2-Carb-oxy-pyridinium maleate.

In the title mol-ecular salt, C(6)H(6)NO(2) (+) (.)C(4)H(3)O(4) (-), the 2-carb-oxy-pyridinium cation is essentially planar with a maximum deviation of 0.003 (3) Å. In the crystal, adjacent cations and anions are linked by an extensive system of weak N-H⋯O, O-H⋯O and C-H⋯O inter-actions, forming a layer parallel to the ab plane.

Related literature

For details of pyridine and its derivatives, see: Banerjee & Murugavel (2004 ▶); Bis et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H6NO2·C4H3O4

M = 239.18

Monoclinic,

a = 14.6498 (9) Å

b = 10.3976 (8) Å

c = 6.9067 (5) Å

β = 100.089 (3)°

V = 1035.78 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 295 K

0.24 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.980

9722 measured reflections

2557 independent reflections

2092 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.199

S = 1.10

2557 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.33 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) global, I. DOI: 10.1107/S1600536812041177/rk2380sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041177/rk2380Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041177/rk2380Isup3.cml

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

C6H6NO2·C4H3O4	F(000) = 496
Mr = 239.18	Dx = 1.534 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4245 reflections
a = 14.6498 (9) Å	θ = 2.4–28.3°
b = 10.3976 (8) Å	µ = 0.13 mm−1
c = 6.9067 (5) Å	T = 295 K
β = 100.089 (3)°	Block, colourless
V = 1035.78 (13) Å3	0.24 × 0.20 × 0.16 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2557 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω– and φ–scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
Tmin = 0.970, Tmax = 0.980	k = −13→13
9722 measured reflections	l = −9→9

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)] = 0.071	H-atom parameters constrained
wR(F2) = 0.199	w = 1/[σ2(Fo2) + (0.0625P)2 + 1.8972P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2557 reflections	Δρmax = 0.43 e Å−3
155 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

	x	y	z	Uiso*/Ueq
C1	0.57261 (18)	−0.0804 (3)	0.3125 (4)	0.0320 (6)
C2	0.6336 (2)	−0.1778 (3)	0.3751 (5)	0.0389 (7)
H2	0.6170	−0.2628	0.3454	0.047*
C3	0.7201 (2)	−0.1492 (3)	0.4825 (5)	0.0438 (7)
H3	0.7618	−0.2149	0.5261	0.053*
C4	0.7440 (2)	−0.0230 (3)	0.5246 (5)	0.0412 (7)
H4	0.8020	−0.0027	0.5963	0.049*
C5	0.6817 (2)	0.0725 (3)	0.4599 (5)	0.0401 (7)
H5	0.6971	0.1582	0.4869	0.048*
N1	0.59856 (15)	0.0413 (2)	0.3575 (4)	0.0342 (5)
H1	0.5599	0.1021	0.3187	0.041*
C6	0.47635 (19)	−0.1001 (3)	0.1946 (4)	0.0346 (6)
C7	0.79780 (19)	0.0490 (3)	0.0421 (4)	0.0354 (6)
C8	0.8827 (2)	−0.0055 (3)	0.1646 (5)	0.0373 (6)
H8	0.8762	−0.0878	0.2130	0.045*
C9	0.9664 (2)	0.0462 (3)	0.2149 (5)	0.0388 (7)
H9	1.0084	−0.0061	0.2955	0.047*
C10	1.0058 (2)	0.1714 (3)	0.1674 (5)	0.0401 (7)
O1	0.45516 (17)	−0.2082 (2)	0.1321 (4)	0.0566 (7)
O2	0.42766 (14)	0.0007 (2)	0.1721 (4)	0.0453 (6)
H2A	0.3766	−0.0161	0.1075	0.068*
O3	0.72935 (14)	−0.0300 (2)	0.0195 (4)	0.0446 (6)
O4	0.79341 (16)	0.1568 (2)	−0.0311 (4)	0.0601 (8)
O5	0.95136 (17)	0.2604 (2)	0.0741 (4)	0.0559 (7)
H5A	0.8978	0.2340	0.0523	0.084*
O6	1.08852 (16)	0.1899 (3)	0.2139 (4)	0.0580 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0282 (13)	0.0299 (13)	0.0366 (14)	−0.0020 (10)	0.0024 (10)	0.0014 (11)
C2	0.0389 (15)	0.0262 (13)	0.0493 (17)	0.0000 (11)	0.0014 (13)	0.0055 (12)
C3	0.0374 (15)	0.0392 (16)	0.0514 (18)	0.0078 (13)	−0.0014 (13)	0.0081 (14)
C4	0.0284 (13)	0.0471 (17)	0.0440 (17)	−0.0014 (12)	−0.0051 (12)	−0.0031 (13)
C5	0.0310 (14)	0.0349 (15)	0.0518 (18)	−0.0029 (11)	0.0001 (12)	−0.0068 (13)
N1	0.0270 (11)	0.0274 (11)	0.0458 (14)	0.0014 (9)	−0.0005 (10)	0.0004 (10)
C6	0.0270 (13)	0.0327 (14)	0.0417 (15)	−0.0060 (10)	−0.0003 (11)	0.0041 (11)
C7	0.0295 (13)	0.0331 (14)	0.0426 (15)	0.0006 (11)	0.0031 (11)	−0.0015 (12)
C8	0.0358 (14)	0.0296 (13)	0.0451 (16)	0.0011 (11)	0.0029 (12)	0.0029 (12)
C9	0.0352 (14)	0.0320 (14)	0.0452 (17)	0.0020 (11)	−0.0041 (12)	0.0017 (12)
C10	0.0378 (15)	0.0350 (15)	0.0459 (17)	−0.0054 (12)	0.0024 (13)	−0.0057 (13)
O1	0.0479 (13)	0.0352 (12)	0.0781 (18)	−0.0090 (10)	−0.0125 (12)	−0.0019 (12)
O2	0.0261 (10)	0.0393 (12)	0.0648 (15)	−0.0008 (9)	−0.0079 (9)	−0.0009 (10)
O3	0.0323 (10)	0.0425 (12)	0.0555 (14)	−0.0055 (9)	−0.0018 (9)	0.0043 (10)
O4	0.0395 (12)	0.0409 (13)	0.092 (2)	−0.0009 (10)	−0.0120 (12)	0.0193 (13)
O5	0.0458 (13)	0.0373 (12)	0.0786 (18)	−0.0083 (10)	−0.0054 (12)	0.0109 (12)
O6	0.0378 (12)	0.0526 (15)	0.0787 (19)	−0.0125 (11)	−0.0037 (12)	−0.0083 (13)

C1—N1	1.342 (4)	C6—O2	1.261 (3)
C1—C2	1.370 (4)	C7—O4	1.227 (4)
C1—C6	1.514 (4)	C7—O3	1.284 (3)
C2—C3	1.384 (4)	C7—C8	1.488 (4)
C2—H2	0.9300	C8—C9	1.328 (4)
C3—C4	1.376 (5)	C8—H8	0.9300
C3—H3	0.9300	C9—C10	1.484 (4)
C4—C5	1.369 (4)	C9—H9	0.9300
C4—H4	0.9300	C10—O6	1.213 (4)
C5—N1	1.336 (4)	C10—O5	1.315 (4)
C5—H5	0.9300	O2—H2A	0.8200
N1—H1	0.8600	O5—H5A	0.8200
C6—O1	1.224 (4)
N1—C1—C2	118.8 (2)	O1—C6—O2	128.0 (3)
N1—C1—C6	116.8 (2)	O1—C6—C1	117.9 (3)
C2—C1—C6	124.4 (3)	O2—C6—C1	114.0 (2)
C1—C2—C3	119.7 (3)	O4—C7—O3	123.4 (3)
C1—C2—H2	120.1	O4—C7—C8	124.1 (3)
C3—C2—H2	120.1	O3—C7—C8	112.5 (3)
C4—C3—C2	119.5 (3)	C9—C8—C7	129.5 (3)
C4—C3—H3	120.2	C9—C8—H8	115.2
C2—C3—H3	120.2	C7—C8—H8	115.2
C5—C4—C3	119.5 (3)	C8—C9—C10	132.4 (3)
C5—C4—H4	120.3	C8—C9—H9	113.8
C3—C4—H4	120.3	C10—C9—H9	113.8
N1—C5—C4	119.4 (3)	O6—C10—O5	120.7 (3)
N1—C5—H5	120.3	O6—C10—C9	119.4 (3)
C4—C5—H5	120.3	O5—C10—C9	120.0 (3)
C5—N1—C1	123.1 (2)	C6—O2—H2A	109.5
C5—N1—H1	118.5	C10—O5—H5A	109.5
C1—N1—H1	118.5
N1—C1—C2—C3	0.0 (5)	C2—C1—C6—O1	−8.5 (5)
C6—C1—C2—C3	−179.9 (3)	N1—C1—C6—O2	−7.8 (4)
C1—C2—C3—C4	−0.3 (5)	C2—C1—C6—O2	172.1 (3)
C2—C3—C4—C5	0.2 (5)	O4—C7—C8—C9	−1.2 (6)
C3—C4—C5—N1	0.2 (5)	O3—C7—C8—C9	178.2 (3)
C4—C5—N1—C1	−0.6 (5)	C7—C8—C9—C10	−1.2 (6)
C2—C1—N1—C5	0.5 (5)	C8—C9—C10—O6	−171.4 (4)
C6—C1—N1—C5	−179.7 (3)	C8—C9—C10—O5	8.0 (6)
N1—C1—C6—O1	171.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.28	2.639 (3)	105
O5—H5A···O4	0.82	1.73	2.540 (3)	168
N1—H1···O1i	0.86	2.02	2.725 (3)	139
O2—H2A···O3ii	0.82	1.71	2.463 (3)	152
C2—H2···O2iii	0.93	2.54	3.462 (4)	170
C3—H3···O6iv	0.93	2.59	3.221 (4)	125
C5—H5···O4v	0.93	2.40	3.251 (4)	152
C8—H8···O6vi	0.93	2.40	3.285 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.28	2.639 (3)	105
O5—H5A⋯O4	0.82	1.73	2.540 (3)	168
N1—H1⋯O1i	0.86	2.02	2.725 (3)	139
O2—H2A⋯O3ii	0.82	1.71	2.463 (3)	152
C2—H2⋯O2iii	0.93	2.54	3.462 (4)	170
C3—H3⋯O6iv	0.93	2.59	3.221 (4)	125
C5—H5⋯O4v	0.93	2.40	3.251 (4)	152
C8—H8⋯O6vi	0.93	2.40	3.285 (4)	158

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