4-(2-Carb-oxy-vin-yl)pyridinium iodide.

In the crystal structure of the title salt, C(8)H(8)NO(2) (+)·I(-), the cations and anions are linked by bifurcated N-H⋯(O,I) hydrogen bonds. A near-linear O-H⋯I hydrogen bond also exists between the cation and anion, resulting in a two-dimensional network. In the cation, the carboxyl group is twisted with respect to the pyridine ring at a dihedral angle of 15.34 (17)°.

Related literature

3-(Pyridin-4-yl)acrylic acid is an inter­mediate in the synthesis of 3-amino-3-(pyridin-4-yl)propanoic acid, which is of inter­est as a precursor for the synthesis of novel biologically active compounds, see: Cohen et al. (2002 ▶); Qu et al. (2004 ▶).

Experimental

Crystal data

C8H8NO2 +·I−

M = 277.05

Monoclinic,

a = 4.9685 (10) Å

b = 15.494 (3) Å

c = 12.123 (2) Å

β = 101.48 (3)°

V = 914.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.46 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.492, T max = 0.518

9130 measured reflections

2099 independent reflections

1786 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.11

2099 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021501/xu2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021501/xu2766Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8NO2+·I−	F(000) = 528.0
Mr = 277.05	Dx = 2.012 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1866 reflections
a = 4.9685 (10) Å	θ = 3.2–27.0°
b = 15.494 (3) Å	µ = 3.46 mm−1
c = 12.123 (2) Å	T = 293 K
β = 101.48 (3)°	Prism, orange
V = 914.6 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2101 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scan	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.492, Tmax = 0.518	l = −15→15
9130 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0215P)2 + 0.0886P] where P = (Fo2 + 2Fc2)/3
2099 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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
N1	0.8838 (5)	0.62959 (16)	0.6895 (2)	0.0397 (6)
H1	1.0091	0.5971	0.7275	0.048*
C8	0.0739 (7)	0.91308 (18)	0.4041 (3)	0.0371 (7)
C3	0.7164 (6)	0.76753 (19)	0.6401 (3)	0.0387 (7)
H3	0.7325	0.8271	0.6486	0.046*
C6	0.2864 (6)	0.78463 (18)	0.4944 (3)	0.0362 (7)
H6	0.1361	0.7556	0.4527	0.043*
C4	0.4734 (6)	0.64341 (19)	0.5602 (3)	0.0396 (8)
H4	0.3229	0.6179	0.5138	0.048*
C5	0.4953 (6)	0.73228 (18)	0.5661 (2)	0.0321 (6)
C2	0.9097 (6)	0.7147 (2)	0.7004 (3)	0.0423 (8)
H2	1.0602	0.7382	0.7492	0.051*
C1	0.6722 (7)	0.59325 (19)	0.6224 (3)	0.0447 (8)
H1A	0.6590	0.5334	0.6176	0.054*
O1	0.1334 (5)	0.99482 (13)	0.3899 (2)	0.0527 (7)
H1B	0.0129	1.0164	0.3417	0.079*
O2	−0.1307 (4)	0.87875 (15)	0.3553 (2)	0.0545 (7)
C9	0.2913 (6)	0.8691 (2)	0.4834 (3)	0.0377 (7)
H9	0.4334	0.9009	0.5262	0.045*
I1	1.17185 (4)	0.413232 (12)	0.682811 (18)	0.04391 (10)

	U11	U22	U33	U12	U13	U23
N1	0.0317 (13)	0.0381 (14)	0.0457 (16)	0.0063 (12)	−0.0011 (12)	0.0076 (12)
C8	0.0352 (17)	0.0361 (17)	0.0362 (18)	0.0011 (13)	−0.0017 (14)	0.0004 (13)
C3	0.0338 (16)	0.0316 (15)	0.0467 (18)	−0.0007 (13)	−0.0019 (13)	−0.0005 (14)
C6	0.0326 (16)	0.0378 (16)	0.0348 (17)	−0.0021 (13)	−0.0019 (13)	−0.0013 (13)
C4	0.0345 (17)	0.0370 (16)	0.0425 (19)	−0.0007 (13)	−0.0042 (14)	−0.0072 (14)
C5	0.0296 (14)	0.0357 (15)	0.0290 (16)	0.0020 (12)	0.0011 (12)	0.0011 (12)
C2	0.0324 (16)	0.0444 (18)	0.044 (2)	−0.0041 (14)	−0.0058 (14)	0.0001 (15)
C1	0.047 (2)	0.0318 (17)	0.052 (2)	−0.0002 (14)	0.0021 (17)	0.0012 (14)
O1	0.0523 (15)	0.0370 (12)	0.0579 (16)	−0.0062 (11)	−0.0152 (12)	0.0125 (11)
O2	0.0441 (14)	0.0390 (12)	0.0663 (17)	−0.0051 (11)	−0.0227 (12)	0.0069 (12)
C9	0.0330 (16)	0.0394 (17)	0.0350 (17)	−0.0017 (13)	−0.0067 (13)	0.0005 (13)
I1	0.04248 (15)	0.03397 (14)	0.04898 (17)	−0.00119 (9)	−0.00609 (11)	−0.00440 (9)

N1—C1	1.321 (4)	C6—C5	1.460 (4)
N1—C2	1.330 (4)	C6—H6	0.9300
N1—H1	0.8600	C4—C1	1.360 (4)
C8—O2	1.195 (4)	C4—C5	1.382 (4)
C8—O1	1.319 (3)	C4—H4	0.9300
C8—C9	1.464 (4)	C2—H2	0.9300
C3—C2	1.359 (4)	C1—H1A	0.9300
C3—C5	1.385 (4)	O1—H1B	0.8200
C3—H3	0.9300	C9—H9	0.9300
C6—C9	1.316 (4)
C1—N1—C2	122.3 (3)	C5—C4—H4	120.0
C1—N1—H1	118.9	C4—C5—C3	118.0 (3)
C2—N1—H1	118.9	C4—C5—C6	118.9 (3)
O2—C8—O1	123.6 (3)	C3—C5—C6	123.0 (3)
O2—C8—C9	124.2 (3)	N1—C2—C3	120.0 (3)
O1—C8—C9	112.2 (3)	N1—C2—H2	120.0
C2—C3—C5	119.7 (3)	C3—C2—H2	120.0
C2—C3—H3	120.1	N1—C1—C4	119.9 (3)
C5—C3—H3	120.1	N1—C1—H1A	120.0
C9—C6—C5	126.0 (3)	C4—C1—H1A	120.0
C9—C6—H6	117.0	C8—O1—H1B	109.5
C5—C6—H6	117.0	C6—C9—C8	120.2 (3)
C1—C4—C5	120.0 (3)	C6—C9—H9	119.9
C1—C4—H4	120.0	C8—C9—H9	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1	0.86	3.04	3.652 (3)	130
N1—H1···O2i	0.86	2.15	2.819 (3)	134
O1—H1B···I1ii	0.82	2.54	3.362 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯I1	0.86	3.04	3.652 (3)	130
N1—H1⋯O2i	0.86	2.15	2.819 (3)	134
O1—H1B⋯I1ii	0.82	2.54	3.362 (2)	175

Symmetry codes: (i) ; (ii) .