1-Methyl-4-[(1E,3E)-4-phenyl-buta-1,3-dien-yl]pyridinium iodide monohydrate.

The asymmetric unit of the title compound, C(16)H(16)N(+)·I(-)·H(2)O, contains two 1-methyl-4-{[(1E,3E)-4-phenyl-buta-1,3-dien-yl]}pyridinium cations, two iodide ions and two solvent water mol-ecules. The cation is twisted slightly, the dihedral angle between the pyridinium and the phenyl rings being 10.68 (18)° in one mol-ecule and 18.9 (3)° in the other. The two water mol-ecules are disordered over three positions with site-occupancy ratio of 0.9/0.7/0.4. In the crystal packing, the cations are arranged into ribbons along the b axis with the iodide ions and water mol-ecules located between adjacent cations. The cations are linked to the iodide ions and water mol-ecules by weak C-H⋯I and C-H⋯O inter-actions, respectively. These inter-actions together with O-H⋯I hydrogen bonds link the mol-ecules into a two-dimensional network parallel to the bc plane. π⋯π inter-actions with a centroid-centroid distance of 3.669 (2) Å are also observed.

Related literature

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

Experimental

Crystal data

C16H16N+·I−·H2O

M = 367.21

Monoclinic,

a = 32.5600 (6) Å

b = 12.6414 (2) Å

c = 16.5602 (3) Å

β = 111.180 (1)°

V = 6355.81 (19) Å3

Z = 16

Mo Kα radiation

μ = 2.01 mm−1

T = 100 K

0.55 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.407, T max = 0.694

36570 measured reflections

9279 independent reflections

6818 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.117

S = 1.02

9279 reflections

357 parameters

H-atom parameters constrained

Δρmax = 2.40 e Å−3

Δρmin = −1.87 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/S1600536810006045/sj2731sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006045/sj2731Isup2.hkl

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

C16H16N+·I−·H2O	F(000) = 2912
Mr = 367.21	Dx = 1.535 Mg m−3
Monoclinic, C2/c	Melting point = 496–498 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 32.5600 (6) Å	Cell parameters from 9279 reflections
b = 12.6414 (2) Å	θ = 1.7–30.0°
c = 16.5602 (3) Å	µ = 2.01 mm−1
β = 111.180 (1)°	T = 100 K
V = 6355.81 (19) Å3	Block, yellow
Z = 16	0.55 × 0.20 × 0.20 mm

Bruker APEXII CCD area detector diffractometer	9279 independent reflections
Radiation source: sealed tube	6818 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −39→45
Tmin = 0.407, Tmax = 0.694	k = −17→17
36570 measured reflections	l = −23→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0415P)2 + 36.1246P] where P = (Fo2 + 2Fc2)/3
9279 reflections	(Δ/σ)max = 0.003
357 parameters	Δρmax = 2.40 e Å−3
0 restraints	Δρmin = −1.87 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)
I1A	0.006481 (8)	0.74812 (2)	0.492960 (16)	0.03922 (8)
I1B	0.825988 (11)	0.71635 (2)	0.18855 (3)	0.06328 (12)
N1A	0.90440 (10)	0.0474 (2)	0.29244 (19)	0.0305 (6)
C1A	0.84641 (12)	0.1693 (3)	0.2688 (2)	0.0302 (7)
H1A	0.8356	0.2302	0.2856	0.036*
C2A	0.88809 (12)	0.1352 (3)	0.3159 (2)	0.0303 (7)
H2A	0.9053	0.1729	0.3646	0.036*
C3A	0.87910 (13)	−0.0101 (3)	0.2239 (2)	0.0368 (8)
H3A	0.8904	−0.0719	0.2094	0.044*
C4A	0.83732 (13)	0.0206 (3)	0.1755 (2)	0.0360 (8)
H4A	0.8204	−0.0206	0.1289	0.043*
C5A	0.81968 (12)	0.1135 (3)	0.1953 (2)	0.0303 (7)
C6A	0.77644 (12)	0.1532 (3)	0.1426 (2)	0.0348 (8)
H6A	0.7662	0.2132	0.1619	0.042*
C7A	0.75006 (13)	0.1094 (3)	0.0677 (3)	0.0378 (8)
H7A	0.7597	0.0476	0.0497	0.045*
C8A	0.70796 (12)	0.1511 (3)	0.0135 (2)	0.0358 (8)
H8A	0.6976	0.2122	0.0310	0.043*
C9A	0.68303 (12)	0.1052 (3)	−0.0615 (2)	0.0340 (7)
H9A	0.6943	0.0438	−0.0765	0.041*
C10A	0.64019 (12)	0.1407 (3)	−0.1220 (2)	0.0311 (7)
C11A	0.62086 (12)	0.0866 (3)	−0.2003 (2)	0.0328 (7)
H11A	0.6352	0.0286	−0.2125	0.039*
C12A	0.58082 (12)	0.1182 (3)	−0.2597 (3)	0.0367 (8)
H12A	0.5686	0.0817	−0.3117	0.044*
C13A	0.55865 (12)	0.2036 (3)	−0.2427 (3)	0.0361 (8)
H13A	0.5318	0.2254	−0.2832	0.043*
C14A	0.57699 (12)	0.2566 (3)	−0.1641 (2)	0.0338 (7)
H14A	0.5618	0.3126	−0.1513	0.041*
C15A	0.61757 (12)	0.2269 (3)	−0.1047 (2)	0.0320 (7)
H15A	0.6299	0.2642	−0.0532	0.038*
C16A	0.95039 (13)	0.0138 (3)	0.3392 (3)	0.0380 (8)
H16A	0.9642	0.0618	0.3861	0.057*
H16B	0.9662	0.0141	0.3002	0.057*
H16C	0.9506	−0.0563	0.3617	0.057*
N1B	0.07132 (13)	0.4780 (3)	−0.0525 (3)	0.0509 (9)
C1B	0.12480 (15)	0.5134 (4)	0.0860 (3)	0.0503 (11)
H1B	0.1340	0.5532	0.1366	0.060*
C2B	0.08526 (15)	0.5343 (4)	0.0221 (3)	0.0490 (11)
H2B	0.0676	0.5881	0.0300	0.059*
C3B	0.09613 (17)	0.4012 (4)	−0.0651 (4)	0.0586 (12)
H3B	0.0864	0.3634	−0.1168	0.070*
C4B	0.13613 (17)	0.3770 (4)	−0.0025 (4)	0.0595 (13)
H4B	0.1531	0.3229	−0.0125	0.071*
C5B	0.15160 (14)	0.4319 (4)	0.0753 (3)	0.0496 (11)
C6B	0.19467 (14)	0.4065 (4)	0.1392 (3)	0.0517 (11)
H6B	0.2101	0.3507	0.1270	0.062*
C7B	0.21354 (13)	0.4573 (4)	0.2139 (3)	0.0488 (11)
H7B	0.1972	0.5097	0.2280	0.059*
C8B	0.25747 (14)	0.4369 (4)	0.2747 (3)	0.0491 (11)
H8B	0.2734	0.3806	0.2646	0.059*
C9B	0.27587 (14)	0.4970 (4)	0.3451 (3)	0.0509 (12)
H9B	0.2578	0.5473	0.3563	0.061*
C10B	0.32147 (15)	0.4919 (4)	0.4064 (3)	0.0519 (12)
C11B	0.35014 (14)	0.4109 (4)	0.4035 (3)	0.0550 (13)
H11B	0.3402	0.3554	0.3644	0.066*
C12B	0.39410 (16)	0.4145 (5)	0.4602 (4)	0.0646 (16)
H12B	0.4134	0.3607	0.4593	0.077*
C13B	0.40872 (18)	0.4975 (5)	0.5174 (4)	0.0699 (17)
H13B	0.4381	0.4997	0.5539	0.084*
C14B	0.3806 (2)	0.5774 (5)	0.5217 (3)	0.0703 (16)
H14B	0.3908	0.6328	0.5609	0.084*
C15B	0.33693 (17)	0.5734 (5)	0.4665 (3)	0.0601 (13)
H15B	0.3176	0.6260	0.4697	0.072*
C16B	0.02813 (16)	0.5012 (4)	−0.1198 (3)	0.0622 (14)
H16D	0.0291	0.4851	−0.1758	0.093*
H16E	0.0213	0.5748	−0.1175	0.093*
H16F	0.0059	0.4589	−0.1100	0.093*
O1W	0.05902 (16)	0.3235 (5)	0.7242 (3)	0.104 (2)	0.90
H1W1	0.0640	0.2698	0.7188	0.156*	0.90
H2W1	0.0761	0.3618	0.7007	0.156*	0.90
O2W	0.4677 (3)	0.6439 (6)	0.6879 (4)	0.103 (2)	0.70
H1W2	0.4610	0.6930	0.7206	0.154*	0.70
H2W2	0.4770	0.6733	0.6557	0.154*	0.70
O3W	0.2541 (4)	0.6530 (9)	0.5171 (7)	0.087 (3)	0.40
H1W3	0.2374	0.6726	0.4678	0.130*	0.40
H2W3	0.2766	0.6895	0.5289	0.130*	0.40

	U11	U22	U33	U12	U13	U23
I1A	0.03478 (13)	0.03914 (14)	0.03595 (13)	0.00447 (10)	0.00338 (9)	−0.00831 (10)
I1B	0.04728 (17)	0.03069 (15)	0.0990 (3)	0.00016 (12)	0.01098 (17)	−0.00940 (15)
N1A	0.0356 (15)	0.0254 (14)	0.0325 (15)	0.0005 (11)	0.0145 (13)	0.0036 (11)
C1A	0.0348 (18)	0.0286 (17)	0.0318 (17)	−0.0008 (13)	0.0177 (14)	−0.0004 (13)
C2A	0.0353 (18)	0.0287 (17)	0.0301 (17)	−0.0033 (13)	0.0157 (14)	−0.0020 (13)
C3A	0.047 (2)	0.0248 (17)	0.0371 (19)	0.0014 (15)	0.0132 (17)	−0.0033 (14)
C4A	0.044 (2)	0.0291 (18)	0.0315 (18)	−0.0033 (15)	0.0096 (16)	−0.0054 (14)
C5A	0.0333 (17)	0.0289 (17)	0.0303 (16)	−0.0024 (13)	0.0134 (14)	0.0044 (13)
C6A	0.0359 (19)	0.0325 (18)	0.0377 (19)	−0.0001 (14)	0.0152 (16)	0.0025 (14)
C7A	0.039 (2)	0.0339 (19)	0.041 (2)	0.0024 (15)	0.0151 (17)	0.0042 (15)
C8A	0.0372 (19)	0.0327 (18)	0.0389 (19)	0.0021 (15)	0.0154 (16)	0.0020 (15)
C9A	0.0367 (19)	0.0281 (17)	0.0390 (19)	0.0029 (14)	0.0160 (16)	0.0028 (14)
C10A	0.0334 (17)	0.0278 (17)	0.0329 (17)	0.0009 (13)	0.0131 (14)	0.0032 (13)
C11A	0.0372 (18)	0.0230 (16)	0.0405 (19)	−0.0008 (13)	0.0170 (16)	−0.0024 (13)
C12A	0.0357 (19)	0.0347 (19)	0.040 (2)	−0.0062 (15)	0.0138 (16)	−0.0064 (15)
C13A	0.0297 (17)	0.037 (2)	0.042 (2)	−0.0003 (14)	0.0136 (15)	0.0001 (15)
C14A	0.0335 (17)	0.0332 (18)	0.0379 (18)	0.0049 (14)	0.0166 (15)	−0.0010 (15)
C15A	0.0348 (18)	0.0308 (18)	0.0323 (17)	0.0005 (13)	0.0143 (15)	−0.0030 (13)
C16A	0.040 (2)	0.0333 (19)	0.038 (2)	0.0058 (15)	0.0110 (16)	0.0007 (15)
N1B	0.046 (2)	0.044 (2)	0.062 (2)	−0.0065 (16)	0.0187 (19)	0.0218 (18)
C1B	0.046 (2)	0.048 (3)	0.057 (3)	0.0014 (19)	0.019 (2)	0.020 (2)
C2B	0.046 (2)	0.044 (2)	0.061 (3)	0.0042 (19)	0.025 (2)	0.022 (2)
C3B	0.056 (3)	0.053 (3)	0.070 (3)	−0.011 (2)	0.027 (3)	0.002 (2)
C4B	0.050 (3)	0.055 (3)	0.082 (4)	−0.001 (2)	0.033 (3)	0.007 (3)
C5B	0.040 (2)	0.045 (2)	0.069 (3)	−0.0013 (18)	0.025 (2)	0.020 (2)
C6B	0.039 (2)	0.045 (2)	0.077 (3)	0.0034 (18)	0.027 (2)	0.017 (2)
C7B	0.034 (2)	0.047 (2)	0.073 (3)	0.0072 (18)	0.028 (2)	0.026 (2)
C8B	0.038 (2)	0.049 (3)	0.068 (3)	0.0052 (18)	0.027 (2)	0.024 (2)
C9B	0.037 (2)	0.060 (3)	0.066 (3)	0.0106 (19)	0.031 (2)	0.026 (2)
C10B	0.038 (2)	0.067 (3)	0.057 (3)	0.006 (2)	0.025 (2)	0.031 (2)
C11B	0.041 (2)	0.064 (3)	0.066 (3)	0.009 (2)	0.026 (2)	0.037 (2)
C12B	0.045 (3)	0.074 (4)	0.083 (4)	0.011 (2)	0.032 (3)	0.050 (3)
C13B	0.050 (3)	0.096 (5)	0.059 (3)	−0.005 (3)	0.013 (2)	0.043 (3)
C14B	0.071 (4)	0.097 (5)	0.047 (3)	0.002 (3)	0.026 (3)	0.024 (3)
C15B	0.057 (3)	0.083 (4)	0.051 (3)	0.008 (3)	0.033 (2)	0.021 (3)
C16B	0.052 (3)	0.059 (3)	0.065 (3)	−0.009 (2)	0.009 (2)	0.027 (2)
O1W	0.062 (3)	0.163 (6)	0.068 (3)	0.025 (3)	0.000 (2)	−0.037 (3)
O2W	0.143 (7)	0.107 (5)	0.084 (4)	−0.027 (5)	0.073 (5)	−0.010 (4)
O3W	0.109 (9)	0.064 (6)	0.071 (7)	0.016 (6)	0.014 (6)	−0.001 (5)

N1A—C2A	1.346 (4)	C1B—C2B	1.364 (6)
N1A—C3A	1.349 (5)	C1B—C5B	1.402 (7)
N1A—C16A	1.478 (5)	C1B—H1B	0.9300
C1A—C2A	1.368 (5)	C2B—H2B	0.9300
C1A—C5A	1.403 (5)	C3B—C4B	1.374 (7)
C1A—H1A	0.9300	C3B—H3B	0.9300
C2A—H2A	0.9300	C4B—C5B	1.388 (7)
C3A—C4A	1.362 (5)	C4B—H4B	0.9300
C3A—H3A	0.9300	C5B—C6B	1.456 (6)
C4A—C5A	1.397 (5)	C6B—C7B	1.330 (7)
C4A—H4A	0.9300	C6B—H6B	0.9300
C5A—C6A	1.452 (5)	C7B—C8B	1.444 (6)
C6A—C7A	1.347 (5)	C7B—H7B	0.9300
C6A—H6A	0.9300	C8B—C9B	1.338 (7)
C7A—C8A	1.440 (5)	C8B—H8B	0.9300
C7A—H7A	0.9300	C9B—C10B	1.466 (6)
C8A—C9A	1.345 (5)	C9B—H9B	0.9300
C8A—H8A	0.9300	C10B—C15B	1.394 (8)
C9A—C10A	1.464 (5)	C10B—C11B	1.399 (7)
C9A—H9A	0.9300	C11B—C12B	1.401 (7)
C10A—C11A	1.398 (5)	C11B—H11B	0.9300
C10A—C15A	1.401 (5)	C12B—C13B	1.378 (9)
C11A—C12A	1.378 (5)	C12B—H12B	0.9300
C11A—H11A	0.9300	C13B—C14B	1.382 (9)
C12A—C13A	1.384 (5)	C13B—H13B	0.9300
C12A—H12A	0.9300	C14B—C15B	1.387 (8)
C13A—C14A	1.392 (5)	C14B—H14B	0.9300
C13A—H13A	0.9300	C15B—H15B	0.9300
C14A—C15A	1.384 (5)	C16B—H16D	0.9600
C14A—H14A	0.9300	C16B—H16E	0.9600
C15A—H15A	0.9300	C16B—H16F	0.9600
C16A—H16A	0.9600	O1W—H1W1	0.7106
C16A—H16B	0.9600	O1W—H2W1	0.9232
C16A—H16C	0.9600	O2W—H1W2	0.8994
N1B—C3B	1.326 (6)	O2W—H2W2	0.7950
N1B—C2B	1.355 (6)	O3W—H1W3	0.8376
N1B—C16B	1.474 (6)	O3W—H2W3	0.8268
C2A—N1A—C3A	120.2 (3)	C2B—N1B—C16B	119.9 (4)
C2A—N1A—C16A	121.1 (3)	C2B—C1B—C5B	120.0 (5)
C3A—N1A—C16A	118.7 (3)	C2B—C1B—H1B	120.0
C2A—C1A—C5A	120.9 (3)	C5B—C1B—H1B	120.0
C2A—C1A—H1A	119.6	N1B—C2B—C1B	121.1 (5)
C5A—C1A—H1A	119.6	N1B—C2B—H2B	119.5
N1A—C2A—C1A	120.5 (3)	C1B—C2B—H2B	119.5
N1A—C2A—H2A	119.7	N1B—C3B—C4B	120.7 (5)
C1A—C2A—H2A	119.7	N1B—C3B—H3B	119.7
N1A—C3A—C4A	121.1 (3)	C4B—C3B—H3B	119.7
N1A—C3A—H3A	119.4	C3B—C4B—C5B	121.0 (5)
C4A—C3A—H3A	119.4	C3B—C4B—H4B	119.5
C3A—C4A—C5A	120.6 (3)	C5B—C4B—H4B	119.5
C3A—C4A—H4A	119.7	C4B—C5B—C1B	116.8 (4)
C5A—C4A—H4A	119.7	C4B—C5B—C6B	119.7 (5)
C4A—C5A—C1A	116.5 (3)	C1B—C5B—C6B	123.4 (5)
C4A—C5A—C6A	122.8 (3)	C7B—C6B—C5B	124.7 (5)
C1A—C5A—C6A	120.7 (3)	C7B—C6B—H6B	117.6
C7A—C6A—C5A	124.6 (4)	C5B—C6B—H6B	117.6
C7A—C6A—H6A	117.7	C6B—C7B—C8B	124.8 (5)
C5A—C6A—H6A	117.7	C6B—C7B—H7B	117.6
C6A—C7A—C8A	124.7 (4)	C8B—C7B—H7B	117.6
C6A—C7A—H7A	117.6	C9B—C8B—C7B	121.7 (5)
C8A—C7A—H7A	117.6	C9B—C8B—H8B	119.1
C9A—C8A—C7A	122.6 (4)	C7B—C8B—H8B	119.1
C9A—C8A—H8A	118.7	C8B—C9B—C10B	127.0 (5)
C7A—C8A—H8A	118.7	C8B—C9B—H9B	116.5
C8A—C9A—C10A	127.4 (3)	C10B—C9B—H9B	116.5
C8A—C9A—H9A	116.3	C15B—C10B—C11B	119.5 (5)
C10A—C9A—H9A	116.3	C15B—C10B—C9B	118.5 (5)
C11A—C10A—C15A	118.4 (3)	C11B—C10B—C9B	122.0 (5)
C11A—C10A—C9A	118.9 (3)	C10B—C11B—C12B	119.1 (6)
C15A—C10A—C9A	122.7 (3)	C10B—C11B—H11B	120.5
C12A—C11A—C10A	120.9 (3)	C12B—C11B—H11B	120.5
C12A—C11A—H11A	119.6	C13B—C12B—C11B	120.1 (5)
C10A—C11A—H11A	119.6	C13B—C12B—H12B	120.0
C11A—C12A—C13A	120.6 (4)	C11B—C12B—H12B	120.0
C11A—C12A—H12A	119.7	C12B—C13B—C14B	121.4 (5)
C13A—C12A—H12A	119.7	C12B—C13B—H13B	119.3
C12A—C13A—C14A	119.2 (4)	C14B—C13B—H13B	119.3
C12A—C13A—H13A	120.4	C13B—C14B—C15B	118.7 (6)
C14A—C13A—H13A	120.4	C13B—C14B—H14B	120.7
C15A—C14A—C13A	120.7 (3)	C15B—C14B—H14B	120.7
C15A—C14A—H14A	119.7	C14B—C15B—C10B	121.2 (5)
C13A—C14A—H14A	119.7	C14B—C15B—H15B	119.4
C14A—C15A—C10A	120.2 (3)	C10B—C15B—H15B	119.4
C14A—C15A—H15A	119.9	N1B—C16B—H16D	109.5
C10A—C15A—H15A	119.9	N1B—C16B—H16E	109.5
N1A—C16A—H16A	109.5	H16D—C16B—H16E	109.5
N1A—C16A—H16B	109.5	N1B—C16B—H16F	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16F	109.5
N1A—C16A—H16C	109.5	H16E—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H1W1—O1W—H2W1	104.4
H16B—C16A—H16C	109.5	H1W2—O2W—H2W2	108.4
C3B—N1B—C2B	120.4 (4)	H1W3—O3W—H2W3	105.9
C3B—N1B—C16B	119.7 (5)
C3A—N1A—C2A—C1A	−2.6 (5)	C3B—N1B—C2B—C1B	−0.3 (6)
C16A—N1A—C2A—C1A	175.8 (3)	C16B—N1B—C2B—C1B	179.0 (4)
C5A—C1A—C2A—N1A	0.3 (5)	C5B—C1B—C2B—N1B	−0.5 (6)
C2A—N1A—C3A—C4A	2.1 (5)	C2B—N1B—C3B—C4B	0.5 (7)
C16A—N1A—C3A—C4A	−176.2 (4)	C16B—N1B—C3B—C4B	−178.8 (4)
N1A—C3A—C4A—C5A	0.6 (6)	N1B—C3B—C4B—C5B	0.0 (7)
C3A—C4A—C5A—C1A	−2.7 (5)	C3B—C4B—C5B—C1B	−0.8 (7)
C3A—C4A—C5A—C6A	176.0 (4)	C3B—C4B—C5B—C6B	−178.2 (4)
C2A—C1A—C5A—C4A	2.3 (5)	C2B—C1B—C5B—C4B	1.0 (6)
C2A—C1A—C5A—C6A	−176.4 (3)	C2B—C1B—C5B—C6B	178.3 (4)
C4A—C5A—C6A—C7A	−3.9 (6)	C4B—C5B—C6B—C7B	176.7 (4)
C1A—C5A—C6A—C7A	174.8 (4)	C1B—C5B—C6B—C7B	−0.6 (7)
C5A—C6A—C7A—C8A	−177.3 (3)	C5B—C6B—C7B—C8B	−175.5 (4)
C6A—C7A—C8A—C9A	179.1 (4)	C6B—C7B—C8B—C9B	174.2 (4)
C7A—C8A—C9A—C10A	−179.3 (4)	C7B—C8B—C9B—C10B	−173.0 (4)
C8A—C9A—C10A—C11A	175.0 (4)	C8B—C9B—C10B—C15B	168.2 (4)
C8A—C9A—C10A—C15A	−5.1 (6)	C8B—C9B—C10B—C11B	−8.8 (7)
C15A—C10A—C11A—C12A	1.0 (5)	C15B—C10B—C11B—C12B	−1.1 (6)
C9A—C10A—C11A—C12A	−179.2 (3)	C9B—C10B—C11B—C12B	175.8 (4)
C10A—C11A—C12A—C13A	−0.7 (6)	C10B—C11B—C12B—C13B	−0.6 (6)
C11A—C12A—C13A—C14A	−0.9 (6)	C11B—C12B—C13B—C14B	1.4 (7)
C12A—C13A—C14A—C15A	2.2 (6)	C12B—C13B—C14B—C15B	−0.4 (7)
C13A—C14A—C15A—C10A	−1.9 (6)	C13B—C14B—C15B—C10B	−1.3 (7)
C11A—C10A—C15A—C14A	0.3 (5)	C11B—C10B—C15B—C14B	2.1 (6)
C9A—C10A—C15A—C14A	−179.5 (3)	C9B—C10B—C15B—C14B	−175.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2W2···I1Ai	0.79	2.88	3.655 (8)	166
C3B—H3B···O1Wii	0.93	2.51	3.399 (8)	161
C16A—H16A···I1Aiii	0.96	3.05	3.992 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2W2⋯I1Ai	0.79	2.88	3.655 (8)	166
C3B—H3B⋯O1Wii	0.93	2.51	3.399 (8)	161
C16A—H16A⋯I1Aiii	0.96	3.05	3.992 (4)	167

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