4-Carboxy­pyridinium 3-carb­oxy-4-hydroxy­benzene­sulfonate

Wang, Z.; Yao, K.; Liu, Z.; Xu, H.

doi:10.1107/S1600536808015882

organic compounds

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Volume 64| Part 7| July 2008| Page o1192

doi:10.1107/S1600536808015882

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4-Carboxypyridinium 3-carboxy-4-hydroxybenzenesulfonate

Zhong-long Wang,^a,^b ^* Kai-lun Yao,^a Zu-li Liu ^a and Hui-jin Xu ^b

^aDepartment of Physics, Huazhong University of Science and Technology, Wuhan 430074, People's Republic of China, and ^bScience College, China Three Gorges University, Yichang 443002, People's Republic of China
^*Correspondence e-mail: zhonglong_wang@126.com

(Received 22 May 2008; accepted 27 May 2008; online 7 June 2008)

Cocrystallization of 4-carboxypyridine (4-CPY) and 5-sulfosalicylic acid (5-H₂SSA) yields the title salt, C₆H₆NO₂⁺·C₇H₅O₆S⁻. In the crystal structure, the components of the salt are linked by a combination of intermolecular 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⁺·C₇H₅O₆S⁻
M_r = 341.29
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.168
S = 0.97
2545 reflections
220 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1056 Friedel pairs
Flack parameter: −0.1 (2)

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⋯O4^iv	0.83 (5)	1.87 (4)	2.654 (5)	155 (8)
C10—H10⋯O8^v	0.93	2.46	3.152 (8)	132
C11—H11⋯O4^vi	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) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

As awareness of the importance of pharmaceutical molecular adducts grows, it becomes imperative to fully understand and investigate the intermolecular interactions in a binary, ternary or multi-component organic adducts (Aakeröy and Salmon, 2005). 5-sulfosalicylic acid (5-H₂SSA), is a particularly strong acid which is capable of donating its sulfonic protons to many N-containing heterocycles, forming organic salts (Smith et al., 2006; Meng et al., 2007 and 2008; Fan et al., 2005). With the aim of gaining more insight into hydrogen-bonding interactions involving 5-H₂SSA and pyridine derivatives, we report here the molecular and supramolecular structure of the title compound.

In the asymmetric unit of title compound (I), contains one 5-HSSA^-and one 4-CPY⁺ ion. Similar to the analogous organic adducts reported (Meng et al., 2007), the H atom is transferred from the sulfonic acid group to the pyridine N atom forming an 1:1 organic salt.

In the crystal structure, the component ions are linked by a combination of O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig.2). An analysis using PLATON (Spek, 2003), showed that there are no other interactions (e.g. C—H···π and π-π) observed in the crystal structure.

Related literature top

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

Experimental top

All reagents and solvents were used as obtained without further purification. Equivalent molar amount of 4-carboxypyridine and 5-sulfosalicylic acid dihydrate were dissolved in 95% methanol (20 ml). The mixture was stirred for 10 minutes at 330 K and then filtered. Colorless needles of (I) suitable for single-crystal X-ray diffraction analysis grew at the bottom of the vessel in one week after slow evaporation of the solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H-bonds are shown as dashed lines.
	Fig. 2. Part of the crystal structure of (I), showing the formation of the three-dimensional framework structure. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted from the drawing.

4-Carboxypyridinium 3-carboxy-4-hydroxybenzenesulfonate top

Crystal data top

C₆H₆NO₂⁺·C₇H₅O₆S⁻	F(000) = 704
M_r = 341.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0554P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
2545 reflections	Δρ_max = 0.45 e Å⁻³
220 parameters	Δρ_min = −0.37 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 1056 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (2)

Crystal data top

C₆H₆NO₂⁺·C₇H₅O₆S⁻	V = 1449.9 (2) Å³
M_r = 341.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6358 (6) Å	µ = 0.27 mm⁻¹
b = 13.0514 (12) Å	T = 298 K
c = 16.7415 (14) Å	0.30 × 0.04 × 0.02 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1522 reflections with I > 2σ(I)
13287 measured reflections	R_int = 0.143
2545 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	Δρ_max = 0.45 e Å⁻³
S = 0.97	Δρ_min = −0.37 e Å⁻³
2545 reflections	Absolute structure: Flack (1983), 1056 Friedel pairs
220 parameters	Absolute structure parameter: −0.1 (2)
5 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.83 (5)	1.87 (4)	2.654 (5)	155 (8)
C10—H10···O8^v	0.93	2.46	3.152 (8)	132
C11—H11···O4^vi	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) −x+1/2, −y+1, z−1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₆H₆NO₂⁺·C₇H₅O₆S⁻
M_r	341.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	6.6358 (6), 13.0514 (12), 16.7415 (14)
V (Å³)	1449.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13287, 2545, 1522
R_int	0.143
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.168, 0.97
No. of reflections	2545
No. of parameters	220
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.37
Absolute structure	Flack (1983), 1056 Friedel pairs
Absolute structure parameter	−0.1 (2)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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)	156.3
O3—H3A···O6ⁱⁱⁱ	0.82 (2)	2.57 (5)	3.140 (5)	127 (6)
O7—H7···O4^iv	0.83 (5)	1.87 (4)	2.654 (5)	155 (8)
C10—H10···O8^v	0.93	2.46	3.152 (8)	131.6
C11—H11···O4^vi	0.93	2.57	3.257 (7)	130.6
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)	142.6

Acknowledgements

This work was supported by the National Natural Science Foundation of China under grants No. 10574047, No. 10574048 and No. 20490210. This work was also supported by the National 973 Project under grant No. 2006CB921605.

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