2,4-Dioxo-1-(prop-2-yn-yl)-1,2,3,4-tetra-hydro-pyrimidine-5-carbaldehyde.

In the crystal structure of the title compound, C(8)H(6)N(2)O(3), the mol-ecules are linked by a pairs of inter-molecular N-H⋯O hydrogen bonds, forming inversion dimers. The aldehyde group is in the same plane as the pyrimidine ring [with a maximum deviation of 0.083 (2) Å for the O atom), and the linear propargyl group [C-C-C = 178.99 (19)°] makes a dihedral angle of 74.36 (13)° with the ring.

Related literature

For applications of acyclic pyrimidine nucleosides, see: De Clercq (2009 ▶, 2010a ▶,b ▶); Fan et al. (2011 ▶).

Experimental

Crystal data

C8H6N2O3

M = 178.15

Monoclinic,

a = 5.1756 (7) Å

b = 8.4877 (12) Å

c = 18.565 (3) Å

β = 90.611 (2)°

V = 815.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.41 × 0.37 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.955, T max = 0.972

5826 measured reflections

1520 independent reflections

1261 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.08

1520 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811032272/is2760sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032272/is2760Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032272/is2760Isup3.cml

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

C8H6N2O3	F(000) = 368
Mr = 178.15	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2188 reflections
a = 5.1756 (7) Å	θ = 2.6–26.7°
b = 8.4877 (12) Å	µ = 0.11 mm−1
c = 18.565 (3) Å	T = 296 K
β = 90.611 (2)°	Block, colourless
V = 815.5 (2) Å3	0.41 × 0.37 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1520 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
graphite	Rint = 0.020
phi and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→6
Tmin = 0.955, Tmax = 0.972	k = −10→10
5826 measured reflections	l = −22→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1695P] where P = (Fo2 + 2Fc2)/3
1520 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.23 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
C1	0.7042 (3)	0.8893 (2)	0.44458 (8)	0.0374 (4)
C2	0.5046 (3)	0.8128 (2)	0.40196 (8)	0.0376 (4)
C3	0.4934 (3)	0.84333 (19)	0.33033 (8)	0.0372 (4)
H3	0.3631	0.7959	0.3031	0.045*
C4	0.8652 (3)	1.01190 (19)	0.33360 (8)	0.0368 (4)
C5	0.3180 (4)	0.7061 (2)	0.43522 (10)	0.0510 (5)
H5	0.3435	0.6787	0.4833	0.061*
C6	0.6377 (3)	0.9724 (2)	0.21870 (8)	0.0432 (4)
H6A	0.4685	0.9390	0.2017	0.052*
H6B	0.6512	1.0851	0.2110	0.052*
C7	0.8363 (4)	0.8923 (2)	0.17686 (9)	0.0464 (5)
C8	0.9931 (4)	0.8282 (3)	0.14242 (11)	0.0612 (6)
H8	1.1175	0.7773	0.1151	0.073*
N1	0.6616 (2)	0.93903 (17)	0.29646 (7)	0.0370 (4)
N2	0.8664 (3)	0.98582 (16)	0.40649 (7)	0.0398 (4)
H2	0.9818	1.0356	0.4312	0.048*
O1	0.7344 (2)	0.87340 (16)	0.51012 (6)	0.0490 (4)
O2	1.0262 (2)	1.09061 (15)	0.30334 (6)	0.0472 (4)
O3	0.1324 (3)	0.65141 (19)	0.40376 (8)	0.0685 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0360 (8)	0.0454 (9)	0.0308 (8)	0.0027 (7)	−0.0031 (6)	−0.0023 (7)
C2	0.0353 (8)	0.0442 (9)	0.0333 (8)	0.0011 (7)	−0.0018 (6)	−0.0066 (7)
C3	0.0326 (8)	0.0439 (9)	0.0350 (8)	0.0021 (7)	−0.0041 (6)	−0.0089 (7)
C4	0.0365 (8)	0.0414 (9)	0.0323 (8)	0.0027 (7)	−0.0036 (7)	−0.0023 (7)
C5	0.0503 (10)	0.0600 (11)	0.0427 (10)	−0.0103 (9)	−0.0011 (8)	−0.0042 (8)
C6	0.0451 (10)	0.0551 (10)	0.0294 (8)	0.0008 (8)	−0.0085 (7)	0.0013 (7)
C7	0.0533 (11)	0.0548 (11)	0.0311 (8)	−0.0078 (9)	−0.0027 (8)	−0.0019 (8)
C8	0.0625 (13)	0.0738 (14)	0.0474 (11)	−0.0033 (11)	0.0076 (10)	−0.0125 (10)
N1	0.0366 (7)	0.0471 (8)	0.0272 (7)	0.0016 (6)	−0.0044 (5)	−0.0029 (6)
N2	0.0402 (8)	0.0494 (8)	0.0297 (7)	−0.0079 (6)	−0.0084 (5)	−0.0014 (6)
O1	0.0500 (7)	0.0683 (8)	0.0285 (6)	−0.0120 (6)	−0.0057 (5)	0.0017 (5)
O2	0.0470 (7)	0.0566 (8)	0.0378 (7)	−0.0094 (6)	−0.0019 (5)	0.0039 (5)
O3	0.0592 (9)	0.0805 (11)	0.0658 (10)	−0.0216 (7)	0.0004 (7)	−0.0139 (8)

C1—O1	1.2325 (19)	C5—O3	1.211 (2)
C1—N2	1.374 (2)	C5—H5	0.9300
C1—C2	1.449 (2)	C6—C7	1.462 (3)
C2—C3	1.356 (2)	C6—N1	1.475 (2)
C2—C5	1.465 (3)	C6—H6A	0.9700
C3—N1	1.351 (2)	C6—H6B	0.9700
C3—H3	0.9300	C7—C8	1.173 (3)
C4—O2	1.211 (2)	C8—H8	0.9300
C4—N2	1.371 (2)	N2—H2	0.8600
C4—N1	1.397 (2)
O1—C1—N2	120.11 (14)	C7—C6—N1	112.24 (14)
O1—C1—C2	124.91 (15)	C7—C6—H6A	109.2
N2—C1—C2	114.98 (13)	N1—C6—H6A	109.2
C3—C2—C1	118.22 (15)	C7—C6—H6B	109.2
C3—C2—C5	120.68 (15)	N1—C6—H6B	109.2
C1—C2—C5	121.10 (15)	H6A—C6—H6B	107.9
N1—C3—C2	123.42 (14)	C8—C7—C6	178.99 (19)
N1—C3—H3	118.3	C7—C8—H8	180.0
C2—C3—H3	118.3	C3—N1—C4	121.52 (13)
O2—C4—N2	123.44 (14)	C3—N1—C6	121.56 (13)
O2—C4—N1	122.30 (14)	C4—N1—C6	116.91 (14)
N2—C4—N1	114.26 (14)	C4—N2—C1	127.43 (13)
O3—C5—C2	123.80 (18)	C4—N2—H2	116.3
O3—C5—H5	118.1	C1—N2—H2	116.3
C2—C5—H5	118.1
O1—C1—C2—C3	179.16 (16)	O2—C4—N1—C3	175.63 (15)
N2—C1—C2—C3	−0.7 (2)	N2—C4—N1—C3	−4.1 (2)
O1—C1—C2—C5	−0.4 (3)	O2—C4—N1—C6	−4.8 (2)
N2—C1—C2—C5	179.81 (15)	N2—C4—N1—C6	175.44 (14)
C1—C2—C3—N1	1.3 (2)	C7—C6—N1—C3	−106.92 (18)
C5—C2—C3—N1	−179.19 (15)	C7—C6—N1—C4	73.53 (19)
C3—C2—C5—O3	−7.1 (3)	O2—C4—N2—C1	−174.72 (16)
C1—C2—C5—O3	172.38 (18)	N1—C4—N2—C1	5.0 (2)
C2—C3—N1—C4	1.3 (2)	O1—C1—N2—C4	177.47 (15)
C2—C3—N1—C6	−178.27 (15)	C2—C1—N2—C4	−2.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	1.98	2.8329 (18)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	1.98	2.8329 (18)	174

Symmetry code: (i) .