(E)-4-[2-(4-Eth-oxy-phen-yl)ethen-yl]-1-methyl-pyridinium 4-bromo-benzene-sulfonate methanol hemisolvate.

In the title compound, C(16)H(18)NO(+)·C(6)H(4)BrO(3)S(-)·0.5CH(3)OH, the cation exists in the E configuration and the whole mol-ecule of the cation, except for the O atom of the eth-oxy group, is disordered with a site-occupancy ratio of 0.695 (5):0.305 (5). The cation is disordered in such a way that the ethenyl units of the major and minor components are related by 180° around the long mol-ecular axis. In the major component, the cation is almost planar, the dihedral angle between the pyridinium and benzene rings being 0.8 (3)°, whereas in the minor component, the dihedral angle between the two aromatic rings is 4.2 (6)°. In the crystal, the cations are stacked in an anti-parallel manner along the a axis, while the anions and methanol mol-ecules are linked through O-H⋯O hydrogen bonds and Br⋯O short contacts [3.0248 (13) Å] into a tape along the same direction. The three components are further linked by weak C-H⋯O, C-H⋯Br and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to non-linear optical materials research, see: Cheng, Tam, Marder et al. (1991 ▶); Cheng, Tam, Stevenson et al. (1991 ▶); Ogawa et al. (2008 ▶); Ruanwas et al. (2010 ▶); Yang et al. (2007 ▶). For related structures, see: Chantrapromma et al. (2006 ▶); Chantrapromma, Chanawanno & Fun (2009 ▶); Chantra­promma, Jansrisewangwong 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

2C16H18NO+·2C6H4BrO3S−·CH4O

M = 984.79

Triclinic,

a = 9.9270 (4) Å

b = 9.9813 (4) Å

c = 11.5293 (4) Å

α = 75.703 (2)°

β = 76.965 (2)°

γ = 88.395 (2)°

V = 1078.00 (7) Å3

Z = 1

Mo Kα radiation

μ = 2.04 mm−1

T = 100 K

0.58 × 0.41 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.383, T max = 0.721

24757 measured reflections

6214 independent reflections

5389 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.03

6214 reflections

354 parameters

6 restraints

H-atom parameters constrained

Δρmax = 1.47 e Å−3

Δρmin = −0.54 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/S1600536810050944/is2636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050944/is2636Isup2.hkl

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

2C16H18NO+·2C6H4BrO3S−·CH4O	Z = 1
Mr = 984.79	F(000) = 506
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Melting point = 513–515 K
a = 9.9270 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9813 (4) Å	Cell parameters from 6214 reflections
c = 11.5293 (4) Å	θ = 1.9–30.0°
α = 75.703 (2)°	µ = 2.04 mm−1
β = 76.965 (2)°	T = 100 K
γ = 88.395 (2)°	Plate, yellow
V = 1078.00 (7) Å3	0.58 × 0.41 × 0.17 mm

Bruker APEXII CCD area-detector diffractometer	6214 independent reflections
Radiation source: sealed tube	5389 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.383, Tmax = 0.721	k = −14→14
24757 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.6369P] where P = (Fo2 + 2Fc2)/3
6214 reflections	(Δ/σ)max = 0.002
354 parameters	Δρmax = 1.47 e Å−3
6 restraints	Δρmin = −0.54 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)
Br1	0.611495 (18)	0.152815 (19)	0.312050 (17)	0.02878 (6)
S1	−0.01349 (4)	0.19135 (4)	0.23886 (4)	0.02485 (9)
O1	0.57929 (15)	0.21814 (14)	0.88911 (12)	0.0318 (3)
O2	−0.09844 (13)	0.10914 (14)	0.35315 (12)	0.0314 (3)
O3	−0.04752 (16)	0.33740 (14)	0.21612 (16)	0.0415 (4)
O4	−0.00778 (15)	0.13368 (18)	0.13490 (14)	0.0396 (3)
O5	0.8900 (4)	0.4976 (3)	0.0154 (3)	0.0435 (7)	0.50
H5	0.9371	0.4481	0.0578	0.065*	0.50
N1A	−0.0147 (7)	0.7395 (6)	0.2448 (5)	0.0267 (12)	0.695 (5)
C1A	0.0554 (4)	0.7375 (4)	0.4310 (3)	0.0239 (6)	0.695 (5)
H1AA	0.0530	0.7777	0.4961	0.029*	0.695 (5)
C2A	−0.0181 (6)	0.7948 (5)	0.3438 (4)	0.0228 (8)	0.695 (5)
H2AA	−0.0707	0.8720	0.3517	0.027*	0.695 (5)
C3A	0.0609 (9)	0.6259 (8)	0.2357 (7)	0.0367 (15)	0.695 (5)
H3AA	0.0643	0.5885	0.1688	0.044*	0.695 (5)
C4A	0.1331 (4)	0.5640 (3)	0.3233 (4)	0.0332 (8)	0.695 (5)
H4AA	0.1818	0.4845	0.3157	0.040*	0.695 (5)
C5A	0.1341 (3)	0.6195 (3)	0.4234 (3)	0.0237 (6)	0.695 (5)
C6A	0.2090 (3)	0.5626 (3)	0.5195 (2)	0.0270 (7)	0.695 (5)
H6AA	0.1987	0.6051	0.5841	0.032*	0.695 (5)
C7A	0.2907 (3)	0.4544 (3)	0.5214 (2)	0.0261 (7)	0.695 (5)
H7AA	0.3008	0.4130	0.4561	0.031*	0.695 (5)
C8A	0.3662 (3)	0.3946 (3)	0.6161 (3)	0.0243 (6)	0.695 (5)
C9A	0.4440 (3)	0.2777 (4)	0.6085 (3)	0.0283 (7)	0.695 (5)
H9AA	0.4482	0.2397	0.5418	0.034*	0.695 (5)
C10A	0.5148 (6)	0.2167 (6)	0.6964 (5)	0.0294 (10)	0.695 (5)
H10A	0.5643	0.1378	0.6884	0.035*	0.695 (5)
C11A	0.5143 (8)	0.2692 (7)	0.7955 (6)	0.0287 (13)	0.695 (5)
C12A	0.4362 (6)	0.3892 (5)	0.8051 (5)	0.0348 (11)	0.695 (5)
H12A	0.4333	0.4268	0.8718	0.042*	0.695 (5)
C13A	0.3649 (3)	0.4505 (3)	0.7172 (4)	0.0302 (7)	0.695 (5)
H13A	0.3154	0.5295	0.7247	0.036*	0.695 (5)
C14A	−0.0929 (6)	0.8055 (6)	0.1557 (5)	0.0371 (11)	0.695 (5)
H14A	−0.0579	0.7792	0.0800	0.056*	0.695 (5)
H14B	−0.0841	0.9041	0.1414	0.056*	0.695 (5)
H14C	−0.1885	0.7771	0.1864	0.056*	0.695 (5)
C15A	0.6589 (7)	0.0983 (6)	0.8757 (7)	0.0231 (17)	0.695 (5)
H15A	0.7289	0.1197	0.7994	0.028*	0.695 (5)
H15B	0.5994	0.0236	0.8743	0.028*	0.695 (5)
C16A	0.7260 (12)	0.0566 (17)	0.9834 (10)	0.034 (2)	0.695 (5)
H16A	0.7892	−0.0160	0.9718	0.051*	0.695 (5)
H16B	0.6561	0.0243	1.0573	0.051*	0.695 (5)
H16C	0.7753	0.1349	0.9897	0.051*	0.695 (5)
N1B	−0.0172 (14)	0.7490 (16)	0.2597 (13)	0.020 (2)*	0.305 (5)
C1B	0.0848 (8)	0.7018 (9)	0.4259 (7)	0.0201 (18)*	0.305 (5)
H1BA	0.0962	0.7236	0.4971	0.024*	0.305 (5)
C2B	0.0053 (12)	0.7800 (14)	0.3562 (12)	0.024 (3)*	0.305 (5)
H2BA	−0.0344	0.8582	0.3782	0.029*	0.305 (5)
C3B	0.0405 (19)	0.638 (2)	0.2234 (19)	0.029 (3)*	0.305 (5)
H3BA	0.0207	0.6149	0.1556	0.035*	0.305 (5)
C4B	0.1273 (10)	0.5607 (11)	0.2859 (9)	0.030 (2)*	0.305 (5)
H4BA	0.1720	0.4881	0.2574	0.036*	0.305 (5)
C5B	0.1499 (7)	0.5881 (8)	0.3903 (8)	0.0212 (15)*	0.305 (5)
C6B	0.2386 (6)	0.5015 (6)	0.4641 (5)	0.0226 (14)*	0.305 (5)
H6BA	0.2810	0.4282	0.4351	0.027*	0.305 (5)
C7B	0.2637 (6)	0.5186 (6)	0.5688 (5)	0.0211 (14)*	0.305 (5)
H7BA	0.2213	0.5926	0.5966	0.025*	0.305 (5)
C8B	0.3503 (7)	0.4341 (8)	0.6447 (7)	0.0210 (14)*	0.305 (5)
C9B	0.4213 (8)	0.3225 (9)	0.6190 (7)	0.0241 (16)*	0.305 (5)
H9BA	0.4174	0.2964	0.5477	0.029*	0.305 (5)
C10B	0.5018 (16)	0.2447 (14)	0.6990 (15)	0.035 (4)*	0.305 (5)
H10B	0.5512	0.1691	0.6808	0.042*	0.305 (5)
C11B	0.5034 (16)	0.2863 (15)	0.8051 (13)	0.018 (3)*	0.305 (5)
C12B	0.4343 (11)	0.3971 (12)	0.8312 (10)	0.021 (2)*	0.305 (5)
H12B	0.4399	0.4246	0.9014	0.026*	0.305 (5)
C13B	0.3546 (9)	0.4703 (9)	0.7531 (8)	0.030 (2)*	0.305 (5)
H13B	0.3037	0.5442	0.7734	0.036*	0.305 (5)
C14B	−0.1068 (15)	0.8318 (13)	0.1724 (13)	0.028 (3)*	0.305 (5)
H14D	−0.1681	0.7690	0.1567	0.042*	0.305 (5)
H14E	−0.0475	0.8797	0.0963	0.042*	0.305 (5)
H14F	−0.1601	0.8975	0.2106	0.042*	0.305 (5)
C15B	0.659 (3)	0.098 (2)	0.877 (3)	0.054 (8)*	0.305 (5)
H15C	0.7338	0.1217	0.8046	0.065*	0.305 (5)
H15D	0.6004	0.0271	0.8673	0.065*	0.305 (5)
C16B	0.716 (3)	0.044 (4)	0.990 (3)	0.047 (9)*	0.305 (5)
H16D	0.7610	−0.0419	0.9852	0.071*	0.305 (5)
H16E	0.6426	0.0291	1.0619	0.071*	0.305 (5)
H16F	0.7825	0.1101	0.9937	0.071*	0.305 (5)
C17	0.42651 (18)	0.16977 (18)	0.29296 (16)	0.0244 (3)
C18	0.39864 (19)	0.25307 (19)	0.18576 (17)	0.0288 (4)
H18A	0.4697	0.3034	0.1249	0.035*
C19	0.26369 (19)	0.26051 (19)	0.17041 (17)	0.0285 (4)
H19A	0.2439	0.3161	0.0990	0.034*
C20	0.15803 (18)	0.18491 (17)	0.26178 (16)	0.0233 (3)
C21	0.18730 (19)	0.10245 (18)	0.36949 (16)	0.0252 (3)
H21A	0.1163	0.0524	0.4307	0.030*
C22	0.32179 (19)	0.09490 (18)	0.38552 (16)	0.0262 (3)
H22A	0.3416	0.0404	0.4573	0.031*
C23	0.7489 (5)	0.4042 (5)	0.0126 (4)	0.0433 (10)	0.50
H23A	0.7764	0.3470	−0.0440	0.065*	0.50
H23B	0.6475	0.4335	−0.0202	0.065*	0.50
H23C	0.7118	0.3469	0.0933	0.065*	0.50

	U11	U22	U33	U12	U13	U23
Br1	0.02518 (9)	0.02959 (10)	0.03098 (10)	−0.00350 (7)	−0.00640 (7)	−0.00585 (7)
S1	0.0239 (2)	0.02263 (19)	0.0257 (2)	−0.00041 (15)	−0.00211 (16)	−0.00470 (16)
O1	0.0433 (8)	0.0253 (6)	0.0284 (7)	0.0050 (6)	−0.0099 (6)	−0.0086 (5)
O2	0.0247 (6)	0.0336 (7)	0.0307 (7)	−0.0064 (5)	−0.0021 (5)	−0.0010 (5)
O3	0.0341 (8)	0.0242 (7)	0.0566 (10)	0.0035 (6)	−0.0008 (7)	−0.0009 (6)
O4	0.0318 (7)	0.0584 (10)	0.0357 (8)	0.0039 (7)	−0.0091 (6)	−0.0239 (7)
O5	0.0519 (19)	0.0435 (17)	0.0314 (15)	0.0016 (14)	−0.0150 (14)	0.0030 (13)
N1A	0.044 (2)	0.0231 (18)	0.0148 (18)	−0.0134 (11)	−0.0077 (13)	−0.0057 (12)
C1A	0.0287 (14)	0.0213 (14)	0.0223 (14)	0.0016 (13)	−0.0060 (11)	−0.0064 (11)
C2A	0.0265 (19)	0.0225 (17)	0.0199 (17)	−0.0026 (14)	−0.0077 (14)	−0.0036 (12)
C3A	0.060 (4)	0.022 (2)	0.032 (2)	−0.004 (2)	−0.011 (3)	−0.0119 (18)
C4A	0.052 (2)	0.0206 (13)	0.0271 (18)	0.0008 (11)	−0.0114 (16)	−0.0042 (13)
C5A	0.0283 (13)	0.0190 (12)	0.0216 (14)	−0.0059 (10)	−0.0012 (10)	−0.0043 (11)
C6A	0.0322 (14)	0.0231 (12)	0.0256 (13)	−0.0034 (10)	−0.0039 (10)	−0.0079 (10)
C7A	0.0302 (13)	0.0231 (12)	0.0231 (12)	−0.0060 (10)	−0.0001 (10)	−0.0067 (10)
C8A	0.0284 (13)	0.0187 (13)	0.0230 (13)	−0.0032 (11)	0.0006 (10)	−0.0051 (11)
C9A	0.0327 (15)	0.0245 (15)	0.0274 (14)	0.0011 (12)	−0.0010 (11)	−0.0110 (12)
C10A	0.0321 (19)	0.026 (2)	0.0288 (18)	0.0007 (16)	−0.0019 (12)	−0.0084 (16)
C11A	0.034 (2)	0.018 (2)	0.030 (2)	0.0008 (14)	−0.0010 (16)	−0.0034 (15)
C12A	0.054 (2)	0.0253 (17)	0.028 (2)	−0.0017 (12)	−0.0086 (18)	−0.0111 (16)
C13A	0.0373 (16)	0.0173 (13)	0.0323 (19)	0.0016 (10)	−0.0011 (14)	−0.0057 (13)
C14A	0.045 (3)	0.033 (3)	0.030 (2)	−0.012 (2)	−0.0155 (19)	0.0052 (18)
C15A	0.0195 (18)	0.0215 (19)	0.026 (2)	0.0024 (9)	−0.0013 (9)	−0.0062 (10)
C16A	0.025 (2)	0.040 (3)	0.032 (3)	0.002 (2)	−0.0059 (15)	0.0003 (18)
C17	0.0246 (8)	0.0231 (8)	0.0259 (8)	−0.0016 (6)	−0.0043 (6)	−0.0078 (6)
C18	0.0267 (8)	0.0268 (8)	0.0277 (9)	−0.0070 (7)	−0.0015 (7)	−0.0005 (7)
C19	0.0298 (9)	0.0262 (8)	0.0255 (8)	−0.0041 (7)	−0.0046 (7)	0.0001 (7)
C20	0.0234 (8)	0.0204 (7)	0.0255 (8)	−0.0028 (6)	−0.0018 (6)	−0.0074 (6)
C21	0.0264 (8)	0.0243 (8)	0.0226 (8)	−0.0034 (6)	0.0000 (6)	−0.0060 (6)
C22	0.0294 (9)	0.0249 (8)	0.0231 (8)	−0.0024 (7)	−0.0040 (7)	−0.0050 (6)
C23	0.057 (3)	0.033 (2)	0.032 (2)	0.0013 (19)	0.0035 (19)	−0.0064 (17)

Br1—C17	1.8962 (18)	N1B—C3B	1.35 (2)
S1—O4	1.4420 (15)	N1B—C14B	1.56 (2)
S1—O2	1.4575 (14)	C1B—C2B	1.349 (12)
S1—O3	1.4600 (14)	C1B—C5B	1.394 (10)
S1—C20	1.7780 (18)	C1B—H1BA	0.9300
O1—C11A	1.366 (5)	C2B—H2BA	0.9300
O1—C11B	1.394 (8)	C3B—C4B	1.351 (17)
O1—C15B	1.434 (9)	C3B—H3BA	0.9300
O1—C15A	1.436 (3)	C4B—C5B	1.364 (10)
O5—C23	1.716 (6)	C4B—H4BA	0.9300
O5—H5	0.8200	C5B—C6B	1.476 (9)
N1A—C3A	1.355 (10)	C6B—C7B	1.336 (8)
N1A—C2A	1.379 (6)	C6B—H6BA	0.9300
N1A—C14A	1.445 (8)	C7B—C8B	1.467 (9)
C1A—C2A	1.376 (6)	C7B—H7BA	0.9300
C1A—C5A	1.405 (5)	C8B—C9B	1.360 (10)
C1A—H1AA	0.9300	C8B—C13B	1.394 (10)
C2A—H2AA	0.9300	C9B—C10B	1.427 (17)
C3A—C4A	1.381 (8)	C9B—H9BA	0.9300
C3A—H3AA	0.9300	C10B—C11B	1.39 (2)
C4A—C5A	1.400 (5)	C10B—H10B	0.9300
C4A—H4AA	0.9300	C11B—C12B	1.346 (17)
C5A—C6A	1.463 (4)	C12B—C13B	1.391 (14)
C6A—C7A	1.331 (4)	C12B—H12B	0.9300
C6A—H6AA	0.9300	C13B—H13B	0.9300
C7A—C8A	1.460 (4)	C14B—H14D	0.9600
C7A—H7AA	0.9300	C14B—H14E	0.9600
C8A—C9A	1.391 (4)	C14B—H14F	0.9600
C8A—C13A	1.408 (5)	C15B—C16B	1.511 (10)
C9A—C10A	1.373 (7)	C15B—H15C	0.9700
C9A—H9AA	0.9300	C15B—H15D	0.9700
C10A—C11A	1.368 (8)	C16B—H16D	0.9600
C10A—H10A	0.9300	C16B—H16E	0.9600
C11A—C12A	1.422 (8)	C16B—H16F	0.9600
C12A—C13A	1.377 (6)	C17—C22	1.388 (2)
C12A—H12A	0.9300	C17—C18	1.389 (3)
C13A—H13A	0.9300	C18—C19	1.388 (3)
C14A—H14A	0.9600	C18—H18A	0.9300
C14A—H14B	0.9600	C19—C20	1.390 (2)
C14A—H14C	0.9600	C19—H19A	0.9300
C15A—C16A	1.503 (5)	C20—C21	1.396 (2)
C15A—H15A	0.9700	C21—C22	1.386 (3)
C15A—H15B	0.9700	C21—H21A	0.9300
C16A—H16A	0.9600	C22—H22A	0.9300
C16A—H16B	0.9600	C23—H23A	0.9600
C16A—H16C	0.9600	C23—H23B	1.1586
N1B—C2B	1.291 (17)	C23—H23C	0.9600
O4—S1—O2	113.62 (9)	C3B—C4B—H4BA	119.7
O4—S1—O3	113.59 (10)	C5B—C4B—H4BA	119.7
O2—S1—O3	112.28 (9)	C4B—C5B—C1B	117.3 (8)
O4—S1—C20	105.52 (8)	C4B—C5B—C6B	122.1 (8)
O2—S1—C20	105.47 (8)	C1B—C5B—C6B	120.6 (8)
O3—S1—C20	105.41 (9)	C7B—C6B—C5B	126.1 (6)
C11A—O1—C15B	114.3 (11)	C7B—C6B—H6BA	116.9
C11B—O1—C15B	124.0 (12)	C5B—C6B—H6BA	116.9
C11A—O1—C15A	113.7 (4)	C6B—C7B—C8B	127.5 (6)
C11B—O1—C15A	123.5 (7)	C6B—C7B—H7BA	116.2
C23—O5—H5	109.5	C8B—C7B—H7BA	116.2
C3A—N1A—C2A	118.7 (6)	C9B—C8B—C13B	118.8 (7)
C3A—N1A—C14A	123.1 (6)	C9B—C8B—C7B	125.0 (7)
C2A—N1A—C14A	118.2 (6)	C13B—C8B—C7B	116.2 (7)
C2A—C1A—C5A	121.2 (3)	C8B—C9B—C10B	121.4 (9)
C2A—C1A—H1AA	119.4	C8B—C9B—H9BA	119.3
C5A—C1A—H1AA	119.4	C10B—C9B—H9BA	119.3
C1A—C2A—N1A	120.9 (5)	C11B—C10B—C9B	117.4 (10)
C1A—C2A—H2AA	119.5	C11B—C10B—H10B	121.3
N1A—C2A—H2AA	119.5	C9B—C10B—H10B	121.3
N1A—C3A—C4A	121.8 (7)	C12B—C11B—C10B	121.8 (9)
N1A—C3A—H3AA	119.1	C12B—C11B—O1	116.1 (10)
C4A—C3A—H3AA	119.1	C10B—C11B—O1	122.1 (11)
C3A—C4A—C5A	120.9 (4)	C11B—C12B—C13B	120.0 (9)
C3A—C4A—H4AA	119.6	C11B—C12B—H12B	120.0
C5A—C4A—H4AA	119.6	C13B—C12B—H12B	120.0
C4A—C5A—C1A	116.6 (3)	C12B—C13B—C8B	120.6 (8)
C4A—C5A—C6A	124.8 (3)	C12B—C13B—H13B	119.7
C1A—C5A—C6A	118.7 (3)	C8B—C13B—H13B	119.7
C7A—C6A—C5A	124.9 (3)	N1B—C14B—H14D	109.5
C7A—C6A—H6AA	117.6	N1B—C14B—H14E	109.5
C5A—C6A—H6AA	117.6	H14D—C14B—H14E	109.5
C6A—C7A—C8A	126.2 (3)	N1B—C14B—H14F	109.5
C6A—C7A—H7AA	116.9	H14D—C14B—H14F	109.5
C8A—C7A—H7AA	116.9	H14E—C14B—H14F	109.5
C9A—C8A—C13A	117.2 (3)	O1—C15B—C16B	110 (2)
C9A—C8A—C7A	120.0 (3)	O1—C15B—H15C	109.7
C13A—C8A—C7A	122.8 (3)	C16B—C15B—H15C	109.7
C10A—C9A—C8A	122.0 (4)	O1—C15B—H15D	109.7
C10A—C9A—H9AA	119.0	C16B—C15B—H15D	109.7
C8A—C9A—H9AA	119.0	H15C—C15B—H15D	108.2
C11A—C10A—C9A	121.6 (5)	C15B—C16B—H16D	109.5
C11A—C10A—H10A	119.2	C15B—C16B—H16E	109.5
C9A—C10A—H10A	119.2	H16D—C16B—H16E	109.5
O1—C11A—C10A	127.3 (5)	C15B—C16B—H16F	109.5
O1—C11A—C12A	115.1 (5)	H16D—C16B—H16F	109.5
C10A—C11A—C12A	117.5 (4)	H16E—C16B—H16F	109.5
C13A—C12A—C11A	121.0 (4)	C22—C17—C18	121.26 (17)
C13A—C12A—H12A	119.5	C22—C17—Br1	119.00 (13)
C11A—C12A—H12A	119.5	C18—C17—Br1	119.71 (13)
C12A—C13A—C8A	120.7 (3)	C19—C18—C17	119.35 (16)
C12A—C13A—H13A	119.7	C19—C18—H18A	120.3
C8A—C13A—H13A	119.7	C17—C18—H18A	120.3
O1—C15A—C16A	107.4 (7)	C18—C19—C20	120.00 (17)
O1—C15A—H15A	110.2	C18—C19—H19A	120.0
C16A—C15A—H15A	110.2	C20—C19—H19A	120.0
O1—C15A—H15B	110.2	C19—C20—C21	120.06 (16)
C16A—C15A—H15B	110.2	C19—C20—S1	119.50 (14)
H15A—C15A—H15B	108.5	C21—C20—S1	120.42 (13)
C2B—N1B—C3B	121.0 (14)	C22—C21—C20	120.21 (16)
C2B—N1B—C14B	126.1 (12)	C22—C21—H21A	119.9
C3B—N1B—C14B	112.9 (13)	C20—C21—H21A	119.9
C2B—C1B—C5B	119.4 (9)	C21—C22—C17	119.11 (16)
C2B—C1B—H1BA	120.3	C21—C22—H22A	120.4
C5B—C1B—H1BA	120.3	C17—C22—H22A	120.4
N1B—C2B—C1B	121.7 (12)	O5—C23—H23A	109.3
N1B—C2B—H2BA	119.1	O5—C23—H23B	133.8
C1B—C2B—H2BA	119.1	H23A—C23—H23B	92.4
N1B—C3B—C4B	119.7 (18)	O5—C23—H23C	109.5
N1B—C3B—H3BA	120.1	H23A—C23—H23C	109.5
C4B—C3B—H3BA	120.1	H23B—C23—H23C	100.1
C3B—C4B—C5B	120.7 (13)
C5A—C1A—C2A—N1A	−1.2 (6)	C2B—C1B—C5B—C4B	−0.9 (12)
C3A—N1A—C2A—C1A	1.0 (9)	C2B—C1B—C5B—C6B	179.4 (8)
C14A—N1A—C2A—C1A	−179.3 (4)	C4B—C5B—C6B—C7B	−178.3 (7)
C2A—N1A—C3A—C4A	0.6 (11)	C1B—C5B—C6B—C7B	1.4 (10)
C14A—N1A—C3A—C4A	−179.2 (6)	C5B—C6B—C7B—C8B	179.5 (6)
N1A—C3A—C4A—C5A	−2.0 (10)	C6B—C7B—C8B—C9B	0.5 (11)
C3A—C4A—C5A—C1A	1.6 (6)	C6B—C7B—C8B—C13B	−177.2 (7)
C3A—C4A—C5A—C6A	−179.0 (5)	C13B—C8B—C9B—C10B	−1.4 (13)
C2A—C1A—C5A—C4A	−0.1 (5)	C7B—C8B—C9B—C10B	−179.1 (9)
C2A—C1A—C5A—C6A	−179.5 (3)	C8B—C9B—C10B—C11B	0.8 (19)
C4A—C5A—C6A—C7A	3.1 (4)	C9B—C10B—C11B—C12B	−1(2)
C1A—C5A—C6A—C7A	−177.6 (3)	C9B—C10B—C11B—O1	−179.6 (12)
C5A—C6A—C7A—C8A	−179.6 (2)	C11A—O1—C11B—C12B	−176 (8)
C6A—C7A—C8A—C9A	177.5 (3)	C15B—O1—C11B—C12B	179.7 (18)
C6A—C7A—C8A—C13A	−2.7 (4)	C15A—O1—C11B—C12B	180.0 (10)
C13A—C8A—C9A—C10A	1.2 (5)	C11A—O1—C11B—C10B	2(5)
C7A—C8A—C9A—C10A	−179.0 (3)	C15B—O1—C11B—C10B	−2(3)
C8A—C9A—C10A—C11A	−1.0 (7)	C15A—O1—C11B—C10B	−2(2)
C11B—O1—C11A—C10A	−175 (7)	C10B—C11B—C12B—C13B	2(2)
C15B—O1—C11A—C10A	1.7 (17)	O1—C11B—C12B—C13B	−179.3 (11)
C15A—O1—C11A—C10A	1.9 (10)	C11B—C12B—C13B—C8B	−2.9 (17)
C11B—O1—C11A—C12A	4(6)	C9B—C8B—C13B—C12B	2.4 (13)
C15B—O1—C11A—C12A	−179.4 (15)	C7B—C8B—C13B—C12B	−179.6 (8)
C15A—O1—C11A—C12A	−179.1 (6)	C11A—O1—C15B—C16B	−176 (2)
C9A—C10A—C11A—O1	179.6 (5)	C11B—O1—C15B—C16B	−175 (2)
C9A—C10A—C11A—C12A	0.6 (9)	C15A—O1—C15B—C16B	158 (100)
O1—C11A—C12A—C13A	−179.6 (5)	C22—C17—C18—C19	−0.6 (3)
C10A—C11A—C12A—C13A	−0.5 (9)	Br1—C17—C18—C19	177.40 (14)
C11A—C12A—C13A—C8A	0.8 (7)	C17—C18—C19—C20	−0.1 (3)
C9A—C8A—C13A—C12A	−1.1 (5)	C18—C19—C20—C21	0.6 (3)
C7A—C8A—C13A—C12A	179.1 (3)	C18—C19—C20—S1	−178.10 (14)
C11A—O1—C15A—C16A	178.8 (8)	O4—S1—C20—C19	62.92 (17)
C11B—O1—C15A—C16A	179.5 (11)	O2—S1—C20—C19	−176.53 (14)
C15B—O1—C15A—C16A	−27 (100)	O3—S1—C20—C19	−57.57 (17)
C3B—N1B—C2B—C1B	−1(2)	O4—S1—C20—C21	−115.77 (15)
C14B—N1B—C2B—C1B	−179.9 (12)	O2—S1—C20—C21	4.79 (16)
C5B—C1B—C2B—N1B	3.0 (18)	O3—S1—C20—C21	123.75 (15)
C2B—N1B—C3B—C4B	−2(3)	C19—C20—C21—C22	−0.4 (3)
C14B—N1B—C3B—C4B	176.3 (14)	S1—C20—C21—C22	178.28 (13)
N1B—C3B—C4B—C5B	4(2)	C20—C21—C22—C17	−0.3 (3)
C3B—C4B—C5B—C1B	−2.7 (16)	C18—C17—C22—C21	0.8 (3)
C3B—C4B—C5B—C6B	176.9 (12)	Br1—C17—C22—C21	−177.23 (13)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N1A/C1A–C5A, C8A–C13A, N1B/C1B–C5B, C8B–C13B and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3i	0.82	1.92	2.657 (4)	149
C1A—H1AA···O2ii	0.93	2.42	3.334 (4)	168
C2A—H2AA···O2iii	0.93	2.38	3.237 (5)	153
C14A—H14A···O4iv	0.96	2.36	3.180 (6)	143
C14A—H14B···O4iii	0.96	2.41	3.343 (6)	163
C19—H19A···O5v	0.93	2.53	3.385 (4)	153
C21—H21A···O2vi	0.93	2.58	3.311 (2)	135
C23—H23C···Br1	0.96	2.77	3.724 (5)	173
C14A—H14C···Cg2ii	0.96	2.66	3.609 (6)	172
C14A—H14C···Cg4ii	0.96	2.63	3.572 (8)	167
C15A—H15A···Cg1vii	0.97	2.84	3.639 (8)	140
C15A—H15A···Cg3vii	0.97	2.84	3.611 (9)	137
C14B—H14D···Cg2ii	0.96	2.87	3.562 (15)	129
C14B—H14D···Cg4ii	0.96	2.80	3.564 (16)	137
C15B—H15C···Cg1vii	0.97	2.81	3.65 (3)	145
C15B—H15C···Cg3vii	0.97	2.81	3.62 (3)	141
C15B—H15D···Cg5viii	0.97	2.98	3.60 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N1A/C1A–C5A, C8A–C13A, N1B/C1B–C5B, C8B–C13B and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O3i	0.82	1.92	2.657 (4)	149
C1A—H1AA⋯O2ii	0.93	2.42	3.334 (4)	168
C2A—H2AA⋯O2iii	0.93	2.38	3.237 (5)	153
C14A—H14A⋯O4iv	0.96	2.36	3.180 (6)	143
C14A—H14B⋯O4iii	0.96	2.41	3.343 (6)	163
C19—H19A⋯O5v	0.93	2.53	3.385 (4)	153
C21—H21A⋯O2vi	0.93	2.58	3.311 (2)	135
C23—H23C⋯Br1	0.96	2.77	3.724 (5)	173
C14A—H14C⋯Cg2ii	0.96	2.66	3.609 (6)	172
C14A—H14C⋯Cg4ii	0.96	2.63	3.572 (8)	167
C15A—H15A⋯Cg1vii	0.97	2.84	3.639 (8)	140
C15A—H15A⋯Cg3vii	0.97	2.84	3.611 (9)	137
C14B—H14D⋯Cg2ii	0.96	2.87	3.562 (15)	129
C14B—H14D⋯Cg4ii	0.96	2.80	3.564 (16)	137
C15B—H15C⋯Cg1vii	0.97	2.81	3.65 (3)	145
C15B—H15C⋯Cg3vii	0.97	2.81	3.62 (3)	141
C15B—H15D⋯Cg5viii	0.97	2.98	3.60 (2)	123

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