1,1'-Dimethyl-4,4'-[(2,4-diphenyl-cyclo-butane-1,3-di-yl)dipyridinium-(E)-1-methyl-4-styrylpyridinium-benzene-sulfonate (0.15/1.70/2).

In the title compound, 1.70C(14)H(14)N(+)·0.15C(28)H(28)N(2) (2+)·2C(6)H(5)O(3)S(-), the monocation exists in the E configuration with respect to the ethenyl C=C double bond and is close to planar, the dihedral angle between the pyridinium and phenyl ring being 5.20 (13)°. The dication lies about an inversion centre. In the crystal, the dication occupies almost the same site occupied by monocations at (x, y, z) and (2 - x, 1 - y, 1 - z). The O atoms of the anion are disordered over two positions with occupancies of 0.75 and 0.25. In the crystal, the cations are stacked in an anti-parallel manner along the a axis, whereas the anions are linked into chains along the same direction by C-H⋯O hydrogen bonds. In addition, C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.593 (9) or 3.6705 (16) Å] are observed.

Related literature

The title compound was synthesized in as part of our search for non-linear optical materials. For background to non-linear optical materials, see: Lin et al. (2002 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Chantrapromma et al. (2009a ▶,b ▶); Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

1.70C14H14N+·0.15C28H28n class="Chemical">N2 2+·2C6H5O3S−

M = 353.43

Triclinic,

a = 8.4037 (1) Å

b = 9.8505 (1) Å

c = 11.0869 (1) Å

α = 68.677 (1)°

β = 88.968 (1)°

γ = 86.134 (1)°

V = 852.99 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.36 × 0.19 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.930, T max = 0.982

19913 measured reflections

4962 independent reflections

4045 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.120

S = 1.03

4962 reflections

387 parameters

165 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034588/ci2884sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034588/ci2884Isup2.hkl

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

1.70C14H14N+·0.15C28H28N22+·2C6H5O3S−	Z = 2
Mr = 353.43	F(000) = 372
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Melting point = 493–495 K
a = 8.4037 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8505 (1) Å	Cell parameters from 4962 reflections
c = 11.0869 (1) Å	θ = 2.2–30.0°
α = 68.677 (1)°	µ = 0.21 mm−1
β = 88.968 (1)°	T = 100 K
γ = 86.134 (1)°	Needle, pale orange
V = 852.99 (2) Å3	0.36 × 0.19 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	4962 independent reflections
Radiation source: sealed tube	4045 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.930, Tmax = 0.982	k = −13→13
19913 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4388P] where P = (Fo2 + 2Fc2)/3
4962 reflections	(Δ/σ)max = 0.001
387 parameters	Δρmax = 0.50 e Å−3
165 restraints	Δρmin = −0.46 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)
S1	0.38722 (5)	0.23951 (5)	0.21176 (4)	0.02809 (13)
O1	0.3721 (6)	0.1603 (4)	0.1270 (3)	0.0343 (9)	0.75
O2	0.3317 (3)	0.3895 (2)	0.1626 (3)	0.0552 (7)	0.75
O3	0.3175 (2)	0.1588 (3)	0.33964 (19)	0.0479 (6)	0.75
O1A	0.362 (2)	0.1280 (10)	0.1600 (10)	0.030 (2)	0.25
O2A	0.3693 (9)	0.3811 (5)	0.1020 (6)	0.0475 (18)	0.25
O3A	0.3015 (8)	0.2458 (10)	0.3210 (6)	0.0534 (19)	0.25
C1	0.59528 (18)	0.22888 (18)	0.24520 (16)	0.0232 (3)
C2	0.6978 (2)	0.3149 (2)	0.15391 (18)	0.0306 (4)
H2	0.6591	0.3825	0.0716	0.037*
C3	0.8603 (2)	0.3013 (2)	0.1834 (2)	0.0403 (5)
H3	0.9334	0.3593	0.1215	0.048*
C4	0.9193 (2)	0.2050 (2)	0.3008 (2)	0.0421 (5)
H4	1.0310	0.1970	0.3208	0.050*
C5	0.8174 (2)	0.1197 (2)	0.3909 (2)	0.0368 (4)
H5	0.8567	0.0515	0.4728	0.044*
C6	0.6546 (2)	0.13117 (19)	0.36360 (17)	0.0273 (3)
H6	0.5819	0.0721	0.4251	0.033*
N1	0.4628 (3)	0.7537 (2)	0.2108 (2)	0.0218 (4)	0.85
C7	0.5822 (3)	0.7427 (2)	0.4060 (2)	0.0268 (4)	0.85
H7	0.5987	0.7876	0.4681	0.032*	0.85
C8	0.4883 (3)	0.8152 (2)	0.2988 (2)	0.0272 (4)	0.85
H8	0.4400	0.9104	0.2865	0.033*	0.85
C9	0.5281 (3)	0.6190 (3)	0.2275 (3)	0.0261 (5)	0.85
H9	0.5083	0.5765	0.1643	0.031*	0.85
C10	0.6229 (3)	0.5432 (3)	0.3327 (3)	0.0272 (5)	0.85
H10	0.6683	0.4474	0.3436	0.033*	0.85
C11	0.6538 (3)	0.6040 (2)	0.42569 (19)	0.0223 (4)	0.85
C12	0.7539 (2)	0.5306 (2)	0.54043 (18)	0.0239 (4)	0.85
H12	0.7649	0.5800	0.5999	0.029*	0.85
C13	0.8318 (2)	0.3999 (2)	0.56868 (18)	0.0231 (4)	0.85
H13	0.8198	0.3505	0.5093	0.028*	0.85
C14	0.9343 (3)	0.3252 (3)	0.6822 (3)	0.0215 (5)	0.85
C15	0.9935 (5)	0.1826 (4)	0.7056 (3)	0.0363 (8)	0.85
H15	0.9662	0.1352	0.6477	0.044*	0.85
C16	1.0892 (4)	0.1066 (3)	0.8133 (3)	0.0474 (7)	0.85
H16	1.1286	0.0078	0.8288	0.057*	0.85
C17	1.1285 (3)	0.1741 (3)	0.8976 (2)	0.0385 (5)	0.85
H17	1.1958	0.1225	0.9713	0.046*	0.85
C18	1.0712 (3)	0.3162 (3)	0.8752 (3)	0.0281 (5)	0.85
H18	1.1004	0.3634	0.9329	0.034*	0.85
C19	0.9729 (3)	0.3915 (3)	0.7698 (3)	0.0241 (5)	0.85
H19	0.9302	0.4888	0.7564	0.029*	0.85
C20	0.3651 (3)	0.8339 (3)	0.0942 (2)	0.0270 (5)	0.85
H20A	0.3270	0.9271	0.0964	0.041*	0.85
H20B	0.2760	0.7787	0.0921	0.041*	0.85
H20C	0.4287	0.8481	0.0183	0.041*	0.85
N1A	0.5061 (15)	0.7265 (13)	0.2395 (13)	0.024 (3)	0.15
C7A	0.6724 (16)	0.7404 (12)	0.4039 (11)	0.027 (2)	0.15
H7A	0.7074	0.7971	0.4517	0.032*	0.15
C8A	0.5608 (16)	0.8010 (13)	0.3109 (13)	0.025 (3)	0.15
H8A	0.5184	0.8988	0.2960	0.030*	0.15
C9A	0.5571 (17)	0.5844 (14)	0.2726 (15)	0.023 (3)	0.15
H9A	0.5077	0.5263	0.2325	0.027*	0.15
C10A	0.6715 (19)	0.5233 (17)	0.3631 (16)	0.032 (4)	0.15
H10A	0.7116	0.4250	0.3774	0.038*	0.15
C11A	0.7364 (15)	0.5981 (10)	0.4331 (10)	0.020 (2)	0.15
C12A	0.8830 (9)	0.5488 (8)	0.5165 (7)	0.0196 (18)	0.15
H12A	0.8685	0.5734	0.5942	0.023*	0.15
C13A	0.9561 (9)	0.3890 (8)	0.5544 (7)	0.0198 (19)	0.15
H13A	0.9026	0.3369	0.5081	0.024*	0.15
C14A	0.9758 (18)	0.2928 (16)	0.6965 (15)	0.021 (4)	0.15
C15A	0.982 (3)	0.1440 (16)	0.7350 (16)	0.027 (4)	0.15
H15A	0.9775	0.1021	0.6694	0.032*	0.15
C16A	1.017 (2)	0.0508 (17)	0.8616 (14)	0.046 (4)	0.15
H16A	1.0048	−0.0523	0.8893	0.055*	0.15
C17A	1.0613 (17)	0.1138 (14)	0.9484 (13)	0.038 (3)	0.15
H17A	1.0972	0.0537	1.0342	0.046*	0.15
C18A	1.0605 (19)	0.2637 (15)	0.9108 (14)	0.027 (3)	0.15
H18A	1.0929	0.3049	0.9721	0.033*	0.15
C19A	1.0153 (17)	0.3559 (15)	0.7900 (14)	0.019 (3)	0.15
H19A	1.0087	0.4600	0.7667	0.023*	0.15
C20A	0.3969 (16)	0.7947 (15)	0.1336 (14)	0.021 (3)	0.15
H20D	0.3415	0.8783	0.1438	0.032*	0.15
H20E	0.3212	0.7264	0.1323	0.032*	0.15
H20F	0.4547	0.8251	0.0537	0.032*	0.15

	U11	U22	U33	U12	U13	U23
S1	0.02068 (19)	0.0370 (2)	0.0368 (2)	0.00345 (15)	−0.00828 (16)	−0.02605 (19)
O1	0.0272 (13)	0.0477 (18)	0.0420 (19)	−0.0018 (16)	−0.0071 (15)	−0.0326 (18)
O2	0.0356 (12)	0.0368 (11)	0.106 (2)	0.0157 (8)	−0.0242 (13)	−0.0432 (13)
O3	0.0190 (9)	0.0943 (18)	0.0353 (11)	−0.0045 (11)	−0.0001 (7)	−0.0294 (12)
O1A	0.033 (3)	0.023 (3)	0.037 (4)	−0.009 (3)	−0.004 (4)	−0.013 (3)
O2A	0.044 (4)	0.025 (3)	0.077 (4)	0.010 (2)	−0.027 (3)	−0.024 (3)
O3A	0.034 (3)	0.095 (4)	0.055 (4)	0.007 (3)	−0.005 (3)	−0.057 (4)
C1	0.0198 (7)	0.0268 (7)	0.0316 (8)	0.0003 (5)	−0.0027 (6)	−0.0211 (7)
C2	0.0381 (9)	0.0303 (9)	0.0331 (9)	−0.0070 (7)	0.0059 (7)	−0.0225 (7)
C3	0.0332 (9)	0.0466 (11)	0.0616 (13)	−0.0180 (8)	0.0200 (9)	−0.0424 (11)
C4	0.0207 (8)	0.0537 (12)	0.0730 (15)	0.0012 (8)	−0.0049 (9)	−0.0486 (12)
C5	0.0316 (9)	0.0407 (10)	0.0492 (11)	0.0103 (8)	−0.0159 (8)	−0.0309 (9)
C6	0.0253 (8)	0.0295 (8)	0.0333 (9)	0.0009 (6)	−0.0033 (7)	−0.0192 (7)
N1	0.0221 (10)	0.0240 (10)	0.0210 (11)	0.0002 (8)	−0.0028 (9)	−0.0105 (9)
C7	0.0339 (12)	0.0246 (9)	0.0262 (11)	0.0034 (8)	−0.0077 (9)	−0.0149 (8)
C8	0.0339 (12)	0.0224 (10)	0.0281 (11)	0.0034 (9)	−0.0082 (10)	−0.0130 (8)
C9	0.0301 (11)	0.0274 (12)	0.0252 (12)	0.0019 (9)	−0.0047 (10)	−0.0152 (10)
C10	0.0313 (13)	0.0250 (11)	0.0304 (13)	0.0037 (10)	−0.0049 (11)	−0.0168 (10)
C11	0.0218 (9)	0.0237 (9)	0.0230 (9)	0.0005 (7)	−0.0020 (8)	−0.0108 (7)
C12	0.0258 (9)	0.0251 (9)	0.0238 (9)	−0.0006 (7)	−0.0024 (7)	−0.0125 (7)
C13	0.0257 (9)	0.0240 (9)	0.0222 (9)	−0.0005 (7)	−0.0015 (7)	−0.0115 (7)
C14	0.0232 (13)	0.0210 (11)	0.0202 (11)	0.0000 (10)	−0.0010 (9)	−0.0076 (9)
C15	0.0510 (19)	0.0297 (17)	0.0318 (16)	0.0117 (14)	−0.0175 (15)	−0.0170 (14)
C16	0.0700 (19)	0.0296 (12)	0.0459 (15)	0.0200 (12)	−0.0285 (14)	−0.0202 (11)
C17	0.0519 (14)	0.0311 (11)	0.0307 (12)	0.0068 (11)	−0.0183 (11)	−0.0099 (10)
C18	0.0368 (12)	0.0264 (13)	0.0231 (13)	−0.0054 (11)	−0.0040 (10)	−0.0105 (10)
C19	0.0260 (13)	0.0221 (12)	0.0250 (11)	−0.0014 (10)	−0.0030 (10)	−0.0095 (9)
C20	0.0292 (12)	0.0302 (13)	0.0203 (11)	0.0006 (10)	−0.0077 (9)	−0.0078 (10)
N1A	0.018 (5)	0.024 (5)	0.022 (5)	0.000 (4)	−0.004 (4)	−0.001 (4)
C7A	0.028 (4)	0.028 (4)	0.026 (4)	0.003 (4)	−0.001 (4)	−0.012 (3)
C8A	0.025 (4)	0.022 (4)	0.034 (5)	0.004 (4)	−0.007 (4)	−0.017 (4)
C9A	0.027 (5)	0.023 (5)	0.020 (5)	0.003 (4)	−0.012 (4)	−0.010 (4)
C10A	0.032 (6)	0.027 (5)	0.035 (6)	−0.003 (4)	−0.003 (4)	−0.009 (4)
C11A	0.023 (4)	0.019 (4)	0.025 (4)	0.000 (3)	−0.001 (4)	−0.017 (3)
C12A	0.025 (4)	0.021 (4)	0.016 (4)	0.001 (3)	0.004 (3)	−0.012 (3)
C13A	0.024 (4)	0.017 (3)	0.021 (4)	0.000 (3)	−0.003 (3)	−0.010 (3)
C14A	0.017 (5)	0.025 (6)	0.017 (5)	0.002 (4)	−0.003 (4)	−0.004 (4)
C15A	0.031 (5)	0.019 (6)	0.031 (6)	0.007 (4)	0.011 (4)	−0.012 (4)
C16A	0.049 (6)	0.042 (5)	0.046 (6)	−0.003 (4)	−0.001 (4)	−0.014 (4)
C17A	0.037 (5)	0.035 (5)	0.037 (5)	0.000 (4)	0.001 (4)	−0.006 (4)
C18A	0.028 (5)	0.029 (6)	0.024 (5)	−0.007 (4)	−0.004 (4)	−0.007 (4)
C19A	0.020 (5)	0.015 (5)	0.024 (5)	−0.001 (4)	0.000 (4)	−0.010 (4)
C20A	0.022 (5)	0.019 (5)	0.022 (5)	−0.001 (4)	−0.003 (4)	−0.006 (4)

S1—O3A	1.417 (4)	C17—C18	1.384 (3)
S1—O2	1.424 (2)	C17—H17	0.96
S1—O1	1.435 (2)	C18—C19	1.386 (3)
S1—O1A	1.440 (4)	C18—H18	0.96
S1—O2A	1.481 (4)	C19—H19	0.96
S1—O3	1.483 (2)	C20—H20A	0.96
S1—C1	1.7821 (15)	C20—H20B	0.96
C1—C2	1.389 (3)	C20—H20C	0.96
C1—C6	1.392 (2)	N1A—C9A	1.353 (14)
C2—C3	1.396 (3)	N1A—C8A	1.362 (14)
C2—H2	0.96	N1A—C20A	1.434 (16)
C3—C4	1.379 (3)	C7A—C8A	1.346 (14)
C3—H3	0.96	C7A—C11A	1.391 (13)
C4—C5	1.377 (3)	C7A—H7A	0.96
C4—H4	0.96	C8A—H8A	0.96
C5—C6	1.394 (2)	C9A—C10A	1.345 (15)
C5—H5	0.96	C9A—H9A	0.96
C6—H6	0.96	C10A—C11A	1.390 (14)
N1—C8	1.348 (3)	C10A—H10A	0.96
N1—C9	1.350 (3)	C11A—C12A	1.497 (13)
N1—C20	1.476 (3)	C12A—C13A	1.5587
C7—C8	1.373 (3)	C12A—C13Ai	1.596 (15)
C7—C11	1.398 (3)	C12A—H12A	0.98
C7—H7	0.96	C13A—C14A	1.519 (16)
C8—H8	0.96	C13A—C12Ai	1.596 (15)
C9—C10	1.368 (3)	C13A—H13A	0.98
C9—H9	0.96	C14A—C15A	1.368 (16)
C10—C11	1.403 (3)	C14A—C19A	1.443 (15)
C10—H10	0.96	C15A—C16A	1.394 (16)
C11—C12	1.462 (3)	C15A—H15A	0.96
C12—C13	1.337 (3)	C16A—C17A	1.388 (15)
C12—H12	0.96	C16A—H16A	0.96
C13—C14	1.465 (3)	C17A—C18A	1.381 (15)
C13—H13	0.96	C17A—H17A	0.96
C14—C15	1.391 (4)	C18A—C19A	1.360 (15)
C14—C19	1.405 (3)	C18A—H18A	0.96
C15—C16	1.391 (4)	C19A—H19A	0.96
C15—H15	0.96	C20A—H20D	0.96
C16—C17	1.386 (3)	C20A—H20E	0.96
C16—H16	0.96	C20A—H20F	0.96
O2—S1—O1	116.5 (2)	C15—C16—H16	120.2
O3A—S1—O1A	121.0 (7)	C18—C17—C16	119.9 (2)
O3A—S1—O2A	110.9 (5)	C18—C17—H17	120.1
O1A—S1—O2A	106.6 (5)	C16—C17—H17	120.0
O2—S1—O3	112.08 (18)	C17—C18—C19	120.6 (2)
O1—S1—O3	109.9 (2)	C17—C18—H18	119.7
O2—S1—C1	108.27 (12)	C19—C18—H18	119.7
O1—S1—C1	105.4 (2)	C18—C19—C14	120.1 (2)
O3—S1—C1	103.69 (10)	C18—C19—H19	120.3
C2—C1—C6	120.17 (15)	C14—C19—H19	119.6
C2—C1—S1	120.70 (13)	C18—C19—H19A	88.2
C6—C1—S1	119.12 (13)	C14—C19—H19A	137.1
C1—C2—C3	118.75 (18)	H19—C19—H19A	46.0
C1—C2—H2	121.3	C9A—N1A—C8A	117.7 (11)
C3—C2—H2	119.9	C9A—N1A—C20A	120.6 (12)
C4—C3—C2	121.21 (19)	C8A—N1A—C20A	121.7 (11)
C4—C3—H3	118.7	C8A—C7A—C11A	121.7 (10)
C2—C3—H3	120.1	C8A—C7A—H7A	118.8
C5—C4—C3	119.89 (17)	C11A—C7A—H7A	119.5
C5—C4—H4	119.4	C7A—C8A—N1A	121.7 (11)
C3—C4—H4	120.7	C7A—C8A—H8A	118.5
C4—C5—C6	119.96 (19)	N1A—C8A—H8A	119.8
C4—C5—H5	120.9	C10A—C9A—N1A	121.0 (12)
C6—C5—H5	119.1	C10A—C9A—H9A	120.1
C1—C6—C5	120.02 (18)	N1A—C9A—H9A	118.8
C1—C6—H6	118.9	C9A—C10A—C11A	122.6 (13)
C5—C6—H6	121.1	C9A—C10A—H10A	118.2
C8—N1—C9	120.4 (2)	C11A—C10A—H10A	119.1
C8—N1—C20	120.3 (2)	C10A—C11A—C7A	114.8 (11)
C9—N1—C20	119.3 (2)	C10A—C11A—C12A	125.6 (10)
C8—C7—C11	120.58 (18)	C7A—C11A—C12A	118.6 (9)
C8—C7—H7	119.7	C11A—C12A—C13A	120.2 (4)
C11—C7—H7	119.7	C11A—C12A—C13Ai	114.7 (8)
C8—C7—H7A	127.2	C13A—C12A—C13Ai	90.9 (5)
C11—C7—H7A	97.8	C11A—C12A—H12A	109.9
N1—C8—C7	120.7 (2)	C13A—C12A—H12A	109.9
N1—C8—H8	119.7	C13Ai—C12A—H12A	109.9
C7—C8—H8	119.7	C14A—C13A—C12A	119.6 (6)
N1—C9—C10	120.8 (2)	C14A—C13A—C12Ai	114.8 (9)
N1—C9—H9	119.4	C12A—C13A—C12Ai	89.1 (5)
C10—C9—H9	119.8	C14A—C13A—H13A	109.9
C9—C10—C11	120.5 (2)	C12A—C13A—H13A	111.0
C9—C10—H10	120.0	C12Ai—C13A—H13A	110.9
C11—C10—H10	119.5	C15A—C14A—C19A	118.3 (13)
C7—C11—C10	117.0 (2)	C15A—C14A—C13A	120.9 (12)
C7—C11—C12	119.05 (17)	C19A—C14A—C13A	120.0 (12)
C10—C11—C12	123.97 (19)	C14A—C15A—C16A	123.1 (16)
C13—C12—C11	124.87 (17)	C14A—C15A—H15A	118.0
C13—C12—H12	117.4	C16A—C15A—H15A	118.2
C11—C12—H12	117.7	C17A—C16A—C15A	117.4 (14)
C12—C13—C14	125.76 (19)	C17A—C16A—H16A	121.1
C12—C13—H13	117.2	C15A—C16A—H16A	121.4
C14—C13—H13	117.1	C18A—C17A—C16A	120.4 (12)
C15—C14—C19	118.6 (3)	C18A—C17A—H17A	119.1
C15—C14—C13	118.9 (2)	C16A—C17A—H17A	120.5
C19—C14—C13	122.4 (2)	C19A—C18A—C17A	122.6 (13)
C14—C15—C16	121.0 (3)	C19A—C18A—H18A	118.5
C14—C15—H15	119.5	C17A—C18A—H18A	118.9
C16—C15—H15	119.5	C18A—C19A—C14A	118.0 (12)
C17—C16—C15	119.8 (2)	C18A—C19A—H19A	121.8
C17—C16—H16	120.0	C14A—C19A—H19A	120.2
O3A—S1—C1—C2	−134.7 (4)	C14—C15—C16—C17	−1.0 (6)
O2—S1—C1—C2	−48.72 (19)	C15—C16—C17—C18	0.7 (5)
O1—S1—C1—C2	76.6 (2)	C16—C17—C18—C19	0.7 (4)
O1A—S1—C1—C2	93.2 (5)	C17—C18—C19—C14	−1.9 (4)
O2A—S1—C1—C2	−18.1 (3)	C15—C14—C19—C18	1.6 (4)
O3—S1—C1—C2	−167.91 (17)	C13—C14—C19—C18	−179.6 (2)
O3A—S1—C1—C6	46.3 (4)	C11A—C7A—C8A—N1A	−1(2)
O2—S1—C1—C6	132.32 (18)	C9A—N1A—C8A—C7A	6(2)
O1—S1—C1—C6	−102.4 (2)	C20A—N1A—C8A—C7A	−174.9 (13)
O1A—S1—C1—C6	−85.8 (5)	C8A—N1A—C9A—C10A	−7(2)
O2A—S1—C1—C6	163.0 (3)	C20A—N1A—C9A—C10A	173.3 (15)
O3—S1—C1—C6	13.13 (18)	N1A—C9A—C10A—C11A	4(3)
C6—C1—C2—C3	0.0 (2)	C9A—C10A—C11A—C7A	1(2)
S1—C1—C2—C3	−178.99 (12)	C9A—C10A—C11A—C12A	−167.9 (13)
C1—C2—C3—C4	−0.2 (3)	C8A—C7A—C11A—C10A	−3(2)
C2—C3—C4—C5	0.3 (3)	C8A—C7A—C11A—C12A	167.1 (12)
C3—C4—C5—C6	−0.2 (3)	C10A—C11A—C12A—C13A	−13.1 (15)
C2—C1—C6—C5	0.1 (2)	C7A—C11A—C12A—C13A	178.5 (8)
S1—C1—C6—C5	179.09 (12)	C10A—C11A—C12A—C13Ai	93.6 (15)
C4—C5—C6—C1	0.0 (3)	C7A—C11A—C12A—C13Ai	−74.8 (13)
C9—N1—C8—C7	0.7 (4)	C11A—C12A—C13A—C14A	−122.2 (10)
C20—N1—C8—C7	−178.4 (2)	C13Ai—C12A—C13A—C14A	118.3 (9)
C11—C7—C8—N1	0.3 (4)	C11A—C12A—C13A—C12Ai	119.5 (9)
C8—N1—C9—C10	−1.0 (4)	C13Ai—C12A—C13A—C12Ai	0.0
C20—N1—C9—C10	178.2 (2)	C12A—C13A—C14A—C15A	155.5 (13)
N1—C9—C10—C11	0.3 (4)	C12Ai—C13A—C14A—C15A	−100.4 (16)
C8—C7—C11—C10	−0.9 (3)	C12A—C13A—C14A—C19A	−34.9 (15)
C8—C7—C11—C12	179.6 (2)	C12Ai—C13A—C14A—C19A	69.2 (15)
C9—C10—C11—C7	0.7 (4)	C19A—C14A—C15A—C16A	3(3)
C9—C10—C11—C12	−179.8 (2)	C13A—C14A—C15A—C16A	172.7 (16)
C7—C11—C12—C13	−178.3 (2)	C14A—C15A—C16A—C17A	−6(3)
C10—C11—C12—C13	2.2 (4)	C15A—C16A—C17A—C18A	4(3)
C11—C12—C13—C14	179.2 (2)	C16A—C17A—C18A—C19A	1(3)
C12—C13—C14—C15	173.1 (3)	C17A—C18A—C19A—C14A	−4(2)
C12—C13—C14—C19	−5.7 (4)	C15A—C14A—C19A—C18A	2(2)
C19—C14—C15—C16	−0.1 (6)	C13A—C14A—C19A—C18A	−168.1 (13)
C13—C14—C15—C16	−179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ii	0.96	2.41	3.361 (2)	169
C10—H10···Cg1	0.96	2.72	3.617 (3)	157
C16—H16···Cg1iii	0.96	2.93	3.787 (3)	149
C20—H20B···Cg2iv	0.96	2.86	3.588 (3)	134
C20—H20B···Cg3iv	0.96	2.65	3.343 (7)	130
C10A—H10A···Cg1	0.96	2.70	3.537 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.96	2.41	3.361 (2)	169
C10—H10⋯Cg1	0.96	2.72	3.617 (3)	157
C16—H16⋯Cg1ii	0.96	2.93	3.787 (3)	149
C20—H20B⋯Cg2iii	0.96	2.86	3.588 (3)	134
C20—H20B⋯Cg3iii	0.96	2.65	3.343 (7)	130
C10A—H10A⋯Cg1	0.96	2.70	3.537 (18)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are centroids of the C1–C6, C14–C19 and C14A–C19A rings, respectively.