5-Acetyl-4-(4-methoxy-phen-yl)-6-methyl-3,4-dihydro-pyrimidin-2(1H)-one.

In the title mol-ecule, C(14)H(16)N(2)O(3), the heterocyclic ring adopts a flattened boat conformation, and the plane through its four coplanar atoms makes a dihedral angle of 89.65 (7)° with the benzene ring. The non-H atoms of the carbonyl, acetyl and methyl groups are nearly coplanar with the attached heterocyclic ring. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For chemical and medicinal background, see: Atwal et al. (1989 ▶); Ghorab et al. (2000 ▶); Kappe (1993 ▶, 2000 ▶); Kappe et al. (1997 ▶, 2000 ▶); Shivarama Holla et al. (2004 ▶); Stefani et al. (2006 ▶).

Experimental

Crystal data

C14H16N2O3

M = 260.29

Monoclinic,

a = 23.7948 (12) Å

b = 7.9905 (3) Å

c = 14.4757 (7) Å

β = 108.305 (5)°

V = 2613.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.837, T max = 1.000 (expected range = 0.821–0.981)

26518 measured reflections

2960 independent reflections

2226 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.149

S = 1.10

2960 reflections

183 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-NT (Bruker, 2004 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040270/hb2869sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040270/hb2869Isup2.hkl

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

C14H16N2O3	F(000) = 1104
Mr = 260.29	Dx = 1.323 Mg m−3
Monoclinic, C2/c	Melting point: 474.5 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.7948 (12) Å	Cell parameters from 5096 reflections
b = 7.9905 (3) Å	θ = 2.7–26.4°
c = 14.4757 (7) Å	µ = 0.09 mm−1
β = 108.305 (5)°	T = 293 K
V = 2613.0 (2) Å3	Block, colourless
Z = 8	0.3 × 0.2 × 0.2 mm

Bruker Kappa APEXII CCD diffractometer	2960 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω and φ scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −30→30
Tmin = 0.837, Tmax = 1.000	k = −10→10
26518 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0771P)2 + 1.0144P] where P = (Fo2 + 2Fc2)/3
2960 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O2	0.03463 (6)	0.62339 (16)	−0.06612 (9)	0.0448 (4)
O15	0.06948 (6)	0.98745 (15)	0.31847 (8)	0.0430 (4)
O44	0.27417 (7)	0.4726 (2)	0.44596 (12)	0.0748 (6)
N1	0.07453 (7)	0.86574 (18)	0.00570 (10)	0.0358 (4)
N3	0.04449 (7)	0.66399 (18)	0.09271 (10)	0.0351 (4)
C2	0.05037 (7)	0.7104 (2)	0.00812 (11)	0.0319 (5)
C4	0.06651 (7)	0.75657 (19)	0.18405 (11)	0.0297 (4)
C5	0.07616 (7)	0.93953 (19)	0.16471 (11)	0.0294 (5)
C6	0.08211 (7)	0.98438 (19)	0.07810 (11)	0.0303 (5)
C14	0.27926 (12)	0.4564 (4)	0.54607 (19)	0.0879 (11)
C15	0.07743 (7)	1.0494 (2)	0.24592 (11)	0.0332 (5)
C16	0.08710 (11)	1.2339 (2)	0.24595 (14)	0.0558 (7)
C41	0.12158 (7)	0.67712 (19)	0.25352 (11)	0.0320 (5)
C42	0.17355 (9)	0.6594 (3)	0.23045 (14)	0.0514 (7)
C43	0.22307 (10)	0.5896 (3)	0.29545 (17)	0.0624 (8)
C44	0.22238 (9)	0.5391 (3)	0.38624 (14)	0.0493 (6)
C45	0.17137 (9)	0.5551 (2)	0.41034 (13)	0.0436 (6)
C46	0.12122 (8)	0.6231 (2)	0.34341 (12)	0.0362 (5)
C61	0.09756 (9)	1.1526 (2)	0.04681 (13)	0.0424 (6)
H1	0.0736 (9)	0.901 (3)	−0.0548 (16)	0.048 (6)*
H3	0.0231 (9)	0.572 (3)	0.0913 (14)	0.046 (6)*
H4	0.03559	0.75256	0.21553	0.0356*
H14A	0.27276	0.56325	0.57124	0.1316*
H14B	0.31818	0.41685	0.58148	0.1316*
H14C	0.25029	0.37800	0.55309	0.1316*
H16A	0.08324	1.28140	0.30456	0.0837*
H16B	0.05821	1.28296	0.19064	0.0837*
H16C	0.12608	1.25601	0.24265	0.0837*
H42	0.17493	0.69534	0.17010	0.0616*
H43	0.25728	0.57630	0.27812	0.0749*
H45	0.17030	0.52054	0.47112	0.0523*
H46	0.08658	0.63227	0.35988	0.0434*
H61A	0.06570	1.22943	0.04172	0.0636*
H61B	0.10388	1.14266	−0.01528	0.0636*
H61C	0.13299	1.19346	0.09397	0.0636*

	U11	U22	U33	U12	U13	U23
O2	0.0622 (9)	0.0433 (7)	0.0320 (7)	−0.0143 (6)	0.0191 (6)	−0.0122 (5)
O15	0.0643 (9)	0.0401 (7)	0.0261 (6)	0.0044 (6)	0.0164 (6)	−0.0015 (5)
O44	0.0478 (9)	0.0956 (13)	0.0681 (11)	0.0106 (9)	−0.0003 (8)	0.0305 (10)
N1	0.0501 (9)	0.0354 (7)	0.0249 (7)	−0.0069 (6)	0.0160 (6)	−0.0019 (6)
N3	0.0469 (9)	0.0314 (7)	0.0264 (7)	−0.0105 (6)	0.0108 (6)	−0.0029 (5)
C2	0.0358 (9)	0.0334 (8)	0.0263 (8)	−0.0038 (7)	0.0094 (7)	−0.0037 (6)
C4	0.0380 (9)	0.0294 (7)	0.0233 (7)	−0.0033 (6)	0.0119 (7)	−0.0004 (6)
C5	0.0339 (9)	0.0279 (7)	0.0251 (8)	0.0007 (6)	0.0074 (6)	0.0002 (6)
C6	0.0331 (9)	0.0297 (8)	0.0266 (8)	0.0002 (6)	0.0074 (6)	−0.0003 (6)
C14	0.0716 (18)	0.102 (2)	0.0639 (17)	−0.0019 (16)	−0.0163 (13)	0.0314 (15)
C15	0.0388 (9)	0.0335 (8)	0.0240 (8)	0.0044 (7)	0.0051 (7)	−0.0013 (6)
C16	0.0959 (18)	0.0337 (9)	0.0369 (10)	−0.0012 (10)	0.0196 (11)	−0.0053 (8)
C41	0.0396 (9)	0.0275 (7)	0.0288 (8)	−0.0036 (7)	0.0108 (7)	−0.0002 (6)
C42	0.0474 (12)	0.0697 (13)	0.0400 (10)	0.0058 (10)	0.0181 (9)	0.0166 (9)
C43	0.0406 (12)	0.0861 (17)	0.0623 (14)	0.0084 (11)	0.0188 (10)	0.0201 (12)
C44	0.0436 (11)	0.0487 (11)	0.0469 (11)	0.0012 (9)	0.0017 (9)	0.0111 (9)
C45	0.0548 (12)	0.0399 (9)	0.0329 (9)	0.0014 (9)	0.0090 (8)	0.0082 (8)
C46	0.0454 (10)	0.0330 (8)	0.0314 (9)	0.0005 (7)	0.0139 (7)	0.0022 (7)
C61	0.0613 (12)	0.0324 (8)	0.0360 (9)	−0.0030 (8)	0.0188 (9)	0.0029 (7)

O2—C2	1.235 (2)	C42—C43	1.374 (3)
O15—C15	1.228 (2)	C43—C44	1.380 (3)
O44—C14	1.422 (3)	C44—C45	1.370 (3)
O44—C44	1.371 (3)	C45—C46	1.390 (3)
N1—C2	1.373 (2)	C4—H4	0.9800
N1—C6	1.382 (2)	C14—H14A	0.9600
N3—C2	1.328 (2)	C14—H14B	0.9600
N3—C4	1.461 (2)	C14—H14C	0.9600
N1—H1	0.91 (2)	C16—H16A	0.9600
N3—H3	0.89 (2)	C16—H16B	0.9600
C4—C41	1.518 (2)	C16—H16C	0.9600
C4—C5	1.520 (2)	C42—H42	0.9300
C5—C6	1.354 (2)	C43—H43	0.9300
C5—C15	1.460 (2)	C45—H45	0.9300
C6—C61	1.501 (2)	C46—H46	0.9300
C15—C16	1.492 (2)	C61—H61A	0.9600
C41—C46	1.374 (2)	C61—H61B	0.9600
C41—C42	1.386 (3)	C61—H61C	0.9600
C14—O44—C44	116.75 (19)	C41—C46—C45	121.59 (18)
C2—N1—C6	123.82 (14)	N3—C4—H4	107.00
C2—N3—C4	125.54 (14)	C5—C4—H4	107.00
C2—N1—H1	114.8 (15)	C41—C4—H4	107.00
C6—N1—H1	118.3 (15)	O44—C14—H14A	109.00
C2—N3—H3	115.7 (13)	O44—C14—H14B	109.00
C4—N3—H3	118.6 (13)	O44—C14—H14C	109.00
O2—C2—N3	123.64 (16)	H14A—C14—H14B	109.00
N1—C2—N3	116.24 (14)	H14A—C14—H14C	109.00
O2—C2—N1	120.11 (15)	H14B—C14—H14C	109.00
N3—C4—C5	110.63 (13)	C15—C16—H16A	109.00
N3—C4—C41	112.17 (13)	C15—C16—H16B	109.00
C5—C4—C41	112.06 (13)	C15—C16—H16C	109.00
C4—C5—C15	113.35 (13)	H16A—C16—H16B	109.00
C6—C5—C15	127.23 (14)	H16A—C16—H16C	109.00
C4—C5—C6	119.42 (14)	H16B—C16—H16C	109.00
N1—C6—C5	119.61 (14)	C41—C42—H42	119.00
N1—C6—C61	111.81 (14)	C43—C42—H42	120.00
C5—C6—C61	128.58 (14)	C42—C43—H43	120.00
C5—C15—C16	123.96 (15)	C44—C43—H43	120.00
O15—C15—C5	118.45 (14)	C44—C45—H45	120.00
O15—C15—C16	117.59 (15)	C46—C45—H45	120.00
C4—C41—C46	119.88 (16)	C41—C46—H46	119.00
C42—C41—C46	117.89 (16)	C45—C46—H46	119.00
C4—C41—C42	122.22 (15)	C6—C61—H61A	109.00
C41—C42—C43	120.97 (19)	C6—C61—H61B	109.00
C42—C43—C44	120.4 (2)	C6—C61—H61C	109.00
O44—C44—C43	115.9 (2)	H61A—C61—H61B	109.00
C43—C44—C45	119.5 (2)	H61A—C61—H61C	109.00
O44—C44—C45	124.64 (18)	H61B—C61—H61C	109.00
C44—C45—C46	119.62 (17)
C14—O44—C44—C43	165.7 (2)	C4—C5—C6—N1	5.3 (3)
C14—O44—C44—C45	−15.5 (3)	C4—C5—C6—C61	−173.60 (17)
C6—N1—C2—O2	166.26 (17)	C15—C5—C6—N1	−174.25 (17)
C6—N1—C2—N3	−12.6 (3)	C15—C5—C6—C61	6.9 (3)
C2—N1—C6—C5	12.8 (3)	C4—C5—C15—O15	−1.7 (2)
C2—N1—C6—C61	−168.20 (17)	C4—C5—C15—C16	179.10 (18)
C4—N3—C2—O2	174.99 (17)	C6—C5—C15—O15	177.84 (18)
C4—N3—C2—N1	−6.2 (3)	C6—C5—C15—C16	−1.4 (3)
C2—N3—C4—C5	21.4 (2)	C4—C41—C42—C43	178.86 (19)
C2—N3—C4—C41	−104.54 (19)	C46—C41—C42—C43	0.2 (3)
N3—C4—C5—C6	−20.2 (2)	C4—C41—C46—C45	−177.71 (15)
N3—C4—C5—C15	159.41 (15)	C42—C41—C46—C45	1.0 (3)
C41—C4—C5—C6	105.84 (17)	C41—C42—C43—C44	−1.5 (4)
C41—C4—C5—C15	−74.59 (18)	C42—C43—C44—O44	−179.4 (2)
N3—C4—C41—C42	61.2 (2)	C42—C43—C44—C45	1.7 (3)
N3—C4—C41—C46	−120.13 (16)	O44—C44—C45—C46	−179.37 (19)
C5—C4—C41—C42	−64.0 (2)	C43—C44—C45—C46	−0.5 (3)
C5—C4—C41—C46	114.72 (17)	C44—C45—C46—C41	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15i	0.91 (2)	2.01 (2)	2.9209 (18)	172 (2)
N3—H3···O2ii	0.89 (2)	2.04 (2)	2.917 (2)	170.3 (19)
C16—H16B···O2iii	0.96	2.49	3.425 (3)	165
C61—H61B···O15i	0.96	2.51	3.352 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O15i	0.91 (2)	2.01 (2)	2.9209 (18)	172 (2)
N3—H3⋯O2ii	0.89 (2)	2.04 (2)	2.917 (2)	170.3 (19)
C16—H16B⋯O2iii	0.96	2.49	3.425 (3)	165
C61—H61B⋯O15i	0.96	2.51	3.352 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) .