2-[(E)-2-(4-Chloro­phen­yl)ethen­yl]-1-methylpyridinium iodide monohydrate

Chanawanno, K.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536808027724

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1882-o1883

doi:10.1107/S1600536808027724

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2-[(E)-2-(4-Chlorophenyl)ethenyl]-1-methylpyridinium iodide monohydrate †

Kullapa Chanawanno,^a Suchada Chantrapromma ^b ^* and Hoong-Kun Fun ^c ‡

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 22 August 2008; accepted 29 August 2008; online 6 September 2008)

In the title compound, C₁₄H₁₃ClN⁺·I⁻·H₂O, the cation is nearly planar and exists in an E configuration; the dihedral angle between the pyridinium and benzene rings is 0.98 (17)°. The cations stack in an anti-parallel manner along the a axis through two π–π interactions between the pyridinium and benzene rings [centroid–centroid distances 3.569 (2) and 3.6818 (13) Å, respectively]. The cation, anion and water molecule are linked into a chain along the a axis by weak C—H⋯O and C—H⋯I interactions together with O—H⋯I hydrogen bonds and the chains are further connected into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see, for example: Chantrapromma et al. (2007a ,b ,c ). For background on non-linear optical properties, see, for example: Lakshmanaperumal et al. (2004 ); Marder et al. (1994 ); Qiu et al. (2007 ); Williams (1984 ); Zhai et al. (1999 ); Zhan et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₃ClN⁺·I⁻·H₂O
M_r = 375.62
Monoclinic, P 2₁ /c
a = 7.0876 (1) Å
b = 9.8096 (2) Å
c = 21.0940 (4) Å
β = 95.147 (1)°
V = 1460.68 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.36 mm⁻¹
T = 100.0 (1) K
0.28 × 0.17 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.560, T_max = 0.845
18928 measured reflections
4241 independent reflections
3486 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.13
4241 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 2.13 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1	0.86	2.87	3.592 (4)	143
O1W—H2W1⋯I1ⁱ	0.85	2.87	3.567 (4)	141
C14—H14A⋯O1W	0.96	2.50	3.202 (5)	130
C14—H14D⋯O1Wⁱⁱ	0.96	2.56	3.460 (5)	157
C1—H1A⋯I1ⁱⁱⁱ	0.93	3.20	3.830 (4)	127
C2—H2A⋯I1^iv	0.93	3.17	3.825 (4)	129
C3—H3A⋯I1^iv	0.93	3.21	3.840 (4)	127
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027724/is2329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027724/is2329Isup2.hkl

checkCIF report

Comment top

In the last two decades, many efforts were focused on the discovery of new organic materials which exhibit large nonlinear optical (NLO) properties and would have applications in the fields of optoelectronics and photonics (Lakshmanaperumal et al., 2004; Marder et al., 1994; Qiu et al., 2007; Zhai et al., 1999; Zhan et al., 2006). In order to obtain second-order NLO single crystals, the main requirements should be the choice of molecules with large hyperpolarizability (β) and the alignment of these molecules with optimal orientation into a noncentrosymmetric space group in the crystal (Williams, 1984). Among the known organic NLO materials, ionic chromophores are of great interest because they exhibit large first hyperpolarizabilities (β) and have high melting points and hardness of their crystals. At the molecular level, a generally popular approach towards NLO materials is to design and synthesize compounds with extended conjugated π-systems with donor and acceptor groups because such compounds are likely to exhibit large values of molecular hyperpolarizability (β) and to possess polarization. Styryl pyridinium derivatives are considered to be good conjugated π-systems. In continuation of our on-going research on nonlinear optical materials (Chantrapromma et al., 2007a,b,c), the title compound, (I), was synthesized and the X-ray structure analysis was carried out in order to obtain detailed information about the molecular packing. However, compound (I) crystallizes in monoclinic space group P2₁/c and doesn't exhibit second-order nonlinear optic properties.

The asymmetric unit of the title compound consists of C₁₄H₁₃ClN⁺ cation, I^- anion and one water molecule (Fig. 1). The conformation of the cation is essentially planar as indicated by the dihedral angle between the pyridinium (N1/C1—C5) and the benzene (C8—C13) rings, being 0.98 (17)°. The mean plane through C5/C6/C7/C8 plane makes dihedral angles of 6.1 (4)° and 6.4 (4)° with pyridinium and benzene rings, respectively. The cation exists in the E configuration and the torsion angle C5—C6—C7—C8 = -179.2 (3)°. The bond distances and angles in (I) have normal values (Allen et al., 1987) and comparable with closely related structures (Chantrapromma et al., 2007a,b,c).

The packing of the molecule down the c axis (Fig. 2), showing that the cation is linked with water molecule by weak C—H···O interactions (Table 1) and linked with I^- anions by weak C—H···I interactions (Table 1) whereas the I^- anion is linked with water molecule by O—H···I hydrogen bonds, forming one-dimensional chains along the a axis. These chains are further connected into a three-dimensional network (Fig. 2). π···π interactions involving pyridinium and benzene rings were also observed with Cg₁···Cg₂ distances of 3.662 (2) Å (symmetry code; 1 - x, -y, 1 - z) and 3.569 (2) Å (symmetry code; 2 - x, -y, 1 - z); Cg₁ and Cg₂ are the centroids of the N1/C1–C5 pyridinium and C8–C13 benzene rings, respectively. The crystal is stabilized by O—H···I hydrogen bond, weak C—H···O and C—H···I interactions.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Chantrapromma et al. (2007a,b,c). For background on non-linear optical properties, see, for example: Lakshmanaperumal et al. (2004); Marder et al. (1994); Qiu et al. (2007); Williams (1984); Zhai et al. (1999); Zhan et al. (2006).

Experimental top

The title compound was prepared by mixing solutions of 1,2-dimethylpyridinium iodide, 4-chlorobenzaldehyde and piperidine (1:1:1 molar ratio) in methanol. The resulting solution was refluxed for 12 hr under a nitrogen atmosphere. The solid which formed was filtered and washed with chloroform. Orange plate-like single-crystal suitable for X-ray diffraction analysis was obtained by recrystallization from methanol by slow evaporation of the solvent at ambient temperature after several days, Mp. 492–493 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. The O—H···I hydrogen bond was drawn as dashed line.
	Fig. 2. The packing diagram of the title structure viewed approximately along the c axis. Hydrogen bonds were drawn as dashed lines.

2-[(E)-2-(4-Chlorophenyl)ethenyl]-1-methylpyridinium iodide monohydrate top

Crystal data top

C₁₄H₁₃ClN⁺·I⁻·H₂O	F(000) = 736
M_r = 375.62	D_x = 1.708 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 492-493 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0876 (1) Å	Cell parameters from 4241 reflections
b = 9.8096 (2) Å	θ = 1.9–30.0°
c = 21.0940 (4) Å	µ = 2.36 mm⁻¹
β = 95.147 (1)°	T = 100 K
V = 1460.68 (5) Å³	Plate, orange
Z = 4	0.28 × 0.17 × 0.07 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4241 independent reflections
Radiation source: fine-focus sealed tube	3486 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→12
T_min = 0.561, T_max = 0.845	l = −26→29
18928 measured reflections

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0483P)² + 1.1431P] where P = (F_o² + 2F_c²)/3
4241 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 2.13 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

C₁₄H₁₃ClN⁺·I⁻·H₂O	V = 1460.68 (5) Å³
M_r = 375.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0876 (1) Å	µ = 2.36 mm⁻¹
b = 9.8096 (2) Å	T = 100 K
c = 21.0940 (4) Å	0.28 × 0.17 × 0.07 mm
β = 95.147 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4241 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3486 reflections with I > 2σ(I)
T_min = 0.561, T_max = 0.845	R_int = 0.038
18928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.13	Δρ_max = 2.13 e Å⁻³
4241 reflections	Δρ_min = −0.79 e Å⁻³
164 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.96440 (3)	0.30947 (2)	0.374487 (10)	0.02517 (9)
Cl1	0.65015 (14)	−0.33018 (11)	0.25791 (5)	0.0349 (2)
N1	0.7517 (4)	0.2927 (3)	0.58820 (14)	0.0228 (6)
O1W	0.4685 (5)	0.3289 (4)	0.39663 (18)	0.0589 (10)
H1W1	0.5617	0.2949	0.3782	0.088*
H2W1	0.3691	0.2881	0.3808	0.088*
C1	0.7754 (5)	0.3535 (4)	0.64637 (17)	0.0254 (7)
H1A	0.7521	0.4464	0.6498	0.030*
C2	0.8329 (5)	0.2805 (4)	0.69966 (18)	0.0277 (8)
H2A	0.8473	0.3228	0.7393	0.033*
C3	0.8698 (5)	0.1412 (4)	0.69383 (17)	0.0262 (7)
H3A	0.9115	0.0900	0.7294	0.031*
C4	0.8440 (5)	0.0817 (4)	0.63559 (17)	0.0264 (7)
H4A	0.8674	−0.0111	0.6318	0.032*
C5	0.7828 (5)	0.1569 (4)	0.58078 (17)	0.0221 (7)
C6	0.7492 (5)	0.0969 (4)	0.51828 (17)	0.0256 (7)
H6A	0.7187	0.1548	0.4839	0.031*
C7	0.7592 (5)	−0.0353 (4)	0.50694 (17)	0.0268 (7)
H7A	0.7883	−0.0912	0.5421	0.032*
C8	0.7293 (5)	−0.1035 (4)	0.44465 (16)	0.0235 (7)
C9	0.7663 (5)	−0.2435 (4)	0.44164 (18)	0.0266 (7)
H9A	0.8075	−0.2903	0.4786	0.032*
C10	0.7425 (5)	−0.3135 (4)	0.38414 (19)	0.0271 (8)
H10A	0.7680	−0.4063	0.3824	0.033*
C11	0.6808 (5)	−0.2432 (4)	0.33021 (17)	0.0238 (7)
C12	0.6421 (5)	−0.1050 (4)	0.33059 (17)	0.0258 (7)
H12A	0.6005	−0.0596	0.2932	0.031*
C13	0.6668 (5)	−0.0354 (4)	0.38847 (17)	0.0250 (7)
H13A	0.6414	0.0575	0.3896	0.030*
C14	0.6940 (5)	0.3805 (4)	0.53292 (18)	0.0298 (8)
H14D	0.6802	0.4727	0.5470	0.045*
H14A	0.5754	0.3489	0.5126	0.045*
H14B	0.7889	0.3769	0.5032	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02744 (14)	0.02228 (14)	0.02596 (14)	0.00264 (9)	0.00324 (9)	0.00111 (9)
Cl1	0.0368 (5)	0.0385 (6)	0.0293 (5)	−0.0051 (4)	0.0027 (4)	−0.0126 (4)
N1	0.0206 (13)	0.0229 (16)	0.0249 (15)	0.0010 (11)	0.0027 (11)	0.0046 (12)
O1W	0.0347 (17)	0.083 (3)	0.058 (2)	0.0104 (16)	−0.0028 (15)	−0.028 (2)
C1	0.0246 (17)	0.0238 (18)	0.0278 (18)	0.0003 (14)	0.0028 (14)	0.0000 (15)
C2	0.0255 (17)	0.032 (2)	0.0261 (18)	−0.0004 (14)	0.0028 (14)	−0.0020 (15)
C3	0.0209 (16)	0.031 (2)	0.0263 (17)	0.0017 (14)	−0.0021 (13)	0.0030 (15)
C4	0.0218 (16)	0.0267 (19)	0.0307 (18)	−0.0010 (14)	0.0017 (14)	0.0034 (15)
C5	0.0175 (15)	0.0230 (18)	0.0265 (17)	−0.0009 (12)	0.0050 (12)	−0.0007 (14)
C6	0.0265 (17)	0.0245 (19)	0.0258 (17)	0.0002 (14)	0.0018 (14)	0.0001 (14)
C7	0.0272 (17)	0.0261 (19)	0.0268 (18)	0.0021 (14)	0.0002 (14)	−0.0019 (15)
C8	0.0227 (16)	0.0244 (19)	0.0236 (16)	−0.0012 (13)	0.0027 (13)	−0.0021 (14)
C9	0.0288 (18)	0.0231 (19)	0.0272 (18)	0.0000 (14)	−0.0009 (14)	0.0014 (15)
C10	0.0266 (17)	0.0195 (18)	0.035 (2)	−0.0016 (14)	0.0038 (15)	0.0009 (15)
C11	0.0203 (16)	0.0253 (19)	0.0257 (17)	−0.0029 (13)	0.0025 (13)	−0.0064 (14)
C12	0.0233 (16)	0.027 (2)	0.0267 (17)	0.0026 (14)	−0.0011 (13)	0.0029 (14)
C13	0.0246 (16)	0.0172 (17)	0.0329 (19)	0.0022 (13)	0.0013 (14)	0.0009 (14)
C14	0.037 (2)	0.025 (2)	0.0281 (18)	0.0052 (15)	0.0056 (15)	0.0032 (15)

Geometric parameters (Å, º) top

Cl1—C11	1.744 (4)	C6—H6A	0.9300
N1—C1	1.361 (5)	C7—C8	1.473 (5)
N1—C5	1.361 (5)	C7—H7A	0.9300
N1—C14	1.478 (5)	C8—C13	1.397 (5)
O1W—H1W1	0.8628	C8—C9	1.400 (5)
O1W—H2W1	0.8523	C9—C10	1.391 (5)
C1—C2	1.364 (5)	C9—H9A	0.9300
C1—H1A	0.9300	C10—C11	1.368 (5)
C2—C3	1.399 (6)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.383 (5)
C3—C4	1.358 (5)	C12—C13	1.396 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.407 (5)	C13—H13A	0.9300
C4—H4A	0.9300	C14—H14D	0.9600
C5—C6	1.444 (5)	C14—H14A	0.9600
C6—C7	1.322 (5)	C14—H14B	0.9600

C1—N1—C5	121.6 (3)	C13—C8—C9	118.5 (3)
C1—N1—C14	117.3 (3)	C13—C8—C7	123.3 (3)
C5—N1—C14	121.0 (3)	C9—C8—C7	118.2 (3)
H1W1—O1W—H2W1	106.3	C10—C9—C8	121.0 (3)
N1—C1—C2	121.1 (4)	C10—C9—H9A	119.5
N1—C1—H1A	119.4	C8—C9—H9A	119.5
C2—C1—H1A	119.4	C11—C10—C9	118.8 (3)
C1—C2—C3	119.0 (4)	C11—C10—H10A	120.6
C1—C2—H2A	120.5	C9—C10—H10A	120.6
C3—C2—H2A	120.5	C10—C11—C12	122.5 (3)
C4—C3—C2	119.2 (3)	C10—C11—Cl1	119.1 (3)
C4—C3—H3A	120.4	C12—C11—Cl1	118.4 (3)
C2—C3—H3A	120.4	C11—C12—C13	118.4 (3)
C3—C4—C5	121.7 (4)	C11—C12—H12A	120.8
C3—C4—H4A	119.2	C13—C12—H12A	120.8
C5—C4—H4A	119.2	C12—C13—C8	120.9 (3)
N1—C5—C4	117.4 (3)	C12—C13—H13A	119.6
N1—C5—C6	119.3 (3)	C8—C13—H13A	119.6
C4—C5—C6	123.4 (3)	N1—C14—H14D	109.5
C7—C6—C5	123.9 (3)	N1—C14—H14A	109.5
C7—C6—H6A	118.0	H14D—C14—H14A	109.5
C5—C6—H6A	118.0	N1—C14—H14B	109.5
C6—C7—C8	127.0 (4)	H14D—C14—H14B	109.5
C6—C7—H7A	116.5	H14A—C14—H14B	109.5
C8—C7—H7A	116.5

C5—N1—C1—C2	0.5 (5)	C5—C6—C7—C8	−179.2 (3)
C14—N1—C1—C2	−178.4 (3)	C6—C7—C8—C13	−6.4 (6)
N1—C1—C2—C3	0.7 (5)	C6—C7—C8—C9	173.2 (4)
C1—C2—C3—C4	−1.3 (5)	C13—C8—C9—C10	0.3 (5)
C2—C3—C4—C5	0.6 (5)	C7—C8—C9—C10	−179.4 (3)
C1—N1—C5—C4	−1.1 (5)	C8—C9—C10—C11	−0.4 (5)
C14—N1—C5—C4	177.7 (3)	C9—C10—C11—C12	0.3 (5)
C1—N1—C5—C6	177.9 (3)	C9—C10—C11—Cl1	−179.9 (3)
C14—N1—C5—C6	−3.2 (5)	C10—C11—C12—C13	−0.2 (5)
C3—C4—C5—N1	0.6 (5)	Cl1—C11—C12—C13	−179.9 (3)
C3—C4—C5—C6	−178.4 (3)	C11—C12—C13—C8	0.0 (5)
N1—C5—C6—C7	−173.9 (3)	C9—C8—C13—C12	−0.1 (5)
C4—C5—C6—C7	5.1 (6)	C7—C8—C13—C12	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1	0.86	2.87	3.592 (4)	143
O1W—H2W1···I1ⁱ	0.85	2.87	3.567 (4)	141
C14—H14A···O1W	0.96	2.50	3.202 (5)	130
C14—H14D···O1Wⁱⁱ	0.96	2.56	3.460 (5)	157
C1—H1A···I1ⁱⁱⁱ	0.93	3.20	3.830 (4)	127
C2—H2A···I1^iv	0.93	3.18	3.825 (4)	129
C3—H3A···I1^iv	0.93	3.21	3.840 (4)	127

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃ClN⁺·I⁻·H₂O
M_r	375.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.0876 (1), 9.8096 (2), 21.0940 (4)
β (°)	95.147 (1)
V (Å³)	1460.68 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.36
Crystal size (mm)	0.28 × 0.17 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.561, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	18928, 4241, 3486
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.13
No. of reflections	4241
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.13, −0.79

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1	0.86	2.8658	3.592 (4)	143
O1W—H2W1···I1ⁱ	0.85	2.8672	3.567 (4)	141
C14—H14A···O1W	0.96	2.5028	3.202 (5)	130
C14—H14D···O1Wⁱⁱ	0.96	2.5568	3.460 (5)	157
C1—H1A···I1ⁱⁱⁱ	0.93	3.1968	3.830 (4)	127
C2—H2A···I1^iv	0.93	3.1748	3.825 (4)	129
C3—H3A···I1^iv	0.93	3.2053	3.840 (4)	127

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x, −y+1/2, z+1/2.

Footnotes

†This paper is dedicated to Her Royal Highness the late Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of science in Thailand.

‡Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

KC thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, is gratefully acknowledged. The authors also thank Prince of Songkla University, the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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