4-Carboxy-pyridinium 3-carb-oxy-4-hydroxy-benzene-sulfonate.

Cocrystallization of 4-carboxy-pyridine (4-CPY) and 5-sulfosalicylic acid (5-H(2)SSA) yields the title salt, C(6)H(6)NO(2) (+)·C(7)H(5)O(6)S(-). In the crystal structure, the components of the salt are linked by a combination of inter-molecular O-H⋯O and N-H⋯O, and weak C-H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For related literature, see: Aakeröy & Salmon (2005 ▶); Meng et al. (2007 ▶, 2008 ▶); Fan et al. (2005 ▶); Smith et al. (2006 ▶).

Experimental

Crystal data

C6H6NO2 +·n class="Chemical">C7H5O6S−

M = 341.29

Orthorhombic,

a = 6.6358 (6) Å

b = 13.0514 (12) Å

c = 16.7415 (14) Å

V = 1449.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.30 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

13287 measured reflections

2545 independent reflections

1522 reflections with I > 2σ(I)

R int = 0.143

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.168

S = 0.97

2545 reflections

220 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1056 Friedel pairs

Flack parameter: −0.1 (2)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015882/lh2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015882/lh2633Isup2.hkl

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

C6H6NO2+·C7H5O6S−	F(000) = 704
Mr = 341.29	Dx = 1.563 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 950 reflections
a = 6.6358 (6) Å	θ = 3.1–19.7°
b = 13.0514 (12) Å	µ = 0.27 mm−1
c = 16.7415 (14) Å	T = 298 K
V = 1449.9 (2) Å3	Needle, colorless
Z = 4	0.30 × 0.04 × 0.02 mm

Bruker SMART APEX CCD area-detector diffractometer	1522 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	Rint = 0.143
graphite	θmax = 25.0°, θmin = 2.9°
0.3° wide ω exposures scans	h = −7→7
13287 measured reflections	k = −15→15
2545 independent reflections	l = −19→18

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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2545 reflections	Δρmax = 0.45 e Å−3
220 parameters	Δρmin = −0.37 e Å−3
5 restraints	Absolute structure: Flack (1983), 1056 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (2)

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	0.5027 (9)	0.7437 (4)	0.2884 (4)	0.0404 (15)
C2	0.4566 (8)	0.6435 (4)	0.2645 (3)	0.0334 (13)
C3	0.4291 (9)	0.5677 (4)	0.3235 (3)	0.0362 (13)
H3	0.3988	0.5009	0.3082	0.043*
C4	0.4464 (9)	0.5908 (4)	0.4022 (3)	0.0410 (15)
C5	0.4945 (12)	0.6910 (4)	0.4256 (4)	0.0563 (18)
H5	0.5083	0.7069	0.4794	0.068*
C6	0.5212 (12)	0.7655 (4)	0.3689 (4)	0.062 (2)
H6	0.5524	0.8319	0.3848	0.074*
C7	0.4373 (9)	0.6190 (4)	0.1788 (3)	0.0393 (14)
O1	0.3740 (8)	0.5263 (3)	0.1634 (2)	0.0556 (12)
H1	0.335 (11)	0.517 (5)	0.1176 (19)	0.083*
O2	0.4714 (6)	0.6826 (3)	0.1260 (2)	0.0496 (11)
O3	0.5284 (8)	0.8216 (3)	0.2371 (2)	0.0554 (13)
H3A	0.524 (13)	0.799 (5)	0.1914 (18)	0.083*
O4	0.5754 (7)	0.5082 (3)	0.5343 (2)	0.0524 (11)
O5	0.2154 (6)	0.5225 (3)	0.5150 (2)	0.0519 (11)
O6	0.4088 (7)	0.3976 (2)	0.4391 (2)	0.0474 (10)
S1	0.4079 (2)	0.49700 (10)	0.47738 (8)	0.0424 (4)
C8	0.4478 (9)	0.1284 (4)	0.6933 (4)	0.0466 (15)
C9	0.5068 (10)	0.2291 (5)	0.6931 (4)	0.0551 (18)
H9	0.5412	0.2611	0.7409	0.066*
C10	0.5153 (10)	0.2820 (5)	0.6234 (4)	0.0538 (17)
H10	0.5557	0.3503	0.6230	0.065*
C11	0.4091 (10)	0.1365 (5)	0.5529 (4)	0.0531 (16)
H11	0.3762	0.1060	0.5045	0.064*
C12	0.4005 (9)	0.0804 (4)	0.6229 (4)	0.0474 (15)
H12	0.3635	0.0117	0.6223	0.057*
C13	0.4301 (10)	0.0658 (5)	0.7697 (4)	0.0491 (16)
N1	0.4651 (8)	0.2351 (4)	0.5553 (4)	0.0533 (14)
H1A	0.480 (8)	0.267 (4)	0.511 (2)	0.064*
O7	0.4546 (8)	0.1208 (3)	0.8342 (3)	0.0669 (14)
H7	0.478 (13)	0.078 (4)	0.870 (3)	0.100*
O8	0.3980 (8)	−0.0253 (3)	0.7684 (3)	0.0715 (14)

	U11	U22	U33	U12	U13	U23
C1	0.037 (4)	0.045 (3)	0.040 (3)	−0.008 (3)	0.006 (3)	0.005 (3)
C2	0.025 (3)	0.041 (3)	0.035 (3)	0.003 (2)	0.000 (3)	0.004 (2)
C3	0.028 (3)	0.039 (3)	0.042 (4)	−0.002 (2)	0.002 (3)	0.000 (3)
C4	0.034 (4)	0.046 (3)	0.043 (4)	−0.003 (3)	0.007 (3)	0.002 (3)
C5	0.077 (5)	0.054 (3)	0.038 (3)	−0.006 (4)	−0.006 (4)	−0.005 (3)
C6	0.085 (6)	0.043 (3)	0.057 (4)	−0.017 (4)	0.009 (4)	−0.003 (3)
C7	0.035 (4)	0.043 (3)	0.040 (4)	0.009 (3)	0.001 (3)	0.004 (3)
O1	0.079 (3)	0.047 (2)	0.041 (3)	−0.011 (2)	−0.012 (3)	−0.003 (2)
O2	0.048 (3)	0.057 (2)	0.043 (2)	−0.007 (2)	0.002 (2)	0.003 (2)
O3	0.075 (4)	0.050 (2)	0.042 (2)	−0.010 (2)	−0.003 (3)	0.008 (2)
O4	0.054 (3)	0.066 (2)	0.037 (2)	−0.001 (2)	−0.012 (2)	−0.003 (2)
O5	0.040 (3)	0.064 (3)	0.052 (3)	0.002 (2)	0.021 (2)	0.008 (2)
O6	0.054 (3)	0.047 (2)	0.042 (2)	0.000 (2)	0.000 (3)	−0.0028 (18)
S1	0.0461 (9)	0.0454 (8)	0.0356 (8)	−0.0018 (8)	0.0026 (7)	0.0006 (7)
C8	0.028 (4)	0.051 (3)	0.061 (4)	0.008 (3)	−0.002 (3)	0.002 (3)
C9	0.044 (4)	0.059 (4)	0.063 (5)	0.002 (3)	−0.006 (4)	0.003 (3)
C10	0.031 (4)	0.060 (4)	0.070 (5)	0.000 (3)	−0.001 (4)	0.007 (4)
C11	0.030 (4)	0.070 (4)	0.059 (4)	0.001 (3)	0.002 (4)	−0.009 (3)
C12	0.029 (3)	0.060 (4)	0.053 (4)	−0.001 (3)	−0.003 (4)	0.006 (4)
C13	0.039 (4)	0.053 (4)	0.056 (4)	0.010 (3)	−0.006 (4)	0.009 (3)
N1	0.033 (3)	0.065 (4)	0.062 (4)	0.003 (3)	0.008 (3)	0.011 (3)
O7	0.081 (4)	0.064 (3)	0.055 (3)	−0.001 (3)	−0.007 (3)	0.006 (2)
O8	0.077 (4)	0.062 (3)	0.075 (3)	−0.008 (3)	−0.011 (3)	0.015 (2)

C1—O3	1.343 (6)	O5—S1	1.462 (4)
C1—C6	1.382 (8)	O6—S1	1.446 (3)
C1—C2	1.401 (7)	C8—C12	1.370 (8)
C2—C3	1.409 (7)	C8—C9	1.371 (8)
C2—C7	1.477 (7)	C8—C13	1.523 (8)
C3—C4	1.357 (7)	C9—C10	1.359 (8)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.401 (7)	C10—N1	1.336 (8)
C4—S1	1.775 (5)	C10—H10	0.9300
C5—C6	1.371 (8)	C11—N1	1.340 (7)
C5—H5	0.9300	C11—C12	1.383 (8)
C6—H6	0.9300	C11—H11	0.9300
C7—O2	1.233 (6)	C12—H12	0.9300
C7—O1	1.306 (6)	C13—O8	1.209 (7)
O1—H1	0.82 (2)	C13—O7	1.306 (7)
O3—H3A	0.82 (2)	N1—H1A	0.85 (2)
O4—S1	1.472 (4)	O7—H7	0.83 (5)
O3—C1—C6	117.1 (5)	O6—S1—C4	107.7 (2)
O3—C1—C2	123.5 (5)	O5—S1—C4	105.9 (3)
C6—C1—C2	119.3 (5)	O4—S1—C4	106.4 (3)
C1—C2—C3	118.9 (5)	C12—C8—C9	120.1 (6)
C1—C2—C7	119.9 (5)	C12—C8—C13	117.4 (5)
C3—C2—C7	121.2 (5)	C9—C8—C13	122.5 (6)
C4—C3—C2	120.8 (5)	C10—C9—C8	120.1 (6)
C4—C3—H3	119.6	C10—C9—H9	120.0
C2—C3—H3	119.6	C8—C9—H9	120.0
C3—C4—C5	119.9 (5)	N1—C10—C9	119.3 (6)
C3—C4—S1	121.5 (4)	N1—C10—H10	120.3
C5—C4—S1	118.6 (4)	C9—C10—H10	120.3
C6—C5—C4	119.9 (6)	N1—C11—C12	119.7 (6)
C6—C5—H5	120.1	N1—C11—H11	120.1
C4—C5—H5	120.1	C12—C11—H11	120.1
C5—C6—C1	121.1 (5)	C8—C12—C11	118.5 (5)
C5—C6—H6	119.4	C8—C12—H12	120.8
C1—C6—H6	119.4	C11—C12—H12	120.8
O2—C7—O1	122.8 (5)	O8—C13—O7	125.3 (6)
O2—C7—C2	122.3 (5)	O8—C13—C8	121.7 (6)
O1—C7—C2	114.8 (5)	O7—C13—C8	113.0 (5)
C7—O1—H1	115 (5)	C10—N1—C11	122.3 (6)
C1—O3—H3A	109 (5)	C10—N1—H1A	119 (4)
O6—S1—O5	113.5 (3)	C11—N1—H1A	119 (4)
O6—S1—O4	111.9 (2)	C13—O7—H7	105 (5)
O5—S1—O4	111.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.82 (2)	1.82 (2)	2.632 (5)	170 (7)
N1—H1A···O2ii	0.85 (2)	2.57 (5)	3.140 (7)	125 (5)
C3—H3···O3ii	0.93	2.51	3.379 (7)	156.
O3—H3A···O6iii	0.82 (2)	2.57 (5)	3.140 (5)	127 (6)
O7—H7···O4iv	0.83 (5)	1.87 (4)	2.654 (5)	155 (8)
C10—H10···O8v	0.93	2.46	3.152 (8)	132.
C11—H11···O4vi	0.93	2.57	3.257 (7)	131.
N1—H1A···O6	0.85 (2)	2.14 (3)	2.902 (6)	149 (5)
O3—H3A···O2	0.82 (2)	1.90 (4)	2.626 (5)	146 (6)
C10—H10···O4	0.93	2.54	3.331 (7)	143.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.82 (2)	1.82 (2)	2.632 (5)	170 (7)
N1—H1A⋯O2ii	0.85 (2)	2.57 (5)	3.140 (7)	125 (5)
C3—H3⋯O3ii	0.93	2.51	3.379 (7)	156
O3—H3A⋯O6iii	0.82 (2)	2.57 (5)	3.140 (5)	127 (6)
O7—H7⋯O4iv	0.83 (5)	1.87 (4)	2.654 (5)	155 (8)
C10—H10⋯O8v	0.93	2.46	3.152 (8)	132
C11—H11⋯O4vi	0.93	2.57	3.257 (7)	131
N1—H1A⋯O6	0.85 (2)	2.14 (3)	2.902 (6)	149 (5)
O3—H3A⋯O2	0.82 (2)	1.90 (4)	2.626 (5)	146 (6)
C10—H10⋯O4	0.93	2.54	3.331 (7)	143

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