Bis[(E)-1-methyl-4-styrylpyridinium] 4-chloro-benzene-sulfonate iodide.

In the title compound, 2C(14)H(14)N(+)·C(6)H(4)ClO(3)S(-)·I(-), each cation exists in an E configuration with respect to the ethenyl bond. The dihedral angle between the pyridinium and benzene rings is 3.98 (6)° in one of the cations and 9.88 (7)° in the other. The two cations are arranged in an anti-parallel manner with π-π inter-actions between pyridinium and benzene rings [centroid-centroid distance = 3.5805 (8) Å]. The benzene ring of the anion makes dihedral angles of 61.20 (6) and 64.25 (6)° with the pyridinium rings of the two cations. In the crystal, the cations are stacked in an anti-parallel manner along the a axis, while the anions are linked into chains along the same direction. The ions are linked into a three-dimensional network by C-H⋯I and C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal under investigation was an inversion twin, with a ratio of 61.7 (5):38.3 (5) for the two components.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background to non-linear optical materials, see: Lin et al. (2002 ▶); Prasad et al. (1991 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Chantrapromma et al. (2007 ▶; 2009 ▶); Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

2C14H14N+·C6H4ClO3S−·I−

M = 711.04

Monoclinic,

a = 8.1103 (1) Å

b = 20.5054 (3) Å

c = 9.5549 (2) Å

β = 101.799 (1)°

V = 1555.45 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.22 mm−1

T = 100 K

0.52 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.569, T max = 0.771

30676 measured reflections

13195 independent reflections

12932 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.049

S = 1.05

13195 reflections

382 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.12 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶), 6221 Friedel pairs

Flack parameter: 0.383 (5)

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/S1600536809038896/ci2919sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038896/ci2919Isup2.hkl

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

2C14H14N+·C6H4ClO3S−·I−	F(000) = 720
Mr = 711.04	Dx = 1.518 Mg m−3
Monoclinic, P21	Melting point = 468–469 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.1103 (1) Å	Cell parameters from 13195 reflections
b = 20.5054 (3) Å	θ = 2.0–35.0°
c = 9.5549 (2) Å	µ = 1.22 mm−1
β = 101.799 (1)°	T = 100 K
V = 1555.45 (4) Å3	Needle, yellow
Z = 2	0.52 × 0.23 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	13195 independent reflections
Radiation source: sealed tube	12932 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 35.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→13
Tmin = 0.569, Tmax = 0.771	k = −32→33
30676 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020	H-atom parameters constrained
wR(F2) = 0.049	w = 1/[σ2(Fo2) + (0.0253P)2 + 0.205P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
13195 reflections	Δρmax = 1.12 e Å−3
382 parameters	Δρmin = −0.44 e Å−3
1 restraint	Absolute structure: Flack (1983), 6221 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.383 (5)

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
I1	0.971569 (9)	−0.060603 (4)	0.651289 (7)	0.01701 (2)
Cl1	0.67341 (4)	0.547963 (16)	0.28511 (4)	0.02196 (6)
S1	0.03835 (4)	0.730613 (14)	0.12930 (3)	0.01312 (5)
O1	0.06242 (12)	0.77622 (5)	0.24883 (10)	0.01933 (17)
O2	−0.10740 (12)	0.68847 (5)	0.12227 (11)	0.02079 (18)
O3	0.04572 (13)	0.76183 (5)	−0.00555 (10)	0.02012 (18)
C1	0.37016 (15)	0.69739 (6)	0.13653 (14)	0.0164 (2)
H1A	0.3781	0.7374	0.0925	0.020*
C2	0.51192 (16)	0.65747 (6)	0.17238 (14)	0.0177 (2)
H2A	0.6146	0.6704	0.1524	0.021*
C3	0.49665 (16)	0.59796 (6)	0.23854 (13)	0.0166 (2)
C4	0.34485 (16)	0.57690 (6)	0.26735 (14)	0.0178 (2)
H4A	0.3371	0.5367	0.3104	0.021*
C5	0.20354 (15)	0.61712 (6)	0.23060 (13)	0.0162 (2)
H5A	0.1006	0.6036	0.2489	0.019*
C6	0.21641 (14)	0.67745 (6)	0.16659 (12)	0.01420 (19)
N1A	1.07500 (13)	0.22845 (5)	0.46320 (11)	0.01458 (17)
C1A	0.48773 (16)	−0.01117 (6)	0.08410 (13)	0.0167 (2)
H1AA	0.5010	0.0266	0.0337	0.020*
C2A	0.37605 (13)	−0.05929 (10)	0.02004 (11)	0.01769 (17)
H2AA	0.3156	−0.0535	−0.0729	0.021*
C3A	0.35455 (17)	−0.11606 (7)	0.09470 (15)	0.0190 (2)
H3AA	0.2795	−0.1480	0.0520	0.023*
C4A	0.44606 (18)	−0.12468 (7)	0.23355 (15)	0.0204 (2)
H4AA	0.4319	−0.1625	0.2836	0.024*
C5A	0.55848 (17)	−0.07700 (6)	0.29767 (14)	0.0182 (2)
H5AA	0.6197	−0.0834	0.3901	0.022*
C6A	0.58075 (15)	−0.01937 (6)	0.22463 (13)	0.01479 (19)
C7A	0.70002 (15)	0.02915 (6)	0.29811 (13)	0.01519 (19)
H7AA	0.7571	0.0188	0.3901	0.018*
C8A	0.73513 (15)	0.08732 (6)	0.24553 (13)	0.01525 (19)
H8AA	0.6790	0.0983	0.1536	0.018*
C9A	0.85493 (14)	0.13424 (6)	0.32263 (12)	0.01350 (18)
C10A	0.95355 (16)	0.12280 (6)	0.45995 (12)	0.01550 (19)
H10A	0.9469	0.0829	0.5049	0.019*
C11A	1.05955 (16)	0.17068 (6)	0.52732 (13)	0.0160 (2)
H11A	1.1219	0.1631	0.6189	0.019*
C12A	0.98620 (16)	0.24042 (6)	0.32967 (13)	0.0160 (2)
H12A	0.9998	0.2798	0.2853	0.019*
C13A	0.87579 (15)	0.19443 (6)	0.25929 (13)	0.01551 (19)
H13A	0.8141	0.2035	0.1682	0.019*
C14A	1.19046 (16)	0.27831 (6)	0.53982 (14)	0.0181 (2)
H14A	1.1509	0.3209	0.5072	0.027*
H14B	1.3013	0.2716	0.5215	0.027*
H14C	1.1943	0.2748	0.6406	0.027*
N1B	−0.04690 (13)	−0.05269 (6)	0.10397 (12)	0.0163 (2)
C1B	0.52680 (16)	0.20510 (7)	0.42045 (13)	0.0170 (2)
H1BA	0.5333	0.1669	0.4738	0.020*
C2B	0.62871 (17)	0.25784 (7)	0.47254 (14)	0.0197 (2)
H2BA	0.7030	0.2547	0.5604	0.024*
C3B	0.61999 (19)	0.31539 (7)	0.39368 (16)	0.0242 (3)
H3BA	0.6879	0.3507	0.4289	0.029*
C4B	0.5092 (2)	0.31970 (8)	0.26224 (18)	0.0299 (3)
H4BA	0.5033	0.3580	0.2093	0.036*
C5B	0.4076 (2)	0.26720 (7)	0.20969 (16)	0.0251 (3)
H5BA	0.3341	0.2706	0.1215	0.030*
C6B	0.41412 (15)	0.20902 (6)	0.28785 (13)	0.0160 (2)
C7B	0.30241 (15)	0.15565 (6)	0.22664 (13)	0.0163 (2)
H7BA	0.2387	0.1620	0.1351	0.020*
C8B	0.28271 (15)	0.09829 (6)	0.28959 (13)	0.0160 (2)
H8BA	0.3467	0.0907	0.3806	0.019*
C9B	0.16733 (15)	0.04727 (6)	0.22408 (13)	0.01487 (19)
C10B	0.07550 (16)	0.05083 (6)	0.08199 (13)	0.0167 (2)
H10B	0.0861	0.0872	0.0263	0.020*
C11B	−0.02934 (16)	0.00070 (6)	0.02581 (13)	0.0173 (2)
H11B	−0.0895	0.0036	−0.0679	0.021*
C12B	0.03766 (14)	−0.05758 (10)	0.24086 (12)	0.01881 (19)
H12B	0.0237	−0.0944	0.2941	0.023*
C13B	0.14428 (16)	−0.00860 (6)	0.30211 (13)	0.0178 (2)
H13B	0.2017	−0.0126	0.3965	0.021*
C14B	−0.15834 (18)	−0.10610 (7)	0.03712 (16)	0.0211 (2)
H14D	−0.1210	−0.1215	−0.0460	0.032*
H14E	−0.2717	−0.0902	0.0098	0.032*
H14F	−0.1546	−0.1412	0.1042	0.032*

	U11	U22	U33	U12	U13	U23
I1	0.01966 (3)	0.01429 (3)	0.01623 (3)	−0.00068 (3)	0.00170 (2)	−0.00045 (3)
Cl1	0.01781 (12)	0.01998 (13)	0.02531 (14)	0.00622 (10)	−0.00208 (10)	−0.00453 (11)
S1	0.01285 (11)	0.01510 (12)	0.01106 (10)	0.00126 (9)	0.00161 (8)	−0.00187 (9)
O1	0.0200 (4)	0.0214 (4)	0.0153 (4)	0.0047 (3)	0.0005 (3)	−0.0054 (3)
O2	0.0129 (4)	0.0241 (5)	0.0247 (5)	−0.0027 (3)	0.0023 (3)	−0.0021 (4)
O3	0.0232 (4)	0.0231 (5)	0.0149 (4)	0.0065 (4)	0.0058 (3)	0.0023 (3)
C1	0.0142 (4)	0.0151 (5)	0.0202 (5)	−0.0006 (4)	0.0041 (4)	−0.0008 (4)
C2	0.0135 (4)	0.0182 (5)	0.0211 (5)	0.0002 (4)	0.0028 (4)	−0.0024 (4)
C3	0.0152 (5)	0.0163 (5)	0.0168 (5)	0.0029 (4)	−0.0005 (4)	−0.0044 (4)
C4	0.0185 (5)	0.0150 (5)	0.0189 (5)	0.0005 (4)	0.0012 (4)	−0.0005 (4)
C5	0.0147 (5)	0.0157 (5)	0.0180 (5)	0.0000 (4)	0.0030 (4)	−0.0011 (4)
C6	0.0120 (4)	0.0151 (5)	0.0152 (5)	0.0007 (3)	0.0021 (3)	−0.0024 (4)
N1A	0.0161 (4)	0.0126 (4)	0.0150 (4)	−0.0004 (3)	0.0032 (3)	−0.0001 (3)
C1A	0.0178 (5)	0.0156 (5)	0.0163 (5)	0.0002 (4)	0.0026 (4)	0.0013 (4)
C2A	0.0180 (4)	0.0169 (4)	0.0172 (4)	−0.0002 (6)	0.0014 (3)	−0.0014 (6)
C3A	0.0186 (5)	0.0161 (5)	0.0219 (5)	−0.0018 (4)	0.0028 (4)	−0.0014 (4)
C4A	0.0227 (6)	0.0161 (5)	0.0220 (6)	−0.0035 (4)	0.0035 (4)	0.0028 (4)
C5A	0.0196 (5)	0.0159 (5)	0.0184 (5)	−0.0002 (4)	0.0021 (4)	0.0018 (4)
C6A	0.0139 (4)	0.0141 (5)	0.0162 (5)	−0.0001 (4)	0.0028 (4)	0.0000 (4)
C7A	0.0151 (5)	0.0144 (5)	0.0157 (5)	0.0006 (4)	0.0023 (4)	−0.0002 (4)
C8A	0.0147 (4)	0.0154 (5)	0.0148 (4)	0.0002 (4)	0.0011 (4)	0.0001 (4)
C9A	0.0142 (4)	0.0140 (5)	0.0130 (4)	0.0005 (3)	0.0046 (3)	0.0006 (3)
C10A	0.0186 (5)	0.0137 (5)	0.0139 (4)	−0.0005 (4)	0.0026 (4)	0.0015 (4)
C11A	0.0200 (5)	0.0146 (5)	0.0130 (4)	0.0004 (4)	0.0025 (4)	0.0014 (4)
C12A	0.0179 (5)	0.0148 (5)	0.0153 (5)	−0.0001 (4)	0.0037 (4)	0.0026 (4)
C13A	0.0166 (5)	0.0153 (5)	0.0144 (4)	−0.0004 (4)	0.0025 (4)	0.0030 (4)
C14A	0.0182 (5)	0.0157 (5)	0.0205 (5)	−0.0032 (4)	0.0040 (4)	−0.0026 (4)
N1B	0.0153 (4)	0.0137 (6)	0.0201 (4)	0.0012 (3)	0.0042 (3)	−0.0024 (4)
C1B	0.0158 (5)	0.0200 (5)	0.0145 (5)	0.0018 (4)	0.0016 (4)	−0.0005 (4)
C2B	0.0157 (5)	0.0248 (6)	0.0179 (5)	0.0003 (4)	0.0020 (4)	−0.0047 (4)
C3B	0.0228 (6)	0.0229 (6)	0.0260 (6)	−0.0064 (5)	0.0032 (5)	−0.0038 (5)
C4B	0.0351 (8)	0.0214 (7)	0.0297 (7)	−0.0089 (6)	−0.0018 (6)	0.0058 (5)
C5B	0.0270 (7)	0.0234 (6)	0.0214 (6)	−0.0048 (5)	−0.0032 (5)	0.0053 (5)
C6B	0.0145 (5)	0.0178 (5)	0.0153 (5)	−0.0007 (4)	0.0021 (4)	0.0000 (4)
C7B	0.0152 (4)	0.0181 (5)	0.0146 (4)	0.0003 (4)	0.0009 (4)	−0.0004 (4)
C8B	0.0149 (5)	0.0175 (5)	0.0150 (5)	0.0007 (4)	0.0018 (4)	−0.0004 (4)
C9B	0.0144 (4)	0.0149 (5)	0.0154 (5)	0.0013 (4)	0.0033 (4)	−0.0001 (4)
C10B	0.0184 (5)	0.0161 (5)	0.0153 (5)	−0.0004 (4)	0.0025 (4)	0.0004 (4)
C11B	0.0185 (5)	0.0165 (5)	0.0163 (5)	0.0004 (4)	0.0023 (4)	−0.0008 (4)
C12B	0.0196 (4)	0.0164 (5)	0.0203 (4)	0.0006 (6)	0.0038 (3)	0.0038 (6)
C13B	0.0191 (5)	0.0175 (5)	0.0163 (5)	0.0008 (4)	0.0028 (4)	0.0015 (4)
C14B	0.0206 (5)	0.0154 (5)	0.0267 (6)	−0.0006 (4)	0.0032 (5)	−0.0049 (4)

Cl1—C3	1.7445 (13)	C11A—H11A	0.93
S1—O3	1.4509 (10)	C12A—C13A	1.3775 (18)
S1—O2	1.4547 (10)	C12A—H12A	0.93
S1—O1	1.4581 (10)	C13A—H13A	0.93
S1—C6	1.7861 (12)	C14A—H14A	0.96
C1—C2	1.3958 (18)	C14A—H14B	0.96
C1—C6	1.3968 (17)	C14A—H14C	0.96
C1—H1A	0.93	N1B—C11B	1.3490 (18)
C2—C3	1.3914 (19)	N1B—C12B	1.3507 (15)
C2—H2A	0.93	N1B—C14B	1.4793 (17)
C3—C4	1.3844 (19)	C1B—C2B	1.3901 (19)
C4—C5	1.3972 (18)	C1B—C6B	1.4047 (16)
C4—H4A	0.93	C1B—H1BA	0.93
C5—C6	1.3935 (18)	C2B—C3B	1.394 (2)
C5—H5A	0.93	C2B—H2BA	0.93
N1A—C11A	1.3512 (16)	C3B—C4B	1.389 (2)
N1A—C12A	1.3531 (15)	C3B—H3BA	0.93
N1A—C14A	1.4758 (16)	C4B—C5B	1.386 (2)
C1A—C2A	1.394 (2)	C4B—H4BA	0.93
C1A—C6A	1.4093 (17)	C5B—C6B	1.4026 (19)
C1A—H1AA	0.93	C5B—H5BA	0.93
C2A—C3A	1.395 (2)	C6B—C7B	1.4643 (18)
C2A—H2AA	0.93	C7B—C8B	1.3454 (18)
C3A—C4A	1.3927 (19)	C7B—H7BA	0.93
C3A—H3AA	0.93	C8B—C9B	1.4568 (17)
C4A—C5A	1.3907 (18)	C8B—H8BA	0.93
C4A—H4AA	0.93	C9B—C13B	1.4002 (18)
C5A—C6A	1.4027 (18)	C9B—C10B	1.4105 (17)
C5A—H5AA	0.93	C10B—C11B	1.3716 (18)
C6A—C7A	1.4632 (17)	C10B—H10B	0.93
C7A—C8A	1.3470 (17)	C11B—H11B	0.93
C7A—H7AA	0.93	C12B—C13B	1.375 (2)
C8A—C9A	1.4559 (16)	C12B—H12B	0.93
C8A—H8AA	0.93	C13B—H13B	0.93
C9A—C13A	1.4000 (17)	C14B—H14D	0.96
C9A—C10A	1.4096 (16)	C14B—H14E	0.96
C10A—C11A	1.3751 (17)	C14B—H14F	0.96
C10A—H10A	0.93
O3—S1—O2	113.69 (6)	N1A—C12A—C13A	120.24 (11)
O3—S1—O1	112.92 (6)	N1A—C12A—H12A	119.9
O2—S1—O1	113.24 (6)	C13A—C12A—H12A	119.9
O3—S1—C6	105.54 (6)	C12A—C13A—C9A	121.10 (11)
O2—S1—C6	105.24 (6)	C12A—C13A—H13A	119.4
O1—S1—C6	105.18 (5)	C9A—C13A—H13A	119.4
C2—C1—C6	120.20 (12)	N1A—C14A—H14A	109.5
C2—C1—H1A	119.9	N1A—C14A—H14B	109.5
C6—C1—H1A	119.9	H14A—C14A—H14B	109.5
C3—C2—C1	118.72 (12)	N1A—C14A—H14C	109.5
C3—C2—H2A	120.6	H14A—C14A—H14C	109.5
C1—C2—H2A	120.6	H14B—C14A—H14C	109.5
C4—C3—C2	121.96 (12)	C11B—N1B—C12B	120.41 (12)
C4—C3—Cl1	118.93 (10)	C11B—N1B—C14B	119.09 (11)
C2—C3—Cl1	119.10 (10)	C12B—N1B—C14B	120.50 (12)
C3—C4—C5	118.88 (12)	C2B—C1B—C6B	120.52 (12)
C3—C4—H4A	120.6	C2B—C1B—H1BA	119.7
C5—C4—H4A	120.6	C6B—C1B—H1BA	119.7
C6—C5—C4	120.21 (12)	C1B—C2B—C3B	120.29 (12)
C6—C5—H5A	119.9	C1B—C2B—H2BA	119.9
C4—C5—H5A	119.9	C3B—C2B—H2BA	119.9
C5—C6—C1	120.01 (11)	C4B—C3B—C2B	119.62 (13)
C5—C6—S1	119.96 (9)	C4B—C3B—H3BA	120.2
C1—C6—S1	119.98 (9)	C2B—C3B—H3BA	120.2
C11A—N1A—C12A	120.38 (11)	C5B—C4B—C3B	120.32 (14)
C11A—N1A—C14A	119.39 (10)	C5B—C4B—H4BA	119.8
C12A—N1A—C14A	120.23 (10)	C3B—C4B—H4BA	119.8
C2A—C1A—C6A	120.48 (12)	C4B—C5B—C6B	120.84 (13)
C2A—C1A—H1AA	119.8	C4B—C5B—H5BA	119.6
C6A—C1A—H1AA	119.8	C6B—C5B—H5BA	119.6
C1A—C2A—C3A	120.29 (10)	C5B—C6B—C1B	118.41 (12)
C1A—C2A—H2AA	119.9	C5B—C6B—C7B	118.04 (11)
C3A—C2A—H2AA	119.9	C1B—C6B—C7B	123.55 (11)
C4A—C3A—C2A	119.68 (12)	C8B—C7B—C6B	126.53 (11)
C4A—C3A—H3AA	120.2	C8B—C7B—H7BA	116.7
C2A—C3A—H3AA	120.2	C6B—C7B—H7BA	116.7
C5A—C4A—C3A	120.27 (12)	C7B—C8B—C9B	124.07 (11)
C5A—C4A—H4AA	119.9	C7B—C8B—H8BA	118.0
C3A—C4A—H4AA	119.9	C9B—C8B—H8BA	118.0
C4A—C5A—C6A	120.84 (12)	C13B—C9B—C10B	116.95 (11)
C4A—C5A—H5AA	119.6	C13B—C9B—C8B	120.18 (11)
C6A—C5A—H5AA	119.6	C10B—C9B—C8B	122.87 (11)
C5A—C6A—C1A	118.44 (11)	C11B—C10B—C9B	120.06 (12)
C5A—C6A—C7A	118.29 (11)	C11B—C10B—H10B	120.0
C1A—C6A—C7A	123.27 (11)	C9B—C10B—H10B	120.0
C8A—C7A—C6A	126.34 (11)	N1B—C11B—C10B	121.25 (11)
C8A—C7A—H7AA	116.8	N1B—C11B—H11B	119.4
C6A—C7A—H7AA	116.8	C10B—C11B—H11B	119.4
C7A—C8A—C9A	124.51 (11)	N1B—C12B—C13B	120.56 (14)
C7A—C8A—H8AA	117.7	N1B—C12B—H12B	119.7
C9A—C8A—H8AA	117.7	C13B—C12B—H12B	119.7
C13A—C9A—C10A	116.96 (11)	C12B—C13B—C9B	120.77 (12)
C13A—C9A—C8A	119.41 (10)	C12B—C13B—H13B	119.6
C10A—C9A—C8A	123.64 (11)	C9B—C13B—H13B	119.6
C11A—C10A—C9A	119.89 (11)	N1B—C14B—H14D	109.5
C11A—C10A—H10A	120.1	N1B—C14B—H14E	109.5
C9A—C10A—H10A	120.1	H14D—C14B—H14E	109.5
N1A—C11A—C10A	121.38 (11)	N1B—C14B—H14F	109.5
N1A—C11A—H11A	119.3	H14D—C14B—H14F	109.5
C10A—C11A—H11A	119.3	H14E—C14B—H14F	109.5
C6—C1—C2—C3	−0.17 (18)	C12A—N1A—C11A—C10A	−0.33 (19)
C1—C2—C3—C4	1.13 (19)	C14A—N1A—C11A—C10A	−179.97 (12)
C1—C2—C3—Cl1	−179.50 (10)	C9A—C10A—C11A—N1A	−1.70 (19)
C2—C3—C4—C5	−0.92 (19)	C11A—N1A—C12A—C13A	1.72 (18)
Cl1—C3—C4—C5	179.71 (9)	C14A—N1A—C12A—C13A	−178.65 (12)
C3—C4—C5—C6	−0.26 (18)	N1A—C12A—C13A—C9A	−1.06 (19)
C4—C5—C6—C1	1.19 (18)	C10A—C9A—C13A—C12A	−0.91 (18)
C4—C5—C6—S1	−176.40 (9)	C8A—C9A—C13A—C12A	179.10 (12)
C2—C1—C6—C5	−0.97 (18)	C6B—C1B—C2B—C3B	0.1 (2)
C2—C1—C6—S1	176.61 (10)	C1B—C2B—C3B—C4B	−0.3 (2)
O3—S1—C6—C5	−143.17 (10)	C2B—C3B—C4B—C5B	0.1 (3)
O2—S1—C6—C5	−22.64 (11)	C3B—C4B—C5B—C6B	0.1 (3)
O1—S1—C6—C5	97.21 (11)	C4B—C5B—C6B—C1B	−0.3 (2)
O3—S1—C6—C1	39.25 (11)	C4B—C5B—C6B—C7B	179.55 (15)
O2—S1—C6—C1	159.77 (10)	C2B—C1B—C6B—C5B	0.2 (2)
O1—S1—C6—C1	−80.38 (11)	C2B—C1B—C6B—C7B	−179.66 (12)
C6A—C1A—C2A—C3A	0.28 (19)	C5B—C6B—C7B—C8B	−175.19 (14)
C1A—C2A—C3A—C4A	−0.4 (2)	C1B—C6B—C7B—C8B	4.6 (2)
C2A—C3A—C4A—C5A	0.0 (2)	C6B—C7B—C8B—C9B	178.99 (12)
C3A—C4A—C5A—C6A	0.5 (2)	C7B—C8B—C9B—C13B	−174.52 (13)
C4A—C5A—C6A—C1A	−0.63 (19)	C7B—C8B—C9B—C10B	5.9 (2)
C4A—C5A—C6A—C7A	179.60 (12)	C13B—C9B—C10B—C11B	−0.56 (18)
C2A—C1A—C6A—C5A	0.22 (19)	C8B—C9B—C10B—C11B	179.04 (12)
C2A—C1A—C6A—C7A	179.98 (12)	C12B—N1B—C11B—C10B	0.77 (19)
C5A—C6A—C7A—C8A	−178.90 (13)	C14B—N1B—C11B—C10B	−178.48 (12)
C1A—C6A—C7A—C8A	1.3 (2)	C9B—C10B—C11B—N1B	−0.10 (19)
C6A—C7A—C8A—C9A	179.94 (12)	C11B—N1B—C12B—C13B	−0.73 (19)
C7A—C8A—C9A—C13A	−177.28 (12)	C14B—N1B—C12B—C13B	178.51 (12)
C7A—C8A—C9A—C10A	2.7 (2)	N1B—C12B—C13B—C9B	0.0 (2)
C13A—C9A—C10A—C11A	2.25 (18)	C10B—C9B—C13B—C12B	0.59 (19)
C8A—C9A—C10A—C11A	−177.76 (12)	C8B—C9B—C13B—C12B	−179.02 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.36	3.2818 (17)	171
C2B—H2BA···O1ii	0.93	2.39	3.2829 (17)	161
C10B—H10B···O2iii	0.93	2.54	3.4711 (16)	178
C11A—H11A···O2ii	0.93	2.55	3.3109 (16)	139
C7B—H7BA···O2iii	0.93	2.53	3.4514 (16)	171
C13A—H13A···O3iv	0.93	2.42	2.9706 (16)	118
C14A—H14A···I1v	0.96	2.93	3.8718 (13)	168
C14A—H14C···O1ii	0.96	2.52	3.1591 (16)	124
C14A—H14B···Cg2i	0.96	2.71	3.5804 (15)	152
C14B—H14E···Cg1vi	0.96	2.82	3.5551 (16)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.36	3.2818 (17)	171
C2B—H2BA⋯O1ii	0.93	2.39	3.2829 (17)	161
C10B—H10B⋯O2iii	0.93	2.54	3.4711 (16)	178
C11A—H11A⋯O2ii	0.93	2.55	3.3109 (16)	139
C7B—H7BA⋯O2iii	0.93	2.53	3.4514 (16)	171
C13A—H13A⋯O3iv	0.93	2.42	2.9706 (16)	118
C14A—H14A⋯I1v	0.96	2.93	3.8718 (13)	168
C14A—H14C⋯O1ii	0.96	2.52	3.1591 (16)	124
C14A—H14B⋯Cg2i	0.96	2.71	3.5804 (15)	152
C14B—H14E⋯Cg1vi	0.96	2.82	3.5551 (16)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 and Cg2 are centroids of the C1A--C6A and C1B--C6B rings, respectively.