 (15)	0.0238 (17)	0.0033 (16)	0.0126 (14)
O29	0.108 (2)	0.0632 (16)	0.0888 (17)	0.0013 (15)	0.0326 (16)	−0.0232 (13)
C30	0.060 (3)	0.074 (3)	0.061 (2)	−0.008 (2)	0.0304 (19)	−0.0021 (19)
F31	0.123 (2)	0.0832 (16)	0.0873 (14)	−0.0155 (14)	0.0280 (14)	−0.0331 (12)
F32	0.1056 (19)	0.1177 (19)	0.0672 (13)	0.0148 (15)	0.0119 (13)	0.0236 (13)
F33	0.0587 (15)	0.140 (2)	0.1082 (17)	−0.0275 (14)	0.0301 (13)	−0.0134 (15)

C1—C2	1.343 (4)	C13—C14	1.412 (4)
C1—C11	1.434 (4)	C15—O17	1.192 (3)
C1—H1	0.9300	C15—O16	1.342 (3)
C2—C3	1.397 (5)	O16—C18	1.417 (3)
C2—H2	0.9300	C18—C23	1.372 (4)
C3—C4	1.362 (5)	C18—C19	1.373 (4)
C3—H3	0.9300	C19—C20	1.383 (4)
C4—C12	1.407 (4)	C19—Br24	1.882 (3)
C4—H4	0.9300	C20—C21	1.375 (5)
C5—C6	1.351 (4)	C20—H20	0.9300
C5—C14	1.419 (4)	C21—C22	1.371 (5)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.394 (4)	C22—C23	1.380 (5)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.346 (4)	C23—H23	0.9300
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.424 (4)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C11	1.391 (4)	S26—O27	1.397 (3)
C9—C13	1.406 (4)	S26—O28	1.428 (3)
C9—C15	1.505 (4)	S26—O29	1.430 (2)
N10—C14	1.362 (3)	S26—C30	1.801 (4)
N10—C12	1.378 (3)	C30—F33	1.301 (4)
N10—C25	1.476 (4)	C30—F31	1.334 (4)
C11—C12	1.416 (4)	C30—F32	1.340 (4)
C2—C1—C11	120.7 (3)	C13—C14—C5	118.7 (3)
C2—C1—H1	119.7	O17—C15—O16	124.5 (3)
C11—C1—H1	119.7	O17—C15—C9	124.6 (3)
C1—C2—C3	120.5 (3)	O16—C15—C9	110.8 (2)
C1—C2—H2	119.7	C15—O16—C18	117.1 (2)
C3—C2—H2	119.7	C23—C18—C19	122.0 (3)
C4—C3—C2	121.2 (3)	C23—C18—O16	118.3 (3)
C4—C3—H3	119.4	C19—C18—O16	119.6 (3)
C2—C3—H3	119.4	C18—C19—C20	118.6 (3)
C3—C4—C12	119.8 (3)	C18—C19—Br24	120.5 (2)
C3—C4—H4	120.1	C20—C19—Br24	120.9 (3)
C12—C4—H4	120.1	C21—C20—C19	120.0 (3)
C6—C5—C14	119.6 (3)	C21—C20—H20	120.0
C6—C5—H5	120.2	C19—C20—H20	120.0
C14—C5—H5	120.2	C22—C21—C20	120.7 (3)
C5—C6—C7	122.4 (3)	C22—C21—H21	119.7
C5—C6—H6	118.8	C20—C21—H21	119.7
C7—C6—H6	118.8	C21—C22—C23	120.0 (3)
C8—C7—C6	119.5 (3)	C21—C22—H22	120.0
C8—C7—H7	120.3	C23—C22—H22	120.0
C6—C7—H7	120.3	C18—C23—C22	118.8 (3)
C7—C8—C13	120.9 (3)	C18—C23—H23	120.6
C7—C8—H8	119.5	C22—C23—H23	120.6
C13—C8—H8	119.5	N10—C25—H25A	109.5
C11—C9—C13	120.8 (3)	N10—C25—H25B	109.5
C11—C9—C15	119.5 (2)	H25A—C25—H25B	109.5
C13—C9—C15	119.6 (3)	N10—C25—H25C	109.5
C14—N10—C12	121.7 (2)	H25A—C25—H25C	109.5
C14—N10—C25	120.3 (2)	H25B—C25—H25C	109.5
C12—N10—C25	117.9 (2)	O27—S26—O28	117.6 (2)
C9—C11—C12	119.2 (3)	O27—S26—O29	115.00 (18)
C9—C11—C1	122.7 (3)	O28—S26—O29	112.46 (17)
C12—C11—C1	118.0 (3)	O27—S26—C30	103.37 (18)
N10—C12—C4	121.1 (3)	O28—S26—C30	102.49 (17)
N10—C12—C11	119.3 (3)	O29—S26—C30	103.38 (17)
C4—C12—C11	119.6 (3)	F33—C30—F31	107.6 (3)
C9—C13—C14	118.3 (3)	F33—C30—F32	106.9 (3)
C9—C13—C8	122.8 (3)	F31—C30—F32	106.6 (3)
C14—C13—C8	118.9 (3)	F33—C30—S26	113.8 (2)
N10—C14—C13	120.5 (2)	F31—C30—S26	110.6 (3)
N10—C14—C5	120.9 (3)	F32—C30—S26	110.8 (2)
C11—C1—C2—C3	1.5 (5)	C8—C13—C14—N10	177.1 (2)
C1—C2—C3—C4	−1.9 (5)	C9—C13—C14—C5	177.5 (2)
C2—C3—C4—C12	−0.2 (4)	C8—C13—C14—C5	−2.0 (4)
C14—C5—C6—C7	−0.1 (5)	C6—C5—C14—N10	−177.1 (3)
C5—C6—C7—C8	−1.7 (5)	C6—C5—C14—C13	2.0 (4)
C6—C7—C8—C13	1.6 (4)	C11—C9—C15—O17	−65.8 (3)
C13—C9—C11—C12	1.2 (4)	C13—C9—C15—O17	110.5 (3)
C15—C9—C11—C12	177.5 (2)	C11—C9—C15—O16	113.1 (3)
C13—C9—C11—C1	179.5 (2)	C13—C9—C15—O16	−70.5 (3)
C15—C9—C11—C1	−4.3 (4)	O17—C15—O16—C18	−1.1 (4)
C2—C1—C11—C9	−177.3 (3)	C9—C15—O16—C18	179.9 (2)
C2—C1—C11—C12	1.0 (4)	C15—O16—C18—C23	−94.4 (3)
C14—N10—C12—C4	−175.8 (2)	C15—O16—C18—C19	89.3 (3)
C25—N10—C12—C4	7.3 (4)	C23—C18—C19—C20	−0.9 (4)
C14—N10—C12—C11	4.1 (3)	O16—C18—C19—C20	175.3 (2)
C25—N10—C12—C11	−172.7 (2)	C23—C18—C19—Br24	177.7 (2)
C3—C4—C12—N10	−177.4 (3)	O16—C18—C19—Br24	−6.2 (3)
C3—C4—C12—C11	2.7 (4)	C18—C19—C20—C21	1.0 (4)
C9—C11—C12—N10	−4.6 (3)	Br24—C19—C20—C21	−177.5 (2)
C1—C11—C12—N10	177.0 (2)	C19—C20—C21—C22	−0.4 (5)
C9—C11—C12—C4	175.3 (2)	C20—C21—C22—C23	−0.3 (5)
C1—C11—C12—C4	−3.0 (4)	C19—C18—C23—C22	0.2 (4)
C11—C9—C13—C14	2.7 (3)	O16—C18—C23—C22	−176.0 (2)
C15—C9—C13—C14	−173.5 (2)	C21—C22—C23—C18	0.4 (4)
C11—C9—C13—C8	−177.8 (2)	O27—S26—C30—F33	−175.8 (3)
C15—C9—C13—C8	6.0 (4)	O28—S26—C30—F33	61.5 (3)
C7—C8—C13—C9	−179.3 (2)	O29—S26—C30—F33	−55.6 (3)
C7—C8—C13—C14	0.2 (4)	O27—S26—C30—F31	62.8 (3)
C12—N10—C14—C13	0.0 (3)	O28—S26—C30—F31	−59.9 (3)
C25—N10—C14—C13	176.7 (2)	O29—S26—C30—F31	−177.0 (2)
C12—N10—C14—C5	179.0 (2)	O27—S26—C30—F32	−55.2 (3)
C25—N10—C14—C5	−4.2 (4)	O28—S26—C30—F32	−177.9 (3)
C9—C13—C14—N10	−3.4 (3)	O29—S26—C30—F32	65.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O28i	0.93	2.54	3.289 (5)	137
C7—H7···O27	0.93	2.54	3.200 (5)	128

X—I···J	I···J	X···J	X—I···J
C19—Br24···Cg4ii	3.523 (2)	4.847 (3)	124.6 (1)
C30—F32···Cg4iii	3.648 (2)	4.310 (4)	110.8 (2)
S26—O27···Cg1iv	3.821 (3)	3.708 (2)	74.8 (2)
S26—O28···Cg1iv	3.414 (3)	3.708 (2)	90.3 (2)
S26—O28···Cg2iv	3.358 (3)	4.445 (2)	132.2 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	3v	3.744 (2)	2.74 (13)	3.703 (2)	0.553 (2)
3	1v	3.744 (2)	2.74 (13)	3.717 (2)	0.549 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O28i	0.93	2.54	3.289 (5)	137
C7—H7⋯O27	0.93	2.54	3.200 (5)	128

Symmetry code: (i) .

Table 2

C—F⋯π, C—Br⋯π and S—O⋯π inter­actions (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C18–C23 rings, respectively.

X—I⋯J	I⋯J	X⋯J	X—I⋯J
C19—Br24⋯Cg4ii	3.523 (2)	4.847 (3)	124.6 (1)
C30—F32⋯Cg4iii	3.648 (2)	4.310 (4)	110.8 (2)
S26—O27⋯Cg1iv	3.821 (3)	3.708 (2)	74.8 (2)
S26—O28⋯Cg1iv	3.414 (3)	3.708 (2)	90.3 (2)
S26—O28⋯Cg2iv	3.358 (3)	4.445 (2)	132.2 (2)

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