Pyrimidine-4-carb-oxy-lic acid.

The crystal structure of the title compound, C5H4N2O2, is built of acid mol-ecules located on a mirror plane. They form sheets stacked along the b-axis direction. The mol-ecules inter-act via O-H⋯N hydrogen bonds, forming [001] chains, and weak van der Waals inter-actions.

Related literature

For the structure of a Li complex with pyrimidine-4-carboxyl­ate and aqua ligands, see: Starosta & Leciejewicz (2012 ▶).

Experimental

Crystal data

C5H4N2O2

M = 124.10

Monoclinic,

a = 6.0080 (12) Å

b = 6.3519 (13) Å

c = 7.4834 (15) Å

β = 112.20 (3)°

V = 264.41 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.17 × 0.16 × 0.06 mm

Data collection

Kuma KM-4 four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.973, T max = 0.994

1981 measured reflections

545 independent reflections

349 reflections with I > 2σ(I)

R int = 0.129

3 standard reflections every 200 reflections intensity decay: 0.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.124

S = 1.00

545 reflections

58 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.34 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012610/bt6903sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012610/bt6903Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012610/bt6903Isup3.cml

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

C5H4N2O2	F(000) = 128
Mr = 124.10	Dx = 1.559 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 25 reflections
a = 6.0080 (12) Å	θ = 6–15°
b = 6.3519 (13) Å	µ = 0.12 mm−1
c = 7.4834 (15) Å	T = 293 K
β = 112.20 (3)°	Plate, colourless
V = 264.41 (9) Å3	0.17 × 0.16 × 0.06 mm
Z = 2

Kuma KM-4 four-circle diffractometer	349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.129
Graphite monochromator	θmax = 25.7°, θmin = 2.9°
profile data from ω/2θ scan	h = −7→7
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −7→7
Tmin = 0.973, Tmax = 0.994	l = −9→9
1981 measured reflections	3 standard reflections every 200 reflections
545 independent reflections	intensity decay: 0.9%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3
545 reflections	(Δ/σ)max < 0.001
58 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.34 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
O1	1.0036 (4)	0.2500	0.2735 (3)	0.0416 (6)
C4	0.8398 (5)	0.2500	0.5171 (4)	0.0308 (7)
N1	0.9072 (4)	0.2500	0.8961 (3)	0.0397 (7)
N3	1.0647 (4)	0.2500	0.6476 (3)	0.0371 (7)
O2	0.6049 (4)	0.2500	0.1835 (3)	0.0649 (8)
C7	0.8036 (5)	0.2500	0.3063 (4)	0.0364 (7)
C5	0.6416 (5)	0.2500	0.5672 (4)	0.0403 (8)
H5	0.4860	0.2500	0.4747	0.048*
C6	0.6868 (5)	0.2500	0.7631 (4)	0.0448 (9)
H6	0.5573	0.2500	0.8024	0.054*
C2	1.0847 (5)	0.2500	0.8311 (4)	0.0401 (8)
H4	1.2401	0.2500	0.9240	0.048*
H1	0.967 (6)	0.2500	0.126 (5)	0.064 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0403 (11)	0.0677 (13)	0.0196 (9)	0.000	0.0145 (8)	0.000
C4	0.0308 (14)	0.0389 (14)	0.0225 (13)	0.000	0.0097 (11)	0.000
N1	0.0401 (13)	0.0606 (16)	0.0208 (11)	0.000	0.0142 (11)	0.000
N3	0.0276 (11)	0.0651 (16)	0.0173 (12)	0.000	0.0071 (9)	0.000
O2	0.0364 (12)	0.130 (2)	0.0206 (10)	0.000	0.0020 (9)	0.000
C7	0.0366 (15)	0.0507 (16)	0.0217 (13)	0.000	0.0109 (12)	0.000
C5	0.0287 (14)	0.0613 (19)	0.0293 (15)	0.000	0.0093 (13)	0.000
C6	0.0325 (14)	0.072 (2)	0.0342 (15)	0.000	0.0179 (12)	0.000
C2	0.0304 (13)	0.0718 (19)	0.0160 (12)	0.000	0.0062 (11)	0.000

O1—C7	1.314 (4)	N3—C2	1.332 (3)
O1—H1	1.04 (4)	O2—C7	1.200 (3)
C4—N3	1.335 (3)	C5—C6	1.386 (4)
C4—C5	1.376 (4)	C5—H5	0.9300
C4—C7	1.509 (3)	C6—H6	0.9300
N1—C6	1.322 (4)	C2—H4	0.9300
N1—C2	1.329 (4)
C7—O1—H1	110.9 (19)	C4—C5—C6	116.4 (3)
N3—C4—C5	122.8 (2)	C4—C5—H5	121.8
N3—C4—C7	118.1 (2)	C6—C5—H5	121.8
C5—C4—C7	119.1 (3)	N1—C6—C5	122.4 (3)
C6—N1—C2	116.0 (2)	N1—C6—H6	118.8
C2—N3—C4	115.2 (2)	C5—C6—H6	118.8
O2—C7—O1	124.9 (2)	N1—C2—N3	127.3 (2)
O2—C7—C4	120.6 (3)	N1—C2—H4	116.4
O1—C7—C4	114.5 (2)	N3—C2—H4	116.4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	1.04 (4)	1.62 (4)	2.660 (3)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	1.04 (4)	1.62 (4)	2.660 (3)	179 (3)

Symmetry code: (i) .