2-[(E)-2-(4-Eth-oxy-phen-yl)ethen-yl]-1-methyl-quinolinium 4-fluoro-benzene-sulfonate.

In the structure of the title salt, C20H20NO(+)·C6H4FO3S(-), the 4-(eth-oxy-phen-yl)ethenyl unit is disordered over two positions with a refined site-occupancy ratio of 0.610 (6):0.390 (6). The cation is nearly planar, the dihedral angle between the quinolinium and benzene rings being 6.7 (4) and 1.7 (7)° for the major and minor components, respectively. The eth-oxy group is essentially coplanar with the benzene ring [C-O-C-Cmethy = 177.1 (8) and 177.8 (12)° for the major and minor components, respectively]. In the crystal, cations and anions are linked into chains along the b-axis direction by C-H⋯Osulfon-yl weak inter-actions. These chains are further connected into sheets parallel to (001) by C-H⋯Osulfon-yl weak inter-actions. The chains are also stacked along the a axis through π-π inter-actions involving the quinolinium and benzene rings [centroid-centroid distances = 3.636 (5) Å for the major component and 3.800 (9) Å for the minor component]. C-H⋯π inter-actions are also present.

Related literature

For background to the bioactivity and non-linear optical properties of quinolinium derivatives, see: Chanawanno et al. (2010 ▶); Hopkins et al. (2005 ▶); Musiol et al. (2006 ▶); O’Donnell et al. (2010 ▶); Ruanwas et al. (2010 ▶). For related structures, see: Chantrapromma et al. (2011 ▶); Fun et al. (2010 ▶); Ruanwas et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H20NO+·C6H4FO3S−

M = 465.52

Monoclinic,

a = 6.4366 (3) Å

b = 9.8909 (5) Å

c = 34.3628 (15) Å

β = 95.102 (2)°

V = 2179.00 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.37 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.932, T max = 0.991

19050 measured reflections

4993 independent reflections

3609 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.154

S = 1.09

4993 reflections

392 parameters

418 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032509/rz5097sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032509/rz5097Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032509/rz5097Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H20NO+·C6H4FO3S−	F(000) = 976
Mr = 465.52	Dx = 1.419 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4993 reflections
a = 6.4366 (3) Å	θ = 2.1–27.5°
b = 9.8909 (5) Å	µ = 0.19 mm−1
c = 34.3628 (15) Å	T = 100 K
β = 95.102 (2)°	Plate, yellow
V = 2179.00 (18) Å3	0.37 × 0.12 × 0.05 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4993 independent reflections
Radiation source: sealed tube	3609 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.932, Tmax = 0.991	k = −12→11
19050 measured reflections	l = −44→44

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0388P)2 + 4.3613P] where P = (Fo2 + 2Fc2)/3
4993 reflections	(Δ/σ)max < 0.001
392 parameters	Δρmax = 0.39 e Å−3
418 restraints	Δρmin = −0.49 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	1.5593 (3)	0.1235 (2)	0.18311 (7)	0.0173 (5)
C1	1.7488 (4)	0.0857 (3)	0.20382 (8)	0.0170 (6)
C2	1.8922 (4)	0.1828 (3)	0.22024 (9)	0.0211 (6)
H2A	1.8655	0.2748	0.2173	0.025*
C3	2.0733 (4)	0.1375 (3)	0.24085 (9)	0.0233 (6)
H3A	2.1660	0.2008	0.2524	0.028*
C4	2.1223 (4)	0.0006 (3)	0.24491 (9)	0.0214 (6)
H4A	2.2460	−0.0267	0.2587	0.026*
C5	1.9854 (4)	−0.0928 (3)	0.22830 (9)	0.0205 (6)
H5A	2.0182	−0.1842	0.2303	0.025*
C6	1.7957 (4)	−0.0528 (3)	0.20815 (8)	0.0184 (6)
C7	1.6492 (4)	−0.1489 (3)	0.19255 (9)	0.0191 (6)
H7A	1.6790	−0.2406	0.1952	0.023*
C8	1.4663 (4)	−0.1090 (3)	0.17380 (9)	0.0198 (6)
H8A	1.3698	−0.1738	0.1644	0.024*
C9	1.4191 (4)	0.0300 (3)	0.16827 (8)	0.0163 (5)
C10	1.2247 (4)	0.0745 (3)	0.14715 (9)	0.0197 (6)
H10A	1.1959	0.1693	0.1442	0.024*	0.610 (6)
H10B	1.1971	0.1699	0.1466	0.024*	0.390 (6)
C20	1.5120 (5)	0.2681 (3)	0.17700 (10)	0.0245 (7)
H20A	1.4912	0.2865	0.1495	0.037*
H20B	1.6262	0.3213	0.1884	0.037*
H20C	1.3876	0.2905	0.1891	0.037*
O1A	0.3281 (9)	0.0972 (6)	0.04235 (19)	0.0386 (14)	0.610 (6)
C11A	1.086 (2)	−0.0139 (19)	0.1318 (6)	0.0169 (19)	0.610 (6)
H11A	1.1156	−0.1053	0.1356	0.020*	0.610 (6)
C12A	0.889 (2)	0.0214 (10)	0.1092 (4)	0.0174 (16)	0.610 (6)
C13A	0.7675 (19)	−0.0815 (10)	0.0915 (5)	0.0235 (16)	0.610 (6)
H13A	0.8105	−0.1708	0.0950	0.028*	0.610 (6)
C14A	0.5834 (16)	−0.0542 (8)	0.0687 (4)	0.0250 (16)	0.610 (6)
H14A	0.5068	−0.1244	0.0565	0.030*	0.610 (6)
C15A	0.5146 (15)	0.0770 (8)	0.0641 (4)	0.0246 (16)	0.610 (6)
C16A	0.6277 (15)	0.1820 (9)	0.0829 (3)	0.0246 (18)	0.610 (6)
H16A	0.5789	0.2703	0.0805	0.030*	0.610 (6)
C17A	0.8141 (15)	0.1543 (10)	0.1054 (3)	0.0190 (18)	0.610 (6)
H17A	0.8891	0.2246	0.1179	0.023*	0.610 (6)
C18A	0.2520 (9)	0.2376 (8)	0.03791 (18)	0.0459 (17)	0.610 (6)
H18A	0.3556	0.2933	0.0267	0.055*	0.610 (6)
H18B	0.2271	0.2745	0.0632	0.055*	0.610 (6)
C19A	0.0542 (11)	0.2371 (11)	0.0117 (2)	0.061 (2)	0.610 (6)
H19A	−0.0053	0.3262	0.0108	0.092*	0.610 (6)
H19B	−0.0423	0.1745	0.0216	0.092*	0.610 (6)
H19C	0.0832	0.2104	−0.0141	0.092*	0.610 (6)
O1B	0.3343 (14)	0.1530 (7)	0.0407 (3)	0.0238 (16)	0.390 (6)
C11B	1.076 (4)	−0.005 (3)	0.1270 (9)	0.019 (3)	0.390 (6)
H11B	1.1013	−0.0980	0.1272	0.023*	0.390 (6)
C12B	0.883 (3)	0.0408 (17)	0.1054 (8)	0.019 (2)	0.390 (6)
C13B	0.748 (3)	−0.0595 (16)	0.0880 (7)	0.022 (2)	0.390 (6)
H13B	0.7842	−0.1504	0.0903	0.026*	0.390 (6)
C14B	0.561 (3)	−0.0215 (13)	0.0672 (6)	0.022 (2)	0.390 (6)
H14B	0.4692	−0.0872	0.0564	0.027*	0.390 (6)
C15B	0.512 (2)	0.1117 (12)	0.0627 (6)	0.0188 (19)	0.390 (6)
C16B	0.647 (2)	0.2108 (13)	0.0783 (5)	0.020 (2)	0.390 (6)
H16B	0.6125	0.3016	0.0747	0.024*	0.390 (6)
C17B	0.831 (2)	0.1749 (15)	0.0993 (5)	0.017 (2)	0.390 (6)
H17B	0.9209	0.2421	0.1094	0.020*	0.390 (6)
C18B	0.1886 (13)	0.0568 (9)	0.0237 (3)	0.038 (2)	0.390 (6)
H18C	0.1379	−0.0008	0.0436	0.046*	0.390 (6)
H18D	0.2530	0.0005	0.0050	0.046*	0.390 (6)
C19B	0.0125 (13)	0.1380 (12)	0.0035 (3)	0.038 (2)	0.390 (6)
H19D	−0.0927	0.0778	−0.0080	0.057*	0.390 (6)
H19E	0.0647	0.1929	−0.0165	0.057*	0.390 (6)
H19F	−0.0468	0.1950	0.0223	0.057*	0.390 (6)
S1	0.97568 (10)	0.53446 (7)	0.16403 (2)	0.02062 (19)
F1	0.3508 (3)	0.6116 (3)	0.03020 (7)	0.0605 (7)
O2	0.8648 (3)	0.5242 (2)	0.19899 (6)	0.0262 (5)
O3	1.0931 (3)	0.4139 (2)	0.15628 (7)	0.0337 (6)
O4	1.0969 (3)	0.6584 (2)	0.16254 (6)	0.0261 (5)
C21	0.7812 (4)	0.5484 (3)	0.12372 (9)	0.0223 (6)
C22	0.8393 (5)	0.5361 (4)	0.08595 (10)	0.0331 (8)
H22A	0.9763	0.5141	0.0820	0.040*
C23	0.6945 (5)	0.5564 (4)	0.05408 (11)	0.0436 (10)
H23A	0.7320	0.5488	0.0287	0.052*
C24	0.4930 (5)	0.5883 (4)	0.06144 (11)	0.0378 (9)
C25	0.4299 (5)	0.5984 (3)	0.09833 (10)	0.0286 (7)
H25A	0.2922	0.6191	0.1021	0.034*
C26	0.5755 (4)	0.5771 (3)	0.12989 (9)	0.0212 (6)
H26A	0.5355	0.5819	0.1552	0.025*

	U11	U22	U33	U12	U13	U23
N1	0.0140 (11)	0.0130 (11)	0.0247 (13)	−0.0001 (8)	0.0009 (9)	−0.0002 (10)
C1	0.0109 (12)	0.0221 (13)	0.0181 (15)	0.0002 (10)	0.0016 (10)	−0.0002 (11)
C2	0.0206 (14)	0.0151 (13)	0.0278 (17)	0.0008 (11)	0.0031 (12)	−0.0024 (12)
C3	0.0174 (14)	0.0256 (15)	0.0268 (17)	−0.0101 (12)	0.0008 (12)	−0.0069 (13)
C4	0.0159 (13)	0.0268 (16)	0.0209 (16)	0.0014 (11)	−0.0011 (11)	0.0017 (12)
C5	0.0213 (14)	0.0170 (13)	0.0231 (16)	0.0033 (11)	0.0013 (12)	0.0011 (12)
C6	0.0154 (13)	0.0196 (14)	0.0201 (15)	−0.0023 (11)	0.0006 (11)	−0.0027 (12)
C7	0.0193 (14)	0.0132 (13)	0.0250 (16)	−0.0004 (10)	0.0031 (11)	−0.0014 (11)
C8	0.0167 (13)	0.0167 (13)	0.0261 (17)	−0.0056 (11)	0.0019 (12)	−0.0019 (12)
C9	0.0100 (12)	0.0209 (13)	0.0184 (14)	−0.0014 (11)	0.0026 (10)	−0.0023 (12)
C10	0.0144 (13)	0.0206 (14)	0.0242 (16)	0.0010 (11)	0.0020 (11)	−0.0012 (12)
C20	0.0198 (14)	0.0152 (13)	0.0371 (19)	0.0009 (11)	−0.0052 (13)	0.0016 (13)
O1A	0.019 (2)	0.065 (3)	0.030 (2)	0.010 (3)	−0.0085 (17)	0.005 (3)
C11A	0.013 (3)	0.019 (3)	0.018 (5)	0.005 (2)	−0.001 (3)	0.003 (3)
C12A	0.013 (2)	0.024 (3)	0.015 (3)	0.006 (2)	0.000 (2)	0.004 (3)
C13A	0.018 (3)	0.026 (3)	0.026 (3)	0.003 (2)	−0.006 (2)	0.005 (3)
C14A	0.019 (3)	0.027 (3)	0.029 (3)	0.004 (3)	−0.003 (2)	−0.002 (3)
C15A	0.016 (2)	0.035 (4)	0.022 (2)	0.006 (3)	−0.003 (2)	0.003 (3)
C16A	0.019 (3)	0.026 (4)	0.030 (3)	0.010 (3)	0.005 (2)	0.008 (3)
C17A	0.014 (3)	0.025 (4)	0.018 (3)	0.000 (2)	0.004 (2)	0.003 (3)
C18A	0.029 (3)	0.077 (4)	0.030 (3)	0.035 (3)	−0.002 (2)	0.009 (3)
C19A	0.037 (3)	0.110 (6)	0.036 (4)	0.033 (4)	−0.006 (3)	0.005 (4)
O1B	0.021 (3)	0.023 (3)	0.026 (3)	−0.008 (3)	−0.006 (2)	0.003 (3)
C11B	0.018 (4)	0.022 (5)	0.017 (5)	−0.004 (4)	0.000 (4)	0.002 (4)
C12B	0.011 (3)	0.027 (4)	0.019 (4)	0.000 (3)	0.001 (3)	0.003 (3)
C13B	0.021 (4)	0.018 (4)	0.025 (4)	0.003 (3)	−0.001 (3)	0.003 (4)
C14B	0.019 (4)	0.025 (4)	0.021 (3)	−0.002 (4)	−0.008 (3)	0.001 (4)
C15B	0.015 (3)	0.022 (4)	0.019 (3)	0.006 (3)	0.002 (3)	0.004 (3)
C16B	0.015 (3)	0.019 (4)	0.026 (4)	−0.001 (3)	0.005 (3)	0.005 (3)
C17B	0.013 (3)	0.015 (4)	0.023 (4)	−0.001 (3)	0.004 (3)	0.008 (3)
C18B	0.031 (4)	0.046 (4)	0.036 (4)	−0.007 (3)	−0.002 (3)	0.002 (4)
C19B	0.017 (4)	0.057 (5)	0.039 (5)	0.006 (4)	−0.007 (3)	0.013 (4)
S1	0.0126 (3)	0.0153 (3)	0.0329 (4)	0.0008 (3)	−0.0040 (3)	−0.0043 (3)
F1	0.0400 (13)	0.096 (2)	0.0406 (14)	0.0180 (13)	−0.0222 (10)	−0.0190 (13)
O2	0.0217 (10)	0.0269 (11)	0.0298 (13)	−0.0014 (9)	0.0015 (9)	0.0035 (10)
O3	0.0195 (11)	0.0232 (11)	0.0559 (16)	0.0070 (9)	−0.0105 (10)	−0.0129 (11)
O4	0.0193 (10)	0.0225 (11)	0.0355 (13)	−0.0056 (8)	−0.0031 (9)	−0.0040 (9)
C21	0.0145 (13)	0.0160 (13)	0.0353 (18)	−0.0031 (11)	−0.0050 (12)	−0.0068 (13)
C22	0.0163 (14)	0.049 (2)	0.0331 (19)	0.0027 (14)	−0.0005 (13)	−0.0184 (17)
C23	0.0313 (18)	0.067 (3)	0.032 (2)	0.0029 (18)	−0.0008 (15)	−0.0210 (19)
C24	0.0289 (17)	0.048 (2)	0.033 (2)	0.0046 (16)	−0.0146 (15)	−0.0118 (17)
C25	0.0139 (14)	0.0277 (16)	0.043 (2)	0.0015 (12)	−0.0054 (13)	−0.0066 (15)
C26	0.0171 (13)	0.0151 (13)	0.0311 (17)	−0.0014 (11)	0.0011 (12)	−0.0029 (12)

N1—C9	1.359 (3)	C18A—H18A	0.9700
N1—C1	1.407 (3)	C18A—H18B	0.9700
N1—C20	1.473 (3)	C19A—H19A	0.9600
C1—C6	1.407 (4)	C19A—H19B	0.9600
C1—C2	1.414 (4)	C19A—H19C	0.9600
C2—C3	1.383 (4)	O1B—C15B	1.375 (11)
C2—H2A	0.9300	O1B—C18B	1.425 (10)
C3—C4	1.394 (4)	C11B—C12B	1.463 (12)
C3—H3A	0.9300	C11B—H11B	0.9300
C4—C5	1.366 (4)	C12B—C17B	1.380 (12)
C4—H4A	0.9300	C12B—C13B	1.417 (12)
C5—C6	1.406 (4)	C13B—C14B	1.399 (12)
C5—H5A	0.9300	C13B—H13B	0.9300
C6—C7	1.411 (4)	C14B—C15B	1.360 (11)
C7—C8	1.350 (4)	C14B—H14B	0.9300
C7—H7A	0.9300	C15B—C16B	1.385 (11)
C8—C9	1.418 (4)	C16B—C17B	1.377 (11)
C8—H8A	0.9300	C16B—H16B	0.9300
C9—C10	1.457 (4)	C17B—H17B	0.9300
C10—C11A	1.326 (18)	C18B—C19B	1.506 (10)
C10—C11B	1.38 (3)	C18B—H18C	0.9700
C10—H10A	0.9600	C18B—H18D	0.9700
C10—H10B	0.9600	C19B—H19D	0.9600
C20—H20A	0.9600	C19B—H19E	0.9600
C20—H20B	0.9600	C19B—H19F	0.9600
C20—H20C	0.9600	S1—O3	1.449 (2)
O1A—C15A	1.371 (7)	S1—O2	1.454 (2)
O1A—C18A	1.475 (8)	S1—O4	1.457 (2)
C11A—C12A	1.467 (8)	S1—C21	1.788 (3)
C11A—H11A	0.9300	F1—C24	1.367 (4)
C12A—C13A	1.392 (8)	C21—C22	1.388 (5)
C12A—C17A	1.403 (8)	C21—C26	1.389 (4)
C13A—C14A	1.388 (8)	C22—C23	1.388 (5)
C13A—H13A	0.9300	C22—H22A	0.9300
C14A—C15A	1.375 (8)	C23—C24	1.380 (5)
C14A—H14A	0.9300	C23—H23A	0.9300
C15A—C16A	1.394 (9)	C24—C25	1.369 (5)
C16A—C17A	1.394 (8)	C25—C26	1.385 (4)
C16A—H16A	0.9300	C25—H25A	0.9300
C17A—H17A	0.9300	C26—H26A	0.9300
C18A—C19A	1.492 (8)
C9—N1—C1	121.7 (2)	C12A—C17A—H17A	119.7
C9—N1—C20	119.0 (2)	O1A—C18A—C19A	108.5 (6)
C1—N1—C20	119.3 (2)	O1A—C18A—H18A	110.0
C6—C1—N1	118.7 (2)	C19A—C18A—H18A	110.0
C6—C1—C2	119.5 (2)	O1A—C18A—H18B	110.0
N1—C1—C2	121.8 (2)	C19A—C18A—H18B	110.0
C3—C2—C1	118.3 (3)	H18A—C18A—H18B	108.4
C3—C2—H2A	120.8	C15B—O1B—C18B	120.8 (8)
C1—C2—H2A	120.8	C10—C11B—C12B	127 (2)
C2—C3—C4	122.6 (3)	C10—C11B—H11B	116.7
C2—C3—H3A	118.7	C12B—C11B—H11B	116.7
C4—C3—H3A	118.7	C17B—C12B—C13B	118.3 (11)
C5—C4—C3	118.9 (3)	C17B—C12B—C11B	124.3 (14)
C5—C4—H4A	120.6	C13B—C12B—C11B	117.2 (13)
C3—C4—H4A	120.6	C14B—C13B—C12B	119.8 (11)
C4—C5—C6	121.0 (3)	C14B—C13B—H13B	120.1
C4—C5—H5A	119.5	C12B—C13B—H13B	120.1
C6—C5—H5A	119.5	C15B—C14B—C13B	119.8 (11)
C5—C6—C1	119.6 (2)	C15B—C14B—H14B	120.1
C5—C6—C7	121.3 (3)	C13B—C14B—H14B	120.1
C1—C6—C7	119.1 (2)	C14B—C15B—O1B	121.5 (10)
C8—C7—C6	120.6 (3)	C14B—C15B—C16B	120.8 (10)
C8—C7—H7A	119.7	O1B—C15B—C16B	117.6 (9)
C6—C7—H7A	119.7	C17B—C16B—C15B	120.0 (10)
C7—C8—C9	121.0 (2)	C17B—C16B—H16B	120.0
C7—C8—H8A	119.5	C15B—C16B—H16B	120.0
C9—C8—H8A	119.5	C16B—C17B—C12B	121.1 (11)
N1—C9—C8	118.8 (2)	C16B—C17B—H17B	119.5
N1—C9—C10	119.6 (2)	C12B—C17B—H17B	119.5
C8—C9—C10	121.6 (2)	O1B—C18B—C19B	105.9 (8)
C11A—C10—C9	121.2 (6)	O1B—C18B—H18C	110.6
C11B—C10—C9	127.1 (10)	C19B—C18B—H18C	110.6
C11A—C10—H10A	119.1	O1B—C18B—H18D	110.6
C11B—C10—H10A	112.9	C19B—C18B—H18D	110.6
C9—C10—H10A	119.8	H18C—C18B—H18D	108.7
C11A—C10—H10B	121.6	C18B—C19B—H19D	109.5
C11B—C10—H10B	115.8	C18B—C19B—H19E	109.5
C9—C10—H10B	117.1	H19D—C19B—H19E	109.5
N1—C20—H20A	109.5	C18B—C19B—H19F	109.5
N1—C20—H20B	109.5	H19D—C19B—H19F	109.5
H20A—C20—H20B	109.5	H19E—C19B—H19F	109.5
N1—C20—H20C	109.5	O3—S1—O2	113.38 (14)
H20A—C20—H20C	109.5	O3—S1—O4	113.36 (13)
H20B—C20—H20C	109.5	O2—S1—O4	113.04 (13)
C15A—O1A—C18A	117.4 (6)	O3—S1—C21	105.18 (13)
C10—C11A—C12A	124.9 (12)	O2—S1—C21	106.51 (13)
C10—C11A—H11A	117.5	O4—S1—C21	104.35 (13)
C12A—C11A—H11A	117.5	C22—C21—C26	120.1 (3)
C13A—C12A—C17A	117.9 (7)	C22—C21—S1	119.3 (2)
C13A—C12A—C11A	118.9 (8)	C26—C21—S1	120.6 (2)
C17A—C12A—C11A	123.2 (9)	C21—C22—C23	120.5 (3)
C14A—C13A—C12A	121.6 (7)	C21—C22—H22A	119.8
C14A—C13A—H13A	119.2	C23—C22—H22A	119.8
C12A—C13A—H13A	119.2	C24—C23—C22	117.7 (3)
C15A—C14A—C13A	119.9 (7)	C24—C23—H23A	121.2
C15A—C14A—H14A	120.0	C22—C23—H23A	121.2
C13A—C14A—H14A	120.0	F1—C24—C25	118.8 (3)
O1A—C15A—C14A	117.2 (7)	F1—C24—C23	118.0 (3)
O1A—C15A—C16A	122.7 (7)	C25—C24—C23	123.2 (3)
C14A—C15A—C16A	120.0 (7)	C24—C25—C26	118.5 (3)
C15A—C16A—C17A	119.9 (7)	C24—C25—H25A	120.7
C15A—C16A—H16A	120.0	C26—C25—H25A	120.7
C17A—C16A—H16A	120.0	C25—C26—C21	120.0 (3)
C16A—C17A—C12A	120.5 (7)	C25—C26—H26A	120.0
C16A—C17A—H17A	119.7	C21—C26—H26A	120.0
C9—N1—C1—C6	1.9 (4)	O1A—C15A—C16A—C17A	178.5 (10)
C20—N1—C1—C6	−177.6 (3)	C14A—C15A—C16A—C17A	2.1 (16)
C9—N1—C1—C2	−178.2 (3)	C15A—C16A—C17A—C12A	0.1 (15)
C20—N1—C1—C2	2.4 (4)	C13A—C12A—C17A—C16A	−3.0 (17)
C6—C1—C2—C3	−1.3 (4)	C11A—C12A—C17A—C16A	178.8 (13)
N1—C1—C2—C3	178.7 (3)	C15A—O1A—C18A—C19A	177.1 (8)
C1—C2—C3—C4	2.1 (5)	C11A—C10—C11B—C12B	140 (19)
C2—C3—C4—C5	−0.7 (5)	C9—C10—C11B—C12B	−179.0 (19)
C3—C4—C5—C6	−1.5 (5)	C10—C11B—C12B—C17B	6 (4)
C4—C5—C6—C1	2.2 (4)	C10—C11B—C12B—C13B	−178 (3)
C4—C5—C6—C7	−176.9 (3)	C17B—C12B—C13B—C14B	−4 (3)
N1—C1—C6—C5	179.2 (3)	C11B—C12B—C13B—C14B	180 (2)
C2—C1—C6—C5	−0.8 (4)	C12B—C13B—C14B—C15B	2 (3)
N1—C1—C6—C7	−1.7 (4)	C13B—C14B—C15B—O1B	176.6 (19)
C2—C1—C6—C7	178.4 (3)	C13B—C14B—C15B—C16B	0 (3)
C5—C6—C7—C8	179.0 (3)	C18B—O1B—C15B—C14B	3 (2)
C1—C6—C7—C8	−0.2 (4)	C18B—O1B—C15B—C16B	180.0 (14)
C6—C7—C8—C9	1.9 (5)	C14B—C15B—C16B—C17B	−1 (3)
C1—N1—C9—C8	−0.2 (4)	O1B—C15B—C16B—C17B	−177.5 (16)
C20—N1—C9—C8	179.3 (3)	C15B—C16B—C17B—C12B	−1 (3)
C1—N1—C9—C10	179.8 (3)	C13B—C12B—C17B—C16B	3 (3)
C20—N1—C9—C10	−0.7 (4)	C11B—C12B—C17B—C16B	180 (2)
C7—C8—C9—N1	−1.7 (4)	C15B—O1B—C18B—C19B	177.8 (12)
C7—C8—C9—C10	178.3 (3)	O3—S1—C21—C22	−48.2 (3)
N1—C9—C10—C11A	178.9 (12)	O2—S1—C21—C22	−168.8 (2)
C8—C9—C10—C11A	−1.0 (12)	O4—S1—C21—C22	71.3 (3)
N1—C9—C10—C11B	173 (2)	O3—S1—C21—C26	134.5 (2)
C8—C9—C10—C11B	−7 (2)	O2—S1—C21—C26	13.9 (3)
C11B—C10—C11A—C12A	−36 (15)	O4—S1—C21—C26	−105.9 (2)
C9—C10—C11A—C12A	−178.3 (12)	C26—C21—C22—C23	2.0 (5)
C10—C11A—C12A—C13A	173.8 (18)	S1—C21—C22—C23	−175.2 (3)
C10—C11A—C12A—C17A	−8 (2)	C21—C22—C23—C24	−0.3 (6)
C17A—C12A—C13A—C14A	4 (2)	C22—C23—C24—F1	178.5 (3)
C11A—C12A—C13A—C14A	−177.8 (15)	C22—C23—C24—C25	−1.1 (6)
C12A—C13A—C14A—C15A	−2 (2)	F1—C24—C25—C26	−178.9 (3)
C18A—O1A—C15A—C14A	179.0 (10)	C23—C24—C25—C26	0.7 (6)
C18A—O1A—C15A—C16A	2.5 (15)	C24—C25—C26—C21	1.1 (4)
C13A—C14A—C15A—O1A	−177.8 (12)	C22—C21—C26—C25	−2.4 (4)
C13A—C14A—C15A—C16A	−1.2 (18)	S1—C21—C26—C25	174.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.55	3.456 (4)	166
C8—H8A···O4ii	0.93	2.41	3.306 (3)	161
C10—H10A···O3	0.96	2.55	3.483 (4)	164
C11A—H11A···O4ii	0.93	2.52	3.408 (19)	159
C17A—H17A···O3	0.93	2.58	3.510 (10)	177
C20—H20B···O2i	0.96	2.53	3.441 (4)	158
C20—H20C···O3	0.96	2.44	3.085 (4)	124
C25—H25A···O4iii	0.93	2.55	3.264 (4)	134
C13A—H13A···Cg5ii	0.93	2.82	3.575 (10)	139
C16A—H16A···Cg5	0.93	2.98	3.826 (9)	151
C19A—H19B···Cg4iii	0.96	2.99	3.862 (11)	152
C13B—H13B···Cg5ii	0.93	2.95	3.765 (16)	147
C16B—H16B···Cg5	0.93	2.70	3.562 (13)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C12B–C17B and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.55	3.456 (4)	166
C8—H8A⋯O4ii	0.93	2.41	3.306 (3)	161
C10—H10A⋯O3	0.96	2.55	3.483 (4)	164
C11A—H11A⋯O4ii	0.93	2.52	3.408 (19)	159
C17A—H17A⋯O3	0.93	2.58	3.510 (10)	177
C20—H20B⋯O2i	0.96	2.53	3.441 (4)	158
C20—H20C⋯O3	0.96	2.44	3.085 (4)	124
C25—H25A⋯O4iii	0.93	2.55	3.264 (4)	134
C13A—H13A⋯Cg5ii	0.93	2.82	3.575 (10)	139
C16A—H16A⋯Cg5	0.93	2.98	3.826 (9)	151
C19A—H19B⋯Cg4iii	0.96	2.99	3.862 (11)	152
C13B—H13B⋯Cg5ii	0.93	2.95	3.765 (16)	147
C16B—H16B⋯Cg5	0.93	2.70	3.562 (13)	155

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