(E)-1-Methyl-4-[2-(1-naphth-yl)vin-yl]pyridinium 4-bromo-benzene-sulfonate.

In the title compound, C(18)H(16)N(+)·C(6)H(4)BrO(3)S(-), the cation exists in the E configuration and the whole mol-ecule of the cation is disordered with a refined site-occupancy ratio of 0.733 (1):0.267 (1). The naphthalene system is not planar, the inter-planar angle between the two aromatic rings being 5.0 (5)° for the major component and 5.7 (10)° for the minor component. The cation is twisted with dihedral angles between the pyridinium ring and the two aromatic rings of the naphthalene system of 56.3 (5) and 51.4 (5)° (for the major component) and 52.2 (11) and 53.4 (11)° (for the minor component). The pyridinium ring and the benzene ring of the anion are inclined to each other at inter-planar angles of 85.0 (4) and 71.5 (9)° for the major and minor components, respectively. In the crystal packing, the cations and anions are alternately arranged with the cations stacked in an anti-parallel manner along the c axis and the anions linked together into chains along the same direction. The cations are linked to the anions into chains along [102] by weak C-H⋯O inter-actions. The crystal structure is further stabilized by C-H⋯π inter-actions and π-π contacts, with Cg⋯Cg distances of 3.502 (9) and 3.698 (6) Å. A short Br⋯O contact [3.029 (4) Å] is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to NLO materials research, see: Cheng et al. (1991a ▶; 1991b ▶); Dittrich et al. (2003 ▶); Ogawa et al. (2008 ▶); Weir et al. (2003 ▶); Yang et al. (2007 ▶). For related structures, see, Chanawanno et al. (2008 ▶) and Chantrapromma et al. (2006 ▶; 2007 ▶; 2008 ▶; 2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C18H16N+·C6H4BrO3S−

M = 482.38

Orthorhombic,

a = 12.2195 (2) Å

b = 21.9907 (4) Å

c = 7.6256 (1) Å

V = 2049.12 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.14 mm−1

T = 100 K

0.46 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.437, T max = 0.753

15171 measured reflections

5563 independent reflections

3975 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.107

S = 1.03

5563 reflections

326 parameters

11 restraints

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.49 e Å−3

Absolute structure: Flack (1983 ▶), 2373 Friedel pairs

Flack parameter: −0.003 (11)

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/S1600536809014974/sj2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014974/sj2603Isup2.hkl

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

C18H16N+·C6H4BrO3S−	Dx = 1.564 Mg m−3
Mr = 482.38	Melting point = 495–496 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5563 reflections
a = 12.2195 (2) Å	θ = 2.5–30.0°
b = 21.9907 (4) Å	µ = 2.13 mm−1
c = 7.6256 (1) Å	T = 100 K
V = 2049.12 (6) Å3	Needle, yellow
Z = 4	0.46 × 0.15 × 0.14 mm
F(000) = 984

Bruker APEXII CCD area-detector diffractometer	5563 independent reflections
Radiation source: sealed tube	3975 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→17
Tmin = 0.437, Tmax = 0.753	k = −30→25
15171 measured reflections	l = −10→10

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0268P)2 + 1.3478P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
5563 reflections	Δρmax = 1.11 e Å−3
326 parameters	Δρmin = −0.48 e Å−3
11 restraints	Absolute structure: Flack (1983), 2373 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.003 (11)

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	1.09367 (3)	0.735910 (17)	0.33953 (7)	0.03638 (11)
S1	0.77513 (7)	0.83524 (5)	0.94982 (13)	0.0282 (2)
O1	0.8448 (2)	0.85394 (18)	1.0921 (4)	0.0511 (9)
O2	0.7122 (2)	0.88360 (13)	0.8744 (4)	0.0441 (8)
O3	0.7095 (3)	0.78212 (14)	0.9922 (5)	0.0518 (9)
N1A	0.7710 (6)	0.6185 (4)	0.1666 (13)	0.0408 (19)	0.708 (6)
C1A	0.2235 (8)	0.4733 (4)	0.2313 (16)	0.0658 (14)	0.708 (6)
C2A	0.2047 (9)	0.5344 (4)	0.3012 (16)	0.061 (3)	0.708 (6)
H2AA	0.2583	0.5650	0.2827	0.073*	0.708 (6)
C3A	0.1123 (9)	0.5484 (5)	0.3922 (16)	0.0658 (14)	0.708 (6)
H3AA	0.1022	0.5883	0.4370	0.079*	0.708 (6)
C4A	0.0335 (10)	0.5048 (4)	0.4194 (18)	0.0658 (14)	0.708 (6)
H4AA	−0.0282	0.5156	0.4885	0.079*	0.708 (6)
C5A	0.0378 (8)	0.4470 (5)	0.3538 (16)	0.054 (3)	0.708 (6)
H5AA	−0.0208	0.4190	0.3685	0.065*	0.708 (6)
C6A	0.1369 (10)	0.4309 (5)	0.2605 (17)	0.047 (3)	0.708 (6)
C7A	0.1552 (9)	0.3698 (4)	0.1942 (13)	0.057 (3)	0.708 (6)
H7AA	0.0989	0.3401	0.2024	0.069*	0.708 (6)
C8A	0.2557 (7)	0.3547 (3)	0.1185 (10)	0.0410 (18)	0.708 (6)
H8AA	0.2682	0.3142	0.0800	0.049*	0.708 (6)
C9A	0.3383 (7)	0.3982 (3)	0.0984 (10)	0.0401 (18)	0.708 (6)
H9AA	0.4057	0.3868	0.0459	0.048*	0.708 (6)
C10A	0.3236 (5)	0.4569 (3)	0.1531 (12)	0.055 (2)	0.708 (6)
C11A	0.4093 (6)	0.5027 (4)	0.1523 (13)	0.0658 (14)	0.708 (6)
H11A	0.3894	0.5443	0.1429	0.079*	0.708 (6)
C12A	0.5166 (7)	0.4881 (3)	0.1644 (12)	0.0658 (14)	0.708 (6)
H12A	0.5361	0.4470	0.1858	0.079*	0.708 (6)
C13A	0.6044 (5)	0.5338 (3)	0.1455 (9)	0.0354 (15)	0.708 (6)
C14A	0.7055 (6)	0.5194 (3)	0.2165 (8)	0.0304 (14)	0.708 (6)
H14A	0.7179	0.4795	0.2597	0.036*	0.708 (6)
C15A	0.7866 (6)	0.5609 (4)	0.2254 (11)	0.0426 (19)	0.708 (6)
H15A	0.8555	0.5497	0.2734	0.051*	0.708 (6)
C16A	0.6701 (8)	0.6347 (5)	0.0899 (16)	0.032 (2)	0.708 (6)
H16A	0.6591	0.6737	0.0394	0.038*	0.708 (6)
C17A	0.5912 (11)	0.5933 (6)	0.091 (2)	0.034 (2)	0.708 (6)
H17A	0.5207	0.6053	0.0517	0.041*	0.708 (6)
C18A	0.8611 (5)	0.6636 (3)	0.1790 (13)	0.049 (2)	0.708 (6)
H18A	0.8357	0.7030	0.1345	0.074*	0.708 (6)
H18B	0.9235	0.6497	0.1089	0.074*	0.708 (6)
H18C	0.8835	0.6679	0.3017	0.074*	0.708 (6)
N1B	0.7857 (17)	0.6237 (10)	0.118 (3)	0.028 (5)*	0.292 (6)
C1B	0.2380 (11)	0.4829 (7)	0.2936 (15)	0.028 (4)*	0.292 (6)
C2B	0.2071 (16)	0.5389 (8)	0.3799 (19)	0.027 (4)*	0.292 (6)
H2BA	0.2576	0.5711	0.3981	0.032*	0.292 (6)
C3B	0.0975 (14)	0.5426 (9)	0.435 (2)	0.029 (4)*	0.292 (6)
H3BA	0.0726	0.5797	0.4849	0.035*	0.292 (6)
C4B	0.0193 (17)	0.4919 (8)	0.420 (3)	0.032 (4)*	0.292 (6)
H4BA	−0.0524	0.4921	0.4682	0.038*	0.292 (6)
C5B	0.0648 (15)	0.4427 (10)	0.324 (3)	0.020 (4)*	0.292 (6)
H5BA	0.0163	0.4100	0.2996	0.024*	0.292 (6)
C6B	0.1667 (19)	0.4362 (14)	0.264 (4)	0.028 (6)*	0.292 (6)
C7B	0.1927 (16)	0.3832 (10)	0.183 (3)	0.037 (5)*	0.292 (6)
H7BA	0.1410	0.3514	0.1690	0.044*	0.292 (6)
C8B	0.3015 (16)	0.3782 (11)	0.119 (2)	0.025 (4)*	0.292 (6)
H8BA	0.3218	0.3447	0.0472	0.030*	0.292 (6)
C9B	0.3804 (14)	0.4237 (8)	0.164 (2)	0.038 (4)*	0.292 (6)
H9BA	0.4533	0.4190	0.1223	0.045*	0.292 (6)
C10B	0.3572 (12)	0.4713 (7)	0.258 (2)	0.034 (4)*	0.292 (6)
C11B	0.4442 (9)	0.5144 (5)	0.345 (2)	0.027 (3)*	0.292 (6)
H11B	0.4222	0.5506	0.4033	0.032*	0.292 (6)
C12B	0.5668 (9)	0.4966 (6)	0.334 (3)	0.035 (3)*	0.292 (6)
H12B	0.5946	0.4622	0.3948	0.042*	0.292 (6)
C13B	0.6410 (16)	0.5363 (7)	0.221 (2)	0.027 (3)*	0.292 (6)
C14B	0.7498 (16)	0.5288 (9)	0.241 (2)	0.025 (4)*	0.292 (6)
H14B	0.7751	0.4910	0.2865	0.030*	0.292 (6)
C15B	0.8236 (15)	0.5706 (8)	0.202 (2)	0.028 (4)*	0.292 (6)
H15B	0.8988	0.5652	0.2299	0.034*	0.292 (6)
C16B	0.692 (2)	0.6327 (14)	0.111 (4)	0.025 (7)*	0.292 (6)
H16B	0.6727	0.6739	0.0892	0.030*	0.292 (6)
C17B	0.601 (4)	0.594 (2)	0.131 (5)	0.041 (11)*	0.292 (6)
H17B	0.5281	0.6017	0.0944	0.049*	0.292 (6)
C18B	0.8654 (16)	0.6754 (9)	0.083 (3)	0.040 (4)*	0.292 (6)
H18D	0.8352	0.7023	−0.0077	0.061*	0.292 (6)
H18E	0.9353	0.6587	0.0418	0.061*	0.292 (6)
H18F	0.8772	0.6985	0.1908	0.061*	0.292 (6)
C19	0.8411 (3)	0.82014 (19)	0.6071 (6)	0.0318 (9)
H19A	0.7774	0.8426	0.5776	0.038*
C20	0.9073 (3)	0.79817 (19)	0.4741 (6)	0.0336 (9)
H20A	0.8892	0.8048	0.3545	0.040*
C21	1.0008 (3)	0.76615 (19)	0.5203 (6)	0.0336 (9)
C22	1.0283 (3)	0.7563 (2)	0.6960 (6)	0.0342 (9)
H22A	1.0928	0.7344	0.7254	0.041*
C23	0.9611 (3)	0.77848 (16)	0.8261 (7)	0.0322 (8)
H23A	0.9794	0.7723	0.9458	0.039*
C24	0.8656 (3)	0.81016 (17)	0.7818 (5)	0.0265 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.03289 (17)	0.0388 (2)	0.0375 (2)	−0.00330 (17)	0.0114 (2)	−0.0081 (3)
S1	0.0279 (4)	0.0316 (5)	0.0250 (4)	−0.0001 (4)	0.0058 (4)	0.0027 (4)
O1	0.0363 (16)	0.085 (3)	0.0320 (17)	0.0042 (17)	0.0021 (15)	−0.0159 (18)
O2	0.0474 (16)	0.0455 (18)	0.039 (2)	0.0191 (14)	0.0116 (15)	0.0103 (14)
O3	0.059 (2)	0.0385 (18)	0.058 (2)	−0.0128 (15)	0.0293 (18)	−0.0001 (16)
N1A	0.025 (3)	0.037 (4)	0.060 (6)	−0.002 (3)	0.007 (4)	0.006 (4)
C1A	0.068 (3)	0.033 (2)	0.096 (4)	0.0093 (18)	−0.032 (2)	−0.003 (2)
C2A	0.074 (6)	0.034 (4)	0.074 (7)	0.005 (3)	−0.048 (5)	−0.003 (4)
C3A	0.068 (3)	0.033 (2)	0.096 (4)	0.0093 (18)	−0.032 (2)	−0.003 (2)
C4A	0.068 (3)	0.033 (2)	0.096 (4)	0.0093 (18)	−0.032 (2)	−0.003 (2)
C5A	0.054 (6)	0.062 (6)	0.046 (6)	0.019 (5)	0.007 (5)	0.001 (5)
C6A	0.051 (7)	0.033 (5)	0.057 (6)	−0.002 (5)	−0.004 (6)	0.013 (3)
C7A	0.074 (6)	0.034 (5)	0.064 (6)	−0.018 (5)	−0.011 (5)	0.007 (4)
C8A	0.057 (4)	0.019 (3)	0.047 (4)	−0.014 (3)	0.001 (4)	−0.006 (3)
C9A	0.049 (4)	0.025 (4)	0.046 (4)	−0.014 (3)	−0.018 (4)	0.006 (3)
C10A	0.043 (4)	0.015 (3)	0.105 (7)	0.002 (3)	−0.046 (4)	0.001 (4)
C11A	0.068 (3)	0.033 (2)	0.096 (4)	0.0093 (18)	−0.032 (2)	−0.003 (2)
C12A	0.068 (3)	0.033 (2)	0.096 (4)	0.0093 (18)	−0.032 (2)	−0.003 (2)
C13A	0.026 (3)	0.040 (4)	0.040 (4)	0.010 (3)	−0.015 (3)	−0.016 (3)
C14A	0.029 (3)	0.028 (4)	0.034 (3)	−0.005 (3)	−0.006 (3)	−0.002 (3)
C15A	0.020 (3)	0.046 (5)	0.063 (5)	0.002 (3)	−0.001 (3)	0.015 (4)
C16A	0.018 (4)	0.038 (5)	0.040 (5)	0.008 (4)	−0.003 (4)	0.014 (3)
C17A	0.028 (4)	0.039 (5)	0.035 (6)	−0.001 (3)	0.006 (5)	−0.011 (5)
C18A	0.028 (3)	0.043 (4)	0.076 (6)	−0.007 (3)	0.007 (4)	0.002 (4)
C19	0.032 (2)	0.033 (2)	0.030 (2)	0.0022 (17)	0.0073 (18)	0.0056 (18)
C20	0.038 (2)	0.035 (2)	0.028 (2)	0.0010 (18)	0.0026 (19)	−0.0005 (17)
C21	0.0284 (18)	0.034 (2)	0.038 (2)	−0.0001 (18)	0.0107 (17)	−0.0008 (19)
C22	0.0301 (19)	0.038 (2)	0.034 (2)	0.0012 (18)	0.0032 (18)	0.0035 (18)
C23	0.0283 (15)	0.036 (2)	0.032 (2)	−0.0015 (14)	0.004 (2)	0.005 (2)
C24	0.0283 (16)	0.024 (2)	0.0275 (19)	−0.0038 (16)	0.0047 (15)	0.0039 (15)

Br1—C21	1.905 (4)	C1B—C6B	1.37 (3)
S1—O2	1.433 (3)	C1B—C2B	1.45 (2)
S1—O1	1.439 (3)	C1B—C10B	1.50 (2)
S1—O3	1.453 (3)	C2B—C3B	1.41 (3)
S1—C24	1.780 (4)	C2B—H2BA	0.9500
N1A—C15A	1.357 (12)	C3B—C4B	1.47 (2)
N1A—C16A	1.410 (13)	C3B—H3BA	0.9500
N1A—C18A	1.485 (10)	C4B—C5B	1.42 (3)
C1A—C10A	1.407 (13)	C4B—H4BA	0.9500
C1A—C6A	1.428 (14)	C5B—C6B	1.33 (3)
C1A—C2A	1.465 (12)	C5B—H5BA	0.9500
C2A—C3A	1.361 (15)	C6B—C7B	1.36 (4)
C2A—H2AA	0.9500	C7B—C8B	1.42 (3)
C3A—C4A	1.374 (15)	C7B—H7BA	0.9500
C3A—H3AA	0.9500	C8B—C9B	1.43 (3)
C4A—C5A	1.368 (14)	C8B—H8BA	0.9500
C4A—H4AA	0.9500	C9B—C10B	1.30 (2)
C5A—C6A	1.448 (15)	C9B—H9BA	0.9500
C5A—H5AA	0.9500	C10B—C11B	1.57 (2)
C6A—C7A	1.453 (16)	C11B—C12B	1.552 (15)
C7A—C8A	1.398 (13)	C11B—H11B	0.9500
C7A—H7AA	0.9500	C12B—C13B	1.52 (2)
C8A—C9A	1.398 (9)	C12B—H12B	0.9500
C8A—H8AA	0.9500	C13B—C14B	1.35 (2)
C9A—C10A	1.369 (10)	C13B—C17B	1.52 (5)
C9A—H9AA	0.9500	C14B—C15B	1.32 (2)
C10A—C11A	1.454 (10)	C14B—H14B	0.9500
C11A—C12A	1.353 (10)	C15B—H15B	0.9500
C11A—H11A	0.9500	C16B—C17B	1.41 (5)
C12A—C13A	1.477 (10)	C16B—H16B	0.9500
C12A—H12A	0.9500	C17B—H17B	0.9500
C13A—C17A	1.382 (17)	C18B—H18D	0.9800
C13A—C14A	1.385 (9)	C18B—H18E	0.9800
C14A—C15A	1.350 (10)	C18B—H18F	0.9800
C14A—H14A	0.9500	C19—C24	1.383 (6)
C15A—H15A	0.9500	C19—C20	1.383 (6)
C16A—C17A	1.327 (18)	C19—H19A	0.9500
C16A—H16A	0.9500	C20—C21	1.388 (6)
C17A—H17A	0.9500	C20—H20A	0.9500
C18A—H18A	0.9800	C21—C22	1.398 (6)
C18A—H18B	0.9800	C22—C23	1.378 (6)
C18A—H18C	0.9800	C22—H22A	0.9500
N1B—C16B	1.17 (3)	C23—C24	1.399 (5)
N1B—C15B	1.41 (3)	C23—H23A	0.9500
N1B—C18B	1.52 (3)
O2—S1—O1	114.1 (2)	C2B—C3B—C4B	123.4 (18)
O2—S1—O3	112.96 (19)	C2B—C3B—H3BA	118.3
O1—S1—O3	112.9 (2)	C4B—C3B—H3BA	118.3
O2—S1—C24	105.91 (18)	C5B—C4B—C3B	111.3 (17)
O1—S1—C24	105.27 (17)	C5B—C4B—H4BA	124.3
O3—S1—C24	104.71 (18)	C3B—C4B—H4BA	124.3
C15A—N1A—C16A	119.7 (8)	C6B—C5B—C4B	129 (2)
C15A—N1A—C18A	119.9 (7)	C6B—C5B—H5BA	115.7
C16A—N1A—C18A	120.4 (8)	C4B—C5B—H5BA	115.7
C10A—C1A—C6A	122.9 (9)	C5B—C6B—C7B	118 (2)
C10A—C1A—C2A	121.7 (9)	C5B—C6B—C1B	117 (3)
C6A—C1A—C2A	115.2 (10)	C7B—C6B—C1B	125 (2)
C3A—C2A—C1A	121.5 (10)	C6B—C7B—C8B	116 (2)
C3A—C2A—H2AA	119.2	C6B—C7B—H7BA	121.8
C1A—C2A—H2AA	119.2	C8B—C7B—H7BA	121.8
C2A—C3A—C4A	120.1 (10)	C7B—C8B—C9B	119.6 (18)
C2A—C3A—H3AA	119.9	C7B—C8B—H8BA	120.2
C4A—C3A—H3AA	119.9	C9B—C8B—H8BA	120.2
C5A—C4A—C3A	124.5 (12)	C10B—C9B—C8B	123.2 (17)
C5A—C4A—H4AA	117.8	C10B—C9B—H9BA	118.4
C3A—C4A—H4AA	117.8	C8B—C9B—H9BA	118.4
C4A—C5A—C6A	116.0 (11)	C9B—C10B—C1B	116.6 (16)
C4A—C5A—H5AA	122.0	C9B—C10B—C11B	124.9 (15)
C6A—C5A—H5AA	122.0	C1B—C10B—C11B	118.5 (12)
C1A—C6A—C5A	122.5 (10)	C12B—C11B—C10B	118.5 (11)
C1A—C6A—C7A	115.8 (10)	C12B—C11B—H11B	120.7
C5A—C6A—C7A	121.7 (10)	C10B—C11B—H11B	120.7
C8A—C7A—C6A	119.9 (9)	C13B—C12B—C11B	117.4 (13)
C8A—C7A—H7AA	120.0	C13B—C12B—H12B	121.3
C6A—C7A—H7AA	120.0	C11B—C12B—H12B	121.3
C7A—C8A—C9A	121.1 (7)	C14B—C13B—C17B	118 (2)
C7A—C8A—H8AA	119.4	C14B—C13B—C12B	116.9 (16)
C9A—C8A—H8AA	119.4	C17B—C13B—C12B	123 (2)
C10A—C9A—C8A	121.1 (8)	C15B—C14B—C13B	124.2 (18)
C10A—C9A—H9AA	119.4	C15B—C14B—H14B	117.9
C8A—C9A—H9AA	119.4	C13B—C14B—H14B	117.9
C9A—C10A—C1A	119.0 (7)	C14B—C15B—N1B	117.0 (17)
C9A—C10A—C11A	123.9 (8)	C14B—C15B—H15B	121.5
C1A—C10A—C11A	116.8 (7)	N1B—C15B—H15B	121.5
C12A—C11A—C10A	122.2 (7)	N1B—C16B—C17B	132 (3)
C12A—C11A—H11A	118.9	N1B—C16B—H16B	114.1
C10A—C11A—H11A	118.9	C17B—C16B—H16B	114.1
C11A—C12A—C13A	122.4 (7)	C16B—C17B—C13B	108 (3)
C11A—C12A—H12A	118.8	C16B—C17B—H17B	126.2
C13A—C12A—H12A	118.8	C13B—C17B—H17B	126.2
C17A—C13A—C14A	116.0 (8)	N1B—C18B—H18D	109.5
C17A—C13A—C12A	126.0 (8)	N1B—C18B—H18E	109.5
C14A—C13A—C12A	117.0 (6)	H18D—C18B—H18E	109.5
C15A—C14A—C13A	121.3 (6)	N1B—C18B—H18F	109.5
C15A—C14A—H14A	119.3	H18D—C18B—H18F	109.5
C13A—C14A—H14A	119.3	H18E—C18B—H18F	109.5
C14A—C15A—N1A	120.7 (6)	C24—C19—C20	121.6 (4)
C14A—C15A—H15A	119.6	C24—C19—H19A	119.2
N1A—C15A—H15A	119.6	C20—C19—H19A	119.2
C17A—C16A—N1A	117.4 (11)	C19—C20—C21	118.2 (4)
C17A—C16A—H16A	121.3	C19—C20—H20A	120.9
N1A—C16A—H16A	121.3	C21—C20—H20A	120.9
C16A—C17A—C13A	124.5 (13)	C20—C21—C22	121.3 (4)
C16A—C17A—H17A	117.7	C20—C21—Br1	119.0 (3)
C13A—C17A—H17A	117.7	C22—C21—Br1	119.7 (3)
C16B—N1B—C15B	119 (2)	C23—C22—C21	119.4 (4)
C16B—N1B—C18B	120 (2)	C23—C22—H22A	120.3
C15B—N1B—C18B	119.2 (18)	C21—C22—H22A	120.3
C6B—C1B—C2B	123.2 (18)	C22—C23—C24	120.0 (5)
C6B—C1B—C10B	117.5 (17)	C22—C23—H23A	120.0
C2B—C1B—C10B	118.7 (14)	C24—C23—H23A	120.0
C3B—C2B—C1B	115.8 (17)	C19—C24—C23	119.4 (4)
C3B—C2B—H2BA	122.1	C19—C24—S1	120.7 (3)
C1B—C2B—H2BA	122.1	C23—C24—S1	119.9 (3)
C10A—C1A—C2A—C3A	−173.3 (10)	C10B—C1B—C6B—C5B	168.5 (19)
C6A—C1A—C2A—C3A	2.1 (15)	C2B—C1B—C6B—C7B	179.5 (19)
C1A—C2A—C3A—C4A	−0.4 (16)	C10B—C1B—C6B—C7B	−10 (3)
C2A—C3A—C4A—C5A	−3.1 (17)	C5B—C6B—C7B—C8B	179 (2)
C3A—C4A—C5A—C6A	4.5 (17)	C1B—C6B—C7B—C8B	−2(4)
C10A—C1A—C6A—C5A	174.8 (10)	C6B—C7B—C8B—C9B	9(3)
C2A—C1A—C6A—C5A	−0.5 (16)	C7B—C8B—C9B—C10B	−2(3)
C10A—C1A—C6A—C7A	−3.7 (16)	C8B—C9B—C10B—C1B	−11 (2)
C2A—C1A—C6A—C7A	−179.0 (9)	C8B—C9B—C10B—C11B	165.7 (15)
C4A—C5A—C6A—C1A	−2.6 (17)	C6B—C1B—C10B—C9B	16 (2)
C4A—C5A—C6A—C7A	175.9 (10)	C2B—C1B—C10B—C9B	−172.8 (12)
C1A—C6A—C7A—C8A	4.2 (14)	C6B—C1B—C10B—C11B	−160.3 (17)
C5A—C6A—C7A—C8A	−174.4 (10)	C2B—C1B—C10B—C11B	10.7 (16)
C6A—C7A—C8A—C9A	−2.7 (13)	C9B—C10B—C11B—C12B	−6(2)
C7A—C8A—C9A—C10A	0.3 (11)	C1B—C10B—C11B—C12B	170.2 (13)
C8A—C9A—C10A—C1A	0.2 (12)	C10B—C11B—C12B—C13B	111.9 (15)
C8A—C9A—C10A—C11A	173.6 (8)	C11B—C12B—C13B—C14B	166.2 (15)
C6A—C1A—C10A—C9A	1.6 (14)	C11B—C12B—C13B—C17B	4(3)
C2A—C1A—C10A—C9A	176.6 (9)	C17B—C13B—C14B—C15B	7(3)
C6A—C1A—C10A—C11A	−172.3 (9)	C12B—C13B—C14B—C15B	−156.7 (17)
C2A—C1A—C10A—C11A	2.8 (13)	C13B—C14B—C15B—N1B	−7(3)
C9A—C10A—C11A—C12A	−26.5 (14)	C16B—N1B—C15B—C14B	12 (3)
C1A—C10A—C11A—C12A	147.0 (10)	C18B—N1B—C15B—C14B	175.3 (17)
C10A—C11A—C12A—C13A	173.6 (8)	C15B—N1B—C16B—C17B	−20 (5)
C11A—C12A—C13A—C17A	−9.3 (15)	C18B—N1B—C16B—C17B	177 (3)
C11A—C12A—C13A—C14A	158.9 (8)	N1B—C16B—C17B—C13B	18 (5)
C17A—C13A—C14A—C15A	−2.2 (10)	C14B—C13B—C17B—C16B	−9(3)
C12A—C13A—C14A—C15A	−171.6 (7)	C12B—C13B—C17B—C16B	153 (2)
C13A—C14A—C15A—N1A	0.8 (11)	C24—C19—C20—C21	−0.9 (6)
C16A—N1A—C15A—C14A	−2.1 (14)	C19—C20—C21—C22	−0.1 (6)
C18A—N1A—C15A—C14A	179.5 (7)	C19—C20—C21—Br1	−179.6 (3)
C15A—N1A—C16A—C17A	5.0 (16)	C20—C21—C22—C23	0.3 (7)
C18A—N1A—C16A—C17A	−176.6 (10)	Br1—C21—C22—C23	179.7 (3)
N1A—C16A—C17A—C13A	−7.0 (19)	C21—C22—C23—C24	0.6 (6)
C14A—C13A—C17A—C16A	5.6 (17)	C20—C19—C24—C23	1.7 (6)
C12A—C13A—C17A—C16A	173.9 (11)	C20—C19—C24—S1	−176.4 (3)
C6B—C1B—C2B—C3B	0.6 (16)	C22—C23—C24—C19	−1.6 (6)
C10B—C1B—C2B—C3B	−169.9 (11)	C22—C23—C24—S1	176.6 (3)
C1B—C2B—C3B—C4B	4.4 (14)	O2—S1—C24—C19	−23.2 (4)
C2B—C3B—C4B—C5B	−7(2)	O1—S1—C24—C19	−144.4 (3)
C3B—C4B—C5B—C6B	6(3)	O3—S1—C24—C19	96.4 (4)
C4B—C5B—C6B—C7B	177 (2)	O2—S1—C24—C23	158.7 (3)
C4B—C5B—C6B—C1B	−2(4)	O1—S1—C24—C23	37.5 (4)
C2B—C1B—C6B—C5B	−2(3)	O3—S1—C24—C23	−81.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···O1i	0.95	2.53	3.392 (11)	151
C5A—H5AA···O2ii	0.95	2.47	3.362 (10)	157
C11A—H11A···O1i	0.95	2.34	3.282 (10)	175
C14A—H14A···O2iii	0.95	2.44	3.373 (7)	169
C16A—H16A···O3iv	0.95	2.49	3.361 (11)	153
C17A—H17A···O1i	0.95	2.35	3.227 (14)	153
C18A—H18A···O3iv	0.98	2.57	3.501 (8)	159
C19—H19A···O2	0.95	2.56	2.930 (5)	103
C20—H20A···O1iv	0.95	2.34	3.252 (5)	161
C22—H22A···O3v	0.95	2.51	3.274 (6)	137
C4A—H4AA···Cg2vi	0.95	2.84	3.659 (14)	145
C7A—H7AA···Cg4vii	0.95	2.88	3.657 (9)	140
C4B—H4BA···Cg2vi	0.95	2.90	3.59 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯O1i	0.95	2.53	3.392 (11)	151
C5A—H5AA⋯O2ii	0.95	2.47	3.362 (10)	157
C11A—H11A⋯O1i	0.95	2.34	3.282 (10)	175
C14A—H14A⋯O2iii	0.95	2.44	3.373 (7)	169
C16A—H16A⋯O3iv	0.95	2.49	3.361 (11)	153
C17A—H17A⋯O1i	0.95	2.35	3.227 (14)	153
C18A—H18A⋯O3iv	0.98	2.57	3.501 (8)	159
C19—H19A⋯O2	0.95	2.56	2.930 (5)	103
C20—H20A⋯O1iv	0.95	2.34	3.252 (5)	161
C22—H22A⋯O3v	0.95	2.51	3.274 (6)	137
C4A—H4AA⋯Cg2vi	0.95	2.84	3.659 (14)	145
C7A—H7AA⋯Cg4vii	0.95	2.88	3.657 (9)	140
C4B—H4BA⋯Cg2vi	0.95	2.90	3.59 (2)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg2 and Cg4 are the centroids of the C1A–C6A and C19–C24 rings, respectively.