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

In the crystal structure of the title compound, C(21)H(15)FNO(2) (+)·CF(3)SO(3) (-), the cations form inversion dimers through C-H⋯O, C-F⋯π and π-π inter-actions. These dimers are further linked by π-π inter-actions. The cations and anions are connected through 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 74.1 (1)°. The carboxyl-ate group is twisted at an angle of 4.4 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine moieties are parallel or inclined at an angle of 55.4 (1)° in the crystal structure.

Related literature

For general 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: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶). For the synthesis, see: Sato (1996 ▶); Sikorski et al. (2005 ▶).

Experimental

Crystal data

C21H15FNO2 +·CF3SO3 −

M = 481.41

Monoclinic,

a = 20.854 (3) Å

b = 7.8092 (12) Å

c = 25.690 (4) Å

β = 100.893 (15)°

V = 4108.2 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.38 × 0.29 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.676, T max = 0.985

15588 measured reflections

3634 independent reflections

1978 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 0.91

3634 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.17 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: 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/S1600536810039231/ng5037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039231/ng5037Isup2.hkl

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

C21H15FNO2+·CF3SO3−	F(000) = 1968
Mr = 481.41	Dx = 1.557 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3994 reflections
a = 20.854 (3) Å	θ = 3.0–24.9°
b = 7.8092 (12) Å	µ = 0.23 mm−1
c = 25.690 (4) Å	T = 295 K
β = 100.893 (15)°	Plate, yellow
V = 4108.2 (11) Å3	0.38 × 0.29 × 0.05 mm
Z = 8

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3634 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1978 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω scans	h = −23→24
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −9→9
Tmin = 0.676, Tmax = 0.985	l = −30→30
15588 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
3634 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.25 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	0.03283 (13)	0.1193 (3)	0.11048 (10)	0.0600 (7)
H1	0.0011	0.1023	0.0802	0.072*
C2	0.02112 (15)	0.0689 (4)	0.15766 (12)	0.0797 (9)
H2	−0.0186	0.0186	0.1602	0.096*
C3	0.06910 (18)	0.0924 (5)	0.20305 (12)	0.0860 (10)
H3	0.0608	0.0560	0.2356	0.103*
C4	0.12683 (16)	0.1660 (4)	0.20108 (10)	0.0707 (8)
H4	0.1578	0.1792	0.2320	0.085*
C5	0.27041 (13)	0.4437 (4)	0.09888 (12)	0.0660 (7)
H5	0.3020	0.4586	0.1293	0.079*
C6	0.28130 (13)	0.5020 (4)	0.05259 (13)	0.0733 (8)
H6	0.3205	0.5572	0.0514	0.088*
C7	0.23522 (14)	0.4824 (4)	0.00556 (11)	0.0698 (8)
H7	0.2435	0.5262	−0.0262	0.084*
C8	0.17902 (13)	0.3997 (3)	0.00688 (9)	0.0568 (7)
H8	0.1488	0.3852	−0.0244	0.068*
C9	0.10650 (12)	0.2530 (3)	0.05781 (9)	0.0441 (6)
N10	0.19775 (10)	0.3032 (3)	0.14935 (8)	0.0539 (6)
C11	0.09265 (12)	0.1981 (3)	0.10599 (9)	0.0471 (6)
C12	0.14047 (13)	0.2230 (3)	0.15271 (9)	0.0508 (6)
C13	0.16483 (12)	0.3344 (3)	0.05474 (9)	0.0475 (6)
C14	0.21142 (11)	0.3595 (3)	0.10230 (9)	0.0503 (6)
C15	0.05947 (12)	0.2166 (3)	0.00717 (9)	0.0465 (6)
O16	0.00735 (8)	0.3201 (2)	0.00150 (6)	0.0547 (5)
O17	0.06869 (8)	0.1103 (2)	−0.02370 (6)	0.0632 (5)
C18	−0.03879 (12)	0.3069 (3)	−0.04620 (9)	0.0463 (6)
C19	−0.02424 (12)	0.3744 (3)	−0.09170 (9)	0.0544 (6)
H19	0.0161	0.4252	−0.0917	0.065*
C20	−0.07040 (12)	0.3656 (3)	−0.13730 (9)	0.0584 (7)
H20	−0.0619	0.4093	−0.1690	0.070*
C21	−0.12898 (12)	0.2915 (3)	−0.13526 (10)	0.0573 (7)
C22	−0.14428 (12)	0.2281 (3)	−0.09000 (10)	0.0589 (7)
H22	−0.1851	0.1800	−0.0900	0.071*
C23	−0.09828 (12)	0.2366 (3)	−0.04435 (10)	0.0541 (6)
H23	−0.1074	0.1952	−0.0126	0.065*
F24	−0.17440 (7)	0.2840 (2)	−0.18049 (6)	0.0861 (5)
C25	0.24602 (14)	0.3310 (4)	0.19848 (10)	0.0818 (9)
H25A	0.2755	0.4207	0.1930	0.123*
H25B	0.2702	0.2273	0.2079	0.123*
H25C	0.2238	0.3629	0.2265	0.123*
S26	0.15240 (4)	0.38413 (11)	0.35642 (3)	0.0719 (3)
O27	0.15245 (13)	0.2321 (3)	0.32563 (8)	0.1034 (8)
O28	0.11971 (11)	0.3678 (3)	0.40094 (7)	0.0928 (7)
O29	0.21189 (9)	0.4779 (3)	0.36698 (9)	0.1031 (8)
C30	0.09881 (15)	0.5223 (5)	0.31287 (13)	0.0770 (9)
F31	0.11978 (10)	0.5488 (3)	0.26795 (7)	0.1135 (7)
F32	0.09350 (10)	0.6752 (3)	0.33429 (9)	0.1138 (7)
F33	0.03935 (9)	0.4604 (3)	0.30042 (8)	0.1163 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0610 (18)	0.0645 (16)	0.0525 (16)	−0.0065 (14)	0.0053 (13)	−0.0087 (14)
C2	0.078 (2)	0.095 (2)	0.071 (2)	−0.0137 (17)	0.0241 (18)	−0.0010 (17)
C3	0.098 (3)	0.112 (3)	0.0518 (18)	−0.003 (2)	0.0229 (18)	0.0057 (17)
C4	0.077 (2)	0.092 (2)	0.0400 (16)	0.0092 (18)	0.0029 (14)	−0.0005 (15)
C5	0.0481 (16)	0.0763 (19)	0.0671 (19)	−0.0031 (14)	−0.0056 (14)	−0.0100 (16)
C6	0.0557 (18)	0.079 (2)	0.086 (2)	−0.0064 (16)	0.0130 (17)	−0.0049 (18)
C7	0.0716 (19)	0.0736 (19)	0.0665 (18)	−0.0049 (16)	0.0190 (16)	0.0019 (15)
C8	0.0601 (17)	0.0600 (16)	0.0462 (15)	−0.0010 (14)	0.0000 (12)	0.0017 (12)
C9	0.0509 (15)	0.0377 (12)	0.0391 (14)	0.0074 (11)	−0.0028 (11)	−0.0044 (10)
N10	0.0524 (14)	0.0609 (13)	0.0419 (13)	0.0078 (11)	−0.0074 (10)	−0.0062 (10)
C11	0.0519 (15)	0.0430 (13)	0.0439 (15)	0.0066 (12)	0.0026 (12)	−0.0042 (11)
C12	0.0584 (17)	0.0512 (15)	0.0398 (15)	0.0114 (13)	0.0017 (12)	−0.0043 (11)
C13	0.0466 (15)	0.0447 (14)	0.0469 (15)	0.0063 (12)	−0.0016 (12)	−0.0054 (11)
C14	0.0462 (15)	0.0529 (15)	0.0466 (15)	0.0067 (12)	−0.0045 (12)	−0.0038 (12)
C15	0.0499 (15)	0.0449 (14)	0.0409 (14)	0.0005 (12)	−0.0011 (12)	0.0005 (11)
O16	0.0563 (10)	0.0565 (10)	0.0448 (9)	0.0131 (9)	−0.0070 (8)	−0.0087 (8)
O17	0.0652 (12)	0.0623 (11)	0.0540 (11)	0.0152 (9)	−0.0090 (9)	−0.0200 (9)
C18	0.0475 (15)	0.0457 (13)	0.0406 (14)	0.0093 (12)	−0.0047 (11)	−0.0024 (11)
C19	0.0432 (14)	0.0631 (16)	0.0541 (16)	−0.0029 (12)	0.0016 (12)	−0.0018 (13)
C20	0.0553 (17)	0.0742 (17)	0.0432 (14)	0.0011 (14)	0.0027 (13)	0.0031 (13)
C21	0.0463 (16)	0.0646 (17)	0.0527 (16)	0.0050 (13)	−0.0116 (13)	−0.0039 (13)
C22	0.0426 (15)	0.0630 (17)	0.0661 (19)	−0.0024 (13)	−0.0027 (14)	0.0048 (14)
C23	0.0532 (16)	0.0524 (15)	0.0571 (16)	0.0047 (13)	0.0111 (13)	0.0099 (12)
F24	0.0617 (10)	0.1201 (13)	0.0636 (10)	−0.0034 (9)	−0.0210 (8)	0.0016 (9)
C25	0.0658 (19)	0.120 (3)	0.0491 (16)	−0.0003 (18)	−0.0162 (14)	−0.0050 (16)
S26	0.0683 (5)	0.0884 (5)	0.0517 (4)	0.0159 (4)	−0.0074 (4)	−0.0033 (4)
O27	0.145 (2)	0.0928 (16)	0.0634 (13)	0.0384 (15)	−0.0047 (13)	−0.0118 (12)
O28	0.1093 (17)	0.1221 (18)	0.0467 (11)	0.0021 (14)	0.0142 (11)	0.0038 (11)
O29	0.0523 (12)	0.138 (2)	0.1089 (17)	0.0033 (13)	−0.0110 (11)	0.0050 (15)
C30	0.069 (2)	0.095 (3)	0.068 (2)	0.0111 (18)	0.0138 (17)	0.0039 (19)
F31	0.1171 (15)	0.1541 (19)	0.0703 (12)	0.0225 (13)	0.0202 (11)	0.0343 (12)
F32	0.1120 (16)	0.0935 (15)	0.1339 (17)	0.0282 (12)	0.0182 (13)	0.0020 (13)
F33	0.0566 (11)	0.164 (2)	0.1149 (15)	0.0014 (12)	−0.0169 (10)	0.0110 (14)

C1—C2	1.340 (4)	C13—C14	1.423 (3)
C1—C11	1.415 (3)	C15—O17	1.188 (3)
C1—H1	0.9300	C15—O16	1.340 (3)
C2—C3	1.398 (4)	O16—C18	1.412 (3)
C2—H2	0.9300	C18—C23	1.366 (3)
C3—C4	1.344 (4)	C18—C19	1.368 (3)
C3—H3	0.9300	C19—C20	1.370 (3)
C4—C12	1.399 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.362 (4)
C5—C6	1.332 (4)	C20—H20	0.9300
C5—C14	1.412 (4)	C21—F24	1.355 (3)
C5—H5	0.9300	C21—C22	1.356 (3)
C6—C7	1.403 (4)	C22—C23	1.369 (3)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.344 (3)	C23—H23	0.9300
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.413 (3)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C13	1.388 (3)	S26—O29	1.422 (2)
C9—C11	1.391 (3)	S26—O27	1.427 (2)
C9—C15	1.501 (3)	S26—O28	1.444 (2)
N10—C14	1.366 (3)	S26—C30	1.787 (3)
N10—C12	1.366 (3)	C30—F33	1.313 (3)
N10—C25	1.474 (3)	C30—F31	1.325 (3)
C11—C12	1.421 (3)	C30—F32	1.328 (4)
C2—C1—C11	121.0 (2)	C5—C14—C13	118.1 (2)
C2—C1—H1	119.5	O17—C15—O16	125.4 (2)
C11—C1—H1	119.5	O17—C15—C9	123.3 (2)
C1—C2—C3	119.5 (3)	O16—C15—C9	111.3 (2)
C1—C2—H2	120.3	C15—O16—C18	117.11 (17)
C3—C2—H2	120.3	C23—C18—C19	122.3 (2)
C4—C3—C2	122.0 (3)	C23—C18—O16	118.3 (2)
C4—C3—H3	119.0	C19—C18—O16	119.3 (2)
C2—C3—H3	119.0	C18—C19—C20	118.5 (2)
C3—C4—C12	120.2 (3)	C18—C19—H19	120.7
C3—C4—H4	119.9	C20—C19—H19	120.7
C12—C4—H4	119.9	C21—C20—C19	118.6 (2)
C6—C5—C14	120.8 (2)	C21—C20—H20	120.7
C6—C5—H5	119.6	C19—C20—H20	120.7
C14—C5—H5	119.6	F24—C21—C22	118.7 (2)
C5—C6—C7	121.8 (3)	F24—C21—C20	118.2 (2)
C5—C6—H6	119.1	C22—C21—C20	123.1 (2)
C7—C6—H6	119.1	C21—C22—C23	118.4 (2)
C8—C7—C6	119.3 (3)	C21—C22—H22	120.8
C8—C7—H7	120.3	C23—C22—H22	120.8
C6—C7—H7	120.3	C18—C23—C22	118.9 (2)
C7—C8—C13	121.5 (2)	C18—C23—H23	120.5
C7—C8—H8	119.3	C22—C23—H23	120.5
C13—C8—H8	119.3	N10—C25—H25A	109.5
C13—C9—C11	121.6 (2)	N10—C25—H25B	109.5
C13—C9—C15	118.3 (2)	H25A—C25—H25B	109.5
C11—C9—C15	120.1 (2)	N10—C25—H25C	109.5
C14—N10—C12	122.33 (19)	H25A—C25—H25C	109.5
C14—N10—C25	119.2 (2)	H25B—C25—H25C	109.5
C12—N10—C25	118.5 (2)	O29—S26—O27	116.26 (16)
C9—C11—C1	122.8 (2)	O29—S26—O28	114.84 (13)
C9—C11—C12	118.6 (2)	O27—S26—O28	114.55 (15)
C1—C11—C12	118.6 (2)	O29—S26—C30	103.21 (15)
N10—C12—C4	121.9 (2)	O27—S26—C30	102.78 (15)
N10—C12—C11	119.5 (2)	O28—S26—C30	102.50 (14)
C4—C12—C11	118.6 (3)	F33—C30—F31	107.3 (2)
C9—C13—C8	123.0 (2)	F33—C30—F32	106.4 (3)
C9—C13—C14	118.5 (2)	F31—C30—F32	106.7 (3)
C8—C13—C14	118.4 (2)	F33—C30—S26	112.4 (2)
N10—C14—C5	122.3 (2)	F31—C30—S26	111.7 (2)
N10—C14—C13	119.5 (2)	F32—C30—S26	112.0 (2)
C11—C1—C2—C3	−0.9 (4)	C6—C5—C14—C13	1.7 (4)
C1—C2—C3—C4	0.7 (5)	C9—C13—C14—N10	0.1 (3)
C2—C3—C4—C12	0.4 (5)	C8—C13—C14—N10	177.6 (2)
C14—C5—C6—C7	−0.1 (4)	C9—C13—C14—C5	−179.5 (2)
C5—C6—C7—C8	−1.3 (4)	C8—C13—C14—C5	−2.0 (3)
C6—C7—C8—C13	1.1 (4)	C13—C9—C15—O17	71.6 (3)
C13—C9—C11—C1	178.1 (2)	C11—C9—C15—O17	−105.2 (3)
C15—C9—C11—C1	−5.2 (3)	C13—C9—C15—O16	−107.5 (2)
C13—C9—C11—C12	−1.5 (3)	C11—C9—C15—O16	75.7 (3)
C15—C9—C11—C12	175.2 (2)	O17—C15—O16—C18	−3.1 (4)
C2—C1—C11—C9	−179.6 (2)	C9—C15—O16—C18	175.98 (19)
C2—C1—C11—C12	0.0 (4)	C15—O16—C18—C23	109.5 (2)
C14—N10—C12—C4	−179.9 (2)	C15—O16—C18—C19	−74.8 (3)
C25—N10—C12—C4	−0.5 (4)	C23—C18—C19—C20	−2.3 (4)
C14—N10—C12—C11	−0.7 (3)	O16—C18—C19—C20	−177.8 (2)
C25—N10—C12—C11	178.7 (2)	C18—C19—C20—C21	0.6 (4)
C3—C4—C12—N10	177.9 (3)	C19—C20—C21—F24	179.8 (2)
C3—C4—C12—C11	−1.3 (4)	C19—C20—C21—C22	1.0 (4)
C9—C11—C12—N10	1.5 (3)	F24—C21—C22—C23	−179.8 (2)
C1—C11—C12—N10	−178.2 (2)	C20—C21—C22—C23	−1.1 (4)
C9—C11—C12—C4	−179.3 (2)	C19—C18—C23—C22	2.3 (4)
C1—C11—C12—C4	1.1 (3)	O16—C18—C23—C22	177.9 (2)
C11—C9—C13—C8	−176.6 (2)	C21—C22—C23—C18	−0.6 (4)
C15—C9—C13—C8	6.6 (3)	O29—S26—C30—F33	−176.9 (2)
C11—C9—C13—C14	0.8 (3)	O27—S26—C30—F33	61.8 (3)
C15—C9—C13—C14	−176.0 (2)	O28—S26—C30—F33	−57.3 (3)
C7—C8—C13—C9	178.0 (2)	O29—S26—C30—F31	62.5 (3)
C7—C8—C13—C14	0.6 (4)	O27—S26—C30—F31	−58.8 (3)
C12—N10—C14—C5	179.4 (2)	O28—S26—C30—F31	−177.9 (2)
C25—N10—C14—C5	0.1 (4)	O29—S26—C30—F32	−57.1 (3)
C12—N10—C14—C13	−0.1 (3)	O27—S26—C30—F32	−178.4 (2)
C25—N10—C14—C13	−179.5 (2)	O28—S26—C30—F32	62.5 (3)
C6—C5—C14—N10	−177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O17i	0.93	2.49	3.299 (3)	146
C4—H4···O27	0.93	2.46	3.185 (3)	134
C5—H5···O27ii	0.93	2.53	3.200 (4)	130
C22—H22···O29iii	0.93	2.54	3.399 (3)	153

X	I	J	I···J	X···J	X-I···J
C21	F24	Cg2i	3.870 (2)	3.616 (3)	69.12 (12)
C30	F33	Cg2iv	3.835 (2)	4.951 (4)	143.41 (19)
S26	O29	Cg1ii	3.646 (2)	5.055 (15)	170.66 (13)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	4v	3.572 (2)	5.04 (11)	3.408 (1)	1.089 (2)
2	4i	3.856 (2)	4.29 (13)	3.596 (2)	1.392 (2)
3	4v	3.898 (2)	4.66 (12)	3.380 (2)	1.942 (2)
4	1v	3.572 (2)	5.04 (11)	3.472 (1)	0.839 (2)
4	2i	3.856 (2)	4.29 (13)	3.502 (1)	1.614 (2)
4	3v	3.898 (2)	4.66 (12)	3.483 (1)	1.750 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O17i	0.93	2.49	3.299 (3)	146
C4—H4⋯O27	0.93	2.46	3.185 (3)	134
C5—H5⋯O27ii	0.93	2.53	3.200 (4)	130
C22—H22⋯O29iii	0.93	2.54	3.399 (3)	153

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

Table 2

C—F⋯π and S—O⋯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
C21	F24	Cg2i	3.870 (2)	3.616 (3)	69.12 (12)
C30	F33	Cg2iv	3.835 (2)	4.951 (4)	143.41 (19)
S26	O29	Cg1ii	3.646 (2)	5.055 (15)	170.66 (13)

Symmetry codes: (i) −x, −y, −z; (ii) −x + , y + , −z + ; (iv) −x, y, −z + .

Table 3

π–π inter­actions (Å,°)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12, 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
1	4v	3.572 (2)	5.04 (11)	3.408 (1)	1.089 (2)
2	4i	3.856 (2)	4.29 (13)	3.596 (2)	1.392 (2)
3	4v	3.898 (2)	4.66 (12)	3.380 (2)	1.942 (2)
4	1v	3.572 (2)	5.04 (11)	3.472 (1)	0.839 (2)
4	2i	3.856 (2)	4.29 (13)	3.502 (1)	1.614 (2)
4	3v	3.898 (2)	4.66 (12)	3.483 (1)	1.750 (2)

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