1-Methyl-2-[(E)-2,4,5-trimeth-oxy-styr-yl]-pyridinium benzene-sulfonate mono-hydrate.

The asymmetric unit of the title compound, C(17)H(20)NO(3) (+)·C(6)H(5)O(3)S(-)·H(2)O, comprises two 1-methyl-2-[(E)-2,4,5-trimeth-oxy-styr-yl]pyridinium cations, two benzene-sulfonate anions and two water mol-ecules. The cations exist in the E conformation with respect to the C=C bond; one cation is essentially planar while the other is slightly twisted, the dihedral angles between the pyridinium and phenyl rings being 1.23 (14) and 6.64 (13)°, respectively. In the crystal, cations, anions and water mol-ecules are linked by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into chains along the b axis. π-π inter-actions with centroid-centroid distances in the range 3.5557 (16)-3.6876 (16) Å are observed. C-H⋯π inter-actions and a C⋯O short contact [2.94 (4) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to, and applications of, hy­droxy­lated stilbenes, see: Elmali et al. (2006 ▶); Kimura (2005 ▶); Ko et al. (1999 ▶); Nitta et al. (2002 ▶); Olas & Wachowicz (2002 ▶); Park et al. (2008 ▶); Roupe et al. (2006 ▶); Son et al. (2007 ▶). For related structures, see: Chanawanno et al. (2010 ▶); Fun et al. (2011 ▶); Mueangkeaw et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H20NO3 +·C6H5O3S−·H2O

M = 461.53

Triclinic,

a = 11.2458 (4) Å

b = 13.5995 (5) Å

c = 15.3604 (6) Å

α = 73.345 (2)°

β = 84.623 (2)°

γ = 82.842 (2)°

V = 2228.92 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.44 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.920, T max = 0.970

38826 measured reflections

10142 independent reflections

6560 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.180

S = 1.03

10142 reflections

598 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (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 datablock(s) global, I. DOI: 10.1107/S1600536812007805/ez2283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007805/ez2283Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007805/ez2283Isup3.cml

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

C17H20NO3+·C6H5O3S−·H2O	Z = 4
Mr = 461.53	F(000) = 976
Triclinic, P1	Dx = 1.375 Mg m−3
Hall symbol: -P 1	Melting point = 455–456 K
a = 11.2458 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5995 (5) Å	Cell parameters from 10142 reflections
c = 15.3604 (6) Å	θ = 2.2–27.5°
α = 73.345 (2)°	µ = 0.19 mm−1
β = 84.623 (2)°	T = 100 K
γ = 82.842 (2)°	Block, orange
V = 2228.92 (15) Å3	0.44 × 0.22 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	10142 independent reflections
Radiation source: sealed tube	6560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.920, Tmax = 0.970	k = −17→17
38826 measured reflections	l = −19→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0791P)2 + 1.8818P] where P = (Fo2 + 2Fc2)/3
10142 reflections	(Δ/σ)max = 0.001
598 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.45 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)
O1A	0.64507 (17)	0.11731 (17)	0.51621 (14)	0.0336 (5)
O2A	0.69138 (17)	0.04628 (17)	0.83918 (14)	0.0327 (5)
O3A	0.91709 (17)	0.06224 (17)	0.81037 (14)	0.0314 (5)
N1A	1.15749 (19)	0.16459 (17)	0.32746 (16)	0.0220 (5)
C1A	1.1978 (3)	0.1857 (2)	0.2393 (2)	0.0290 (7)
H1AA	1.2795	0.1901	0.2246	0.035*
C2A	1.1220 (3)	0.2008 (3)	0.1707 (2)	0.0335 (7)
H2AA	1.1512	0.2154	0.1101	0.040*
C3A	1.0001 (3)	0.1937 (2)	0.1943 (2)	0.0341 (7)
H3AA	0.9465	0.2026	0.1494	0.041*
C4A	0.9595 (2)	0.1734 (2)	0.2840 (2)	0.0291 (7)
H4AA	0.8779	0.1695	0.2992	0.035*
C5A	1.0373 (2)	0.1587 (2)	0.3530 (2)	0.0247 (6)
C6A	0.9983 (3)	0.1373 (3)	0.4472 (2)	0.0362 (8)
H6AA	1.0555	0.1282	0.4896	0.043*
C7A	0.8816 (3)	0.1295 (2)	0.4777 (2)	0.0351 (7)
H7AA	0.8263	0.1382	0.4341	0.042*
C8A	0.8348 (3)	0.1090 (2)	0.5718 (2)	0.0297 (7)
C9A	0.7104 (2)	0.1028 (2)	0.59021 (19)	0.0252 (6)
C10A	0.6599 (2)	0.0813 (2)	0.67848 (19)	0.0244 (6)
H10A	0.5778	0.0763	0.6895	0.029*
C11A	0.7317 (2)	0.0672 (2)	0.75031 (19)	0.0241 (6)
C12A	0.8564 (2)	0.0750 (2)	0.73381 (19)	0.0241 (6)
C13A	0.9063 (2)	0.0947 (2)	0.6466 (2)	0.0275 (7)
H13A	0.9886	0.0987	0.6362	0.033*
C14A	1.2469 (2)	0.1503 (2)	0.3959 (2)	0.0272 (7)
H14A	1.3256	0.1562	0.3659	0.041*
H14B	1.2446	0.0832	0.4385	0.041*
H14C	1.2286	0.2022	0.4276	0.041*
C15A	0.5171 (3)	0.1185 (3)	0.5306 (2)	0.0331 (7)
H15A	0.4818	0.1344	0.4730	0.050*
H15B	0.4865	0.1698	0.5610	0.050*
H15C	0.4972	0.0519	0.5674	0.050*
C16A	0.5639 (3)	0.0492 (3)	0.8575 (2)	0.0336 (7)
H16A	0.5454	0.0371	0.9218	0.050*
H16B	0.5344	−0.0033	0.8373	0.050*
H16C	0.5266	0.1156	0.8258	0.050*
C17A	1.0434 (3)	0.0711 (3)	0.7967 (2)	0.0334 (7)
H17A	1.0760	0.0636	0.8541	0.050*
H17B	1.0570	0.1376	0.7562	0.050*
H17C	1.0819	0.0181	0.7707	0.050*
S1A	0.59991 (6)	0.15568 (6)	0.23898 (5)	0.02814 (19)
O4A	0.47821 (19)	0.1975 (2)	0.21697 (16)	0.0399 (7)	0.948 (4)
O5A	0.6119 (2)	0.04475 (18)	0.28039 (16)	0.0383 (7)	0.948 (4)
O6A	0.65514 (19)	0.21139 (17)	0.29030 (15)	0.0328 (6)	0.948 (4)
O4AA	0.488 (3)	0.113 (3)	0.221 (3)	0.028 (10)*	0.052 (4)
O5AA	0.665 (4)	0.099 (3)	0.313 (3)	0.036 (12)*	0.052 (4)
O6AA	0.558 (3)	0.262 (3)	0.245 (2)	0.021 (9)*	0.052 (4)
C18A	0.6856 (2)	0.1748 (2)	0.1330 (2)	0.0250 (6)
C19A	0.7215 (2)	0.2718 (2)	0.0885 (2)	0.0290 (7)
H19A	0.6977	0.3272	0.1123	0.035*
C20A	0.7934 (3)	0.2851 (3)	0.0081 (2)	0.0335 (7)
H20A	0.8191	0.3494	−0.0214	0.040*
C21A	0.8267 (3)	0.2032 (3)	−0.0279 (2)	0.0356 (8)
H21A	0.8757	0.2124	−0.0812	0.043*
C22A	0.7880 (3)	0.1078 (3)	0.0144 (2)	0.0347 (7)
H22A	0.8091	0.0533	−0.0111	0.042*
C23A	0.7177 (2)	0.0935 (2)	0.0952 (2)	0.0304 (7)
H23A	0.6919	0.0291	0.1241	0.036*
O1B	0.28112 (17)	0.39190 (17)	0.41584 (14)	0.0330 (5)
O2B	0.25360 (17)	0.45714 (16)	0.09077 (14)	0.0303 (5)
O3B	0.02436 (17)	0.47482 (17)	0.11018 (14)	0.0304 (5)
N1B	−0.2427 (2)	0.35988 (18)	0.58282 (16)	0.0244 (5)
C1B	−0.2907 (3)	0.3367 (2)	0.6690 (2)	0.0306 (7)
H1BA	−0.3726	0.3304	0.6795	0.037*
C2B	−0.2229 (3)	0.3223 (2)	0.7410 (2)	0.0317 (7)
H2BA	−0.2574	0.3066	0.8001	0.038*
C3B	−0.1002 (3)	0.3315 (2)	0.7243 (2)	0.0280 (7)
H3BA	−0.0518	0.3228	0.7724	0.034*
C4B	−0.0510 (2)	0.3535 (2)	0.6363 (2)	0.0265 (6)
H4BA	0.0311	0.3586	0.6255	0.032*
C5B	−0.1224 (2)	0.3684 (2)	0.5628 (2)	0.0246 (6)
C6B	−0.0768 (3)	0.3963 (2)	0.4691 (2)	0.0328 (7)
H6BA	−0.1313	0.4195	0.4238	0.039*
C7B	0.0418 (3)	0.3905 (2)	0.4439 (2)	0.0300 (7)
H7BA	0.0944	0.3715	0.4905	0.036*
C8B	0.0947 (2)	0.4104 (2)	0.3527 (2)	0.0272 (6)
C9B	0.2210 (2)	0.4087 (2)	0.3390 (2)	0.0262 (6)
C10B	0.2777 (2)	0.4236 (2)	0.2528 (2)	0.0255 (6)
H10B	0.3610	0.4201	0.2451	0.031*
C11B	0.2087 (2)	0.4438 (2)	0.17786 (19)	0.0239 (6)
C12B	0.0817 (2)	0.4511 (2)	0.18900 (19)	0.0239 (6)
C13B	0.0278 (2)	0.4331 (2)	0.2751 (2)	0.0273 (7)
H13B	−0.0555	0.4359	0.2825	0.033*
C14B	−0.3247 (3)	0.3742 (3)	0.5090 (2)	0.0344 (7)
H14D	−0.4046	0.3629	0.5350	0.052*
H14E	−0.2981	0.3259	0.4746	0.052*
H14F	−0.3246	0.4432	0.4696	0.052*
C15B	0.4093 (3)	0.3863 (3)	0.4067 (2)	0.0378 (8)
H15D	0.4404	0.3683	0.4659	0.057*
H15E	0.4335	0.4521	0.3716	0.057*
H15F	0.4399	0.3348	0.3764	0.057*
C16B	0.3813 (3)	0.4530 (3)	0.0747 (2)	0.0348 (7)
H16D	0.4017	0.4661	0.0106	0.052*
H16E	0.4172	0.3858	0.1062	0.052*
H16F	0.4107	0.5042	0.0967	0.052*
C17B	−0.1048 (3)	0.4897 (3)	0.1180 (2)	0.0365 (8)
H17D	−0.1351	0.5106	0.0583	0.055*
H17E	−0.1300	0.5423	0.1482	0.055*
H17F	−0.1353	0.4263	0.1526	0.055*
S1B	0.68516 (6)	0.65230 (6)	0.30445 (5)	0.02695 (19)
O4B	0.77426 (19)	0.71188 (18)	0.32296 (16)	0.0391 (6)
O5B	0.7331 (2)	0.54663 (17)	0.31094 (15)	0.0401 (6)
O6B	0.57193 (19)	0.6606 (2)	0.35600 (15)	0.0437 (6)
C18B	0.6532 (2)	0.7081 (2)	0.1882 (2)	0.0249 (6)
C19B	0.7214 (3)	0.7823 (2)	0.1321 (2)	0.0306 (7)
H19B	0.7838	0.8042	0.1551	0.037*
C20B	0.6959 (3)	0.8236 (2)	0.0415 (2)	0.0354 (8)
H20B	0.7413	0.8737	0.0037	0.042*
C21B	0.6034 (3)	0.7910 (2)	0.0068 (2)	0.0362 (8)
H21B	0.5877	0.8179	−0.0543	0.043*
C22B	0.5352 (3)	0.7188 (2)	0.0632 (2)	0.0354 (8)
H22B	0.4719	0.6979	0.0403	0.043*
C23B	0.5593 (3)	0.6767 (2)	0.1536 (2)	0.0296 (7)
H23B	0.5128	0.6275	0.1912	0.035*
O1W	0.6043 (2)	0.42912 (18)	0.22536 (18)	0.0468 (6)
H1W1	0.6480	0.4851	0.2442	0.070*
H2W1	0.6213	0.3548	0.2557	0.070*
O2W	0.77573 (19)	0.88811 (19)	0.39160 (16)	0.0427 (6)
H1W2	0.7312	0.9433	0.3541	0.064*
H2W2	0.7657	0.8252	0.3799	0.064*

	U11	U22	U33	U12	U13	U23
O1A	0.0137 (10)	0.0592 (15)	0.0269 (12)	−0.0028 (9)	−0.0017 (9)	−0.0104 (10)
O2A	0.0171 (10)	0.0534 (14)	0.0271 (12)	−0.0036 (9)	0.0021 (9)	−0.0116 (10)
O3A	0.0152 (10)	0.0482 (13)	0.0315 (12)	−0.0024 (9)	−0.0026 (9)	−0.0124 (10)
N1A	0.0116 (11)	0.0283 (13)	0.0278 (13)	−0.0014 (9)	−0.0013 (9)	−0.0108 (10)
C1A	0.0155 (14)	0.0363 (17)	0.0338 (18)	−0.0023 (12)	0.0013 (12)	−0.0085 (13)
C2A	0.0217 (16)	0.048 (2)	0.0299 (17)	−0.0001 (14)	0.0000 (13)	−0.0118 (14)
C3A	0.0200 (15)	0.0418 (19)	0.042 (2)	−0.0007 (13)	−0.0065 (14)	−0.0134 (15)
C4A	0.0113 (13)	0.0309 (16)	0.048 (2)	−0.0026 (11)	−0.0018 (13)	−0.0151 (14)
C5A	0.0136 (13)	0.0267 (15)	0.0339 (17)	−0.0002 (11)	0.0028 (12)	−0.0105 (12)
C6A	0.0216 (16)	0.051 (2)	0.0359 (19)	0.0008 (14)	−0.0031 (14)	−0.0124 (15)
C7A	0.0245 (16)	0.0383 (18)	0.042 (2)	−0.0007 (13)	−0.0031 (14)	−0.0109 (15)
C8A	0.0156 (14)	0.0431 (18)	0.0293 (17)	−0.0003 (12)	0.0017 (12)	−0.0105 (14)
C9A	0.0148 (14)	0.0338 (16)	0.0250 (16)	0.0005 (11)	−0.0014 (12)	−0.0066 (12)
C10A	0.0109 (13)	0.0313 (16)	0.0311 (16)	−0.0005 (11)	0.0007 (11)	−0.0101 (12)
C11A	0.0168 (14)	0.0291 (15)	0.0258 (16)	0.0000 (11)	0.0007 (12)	−0.0084 (12)
C12A	0.0165 (14)	0.0294 (16)	0.0276 (16)	0.0021 (11)	−0.0046 (12)	−0.0108 (12)
C13A	0.0099 (13)	0.0369 (17)	0.0361 (18)	−0.0007 (11)	0.0009 (12)	−0.0121 (13)
C14A	0.0117 (13)	0.0373 (17)	0.0337 (17)	−0.0022 (11)	−0.0025 (12)	−0.0116 (13)
C15A	0.0161 (15)	0.047 (2)	0.0345 (18)	−0.0027 (13)	−0.0033 (13)	−0.0081 (15)
C16A	0.0179 (15)	0.049 (2)	0.0298 (17)	−0.0017 (13)	0.0061 (13)	−0.0072 (14)
C17A	0.0192 (15)	0.0418 (19)	0.0412 (19)	−0.0030 (13)	−0.0063 (13)	−0.0136 (15)
S1A	0.0132 (3)	0.0387 (4)	0.0323 (4)	−0.0053 (3)	0.0019 (3)	−0.0095 (3)
O4A	0.0122 (11)	0.0612 (19)	0.0437 (15)	−0.0014 (10)	−0.0004 (10)	−0.0118 (12)
O5A	0.0338 (14)	0.0379 (14)	0.0404 (14)	−0.0093 (11)	0.0037 (11)	−0.0058 (11)
O6A	0.0225 (12)	0.0429 (14)	0.0344 (13)	−0.0051 (10)	0.0005 (10)	−0.0130 (10)
C18A	0.0094 (13)	0.0361 (17)	0.0298 (16)	−0.0019 (11)	−0.0042 (11)	−0.0090 (13)
C19A	0.0155 (14)	0.0365 (17)	0.0346 (18)	0.0020 (12)	−0.0041 (12)	−0.0102 (14)
C20A	0.0225 (16)	0.0401 (18)	0.0318 (18)	−0.0013 (13)	−0.0058 (13)	−0.0002 (14)
C21A	0.0243 (16)	0.054 (2)	0.0238 (17)	0.0044 (14)	−0.0034 (13)	−0.0061 (15)
C22A	0.0223 (16)	0.046 (2)	0.0379 (19)	0.0052 (14)	−0.0034 (14)	−0.0172 (15)
C23A	0.0160 (14)	0.0363 (17)	0.0384 (18)	−0.0016 (12)	−0.0048 (13)	−0.0092 (14)
O1B	0.0129 (10)	0.0563 (14)	0.0323 (12)	0.0006 (9)	−0.0038 (9)	−0.0173 (10)
O2B	0.0137 (10)	0.0456 (13)	0.0300 (12)	−0.0013 (9)	0.0022 (8)	−0.0098 (10)
O3B	0.0141 (10)	0.0513 (14)	0.0253 (11)	0.0014 (9)	−0.0014 (8)	−0.0120 (10)
N1B	0.0141 (11)	0.0302 (13)	0.0276 (13)	−0.0003 (9)	−0.0019 (10)	−0.0069 (10)
C1B	0.0160 (14)	0.0375 (17)	0.0322 (17)	0.0010 (12)	0.0035 (13)	−0.0033 (13)
C2B	0.0215 (16)	0.0378 (18)	0.0302 (17)	0.0049 (13)	0.0010 (13)	−0.0049 (13)
C3B	0.0243 (16)	0.0305 (16)	0.0289 (17)	0.0017 (12)	−0.0069 (13)	−0.0079 (13)
C4B	0.0137 (14)	0.0305 (16)	0.0343 (17)	−0.0014 (11)	−0.0035 (12)	−0.0070 (13)
C5B	0.0138 (13)	0.0296 (16)	0.0296 (16)	0.0005 (11)	−0.0018 (12)	−0.0077 (12)
C6B	0.0184 (15)	0.0451 (19)	0.0331 (18)	0.0004 (13)	−0.0028 (13)	−0.0093 (14)
C7B	0.0216 (15)	0.0335 (17)	0.0354 (18)	−0.0010 (12)	−0.0033 (13)	−0.0105 (14)
C8B	0.0147 (14)	0.0395 (17)	0.0269 (16)	0.0001 (12)	−0.0006 (12)	−0.0099 (13)
C9B	0.0169 (14)	0.0324 (16)	0.0304 (17)	0.0026 (12)	−0.0060 (12)	−0.0112 (13)
C10B	0.0115 (13)	0.0299 (16)	0.0359 (17)	−0.0022 (11)	−0.0009 (12)	−0.0108 (13)
C11B	0.0190 (14)	0.0254 (15)	0.0278 (16)	−0.0014 (11)	0.0015 (12)	−0.0093 (12)
C12B	0.0145 (14)	0.0296 (15)	0.0285 (16)	−0.0006 (11)	−0.0016 (12)	−0.0102 (12)
C13B	0.0116 (13)	0.0364 (17)	0.0355 (18)	−0.0021 (12)	−0.0003 (12)	−0.0130 (13)
C14B	0.0170 (15)	0.051 (2)	0.0311 (18)	−0.0070 (14)	−0.0045 (13)	−0.0032 (15)
C15B	0.0157 (15)	0.060 (2)	0.0381 (19)	0.0010 (14)	−0.0078 (13)	−0.0147 (16)
C16B	0.0153 (15)	0.050 (2)	0.0388 (19)	−0.0040 (13)	0.0076 (13)	−0.0154 (15)
C17B	0.0139 (15)	0.061 (2)	0.0354 (19)	0.0030 (14)	−0.0036 (13)	−0.0176 (16)
S1B	0.0133 (3)	0.0366 (4)	0.0299 (4)	0.0012 (3)	−0.0015 (3)	−0.0090 (3)
O4B	0.0249 (12)	0.0504 (14)	0.0442 (14)	−0.0071 (10)	−0.0092 (10)	−0.0132 (11)
O5B	0.0397 (14)	0.0389 (13)	0.0370 (13)	0.0040 (10)	−0.0056 (10)	−0.0055 (10)
O6B	0.0162 (11)	0.0790 (18)	0.0346 (13)	0.0030 (11)	0.0001 (10)	−0.0177 (12)
C18B	0.0122 (13)	0.0318 (16)	0.0308 (16)	0.0032 (11)	−0.0013 (12)	−0.0109 (13)
C19B	0.0205 (15)	0.0369 (17)	0.0364 (18)	−0.0037 (12)	0.0019 (13)	−0.0143 (14)
C20B	0.0334 (18)	0.0330 (18)	0.0363 (19)	−0.0030 (14)	0.0055 (15)	−0.0064 (14)
C21B	0.0385 (19)	0.0379 (19)	0.0302 (18)	0.0074 (14)	−0.0064 (15)	−0.0097 (14)
C22B	0.0295 (18)	0.0363 (18)	0.044 (2)	0.0029 (14)	−0.0119 (15)	−0.0160 (15)
C23B	0.0188 (15)	0.0335 (17)	0.0368 (18)	−0.0015 (12)	−0.0022 (13)	−0.0110 (14)
O1W	0.0363 (14)	0.0420 (14)	0.0641 (17)	−0.0029 (11)	−0.0015 (12)	−0.0189 (12)
O2W	0.0273 (13)	0.0596 (16)	0.0433 (14)	0.0019 (11)	−0.0062 (10)	−0.0191 (12)

O1A—C9A	1.365 (3)	O1B—C15B	1.429 (3)
O1A—C15A	1.435 (3)	O2B—C11B	1.354 (3)
O2A—C11A	1.358 (3)	O2B—C16B	1.431 (3)
O2A—C16A	1.433 (3)	O3B—C12B	1.363 (3)
O3A—C12A	1.372 (3)	O3B—C17B	1.439 (3)
O3A—C17A	1.431 (3)	N1B—C1B	1.347 (4)
N1A—C1A	1.347 (4)	N1B—C5B	1.370 (3)
N1A—C5A	1.377 (3)	N1B—C14B	1.483 (4)
N1A—C14A	1.478 (4)	C1B—C2B	1.356 (4)
C1A—C2A	1.372 (4)	C1B—H1BA	0.9300
C1A—H1AA	0.9300	C2B—C3B	1.394 (4)
C2A—C3A	1.393 (4)	C2B—H2BA	0.9300
C2A—H2AA	0.9300	C3B—C4B	1.374 (4)
C3A—C4A	1.371 (4)	C3B—H3BA	0.9300
C3A—H3AA	0.9300	C4B—C5B	1.400 (4)
C4A—C5A	1.391 (4)	C4B—H4BA	0.9300
C4A—H4AA	0.9300	C5B—C6B	1.441 (4)
C5A—C6A	1.430 (4)	C6B—C7B	1.352 (4)
C6A—C7A	1.358 (4)	C6B—H6BA	0.9300
C6A—H6AA	0.9300	C7B—C8B	1.433 (4)
C7A—C8A	1.451 (4)	C7B—H7BA	0.9300
C7A—H7AA	0.9300	C8B—C13B	1.408 (4)
C8A—C9A	1.409 (4)	C8B—C9B	1.415 (4)
C8A—C13A	1.418 (4)	C9B—C10B	1.386 (4)
C9A—C10A	1.384 (4)	C10B—C11B	1.390 (4)
C10A—C11A	1.383 (4)	C10B—H10B	0.9300
C10A—H10A	0.9300	C11B—C12B	1.417 (4)
C11A—C12A	1.414 (4)	C12B—C13B	1.371 (4)
C12A—C13A	1.368 (4)	C13B—H13B	0.9300
C13A—H13A	0.9300	C14B—H14D	0.9600
C14A—H14A	0.9600	C14B—H14E	0.9600
C14A—H14B	0.9600	C14B—H14F	0.9600
C14A—H14C	0.9600	C15B—H15D	0.9600
C15A—H15A	0.9600	C15B—H15E	0.9600
C15A—H15B	0.9600	C15B—H15F	0.9600
C15A—H15C	0.9600	C16B—H16D	0.9600
C16A—H16A	0.9600	C16B—H16E	0.9600
C16A—H16B	0.9600	C16B—H16F	0.9600
C16A—H16C	0.9600	C17B—H17D	0.9600
C17A—H17A	0.9600	C17B—H17E	0.9600
C17A—H17B	0.9600	C17B—H17F	0.9600
C17A—H17C	0.9600	S1B—O6B	1.445 (2)
S1A—O5AA	1.40 (4)	S1B—O5B	1.449 (2)
S1A—O4A	1.447 (2)	S1B—O4B	1.459 (2)
S1A—O5A	1.454 (2)	S1B—C18B	1.780 (3)
S1A—O6A	1.460 (2)	C18B—C19B	1.384 (4)
S1A—O6AA	1.49 (3)	C18B—C23B	1.389 (4)
S1A—O4AA	1.53 (4)	C19B—C20B	1.387 (5)
S1A—C18A	1.781 (3)	C19B—H19B	0.9300
C18A—C23A	1.385 (4)	C20B—C21B	1.384 (5)
C18A—C19A	1.391 (4)	C20B—H20B	0.9300
C19A—C20A	1.390 (4)	C21B—C22B	1.371 (5)
C19A—H19A	0.9300	C21B—H21B	0.9300
C20A—C21A	1.377 (5)	C22B—C23B	1.380 (4)
C20A—H20A	0.9300	C22B—H22B	0.9300
C21A—C22A	1.377 (5)	C23B—H23B	0.9300
C21A—H21A	0.9300	O1W—H1W1	1.0725
C22A—C23A	1.386 (4)	O1W—H2W1	0.9868
C22A—H22A	0.9300	O2W—H1W2	0.9268
C23A—H23A	0.9300	O2W—H2W2	0.9445
O1B—C9B	1.363 (3)
C9A—O1A—C15A	117.9 (2)	C21A—C22A—C23A	119.7 (3)
C11A—O2A—C16A	116.5 (2)	C21A—C22A—H22A	120.2
C12A—O3A—C17A	116.5 (2)	C23A—C22A—H22A	120.2
C1A—N1A—C5A	121.4 (2)	C22A—C23A—C18A	120.2 (3)
C1A—N1A—C14A	117.5 (2)	C22A—C23A—H23A	119.9
C5A—N1A—C14A	121.1 (2)	C18A—C23A—H23A	119.9
N1A—C1A—C2A	122.0 (3)	C9B—O1B—C15B	117.9 (2)
N1A—C1A—H1AA	119.0	C11B—O2B—C16B	117.3 (2)
C2A—C1A—H1AA	119.0	C12B—O3B—C17B	116.7 (2)
C1A—C2A—C3A	118.1 (3)	C1B—N1B—C5B	122.1 (2)
C1A—C2A—H2AA	121.0	C1B—N1B—C14B	117.5 (2)
C3A—C2A—H2AA	121.0	C5B—N1B—C14B	120.4 (2)
C4A—C3A—C2A	119.7 (3)	N1B—C1B—C2B	121.7 (3)
C4A—C3A—H3AA	120.2	N1B—C1B—H1BA	119.1
C2A—C3A—H3AA	120.2	C2B—C1B—H1BA	119.1
C3A—C4A—C5A	121.7 (3)	C1B—C2B—C3B	118.5 (3)
C3A—C4A—H4AA	119.1	C1B—C2B—H2BA	120.7
C5A—C4A—H4AA	119.1	C3B—C2B—H2BA	120.7
N1A—C5A—C4A	117.2 (3)	C4B—C3B—C2B	119.6 (3)
N1A—C5A—C6A	119.6 (3)	C4B—C3B—H3BA	120.2
C4A—C5A—C6A	123.3 (3)	C2B—C3B—H3BA	120.2
C7A—C6A—C5A	123.0 (3)	C3B—C4B—C5B	121.1 (3)
C7A—C6A—H6AA	118.5	C3B—C4B—H4BA	119.4
C5A—C6A—H6AA	118.5	C5B—C4B—H4BA	119.4
C6A—C7A—C8A	126.4 (3)	N1B—C5B—C4B	116.9 (3)
C6A—C7A—H7AA	116.8	N1B—C5B—C6B	119.6 (3)
C8A—C7A—H7AA	116.8	C4B—C5B—C6B	123.5 (3)
C9A—C8A—C13A	117.8 (3)	C7B—C6B—C5B	123.0 (3)
C9A—C8A—C7A	118.1 (3)	C7B—C6B—H6BA	118.5
C13A—C8A—C7A	124.1 (3)	C5B—C6B—H6BA	118.5
O1A—C9A—C10A	123.1 (2)	C6B—C7B—C8B	126.7 (3)
O1A—C9A—C8A	115.8 (2)	C6B—C7B—H7BA	116.6
C10A—C9A—C8A	121.2 (3)	C8B—C7B—H7BA	116.6
C11A—C10A—C9A	119.9 (3)	C13B—C8B—C9B	117.6 (3)
C11A—C10A—H10A	120.0	C13B—C8B—C7B	123.6 (3)
C9A—C10A—H10A	120.0	C9B—C8B—C7B	118.8 (3)
O2A—C11A—C10A	124.7 (2)	O1B—C9B—C10B	123.3 (2)
O2A—C11A—C12A	115.1 (2)	O1B—C9B—C8B	115.3 (3)
C10A—C11A—C12A	120.2 (3)	C10B—C9B—C8B	121.4 (3)
C13A—C12A—O3A	125.7 (3)	C9B—C10B—C11B	119.3 (3)
C13A—C12A—C11A	119.7 (3)	C9B—C10B—H10B	120.3
O3A—C12A—C11A	114.6 (2)	C11B—C10B—H10B	120.3
C12A—C13A—C8A	121.2 (3)	O2B—C11B—C10B	124.8 (2)
C12A—C13A—H13A	119.4	O2B—C11B—C12B	114.6 (2)
C8A—C13A—H13A	119.4	C10B—C11B—C12B	120.6 (3)
N1A—C14A—H14A	109.5	O3B—C12B—C13B	126.0 (2)
N1A—C14A—H14B	109.5	O3B—C12B—C11B	114.9 (2)
H14A—C14A—H14B	109.5	C13B—C12B—C11B	119.1 (3)
N1A—C14A—H14C	109.5	C12B—C13B—C8B	121.9 (3)
H14A—C14A—H14C	109.5	C12B—C13B—H13B	119.0
H14B—C14A—H14C	109.5	C8B—C13B—H13B	119.0
O1A—C15A—H15A	109.5	N1B—C14B—H14D	109.5
O1A—C15A—H15B	109.5	N1B—C14B—H14E	109.5
H15A—C15A—H15B	109.5	H14D—C14B—H14E	109.5
O1A—C15A—H15C	109.5	N1B—C14B—H14F	109.5
H15A—C15A—H15C	109.5	H14D—C14B—H14F	109.5
H15B—C15A—H15C	109.5	H14E—C14B—H14F	109.5
O2A—C16A—H16A	109.5	O1B—C15B—H15D	109.5
O2A—C16A—H16B	109.5	O1B—C15B—H15E	109.5
H16A—C16A—H16B	109.5	H15D—C15B—H15E	109.5
O2A—C16A—H16C	109.5	O1B—C15B—H15F	109.5
H16A—C16A—H16C	109.5	H15D—C15B—H15F	109.5
H16B—C16A—H16C	109.5	H15E—C15B—H15F	109.5
O3A—C17A—H17A	109.5	O2B—C16B—H16D	109.5
O3A—C17A—H17B	109.5	O2B—C16B—H16E	109.5
H17A—C17A—H17B	109.5	H16D—C16B—H16E	109.5
O3A—C17A—H17C	109.5	O2B—C16B—H16F	109.5
H17A—C17A—H17C	109.5	H16D—C16B—H16F	109.5
H17B—C17A—H17C	109.5	H16E—C16B—H16F	109.5
O5AA—S1A—O4A	140.5 (17)	O3B—C17B—H17D	109.5
O5AA—S1A—O5A	51.4 (18)	O3B—C17B—H17E	109.5
O4A—S1A—O5A	113.11 (15)	H17D—C17B—H17E	109.5
O5AA—S1A—O6A	61.6 (18)	O3B—C17B—H17F	109.5
O4A—S1A—O6A	113.33 (14)	H17D—C17B—H17F	109.5
O5A—S1A—O6A	112.66 (14)	H17E—C17B—H17F	109.5
O5AA—S1A—O6AA	112 (2)	O6B—S1B—O5B	113.29 (15)
O4A—S1A—O6AA	61.6 (14)	O6B—S1B—O4B	113.51 (14)
O5A—S1A—O6AA	150.0 (13)	O5B—S1B—O4B	111.97 (14)
O6A—S1A—O6AA	54.4 (14)	O6B—S1B—C18B	105.69 (13)
O5AA—S1A—O4AA	118 (2)	O5B—S1B—C18B	105.38 (13)
O5A—S1A—O4AA	72.0 (15)	O4B—S1B—C18B	106.17 (14)
O6A—S1A—O4AA	148.6 (15)	C19B—C18B—C23B	119.8 (3)
O6AA—S1A—O4AA	105 (2)	C19B—C18B—S1B	120.6 (2)
O5AA—S1A—C18A	113.1 (17)	C23B—C18B—S1B	119.6 (2)
O4A—S1A—C18A	105.98 (14)	C18B—C19B—C20B	119.6 (3)
O5A—S1A—C18A	105.38 (14)	C18B—C19B—H19B	120.2
O6A—S1A—C18A	105.50 (13)	C20B—C19B—H19B	120.2
O6AA—S1A—C18A	104.4 (13)	C21B—C20B—C19B	120.5 (3)
O4AA—S1A—C18A	102.7 (14)	C21B—C20B—H20B	119.8
C23A—C18A—C19A	119.8 (3)	C19B—C20B—H20B	119.8
C23A—C18A—S1A	120.4 (2)	C22B—C21B—C20B	119.6 (3)
C19A—C18A—S1A	119.7 (2)	C22B—C21B—H21B	120.2
C20A—C19A—C18A	119.5 (3)	C20B—C21B—H21B	120.2
C20A—C19A—H19A	120.2	C21B—C22B—C23B	120.7 (3)
C18A—C19A—H19A	120.3	C21B—C22B—H22B	119.7
C21A—C20A—C19A	120.1 (3)	C23B—C22B—H22B	119.7
C21A—C20A—H20A	120.0	C22B—C23B—C18B	119.9 (3)
C19A—C20A—H20A	120.0	C22B—C23B—H23B	120.1
C20A—C21A—C22A	120.7 (3)	C18B—C23B—H23B	120.1
C20A—C21A—H21A	119.7	H1W1—O1W—H2W1	120.7
C22A—C21A—H21A	119.7	H1W2—O2W—H2W2	111.6
C5A—N1A—C1A—C2A	−1.0 (4)	C21A—C22A—C23A—C18A	0.4 (4)
C14A—N1A—C1A—C2A	−179.6 (3)	C19A—C18A—C23A—C22A	1.7 (4)
N1A—C1A—C2A—C3A	−0.1 (5)	S1A—C18A—C23A—C22A	−177.6 (2)
C1A—C2A—C3A—C4A	0.9 (5)	C5B—N1B—C1B—C2B	1.2 (4)
C2A—C3A—C4A—C5A	−0.6 (5)	C14B—N1B—C1B—C2B	−179.9 (3)
C1A—N1A—C5A—C4A	1.2 (4)	N1B—C1B—C2B—C3B	−0.3 (5)
C14A—N1A—C5A—C4A	179.8 (2)	C1B—C2B—C3B—C4B	−0.8 (4)
C1A—N1A—C5A—C6A	−179.3 (3)	C2B—C3B—C4B—C5B	0.9 (4)
C14A—N1A—C5A—C6A	−0.7 (4)	C1B—N1B—C5B—C4B	−1.0 (4)
C3A—C4A—C5A—N1A	−0.4 (4)	C14B—N1B—C5B—C4B	−179.8 (3)
C3A—C4A—C5A—C6A	−179.9 (3)	C1B—N1B—C5B—C6B	−178.2 (3)
N1A—C5A—C6A—C7A	−179.5 (3)	C14B—N1B—C5B—C6B	2.9 (4)
C4A—C5A—C6A—C7A	−0.1 (5)	C3B—C4B—C5B—N1B	−0.1 (4)
C5A—C6A—C7A—C8A	−179.4 (3)	C3B—C4B—C5B—C6B	177.0 (3)
C6A—C7A—C8A—C9A	−179.4 (3)	N1B—C5B—C6B—C7B	−169.2 (3)
C6A—C7A—C8A—C13A	0.5 (5)	C4B—C5B—C6B—C7B	13.8 (5)
C15A—O1A—C9A—C10A	5.2 (4)	C5B—C6B—C7B—C8B	175.8 (3)
C15A—O1A—C9A—C8A	−176.0 (3)	C6B—C7B—C8B—C13B	−4.4 (5)
C13A—C8A—C9A—O1A	179.8 (3)	C6B—C7B—C8B—C9B	174.8 (3)
C7A—C8A—C9A—O1A	−0.2 (4)	C15B—O1B—C9B—C10B	−2.0 (4)
C13A—C8A—C9A—C10A	−1.3 (4)	C15B—O1B—C9B—C8B	178.2 (3)
C7A—C8A—C9A—C10A	178.6 (3)	C13B—C8B—C9B—O1B	176.6 (3)
O1A—C9A—C10A—C11A	179.9 (3)	C7B—C8B—C9B—O1B	−2.7 (4)
C8A—C9A—C10A—C11A	1.1 (4)	C13B—C8B—C9B—C10B	−3.2 (4)
C16A—O2A—C11A—C10A	−6.3 (4)	C7B—C8B—C9B—C10B	177.6 (3)
C16A—O2A—C11A—C12A	173.3 (3)	O1B—C9B—C10B—C11B	−177.8 (3)
C9A—C10A—C11A—O2A	179.7 (3)	C8B—C9B—C10B—C11B	2.0 (4)
C9A—C10A—C11A—C12A	0.2 (4)	C16B—O2B—C11B—C10B	−1.9 (4)
C17A—O3A—C12A—C13A	0.4 (4)	C16B—O2B—C11B—C12B	178.6 (2)
C17A—O3A—C12A—C11A	−179.1 (2)	C9B—C10B—C11B—O2B	−178.3 (3)
O2A—C11A—C12A—C13A	179.2 (3)	C9B—C10B—C11B—C12B	1.2 (4)
C10A—C11A—C12A—C13A	−1.2 (4)	C17B—O3B—C12B—C13B	4.9 (4)
O2A—C11A—C12A—O3A	−1.3 (4)	C17B—O3B—C12B—C11B	−176.0 (3)
C10A—C11A—C12A—O3A	178.3 (2)	O2B—C11B—C12B—O3B	−2.8 (4)
O3A—C12A—C13A—C8A	−178.5 (3)	C10B—C11B—C12B—O3B	177.7 (2)
C11A—C12A—C13A—C8A	1.0 (4)	O2B—C11B—C12B—C13B	176.5 (3)
C9A—C8A—C13A—C12A	0.2 (4)	C10B—C11B—C12B—C13B	−3.1 (4)
C7A—C8A—C13A—C12A	−179.7 (3)	O3B—C12B—C13B—C8B	−179.1 (3)
O5AA—S1A—C18A—C23A	71.9 (19)	C11B—C12B—C13B—C8B	1.8 (4)
O4A—S1A—C18A—C23A	−102.4 (3)	C9B—C8B—C13B—C12B	1.2 (4)
O5A—S1A—C18A—C23A	17.8 (3)	C7B—C8B—C13B—C12B	−179.5 (3)
O6A—S1A—C18A—C23A	137.2 (2)	O6B—S1B—C18B—C19B	129.7 (2)
O6AA—S1A—C18A—C23A	−166.4 (14)	O5B—S1B—C18B—C19B	−110.1 (3)
O4AA—S1A—C18A—C23A	−56.8 (16)	O4B—S1B—C18B—C19B	8.8 (3)
O5AA—S1A—C18A—C19A	−107.5 (19)	O6B—S1B—C18B—C23B	−50.5 (3)
O4A—S1A—C18A—C19A	78.3 (3)	O5B—S1B—C18B—C23B	69.7 (3)
O5A—S1A—C18A—C19A	−161.6 (2)	O4B—S1B—C18B—C23B	−171.4 (2)
O6A—S1A—C18A—C19A	−42.2 (3)	C23B—C18B—C19B—C20B	−0.7 (4)
O6AA—S1A—C18A—C19A	14.2 (14)	S1B—C18B—C19B—C20B	179.1 (2)
O4AA—S1A—C18A—C19A	123.9 (16)	C18B—C19B—C20B—C21B	−0.3 (5)
C23A—C18A—C19A—C20A	−2.5 (4)	C19B—C20B—C21B—C22B	1.3 (5)
S1A—C18A—C19A—C20A	176.8 (2)	C20B—C21B—C22B—C23B	−1.4 (5)
C18A—C19A—C20A—C21A	1.2 (4)	C21B—C22B—C23B—C18B	0.4 (5)
C19A—C20A—C21A—C22A	0.9 (5)	C19B—C18B—C23B—C22B	0.7 (4)
C20A—C21A—C22A—C23A	−1.7 (5)	S1B—C18B—C23B—C22B	−179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O5B	1.07	1.88	2.919 (3)	161
O1W—H2W1···O6A	0.99	1.87	2.843 (3)	169
O2W—H1W2···O5Ai	0.93	1.98	2.894 (3)	169
O2W—H2W2···O4B	0.94	1.97	2.884 (4)	163
C1A—H1AA···O4Aii	0.93	2.24	3.159 (4)	169
C4A—H4AA···O6A	0.93	2.51	3.394 (3)	160
C1B—H1BA···O6Biii	0.93	2.34	3.216 (4)	157
C4B—H4BA···O4Biv	0.93	2.39	3.198 (3)	145
C6B—H6BA···O5Bv	0.93	2.54	3.419 (4)	158
C14B—H14D···O6Biii	0.96	2.39	3.307 (4)	160
C14B—H14F···O5Bv	0.96	2.51	3.331 (4)	143
C19A—H19A···O1W	0.93	2.59	3.477 (4)	160
C20A—H20A···O2Bvi	0.93	2.60	3.393 (5)	144
C3A—H3AA···Cg5	0.93	2.78	3.688 (3)	164
C16A—H16C···Cg6iv	0.96	2.79	3.453 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the C18A–C23A and C18B–C23B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O5B	1.07	1.88	2.919 (3)	161
O1W—H2W1⋯O6A	0.99	1.87	2.843 (3)	169
O2W—H1W2⋯O5Ai	0.93	1.98	2.894 (3)	169
O2W—H2W2⋯O4B	0.94	1.97	2.884 (4)	163
C1A—H1AA⋯O4Aii	0.93	2.24	3.159 (4)	169
C4A—H4AA⋯O6A	0.93	2.51	3.394 (3)	160
C1B—H1BA⋯O6Biii	0.93	2.34	3.216 (4)	157
C4B—H4BA⋯O4Biv	0.93	2.39	3.198 (3)	145
C6B—H6BA⋯O5Bv	0.93	2.54	3.419 (4)	158
C14B—H14D⋯O6Biii	0.96	2.39	3.307 (4)	160
C14B—H14F⋯O5Bv	0.96	2.51	3.331 (4)	143
C19A—H19A⋯O1W	0.93	2.59	3.477 (4)	160
C20A—H20A⋯O2Bvi	0.93	2.60	3.393 (5)	144
C3A—H3AA⋯Cg5	0.93	2.78	3.688 (3)	164
C16A—H16C⋯Cg6iv	0.96	2.79	3.453 (4)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .