9-Ethyl-10-methyl-acridinium trifluoro-methane-sulfonate.

In the mol-ecule of the title compound, C(16)H(16)N(+)·CF(3)SO(3) (-), the central ring adopts a flattened-boat conformation, and the two aromatic rings are oriented at a dihedral angle of 3.94 (2)°. In the crystal structure, weak inter-molecular hydrogen bonds link the mol-ecules. There are π-π contacts between the aromatic rings and the central ring and one of the aromatic rings [centroid-centroid distances = 3.874 (2), 3.945 (2) and 3.814 (2) Å]. There is also an S-O⋯π contact between the central ring and one of the O atoms of the anion.

Related literature

For general background, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter & Sanders (1990 ▶); Steiner (1991 ▶); Suzuki & Tanaka (2001 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Huta et al. (2002 ▶); Krzymiński et al. (2007 ▶); Meszko et al. (2002 ▶); Sikorski et al. (2005a ▶,b ▶,c ▶, 2006 ▶, 2008 ▶); Storoniak et al. (2000 ▶); Tsuge et al. (1965 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H16N+·CF3SO3 −

M = 371.37

Triclinic,

a = 7.771 (2) Å

b = 9.440 (2) Å

c = 11.898 (2) Å

α = 76.76 (3)°

β = 74.04 (3)°

γ = 82.14 (3)°

V = 814.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 295 (2) K

0.5 × 0.5 × 0.05 mm

Data collection

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.870, T max = 0.988

7781 measured reflections

2857 independent reflections

2078 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.102

S = 1.08

2857 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 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: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039676/hk2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039676/hk2577Isup2.hkl

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

C16H16N+·CF3SO3−	Z = 2
Mr = 371.37	F(000) = 384
Triclinic, P1	Dx = 1.515 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.771 (2) Å	Cell parameters from 2857 reflections
b = 9.440 (2) Å	θ = 3.1–25.0°
c = 11.898 (2) Å	µ = 0.25 mm−1
α = 76.76 (3)°	T = 295 K
β = 74.04 (3)°	Plate, pale-yellow
γ = 82.14 (3)°	0.5 × 0.5 × 0.05 mm
V = 814.3 (3) Å3

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer	2857 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2078 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.4002 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→11
Tmin = 0.870, Tmax = 0.988	l = −13→14
7781 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2857 reflections	Δρmax = 0.22 e Å−3
229 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.3057 (2)	0.6242 (2)	0.97192 (18)	0.0479 (5)
H1	0.3455	0.7172	0.9413	0.057*
C2	0.2727 (3)	0.5708 (2)	1.09064 (19)	0.0541 (5)
H2	0.2876	0.6276	1.1411	0.065*
C3	0.2161 (3)	0.4299 (2)	1.13769 (19)	0.0551 (5)
H3	0.1946	0.3940	1.2195	0.066*
C4	0.1918 (3)	0.3445 (2)	1.06641 (18)	0.0490 (5)
H4	0.1571	0.2503	1.0993	0.059*
C5	0.1504 (3)	0.2917 (2)	0.68005 (19)	0.0526 (5)
H5	0.1046	0.2013	0.7141	0.063*
C6	0.1686 (3)	0.3478 (2)	0.5618 (2)	0.0616 (6)
H6	0.1340	0.2947	0.5159	0.074*
C7	0.2377 (3)	0.4825 (2)	0.50750 (19)	0.0594 (6)
H7	0.2505	0.5175	0.4262	0.071*
C8	0.2859 (3)	0.5621 (2)	0.57323 (17)	0.0509 (5)
H8	0.3312	0.6522	0.5364	0.061*
C9	0.3131 (2)	0.59454 (18)	0.76881 (17)	0.0397 (4)
N10	0.18592 (19)	0.31700 (15)	0.86993 (13)	0.0387 (4)
C11	0.2806 (2)	0.54049 (18)	0.89252 (17)	0.0394 (4)
C12	0.2190 (2)	0.39871 (18)	0.94283 (16)	0.0388 (4)
C13	0.2688 (2)	0.51098 (19)	0.69798 (16)	0.0398 (4)
C14	0.2018 (2)	0.37195 (19)	0.75118 (17)	0.0397 (4)
C15	0.1358 (3)	0.1658 (2)	0.92047 (19)	0.0548 (5)
H15A	0.1862	0.1064	0.8619	0.082*
H15B	0.0074	0.1650	0.9426	0.082*
H15C	0.1813	0.1277	0.9897	0.082*
C16	0.3835 (3)	0.7413 (2)	0.71458 (19)	0.0492 (5)
H16A	0.4536	0.7416	0.6333	0.059*
H16B	0.4621	0.7601	0.7594	0.059*
C17	0.2316 (3)	0.8623 (2)	0.7141 (2)	0.0590 (6)
H17A	0.2808	0.9541	0.6753	0.088*
H17B	0.1670	0.8665	0.7948	0.088*
H17C	0.1515	0.8423	0.6720	0.088*
C18	0.2605 (3)	0.9709 (2)	0.36020 (18)	0.0563 (5)
F19	0.12725 (18)	0.89034 (15)	0.42780 (11)	0.0835 (4)
F20	0.19886 (19)	1.11050 (15)	0.35499 (12)	0.0838 (4)
F21	0.3880 (2)	0.94796 (18)	0.41894 (12)	0.0913 (5)
S22	0.34301 (7)	0.92827 (5)	0.21309 (4)	0.0488 (2)
O23	0.4120 (2)	0.77973 (17)	0.23799 (17)	0.0817 (5)
O24	0.18424 (19)	0.95139 (17)	0.17045 (13)	0.0650 (4)
O25	0.47217 (19)	1.03268 (17)	0.15403 (13)	0.0688 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0441 (11)	0.0382 (11)	0.0692 (14)	−0.0014 (8)	−0.0219 (10)	−0.0183 (10)
C2	0.0527 (13)	0.0543 (13)	0.0663 (14)	0.0040 (10)	−0.0248 (11)	−0.0271 (11)
C3	0.0548 (13)	0.0607 (14)	0.0535 (12)	0.0015 (10)	−0.0206 (10)	−0.0138 (10)
C4	0.0473 (12)	0.0422 (11)	0.0587 (13)	−0.0025 (9)	−0.0182 (9)	−0.0072 (9)
C5	0.0559 (13)	0.0417 (12)	0.0660 (14)	−0.0073 (9)	−0.0171 (10)	−0.0182 (10)
C6	0.0667 (15)	0.0633 (15)	0.0669 (15)	−0.0079 (12)	−0.0235 (12)	−0.0275 (12)
C7	0.0609 (14)	0.0682 (15)	0.0523 (12)	−0.0046 (11)	−0.0177 (11)	−0.0147 (11)
C8	0.0478 (12)	0.0491 (12)	0.0555 (13)	−0.0064 (9)	−0.0130 (10)	−0.0083 (10)
C9	0.0296 (10)	0.0320 (10)	0.0584 (12)	−0.0004 (7)	−0.0121 (8)	−0.0107 (8)
N10	0.0355 (8)	0.0285 (8)	0.0541 (10)	−0.0026 (6)	−0.0129 (7)	−0.0103 (7)
C11	0.0288 (9)	0.0336 (10)	0.0600 (12)	0.0019 (7)	−0.0154 (8)	−0.0155 (8)
C12	0.0305 (9)	0.0329 (10)	0.0557 (12)	0.0018 (7)	−0.0145 (8)	−0.0124 (8)
C13	0.0318 (10)	0.0346 (10)	0.0540 (11)	−0.0005 (7)	−0.0108 (8)	−0.0124 (8)
C14	0.0330 (10)	0.0340 (10)	0.0547 (12)	0.0009 (7)	−0.0125 (8)	−0.0146 (8)
C15	0.0676 (14)	0.0329 (11)	0.0676 (13)	−0.0116 (10)	−0.0219 (11)	−0.0070 (9)
C16	0.0468 (12)	0.0394 (11)	0.0621 (12)	−0.0107 (9)	−0.0124 (9)	−0.0093 (9)
C17	0.0638 (14)	0.0367 (12)	0.0740 (14)	−0.0036 (10)	−0.0152 (11)	−0.0091 (10)
C18	0.0564 (13)	0.0557 (14)	0.0565 (13)	−0.0210 (11)	−0.0115 (11)	−0.0041 (10)
F19	0.0803 (10)	0.0913 (11)	0.0695 (9)	−0.0423 (8)	0.0020 (7)	−0.0019 (7)
F20	0.0990 (11)	0.0619 (9)	0.0841 (9)	−0.0101 (8)	0.0033 (8)	−0.0317 (7)
F21	0.0951 (11)	0.1268 (13)	0.0649 (9)	−0.0367 (10)	−0.0363 (8)	−0.0091 (8)
S22	0.0461 (3)	0.0466 (3)	0.0603 (3)	−0.0064 (2)	−0.0172 (2)	−0.0179 (2)
O23	0.0841 (12)	0.0528 (10)	0.1235 (14)	0.0168 (8)	−0.0476 (11)	−0.0355 (9)
O24	0.0598 (9)	0.0738 (10)	0.0708 (9)	−0.0122 (8)	−0.0342 (8)	−0.0078 (8)
O25	0.0612 (10)	0.0840 (11)	0.0630 (9)	−0.0324 (8)	0.0022 (7)	−0.0248 (8)

C1—C2	1.351 (3)	N10—C14	1.366 (2)
C1—C11	1.428 (2)	N10—C12	1.377 (2)
C1—H1	0.9300	N10—C15	1.477 (2)
C2—C3	1.399 (3)	C11—C12	1.424 (2)
C2—H2	0.9300	C13—C14	1.421 (3)
C3—C4	1.359 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C12	1.408 (3)	C15—H15C	0.9600
C4—H4	0.9300	C16—C17	1.526 (3)
C5—C6	1.360 (3)	C16—H16A	0.9700
C5—C14	1.418 (3)	C16—H16B	0.9700
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.394 (3)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.351 (3)	F19—C18	1.332 (2)
C7—H7	0.9300	F20—C18	1.333 (3)
C8—C13	1.426 (3)	F21—C18	1.331 (2)
C8—H8	0.9300	S22—O25	1.4276 (15)
C9—C11	1.406 (3)	S22—O24	1.4308 (14)
C9—C13	1.411 (2)	S22—C18	1.809 (2)
C9—C16	1.496 (3)	O23—S22	1.4257 (16)
C2—C1—C11	121.23 (19)	C9—C13—C14	119.89 (17)
C2—C1—H1	119.4	C9—C13—C8	122.18 (17)
C11—C1—H1	119.4	C14—C13—C8	117.92 (16)
C1—C2—C3	120.02 (18)	N10—C14—C5	120.50 (17)
C1—C2—H2	120.0	N10—C14—C13	120.14 (15)
C3—C2—H2	120.0	C5—C14—C13	119.36 (18)
C4—C3—C2	121.4 (2)	N10—C15—H15A	109.5
C4—C3—H3	119.3	N10—C15—H15B	109.5
C2—C3—H3	119.3	H15A—C15—H15B	109.5
C3—C4—C12	120.01 (19)	N10—C15—H15C	109.5
C3—C4—H4	120.0	H15A—C15—H15C	109.5
C12—C4—H4	120.0	H15B—C15—H15C	109.5
C6—C5—C14	119.59 (19)	C9—C16—C17	111.60 (16)
C6—C5—H5	120.2	C9—C16—H16A	109.3
C14—C5—H5	120.2	C17—C16—H16A	109.3
C5—C6—C7	121.87 (18)	C9—C16—H16B	109.3
C5—C6—H6	119.1	C17—C16—H16B	109.3
C7—C6—H6	119.1	H16A—C16—H16B	108.0
C8—C7—C6	119.9 (2)	C16—C17—H17A	109.5
C8—C7—H7	120.1	C16—C17—H17B	109.5
C6—C7—H7	120.1	H17A—C17—H17B	109.5
C7—C8—C13	121.37 (19)	C16—C17—H17C	109.5
C7—C8—H8	119.3	H17A—C17—H17C	109.5
C13—C8—H8	119.3	H17B—C17—H17C	109.5
C11—C9—C13	118.54 (16)	F21—C18—F19	106.83 (16)
C11—C9—C16	120.65 (16)	F21—C18—F20	106.57 (17)
C13—C9—C16	120.72 (17)	F19—C18—F20	107.29 (19)
C14—N10—C12	121.38 (15)	F21—C18—S22	112.10 (16)
C14—N10—C15	119.21 (14)	F19—C18—S22	112.04 (14)
C12—N10—C15	119.40 (16)	F20—C18—S22	111.67 (14)
C9—C11—C12	120.23 (15)	O23—S22—O25	116.29 (11)
C9—C11—C1	122.06 (17)	O23—S22—O24	115.01 (10)
C12—C11—C1	117.71 (18)	O25—S22—O24	114.73 (10)
N10—C12—C4	120.96 (17)	O23—S22—C18	102.68 (11)
N10—C12—C11	119.48 (17)	O25—S22—C18	102.77 (9)
C4—C12—C11	119.55 (16)	O24—S22—C18	102.49 (10)
C11—C1—C2—C3	1.2 (3)	C16—C9—C13—C8	−0.9 (3)
C1—C2—C3—C4	−0.5 (3)	C7—C8—C13—C9	−177.97 (18)
C2—C3—C4—C12	−1.7 (3)	C7—C8—C13—C14	1.0 (3)
C14—C5—C6—C7	0.3 (3)	C12—N10—C14—C5	−173.83 (16)
C5—C6—C7—C8	−1.1 (3)	C15—N10—C14—C5	7.4 (3)
C6—C7—C8—C13	0.4 (3)	C12—N10—C14—C13	5.7 (2)
C13—C9—C11—C12	5.4 (2)	C15—N10—C14—C13	−173.07 (16)
C16—C9—C11—C12	−178.00 (15)	C6—C5—C14—N10	−179.46 (17)
C13—C9—C11—C1	−174.00 (16)	C6—C5—C14—C13	1.0 (3)
C16—C9—C11—C1	2.6 (3)	C9—C13—C14—N10	−2.2 (3)
C2—C1—C11—C9	179.61 (16)	C8—C13—C14—N10	178.83 (16)
C2—C1—C11—C12	0.2 (3)	C9—C13—C14—C5	177.31 (17)
C14—N10—C12—C4	176.08 (16)	C8—C13—C14—C5	−1.7 (3)
C15—N10—C12—C4	−5.2 (2)	C11—C9—C16—C17	−87.9 (2)
C14—N10—C12—C11	−3.5 (2)	C13—C9—C16—C17	88.5 (2)
C15—N10—C12—C11	175.24 (16)	O23—S22—C18—F21	56.86 (17)
C3—C4—C12—N10	−176.51 (16)	O25—S22—C18—F21	−64.24 (17)
C3—C4—C12—C11	3.1 (3)	O24—S22—C18—F21	176.45 (14)
C9—C11—C12—N10	−2.2 (2)	O23—S22—C18—F19	−63.24 (18)
C1—C11—C12—N10	177.29 (15)	O25—S22—C18—F19	175.66 (15)
C9—C11—C12—C4	178.25 (16)	O24—S22—C18—F19	56.35 (18)
C1—C11—C12—C4	−2.3 (2)	O23—S22—C18—F20	176.37 (14)
C11—C9—C13—C14	−3.3 (3)	O25—S22—C18—F20	55.27 (17)
C16—C9—C13—C14	−179.86 (15)	O24—S22—C18—F20	−64.04 (16)
C11—C9—C13—C8	175.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O23i	0.93	2.47	3.369 (3)	164
C15—H15C···O24ii	0.96	2.40	3.276 (3)	151
C16—H16B···O25iii	0.97	2.58	3.377 (3)	140

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
1	2iv	3.814 (2)	3.88	3.517 (2)	5.188
2	1iv	3.814 (2)	3.88	3.542 (2)	5.205
2	2iv	3.945 (2)	0.02	3.578 (2)	5.326
2	2v	3.874 (2)	0.02	3.440 (2)	5.181

X	I	J	I···J	X···J	X-I···J
S22	O23	1vi	3.255 (2)	3.072 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O23i	0.93	2.47	3.369 (3)	164
C15—H15C⋯O24ii	0.96	2.40	3.276 (3)	151
C16—H16B⋯O25iii	0.97	2.58	3.377 (3)	140

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

Table 2

π–π Interactions (Å, °)

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
1	2iv	3.814 (2)	3.88	3.517 (2)	5.188
2	1iv	3.814 (2)	3.88	3.542 (2)	5.205
2	2iv	3.945 (2)	0.02	3.578 (2)	5.326
2	2v	3.874 (2)	0.02	3.440 (2)	5.181

Symmetry codes: (iv) ; (v) Cg1 and Cg2 are the centroids of the C9/N10/C11–C14 and C1–C4/C11/C12 rings, respectively. Cg⋯Cg is the distance between ring centroids. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.

Table 3

S—O⋯π Interactions (Å, °)

X	I	J	I⋯J	X⋯J	X—I⋯J
S22	O23	Cg1vi	3.255 (2)	3.072 (2)	146

Symmetry codes: (vi) , , . Cg1 is the centroid of the C9/N10/C11–C14 ring.