3-Methyl-2-vinyl-pyridinium phosphate.

In the title salt, C8H10N(+)·H2PO4 (-), the cation is essentially planar (r.m.s. deviation = 0.063 Å). In the crystal, the phosphate anions form inversion R 2 (2)(8) dimers via pairs of O-H⋯O hydrogen bonds. These dimers are further linked by pairs of O-H⋯O hydrogen bonds, also enclosing R 2 (2)(8) loops, forming chains running along [001]. The cations are bonded to the anions via N-H⋯O hydrogen bonds and C-H⋯O contacts.

Related literature

For the biological activity of 4-amino­pyridine, see: Judge & Bever (2006 ▶); Schwid et al. (1997 ▶); Strupp et al. (2004 ▶). For related structures, see: Anderson et al. (2005 ▶); Fun et al. (2009 ▶); Sabari et al. (2012 ▶).

Experimental

Crystal data

C8H10N+·H2PO4 −

M = 217.16

Monoclinic,

a = 7.7089 (6) Å

b = 16.3668 (13) Å

c = 8.0649 (6) Å

β = 109.689 (4)°

V = 958.06 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2008 ▶) T min = 0.922, T max = 0.947

8970 measured reflections

2362 independent reflections

2052 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.114

S = 1.08

2362 reflections

136 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300576X/bt6887sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300576X/bt6887Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300576X/bt6887Isup3.cml

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

C8H10N+·H2O4P−	F(000) = 456
Mr = 217.16	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8834 reflections
a = 7.7089 (6) Å	θ = 2.1–31.2°
b = 16.3668 (13) Å	µ = 0.28 mm−1
c = 8.0649 (6) Å	T = 293 K
β = 109.689 (4)°	Block, colourless
V = 958.06 (13) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2362 independent reflections
Radiation source: fine-focus sealed tube	2052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker 2008)	h = −10→10
Tmin = 0.922, Tmax = 0.947	k = −21→17
8970 measured reflections	l = −10→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2803P] where P = (Fo2 + 2Fc2)/3
2362 reflections	(Δ/σ)max = 0.003
136 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.33 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
C1	0.5293 (2)	0.35216 (10)	0.9141 (2)	0.0394 (4)
H1A	0.5318	0.4089	0.9225	0.047*
C2	0.6707 (3)	0.30687 (12)	1.0253 (3)	0.0446 (4)
H2	0.7706	0.3322	1.1082	0.054*
C3	0.6608 (2)	0.22259 (11)	1.0112 (3)	0.0420 (4)
H3	0.7546	0.1911	1.0870	0.050*
C4	0.5138 (2)	0.18417 (10)	0.8859 (2)	0.0349 (4)
C5	0.3751 (2)	0.23315 (9)	0.7738 (2)	0.0304 (3)
C6	0.2165 (2)	0.19908 (11)	0.6336 (2)	0.0404 (4)
H6	0.1973	0.1432	0.6382	0.048*
C7	0.1003 (3)	0.23843 (13)	0.5042 (3)	0.0514 (5)
H7A	0.1131	0.2945	0.4934	0.062*
H7B	0.0040	0.2106	0.4221	0.062*
C8	0.5063 (3)	0.09263 (11)	0.8732 (3)	0.0545 (5)
H8A	0.3981	0.0732	0.8944	0.082*
H8B	0.6139	0.0699	0.9594	0.082*
H8C	0.5020	0.0762	0.7576	0.082*
N1	0.38850 (18)	0.31502 (8)	0.79424 (17)	0.0319 (3)
H1	0.3015	0.3448	0.7263	0.038*
O1	0.20750 (17)	0.49478 (7)	0.95492 (15)	0.0374 (3)
O2	0.12761 (18)	0.42554 (7)	0.65535 (15)	0.0414 (3)
O3	−0.11397 (18)	0.44558 (8)	0.78857 (17)	0.0460 (3)
O4	0.0217 (2)	0.56754 (7)	0.68547 (16)	0.0446 (3)
P1	0.06935 (6)	0.48168 (2)	0.77599 (5)	0.03024 (15)
H3A	−0.143 (4)	0.4698 (16)	0.875 (3)	0.082 (9)*
H4A	−0.032 (4)	0.5639 (19)	0.5694 (14)	0.093 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0427 (9)	0.0273 (8)	0.0485 (10)	−0.0054 (6)	0.0156 (8)	−0.0067 (7)
C2	0.0361 (9)	0.0435 (10)	0.0475 (10)	−0.0078 (7)	0.0052 (8)	−0.0079 (8)
C3	0.0358 (9)	0.0410 (10)	0.0443 (10)	0.0033 (7)	0.0070 (8)	0.0046 (8)
C4	0.0373 (8)	0.0276 (8)	0.0396 (9)	0.0001 (6)	0.0127 (7)	0.0030 (6)
C5	0.0335 (8)	0.0259 (7)	0.0333 (8)	−0.0020 (6)	0.0132 (6)	0.0008 (6)
C6	0.0433 (9)	0.0311 (8)	0.0416 (9)	−0.0076 (7)	0.0075 (8)	−0.0013 (7)
C7	0.0503 (11)	0.0437 (10)	0.0529 (11)	0.0008 (8)	0.0077 (9)	−0.0073 (9)
C8	0.0614 (12)	0.0271 (9)	0.0652 (13)	0.0024 (8)	0.0085 (10)	0.0084 (9)
N1	0.0333 (7)	0.0259 (7)	0.0360 (7)	0.0012 (5)	0.0113 (6)	0.0007 (5)
O1	0.0367 (6)	0.0395 (6)	0.0296 (6)	−0.0004 (5)	0.0028 (5)	−0.0013 (5)
O2	0.0573 (8)	0.0318 (6)	0.0308 (6)	0.0166 (5)	0.0092 (5)	0.0004 (5)
O3	0.0444 (7)	0.0518 (8)	0.0377 (7)	−0.0129 (6)	0.0083 (6)	−0.0120 (6)
O4	0.0703 (9)	0.0243 (6)	0.0330 (6)	0.0110 (5)	0.0093 (6)	0.0008 (5)
P1	0.0375 (2)	0.0230 (2)	0.0260 (2)	0.00340 (14)	0.00509 (17)	−0.00119 (14)

C1—N1	1.333 (2)	C7—H7A	0.9300
C1—C2	1.372 (3)	C7—H7B	0.9300
C1—H1A	0.9300	C8—H8A	0.9600
C2—C3	1.384 (3)	C8—H8B	0.9600
C2—H2	0.9300	C8—H8C	0.9600
C3—C4	1.389 (2)	N1—H1	0.8600
C3—H3	0.9300	O1—P1	1.4923 (12)
C4—C5	1.397 (2)	O2—P1	1.5122 (12)
C4—C8	1.502 (2)	O3—P1	1.5663 (13)
C5—N1	1.350 (2)	O3—H3A	0.889 (10)
C5—C6	1.467 (2)	O4—P1	1.5691 (12)
C6—C7	1.295 (3)	O4—H4A	0.889 (10)
C6—H6	0.9300
N1—C1—C2	120.08 (16)	C6—C7—H7B	120.0
N1—C1—H1A	120.0	H7A—C7—H7B	120.0
C2—C1—H1A	120.0	C4—C8—H8A	109.5
C1—C2—C3	118.37 (17)	C4—C8—H8B	109.5
C1—C2—H2	120.8	H8A—C8—H8B	109.5
C3—C2—H2	120.8	C4—C8—H8C	109.5
C2—C3—C4	121.31 (17)	H8A—C8—H8C	109.5
C2—C3—H3	119.3	H8B—C8—H8C	109.5
C4—C3—H3	119.3	C1—N1—C5	123.48 (14)
C3—C4—C5	118.04 (15)	C1—N1—H1	118.3
C3—C4—C8	120.31 (16)	C5—N1—H1	118.3
C5—C4—C8	121.65 (16)	P1—O3—H3A	110.5 (19)
N1—C5—C4	118.69 (14)	P1—O4—H4A	113 (2)
N1—C5—C6	118.75 (14)	O1—P1—O2	116.08 (7)
C4—C5—C6	122.55 (15)	O1—P1—O3	110.92 (7)
C7—C6—C5	127.06 (17)	O2—P1—O3	106.41 (8)
C7—C6—H6	116.5	O1—P1—O4	107.46 (7)
C5—C6—H6	116.5	O2—P1—O4	108.58 (7)
C6—C7—H7A	120.0	O3—P1—O4	107.04 (8)
N1—C1—C2—C3	−1.1 (3)	C8—C4—C5—C6	−1.8 (2)
C1—C2—C3—C4	1.1 (3)	N1—C5—C6—C7	13.1 (3)
C2—C3—C4—C5	0.1 (3)	C4—C5—C6—C7	−166.36 (19)
C2—C3—C4—C8	−179.99 (18)	C2—C1—N1—C5	−0.2 (2)
C3—C4—C5—N1	−1.3 (2)	C4—C5—N1—C1	1.3 (2)
C8—C4—C5—N1	178.81 (16)	C6—C5—N1—C1	−178.12 (15)
C3—C4—C5—C6	178.18 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.83	2.6558 (18)	160
O3—H3A···O1i	0.89 (1)	1.72 (1)	2.5995 (18)	173 (3)
O4—H4A···O2ii	0.89 (1)	1.72 (1)	2.6002 (17)	170 (3)
C1—H1A···O1iii	0.93	2.48	3.172 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.83	2.6558 (18)	160
O3—H3A⋯O1i	0.89 (1)	1.72 (1)	2.5995 (18)	173 (3)
O4—H4A⋯O2ii	0.89 (1)	1.72 (1)	2.6002 (17)	170 (3)
C1—H1A⋯O1iii	0.93	2.48	3.172 (2)	131

Symmetry codes: (i) ; (ii) ; (iii) .