4-{(1E,3E)-4-[4-(Di­methyl­amino)­phen­yl]buta-1,3-dien-1-yl}-1-methyl­pyridin-1-ium iodide

John Sundaram, S.; Sagayaraj, P.; Antony Raj, A.; Dravida Thendral, E.R.A.; Usha, G.

doi:10.1107/S2414314616014632

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161463

doi:10.1107/S2414314616014632

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4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide

S. John Sundaram,^a P. Sagayaraj,^a A. Antony Raj,^a E. R. A. Dravida Thendral ^b and G. Usha ^b ^*

^aDepartment of Physics, Loyola College, Chennai-34, Tamilnadu, India, and ^bPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 September 2016; accepted 15 September 2016; online 27 September 2016)

The title molecular salt, C₁₈H₂₁N₂⁺·I⁻, consists of a pyridinium cation and an I⁻ anion. The cation exists in an E,E conformation with respect to the two C=C double bonds, and is roughly planar with the pyridinium ring being inclined to the benzene ring by 10.8 (2) °. In the crystal, the ions are linked by a C—H⋯I hydrogen bond, and the cations are linked by C—H⋯π interactions, forming zigzag chains propagating along [010].

Keywords: crystal structure; pyridinium; iodide; C–H⋯I hydrogen bonds; C–H⋯π interactions.

CCDC reference: 1487591

Structure description

Pyridinium derivatives have long been observed to exhibit antiseptic properties (Browning et al., 1923 ). Pyridinium chromophore compounds are particularly important because of their activity against methicillin-resistant Staphylococcus aureus (MRSA),which is a drug-resistant bacterium (Wainwright & Kristiansen, 2003 ; Chanawanno et al., 2010 ). Pyridinium halide salts possess promising antimicrobial properties due to the reactive functional groups covalently bonded to the long hydrophobic chain (Fisicaro et al., 1990 ; Chanawanno et al., 2010). Anions in pyridinium derivatives have been proven to control their antimicrobial activity and different anion kinds can exhibit different antimicrobial activities (Pernak et al., 2001 ). The crystal structures of some closely related pyridinium iodide salts have been reported, viz. (E)-2-[4-(dimethylamino)styryl]-1-methylpyridinium triiodide (Fun et al., 2011 ), 2-[(E)-4-(diethylamino)styryl]-1-methylpyridinium iodide (Kaewmanee et al., 2010 ), (E)-1-methyl-2-styrylpyridinium iodide (Fun et al., 2009 ) and 2-[(E)-2-(4-chlorophenyl)ethenyl]-1-methylpyridinium iodide monohydrate (Chanawanno et al. 2008 ).

The asymmetric unit of the title molecular salt, Fig. 1, comprises a pyridinium cation and an I⁻ anion. The bond lengths and angles for the cation are comparable with those of the closely related structures mentioned above. The cation exists in an E,E conformation with respect to the two C=C double bonds, C6=C7 and C8=C9. It is roughly planar with the pyridinium ring (N1/C1–C5) being inclined to the benzene ring (C10–C15) by 10.8 (2)°.

Figure 1
The molecular structure of the title molecular salt, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, the ions are linked by a C—H⋯I hydrogen bond, and the cations are linked by C—H⋯π interactions, forming zigzag chains propagating along the b-axis direction (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯I1	0.93	2.99	3.855 (5)	154
C12—H12⋯Cgⁱ	0.93	2.95	3.577 (5)	126
Symmetry code: (i) $[-x-1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A partial view along the c axis of the crystal packing of the title molecular salt. The C—H⋯I hydrogen bond and the C—H⋯π interactions are shown as dashed lines (see Table 1

), and for clarity only H atoms H3 and H12 have been included.

Synthesis and crystallization

The title molecular salt was synthesized by the Knoevenagel condensation of 1,4-dimethyl pyridinium iodide (2.35 g, 10 mmol) in methanol (30 ml) and 4-N,N-dimethylamino cinnamaldehyde (1.75 g, 10 mmol) in the presence of piperidine (0.2 ml). The total mixture was taken in a round-bottom flask (1000 ml capacity) of a Dean–Stark apparatus. The mixture was refluxed for 12 h and then cooled to room temperature. The product was filtered and recrystallized three times from methanol solution yielding black block-like crystals (m.p. 539 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₂⁺·I⁻
M_r	392.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.6659 (4), 7.4965 (5), 34.7364 (17)
β (°)	94.7132 (19)
V (Å³)	1729.94 (18)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.85
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.636, 0.732
No. of measured, independent and observed [I > 2σ(I)] reflections	12906, 3028, 2887
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.080, 1.33
No. of reflections	3022
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −1.04
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick 2008 ), SHELXL-2014/7 (Sheldrick, 2015 ), SHELXTL (Sheldrick 2008) and Mercury (Macrae et al., 2008 ), SHELXTL (Sheldrick 2008).

Structural data

CCDC reference: 1487591

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616014632/su4072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014632/su4072Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616014632/su4072Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL-2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide top

Crystal data top

C₁₈H₂₁N₂⁺·I⁻	D_x = 1.506 Mg m⁻³
M_r = 392.27	Melting point: 539 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6659 (4) Å	Cell parameters from 7371 reflections
b = 7.4965 (5) Å	θ = 2.8–26.8°
c = 34.7364 (17) Å	µ = 1.85 mm⁻¹
β = 94.7132 (19)°	T = 296 K
V = 1729.94 (18) Å³	Block, black
Z = 4	0.25 × 0.22 × 0.18 mm
F(000) = 784

Data collection top

Bruker APEXII CCD diffractometer	2887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
φ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
T_min = 0.636, T_max = 0.732	k = −7→8
12906 measured reflections	l = −41→38
3028 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0122P)² + 3.3223P] where P = (F_o² + 2F_c²)/3
S = 1.33	(Δ/σ)_max = 0.002
3022 reflections	Δρ_max = 0.35 e Å⁻³
193 parameters	Δρ_min = −1.04 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.6000 (7)	0.9316 (6)	0.58510 (14)	0.0499 (12)
H1	0.6626	1.0027	0.6045	0.060*
C2	0.6891 (7)	0.9085 (7)	0.55189 (15)	0.0531 (12)
H2	0.8120	0.9635	0.5490	0.064*
C3	0.4274 (7)	0.7278 (6)	0.52763 (13)	0.0458 (11)
H3	0.3689	0.6573	0.5077	0.055*
C4	0.3317 (7)	0.7466 (6)	0.56030 (13)	0.0445 (11)
H4	0.2091	0.6897	0.5624	0.053*
C5	0.4162 (6)	0.8511 (5)	0.59099 (12)	0.0374 (10)
C6	0.3244 (7)	0.8776 (6)	0.62645 (13)	0.0435 (11)
H6	0.3955	0.9468	0.6451	0.052*
C7	0.1463 (7)	0.8128 (6)	0.63545 (13)	0.0402 (10)
H7	0.0702	0.7484	0.6166	0.048*
C8	0.0656 (7)	0.8357 (6)	0.67190 (13)	0.0427 (11)
H8	0.1385	0.9038	0.6906	0.051*
C9	−0.1093 (6)	0.7647 (6)	0.68079 (12)	0.0392 (10)
H9	−0.1829	0.7036	0.6611	0.047*
C10	−0.1968 (6)	0.7721 (5)	0.71744 (12)	0.0346 (9)
C11	−0.3882 (7)	0.6997 (6)	0.72128 (12)	0.0395 (10)
H11	−0.4579	0.6484	0.6998	0.047*
C12	−0.4762 (6)	0.7016 (6)	0.75548 (12)	0.0394 (10)
H12	−0.6042	0.6535	0.7565	0.047*
C13	−0.3763 (6)	0.7755 (5)	0.78926 (12)	0.0327 (9)
C14	−0.1835 (6)	0.8477 (6)	0.78520 (13)	0.0393 (10)
H14	−0.1121	0.8973	0.8067	0.047*
C15	−0.0986 (6)	0.8470 (6)	0.75079 (13)	0.0404 (10)
H15	0.0280	0.8977	0.7494	0.048*
C16	−0.6777 (6)	0.7474 (7)	0.82429 (13)	0.0485 (12)
H16A	−0.7505	0.8254	0.8062	0.073*
H16B	−0.7169	0.7704	0.8498	0.073*
H16C	−0.7076	0.6257	0.8174	0.073*
C17	−0.3576 (8)	0.8521 (7)	0.85801 (13)	0.0516 (13)
H17A	−0.2294	0.7944	0.8627	0.077*
H17B	−0.4360	0.8327	0.8796	0.077*
H17C	−0.3378	0.9778	0.8546	0.077*
C18	0.7111 (8)	0.7743 (8)	0.48821 (15)	0.0601 (14)
H18A	0.8084	0.6812	0.4934	0.090*
H18B	0.7783	0.8812	0.4811	0.090*
H18C	0.6160	0.7384	0.4674	0.090*
I1	0.14120 (5)	0.59463 (4)	0.43097 (2)	0.04734 (12)
N1	0.6043 (6)	0.8081 (5)	0.52308 (11)	0.0443 (9)
N2	−0.4628 (5)	0.7789 (5)	0.82341 (10)	0.0389 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.042 (3)	0.054 (3)	−0.015 (2)	0.005 (2)	−0.009 (2)
C2	0.050 (3)	0.045 (3)	0.066 (3)	−0.014 (2)	0.012 (2)	0.002 (3)
C3	0.053 (3)	0.045 (3)	0.040 (2)	−0.003 (2)	0.002 (2)	−0.002 (2)
C4	0.043 (3)	0.040 (3)	0.051 (3)	−0.008 (2)	0.004 (2)	−0.001 (2)
C5	0.042 (2)	0.028 (2)	0.042 (2)	−0.0023 (18)	0.0025 (19)	0.0016 (18)
C6	0.054 (3)	0.034 (3)	0.042 (2)	−0.005 (2)	0.004 (2)	−0.004 (2)
C7	0.047 (3)	0.033 (2)	0.041 (2)	0.000 (2)	0.004 (2)	−0.002 (2)
C8	0.050 (3)	0.037 (2)	0.041 (2)	0.001 (2)	0.005 (2)	−0.004 (2)
C9	0.044 (3)	0.032 (2)	0.040 (2)	0.0036 (19)	0.0011 (19)	−0.0025 (19)
C10	0.036 (2)	0.028 (2)	0.039 (2)	0.0037 (18)	0.0005 (18)	−0.0025 (18)
C11	0.047 (3)	0.032 (2)	0.038 (2)	−0.006 (2)	−0.0032 (19)	−0.0099 (19)
C12	0.036 (2)	0.038 (2)	0.043 (2)	−0.009 (2)	0.0010 (19)	−0.004 (2)
C13	0.033 (2)	0.025 (2)	0.038 (2)	0.0037 (17)	−0.0066 (17)	0.0030 (18)
C14	0.032 (2)	0.043 (3)	0.041 (2)	−0.0004 (19)	−0.0071 (18)	−0.007 (2)
C15	0.030 (2)	0.044 (3)	0.046 (3)	−0.0022 (18)	−0.0033 (19)	−0.003 (2)
C16	0.041 (3)	0.063 (3)	0.041 (3)	−0.006 (2)	0.005 (2)	0.003 (2)
C17	0.061 (3)	0.054 (3)	0.038 (3)	−0.010 (2)	−0.007 (2)	−0.002 (2)
C18	0.070 (4)	0.058 (3)	0.055 (3)	0.007 (3)	0.028 (3)	0.010 (3)
I1	0.04592 (18)	0.0529 (2)	0.04281 (18)	−0.01053 (15)	0.00116 (12)	0.00207 (16)
N1	0.054 (2)	0.036 (2)	0.044 (2)	0.0072 (18)	0.0102 (18)	0.0074 (18)
N2	0.0374 (19)	0.044 (2)	0.0345 (19)	−0.0011 (17)	−0.0022 (15)	−0.0032 (17)

Geometric parameters (Å, º) top

C1—C2	1.351 (7)	C11—C12	1.367 (6)
C1—C5	1.396 (6)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.414 (6)
C2—N1	1.339 (6)	C12—H12	0.9300
C2—H2	0.9300	C13—N2	1.361 (5)
C3—N1	1.345 (6)	C13—C14	1.412 (6)
C3—C4	1.354 (6)	C14—C15	1.364 (6)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.403 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—N2	1.455 (5)
C5—C6	1.433 (6)	C16—H16A	0.9600
C6—C7	1.344 (6)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.426 (6)	C17—N2	1.449 (5)
C7—H7	0.9300	C17—H17A	0.9600
C8—C9	1.341 (6)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C10	1.444 (6)	C18—N1	1.476 (6)
C9—H9	0.9300	C18—H18A	0.9600
C10—C15	1.401 (6)	C18—H18B	0.9600
C10—C11	1.403 (6)	C18—H18C	0.9600

C2—C1—C5	121.5 (4)	C13—C12—H12	119.4
C2—C1—H1	119.3	N2—C13—C14	122.3 (4)
C5—C1—H1	119.3	N2—C13—C12	121.8 (4)
N1—C2—C1	121.5 (4)	C14—C13—C12	115.9 (4)
N1—C2—H2	119.3	C15—C14—C13	122.2 (4)
C1—C2—H2	119.3	C15—C14—H14	118.9
N1—C3—C4	122.0 (4)	C13—C14—H14	118.9
N1—C3—H3	119.0	C14—C15—C10	121.8 (4)
C4—C3—H3	119.0	C14—C15—H15	119.1
C3—C4—C5	120.5 (4)	C10—C15—H15	119.1
C3—C4—H4	119.7	N2—C16—H16A	109.5
C5—C4—H4	119.7	N2—C16—H16B	109.5
C1—C5—C4	115.6 (4)	H16A—C16—H16B	109.5
C1—C5—C6	120.5 (4)	N2—C16—H16C	109.5
C4—C5—C6	123.9 (4)	H16A—C16—H16C	109.5
C7—C6—C5	126.7 (4)	H16B—C16—H16C	109.5
C7—C6—H6	116.7	N2—C17—H17A	109.5
C5—C6—H6	116.7	N2—C17—H17B	109.5
C6—C7—C8	124.6 (4)	H17A—C17—H17B	109.5
C6—C7—H7	117.7	N2—C17—H17C	109.5
C8—C7—H7	117.7	H17A—C17—H17C	109.5
C9—C8—C7	123.7 (4)	H17B—C17—H17C	109.5
C9—C8—H8	118.1	N1—C18—H18A	109.5
C7—C8—H8	118.1	N1—C18—H18B	109.5
C8—C9—C10	127.6 (4)	H18A—C18—H18B	109.5
C8—C9—H9	116.2	N1—C18—H18C	109.5
C10—C9—H9	116.2	H18A—C18—H18C	109.5
C15—C10—C11	116.3 (4)	H18B—C18—H18C	109.5
C15—C10—C9	123.3 (4)	C2—N1—C3	118.9 (4)
C11—C10—C9	120.3 (4)	C2—N1—C18	120.5 (4)
C12—C11—C10	122.5 (4)	C3—N1—C18	120.4 (4)
C12—C11—H11	118.8	C13—N2—C17	121.3 (4)
C10—C11—H11	118.8	C13—N2—C16	120.2 (3)
C11—C12—C13	121.3 (4)	C17—N2—C16	117.0 (4)
C11—C12—H12	119.4

C5—C1—C2—N1	0.4 (8)	C11—C12—C13—N2	179.7 (4)
N1—C3—C4—C5	−0.4 (7)	C11—C12—C13—C14	0.7 (6)
C2—C1—C5—C4	−0.2 (7)	N2—C13—C14—C15	−178.8 (4)
C2—C1—C5—C6	−180.0 (5)	C12—C13—C14—C15	0.2 (6)
C3—C4—C5—C1	0.2 (7)	C13—C14—C15—C10	−0.9 (7)
C3—C4—C5—C6	179.9 (4)	C11—C10—C15—C14	0.7 (6)
C1—C5—C6—C7	178.0 (5)	C9—C10—C15—C14	−178.3 (4)
C4—C5—C6—C7	−1.8 (7)	C1—C2—N1—C3	−0.5 (7)
C5—C6—C7—C8	176.8 (4)	C1—C2—N1—C18	−175.6 (5)
C6—C7—C8—C9	−177.6 (5)	C4—C3—N1—C2	0.5 (7)
C7—C8—C9—C10	176.1 (4)	C4—C3—N1—C18	175.6 (5)
C8—C9—C10—C15	−5.0 (7)	C14—C13—N2—C17	−2.1 (6)
C8—C9—C10—C11	176.1 (4)	C12—C13—N2—C17	178.9 (4)
C15—C10—C11—C12	0.2 (6)	C14—C13—N2—C16	163.7 (4)
C9—C10—C11—C12	179.2 (4)	C12—C13—N2—C16	−15.2 (6)
C10—C11—C12—C13	−0.9 (7)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···I1	0.93	2.99	3.855 (5)	154
C12—H12···Cgⁱ	0.93	2.95	3.577 (5)	126

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

Acknowledgements

The authors thank DST–SERB, India for funding, the Central Instrumentation Facility, Queen Mary's College, Chennai-4 for computing facilities and V. Ramkumar, Department of Chemistry, IIT, Madras, for the X-ray data collection facility.

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IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161463

doi:10.1107/S2414314616014632

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

4-{(1E,3E)-4-[4-(Di­methyl­amino)­phen­yl]buta-1,3-dien-1-yl}-1-methyl­pyridin-1-ium iodide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide