9-(3-Fluoro-phen-oxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate monohydrate.

In the crystal structure of the title mol-ecular salt, C(21)H(15)FNO(2) (+)·CF(3)SO(3) (-)·H(2)O, the cations form inversion dimers through π-π inter-actions between the acridine ring systems. These dimers are linked via C-H⋯O and C-F⋯π inter-actions to adjacent anions, and by C-H⋯π and C-F⋯π inter-actions to neighbouring cations. The water mol-ecule links two sites of the cation by C-H⋯O inter-actions and two adjacent anions by O-H⋯O hydrogen bonds. The mean planes of the acridine and benzene ring systems are oriented at a dihedral angle of 15.1 (1)°. The carboxyl group is twisted at an angle of 84.5 (1)° relative to the acridine skeleton. The mean planes of the acridine ring systems are parallel in the crystal.

Related literature

For general background to the chemiluminogenic features of 9-phen­oxy­carbonyl-10-methyl­acridinium trifluoro­methane­sulfonates, see: King et al. (2007 ▶); Krzymiński et al. (2011 ▶); Roda et al. (2003 ▶). For related structures, see: Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); 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

C21H15FNO2 +·CF3O3S−·H2O

M = 499.44

Triclinic,

a = 9.5144 (10) Å

b = 11.5654 (11) Å

c = 11.9680 (12) Å

α = 109.975 (9)°

β = 97.838 (8)°

γ = 113.197 (9)°

V = 1080.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.40 × 0.15 × 0.10 mm

Data collection

Oxford Gemini R Ultra Ruby CCD diffractometer

9148 measured reflections

3769 independent reflections

1647 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.129

S = 0.81

3769 reflections

314 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 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/S1600536812003054/xu5452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003054/xu5452Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003054/xu5452Isup3.cml

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

C21H15FNO2+·CF3O3S−·H2O	Z = 2
Mr = 499.44	F(000) = 512
Triclinic, P1	Dx = 1.535 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5144 (10) Å	Cell parameters from 2551 reflections
b = 11.5654 (11) Å	θ = 3.1–29.0°
c = 11.9680 (12) Å	µ = 0.23 mm−1
α = 109.975 (9)°	T = 295 K
β = 97.838 (8)°	Prism, light yellow
γ = 113.197 (9)°	0.40 × 0.15 × 0.10 mm
V = 1080.3 (2) Å3

Oxford Gemini R Ultra Ruby CCD diffractometer	1647 reflections with I > 2σ(I)
Radiation source: Enhanced (Mo) X-ray Source	Rint = 0.050
Graphite monochromator	θmax = 25.1°, θmin = 3.1°
Detector resolution: 10.4002 pixels mm-1	h = −11→11
ω scans	k = −13→13
9148 measured reflections	l = −13→14
3769 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ2(Fo2) + (0.0706P)2] where P = (Fo2 + 2Fc2)/3
3769 reflections	(Δ/σ)max = 0.003
314 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.28 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	0.6064 (4)	0.6768 (4)	0.3644 (3)	0.0694 (10)
H1	0.5226	0.6930	0.3842	0.083*
O1W	0.2866 (5)	0.6414 (4)	0.4672 (4)	0.1503 (14)
H1W	0.229 (7)	0.553 (3)	0.420 (5)	0.225*
H2W	0.258 (8)	0.655 (6)	0.535 (4)	0.225*
C2	0.6940 (5)	0.6521 (4)	0.4419 (3)	0.0774 (11)
H2	0.6694	0.6494	0.5139	0.093*
C3	0.8221 (5)	0.6303 (4)	0.4147 (4)	0.0780 (11)
H3	0.8836	0.6155	0.4703	0.094*
C4	0.8587 (4)	0.6302 (4)	0.3100 (3)	0.0669 (9)
H4	0.9441	0.6147	0.2938	0.080*
C5	0.7416 (4)	0.6647 (3)	−0.0808 (3)	0.0610 (9)
H5	0.8279	0.6514	−0.0982	0.073*
C6	0.6469 (5)	0.6792 (4)	−0.1633 (3)	0.0701 (10)
H6	0.6688	0.6748	−0.2376	0.084*
C7	0.5172 (4)	0.7005 (4)	−0.1417 (3)	0.0712 (10)
H7	0.4535	0.7095	−0.2011	0.085*
C8	0.4848 (4)	0.7081 (3)	−0.0346 (3)	0.0619 (9)
H8	0.3984	0.7228	−0.0200	0.074*
C9	0.5504 (4)	0.7021 (3)	0.1689 (3)	0.0519 (8)
N10	0.8010 (3)	0.6524 (3)	0.1173 (2)	0.0524 (7)
C11	0.6393 (4)	0.6788 (3)	0.2530 (3)	0.0539 (8)
C12	0.7684 (4)	0.6534 (3)	0.2251 (3)	0.0521 (8)
C13	0.5797 (3)	0.6941 (3)	0.0564 (3)	0.0502 (8)
C14	0.7103 (4)	0.6698 (3)	0.0315 (3)	0.0501 (8)
C15	0.4158 (5)	0.7316 (4)	0.1978 (3)	0.0609 (9)
O16	0.4730 (3)	0.8678 (2)	0.2685 (2)	0.0703 (7)
O17	0.2782 (3)	0.6459 (3)	0.1585 (3)	0.0872 (8)
C18	0.3576 (4)	0.9124 (3)	0.2952 (3)	0.0613 (9)
C19	0.3045 (4)	0.9060 (4)	0.3932 (3)	0.0672 (9)
H19	0.3389	0.8693	0.4426	0.081*
C20	0.1975 (4)	0.9564 (4)	0.4164 (4)	0.0749 (10)
C21	0.1428 (5)	1.0080 (4)	0.3448 (4)	0.0842 (12)
H21	0.0687	1.0395	0.3624	0.101*
C22	0.1981 (5)	1.0130 (4)	0.2468 (4)	0.0915 (13)
H22	0.1613	1.0478	0.1966	0.110*
C23	0.3089 (5)	0.9664 (4)	0.2211 (4)	0.0816 (11)
H23	0.3492	0.9716	0.1554	0.098*
F24	0.1452 (3)	0.9541 (3)	0.5144 (2)	0.1166 (9)
C25	0.9405 (4)	0.6317 (4)	0.0943 (3)	0.0695 (10)
H25A	0.9560	0.6413	0.0197	0.104*
H25B	0.9204	0.5401	0.0843	0.104*
H25C	1.0355	0.7005	0.1642	0.104*
S26	0.08915 (12)	0.70895 (10)	0.76540 (9)	0.0699 (3)
O27	0.1099 (3)	0.6733 (3)	0.8669 (2)	0.0903 (8)
O28	0.1777 (3)	0.6826 (3)	0.6828 (2)	0.1036 (9)
O29	−0.0729 (3)	0.6712 (3)	0.7054 (2)	0.0931 (8)
C30	0.1857 (6)	0.8973 (5)	0.8431 (4)	0.0860 (12)
F31	0.1788 (4)	0.9507 (3)	0.7638 (3)	0.1385 (10)
F32	0.3375 (3)	0.9479 (3)	0.9058 (3)	0.1292 (9)
F33	0.1148 (4)	0.9392 (3)	0.9240 (3)	0.1307 (10)

	U11	U22	U33	U12	U13	U23
C1	0.066 (3)	0.071 (3)	0.065 (2)	0.030 (2)	0.023 (2)	0.025 (2)
O1W	0.182 (4)	0.113 (3)	0.147 (3)	0.046 (3)	0.105 (3)	0.056 (3)
C2	0.093 (3)	0.077 (3)	0.058 (2)	0.037 (3)	0.021 (2)	0.029 (2)
C3	0.084 (3)	0.074 (3)	0.070 (3)	0.039 (2)	0.009 (2)	0.030 (2)
C4	0.062 (2)	0.070 (3)	0.068 (2)	0.034 (2)	0.015 (2)	0.028 (2)
C5	0.056 (2)	0.059 (2)	0.063 (2)	0.023 (2)	0.021 (2)	0.0251 (19)
C6	0.075 (3)	0.069 (3)	0.066 (2)	0.029 (2)	0.024 (2)	0.034 (2)
C7	0.069 (3)	0.073 (3)	0.074 (3)	0.033 (2)	0.013 (2)	0.039 (2)
C8	0.054 (2)	0.063 (2)	0.073 (2)	0.030 (2)	0.018 (2)	0.031 (2)
C9	0.0383 (19)	0.041 (2)	0.063 (2)	0.0149 (17)	0.0100 (18)	0.0155 (17)
N10	0.0393 (16)	0.0494 (17)	0.0600 (17)	0.0198 (14)	0.0128 (14)	0.0170 (14)
C11	0.049 (2)	0.047 (2)	0.055 (2)	0.0186 (18)	0.0146 (18)	0.0156 (17)
C12	0.046 (2)	0.047 (2)	0.053 (2)	0.0194 (18)	0.0093 (17)	0.0160 (17)
C13	0.0399 (19)	0.046 (2)	0.058 (2)	0.0177 (17)	0.0096 (17)	0.0199 (17)
C14	0.0427 (19)	0.043 (2)	0.057 (2)	0.0176 (17)	0.0115 (17)	0.0187 (17)
C15	0.052 (2)	0.062 (3)	0.069 (2)	0.029 (2)	0.019 (2)	0.026 (2)
O16	0.0491 (15)	0.0527 (17)	0.0950 (18)	0.0241 (14)	0.0246 (14)	0.0159 (14)
O17	0.0458 (17)	0.0675 (18)	0.120 (2)	0.0229 (16)	0.0242 (16)	0.0149 (16)
C18	0.047 (2)	0.050 (2)	0.075 (2)	0.0228 (19)	0.019 (2)	0.0160 (19)
C19	0.053 (2)	0.062 (2)	0.070 (2)	0.023 (2)	0.017 (2)	0.017 (2)
C20	0.063 (2)	0.078 (3)	0.067 (3)	0.029 (2)	0.029 (2)	0.015 (2)
C21	0.076 (3)	0.075 (3)	0.101 (3)	0.047 (3)	0.030 (3)	0.024 (3)
C22	0.088 (3)	0.091 (3)	0.115 (4)	0.054 (3)	0.042 (3)	0.049 (3)
C23	0.084 (3)	0.079 (3)	0.099 (3)	0.043 (3)	0.050 (3)	0.044 (3)
F24	0.1057 (19)	0.148 (2)	0.0961 (18)	0.0634 (18)	0.0560 (16)	0.0400 (16)
C25	0.053 (2)	0.084 (3)	0.077 (2)	0.042 (2)	0.023 (2)	0.029 (2)
S26	0.0717 (7)	0.0774 (7)	0.0647 (6)	0.0376 (6)	0.0255 (6)	0.0312 (5)
O27	0.104 (2)	0.111 (2)	0.0891 (19)	0.0613 (19)	0.0385 (17)	0.0646 (18)
O28	0.124 (2)	0.117 (2)	0.099 (2)	0.073 (2)	0.067 (2)	0.0466 (18)
O29	0.0619 (18)	0.116 (2)	0.0755 (18)	0.0298 (17)	0.0063 (14)	0.0341 (17)
C30	0.084 (3)	0.096 (3)	0.093 (3)	0.050 (3)	0.028 (3)	0.048 (3)
F31	0.149 (3)	0.122 (2)	0.169 (3)	0.059 (2)	0.039 (2)	0.101 (2)
F32	0.0778 (19)	0.102 (2)	0.152 (2)	0.0157 (16)	−0.0044 (17)	0.0420 (18)
F33	0.152 (3)	0.104 (2)	0.129 (2)	0.077 (2)	0.047 (2)	0.0220 (17)

C1—C2	1.340 (4)	C11—C12	1.427 (4)
C1—C11	1.416 (4)	C13—C14	1.425 (4)
C1—H1	0.9300	C15—O17	1.187 (4)
O1W—H1W	0.86 (2)	C15—O16	1.335 (4)
O1W—H2W	0.874 (19)	O16—C18	1.415 (3)
C2—C3	1.396 (5)	C18—C19	1.352 (4)
C2—H2	0.9300	C18—C23	1.373 (5)
C3—C4	1.345 (4)	C19—C20	1.375 (4)
C3—H3	0.9300	C19—H19	0.9300
C4—C12	1.404 (4)	C20—F24	1.339 (4)
C4—H4	0.9300	C20—C21	1.354 (5)
C5—C6	1.343 (4)	C21—C22	1.359 (5)
C5—C14	1.404 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.385 (5)
C6—C7	1.390 (4)	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.342 (4)	C25—H25A	0.9600
C7—H7	0.9300	C25—H25B	0.9600
C8—C13	1.412 (4)	C25—H25C	0.9600
C8—H8	0.9300	S26—O28	1.415 (2)
C9—C13	1.391 (4)	S26—O27	1.423 (2)
C9—C11	1.391 (4)	S26—O29	1.427 (2)
C9—C15	1.504 (4)	S26—C30	1.806 (5)
N10—C12	1.365 (4)	C30—F31	1.304 (4)
N10—C14	1.369 (4)	C30—F32	1.315 (4)
N10—C25	1.484 (3)	C30—F33	1.320 (4)
C2—C1—C11	121.1 (3)	C5—C14—C13	118.5 (3)
C2—C1—H1	119.4	O17—C15—O16	125.6 (3)
C11—C1—H1	119.4	O17—C15—C9	124.2 (3)
H1W—O1W—H2W	105 (3)	O16—C15—C9	110.2 (3)
C1—C2—C3	120.1 (3)	C15—O16—C18	116.3 (3)
C1—C2—H2	120.0	C19—C18—C23	122.6 (3)
C3—C2—H2	120.0	C19—C18—O16	120.1 (3)
C4—C3—C2	121.6 (3)	C23—C18—O16	117.2 (3)
C4—C3—H3	119.2	C18—C19—C20	116.8 (3)
C2—C3—H3	119.2	C18—C19—H19	121.6
C3—C4—C12	120.3 (3)	C20—C19—H19	121.6
C3—C4—H4	119.8	F24—C20—C21	118.8 (3)
C12—C4—H4	119.8	F24—C20—C19	118.2 (4)
C6—C5—C14	119.9 (3)	C21—C20—C19	123.0 (4)
C6—C5—H5	120.0	C20—C21—C22	118.8 (3)
C14—C5—H5	120.0	C20—C21—H21	120.6
C5—C6—C7	122.4 (3)	C22—C21—H21	120.6
C5—C6—H6	118.8	C21—C22—C23	120.4 (4)
C7—C6—H6	118.8	C21—C22—H22	119.8
C8—C7—C6	119.4 (3)	C23—C22—H22	119.8
C8—C7—H7	120.3	C18—C23—C22	118.2 (4)
C6—C7—H7	120.3	C18—C23—H23	120.9
C7—C8—C13	121.2 (3)	C22—C23—H23	120.9
C7—C8—H8	119.4	N10—C25—H25A	109.5
C13—C8—H8	119.4	N10—C25—H25B	109.5
C13—C9—C11	121.5 (3)	H25A—C25—H25B	109.5
C13—C9—C15	119.1 (3)	N10—C25—H25C	109.5
C11—C9—C15	119.4 (3)	H25A—C25—H25C	109.5
C12—N10—C14	122.5 (2)	H25B—C25—H25C	109.5
C12—N10—C25	117.7 (2)	O28—S26—O27	115.73 (15)
C14—N10—C25	119.8 (3)	O28—S26—O29	114.66 (17)
C9—C11—C1	123.2 (3)	O27—S26—O29	115.01 (16)
C9—C11—C12	118.6 (3)	O28—S26—C30	102.91 (19)
C1—C11—C12	118.2 (3)	O27—S26—C30	102.55 (19)
N10—C12—C4	121.9 (3)	O29—S26—C30	103.36 (18)
N10—C12—C11	119.4 (3)	F31—C30—F32	109.0 (4)
C4—C12—C11	118.7 (3)	F31—C30—F33	107.7 (3)
C9—C13—C8	122.8 (3)	F32—C30—F33	107.5 (4)
C9—C13—C14	118.6 (3)	F31—C30—S26	111.8 (3)
C8—C13—C14	118.6 (3)	F32—C30—S26	110.4 (3)
N10—C14—C5	122.2 (3)	F33—C30—S26	110.3 (3)
N10—C14—C13	119.3 (3)
C11—C1—C2—C3	1.2 (6)	C6—C5—C14—C13	−1.7 (5)
C1—C2—C3—C4	−1.6 (6)	C9—C13—C14—N10	1.2 (4)
C2—C3—C4—C12	0.5 (6)	C8—C13—C14—N10	−178.4 (3)
C14—C5—C6—C7	0.6 (5)	C9—C13—C14—C5	−178.6 (3)
C5—C6—C7—C8	0.4 (5)	C8—C13—C14—C5	1.8 (4)
C6—C7—C8—C13	−0.3 (5)	C13—C9—C15—O17	81.3 (5)
C13—C9—C11—C1	−175.7 (3)	C11—C9—C15—O17	−96.5 (4)
C15—C9—C11—C1	2.1 (5)	C13—C9—C15—O16	−95.9 (3)
C13—C9—C11—C12	3.3 (5)	C11—C9—C15—O16	86.3 (4)
C15—C9—C11—C12	−178.9 (3)	O17—C15—O16—C18	−1.8 (5)
C2—C1—C11—C9	179.1 (3)	C9—C15—O16—C18	175.4 (3)
C2—C1—C11—C12	0.1 (5)	C15—O16—C18—C19	85.5 (4)
C14—N10—C12—C4	177.5 (3)	C15—O16—C18—C23	−97.1 (4)
C25—N10—C12—C4	−2.5 (4)	C23—C18—C19—C20	0.1 (5)
C14—N10—C12—C11	−2.5 (4)	O16—C18—C19—C20	177.4 (3)
C25—N10—C12—C11	177.4 (3)	C18—C19—C20—F24	−178.7 (3)
C3—C4—C12—N10	−179.2 (3)	C18—C19—C20—C21	1.3 (6)
C3—C4—C12—C11	0.8 (5)	F24—C20—C21—C22	178.7 (3)
C9—C11—C12—N10	−0.1 (4)	C19—C20—C21—C22	−1.3 (6)
C1—C11—C12—N10	178.9 (3)	C20—C21—C22—C23	−0.2 (6)
C9—C11—C12—C4	179.8 (3)	C19—C18—C23—C22	−1.5 (6)
C1—C11—C12—C4	−1.1 (4)	O16—C18—C23—C22	−178.9 (3)
C11—C9—C13—C8	175.7 (3)	C21—C22—C23—C18	1.6 (6)
C15—C9—C13—C8	−2.0 (5)	O28—S26—C30—F31	59.7 (3)
C11—C9—C13—C14	−3.9 (4)	O27—S26—C30—F31	−179.8 (3)
C15—C9—C13—C14	178.4 (3)	O29—S26—C30—F31	−60.0 (3)
C7—C8—C13—C9	179.6 (3)	O28—S26—C30—F32	−61.8 (3)
C7—C8—C13—C14	−0.8 (5)	O27—S26—C30—F32	58.7 (3)
C12—N10—C14—C5	−178.2 (3)	O29—S26—C30—F32	178.6 (3)
C25—N10—C14—C5	1.9 (4)	O28—S26—C30—F33	179.5 (3)
C12—N10—C14—C13	2.0 (4)	O27—S26—C30—F33	−60.0 (3)
C25—N10—C14—C13	−178.0 (3)	O29—S26—C30—F33	59.8 (3)
C6—C5—C14—N10	178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O29i	0.85 (3)	2.24 (3)	3.071 (5)	172 (4)
O1W—H2W···O28	0.89 (3)	1.99 (3)	2.873 (5)	176 (8)
C1—H1···O1W	0.93	2.51	3.365 (7)	152
C3—H3···O29ii	0.93	2.60	3.298 (5)	133
C19—H19···O1W	0.93	2.60	3.415 (7)	145
C25—H25A···O27iii	0.96	2.53	3.424 (5)	155
C25—H25C···Cg4ii	0.96	2.64	3.527 (4)	154

X	I	J	I···J	X···J	X—I···J
C20	F24	Cg2iv	3.743 (3)	4.139 (5)	97.6 (2)
C20	F24	Cg2v	3.854 (4)	4.188 (5)	94.9 (3)
C30	F31	Cg1v	3.665 (4)	4.519 (6)	123.6 (3)
C30	F31	Cg3v	3.910 (4)	4.049 (6)	86.7 (3)
C30	F33	Cg3v	3.654 (4)	4.049 (6)	97.7 (3)

I	J	CgI···CgJ	Dihedral angle	CgIPerp	CgIOffset
1	1vi	3.990 (2)	0	3.591 (2)	1.739 (2)
1	3vi	3.645 (2)	2.08 (17)	3.557 (2)	0.796 (2)
2	3vi	3.907 (2)	3.85 (19)	3.431 (2)	1.863 (2)
3	1vi	3.645 (2)	2.08 (17)	3.546 (2)	0.844 (2)
3	2vi	3.907 (2)	3.85 (19)	3.548 (2)	1.629 (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
O1W—H1W⋯O29i	0.85 (3)	2.24 (3)	3.071 (5)	172 (4)
O1W—H2W⋯O28	0.89 (3)	1.99 (3)	2.873 (5)	176 (8)
C1—H1⋯O1W	0.93	2.51	3.365 (7)	152
C3—H3⋯O29ii	0.93	2.60	3.298 (5)	133
C19—H19⋯O1W	0.93	2.60	3.415 (7)	145
C25—H25A⋯O27iii	0.96	2.53	3.424 (5)	155
C25—H25C⋯Cg4ii	0.96	2.64	3.527 (4)	154

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

Table 2

C—F⋯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.

X	I	J	I⋯J	X⋯J	X—I⋯J
C20	F24	Cg2iv	3.743 (3)	4.139 (5)	97.6 (2)
C20	F24	Cg2v	3.854 (4)	4.188 (5)	94.9 (3)
C30	F31	Cg1v	3.665 (4)	4.519 (6)	123.6 (3)
C30	F31	Cg3v	3.910 (4)	4.049 (6)	86.7 (3)
C30	F33	Cg3v	3.654 (4)	4.049 (6)	97.7 (3)

Symmetry codes: (iv) x − 1, y, z; (v) −x + 1, −y + 2, −z + 1.

Table 3

π–π inter­actions (Å,°)

Cg1, Cg2 and Cg3 are as defined in Table 2. 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 the perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgIPerp	CgIOffset
1	1vi	3.990 (2)		3.591 (2)	1.739 (2)
1	3vi	3.645 (2)	2.08 (17)	3.557 (2)	0.796 (2)
2	3vi	3.907 (2)	3.85 (19)	3.431 (2)	1.863 (2)
3	1vi	3.645 (2)	2.08 (17)	3.546 (2)	0.844 (2)
3	2vi	3.907 (2)	3.85 (19)	3.548 (2)	1.629 (2)

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