(E)-1-Methyl-4-[2-(2-naphth-yl)vin-yl]pyridinium iodide.

In the title compound, C(18)H(16)N(+)·I(-), the cation is disordered over two orientations related by a 180° rotation about its long axis with occupancies of 0.554 (7) and 0.446 (7). Both disorder components exist in an E configuration. The dihedral angle between the pyridinium ring and the naphthalene ring system is 4.7 (6)° in the major disorder component and 1.6 (8)° in the minor component. In the crystal structure, centrosymmetrically related cations are stacked along the a axis, with significant π-π inter-actions between the pyridinium ring and the naphthalene ring system [centroid-centroid distance = 3.442 (9) Å]. The iodide ions are located between adjacent columns of cations. The cations are linked to the iodide ions by C-H⋯I inter-actions. Weak C-H⋯π inter-actions involving the methyl group are also observed.

Related literature

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

Experimental

Crystal data

C18H16N+·I−

M = 373.29

Monoclinic,

a = 7.2789 (1) Å

b = 10.9363 (2) Å

c = 20.0883 (4) Å

β = 101.280 (1)°

V = 1568.22 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.03 mm−1

T = 100 K

0.53 × 0.30 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.412, T max = 0.838

34203 measured reflections

6896 independent reflections

5373 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.06

6896 reflections

338 parameters

91 restraints

H-atom parameters constrained

Δρmax = 3.51 e Å−3

Δρmin = −2.42 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/S1600536809019114/ci2807sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019114/ci2807Isup2.hkl

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

C18H16N+·I−	F(000) = 736
Mr = 373.29	Dx = 1.581 Mg m−3
Monoclinic, P21/c	Melting point = 557–558 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.2789 (1) Å	Cell parameters from 6896 reflections
b = 10.9363 (2) Å	θ = 2.1–35.0°
c = 20.0883 (4) Å	µ = 2.03 mm−1
β = 101.280 (1)°	T = 100 K
V = 1568.22 (5) Å3	Plate, yellow
Z = 4	0.53 × 0.30 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	6896 independent reflections
Radiation source: sealed tube	5373 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 35.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.412, Tmax = 0.838	k = −17→16
34203 measured reflections	l = −32→27

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0586P)2 + 4.6136P] where P = (Fo2 + 2Fc2)/3
6896 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 3.51 e Å−3
91 restraints	Δρmin = −2.42 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)
I1	0.48129 (4)	0.73286 (2)	0.633723 (12)	0.03874 (9)
N1A	0.520 (4)	0.174 (3)	1.153 (2)	0.022 (2)	0.555 (7)
C1A	0.3651 (10)	0.1993 (7)	1.0385 (4)	0.0268 (12)	0.555 (7)
H1AA	0.3113	0.1634	0.9973	0.032*	0.555 (7)
C2A	0.452 (2)	0.1269 (8)	1.0898 (7)	0.0230 (16)	0.555 (7)
H2AA	0.4665	0.0440	1.0820	0.028*	0.555 (7)
C3A	0.516 (2)	0.2966 (15)	1.1600 (7)	0.033 (2)	0.555 (7)
H3AA	0.5689	0.3307	1.2018	0.039*	0.555 (7)
C4A	0.4359 (12)	0.3744 (8)	1.1076 (5)	0.0290 (15)	0.555 (7)
H4AA	0.4382	0.4586	1.1145	0.035*	0.555 (7)
C5A	0.3533 (8)	0.3270 (6)	1.0454 (4)	0.0238 (11)	0.555 (7)
C6A	0.2561 (8)	0.4011 (5)	0.9884 (3)	0.0283 (12)	0.555 (7)
H6AA	0.2049	0.3616	0.9480	0.034*	0.555 (7)
C7A	0.2374 (8)	0.5225 (5)	0.9915 (3)	0.0282 (12)	0.555 (7)
H7AA	0.2908	0.5591	1.0325	0.034*	0.555 (7)
C8A	0.1433 (9)	0.6045 (7)	0.9383 (4)	0.0268 (11)	0.555 (7)
C9A	0.1464 (11)	0.7284 (8)	0.9532 (4)	0.0263 (12)	0.555 (7)
H9AA	0.2117	0.7573	0.9947	0.032*	0.555 (7)
C10A	0.047 (3)	0.8108 (13)	0.9036 (9)	0.028 (2)	0.555 (7)
C11A	0.0570 (16)	0.9380 (9)	0.9171 (5)	0.0303 (17)	0.555 (7)
H11A	0.1258	0.9661	0.9582	0.036*	0.555 (7)
C12A	−0.0330 (19)	1.0196 (11)	0.8709 (6)	0.041 (2)	0.555 (7)
H12A	−0.0320	1.1026	0.8811	0.049*	0.555 (7)
C13A	−0.128 (4)	0.976 (2)	0.8070 (8)	0.047 (4)	0.555 (7)
H13A	−0.1882	1.0300	0.7738	0.056*	0.555 (7)
C14A	−0.129 (4)	0.852 (2)	0.7955 (13)	0.047 (3)	0.555 (7)
H14A	−0.1968	0.8284	0.7534	0.057*	0.555 (7)
C15A	−0.0433 (17)	0.7529 (12)	0.8368 (7)	0.0400 (17)	0.555 (7)
C16A	−0.040 (2)	0.6423 (19)	0.8260 (7)	0.0400 (17)	0.555 (7)
H16A	−0.1012	0.6131	0.7840	0.048*	0.555 (7)
C17A	0.0489 (12)	0.5599 (8)	0.8729 (4)	0.0312 (14)	0.555 (7)
H17A	0.0484	0.4769	0.8628	0.037*	0.555 (7)
C18A	0.618 (2)	0.0940 (16)	1.2057 (9)	0.040 (4)	0.555 (7)
H18A	0.6436	0.1367	1.2483	0.061*	0.555 (7)
H18B	0.7343	0.0685	1.1941	0.061*	0.555 (7)
H18C	0.5423	0.0236	1.2095	0.061*	0.555 (7)
N1B	0.544 (5)	0.186 (3)	1.151 (3)	0.022 (2)	0.45
C1B	0.3643 (13)	0.2454 (8)	1.0446 (5)	0.0262 (16)	0.445 (7)
H1BA	0.3072	0.2232	1.0007	0.031*	0.445 (7)
C2B	0.443 (3)	0.1573 (12)	1.0917 (10)	0.029 (2)	0.445 (7)
H2BA	0.4241	0.0752	1.0805	0.034*	0.445 (7)
C3B	0.546 (3)	0.3028 (12)	1.1733 (8)	0.021 (2)	0.445 (7)
H3BA	0.6026	0.3218	1.2177	0.025*	0.445 (7)
C4B	0.4663 (15)	0.3915 (9)	1.1306 (5)	0.0257 (15)	0.445 (7)
H4BA	0.4740	0.4721	1.1457	0.031*	0.445 (7)
C5B	0.3727 (11)	0.3669 (8)	1.0646 (4)	0.0246 (14)	0.445 (7)
C6B	0.2907 (10)	0.4672 (7)	1.0211 (4)	0.0276 (14)	0.445 (7)
H6BA	0.3067	0.5450	1.0401	0.033*	0.445 (7)
C7B	0.1948 (10)	0.4609 (7)	0.9569 (4)	0.0277 (14)	0.445 (7)
H7BA	0.1786	0.3843	0.9366	0.033*	0.445 (7)
C8B	0.1140 (11)	0.5666 (8)	0.9168 (5)	0.0258 (14)	0.445 (7)
C9B	0.1359 (14)	0.6857 (9)	0.9432 (5)	0.0248 (16)	0.445 (7)
H9BA	0.1989	0.6971	0.9877	0.030*	0.445 (7)
C10B	0.066 (3)	0.7876 (14)	0.9045 (12)	0.024 (2)	0.445 (7)
C11B	0.073 (2)	0.9053 (11)	0.9303 (6)	0.031 (2)	0.445 (7)
H11B	0.1359	0.9193	0.9747	0.037*	0.445 (7)
C12B	−0.009 (2)	1.0020 (13)	0.8918 (6)	0.035 (2)	0.445 (7)
H12B	0.0004	1.0804	0.9101	0.042*	0.445 (7)
C13B	−0.110 (4)	0.983 (2)	0.8243 (10)	0.033 (3)	0.445 (7)
H13B	−0.1654	1.0503	0.8000	0.040*	0.445 (7)
C14B	−0.128 (5)	0.8686 (15)	0.7928 (12)	0.024 (3)	0.445 (7)
H14B	−0.1891	0.8547	0.7483	0.029*	0.445 (7)
C15B	−0.0405 (15)	0.7753 (7)	0.8384 (5)	0.0125 (13)*	0.445 (7)
C16B	−0.056 (2)	0.6447 (17)	0.8116 (6)	0.031 (2)	0.445 (7)
H16B	−0.1177	0.6311	0.7671	0.037*	0.445 (7)
C17B	0.0140 (14)	0.5504 (11)	0.8485 (5)	0.0323 (19)	0.445 (7)
H17B	−0.0016	0.4722	0.8301	0.039*	0.445 (7)
C18B	0.624 (3)	0.0915 (12)	1.2029 (8)	0.026 (3)	0.445 (7)
H18G	0.5790	0.0120	1.1874	0.039*	0.445 (7)
H18D	0.5873	0.1095	1.2451	0.039*	0.445 (7)
H18E	0.7586	0.0928	1.2093	0.039*	0.445 (7)

	U11	U22	U33	U12	U13	U23
I1	0.05884 (17)	0.02652 (11)	0.03108 (12)	−0.00509 (9)	0.00937 (10)	0.00240 (8)
N1A	0.014 (7)	0.019 (5)	0.037 (3)	−0.005 (4)	0.014 (4)	0.003 (3)
C1A	0.029 (3)	0.021 (3)	0.033 (3)	−0.003 (3)	0.013 (2)	0.000 (3)
C2A	0.024 (3)	0.015 (4)	0.032 (3)	0.000 (3)	0.011 (2)	−0.005 (3)
C3A	0.020 (5)	0.044 (4)	0.034 (5)	−0.010 (3)	0.004 (3)	−0.011 (3)
C4A	0.030 (4)	0.022 (3)	0.037 (4)	0.002 (2)	0.012 (3)	−0.005 (3)
C5A	0.027 (3)	0.017 (3)	0.030 (3)	0.000 (2)	0.012 (2)	0.002 (2)
C6A	0.029 (3)	0.025 (2)	0.033 (3)	0.0001 (19)	0.009 (2)	0.001 (2)
C7A	0.026 (2)	0.026 (2)	0.033 (3)	−0.0007 (19)	0.007 (2)	0.000 (2)
C8A	0.028 (3)	0.025 (3)	0.030 (3)	−0.003 (2)	0.012 (2)	0.000 (2)
C9A	0.026 (3)	0.025 (3)	0.030 (3)	−0.001 (3)	0.011 (2)	0.000 (3)
C10A	0.020 (5)	0.039 (5)	0.026 (3)	0.013 (4)	0.010 (3)	0.008 (4)
C11A	0.029 (3)	0.027 (4)	0.037 (4)	0.002 (3)	0.011 (3)	0.008 (3)
C12A	0.032 (5)	0.035 (4)	0.058 (7)	0.005 (3)	0.017 (5)	0.018 (4)
C13A	0.027 (5)	0.066 (7)	0.049 (8)	0.011 (6)	0.012 (6)	0.025 (6)
C14A	0.027 (7)	0.073 (8)	0.045 (7)	−0.001 (8)	0.013 (5)	0.008 (6)
C15A	0.027 (3)	0.055 (4)	0.042 (3)	−0.009 (3)	0.015 (2)	−0.007 (3)
C16A	0.027 (3)	0.055 (4)	0.042 (3)	−0.009 (3)	0.015 (2)	−0.007 (3)
C17A	0.032 (4)	0.030 (3)	0.033 (4)	−0.008 (2)	0.011 (3)	−0.008 (3)
C18A	0.019 (5)	0.049 (7)	0.050 (7)	0.000 (4)	−0.001 (5)	−0.001 (5)
N1B	0.014 (7)	0.019 (5)	0.037 (3)	−0.005 (4)	0.014 (4)	0.003 (3)
C1B	0.030 (3)	0.017 (4)	0.033 (4)	−0.003 (3)	0.011 (3)	−0.001 (3)
C2B	0.030 (4)	0.018 (5)	0.042 (4)	0.003 (5)	0.019 (3)	−0.007 (4)
C3B	0.016 (5)	0.012 (3)	0.035 (6)	−0.005 (3)	0.004 (4)	−0.007 (3)
C4B	0.031 (4)	0.019 (3)	0.031 (4)	−0.006 (3)	0.017 (3)	−0.003 (3)
C5B	0.030 (3)	0.021 (3)	0.026 (3)	−0.003 (3)	0.012 (3)	−0.007 (2)
C6B	0.029 (3)	0.022 (3)	0.032 (3)	0.001 (2)	0.009 (2)	0.001 (2)
C7B	0.028 (3)	0.025 (3)	0.032 (3)	0.001 (2)	0.009 (2)	−0.004 (2)
C8B	0.024 (3)	0.022 (3)	0.031 (4)	0.000 (3)	0.007 (3)	0.000 (3)
C9B	0.029 (3)	0.024 (4)	0.022 (3)	0.000 (3)	0.008 (2)	−0.003 (3)
C10B	0.009 (4)	0.031 (5)	0.032 (4)	0.007 (4)	0.007 (3)	−0.004 (4)
C11B	0.031 (4)	0.032 (5)	0.030 (5)	0.000 (4)	0.008 (4)	0.002 (4)
C12B	0.036 (5)	0.032 (5)	0.039 (6)	0.003 (4)	0.014 (5)	0.000 (4)
C13B	0.026 (7)	0.037 (5)	0.041 (7)	0.006 (4)	0.015 (6)	0.005 (5)
C14B	0.018 (6)	0.028 (4)	0.026 (4)	0.007 (3)	0.003 (4)	0.015 (3)
C16B	0.030 (5)	0.029 (4)	0.035 (5)	0.002 (3)	0.009 (4)	−0.003 (4)
C17B	0.026 (4)	0.045 (5)	0.026 (4)	−0.003 (3)	0.006 (3)	−0.011 (4)
C18B	0.039 (8)	0.014 (4)	0.032 (5)	0.012 (4)	0.022 (5)	0.012 (4)

N1A—C3A	1.34 (3)	N1B—C2B	1.31 (6)
N1A—C2A	1.38 (4)	N1B—C3B	1.36 (4)
N1A—C18A	1.45 (4)	N1B—C18B	1.50 (5)
C1A—C2A	1.354 (13)	C1B—C5B	1.385 (12)
C1A—C5A	1.408 (10)	C1B—C2B	1.393 (18)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.390 (17)	C3B—C4B	1.350 (17)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.378 (10)	C4B—C5B	1.393 (12)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.467 (8)	C5B—C6B	1.456 (11)
C6A—C7A	1.337 (8)	C6B—C7B	1.342 (10)
C6A—H6AA	0.93	C6B—H6BA	0.93
C7A—C8A	1.460 (9)	C7B—C8B	1.465 (11)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.386 (10)	C8B—C9B	1.404 (12)
C8A—C17A	1.442 (10)	C8B—C17B	1.432 (12)
C9A—C10A	1.429 (15)	C9B—C10B	1.397 (19)
C9A—H9AA	0.93	C9B—H9BA	0.93
C10A—C11A	1.417 (16)	C10B—C11B	1.385 (19)
C10A—C15A	1.51 (2)	C10B—C15B	1.41 (2)
C11A—C12A	1.360 (11)	C11B—C12B	1.378 (15)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.416 (17)	C12B—C13B	1.424 (17)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.38 (3)	C13B—C14B	1.40 (2)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—C15A	1.43 (2)	C14B—C15B	1.435 (15)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—C16A	1.23 (2)	C15B—C16B	1.52 (2)
C16A—C17A	1.372 (18)	C16B—C17B	1.313 (19)
C16A—H16A	0.93	C16B—H16B	0.93
C17A—H17A	0.93	C17B—H17B	0.93
C18A—H18A	0.96	C18B—H18G	0.96
C18A—H18B	0.96	C18B—H18D	0.96
C18A—H18C	0.96	C18B—H18E	0.96
C3A—N1A—C2A	117 (3)	C5B—C1B—C2B	118.5 (10)
C3A—N1A—C18A	123 (3)	C5B—C1B—H1BA	120.7
C2A—N1A—C18A	119 (2)	C2B—C1B—H1BA	120.7
C2A—C1A—C5A	122.2 (7)	N1B—C2B—C1B	123 (2)
C2A—C1A—H1AA	118.9	N1B—C2B—H2BA	118.7
C5A—C1A—H1AA	118.9	C1B—C2B—H2BA	118.7
C1A—C2A—N1A	120.9 (15)	C4B—C3B—N1B	120 (2)
C1A—C2A—H2AA	119.5	C4B—C3B—H3BA	120.2
N1A—C2A—H2AA	119.5	N1B—C3B—H3BA	120.2
N1A—C3A—C4A	123 (2)	C3B—C4B—C5B	122.4 (9)
N1A—C3A—H3AA	118.4	C3B—C4B—H4BA	118.8
C4A—C3A—H3AA	118.4	C5B—C4B—H4BA	118.8
C5A—C4A—C3A	120.0 (9)	C1B—C5B—C4B	116.6 (8)
C5A—C4A—H4AA	120.0	C1B—C5B—C6B	124.0 (8)
C3A—C4A—H4AA	120.0	C4B—C5B—C6B	119.5 (8)
C4A—C5A—C1A	116.0 (6)	C7B—C6B—C5B	127.8 (7)
C4A—C5A—C6A	123.9 (7)	C7B—C6B—H6BA	116.1
C1A—C5A—C6A	120.0 (7)	C5B—C6B—H6BA	116.1
C7A—C6A—C5A	123.4 (6)	C6B—C7B—C8B	124.5 (7)
C7A—C6A—H6AA	118.3	C6B—C7B—H7BA	117.8
C5A—C6A—H6AA	118.3	C8B—C7B—H7BA	117.8
C6A—C7A—C8A	127.9 (6)	C9B—C8B—C17B	118.4 (8)
C6A—C7A—H7AA	116.1	C9B—C8B—C7B	121.3 (8)
C8A—C7A—H7AA	116.1	C17B—C8B—C7B	120.3 (9)
C9A—C8A—C17A	120.8 (6)	C10B—C9B—C8B	121.8 (11)
C9A—C8A—C7A	117.2 (7)	C10B—C9B—H9BA	119.1
C17A—C8A—C7A	122.0 (7)	C8B—C9B—H9BA	119.1
C8A—C9A—C10A	118.7 (10)	C11B—C10B—C9B	123.3 (17)
C8A—C9A—H9AA	120.6	C11B—C10B—C15B	114.6 (13)
C10A—C9A—H9AA	120.6	C9B—C10B—C15B	121.6 (13)
C11A—C10A—C9A	119.1 (14)	C12B—C11B—C10B	121.5 (13)
C11A—C10A—C15A	125.2 (12)	C12B—C11B—H11B	119.3
C9A—C10A—C15A	115.3 (11)	C10B—C11B—H11B	119.3
C12A—C11A—C10A	121.0 (12)	C11B—C12B—C13B	120.7 (13)
C12A—C11A—H11A	119.5	C11B—C12B—H12B	119.7
C10A—C11A—H11A	119.5	C13B—C12B—H12B	119.7
C11A—C12A—C13A	119.0 (13)	C14B—C13B—C12B	123.1 (17)
C11A—C12A—H12A	120.5	C14B—C13B—H13B	118.4
C13A—C12A—H12A	120.5	C12B—C13B—H13B	118.4
C14A—C13A—C12A	117.7 (18)	C13B—C14B—C15B	110.9 (17)
C14A—C13A—H13A	121.1	C13B—C14B—H14B	124.6
C12A—C13A—H13A	121.1	C15B—C14B—H14B	124.6
C13A—C14A—C15A	132 (2)	C10B—C15B—C14B	129.0 (13)
C13A—C14A—H14A	114.2	C10B—C15B—C16B	114.3 (9)
C15A—C14A—H14A	114.2	C14B—C15B—C16B	116.6 (12)
C16A—C15A—C14A	131.7 (17)	C17B—C16B—C15B	122.9 (12)
C16A—C15A—C10A	123.1 (14)	C17B—C16B—H16B	118.5
C14A—C15A—C10A	105.1 (14)	C15B—C16B—H16B	118.5
C15A—C16A—C17A	123.3 (14)	C16B—C17B—C8B	120.8 (11)
C15A—C16A—H16A	118.4	C16B—C17B—H17B	119.6
C17A—C16A—H16A	118.4	C8B—C17B—H17B	119.6
C16A—C17A—C8A	118.6 (10)	N1B—C18B—H18G	109.5
C16A—C17A—H17A	120.7	N1B—C18B—H18D	109.5
C8A—C17A—H17A	120.7	H18G—C18B—H18D	109.5
C2B—N1B—C3B	120 (3)	N1B—C18B—H18E	109.5
C2B—N1B—C18B	123 (3)	H18G—C18B—H18E	109.5
C3B—N1B—C18B	116 (4)	H18D—C18B—H18E	109.5
C5A—C1A—C2A—N1A	6(2)	C3B—N1B—C2B—C1B	12 (4)
C3A—N1A—C2A—C1A	−8(3)	C18B—N1B—C2B—C1B	178 (2)
C18A—N1A—C2A—C1A	−177.7 (16)	C5B—C1B—C2B—N1B	−8(3)
C2A—N1A—C3A—C4A	4(3)	C2B—N1B—C3B—C4B	−9(4)
C18A—N1A—C3A—C4A	174.0 (18)	C18B—N1B—C3B—C4B	−176.2 (19)
N1A—C3A—C4A—C5A	1(3)	N1B—C3B—C4B—C5B	3(3)
C3A—C4A—C5A—C1A	−3.3 (14)	C2B—C1B—C5B—C4B	2.0 (16)
C3A—C4A—C5A—C6A	176.4 (11)	C2B—C1B—C5B—C6B	−178.1 (12)
C2A—C1A—C5A—C4A	0.1 (13)	C3B—C4B—C5B—C1B	0.3 (17)
C2A—C1A—C5A—C6A	−179.6 (10)	C3B—C4B—C5B—C6B	−179.6 (13)
C4A—C5A—C6A—C7A	−0.4 (10)	C1B—C5B—C6B—C7B	0.7 (13)
C1A—C5A—C6A—C7A	179.2 (6)	C4B—C5B—C6B—C7B	−179.4 (8)
C5A—C6A—C7A—C8A	−179.7 (6)	C5B—C6B—C7B—C8B	179.0 (7)
C6A—C7A—C8A—C9A	−178.5 (6)	C6B—C7B—C8B—C9B	1.5 (12)
C6A—C7A—C8A—C17A	2.1 (10)	C6B—C7B—C8B—C17B	179.9 (8)
C17A—C8A—C9A—C10A	2.7 (14)	C17B—C8B—C9B—C10B	−1.0 (18)
C7A—C8A—C9A—C10A	−176.7 (12)	C7B—C8B—C9B—C10B	177.5 (14)
C8A—C9A—C10A—C11A	−177.1 (13)	C8B—C9B—C10B—C11B	175.4 (16)
C8A—C9A—C10A—C15A	−4(2)	C8B—C9B—C10B—C15B	4(3)
C9A—C10A—C11A—C12A	179.0 (13)	C9B—C10B—C11B—C12B	−175.2 (17)
C15A—C10A—C11A—C12A	6(3)	C15B—C10B—C11B—C12B	−3(3)
C10A—C11A—C12A—C13A	−4(2)	C10B—C11B—C12B—C13B	1(3)
C11A—C12A—C13A—C14A	2(4)	C11B—C12B—C13B—C14B	−1(4)
C12A—C13A—C14A—C15A	−2(5)	C12B—C13B—C14B—C15B	2(4)
C13A—C14A—C15A—C16A	−178 (3)	C11B—C10B—C15B—C14B	6(3)
C13A—C14A—C15A—C10A	4(4)	C9B—C10B—C15B—C14B	178 (2)
C11A—C10A—C15A—C16A	176.1 (17)	C11B—C10B—C15B—C16B	−177.2 (17)
C9A—C10A—C15A—C16A	3(2)	C9B—C10B—C15B—C16B	−5(3)
C11A—C10A—C15A—C14A	−6(3)	C13B—C14B—C15B—C10B	−5(4)
C9A—C10A—C15A—C14A	−178.7 (19)	C13B—C14B—C15B—C16B	178 (2)
C14A—C15A—C16A—C17A	−179 (2)	C10B—C15B—C16B—C17B	4(2)
C10A—C15A—C16A—C17A	−1(2)	C14B—C15B—C16B—C17B	−178 (2)
C15A—C16A—C17A—C8A	0(2)	C15B—C16B—C17B—C8B	−1(2)
C9A—C8A—C17A—C16A	−0.9 (13)	C9B—C8B—C17B—C16B	−0.2 (16)
C7A—C8A—C17A—C16A	178.5 (10)	C7B—C8B—C17B—C16B	−178.7 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C18A—H18A···I1i	0.96	3.05	3.928 (17)	152
C18A—H18B···Cg1i	0.96	2.63	3.513 (18)	153
C18A—H18B···Cg2i	0.96	2.65	3.517 (18)	150
C18B—H18E···Cg1i	0.96	2.62	3.44 (2)	143
C18B—H18E···Cg2i	0.96	2.66	3.45 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18A—H18A⋯I1i	0.96	3.05	3.928 (17)	152
C18A—H18B⋯Cg1i	0.96	2.63	3.513 (18)	153
C18A—H18B⋯Cg2i	0.96	2.65	3.517 (18)	150
C18B—H18E⋯Cg1i	0.96	2.62	3.44 (2)	143
C18B—H18E⋯Cg2i	0.96	2.66	3.45 (2)	139

Symmetry code: (i) . Cg1 and Cg2 are centroids of the C10A–C15A and C10B–C15B rings, respectively.