1,1'-Dimethyl-4,4'-(2,4-di-1-naphthyl-cyclo-butane-1,3-di-yl)dipyridinium-(E)-1-methyl-4-[2-(1-naphth-yl)vin-yl]pyridinium-4-amino-benzene-sulfonate-water (0.25/1.50/2/2).

In the title compound, 1.5C(18)H(16)N(+)·0.25C(36)H(32)N(2) (2+)·2C(6)H(6)NO(3)S(-)·2H(2)O, the monocation exists in the E configuration with respect to the ethenyl C=C double bond and is almost planar, the dihedral angles between the pyridinium and the fused six-membered rings being 3.1 (7) and 3.8 (8)°. 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 (-x, 1 - y, 1 - z). The anions and water mol-ecules are linked into a chain along the a axis by O-H⋯O and N-H⋯O hydrogen bonds. The structure is further stabilized by C-H⋯O hydrogen bonds and π-π inter-actions between pyridinium and benzene rings, with centroid-centroid distances in the range 3.516 (9)-3.553 (8) Å. The crystal is a twin with twin law, TWIN 0 0 0 0 1 0 1. The monocation and dication are disordered with fractional site occupancy ratio of 0.75:0.25.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to non-linear optical materials, see: Williams (1984 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Fun et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

1.5C18H16N+·0.25C36H32N2 2+·2C6H6NO3S−·2H2O

M = 873.04

Monoclinic,

a = 6.6352 (4) Å

b = 14.8824 (8) Å

c = 20.9347 (13) Å

β = 97.921 (3)°

V = 2047.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.52 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.906, T max = 0.986

21302 measured reflections

4099 independent reflections

3550 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.097

wR(F 2) = 0.275

S = 1.07

4099 reflections

440 parameters

300 restraints

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −0.62 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 datablocks global, I. DOI: 10.1107/S1600536809029730/ci2847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029730/ci2847Isup2.hkl

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

1.5C18H16N+·0.25C36H32N22+·2C6H6NO3S−·2H2O	F(000) = 920
Mr = 873.04	Dx = 1.416 Mg m−3
Monoclinic, P21/c	Melting point = 513–514 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.6352 (4) Å	Cell parameters from 4099 reflections
b = 14.8824 (8) Å	θ = 1.0–26.0°
c = 20.9347 (13) Å	µ = 0.19 mm−1
β = 97.921 (3)°	T = 100 K
V = 2047.5 (2) Å3	Needle, green
Z = 2	0.52 × 0.13 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	4099 independent reflections
Radiation source: sealed tube	3550 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 26.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.906, Tmax = 0.986	k = −16→18
21302 measured reflections	l = −25→23

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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.275	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1017P)2 + 16.5792P] where P = (Fo2 + 2Fc2)/3
4099 reflections	(Δ/σ)max = 0.001
440 parameters	Δρmax = 1.20 e Å−3
300 restraints	Δρmin = −0.61 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	0.3679 (2)	0.09002 (8)	0.28289 (6)	0.0218 (3)
O1	0.5862 (6)	0.0903 (2)	0.28680 (19)	0.0275 (9)
O2	0.2700 (6)	0.0497 (3)	0.2232 (2)	0.0298 (9)
O3	0.2958 (7)	0.0516 (3)	0.3399 (2)	0.0352 (10)
N2	0.1545 (7)	0.4776 (3)	0.2898 (2)	0.0245 (10)
H2B	0.2400	0.5174	0.2807	0.029*
H2C	0.0426	0.4940	0.3028	0.029*
C19	0.2965 (8)	0.2043 (3)	0.2812 (2)	0.0197 (10)
C20	0.4260 (8)	0.2701 (4)	0.2610 (2)	0.0227 (11)
H20	0.5461	0.2529	0.2461	0.027*
C21	0.3758 (8)	0.3600 (4)	0.2630 (3)	0.0226 (11)
H21	0.4642	0.4028	0.2501	0.027*
C22	0.1966 (8)	0.3877 (3)	0.2838 (2)	0.0197 (10)
C23	0.0644 (8)	0.3219 (4)	0.3019 (2)	0.0212 (11)
H23	−0.0585	0.3393	0.3148	0.025*
C24	0.1135 (8)	0.2316 (4)	0.3009 (2)	0.0224 (11)
H24	0.0242	0.1889	0.3134	0.027*
N1	0.2543 (17)	0.1774 (6)	0.5190 (5)	0.024 (2)	0.75
C1	0.2403 (16)	0.6807 (6)	0.4633 (4)	0.0197 (19)	0.75
C2	0.2154 (18)	0.6500 (6)	0.3985 (4)	0.0223 (17)	0.75
H2	0.2124	0.5866	0.3900	0.027*	0.75
C3	0.1902 (17)	0.7092 (5)	0.3482 (5)	0.0228 (19)	0.75
H3	0.1750	0.6867	0.3048	0.027*	0.75
C4	0.191 (2)	0.8026 (7)	0.3597 (5)	0.025 (3)	0.75
H4	0.1721	0.8437	0.3240	0.030*	0.75
C5	0.215 (3)	0.8344 (7)	0.4214 (6)	0.028 (3)	0.75
H5	0.2177	0.8980	0.4290	0.033*	0.75
C6	0.240 (3)	0.7748 (6)	0.4755 (5)	0.022 (2)	0.75
C7	0.264 (4)	0.8077 (7)	0.5393 (6)	0.025 (3)	0.75
H7	0.2570	0.8712	0.5468	0.030*	0.75
C8	0.294 (3)	0.7491 (7)	0.5904 (5)	0.021 (2)	0.75
H8	0.3159	0.7714	0.6338	0.026*	0.75
C9	0.294 (2)	0.6548 (7)	0.5788 (4)	0.020 (2)	0.75
H9	0.3097	0.6144	0.6149	0.024*	0.75
C10	0.269 (2)	0.6203 (6)	0.5185 (4)	0.025 (2)	0.75
C11	0.2690 (12)	0.5210 (5)	0.5082 (4)	0.0316 (18)	0.75
H11	0.2690	0.5006	0.4647	0.038*	0.75
C12	0.2670 (11)	0.4559 (5)	0.5546 (4)	0.0280 (16)	0.75
H12	0.2651	0.4745	0.5984	0.034*	0.75
C13	0.2678 (15)	0.3597 (6)	0.5405 (4)	0.032 (2)	0.75
C14	0.2476 (19)	0.3249 (8)	0.4777 (5)	0.027 (3)	0.75
H14	0.2419	0.3647	0.4414	0.032*	0.75
C15	0.239 (3)	0.2339 (7)	0.4682 (6)	0.026 (3)	0.75
H15	0.2190	0.2103	0.4251	0.031*	0.75
C16	0.274 (2)	0.2081 (7)	0.5799 (5)	0.028 (3)	0.75
H16	0.2816	0.1666	0.6153	0.034*	0.75
C17	0.2813 (15)	0.2983 (7)	0.5916 (4)	0.025 (2)	0.75
H17	0.2945	0.3197	0.6352	0.030*	0.75
C18	0.259 (2)	0.0794 (7)	0.5068 (6)	0.035 (3)	0.75
H18A	0.1841	0.0665	0.4652	0.053*	0.75
H18B	0.1984	0.0482	0.5395	0.053*	0.75
H18C	0.3974	0.0602	0.5078	0.053*	0.75
N1A	0.285 (6)	0.1907 (16)	0.5264 (14)	0.018 (5)	0.25
C1A	0.239 (4)	0.6868 (16)	0.4553 (14)	0.024 (4)	0.25
C2A	0.208 (6)	0.6680 (19)	0.3881 (14)	0.0223 (17)	0.25
H2A	0.1985	0.6086	0.3742	0.027*	0.25
C3A	0.193 (5)	0.735 (2)	0.3437 (15)	0.0228 (19)	0.25
H3A	0.1732	0.7209	0.3000	0.027*	0.25
C4A	0.206 (7)	0.826 (2)	0.3629 (17)	0.024 (5)	0.25
H4A	0.1959	0.8710	0.3320	0.028*	0.25
C5A	0.233 (10)	0.8472 (19)	0.4267 (17)	0.023 (6)	0.25
H5A	0.2386	0.9073	0.4390	0.028*	0.25
C6A	0.254 (11)	0.7784 (17)	0.4752 (15)	0.025 (5)	0.25
C7A	0.285 (12)	0.801 (2)	0.5412 (16)	0.025 (6)	0.25
H7A	0.2940	0.8613	0.5538	0.030*	0.25
C8A	0.300 (10)	0.734 (2)	0.5867 (16)	0.026 (6)	0.25
H8A	0.3174	0.7491	0.6303	0.031*	0.25
C9A	0.290 (8)	0.643 (2)	0.5675 (15)	0.026 (6)	0.25
H9A	0.3136	0.5984	0.5990	0.031*	0.25
C10A	0.248 (7)	0.6176 (16)	0.5052 (15)	0.025 (5)	0.25
C11A	0.138 (4)	0.5304 (12)	0.4899 (10)	0.026 (4)	0.25
H11A	0.2028	0.5009	0.4561	0.031*	0.25
C12A	0.108 (3)	0.4637 (11)	0.5361 (9)	0.023 (3)	0.25
H12A	0.1363	0.4886	0.5797	0.028*	0.25
C13A	0.204 (4)	0.3737 (12)	0.5336 (10)	0.014 (4)	0.25
C14A	0.208 (5)	0.3306 (17)	0.4740 (11)	0.012 (5)	0.25
H14A	0.1831	0.3634	0.4359	0.015*	0.25
C15A	0.247 (8)	0.2405 (17)	0.4719 (14)	0.016 (6)	0.25
H15A	0.2481	0.2128	0.4322	0.019*	0.25
C16A	0.284 (6)	0.2299 (17)	0.5844 (13)	0.012 (5)	0.25
H16A	0.3106	0.1956	0.6218	0.014*	0.25
C17A	0.244 (4)	0.3190 (16)	0.5887 (11)	0.011 (5)	0.25
H17A	0.2423	0.3446	0.6292	0.014*	0.25
C18A	0.300 (6)	0.0916 (17)	0.5214 (19)	0.033 (8)	0.25
H18D	0.3278	0.0661	0.5639	0.049*	0.25
H18E	0.4090	0.0766	0.4974	0.049*	0.25
H18F	0.1747	0.0680	0.4998	0.049*	0.25
O1W	−0.0921 (7)	0.0188 (3)	0.3769 (2)	0.0447 (12)
H1W1	0.0098	0.0320	0.3590	0.067*
H2W1	−0.1996	0.0310	0.3525	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0227 (7)	0.0165 (6)	0.0267 (7)	0.0017 (5)	0.0054 (5)	0.0013 (5)
O1	0.034 (2)	0.0158 (18)	0.032 (2)	0.0041 (16)	0.0041 (17)	−0.0007 (16)
O2	0.031 (2)	0.022 (2)	0.035 (2)	−0.0017 (16)	0.0011 (17)	−0.0079 (17)
O3	0.049 (3)	0.025 (2)	0.034 (2)	0.0064 (18)	0.015 (2)	0.0102 (18)
N2	0.028 (2)	0.014 (2)	0.033 (2)	0.0018 (18)	0.008 (2)	−0.0024 (18)
C19	0.019 (2)	0.021 (3)	0.018 (2)	0.000 (2)	0.0002 (19)	0.001 (2)
C20	0.021 (3)	0.026 (3)	0.022 (3)	0.001 (2)	0.006 (2)	0.001 (2)
C21	0.022 (3)	0.021 (3)	0.025 (3)	−0.003 (2)	0.003 (2)	0.005 (2)
C22	0.030 (3)	0.018 (2)	0.010 (2)	0.001 (2)	−0.0016 (19)	0.0020 (18)
C23	0.021 (3)	0.024 (3)	0.020 (2)	0.003 (2)	0.007 (2)	0.000 (2)
C24	0.022 (3)	0.027 (3)	0.019 (2)	−0.001 (2)	0.002 (2)	0.000 (2)
N1	0.019 (5)	0.024 (4)	0.027 (4)	−0.009 (3)	0.001 (3)	−0.002 (3)
C1	0.014 (3)	0.025 (4)	0.020 (4)	−0.003 (3)	0.003 (3)	−0.007 (3)
C2	0.020 (3)	0.024 (4)	0.023 (4)	0.001 (3)	0.003 (3)	−0.002 (3)
C3	0.023 (3)	0.027 (5)	0.019 (3)	−0.003 (4)	0.002 (2)	−0.001 (4)
C4	0.021 (5)	0.032 (7)	0.021 (4)	0.000 (5)	−0.002 (3)	0.001 (4)
C5	0.029 (6)	0.025 (5)	0.028 (5)	0.001 (5)	0.000 (4)	−0.004 (4)
C6	0.014 (5)	0.027 (4)	0.027 (4)	0.002 (3)	0.002 (3)	−0.004 (3)
C7	0.029 (8)	0.016 (4)	0.029 (5)	0.001 (4)	0.004 (4)	−0.004 (3)
C8	0.020 (4)	0.016 (5)	0.026 (4)	0.000 (4)	−0.001 (3)	−0.010 (3)
C9	0.022 (4)	0.022 (5)	0.019 (4)	0.002 (3)	0.007 (4)	−0.007 (3)
C10	0.027 (5)	0.026 (4)	0.022 (6)	−0.003 (3)	0.006 (4)	−0.008 (3)
C11	0.029 (4)	0.040 (5)	0.024 (4)	0.008 (3)	−0.004 (3)	−0.004 (3)
C12	0.020 (4)	0.041 (4)	0.023 (4)	0.002 (3)	0.000 (3)	0.000 (3)
C13	0.034 (5)	0.031 (5)	0.027 (5)	0.015 (4)	−0.010 (4)	−0.001 (4)
C14	0.026 (7)	0.032 (5)	0.022 (4)	0.006 (4)	0.000 (4)	0.001 (4)
C15	0.020 (5)	0.033 (5)	0.023 (5)	−0.004 (4)	0.002 (4)	−0.005 (4)
C16	0.021 (5)	0.033 (6)	0.030 (5)	−0.004 (5)	0.005 (4)	0.002 (4)
C17	0.021 (5)	0.034 (7)	0.019 (4)	0.012 (4)	−0.001 (3)	0.001 (4)
C18	0.044 (7)	0.026 (5)	0.034 (6)	−0.007 (4)	−0.002 (5)	−0.002 (4)
N1A	0.018 (7)	0.017 (7)	0.020 (7)	−0.003 (6)	0.001 (5)	0.000 (5)
C1A	0.023 (6)	0.026 (6)	0.024 (6)	0.001 (5)	0.004 (5)	0.001 (5)
C2A	0.020 (3)	0.024 (4)	0.023 (4)	0.001 (3)	0.003 (3)	−0.002 (3)
C3A	0.023 (3)	0.027 (5)	0.019 (3)	−0.003 (4)	0.002 (2)	−0.001 (4)
C4A	0.022 (7)	0.026 (7)	0.022 (7)	−0.001 (6)	0.002 (5)	0.001 (6)
C5A	0.023 (7)	0.027 (8)	0.019 (8)	0.000 (6)	0.003 (6)	−0.001 (6)
C6A	0.024 (7)	0.026 (7)	0.024 (7)	0.001 (6)	0.004 (6)	0.000 (6)
C7A	0.026 (8)	0.025 (8)	0.025 (8)	0.000 (6)	0.004 (6)	0.000 (6)
C8A	0.024 (8)	0.026 (8)	0.028 (8)	−0.001 (6)	0.004 (6)	0.002 (6)
C9A	0.025 (8)	0.026 (8)	0.026 (8)	−0.002 (6)	0.004 (6)	0.002 (6)
C10A	0.025 (6)	0.029 (7)	0.023 (6)	−0.002 (5)	0.004 (5)	−0.003 (5)
C11A	0.026 (6)	0.027 (6)	0.025 (6)	−0.001 (5)	0.003 (5)	−0.001 (5)
C12A	0.025 (6)	0.025 (6)	0.021 (6)	0.002 (5)	0.005 (5)	0.001 (5)
C13A	0.016 (6)	0.013 (6)	0.014 (6)	0.002 (5)	0.005 (5)	0.006 (5)
C14A	0.012 (7)	0.012 (7)	0.013 (7)	−0.003 (5)	0.004 (5)	0.003 (6)
C15A	0.015 (8)	0.017 (8)	0.016 (8)	−0.003 (6)	0.001 (6)	0.002 (6)
C16A	0.010 (7)	0.014 (8)	0.012 (7)	0.002 (6)	0.003 (5)	0.004 (5)
C17A	0.012 (7)	0.010 (7)	0.012 (7)	0.004 (6)	0.001 (5)	0.004 (5)
C18A	0.031 (11)	0.033 (11)	0.034 (11)	−0.010 (8)	0.006 (8)	−0.007 (8)
O1W	0.041 (3)	0.061 (3)	0.034 (2)	0.017 (2)	0.012 (2)	0.015 (2)

S1—O1	1.439 (4)	C16—C17	1.363 (12)
S1—O2	1.456 (4)	C16—H16	0.96
S1—O3	1.462 (4)	C17—H17	0.96
S1—C19	1.765 (5)	C18—H18A	0.96
N2—C22	1.376 (7)	C18—H18B	0.96
N2—H2B	0.86	C18—H18C	0.96
N2—H2C	0.86	N1A—C16A	1.348 (17)
C19—C24	1.395 (7)	N1A—C15A	1.354 (16)
C19—C20	1.406 (7)	N1A—C18A	1.484 (18)
C20—C21	1.381 (8)	C1A—C2A	1.421 (16)
C20—H20	0.93	C1A—C6A	1.425 (16)
C21—C22	1.385 (8)	C1A—C10A	1.463 (17)
C21—H21	0.93	C2A—C3A	1.358 (18)
C22—C23	1.401 (7)	C2A—H2A	0.93
C23—C24	1.384 (8)	C3A—C4A	1.407 (19)
C23—H23	0.93	C3A—H3A	0.93
C24—H24	0.93	C4A—C5A	1.361 (18)
N1—C16	1.344 (10)	C4A—H4A	0.93
N1—C15	1.350 (9)	C5A—C6A	1.435 (16)
N1—C18	1.481 (11)	C5A—H5A	0.93
C1—C2	1.419 (9)	C6A—C7A	1.411 (16)
C1—C6	1.423 (9)	C7A—C8A	1.373 (17)
C1—C10	1.457 (10)	C7A—H7A	0.93
C2—C3	1.364 (10)	C8A—C9A	1.422 (18)
C2—H2	0.96	C8A—H8A	0.93
C3—C4	1.411 (11)	C9A—C10A	1.348 (18)
C3—H3	0.96	C9A—H9A	0.93
C4—C5	1.364 (10)	C10A—C11A	1.500 (9)
C4—H4	0.96	C11A—C12A	1.421 (18)
C5—C6	1.431 (9)	C11A—C12Ai	1.65 (3)
C5—H5	0.96	C11A—H11A	0.98
C6—C7	1.411 (9)	C12A—C13A	1.488 (18)
C7—C8	1.373 (10)	C12A—C11Ai	1.65 (3)
C7—H7	0.96	C12A—H12A	0.98
C8—C9	1.424 (10)	C13A—C17A	1.406 (18)
C8—H8	0.96	C13A—C14A	1.407 (16)
C9—C10	1.351 (10)	C14A—C15A	1.368 (17)
C9—H9	0.96	C14A—H14A	0.93
C10—C11	1.493 (11)	C15A—H15A	0.93
C11—C12	1.374 (11)	C16A—C17A	1.359 (19)
C11—H11	0.96	C16A—H16A	0.93
C12—C13	1.462 (11)	C17A—H17A	0.93
C12—H12	0.96	C18A—H18D	0.96
C13—C17	1.401 (11)	C18A—H18E	0.96
C13—C14	1.402 (10)	C18A—H18F	0.96
C14—C15	1.368 (10)	O1W—H1W1	0.84
C14—H14	0.96	O1W—H2W1	0.84
C15—H15	0.96
O1—S1—O2	112.1 (2)	C17—C16—H16	119.9
O1—S1—O3	113.2 (3)	C16—C17—C13	120.6 (8)
O2—S1—O3	112.5 (3)	C16—C17—H17	119.6
O1—S1—C19	105.2 (2)	C13—C17—H17	119.8
O2—S1—C19	107.1 (2)	N1—C18—H18A	109.5
O3—S1—C19	106.0 (2)	N1—C18—H18B	109.5
C22—N2—H2B	120.0	H18A—C18—H18B	109.5
C22—N2—H2C	120.0	N1—C18—H18C	109.5
H2B—N2—H2C	120.0	H18A—C18—H18C	109.5
C24—C19—C20	118.6 (5)	H18B—C18—H18C	109.5
C24—C19—S1	121.1 (4)	C16A—N1A—C15A	120.0 (18)
C20—C19—S1	120.2 (4)	C16A—N1A—C18A	120 (2)
C21—C20—C19	120.4 (5)	C15A—N1A—C18A	119.4 (19)
C21—C20—H20	119.8	C2A—C1A—C6A	118.2 (16)
C19—C20—H20	119.8	C2A—C1A—C10A	123.7 (18)
C20—C21—C22	121.3 (5)	C6A—C1A—C10A	118.0 (16)
C20—C21—H21	119.4	C3A—C2A—C1A	121.3 (19)
C22—C21—H21	119.4	C3A—C2A—H2A	119.4
N2—C22—C21	120.8 (5)	C1A—C2A—H2A	119.4
N2—C22—C23	120.8 (5)	C2A—C3A—C4A	120.9 (19)
C21—C22—C23	118.3 (5)	C2A—C3A—H3A	119.5
C24—C23—C22	121.2 (5)	C4A—C3A—H3A	119.5
C24—C23—H23	119.4	C5A—C4A—C3A	120 (2)
C22—C23—H23	119.4	C5A—C4A—H4A	120.0
C23—C24—C19	120.2 (5)	C3A—C4A—H4A	120.0
C23—C24—H24	119.9	C4A—C5A—C6A	121 (2)
C19—C24—H24	119.9	C4A—C5A—H5A	119.5
C16—N1—C15	121.5 (8)	C6A—C5A—H5A	119.5
C16—N1—C18	119.8 (8)	C7A—C6A—C1A	120.8 (17)
C15—N1—C18	118.6 (8)	C7A—C6A—C5A	120.5 (18)
C2—C1—C6	119.1 (7)	C1A—C6A—C5A	118.6 (16)
C2—C1—C10	123.1 (7)	C8A—C7A—C6A	119.4 (19)
C6—C1—C10	117.8 (7)	C8A—C7A—H7A	120.3
C3—C2—C1	121.0 (7)	C6A—C7A—H7A	120.3
C3—C2—H2	119.7	C7A—C8A—C9A	120 (2)
C1—C2—H2	119.3	C7A—C8A—H8A	119.9
C2—C3—C4	120.5 (7)	C9A—C8A—H8A	119.9
C2—C3—H3	119.4	C10A—C9A—C8A	122 (2)
C4—C3—H3	120.1	C10A—C9A—H9A	118.8
C5—C4—C3	120.1 (8)	C8A—C9A—H9A	118.8
C5—C4—H4	120.0	C9A—C10A—C1A	118.6 (17)
C3—C4—H4	119.9	C9A—C10A—C11A	118 (2)
C4—C5—C6	121.3 (8)	C1A—C10A—C11A	119.0 (18)
C4—C5—H5	119.8	C12A—C11A—C10A	124.7 (17)
C6—C5—H5	118.9	C12A—C11A—C12Ai	91.9 (16)
C7—C6—C1	120.6 (7)	C10A—C11A—C12Ai	117 (2)
C7—C6—C5	121.3 (8)	C12A—C11A—H11A	107.2
C1—C6—C5	118.1 (7)	C10A—C11A—H11A	107.2
C8—C7—C6	120.1 (7)	C12Ai—C11A—H11A	107.2
C8—C7—H7	120.1	C11A—C12A—C13A	120.2 (16)
C6—C7—H7	119.7	C11A—C12A—C11Ai	88.1 (16)
C7—C8—C9	119.8 (7)	C13A—C12A—C11Ai	116.5 (17)
C7—C8—H8	120.3	C11A—C12A—H12A	110.1
C9—C8—H8	119.9	C13A—C12A—H12A	110.1
C10—C9—C8	122.0 (7)	C11Ai—C12A—H12A	110.1
C10—C9—H9	118.9	C17A—C13A—C14A	116.1 (16)
C8—C9—H9	119.1	C17A—C13A—C12A	121.7 (16)
C9—C10—C1	119.6 (7)	C14A—C13A—C12A	120.1 (16)
C9—C10—C11	120.6 (7)	C15A—C14A—C13A	120.1 (18)
C1—C10—C11	119.9 (7)	C15A—C14A—H14A	120.0
C12—C11—C10	126.6 (7)	C13A—C14A—H14A	120.0
C12—C11—H11	116.6	N1A—C15A—C14A	121.6 (19)
C10—C11—H11	116.8	N1A—C15A—H15A	119.2
C11—C12—C13	123.2 (7)	C14A—C15A—H15A	119.2
C11—C12—H12	118.3	N1A—C16A—C17A	120.4 (19)
C13—C12—H12	118.5	N1A—C16A—H16A	119.8
C17—C13—C14	117.6 (8)	C17A—C16A—H16A	119.8
C17—C13—C12	119.1 (8)	C16A—C17A—C13A	121.9 (18)
C14—C13—C12	123.3 (8)	C16A—C17A—H17A	119.1
C15—C14—C13	119.9 (9)	C13A—C17A—H17A	119.1
C15—C14—H14	120.0	N1A—C18A—H18D	109.5
C13—C14—H14	120.0	N1A—C18A—H18E	109.5
N1—C15—C14	120.4 (9)	H18D—C18A—H18E	109.5
N1—C15—H15	119.8	N1A—C18A—H18F	109.5
C14—C15—H15	119.8	H18D—C18A—H18F	109.5
N1—C16—C17	120.1 (8)	H18E—C18A—H18F	109.5
N1—C16—H16	120.1	H1W1—O1W—H2W1	110.2
O1—S1—C19—C24	−156.2 (4)	C18—N1—C16—C17	176.2 (12)
O2—S1—C19—C24	84.3 (5)	N1—C16—C17—C13	0.3 (16)
O3—S1—C19—C24	−36.0 (5)	C14—C13—C17—C16	−0.3 (15)
O1—S1—C19—C20	22.6 (5)	C12—C13—C17—C16	177.2 (11)
O2—S1—C19—C20	−96.9 (4)	C6A—C1A—C2A—C3A	0(3)
O3—S1—C19—C20	142.9 (4)	C10A—C1A—C2A—C3A	177 (2)
C24—C19—C20—C21	2.4 (8)	C1A—C2A—C3A—C4A	0(2)
S1—C19—C20—C21	−176.4 (4)	C2A—C3A—C4A—C5A	0(5)
C19—C20—C21—C22	−1.1 (8)	C3A—C4A—C5A—C6A	2(7)
C20—C21—C22—N2	175.5 (5)	C2A—C1A—C6A—C7A	180 (4)
C20—C21—C22—C23	−1.0 (8)	C10A—C1A—C6A—C7A	2(6)
N2—C22—C23—C24	−174.7 (5)	C2A—C1A—C6A—C5A	1(6)
C21—C22—C23—C24	1.8 (7)	C10A—C1A—C6A—C5A	−176 (4)
C22—C23—C24—C19	−0.5 (8)	C4A—C5A—C6A—C7A	179 (5)
C20—C19—C24—C23	−1.7 (7)	C4A—C5A—C6A—C1A	−2(7)
S1—C19—C24—C23	177.2 (4)	C1A—C6A—C7A—C8A	0(8)
C6—C1—C2—C3	−0.4 (13)	C5A—C6A—C7A—C8A	179 (5)
C10—C1—C2—C3	−179.7 (9)	C6A—C7A—C8A—C9A	1(8)
C1—C2—C3—C4	0.9 (12)	C7A—C8A—C9A—C10A	−6(7)
C2—C3—C4—C5	−0.9 (17)	C8A—C9A—C10A—C1A	8(6)
C3—C4—C5—C6	0(2)	C8A—C9A—C10A—C11A	−149 (4)
C2—C1—C6—C7	179.9 (13)	C2A—C1A—C10A—C9A	176 (3)
C10—C1—C6—C7	−1(2)	C6A—C1A—C10A—C9A	−6(5)
C2—C1—C6—C5	−0.1 (19)	C2A—C1A—C10A—C11A	−27 (4)
C10—C1—C6—C5	179.3 (13)	C6A—C1A—C10A—C11A	151 (4)
C4—C5—C6—C7	−179.9 (16)	C9A—C10A—C11A—C12A	−12 (5)
C4—C5—C6—C1	0(2)	C1A—C10A—C11A—C12A	−170 (2)
C1—C6—C7—C8	2(2)	C9A—C10A—C11A—C12Ai	101 (4)
C5—C6—C7—C8	−178.0 (16)	C1A—C10A—C11A—C12Ai	−56 (4)
C6—C7—C8—C9	−2(2)	C10A—C11A—C12A—C13A	−115 (3)
C7—C8—C9—C10	1(2)	C12Ai—C11A—C12A—C13A	120 (2)
C8—C9—C10—C1	−0.1 (19)	C10A—C11A—C12A—C11Ai	125 (3)
C8—C9—C10—C11	−179.9 (13)	C12Ai—C11A—C12A—C11Ai	0.000 (2)
C2—C1—C10—C9	179.2 (10)	C11A—C12A—C13A—C17A	156 (2)
C6—C1—C10—C9	−0.2 (17)	C11Ai—C12A—C13A—C17A	−100 (2)
C2—C1—C10—C11	−1.0 (15)	C11A—C12A—C13A—C14A	−41 (3)
C6—C1—C10—C11	179.7 (13)	C11Ai—C12A—C13A—C14A	63 (2)
C9—C10—C11—C12	9.0 (18)	C17A—C13A—C14A—C15A	0.4 (19)
C1—C10—C11—C12	−170.9 (9)	C12A—C13A—C14A—C15A	−163 (3)
C10—C11—C12—C13	−179.9 (10)	C16A—N1A—C15A—C14A	0(3)
C11—C12—C13—C17	175.2 (8)	C18A—N1A—C15A—C14A	172 (4)
C11—C12—C13—C14	−7.4 (14)	C13A—C14A—C15A—N1A	−1(3)
C17—C13—C14—C15	0.9 (15)	C15A—N1A—C16A—C17A	0(3)
C12—C13—C14—C15	−176.6 (12)	C18A—N1A—C16A—C17A	−172 (4)
C16—N1—C15—C14	1.4 (18)	N1A—C16A—C17A—C13A	−1(4)
C18—N1—C15—C14	−175.7 (13)	C14A—C13A—C17A—C16A	0(3)
C13—C14—C15—N1	−1.4 (18)	C12A—C13A—C17A—C16A	164 (3)
C15—N1—C16—C17	−0.9 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.84	2.01	2.831 (7)	164
O1W—H2W1···O1ii	0.84	2.04	2.853 (6)	164
N2—H2B···O1iii	0.86	2.23	3.018 (6)	153
N2—H2C···O2iv	0.86	2.23	2.991 (6)	147
C18—H18A···O1W	0.96	2.52	3.448 (13)	163
C18—H18B···O1Wv	0.96	2.21	3.168 (13)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3	0.84	2.01	2.831 (7)	164
O1W—H2W1⋯O1i	0.84	2.04	2.853 (6)	164
N2—H2B⋯O1ii	0.86	2.23	3.018 (6)	153
N2—H2C⋯O2iii	0.86	2.23	2.991 (6)	147
C18—H18A⋯O1W	0.96	2.52	3.448 (13)	163
C18—H18B⋯O1Wiv	0.96	2.21	3.168 (13)	173

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