9-(Biphenyl-4-yl-oxycarbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

In the crystal structure of the title compound, C(27)H(20)NO(2) (+)·CF(3)SO(3) (-), the cations form inversion dimers through π-π inter-actions between the acridine ring systems [centroid-centroid distances = 3.668 (2)-3.994 (2) Å]. These dimers are further linked by C-H⋯O and C-H⋯π inter-actions. The cation and the anion are connected by C-H⋯O inter-actions. The mean plane of the acridine ring system makes dihedral angles of 10.6 (1) and 82.5 (1)°, respectively, with the adjacent phenyl ring and the carb-oxy group. The two phenyl rings of the biphenyl group are oriented at 42.9 (1)°.

Related literature

For general background, see: Adamczyk et al. (2004 ▶); Becker et al. (1999 ▶); Dodeigne et al. (2000 ▶); Rak et al. (1999 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2007 ▶, 2008 ▶). For mol­ecular inter­actions, see: Bianchi et al. (2004 ▶); Hunter & Sanders (1990 ▶); Steiner (1999 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Sikorski et al. (2007 ▶).

Experimental

Crystal data

C27H20NO2 +·CF3SO3 −

M = 539.52

Monoclinic,

a = 9.4619 (2) Å

b = 12.4558 (5) Å

c = 20.7903 (7) Å

β = 94.559 (3)°

V = 2442.50 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.6 × 0.12 × 0.1 mm

Data collection

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer

Absorption correction: multi-scan (; Oxford Diffraction, 2008 ▶) T min = 0.887, T max = 0.977

42490 measured reflections

4408 independent reflections

3454 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.05

4408 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.39 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/S1600536809007569/is2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007569/is2396Isup2.hkl

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

C27H20NO2+·CF3SO3−	F(000) = 1112
Mr = 539.52	Dx = 1.467 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1909 reflections
a = 9.4619 (2) Å	θ = 3.0–29.2°
b = 12.4558 (5) Å	µ = 0.20 mm−1
c = 20.7903 (7) Å	T = 295 K
β = 94.559 (3)°	Needle, yellow
V = 2442.50 (14) Å3	0.6 × 0.12 × 0.1 mm
Z = 4

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer	4408 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3454 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.4002 pixels mm-1	θmax = 25.3°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→14
Tmin = 0.887, Tmax = 0.977	l = −24→24
42490 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.3778P] where P = (Fo2 + 2Fc2)/3
4408 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0826 (2)	0.85546 (17)	0.66803 (10)	0.0559 (5)
H1	0.1794	0.8419	0.6743	0.067*
C2	0.0070 (2)	0.8721 (2)	0.71966 (11)	0.0666 (6)
H2	0.0516	0.8705	0.7612	0.080*
C3	−0.1399 (2)	0.8920 (2)	0.71009 (11)	0.0661 (6)
H3	−0.1913	0.9025	0.7459	0.079*
C4	−0.2082 (2)	0.89610 (17)	0.65079 (10)	0.0556 (5)
H4	−0.3052	0.9097	0.6462	0.067*
C5	−0.1940 (2)	0.87413 (17)	0.41735 (10)	0.0533 (5)
H5	−0.2913	0.8854	0.4114	0.064*
C6	−0.1171 (2)	0.86205 (18)	0.36536 (11)	0.0608 (6)
H6	−0.1632	0.8652	0.3242	0.073*
C7	0.0303 (2)	0.84498 (17)	0.37199 (11)	0.0589 (5)
H7	0.0807	0.8385	0.3356	0.071*
C8	0.0983 (2)	0.83809 (16)	0.43131 (10)	0.0506 (5)
H8	0.1956	0.8261	0.4355	0.061*
C9	0.08977 (17)	0.84149 (13)	0.54978 (9)	0.0411 (4)
N10	−0.19839 (14)	0.88388 (11)	0.53452 (7)	0.0409 (4)
C11	0.01625 (17)	0.85832 (14)	0.60431 (9)	0.0426 (4)
C12	−0.13276 (18)	0.87986 (14)	0.59538 (9)	0.0432 (4)
C13	0.02305 (17)	0.84892 (13)	0.48766 (9)	0.0407 (4)
C14	−0.12638 (17)	0.86960 (13)	0.48029 (9)	0.0405 (4)
C15	0.24609 (17)	0.81633 (15)	0.55824 (9)	0.0442 (4)
O16	0.26663 (11)	0.71126 (10)	0.55470 (6)	0.0468 (3)
O17	0.33626 (14)	0.88239 (12)	0.56714 (9)	0.0750 (5)
C18	0.40924 (17)	0.67406 (14)	0.56630 (9)	0.0397 (4)
C19	0.48541 (18)	0.65153 (15)	0.51460 (9)	0.0453 (4)
H19	0.4465	0.6623	0.4726	0.054*
C20	0.62226 (18)	0.61225 (15)	0.52661 (8)	0.0443 (4)
H20	0.6754	0.5962	0.4921	0.053*
C21	0.68130 (17)	0.59638 (14)	0.58923 (8)	0.0378 (4)
C22	0.59895 (19)	0.61933 (16)	0.63985 (9)	0.0472 (4)
H22	0.6366	0.6088	0.6821	0.057*
C23	0.46215 (19)	0.65756 (16)	0.62865 (9)	0.0493 (5)
H23	0.4072	0.6718	0.6628	0.059*
C24	0.82954 (17)	0.55657 (14)	0.60215 (8)	0.0385 (4)
C25	0.88247 (19)	0.47452 (16)	0.56618 (9)	0.0497 (5)
H25	0.8243	0.4422	0.5336	0.060*
C26	1.0212 (2)	0.44002 (18)	0.57816 (11)	0.0587 (5)
H26	1.0549	0.3842	0.5539	0.070*
C27	1.1092 (2)	0.48737 (19)	0.62543 (11)	0.0603 (6)
H27	1.2029	0.4649	0.6327	0.072*
C28	1.0580 (2)	0.56810 (19)	0.66193 (11)	0.0607 (6)
H28	1.1171	0.6003	0.6943	0.073*
C29	0.91906 (19)	0.60188 (16)	0.65086 (9)	0.0505 (5)
H29	0.8850	0.6558	0.6765	0.061*
C30	−0.35306 (18)	0.90607 (18)	0.52817 (11)	0.0586 (5)
H30A	−0.4013	0.8538	0.5524	0.088*
H30B	−0.3875	0.9021	0.4835	0.088*
H30C	−0.3703	0.9766	0.5445	0.088*
S31	0.43886 (5)	0.83310 (5)	0.31913 (2)	0.05338 (17)
O32	0.42879 (16)	0.85116 (15)	0.38681 (7)	0.0738 (5)
O33	0.56626 (19)	0.87108 (17)	0.29520 (8)	0.0896 (6)
O34	0.31337 (17)	0.85327 (16)	0.27869 (8)	0.0865 (6)
C35	0.4565 (3)	0.6904 (2)	0.31430 (13)	0.0827 (8)
F36	0.3429 (3)	0.64219 (17)	0.33492 (13)	0.1497 (9)
F37	0.5652 (2)	0.65377 (17)	0.35025 (10)	0.1352 (8)
F38	0.4689 (3)	0.65853 (16)	0.25421 (10)	0.1447 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0429 (10)	0.0619 (13)	0.0621 (13)	0.0029 (9)	−0.0010 (9)	−0.0086 (10)
C2	0.0657 (14)	0.0780 (16)	0.0557 (13)	0.0022 (12)	0.0015 (11)	−0.0135 (11)
C3	0.0630 (13)	0.0762 (16)	0.0614 (14)	0.0035 (11)	0.0188 (11)	−0.0153 (11)
C4	0.0403 (10)	0.0604 (13)	0.0681 (14)	0.0041 (9)	0.0168 (10)	−0.0122 (10)
C5	0.0399 (10)	0.0544 (12)	0.0645 (13)	0.0030 (9)	−0.0023 (9)	−0.0015 (10)
C6	0.0603 (13)	0.0672 (15)	0.0542 (12)	0.0026 (11)	−0.0006 (10)	−0.0018 (10)
C7	0.0614 (13)	0.0612 (13)	0.0559 (13)	−0.0003 (10)	0.0170 (10)	−0.0024 (10)
C8	0.0394 (9)	0.0508 (12)	0.0631 (13)	0.0009 (8)	0.0135 (9)	−0.0019 (9)
C9	0.0294 (8)	0.0343 (10)	0.0597 (11)	−0.0011 (7)	0.0052 (8)	−0.0027 (8)
N10	0.0263 (7)	0.0368 (8)	0.0598 (10)	0.0017 (6)	0.0048 (6)	−0.0044 (7)
C11	0.0323 (8)	0.0389 (10)	0.0568 (11)	0.0007 (7)	0.0045 (8)	−0.0047 (8)
C12	0.0357 (9)	0.0346 (10)	0.0600 (12)	−0.0001 (7)	0.0095 (8)	−0.0063 (8)
C13	0.0317 (8)	0.0333 (9)	0.0577 (11)	−0.0008 (7)	0.0079 (8)	−0.0023 (8)
C14	0.0328 (8)	0.0312 (9)	0.0575 (11)	−0.0004 (7)	0.0048 (8)	−0.0028 (7)
C15	0.0292 (9)	0.0450 (11)	0.0588 (12)	0.0014 (8)	0.0070 (8)	−0.0039 (8)
O16	0.0289 (6)	0.0435 (7)	0.0673 (8)	0.0036 (5)	−0.0001 (5)	−0.0044 (6)
O17	0.0305 (7)	0.0491 (9)	0.1453 (16)	−0.0025 (6)	0.0065 (8)	−0.0091 (9)
C18	0.0279 (8)	0.0392 (10)	0.0518 (11)	0.0032 (7)	0.0021 (7)	−0.0023 (7)
C19	0.0388 (9)	0.0560 (12)	0.0401 (10)	0.0052 (8)	−0.0025 (8)	0.0003 (8)
C20	0.0368 (9)	0.0562 (12)	0.0403 (10)	0.0056 (8)	0.0063 (8)	−0.0029 (8)
C21	0.0356 (9)	0.0363 (9)	0.0413 (9)	0.0008 (7)	0.0020 (7)	−0.0009 (7)
C22	0.0426 (10)	0.0601 (12)	0.0383 (10)	0.0084 (9)	−0.0003 (8)	0.0004 (8)
C23	0.0426 (10)	0.0609 (12)	0.0456 (11)	0.0071 (9)	0.0108 (8)	−0.0043 (9)
C24	0.0335 (8)	0.0389 (10)	0.0429 (10)	0.0022 (7)	0.0016 (7)	0.0068 (7)
C25	0.0396 (9)	0.0508 (12)	0.0589 (12)	0.0032 (8)	0.0044 (8)	−0.0043 (9)
C26	0.0483 (11)	0.0570 (13)	0.0730 (14)	0.0149 (10)	0.0175 (10)	0.0068 (10)
C27	0.0351 (10)	0.0697 (15)	0.0759 (14)	0.0100 (10)	0.0028 (10)	0.0266 (12)
C28	0.0449 (11)	0.0656 (14)	0.0683 (14)	−0.0025 (10)	−0.0171 (10)	0.0106 (11)
C29	0.0460 (10)	0.0477 (11)	0.0562 (12)	0.0035 (9)	−0.0062 (9)	0.0011 (9)
C30	0.0273 (9)	0.0701 (14)	0.0787 (15)	0.0081 (9)	0.0060 (9)	−0.0022 (11)
S31	0.0446 (3)	0.0750 (4)	0.0403 (3)	0.0105 (2)	0.0021 (2)	0.0059 (2)
O32	0.0688 (10)	0.1071 (13)	0.0460 (9)	0.0136 (9)	0.0071 (7)	−0.0074 (8)
O33	0.0748 (11)	0.1331 (16)	0.0616 (10)	−0.0285 (11)	0.0099 (8)	0.0162 (10)
O34	0.0632 (10)	0.1304 (16)	0.0636 (10)	0.0386 (10)	−0.0095 (8)	0.0109 (10)
C35	0.094 (2)	0.0887 (19)	0.0651 (16)	0.0174 (16)	0.0063 (14)	0.0031 (14)
F36	0.160 (2)	0.1052 (16)	0.185 (2)	−0.0438 (14)	0.0162 (17)	0.0355 (14)
F37	0.1460 (17)	0.1334 (16)	0.1238 (16)	0.0835 (14)	−0.0050 (13)	0.0290 (12)
F38	0.231 (3)	0.1055 (14)	0.0970 (14)	0.0430 (15)	0.0084 (15)	−0.0326 (11)

C1—C2	1.352 (3)	C19—C20	1.388 (2)
C1—C11	1.421 (3)	C19—H19	0.9300
C1—H1	0.9300	C20—C21	1.389 (2)
C2—C3	1.411 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.388 (2)
C3—C4	1.347 (3)	C21—C24	1.492 (2)
C3—H3	0.9300	C22—C23	1.382 (3)
C4—C12	1.418 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.358 (3)	C24—C25	1.384 (3)
C5—C14	1.411 (3)	C24—C29	1.388 (3)
C5—H5	0.9300	C25—C26	1.385 (3)
C6—C7	1.407 (3)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.370 (3)
C7—C8	1.347 (3)	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.371 (3)
C8—C13	1.425 (3)	C27—H27	0.9300
C8—H8	0.9300	C28—C29	1.383 (3)
C9—C11	1.392 (3)	C28—H28	0.9300
C9—C13	1.395 (3)	C29—H29	0.9300
C9—C15	1.508 (2)	C30—H30A	0.9600
N10—C12	1.365 (2)	C30—H30B	0.9600
N10—C14	1.374 (2)	C30—H30C	0.9600
N10—C30	1.485 (2)	S31—O33	1.4212 (17)
C11—C12	1.433 (2)	S31—O34	1.4216 (16)
C13—C14	1.433 (2)	S31—O32	1.4356 (15)
C15—O17	1.189 (2)	S31—C35	1.788 (3)
C15—O16	1.326 (2)	C35—F37	1.305 (3)
O16—C18	1.4289 (19)	C35—F38	1.325 (3)
C18—C23	1.368 (3)	C35—F36	1.332 (3)
C18—C19	1.370 (3)
C2—C1—C11	120.93 (19)	C18—C19—H19	120.9
C2—C1—H1	119.5	C20—C19—H19	120.9
C11—C1—H1	119.5	C19—C20—C21	121.24 (16)
C1—C2—C3	119.5 (2)	C19—C20—H20	119.4
C1—C2—H2	120.3	C21—C20—H20	119.4
C3—C2—H2	120.3	C22—C21—C20	118.23 (15)
C4—C3—C2	122.1 (2)	C22—C21—C24	120.56 (15)
C4—C3—H3	118.9	C20—C21—C24	121.21 (15)
C2—C3—H3	118.9	C23—C22—C21	121.20 (17)
C3—C4—C12	120.16 (18)	C23—C22—H22	119.4
C3—C4—H4	119.9	C21—C22—H22	119.4
C12—C4—H4	119.9	C18—C23—C22	118.63 (17)
C6—C5—C14	120.09 (18)	C18—C23—H23	120.7
C6—C5—H5	120.0	C22—C23—H23	120.7
C14—C5—H5	120.0	C25—C24—C29	117.95 (16)
C5—C6—C7	121.9 (2)	C25—C24—C21	121.59 (16)
C5—C6—H6	119.0	C29—C24—C21	120.46 (16)
C7—C6—H6	119.0	C24—C25—C26	120.71 (19)
C8—C7—C6	119.76 (19)	C24—C25—H25	119.6
C8—C7—H7	120.1	C26—C25—H25	119.6
C6—C7—H7	120.1	C27—C26—C25	120.6 (2)
C7—C8—C13	120.91 (18)	C27—C26—H26	119.7
C7—C8—H8	119.5	C25—C26—H26	119.7
C13—C8—H8	119.5	C26—C27—C28	119.42 (18)
C11—C9—C13	121.68 (16)	C26—C27—H27	120.3
C11—C9—C15	119.01 (17)	C28—C27—H27	120.3
C13—C9—C15	119.29 (16)	C27—C28—C29	120.3 (2)
C12—N10—C14	122.46 (14)	C27—C28—H28	119.9
C12—N10—C30	117.50 (15)	C29—C28—H28	119.9
C14—N10—C30	120.04 (16)	C28—C29—C24	121.01 (19)
C9—C11—C1	122.90 (17)	C28—C29—H29	119.5
C9—C11—C12	118.22 (17)	C24—C29—H29	119.5
C1—C11—C12	118.87 (17)	N10—C30—H30A	109.5
N10—C12—C4	121.77 (16)	N10—C30—H30B	109.5
N10—C12—C11	119.83 (15)	H30A—C30—H30B	109.5
C4—C12—C11	118.40 (18)	N10—C30—H30C	109.5
C9—C13—C8	122.43 (16)	H30A—C30—H30C	109.5
C9—C13—C14	118.75 (16)	H30B—C30—H30C	109.5
C8—C13—C14	118.82 (17)	O33—S31—O34	115.21 (11)
N10—C14—C5	122.53 (16)	O33—S31—O32	114.53 (10)
N10—C14—C13	118.99 (16)	O34—S31—O32	115.76 (10)
C5—C14—C13	118.47 (16)	O33—S31—C35	103.03 (14)
O17—C15—O16	125.81 (16)	O34—S31—C35	102.70 (13)
O17—C15—C9	123.99 (17)	O32—S31—C35	102.97 (12)
O16—C15—C9	110.20 (15)	F37—C35—F38	108.1 (2)
C15—O16—C18	116.83 (13)	F37—C35—F36	106.1 (2)
C23—C18—C19	122.49 (16)	F38—C35—F36	107.6 (3)
C23—C18—O16	118.58 (15)	F37—C35—S31	112.9 (2)
C19—C18—O16	118.86 (16)	F38—C35—S31	111.5 (2)
C18—C19—C20	118.19 (17)	F36—C35—S31	110.4 (2)
C11—C1—C2—C3	0.4 (3)	C13—C9—C15—O17	97.2 (2)
C1—C2—C3—C4	−0.7 (4)	C11—C9—C15—O16	97.79 (19)
C2—C3—C4—C12	0.3 (3)	C13—C9—C15—O16	−83.2 (2)
C14—C5—C6—C7	−0.1 (3)	O17—C15—O16—C18	3.8 (3)
C5—C6—C7—C8	1.4 (3)	C9—C15—O16—C18	−175.79 (14)
C6—C7—C8—C13	−0.6 (3)	C15—O16—C18—C23	84.4 (2)
C13—C9—C11—C1	−177.44 (17)	C15—O16—C18—C19	−98.6 (2)
C15—C9—C11—C1	1.6 (3)	C23—C18—C19—C20	−1.1 (3)
C13—C9—C11—C12	2.3 (3)	O16—C18—C19—C20	−178.00 (16)
C15—C9—C11—C12	−178.69 (16)	C18—C19—C20—C21	−0.2 (3)
C2—C1—C11—C9	−179.9 (2)	C19—C20—C21—C22	1.0 (3)
C2—C1—C11—C12	0.4 (3)	C19—C20—C21—C24	−178.56 (17)
C14—N10—C12—C4	179.19 (17)	C20—C21—C22—C23	−0.4 (3)
C30—N10—C12—C4	0.0 (2)	C24—C21—C22—C23	179.15 (18)
C14—N10—C12—C11	−1.1 (2)	C19—C18—C23—C22	1.7 (3)
C30—N10—C12—C11	179.76 (16)	O16—C18—C23—C22	178.58 (17)
C3—C4—C12—N10	−179.76 (19)	C21—C22—C23—C18	−0.9 (3)
C3—C4—C12—C11	0.5 (3)	C22—C21—C24—C25	137.96 (19)
C9—C11—C12—N10	−0.3 (2)	C20—C21—C24—C25	−42.5 (3)
C1—C11—C12—N10	179.44 (16)	C22—C21—C24—C29	−42.4 (3)
C9—C11—C12—C4	179.45 (17)	C20—C21—C24—C29	137.10 (19)
C1—C11—C12—C4	−0.8 (3)	C29—C24—C25—C26	−0.8 (3)
C11—C9—C13—C8	176.29 (17)	C21—C24—C25—C26	178.82 (17)
C15—C9—C13—C8	−2.7 (3)	C24—C25—C26—C27	−0.7 (3)
C11—C9—C13—C14	−2.9 (2)	C25—C26—C27—C28	1.4 (3)
C15—C9—C13—C14	178.10 (15)	C26—C27—C28—C29	−0.4 (3)
C7—C8—C13—C9	179.55 (18)	C27—C28—C29—C24	−1.2 (3)
C7—C8—C13—C14	−1.3 (3)	C25—C24—C29—C28	1.8 (3)
C12—N10—C14—C5	−179.76 (16)	C21—C24—C29—C28	−177.87 (17)
C30—N10—C14—C5	−0.6 (3)	O33—S31—C35—F37	61.9 (2)
C12—N10—C14—C13	0.5 (2)	O34—S31—C35—F37	−178.0 (2)
C30—N10—C14—C13	179.62 (16)	O32—S31—C35—F37	−57.4 (2)
C6—C5—C14—N10	178.39 (19)	O33—S31—C35—F38	−60.0 (2)
C6—C5—C14—C13	−1.8 (3)	O34—S31—C35—F38	60.1 (2)
C9—C13—C14—N10	1.5 (2)	O32—S31—C35—F38	−179.3 (2)
C8—C13—C14—N10	−177.72 (16)	O33—S31—C35—F36	−179.51 (19)
C9—C13—C14—C5	−178.30 (16)	O34—S31—C35—F36	−59.5 (2)
C8—C13—C14—C5	2.5 (2)	O32—S31—C35—F36	61.1 (2)
C11—C9—C15—O17	−81.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O33i	0.93	2.58	3.228 (3)	127
C7—H7···O34	0.93	2.59	3.431 (3)	151
C8—H8···O32	0.93	2.52	3.335 (2)	147
C22—H22···O33ii	0.93	2.51	3.271 (3)	140
C28—H28···O34iii	0.93	2.52	3.429 (3)	166
C30—H30A···O17i	0.96	2.55	3.125 (2)	118
C29—H29···Cg2iv	0.93	2.81	3.417 (2)	123
C30—H30A···Cg4i	0.96	2.83	3.683 (2)	148

I	J	CgI···CgJ	Dihedral angle	CgIPerp	CgJPerp	CgIOffset	CgJOffset
1	1v	3.993 (2)	0	3.609 (2)	3.609 (2)	1.709 (2)	1.709 (2)
1	3v	3.668 (2)	2.0	3.583 (2)	3.578 (2)	0.785 (2)	0.807 (2)
2	3v	3.944 (2)	2.4	3.507 (2)	3.577 (2)	1.804 (2)	1.661 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O33i	0.93	2.58	3.228 (3)	127
C7—H7⋯O34	0.93	2.59	3.431 (3)	151
C8—H8⋯O32	0.93	2.52	3.335 (2)	147
C22—H22⋯O33ii	0.93	2.51	3.271 (3)	140
C28—H28⋯O34iii	0.93	2.52	3.429 (3)	166
C30—H30A⋯O17i	0.96	2.55	3.125 (2)	118
C29—H29⋯Cg2iv	0.93	2.81	3.417 (2)	123
C30—H30A⋯Cg4i	0.96	2.83	3.683 (2)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 and Cg4 are the centroids of the C1–C4/C11/C12 and C18–C23 rings, respectively.

Table 2

π–π Interactions (Å,°)

I	J	CgI⋯CgJ	Dihedral angle	CgIPerp	CgJPerp	CgIOffset	CgJOffset
1	1v	3.993 (2)		3.609 (2)	3.609 (2)	1.709 (2)	1.709 (2)
1	3v	3.668 (2)	2.0	3.583 (2)	3.578 (2)	0.785 (2)	0.807 (2)
2	3v	3.944 (2)	2.4	3.507 (2)	3.577 (2)	1.804 (2)	1.661 (2)

Symmetry codes: (v)

Notes: Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 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 and CgJ Perp are the perpendicular distances of CgI from ring J and of CgJ from ring I, respectively. CgI Offset and CgJ Offset are the distances between CgI and the perpendicular projection of CgJ on ring I, and between CgJ and the perpendicular projection of CgI on ring J, respectively.