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

Laksana, C.; Ruanwas, P.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536807061375

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o145-o146

https://doi.org/10.1107/S1600536807061375

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

Chotika Laksana,^a Pumsak Ruanwas,^a Suchada Chantrapromma ^a ^* and Hoong-Kun Fun ^b ^*

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th, hkfun@usm.my

(Received 13 November 2007; accepted 20 November 2007; online 6 December 2007)

In the title compound, C₁₆H₁₈NO⁺·I⁻·H₂O, the cation is essentially planar, with a dihedral angle of 3.13 (16)° between the pyridinium and benzene rings. The molecule adopts an E configuration with respect to the alkene double bond. In the crystal structure, the cations are packed in an anti-parallel manner through π–π interactions between adjacent pyridinium and benzene rings along the a axis, with centroid-to-centroid distances of 3.615 (2) and 3.630 (2) Å. Water molecules bind the iodide ions through O—H⋯I hydrogen bonds into layers. These layers link with the cations through weak C—H⋯O and C—H⋯I interactions.

Related literature

For values of bond lengths, see Allen et al. (1987 ). For related structures, see, for example: Chantrapromma et al. (2005 , 2006 ); Chantrapromma, Jindawong & Fun (2007 ); Chantrapromma, Jindawong, Fun & Patil (2007 ); Chantrapromma, Jindawong, Fun, Patil & Karalai (2007 ); Jindawong et al. (2005 ); Zhang et al. (2000 ). For background to nonlinear optics, see, for example: Oudar & Chemla (1977 ); Williams (1984 ).

Experimental

Crystal data

C₁₆H₁₈NO⁺·I⁻·H₂O
M_r = 385.23
Triclinic, $[P \overline 1]$
a = 6.9261 (4) Å
b = 10.1857 (6) Å
c = 11.6303 (6) Å
α = 100.829 (2)°
β = 97.399 (2)°
γ = 92.892 (2)°
V = 796.81 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.01 mm⁻¹
T = 100.0 (1) K
0.36 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.528, T_max = 0.797
18790 measured reflections
4635 independent reflections
4333 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.14
4635 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 2.16 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1	0.85	2.88	3.681 (3)	158
O1W—H2W1⋯I1ⁱ	0.85	2.88	3.690 (3)	159
C16—H16B⋯O1Wⁱⁱ	0.96	2.49	3.346 (5)	148
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997 ); 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: https://doi.org/10.1107/S1600536807061375/sj2440sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061375/sj2440Isup2.hkl

checkCIF report

Comment top

The design of nonlinear optical (NLO) materials is of great interest due to the various applications of NLO materials. At molecular level, such compounds are likely to exhibit large values of molecular hyperpolarizability (β) and they have to have polarizable electrons (conjugated π system) spread over a large distance (Oudar & Chemla, 1977). We have been previously synthesized pyridinium and quinolinium derivatives to study their non-linear optical properties (Chantrapromma et al., 2005, 2006; Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007; Chantrapromma, Jindawong, Fun, Patil & Karalai, 2007; Jindawong et al., 2005). The single-crystal x-ray structural study of the title compound was undertaken in order to establish the structure and conformation of the various groups. However, the title compound crystallized in the centrosymmetric P1 triclinic space group and therefore does not exhibit non-linear optical properties (Williams, 1984).

The asymmetric unit of the title compound consists of the pyridinium cation, iodide anion and one water molecule (Fig. 1). The water molecule forms an O1W—H1W1···I1 hydrogen bond to the iodide ion (Table 1). The cation is essentially planar and exist in E configuration with respect to the C6?C7 double bond [1.342 (5) Å]. The dihedral angle between the pyridinium and benzene rings is 3.13 (16)°. The ethenyl unit is also planar with respect to the two aromatic rings with the torsion angles C4—C5—C6—C7 = -1.1 (5)° and C6—C7—C8—C13 = 3.8 (6)°. The ethoxy substituent deviates only slightly from the benzene ring plane, with a C14—O1—C11—C10 torsion angle of 5.3 (5)°. Bond lengths and angles are in normal ranges (Allen et al., 1987) and the bond lengths and angles of the cation are comparable with those for closely related structures (Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007; Zhang et al., 2000).

In the crystal structure, the cations are packed in an anti-parallel fashion through π···π interactions along the a axis with Cg₁···Cg₂ distances 3.615 (2) Å (symmetry code -x, 1 - y, 1 - z) and 3.630 (2) Å (symmetry code 1 - x,1 - y, 1 - z) where Cg₁ is the centroid of the C1–C5/N1 pyridinium ring Cg₂ is the centroid of the C8–C13 benzene ring. Water molecules bind to iodide ions by O—H···I hydrogen bonds forming layers. These layers are linked with the cations through weak C—H···O and C—H···I interactions, Table 1.

Related literature top

For values of bond lengths, see Allen et al. (1987). For related structures, see, for example: Chantrapromma et al. (2005, 2006); Chantrapromma, Jindawong & Fun (2007); Chantrapromma, Jindawong, Fun & Patil (2007); Chantrapromma, Jindawong, Fun, Patil & Karalai (2007); Jindawong et al. (2005); Zhang et al. (2000). For background to nonlinear optics, see, for example: Oudar & Chemla (1977); Williams (1984).

Experimental top

The title compound was synthesized by mixing a solution (1:1:1 molar ratio) of 1,2-dimethylpyridinium iodide (2.00 g, 8.51 mmol), 4-ethoxybenzaldehyde (1.28 g, 8.51 mmol) and piperidine (0.72 g, 8.51 mmol) in hot methanol (45 ml) and refluxing for 3 hrs under a nitrogen atmosphere. The solid which formed was filtered, washed with cold ethanol and dried. Yellow single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol by slow evaporation of the solvent at room temperature over several days (Mp. 481–483 K).

Structure description top

For values of bond lengths, see Allen et al. (1987). For related structures, see, for example: Chantrapromma et al. (2005, 2006); Chantrapromma, Jindawong & Fun (2007); Chantrapromma, Jindawong, Fun & Patil (2007); Chantrapromma, Jindawong, Fun, Patil & Karalai (2007); Jindawong et al. (2005); Zhang et al. (2000). For background to nonlinear optics, see, for example: Oudar & Chemla (1977); Williams (1984).

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, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. The O—H···I hydrogen bond is drawn as a dashed line.
	Fig. 2. The crystal packing of (I). The O—H···I hydrogen bond and weak C—H···O and C—H···I interactions are drawn as dashed lines.

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

Crystal data top

C₁₆H₁₈NO⁺·I⁻·H₂O	Z = 2
M_r = 385.23	F(000) = 384
Triclinic, P1	D_x = 1.606 Mg m⁻³
Hall symbol: -P 1	Melting point = 481–483 K
a = 6.9261 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1857 (6) Å	Cell parameters from 4635 reflections
c = 11.6303 (6) Å	θ = 1.8–30.0°
α = 100.829 (2)°	µ = 2.01 mm⁻¹
β = 97.399 (2)°	T = 100 K
γ = 92.892 (2)°	Block, yellow
V = 796.81 (8) Å³	0.36 × 0.15 × 0.12 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4635 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
T_min = 0.528, T_max = 0.797	l = −16→16
18790 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0521P)² + 1.6362P] where P = (F_o² + 2F_c²)/3
4635 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 2.16 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

C₁₆H₁₈NO⁺·I⁻·H₂O	γ = 92.892 (2)°
M_r = 385.23	V = 796.81 (8) Å³
Triclinic, P1	Z = 2
a = 6.9261 (4) Å	Mo Kα radiation
b = 10.1857 (6) Å	µ = 2.01 mm⁻¹
c = 11.6303 (6) Å	T = 100 K
α = 100.829 (2)°	0.36 × 0.15 × 0.12 mm
β = 97.399 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4635 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4333 reflections with I > 2σ(I)
T_min = 0.528, T_max = 0.797	R_int = 0.028
18790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.14	Δρ_max = 2.16 e Å⁻³
4635 reflections	Δρ_min = −0.83 e Å⁻³
184 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	0.46635 (3)	0.14640 (2)	0.24655 (2)	0.02735 (8)
O1	0.1292 (4)	0.6828 (2)	0.0835 (2)	0.0265 (5)
N1	0.3219 (4)	0.2513 (3)	0.6774 (2)	0.0246 (5)
C1	0.3453 (5)	0.2172 (4)	0.7851 (3)	0.0283 (7)
H1A	0.3605	0.1281	0.7900	0.034*
C2	0.3471 (5)	0.3101 (4)	0.8871 (3)	0.0287 (7)
H2A	0.3621	0.2850	0.9604	0.034*
C3	0.3261 (5)	0.4426 (4)	0.8781 (3)	0.0293 (7)
H3A	0.3244	0.5075	0.9458	0.035*
C4	0.3077 (5)	0.4781 (3)	0.7687 (3)	0.0270 (6)
H4A	0.2993	0.5677	0.7632	0.032*
C5	0.3015 (5)	0.3798 (3)	0.6650 (3)	0.0238 (6)
C6	0.2736 (5)	0.4093 (3)	0.5481 (3)	0.0258 (6)
H6A	0.2734	0.3395	0.4837	0.031*
C7	0.2478 (5)	0.5331 (3)	0.5277 (3)	0.0261 (6)
H7A	0.2481	0.6010	0.5935	0.031*
C8	0.2192 (5)	0.5716 (3)	0.4114 (3)	0.0240 (6)
C9	0.2019 (5)	0.7071 (3)	0.4050 (3)	0.0268 (6)
H9A	0.2116	0.7703	0.4749	0.032*
C10	0.1712 (5)	0.7494 (3)	0.2986 (3)	0.0269 (6)
H10A	0.1592	0.8396	0.2969	0.032*
C11	0.1585 (5)	0.6551 (3)	0.1938 (3)	0.0222 (6)
C12	0.1731 (5)	0.5193 (3)	0.1975 (3)	0.0243 (6)
H12A	0.1616	0.4560	0.1275	0.029*
C13	0.2042 (5)	0.4792 (3)	0.3044 (3)	0.0246 (6)
H13A	0.2156	0.3889	0.3057	0.029*
C14	0.1273 (5)	0.8225 (3)	0.0753 (3)	0.0269 (6)
H14A	0.2506	0.8705	0.1130	0.032*
H14B	0.0233	0.8631	0.1145	0.032*
C15	0.0951 (6)	0.8291 (4)	−0.0538 (3)	0.0322 (7)
H15A	0.1122	0.9207	−0.0624	0.048*
H15B	−0.0351	0.7933	−0.0875	0.048*
H15C	0.1875	0.7775	−0.0939	0.048*
C16	0.3131 (6)	0.1419 (3)	0.5723 (3)	0.0306 (7)
H16A	0.4084	0.1630	0.5241	0.046*
H16B	0.1852	0.1326	0.5273	0.046*
H16D	0.3401	0.0594	0.5975	0.046*
O1W	0.9790 (4)	0.0827 (4)	0.3301 (3)	0.0424 (7)
H1W1	0.8765	0.1147	0.3016	0.064*
H2W1	1.0745	0.1130	0.3010	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02420 (12)	0.01775 (11)	0.03903 (14)	0.00238 (7)	0.00703 (8)	0.00088 (8)
O1	0.0389 (13)	0.0160 (10)	0.0252 (11)	−0.0005 (9)	0.0091 (9)	0.0027 (8)
N1	0.0246 (13)	0.0208 (12)	0.0261 (13)	0.0056 (10)	0.0014 (10)	−0.0005 (10)
C1	0.0253 (15)	0.0303 (17)	0.0294 (16)	0.0034 (13)	0.0053 (12)	0.0052 (13)
C2	0.0282 (16)	0.0319 (17)	0.0259 (15)	0.0016 (13)	0.0069 (12)	0.0037 (13)
C3	0.0275 (16)	0.0299 (17)	0.0289 (16)	−0.0004 (13)	0.0080 (13)	−0.0005 (13)
C4	0.0228 (15)	0.0164 (13)	0.0381 (17)	0.0012 (11)	0.0019 (12)	−0.0019 (12)
C5	0.0202 (13)	0.0215 (14)	0.0286 (15)	0.0041 (11)	0.0014 (11)	0.0025 (12)
C6	0.0291 (16)	0.0233 (15)	0.0249 (14)	0.0042 (12)	0.0036 (12)	0.0042 (12)
C7	0.0277 (15)	0.0236 (15)	0.0266 (15)	−0.0001 (12)	0.0021 (12)	0.0054 (12)
C8	0.0223 (14)	0.0207 (14)	0.0268 (15)	0.0037 (11)	−0.0014 (11)	0.0015 (11)
C9	0.0326 (17)	0.0175 (14)	0.0267 (15)	0.0008 (12)	0.0012 (12)	−0.0027 (11)
C10	0.0360 (17)	0.0137 (13)	0.0294 (15)	−0.0009 (12)	0.0062 (13)	0.0002 (11)
C11	0.0234 (14)	0.0175 (13)	0.0261 (14)	0.0002 (11)	0.0075 (11)	0.0028 (11)
C12	0.0280 (15)	0.0161 (13)	0.0274 (14)	0.0022 (11)	0.0092 (12)	−0.0030 (11)
C13	0.0245 (15)	0.0172 (13)	0.0311 (15)	0.0053 (11)	0.0030 (12)	0.0021 (11)
C14	0.0357 (17)	0.0156 (13)	0.0297 (15)	0.0001 (12)	0.0073 (13)	0.0037 (11)
C15	0.048 (2)	0.0227 (16)	0.0302 (16)	0.0060 (14)	0.0148 (15)	0.0080 (13)
C16	0.042 (2)	0.0209 (15)	0.0265 (15)	0.0068 (14)	0.0019 (14)	−0.0004 (12)
O1W	0.0321 (14)	0.060 (2)	0.0382 (15)	0.0036 (13)	0.0045 (11)	0.0178 (14)

Geometric parameters (Å, º) top

O1—C11	1.357 (4)	C9—C10	1.381 (5)
O1—C14	1.445 (4)	C9—H9A	0.9300
N1—C1	1.353 (4)	C10—C11	1.393 (4)
N1—C5	1.357 (4)	C10—H10A	0.9300
N1—C16	1.483 (4)	C11—C12	1.400 (4)
C1—C2	1.370 (5)	C12—C13	1.374 (5)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.387 (5)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.504 (5)
C3—C4	1.380 (5)	C14—H14A	0.9700
C3—H3A	0.9300	C14—H14B	0.9700
C4—C5	1.410 (5)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.438 (5)	C15—H15C	0.9600
C6—C7	1.342 (5)	C16—H16A	0.9600
C6—H6A	0.9300	C16—H16B	0.9600
C7—C8	1.470 (5)	C16—H16D	0.9600
C7—H7A	0.9300	O1W—H1W1	0.8501
C8—C13	1.401 (5)	O1W—H2W1	0.8500
C8—C9	1.406 (4)

C11—O1—C14	116.9 (3)	C9—C10—C11	119.0 (3)
C1—N1—C5	121.6 (3)	C9—C10—H10A	120.5
C1—N1—C16	117.5 (3)	C11—C10—H10A	120.5
C5—N1—C16	120.8 (3)	O1—C11—C10	125.1 (3)
N1—C1—C2	121.9 (3)	O1—C11—C12	114.9 (3)
N1—C1—H1A	119.1	C10—C11—C12	120.0 (3)
C2—C1—H1A	119.1	C13—C12—C11	120.1 (3)
C1—C2—C3	118.2 (3)	C13—C12—H12A	119.9
C1—C2—H2A	120.9	C11—C12—H12A	119.9
C3—C2—H2A	120.9	C12—C13—C8	121.4 (3)
C4—C3—C2	119.9 (3)	C12—C13—H13A	119.3
C4—C3—H3A	120.0	C8—C13—H13A	119.3
C2—C3—H3A	120.0	O1—C14—C15	107.6 (3)
C3—C4—C5	120.5 (3)	O1—C14—H14A	110.2
C3—C4—H4A	119.7	C15—C14—H14A	110.2
C5—C4—H4A	119.7	O1—C14—H14B	110.2
N1—C5—C4	117.7 (3)	C15—C14—H14B	110.2
N1—C5—C6	119.0 (3)	H14A—C14—H14B	108.5
C4—C5—C6	123.3 (3)	C14—C15—H15A	109.5
C7—C6—C5	122.9 (3)	C14—C15—H15B	109.5
C7—C6—H6A	118.5	H15A—C15—H15B	109.5
C5—C6—H6A	118.5	C14—C15—H15C	109.5
C6—C7—C8	126.3 (3)	H15A—C15—H15C	109.5
C6—C7—H7A	116.9	H15B—C15—H15C	109.5
C8—C7—H7A	116.9	N1—C16—H16A	109.5
C13—C8—C9	117.3 (3)	N1—C16—H16B	109.5
C13—C8—C7	123.3 (3)	H16A—C16—H16B	109.5
C9—C8—C7	119.4 (3)	N1—C16—H16D	109.5
C10—C9—C8	122.3 (3)	H16A—C16—H16D	109.5
C10—C9—H9A	118.9	H16B—C16—H16D	109.5
C8—C9—H9A	118.9	H1W1—O1W—H2W1	107.7

C5—N1—C1—C2	0.8 (5)	C6—C7—C8—C9	−177.4 (4)
C16—N1—C1—C2	−177.3 (3)	C13—C8—C9—C10	0.1 (5)
N1—C1—C2—C3	−0.6 (5)	C7—C8—C9—C10	−178.8 (3)
C1—C2—C3—C4	−1.2 (5)	C8—C9—C10—C11	−0.6 (5)
C2—C3—C4—C5	2.8 (5)	C14—O1—C11—C10	5.3 (5)
C1—N1—C5—C4	0.8 (5)	C14—O1—C11—C12	−175.7 (3)
C16—N1—C5—C4	178.8 (3)	C9—C10—C11—O1	−179.8 (3)
C1—N1—C5—C6	−178.9 (3)	C9—C10—C11—C12	1.2 (5)
C16—N1—C5—C6	−0.8 (5)	O1—C11—C12—C13	179.5 (3)
C3—C4—C5—N1	−2.5 (5)	C10—C11—C12—C13	−1.5 (5)
C3—C4—C5—C6	177.1 (3)	C11—C12—C13—C8	1.0 (5)
N1—C5—C6—C7	178.5 (3)	C9—C8—C13—C12	−0.3 (5)
C4—C5—C6—C7	−1.1 (5)	C7—C8—C13—C12	178.5 (3)
C5—C6—C7—C8	179.8 (3)	C11—O1—C14—C15	179.4 (3)
C6—C7—C8—C13	3.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1	0.85	2.88	3.681 (3)	158
O1W—H2W1···I1ⁱ	0.85	2.88	3.690 (3)	159
C16—H16B···O1Wⁱⁱ	0.96	2.49	3.346 (5)	148

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈NO⁺·I⁻·H₂O
M_r	385.23
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9261 (4), 10.1857 (6), 11.6303 (6)
α, β, γ (°)	100.829 (2), 97.399 (2), 92.892 (2)
V (Å³)	796.81 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.36 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.528, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	18790, 4635, 4333
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.14
No. of reflections	4635
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.16, −0.83

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1997) 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	0.85	2.8785	3.681 (3)	158
O1W—H2W1···I1ⁱ	0.85	2.8832	3.690 (3)	159
C16—H16B···O1Wⁱⁱ	0.96	2.4906	3.346 (5)	148

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

Acknowledgements

The authors thank Prince of Songkla University for financial support. The authors also thank the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) No. 304/PFIZIK/653003/A118.

References

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