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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2394.
Published online 2009 September 9. doi:  10.1107/S1600536809035521
PMCID: PMC2970469

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

Abstract

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 π–π inter­action [centroid–centroid distance = 3.575 (3) Å].

Related literature

For the biological activity of pyrimidine derivatives, see: Cody et al. (1997 [triangle]); Li et al. (1995 [triangle]). For related structures, see: Da Silva et al. (2005 [triangle]); Rezende et al. (2005 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2394-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O3
  • M r = 258.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2394-efi1.jpg
  • a = 8.182 (5) Å
  • b = 8.334 (4) Å
  • c = 18.202 (5) Å
  • β = 94.267 (5)°
  • V = 1237.7 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 K
  • 0.30 × 0.28 × 0.18 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.971, T max = 0.982
  • 16198 measured reflections
  • 3837 independent reflections
  • 2517 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.238
  • S = 1.04
  • 3837 reflections
  • 175 parameters
  • H-atom parameters constrained
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035521/bt5051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035521/bt5051Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C14H14N2O3F(000) = 544
Mr = 258.27Dx = 1.386 Mg m3
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 mm1
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

Bruker Kappa APEXII diffractometer3837 independent reflections
Radiation source: fine-focus sealed tube2517 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and [var phi] 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

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.34 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5051).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cody, V., Galitsky, N., Luft, J. R., Pangborn, W., Gangjee, A., Devraj, R., Queener, S. F. & Blakley, R. L. (1997). Acta Cryst. D53, 638–649. [PubMed]
  • Li, J. J., Anderson, D., Burton, E. G. & Cogburn, J. N. (1995). J. Med. Chem.38, 4570–4578. [PubMed]
  • Rezende, M. C., Dominguez, M., Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o306–o311. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Silva, E. T. da, Ribiero, R. S., Lima, E. L. S., Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o15–o20. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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