9-Phenyl-10H-acridinium trifluoro-methane-sulfonate.

In the crystal structure of the title compound, C(19)H(14)N(+)·CF(3)SO(3) (-), the cations are linked to each other by very weak C-H⋯π inter-actions, while the cations and anions are connected by N-H⋯O, C-H⋯O and S-O⋯π inter-actions. The acridine ring system and the phenyl ring are oriented at an angle of 80.1 (1)° with respect to each other. The mean planes of adjacent acridine units are either parallel or inclined at an angle of 35.6 (1)°. The trifluoro-methane-sulfonate anions are disordered over two positions; the site occupancy factors are 0.591 (8) and 0.409 (8).

Related literature

For general background to chemiluminescence, see: Sato (1996 ▶); Wróblewska et al. (2004 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Huta et al. (2002 ▶); Magnussen et al. (2007 ▶); Stowell et al. (1991 ▶); Toma et al. (1994 ▶); Trzybiński et al. (2010 ▶); Zadykowicz et al. (2009a ▶,b ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Dorn et al. (2005 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Tsuge et al. (1965 ▶); Zadykowicz et al. (2009b ▶). For the treatment of the disorder, see: Müller et al. (2006 ▶).

Experimental

Crystal data

C19H14N+·CF3SO3 −

M = 405.39

Monoclinic,

a = 9.7064 (5) Å

b = 8.9220 (3) Å

c = 21.8665 (9) Å

β = 100.902 (4)°

V = 1859.47 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.40 × 0.15 × 0.04 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.895, T max = 1.000

35783 measured reflections

3296 independent reflections

1565 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.184

S = 1.03

3296 reflections

281 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.30 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/S1600536810040900/vm2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040900/vm2046Isup2.hkl

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

C19H14N+·CF3SO3−	F(000) = 832
Mr = 405.39	Dx = 1.448 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7503 reflections
a = 9.7064 (5) Å	θ = 3.0–29.2°
b = 8.9220 (3) Å	µ = 0.22 mm−1
c = 21.8665 (9) Å	T = 295 K
β = 100.902 (4)°	Plate, yellow
V = 1859.47 (14) Å3	0.40 × 0.15 × 0.04 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3296 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1565 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −10→10
Tmin = 0.895, Tmax = 1.000	l = −26→26
35783 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3
3296 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.31 e Å−3
18 restraints	Δρmin = −0.30 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	Occ. (<1)
C1	0.4643 (5)	0.6284 (4)	0.27061 (19)	0.0756 (12)
H1	0.4534	0.5817	0.2320	0.091*
C2	0.4201 (5)	0.7706 (4)	0.2742 (2)	0.0851 (13)
H2	0.3797	0.8207	0.2379	0.102*
C3	0.4339 (5)	0.8442 (5)	0.3312 (3)	0.0909 (14)
H3	0.4027	0.9425	0.3325	0.109*
C4	0.4925 (5)	0.7740 (4)	0.3849 (2)	0.0791 (12)
H4	0.5011	0.8233	0.4229	0.095*
C5	0.6975 (5)	0.3417 (5)	0.4947 (2)	0.0798 (12)
H5	0.7091	0.3970	0.5314	0.096*
C6	0.7339 (5)	0.1953 (6)	0.4955 (2)	0.0906 (14)
H6	0.7685	0.1494	0.5335	0.109*
C7	0.7211 (5)	0.1098 (5)	0.4403 (2)	0.0840 (13)
H7	0.7474	0.0094	0.4426	0.101*
C8	0.6709 (4)	0.1728 (4)	0.3841 (2)	0.0713 (11)
H8	0.6639	0.1162	0.3479	0.086*
C9	0.5736 (4)	0.3985 (4)	0.32456 (16)	0.0580 (10)
N10	0.6000 (4)	0.5519 (4)	0.43513 (16)	0.0716 (10)
H10	0.611 (5)	0.600 (4)	0.4680 (19)	0.086*
C11	0.5279 (4)	0.5477 (4)	0.32528 (17)	0.0615 (10)
C12	0.5403 (4)	0.6246 (4)	0.38231 (18)	0.0661 (11)
C13	0.6286 (4)	0.3275 (4)	0.38061 (18)	0.0608 (10)
C14	0.6417 (4)	0.4080 (4)	0.43728 (18)	0.0660 (11)
C15	0.5655 (4)	0.3198 (4)	0.26420 (17)	0.0625 (10)
C16	0.6630 (6)	0.3472 (5)	0.2280 (2)	0.0960 (15)
H16	0.7368	0.4127	0.2420	0.115*
C17	0.6528 (7)	0.2784 (6)	0.1707 (3)	0.1125 (18)
H17	0.7200	0.2972	0.1465	0.135*
C18	0.5456 (8)	0.1840 (6)	0.1498 (2)	0.1074 (18)
H18	0.5393	0.1384	0.1111	0.129*
C19	0.4483 (7)	0.1554 (5)	0.1842 (2)	0.1045 (17)
H19	0.3748	0.0901	0.1696	0.125*
C20	0.4578 (5)	0.2241 (4)	0.24210 (19)	0.0828 (13)
H20	0.3900	0.2045	0.2660	0.099*
S21	0.73545 (11)	0.75830 (11)	0.58719 (4)	0.0664 (4)
O22A	0.6636 (9)	0.8243 (11)	0.5314 (3)	0.218 (6)	0.591 (8)
O22B	0.6445 (7)	0.7598 (6)	0.5283 (3)	0.0458 (19)*	0.409 (8)
O23A	0.7106 (11)	0.6045 (7)	0.5921 (4)	0.218 (6)	0.591 (8)
O23B	0.7280 (9)	0.6199 (7)	0.6195 (2)	0.052 (2)*	0.409 (8)
O24A	0.7300 (9)	0.8420 (9)	0.6409 (3)	0.136 (3)	0.591 (8)
O24B	0.7450 (11)	0.8840 (7)	0.6215 (3)	0.074 (2)*	0.409 (8)
C25	0.9128 (6)	0.7584 (6)	0.5725 (3)	0.0964 (15)
F26A	0.9168 (11)	0.6857 (11)	0.5215 (3)	0.298 (9)	0.591 (8)
F27A	0.9485 (9)	0.8946 (5)	0.5642 (4)	0.200 (5)	0.591 (8)
F28A	1.0032 (6)	0.7006 (8)	0.6159 (3)	0.126 (3)	0.591 (8)
F26B	0.9370 (13)	0.6408 (7)	0.5392 (4)	0.102 (3)*	0.409 (8)
F27B	0.940 (2)	0.8798 (10)	0.5386 (3)	0.134 (4)*	0.409 (8)
F28B	1.0068 (14)	0.7612 (8)	0.6237 (4)	0.108 (4)*	0.409 (8)

	U11	U22	U33	U12	U13	U23
C1	0.089 (3)	0.070 (2)	0.066 (3)	0.001 (2)	0.010 (2)	0.001 (2)
C2	0.099 (3)	0.069 (3)	0.083 (3)	0.015 (2)	0.007 (3)	0.002 (2)
C3	0.098 (4)	0.071 (3)	0.105 (4)	0.009 (2)	0.022 (3)	0.003 (3)
C4	0.088 (3)	0.069 (3)	0.084 (3)	−0.008 (2)	0.023 (3)	−0.024 (2)
C5	0.073 (3)	0.098 (3)	0.061 (3)	−0.005 (2)	−0.004 (2)	−0.004 (2)
C6	0.076 (3)	0.116 (4)	0.071 (3)	−0.003 (3)	−0.008 (2)	0.017 (3)
C7	0.080 (3)	0.078 (3)	0.088 (3)	−0.002 (2)	0.002 (3)	0.012 (3)
C8	0.067 (3)	0.069 (2)	0.074 (3)	0.001 (2)	0.003 (2)	0.004 (2)
C9	0.056 (2)	0.061 (2)	0.056 (2)	−0.0061 (17)	0.0074 (19)	0.0001 (18)
N10	0.071 (2)	0.078 (2)	0.063 (2)	−0.0116 (17)	0.0054 (19)	−0.0177 (18)
C11	0.061 (2)	0.060 (2)	0.064 (2)	−0.0055 (17)	0.0114 (19)	−0.0064 (19)
C12	0.069 (3)	0.068 (2)	0.059 (3)	−0.0110 (19)	0.007 (2)	−0.006 (2)
C13	0.053 (2)	0.067 (2)	0.060 (3)	−0.0068 (17)	0.0047 (19)	−0.001 (2)
C14	0.057 (3)	0.074 (3)	0.063 (3)	−0.0089 (19)	0.002 (2)	−0.001 (2)
C15	0.073 (3)	0.057 (2)	0.057 (2)	−0.0023 (19)	0.011 (2)	−0.0020 (18)
C16	0.100 (4)	0.106 (3)	0.088 (3)	−0.018 (3)	0.034 (3)	−0.020 (3)
C17	0.136 (5)	0.112 (4)	0.105 (4)	−0.001 (4)	0.064 (4)	−0.018 (3)
C18	0.166 (6)	0.089 (3)	0.072 (3)	0.014 (4)	0.034 (4)	−0.010 (3)
C19	0.140 (5)	0.092 (3)	0.072 (3)	−0.029 (3)	−0.004 (3)	−0.015 (3)
C20	0.098 (3)	0.088 (3)	0.063 (3)	−0.021 (2)	0.015 (2)	−0.007 (2)
S21	0.0669 (7)	0.0723 (7)	0.0562 (6)	−0.0034 (5)	0.0017 (5)	−0.0060 (5)
O22A	0.114 (6)	0.346 (13)	0.158 (7)	−0.095 (8)	−0.068 (5)	0.157 (8)
O23A	0.170 (9)	0.106 (5)	0.417 (17)	−0.067 (5)	0.158 (11)	−0.110 (8)
O24A	0.105 (5)	0.222 (8)	0.079 (5)	−0.008 (6)	0.011 (4)	−0.081 (5)
C25	0.089 (4)	0.111 (4)	0.089 (4)	−0.023 (3)	0.016 (3)	−0.006 (3)
F26A	0.155 (9)	0.60 (3)	0.167 (8)	−0.020 (12)	0.108 (8)	−0.114 (11)
F27A	0.068 (4)	0.171 (6)	0.355 (12)	−0.011 (4)	0.028 (7)	0.181 (8)
F28A	0.056 (3)	0.101 (4)	0.209 (7)	0.025 (3)	−0.002 (3)	0.055 (4)

C1—C2	1.347 (5)	C13—C14	1.417 (5)
C1—C11	1.431 (5)	C15—C20	1.365 (5)
C1—H1	0.9300	C15—C16	1.367 (6)
C2—C3	1.393 (6)	C16—C17	1.381 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.358 (6)	C17—C18	1.349 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C12	1.415 (5)	C18—C19	1.339 (7)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.353 (6)	C19—C20	1.394 (6)
C5—C14	1.401 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.412 (6)	S21—O24B	1.342 (6)
C6—H6	0.9300	S21—O23A	1.401 (7)
C7—C8	1.356 (5)	S21—O24A	1.401 (5)
C7—H7	0.9300	S21—O22A	1.413 (6)
C8—C13	1.438 (5)	S21—O22B	1.417 (6)
C8—H8	0.9300	S21—O23B	1.431 (6)
C9—C13	1.393 (5)	S21—C25	1.810 (5)
C9—C11	1.404 (5)	C25—F28A	1.274 (7)
C9—C15	1.484 (5)	C25—F27A	1.286 (7)
N10—C14	1.344 (5)	C25—F26A	1.296 (8)
N10—C12	1.356 (5)	C25—F28B	1.305 (10)
N10—H10	0.83 (4)	C25—F26B	1.322 (10)
C11—C12	1.409 (5)	C25—F27B	1.366 (11)
C2—C1—C11	121.1 (4)	C19—C18—C17	120.6 (5)
C2—C1—H1	119.4	C19—C18—H18	119.7
C11—C1—H1	119.4	C17—C18—H18	119.7
C1—C2—C3	121.2 (4)	C18—C19—C20	119.6 (5)
C1—C2—H2	119.4	C18—C19—H19	120.2
C3—C2—H2	119.4	C20—C19—H19	120.2
C4—C3—C2	120.7 (4)	C15—C20—C19	120.7 (5)
C4—C3—H3	119.7	C15—C20—H20	119.6
C2—C3—H3	119.7	C19—C20—H20	119.6
C3—C4—C12	119.1 (4)	O24B—S21—O23A	140.3 (5)
C3—C4—H4	120.5	O24B—S21—O24A	25.3 (4)
C12—C4—H4	120.5	O23A—S21—O24A	115.0 (3)
C6—C5—C14	118.3 (4)	O24B—S21—O22A	96.0 (5)
C6—C5—H5	120.9	O23A—S21—O22A	114.2 (2)
C14—C5—H5	120.9	O24A—S21—O22A	114.2 (4)
C5—C6—C7	122.1 (4)	O24B—S21—O22B	117.7 (4)
C5—C6—H6	119.0	O23A—S21—O22B	89.6 (4)
C7—C6—H6	119.0	O24A—S21—O22B	129.9 (4)
C8—C7—C6	120.6 (4)	O22A—S21—O22B	24.7 (4)
C8—C7—H7	119.7	O24B—S21—O23B	116.8 (2)
C6—C7—H7	119.7	O23A—S21—O23B	24.6 (4)
C7—C8—C13	119.7 (4)	O24A—S21—O23B	91.9 (4)
C7—C8—H8	120.1	O22A—S21—O23B	136.2 (4)
C13—C8—H8	120.1	O22B—S21—O23B	112.0 (2)
C13—C9—C11	119.4 (3)	O24B—S21—C25	97.5 (5)
C13—C9—C15	121.0 (3)	O23A—S21—C25	101.4 (5)
C11—C9—C15	119.6 (3)	O24A—S21—C25	109.7 (4)
C14—N10—C12	124.4 (3)	O22A—S21—C25	100.2 (4)
C14—N10—H10	118 (3)	O22B—S21—C25	106.7 (3)
C12—N10—H10	117 (3)	O23B—S21—C25	103.1 (4)
C9—C11—C12	119.8 (4)	F28A—C25—F27A	108.7 (5)
C9—C11—C1	123.7 (3)	F28A—C25—F26A	108.1 (5)
C12—C11—C1	116.5 (3)	F27A—C25—F26A	107.4 (5)
N10—C12—C11	118.2 (4)	F28A—C25—F28B	25.3 (4)
N10—C12—C4	120.4 (4)	F27A—C25—F28B	86.5 (6)
C11—C12—C4	121.4 (4)	F26A—C25—F28B	128.2 (8)
C9—C13—C14	119.7 (3)	F28A—C25—F26B	85.4 (5)
C9—C13—C8	122.7 (4)	F27A—C25—F26B	126.3 (8)
C14—C13—C8	117.5 (4)	F26A—C25—F26B	25.0 (4)
N10—C14—C5	119.8 (4)	F28B—C25—F26B	108.6 (6)
N10—C14—C13	118.4 (3)	F28A—C25—F27B	123.3 (9)
C5—C14—C13	121.7 (4)	F27A—C25—F27B	24.4 (4)
C20—C15—C16	118.3 (4)	F26A—C25—F27B	83.7 (5)
C20—C15—C9	121.3 (4)	F28B—C25—F27B	105.9 (7)
C16—C15—C9	120.3 (4)	F26B—C25—F27B	105.0 (6)
C15—C16—C17	120.5 (5)	F28A—C25—S21	114.3 (5)
C15—C16—H16	119.8	F27A—C25—S21	108.4 (5)
C17—C16—H16	119.8	F26A—C25—S21	109.7 (6)
C18—C17—C16	120.2 (5)	F28B—C25—S21	112.4 (7)
C18—C17—H17	119.9	F26B—C25—S21	111.8 (6)
C16—C17—H17	119.9	F27B—C25—S21	112.6 (9)
C11—C1—C2—C3	−0.3 (7)	C16—C17—C18—C19	−0.2 (9)
C1—C2—C3—C4	−0.1 (7)	C17—C18—C19—C20	0.1 (8)
C2—C3—C4—C12	0.3 (7)	C16—C15—C20—C19	0.4 (7)
C14—C5—C6—C7	1.8 (7)	C9—C15—C20—C19	177.4 (4)
C5—C6—C7—C8	−0.1 (7)	C18—C19—C20—C15	−0.2 (8)
C6—C7—C8—C13	−0.8 (7)	O24B—S21—C25—F28A	83.8 (5)
C13—C9—C11—C12	1.2 (5)	O23A—S21—C25—F28A	−61.2 (5)
C15—C9—C11—C12	−177.6 (3)	O24A—S21—C25—F28A	60.8 (6)
C13—C9—C11—C1	−177.2 (4)	O22A—S21—C25—F28A	−178.7 (5)
C15—C9—C11—C1	4.0 (6)	O22B—S21—C25—F28A	−154.2 (5)
C2—C1—C11—C9	178.8 (4)	O23B—S21—C25—F28A	−36.0 (5)
C2—C1—C11—C12	0.4 (6)	O24B—S21—C25—F27A	−37.7 (6)
C14—N10—C12—C11	−3.7 (6)	O23A—S21—C25—F27A	177.4 (5)
C14—N10—C12—C4	176.5 (4)	O24A—S21—C25—F27A	−60.6 (6)
C9—C11—C12—N10	1.6 (5)	O22A—S21—C25—F27A	59.9 (6)
C1—C11—C12—N10	−180.0 (4)	O22B—S21—C25—F27A	84.3 (5)
C9—C11—C12—C4	−178.6 (4)	O23B—S21—C25—F27A	−157.5 (5)
C1—C11—C12—C4	−0.1 (6)	O24B—S21—C25—F26A	−154.7 (6)
C3—C4—C12—N10	179.6 (4)	O23A—S21—C25—F26A	60.4 (6)
C3—C4—C12—C11	−0.2 (6)	O24A—S21—C25—F26A	−177.6 (6)
C11—C9—C13—C14	−2.0 (5)	O22A—S21—C25—F26A	−57.1 (6)
C15—C9—C13—C14	176.7 (3)	O22B—S21—C25—F26A	−32.7 (6)
C11—C9—C13—C8	176.7 (4)	O23B—S21—C25—F26A	85.5 (6)
C15—C9—C13—C8	−4.5 (6)	O24B—S21—C25—F28B	56.2 (5)
C7—C8—C13—C9	−178.7 (4)	O23A—S21—C25—F28B	−88.7 (6)
C7—C8—C13—C14	0.0 (6)	O24A—S21—C25—F28B	33.3 (6)
C12—N10—C14—C5	−177.6 (4)	O22A—S21—C25—F28B	153.7 (6)
C12—N10—C14—C13	2.8 (6)	O22B—S21—C25—F28B	178.2 (5)
C6—C5—C14—N10	177.8 (4)	O23B—S21—C25—F28B	−63.6 (5)
C6—C5—C14—C13	−2.7 (6)	O24B—S21—C25—F26B	178.7 (5)
C9—C13—C14—N10	0.1 (5)	O23A—S21—C25—F26B	33.7 (6)
C8—C13—C14—N10	−178.7 (4)	O24A—S21—C25—F26B	155.8 (5)
C9—C13—C14—C5	−179.5 (4)	O22A—S21—C25—F26B	−83.8 (6)
C8—C13—C14—C5	1.8 (5)	O22B—S21—C25—F26B	−59.3 (5)
C13—C9—C15—C20	82.2 (5)	O23B—S21—C25—F26B	58.9 (5)
C11—C9—C15—C20	−99.1 (5)	O24B—S21—C25—F27B	−63.4 (6)
C13—C9—C15—C16	−100.9 (5)	O23A—S21—C25—F27B	151.7 (5)
C11—C9—C15—C16	77.9 (5)	O24A—S21—C25—F27B	−86.3 (6)
C20—C15—C16—C17	−0.6 (7)	O22A—S21—C25—F27B	34.1 (6)
C9—C15—C16—C17	−177.6 (4)	O22B—S21—C25—F27B	58.6 (5)
C15—C16—C17—C18	0.5 (8)	O23B—S21—C25—F27B	176.8 (5)

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O24Ai	0.93	2.44	3.333 (9)	160
C4—H4···O22A	0.93	2.59	3.348 (8)	139
C5—H5···O23A	0.93	2.28	3.154 (9)	157
N10—H10···O22A	0.83 (4)	2.43 (4)	3.198 (9)	154 (3)
C17—H17···Cg2ii	0.93	2.99	3.632 (7)	127
C20—H20···O24Aiii	0.93	2.56	3.461 (9)	162

X	I	J	I···J	X···J	X–I···J
C25	F26A	Cg3iv	3.855 (11)	3.987 (6)	86.3 (5)
C25	F28A	Cg3iv	3.501 (6)	3.987 (6)	103.1 (4)
S21	O22A	Cg3iii	3.617 (9)	3.990 (2)	94.7 (4)
S21	O23A	Cg1iii	3.125 (11)	3.923 (2)	114.7 (5)
C25	F26B	Cg3iv	3.743 (13)	3.987 (6)	90.8 (6)
C25	F28B	Cg3iii	3.545 (13)	3.987 (6)	100.2 (6)
S21	O22B	Cg3iii	3.387 (7)	3.990 (2)	104.7 (3)
S21	O23B	Cg1iii	3.159 (9)	3.923 (2)	111.8 (4)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O24Ai	0.93	2.44	3.333 (9)	160
C4—H4⋯O22A	0.93	2.59	3.348 (8)	139
C5—H5⋯O23A	0.93	2.28	3.154 (9)	157
N10—H10⋯O22A	0.83 (4)	2.43 (4)	3.198 (9)	154 (3)
C17—H17⋯Cg2ii	0.93	2.99	3.632 (7)	127
C20—H20⋯O24Aiii	0.93	2.56	3.461 (9)	162

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

Table 2

S–O⋯π inter­actions (Å, °)

Cg1 and Cg3 are the centroids of the C9/N10/C11–C14 and C5–C8/C13/C14 rings, respectively.

X	I	J	I⋯J	X⋯J	X–I⋯J
S21	O23A	Cg1iii	3.125 (11)	3.923 (2)	114.7 (5)
S21	O22B	Cg3iii	3.387 (7)	3.990 (2)	104.7 (3)
S21	O23B	Cg1iii	3.159 (9)	3.923 (2)	111.8 (4)

Symmetry code: (iii) .