4-(4-Pyrid­yl)pyridinium 3′,4,4′-tricarboxy­biphenyl-3-carboxyl­ate dihydrate

Han, L.; Luo, H.-M.; Meng, Q.-H.; Luo, Y.-F.; Zeng, R.-H.

doi:10.1107/S1600536809050831

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o68-o69

doi:10.1107/S1600536809050831

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4-(4-Pyridyl)pyridinium 3′,4,4′-tricarboxybiphenyl-3-carboxylate dihydrate

Lu Han,^a Huan-Mian Luo,^a Qiu-Hui Meng,^a Yi-Fan Luo ^a ^* and Rong-Hua Zeng ^a,^b

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and, South China Normal University, Key Laboratory of Technology of Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: luoyf2004@yahoo.com.cn

(Received 1 November 2009; accepted 25 November 2009; online 9 December 2009)

In the title compound, C₁₀H₉N₂⁺·C₁₆H₉O₈⁻·2H₂O, both the cation and anion possess crystallographically imposed centres of symmetry, causing the nitrogen-bound H atom in the 4-(4-pyridyl)pyridinium cation and the acidic H atom of the carboxylate groups at the 3 and 3′ positions in the anion to be disordered over two positions with equal occupancies. In the crystal packing, the cations, anions and water molecules are connected by O—H⋯O, C—H⋯O and N—H⋯N hydrogen bonds, forming layers parallel to (2 $[\overline{1}]$ 0). These layer are further connected into a three-dimensional supramolecular network by O—H⋯O hydrogen bonds involving the water molecules as H-atom donors and by weak π–π stacking interactions between neighbouring benzene and pyridine rings, with centroid–centroid distances of 3.756 (5) Å.

Related literature

For related structures, see: Wang et al. (2006 , 2007 ); Yang et al. (2007 ).

Experimental

Crystal data

C₁₀H₉N₂⁺·C₁₆H₉O₈⁻·2H₂O
M_r = 522.46
Triclinic, $[P \overline 1]$
a = 7.1955 (8) Å
b = 8.935 (1) Å
c = 9.8847 (11) Å
α = 90.7920 (11)°
β = 106.4850 (13)°
γ = 107.1180 (15)°
V = 579.09 (11) Å³
Z = 1
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
2990 measured reflections
2050 independent reflections
1818 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.03
2050 reflections
180 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N1ⁱ	0.92 (2)	1.89 (2)	2.814 (3)	177 (4)
O4—H4A⋯O1W	0.82	1.75	2.5657 (19)	176
O1W—H1W⋯O1ⁱⁱ	0.83	1.86	2.642 (2)	157
O1W—H2W⋯O3ⁱⁱⁱ	0.84	2.03	2.841 (2)	165
O2—H2A⋯O2^iv	0.91 (2)	1.54 (2)	2.446 (3)	173 (7)
C3—H3⋯O1^v	0.93	2.54	3.270 (2)	135
C13—H13⋯O2^vi	0.93	2.57	3.448 (2)	159
C9—H9⋯O2^vii	0.93	2.36	3.246 (2)	160
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1; (iv) -x, -y+1, -z; (v) -x+1, -y+1, -z; (vi) x+1, y, z; (vii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050831/rz2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050831/rz2388Isup2.hkl

checkCIF report

Comment top

In recent years, research on coordination polymers has made considerable progress in the fields of supramolecular chemistry and crystal engineering, because of their intriguing structural motifs and functional properties, such as molecular adsorption, magnetism, and luminescence. In general, hydrogen bonding interactions between ligands are specific and directional. In this context, biphenyl-3,3',4,4'-tetracarboxylic acid and 4,4'-bipyridine are excellent candidates for the construction of three-dimensional network motifs (Wang et al., 2006; Wang et al., 2007; Yang et al., 2007). Recently, we obtained the title compound under hydrothermal conditions and report its crystal structure here.

The asymmetric unit of the title compound contains one half of a monoprotic 4-4'-bipyridinium cation, one half of a 3-3'-4-tricarboxybiphenyl-4'-carboxylato anion and a water molecule, with both cation and anion possessing crystallographically imposed centre of symmetry (Fig. 1). As a result, the H1A nitrogen-bound hydrogen atom in the cation and acidic H2A hydrogen atom in the anion are disordered over two positions with site occupancies of 0.5. Bond lengths and angles are unexceptional. In the crystal packing (Fig. 2), cations, anions and lattice water molecules are linked by intermolecular O—H···O, C—H···O and N—H···N hydrogen bonds (Table 1) into layers parallel to (2 1 0). The layers are further connected into a three-dimensional network by O—H···O hydrogen bonds involving the water molecules as H-donors and by weak π–π stacking interactions involving neighbouring benzene and pyridine rings, with centroid-to-centroid distances of 3.756 (5) Å.

Related literature top

For related structures, see: Wang et al. (2006, 2007); Yang et al. (2007).

Experimental top

A mixture of 4,4'-bipyridine (0.078 g, 0.5 mmol), 4-4'-dicarboxybiphenyl-3-3'dicarboxylic acid (0.165 g; 0.5 mmol), water (10 mL) was stirred vigorously for 30 min and then sealed in a Teflon-lined stainless-steel autoclave (25 mL capacity). The autoclave was heated and maintained at 433K for 3 days, and then cooled to room temperature at 5Kh^-1 to obtain colourless block crystals suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic-numbering scheme and 50% probability ellipsoids. Only one position of the disordered H atoms in the cation and anion is shown. Symmetry codes: (i) 1-x, 2-y, -z; (ii) 2-x, -y, 1-z; (iii) -x, 1-y, -z.
	Fig. 2. Partial packing diagram of the title compound showing the layered network formed by intermolecular O—H···O, C—H···O and N—H···N hydrogen bonds (dashed lines). Both positions of the disordered H atoms in the cation and anions are shown.

4-(4-Pyridyl)pyridinium 3',4,4'-tricarboxybiphenyl-3-carboxylate dihydrate top

Crystal data top

C₁₀H₉N₂⁺·C₁₆H₉O₈⁻·2H₂O	Z = 1
M_r = 522.46	F(000) = 272
Triclinic, P1	D_x = 1.498 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1955 (8) Å	Cell parameters from 2061 reflections
b = 8.935 (1) Å	θ = 2.4–28.2°
c = 9.8847 (11) Å	µ = 0.12 mm⁻¹
α = 90.7920 (11)°	T = 296 K
β = 106.4850 (13)°	Block, colourless
γ = 107.1180 (15)°	0.23 × 0.21 × 0.19 mm
V = 579.09 (11) Å³

Data collection top

Bruker APEXII area-detector diffractometer	1818 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 25.2°, θ_min = 2.2°
ϕ and ω scan	h = −7→8
2990 measured reflections	k = −10→9
2050 independent reflections	l = −11→11

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0562P)² + 0.2257P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2050 reflections	Δρ_max = 0.32 e Å⁻³
180 parameters	Δρ_min = −0.25 e Å⁻³
3 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: 0.071 (9)

Crystal data top

C₁₀H₉N₂⁺·C₁₆H₉O₈⁻·2H₂O	γ = 107.1180 (15)°
M_r = 522.46	V = 579.09 (11) Å³
Triclinic, P1	Z = 1
a = 7.1955 (8) Å	Mo Kα radiation
b = 8.935 (1) Å	µ = 0.12 mm⁻¹
c = 9.8847 (11) Å	T = 296 K
α = 90.7920 (11)°	0.23 × 0.21 × 0.19 mm
β = 106.4850 (13)°

Data collection top

Bruker APEXII area-detector diffractometer	1818 reflections with I > 2σ(I)
2990 measured reflections	R_int = 0.014
2050 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.32 e Å⁻³
2050 reflections	Δρ_min = −0.25 e Å⁻³
180 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.4881 (3)	1.01415 (19)	0.18864 (18)	0.0405 (4)
H1	0.5318	1.1230	0.2095	0.049*
C2	0.4740 (2)	0.94960 (17)	0.05542 (16)	0.0321 (4)
C3	0.4103 (3)	0.78512 (18)	0.03012 (17)	0.0361 (4)
H3	0.4008	0.7393	−0.0576	0.043*
C4	0.3611 (2)	0.68843 (17)	0.13133 (17)	0.0333 (4)
C5	0.3102 (3)	0.51258 (19)	0.09704 (18)	0.0397 (4)
C6	0.3725 (2)	0.75584 (18)	0.26291 (16)	0.0344 (4)
C7	0.3003 (3)	0.65386 (19)	0.36673 (18)	0.0389 (4)
C8	0.4384 (3)	0.91911 (19)	0.28990 (18)	0.0407 (4)
H8	0.4490	0.9650	0.3779	0.049*
C9	0.9236 (3)	−0.1318 (2)	0.19327 (19)	0.0447 (4)
H9	0.8726	−0.2254	0.1336	0.054*
C10	0.9232 (3)	−0.13691 (19)	0.33220 (18)	0.0412 (4)
H10	0.8722	−0.2331	0.3647	0.049*
C11	0.9987 (2)	0.00096 (18)	0.42445 (17)	0.0351 (4)
C12	1.0714 (3)	0.1400 (2)	0.3674 (2)	0.0490 (5)
H12	1.1234	0.2355	0.4243	0.059*
C13	1.0666 (3)	0.1367 (2)	0.2273 (2)	0.0524 (5)
H13	1.1151	0.2311	0.1914	0.063*
N1	0.9947 (2)	0.00297 (17)	0.14119 (15)	0.0428 (4)
H1A	0.997 (7)	0.004 (5)	0.049 (2)	0.051*	0.50
O1	0.4404 (2)	0.44851 (15)	0.14281 (16)	0.0572 (4)
O3	0.1949 (2)	0.51807 (15)	0.33352 (14)	0.0596 (4)
O4	0.3524 (3)	0.72538 (16)	0.49433 (14)	0.0647 (5)
H4A	0.3092	0.6627	0.5465	0.097*
O1W	0.2145 (3)	0.5413 (2)	0.66452 (17)	0.0799 (6)
H1W	0.3004	0.5290	0.7356	0.120*
H2W	0.1031	0.5241	0.6817	0.120*
O2	0.1336 (2)	0.43770 (14)	0.01377 (15)	0.0520 (4)
H2A	0.040 (8)	0.490 (8)	0.001 (8)	0.078*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0520 (10)	0.0255 (8)	0.0388 (9)	0.0025 (7)	0.0159 (8)	−0.0015 (7)
C2	0.0325 (8)	0.0276 (8)	0.0339 (8)	0.0060 (6)	0.0100 (6)	0.0017 (6)
C3	0.0467 (9)	0.0279 (8)	0.0327 (8)	0.0081 (7)	0.0141 (7)	−0.0006 (6)
C4	0.0346 (8)	0.0277 (8)	0.0352 (8)	0.0066 (6)	0.0102 (6)	0.0025 (6)
C5	0.0549 (10)	0.0293 (8)	0.0396 (9)	0.0115 (8)	0.0231 (8)	0.0057 (7)
C6	0.0353 (8)	0.0308 (8)	0.0339 (8)	0.0054 (6)	0.0104 (7)	0.0027 (6)
C7	0.0447 (9)	0.0324 (8)	0.0376 (9)	0.0063 (7)	0.0152 (7)	0.0023 (7)
C8	0.0526 (10)	0.0325 (8)	0.0323 (9)	0.0041 (7)	0.0153 (7)	−0.0022 (7)
C9	0.0530 (11)	0.0371 (9)	0.0421 (10)	0.0122 (8)	0.0135 (8)	−0.0016 (7)
C10	0.0513 (10)	0.0285 (8)	0.0431 (10)	0.0093 (7)	0.0163 (8)	0.0035 (7)
C11	0.0373 (8)	0.0286 (8)	0.0391 (9)	0.0092 (6)	0.0119 (7)	0.0039 (6)
C12	0.0691 (13)	0.0293 (9)	0.0425 (10)	0.0041 (8)	0.0190 (9)	0.0022 (7)
C13	0.0714 (13)	0.0379 (10)	0.0451 (10)	0.0079 (9)	0.0226 (9)	0.0093 (8)
N1	0.0516 (9)	0.0454 (8)	0.0332 (8)	0.0152 (7)	0.0151 (7)	0.0064 (6)
O1	0.0725 (10)	0.0442 (7)	0.0666 (9)	0.0307 (7)	0.0254 (7)	0.0142 (6)
O3	0.0830 (10)	0.0355 (7)	0.0522 (8)	−0.0054 (7)	0.0330 (7)	0.0011 (6)
O4	0.0976 (11)	0.0443 (8)	0.0368 (7)	−0.0065 (7)	0.0266 (7)	0.0019 (6)
O1W	0.0693 (10)	0.0986 (13)	0.0630 (10)	0.0071 (9)	0.0252 (8)	0.0340 (9)
O2	0.0599 (9)	0.0273 (6)	0.0601 (8)	0.0046 (6)	0.0146 (7)	−0.0086 (6)

Geometric parameters (Å, º) top

C1—C8	1.378 (2)	C9—N1	1.334 (2)
C1—C2	1.395 (2)	C9—C10	1.375 (3)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.400 (2)	C10—C11	1.392 (2)
C2—C2ⁱ	1.488 (3)	C10—H10	0.9300
C3—C4	1.385 (2)	C11—C12	1.392 (2)
C3—H3	0.9300	C11—C11ⁱⁱ	1.489 (3)
C4—C6	1.397 (2)	C12—C13	1.375 (3)
C4—C5	1.514 (2)	C12—H12	0.9300
C5—O1	1.222 (2)	C13—N1	1.334 (2)
C5—O2	1.277 (2)	C13—H13	0.9300
C6—C8	1.391 (2)	N1—H1A	0.921 (18)
C6—C7	1.484 (2)	O4—H4A	0.8200
C7—O3	1.209 (2)	O1W—H1W	0.8263
C7—O4	1.307 (2)	O1W—H2W	0.8370
C8—H8	0.9300	O2—H2A	0.911 (19)

C8—C1—C2	121.02 (15)	C6—C8—H8	119.4
C8—C1—H1	119.5	N1—C9—C10	122.24 (16)
C2—C1—H1	119.5	N1—C9—H9	118.9
C1—C2—C3	117.26 (15)	C10—C9—H9	118.9
C1—C2—C2ⁱ	121.74 (17)	C9—C10—C11	120.39 (16)
C3—C2—C2ⁱ	121.00 (17)	C9—C10—H10	119.8
C4—C3—C2	122.24 (15)	C11—C10—H10	119.8
C4—C3—H3	118.9	C10—C11—C12	116.23 (16)
C2—C3—H3	118.9	C10—C11—C11ⁱⁱ	121.63 (18)
C3—C4—C6	119.43 (14)	C12—C11—C11ⁱⁱ	122.14 (18)
C3—C4—C5	117.83 (14)	C13—C12—C11	120.36 (16)
C6—C4—C5	122.62 (14)	C13—C12—H12	119.8
O1—C5—O2	122.14 (16)	C11—C12—H12	119.8
O1—C5—C4	119.75 (16)	N1—C13—C12	122.31 (17)
O2—C5—C4	117.99 (15)	N1—C13—H13	118.8
C8—C6—C4	118.80 (15)	C12—C13—H13	118.8
C8—C6—C7	121.15 (14)	C13—N1—C9	118.47 (15)
C4—C6—C7	119.90 (14)	C13—N1—H1A	120 (3)
O3—C7—O4	123.27 (16)	C9—N1—H1A	121 (3)
O3—C7—C6	122.33 (15)	C7—O4—H4A	109.5
O4—C7—C6	114.33 (14)	H1W—O1W—H2W	109.1
C1—C8—C6	121.24 (15)	C5—O2—H2A	115 (5)
C1—C8—H8	119.4

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1ⁱⁱⁱ	0.92 (2)	1.89 (2)	2.814 (3)	177 (4)
O4—H4A···O1W	0.82	1.75	2.5657 (19)	176
O1W—H1W···O1^iv	0.83	1.86	2.642 (2)	157
O1W—H2W···O3^v	0.84	2.03	2.841 (2)	165
O2—H2A···O2^vi	0.91 (2)	1.54 (2)	2.446 (3)	173 (7)
C3—H3···O1^vii	0.93	2.54	3.270 (2)	135
C13—H13···O2^viii	0.93	2.57	3.448 (2)	159
C9—H9···O2^ix	0.93	2.36	3.246 (2)	160

Symmetry codes: (iii) −x+2, −y, −z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y+1, −z; (vii) −x+1, −y+1, −z; (viii) x+1, y, z; (ix) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₂⁺·C₁₆H₉O₈⁻·2H₂O
M_r	522.46
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1955 (8), 8.935 (1), 9.8847 (11)
α, β, γ (°)	90.7920 (11), 106.4850 (13), 107.1180 (15)
V (Å³)	579.09 (11)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2990, 2050, 1818
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.03
No. of reflections	2050
No. of parameters	180
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1ⁱ	0.921 (18)	1.894 (19)	2.814 (3)	177 (4)
O4—H4A···O1W	0.82	1.75	2.5657 (19)	175.5
O1W—H1W···O1ⁱⁱ	0.83	1.86	2.642 (2)	157.0
O1W—H2W···O3ⁱⁱⁱ	0.84	2.03	2.841 (2)	164.7
O2—H2A···O2^iv	0.911 (19)	1.54 (2)	2.446 (3)	173 (7)
C3—H3···O1^v	0.93	2.54	3.270 (2)	135.4
C13—H13···O2^vi	0.93	2.57	3.448 (2)	158.6
C9—H9···O2^vii	0.93	2.36	3.246 (2)	159.6

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) −x+1, −y+1, −z; (vi) x+1, y, z; (vii) −x+1, −y, −z.

Acknowledgements

The authors acknowledge the Chan Xue Yan Cooperative Special Project of Guangdong Province, the Ministry of Science and Technology (project No. 2007A090302046), the Project of Science and Technology of Guangdong Province (project No. 2007A020200002-4) and the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for supporting this work.

References

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o68-o69

doi:10.1107/S1600536809050831

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Pyrid­yl)pyridinium 3′,4,4′-tri­carb­oxy­bi­phenyl-3-carboxyl­ate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Pyridyl)pyridinium 3′,4,4′-tricarboxybiphenyl-3-carboxylate dihydrate