2-Amino-5-methyl-pyridinium 4-carb-oxy-butano-ate.

In the title salt, C(6)H(9)N(2) (+)·C(5)H(7)O(4) (-), the 2-amino-5-methyl-pyridinium cation is essentially planar, with a maximum deviation of 0.008 (1) Å. In the crystal, the protonated N atom and the 2-amino group are hydrogen bonded to the carboxyl-ate O atoms via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The 4-carb-oxy-butano-ate anions are linked via O-H⋯O hydrogen bonds. The crystal structure is further stabilized by weak C-H⋯O inter-actions.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For applications of glutaric acid, see: Windholz (1976 ▶); Saraswathi et al. (2001 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For related structures, see: Hemamalini & Fun (2010 ▶); Fun et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C6H9N2 +·C5H7O4 −

M = 240.26

Orthorhombic,

a = 5.3159 (10) Å

b = 14.383 (3) Å

c = 15.625 (3) Å

V = 1194.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.29 × 0.17 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.990

7996 measured reflections

2028 independent reflections

1752 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.05

2028 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024451/bv2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024451/bv2141Isup2.hkl

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

C6H9N2+·C5H7O4−	F(000) = 512
Mr = 240.26	Dx = 1.336 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2351 reflections
a = 5.3159 (10) Å	θ = 3.1–29.9°
b = 14.383 (3) Å	µ = 0.10 mm−1
c = 15.625 (3) Å	T = 100 K
V = 1194.7 (4) Å3	Block, colourless
Z = 4	0.29 × 0.17 × 0.10 mm

Bruker APEXII DUO CCD area-detector diffractometer	2028 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.971, Tmax = 0.990	k = −13→20
7996 measured reflections	l = −21→21

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) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.0024P] where P = (Fo2 + 2Fc2)/3
2028 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1366 (3)	0.23633 (10)	0.72155 (9)	0.0178 (3)
H1	0.2568	0.1970	0.7149	0.021*
N2	0.2291 (4)	0.29299 (12)	0.58707 (9)	0.0238 (4)
H2A	0.3451	0.2516	0.5828	0.029*
H2B	0.2030	0.3313	0.5457	0.029*
C1	0.0899 (4)	0.29783 (12)	0.65773 (10)	0.0187 (4)
C2	−0.1037 (4)	0.36383 (13)	0.67157 (11)	0.0232 (4)
H2	−0.1392	0.4084	0.6301	0.028*
C3	−0.2378 (4)	0.36172 (14)	0.74603 (12)	0.0237 (4)
H3	−0.3653	0.4051	0.7543	0.028*
C4	−0.1888 (4)	0.29528 (12)	0.81139 (11)	0.0198 (4)
C5	0.0019 (4)	0.23393 (12)	0.79573 (10)	0.0184 (3)
H5	0.0408	0.1894	0.8368	0.022*
C6	−0.3412 (4)	0.29045 (14)	0.89247 (13)	0.0266 (4)
H6A	−0.5064	0.2673	0.8797	0.040*
H6B	−0.3544	0.3514	0.9170	0.040*
H6C	−0.2601	0.2495	0.9324	0.040*
O1	−0.0252 (3)	0.40052 (9)	0.28998 (7)	0.0196 (3)
O2	0.0882 (3)	0.35424 (10)	0.42007 (7)	0.0238 (3)
O3	0.7031 (3)	0.57159 (10)	0.58440 (8)	0.0245 (3)
O4	0.3325 (3)	0.54500 (10)	0.64750 (8)	0.0240 (3)
H4	0.4108	0.5588	0.6909	0.036*
C7	0.1204 (4)	0.40279 (12)	0.35520 (10)	0.0160 (3)
C8	0.3451 (4)	0.46878 (12)	0.34924 (10)	0.0172 (3)
H8A	0.4587	0.4460	0.3054	0.021*
H8B	0.2852	0.5294	0.3311	0.021*
C9	0.4914 (4)	0.48016 (12)	0.43228 (10)	0.0177 (3)
H9A	0.6509	0.5102	0.4205	0.021*
H9B	0.5261	0.4194	0.4565	0.021*
C10	0.3435 (4)	0.53813 (13)	0.49684 (10)	0.0191 (4)
H10A	0.3062	0.5982	0.4717	0.023*
H10B	0.1847	0.5074	0.5086	0.023*
C11	0.4815 (4)	0.55288 (11)	0.58018 (10)	0.0167 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0184 (8)	0.0183 (7)	0.0169 (6)	0.0033 (6)	−0.0006 (6)	0.0006 (5)
N2	0.0275 (9)	0.0264 (8)	0.0176 (6)	0.0062 (7)	−0.0001 (7)	0.0053 (5)
C1	0.0203 (9)	0.0176 (7)	0.0181 (7)	−0.0002 (7)	−0.0050 (7)	0.0006 (6)
C2	0.0236 (9)	0.0193 (8)	0.0268 (8)	0.0038 (8)	−0.0040 (8)	0.0049 (7)
C3	0.0194 (9)	0.0179 (8)	0.0339 (9)	0.0052 (8)	−0.0008 (9)	−0.0002 (7)
C4	0.0185 (9)	0.0177 (7)	0.0233 (8)	−0.0028 (7)	0.0012 (8)	−0.0017 (6)
C5	0.0206 (9)	0.0175 (7)	0.0170 (7)	−0.0001 (7)	−0.0010 (7)	−0.0002 (5)
C6	0.0259 (10)	0.0230 (9)	0.0308 (9)	−0.0021 (9)	0.0070 (9)	−0.0045 (7)
O1	0.0215 (7)	0.0246 (6)	0.0126 (5)	−0.0056 (6)	−0.0017 (5)	0.0022 (4)
O2	0.0298 (8)	0.0269 (6)	0.0146 (5)	−0.0080 (6)	−0.0044 (6)	0.0058 (5)
O3	0.0200 (7)	0.0339 (7)	0.0195 (6)	−0.0022 (6)	−0.0026 (6)	−0.0033 (5)
O4	0.0230 (7)	0.0354 (7)	0.0136 (5)	−0.0054 (6)	−0.0003 (6)	−0.0058 (5)
C7	0.0175 (8)	0.0166 (7)	0.0138 (6)	−0.0002 (7)	0.0006 (7)	−0.0015 (5)
C8	0.0176 (8)	0.0204 (8)	0.0136 (6)	−0.0029 (7)	0.0003 (7)	−0.0017 (6)
C9	0.0172 (8)	0.0196 (7)	0.0163 (7)	0.0013 (7)	−0.0008 (7)	−0.0027 (6)
C10	0.0182 (9)	0.0236 (8)	0.0155 (7)	0.0037 (7)	−0.0045 (7)	−0.0054 (6)
C11	0.0198 (8)	0.0154 (7)	0.0150 (6)	0.0028 (7)	−0.0022 (7)	−0.0012 (5)

N1—C1	1.356 (2)	C6—H6C	0.9600
N1—C5	1.363 (2)	O1—C7	1.280 (2)
N1—H1	0.8600	O2—C7	1.243 (2)
N2—C1	1.331 (2)	O3—C11	1.210 (2)
N2—H2A	0.8600	O4—C11	1.321 (2)
N2—H2B	0.8600	O4—H4	0.8200
C1—C2	1.417 (3)	C7—C8	1.528 (3)
C2—C3	1.365 (3)	C8—C9	1.522 (2)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.423 (3)	C8—H8B	0.9700
C3—H3	0.9300	C9—C10	1.527 (2)
C4—C5	1.366 (3)	C9—H9A	0.9700
C4—C6	1.505 (3)	C9—H9B	0.9700
C5—H5	0.9300	C10—C11	1.509 (2)
C6—H6A	0.9600	C10—H10A	0.9700
C6—H6B	0.9600	C10—H10B	0.9700
C1—N1—C5	123.09 (16)	H6B—C6—H6C	109.5
C1—N1—H1	118.5	C11—O4—H4	109.5
C5—N1—H1	118.5	O2—C7—O1	123.48 (17)
C1—N2—H2A	120.0	O2—C7—C8	120.42 (15)
C1—N2—H2B	120.0	O1—C7—C8	116.09 (14)
H2A—N2—H2B	120.0	C9—C8—C7	114.48 (13)
N2—C1—N1	118.31 (16)	C9—C8—H8A	108.6
N2—C1—C2	124.45 (16)	C7—C8—H8A	108.6
N1—C1—C2	117.24 (16)	C9—C8—H8B	108.6
C3—C2—C1	119.66 (16)	C7—C8—H8B	108.6
C3—C2—H2	120.2	H8A—C8—H8B	107.6
C1—C2—H2	120.2	C8—C9—C10	111.04 (15)
C2—C3—C4	122.08 (18)	C8—C9—H9A	109.4
C2—C3—H3	119.0	C10—C9—H9A	109.4
C4—C3—H3	119.0	C8—C9—H9B	109.4
C5—C4—C3	116.18 (16)	C10—C9—H9B	109.4
C5—C4—C6	121.36 (16)	H9A—C9—H9B	108.0
C3—C4—C6	122.44 (17)	C11—C10—C9	113.37 (15)
N1—C5—C4	121.73 (16)	C11—C10—H10A	108.9
N1—C5—H5	119.1	C9—C10—H10A	108.9
C4—C5—H5	119.1	C11—C10—H10B	108.9
C4—C6—H6A	109.5	C9—C10—H10B	108.9
C4—C6—H6B	109.5	H10A—C10—H10B	107.7
H6A—C6—H6B	109.5	O3—C11—O4	123.98 (16)
C4—C6—H6C	109.5	O3—C11—C10	123.45 (17)
H6A—C6—H6C	109.5	O4—C11—C10	112.56 (15)
C5—N1—C1—N2	−178.57 (16)	C3—C4—C5—N1	−0.2 (3)
C5—N1—C1—C2	2.0 (3)	C6—C4—C5—N1	178.30 (16)
N2—C1—C2—C3	178.99 (19)	O2—C7—C8—C9	−9.4 (2)
N1—C1—C2—C3	−1.7 (3)	O1—C7—C8—C9	171.50 (15)
C1—C2—C3—C4	0.4 (3)	C7—C8—C9—C10	−72.74 (19)
C2—C3—C4—C5	0.5 (3)	C8—C9—C10—C11	−179.18 (14)
C2—C3—C4—C6	−177.97 (18)	C9—C10—C11—O3	42.8 (2)
C1—N1—C5—C4	−1.1 (3)	C9—C10—C11—O4	−138.56 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.82	2.672 (2)	170
N2—H2A···O2i	0.86	2.00	2.853 (3)	174
N2—H2B···O2	0.86	2.08	2.854 (2)	149
O4—H4···O1ii	0.82	1.76	2.5729 (19)	169
C2—H2···O3iii	0.93	2.59	3.441 (2)	152
C5—H5···O3iv	0.93	2.50	3.379 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.82	2.672 (2)	170
N2—H2A⋯O2i	0.86	2.00	2.853 (3)	174
N2—H2B⋯O2	0.86	2.08	2.854 (2)	149
O4—H4⋯O1ii	0.82	1.76	2.5729 (19)	169
C2—H2⋯O3iii	0.93	2.59	3.441 (2)	152
C5—H5⋯O3iv	0.93	2.50	3.379 (2)	158

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