organic compounds
2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylpyridinium iodide monohydrate
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
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 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
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell 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
https://doi.org/10.1107/S1600536807061375/sj2440sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061375/sj2440Isup2.hkl
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
were recrystalized from methanol by slow evaporation of the solvent at room temperature over several days (Mp. 481–483 K).All H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H = 0.85 ° and C—H distances in the range 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq of the
for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.85 Å from I1 and the deepest hole is located at 0.63 Å from I1.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 and therefore does not exhibit non-linear optical properties (Williams, 1984).
The
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 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.
the cations are packed in an anti-parallel fashion throughFor 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).
Data collection: APEX2 (Bruker, 2005); cell
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).C16H18NO+·I−·H2O | Z = 2 |
Mr = 385.23 | F(000) = 384 |
Triclinic, P1 | Dx = 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 |
Bruker APEXII CCD area-detector diffractometer | 4635 independent reflections |
Radiation source: fine-focus sealed tube | 4333 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 1.8° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.528, Tmax = 0.797 | l = −16→16 |
18790 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0521P)2 + 1.6362P] where P = (Fo2 + 2Fc2)/3 |
4635 reflections | (Δ/σ)max < 0.001 |
184 parameters | Δρmax = 2.16 e Å−3 |
0 restraints | Δρmin = −0.83 e Å−3 |
C16H18NO+·I−·H2O | γ = 92.892 (2)° |
Mr = 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)° |
Bruker APEXII CCD area-detector diffractometer | 4635 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4333 reflections with I > 2σ(I) |
Tmin = 0.528, Tmax = 0.797 | Rint = 0.028 |
18790 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.14 | Δρmax = 2.16 e Å−3 |
4635 reflections | Δρmin = −0.83 e Å−3 |
184 parameters |
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 | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.528, 0.797 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18790, 4635, 4333 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 2.16, −0.83 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1997) and PLATON (Spek, 2003).
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.
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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.