Pyrimidine-2-carboxamide.

In the crystal strucuture of the title compound, C(5)H(5)N(3)O, which was obtained upon recrystallization of 2-cyano-pyrimidine from aqueous sodium hydroxide, the amide group is twisted with respect to the aromatic ring by 24.9 (1)°. π-π stacking is observed between partially overlapped rings at a face-to-face separation of 3.439 (6) Å. The structure features a centrosymmetric pair of inter-molecular N-H⋯O hydrogen bonds. Another N-H⋯O hydrogen bond between adjacent mol-ecules links them into a helical chain motif.

Related literature

For general background, see: Cheng et al. (2000 ▶); Xu & Xu (2004 ▶); Zhang et al. (2008 ▶). For a similar structure, see: Zhang et al. (2007 ▶).

Experimental

Crystal data

C5H5N3O

M = 123.12

Monoclinic,

a = 7.9241 (7) Å

b = 7.3059 (7) Å

c = 9.8223 (9) Å

β = 103.512 (6)°

V = 552.90 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 291 (2) K

0.34 × 0.26 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

7501 measured reflections

1365 independent reflections

1202 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.01

1365 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062770/ng2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062770/ng2399Isup2.hkl

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

C5H5N3O	F000 = 256
Mr = 123.12	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2086 reflections
a = 7.9241 (7) Å	θ = 3.0–25.5º
b = 7.3059 (7) Å	µ = 0.11 mm−1
c = 9.8223 (9) Å	T = 291 (2) K
β = 103.512 (6)º	Prism, yellow
V = 552.90 (9) Å3	0.34 × 0.26 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	1202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 28.3º
T = 293(2) K	θmin = 2.6º
ω scans	h = −10→10
Absorption correction: none	k = −9→9
7501 measured reflections	l = −12→13
1365 independent reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1258P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1365 reflections	Δρmax = 0.25 e Å−3
82 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.35320 (14)	0.45375 (15)	0.64547 (11)	0.0431 (3)
N2	0.18202 (13)	0.54314 (14)	0.42171 (10)	0.0383 (3)
O1	0.13605 (12)	0.15236 (12)	0.61860 (8)	0.0431 (3)
N3	0.07527 (15)	0.18634 (15)	0.38330 (10)	0.0435 (3)
H1A	0.0949	0.2477	0.3043	0.065*
H1B	0.0039	0.0783	0.3675	0.065*
C1	0.23238 (14)	0.42647 (15)	0.52761 (11)	0.0315 (2)
C2	0.43153 (18)	0.6167 (2)	0.65658 (14)	0.0495 (3)
H2	0.5193	0.6412	0.7355	0.059*
C3	0.38709 (19)	0.74967 (19)	0.55555 (15)	0.0502 (3)
H3	0.4405	0.8638	0.5659	0.060*
C4	0.26039 (18)	0.70681 (18)	0.43855 (14)	0.0462 (3)
H4	0.2279	0.7944	0.3686	0.055*
C5	0.14304 (14)	0.24129 (15)	0.51331 (11)	0.0325 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0446 (6)	0.0418 (6)	0.0383 (5)	−0.0037 (4)	0.0002 (4)	−0.0014 (4)
N2	0.0417 (5)	0.0350 (5)	0.0375 (5)	0.0003 (4)	0.0080 (4)	0.0046 (4)
O1	0.0602 (6)	0.0366 (5)	0.0316 (4)	−0.0065 (4)	0.0087 (4)	0.0025 (3)
N3	0.0593 (7)	0.0389 (6)	0.0304 (5)	−0.0120 (5)	0.0065 (4)	−0.0018 (4)
C1	0.0325 (5)	0.0315 (5)	0.0311 (5)	0.0019 (4)	0.0085 (4)	−0.0016 (4)
C2	0.0478 (7)	0.0501 (8)	0.0473 (7)	−0.0108 (6)	0.0046 (5)	−0.0103 (6)
C3	0.0530 (8)	0.0377 (7)	0.0628 (9)	−0.0123 (5)	0.0194 (6)	−0.0072 (6)
C4	0.0506 (7)	0.0367 (6)	0.0538 (7)	0.0001 (5)	0.0175 (6)	0.0084 (5)
C5	0.0362 (5)	0.0304 (5)	0.0302 (5)	0.0018 (4)	0.0067 (4)	−0.0001 (4)

N1—C1	1.3336 (14)	N3—H1B	0.9622
N1—C2	1.3355 (18)	C1—C5	1.5182 (15)
N2—C1	1.3319 (14)	C2—C3	1.374 (2)
N2—C4	1.3397 (17)	C2—H2	0.9300
O1—C5	1.2335 (13)	C3—C4	1.374 (2)
N3—C5	1.3265 (14)	C3—H3	0.9300
N3—H1A	0.9406	C4—H4	0.9300
C1—N1—C2	115.46 (11)	C3—C2—H2	118.8
C1—N2—C4	115.41 (10)	C2—C3—C4	117.18 (12)
C5—N3—H1A	122.9	C2—C3—H3	121.4
C5—N3—H1B	119.6	C4—C3—H3	121.4
H1A—N3—H1B	117.5	N2—C4—C3	122.26 (12)
N2—C1—N1	127.28 (11)	N2—C4—H4	118.9
N2—C1—C5	116.74 (9)	C3—C4—H4	118.9
N1—C1—C5	115.99 (10)	O1—C5—N3	124.08 (11)
N1—C2—C3	122.37 (12)	O1—C5—C1	120.20 (9)
N1—C2—H2	118.8	N3—C5—C1	115.72 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1A···O1i	0.94	2.06	2.994 (1)	172
N3—H1B···O1ii	0.96	2.04	2.986 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1A⋯O1i	0.94	2.06	2.994 (1)	172
N3—H1B⋯O1ii	0.96	2.04	2.986 (2)	167

Symmetry codes: (i) ; (ii) .