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Acta Cryst. (2010). E66, o651-o652    [ doi:10.1107/S1600536810006045 ]

1-Methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]pyridinium iodide monohydrate

H.-K. Fun, K. Chanawanno, C. Surasit and S. Chantrapromma

Abstract top

The asymmetric unit of the title compound, C16H16N+·I-·H2O, contains two 1-methyl-4-{[(1E,3E)-4-phenylbuta-1,3-dienyl]}pyridinium cations, two iodide ions and two solvent water molecules. The cation is twisted slightly, the dihedral angle between the pyridinium and the phenyl rings being 10.68 (18)° in one molecule and 18.9 (3)° in the other. The two water molecules 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 molecules located between adjacent cations. The cations are linked to the iodide ions and water molecules by weak C-H...I and C-H...O interactions, respectively. These interactions together with O-H...I hydrogen bonds link the molecules into a two-dimensional network parallel to the bc plane. [pi]...[pi] interactions with a centroid-centroid distance of 3.669 (2) Å are also observed.

Comment top

It was known that the non-linear optic (NLO) materials require molecular first hyperpolarizability (β) and at the molecular level, compounds likely to exhibit large β values must have polarizable electrons (i.e. π-electrons) spread over a large distance. Thus, organic dipolar compounds with extended π systems having terminal donor and acceptor groups are likely to exhibit large π values (Raimundo et al., 2002). We have previous reported the crystal structures of the NLO-active compounds (Chantrapromma et al., 2009a, b; Fun et al., 2009) in which the cations consist of an ethenyl bridge between two rings. The title compound was designed and synthesized by extending the π-conjugate systems of the cation with an expectation for better NLO properties. However, the title compound crystallizes in centrosymmetric C2/c space group and does not exhibit second-order nonlinear optical properties.

The asymmetric unit of the title compound, C16H16N+.I-.H2O, Fig 1, comprises two 1-methyl-4-{[(1E,3E)-4-phenylbuta-1,3-dienyl]}pyridinium cations, two iodide ions and two solvent water molecules. The cation is slightly twisted with the dihedral angle between the pyridinium and phenyl rings being 10.68 (18) ° in molecule A [18.9 (3)° in molecule B]. The buta-1,3-dienyl moiety (C6–C9) is almost planar with the r.m.s of 0.0046 (5) Å in molecule A [0.0283 (5) Å in molecule B] and the torsion angles C6–C7–C8–C9 = 179.1 (4)° in molecule A [174.2 (4)° in molecule B]. This unit makes the dihedral angles of 6.4 (4) and 5.4 (4)° with the pyridinium and phenyl ring, respectively in molecule A [the corresponding values are 5.7 (5) and 13.4 (5)° in molecule B]. The two water molecules are disordered over three positions with the site-occupancy ratio of 0.9/0.7/0.4. The bond lengths of cations are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Chantrapromma et al., 2009a, b, Fun et al., 2009).

In the crystal packing (Fig. 2), the cations are arranged into ribbons along the b axis with the iodide ions and water molecules located between adjacent cations. The cations are linked to the iodide ions and water molecules by C—H···I and C—H···O weak interactions (Table 1), respectively whereas water molecules form O—H···I hydrogen bonds (Table 1) with iodide ions. These interactions linked the molecules into two-dimensional networks parallel to the bc plane. π···π interactions involving pyridinium and phenyl rings was also observed with the distance of Cg1···Cg2 = 3.669 (2) Å (symmetry code: 3/2-x, 1/2-y, -z); Cg1 and Cg2 are the centroids of N1A/C1A–C5A and C10A–C15A rings, respectively.

Related literature top

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 top

The title compound was prepared by mixing 1:1:1 molar ratio solutions of 1,4-dimethylpyridinium iodide (2 g, 8.5 mmol), cinnamaldehyde (1.1 g, 8.5 mmol) and piperidine (0.84 ml, 8.5 mmol) in methanol (40 ml). The resulting solution was refluxed for 3 h under a nitrogen atmosphere. The yellow solid which formed was filtered, washed with diethylether and recrystallized from methanol by slow evaporation at room temperature to yield the yellow block-shaped single crystals suitable for x-ray diffraction analysis over a few weeks (Mp. 496-498 K).

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(O-H) = 0.71-0.92 Å, d(C-H) = 0.93 Å for aromatic and CH and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The two water molecules are disordered over three sites with occupancies 0.931 (9), 0.695 (9) and 0.354 (9), respectively. In the final refinement, this ratio was fixed as 0.90 : 0.70 : 0.40. The highest residual electron density peak is located at 0.84 Å from I1B and the deepest hole is located at 0.83 Å from I1B.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the a axis. Hydrogen bonds, weak C—H···O and C—H···I interactions are shown as dashed lines.
1-Methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]pyridinium iodide monohydrate top
Crystal data top
C16H16N+·I−·H2OF(000) = 2912
Mr = 367.21Dx = 1.535 Mg m−3
Monoclinic, C2/cMelting point = 496–498 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 32.5600 (6) ÅCell parameters from 9279 reflections
b = 12.6414 (2) Åθ = 1.7–30.0°
c = 16.5602 (3) ŵ = 2.01 mm−1
β = 111.180 (1)°T = 100 K
V = 6355.81 (19) Å3Block, yellow
Z = 160.55 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer		9279 independent reflections
Radiation source: sealed tube6818 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −39→45
Tmin = 0.407, Tmax = 0.694k = −17→17
36570 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-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 parametersΔρmax = 2.40 e Å−3
0 restraintsΔρmin = −1.87 e Å−3
Crystal data top
C16H16N+·I−·H2OV = 6355.81 (19) Å3
Mr = 367.21Z = 16
Monoclinic, C2/cMo Kα radiation
a = 32.5600 (6) ŵ = 2.01 mm−1
b = 12.6414 (2) ÅT = 100 K
c = 16.5602 (3) Å0.55 × 0.20 × 0.20 mm
β = 111.180 (1)°
Data collection top
Bruker APEXII CCD area detector
diffractometer		9279 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		6818 reflections with I > 2σ(I)
Tmin = 0.407, Tmax = 0.694Rint = 0.031
36570 measured reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0415P)2 + 36.1246P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117Δρmax = 2.40 e Å−3
S = 1.01Δρmin = −1.87 e Å−3
9279 reflectionsAbsolute structure: ?
357 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I1A0.006481 (8)0.74812 (2)0.492960 (16)0.03922 (8)
I1B0.825988 (11)0.71635 (2)0.18855 (3)0.06328 (12)
N1A0.90440 (10)0.0474 (2)0.29244 (19)0.0305 (6)
C1A0.84641 (12)0.1693 (3)0.2688 (2)0.0302 (7)
H1A0.83560.23020.28560.036*
C2A0.88809 (12)0.1352 (3)0.3159 (2)0.0303 (7)
H2A0.90530.17290.36460.036*
C3A0.87910 (13)−0.0101 (3)0.2239 (2)0.0368 (8)
H3A0.8904−0.07190.20940.044*
C4A0.83732 (13)0.0206 (3)0.1755 (2)0.0360 (8)
H4A0.8204−0.02060.12890.043*
C5A0.81968 (12)0.1135 (3)0.1953 (2)0.0303 (7)
C6A0.77644 (12)0.1532 (3)0.1426 (2)0.0348 (8)
H6A0.76620.21320.16190.042*
C7A0.75006 (13)0.1094 (3)0.0677 (3)0.0378 (8)
H7A0.75970.04760.04970.045*
C8A0.70796 (12)0.1511 (3)0.0135 (2)0.0358 (8)
H8A0.69760.21220.03100.043*
C9A0.68303 (12)0.1052 (3)−0.0615 (2)0.0340 (7)
H9A0.69430.0438−0.07650.041*
C10A0.64019 (12)0.1407 (3)−0.1220 (2)0.0311 (7)
C11A0.62086 (12)0.0866 (3)−0.2003 (2)0.0328 (7)
H11A0.63520.0286−0.21250.039*
C12A0.58082 (12)0.1182 (3)−0.2597 (3)0.0367 (8)
H12A0.56860.0817−0.31170.044*
C13A0.55865 (12)0.2036 (3)−0.2427 (3)0.0361 (8)
H13A0.53180.2254−0.28320.043*
C14A0.57699 (12)0.2566 (3)−0.1641 (2)0.0338 (7)
H14A0.56180.3126−0.15130.041*
C15A0.61757 (12)0.2269 (3)−0.1047 (2)0.0320 (7)
H15A0.62990.2642−0.05320.038*
C16A0.95039 (13)0.0138 (3)0.3392 (3)0.0380 (8)
H16A0.96420.06180.38610.057*
H16B0.96620.01410.30020.057*
H16C0.9506−0.05630.36170.057*
N1B0.07132 (13)0.4780 (3)−0.0525 (3)0.0509 (9)
C1B0.12480 (15)0.5134 (4)0.0860 (3)0.0503 (11)
H1B0.13400.55320.13660.060*
C2B0.08526 (15)0.5343 (4)0.0221 (3)0.0490 (11)
H2B0.06760.58810.03000.059*
C3B0.09613 (17)0.4012 (4)−0.0651 (4)0.0586 (12)
H3B0.08640.3634−0.11680.070*
C4B0.13613 (17)0.3770 (4)−0.0025 (4)0.0595 (13)
H4B0.15310.3229−0.01250.071*
C5B0.15160 (14)0.4319 (4)0.0753 (3)0.0496 (11)
C6B0.19467 (14)0.4065 (4)0.1392 (3)0.0517 (11)
H6B0.21010.35070.12700.062*
C7B0.21354 (13)0.4573 (4)0.2139 (3)0.0488 (11)
H7B0.19720.50970.22800.059*
C8B0.25747 (14)0.4369 (4)0.2747 (3)0.0491 (11)
H8B0.27340.38060.26460.059*
C9B0.27587 (14)0.4970 (4)0.3451 (3)0.0509 (12)
H9B0.25780.54730.35630.061*
C10B0.32147 (15)0.4919 (4)0.4064 (3)0.0519 (12)
C11B0.35014 (14)0.4109 (4)0.4035 (3)0.0550 (13)
H11B0.34020.35540.36440.066*
C12B0.39410 (16)0.4145 (5)0.4602 (4)0.0646 (16)
H12B0.41340.36070.45930.077*
C13B0.40872 (18)0.4975 (5)0.5174 (4)0.0699 (17)
H13B0.43810.49970.55390.084*
C14B0.3806 (2)0.5774 (5)0.5217 (3)0.0703 (16)
H14B0.39080.63280.56090.084*
C15B0.33693 (17)0.5734 (5)0.4665 (3)0.0601 (13)
H15B0.31760.62600.46970.072*
C16B0.02813 (16)0.5012 (4)−0.1198 (3)0.0622 (14)
H16D0.02910.4851−0.17580.093*
H16E0.02130.5748−0.11750.093*
H16F0.00590.4589−0.11000.093*
O1W0.05902 (16)0.3235 (5)0.7242 (3)0.104 (2)0.90
H1W10.06400.26980.71880.156*0.90
H2W10.07610.36180.70070.156*0.90
O2W0.4677 (3)0.6439 (6)0.6879 (4)0.103 (2)0.70
H1W20.46100.69300.72060.154*0.70
H2W20.47700.67330.65570.154*0.70
O3W0.2541 (4)0.6530 (9)0.5171 (7)0.087 (3)0.40
H1W30.23740.67260.46780.130*0.40
H2W30.27660.68950.52890.130*0.40
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1A0.03478 (13)0.03914 (14)0.03595 (13)0.00447 (10)0.00338 (9)−0.00831 (10)
I1B0.04728 (17)0.03069 (15)0.0990 (3)0.00016 (12)0.01098 (17)−0.00940 (15)
N1A0.0356 (15)0.0254 (14)0.0325 (15)0.0005 (11)0.0145 (13)0.0036 (11)
C1A0.0348 (18)0.0286 (17)0.0318 (17)−0.0008 (13)0.0177 (14)−0.0004 (13)
C2A0.0353 (18)0.0287 (17)0.0301 (17)−0.0033 (13)0.0157 (14)−0.0020 (13)
C3A0.047 (2)0.0248 (17)0.0371 (19)0.0014 (15)0.0132 (17)−0.0033 (14)
C4A0.044 (2)0.0291 (18)0.0315 (18)−0.0033 (15)0.0096 (16)−0.0054 (14)
C5A0.0333 (17)0.0289 (17)0.0303 (16)−0.0024 (13)0.0134 (14)0.0044 (13)
C6A0.0359 (19)0.0325 (18)0.0377 (19)−0.0001 (14)0.0152 (16)0.0025 (14)
C7A0.039 (2)0.0339 (19)0.041 (2)0.0024 (15)0.0151 (17)0.0042 (15)
C8A0.0372 (19)0.0327 (18)0.0389 (19)0.0021 (15)0.0154 (16)0.0020 (15)
C9A0.0367 (19)0.0281 (17)0.0390 (19)0.0029 (14)0.0160 (16)0.0028 (14)
C10A0.0334 (17)0.0278 (17)0.0329 (17)0.0009 (13)0.0131 (14)0.0032 (13)
C11A0.0372 (18)0.0230 (16)0.0405 (19)−0.0008 (13)0.0170 (16)−0.0024 (13)
C12A0.0357 (19)0.0347 (19)0.040 (2)−0.0062 (15)0.0138 (16)−0.0064 (15)
C13A0.0297 (17)0.037 (2)0.042 (2)−0.0003 (14)0.0136 (15)0.0001 (15)
C14A0.0335 (17)0.0332 (18)0.0379 (18)0.0049 (14)0.0166 (15)−0.0010 (15)
C15A0.0348 (18)0.0308 (18)0.0323 (17)0.0005 (13)0.0143 (15)−0.0030 (13)
C16A0.040 (2)0.0333 (19)0.038 (2)0.0058 (15)0.0110 (16)0.0007 (15)
N1B0.046 (2)0.044 (2)0.062 (2)−0.0065 (16)0.0187 (19)0.0218 (18)
C1B0.046 (2)0.048 (3)0.057 (3)0.0014 (19)0.019 (2)0.020 (2)
C2B0.046 (2)0.044 (2)0.061 (3)0.0042 (19)0.025 (2)0.022 (2)
C3B0.056 (3)0.053 (3)0.070 (3)−0.011 (2)0.027 (3)0.002 (2)
C4B0.050 (3)0.055 (3)0.082 (4)−0.001 (2)0.033 (3)0.007 (3)
C5B0.040 (2)0.045 (2)0.069 (3)−0.0013 (18)0.025 (2)0.020 (2)
C6B0.039 (2)0.045 (2)0.077 (3)0.0034 (18)0.027 (2)0.017 (2)
C7B0.034 (2)0.047 (2)0.073 (3)0.0072 (18)0.028 (2)0.026 (2)
C8B0.038 (2)0.049 (3)0.068 (3)0.0052 (18)0.027 (2)0.024 (2)
C9B0.037 (2)0.060 (3)0.066 (3)0.0106 (19)0.031 (2)0.026 (2)
C10B0.038 (2)0.067 (3)0.057 (3)0.006 (2)0.025 (2)0.031 (2)
C11B0.041 (2)0.064 (3)0.066 (3)0.009 (2)0.026 (2)0.037 (2)
C12B0.045 (3)0.074 (4)0.083 (4)0.011 (2)0.032 (3)0.050 (3)
C13B0.050 (3)0.096 (5)0.059 (3)−0.005 (3)0.013 (2)0.043 (3)
C14B0.071 (4)0.097 (5)0.047 (3)0.002 (3)0.026 (3)0.024 (3)
C15B0.057 (3)0.083 (4)0.051 (3)0.008 (3)0.033 (2)0.021 (3)
C16B0.052 (3)0.059 (3)0.065 (3)−0.009 (2)0.009 (2)0.027 (2)
O1W0.062 (3)0.163 (6)0.068 (3)0.025 (3)0.000 (2)−0.037 (3)
O2W0.143 (7)0.107 (5)0.084 (4)−0.027 (5)0.073 (5)−0.010 (4)
O3W0.109 (9)0.064 (6)0.071 (7)0.016 (6)0.014 (6)−0.001 (5)
Geometric parameters (Å, °) top
N1A—C2A1.346 (4)C1B—C2B1.364 (6)
N1A—C3A1.349 (5)C1B—C5B1.402 (7)
N1A—C16A1.478 (5)C1B—H1B0.9300
C1A—C2A1.368 (5)C2B—H2B0.9300
C1A—C5A1.403 (5)C3B—C4B1.374 (7)
C1A—H1A0.9300C3B—H3B0.9300
C2A—H2A0.9300C4B—C5B1.388 (7)
C3A—C4A1.362 (5)C4B—H4B0.9300
C3A—H3A0.9300C5B—C6B1.456 (6)
C4A—C5A1.397 (5)C6B—C7B1.330 (7)
C4A—H4A0.9300C6B—H6B0.9300
C5A—C6A1.452 (5)C7B—C8B1.444 (6)
C6A—C7A1.347 (5)C7B—H7B0.9300
C6A—H6A0.9300C8B—C9B1.338 (7)
C7A—C8A1.440 (5)C8B—H8B0.9300
C7A—H7A0.9300C9B—C10B1.466 (6)
C8A—C9A1.345 (5)C9B—H9B0.9300
C8A—H8A0.9300C10B—C15B1.394 (8)
C9A—C10A1.464 (5)C10B—C11B1.399 (7)
C9A—H9A0.9300C11B—C12B1.401 (7)
C10A—C11A1.398 (5)C11B—H11B0.9300
C10A—C15A1.401 (5)C12B—C13B1.378 (9)
C11A—C12A1.378 (5)C12B—H12B0.9300
C11A—H11A0.9300C13B—C14B1.382 (9)
C12A—C13A1.384 (5)C13B—H13B0.9300
C12A—H12A0.9300C14B—C15B1.387 (8)
C13A—C14A1.392 (5)C14B—H14B0.9300
C13A—H13A0.9300C15B—H15B0.9300
C14A—C15A1.384 (5)C16B—H16D0.9600
C14A—H14A0.9300C16B—H16E0.9600
C15A—H15A0.9300C16B—H16F0.9600
C16A—H16A0.9600O1W—H1W10.7106
C16A—H16B0.9600O1W—H2W10.9232
C16A—H16C0.9600O2W—H1W20.8994
N1B—C3B1.326 (6)O2W—H2W20.7950
N1B—C2B1.355 (6)O3W—H1W30.8376
N1B—C16B1.474 (6)O3W—H2W30.8268
C2A—N1A—C3A120.2 (3)C2B—N1B—C16B119.9 (4)
C2A—N1A—C16A121.1 (3)C2B—C1B—C5B120.0 (5)
C3A—N1A—C16A118.7 (3)C2B—C1B—H1B120.0
C2A—C1A—C5A120.9 (3)C5B—C1B—H1B120.0
C2A—C1A—H1A119.6N1B—C2B—C1B121.1 (5)
C5A—C1A—H1A119.6N1B—C2B—H2B119.5
N1A—C2A—C1A120.5 (3)C1B—C2B—H2B119.5
N1A—C2A—H2A119.7N1B—C3B—C4B120.7 (5)
C1A—C2A—H2A119.7N1B—C3B—H3B119.7
N1A—C3A—C4A121.1 (3)C4B—C3B—H3B119.7
N1A—C3A—H3A119.4C3B—C4B—C5B121.0 (5)
C4A—C3A—H3A119.4C3B—C4B—H4B119.5
C3A—C4A—C5A120.6 (3)C5B—C4B—H4B119.5
C3A—C4A—H4A119.7C4B—C5B—C1B116.8 (4)
C5A—C4A—H4A119.7C4B—C5B—C6B119.7 (5)
C4A—C5A—C1A116.5 (3)C1B—C5B—C6B123.4 (5)
C4A—C5A—C6A122.8 (3)C7B—C6B—C5B124.7 (5)
C1A—C5A—C6A120.7 (3)C7B—C6B—H6B117.6
C7A—C6A—C5A124.6 (4)C5B—C6B—H6B117.6
C7A—C6A—H6A117.7C6B—C7B—C8B124.8 (5)
C5A—C6A—H6A117.7C6B—C7B—H7B117.6
C6A—C7A—C8A124.7 (4)C8B—C7B—H7B117.6
C6A—C7A—H7A117.6C9B—C8B—C7B121.7 (5)
C8A—C7A—H7A117.6C9B—C8B—H8B119.1
C9A—C8A—C7A122.6 (4)C7B—C8B—H8B119.1
C9A—C8A—H8A118.7C8B—C9B—C10B127.0 (5)
C7A—C8A—H8A118.7C8B—C9B—H9B116.5
C8A—C9A—C10A127.4 (3)C10B—C9B—H9B116.5
C8A—C9A—H9A116.3C15B—C10B—C11B119.5 (5)
C10A—C9A—H9A116.3C15B—C10B—C9B118.5 (5)
C11A—C10A—C15A118.4 (3)C11B—C10B—C9B122.0 (5)
C11A—C10A—C9A118.9 (3)C10B—C11B—C12B119.1 (6)
C15A—C10A—C9A122.7 (3)C10B—C11B—H11B120.5
C12A—C11A—C10A120.9 (3)C12B—C11B—H11B120.5
C12A—C11A—H11A119.6C13B—C12B—C11B120.1 (5)
C10A—C11A—H11A119.6C13B—C12B—H12B120.0
C11A—C12A—C13A120.6 (4)C11B—C12B—H12B120.0
C11A—C12A—H12A119.7C12B—C13B—C14B121.4 (5)
C13A—C12A—H12A119.7C12B—C13B—H13B119.3
C12A—C13A—C14A119.2 (4)C14B—C13B—H13B119.3
C12A—C13A—H13A120.4C13B—C14B—C15B118.7 (6)
C14A—C13A—H13A120.4C13B—C14B—H14B120.7
C15A—C14A—C13A120.7 (3)C15B—C14B—H14B120.7
C15A—C14A—H14A119.7C14B—C15B—C10B121.2 (5)
C13A—C14A—H14A119.7C14B—C15B—H15B119.4
C14A—C15A—C10A120.2 (3)C10B—C15B—H15B119.4
C14A—C15A—H15A119.9N1B—C16B—H16D109.5
C10A—C15A—H15A119.9N1B—C16B—H16E109.5
N1A—C16A—H16A109.5H16D—C16B—H16E109.5
N1A—C16A—H16B109.5N1B—C16B—H16F109.5
H16A—C16A—H16B109.5H16D—C16B—H16F109.5
N1A—C16A—H16C109.5H16E—C16B—H16F109.5
H16A—C16A—H16C109.5H1W1—O1W—H2W1104.4
H16B—C16A—H16C109.5H1W2—O2W—H2W2108.4
C3B—N1B—C2B120.4 (4)H1W3—O3W—H2W3105.9
C3B—N1B—C16B119.7 (5)
C3A—N1A—C2A—C1A−2.6 (5)C3B—N1B—C2B—C1B−0.3 (6)
C16A—N1A—C2A—C1A175.8 (3)C16B—N1B—C2B—C1B179.0 (4)
C5A—C1A—C2A—N1A0.3 (5)C5B—C1B—C2B—N1B−0.5 (6)
C2A—N1A—C3A—C4A2.1 (5)C2B—N1B—C3B—C4B0.5 (7)
C16A—N1A—C3A—C4A−176.2 (4)C16B—N1B—C3B—C4B−178.8 (4)
N1A—C3A—C4A—C5A0.6 (6)N1B—C3B—C4B—C5B0.0 (7)
C3A—C4A—C5A—C1A−2.7 (5)C3B—C4B—C5B—C1B−0.8 (7)
C3A—C4A—C5A—C6A176.0 (4)C3B—C4B—C5B—C6B−178.2 (4)
C2A—C1A—C5A—C4A2.3 (5)C2B—C1B—C5B—C4B1.0 (6)
C2A—C1A—C5A—C6A−176.4 (3)C2B—C1B—C5B—C6B178.3 (4)
C4A—C5A—C6A—C7A−3.9 (6)C4B—C5B—C6B—C7B176.7 (4)
C1A—C5A—C6A—C7A174.8 (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—C9A179.1 (4)C6B—C7B—C8B—C9B174.2 (4)
C7A—C8A—C9A—C10A−179.3 (4)C7B—C8B—C9B—C10B−173.0 (4)
C8A—C9A—C10A—C11A175.0 (4)C8B—C9B—C10B—C15B168.2 (4)
C8A—C9A—C10A—C15A−5.1 (6)C8B—C9B—C10B—C11B−8.8 (7)
C15A—C10A—C11A—C12A1.0 (5)C15B—C10B—C11B—C12B−1.1 (6)
C9A—C10A—C11A—C12A−179.2 (3)C9B—C10B—C11B—C12B175.8 (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—C14B1.4 (7)
C12A—C13A—C14A—C15A2.2 (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—C14A0.3 (5)C11B—C10B—C15B—C14B2.1 (6)
C9A—C10A—C15A—C14A−179.5 (3)C9B—C10B—C15B—C14B−175.0 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2W—H2W2···I1Ai0.792.883.655 (8)166
C3B—H3B···O1Wii0.932.513.399 (8)161
C16A—H16A···I1Aiii0.963.053.992 (4)167
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2W—H2W2···I1Ai0.792.883.655 (8)166
C3B—H3B···O1Wii0.932.513.399 (8)161
C16A—H16A···I1Aiii0.963.053.992 (4)167
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

KC thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. The authors thank Prince of Songkla University for financial support and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

references
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