(E)-2-[4-(Diethyl-amino)-styr-yl]-1-ethyl-pyridinium iodide monohydrate.

In the title hydrated salt, C19H25N2(+)·I(-)·H2O, the 4-(diethyl-amino)-phenyl unit of the cation is disordered over two positions in a 0.847 (3):0.153 (3) ratio. The cation is twisted, with dihedral angles between the pyridinium and benzene rings of 11.25 (13) and 10.7 (8)° for the major and minor components, respectively. In the crystal, the three components are linked into a centrosymmetric 2:2:2 unit by O-H⋯I and C-H⋯O hydrogen bonds. π-π inter-actions with centroid-centroid distances of 3.5065 (7)-3.790 (9) Å are also present.

Related literature

For background to and applications of amino­styrylpyridinium compounds, see: Chanawanno et al. (2010 ▶); Larnbert et al. (1996 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶); Kaewmanee et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H25N2 +·I−·H2O

M = 426.33

Triclinic,

a = 7.9969 (1) Å

b = 9.1336 (1) Å

c = 14.7740 (2) Å

α = 96.220 (1)°

β = 105.430 (1)°

γ = 105.060 (1)°

V = 986.05 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.63 mm−1

T = 100 K

0.26 × 0.23 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.677, T max = 0.816

32289 measured reflections

8664 independent reflections

7821 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.055

S = 1.08

8664 reflections

254 parameters

20 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.99 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300528X/is5238sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300528X/is5238Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300528X/is5238Isup3.cml

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

C19H25N2+·I−·H2O	Z = 2
Mr = 426.33	F(000) = 432
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Melting point = 466–468 K
a = 7.9969 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1336 (1) Å	Cell parameters from 8664 reflections
c = 14.7740 (2) Å	θ = 1.5–35.2°
α = 96.220 (1)°	µ = 1.63 mm−1
β = 105.430 (1)°	T = 100 K
γ = 105.060 (1)°	Block, orange
V = 986.05 (2) Å3	0.26 × 0.23 × 0.13 mm

Bruker SMART APEXII CCD area-detector diffractometer	8664 independent reflections
Radiation source: fine-focus sealed tube	7821 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm-1	θmax = 35.2°, θmin = 1.5°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.677, Tmax = 0.816	l = −23→23
32289 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0222P)2 + 0.355P] where P = (Fo2 + 2Fc2)/3
8664 reflections	(Δ/σ)max = 0.002
254 parameters	Δρmax = 0.78 e Å−3
20 restraints	Δρmin = −0.99 e Å−3

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.748096 (12)	0.409068 (8)	0.331067 (6)	0.02160 (3)
O1W	0.11907 (16)	0.28996 (13)	0.46705 (9)	0.0284 (2)
H1W	0.155 (3)	0.359 (3)	0.5168 (17)	0.043*
H2W	0.029 (3)	0.310 (3)	0.4293 (17)	0.043*
N1	0.35581 (14)	0.74599 (11)	0.39233 (7)	0.01566 (17)
C1	0.22228 (17)	0.76646 (14)	0.42876 (9)	0.0186 (2)
H1A	0.1520	0.6823	0.4484	0.022*
C2	0.18657 (17)	0.90514 (14)	0.43787 (9)	0.0197 (2)
H2A	0.0926	0.9176	0.4632	0.024*
C3	0.29171 (17)	1.02765 (14)	0.40898 (9)	0.0191 (2)
H3A	0.2723	1.1260	0.4160	0.023*
C4	0.42409 (17)	1.00497 (13)	0.37018 (9)	0.0175 (2)
H4A	0.4942	1.0884	0.3498	0.021*
C5	0.45769 (16)	0.86130 (12)	0.36008 (8)	0.01505 (19)
C6	0.59165 (16)	0.83175 (13)	0.31664 (9)	0.0161 (2)
H6A	0.5979	0.7292	0.3053	0.019*
C7	0.70797 (16)	0.94503 (13)	0.29176 (8)	0.01576 (19)
H7A	0.7022	1.0469	0.3076	0.019*
C8	0.83991 (16)	0.92867 (12)	0.24387 (8)	0.01542 (19)
C14	0.38311 (18)	0.59060 (13)	0.38875 (10)	0.0191 (2)
H14A	0.3470	0.5438	0.4407	0.023*
H14B	0.5137	0.6016	0.3994	0.023*
C15	0.2723 (2)	0.48452 (15)	0.29321 (11)	0.0260 (3)
H15A	0.2873	0.3816	0.2947	0.039*
H15B	0.3145	0.5264	0.2421	0.039*
H15C	0.1435	0.4771	0.2812	0.039*
N2A	1.2553 (2)	0.91163 (15)	0.11947 (12)	0.0199 (3)	0.847 (3)
C9A	0.9548 (3)	1.0628 (4)	0.22893 (14)	0.0158 (4)	0.847 (3)
H9A	0.9404	1.1600	0.2487	0.019*	0.847 (3)
C10A	1.0880 (2)	1.0578 (2)	0.18638 (12)	0.0167 (3)	0.847 (3)
H10A	1.1620	1.1511	0.1770	0.020*	0.847 (3)
C11A	1.1162 (2)	0.9159 (2)	0.15659 (11)	0.0162 (3)	0.847 (3)
C12A	0.9984 (7)	0.7803 (5)	0.1698 (5)	0.0183 (9)	0.847 (3)
H12A	1.0092	0.6826	0.1477	0.022*	0.847 (3)
C13A	0.8679 (6)	0.7869 (6)	0.2142 (4)	0.0168 (7)	0.847 (3)
H13A	0.7954	0.6941	0.2249	0.020*	0.847 (3)
C16A	1.3859 (2)	1.05464 (18)	0.11576 (11)	0.0219 (3)	0.847 (3)
H16A	1.4992	1.0323	0.1127	0.026*	0.847 (3)
H16B	1.4162	1.1291	0.1759	0.026*	0.847 (3)
C17A	1.3210 (3)	1.1305 (2)	0.03204 (13)	0.0289 (4)	0.847 (3)
H17A	1.4122	1.2292	0.0378	0.043*	0.847 (3)
H17B	1.2056	1.1488	0.0324	0.043*	0.847 (3)
H17C	1.3031	1.0625	−0.0280	0.043*	0.847 (3)
C18A	1.2781 (3)	0.7663 (2)	0.08186 (18)	0.0221 (4)	0.847 (3)
H18A	1.2523	0.6923	0.1243	0.027*	0.847 (3)
H18B	1.4067	0.7846	0.0838	0.027*	0.847 (3)
C19A	1.1561 (5)	0.6927 (4)	−0.02058 (19)	0.0335 (5)	0.847 (3)
H19A	1.1788	0.5957	−0.0405	0.050*	0.847 (3)
H19B	1.1832	0.7635	−0.0637	0.050*	0.847 (3)
H19C	1.0282	0.6718	−0.0231	0.050*	0.847 (3)
N2B	1.1981 (11)	0.9042 (8)	0.0815 (6)	0.016*	0.153 (3)
C9B	0.932 (2)	1.059 (2)	0.2133 (12)	0.016*	0.153 (3)
H9B	0.9092	1.1547	0.2278	0.019*	0.153 (3)
C10B	1.0539 (16)	1.0528 (13)	0.1633 (8)	0.016*	0.153 (3)
H10B	1.1190	1.1446	0.1479	0.019*	0.153 (3)
C11B	1.0830 (16)	0.9109 (13)	0.1347 (8)	0.016*	0.153 (3)
C12B	0.982 (5)	0.779 (3)	0.161 (3)	0.016*	0.153 (3)
H12B	1.0049	0.6830	0.1481	0.019*	0.153 (3)
C13B	0.851 (4)	0.788 (4)	0.204 (2)	0.016*	0.153 (3)
H13B	0.7665	0.6950	0.2076	0.019*	0.153 (3)
C16B	1.2738 (12)	1.0334 (9)	0.0393 (6)	0.0224 (18)*	0.153 (3)
H16C	1.1818	1.0880	0.0200	0.027*	0.153 (3)
H16D	1.2972	0.9918	−0.0192	0.027*	0.153 (3)
C17B	1.4473 (13)	1.1485 (11)	0.1044 (7)	0.028 (2)*	0.153 (3)
H37D	1.4800	1.2380	0.0745	0.042*	0.153 (3)
H37E	1.5451	1.1002	0.1156	0.042*	0.153 (3)
H37F	1.4297	1.1822	0.1656	0.042*	0.153 (3)
C18B	1.246 (2)	0.7623 (14)	0.0573 (9)	0.024 (3)*	0.153 (3)
H18C	1.2383	0.7014	0.1084	0.029*	0.153 (3)
H18D	1.3733	0.7919	0.0565	0.029*	0.153 (3)
C19B	1.129 (4)	0.662 (3)	−0.0358 (16)	0.068 (9)*	0.153 (3)
H39D	1.1699	0.5718	−0.0466	0.102*	0.153 (3)
H39E	1.1363	0.7206	−0.0873	0.102*	0.153 (3)
H39F	1.0023	0.6287	−0.0351	0.102*	0.153 (3)

	U11	U22	U33	U12	U13	U23
I1	0.02157 (4)	0.01510 (3)	0.03178 (5)	0.00740 (3)	0.01155 (3)	0.00642 (3)
O1W	0.0277 (5)	0.0287 (5)	0.0332 (6)	0.0139 (4)	0.0125 (5)	0.0033 (4)
N1	0.0139 (4)	0.0150 (4)	0.0190 (4)	0.0045 (3)	0.0065 (4)	0.0034 (3)
C1	0.0151 (5)	0.0207 (5)	0.0214 (5)	0.0051 (4)	0.0082 (4)	0.0039 (4)
C2	0.0163 (5)	0.0230 (5)	0.0211 (5)	0.0078 (4)	0.0072 (4)	0.0016 (4)
C3	0.0195 (5)	0.0194 (5)	0.0196 (5)	0.0093 (4)	0.0055 (4)	0.0019 (4)
C4	0.0189 (5)	0.0148 (4)	0.0200 (5)	0.0061 (4)	0.0070 (4)	0.0030 (4)
C5	0.0144 (5)	0.0140 (4)	0.0170 (5)	0.0039 (3)	0.0056 (4)	0.0028 (3)
C6	0.0165 (5)	0.0146 (4)	0.0193 (5)	0.0050 (4)	0.0084 (4)	0.0035 (4)
C7	0.0161 (5)	0.0146 (4)	0.0179 (5)	0.0049 (4)	0.0069 (4)	0.0035 (4)
C8	0.0165 (5)	0.0141 (4)	0.0168 (5)	0.0044 (4)	0.0070 (4)	0.0036 (4)
C14	0.0192 (5)	0.0148 (4)	0.0275 (6)	0.0064 (4)	0.0114 (5)	0.0077 (4)
C15	0.0231 (6)	0.0165 (5)	0.0362 (7)	0.0032 (4)	0.0100 (6)	0.0000 (5)
N2A	0.0189 (6)	0.0213 (5)	0.0225 (7)	0.0066 (5)	0.0114 (6)	0.0030 (5)
C9A	0.0178 (10)	0.0138 (5)	0.0158 (10)	0.0042 (7)	0.0062 (8)	0.0022 (8)
C10A	0.0172 (8)	0.0160 (5)	0.0169 (8)	0.0030 (5)	0.0071 (6)	0.0025 (6)
C11A	0.0161 (8)	0.0184 (5)	0.0150 (7)	0.0057 (6)	0.0061 (6)	0.0026 (6)
C12A	0.0204 (17)	0.0155 (5)	0.021 (2)	0.0068 (7)	0.0088 (17)	0.0031 (7)
C13A	0.0179 (13)	0.0137 (5)	0.0203 (17)	0.0051 (7)	0.0076 (13)	0.0045 (8)
C16A	0.0166 (7)	0.0262 (7)	0.0224 (7)	0.0040 (5)	0.0082 (5)	0.0035 (5)
C17A	0.0342 (9)	0.0323 (8)	0.0247 (8)	0.0097 (7)	0.0151 (7)	0.0087 (6)
C18A	0.0256 (10)	0.0258 (8)	0.0205 (10)	0.0122 (7)	0.0120 (9)	0.0036 (7)
C19A	0.0454 (14)	0.0327 (10)	0.0234 (9)	0.0128 (10)	0.0124 (9)	0.0023 (8)

O1W—H1W	0.84 (2)	C12A—H12A	0.9500
O1W—H2W	0.86 (3)	C13A—H13A	0.9500
N1—C1	1.3611 (15)	C16A—C17A	1.520 (3)
N1—C5	1.3672 (15)	C16A—H16A	0.9900
N1—C14	1.4886 (15)	C16A—H16B	0.9900
C1—C2	1.3695 (17)	C17A—H17A	0.9800
C1—H1A	0.9500	C17A—H17B	0.9800
C2—C3	1.3953 (18)	C17A—H17C	0.9800
C2—H2A	0.9500	C18A—C19A	1.532 (4)
C3—C4	1.3796 (17)	C18A—H18A	0.9900
C3—H3A	0.9500	C18A—H18B	0.9900
C4—C5	1.4066 (16)	C19A—H19A	0.9800
C4—H4A	0.9500	C19A—H19B	0.9800
C5—C6	1.4529 (16)	C19A—H19C	0.9800
C6—C7	1.3548 (16)	N2B—C11B	1.369 (11)
C6—H6A	0.9500	N2B—C16B	1.462 (10)
C7—C8	1.4465 (16)	N2B—C18B	1.477 (12)
C7—H7A	0.9500	C9B—C10B	1.379 (15)
C8—C13B	1.39 (3)	C9B—H9B	0.9500
C8—C9A	1.405 (3)	C10B—C11B	1.415 (12)
C8—C13A	1.414 (5)	C10B—H10B	0.9500
C8—C9B	1.42 (2)	C11B—C12B	1.419 (15)
C14—C15	1.5193 (19)	C12B—C13B	1.383 (17)
C14—H14A	0.9900	C12B—H12B	0.9500
C14—H14B	0.9900	C13B—H13B	0.9500
C15—H15A	0.9800	C16B—C17B	1.506 (11)
C15—H15B	0.9800	C16B—H16C	0.9900
C15—H15C	0.9800	C16B—H16D	0.9900
N2A—C11A	1.372 (2)	C17B—H37D	0.9800
N2A—C18A	1.457 (2)	C17B—H37E	0.9800
N2A—C16A	1.462 (2)	C17B—H37F	0.9800
C9A—C10A	1.381 (3)	C18B—C19B	1.484 (16)
C9A—H9A	0.9500	C18B—H18C	0.9900
C10A—C11A	1.416 (2)	C18B—H18D	0.9900
C10A—H10A	0.9500	C19B—H39D	0.9800
C11A—C12A	1.416 (3)	C19B—H39E	0.9800
C12A—C13A	1.382 (3)	C19B—H39F	0.9800
H1W—O1W—H2W	105 (2)	C11A—C12A—H12A	119.3
C1—N1—C5	121.81 (10)	C12A—C13A—C8	121.4 (4)
C1—N1—C14	116.17 (10)	C12A—C13A—H13A	119.3
C5—N1—C14	122.02 (10)	C8—C13A—H13A	119.3
N1—C1—C2	121.79 (12)	N2A—C16A—C17A	114.86 (15)
N1—C1—H1A	119.1	N2A—C16A—H16A	108.6
C2—C1—H1A	119.1	C17A—C16A—H16A	108.6
C1—C2—C3	118.30 (11)	N2A—C16A—H16B	108.6
C1—C2—H2A	120.9	C17A—C16A—H16B	108.6
C3—C2—H2A	120.9	H16A—C16A—H16B	107.5
C4—C3—C2	119.53 (11)	N2A—C18A—C19A	114.4 (2)
C4—C3—H3A	120.2	N2A—C18A—H18A	108.7
C2—C3—H3A	120.2	C19A—C18A—H18A	108.7
C3—C4—C5	121.55 (11)	N2A—C18A—H18B	108.7
C3—C4—H4A	119.2	C19A—C18A—H18B	108.7
C5—C4—H4A	119.2	H18A—C18A—H18B	107.6
N1—C5—C4	116.96 (10)	C11B—N2B—C16B	122.6 (7)
N1—C5—C6	119.97 (10)	C11B—N2B—C18B	122.3 (9)
C4—C5—C6	123.06 (11)	C16B—N2B—C18B	115.0 (8)
C7—C6—C5	122.42 (10)	C10B—C9B—C8	122.4 (15)
C7—C6—H6A	118.8	C10B—C9B—H9B	118.8
C5—C6—H6A	118.8	C8—C9B—H9B	118.8
C6—C7—C8	127.43 (10)	C9B—C10B—C11B	120.6 (13)
C6—C7—H7A	116.3	C9B—C10B—H10B	119.7
C8—C7—H7A	116.3	C11B—C10B—H10B	119.7
C13B—C8—C9A	117.3 (10)	N2B—C11B—C10B	120.3 (10)
C9A—C8—C13A	116.9 (2)	N2B—C11B—C12B	123.1 (14)
C13B—C8—C9B	115.7 (12)	C10B—C11B—C12B	116.6 (14)
C13A—C8—C9B	116.6 (7)	C13B—C12B—C11B	121 (2)
C13B—C8—C7	124.1 (10)	C13B—C12B—H12B	119.4
C9A—C8—C7	118.43 (13)	C11B—C12B—H12B	119.4
C13A—C8—C7	124.64 (19)	C12B—C13B—C8	122 (2)
C9B—C8—C7	118.3 (7)	C12B—C13B—H13B	119.2
N1—C14—C15	111.56 (11)	C8—C13B—H13B	119.2
N1—C14—H14A	109.3	N2B—C16B—C17B	114.5 (8)
C15—C14—H14A	109.3	N2B—C16B—H16C	108.6
N1—C14—H14B	109.3	C17B—C16B—H16C	108.6
C15—C14—H14B	109.3	N2B—C16B—H16D	108.6
H14A—C14—H14B	108.0	C17B—C16B—H16D	108.6
C14—C15—H15A	109.5	H16C—C16B—H16D	107.6
C14—C15—H15B	109.5	C16B—C17B—H37D	109.5
H15A—C15—H15B	109.5	C16B—C17B—H37E	109.5
C14—C15—H15C	109.5	H37D—C17B—H37E	109.5
H15A—C15—H15C	109.5	C16B—C17B—H37F	109.5
H15B—C15—H15C	109.5	H37D—C17B—H37F	109.5
C11A—N2A—C18A	121.83 (15)	H37E—C17B—H37F	109.5
C11A—N2A—C16A	120.56 (13)	N2B—C18B—C19B	114.7 (14)
C18A—N2A—C16A	117.61 (13)	N2B—C18B—H18C	108.6
C10A—C9A—C8	122.1 (2)	C19B—C18B—H18C	108.6
C10A—C9A—H9A	118.9	N2B—C18B—H18D	108.6
C8—C9A—H9A	118.9	C19B—C18B—H18D	108.6
C9A—C10A—C11A	121.06 (19)	H18C—C18B—H18D	107.6
C9A—C10A—H10A	119.5	C18B—C19B—H39D	109.5
C11A—C10A—H10A	119.5	C18B—C19B—H39E	109.5
N2A—C11A—C12A	121.9 (2)	H39D—C19B—H39E	109.5
N2A—C11A—C10A	121.11 (16)	C18B—C19B—H39F	109.5
C12A—C11A—C10A	116.9 (2)	H39D—C19B—H39F	109.5
C13A—C12A—C11A	121.5 (4)	H39E—C19B—H39F	109.5
C13A—C12A—H12A	119.3
C5—N1—C1—C2	−2.09 (19)	C10A—C11A—C12A—C13A	−3.2 (7)
C14—N1—C1—C2	178.50 (12)	C11A—C12A—C13A—C8	3.3 (8)
N1—C1—C2—C3	−0.24 (19)	C13B—C8—C13A—C12A	93 (10)
C1—C2—C3—C4	1.65 (19)	C9A—C8—C13A—C12A	−2.0 (6)
C2—C3—C4—C5	−0.85 (19)	C9B—C8—C13A—C12A	9.2 (10)
C1—N1—C5—C4	2.81 (17)	C7—C8—C13A—C12A	−179.1 (4)
C14—N1—C5—C4	−177.81 (11)	C11A—N2A—C16A—C17A	−81.12 (19)
C1—N1—C5—C6	−176.43 (11)	C18A—N2A—C16A—C17A	98.4 (2)
C14—N1—C5—C6	2.94 (17)	C11A—N2A—C18A—C19A	81.4 (2)
C3—C4—C5—N1	−1.35 (18)	C16A—N2A—C18A—C19A	−98.1 (2)
C3—C4—C5—C6	177.87 (12)	C13B—C8—C9B—C10B	−12 (2)
N1—C5—C6—C7	−173.61 (12)	C9A—C8—C9B—C10B	89 (5)
C4—C5—C6—C7	7.19 (19)	C13A—C8—C9B—C10B	−4.8 (18)
C5—C6—C7—C8	−176.54 (12)	C7—C8—C9B—C10B	−177.0 (11)
C6—C7—C8—C13B	8.8 (18)	C8—C9B—C10B—C11B	4 (2)
C6—C7—C8—C9A	−176.71 (14)	C16B—N2B—C11B—C10B	−9.6 (15)
C6—C7—C8—C13A	0.4 (3)	C18B—N2B—C11B—C10B	174.4 (10)
C6—C7—C8—C9B	172.0 (8)	C16B—N2B—C11B—C12B	168 (2)
C1—N1—C14—C15	92.46 (13)	C18B—N2B—C11B—C12B	−8 (3)
C5—N1—C14—C15	−86.95 (14)	C9B—C10B—C11B—N2B	177.1 (12)
C13B—C8—C9A—C10A	−7.1 (16)	C9B—C10B—C11B—C12B	0 (3)
C13A—C8—C9A—C10A	0.7 (3)	N2B—C11B—C12B—C13B	−172 (3)
C9B—C8—C9A—C10A	−90 (4)	C10B—C11B—C12B—C13B	5 (5)
C7—C8—C9A—C10A	178.03 (14)	C11B—C12B—C13B—C8	−15 (6)
C8—C9A—C10A—C11A	−0.7 (2)	C9A—C8—C13B—C12B	6 (4)
C18A—N2A—C11A—C12A	6.8 (4)	C13A—C8—C13B—C12B	−82 (10)
C16A—N2A—C11A—C12A	−173.7 (4)	C9B—C8—C13B—C12B	17 (4)
C18A—N2A—C11A—C10A	−175.31 (17)	C7—C8—C13B—C12B	−179 (3)
C16A—N2A—C11A—C10A	4.2 (2)	C11B—N2B—C16B—C17B	87.0 (11)
C9A—C10A—C11A—N2A	−176.13 (15)	C18B—N2B—C16B—C17B	−96.8 (10)
C9A—C10A—C11A—C12A	1.9 (4)	C11B—N2B—C18B—C19B	93.0 (19)
N2A—C11A—C12A—C13A	174.8 (4)	C16B—N2B—C18B—C19B	−83.3 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···I1i	0.85 (3)	2.71 (2)	3.5498 (12)	176 (2)
O1W—H2W···I1ii	0.86 (3)	2.75 (3)	3.6055 (13)	171 (2)
C3—H3A···O1Wiii	0.95	2.35	3.2072 (19)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯I1i	0.85 (3)	2.71 (2)	3.5498 (12)	176 (2)
O1W—H2W⋯I1ii	0.86 (3)	2.75 (3)	3.6055 (13)	171 (2)
C3—H3A⋯O1W iii	0.95	2.35	3.2072 (19)	150

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