N-(4,6-Dimeth-oxy-pyrimidin-2-yl)-2-(3-methyl-phen-yl)acetamide.

In the title compound, C(15)H(17)N(3)O(3), the dihedral angle between the pyrimidine and benzene rings is 87.0 (7)°. In the crystal, mol-ecules are linked into inversion dimers with R(2) (2)(8) graph-set motifs by a pair of N-H⋯O hydrogen bonds. Weak C-H⋯O hydrogen bonds and inter-molecular π-π inter-actions [centroid-centroid distance = 3.544 (1) Å] are also observed.

Related literature

For the pyrimidine ring in vitamins, see: Cox (1968 ▶). For barbitone, the first barbiturate hypnotic sedative, see: Russell (1945 ▶). For the similarity of related N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: John et al. (2010 ▶); Nogueira et al. (2010 ▶); Praveen et al. (2011 ▶); Selig et al. (2010 ▶); Wen et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H17N3O3

M = 287.32

Triclinic,

a = 7.1536 (6) Å

b = 8.2070 (7) Å

c = 13.8259 (10) Å

α = 74.420 (7)°

β = 86.540 (6)°

γ = 69.186 (8)°

V = 730.30 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.42 × 0.34 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.961, T max = 0.980

8350 measured reflections

4735 independent reflections

3887 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.132

S = 1.02

4735 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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) global, I. DOI: 10.1107/S1600536811054493/is5034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054493/is5034Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054493/is5034Isup3.cml

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

C15H17N3O3	Z = 2
Mr = 287.32	F(000) = 304
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1536 (6) Å	Cell parameters from 3427 reflections
b = 8.2070 (7) Å	θ = 3.1–32.3°
c = 13.8259 (10) Å	µ = 0.09 mm−1
α = 74.420 (7)°	T = 173 K
β = 86.540 (6)°	Chunk, colorless
γ = 69.186 (8)°	0.42 × 0.34 × 0.22 mm
V = 730.30 (10) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4735 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3887 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.1500 pixels mm-1	θmax = 32.3°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −10→12
Tmin = 0.961, Tmax = 0.980	l = −20→20
8350 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.156P] where P = (Fo2 + 2Fc2)/3
4735 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.53082 (13)	0.72818 (11)	−0.19967 (6)	0.03281 (19)
O2	0.68411 (13)	0.78056 (10)	0.11132 (7)	0.03380 (19)
O3	1.08112 (15)	−0.05781 (10)	0.12226 (7)	0.0384 (2)
N1	0.71599 (12)	0.47480 (11)	−0.07942 (6)	0.02315 (17)
N2	0.79478 (12)	0.50033 (10)	0.08008 (6)	0.02230 (17)
N3	0.90035 (13)	0.22301 (11)	0.03696 (7)	0.02455 (18)
H3N	0.902 (2)	0.177 (2)	−0.0136 (11)	0.029 (3)*
C1	0.5650 (2)	0.60945 (19)	−0.26389 (9)	0.0382 (3)
H1A	0.7060	0.5570	−0.2723	0.057*
H1B	0.4987	0.6768	−0.3282	0.057*
H1C	0.5130	0.5152	−0.2340	0.057*
C2	0.61661 (14)	0.65189 (13)	−0.10610 (8)	0.0241 (2)
C3	0.59691 (16)	0.76447 (13)	−0.04444 (8)	0.0276 (2)
H3	0.5249	0.8880	−0.0642	0.033*
C4	0.69324 (15)	0.67809 (13)	0.04902 (8)	0.02425 (19)
C5	0.79884 (13)	0.40869 (12)	0.01346 (7)	0.02076 (18)
C6	0.80040 (19)	0.69559 (16)	0.20397 (9)	0.0340 (2)
H6A	0.7555	0.6020	0.2436	0.051*
H6B	0.7846	0.7839	0.2404	0.051*
H6C	0.9389	0.6440	0.1900	0.051*
C7	0.99644 (15)	0.09987 (13)	0.12367 (8)	0.0244 (2)
C8	0.99476 (16)	0.15771 (13)	0.21836 (8)	0.0254 (2)
H8A	1.0698	0.2384	0.2088	0.030*
H8B	0.8580	0.2239	0.2317	0.030*
C9	1.08408 (16)	−0.00098 (13)	0.30737 (8)	0.0268 (2)
C10	0.96179 (18)	−0.06648 (14)	0.37637 (8)	0.0291 (2)
H10	0.8237	−0.0125	0.3662	0.035*
C11	1.0405 (2)	−0.21160 (16)	0.46093 (9)	0.0365 (3)
C12	1.2469 (2)	−0.28988 (17)	0.47418 (10)	0.0465 (3)
H12	1.3028	−0.3863	0.5299	0.056*
C13	1.3710 (2)	−0.22672 (19)	0.40569 (13)	0.0509 (4)
H13	1.5091	−0.2811	0.4158	0.061*
C14	1.29121 (19)	−0.08320 (17)	0.32224 (11)	0.0395 (3)
H14	1.3754	−0.0418	0.2763	0.047*
C15	0.9033 (3)	−0.2773 (2)	0.53551 (11)	0.0532 (4)
H15A	0.8517	−0.3510	0.5095	0.080*
H15B	0.7944	−0.1755	0.5467	0.080*
H15C	0.9765	−0.3474	0.5978	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0345 (4)	0.0291 (4)	0.0288 (4)	−0.0088 (3)	−0.0081 (3)	0.0008 (3)
O2	0.0394 (4)	0.0197 (3)	0.0398 (5)	−0.0029 (3)	−0.0054 (3)	−0.0126 (3)
O3	0.0558 (5)	0.0174 (3)	0.0345 (4)	−0.0007 (3)	−0.0127 (4)	−0.0084 (3)
N1	0.0225 (4)	0.0204 (4)	0.0253 (4)	−0.0070 (3)	−0.0003 (3)	−0.0044 (3)
N2	0.0225 (4)	0.0166 (3)	0.0269 (4)	−0.0053 (3)	0.0003 (3)	−0.0064 (3)
N3	0.0291 (4)	0.0165 (3)	0.0264 (4)	−0.0042 (3)	−0.0036 (3)	−0.0072 (3)
C1	0.0366 (6)	0.0473 (7)	0.0269 (5)	−0.0117 (5)	−0.0025 (4)	−0.0072 (5)
C2	0.0207 (4)	0.0226 (4)	0.0264 (5)	−0.0082 (3)	−0.0015 (3)	−0.0007 (4)
C3	0.0272 (5)	0.0162 (4)	0.0343 (5)	−0.0042 (3)	−0.0032 (4)	−0.0021 (4)
C4	0.0231 (4)	0.0177 (4)	0.0315 (5)	−0.0058 (3)	0.0008 (4)	−0.0077 (4)
C5	0.0192 (4)	0.0170 (4)	0.0257 (4)	−0.0065 (3)	0.0009 (3)	−0.0049 (3)
C6	0.0396 (6)	0.0300 (5)	0.0348 (6)	−0.0103 (5)	−0.0018 (5)	−0.0148 (4)
C7	0.0264 (5)	0.0181 (4)	0.0277 (5)	−0.0061 (3)	−0.0028 (4)	−0.0061 (3)
C8	0.0285 (5)	0.0194 (4)	0.0254 (5)	−0.0042 (4)	−0.0018 (4)	−0.0066 (3)
C9	0.0311 (5)	0.0195 (4)	0.0272 (5)	−0.0044 (4)	−0.0052 (4)	−0.0067 (4)
C10	0.0358 (5)	0.0253 (5)	0.0268 (5)	−0.0091 (4)	−0.0025 (4)	−0.0092 (4)
C11	0.0591 (8)	0.0274 (5)	0.0258 (5)	−0.0168 (5)	−0.0020 (5)	−0.0084 (4)
C12	0.0640 (9)	0.0279 (6)	0.0379 (7)	−0.0077 (6)	−0.0185 (6)	−0.0002 (5)
C13	0.0398 (7)	0.0373 (7)	0.0596 (9)	0.0001 (5)	−0.0188 (6)	−0.0012 (6)
C14	0.0319 (6)	0.0319 (6)	0.0466 (7)	−0.0050 (5)	−0.0050 (5)	−0.0044 (5)
C15	0.0867 (12)	0.0447 (8)	0.0335 (7)	−0.0317 (8)	0.0095 (7)	−0.0086 (6)

O1—C2	1.3528 (12)	C6—H6C	0.9600
O1—C1	1.4376 (16)	C7—C8	1.5058 (14)
O2—C4	1.3404 (12)	C8—C9	1.5038 (14)
O2—C6	1.4338 (14)	C8—H8A	0.9700
O3—C7	1.2235 (12)	C8—H8B	0.9700
N1—C2	1.3279 (12)	C9—C10	1.3865 (16)
N1—C5	1.3356 (12)	C9—C14	1.3947 (16)
N2—C5	1.3298 (12)	C10—C11	1.3991 (16)
N2—C4	1.3373 (12)	C10—H10	0.9300
N3—C7	1.3734 (13)	C11—C12	1.386 (2)
N3—C5	1.3897 (12)	C11—C15	1.507 (2)
N3—H3N	0.875 (15)	C12—C13	1.384 (2)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.3842 (19)
C1—H1C	0.9600	C13—H13	0.9300
C2—C3	1.3843 (15)	C14—H14	0.9300
C3—C4	1.3839 (15)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C6—H6A	0.9600	C15—H15C	0.9600
C6—H6B	0.9600
C2—O1—C1	116.20 (9)	O3—C7—C8	121.00 (9)
C4—O2—C6	117.71 (8)	N3—C7—C8	120.60 (8)
C2—N1—C5	115.15 (8)	C9—C8—C7	111.97 (8)
C5—N2—C4	114.87 (9)	C9—C8—H8A	109.2
C7—N3—C5	132.24 (9)	C7—C8—H8A	109.2
C7—N3—H3N	114.9 (10)	C9—C8—H8B	109.2
C5—N3—H3N	112.9 (10)	C7—C8—H8B	109.2
O1—C1—H1A	109.5	H8A—C8—H8B	107.9
O1—C1—H1B	109.5	C10—C9—C14	119.05 (10)
H1A—C1—H1B	109.5	C10—C9—C8	120.50 (10)
O1—C1—H1C	109.5	C14—C9—C8	120.45 (10)
H1A—C1—H1C	109.5	C9—C10—C11	121.81 (11)
H1B—C1—H1C	109.5	C9—C10—H10	119.1
N1—C2—O1	118.26 (9)	C11—C10—H10	119.1
N1—C2—C3	124.09 (9)	C12—C11—C10	117.89 (12)
O1—C2—C3	117.65 (9)	C12—C11—C15	121.62 (12)
C4—C3—C2	114.49 (9)	C10—C11—C15	120.48 (13)
C4—C3—H3	122.8	C13—C12—C11	121.00 (11)
C2—C3—H3	122.8	C13—C12—H12	119.5
N2—C4—O2	118.59 (9)	C11—C12—H12	119.5
N2—C4—C3	124.04 (9)	C14—C13—C12	120.53 (13)
O2—C4—C3	117.37 (9)	C14—C13—H13	119.7
N2—C5—N1	127.35 (8)	C12—C13—H13	119.7
N2—C5—N3	120.21 (9)	C13—C14—C9	119.71 (13)
N1—C5—N3	112.44 (8)	C13—C14—H14	120.1
O2—C6—H6A	109.5	C9—C14—H14	120.1
O2—C6—H6B	109.5	C11—C15—H15A	109.5
H6A—C6—H6B	109.5	C11—C15—H15B	109.5
O2—C6—H6C	109.5	H15A—C15—H15B	109.5
H6A—C6—H6C	109.5	C11—C15—H15C	109.5
H6B—C6—H6C	109.5	H15A—C15—H15C	109.5
O3—C7—N3	118.39 (9)	H15B—C15—H15C	109.5
C5—N1—C2—O1	179.26 (8)	C7—N3—C5—N1	−176.03 (10)
C5—N1—C2—C3	0.03 (14)	C5—N3—C7—O3	−177.41 (11)
C1—O1—C2—N1	−3.14 (14)	C5—N3—C7—C8	3.42 (17)
C1—O1—C2—C3	176.14 (9)	O3—C7—C8—C9	−6.82 (15)
N1—C2—C3—C4	1.02 (15)	N3—C7—C8—C9	172.33 (9)
O1—C2—C3—C4	−178.21 (9)	C7—C8—C9—C10	−101.24 (11)
C5—N2—C4—O2	−179.18 (9)	C7—C8—C9—C14	79.42 (13)
C5—N2—C4—C3	0.40 (14)	C14—C9—C10—C11	0.61 (16)
C6—O2—C4—N2	5.94 (15)	C8—C9—C10—C11	−178.73 (10)
C6—O2—C4—C3	−173.67 (10)	C9—C10—C11—C12	−0.16 (17)
C2—C3—C4—N2	−1.26 (15)	C9—C10—C11—C15	178.87 (11)
C2—C3—C4—O2	178.33 (9)	C10—C11—C12—C13	−0.20 (19)
C4—N2—C5—N1	0.87 (14)	C15—C11—C12—C13	−179.23 (13)
C4—N2—C5—N3	179.79 (9)	C11—C12—C13—C14	0.1 (2)
C2—N1—C5—N2	−1.08 (14)	C12—C13—C14—C9	0.4 (2)
C2—N1—C5—N3	179.93 (8)	C10—C9—C14—C13	−0.70 (19)
C7—N3—C5—N2	4.91 (16)	C8—C9—C14—C13	178.65 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3i	0.875 (15)	1.979 (15)	2.8535 (12)	176.0 (14)
C3—H3···O2ii	0.93	2.52	3.4459 (12)	177.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3i	0.875 (15)	1.979 (15)	2.8535 (12)	176.0 (14)
C3—H3⋯O2ii	0.93	2.52	3.4459 (12)	177

Symmetry codes: (i) ; (ii) .