Bis(2-amino-pyridinium) 2,5-dicarb-oxy-benzene-1,4-dicarboxyl-ate.

In the title compound, 2C(5)H(7)N(2) (+)·C(10)H(4)O(8) (2-), the 2-amino-pyridinium (2-apyH) cation and 2,5-dicarb-oxy-benzene-1,4-dicarboxyl-ate (btcH2) anion are both nearly planar, with r.m.s. deviations of 0.015 and 0.050 Å, respectively. The angle between the latter least-squares planes is 17.68 (9)°. The overall crystal structure results from the packing of two-dimensional networks, formed by alternating 2-apyH and btcH2 linked by hydrogen bonds, parallel to (100).

Related literature

For similar and most common conformations of 2-amino­pyridinium, see: Guelmami & Jouini (2011 ▶); Chitra et al. (2008 ▶); Quah et al. (2008 ▶); Bis & Zaworotko (2005 ▶); Büyükgüngör & Odabas˛ogˇlu (2002 ▶); Odabas˛ogˇlu et al. (2003 ▶); Acheson (1967 ▶). For similar and most common conformations of 2,5-dicarb­oxy­benzene-1,4-dicarboxyl­ate, see: Dong et al. (2011 ▶); Wang & Tang (2010 ▶). For graph-set analysis of hydrogen-bond patterns in organic crystals, see: Etter et al. (1990 ▶).

Experimental

Crystal data

2C5H7N2 +·C10H4O8 2−

M = 442.38

Monoclinic,

a = 4.0165 (1) Å

b = 10.8098 (4) Å

c = 21.4036 (7) Å

β = 99.535 (2)°

V = 916.45 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 273 K

0.3 × 0.2 × 0.15 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.755, T max = 1.000

18838 measured reflections

2209 independent reflections

1652 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.01

2209 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker–Nonius, 2004 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017254/bt5880sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017254/bt5880Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017254/bt5880Isup3.cml

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

2C5H7N2+·C10H4O82−	F(000) = 460
Mr = 442.38	Dx = 1.603 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7209 reflections
a = 4.0165 (1) Å	θ = 2.7–24.9°
b = 10.8098 (4) Å	µ = 0.13 mm−1
c = 21.4036 (7) Å	T = 273 K
β = 99.535 (2)°	Block, yellow
V = 916.45 (5) Å3	0.3 × 0.2 × 0.15 mm
Z = 2

Bruker–Nonius APEXII CCD area-detector diffractometer	2209 independent reflections
Radiation source: fine-focus sealed tube	1652 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −4→5
Tmin = 0.755, Tmax = 1.000	k = −13→14
18838 measured reflections	l = −27→23

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.1584P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2209 reflections	Δρmax = 0.20 e Å−3
158 parameters	Δρmin = −0.15 e Å−3
0 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: 0.014 (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
N1	1.1547 (3)	0.04940 (11)	0.38178 (5)	0.0424 (3)
H1A	1.040 (4)	0.1095 (15)	0.3993 (8)	0.051*
C1	1.1679 (3)	0.04905 (12)	0.32019 (6)	0.0370 (3)
N2	1.0229 (4)	0.14007 (12)	0.28496 (6)	0.0511 (3)
H2A	1.021 (4)	0.1363 (16)	0.2461 (9)	0.061*
H2B	0.916 (5)	0.1990 (16)	0.3019 (9)	0.061*
C3	1.3390 (4)	−0.04878 (13)	0.29700 (7)	0.0469 (4)
H3	1.3508	−0.0532	0.2540	0.056*
C4	1.4882 (4)	−0.13741 (15)	0.33704 (9)	0.0569 (4)
H4	1.6042	−0.2019	0.3215	0.068*
C5	1.4684 (4)	−0.13228 (16)	0.40058 (9)	0.0587 (4)
H5	1.5712	−0.1922	0.4285	0.070*
C6	1.2984 (4)	−0.03922 (15)	0.42096 (7)	0.0523 (4)
H6	1.2786	−0.0356	0.4636	0.063*
C7	0.7030 (3)	0.40755 (11)	0.52514 (6)	0.0325 (3)
H7	0.8444	0.3440	0.5427	0.039*
C8	0.5869 (3)	0.40386 (11)	0.46123 (5)	0.0312 (3)
C9	0.7148 (3)	0.29317 (12)	0.42838 (6)	0.0380 (3)
O1	0.6529 (3)	0.28618 (10)	0.36938 (5)	0.0588 (3)
O2	0.8806 (3)	0.21344 (9)	0.45984 (5)	0.0591 (3)
C10	0.3760 (3)	0.50071 (11)	0.43487 (5)	0.0315 (3)
C11	0.2130 (3)	0.52081 (12)	0.36717 (6)	0.0386 (3)
O3	0.0283 (3)	0.60888 (10)	0.35332 (5)	0.0571 (3)
O4	0.2721 (3)	0.44339 (10)	0.32502 (4)	0.0556 (3)
H4A	0.448 (5)	0.3738 (17)	0.3439 (8)	0.067*

	U11	U22	U33	U12	U13	U23
N1	0.0464 (7)	0.0473 (7)	0.0338 (6)	−0.0050 (5)	0.0072 (5)	−0.0078 (5)
C1	0.0391 (7)	0.0395 (7)	0.0316 (7)	−0.0064 (5)	0.0038 (5)	−0.0049 (5)
N2	0.0690 (9)	0.0481 (7)	0.0339 (6)	0.0058 (6)	0.0017 (6)	−0.0040 (6)
C3	0.0463 (8)	0.0510 (9)	0.0452 (8)	−0.0037 (7)	0.0129 (6)	−0.0118 (7)
C4	0.0450 (8)	0.0447 (8)	0.0820 (12)	0.0006 (7)	0.0131 (8)	−0.0058 (8)
C5	0.0511 (9)	0.0552 (9)	0.0664 (11)	−0.0078 (7)	0.0001 (8)	0.0187 (8)
C6	0.0516 (9)	0.0648 (10)	0.0387 (8)	−0.0144 (8)	0.0025 (7)	0.0090 (7)
C7	0.0367 (6)	0.0310 (6)	0.0303 (6)	−0.0027 (5)	0.0067 (5)	0.0019 (5)
C8	0.0349 (6)	0.0316 (6)	0.0284 (6)	−0.0069 (5)	0.0091 (5)	−0.0015 (5)
C9	0.0437 (7)	0.0364 (7)	0.0351 (7)	−0.0050 (6)	0.0102 (6)	−0.0056 (5)
O1	0.0832 (8)	0.0600 (7)	0.0336 (6)	0.0173 (6)	0.0113 (5)	−0.0114 (5)
O2	0.0841 (8)	0.0469 (6)	0.0453 (6)	0.0203 (6)	0.0074 (5)	−0.0048 (5)
C10	0.0358 (6)	0.0336 (6)	0.0259 (6)	−0.0087 (5)	0.0069 (5)	0.0005 (5)
C11	0.0451 (7)	0.0429 (7)	0.0275 (6)	−0.0065 (6)	0.0055 (5)	0.0006 (5)
O3	0.0777 (7)	0.0550 (7)	0.0336 (6)	0.0151 (6)	−0.0053 (5)	0.0017 (4)
O4	0.0763 (8)	0.0634 (7)	0.0257 (5)	0.0096 (6)	0.0045 (5)	−0.0065 (5)

N1—C1	1.3281 (17)	C6—H6	0.9300
N1—C6	1.3392 (19)	C7—C8	1.3707 (17)
N1—H1A	0.913 (16)	C7—C10i	1.3809 (17)
C1—N2	1.3154 (19)	C7—H7	0.9300
C1—C3	1.3964 (19)	C8—C10	1.4049 (18)
N2—H2A	0.831 (19)	C8—C9	1.5197 (17)
N2—H2B	0.880 (19)	C9—O2	1.2212 (16)
C3—C4	1.357 (2)	C9—O1	1.2483 (16)
C3—H3	0.9300	C10—C7i	1.3809 (17)
C4—C5	1.377 (2)	C10—C11	1.5037 (17)
C4—H4	0.9300	C11—O3	1.2133 (17)
C5—C6	1.329 (2)	C11—O4	1.2811 (16)
C5—H5	0.9300	O4—H4A	1.06 (2)
C1—N1—C6	122.39 (13)	C5—C6—H6	119.1
C1—N1—H1A	121.0 (10)	N1—C6—H6	119.1
C6—N1—H1A	116.6 (10)	C8—C7—C10i	124.36 (12)
N2—C1—N1	118.70 (13)	C8—C7—H7	117.8
N2—C1—C3	124.06 (13)	C10i—C7—H7	117.8
N1—C1—C3	117.24 (13)	C7—C8—C10	117.52 (11)
C1—N2—H2A	117.8 (12)	C7—C8—C9	113.54 (11)
C1—N2—H2B	120.4 (12)	C10—C8—C9	128.93 (11)
H2A—N2—H2B	121.5 (17)	O2—C9—O1	120.93 (12)
C4—C3—C1	120.15 (14)	O2—C9—C8	119.73 (11)
C4—C3—H3	119.9	O1—C9—C8	119.33 (12)
C1—C3—H3	119.9	C7i—C10—C8	118.12 (11)
C3—C4—C5	120.25 (15)	C7i—C10—C11	112.67 (11)
C3—C4—H4	119.9	C8—C10—C11	129.20 (11)
C5—C4—H4	119.9	O3—C11—O4	121.18 (12)
C6—C5—C4	118.13 (15)	O3—C11—C10	119.99 (12)
C6—C5—H5	120.9	O4—C11—C10	118.83 (12)
C4—C5—H5	120.9	C11—O4—H4A	112.5 (9)
C5—C6—N1	121.83 (15)
C6—N1—C1—N2	−179.42 (13)	C10—C8—C9—O2	−175.39 (13)
C6—N1—C1—C3	0.14 (19)	C7—C8—C9—O1	−173.10 (12)
N2—C1—C3—C4	178.46 (14)	C10—C8—C9—O1	5.7 (2)
N1—C1—C3—C4	−1.1 (2)	C7—C8—C10—C7i	−0.56 (18)
C1—C3—C4—C5	0.8 (2)	C9—C8—C10—C7i	−179.36 (11)
C3—C4—C5—C6	0.5 (2)	C7—C8—C10—C11	−179.96 (11)
C4—C5—C6—N1	−1.4 (2)	C9—C8—C10—C11	1.2 (2)
C1—N1—C6—C5	1.1 (2)	C7i—C10—C11—O3	−1.71 (17)
C10i—C7—C8—C10	0.60 (19)	C8—C10—C11—O3	177.72 (13)
C10i—C7—C8—C9	179.58 (11)	C7i—C10—C11—O4	178.55 (12)
C7—C8—C9—O2	5.76 (17)	C8—C10—C11—O4	−2.01 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.913 (16)	1.904 (17)	2.7852 (15)	161.6 (15)
N1—H1A···O1	0.913 (16)	2.478 (16)	3.2413 (16)	141.4 (13)
N2—H2A···O3ii	0.831 (19)	2.125 (19)	2.9520 (17)	173.0 (17)
N2—H2B···O1	0.880 (19)	2.14 (2)	2.9759 (17)	157.6 (16)
O4—H4A···O1	1.06 (2)	1.31 (2)	2.3766 (15)	176.8 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.913 (16)	1.904 (17)	2.7852 (15)	161.6 (15)
N1—H1A⋯O1	0.913 (16)	2.478 (16)	3.2413 (16)	141.4 (13)
N2—H2A⋯O3i	0.831 (19)	2.125 (19)	2.9520 (17)	173.0 (17)
N2—H2B⋯O1	0.880 (19)	2.14 (2)	2.9759 (17)	157.6 (16)
O4—H4A⋯O1	1.06 (2)	1.31 (2)	2.3766 (15)	176.8 (17)

Symmetry code: (i) .