9-(4-Chloro-phen-oxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

In the crystal of the title compound, C(21)H(15)ClNO(2) (+)·CF(3)SO(3) (-), adjacent cations are linked through C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.987 (2) Å], and neighboring cations and anions via C-H⋯O and C-F⋯π inter-actions. The acridine ring system and benzene ring are oriented at a dihedral angle of 1.0 (1)° while the carboxyl group is twisted at an angle of 85.0 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are either parallel or inclined at an angle of 78.2 (1)° in the crystal structure.

Related literature

For background to the chemiluminogenic properties of 9-phen­oxy­carbonyl-10-methyl­acridinium trifluoro­methane­sulfonates, see: Brown et al. (2009 ▶); King et al. (2007 ▶); Rak et al. (1999 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2005 ▶); Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C21H15ClNO2 +·CF3SO3 −

M = 497.87

Monoclinic,

a = 13.3025 (11) Å

b = 8.6750 (9) Å

c = 19.6191 (18) Å

β = 106.577 (10)°

V = 2169.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 295 K

0.35 × 0.28 × 0.06 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

11162 measured reflections

3777 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.112

S = 1.08

3777 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 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 datablocks global, I. DOI: 10.1107/S1600536810039541/xu5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039541/xu5039Isup2.hkl

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

C21H15ClNO2+·CF3SO3−	F(000) = 1016
Mr = 497.87	Dx = 1.524 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1665 reflections
a = 13.3025 (11) Å	θ = 3.0–29.1°
b = 8.6750 (9) Å	µ = 0.33 mm−1
c = 19.6191 (18) Å	T = 295 K
β = 106.577 (10)°	Plate, yellow
V = 2169.9 (4) Å3	0.35 × 0.28 × 0.06 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2679 reflections with I > 2σ(I)
Radiation source: Enhanced (Mo) X-ray Source	Rint = 0.031
graphite	θmax = 25.1°, θmin = 3.2°
Detector resolution: 10.4002 pixels mm-1	h = −15→15
ω scans	k = −10→8
11162 measured reflections	l = −23→23
3777 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0386P)2 + 1.4339P] where P = (Fo2 + 2Fc2)/3
3777 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 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	0.6412 (3)	0.7757 (4)	0.51159 (16)	0.0551 (8)
H1	0.5968	0.8280	0.5327	0.066*
C2	0.7459 (3)	0.7893 (4)	0.53941 (18)	0.0655 (9)
H2	0.7736	0.8503	0.5794	0.079*
C3	0.8127 (3)	0.7105 (4)	0.50748 (19)	0.0642 (9)
H3	0.8848	0.7193	0.5274	0.077*
C4	0.7761 (2)	0.6220 (4)	0.44874 (17)	0.0545 (8)
H4	0.8226	0.5731	0.4284	0.065*
C5	0.4792 (3)	0.3888 (4)	0.27537 (17)	0.0610 (9)
H5	0.5241	0.3355	0.2551	0.073*
C6	0.3742 (3)	0.3699 (5)	0.2497 (2)	0.0827 (12)
H6	0.3480	0.3034	0.2116	0.099*
C7	0.3035 (3)	0.4472 (5)	0.2787 (2)	0.0811 (12)
H7	0.2316	0.4327	0.2597	0.097*
C8	0.3403 (2)	0.5423 (4)	0.33414 (19)	0.0610 (9)
H8	0.2933	0.5927	0.3536	0.073*
C9	0.4901 (2)	0.6658 (3)	0.42070 (14)	0.0407 (7)
N10	0.62580 (17)	0.5155 (3)	0.35967 (12)	0.0408 (5)
C11	0.5976 (2)	0.6831 (3)	0.45086 (14)	0.0408 (7)
C12	0.6666 (2)	0.6045 (3)	0.41855 (15)	0.0416 (7)
C13	0.4494 (2)	0.5676 (3)	0.36378 (15)	0.0426 (7)
C14	0.5202 (2)	0.4893 (3)	0.33286 (14)	0.0421 (7)
C15	0.4160 (2)	0.7658 (3)	0.44662 (15)	0.0451 (7)
O16	0.39162 (15)	0.7040 (2)	0.50208 (10)	0.0497 (5)
O17	0.3831 (2)	0.8846 (3)	0.41934 (13)	0.0785 (8)
C18	0.3180 (2)	0.7867 (3)	0.52827 (14)	0.0410 (7)
C19	0.2135 (2)	0.7596 (4)	0.49788 (15)	0.0503 (8)
H19	0.1910	0.6928	0.4594	0.060*
C20	0.1421 (2)	0.8339 (4)	0.52579 (16)	0.0566 (8)
H20	0.0706	0.8176	0.5063	0.068*
C21	0.1776 (3)	0.9314 (4)	0.58220 (15)	0.0535 (8)
C22	0.2823 (3)	0.9565 (4)	0.61275 (15)	0.0558 (8)
H22	0.3049	1.0220	0.6516	0.067*
C23	0.3544 (2)	0.8829 (3)	0.58496 (15)	0.0484 (7)
H23	0.4259	0.8987	0.6045	0.058*
Cl24	0.08737 (9)	1.02661 (14)	0.61618 (5)	0.0951 (4)
C25	0.6984 (2)	0.4487 (4)	0.32249 (17)	0.0568 (8)
H25A	0.6590	0.4126	0.2763	0.085*
H25B	0.7360	0.3641	0.3497	0.085*
H25C	0.7473	0.5262	0.3173	0.085*
S26	0.99146 (6)	0.51449 (9)	0.33370 (4)	0.0456 (2)
O27	0.91136 (17)	0.6102 (2)	0.28913 (11)	0.0578 (6)
O28	0.96649 (17)	0.4501 (3)	0.39381 (11)	0.0709 (7)
O29	1.09667 (17)	0.5708 (3)	0.34719 (12)	0.0704 (7)
C30	0.9908 (3)	0.3493 (4)	0.27794 (18)	0.0641 (9)
F31	0.89748 (18)	0.2801 (2)	0.25860 (13)	0.0971 (7)
F32	1.01300 (19)	0.3885 (3)	0.21805 (11)	0.0974 (8)
F33	1.06074 (19)	0.2433 (3)	0.30961 (12)	0.0989 (8)

	U11	U22	U33	U12	U13	U23
C1	0.056 (2)	0.0547 (19)	0.0543 (19)	0.0055 (16)	0.0160 (16)	0.0022 (16)
C2	0.064 (2)	0.065 (2)	0.059 (2)	−0.0006 (19)	0.0042 (18)	−0.0015 (17)
C3	0.0434 (19)	0.072 (2)	0.071 (2)	0.0002 (18)	0.0048 (17)	0.0125 (19)
C4	0.0419 (19)	0.0549 (19)	0.069 (2)	0.0081 (15)	0.0189 (16)	0.0107 (17)
C5	0.057 (2)	0.058 (2)	0.076 (2)	−0.0016 (17)	0.0320 (18)	−0.0180 (18)
C6	0.063 (3)	0.088 (3)	0.098 (3)	−0.015 (2)	0.024 (2)	−0.044 (2)
C7	0.043 (2)	0.094 (3)	0.108 (3)	−0.013 (2)	0.024 (2)	−0.034 (2)
C8	0.0386 (18)	0.065 (2)	0.086 (2)	0.0017 (16)	0.0285 (17)	−0.0115 (19)
C9	0.0458 (18)	0.0348 (15)	0.0479 (16)	0.0071 (13)	0.0235 (14)	0.0073 (13)
N10	0.0377 (13)	0.0403 (13)	0.0514 (13)	0.0090 (11)	0.0240 (11)	0.0084 (11)
C11	0.0454 (18)	0.0338 (15)	0.0455 (16)	0.0060 (13)	0.0167 (14)	0.0081 (12)
C12	0.0377 (17)	0.0388 (16)	0.0512 (17)	0.0065 (13)	0.0172 (13)	0.0121 (14)
C13	0.0396 (17)	0.0387 (15)	0.0554 (17)	0.0060 (13)	0.0227 (14)	0.0039 (13)
C14	0.0396 (17)	0.0370 (15)	0.0560 (17)	0.0045 (13)	0.0237 (14)	0.0027 (13)
C15	0.0490 (18)	0.0407 (17)	0.0517 (17)	0.0095 (14)	0.0239 (15)	0.0049 (14)
O16	0.0550 (13)	0.0479 (12)	0.0560 (12)	0.0168 (10)	0.0316 (10)	0.0107 (9)
O17	0.110 (2)	0.0622 (15)	0.0876 (17)	0.0457 (15)	0.0674 (15)	0.0311 (13)
C18	0.0443 (18)	0.0428 (16)	0.0401 (15)	0.0089 (13)	0.0188 (14)	0.0044 (13)
C19	0.053 (2)	0.0585 (19)	0.0414 (16)	−0.0012 (15)	0.0157 (15)	−0.0035 (14)
C20	0.0387 (18)	0.081 (2)	0.0514 (18)	0.0058 (16)	0.0144 (15)	0.0060 (17)
C21	0.057 (2)	0.068 (2)	0.0418 (16)	0.0242 (17)	0.0241 (15)	0.0113 (15)
C22	0.068 (2)	0.057 (2)	0.0411 (16)	0.0115 (17)	0.0140 (16)	−0.0056 (14)
C23	0.0401 (17)	0.0562 (19)	0.0464 (16)	0.0050 (15)	0.0081 (14)	0.0026 (15)
Cl24	0.0976 (8)	0.1281 (9)	0.0771 (6)	0.0595 (7)	0.0531 (6)	0.0170 (6)
C25	0.0459 (19)	0.069 (2)	0.066 (2)	0.0127 (16)	0.0333 (16)	0.0015 (16)
S26	0.0369 (4)	0.0554 (5)	0.0466 (4)	−0.0024 (4)	0.0151 (3)	−0.0039 (4)
O27	0.0521 (13)	0.0545 (13)	0.0673 (14)	0.0069 (11)	0.0176 (11)	0.0104 (11)
O28	0.0590 (15)	0.1053 (19)	0.0566 (13)	0.0177 (13)	0.0296 (11)	0.0210 (13)
O29	0.0442 (13)	0.0904 (17)	0.0758 (15)	−0.0218 (12)	0.0157 (11)	−0.0182 (13)
C30	0.053 (2)	0.069 (2)	0.063 (2)	0.0070 (19)	0.0048 (17)	−0.0033 (18)
F31	0.0796 (16)	0.0704 (14)	0.1195 (18)	−0.0186 (12)	−0.0069 (14)	−0.0203 (13)
F32	0.1092 (19)	0.130 (2)	0.0568 (12)	0.0208 (15)	0.0297 (12)	−0.0186 (13)
F33	0.0931 (17)	0.0805 (15)	0.1065 (17)	0.0384 (13)	0.0016 (14)	−0.0116 (13)

C1—C2	1.349 (4)	C13—C14	1.428 (4)
C1—C11	1.417 (4)	C15—O17	1.186 (3)
C1—H1	0.9300	C15—O16	1.334 (3)
C2—C3	1.402 (5)	O16—C18	1.423 (3)
C2—H2	0.9300	C18—C23	1.364 (4)
C3—C4	1.354 (5)	C18—C19	1.367 (4)
C3—H3	0.9300	C19—C20	1.384 (4)
C4—C12	1.415 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.366 (4)
C5—C6	1.353 (5)	C20—H20	0.9300
C5—C14	1.407 (4)	C21—C22	1.368 (4)
C5—H5	0.9300	C21—Cl24	1.739 (3)
C6—C7	1.401 (5)	C22—C23	1.386 (4)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.341 (5)	C23—H23	0.9300
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.418 (4)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C13	1.386 (4)	S26—O28	1.427 (2)
C9—C11	1.391 (4)	S26—O29	1.434 (2)
C9—C15	1.506 (4)	S26—O27	1.434 (2)
N10—C12	1.367 (4)	S26—C30	1.801 (4)
N10—C14	1.372 (3)	C30—F33	1.330 (4)
N10—C25	1.485 (3)	C30—F31	1.333 (4)
C11—C12	1.429 (4)	C30—F32	1.335 (4)
C2—C1—C11	121.2 (3)	C5—C14—C13	118.9 (3)
C2—C1—H1	119.4	O17—C15—O16	125.0 (3)
C11—C1—H1	119.4	O17—C15—C9	122.7 (3)
C1—C2—C3	119.3 (3)	O16—C15—C9	112.2 (2)
C1—C2—H2	120.4	C15—O16—C18	116.4 (2)
C3—C2—H2	120.4	C23—C18—C19	122.7 (3)
C4—C3—C2	122.5 (3)	C23—C18—O16	118.8 (3)
C4—C3—H3	118.8	C19—C18—O16	118.3 (2)
C2—C3—H3	118.8	C18—C19—C20	118.3 (3)
C3—C4—C12	119.6 (3)	C18—C19—H19	120.8
C3—C4—H4	120.2	C20—C19—H19	120.8
C12—C4—H4	120.2	C21—C20—C19	119.5 (3)
C6—C5—C14	119.7 (3)	C21—C20—H20	120.3
C6—C5—H5	120.1	C19—C20—H20	120.3
C14—C5—H5	120.1	C20—C21—C22	121.8 (3)
C5—C6—C7	122.2 (3)	C20—C21—Cl24	119.2 (3)
C5—C6—H6	118.9	C22—C21—Cl24	119.0 (2)
C7—C6—H6	118.9	C21—C22—C23	119.1 (3)
C8—C7—C6	119.4 (3)	C21—C22—H22	120.4
C8—C7—H7	120.3	C23—C22—H22	120.4
C6—C7—H7	120.3	C18—C23—C22	118.6 (3)
C7—C8—C13	121.5 (3)	C18—C23—H23	120.7
C7—C8—H8	119.3	C22—C23—H23	120.7
C13—C8—H8	119.3	N10—C25—H25A	109.5
C13—C9—C11	121.7 (2)	N10—C25—H25B	109.5
C13—C9—C15	118.9 (3)	H25A—C25—H25B	109.5
C11—C9—C15	119.1 (3)	N10—C25—H25C	109.5
C12—N10—C14	122.3 (2)	H25A—C25—H25C	109.5
C12—N10—C25	118.6 (2)	H25B—C25—H25C	109.5
C14—N10—C25	119.1 (2)	O28—S26—O29	115.20 (14)
C9—C11—C1	122.9 (3)	O28—S26—O27	115.00 (13)
C9—C11—C12	118.2 (3)	O29—S26—O27	115.57 (14)
C1—C11—C12	118.9 (3)	O28—S26—C30	103.23 (17)
N10—C12—C4	121.8 (3)	O29—S26—C30	102.62 (16)
N10—C12—C11	119.6 (3)	O27—S26—C30	102.48 (14)
C4—C12—C11	118.6 (3)	F33—C30—F31	107.0 (3)
C9—C13—C8	122.9 (3)	F33—C30—F32	106.6 (3)
C9—C13—C14	118.8 (3)	F31—C30—F32	106.6 (3)
C8—C13—C14	118.3 (3)	F33—C30—S26	112.6 (2)
N10—C14—C5	122.0 (2)	F31—C30—S26	112.0 (2)
N10—C14—C13	119.1 (2)	F32—C30—S26	111.6 (3)
C11—C1—C2—C3	0.1 (5)	C6—C5—C14—C13	1.1 (5)
C1—C2—C3—C4	0.9 (5)	C9—C13—C14—N10	−1.0 (4)
C2—C3—C4—C12	−1.3 (5)	C8—C13—C14—N10	178.3 (3)
C14—C5—C6—C7	−0.3 (6)	C9—C13—C14—C5	179.6 (3)
C5—C6—C7—C8	−0.6 (7)	C8—C13—C14—C5	−1.1 (4)
C6—C7—C8—C13	0.6 (6)	C13—C9—C15—O17	−82.2 (4)
C13—C9—C11—C1	−176.2 (3)	C11—C9—C15—O17	92.9 (4)
C15—C9—C11—C1	8.8 (4)	C13—C9—C15—O16	96.9 (3)
C13—C9—C11—C12	4.3 (4)	C11—C9—C15—O16	−88.0 (3)
C15—C9—C11—C12	−170.7 (2)	O17—C15—O16—C18	1.9 (4)
C2—C1—C11—C9	179.9 (3)	C9—C15—O16—C18	−177.1 (2)
C2—C1—C11—C12	−0.6 (4)	C15—O16—C18—C23	−96.8 (3)
C14—N10—C12—C4	175.5 (2)	C15—O16—C18—C19	86.8 (3)
C25—N10—C12—C4	−6.3 (4)	C23—C18—C19—C20	0.4 (4)
C14—N10—C12—C11	−4.7 (4)	O16—C18—C19—C20	176.7 (3)
C25—N10—C12—C11	173.5 (2)	C18—C19—C20—C21	0.1 (5)
C3—C4—C12—N10	−179.4 (3)	C19—C20—C21—C22	−0.9 (5)
C3—C4—C12—C11	0.8 (4)	C19—C20—C21—Cl24	179.1 (2)
C9—C11—C12—N10	−0.1 (4)	C20—C21—C22—C23	1.1 (5)
C1—C11—C12—N10	−179.6 (2)	Cl24—C21—C22—C23	−178.9 (2)
C9—C11—C12—C4	179.7 (2)	C19—C18—C23—C22	−0.2 (4)
C1—C11—C12—C4	0.2 (4)	O16—C18—C23—C22	−176.4 (2)
C11—C9—C13—C8	177.0 (3)	C21—C22—C23—C18	−0.6 (4)
C15—C9—C13—C8	−8.0 (4)	O28—S26—C30—F33	−60.1 (3)
C11—C9—C13—C14	−3.8 (4)	O29—S26—C30—F33	60.0 (3)
C15—C9—C13—C14	171.2 (2)	O27—S26—C30—F33	−179.9 (3)
C7—C8—C13—C9	179.5 (3)	O28—S26—C30—F31	60.5 (3)
C7—C8—C13—C14	0.3 (5)	O29—S26—C30—F31	−179.4 (2)
C12—N10—C14—C5	−175.4 (3)	O27—S26—C30—F31	−59.2 (3)
C25—N10—C14—C5	6.4 (4)	O28—S26—C30—F32	180.0 (2)
C12—N10—C14—C13	5.2 (4)	O29—S26—C30—F32	−60.0 (3)
C25—N10—C14—C13	−173.0 (2)	O27—S26—C30—F32	60.2 (3)
C6—C5—C14—N10	−178.3 (3)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O28i	0.93	2.59	3.328 (5)	136
C4—H4···O28	0.93	2.45	3.370 (4)	171
C5—H5···O27ii	0.93	2.39	3.258 (4)	154
C6—H6···O29ii	0.93	2.54	3.304 (5)	140
C8—H8···O29iii	0.93	2.59	3.332 (4)	137
C19—H19···O29iii	0.93	2.44	3.349 (4)	165
C25—H25C···O27	0.96	2.51	3.387 (4)	152
C25—H25B···Cg4iv	0.96	2.65	3.519 (4)	151

X	I	J	I···J	X···J	X–I···J
C30	F31	Cg1ii	3.570 (3)	3.916 (4)	94.4 (2)
C30	F32	Cg1ii	3.337 (3)	3.916 (4)	105.8 (2)
C30	F33	Cg3ii	3.387 (3)	4.073 (4)	111.9 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
2	4v	3.987 (2)	2.96 (15)	3.477 (2)	1.951 (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
C3—H3⋯O28i	0.93	2.59	3.328 (5)	136
C4—H4⋯O28	0.93	2.45	3.370 (4)	171
C5—H5⋯O27ii	0.93	2.39	3.258 (4)	154
C6—H6⋯O29ii	0.93	2.54	3.304 (5)	140
C8—H8⋯O29iii	0.93	2.59	3.332 (4)	137
C19—H19⋯O29iii	0.93	2.44	3.349 (4)	165
C25—H25C⋯O27	0.96	2.51	3.387 (4)	152
C25—H25B⋯Cg4iv	0.96	2.65	3.519 (4)	151

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

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
C30	F31	Cg1ii	3.570 (3)	3.916 (4)	94.4 (2)
C30	F32	Cg1ii	3.337 (3)	3.916 (4)	105.8 (2)
C30	F33	Cg3ii	3.387 (3)	4.073 (4)	111.9 (2)

Symmetry code: (ii) .