Crystal structure of ethyl 6-methyl-2-oxo-4-(3,4,5-tri-meth-oxy-phen-yl)-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

In the title compound, C17H22N2O6, the di-hydro-pyrimidine ring adopts a flattened boat conformation. The dihedral angle between the benzene ring and the mean plane of the di-hydro-pyrimidine ring is 75.25 (6)°. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif which are linked through N-H⋯O and weak C-H⋯O hydrogen bonds. These, together with π-π ring inter-actions [centroid-centroid distance = 3.7965 (10) Å], give an overall three-dimensional structure.

Related literature

For general background and the biological activity of di­hydro­pyrimidino­nes, see: Jawale et al. (2011 ▸); Beşoluk et al. (2010 ▸); Karade et al. (2007 ▸).

Experimental

Crystal data

C17H22N2O6

M = 350.37

Triclinic,

a = 10.1447 (3) Å

b = 10.1919 (2) Å

c = 10.8724 (2) Å

α = 117.882 (1)°

β = 101.371 (1)°

γ = 105.498 (1)°

V = 886.40 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.970, T max = 0.995

13060 measured reflections

3659 independent reflections

3009 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.06

3659 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: APEX2 and SAINT (Bruker, 2008 ▸); data reduction: SAINT and XPREP (Bruker, 2008 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015003576/zs2327sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003576/zs2327Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015003576/zs2327Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015003576/zs2327fig1.tif

The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015003576/zs2327fig2.tif

Cystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines (Table 1). For clarity only the H atoms participating in these inter­actions are shown.

Click here for additional data file.

. DOI: 10.1107/S2056989015003576/zs2327fig3.tif

A view showing the π–π inter­actions. The H atoms are omitted for the sake of clarity.

CCDC reference: 1050728

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H22N2O6	Z = 2
Mr = 350.37	F(000) = 372
Triclinic, P1	Dx = 1.313 Mg m−3
Hall symbol: -P 1	Melting point: 445 K
a = 10.1447 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1919 (2) Å	Cell parameters from 3659 reflections
c = 10.8724 (2) Å	θ = 1.0–26.5°
α = 117.882 (1)°	µ = 0.10 mm−1
β = 101.371 (1)°	T = 293 K
γ = 105.498 (1)°	Block, colourless
V = 886.40 (4) Å3	0.20 × 0.15 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3009 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.970, Tmax = 0.995	k = −12→12
13060 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0769P)2 + 0.2863P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3659 reflections	Δρmax = 0.60 e Å−3
228 parameters	Δρmin = −0.30 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
C1	0.37112 (18)	0.3299 (2)	0.72474 (17)	0.0394 (4)
C2	0.44867 (19)	0.2873 (2)	0.80886 (18)	0.0410 (4)
H2	0.4009	0.1946	0.8073	0.049*
C3	0.59827 (19)	0.3837 (2)	0.89570 (18)	0.0415 (4)
C4	0.66902 (18)	0.5242 (2)	0.90186 (18)	0.0429 (4)
C5	0.5914 (2)	0.5645 (2)	0.8146 (2)	0.0477 (4)
C6	0.4429 (2)	0.4661 (2)	0.7249 (2)	0.0466 (4)
H6	0.3916	0.4918	0.6647	0.056*
C7	0.6280 (3)	0.2077 (3)	0.9753 (3)	0.0698 (6)
H7A	0.7016	0.2040	1.0427	0.105*
H7B	0.5992	0.1174	0.8743	0.105*
H7C	0.5433	0.2011	1.0028	0.105*
C8	0.9201 (2)	0.6153 (3)	0.9346 (2)	0.0652 (6)
H8A	1.0172	0.6907	1.0103	0.098*
H8B	0.9011	0.6404	0.8599	0.098*
H8C	0.9141	0.5062	0.8882	0.098*
C9	0.5979 (3)	0.7486 (3)	0.7382 (4)	0.0828 (8)
H9A	0.6640	0.8501	0.7591	0.124*
H9B	0.5124	0.7596	0.7590	0.124*
H9C	0.5679	0.6647	0.6343	0.124*
C10	0.0111 (2)	0.1030 (3)	0.2264 (2)	0.0599 (5)
H10A	−0.0726	0.1254	0.2006	0.090*
H10B	−0.0203	−0.0123	0.1806	0.090*
H10C	0.0824	0.1408	0.1908	0.090*
C11	0.07976 (19)	0.1893 (2)	0.39399 (19)	0.0445 (4)
C12	0.15090 (18)	0.1416 (2)	0.47179 (19)	0.0425 (4)
C13	0.20307 (18)	0.2357 (2)	0.64192 (18)	0.0410 (4)
H13	0.1699	0.1573	0.6694	0.049*
C14	0.0864 (2)	0.4142 (2)	0.62100 (19)	0.0455 (4)
C15	0.1840 (2)	−0.0008 (2)	0.3951 (2)	0.0496 (4)
C16	0.2722 (3)	−0.1808 (3)	0.4190 (3)	0.0833 (8)
H16A	0.3437	−0.1572	0.3764	0.100*
H16B	0.1855	−0.2781	0.3388	0.100*
C17	0.3362 (5)	−0.2078 (4)	0.5344 (4)	0.1191 (13)
H17A	0.3634	−0.2977	0.4898	0.179*
H17B	0.2647	−0.2321	0.5754	0.179*
H17C	0.4223	−0.1113	0.6131	0.179*
N1	0.06044 (18)	0.33131 (19)	0.47041 (16)	0.0507 (4)
H1N	0.0304	0.3699	0.4205	0.061*
N2	0.13307 (16)	0.34918 (19)	0.69333 (16)	0.0447 (4)
H2N	0.1210	0.3761	0.7766	0.054*
O1	0.1753 (2)	−0.07004 (19)	0.26618 (17)	0.0744 (5)
O2	0.23206 (16)	−0.04531 (16)	0.48721 (16)	0.0609 (4)
O3	0.68614 (15)	0.35473 (16)	0.98399 (14)	0.0559 (4)
O4	0.81300 (14)	0.62806 (16)	1.00213 (14)	0.0542 (4)
O5	0.67016 (17)	0.70646 (19)	0.8294 (2)	0.0717 (5)
O6	0.06186 (17)	0.53697 (18)	0.68139 (15)	0.0598 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0405 (8)	0.0409 (8)	0.0349 (8)	0.0214 (7)	0.0128 (7)	0.0178 (7)
C2	0.0455 (9)	0.0391 (8)	0.0371 (8)	0.0222 (7)	0.0126 (7)	0.0189 (7)
C3	0.0465 (9)	0.0450 (9)	0.0316 (8)	0.0272 (7)	0.0116 (7)	0.0170 (7)
C4	0.0390 (8)	0.0457 (9)	0.0338 (8)	0.0192 (7)	0.0105 (6)	0.0153 (7)
C5	0.0468 (9)	0.0465 (9)	0.0505 (10)	0.0197 (8)	0.0179 (8)	0.0273 (8)
C6	0.0450 (9)	0.0532 (10)	0.0487 (10)	0.0246 (8)	0.0138 (8)	0.0324 (8)
C7	0.0782 (15)	0.0662 (13)	0.0680 (13)	0.0347 (12)	0.0081 (11)	0.0440 (11)
C8	0.0440 (10)	0.0744 (14)	0.0590 (12)	0.0240 (10)	0.0159 (9)	0.0256 (11)
C9	0.0771 (16)	0.0827 (17)	0.117 (2)	0.0329 (14)	0.0329 (15)	0.0762 (17)
C10	0.0654 (12)	0.0652 (12)	0.0397 (10)	0.0334 (10)	0.0109 (9)	0.0223 (9)
C11	0.0431 (9)	0.0451 (9)	0.0386 (9)	0.0197 (7)	0.0121 (7)	0.0190 (7)
C12	0.0385 (8)	0.0399 (8)	0.0397 (9)	0.0160 (7)	0.0099 (7)	0.0174 (7)
C13	0.0402 (8)	0.0438 (9)	0.0409 (9)	0.0207 (7)	0.0127 (7)	0.0240 (7)
C14	0.0454 (9)	0.0535 (10)	0.0405 (9)	0.0290 (8)	0.0156 (7)	0.0237 (8)
C15	0.0433 (9)	0.0399 (9)	0.0471 (10)	0.0154 (7)	0.0070 (7)	0.0157 (8)
C16	0.0882 (17)	0.0513 (12)	0.0835 (17)	0.0417 (12)	0.0098 (13)	0.0202 (12)
C17	0.142 (3)	0.094 (2)	0.107 (2)	0.079 (2)	0.012 (2)	0.0433 (19)
N1	0.0662 (10)	0.0574 (9)	0.0382 (8)	0.0390 (8)	0.0178 (7)	0.0269 (7)
N2	0.0461 (8)	0.0586 (9)	0.0364 (7)	0.0312 (7)	0.0170 (6)	0.0257 (7)
O1	0.0979 (12)	0.0630 (9)	0.0499 (9)	0.0456 (9)	0.0243 (8)	0.0172 (7)
O2	0.0668 (9)	0.0449 (7)	0.0571 (8)	0.0302 (7)	0.0086 (7)	0.0203 (6)
O3	0.0544 (8)	0.0581 (8)	0.0487 (7)	0.0271 (6)	0.0034 (6)	0.0289 (6)
O4	0.0419 (7)	0.0570 (8)	0.0397 (7)	0.0149 (6)	0.0088 (5)	0.0152 (6)
O5	0.0554 (8)	0.0653 (9)	0.0974 (12)	0.0163 (7)	0.0160 (8)	0.0564 (9)
O6	0.0778 (10)	0.0686 (9)	0.0446 (7)	0.0525 (8)	0.0231 (7)	0.0277 (7)

C1—C2	1.384 (2)	C10—C11	1.501 (2)
C1—C6	1.384 (2)	C10—H10A	0.9600
C1—C13	1.533 (2)	C10—H10B	0.9600
C2—C3	1.389 (2)	C10—H10C	0.9600
C2—H2	0.9300	C11—C12	1.344 (2)
C3—O3	1.368 (2)	C11—N1	1.383 (2)
C3—C4	1.383 (3)	C12—C15	1.468 (2)
C4—O4	1.382 (2)	C12—C13	1.518 (2)
C4—C5	1.390 (3)	C13—N2	1.464 (2)
C5—O5	1.368 (2)	C13—H13	0.9800
C5—C6	1.387 (3)	C14—O6	1.233 (2)
C6—H6	0.9300	C14—N2	1.338 (2)
C7—O3	1.406 (3)	C14—N1	1.371 (2)
C7—H7A	0.9600	C15—O1	1.210 (2)
C7—H7B	0.9600	C15—O2	1.340 (2)
C7—H7C	0.9600	C16—O2	1.444 (3)
C8—O4	1.428 (2)	C16—C17	1.472 (3)
C8—H8A	0.9600	C16—H16A	0.9700
C8—H8B	0.9600	C16—H16B	0.9700
C8—H8C	0.9600	C17—H17A	0.9600
C9—O5	1.410 (3)	C17—H17B	0.9600
C9—H9A	0.9600	C17—H17C	0.9600
C9—H9B	0.9600	N1—H1N	0.8600
C9—H9C	0.9600	N2—H2N	0.8600
C2—C1—C6	120.13 (15)	H10B—C10—H10C	109.5
C2—C1—C13	120.26 (15)	C12—C11—N1	119.53 (15)
C6—C1—C13	119.40 (15)	C12—C11—C10	127.51 (17)
C1—C2—C3	119.70 (16)	N1—C11—C10	112.94 (15)
C1—C2—H2	120.1	C11—C12—C15	120.97 (16)
C3—C2—H2	120.2	C11—C12—C13	121.07 (15)
O3—C3—C4	114.49 (15)	C15—C12—C13	117.94 (15)
O3—C3—C2	125.05 (16)	N2—C13—C12	109.34 (13)
C4—C3—C2	120.42 (15)	N2—C13—C1	109.29 (14)
O4—C4—C3	119.43 (15)	C12—C13—C1	114.52 (14)
O4—C4—C5	120.85 (16)	N2—C13—H13	107.8
C3—C4—C5	119.58 (16)	C12—C13—H13	107.8
O5—C5—C6	124.58 (17)	C1—C13—H13	107.8
O5—C5—C4	115.35 (16)	O6—C14—N2	123.56 (16)
C6—C5—C4	120.03 (17)	O6—C14—N1	120.72 (16)
C1—C6—C5	120.03 (16)	N2—C14—N1	115.66 (15)
C1—C6—H6	120.0	O1—C15—O2	122.09 (18)
C5—C6—H6	120.0	O1—C15—C12	125.98 (18)
O3—C7—H7A	109.5	O2—C15—C12	111.89 (16)
O3—C7—H7B	109.5	O2—C16—C17	109.0 (2)
H7A—C7—H7B	109.5	O2—C16—H16A	109.9
O3—C7—H7C	109.5	C17—C16—H16A	109.9
H7A—C7—H7C	109.5	O2—C16—H16B	109.9
H7B—C7—H7C	109.5	C17—C16—H16B	109.9
O4—C8—H8A	109.5	H16A—C16—H16B	108.3
O4—C8—H8B	109.5	C16—C17—H17A	109.5
H8A—C8—H8B	109.5	C16—C17—H17B	109.5
O4—C8—H8C	109.5	H17A—C17—H17B	109.5
H8A—C8—H8C	109.5	C16—C17—H17C	109.5
H8B—C8—H8C	109.5	H17A—C17—H17C	109.5
O5—C9—H9A	109.5	H17B—C17—H17C	109.5
O5—C9—H9B	109.5	C14—N1—C11	123.90 (15)
H9A—C9—H9B	109.5	C14—N1—H1N	118.1
O5—C9—H9C	109.5	C11—N1—H1N	118.1
H9A—C9—H9C	109.5	C14—N2—C13	125.19 (14)
H9B—C9—H9C	109.5	C14—N2—H2N	117.4
C11—C10—H10A	109.5	C13—N2—H2N	117.4
C11—C10—H10B	109.5	C15—O2—C16	114.13 (17)
H10A—C10—H10B	109.5	C3—O3—C7	118.70 (15)
C11—C10—H10C	109.5	C4—O4—C8	113.93 (14)
H10A—C10—H10C	109.5	C5—O5—C9	117.35 (17)
C6—C1—C2—C3	1.3 (2)	C6—C1—C13—N2	−52.6 (2)
C13—C1—C2—C3	−173.41 (15)	C2—C1—C13—C12	−114.87 (17)
C1—C2—C3—O3	179.57 (16)	C6—C1—C13—C12	70.4 (2)
C1—C2—C3—C4	1.8 (2)	C11—C12—C15—O1	12.9 (3)
O3—C3—C4—O4	−5.5 (2)	C13—C12—C15—O1	−165.48 (19)
C2—C3—C4—O4	172.46 (15)	C11—C12—C15—O2	−169.40 (16)
O3—C3—C4—C5	178.81 (15)	C13—C12—C15—O2	12.2 (2)
C2—C3—C4—C5	−3.2 (3)	O6—C14—N1—C11	−177.32 (18)
O4—C4—C5—O5	3.7 (3)	N2—C14—N1—C11	0.0 (3)
C3—C4—C5—O5	179.34 (16)	C12—C11—N1—C14	−11.8 (3)
O4—C4—C5—C6	−174.07 (16)	C10—C11—N1—C14	166.62 (18)
C3—C4—C5—C6	1.6 (3)	O6—C14—N2—C13	−161.54 (18)
C2—C1—C6—C5	−2.9 (3)	N1—C14—N2—C13	21.2 (3)
C13—C1—C6—C5	171.79 (16)	C12—C13—N2—C14	−27.1 (2)
O5—C5—C6—C1	−176.06 (17)	C1—C13—N2—C14	98.96 (19)
C4—C5—C6—C1	1.5 (3)	O1—C15—O2—C16	0.3 (3)
N1—C11—C12—C15	−174.94 (16)	C12—C15—O2—C16	−177.52 (18)
C10—C11—C12—C15	6.9 (3)	C17—C16—O2—C15	174.6 (2)
N1—C11—C12—C13	3.4 (3)	C4—C3—O3—C7	−174.43 (18)
C10—C11—C12—C13	−174.76 (18)	C2—C3—O3—C7	7.7 (3)
C11—C12—C13—N2	13.6 (2)	C3—C4—O4—C8	102.7 (2)
C15—C12—C13—N2	−167.97 (15)	C5—C4—O4—C8	−81.7 (2)
C11—C12—C13—C1	−109.38 (18)	C6—C5—O5—C9	−5.1 (3)
C15—C12—C13—C1	69.0 (2)	C4—C5—O5—C9	177.3 (2)
C2—C1—C13—N2	122.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6i	0.86	2.01	2.867 (2)	171
N2—H2N···O3ii	0.86	2.56	3.0629 (19)	118
N2—H2N···O4ii	0.86	2.39	3.1331 (19)	145
C8—H8A···O1iii	0.96	2.46	3.325 (3)	149
C9—H9A···O1iv	0.96	2.56	3.491 (3)	163

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO6i	0.86	2.01	2.867(2)	171
N2H2NO4ii	0.86	2.39	3.1331(19)	145
C8H8AO1iii	0.96	2.46	3.325(3)	149
C9H9AO1iv	0.96	2.56	3.491(3)	163

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