Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Pages o2676-o2677
https://doi.org/10.1107/S1600536809040446

(E)-1-Methyl-4-styrylpyridinium iodide monohydrate

Hoong-Kun Fun,a*‡ Suchada Chantrapromma,b§ Chanasuk Surasitb and Kullapa Chanawannob

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my

(Received 29 September 2009; accepted 4 October 2009; online 10 October 2009)

In the title compound, C14H14N+·I−·H2O, the cation is essentially planar, with a dihedral angle of 2.55 (7)° between the pyridinium and phenyl rings, and exists in an E configuration with respect to the ethenyl bond. In the crystal structure, the cations are stacked in an anti­parallel manner along the a axis. The cation is linked to the water mol­ecule by a weak C—H⋯O inter­action, and the water mol­ecule is further linked to the I− ion by O—H⋯I hydrogen bonds. The crystal structure is consolidated by these inter­actions and is further stabilized by a π–π inter­action between the pyridinium and phenyl rings with a centroid–centroid distance of 3.6850 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to non-linear optical materials research, see: Chemla & Zyss (1987[Chemla, D. S. & Zyss, J. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals, pp. 32-198. New York: Academic Press.]); Chia et al. (1995[Chia, W.-L., Chen, C.-N. & Sheu, H.-J. (1995). Mater. Res. Bull. 30, 1421-1430.]); Dittrich et al. (2003[Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.]); Lin et al. (2002[Lin, Y. Y., Rajesh, N. P., Raghavan, P., Ramasamy, P. & Huang, Y. C. (2002). Mater. Lett. 56, 1074-1077.]); Prasad & Williams (1991[Prasad, P. N. & Williams, D. J. (1991). Introduction to Nonlinear Optical Effects in Molecules and Polymers. New York: John Wiley.]). For related structures, see: Chanawanno et al. (2008[Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1882-o1883.]); Chantrapromma, Jindawong & Fun (2007[Chantrapromma, S., Jindawong, B. & Fun, H.-K. (2007). Acta Cryst. E63, o2020-o2022.]); Chantrapromma, Jindawong, Fun & Patil (2007[Chantrapromma, S., Jindawong, B., Fun, H.-K. & Patil, P. S. (2007). Acta Cryst. E63, o2321-o2323.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C14H14N+·I−·H2O

  • Mr = 341.18

  • Monoclinic, P 21 /c

  • a = 7.3636 (1) Å

  • b = 10.5929 (1) Å

  • c = 18.2807 (2) Å

  • β = 106.770 (1)°

  • V = 1365.29 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.33 mm−1

  • T = 100 K

  • 0.32 × 0.22 × 0.20 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.524, Tmax = 0.649

  • 27548 measured reflections

  • 6004 independent reflections

  • 5307 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.058

  • S = 1.05

  • 6004 reflections

  • 163 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.32 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1W1⋯I1i 0.94 (3) 2.70 (3) 3.6458 (14) 177 (3)
O1W—H2W1⋯I1ii 0.93 (3) 2.66 (2) 3.5826 (12) 174 (2)
C14—H14A⋯O1Wii 0.96 2.52 3.3775 (19) 149
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809040446/is2467sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040446/is2467Isup2.hkl

checkCIF report


Comment top

The design and synthesis of nonlinear optical (NLO) materials have been receiving much attention due to their numerous applications (Chemla & Zyss, 1987; Prasad & Williams, 1991). In the search for new organic NLO materials, aromatic compounds with extended π-conjugation system are extensively studied (Chia et al., 1995; Dittrich et al., 2003). Such materials require molecular hyperpolarizability and orientation in a noncentrosymmetric arrangement of the bulk material (Lin et al., 2002; Prasad & Williams, 1991). During the course of our systematic studies of organic NLO materials, we have previously synthesized and reported the crystal structures of pyridinium and quinolinium iodide (Chanawanno et al., 2008; Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007). Herein we report the crystal structure of the title pyridinium derivative (I). However (I) crystallizes in centrosymmetric P21/c space group which precludes the second-order nonlinear optical properties.

The title compound consists of a C14H14N+ cation, an I- anion and one water molecule (Fig. 1). The cation exists in an E configuration with respect to the C6═C7 ethenyl bond [1.3429 (18) Å] with the torsion angle of C5–C6–C7–C8 = -179.95 (13)°. The cation is essentially planar with the dihedral angles between the pyridinium [C1–C5/N1] and benzene rings being 2.55 (7)°. The ethenyl unit is co-planar with the pyridinium and benzene rings as indicated by the torsion angles C1–C5–C6–C7 = -1.4 (2)° and C6–C7–C8–C9 = 1.6 (2)°. The rms deviation from the plane through the cation is 0.027 (15) Å. The bond distances in the cation have normal values (Allen et al., 1987) and comparable with the closely related compounds (Chanawanno et al., 2008; Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007).

In the crystal packing (Fig. 2), the cations are stacked in an antiparallel manner along the a axis. The cation is linked with the water molecule by a C—H···O weak interaction. The water molecule is further linked with the I- ion by O—H···I hydrogen bonds, forming a 3D network (Table 1). The crystal is consolidated by these interactions and further stabilized by π–π interactions with a distance of Cg1···Cg2iii = 3.6850 (8) Å [symmetry code: (iii) -x, 1-y, 2-z]; Cg1 and Cg2 are the centroids of the C1–C5/N1 and C8–C13 rings, respectively.

Related literature top

For bond-length data, see: Allen et al. (1987). For background to non-linerar optical materials research, see: Chemla & Zyss (1987); Chia et al. (1995); Dittrich et al. (2003); Lin et al. (2002); Prasad & Williams (1991). For related structures, see: Chanawanno et al. (2008); Chantrapromma, Jindawong & Fun (2007); Chantrapromma, Jindawong, Fun & Patil (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

(E)-1-Methyl-4-styrylpyridinium iodide was prepared by mixing 1:1:1 molar ratio solutions of 1,4-dimethylpyridinium iodide (2 g, 8.5 mmol), benzaldehyde (0.86 ml, 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 and washed with diethylether. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from methanol by slow evaporation at room temperature over a few weeks (m.p. 489-490 K).

Refinement top

Water H atoms were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with 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 highest residual electron density peak is located at 0.70 Å from I1 and the deepest hole is located at 0.54 Å from I1.

Structure description top

The design and synthesis of nonlinear optical (NLO) materials have been receiving much attention due to their numerous applications (Chemla & Zyss, 1987; Prasad & Williams, 1991). In the search for new organic NLO materials, aromatic compounds with extended π-conjugation system are extensively studied (Chia et al., 1995; Dittrich et al., 2003). Such materials require molecular hyperpolarizability and orientation in a noncentrosymmetric arrangement of the bulk material (Lin et al., 2002; Prasad & Williams, 1991). During the course of our systematic studies of organic NLO materials, we have previously synthesized and reported the crystal structures of pyridinium and quinolinium iodide (Chanawanno et al., 2008; Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007). Herein we report the crystal structure of the title pyridinium derivative (I). However (I) crystallizes in centrosymmetric P21/c space group which precludes the second-order nonlinear optical properties.

The title compound consists of a C14H14N+ cation, an I- anion and one water molecule (Fig. 1). The cation exists in an E configuration with respect to the C6═C7 ethenyl bond [1.3429 (18) Å] with the torsion angle of C5–C6–C7–C8 = -179.95 (13)°. The cation is essentially planar with the dihedral angles between the pyridinium [C1–C5/N1] and benzene rings being 2.55 (7)°. The ethenyl unit is co-planar with the pyridinium and benzene rings as indicated by the torsion angles C1–C5–C6–C7 = -1.4 (2)° and C6–C7–C8–C9 = 1.6 (2)°. The rms deviation from the plane through the cation is 0.027 (15) Å. The bond distances in the cation have normal values (Allen et al., 1987) and comparable with the closely related compounds (Chanawanno et al., 2008; Chantrapromma, Jindawong & Fun, 2007; Chantrapromma, Jindawong, Fun & Patil, 2007).

In the crystal packing (Fig. 2), the cations are stacked in an antiparallel manner along the a axis. The cation is linked with the water molecule by a C—H···O weak interaction. The water molecule is further linked with the I- ion by O—H···I hydrogen bonds, forming a 3D network (Table 1). The crystal is consolidated by these interactions and further stabilized by π–π interactions with a distance of Cg1···Cg2iii = 3.6850 (8) Å [symmetry code: (iii) -x, 1-y, 2-z]; Cg1 and Cg2 are the centroids of the C1–C5/N1 and C8–C13 rings, respectively.

For bond-length data, see: Allen et al. (1987). For background to non-linerar optical materials research, see: Chemla & Zyss (1987); Chia et al. (1995); Dittrich et al. (2003); Lin et al. (2002); Prasad & Williams (1991). For related structures, see: Chanawanno et al. (2008); Chantrapromma, Jindawong & Fun (2007); Chantrapromma, Jindawong, Fun & Patil (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 molecular structure 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 c axis. O—H···I hydrogen bonds and C—H···O interactions are shown as dashed lines.
(E)-1-Methyl-4-styrylpyridinium iodide monohydrate top
Crystal data top
C14H14N+·I−·H2OF(000) = 672
Mr = 341.18Dx = 1.660 Mg m−3
Monoclinic, P21/cMelting point = 489–490 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.3636 (1) ÅCell parameters from 6004 reflections
b = 10.5929 (1) Åθ = 2.3–35.0°
c = 18.2807 (2) ŵ = 2.33 mm−1
β = 106.770 (1)°T = 100 K
V = 1365.29 (3) Å3Block, yellow
Z = 40.32 × 0.22 × 0.20 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6004 independent reflections
Radiation source: sealed tube5307 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 35.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −11→11
Tmin = 0.524, Tmax = 0.649k = −17→16
27548 measured reflectionsl = −29→28
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0248P)2 + 0.8184P]
where P = (Fo2 + 2Fc2)/3
6004 reflections(Δ/σ)max = 0.004
163 parametersΔρmax = 1.32 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C14H14N+·I−·H2OV = 1365.29 (3) Å3
Mr = 341.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.3636 (1) ŵ = 2.33 mm−1
b = 10.5929 (1) ÅT = 100 K
c = 18.2807 (2) Å0.32 × 0.22 × 0.20 mm
β = 106.770 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6004 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5307 reflections with I > 2σ(I)
Tmin = 0.524, Tmax = 0.649Rint = 0.021
27548 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 1.32 e Å−3
6004 reflectionsΔρmin = −0.56 e Å−3
163 parameters
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*/Ueq
I10.742589 (15)0.831113 (9)0.885210 (5)0.02548 (3)
O1W0.20711 (19)0.98174 (12)0.94686 (7)0.0308 (2)
H1W10.086 (4)0.944 (3)0.9327 (16)0.060 (8)*
H2W10.210 (4)1.028 (2)0.9901 (15)0.048 (7)*
N10.53960 (16)0.74866 (11)1.12888 (6)0.01776 (19)
C10.3622 (2)0.68934 (13)1.00380 (8)0.0219 (2)
H1A0.31460.70960.95230.026*
C20.4699 (2)0.77624 (13)1.05393 (8)0.0218 (2)
H2A0.49480.85461.03600.026*
C30.5064 (2)0.63509 (12)1.15607 (7)0.0185 (2)
H3A0.55560.61741.20790.022*
C40.4006 (2)0.54563 (12)1.10806 (7)0.0187 (2)
H4A0.37960.46761.12750.022*
C50.32393 (19)0.57076 (12)1.02979 (7)0.0176 (2)
C60.2111 (2)0.47325 (12)0.98062 (7)0.0191 (2)
H6A0.19600.39671.00310.023*
C70.12773 (19)0.48617 (12)0.90531 (7)0.0188 (2)
H7A0.14340.56290.88320.023*
C80.01415 (19)0.38969 (12)0.85514 (7)0.0175 (2)
C9−0.0249 (2)0.27106 (12)0.88126 (8)0.0195 (2)
H9A0.02590.24960.93240.023*
C10−0.1394 (2)0.18542 (12)0.83081 (9)0.0214 (2)
H10A−0.16340.10650.84820.026*
C11−0.2182 (2)0.21752 (13)0.75423 (8)0.0214 (2)
H11A−0.29750.16090.72100.026*
C12−0.1783 (2)0.33396 (13)0.72750 (8)0.0226 (2)
H12A−0.22970.35510.67630.027*
C13−0.0616 (2)0.41849 (13)0.77750 (8)0.0206 (2)
H13A−0.03310.49560.75920.025*
C140.6473 (2)0.84639 (13)1.18135 (8)0.0234 (3)
H14A0.73490.88661.15880.035*
H14B0.71600.80791.22880.035*
H14C0.56110.90821.19060.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03493 (6)0.02076 (4)0.01682 (4)−0.00883 (3)0.00120 (3)0.00305 (3)
O1W0.0324 (6)0.0315 (6)0.0294 (5)0.0025 (5)0.0103 (5)−0.0004 (4)
N10.0178 (5)0.0184 (4)0.0172 (4)−0.0012 (4)0.0054 (4)−0.0003 (3)
C10.0249 (7)0.0220 (6)0.0176 (5)−0.0017 (5)0.0043 (5)0.0029 (4)
C20.0247 (7)0.0209 (6)0.0199 (5)−0.0022 (5)0.0065 (5)0.0038 (4)
C30.0203 (6)0.0177 (5)0.0183 (5)0.0011 (4)0.0068 (4)0.0015 (4)
C40.0207 (6)0.0174 (5)0.0191 (5)0.0005 (4)0.0074 (4)0.0018 (4)
C50.0166 (5)0.0181 (5)0.0182 (5)0.0008 (4)0.0055 (4)0.0011 (4)
C60.0202 (6)0.0177 (5)0.0194 (5)0.0002 (4)0.0060 (4)0.0017 (4)
C70.0193 (6)0.0181 (5)0.0192 (5)0.0008 (4)0.0058 (4)0.0025 (4)
C80.0159 (5)0.0178 (5)0.0188 (5)0.0006 (4)0.0051 (4)0.0005 (4)
C90.0186 (6)0.0181 (5)0.0212 (5)0.0024 (4)0.0049 (4)0.0033 (4)
C100.0207 (6)0.0158 (5)0.0281 (6)0.0012 (4)0.0077 (5)0.0023 (4)
C110.0198 (6)0.0208 (6)0.0238 (6)−0.0012 (5)0.0068 (5)−0.0047 (4)
C120.0243 (7)0.0251 (6)0.0178 (5)−0.0005 (5)0.0054 (5)0.0005 (4)
C130.0212 (6)0.0207 (5)0.0200 (5)−0.0015 (5)0.0064 (5)0.0026 (4)
C140.0248 (7)0.0228 (6)0.0224 (6)−0.0050 (5)0.0065 (5)−0.0044 (4)
Geometric parameters (Å, º) top
O1W—H1W10.94 (3)C7—C81.4637 (18)
O1W—H2W10.93 (3)C7—H7A0.9300
N1—C21.3491 (17)C8—C131.4005 (18)
N1—C31.3507 (17)C8—C91.4032 (19)
N1—C141.4772 (18)C9—C101.391 (2)
C1—C21.377 (2)C9—H9A0.9300
C1—C51.4003 (19)C10—C111.394 (2)
C1—H1A0.9300C10—H10A0.9300
C2—H2A0.9300C11—C121.389 (2)
C3—C41.3711 (19)C11—H11A0.9300
C3—H3A0.9300C12—C131.387 (2)
C4—C51.4039 (18)C12—H12A0.9300
C4—H4A0.9300C13—H13A0.9300
C5—C61.4608 (19)C14—H14A0.9600
C6—C71.3429 (18)C14—H14B0.9600
C6—H6A0.9300C14—H14C0.9600
H1W1—O1W—H2W1104 (2)C13—C8—C9118.63 (12)
C2—N1—C3120.69 (12)C13—C8—C7118.12 (12)
C2—N1—C14118.90 (12)C9—C8—C7123.24 (11)
C3—N1—C14120.37 (11)C10—C9—C8120.19 (12)
C2—C1—C5120.49 (12)C10—C9—H9A119.9
C2—C1—H1A119.8C8—C9—H9A119.9
C5—C1—H1A119.8C9—C10—C11120.24 (12)
N1—C2—C1120.55 (12)C9—C10—H10A119.9
N1—C2—H2A119.7C11—C10—H10A119.9
C1—C2—H2A119.7C12—C11—C10120.06 (13)
N1—C3—C4120.65 (12)C12—C11—H11A120.0
N1—C3—H3A119.7C10—C11—H11A120.0
C4—C3—H3A119.7C13—C12—C11119.69 (13)
C3—C4—C5120.56 (12)C13—C12—H12A120.2
C3—C4—H4A119.7C11—C12—H12A120.2
C5—C4—H4A119.7C12—C13—C8121.14 (12)
C1—C5—C4117.05 (12)C12—C13—H13A119.4
C1—C5—C6124.05 (12)C8—C13—H13A119.4
C4—C5—C6118.90 (12)N1—C14—H14A109.5
C7—C6—C5124.71 (12)N1—C14—H14B109.5
C7—C6—H6A117.6H14A—C14—H14B109.5
C5—C6—H6A117.6N1—C14—H14C109.5
C6—C7—C8125.51 (12)H14A—C14—H14C109.5
C6—C7—H7A117.2H14B—C14—H14C109.5
C8—C7—H7A117.2
C3—N1—C2—C10.5 (2)C5—C6—C7—C8−179.95 (13)
C14—N1—C2—C1−177.34 (14)C6—C7—C8—C13−179.47 (14)
C5—C1—C2—N1−0.2 (2)C6—C7—C8—C91.6 (2)
C2—N1—C3—C4−0.2 (2)C13—C8—C9—C10−1.1 (2)
C14—N1—C3—C4177.64 (13)C7—C8—C9—C10177.78 (13)
N1—C3—C4—C5−0.4 (2)C8—C9—C10—C11−0.9 (2)
C2—C1—C5—C4−0.3 (2)C9—C10—C11—C121.8 (2)
C2—C1—C5—C6179.97 (14)C10—C11—C12—C13−0.7 (2)
C3—C4—C5—C10.7 (2)C11—C12—C13—C8−1.3 (2)
C3—C4—C5—C6−179.63 (13)C9—C8—C13—C122.2 (2)
C1—C5—C6—C7−1.4 (2)C7—C8—C13—C12−176.72 (13)
C4—C5—C6—C7178.88 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···I1i0.94 (3)2.70 (3)3.6458 (14)177 (3)
O1W—H2W1···I1ii0.93 (3)2.66 (2)3.5826 (12)174 (2)
C14—H14A···O1Wii0.962.523.3775 (19)149
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formulaC14H14N+·I−·H2O
Mr341.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.3636 (1), 10.5929 (1), 18.2807 (2)
β (°) 106.770 (1)
V (Å3)1365.29 (3)
Z4
Radiation typeMo Kα
µ (mm−1)2.33
Crystal size (mm)0.32 × 0.22 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.524, 0.649
No. of measured, independent and
observed [I > 2σ(I)] reflections		27548, 6004, 5307
Rint0.021
(sin θ/λ)max (Å−1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.058, 1.05
No. of reflections6004
No. of parameters163
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.32, −0.56

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···I1i0.94 (3)2.70 (3)3.6458 (14)177 (3)
O1W—H2W1···I1ii0.93 (3)2.66 (2)3.5826 (12)174 (2)
C14—H14A···O1Wii0.962.523.3775 (19)149
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChanawanno, K., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1882–o1883.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChantrapromma, S., Jindawong, B. & Fun, H.-K. (2007). Acta Cryst. E63, o2020–o2022.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChantrapromma, S., Jindawong, B., Fun, H.-K. & Patil, P. S. (2007). Acta Cryst. E63, o2321–o2323.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChemla, D. S. & Zyss, J. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals, pp. 32–198. New York: Academic Press.  Google Scholar
 First citationChia, W.-L., Chen, C.-N. & Sheu, H.-J. (1995). Mater. Res. Bull. 30, 1421–1430.  CrossRef CAS Web of Science Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationDittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88–95.  Web of Science CrossRef CAS Google Scholar
 First citationLin, Y. Y., Rajesh, N. P., Raghavan, P., Ramasamy, P. & Huang, Y. C. (2002). Mater. Lett. 56, 1074–1077.  Web of Science CrossRef CAS Google Scholar
 First citationPrasad, P. N. & Williams, D. J. (1991). Introduction to Nonlinear Optical Effects in Molecules and Polymers. New York: John Wiley.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Pages o2676-o2677
https://doi.org/10.1107/S1600536809040446
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS