1,3-Dimethyl-5-(2-methyl-benzyl-idene)pyrimidine-2,4,6(1H,3H,5H)-trione.

In the title compound, C(14)H(14)N(2)O(3), the dihedral angle between the pyrimidine and benzene rings is 14.9 (1)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal structure exhibits a weak inter-molecular π-π inter-action [centroid-centroid distance = 3.575 (3) Å].

Related literature

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

Experimental

Crystal data

C14H14N2O3

M = 258.27

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

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

C14H14N2O3	F(000) = 544
Mr = 258.27	Dx = 1.386 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6022 reflections
a = 8.182 (5) Å	θ = 2.2–29.8°
b = 8.334 (4) Å	µ = 0.10 mm−1
c = 18.202 (5) Å	T = 295 K
β = 94.267 (5)°	Block, colourless
V = 1237.7 (10) Å3	0.30 × 0.28 × 0.18 mm
Z = 4

Bruker Kappa APEXII diffractometer	3837 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 30.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.971, Tmax = 0.982	k = −8→11
16198 measured reflections	l = −26→26

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.238	H-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 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.0138 (2)	0.2553 (2)	0.49118 (10)	0.0391 (4)
C2	−0.1183 (3)	0.2104 (3)	0.44177 (12)	0.0547 (6)
H2	−0.1974	0.1406	0.4573	0.066*
C3	−0.1326 (3)	0.2681 (4)	0.37060 (12)	0.0589 (6)
H3	−0.2205	0.2370	0.3384	0.071*
C4	−0.0168 (3)	0.3713 (3)	0.34746 (12)	0.0548 (6)
H4	−0.0285	0.4147	0.3003	0.066*
C5	0.1166 (3)	0.4106 (3)	0.39422 (12)	0.0519 (5)
H5	0.1961	0.4785	0.3775	0.062*
C6	0.1363 (2)	0.3521 (3)	0.46527 (11)	0.0424 (5)
C7	0.2861 (3)	0.4007 (4)	0.51198 (15)	0.0714 (8)
H7A	0.3586	0.3105	0.5188	0.107*
H7B	0.2552	0.4370	0.5590	0.107*
H7C	0.3408	0.4859	0.4881	0.107*
C8	0.0343 (3)	0.2024 (3)	0.56714 (11)	0.0447 (5)
H8	0.1412	0.2161	0.5873	0.054*
C9	−0.0641 (2)	0.1379 (2)	0.61602 (10)	0.0390 (4)
C10	0.0217 (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)
C13	0.0281 (3)	−0.0647 (3)	0.79980 (12)	0.0584 (6)
H13A	0.1247	−0.1223	0.7885	0.088*
H13B	−0.0416	−0.1340	0.8257	0.088*
H13C	0.0589	0.0263	0.8300	0.088*
C14	−0.4706 (3)	−0.0581 (4)	0.63701 (16)	0.0715 (8)
H14A	−0.4822	−0.1675	0.6524	0.107*
H14B	−0.5004	−0.0496	0.5851	0.107*
H14C	−0.5409	0.0093	0.6636	0.107*
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)
O1	0.1595 (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)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (9)	0.0465 (10)	0.0326 (8)	0.0012 (8)	0.0033 (7)	0.0046 (7)
C2	0.0453 (11)	0.0775 (16)	0.0407 (10)	−0.0112 (11)	−0.0004 (9)	0.0047 (11)
C3	0.0505 (12)	0.0883 (18)	0.0367 (10)	0.0003 (12)	−0.0041 (9)	0.0010 (11)
C4	0.0654 (14)	0.0672 (15)	0.0323 (9)	0.0100 (11)	0.0064 (9)	0.0082 (9)
C5	0.0614 (13)	0.0556 (13)	0.0403 (10)	−0.0084 (10)	0.0144 (9)	0.0035 (9)
C6	0.0407 (10)	0.0498 (11)	0.0371 (9)	−0.0012 (8)	0.0061 (7)	−0.0031 (8)
C7	0.0539 (14)	0.104 (2)	0.0549 (14)	−0.0309 (15)	−0.0017 (11)	0.0038 (14)
C8	0.0417 (10)	0.0534 (12)	0.0382 (9)	−0.0060 (9)	−0.0016 (8)	0.0071 (9)
C9	0.0413 (10)	0.0433 (10)	0.0320 (8)	−0.0013 (8)	−0.0009 (7)	0.0049 (7)
C10	0.0415 (10)	0.0535 (11)	0.0330 (9)	−0.0047 (9)	−0.0017 (7)	0.0061 (8)
C11	0.0460 (10)	0.0390 (10)	0.0350 (9)	−0.0009 (8)	0.0100 (7)	−0.0014 (7)
C12	0.0391 (10)	0.0608 (13)	0.0345 (9)	0.0025 (9)	0.0008 (7)	0.0053 (9)
C13	0.0598 (14)	0.0761 (16)	0.0384 (10)	0.0067 (12)	−0.0022 (9)	0.0186 (11)
C14	0.0449 (13)	0.108 (2)	0.0611 (15)	−0.0255 (14)	0.0006 (11)	−0.0008 (15)
N1	0.0378 (8)	0.0532 (10)	0.0387 (8)	−0.0071 (7)	0.0025 (6)	−0.0027 (7)
N2	0.0408 (8)	0.0466 (9)	0.0315 (7)	0.0021 (7)	0.0020 (6)	0.0070 (6)
O1	0.0512 (9)	0.1035 (15)	0.0473 (9)	−0.0257 (9)	−0.0139 (7)	0.0199 (9)
O2	0.0443 (9)	0.1221 (17)	0.0570 (10)	0.0125 (10)	−0.0022 (8)	0.0328 (11)
O3	0.0673 (11)	0.0574 (10)	0.0536 (9)	−0.0123 (8)	0.0186 (8)	0.0089 (7)

C1—C6	1.396 (3)	C9—C12	1.457 (3)
C1—C2	1.404 (3)	C9—C10	1.482 (3)
C1—C8	1.449 (3)	C10—O1	1.217 (3)
C2—C3	1.379 (3)	C10—N2	1.371 (3)
C2—H2	0.9300	C11—O3	1.212 (2)
C3—C4	1.369 (4)	C11—N2	1.376 (3)
C3—H3	0.9300	C11—N1	1.380 (3)
C4—C5	1.373 (4)	C12—O2	1.214 (3)
C4—H4	0.9300	C12—N1	1.391 (3)
C5—C6	1.380 (3)	C13—N2	1.467 (3)
C5—H5	0.9300	C13—H13A	0.9600
C6—C7	1.495 (3)	C13—H13B	0.9600
C7—H7A	0.9600	C13—H13C	0.9600
C7—H7B	0.9600	C14—N1	1.460 (3)
C7—H7C	0.9600	C14—H14A	0.9600
C8—C9	1.355 (3)	C14—H14B	0.9600
C8—H8	0.9300	C14—H14C	0.9600
C6—C1—C2	118.38 (18)	C12—C9—C10	117.69 (17)
C6—C1—C8	117.61 (18)	O1—C10—N2	120.04 (18)
C2—C1—C8	123.97 (19)	O1—C10—C9	123.19 (19)
C3—C2—C1	121.1 (2)	N2—C10—C9	116.74 (18)
C3—C2—H2	119.5	O3—C11—N2	121.34 (19)
C1—C2—H2	119.5	O3—C11—N1	121.6 (2)
C4—C3—C2	119.7 (2)	N2—C11—N1	117.08 (17)
C4—C3—H3	120.1	O2—C12—N1	119.8 (2)
C2—C3—H3	120.1	O2—C12—C9	124.2 (2)
C3—C4—C5	119.7 (2)	N1—C12—C9	116.06 (17)
C3—C4—H4	120.1	N2—C13—H13A	109.5
C5—C4—H4	120.1	N2—C13—H13B	109.5
C4—C5—C6	121.9 (2)	H13A—C13—H13B	109.5
C4—C5—H5	119.0	N2—C13—H13C	109.5
C6—C5—H5	119.0	H13A—C13—H13C	109.5
C5—C6—C1	118.95 (19)	H13B—C13—H13C	109.5
C5—C6—C7	118.1 (2)	N1—C14—H14A	109.5
C1—C6—C7	122.9 (2)	N1—C14—H14B	109.5
C6—C7—H7A	109.5	H14A—C14—H14B	109.5
C6—C7—H7B	109.5	N1—C14—H14C	109.5
H7A—C7—H7B	109.5	H14A—C14—H14C	109.5
C6—C7—H7C	109.5	H14B—C14—H14C	109.5
H7A—C7—H7C	109.5	C11—N1—C12	124.58 (17)
H7B—C7—H7C	109.5	C11—N1—C14	117.58 (19)
C9—C8—C1	135.66 (19)	C12—N1—C14	117.7 (2)
C9—C8—H8	112.2	C10—N2—C11	124.92 (16)
C1—C8—H8	112.2	C10—N2—C13	117.15 (18)
C8—C9—C12	127.86 (18)	C11—N2—C13	117.91 (18)
C8—C9—C10	114.43 (18)
C6—C1—C2—C3	−4.0 (4)	C10—C9—C12—O2	159.2 (2)
C8—C1—C2—C3	178.4 (2)	C8—C9—C12—N1	158.5 (2)
C1—C2—C3—C4	−0.2 (4)	C10—C9—C12—N1	−20.2 (3)
C2—C3—C4—C5	3.1 (4)	O3—C11—N1—C12	178.2 (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—C14	2.9 (3)
C4—C5—C6—C7	179.6 (3)	N2—C11—N1—C14	−175.4 (2)
C2—C1—C6—C5	5.2 (3)	O2—C12—N1—C11	−166.3 (2)
C8—C1—C6—C5	−177.0 (2)	C9—C12—N1—C11	13.1 (3)
C2—C1—C6—C7	−177.0 (3)	O2—C12—N1—C14	8.9 (4)
C8—C1—C6—C7	0.7 (3)	C9—C12—N1—C14	−171.7 (2)
C6—C1—C8—C9	164.5 (3)	O1—C10—N2—C11	179.7 (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—C10	175.4 (2)	C9—C10—N2—C13	176.01 (19)
C8—C9—C10—O1	14.5 (3)	O3—C11—N2—C10	176.1 (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—N2	15.4 (3)	N1—C11—N2—C13	176.12 (18)
C8—C9—C12—O2	−22.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.26	2.893 (3)	125
C8—H8···O1	0.93	2.28	2.732 (3)	110
C13—H13B···O3	0.96	2.26	2.706 (4)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.26	2.893 (3)	125