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

In the title compound, C(14)H(16)N(2)O(4)·H(2)O, the dihedral angles between the planes of the 4-hydroxy-phenyl and ester groups with the plane of the six-membered tetra-hydro-pyrimidine ring are 87.3 (1) and 75.9 (1)°, respectively. The crystal structure is stabilized by O-H⋯O and N-H⋯O hydrogen bonding between the water mol-ecule and the organic functionalities.

Related literature

Bignelli compounds are poly-functionalized dihydro­pyrimidines exhibiting a broad range of therapeutic and pharmacological properties, see: Atwal et al. (1991 ▶); Jauk et al. (2000 ▶); Kappe (2000 ▶); Kato (1984 ▶).

Experimental

Crystal data

C14H16N2O4·H2O

M = 294.30

Triclinic,

a = 5.6859 (2) Å

b = 10.7190 (5) Å

c = 12.1980 (5) Å

α = 85.267 (3)°

β = 83.990 (3)°

γ = 74.936 (4)°

V = 712.76 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 292 K

0.38 × 0.24 × 0.15 mm

Data collection

Goniometer Xcalibur with Eos (Nova) detector diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.951, T max = 0.984

18207 measured reflections

2792 independent reflections

2109 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.09

2792 reflections

201 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037441/hg2566sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037441/hg2566Isup2.hkl

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

C14H16N2O4·H2O	Z = 2
Mr = 294.30	F(000) = 312
Triclinic, P1	Dx = 1.371 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 5.6859 (2) Å	Cell parameters from 400 reflections
b = 10.7190 (5) Å	θ = 1.0–28.0°
c = 12.1980 (5) Å	µ = 0.11 mm−1
α = 85.267 (3)°	T = 292 K
β = 83.990 (3)°	Plate, colorless
γ = 74.936 (4)°	0.38 × 0.24 × 0.15 mm
V = 712.76 (6) Å3

Goniometer Xcalibur with Eos (Nova) detector diffractometer	2792 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2109 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.951, Tmax = 0.984	l = −15→15
18207 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.046P)2 + 0.1184P] where P = (Fo2 + 2Fc2)/3
2792 reflections	(Δ/σ)max < 0.000
201 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
H1W	0.159 (5)	0.640 (3)	0.786 (2)	0.096 (9)*
H2W	0.059 (4)	0.773 (3)	0.799 (2)	0.096 (8)*
O1	0.9249 (2)	−0.09595 (10)	0.89786 (9)	0.0468 (3)
O4	0.4417 (2)	0.21103 (11)	0.32278 (8)	0.0479 (3)
H4	0.5634	0.2371	0.3022	0.072*
O3	−0.0136 (2)	0.32510 (10)	0.79355 (9)	0.0446 (3)
C9	0.3842 (3)	0.14292 (13)	0.66438 (12)	0.0322 (3)
C4	0.3717 (3)	0.11045 (13)	0.78842 (12)	0.0346 (3)
H4A	0.2225	0.0817	0.8101	0.041*
N2	0.5830 (2)	0.00283 (11)	0.81312 (10)	0.0400 (3)
H2	0.6038	−0.0650	0.7766	0.048*
C5	0.1804 (3)	0.34545 (15)	0.83520 (12)	0.0391 (4)
C1	0.7456 (3)	−0.00217 (14)	0.88495 (12)	0.0352 (3)
N1	0.7088 (2)	0.10279 (12)	0.94695 (10)	0.0416 (3)
H1	0.8040	0.0987	0.9982	0.050*
C3	0.3665 (3)	0.22455 (14)	0.85610 (12)	0.0348 (3)
C12	0.4247 (3)	0.19198 (14)	0.43558 (12)	0.0366 (4)
C13	0.5795 (3)	0.22773 (15)	0.50023 (12)	0.0396 (4)
H13	0.6971	0.2686	0.4677	0.047*
C14	0.5585 (3)	0.20247 (14)	0.61345 (12)	0.0378 (4)
H14	0.6642	0.2261	0.6563	0.045*
C11	0.2467 (3)	0.13405 (15)	0.48509 (13)	0.0407 (4)
H11	0.1395	0.1117	0.4423	0.049*
C2	0.5263 (3)	0.21559 (14)	0.93180 (12)	0.0368 (4)
C10	0.2282 (3)	0.10937 (14)	0.59840 (13)	0.0379 (4)
H10	0.1090	0.0696	0.6309	0.046*
C6	−0.1877 (3)	0.43911 (17)	0.74982 (15)	0.0515 (4)
H6A	−0.1987	0.5121	0.7938	0.062*
H6B	−0.3484	0.4227	0.7537	0.062*
O2	0.1978 (2)	0.45309 (11)	0.85073 (11)	0.0594 (4)
C8	0.5280 (4)	0.31579 (16)	1.01034 (14)	0.0541 (5)
H8A	0.3836	0.3856	1.0053	0.081*
H8B	0.6701	0.3484	0.9917	0.081*
H8C	0.5316	0.2776	1.0843	0.081*
C7	−0.1064 (4)	0.47022 (19)	0.63274 (16)	0.0673 (6)
H7A	−0.0706	0.3936	0.5920	0.101*
H7B	0.0377	0.5015	0.6304	0.101*
H7C	−0.2341	0.5355	0.6005	0.101*
O5W	0.1583 (3)	0.71105 (16)	0.75335 (11)	0.0583 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0563 (7)	0.0347 (6)	0.0454 (6)	0.0015 (5)	−0.0149 (5)	−0.0075 (5)
O4	0.0647 (8)	0.0479 (7)	0.0323 (6)	−0.0128 (6)	−0.0113 (5)	−0.0060 (5)
O3	0.0406 (6)	0.0380 (6)	0.0526 (7)	−0.0044 (5)	−0.0058 (5)	−0.0040 (5)
C9	0.0347 (8)	0.0270 (7)	0.0340 (8)	−0.0034 (6)	−0.0057 (6)	−0.0065 (6)
C4	0.0376 (8)	0.0309 (8)	0.0355 (8)	−0.0085 (6)	−0.0030 (6)	−0.0040 (6)
N2	0.0543 (8)	0.0273 (7)	0.0376 (7)	−0.0035 (6)	−0.0129 (6)	−0.0076 (5)
C5	0.0446 (9)	0.0366 (9)	0.0337 (8)	−0.0068 (7)	0.0009 (7)	−0.0055 (6)
C1	0.0470 (9)	0.0292 (8)	0.0282 (7)	−0.0077 (7)	−0.0026 (7)	−0.0009 (6)
N1	0.0540 (9)	0.0349 (7)	0.0351 (7)	−0.0043 (6)	−0.0139 (6)	−0.0075 (5)
C3	0.0422 (9)	0.0321 (8)	0.0291 (7)	−0.0082 (7)	0.0005 (6)	−0.0046 (6)
C12	0.0457 (9)	0.0292 (8)	0.0323 (8)	−0.0008 (7)	−0.0097 (7)	−0.0071 (6)
C13	0.0460 (9)	0.0399 (9)	0.0357 (8)	−0.0154 (7)	−0.0034 (7)	−0.0053 (6)
C14	0.0416 (9)	0.0406 (9)	0.0352 (8)	−0.0131 (7)	−0.0096 (7)	−0.0081 (6)
C11	0.0390 (9)	0.0409 (9)	0.0440 (9)	−0.0057 (7)	−0.0170 (7)	−0.0106 (7)
C2	0.0491 (9)	0.0305 (8)	0.0291 (7)	−0.0073 (7)	−0.0014 (7)	−0.0039 (6)
C10	0.0342 (8)	0.0362 (8)	0.0442 (9)	−0.0080 (7)	−0.0066 (7)	−0.0057 (7)
C6	0.0433 (10)	0.0427 (10)	0.0637 (11)	0.0012 (8)	−0.0094 (8)	−0.0089 (8)
O2	0.0660 (8)	0.0335 (7)	0.0786 (9)	−0.0046 (6)	−0.0223 (7)	−0.0095 (6)
C8	0.0767 (13)	0.0410 (10)	0.0427 (9)	−0.0033 (9)	−0.0164 (9)	−0.0146 (7)
C7	0.0882 (16)	0.0475 (11)	0.0607 (12)	−0.0030 (10)	−0.0195 (11)	−0.0001 (9)
O5W	0.0737 (10)	0.0535 (9)	0.0480 (8)	−0.0163 (7)	−0.0009 (7)	−0.0085 (7)

O1—C1	1.2450 (18)	C12—C13	1.383 (2)
O4—C12	1.3712 (18)	C13—C14	1.384 (2)
O4—H4	0.8200	C13—H13	0.9300
O3—C5	1.3354 (19)	C14—H14	0.9300
O3—C6	1.4601 (19)	C11—C10	1.384 (2)
C9—C14	1.382 (2)	C11—H11	0.9300
C9—C10	1.388 (2)	C2—C8	1.500 (2)
C9—C4	1.523 (2)	C10—H10	0.9300
C4—N2	1.4710 (18)	C6—C7	1.493 (3)
C4—C3	1.523 (2)	C6—H6A	0.9700
C4—H4A	0.9800	C6—H6B	0.9700
N2—C1	1.3268 (19)	C8—H8A	0.9600
N2—H2	0.8600	C8—H8B	0.9600
C5—O2	1.2150 (19)	C8—H8C	0.9600
C5—C3	1.467 (2)	C7—H7A	0.9600
C1—N1	1.3662 (19)	C7—H7B	0.9600
N1—C2	1.3872 (19)	C7—H7C	0.9600
N1—H1	0.8600	O5W—H1W	0.83 (3)
C3—C2	1.343 (2)	O5W—H2W	0.93 (3)
C12—C11	1.382 (2)
C12—O4—H4	109.5	C9—C14—C13	121.54 (14)
C5—O3—C6	116.65 (13)	C9—C14—H14	119.2
C14—C9—C10	117.91 (13)	C13—C14—H14	119.2
C14—C9—C4	120.72 (13)	C12—C11—C10	119.95 (14)
C10—C9—C4	121.32 (13)	C12—C11—H11	120.0
N2—C4—C9	108.75 (11)	C10—C11—H11	120.0
N2—C4—C3	109.61 (12)	C3—C2—N1	120.40 (13)
C9—C4—C3	113.46 (12)	C3—C2—C8	126.94 (14)
N2—C4—H4A	108.3	N1—C2—C8	112.60 (13)
C9—C4—H4A	108.3	C11—C10—C9	121.23 (14)
C3—C4—H4A	108.3	C11—C10—H10	119.4
C1—N2—C4	127.84 (12)	C9—C10—H10	119.4
C1—N2—H2	116.1	O3—C6—C7	109.76 (14)
C4—N2—H2	116.1	O3—C6—H6A	109.7
O2—C5—O3	122.53 (15)	C7—C6—H6A	109.7
O2—C5—C3	125.31 (15)	O3—C6—H6B	109.7
O3—C5—C3	112.14 (13)	C7—C6—H6B	109.7
O1—C1—N2	123.60 (13)	H6A—C6—H6B	108.2
O1—C1—N1	119.71 (14)	C2—C8—H8A	109.5
N2—C1—N1	116.69 (13)	C2—C8—H8B	109.5
C1—N1—C2	123.59 (13)	H8A—C8—H8B	109.5
C1—N1—H1	118.2	C2—C8—H8C	109.5
C2—N1—H1	118.2	H8A—C8—H8C	109.5
C2—C3—C5	120.99 (13)	H8B—C8—H8C	109.5
C2—C3—C4	121.53 (13)	C6—C7—H7A	109.5
C5—C3—C4	117.47 (13)	C6—C7—H7B	109.5
O4—C12—C11	118.08 (13)	H7A—C7—H7B	109.5
O4—C12—C13	122.33 (15)	C6—C7—H7C	109.5
C11—C12—C13	119.58 (14)	H7A—C7—H7C	109.5
C12—C13—C14	119.76 (15)	H7B—C7—H7C	109.5
C12—C13—H13	120.1	H1W—O5W—H2W	105 (2)
C14—C13—H13	120.1
C14—C9—C4—N2	−71.27 (17)	C9—C4—C3—C5	52.91 (18)
C10—C9—C4—N2	106.19 (15)	O4—C12—C13—C14	−178.02 (14)
C14—C9—C4—C3	50.98 (18)	C11—C12—C13—C14	1.5 (2)
C10—C9—C4—C3	−131.56 (14)	C10—C9—C14—C13	−0.3 (2)
C9—C4—N2—C1	126.81 (16)	C4—C9—C14—C13	177.20 (13)
C3—C4—N2—C1	2.3 (2)	C12—C13—C14—C9	−0.6 (2)
C6—O3—C5—O2	10.0 (2)	O4—C12—C11—C10	177.99 (13)
C6—O3—C5—C3	−168.50 (13)	C13—C12—C11—C10	−1.6 (2)
C4—N2—C1—O1	−177.32 (14)	C5—C3—C2—N1	−176.83 (13)
C4—N2—C1—N1	2.8 (2)	C4—C3—C2—N1	2.9 (2)
O1—C1—N1—C2	174.44 (14)	C5—C3—C2—C8	5.9 (2)
N2—C1—N1—C2	−5.6 (2)	C4—C3—C2—C8	−174.35 (15)
O2—C5—C3—C2	26.2 (2)	C1—N1—C2—C3	2.9 (2)
O3—C5—C3—C2	−155.34 (14)	C1—N1—C2—C8	−179.51 (15)
O2—C5—C3—C4	−153.49 (16)	C12—C11—C10—C9	0.7 (2)
O3—C5—C3—C4	24.92 (18)	C14—C9—C10—C11	0.3 (2)
N2—C4—C3—C2	−5.05 (19)	C4—C9—C10—C11	−177.23 (13)
C9—C4—C3—C2	−126.82 (15)	C5—O3—C6—C7	85.59 (18)
N2—C4—C3—C5	174.68 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.09	2.9411 (17)	171
O5W—H1W···O2	0.83 (3)	2.06 (3)	2.881 (2)	172 (3)
N2—H2···O4ii	0.86	2.14	2.978 (2)	165
O5W—H2W···O1iii	0.93 (3)	1.88 (3)	2.799 (2)	167 (2)
O4—H4···O5Wiv	0.82	1.86	2.674 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.09	2.9411 (17)	171
N2—H2⋯O4ii	0.86	2.14	2.978 (2)	165
O4—H4⋯O5Wiv	0.82	1.86	2.674 (2)	176
O5W—H1W⋯O2	0.83 (3)	2.06 (3)	2.881 (2)	172 (3)
O5W—H2W⋯O1iii	0.93 (3)	1.88 (3)	2.799 (2)	167 (2)

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