4-Methyl-pyridinium 4-hy-droxy-benzoate.

In the crystal structure of the title salt, C(6)H(8)N(+)·C(7)H(5)O(3) (-), the anions and cations are linked by classical N-H⋯O hydrogen bonds. The anions are connected by pairs of C-H⋯O hydrogen bonds into inversion dimers and further linked by classical O-H⋯O hydrogen bonds. Weak π-π inter-actions [centroid-centroid distances = 3.740 (3) and 3.855 (3) Å] also occur. The dihedral angle between the CO(2) (-) group and the benzene ring to which it is attached is 20.95 (8)°.

Related literature

For biological applications of picolinium-containing compounds, see: Butler & Walker (1993 ▶); Roy et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H8N+·C7H5O3 −

M = 231.24

Monoclinic,

a = 7.479 (5) Å

b = 11.671 (4) Å

c = 13.520 (5) Å

β = 100.217 (5)°

V = 1161.4 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

11741 measured reflections

2564 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.06

2564 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001785/rk2392sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001785/rk2392Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001785/rk2392Isup3.cml

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

C6H8N+·C7H5O3−	F(000) = 488
Mr = 231.24	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Melting point = 470.4–481.2 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.479 (5) Å	Cell parameters from 7082 reflections
b = 11.671 (4) Å	θ = 2.3–27.1°
c = 13.520 (5) Å	µ = 0.10 mm−1
β = 100.217 (5)°	T = 295 K
V = 1161.4 (10) Å3	Block, colourless
Z = 4	0.24 × 0.20 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	2564 independent reflections
Radiation source: fine–focus sealed tube	1939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 27.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.978, Tmax = 0.983	k = −14→8
11741 measured reflections	l = −17→17

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.058P)2 + 0.3003P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2564 reflections	Δρmax = 0.38 e Å−3
156 parameters	Δρmin = −0.34 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: 0.010 (2)

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 > 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
O1	0.55020 (18)	0.18454 (10)	0.02055 (8)	0.0578 (4)
H1	0.5981	0.2464	0.0131	0.087*
O2	0.7215 (2)	0.11967 (10)	0.49538 (9)	0.0599 (4)
O3	0.71511 (18)	−0.05893 (9)	0.44053 (8)	0.0563 (4)
C1	0.5832 (2)	0.15548 (13)	0.11952 (11)	0.0396 (4)
C2	0.5407 (2)	0.04549 (13)	0.14510 (11)	0.0435 (4)
H2	0.4883	−0.0056	0.0955	0.052*
C3	0.5761 (2)	0.01174 (12)	0.24435 (11)	0.0394 (4)
H3	0.5492	−0.0628	0.2612	0.047*
C4	0.6512 (2)	0.08716 (12)	0.31929 (10)	0.0356 (3)
C5	0.6894 (2)	0.19833 (12)	0.29287 (11)	0.0394 (4)
H5	0.7375	0.2503	0.3427	0.047*
C6	0.6571 (2)	0.23261 (13)	0.19390 (11)	0.0397 (4)
H6	0.6846	0.3070	0.1769	0.048*
C7	0.6972 (2)	0.05049 (13)	0.42610 (11)	0.0412 (4)
N1	0.18709 (19)	0.10699 (12)	0.37067 (10)	0.0475 (4)
H1A	0.2170	0.0966	0.4344	0.057*
C8	0.2266 (2)	0.20451 (14)	0.32853 (13)	0.0490 (4)
H8	0.2872	0.2617	0.3692	0.059*
C9	0.1813 (2)	0.22368 (14)	0.22732 (12)	0.0473 (4)
H9	0.2099	0.2933	0.2005	0.057*
C10	0.0932 (2)	0.13982 (14)	0.16510 (11)	0.0446 (4)
C11	0.0517 (2)	0.03949 (14)	0.20988 (13)	0.0480 (4)
H11	−0.0091	−0.0190	0.1709	0.058*
C12	0.1000 (2)	0.02581 (14)	0.31174 (13)	0.0478 (4)
H12	0.0710	−0.0424	0.3407	0.057*
C13	0.0475 (3)	0.15746 (19)	0.05391 (14)	0.0686 (6)
H13A	0.0259	0.2374	0.0398	0.103*
H13B	−0.0596	0.1145	0.0272	0.103*
H13C	0.1469	0.1318	0.0234	0.103*

	U11	U22	U33	U12	U13	U23
O1	0.0913 (9)	0.0446 (7)	0.0328 (6)	−0.0132 (6)	−0.0014 (6)	0.0060 (5)
O2	0.1019 (10)	0.0430 (7)	0.0334 (6)	0.0124 (6)	0.0079 (6)	−0.0037 (5)
O3	0.0980 (10)	0.0342 (6)	0.0363 (6)	0.0073 (6)	0.0106 (6)	0.0038 (5)
C1	0.0502 (9)	0.0365 (8)	0.0309 (7)	0.0008 (6)	0.0040 (6)	0.0032 (6)
C2	0.0561 (9)	0.0357 (8)	0.0363 (8)	−0.0062 (7)	0.0014 (7)	−0.0028 (6)
C3	0.0509 (9)	0.0283 (7)	0.0391 (8)	−0.0019 (6)	0.0081 (7)	0.0025 (6)
C4	0.0440 (8)	0.0316 (7)	0.0320 (7)	0.0046 (6)	0.0091 (6)	0.0012 (6)
C5	0.0520 (9)	0.0325 (8)	0.0339 (8)	−0.0003 (6)	0.0085 (6)	−0.0050 (6)
C6	0.0537 (9)	0.0282 (7)	0.0383 (8)	−0.0022 (6)	0.0106 (7)	0.0016 (6)
C7	0.0554 (9)	0.0357 (8)	0.0343 (8)	0.0052 (7)	0.0123 (7)	−0.0005 (6)
N1	0.0592 (9)	0.0506 (8)	0.0323 (7)	0.0066 (6)	0.0073 (6)	0.0070 (6)
C8	0.0561 (10)	0.0450 (9)	0.0441 (9)	−0.0015 (7)	0.0036 (7)	−0.0009 (7)
C9	0.0550 (10)	0.0417 (9)	0.0454 (9)	−0.0008 (7)	0.0089 (7)	0.0087 (7)
C10	0.0468 (9)	0.0502 (10)	0.0365 (8)	0.0059 (7)	0.0068 (7)	0.0045 (7)
C11	0.0544 (10)	0.0446 (9)	0.0440 (9)	−0.0011 (7)	0.0057 (7)	−0.0018 (7)
C12	0.0563 (10)	0.0415 (9)	0.0474 (9)	0.0016 (7)	0.0138 (8)	0.0070 (7)
C13	0.0898 (15)	0.0731 (13)	0.0400 (10)	0.0027 (11)	0.0039 (9)	0.0092 (9)

O1—C1	1.3599 (18)	N1—C8	1.329 (2)
O1—H1	0.8200	N1—C12	1.331 (2)
O2—C7	1.2255 (19)	N1—H1A	0.8600
O3—C7	1.2953 (19)	C8—C9	1.369 (2)
C1—C2	1.381 (2)	C8—H8	0.9300
C1—C6	1.389 (2)	C9—C10	1.379 (2)
C2—C3	1.378 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.379 (2)
C3—C4	1.384 (2)	C10—C13	1.496 (2)
C3—H3	0.9300	C11—C12	1.370 (2)
C4—C5	1.389 (2)	C11—H11	0.9300
C4—C7	1.487 (2)	C12—H12	0.9300
C5—C6	1.376 (2)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
C1—O1—H1	109.5	C8—N1—H1A	120.8
O1—C1—C2	117.94 (13)	C12—N1—H1A	120.8
O1—C1—C6	122.02 (14)	N1—C8—C9	122.28 (16)
C2—C1—C6	120.05 (14)	N1—C8—H8	118.9
C3—C2—C1	119.75 (14)	C9—C8—H8	118.9
C3—C2—H2	120.1	C8—C9—C10	120.04 (15)
C1—C2—H2	120.1	C8—C9—H9	120.0
C2—C3—C4	120.93 (14)	C10—C9—H9	120.0
C2—C3—H3	119.5	C11—C10—C9	117.07 (15)
C4—C3—H3	119.5	C11—C10—C13	121.95 (16)
C3—C4—C5	118.77 (13)	C9—C10—C13	120.97 (16)
C3—C4—C7	121.46 (13)	C12—C11—C10	120.06 (16)
C5—C4—C7	119.74 (13)	C12—C11—H11	120.0
C6—C5—C4	120.85 (14)	C10—C11—H11	120.0
C6—C5—H5	119.6	N1—C12—C11	122.17 (15)
C4—C5—H5	119.6	N1—C12—H12	118.9
C5—C6—C1	119.62 (14)	C11—C12—H12	118.9
C5—C6—H6	120.2	C10—C13—H13A	109.5
C1—C6—H6	120.2	C10—C13—H13B	109.5
O2—C7—O3	122.48 (15)	H13A—C13—H13B	109.5
O2—C7—C4	122.01 (14)	C10—C13—H13C	109.5
O3—C7—C4	115.47 (13)	H13A—C13—H13C	109.5
C8—N1—C12	118.37 (14)	H13B—C13—H13C	109.5
O1—C1—C2—C3	178.41 (14)	C5—C4—C7—O2	20.1 (2)
C6—C1—C2—C3	−1.7 (2)	C3—C4—C7—O3	20.0 (2)
C1—C2—C3—C4	1.1 (2)	C5—C4—C7—O3	−157.84 (15)
C2—C3—C4—C5	0.4 (2)	C12—N1—C8—C9	−0.1 (2)
C2—C3—C4—C7	−177.46 (14)	N1—C8—C9—C10	−0.7 (3)
C3—C4—C5—C6	−1.4 (2)	C8—C9—C10—C11	1.2 (2)
C7—C4—C5—C6	176.54 (14)	C8—C9—C10—C13	−178.06 (16)
C4—C5—C6—C1	0.8 (2)	C9—C10—C11—C12	−0.9 (2)
O1—C1—C6—C5	−179.34 (14)	C13—C10—C11—C12	178.39 (17)
C2—C1—C6—C5	0.7 (2)	C8—N1—C12—C11	0.5 (2)
C3—C4—C7—O2	−162.01 (16)	C10—C11—C12—N1	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.85	2.6707 (19)	176
N1—H1A···O3ii	0.86	1.73	2.5889 (19)	173
C2—H2···O1iii	0.93	2.60	3.485 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.85	2.6707 (19)	176
N1—H1A⋯O3ii	0.86	1.73	2.5889 (19)	173
C2—H2⋯O1iii	0.93	2.60	3.485 (2)	160

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