Poly[(μ(2)-nitrato-κO:O')(μ(2)-pyrimidin-ium-2-carboxyl-ato-κO:O')lithium(I)].

In the structure of the title compound, [Li(C(5)H(4)N(2)O(2))(NO(3))](n), the Li(I) ion is coordinated by two carboxyl-ate O atoms donated by two ligands and two nitrate O atoms in a distorted tetrahedral geometry. Li(I) ions, bridged by carboxyl-ate O atoms, form mol-ecular ribbons composed of dimeric units. Two nitrate O atoms link the ribbons into mol-ecular layers parallel to (001). Hydrogen bonds are active between protonated heterocyclic N atoms as donors and carboxyl-ate O atoms as acceptors. The layers are held together by van der Waals inter-actions.

Related literature

For the polymeric structures of some metal complexes with a pyrimidine-2-carboxyl­ate ligand, see: Rodríguez-Diéguez et al. (2007 ▶, 2008 ▶); Zhao & Liu (2010 ▶); Zhang et al. (2008a ▶). For structures built of monomeric mol­ecules, see: Kokunov & Gorbunova (2007 ▶); Antolić et al. (2000 ▶); Zhang et al. (2008b ▶); Suares-Varela et al. (2008 ▶).

Experimental

Crystal data

[Li(C5H4N2O2)(NO3)]

M = 193.05

Orthorhombic,

a = 12.403 (3) Å

b = 9.3290 (19) Å

c = 12.810 (3) Å

V = 1482.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.49 × 0.48 × 0.14 mm

Data collection

Kuma KM-4 four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction,2008 ▶) T min = 0.782, T max = 0.939

4248 measured reflections

2179 independent reflections

1504 reflections with I > 2σ(I)

R int = 0.158

3 standard reflections every 200 reflections intensity decay: 3.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.153

S = 0.97

2179 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.32 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 ▶); 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 I, global. DOI: 10.1107/S1600536811019520/kp2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019520/kp2322Isup2.hkl

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

[Li(C5H4N2O2)(NO3)]	F(000) = 784
Mr = 193.05	Dx = 1.730 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 12.403 (3) Å	θ = 6–15°
b = 9.3290 (19) Å	µ = 0.15 mm−1
c = 12.810 (3) Å	T = 293 K
V = 1482.2 (5) Å3	Plates, colorless
Z = 8	0.49 × 0.48 × 0.14 mm

Kuma KM-4 four-circle diffractometer	1504 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.158
graphite	θmax = 30.1°, θmin = 3.2°
profile data from ω/2θ scans	h = 0→17
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction,2008)	k = 0→13
Tmin = 0.782, Tmax = 0.939	l = −18→18
4248 measured reflections	3 standard reflections every 200 reflections
2179 independent reflections	intensity decay: 3.8%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.2975P] where P = (Fo2 + 2Fc2)/3
2179 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.32 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
N2	0.61057 (10)	0.04538 (11)	0.35126 (12)	0.0250 (3)
O1	0.71796 (9)	0.39321 (10)	0.32671 (12)	0.0323 (3)
O11	0.47373 (9)	0.63026 (13)	0.36709 (13)	0.0400 (4)
N1	0.52999 (10)	0.27071 (12)	0.37133 (13)	0.0294 (3)
C2	0.61507 (11)	0.18883 (13)	0.35586 (13)	0.0236 (3)
N11	0.38359 (10)	0.62115 (13)	0.40961 (13)	0.0300 (3)
C4	0.51530 (13)	−0.02147 (14)	0.35905 (15)	0.0290 (4)
H4	0.5115	−0.1208	0.3538	0.035*
O2	0.80624 (9)	0.18762 (11)	0.35001 (13)	0.0378 (4)
C7	0.72441 (11)	0.26027 (14)	0.34338 (14)	0.0258 (3)
C5	0.42357 (12)	0.05728 (16)	0.37473 (16)	0.0332 (4)
H5	0.3565	0.0135	0.3806	0.040*
C6	0.43471 (12)	0.20546 (16)	0.38159 (17)	0.0350 (4)
H6	0.3737	0.2610	0.3937	0.042*
O12	0.35866 (13)	0.51255 (13)	0.45999 (13)	0.0464 (4)
O13	0.32128 (12)	0.72177 (17)	0.4017 (2)	0.0755 (7)
Li1	0.6045 (2)	0.5149 (3)	0.3893 (3)	0.0362 (7)
H2	0.671 (2)	−0.005 (3)	0.339 (2)	0.044 (6)*

	U11	U22	U33	U12	U13	U23
N2	0.0196 (5)	0.0171 (5)	0.0382 (8)	−0.0002 (4)	−0.0020 (5)	−0.0003 (5)
O1	0.0227 (5)	0.0175 (4)	0.0567 (8)	−0.0023 (3)	0.0012 (5)	0.0000 (4)
O11	0.0233 (6)	0.0398 (6)	0.0568 (10)	0.0039 (4)	0.0078 (5)	0.0067 (6)
N1	0.0190 (6)	0.0212 (5)	0.0479 (9)	0.0021 (4)	−0.0008 (5)	−0.0048 (5)
C2	0.0200 (6)	0.0184 (5)	0.0323 (8)	−0.0005 (4)	−0.0018 (6)	−0.0018 (5)
N11	0.0230 (6)	0.0287 (6)	0.0384 (8)	−0.0003 (4)	−0.0009 (6)	0.0007 (5)
C4	0.0260 (7)	0.0200 (5)	0.0410 (10)	−0.0042 (5)	−0.0013 (7)	0.0014 (5)
O2	0.0183 (5)	0.0241 (5)	0.0710 (10)	0.0023 (4)	0.0002 (6)	0.0032 (5)
C7	0.0199 (6)	0.0186 (5)	0.0388 (8)	−0.0011 (4)	−0.0017 (6)	−0.0029 (5)
C5	0.0193 (6)	0.0304 (6)	0.0499 (11)	−0.0065 (5)	−0.0018 (7)	0.0000 (7)
C6	0.0191 (6)	0.0308 (7)	0.0551 (12)	0.0021 (5)	0.0020 (7)	−0.0064 (7)
O12	0.0557 (8)	0.0362 (6)	0.0474 (9)	−0.0142 (6)	0.0041 (8)	0.0043 (6)
O13	0.0321 (7)	0.0554 (8)	0.139 (2)	0.0210 (6)	0.0136 (10)	0.0267 (11)
Li1	0.0294 (13)	0.0305 (11)	0.0486 (19)	0.0042 (10)	0.0029 (13)	0.0051 (12)

N2—C4	1.3399 (19)	N11—O12	1.2404 (18)
N2—C2	1.3406 (16)	C4—C5	1.369 (2)
N2—H2	0.90 (3)	C4—H4	0.9300
O1—C7	1.2610 (16)	O2—C7	1.2234 (17)
O1—Li1	1.978 (3)	O2—Li1i	2.019 (3)
O11—N11	1.2466 (18)	C5—C6	1.392 (2)
O11—Li1	1.967 (3)	C5—H5	0.9300
N1—C2	1.3178 (18)	C6—H6	0.9300
N1—C6	1.3357 (19)	O12—Li1ii	2.001 (4)
N1—Li1	2.469 (3)	Li1—O12ii	2.001 (4)
C2—C7	1.5194 (19)	Li1—O2iii	2.019 (3)
N11—O13	1.2201 (18)
C4—N2—C2	119.87 (13)	O2—C7—C2	119.35 (12)
C4—N2—H2	120.5 (15)	O1—C7—C2	113.12 (11)
C2—N2—H2	119.5 (15)	C4—C5—C6	117.36 (14)
C7—O1—Li1	122.76 (14)	C4—C5—H5	121.3
N11—O11—Li1	129.73 (15)	C6—C5—H5	121.3
C2—N1—C6	117.33 (11)	N1—C6—C5	122.29 (14)
C2—N1—Li1	104.42 (11)	N1—C6—H6	118.9
C6—N1—Li1	137.95 (11)	C5—C6—H6	118.9
N1—C2—N2	123.50 (13)	N11—O12—Li1ii	123.35 (15)
N1—C2—C7	118.44 (11)	O11—Li1—O1	147.4 (2)
N2—C2—C7	118.06 (12)	O11—Li1—O12ii	113.43 (18)
O13—N11—O12	120.90 (16)	O1—Li1—O12ii	98.94 (15)
O13—N11—O11	118.66 (15)	O11—Li1—O2iii	88.82 (12)
O12—N11—O11	120.44 (14)	O1—Li1—O2iii	88.11 (14)
N2—C4—C5	119.61 (12)	O12ii—Li1—O2iii	102.57 (16)
N2—C4—H4	120.2	O11—Li1—N1	100.51 (13)
C5—C4—H4	120.2	O1—Li1—N1	72.49 (10)
C7—O2—Li1i	156.13 (14)	O12ii—Li1—N1	93.28 (13)
O2—C7—O1	127.53 (13)	O2iii—Li1—N1	156.71 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (3)	1.68 (3)	2.5762 (17)	174 (3)

Table 1

Selected bond lengths (Å)

O1—Li1	1.978 (3)
O11—Li1	1.967 (3)
Li1—O12i	2.001 (4)
Li1—O2ii	2.019 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1iii	0.90 (3)	1.68 (3)	2.5762 (17)	174 (3)

Symmetry code: (iii) .