2-[(E)-4-(Diethyl­amino)­styr­yl]-1-methyl­pyridinium iodide

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

doi:10.1107/S1600536810037505

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2639-o2640

doi:10.1107/S1600536810037505

Open

access

2-[(E)-4-(Diethylamino)styryl]-1-methylpyridinium iodide

Narissara Kaewmanee,^a Kullapa Chanawanno,^a Suchada Chantrapromma ^a ^*‡ and Hoong-Kun Fun ^b §

^aCrystal Materials Research Unit, Department 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

(Received 6 September 2010; accepted 19 September 2010; online 25 September 2010)

In the title compound, C₁₈H₂₃N₂⁺·I⁻, the cation exists in the E configuration with respect to the ethenyl C=C bond. The pyridinium and benzene rings are nearly coplanar, making a dihedral angle of 4.63 (7)°. The two ethyl groups of the diethylamino substituent point in opposite directions with respect to the benzene plane. In the crystal, the cation and the iodide anion are linked by a weak C—H⋯I interaction. The cations are stacked in an anti-parallel manner along the a axis by a π–π interaction with a centroid–centroid distance of 3.5262 (9) Å. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to styryl pyridinium quaternary ammonium compounds, see: Browning et al. (1922 , 1923 ); Chanawanno et al. (2010 ); Wainwright & Kristiansen (2003 ). For related structures, see: Chanawanno et al. (2008 ); Fun et al. (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₂₃N₂⁺·I⁻
M_r = 394.28
Monoclinic, P 2₁ /c
a = 7.7099 (1) Å
b = 20.2780 (4) Å
c = 10.9375 (2) Å
β = 92.527 (1)°
V = 1708.32 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.87 mm⁻¹
T = 100 K
0.34 × 0.30 × 0.21 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.570, T_max = 0.691
23707 measured reflections
6198 independent reflections
5765 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.070
S = 1.10
6198 reflections
282 parameters
All H-atom parameters refined
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯I1ⁱ	0.91 (3)	2.99 (3)	3.7980 (18)	148.8 (19)
C18—H18B⋯Cg2ⁱⁱ	0.94 (3)	2.79 (3)	3.6270 (17)	149 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037505/is2599sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037505/is2599Isup2.hkl

checkCIF report

Comment top

For a long time, styryl pyridinium quaternary ammonium compounds were known to exhibit antiseptic properties (Browning et al., 1922, 1923). However medicinal researchers have long neglected to further develop the styryl pyridinium chromophore compounds for use as antibacterial agents due to the superior properties of penicillin until the incoming of the penicillin-resistant bacteria phenomenon, for example, methicillin-resistant Staphylococcus aureus, MRSA. The most interesting feature of styryl pyridinium quaternary ammonium compounds is their very specific activity to MRSA which is a vital drug-resistant bacteria (Wainwright & Kristiansen, 2003; Chanawanno et al., 2010). From this significant reason, our research group has synthesized and characterized several styryl pyridinium derivatives including the title compound (I) in order to search for new potent antibacterial agents. Herein we report the crystal structure of (I).

Figure 1 shows the asymmetric unit of (I), which consists of a C₁₈H₂₃N₂⁺ cation and an I^- anion. The cation exists in the E configuration with respect to the C6═C7 double bond [1.350 (2) Å] with the torsion angle C5–C6–C7–C8 = -179.29 (16)°. The pyridinium and benzene rings are nearly coplanar with the ethenyl bridge with the dihedral angle between the pyridinium and benzene rings being 4.63 (7)°. The two ethyl groups of the diethylamino substituent pointed towards the opposite directions with respect to the plane of benzene ring. The conformation of the diethylamino can be indicated by the torsion angles C11–N2–C14–C15 = 84.7 (2)° and C11–N2–C16–C17 = 79.0 (2)°. The bond lengths of cation in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Chanawanno et al., 2008; Fun et al., 2009).

In the crystal packing (Fig. 2), the cations are arranged in a zig-zag manner along the b axis with the iodide ions located in the interstitials of the cations and linked to the cations by a C—H···I weak interaction (Table 1). The cations stacked approximately along the a axis in an antiparallel manner by π–π interaction with the Cg1···Cg2ⁱⁱⁱ distance of 3.5262 (9) Å [symmetry code: (iii) 1-x, 1-y, 1-z]; Cg1 and Cg2 are centroids of N1/C1–C5 and C8–C13 rings, respectively. The crystal structure is further stabilized by C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For background to styryl pyridinium quaternary ammonium compounds, see: Browning et al. (1922, 1923); Chanawanno et al. (2010); Wainwright & Kristiansen (2003). For related structures, see: Chanawanno et al. (2008); 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 (I) was prepared by mixing 1:1:1 molar ratio solutions of 1,2-dimethylpyridinium iodide (2 g, 8.5 mmol), 4-diethylaminobenzaldehyde (1.52 ml, 8.5 mmol) and piperidine (0.84 ml, 8.5 mmol) in methanol (40 ml). The resulting solution was refluxed for 6 hours under a nitrogen atmosphere. The orange solid which formed was filtered and washed with diethylether. Orange block-shaped single crystals of (I) suitable for x-ray structure determination were recrystallized from methanol by slow evaporation at room temperature over a few weeks (m.p. 527-529 K).

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

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed down the a axis. Weak C—H···I interactions are shown as dashed lines.

2-[(E)-4-(Diethylamino)styryl]-1-methylpyridinium iodide top

Crystal data top

C₁₈H₂₃N₂⁺·I⁻	F(000) = 792
M_r = 394.28	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 527–529 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7099 (1) Å	Cell parameters from 6198 reflections
b = 20.2780 (4) Å	θ = 2.0–32.6°
c = 10.9375 (2) Å	µ = 1.87 mm⁻¹
β = 92.527 (1)°	T = 100 K
V = 1708.32 (5) Å³	Block, orange
Z = 4	0.34 × 0.30 × 0.21 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	6198 independent reflections
Radiation source: sealed tube	5765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→11
T_min = 0.570, T_max = 0.691	k = −29→30
23707 measured reflections	l = −16→16

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	All H-atom parameters refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0312P)² + 1.8072P] where P = (F_o² + 2F_c²)/3
6198 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₈H₂₃N₂⁺·I⁻	V = 1708.32 (5) Å³
M_r = 394.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7099 (1) Å	µ = 1.87 mm⁻¹
b = 20.2780 (4) Å	T = 100 K
c = 10.9375 (2) Å	0.34 × 0.30 × 0.21 mm
β = 92.527 (1)°

Data collection top

Bruker APEXII CCD area detector diffractometer	6198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5765 reflections with I > 2σ(I)
T_min = 0.570, T_max = 0.691	R_int = 0.026
23707 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.070	All H-atom parameters refined
S = 1.10	Δρ_max = 0.51 e Å⁻³
6198 reflections	Δρ_min = −0.63 e Å⁻³
282 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

	x	y	z	U_iso*/U_eq
I1	0.385998 (14)	0.649927 (5)	0.254076 (9)	0.01744 (4)
N1	0.27082 (18)	0.63425 (7)	0.69740 (12)	0.0128 (2)
N2	0.1456 (2)	0.33502 (7)	0.09996 (13)	0.0165 (3)
C1	0.3117 (2)	0.66702 (9)	0.80338 (15)	0.0156 (3)
C2	0.3971 (2)	0.63637 (9)	0.89989 (15)	0.0169 (3)
C3	0.4439 (2)	0.57021 (9)	0.88598 (15)	0.0181 (3)
C4	0.4023 (2)	0.53711 (8)	0.77893 (15)	0.0159 (3)
C5	0.3120 (2)	0.56923 (8)	0.68124 (14)	0.0130 (3)
C6	0.2616 (2)	0.53758 (8)	0.56679 (15)	0.0149 (3)
C7	0.3027 (2)	0.47469 (8)	0.53980 (14)	0.0141 (3)
C8	0.2575 (2)	0.44086 (8)	0.42673 (14)	0.0136 (3)
C9	0.1595 (2)	0.46906 (8)	0.32844 (15)	0.0144 (3)
C10	0.1223 (2)	0.43480 (8)	0.22166 (15)	0.0150 (3)
C11	0.1815 (2)	0.36902 (8)	0.20590 (14)	0.0135 (3)
C12	0.2802 (2)	0.34044 (8)	0.30475 (15)	0.0131 (3)
C13	0.3169 (2)	0.37578 (8)	0.41093 (14)	0.0133 (3)
C14	0.0388 (2)	0.36290 (9)	−0.00116 (15)	0.0173 (3)
C15	0.1390 (3)	0.40606 (10)	−0.08716 (17)	0.0216 (3)
C16	0.2067 (2)	0.26717 (8)	0.08518 (15)	0.0164 (3)
C17	0.0948 (3)	0.21691 (9)	0.14881 (17)	0.0201 (3)
C18	0.1817 (2)	0.67224 (9)	0.59821 (16)	0.0182 (3)
H1A	0.285 (3)	0.7107 (13)	0.805 (2)	0.020 (6)*
H2A	0.426 (4)	0.6591 (13)	0.971 (3)	0.029 (7)*
H3A	0.512 (4)	0.5499 (14)	0.954 (3)	0.031 (7)*
H4A	0.434 (3)	0.4942 (13)	0.774 (2)	0.019 (6)*
H6A	0.198 (3)	0.5628 (12)	0.507 (2)	0.014 (5)*
H7A	0.369 (3)	0.4489 (13)	0.598 (2)	0.020 (6)*
H9A	0.120 (3)	0.5160 (13)	0.332 (2)	0.021 (6)*
H10A	0.055 (4)	0.4541 (14)	0.158 (3)	0.027 (7)*
H12A	0.325 (3)	0.2966 (13)	0.298 (2)	0.020 (6)*
H14A	−0.057 (3)	0.3869 (13)	0.030 (2)	0.017 (6)*
H13A	0.384 (3)	0.3571 (11)	0.476 (2)	0.015 (6)*
H14B	−0.013 (3)	0.3265 (13)	−0.047 (2)	0.021 (6)*
H15A	0.061 (4)	0.4195 (15)	−0.156 (3)	0.037 (8)*
H15B	0.238 (4)	0.3824 (14)	−0.117 (2)	0.026 (7)*
H15C	0.180 (4)	0.4425 (15)	−0.047 (3)	0.028 (7)*
H16A	0.323 (3)	0.2637 (13)	0.115 (2)	0.022 (6)*
H16B	0.202 (3)	0.2567 (13)	0.002 (2)	0.020 (6)*
H17A	0.139 (4)	0.1730 (15)	0.135 (3)	0.029 (7)*
H17B	0.098 (3)	0.2228 (14)	0.236 (2)	0.021 (6)*
H17C	−0.022 (4)	0.2207 (14)	0.121 (2)	0.027 (7)*
H18A	0.176 (4)	0.7175 (14)	0.623 (2)	0.027 (7)*
H18B	0.069 (4)	0.6552 (14)	0.586 (3)	0.032 (8)*
H18C	0.244 (4)	0.6682 (14)	0.525 (3)	0.023 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02091 (6)	0.01714 (6)	0.01425 (6)	0.00473 (4)	0.00049 (4)	0.00028 (3)
N1	0.0135 (6)	0.0121 (6)	0.0130 (5)	0.0000 (4)	0.0022 (4)	0.0001 (4)
N2	0.0239 (7)	0.0128 (6)	0.0126 (6)	0.0009 (5)	−0.0015 (5)	−0.0015 (5)
C1	0.0179 (7)	0.0143 (7)	0.0147 (6)	−0.0003 (5)	0.0036 (5)	−0.0022 (5)
C2	0.0183 (7)	0.0200 (7)	0.0126 (6)	−0.0052 (6)	0.0026 (5)	−0.0017 (5)
C3	0.0205 (7)	0.0187 (7)	0.0149 (6)	−0.0030 (6)	−0.0018 (5)	0.0035 (6)
C4	0.0196 (7)	0.0125 (7)	0.0154 (6)	−0.0013 (5)	−0.0016 (5)	0.0020 (5)
C5	0.0121 (6)	0.0129 (6)	0.0140 (6)	−0.0011 (5)	0.0019 (5)	−0.0003 (5)
C6	0.0161 (7)	0.0143 (7)	0.0142 (6)	0.0000 (5)	−0.0013 (5)	−0.0013 (5)
C7	0.0142 (6)	0.0140 (7)	0.0141 (6)	−0.0010 (5)	0.0006 (5)	−0.0007 (5)
C8	0.0144 (6)	0.0128 (6)	0.0136 (6)	0.0001 (5)	0.0013 (5)	−0.0011 (5)
C9	0.0143 (6)	0.0128 (6)	0.0160 (6)	0.0015 (5)	0.0014 (5)	−0.0003 (5)
C10	0.0168 (7)	0.0137 (7)	0.0146 (6)	0.0021 (5)	−0.0005 (5)	0.0014 (5)
C11	0.0150 (6)	0.0128 (6)	0.0127 (6)	−0.0012 (5)	0.0011 (5)	−0.0010 (5)
C12	0.0134 (6)	0.0122 (6)	0.0140 (6)	−0.0014 (5)	0.0016 (5)	0.0012 (5)
C13	0.0136 (6)	0.0126 (6)	0.0138 (6)	0.0009 (5)	0.0011 (5)	0.0003 (5)
C14	0.0184 (7)	0.0195 (7)	0.0137 (6)	−0.0006 (6)	−0.0029 (5)	−0.0005 (6)
C15	0.0229 (8)	0.0255 (9)	0.0166 (7)	0.0000 (7)	0.0018 (6)	0.0029 (6)
C16	0.0208 (7)	0.0134 (7)	0.0150 (6)	0.0005 (6)	0.0019 (5)	−0.0033 (5)
C17	0.0229 (8)	0.0172 (8)	0.0205 (7)	−0.0029 (6)	0.0025 (6)	−0.0042 (6)
C18	0.0213 (8)	0.0171 (7)	0.0161 (7)	0.0037 (6)	−0.0008 (6)	0.0014 (6)

Geometric parameters (Å, º) top

N1—C1	1.361 (2)	C9—H9A	1.00 (3)
N1—C5	1.369 (2)	C10—C11	1.423 (2)
N1—C18	1.475 (2)	C10—H10A	0.93 (3)
N2—C11	1.366 (2)	C11—C12	1.418 (2)
N2—C14	1.463 (2)	C12—C13	1.383 (2)
N2—C16	1.466 (2)	C12—H12A	0.96 (3)
C1—C2	1.368 (2)	C13—H13A	0.94 (2)
C1—H1A	0.91 (3)	C14—C15	1.521 (3)
C2—C3	1.399 (3)	C14—H14A	0.96 (3)
C2—H2A	0.92 (3)	C14—H14B	0.97 (3)
C3—C4	1.375 (2)	C15—H15A	0.99 (3)
C3—H3A	0.98 (3)	C15—H15B	0.97 (3)
C4—C5	1.409 (2)	C15—H15C	0.91 (3)
C4—H4A	0.91 (3)	C16—C17	1.523 (3)
C5—C6	1.445 (2)	C16—H16A	0.94 (3)
C6—C7	1.350 (2)	C16—H16B	0.94 (2)
C6—H6A	0.95 (2)	C17—H17A	0.97 (3)
C7—C8	1.443 (2)	C17—H17B	0.96 (2)
C7—H7A	0.95 (3)	C17—H17C	0.94 (3)
C8—C9	1.408 (2)	C18—H18A	0.96 (3)
C8—C13	1.410 (2)	C18—H18B	0.94 (3)
C9—C10	1.378 (2)	C18—H18C	0.95 (3)

C1—N1—C5	122.25 (14)	C12—C11—C10	117.06 (14)
C1—N1—C18	117.02 (14)	C13—C12—C11	120.75 (15)
C5—N1—C18	120.72 (14)	C13—C12—H12A	119.0 (15)
C11—N2—C14	122.16 (15)	C11—C12—H12A	120.2 (15)
C11—N2—C16	120.88 (14)	C12—C13—C8	122.16 (14)
C14—N2—C16	116.90 (13)	C12—C13—H13A	120.7 (15)
N1—C1—C2	121.39 (16)	C8—C13—H13A	117.1 (15)
N1—C1—H1A	116.3 (16)	N2—C14—C15	113.93 (15)
C2—C1—H1A	122.2 (16)	N2—C14—H14A	110.1 (15)
C1—C2—C3	117.98 (15)	C15—C14—H14A	110.4 (15)
C1—C2—H2A	120.7 (18)	N2—C14—H14B	107.8 (16)
C3—C2—H2A	121.3 (18)	C15—C14—H14B	109.0 (16)
C4—C3—C2	120.60 (15)	H14A—C14—H14B	105 (2)
C4—C3—H3A	122.5 (17)	C14—C15—H15A	108.9 (18)
C2—C3—H3A	116.9 (17)	C14—C15—H15B	110.5 (17)
C3—C4—C5	120.59 (16)	H15A—C15—H15B	110 (2)
C3—C4—H4A	118.0 (16)	C14—C15—H15C	110.0 (18)
C5—C4—H4A	121.4 (16)	H15A—C15—H15C	109 (2)
N1—C5—C4	117.18 (14)	H15B—C15—H15C	108 (2)
N1—C5—C6	118.99 (14)	N2—C16—C17	112.73 (15)
C4—C5—C6	123.83 (15)	N2—C16—H16A	109.7 (16)
C7—C6—C5	123.55 (15)	C17—C16—H16A	109.9 (16)
C7—C6—H6A	118.6 (15)	N2—C16—H16B	108.7 (16)
C5—C6—H6A	117.8 (15)	C17—C16—H16B	107.1 (16)
C6—C7—C8	125.91 (15)	H16A—C16—H16B	109 (2)
C6—C7—H7A	119.8 (15)	C16—C17—H17A	109.6 (17)
C8—C7—H7A	114.3 (15)	C16—C17—H17B	112.3 (16)
C9—C8—C13	116.92 (14)	H17A—C17—H17B	106 (2)
C9—C8—C7	124.21 (15)	C16—C17—H17C	110.5 (17)
C13—C8—C7	118.86 (14)	H17A—C17—H17C	111 (2)
C10—C9—C8	121.80 (15)	H17B—C17—H17C	107 (2)
C10—C9—H9A	117.3 (14)	N1—C18—H18A	108.7 (16)
C8—C9—H9A	120.8 (14)	N1—C18—H18B	107.8 (18)
C9—C10—C11	121.30 (15)	H18A—C18—H18B	110 (2)
C9—C10—H10A	120.4 (17)	N1—C18—H18C	109.5 (17)
C11—C10—H10A	118.3 (17)	H18A—C18—H18C	110 (2)
N2—C11—C12	121.47 (15)	H18B—C18—H18C	111 (3)
N2—C11—C10	121.47 (15)

C5—N1—C1—C2	0.1 (2)	C7—C8—C9—C10	179.02 (16)
C18—N1—C1—C2	−178.88 (16)	C8—C9—C10—C11	0.0 (3)
N1—C1—C2—C3	1.0 (3)	C14—N2—C11—C12	177.77 (15)
C1—C2—C3—C4	−1.1 (3)	C16—N2—C11—C12	0.6 (2)
C2—C3—C4—C5	0.1 (3)	C14—N2—C11—C10	−2.6 (3)
C1—N1—C5—C4	−1.1 (2)	C16—N2—C11—C10	−179.73 (15)
C18—N1—C5—C4	177.87 (15)	C9—C10—C11—N2	−179.66 (16)
C1—N1—C5—C6	178.99 (15)	C9—C10—C11—C12	0.0 (2)
C18—N1—C5—C6	−2.1 (2)	N2—C11—C12—C13	179.33 (15)
C3—C4—C5—N1	1.0 (2)	C10—C11—C12—C13	−0.3 (2)
C3—C4—C5—C6	−179.10 (16)	C11—C12—C13—C8	0.6 (2)
N1—C5—C6—C7	176.94 (16)	C9—C8—C13—C12	−0.6 (2)
C4—C5—C6—C7	−3.0 (3)	C7—C8—C13—C12	−179.43 (15)
C5—C6—C7—C8	−179.29 (16)	C11—N2—C14—C15	84.7 (2)
C6—C7—C8—C9	−1.4 (3)	C16—N2—C14—C15	−98.03 (19)
C6—C7—C8—C13	177.33 (16)	C11—N2—C16—C17	79.0 (2)
C13—C8—C9—C10	0.3 (2)	C14—N2—C16—C17	−98.24 (18)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···I1ⁱ	0.91 (3)	2.99 (3)	3.7980 (18)	148.8 (19)
C18—H18B···Cg2ⁱⁱ	0.94 (3)	2.79 (3)	3.6270 (17)	149 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃N₂⁺·I⁻
M_r	394.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.7099 (1), 20.2780 (4), 10.9375 (2)
β (°)	92.527 (1)
V (Å³)	1708.32 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.34 × 0.30 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.570, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	23707, 6198, 5765
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.070, 1.10
No. of reflections	6198
No. of parameters	282
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.63

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···I1ⁱ	0.91 (3)	2.99 (3)	3.7980 (18)	148.8 (19)
C18—H18B···Cg2ⁱⁱ	0.94 (3)	2.79 (3)	3.6270 (17)	149 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, email: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Browning, C. H., Cohen, J. B., Ellingworth, S. & Gulbransen, R. (1923). Br. Med. J. 25, 326. CrossRef Google Scholar
Browning, C. H., Cohen, J. B. & Gulbransen, R. (1922). Br. Med. J. 1, 514–515. CrossRef CAS PubMed Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199–4208. Web of Science CSD CrossRef CAS PubMed Google Scholar
Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1882–o1883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o1934–o1935. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wainwright, M. & Kristiansen, J. E. (2003). Int. J. Antimicrob. Agents, 22, 479–486. Web of Science CrossRef PubMed CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2639-o2640

doi:10.1107/S1600536810037505

Open

access