4,4′-Bipyridinium 1,4-phenyl­ene­diacetate

Jia, M.; Liu, X.; Miao, J.; Xiong, W.; Chen, Z.

doi:10.1107/S1600536809036836

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2490

doi:10.1107/S1600536809036836

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4,4′-Bipyridinium 1,4-phenylenediacetate

Maomao Jia,^a Xianlin Liu,^a Jing Miao,^a Wei Xiong ^a and Zilu Chen ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People's Republic of China
^*Correspondence e-mail: chenziluczl@yahoo.co.uk

(Received 30 August 2009; accepted 11 September 2009; online 19 September 2009)

The title compound, C₁₀H₁₀N₂²⁺·C₁₀H₈O₄²⁻, has inversion centres located at the geometric centres of the 1,4-phenylenediacetate anion and 4,4′-bipyridinium cation. The anions and cations are connected by N—H⋯O hydrogen bonds, forming one-dimensional supramolecular chains, which interact with each other via π–π interactions [centroid–centroid distance = 3.938 (2) Å], building a two-dimensional supramolecular sheet.

Related literature

For related complexes of 1,4-phenylenediacetic acid, see: Braverman & LaDuca (2007 ); Soares-Santos et al. (2008 ); Liu et al. (2009 ); Chen et al. (2006a ,b ).

Experimental

Crystal data

C₁₀H₁₀N₂²⁺·C₁₀H₈O₄²⁻
M_r = 350.36
Triclinic, $[P \overline 1]$
a = 4.579 (3) Å
b = 6.950 (5) Å
c = 13.859 (10) Å
α = 99.618 (9)°
β = 93.672 (9)°
γ = 97.373 (8)°
V = 429.6 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.977, T_max = 0.983
2241 measured reflections
1499 independent reflections
1052 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.193
S = 1.07
1499 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.41 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—H1⋯O2	0.86	1.75	2.613 (3)	176

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036836/jh2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036836/jh2103Isup2.hkl

checkCIF report

Comment top

The flexible ligand of 1,4-phenylenediacetate is drawing much interest in constructing metal–organic framework or supramolecular molecules due to its flexibility and its multifunctional groups of carboxylato group and phenyl ring (Braverman & LaDuca 2007; Soares-Santos et al., 2008; Liu et al., 2009; Chen et al., 2006a,b). We thus report here a supramolecular structrure formed by 4,4'-bipyridine and 1,4-phenylenediacetic acid. The title compound 4,4'-bipyridinium 1,4-phenylenediacetate (Fig. 1), [C₁₀H₁₀N₂][C₁₀H₈O₄], has inversion centres located on the geometric centres of the 1,4-phenylenediacetate anion and 4,4'-bipyridinium cation. Each 4,4'-bipyridinium cation connects two 1,4-phenylenediacetate anions via N—H···O hydrogen bonds (Table 1), and vice versa. This leads to the formation of one dimensional supramolecular chains as shown in Fig. 2. The neighboring pyridyl rings from the adjacent one chains parallel to each other with perpendicular distance of 3.5654 (4) Å, a centre-to-centre distance of 3.938 (2) Å and an off-set angle of 25.135 (7)°. These information suggest the existence of significant π···π stacking interaction between the two pyridyl rings, which results in the construction of two dimensional supramolecular sheets (Fig. 2) from the one dimensional chains.

Related literature top

For related complexes of 1,4-phenylenediacetic acid, see: Braverman & LaDuca (2007); Soares-Santos et al. (2008); Liu et al. (2009); Chen et al. (2006a,b).

Experimental top

A mixture of 1,4-phenylenediacetic acid (0.0584 g, 0.3 mmol), 4,4'-bipyridine (0.0312 g, 0.2 mmol), Mn(CH₃COO)₂.4H₂O (0.0735 g, 0.3 mmol) and ethanol (2 ml) was sealed in a 23 ml Teflon-lined autoclave, heated at 140 °C for 4 d and cooled over a period of 48 h. Colorless crystals of the title compound were collected in a yield of 60% (0.0802 g). Found: C, 68.26; H, 5.40; N, 7.28. C₂₀H₁₈N₂O₄ requires C, 68.56; H, 5.18; N, 7.52%.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 with the atom-numbering scheme and 30% displacement ellipsoids.
	Fig. 2. A view of the two-dimensional supramolecular sheet assembled by hydrogen bonds and π···π stacking interactions.

4,4'-Bipyridinium 1,4-phenylenediacetate top

Crystal data top

C₁₀H₁₀N₂²⁺·C₁₀H₈O₄²⁻	Z = 1
M_r = 350.36	F(000) = 184
Triclinic, P1	D_x = 1.354 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.579 (3) Å	Cell parameters from 736 reflections
b = 6.950 (5) Å	θ = 3.0–23.8°
c = 13.859 (10) Å	µ = 0.10 mm⁻¹
α = 99.618 (9)°	T = 296 K
β = 93.672 (9)°	Block, colourless
γ = 97.373 (8)°	0.25 × 0.20 × 0.18 mm
V = 429.6 (5) Å³

Data collection top

Bruker SMART CCD area detector diffractometer	1499 independent reflections
Radiation source: fine-focus sealed tube	1052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→5
T_min = 0.977, T_max = 0.983	k = −8→7
2241 measured reflections	l = −10→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0979P)² + 0.1429P] where P = (F_o² + 2F_c²)/3
1499 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₁₀N₂²⁺·C₁₀H₈O₄²⁻	γ = 97.373 (8)°
M_r = 350.36	V = 429.6 (5) Å³
Triclinic, P1	Z = 1
a = 4.579 (3) Å	Mo Kα radiation
b = 6.950 (5) Å	µ = 0.10 mm⁻¹
c = 13.859 (10) Å	T = 296 K
α = 99.618 (9)°	0.25 × 0.20 × 0.18 mm
β = 93.672 (9)°

Data collection top

Bruker SMART CCD area detector diffractometer	1499 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1052 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.983	R_int = 0.014
2241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.193	H-atom parameters constrained
S = 1.07	Δρ_max = 0.41 e Å⁻³
1499 reflections	Δρ_min = −0.25 e Å⁻³
118 parameters

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
O2	0.6746 (5)	0.5442 (3)	0.19005 (15)	0.0691 (7)
O1	0.7402 (6)	0.3340 (3)	0.28869 (16)	0.0812 (8)
N1	0.3813 (5)	0.7303 (4)	0.32281 (18)	0.0628 (7)
H1	0.4734	0.6645	0.2794	0.075*
C8	0.0807 (6)	0.9428 (4)	0.46281 (19)	0.0511 (7)
C4	0.6539 (6)	−0.0571 (4)	0.0761 (2)	0.0568 (8)
H4	0.7572	−0.0977	0.1273	0.068*
C5	0.4446 (7)	−0.1901 (4)	0.0152 (2)	0.0583 (8)
H5	0.4078	−0.3191	0.0262	0.070*
C3	0.7125 (6)	0.1349 (4)	0.06220 (19)	0.0522 (7)
C7	0.1869 (7)	0.7720 (4)	0.4784 (2)	0.0644 (8)
H7	0.1595	0.7255	0.5367	0.077*
C9	0.1311 (8)	1.0030 (5)	0.3742 (2)	0.0709 (9)
H9	0.0632	1.1163	0.3597	0.085*
C6	0.3343 (7)	0.6709 (4)	0.4066 (2)	0.0689 (9)
H6	0.4032	0.5558	0.4179	0.083*
C2	0.9333 (7)	0.2827 (5)	0.1320 (2)	0.0642 (8)
H2A	1.0804	0.2150	0.1606	0.077*
H2B	1.0338	0.3765	0.0963	0.077*
C1	0.7762 (6)	0.3900 (4)	0.2123 (2)	0.0524 (7)
C10	0.2832 (7)	0.8930 (5)	0.3077 (2)	0.0739 (10)
H10	0.3182	0.9365	0.2490	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0924 (16)	0.0590 (13)	0.0641 (14)	0.0268 (11)	0.0119 (11)	0.0198 (10)
O1	0.119 (2)	0.0764 (15)	0.0619 (14)	0.0402 (14)	0.0238 (13)	0.0264 (12)
N1	0.0687 (16)	0.0644 (16)	0.0565 (15)	0.0193 (12)	0.0133 (12)	0.0033 (12)
C8	0.0531 (16)	0.0494 (15)	0.0509 (16)	0.0097 (12)	0.0035 (12)	0.0074 (12)
C4	0.0694 (18)	0.0581 (17)	0.0498 (16)	0.0235 (14)	0.0140 (14)	0.0151 (13)
C5	0.0774 (19)	0.0476 (16)	0.0568 (17)	0.0191 (14)	0.0214 (15)	0.0157 (13)
C3	0.0563 (16)	0.0547 (16)	0.0487 (15)	0.0168 (13)	0.0214 (12)	0.0049 (12)
C7	0.085 (2)	0.0583 (18)	0.0566 (18)	0.0252 (15)	0.0140 (15)	0.0156 (14)
C9	0.094 (2)	0.066 (2)	0.066 (2)	0.0364 (17)	0.0240 (17)	0.0240 (15)
C6	0.092 (2)	0.0569 (18)	0.065 (2)	0.0303 (17)	0.0141 (17)	0.0125 (15)
C2	0.0603 (17)	0.0675 (19)	0.0650 (19)	0.0138 (15)	0.0152 (14)	0.0048 (15)
C1	0.0589 (16)	0.0480 (15)	0.0503 (16)	0.0081 (13)	0.0052 (13)	0.0081 (12)
C10	0.095 (2)	0.076 (2)	0.063 (2)	0.0354 (19)	0.0246 (18)	0.0229 (16)

Geometric parameters (Å, º) top

O2—C1	1.296 (3)	C5—H5	0.9300
O1—C1	1.202 (3)	C3—C5ⁱⁱ	1.388 (4)
N1—C10	1.312 (4)	C3—C2	1.513 (4)
N1—C6	1.317 (4)	C7—C6	1.383 (4)
N1—H1	0.8600	C7—H7	0.9300
C8—C7	1.383 (4)	C9—C10	1.379 (4)
C8—C9	1.386 (4)	C9—H9	0.9300
C8—C8ⁱ	1.488 (5)	C6—H6	0.9300
C4—C3	1.375 (4)	C2—C1	1.508 (4)
C4—C5	1.375 (4)	C2—H2A	0.9700
C4—H4	0.9300	C2—H2B	0.9700
C5—C3ⁱⁱ	1.388 (4)	C10—H10	0.9300

C10—N1—C6	117.9 (3)	C10—C9—C8	119.3 (3)
C10—N1—H1	121.0	C10—C9—H9	120.4
C6—N1—H1	121.0	C8—C9—H9	120.4
C7—C8—C9	116.8 (3)	N1—C6—C7	122.9 (3)
C7—C8—C8ⁱ	122.0 (3)	N1—C6—H6	118.5
C9—C8—C8ⁱ	121.3 (3)	C7—C6—H6	118.5
C3—C4—C5	120.9 (3)	C1—C2—C3	109.8 (2)
C3—C4—H4	119.5	C1—C2—H2A	109.7
C5—C4—H4	119.5	C3—C2—H2A	109.7
C4—C5—C3ⁱⁱ	121.1 (3)	C1—C2—H2B	109.7
C4—C5—H5	119.5	C3—C2—H2B	109.7
C3ⁱⁱ—C5—H5	119.5	H2A—C2—H2B	108.2
C4—C3—C5ⁱⁱ	118.0 (3)	O1—C1—O2	123.0 (3)
C4—C3—C2	120.7 (3)	O1—C1—C2	123.0 (3)
C5ⁱⁱ—C3—C2	121.3 (3)	O2—C1—C2	113.9 (3)
C8—C7—C6	119.6 (3)	N1—C10—C9	123.5 (3)
C8—C7—H7	120.2	N1—C10—H10	118.3
C6—C7—H7	120.2	C9—C10—H10	118.3

C3—C4—C5—C3ⁱⁱ	0.3 (4)	C8—C7—C6—N1	0.4 (5)
C5—C4—C3—C5ⁱⁱ	−0.3 (4)	C4—C3—C2—C1	−92.6 (3)
C5—C4—C3—C2	177.3 (2)	C5ⁱⁱ—C3—C2—C1	85.0 (3)
C9—C8—C7—C6	−0.2 (5)	C3—C2—C1—O1	90.7 (4)
C8ⁱ—C8—C7—C6	179.7 (3)	C3—C2—C1—O2	−87.0 (3)
C7—C8—C9—C10	−0.5 (5)	C6—N1—C10—C9	−0.8 (5)
C8ⁱ—C8—C9—C10	179.6 (3)	C8—C9—C10—N1	1.0 (6)
C10—N1—C6—C7	0.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.75	2.613 (3)	176

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂²⁺·C₁₀H₈O₄²⁻
M_r	350.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.579 (3), 6.950 (5), 13.859 (10)
α, β, γ (°)	99.618 (9), 93.672 (9), 97.373 (8)
V (Å³)	429.6 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	2241, 1499, 1052
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.193, 1.07
No. of reflections	1499
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.25

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), 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—H1···O2	0.86	1.75	2.613 (3)	176.4

Acknowledgements

The authors are grateful for financial support from the Guangxi Natural Science Foundation (grant No. 0991008) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, China (grant No. [2006]331).

References

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