Methyl 4-(3-eth­oxy-4-hydroxy­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate monohydrate

Thenmozhi, M.; Kavitha, T.; Satyanarayana, V.S.V.; Vijayakumar, V.; Ponnuswamy, M.N.

doi:10.1107/S160053680902769X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1921-o1922

doi:10.1107/S160053680902769X

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Methyl 4-(3-ethoxy-4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate

M. Thenmozhi,^a T. Kavitha,^a V. S. V. Satyanarayana,^b V. Vijayakumar ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bOrganic Chemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 29 June 2009; accepted 14 July 2009; online 18 July 2009)

In the title compound, C₁₅H₁₈N₂O₅·H₂O, the pyrimidine ring adopts a flattened-boat conformation. The ethoxy group attached to the benzene ring is in an extended conformation. The oxopyrimidine molecules are linked into centrosymmetric R₂²(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 molecules.

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_r = 324.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.04
4719 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻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⋯O5^iv	0.89 (3)	2.19 (3)	3.025 (2)	156 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Pyrimidines are considered to be important not only they form an integral part of the genetic material (viz. DNA and RNA), but also impart numerous biological activities such as bactericides, fungicides, viricides, insecticides and meticides. They have also found applications in agricultural and industrial chemicals (Kidwai et al., 2003).

The pyrimidine ring assumes a flattened-boat conformation with puckering parameters (Cremer & Pople, 1975) q₂ = 0.241 (1) Å, q₃ = 0.077 (1) Å and ϕ= 12.5 (3)°, and the asymmetry parameter (Nardelli, 1983) Δ_s(N1,C4) = 8.4 (2)°. The hydroxyphenyl ring is almost perpendicular to the C2/N3/C5/C6 plane, with a dihedral angle of 85.13 (7)°. The ethoxy [C14—C13—O3—C11 = -177.41 (13)°] and carboxylate [C5—C15—O4—C16 = 179.32 (14)°] groups attached to the pyrimidine ring exhibit extented conformations. The sum of the bond angles around atom N1 [357.4°] of the pyrimidine ring is in accordance with sp² hybridization (Beddoes et al., 1986). The C2═O1 bond length of 1.2420 (18) Å is close to the expected value of 1.225 Å for a free, unbridged bond (Litvinov et al., 1992).

The molecules are linked into centrosymmetric R₂²(20) dimers by O—H···O hydrogen bonds and the dimers are linked by N—H···O hydrogen bonds to form a two-dimensional network parallel to the bc plane. The adjacent networks are cross-linked via N—H···O and O—H···O hydrogen bonds involving the water molecules.

Related literature top

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 top

A mixture of 3-ethoxy-4-hydroxy benzaldehyde (10 mmol), methylacetoacetate (12 mmol), urea (15 mmol) and 1 ml of conc. HCl was placed in a round bottom flask containing 30 ml of acetonitrile. The reaction mixture was refluxed for 5 h at 348-353 K. After completion of the reaction (checked by TLC), the reaction mixture was poured in ice cooled water. The separated solid was filtered, dried and recrystallized with methanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. The dashed line indicates a hydrogen bond.
	Fig. 2. Part of the crystal packing of the title compound, showing hydrogen-bonded (dashed lines) dimers.

Methyl 4-(3-ethoxy-4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4- tetrahydropyrimidine-5-carboxylate monohydrate top

Crystal data top

C₁₅H₁₈N₂O₅·H₂O	F(000) = 688
M_r = 324.33	D_x = 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

Data collection top

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

Refinement top

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 = 1.04	w = 1/[σ²(F_o²) + (0.0643P)² + 0.381P] where P = (F_o² + 2F_c²)/3
4719 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₈N₂O₅·H₂O	V = 1568.49 (15) Å³
M_r = 324.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4927 (6) Å	µ = 0.11 mm⁻¹
b = 15.3756 (8) Å	T = 293 K
c = 8.9240 (5) Å	0.25 × 0.20 × 0.20 mm
β = 95.932 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4719 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3292 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.025
20671 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
4719 reflections	Δρ_min = −0.25 e Å⁻³
231 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O5^iv	0.89 (3)	2.19 (3)	3.025 (2)	156 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₂O₅·H₂O
M_r	324.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.4927 (6), 15.3756 (8), 8.9240 (5)
β (°)	95.932 (2)
V (Å³)	1568.49 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	20671, 4719, 3292
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.04
No. of reflections	4719
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1999), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O5^iv	0.89 (3)	2.19 (3)	3.025 (2)	156 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z+1.

Acknowledgements

MT thanks the University of Madras for a University Research Fellowship.

References

Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
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Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 65| Part 8| August 2009| Pages o1921-o1922

doi:10.1107/S160053680902769X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 4-(3-eth­­oxy-4-hy­droxy­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 4-(3-ethoxy-4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate