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Acta Cryst. (2009). E65, o2394    [ doi:10.1107/S1600536809035521 ]

1,3-Dimethyl-5-(2-methylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

R. Panchatcharam, V. Dhayalan, A. K. Mohanakrishnan, G. Chakkaravarthi and V. Manivannan

Abstract top

In the title compound, C14H14N2O3, the dihedral angle between the pyrimidine and benzene rings is 14.9 (1)°. The molecular structure is stabilized by weak intramolecular C-H...O interactions and the crystal structure exhibits a weak intermolecular [pi]-[pi] interaction [centroid-centroid distance = 3.575 (3) Å].

Comment top

Pyrimidine derivatives show biological activities such as antitumor, antibacterial, insulin releasing and anti-inflammatory activities (Cody et al., 1997; Li et al., 1995). The geometric parameters in (I) (Fig. 1) agree with the reported values of similar structures (Da Silva et al., 2005; Rezende et al., 2005).

The dihedral angle between the pyrimidine ring (N1/C11/N2/C10/C9/C12) and benzene ring (C1—C6) is 14.9 (1)°. The molecular structure is stabilized by weak intramolecular C—H···O interactions. The crystal structure exhibits an intermolecular weak π–π interaction[Cg1···Cg2 = 3.575 (3) Å; symmetry code: -x, -y, 1 - z; Cg1 and Cg2 are the centroids of N1/C11/N2/C10/C9/C12 and C1—C6 rings, respectively].

The intramolecular C8—H8···O1 and C13—H13B···O3 interactions generate five-membered rings, each with graph-set motif S(5) and C2—H2···O2 interaction generates a seven-membered ring, with graph-set motif S(7) (Bernstein et al., 1995).

Related literature top

For related literature, see: Bernstein et al. (1995); Cody et al. (1997); Da Silva et al. (2005); Li et al. (1995); Rezende et al. (2005).

Experimental top

To a solution of o-tolualdehyde (4.0 g, 33.29 mmol) in dry benzene (80 ml), N,N-dimethylbarbituric acid (5.72 g, 36.63 mmol), piperidine (0.6 ml) and acetic acid (0.3 ml) were added and refluxed in a RB flask fitted with Dean-Stark apparatus for 12 h. Removal of solvent followed by recrystallizaton from CDCl3 afforded the compound.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for C—H and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
1,3-Dimethyl-5-(2-methylbenzylidene)pyrimidine- 2,4,6(1H,3H,5H)-trione top
Crystal data top
C14H14N2O3F(000) = 544
Mr = 258.27Dx = 1.386 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6022 reflections
a = 8.182 (5) Åθ = 2.2–29.8°
b = 8.334 (4) ŵ = 0.10 mm−1
c = 18.202 (5) ÅT = 295 K
β = 94.267 (5)°Block, colourless
V = 1237.7 (10) Å30.30 × 0.28 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer		3837 independent reflections
Radiation source: fine-focus sealed tube2517 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and φ scansθmax = 30.7°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.971, Tmax = 0.982k = −8→11
16198 measured reflectionsl = −26→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.238H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1214P)2 + 0.5641P]
where P = (Fo2 + 2Fc2)/3
3837 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C14H14N2O3V = 1237.7 (10) Å3
Mr = 258.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.182 (5) ŵ = 0.10 mm−1
b = 8.334 (4) ÅT = 295 K
c = 18.202 (5) Å0.30 × 0.28 × 0.18 mm
β = 94.267 (5)°
Data collection top
Bruker Kappa APEXII
diffractometer		2517 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.024
Tmin = 0.971, Tmax = 0.982θmax = 30.7°
16198 measured reflectionsStandard reflections: 0
3837 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.072H-atom parameters constrained
wR(F2) = 0.238Δρmax = 0.52 e Å−3
S = 1.04Δρmin = −0.34 e Å−3
3837 reflectionsAbsolute structure: ?
175 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0138 (2)0.2553 (2)0.49118 (10)0.0391 (4)
C2−0.1183 (3)0.2104 (3)0.44177 (12)0.0547 (6)
H2−0.19740.14060.45730.066*
C3−0.1326 (3)0.2681 (4)0.37060 (12)0.0589 (6)
H3−0.22050.23700.33840.071*
C4−0.0168 (3)0.3713 (3)0.34746 (12)0.0548 (6)
H4−0.02850.41470.30030.066*
C50.1166 (3)0.4106 (3)0.39422 (12)0.0519 (5)
H50.19610.47850.37750.062*
C60.1363 (2)0.3521 (3)0.46527 (11)0.0424 (5)
C70.2861 (3)0.4007 (4)0.51198 (15)0.0714 (8)
H7A0.35860.31050.51880.107*
H7B0.25520.43700.55900.107*
H7C0.34080.48590.48810.107*
C80.0343 (3)0.2024 (3)0.56714 (11)0.0447 (5)
H80.14120.21610.58730.054*
C9−0.0641 (2)0.1379 (2)0.61602 (10)0.0390 (4)
C100.0217 (3)0.0920 (3)0.68754 (10)0.0429 (5)
C11−0.2160 (2)−0.0676 (2)0.71455 (10)0.0396 (4)
C12−0.2395 (3)0.1068 (3)0.60570 (11)0.0449 (5)
C130.0281 (3)−0.0647 (3)0.79980 (12)0.0584 (6)
H13A0.1247−0.12230.78850.088*
H13B−0.0416−0.13400.82570.088*
H13C0.05890.02630.83000.088*
C14−0.4706 (3)−0.0581 (4)0.63701 (16)0.0715 (8)
H14A−0.4822−0.16750.65240.107*
H14B−0.5004−0.04960.58510.107*
H14C−0.54090.00930.66360.107*
N1−0.3007 (2)−0.0073 (2)0.65217 (9)0.0433 (4)
N2−0.0600 (2)−0.0100 (2)0.73120 (8)0.0397 (4)
O10.1595 (2)0.1369 (3)0.70726 (9)0.0682 (6)
O2−0.3317 (2)0.1744 (3)0.56044 (11)0.0748 (6)
O3−0.2774 (2)−0.1642 (2)0.75393 (10)0.0587 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0383 (9)0.0465 (10)0.0326 (8)0.0012 (8)0.0033 (7)0.0046 (7)
C20.0453 (11)0.0775 (16)0.0407 (10)−0.0112 (11)−0.0004 (9)0.0047 (11)
C30.0505 (12)0.0883 (18)0.0367 (10)0.0003 (12)−0.0041 (9)0.0010 (11)
C40.0654 (14)0.0672 (15)0.0323 (9)0.0100 (11)0.0064 (9)0.0082 (9)
C50.0614 (13)0.0556 (13)0.0403 (10)−0.0084 (10)0.0144 (9)0.0035 (9)
C60.0407 (10)0.0498 (11)0.0371 (9)−0.0012 (8)0.0061 (7)−0.0031 (8)
C70.0539 (14)0.104 (2)0.0549 (14)−0.0309 (15)−0.0017 (11)0.0038 (14)
C80.0417 (10)0.0534 (12)0.0382 (9)−0.0060 (9)−0.0016 (8)0.0071 (9)
C90.0413 (10)0.0433 (10)0.0320 (8)−0.0013 (8)−0.0009 (7)0.0049 (7)
C100.0415 (10)0.0535 (11)0.0330 (9)−0.0047 (9)−0.0017 (7)0.0061 (8)
C110.0460 (10)0.0390 (10)0.0350 (9)−0.0009 (8)0.0100 (7)−0.0014 (7)
C120.0391 (10)0.0608 (13)0.0345 (9)0.0025 (9)0.0008 (7)0.0053 (9)
C130.0598 (14)0.0761 (16)0.0384 (10)0.0067 (12)−0.0022 (9)0.0186 (11)
C140.0449 (13)0.108 (2)0.0611 (15)−0.0255 (14)0.0006 (11)−0.0008 (15)
N10.0378 (8)0.0532 (10)0.0387 (8)−0.0071 (7)0.0025 (6)−0.0027 (7)
N20.0408 (8)0.0466 (9)0.0315 (7)0.0021 (7)0.0020 (6)0.0070 (6)
O10.0512 (9)0.1035 (15)0.0473 (9)−0.0257 (9)−0.0139 (7)0.0199 (9)
O20.0443 (9)0.1221 (17)0.0570 (10)0.0125 (10)−0.0022 (8)0.0328 (11)
O30.0673 (11)0.0574 (10)0.0536 (9)−0.0123 (8)0.0186 (8)0.0089 (7)
Geometric parameters (Å, °) top
C1—C61.396 (3)C9—C121.457 (3)
C1—C21.404 (3)C9—C101.482 (3)
C1—C81.449 (3)C10—O11.217 (3)
C2—C31.379 (3)C10—N21.371 (3)
C2—H20.9300C11—O31.212 (2)
C3—C41.369 (4)C11—N21.376 (3)
C3—H30.9300C11—N11.380 (3)
C4—C51.373 (4)C12—O21.214 (3)
C4—H40.9300C12—N11.391 (3)
C5—C61.380 (3)C13—N21.467 (3)
C5—H50.9300C13—H13A0.9600
C6—C71.495 (3)C13—H13B0.9600
C7—H7A0.9600C13—H13C0.9600
C7—H7B0.9600C14—N11.460 (3)
C7—H7C0.9600C14—H14A0.9600
C8—C91.355 (3)C14—H14B0.9600
C8—H80.9300C14—H14C0.9600
C6—C1—C2118.38 (18)C12—C9—C10117.69 (17)
C6—C1—C8117.61 (18)O1—C10—N2120.04 (18)
C2—C1—C8123.97 (19)O1—C10—C9123.19 (19)
C3—C2—C1121.1 (2)N2—C10—C9116.74 (18)
C3—C2—H2119.5O3—C11—N2121.34 (19)
C1—C2—H2119.5O3—C11—N1121.6 (2)
C4—C3—C2119.7 (2)N2—C11—N1117.08 (17)
C4—C3—H3120.1O2—C12—N1119.8 (2)
C2—C3—H3120.1O2—C12—C9124.2 (2)
C3—C4—C5119.7 (2)N1—C12—C9116.06 (17)
C3—C4—H4120.1N2—C13—H13A109.5
C5—C4—H4120.1N2—C13—H13B109.5
C4—C5—C6121.9 (2)H13A—C13—H13B109.5
C4—C5—H5119.0N2—C13—H13C109.5
C6—C5—H5119.0H13A—C13—H13C109.5
C5—C6—C1118.95 (19)H13B—C13—H13C109.5
C5—C6—C7118.1 (2)N1—C14—H14A109.5
C1—C6—C7122.9 (2)N1—C14—H14B109.5
C6—C7—H7A109.5H14A—C14—H14B109.5
C6—C7—H7B109.5N1—C14—H14C109.5
H7A—C7—H7B109.5H14A—C14—H14C109.5
C6—C7—H7C109.5H14B—C14—H14C109.5
H7A—C7—H7C109.5C11—N1—C12124.58 (17)
H7B—C7—H7C109.5C11—N1—C14117.58 (19)
C9—C8—C1135.66 (19)C12—N1—C14117.7 (2)
C9—C8—H8112.2C10—N2—C11124.92 (16)
C1—C8—H8112.2C10—N2—C13117.15 (18)
C8—C9—C12127.86 (18)C11—N2—C13117.91 (18)
C8—C9—C10114.43 (18)
C6—C1—C2—C3−4.0 (4)C10—C9—C12—O2159.2 (2)
C8—C1—C2—C3178.4 (2)C8—C9—C12—N1158.5 (2)
C1—C2—C3—C4−0.2 (4)C10—C9—C12—N1−20.2 (3)
C2—C3—C4—C53.1 (4)O3—C11—N1—C12178.2 (2)
C3—C4—C5—C6−1.7 (4)N2—C11—N1—C12−0.2 (3)
C4—C5—C6—C1−2.5 (4)O3—C11—N1—C142.9 (3)
C4—C5—C6—C7179.6 (3)N2—C11—N1—C14−175.4 (2)
C2—C1—C6—C55.2 (3)O2—C12—N1—C11−166.3 (2)
C8—C1—C6—C5−177.0 (2)C9—C12—N1—C1113.1 (3)
C2—C1—C6—C7−177.0 (3)O2—C12—N1—C148.9 (4)
C8—C1—C6—C70.7 (3)C9—C12—N1—C14−171.7 (2)
C6—C1—C8—C9164.5 (3)O1—C10—N2—C11179.7 (2)
C2—C1—C8—C9−17.9 (4)C9—C10—N2—C11−2.3 (3)
C1—C8—C9—C12−3.4 (4)O1—C10—N2—C13−2.0 (3)
C1—C8—C9—C10175.4 (2)C9—C10—N2—C13176.01 (19)
C8—C9—C10—O114.5 (3)O3—C11—N2—C10176.1 (2)
C12—C9—C10—O1−166.7 (2)N1—C11—N2—C10−5.6 (3)
C8—C9—C10—N2−163.5 (2)O3—C11—N2—C13−2.2 (3)
C12—C9—C10—N215.4 (3)N1—C11—N2—C13176.12 (18)
C8—C9—C12—O2−22.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.262.893 (3)125
C8—H8···O10.932.282.732 (3)110
C13—H13B···O30.962.262.706 (4)107
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.262.893 (3)125
C8—H8···O10.932.282.732 (3)110
C13—H13B···O30.962.262.706 (4)107
Acknowledgements top

The authors acknowledge SAIF, IIT, Madras, for the data collection.

references
References top

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