9-(4-Methyl-phenoxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

In the crystal structure of the title compound, C(22)H(18)NO(2) (+)·CF(3)SO(3) (-), adjacent cations are linked through C-H⋯π and π-π inter-actions, and the cations and anions are connected by C-H⋯O and C-F⋯π inter-actions. The acridine and benzene ring systems are oriented at a dihedral angle of 3.0 (1)°. The carboxyl group is twisted at an angle of 83.1 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel or inclined at an angle of 75.2 (1)° in the crystal structure.

Related literature

For background to the chemiluminogenic properties of 9-phenoxy­carbonyl-10-methyl­acridinium trifluoro­methane­sulf­onates, see: Brown et al. (2009 ▶); Rak et al. (1999 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2006 ▶); Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Sikorski et al. (2006 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C22H18NO2 +·CF3O3S−

M = 477.45

Monoclinic,

a = 13.2686 (6) Å

b = 8.4788 (4) Å

c = 20.4078 (10) Å

β = 106.749 (5)°

V = 2198.51 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.50 × 0.40 × 0.10 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.869, T max = 1.000

12172 measured reflections

3892 independent reflections

2096 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.137

S = 0.95

3892 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED; 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/S1600536810016302/ng2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016302/ng2760Isup2.hkl

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

C22H18NO2+·CF3O3S−	F(000) = 984
Mr = 477.45	Dx = 1.442 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3355 reflections
a = 13.2686 (6) Å	θ = 3.1–29.2°
b = 8.4788 (4) Å	µ = 0.21 mm−1
c = 20.4078 (10) Å	T = 295 K
β = 106.749 (5)°	Plate, light-orange
V = 2198.51 (19) Å3	0.50 × 0.40 × 0.10 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3892 independent reflections
Radiation source: enhanced (Mo) X-Ray Source	2096 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −10→10
Tmin = 0.869, Tmax = 1.000	l = −24→24
12172 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3
3892 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.19 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	0.3367 (3)	0.4502 (4)	0.3326 (2)	0.0699 (10)
H1	0.2898	0.4002	0.3519	0.084*
C2	0.2997 (3)	0.5409 (5)	0.2766 (2)	0.0918 (13)
H2	0.2276	0.5502	0.2563	0.110*
C3	0.3705 (3)	0.6211 (5)	0.2491 (2)	0.0957 (14)
H3	0.3441	0.6854	0.2111	0.115*
C4	0.4760 (3)	0.6083 (4)	0.2759 (2)	0.0691 (10)
H4	0.5208	0.6634	0.2565	0.083*
C5	0.7739 (3)	0.3924 (4)	0.44967 (19)	0.0631 (9)
H5	0.8203	0.4433	0.4302	0.076*
C6	0.8115 (3)	0.3064 (5)	0.5083 (2)	0.0735 (10)
H6	0.8838	0.3013	0.5287	0.088*
C7	0.7440 (3)	0.2253 (5)	0.5386 (2)	0.0766 (11)
H7	0.7713	0.1667	0.5783	0.092*
C8	0.6389 (3)	0.2334 (4)	0.50934 (18)	0.0639 (10)
H8	0.5944	0.1786	0.5291	0.077*
C9	0.4876 (3)	0.3337 (4)	0.41922 (16)	0.0479 (8)
N10	0.62352 (19)	0.4910 (3)	0.36094 (13)	0.0486 (7)
C11	0.4461 (2)	0.4303 (4)	0.36217 (16)	0.0498 (8)
C12	0.5177 (2)	0.5109 (4)	0.33342 (16)	0.0495 (8)
C13	0.5948 (3)	0.3229 (4)	0.44951 (16)	0.0507 (8)
C14	0.6651 (2)	0.4037 (4)	0.41908 (16)	0.0473 (8)
C15	0.4137 (3)	0.2312 (4)	0.44360 (17)	0.0548 (9)
O16	0.38896 (18)	0.2932 (3)	0.49667 (12)	0.0648 (7)
O17	0.3828 (2)	0.1080 (3)	0.41764 (13)	0.0858 (9)
C18	0.3185 (3)	0.2065 (4)	0.52390 (16)	0.0500 (8)
C19	0.3597 (3)	0.1129 (4)	0.57992 (17)	0.0609 (9)
H19	0.4321	0.0997	0.5978	0.073*
C20	0.2903 (3)	0.0381 (4)	0.60930 (17)	0.0652 (10)
H20	0.3170	−0.0262	0.6473	0.078*
C21	0.1839 (3)	0.0565 (4)	0.58395 (19)	0.0647 (10)
C22	0.1461 (3)	0.1515 (5)	0.52795 (19)	0.0671 (10)
H22	0.0739	0.1655	0.5102	0.081*
C23	0.2132 (3)	0.2273 (4)	0.49707 (17)	0.0593 (9)
H23	0.1866	0.2908	0.4589	0.071*
C24	0.1088 (4)	−0.0241 (5)	0.6176 (2)	0.1041 (15)
H24A	0.0428	0.0309	0.6055	0.156*
H24B	0.1387	−0.0225	0.6664	0.156*
H24C	0.0978	−0.1313	0.6021	0.156*
C25	0.6972 (3)	0.5623 (4)	0.32692 (17)	0.0655 (10)
H25A	0.7583	0.4964	0.3343	0.098*
H25B	0.7180	0.6650	0.3458	0.098*
H25C	0.6632	0.5715	0.2787	0.098*
S26	0.98783 (7)	0.47984 (11)	0.33273 (4)	0.0560 (3)
O27	1.09157 (18)	0.4193 (3)	0.34606 (12)	0.0801 (8)
O28	0.96339 (18)	0.5485 (3)	0.39004 (12)	0.0844 (8)
O29	0.90554 (18)	0.3856 (3)	0.28984 (12)	0.0688 (7)
C30	0.9911 (3)	0.6484 (5)	0.2789 (2)	0.0737 (11)
F31	1.0614 (2)	0.7536 (3)	0.31098 (15)	0.1247 (10)
F32	1.0156 (2)	0.6073 (4)	0.22295 (13)	0.1123 (9)
F33	0.8988 (2)	0.7204 (3)	0.25876 (13)	0.1117 (9)

	U11	U22	U33	U12	U13	U23
C1	0.057 (2)	0.061 (2)	0.098 (3)	−0.003 (2)	0.033 (2)	0.014 (2)
C2	0.050 (2)	0.096 (3)	0.131 (4)	0.012 (2)	0.029 (2)	0.033 (3)
C3	0.078 (3)	0.090 (3)	0.117 (3)	0.012 (3)	0.027 (3)	0.046 (3)
C4	0.056 (2)	0.060 (2)	0.098 (3)	−0.0012 (19)	0.032 (2)	0.019 (2)
C5	0.060 (2)	0.052 (2)	0.079 (3)	−0.0077 (19)	0.022 (2)	−0.011 (2)
C6	0.061 (2)	0.063 (3)	0.085 (3)	−0.001 (2)	0.003 (2)	−0.010 (2)
C7	0.086 (3)	0.063 (3)	0.073 (3)	−0.001 (2)	0.011 (2)	0.004 (2)
C8	0.071 (3)	0.054 (2)	0.067 (2)	−0.008 (2)	0.020 (2)	−0.003 (2)
C9	0.058 (2)	0.0330 (18)	0.060 (2)	−0.0060 (16)	0.0285 (18)	−0.0113 (17)
N10	0.0474 (17)	0.0375 (15)	0.0676 (17)	−0.0061 (13)	0.0274 (14)	−0.0070 (14)
C11	0.048 (2)	0.0370 (18)	0.071 (2)	−0.0068 (16)	0.0289 (18)	−0.0049 (18)
C12	0.052 (2)	0.0331 (19)	0.067 (2)	−0.0010 (16)	0.0229 (17)	−0.0037 (17)
C13	0.063 (2)	0.0320 (18)	0.060 (2)	−0.0040 (17)	0.0225 (18)	−0.0059 (16)
C14	0.046 (2)	0.0351 (18)	0.063 (2)	−0.0052 (15)	0.0203 (17)	−0.0105 (17)
C15	0.068 (2)	0.040 (2)	0.066 (2)	−0.0062 (18)	0.0334 (19)	−0.0037 (18)
O16	0.0833 (17)	0.0462 (14)	0.0804 (16)	−0.0143 (13)	0.0485 (14)	−0.0130 (12)
O17	0.122 (2)	0.0581 (17)	0.1013 (19)	−0.0380 (16)	0.0701 (18)	−0.0252 (16)
C18	0.066 (2)	0.0374 (19)	0.054 (2)	−0.0074 (18)	0.0285 (19)	−0.0066 (17)
C19	0.061 (2)	0.057 (2)	0.066 (2)	−0.0032 (19)	0.0198 (19)	−0.008 (2)
C20	0.091 (3)	0.054 (2)	0.0529 (19)	−0.004 (2)	0.024 (2)	0.0038 (18)
C21	0.074 (3)	0.068 (3)	0.060 (2)	−0.014 (2)	0.032 (2)	−0.014 (2)
C22	0.061 (2)	0.078 (3)	0.068 (2)	−0.001 (2)	0.027 (2)	−0.004 (2)
C23	0.072 (3)	0.055 (2)	0.053 (2)	0.002 (2)	0.0214 (19)	0.0023 (17)
C24	0.141 (4)	0.097 (3)	0.099 (3)	−0.038 (3)	0.074 (3)	−0.008 (3)
C25	0.058 (2)	0.068 (2)	0.079 (2)	−0.0098 (19)	0.0331 (19)	−0.0052 (19)
S26	0.0511 (5)	0.0592 (6)	0.0605 (5)	0.0019 (5)	0.0208 (4)	0.0024 (5)
O27	0.0581 (15)	0.0891 (19)	0.0933 (18)	0.0225 (14)	0.0221 (13)	0.0194 (15)
O28	0.0716 (16)	0.118 (2)	0.0732 (16)	−0.0188 (16)	0.0366 (14)	−0.0244 (15)
O29	0.0627 (15)	0.0584 (15)	0.0878 (17)	−0.0099 (12)	0.0258 (13)	−0.0128 (13)
C30	0.062 (3)	0.066 (3)	0.087 (3)	−0.012 (2)	0.011 (2)	0.000 (2)
F31	0.122 (2)	0.0878 (19)	0.140 (2)	−0.0465 (17)	0.0005 (17)	0.0175 (16)
F32	0.114 (2)	0.147 (2)	0.0809 (15)	−0.0172 (17)	0.0356 (14)	0.0272 (16)
F33	0.0992 (18)	0.0718 (16)	0.142 (2)	0.0200 (15)	−0.0010 (16)	0.0185 (15)

C1—C2	1.347 (5)	C15—O16	1.327 (4)
C1—C11	1.412 (4)	O16—C18	1.421 (3)
C1—H1	0.9300	C18—C23	1.357 (4)
C2—C3	1.401 (5)	C18—C19	1.370 (4)
C2—H2	0.9300	C19—C20	1.388 (5)
C3—C4	1.352 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.366 (5)
C4—C12	1.411 (5)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.369 (5)
C5—C6	1.366 (5)	C21—C24	1.524 (5)
C5—C14	1.401 (4)	C22—C23	1.388 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.406 (5)	C23—H23	0.9300
C6—H6	0.9300	C24—H24A	0.9600
C7—C8	1.351 (5)	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C8—C13	1.413 (4)	C25—H25A	0.9600
C8—H8	0.9300	C25—H25B	0.9600
C9—C13	1.381 (4)	C25—H25C	0.9600
C9—C11	1.400 (4)	S26—O27	1.420 (2)
C9—C15	1.499 (4)	S26—O28	1.425 (2)
N10—C12	1.364 (4)	S26—O29	1.430 (2)
N10—C14	1.372 (4)	S26—C30	1.811 (4)
N10—C25	1.481 (4)	C30—F32	1.321 (4)
C11—C12	1.427 (4)	C30—F31	1.321 (4)
C13—C14	1.434 (4)	C30—F33	1.324 (4)
C15—O17	1.189 (4)
C2—C1—C11	120.7 (3)	O16—C15—C9	112.4 (3)
C2—C1—H1	119.7	C15—O16—C18	117.3 (2)
C11—C1—H1	119.7	C23—C18—C19	121.9 (3)
C1—C2—C3	119.5 (4)	C23—C18—O16	119.4 (3)
C1—C2—H2	120.2	C19—C18—O16	118.5 (3)
C3—C2—H2	120.2	C18—C19—C20	118.1 (3)
C4—C3—C2	122.3 (4)	C18—C19—H19	121.0
C4—C3—H3	118.9	C20—C19—H19	121.0
C2—C3—H3	118.9	C21—C20—C19	121.8 (3)
C3—C4—C12	119.7 (3)	C21—C20—H20	119.1
C3—C4—H4	120.1	C19—C20—H20	119.1
C12—C4—H4	120.1	C20—C21—C22	118.2 (3)
C6—C5—C14	119.7 (3)	C20—C21—C24	121.1 (4)
C6—C5—H5	120.1	C22—C21—C24	120.7 (4)
C14—C5—H5	120.1	C21—C22—C23	121.5 (3)
C5—C6—C7	121.8 (4)	C21—C22—H22	119.2
C5—C6—H6	119.1	C23—C22—H22	119.2
C7—C6—H6	119.1	C18—C23—C22	118.5 (3)
C8—C7—C6	119.2 (4)	C18—C23—H23	120.7
C8—C7—H7	120.4	C22—C23—H23	120.7
C6—C7—H7	120.4	C21—C24—H24A	109.5
C7—C8—C13	121.7 (3)	C21—C24—H24B	109.5
C7—C8—H8	119.1	H24A—C24—H24B	109.5
C13—C8—H8	119.1	C21—C24—H24C	109.5
C13—C9—C11	121.2 (3)	H24A—C24—H24C	109.5
C13—C9—C15	120.1 (3)	H24B—C24—H24C	109.5
C11—C9—C15	118.5 (3)	N10—C25—H25A	109.4
C12—N10—C14	122.2 (2)	N10—C25—H25B	109.5
C12—N10—C25	119.8 (3)	H25A—C25—H25B	109.5
C14—N10—C25	118.0 (3)	N10—C25—H25C	109.6
C9—C11—C1	122.4 (3)	H25A—C25—H25C	109.5
C9—C11—C12	118.2 (3)	H25B—C25—H25C	109.5
C1—C11—C12	119.4 (3)	O27—S26—O28	115.33 (16)
N10—C12—C4	121.7 (3)	O27—S26—O29	116.23 (16)
N10—C12—C11	120.0 (3)	O28—S26—O29	114.60 (14)
C4—C12—C11	118.3 (3)	O27—S26—C30	102.13 (17)
C9—C13—C8	122.6 (3)	O28—S26—C30	103.11 (19)
C9—C13—C14	119.3 (3)	O29—S26—C30	102.54 (16)
C8—C13—C14	118.2 (3)	F32—C30—F31	107.0 (3)
N10—C14—C5	121.9 (3)	F32—C30—F33	106.9 (3)
N10—C14—C13	118.9 (3)	F31—C30—F33	107.5 (3)
C5—C14—C13	119.3 (3)	F32—C30—S26	111.8 (3)
O17—C15—O16	125.2 (3)	F31—C30—S26	111.7 (3)
O17—C15—C9	122.4 (3)	F33—C30—S26	111.7 (3)
C11—C1—C2—C3	−2.5 (6)	C6—C5—C14—C13	−0.7 (5)
C1—C2—C3—C4	1.5 (7)	C9—C13—C14—N10	0.7 (4)
C2—C3—C4—C12	0.2 (6)	C8—C13—C14—N10	180.0 (3)
C14—C5—C6—C7	1.3 (5)	C9—C13—C14—C5	−179.8 (3)
C5—C6—C7—C8	−0.5 (5)	C8—C13—C14—C5	−0.5 (4)
C6—C7—C8—C13	−0.8 (5)	C13—C9—C15—O17	−94.0 (4)
C13—C9—C11—C1	−176.4 (3)	C11—C9—C15—O17	81.1 (4)
C15—C9—C11—C1	8.5 (4)	C13—C9—C15—O16	85.3 (3)
C13—C9—C11—C12	3.6 (4)	C11—C9—C15—O16	−99.6 (3)
C15—C9—C11—C12	−171.5 (3)	O17—C15—O16—C18	−1.1 (5)
C2—C1—C11—C9	−178.2 (3)	C9—C15—O16—C18	179.6 (3)
C2—C1—C11—C12	1.8 (5)	C15—O16—C18—C23	−87.3 (4)
C14—N10—C12—C4	176.3 (3)	C15—O16—C18—C19	97.4 (3)
C25—N10—C12—C4	−5.0 (4)	C23—C18—C19—C20	0.0 (5)
C14—N10—C12—C11	−4.6 (4)	O16—C18—C19—C20	175.2 (3)
C25—N10—C12—C11	174.0 (3)	C18—C19—C20—C21	−0.3 (5)
C3—C4—C12—N10	178.1 (3)	C19—C20—C21—C22	0.1 (5)
C3—C4—C12—C11	−0.9 (5)	C19—C20—C21—C24	−178.9 (3)
C9—C11—C12—N10	0.9 (4)	C20—C21—C22—C23	0.3 (5)
C1—C11—C12—N10	−179.1 (3)	C24—C21—C22—C23	179.3 (3)
C9—C11—C12—C4	180.0 (3)	C19—C18—C23—C22	0.4 (5)
C1—C11—C12—C4	0.0 (4)	O16—C18—C23—C22	−174.8 (3)
C11—C9—C13—C8	176.4 (3)	C21—C22—C23—C18	−0.5 (5)
C15—C9—C13—C8	−8.6 (4)	O27—S26—C30—F32	58.5 (3)
C11—C9—C13—C14	−4.4 (4)	O28—S26—C30—F32	178.4 (3)
C15—C9—C13—C14	170.6 (3)	O29—S26—C30—F32	−62.3 (3)
C7—C8—C13—C9	−179.4 (3)	O27—S26—C30—F31	−61.3 (3)
C7—C8—C13—C14	1.3 (5)	O28—S26—C30—F31	58.6 (3)
C12—N10—C14—C5	−175.6 (3)	O29—S26—C30—F31	177.9 (3)
C25—N10—C14—C5	5.7 (4)	O27—S26—C30—F33	178.2 (3)
C12—N10—C14—C13	3.8 (4)	O28—S26—C30—F33	−61.8 (3)
C25—N10—C14—C13	−174.8 (3)	O29—S26—C30—F33	57.5 (3)
C6—C5—C14—N10	178.8 (3)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O27i	0.93	2.57	3.314 (5)	137
C4—H4···O29i	0.93	2.44	3.319 (4)	159
C5—H5···O28	0.93	2.44	3.364 (5)	171
C6—H6···O28ii	0.93	2.56	3.342 (5)	142
C23—H23···O27iii	0.93	2.53	3.448 (4)	169
C25—H25A···O29	0.96	2.56	3.415 (5)	149
C25—H25B···Cg4iv	0.96	2.62	3.487 (4)	151

X	I	J	I···J	X···J	X–I···J
C30	F31	Cg2i	3.420 (3)	4.044 (4)	108.9 (2)
C30	F32	Cg1i	3.441 (3)	4.032 (4)	107.1 (2)
C30	F32	Cg2i	3.788 (4)	4.044 (4)	91.5 (2)
C30	F33	Cg1i	3.669 (3)	4.032 (4)	96.2 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
3	4v	3.913 (2)	4.80 (17)	3.472 (2)	1.805 (2)
4	3v	3.913 (2)	4.80 (17)	3.565 (2)	1.613 (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⋯O27i	0.93	2.57	3.314 (5)	137
C4—H4⋯O29i	0.93	2.44	3.319 (4)	159
C5—H5⋯O28	0.93	2.44	3.364 (5)	171
C6—H6⋯O28ii	0.93	2.56	3.342 (5)	142
C23—H23⋯O27iii	0.93	2.53	3.448 (4)	169
C25—H25A⋯O29	0.96	2.56	3.415 (5)	149
C25—H25B⋯Cg4iv	0.96	2.62	3.487 (4)	151

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

Table 2

C–F⋯π inter­actions (Å,°)

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

X	I	J	I⋯J	X⋯J	X–I⋯J
C30	F31	Cg2i	3.420 (3)	4.044 (4)	108.9 (2)
C30	F32	Cg1i	3.441 (3)	4.032 (4)	107.1 (2)
C30	F32	Cg2i	3.788 (4)	4.044 (4)	91.5 (2)
C30	F33	Cg1i	3.669 (3)	4.032 (4)	96.2 (2)

Symmetry code: (i) .

Table 3

π–π inter­actions (Å,°)

Cg3 and Cg4 are the centroids of the C5–C8/C13/C14 and C18–C23 rings, respectively. 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 perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
3	4v	3.913 (2)	4.80 (17)	3.472 (2)	1.805 (2)
4	3v	3.913 (2)	4.80 (17)	3.565 (2)	1.613 (2)

Symmetry code: (v) .