10-Methyl-9-[2-(propan-2-yl)phenoxy-carbonyl]-acridinium trifluoro-methane-sulfonate.

In the crystal of the title compound, C(24)H(22)NO(2) (+)·CF(3)SO(3) (-), adjacent cations and anions are connected through C-H⋯O, C-H⋯F and S-O⋯π inter-actions, while neighboring cations via π-π inter-actions [centroid-centroid distance = 3.962 (2) Å]. The acridine and benzene ring systems are oriented at a dihedral angle of 14.6 (1)°. The carboxyl group is twisted at an angle of 87.6 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel or inclined at an angle of 13.4 (1)° in the crystal structure.

Related literature

For background to the chemiluminogenic properties of 9-phen­oxy­carbonyl-10-methyl­acridinium trifluoro­meth­ane­sulfonates, see: Natrajan et al. (2010 ▶); 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. (2006 ▶, 2007 ▶); Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Lyssenko & Anti­pin (2004 ▶); Novoa et al. (2006 ▶). For the synthesis, see: Sato (1996 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C24H22NO2 +·CF3SO3 −

M = 505.51

Monoclinic,

a = 14.4346 (7) Å

b = 12.9677 (5) Å

c = 13.0862 (5) Å

β = 107.160 (5)°

V = 2340.47 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.32 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.955, T max = 1.000

17556 measured reflections

4169 independent reflections

2436 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.116

S = 0.93

4169 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.26 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/S160053681003953X/ng5040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003953X/ng5040Isup2.hkl

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

C24H22NO2+·CF3SO3−	F(000) = 1048
Mr = 505.51	Dx = 1.435 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5919 reflections
a = 14.4346 (7) Å	θ = 3.0–29.2°
b = 12.9677 (5) Å	µ = 0.20 mm−1
c = 13.0862 (5) Å	T = 295 K
β = 107.160 (5)°	Prism, yellow
V = 2340.47 (17) Å3	0.32 × 0.20 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	4169 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	2436 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −15→15
Tmin = 0.955, Tmax = 1.000	l = −15→14
17556 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3
4169 reflections	(Δ/σ)max = 0.002
319 parameters	Δρmax = 0.34 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	0.79663 (19)	0.93471 (19)	0.23882 (19)	0.0538 (6)
H1	0.7585	0.9653	0.2766	0.065*
C2	0.83868 (19)	0.9943 (2)	0.1808 (2)	0.0597 (7)
H2	0.8295	1.0653	0.1783	0.072*
C3	0.89659 (19)	0.9483 (2)	0.12396 (19)	0.0611 (7)
H3	0.9250	0.9899	0.0836	0.073*
C4	0.91234 (18)	0.8453 (2)	0.12618 (18)	0.0543 (7)
H4	0.9516	0.8173	0.0883	0.065*
C5	0.85827 (19)	0.50582 (19)	0.25407 (18)	0.0529 (6)
H5	0.8967	0.4761	0.2162	0.064*
C6	0.8169 (2)	0.4459 (2)	0.3131 (2)	0.0630 (7)
H6	0.8270	0.3750	0.3146	0.076*
C7	0.7591 (2)	0.4880 (2)	0.3722 (2)	0.0615 (7)
H7	0.7319	0.4452	0.4127	0.074*
C8	0.74323 (19)	0.58985 (19)	0.37013 (18)	0.0511 (6)
H8	0.7052	0.6173	0.4098	0.061*
C9	0.76717 (16)	0.76264 (17)	0.30277 (17)	0.0416 (6)
N10	0.88297 (13)	0.67612 (15)	0.18987 (14)	0.0445 (5)
C11	0.80948 (17)	0.82595 (17)	0.24349 (17)	0.0429 (6)
C12	0.86933 (16)	0.78034 (18)	0.18595 (17)	0.0429 (6)
C13	0.78353 (16)	0.65678 (17)	0.30837 (16)	0.0415 (6)
C14	0.84322 (17)	0.61298 (17)	0.24995 (17)	0.0433 (6)
C15	0.70287 (18)	0.80997 (17)	0.3623 (2)	0.0450 (6)
O16	0.61194 (12)	0.81571 (14)	0.29809 (12)	0.0569 (5)
O17	0.72938 (13)	0.83794 (15)	0.45268 (14)	0.0667 (5)
C18	0.54272 (18)	0.8721 (2)	0.33483 (17)	0.0516 (6)
C19	0.48032 (18)	0.8207 (2)	0.37892 (18)	0.0529 (7)
C20	0.4108 (2)	0.8824 (2)	0.4042 (2)	0.0648 (8)
H20	0.3666	0.8514	0.4338	0.078*
C21	0.4053 (2)	0.9861 (3)	0.3872 (2)	0.0688 (8)
H21	0.3582	1.0245	0.4057	0.083*
C22	0.4685 (2)	1.0341 (2)	0.3430 (2)	0.0718 (8)
H22	0.4648	1.1049	0.3313	0.086*
C23	0.5384 (2)	0.9758 (2)	0.3157 (2)	0.0652 (8)
H23	0.5817	1.0070	0.2849	0.078*
C24	0.4878 (2)	0.7061 (2)	0.4025 (2)	0.0665 (8)
H24	0.5264	0.6755	0.3599	0.080*
C25	0.5415 (3)	0.6867 (3)	0.5193 (3)	0.1123 (14)
H25A	0.6038	0.7197	0.5370	0.168*
H25B	0.5500	0.6138	0.5315	0.168*
H25C	0.5047	0.7143	0.5632	0.168*
C26	0.3890 (3)	0.6532 (3)	0.3699 (3)	0.1142 (14)
H26A	0.3566	0.6672	0.2959	0.171*
H26B	0.3506	0.6789	0.4130	0.171*
H26C	0.3976	0.5801	0.3803	0.171*
C27	0.9445 (2)	0.6310 (2)	0.1287 (2)	0.0645 (7)
H27A	0.9342	0.6677	0.0625	0.097*
H27B	0.9277	0.5597	0.1139	0.097*
H27C	1.0114	0.6362	0.1698	0.097*
S28	0.91241 (5)	0.22174 (5)	0.57658 (5)	0.0556 (2)
O29	0.94541 (16)	0.30956 (14)	0.53324 (15)	0.0809 (6)
O30	0.87168 (17)	0.23980 (15)	0.66093 (15)	0.0838 (7)
O31	0.97784 (15)	0.13502 (16)	0.59437 (16)	0.0819 (6)
C32	0.8122 (2)	0.1755 (2)	0.4689 (2)	0.0603 (7)
F33	0.73755 (14)	0.24221 (15)	0.44537 (15)	0.0955 (6)
F34	0.77668 (13)	0.08743 (12)	0.49175 (13)	0.0840 (5)
F35	0.83430 (13)	0.16316 (15)	0.37865 (11)	0.0895 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0500 (17)	0.0489 (16)	0.0643 (15)	0.0028 (13)	0.0195 (14)	−0.0015 (12)
C2	0.0544 (18)	0.0509 (16)	0.0716 (17)	−0.0002 (13)	0.0151 (15)	0.0075 (14)
C3	0.0533 (19)	0.069 (2)	0.0583 (16)	−0.0096 (14)	0.0130 (14)	0.0150 (14)
C4	0.0429 (16)	0.0720 (19)	0.0499 (14)	−0.0010 (13)	0.0166 (12)	0.0044 (13)
C5	0.0505 (17)	0.0518 (16)	0.0532 (14)	0.0114 (13)	0.0101 (13)	−0.0025 (12)
C6	0.073 (2)	0.0457 (16)	0.0642 (16)	0.0109 (14)	0.0110 (15)	0.0028 (13)
C7	0.073 (2)	0.0538 (17)	0.0577 (15)	0.0001 (15)	0.0192 (15)	0.0078 (13)
C8	0.0516 (17)	0.0532 (16)	0.0500 (13)	0.0041 (12)	0.0175 (12)	0.0016 (12)
C9	0.0353 (15)	0.0456 (14)	0.0421 (12)	0.0012 (11)	0.0088 (11)	−0.0043 (10)
N10	0.0327 (12)	0.0512 (13)	0.0496 (11)	0.0048 (9)	0.0122 (10)	−0.0056 (9)
C11	0.0354 (14)	0.0459 (14)	0.0451 (12)	−0.0009 (11)	0.0079 (11)	−0.0033 (10)
C12	0.0313 (14)	0.0520 (16)	0.0419 (12)	0.0005 (11)	0.0057 (11)	−0.0020 (11)
C13	0.0350 (14)	0.0469 (14)	0.0400 (12)	0.0022 (11)	0.0072 (11)	−0.0027 (10)
C14	0.0352 (15)	0.0474 (15)	0.0433 (12)	0.0038 (11)	0.0053 (11)	−0.0011 (10)
C15	0.0448 (17)	0.0431 (14)	0.0491 (14)	0.0012 (11)	0.0168 (13)	−0.0002 (11)
O16	0.0371 (11)	0.0851 (13)	0.0496 (9)	0.0067 (9)	0.0144 (9)	−0.0141 (8)
O17	0.0565 (12)	0.0881 (14)	0.0508 (10)	0.0133 (10)	0.0083 (9)	−0.0208 (9)
C18	0.0415 (16)	0.0713 (18)	0.0416 (13)	0.0115 (13)	0.0117 (12)	−0.0051 (12)
C19	0.0424 (16)	0.0733 (18)	0.0438 (13)	0.0045 (13)	0.0141 (12)	−0.0088 (12)
C20	0.0462 (19)	0.088 (2)	0.0656 (16)	0.0073 (16)	0.0254 (14)	−0.0050 (15)
C21	0.053 (2)	0.092 (2)	0.0599 (17)	0.0258 (17)	0.0146 (15)	−0.0015 (16)
C22	0.073 (2)	0.075 (2)	0.0639 (17)	0.0230 (17)	0.0137 (16)	0.0102 (14)
C23	0.062 (2)	0.081 (2)	0.0571 (16)	0.0124 (16)	0.0234 (15)	0.0095 (14)
C24	0.062 (2)	0.0676 (19)	0.0780 (19)	−0.0062 (15)	0.0340 (16)	−0.0155 (15)
C25	0.169 (4)	0.072 (2)	0.092 (2)	−0.007 (2)	0.032 (3)	0.0148 (18)
C26	0.084 (3)	0.097 (3)	0.177 (4)	−0.025 (2)	0.062 (3)	−0.056 (3)
C27	0.0563 (19)	0.0703 (18)	0.0781 (17)	0.0122 (14)	0.0374 (15)	−0.0050 (14)
S28	0.0708 (5)	0.0511 (4)	0.0508 (4)	−0.0092 (4)	0.0269 (3)	−0.0037 (3)
O29	0.1012 (17)	0.0671 (12)	0.0837 (13)	−0.0311 (11)	0.0416 (13)	0.0000 (10)
O30	0.128 (2)	0.0756 (13)	0.0675 (11)	−0.0128 (12)	0.0596 (13)	−0.0138 (9)
O31	0.0703 (15)	0.0821 (14)	0.0873 (13)	0.0193 (12)	0.0142 (11)	0.0035 (11)
C32	0.061 (2)	0.0637 (18)	0.0655 (17)	0.0012 (15)	0.0326 (16)	0.0020 (13)
F33	0.0703 (13)	0.1043 (14)	0.1154 (14)	0.0249 (11)	0.0328 (11)	0.0228 (11)
F34	0.0793 (13)	0.0644 (11)	0.1129 (13)	−0.0209 (9)	0.0354 (11)	−0.0061 (9)
F35	0.0815 (13)	0.1338 (16)	0.0590 (9)	−0.0108 (11)	0.0300 (9)	−0.0252 (9)

C1—C2	1.347 (3)	C18—C19	1.377 (3)
C1—C11	1.422 (3)	C19—C20	1.397 (3)
C1—H1	0.9300	C19—C24	1.515 (4)
C2—C3	1.405 (3)	C20—C21	1.362 (4)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.354 (4)	C21—C22	1.365 (4)
C3—H3	0.9300	C21—H21	0.9300
C4—C12	1.412 (3)	C22—C23	1.389 (4)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.353 (3)	C23—H23	0.9300
C5—C14	1.405 (3)	C24—C25	1.516 (4)
C5—H5	0.9300	C24—C26	1.527 (4)
C6—C7	1.405 (4)	C24—H24	0.9800
C6—H6	0.9300	C25—H25A	0.9600
C7—C8	1.340 (3)	C25—H25B	0.9600
C7—H7	0.9300	C25—H25C	0.9600
C8—C13	1.422 (3)	C26—H26A	0.9600
C8—H8	0.9300	C26—H26B	0.9600
C9—C11	1.389 (3)	C26—H26C	0.9600
C9—C13	1.391 (3)	C27—H27A	0.9600
C9—C15	1.507 (3)	C27—H27B	0.9600
N10—C12	1.365 (3)	C27—H27C	0.9600
N10—C14	1.373 (3)	S28—O30	1.4148 (17)
N10—C27	1.481 (3)	S28—O29	1.4161 (18)
C11—C12	1.431 (3)	S28—O31	1.443 (2)
C13—C14	1.428 (3)	S28—C32	1.799 (3)
C15—O17	1.188 (3)	C32—F35	1.321 (3)
C15—O16	1.335 (3)	C32—F34	1.322 (3)
O16—C18	1.431 (3)	C32—F33	1.344 (3)
C18—C23	1.366 (4)
C2—C1—C11	121.2 (2)	C18—C19—C24	123.0 (2)
C2—C1—H1	119.4	C20—C19—C24	121.8 (2)
C11—C1—H1	119.4	C21—C20—C19	122.6 (3)
C1—C2—C3	119.5 (2)	C21—C20—H20	118.7
C1—C2—H2	120.2	C19—C20—H20	118.7
C3—C2—H2	120.2	C20—C21—C22	120.3 (3)
C4—C3—C2	122.0 (2)	C20—C21—H21	119.9
C4—C3—H3	119.0	C22—C21—H21	119.9
C2—C3—H3	119.0	C21—C22—C23	119.2 (3)
C3—C4—C12	120.1 (2)	C21—C22—H22	120.4
C3—C4—H4	119.9	C23—C22—H22	120.4
C12—C4—H4	119.9	C18—C23—C22	119.0 (3)
C6—C5—C14	120.1 (2)	C18—C23—H23	120.5
C6—C5—H5	120.0	C22—C23—H23	120.5
C14—C5—H5	120.0	C19—C24—C25	110.7 (2)
C5—C6—C7	121.7 (2)	C19—C24—C26	112.3 (3)
C5—C6—H6	119.2	C25—C24—C26	111.4 (3)
C7—C6—H6	119.2	C19—C24—H24	107.4
C8—C7—C6	119.9 (2)	C25—C24—H24	107.4
C8—C7—H7	120.1	C26—C24—H24	107.4
C6—C7—H7	120.1	C24—C25—H25A	109.5
C7—C8—C13	121.1 (2)	C24—C25—H25B	109.5
C7—C8—H8	119.4	H25A—C25—H25B	109.5
C13—C8—H8	119.4	C24—C25—H25C	109.5
C11—C9—C13	121.1 (2)	H25A—C25—H25C	109.5
C11—C9—C15	119.2 (2)	H25B—C25—H25C	109.5
C13—C9—C15	119.70 (19)	C24—C26—H26A	109.5
C12—N10—C14	122.16 (18)	C24—C26—H26B	109.5
C12—N10—C27	118.31 (19)	H26A—C26—H26B	109.5
C14—N10—C27	119.5 (2)	C24—C26—H26C	109.5
C9—C11—C1	122.5 (2)	H26A—C26—H26C	109.5
C9—C11—C12	118.9 (2)	H26B—C26—H26C	109.5
C1—C11—C12	118.6 (2)	N10—C27—H27A	109.5
N10—C12—C4	122.0 (2)	N10—C27—H27B	109.5
N10—C12—C11	119.5 (2)	H27A—C27—H27B	109.5
C4—C12—C11	118.5 (2)	N10—C27—H27C	109.5
C9—C13—C8	122.7 (2)	H27A—C27—H27C	109.5
C9—C13—C14	119.0 (2)	H27B—C27—H27C	109.5
C8—C13—C14	118.3 (2)	O30—S28—O29	116.47 (12)
N10—C14—C5	121.7 (2)	O30—S28—O31	113.97 (13)
N10—C14—C13	119.3 (2)	O29—S28—O31	114.20 (13)
C5—C14—C13	118.9 (2)	O30—S28—C32	104.08 (13)
O17—C15—O16	125.3 (2)	O29—S28—C32	104.00 (12)
O17—C15—C9	124.9 (2)	O31—S28—C32	101.75 (13)
O16—C15—C9	109.79 (19)	F35—C32—F34	108.1 (2)
C15—O16—C18	118.12 (17)	F35—C32—F33	105.2 (2)
C23—C18—C19	123.6 (2)	F34—C32—F33	105.7 (2)
C23—C18—O16	116.1 (2)	F35—C32—S28	112.96 (19)
C19—C18—O16	120.1 (2)	F34—C32—S28	112.72 (19)
C18—C19—C20	115.2 (2)	F33—C32—S28	111.7 (2)
C11—C1—C2—C3	−0.2 (4)	C8—C13—C14—N10	−179.9 (2)
C1—C2—C3—C4	−0.5 (4)	C9—C13—C14—C5	−178.8 (2)
C2—C3—C4—C12	0.6 (4)	C8—C13—C14—C5	1.2 (3)
C14—C5—C6—C7	−0.6 (4)	C11—C9—C15—O17	−92.5 (3)
C5—C6—C7—C8	0.5 (4)	C13—C9—C15—O17	87.2 (3)
C6—C7—C8—C13	0.4 (4)	C11—C9—C15—O16	87.4 (2)
C13—C9—C11—C1	−178.0 (2)	C13—C9—C15—O16	−92.8 (2)
C15—C9—C11—C1	1.7 (3)	O17—C15—O16—C18	8.9 (3)
C13—C9—C11—C12	1.2 (3)	C9—C15—O16—C18	−171.01 (19)
C15—C9—C11—C12	−179.1 (2)	C15—O16—C18—C23	86.1 (3)
C2—C1—C11—C9	179.9 (2)	C15—O16—C18—C19	−98.8 (3)
C2—C1—C11—C12	0.7 (4)	C23—C18—C19—C20	−0.3 (4)
C14—N10—C12—C4	178.4 (2)	O16—C18—C19—C20	−175.1 (2)
C27—N10—C12—C4	−0.4 (3)	C23—C18—C19—C24	−178.2 (2)
C14—N10—C12—C11	−1.9 (3)	O16—C18—C19—C24	7.0 (4)
C27—N10—C12—C11	179.4 (2)	C18—C19—C20—C21	−0.4 (4)
C3—C4—C12—N10	179.7 (2)	C24—C19—C20—C21	177.5 (3)
C3—C4—C12—C11	−0.1 (3)	C19—C20—C21—C22	0.6 (4)
C9—C11—C12—N10	0.5 (3)	C20—C21—C22—C23	0.0 (4)
C1—C11—C12—N10	179.7 (2)	C19—C18—C23—C22	0.8 (4)
C9—C11—C12—C4	−179.8 (2)	O16—C18—C23—C22	175.8 (2)
C1—C11—C12—C4	−0.6 (3)	C21—C22—C23—C18	−0.6 (4)
C11—C9—C13—C8	178.6 (2)	C18—C19—C24—C25	97.9 (3)
C15—C9—C13—C8	−1.2 (3)	C20—C19—C24—C25	−79.8 (3)
C11—C9—C13—C14	−1.4 (3)	C18—C19—C24—C26	−137.0 (3)
C15—C9—C13—C14	178.9 (2)	C20—C19—C24—C26	45.3 (3)
C7—C8—C13—C9	178.8 (2)	O30—S28—C32—F35	174.13 (19)
C7—C8—C13—C14	−1.2 (3)	O29—S28—C32—F35	51.7 (2)
C12—N10—C14—C5	−179.5 (2)	O31—S28—C32—F35	−67.2 (2)
C27—N10—C14—C5	−0.8 (3)	O30—S28—C32—F34	−63.0 (2)
C12—N10—C14—C13	1.6 (3)	O29—S28—C32—F34	174.54 (18)
C27—N10—C14—C13	−179.6 (2)	O31—S28—C32—F34	55.6 (2)
C6—C5—C14—N10	−179.2 (2)	O30—S28—C32—F33	55.7 (2)
C6—C5—C14—C13	−0.3 (3)	O29—S28—C32—F33	−66.7 (2)
C9—C13—C14—N10	0.0 (3)	O31—S28—C32—F33	174.42 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O29i	0.93	2.48	3.363 (3)	159
C27—H27C···F35i	0.96	2.51	3.250 (4)	134

X	I	J	I···J	X···J	X–I···J
S28	O29	Cg1ii	3.703 (2)	3.879 (2)	86.3 (1)
S28	O31	Cg1ii	3.528 (2)	3.879 (2)	92.9 (1)
S28	O31	Cg2ii	3.208 (2)	4.128 (2)	120.3 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
3	3iii	3.962 (2)	0	3.340 (1)	2.131 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O29i	0.93	2.48	3.363 (3)	159
C27—H27C⋯F35i	0.96	2.51	3.250 (4)	134

Symmetry code: (i) .

Table 2

S–O⋯π inter­actions (Å,°)

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

X	I	J	I⋯J	X⋯J	X–I⋯J
S28	O31	Cg2ii	3.208 (2)	4.128 (2)	120.3 (2)

Symmetry code: (ii) .