1-(2-Carb-oxy-eth-yl)-5-ethyl-2-methyl-pyridinium chloride.

In the crystal structure of the title salt, C(11)H(16)NO(2) (+)·Cl(-), the cations and anions are linked by O-H⋯Cl hydrogen bonds. The structure is further stabilized by weak C-H⋯Cl hydrogen bonds.

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 ▶).

Experimental

Crystal data

C11H16NO2 +·Cl−

M = 229.70

Triclinic,

a = 7.5013 (4) Å

b = 9.0509 (5) Å

c = 9.3452 (5) Å

α = 75.253 (2)°

β = 80.985 (2)°

γ = 72.047 (2)°

V = 581.59 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.992

11668 measured reflections

2772 independent reflections

2363 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.102

S = 0.83

2772 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038809/bt6827sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038809/bt6827Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038809/bt6827Isup3.cml

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

C11H16NO2+·Cl−	Z = 2
Mr = 229.70	F(000) = 244
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5013 (4) Å	Cell parameters from 5710 reflections
b = 9.0509 (5) Å	θ = 1.8–28.5°
c = 9.3452 (5) Å	µ = 0.31 mm−1
α = 75.253 (2)°	T = 293 K
β = 80.985 (2)°	Triclinic, colourless
γ = 72.047 (2)°	0.32 × 0.20 × 0.10 mm
V = 581.59 (5) Å3

Bruker APEXII CCD area-detector diffractometer	2772 independent reflections
Radiation source: fine-focus sealed tube	2363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.972, Tmax = 0.992	k = −11→11
11668 measured reflections	l = −10→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.2215P] where P = (Fo2 + 2Fc2)/3
S = 0.83	(Δ/σ)max < 0.001
2772 reflections	Δρmax = 0.23 e Å−3
142 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (6)

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
O2	1.11724 (18)	0.12433 (14)	0.49990 (13)	0.0607 (3)
Cl1	1.13273 (5)	0.19233 (4)	0.17024 (4)	0.04786 (14)
N1	0.73265 (15)	0.39471 (13)	0.81065 (11)	0.0344 (2)
C1	0.60912 (19)	0.31985 (15)	0.89780 (13)	0.0373 (3)
C8	1.01152 (18)	0.23770 (16)	0.56489 (14)	0.0388 (3)
C5	0.67204 (19)	0.53934 (15)	0.72045 (13)	0.0374 (3)
H5	0.7607	0.5877	0.6639	0.045*
O1	0.92281 (18)	0.36464 (13)	0.49974 (11)	0.0570 (3)
C4	0.4848 (2)	0.61779 (16)	0.70897 (14)	0.0390 (3)
C11	0.6787 (2)	0.16261 (18)	1.00116 (16)	0.0503 (4)
H11A	0.7271	0.0810	0.9453	0.075*
H11B	0.5770	0.1396	1.0707	0.075*
H11C	0.7768	0.1662	1.0539	0.075*
C3	0.3566 (2)	0.54196 (18)	0.79512 (16)	0.0441 (3)
H3	0.2282	0.5900	0.7897	0.053*
C2	0.4195 (2)	0.39556 (17)	0.88856 (15)	0.0430 (3)
H2	0.3323	0.3465	0.9468	0.052*
C6	0.93976 (19)	0.32296 (19)	0.81201 (15)	0.0436 (3)
H6A	0.9709	0.2834	0.9143	0.052*
H6B	1.0014	0.4055	0.7671	0.052*
C7	1.0172 (2)	0.18822 (18)	0.73100 (15)	0.0448 (3)
H7B	1.1466	0.1356	0.7534	0.054*
H7A	0.9463	0.1110	0.7692	0.054*
C9	0.4262 (2)	0.77820 (17)	0.60617 (17)	0.0510 (4)
H9B	0.4899	0.8477	0.6273	0.061*
H9A	0.2920	0.8242	0.6246	0.061*
C10	0.4713 (3)	0.7697 (2)	0.44375 (17)	0.0566 (4)
H10A	0.4327	0.8749	0.3825	0.085*
H10C	0.4054	0.7038	0.4214	0.085*
H10B	0.6042	0.7252	0.4247	0.085*
H2A	1.108 (3)	0.153 (3)	0.399 (3)	0.099 (8)*

	U11	U22	U33	U12	U13	U23
O2	0.0687 (7)	0.0570 (7)	0.0404 (6)	0.0055 (6)	−0.0043 (5)	−0.0115 (5)
Cl1	0.0537 (2)	0.0563 (2)	0.03510 (19)	−0.01908 (17)	0.00042 (14)	−0.01085 (14)
N1	0.0393 (5)	0.0394 (6)	0.0274 (5)	−0.0143 (4)	−0.0016 (4)	−0.0091 (4)
C1	0.0487 (7)	0.0390 (7)	0.0276 (5)	−0.0171 (6)	0.0032 (5)	−0.0114 (5)
C8	0.0357 (6)	0.0436 (7)	0.0364 (6)	−0.0143 (5)	−0.0016 (5)	−0.0048 (5)
C5	0.0470 (7)	0.0387 (7)	0.0306 (6)	−0.0185 (5)	−0.0004 (5)	−0.0088 (5)
O1	0.0768 (8)	0.0457 (6)	0.0376 (5)	−0.0042 (5)	−0.0076 (5)	−0.0044 (4)
C4	0.0499 (7)	0.0368 (6)	0.0329 (6)	−0.0116 (5)	−0.0040 (5)	−0.0124 (5)
C11	0.0660 (9)	0.0424 (8)	0.0364 (7)	−0.0154 (7)	0.0070 (6)	−0.0044 (6)
C3	0.0407 (7)	0.0496 (8)	0.0443 (7)	−0.0111 (6)	−0.0002 (6)	−0.0185 (6)
C2	0.0454 (7)	0.0486 (8)	0.0395 (7)	−0.0211 (6)	0.0081 (6)	−0.0148 (6)
C6	0.0391 (7)	0.0578 (8)	0.0350 (6)	−0.0148 (6)	−0.0088 (5)	−0.0070 (6)
C7	0.0382 (7)	0.0514 (8)	0.0350 (6)	−0.0061 (6)	−0.0022 (5)	−0.0010 (6)
C9	0.0661 (10)	0.0376 (7)	0.0460 (8)	−0.0078 (7)	−0.0099 (7)	−0.0087 (6)
C10	0.0693 (10)	0.0565 (9)	0.0428 (8)	−0.0199 (8)	−0.0084 (7)	−0.0039 (7)

O2—C8	1.3097 (18)	C11—H11C	0.9600
O2—H2A	0.92 (3)	C3—C2	1.377 (2)
N1—C5	1.3499 (17)	C3—H3	0.9300
N1—C1	1.3604 (16)	C2—H2	0.9300
N1—C6	1.4885 (17)	C6—C7	1.514 (2)
C1—C2	1.381 (2)	C6—H6A	0.9700
C1—C11	1.4938 (19)	C6—H6B	0.9700
C8—O1	1.1971 (17)	C7—H7B	0.9700
C8—C7	1.5058 (19)	C7—H7A	0.9700
C5—C4	1.372 (2)	C9—C10	1.519 (2)
C5—H5	0.9300	C9—H9B	0.9700
C4—C3	1.388 (2)	C9—H9A	0.9700
C4—C9	1.5009 (19)	C10—H10A	0.9600
C11—H11A	0.9600	C10—H10C	0.9600
C11—H11B	0.9600	C10—H10B	0.9600
C8—O2—H2A	110.8 (16)	C3—C2—H2	119.3
C5—N1—C1	121.15 (11)	C1—C2—H2	119.3
C5—N1—C6	116.99 (11)	N1—C6—C7	114.17 (11)
C1—N1—C6	121.85 (11)	N1—C6—H6A	108.7
N1—C1—C2	117.68 (12)	C7—C6—H6A	108.7
N1—C1—C11	120.43 (13)	N1—C6—H6B	108.7
C2—C1—C11	121.88 (12)	C7—C6—H6B	108.7
O1—C8—O2	123.99 (13)	H6A—C6—H6B	107.6
O1—C8—C7	124.60 (13)	C8—C7—C6	114.89 (12)
O2—C8—C7	111.41 (12)	C8—C7—H7B	108.5
N1—C5—C4	122.58 (12)	C6—C7—H7B	108.5
N1—C5—H5	118.7	C8—C7—H7A	108.5
C4—C5—H5	118.7	C6—C7—H7A	108.5
C5—C4—C3	117.08 (13)	H7B—C7—H7A	107.5
C5—C4—C9	120.07 (13)	C4—C9—C10	112.48 (12)
C3—C4—C9	122.85 (14)	C4—C9—H9B	109.1
C1—C11—H11A	109.5	C10—C9—H9B	109.1
C1—C11—H11B	109.5	C4—C9—H9A	109.1
H11A—C11—H11B	109.5	C10—C9—H9A	109.1
C1—C11—H11C	109.5	H9B—C9—H9A	107.8
H11A—C11—H11C	109.5	C9—C10—H10A	109.5
H11B—C11—H11C	109.5	C9—C10—H10C	109.5
C2—C3—C4	119.99 (13)	H10A—C10—H10C	109.5
C2—C3—H3	120.0	C9—C10—H10B	109.5
C4—C3—H3	120.0	H10A—C10—H10B	109.5
C3—C2—C1	121.50 (12)	H10C—C10—H10B	109.5
C5—N1—C1—C2	1.26 (17)	C4—C3—C2—C1	−0.9 (2)
C6—N1—C1—C2	−179.81 (11)	N1—C1—C2—C3	−0.25 (19)
C5—N1—C1—C11	−177.69 (11)	C11—C1—C2—C3	178.69 (13)
C6—N1—C1—C11	1.24 (18)	C5—N1—C6—C7	−105.73 (14)
C1—N1—C5—C4	−1.18 (18)	C1—N1—C6—C7	75.30 (15)
C6—N1—C5—C4	179.84 (11)	O1—C8—C7—C6	−14.0 (2)
N1—C5—C4—C3	0.01 (19)	O2—C8—C7—C6	165.58 (13)
N1—C5—C4—C9	−179.76 (11)	N1—C6—C7—C8	69.15 (16)
C5—C4—C3—C2	0.99 (19)	C5—C4—C9—C10	68.80 (18)
C9—C4—C3—C2	−179.24 (13)	C3—C4—C9—C10	−110.95 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1i	0.93	2.72	3.6249 (14)	166
C6—H6A···Cl1ii	0.97	2.68	3.6261 (14)	166
O2—H2A···Cl1	0.92 (3)	2.06 (3)	2.9749 (12)	170 (2)
C11—H11A···Cl1iii	0.96	2.79	3.7410 (16)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯Cl1	0.92 (3)	2.06 (3)	2.9749 (12)	170 (2)
C2—H2⋯Cl1i	0.93	2.72	3.6249 (14)	166
C6—H6A⋯Cl1ii	0.97	2.68	3.6261 (14)	166
C11—H11A⋯Cl1iii	0.96	2.79	3.7410 (16)	170

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