Methyl 4-(3-eth-oxy-4-hydroxy-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate monohydrate.

In the title compound, C(15)H(18)N(2)O(5)·H(2)O, the pyrimidine ring adopts a flattened-boat conformation. The eth-oxy group attached to the benzene ring is in an extended conformation. The oxopyrimidine mol-ecules are linked into centrosymmetric R(2) (2)(20) dimers by O-H⋯O hydrogen bonds. The dimers are linked by N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. Adjacent networks are cross-linked via N-H⋯O and O-H⋯O hydrogen bonds involving the water mol-ecules.

Related literature

For the biological properties of pyrimidine compounds, see: Kidwai et al. (2003 ▶). For C=O bond-length data, see: Litvinov et al. (1992 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H18N2O5·H2O

M = 324.33

Monoclinic,

a = 11.4927 (6) Å

b = 15.3756 (8) Å

c = 8.9240 (5) Å

β = 95.932 (2)°

V = 1568.49 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.977, T max = 0.981

20671 measured reflections

4719 independent reflections

3292 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.04

4719 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902769X/ci2843sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902769X/ci2843Isup2.hkl

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

C15H18N2O5·H2O	F(000) = 688
Mr = 324.33	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4719 reflections
a = 11.4927 (6) Å	θ = 1.8–30.3°
b = 15.3756 (8) Å	µ = 0.11 mm−1
c = 8.9240 (5) Å	T = 293 K
β = 95.932 (2)°	Block, yellow
V = 1568.49 (15) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	4719 independent reflections
Radiation source: fine-focus sealed tube	3292 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 30.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→16
Tmin = 0.977, Tmax = 0.981	k = −21→21
20671 measured reflections	l = −12→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.381P] where P = (Fo2 + 2Fc2)/3
4719 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
C2	0.35042 (12)	0.17029 (9)	0.52062 (17)	0.0356 (3)
C4	0.30165 (12)	0.07826 (8)	0.29487 (15)	0.0323 (3)
H4	0.3447	0.0720	0.2063	0.039*
C5	0.33233 (11)	0.00144 (8)	0.39770 (15)	0.0318 (3)
C6	0.35124 (11)	0.01266 (8)	0.54780 (16)	0.0321 (3)
C7	0.17205 (12)	0.08179 (8)	0.24074 (15)	0.0314 (3)
C8	0.08815 (12)	0.06691 (10)	0.33778 (15)	0.0372 (3)
H8	0.1109	0.0543	0.4385	0.045*
C9	−0.02997 (13)	0.07060 (10)	0.28638 (16)	0.0394 (3)
H9	−0.0858	0.0606	0.3528	0.047*
C10	−0.06474 (12)	0.08894 (9)	0.13824 (15)	0.0347 (3)
C11	0.01924 (12)	0.10656 (9)	0.03979 (15)	0.0329 (3)
C12	0.13663 (12)	0.10213 (9)	0.09088 (15)	0.0337 (3)
H12	0.1925	0.1128	0.0248	0.040*
C13	0.05268 (15)	0.15592 (11)	−0.20597 (17)	0.0458 (4)
H13A	0.1074	0.1099	−0.2233	0.055*
H13B	0.0966	0.2062	−0.1664	0.055*
C14	−0.01997 (19)	0.17865 (13)	−0.34907 (19)	0.0579 (5)
H14A	−0.0642	0.1287	−0.3857	0.087*
H14B	0.0301	0.1968	−0.4229	0.087*
H14C	−0.0725	0.2251	−0.3306	0.087*
C15	0.33489 (12)	−0.08120 (9)	0.31629 (17)	0.0373 (3)
C16	0.3448 (2)	−0.23424 (11)	0.3223 (3)	0.0685 (6)
H16A	0.2807	−0.2358	0.2442	0.103*
H16B	0.3372	−0.2813	0.3913	0.103*
H16C	0.4172	−0.2400	0.2783	0.103*
C17	0.37615 (14)	−0.05489 (10)	0.66793 (17)	0.0422 (3)
H17A	0.3058	−0.0866	0.6803	0.063*
H17B	0.4037	−0.0271	0.7612	0.063*
H17C	0.4348	−0.0942	0.6392	0.063*
N1	0.34801 (11)	0.09613 (8)	0.60651 (15)	0.0381 (3)
N3	0.34091 (11)	0.15896 (8)	0.37262 (14)	0.0371 (3)
O1	0.36409 (10)	0.24219 (7)	0.58341 (13)	0.0474 (3)
O2	−0.18113 (9)	0.09133 (9)	0.09076 (14)	0.0498 (3)
O3	−0.02656 (9)	0.12778 (8)	−0.10273 (11)	0.0444 (3)
O4	0.34354 (12)	−0.15218 (7)	0.40215 (14)	0.0555 (3)
O5	0.32921 (11)	−0.08496 (8)	0.18008 (13)	0.0521 (3)
O6	0.43101 (15)	0.11524 (11)	0.92163 (16)	0.0654 (4)
H1	0.3666 (16)	0.1039 (11)	0.703 (2)	0.045 (5)*
H2	−0.193 (2)	0.0937 (15)	−0.010 (3)	0.077 (7)*
H3	0.3418 (15)	0.2040 (12)	0.317 (2)	0.048 (5)*
H6A	0.418 (2)	0.1623 (17)	0.981 (3)	0.086 (8)*
H6B	0.508 (3)	0.109 (2)	0.921 (4)	0.136 (13)*

	U11	U22	U33	U12	U13	U23
C2	0.0302 (7)	0.0344 (6)	0.0417 (8)	−0.0002 (5)	0.0015 (6)	−0.0002 (5)
C4	0.0312 (6)	0.0350 (6)	0.0301 (7)	−0.0004 (5)	0.0001 (5)	0.0019 (5)
C5	0.0280 (6)	0.0315 (6)	0.0353 (7)	0.0000 (5)	0.0006 (5)	0.0025 (5)
C6	0.0263 (6)	0.0343 (6)	0.0360 (7)	0.0002 (5)	0.0043 (5)	0.0037 (5)
C7	0.0310 (6)	0.0325 (6)	0.0301 (6)	0.0003 (5)	0.0013 (5)	0.0003 (5)
C8	0.0363 (7)	0.0490 (8)	0.0259 (6)	0.0012 (6)	0.0015 (5)	0.0037 (5)
C9	0.0342 (7)	0.0546 (8)	0.0304 (7)	−0.0001 (6)	0.0079 (5)	0.0020 (6)
C10	0.0288 (7)	0.0439 (7)	0.0313 (7)	0.0014 (5)	0.0028 (5)	−0.0031 (5)
C11	0.0350 (7)	0.0379 (7)	0.0254 (6)	0.0002 (5)	0.0010 (5)	0.0012 (5)
C12	0.0322 (7)	0.0400 (7)	0.0294 (6)	−0.0016 (5)	0.0055 (5)	0.0021 (5)
C13	0.0518 (9)	0.0531 (9)	0.0332 (8)	−0.0040 (7)	0.0082 (7)	0.0053 (6)
C14	0.0819 (14)	0.0552 (10)	0.0366 (9)	0.0059 (9)	0.0054 (9)	0.0085 (7)
C15	0.0290 (7)	0.0372 (7)	0.0445 (8)	0.0001 (5)	−0.0020 (6)	−0.0031 (6)
C16	0.0751 (13)	0.0344 (8)	0.0933 (16)	−0.0003 (8)	−0.0045 (11)	−0.0136 (9)
C17	0.0440 (8)	0.0438 (8)	0.0388 (8)	0.0028 (6)	0.0050 (6)	0.0113 (6)
N1	0.0443 (7)	0.0375 (6)	0.0323 (6)	0.0001 (5)	0.0028 (5)	0.0002 (5)
N3	0.0406 (7)	0.0319 (6)	0.0373 (6)	−0.0047 (5)	−0.0026 (5)	0.0063 (5)
O1	0.0557 (7)	0.0356 (5)	0.0501 (7)	−0.0013 (5)	0.0018 (5)	−0.0059 (4)
O2	0.0289 (5)	0.0835 (9)	0.0366 (6)	0.0018 (5)	0.0019 (4)	−0.0008 (6)
O3	0.0380 (6)	0.0664 (7)	0.0281 (5)	−0.0014 (5)	0.0005 (4)	0.0087 (5)
O4	0.0748 (9)	0.0310 (5)	0.0591 (8)	0.0006 (5)	−0.0011 (6)	−0.0010 (5)
O5	0.0593 (7)	0.0524 (7)	0.0431 (7)	0.0062 (5)	−0.0016 (5)	−0.0114 (5)
O6	0.0703 (10)	0.0753 (9)	0.0500 (8)	0.0054 (8)	0.0034 (7)	−0.0158 (7)

C2—O1	1.2421 (16)	C13—O3	1.4279 (19)
C2—N3	1.3255 (19)	C13—C14	1.493 (2)
C2—N1	1.3758 (18)	C13—H13A	0.97
C4—N3	1.4696 (17)	C13—H13B	0.97
C4—C5	1.5149 (18)	C14—H14A	0.96
C4—C7	1.5186 (18)	C14—H14B	0.96
C4—H4	0.98	C14—H14C	0.96
C5—C6	1.3457 (19)	C15—O5	1.2119 (18)
C5—C15	1.4654 (19)	C15—O4	1.3314 (18)
C6—N1	1.3881 (18)	C16—O4	1.450 (2)
C6—C17	1.4988 (19)	C16—H16A	0.96
C7—C8	1.3801 (19)	C16—H16B	0.96
C7—C12	1.3926 (18)	C16—H16C	0.96
C8—C9	1.388 (2)	C17—H17A	0.96
C8—H8	0.93	C17—H17B	0.96
C9—C10	1.370 (2)	C17—H17C	0.96
C9—H9	0.93	N1—H1	0.877 (19)
C10—O2	1.3613 (17)	N3—H3	0.852 (19)
C10—C11	1.3972 (19)	O2—H2	0.90 (2)
C11—O3	1.3648 (16)	O6—H6A	0.92 (3)
C11—C12	1.3804 (19)	O6—H6B	0.89 (4)
C12—H12	0.93
O1—C2—N3	124.06 (13)	C14—C13—H13A	110.4
O1—C2—N1	119.69 (14)	O3—C13—H13B	110.4
N3—C2—N1	116.23 (12)	C14—C13—H13B	110.4
N3—C4—C5	109.36 (11)	H13A—C13—H13B	108.6
N3—C4—C7	111.30 (11)	C13—C14—H14A	109.5
C5—C4—C7	112.32 (11)	C13—C14—H14B	109.5
N3—C4—H4	107.9	H14A—C14—H14B	109.5
C5—C4—H4	107.9	C13—C14—H14C	109.5
C7—C4—H4	107.9	H14A—C14—H14C	109.5
C6—C5—C15	126.53 (12)	H14B—C14—H14C	109.5
C6—C5—C4	120.43 (12)	O5—C15—O4	122.09 (13)
C15—C5—C4	113.02 (12)	O5—C15—C5	122.48 (13)
C5—C6—N1	119.10 (12)	O4—C15—C5	115.44 (13)
C5—C6—C17	128.48 (13)	O4—C16—H16A	109.5
N1—C6—C17	112.41 (12)	O4—C16—H16B	109.5
C8—C7—C12	119.08 (12)	H16A—C16—H16B	109.5
C8—C7—C4	121.36 (12)	O4—C16—H16C	109.5
C12—C7—C4	119.55 (12)	H16A—C16—H16C	109.5
C7—C8—C9	120.57 (13)	H16B—C16—H16C	109.5
C7—C8—H8	119.7	C6—C17—H17A	109.5
C9—C8—H8	119.7	C6—C17—H17B	109.5
C10—C9—C8	120.32 (13)	H17A—C17—H17B	109.5
C10—C9—H9	119.8	C6—C17—H17C	109.5
C8—C9—H9	119.8	H17A—C17—H17C	109.5
O2—C10—C9	119.01 (13)	H17B—C17—H17C	109.5
O2—C10—C11	121.30 (12)	C2—N1—C6	123.58 (13)
C9—C10—C11	119.67 (13)	C2—N1—H1	114.8 (12)
O3—C11—C12	126.10 (12)	C6—N1—H1	119.0 (12)
O3—C11—C10	114.04 (12)	C2—N3—C4	124.82 (12)
C12—C11—C10	119.86 (12)	C2—N3—H3	118.0 (12)
C11—C12—C7	120.46 (12)	C4—N3—H3	115.6 (12)
C11—C12—H12	119.8	C10—O2—H2	111.0 (15)
C7—C12—H12	119.8	C11—O3—C13	117.61 (12)
O3—C13—C14	106.57 (14)	C15—O4—C16	115.74 (14)
O3—C13—H13A	110.4	H6A—O6—H6B	108 (3)
N3—C4—C5—C6	21.65 (17)	O3—C11—C12—C7	178.32 (13)
C7—C4—C5—C6	−102.44 (14)	C10—C11—C12—C7	−1.2 (2)
N3—C4—C5—C15	−159.91 (11)	C8—C7—C12—C11	−0.6 (2)
C7—C4—C5—C15	76.00 (14)	C4—C7—C12—C11	−179.32 (12)
C15—C5—C6—N1	178.59 (12)	C6—C5—C15—O5	−171.98 (14)
C4—C5—C6—N1	−3.19 (19)	C4—C5—C15—O5	9.7 (2)
C15—C5—C6—C17	−1.7 (2)	C6—C5—C15—O4	8.2 (2)
C4—C5—C6—C17	176.53 (13)	C4—C5—C15—O4	−170.10 (12)
N3—C4—C7—C8	−79.50 (16)	O1—C2—N1—C6	−169.74 (13)
C5—C4—C7—C8	43.50 (17)	N3—C2—N1—C6	8.4 (2)
N3—C4—C7—C12	99.20 (14)	C5—C6—N1—C2	−13.8 (2)
C5—C4—C7—C12	−137.80 (13)	C17—C6—N1—C2	166.38 (13)
C12—C7—C8—C9	1.1 (2)	O1—C2—N3—C4	−167.13 (14)
C4—C7—C8—C9	179.85 (13)	N1—C2—N3—C4	14.8 (2)
C7—C8—C9—C10	0.1 (2)	C5—C4—N3—C2	−28.53 (18)
C8—C9—C10—O2	179.40 (14)	C7—C4—N3—C2	96.16 (15)
C8—C9—C10—C11	−1.9 (2)	C12—C11—O3—C13	−6.2 (2)
O2—C10—C11—O3	1.5 (2)	C10—C11—O3—C13	173.34 (13)
C9—C10—C11—O3	−177.11 (13)	C14—C13—O3—C11	−177.41 (13)
O2—C10—C11—C12	−178.89 (13)	O5—C15—O4—C16	−0.5 (2)
C9—C10—C11—C12	2.5 (2)	C5—C15—O4—C16	179.32 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.87 (2)	2.02 (2)	2.890 (2)	172 (2)
N3—H3···O1i	0.85 (2)	2.28 (2)	3.031 (2)	147 (2)
O2—H2···O5ii	0.90 (2)	2.07 (2)	2.810 (2)	139 (2)
O6—H6A···O1iii	0.92 (3)	1.87 (3)	2.777 (2)	170 (2)
O6—H6B···O5iv	0.89 (3)	2.19 (3)	3.025 (2)	156 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.87 (2)	2.02 (2)	2.890 (2)	172 (2)
N3—H3⋯O1i	0.85 (2)	2.28 (2)	3.031 (2)	147 (2)
O2—H2⋯O5ii	0.90 (2)	2.07 (2)	2.810 (2)	139 (2)
O6—H6A⋯O1iii	0.92 (3)	1.87 (3)	2.777 (2)	170 (2)
O6—H6B⋯O5iv	0.89 (3)	2.19 (3)	3.025 (2)	156 (3)

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