4,4'-Bipyridinium 1,4-phenyl-ene-diacetate.

The title compound, C(10)H(10)N(2) (2+)·C(10)H(8)O(4) (2-), has inversion centres located at the geometric centres of the 1,4-phenyl-enediacetate anion and 4,4'-bipyridinium cation. The anions and cations are connected by N-H⋯O hydrogen bonds, forming one-dimensional supra-molecular chains, which inter-act with each other via π-π inter-actions [centroid-centroid distance = 3.938 (2) Å], building a two-dimensional supra-molecular 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

C10H10N2 2+·C10H8O4 2−

M = 350.36

Triclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.193

S = 1.07

1499 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.25 e Å−3

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.

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

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

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

C10H10N22+·C10H8O42−	Z = 1
Mr = 350.36	F(000) = 184
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0979P)2 + 0.1429P] where P = (Fo2 + 2Fc2)/3
1499 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
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*

	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)

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)

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

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