Ethyl 6-ethoxy­carbonyl­methyl-4-(2-hydroxy­phen­yl)-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Kettmann, V.; Světlík, J.; Veizerová, L.

doi:10.1107/S1600536808012683

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1092

doi:10.1107/S1600536808012683

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Ethyl 6-ethoxycarbonylmethyl-4-(2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Viktor Kettmann,^a ^* Jan Světlík ^a and Lucia Veizerová ^a

^aFaculty of Pharmacy, Comenius University, Odbojarov 10, SK-83232 Bratislava, Slovakia
^*Correspondence e-mail: kettmann@fpharm.uniba.sk

(Received 2 April 2008; accepted 30 April 2008; online 17 May 2008)

The title compound, C₁₇H₂₀N₂O₆, belongs to the monastrol-type of anticancer agents and was selected for crystal structure determination in order to confirm its molecular structure and explore some aspects of its structure–activity relationships. The central tetrahydropyrimidine ring has a flat-envelope conformation. The 4-hydroxyphenyl group occupies a pseudo-axial position and is inclined at an angle of 87.7 (2)° to the mean plane of the heterocyclic ring. Of the two ethyl ester groups, one (in the 5-position) is in a coplanar and the other (in the 6-position) is in a perpendicular orientation with respect to the heterocyclic plane. There is a three-dimensional hydrogen-bonding network in which all hydrogen-bond donors and acceptors are involved.

Related literature

For related literature, see: Allen (2002 ); Azizian et al. (2007 ); Qing-Fang et al. (2007 ); Endow & Baker (2003 ); Kettmann & Svetlík (1997 ); Světlík et al. (1991 ); Wood & Bergnes (2004 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₆
M_r = 348.35
Triclinic, $[P \overline 1]$
a = 8.783 (2) Å
b = 9.336 (3) Å
c = 11.415 (4) Å
α = 71.47 (4)°
β = 82.78 (5)°
γ = 75.05 (4)°
V = 856.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
5849 measured reflections
4950 independent reflections
3935 reflections with I > 2σ(I)
R_int = 0.040
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.174
S = 1.04
4950 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.97	2.788 (2)	159
O2—H2⋯O3ⁱⁱ	0.82	1.95	2.772 (2)	177
N3—H3⋯O5ⁱⁱⁱ	0.86	2.20	3.0014 (18)	155
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y, -z+1; (iii) x, y-1, z.

Data collection: XSCANS (Siemens, 1991 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012683/wk2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012683/wk2083Isup2.hkl

checkCIF report

Comment top

Recently, while we have been continuing in our programme aimed at synthesis of monastrol (1) analogues as valuable antitumour drugs (Wood & Bergnes, 2004), a related tetrahydropyrimidine compound (2) has been described by another group (Azizian et al., 2007). As we had reported earlier (Světlík et al., 1991; Kettmann & Svetlík, 1997) that classical Biginelli condensation with salicylaldehyde gives oxygen-bridged pyrimidine (3) rather than the 'open' molecule (4), the formation of (2) was accordingly unexpected. Thus, to verify the correctness of the title structure (2), an X-ray analysis was undertaken. As the cytotoxic activity of these derivatives is related to inhibition of the kinesin Eg5 protein (Endow & Baker, 2003), another purpose of this work was to determine detailed molecular conformation which is indispensable for an analysis of structure-activity relationships.

The structure determination has confirmed (Fig. 1) that the compound studied here has indeed the structure (2) (Fig. 2). As retrieved from the Cambridge Structural Database (Version of 2007; Allen, 2002), the bond lengths and angles (Table 1) within the tetrahydropyrimidine ring are equal within experimental error to those previously reported for a number of structures incorporating this molecular fragment (see, e.g., Qing-Fang et al., 2007). Bonding characteristics in other parts of the molecule also agree with those generally expected.

As noted above, from the biological standpoint, the conformational properties of the molecule are of prime interest here. First, the conformation of the central heterocycle can best be described as a flat envelope with atom C4 (at the flap) deviating by 0.433 (2) Å from the mean plane of the remaining atoms. As to the ring substituents, the 4-hydroxyphenyl group occupies the pseudoaxial position and is in a perpendicular orientation with respect to the tetrahydropyrimidine ring [dihedral angle 87.7 (2)°]; the conformation of the substituent on the exocyclic C4—C7 bond is synperiplanar, i.e. the hydroxy group is on the same side as the H atom on C4 (Fig.1). The ester group on C5 lies approximately in the plane of the C5=C6 double bond, with the carbonyl function oriented cis relative to this double bond. By contrast, the ethoxycarbonyl moiety of the 6-substituent is oriented, due to rather free rotation about the two C16 methylenic bonds, perpendicularly with respect to the mean plane of the heterocycle.

The crystal packing is dominated by hydrogen bonding. As shown in Table 2 and Fig. 3, each molecule forms two pairs of hydrogen bonds (N1-H···O1 and O2-H···O3) across centres of symmetry, which results in formation of chains of hydrogen-bonded molecules. The chains are interconnected by another independent hydrogen bond, N3-H···O5.

Related literature top

For related literature, see: Allen (2002); Azizian et al. (2007); Qing-Fang et al. (2007); Endow & Baker (2003); Kettmann & Svetlík (1997); Světlík et al. (1991); Wood & Bergnes (2004).

Experimental top

Synthesis of the title compound, (2), has been described (Azizian et al., 2007). In short, heating of salicylaldehyde (0.52 ml, 5 mmol) with diethyl acetone-1,3-dicarboxylate (0.91 ml, 5 mmol) and urea (0.36 g, 6 mmol) under p-toluenesulfonic acid (0.04 g, 0.2 mmol) catalysis without solvent at 353–363 K for 3 h gave the desired product (50% yield; m.p. 488–490 K). Crystalssuitable for the X-ray analysis were obtained by a slow crystallization from ethanol.

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS (Siemens, 1991); data reduction: XSCANS (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot of (2) with the labelling scheme for the non-H atoms, which are drawn as 35% probability ellipsoids.
	Fig. 2. The structure of compounds (1)–(4).
	Fig. 3. View of the crystal packing along the a axis, showing system of hydrogen bonds (dashed lines).

Ethyl 6-ethoxycarbonylmethyl-4-(2-hydroxyphenyl)-2-oxo-1,2,3,4- tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₇H₂₀N₂O₆	Z = 2
M_r = 348.35	F(000) = 368
Triclinic, P1	D_x = 1.351 Mg m⁻³
Hall symbol: -P 1	Melting point: 489 K
a = 8.783 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.336 (3) Å	Cell parameters from 20 reflections
c = 11.415 (4) Å	θ = 7–18°
α = 71.47 (4)°	µ = 0.10 mm⁻¹
β = 82.78 (5)°	T = 296 K
γ = 75.05 (4)°	Prism, colourless
V = 856.5 (5) Å³	0.30 × 0.25 × 0.20 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.040
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 1.9°
Graphite monochromator	h = −1→12
ω/2θ scans	k = −12→12
5849 measured reflections	l = −16→16
4950 independent reflections	3 standard reflections every 97 reflections
3935 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0972P)² + 0.1877P] where P = (F_o² + 2F_c²)/3
4950 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₆	γ = 75.05 (4)°
M_r = 348.35	V = 856.5 (5) Å³
Triclinic, P1	Z = 2
a = 8.783 (2) Å	Mo Kα radiation
b = 9.336 (3) Å	µ = 0.10 mm⁻¹
c = 11.415 (4) Å	T = 296 K
α = 71.47 (4)°	0.30 × 0.25 × 0.20 mm
β = 82.78 (5)°

Data collection top

Siemens P4 diffractometer	R_int = 0.040
5849 measured reflections	3 standard reflections every 97 reflections
4950 independent reflections	intensity decay: none
3935 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
4950 reflections	Δρ_min = −0.32 e Å⁻³
229 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
N1	0.10214 (15)	0.47412 (12)	0.13671 (11)	0.0350 (3)
H1	0.0749	0.5465	0.0692	0.042*
C2	0.11515 (15)	0.32189 (14)	0.13967 (13)	0.0315 (3)
O1	0.06497 (13)	0.29448 (11)	0.05495 (10)	0.0408 (3)
N3	0.17844 (14)	0.21317 (12)	0.24052 (11)	0.0344 (3)
H3	0.1615	0.1218	0.2584	0.041*
C4	0.27587 (15)	0.24302 (13)	0.32230 (12)	0.0304 (3)
H4	0.2669	0.1704	0.4051	0.037*
C5	0.21064 (15)	0.40660 (14)	0.33107 (12)	0.0307 (3)
C6	0.13046 (15)	0.51589 (13)	0.23577 (12)	0.0302 (3)
C7	0.44794 (15)	0.21163 (14)	0.27695 (12)	0.0315 (3)
C8	0.51674 (18)	0.32744 (17)	0.19754 (16)	0.0431 (3)
H8	0.4584	0.4297	0.1753	0.052*
C9	0.6717 (2)	0.2929 (2)	0.15072 (18)	0.0521 (4)
H9	0.7161	0.3715	0.0975	0.063*
C10	0.75860 (19)	0.1417 (2)	0.18372 (18)	0.0519 (4)
H10	0.8617	0.1182	0.1519	0.062*
C11	0.69370 (19)	0.02481 (19)	0.26383 (17)	0.0469 (4)
H11	0.7536	−0.0768	0.2867	0.056*
C12	0.53881 (16)	0.05890 (15)	0.31031 (14)	0.0353 (3)
O2	0.46665 (14)	−0.05252 (12)	0.38635 (12)	0.0489 (3)
H2	0.5328	−0.1341	0.4106	0.073*
C13	0.24784 (17)	0.43413 (15)	0.44190 (13)	0.0367 (3)
O3	0.31840 (19)	0.33335 (14)	0.52678 (12)	0.0602 (4)
O4	0.19773 (16)	0.58055 (12)	0.44378 (11)	0.0485 (3)
C14	0.2312 (3)	0.6194 (2)	0.55027 (18)	0.0582 (5)
H14A	0.3441	0.6037	0.5551	0.070*
H14B	0.1912	0.5542	0.6260	0.070*
C15	0.1516 (3)	0.7858 (2)	0.5332 (2)	0.0668 (6)
H15A	0.1992	0.8497	0.4624	0.100*
H15B	0.1627	0.8131	0.6055	0.100*
H15C	0.0417	0.8016	0.5208	0.100*
C16	0.06044 (17)	0.68574 (14)	0.22359 (14)	0.0363 (3)
H16A	−0.0109	0.7274	0.1562	0.044*
H16B	−0.0022	0.6925	0.2988	0.044*
C17	0.17511 (19)	0.78803 (15)	0.20076 (15)	0.0403 (3)
O5	0.13786 (18)	0.91436 (13)	0.21651 (16)	0.0651 (4)
O6	0.31602 (15)	0.72710 (13)	0.15956 (13)	0.0521 (3)
C18	0.4286 (3)	0.8264 (3)	0.1244 (3)	0.0778 (7)
H18A	0.4017	0.9049	0.0460	0.093*
H18B	0.4240	0.8786	0.1864	0.093*
C19	0.5842 (3)	0.7343 (3)	0.1139 (4)	0.0954 (9)
H19A	0.6129	0.6613	0.1931	0.143*
H19B	0.6572	0.8004	0.0864	0.143*
H19C	0.5870	0.6792	0.0553	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0449 (6)	0.0191 (5)	0.0410 (6)	−0.0060 (4)	−0.0108 (5)	−0.0068 (4)
C2	0.0302 (6)	0.0220 (5)	0.0430 (7)	−0.0070 (4)	−0.0017 (5)	−0.0100 (5)
O1	0.0490 (6)	0.0278 (5)	0.0503 (6)	−0.0086 (4)	−0.0120 (5)	−0.0145 (4)
N3	0.0371 (6)	0.0183 (4)	0.0485 (6)	−0.0078 (4)	−0.0076 (5)	−0.0076 (4)
C4	0.0316 (6)	0.0192 (5)	0.0374 (6)	−0.0034 (4)	−0.0032 (5)	−0.0057 (4)
C5	0.0309 (6)	0.0208 (5)	0.0386 (6)	−0.0023 (4)	−0.0031 (5)	−0.0086 (4)
C6	0.0301 (6)	0.0200 (5)	0.0400 (6)	−0.0040 (4)	−0.0043 (5)	−0.0086 (4)
C7	0.0306 (6)	0.0246 (5)	0.0377 (6)	−0.0014 (4)	−0.0050 (5)	−0.0098 (5)
C8	0.0376 (7)	0.0299 (6)	0.0546 (9)	−0.0049 (5)	0.0012 (6)	−0.0062 (6)
C9	0.0421 (8)	0.0477 (9)	0.0610 (10)	−0.0127 (7)	0.0082 (7)	−0.0108 (7)
C10	0.0331 (7)	0.0566 (10)	0.0660 (11)	−0.0028 (7)	0.0024 (7)	−0.0262 (8)
C11	0.0364 (7)	0.0375 (7)	0.0644 (10)	0.0053 (6)	−0.0075 (7)	−0.0210 (7)
C12	0.0345 (6)	0.0257 (6)	0.0450 (7)	−0.0006 (5)	−0.0095 (5)	−0.0118 (5)
O2	0.0458 (6)	0.0227 (5)	0.0677 (8)	−0.0004 (4)	−0.0063 (5)	−0.0039 (5)
C13	0.0402 (7)	0.0268 (6)	0.0403 (7)	−0.0018 (5)	−0.0062 (5)	−0.0094 (5)
O3	0.0838 (10)	0.0372 (6)	0.0517 (7)	0.0105 (6)	−0.0301 (7)	−0.0116 (5)
O4	0.0702 (8)	0.0307 (5)	0.0453 (6)	0.0010 (5)	−0.0188 (5)	−0.0164 (4)
C14	0.0785 (13)	0.0520 (10)	0.0517 (10)	−0.0078 (9)	−0.0171 (9)	−0.0264 (8)
C15	0.0932 (16)	0.0557 (11)	0.0642 (12)	−0.0218 (11)	0.0058 (11)	−0.0351 (10)
C16	0.0368 (6)	0.0207 (5)	0.0507 (8)	0.0016 (5)	−0.0126 (6)	−0.0121 (5)
C17	0.0508 (8)	0.0217 (5)	0.0483 (8)	−0.0047 (5)	−0.0154 (6)	−0.0082 (5)
O5	0.0715 (9)	0.0265 (5)	0.1037 (11)	−0.0072 (5)	−0.0159 (8)	−0.0272 (6)
O6	0.0534 (7)	0.0329 (5)	0.0741 (8)	−0.0180 (5)	0.0064 (6)	−0.0185 (5)
C18	0.0722 (14)	0.0501 (11)	0.116 (2)	−0.0352 (10)	0.0059 (13)	−0.0184 (12)
C19	0.0650 (14)	0.0790 (17)	0.154 (3)	−0.0359 (13)	0.0172 (16)	−0.0439 (18)

Geometric parameters (Å, º) top

N1—C6	1.3761 (18)	C12—O2	1.366 (2)
N1—C2	1.3859 (16)	O2—H2	0.8200
N1—H1	0.8600	C13—O3	1.2161 (19)
C2—O1	1.2319 (17)	C13—O4	1.3299 (17)
C2—N3	1.3385 (19)	O4—C14	1.456 (2)
N3—C4	1.4733 (18)	C14—C15	1.490 (3)
N3—H3	0.8600	C14—H14A	0.9700
C4—C5	1.5172 (17)	C14—H14B	0.9700
C4—C7	1.5196 (19)	C15—H15A	0.9600
C4—H4	0.9800	C15—H15B	0.9600
C5—C6	1.3553 (19)	C15—H15C	0.9600
C5—C13	1.458 (2)	C16—C17	1.505 (2)
C6—C16	1.5134 (17)	C16—H16A	0.9700
C7—C8	1.390 (2)	C16—H16B	0.9700
C7—C12	1.3997 (18)	C17—O5	1.2047 (18)
C8—C9	1.393 (2)	C17—O6	1.318 (2)
C8—H8	0.9300	O6—C18	1.461 (2)
C9—C10	1.376 (3)	C18—C19	1.428 (4)
C9—H9	0.9300	C18—H18A	0.9700
C10—C11	1.381 (3)	C18—H18B	0.9700
C10—H10	0.9300	C19—H19A	0.9600
C11—C12	1.391 (2)	C19—H19B	0.9600
C11—H11	0.9300	C19—H19C	0.9600

C6—N1—C2	123.64 (12)	C12—O2—H2	109.5
C6—N1—H1	118.2	O3—C13—O4	121.72 (14)
C2—N1—H1	118.2	O3—C13—C5	123.83 (13)
O1—C2—N3	124.46 (12)	O4—C13—C5	114.46 (12)
O1—C2—N1	119.97 (13)	C13—O4—C14	118.33 (13)
N3—C2—N1	115.52 (12)	O4—C14—C15	107.06 (16)
C2—N3—C4	122.97 (11)	O4—C14—H14A	110.3
C2—N3—H3	118.5	C15—C14—H14A	110.3
C4—N3—H3	118.5	O4—C14—H14B	110.3
N3—C4—C5	109.07 (11)	C15—C14—H14B	110.3
N3—C4—C7	109.88 (11)	H14A—C14—H14B	108.6
C5—C4—C7	113.81 (11)	C14—C15—H15A	109.5
N3—C4—H4	108.0	C14—C15—H15B	109.5
C5—C4—H4	108.0	H15A—C15—H15B	109.5
C7—C4—H4	108.0	C14—C15—H15C	109.5
C6—C5—C13	125.23 (12)	H15A—C15—H15C	109.5
C6—C5—C4	119.05 (12)	H15B—C15—H15C	109.5
C13—C5—C4	115.65 (11)	C17—C16—C6	116.62 (12)
C5—C6—N1	119.39 (11)	C17—C16—H16A	108.1
C5—C6—C16	127.74 (12)	C6—C16—H16A	108.1
N1—C6—C16	112.86 (11)	C17—C16—H16B	108.1
C8—C7—C12	118.38 (13)	C6—C16—H16B	108.1
C8—C7—C4	122.55 (12)	H16A—C16—H16B	107.3
C12—C7—C4	118.97 (12)	O5—C17—O6	124.41 (16)
C7—C8—C9	121.11 (15)	O5—C17—C16	122.19 (16)
C7—C8—H8	119.4	O6—C17—C16	113.38 (12)
C9—C8—H8	119.4	C17—O6—C18	116.16 (15)
C10—C9—C8	119.64 (16)	C19—C18—O6	109.59 (19)
C10—C9—H9	120.2	C19—C18—H18A	109.8
C8—C9—H9	120.2	O6—C18—H18A	109.8
C9—C10—C11	120.39 (15)	C19—C18—H18B	109.8
C9—C10—H10	119.8	O6—C18—H18B	109.8
C11—C10—H10	119.8	H18A—C18—H18B	108.2
C10—C11—C12	120.09 (15)	C18—C19—H19A	109.5
C10—C11—H11	120.0	C18—C19—H19B	109.5
C12—C11—H11	120.0	H19A—C19—H19B	109.5
O2—C12—C11	122.69 (13)	C18—C19—H19C	109.5
O2—C12—C7	116.89 (13)	H19A—C19—H19C	109.5
C11—C12—C7	120.39 (15)	H19B—C19—H19C	109.5

C6—N1—C2—O1	168.78 (13)	C8—C9—C10—C11	−0.7 (3)
C6—N1—C2—N3	−8.8 (2)	C9—C10—C11—C12	1.0 (3)
O1—C2—N3—C4	162.57 (13)	C10—C11—C12—O2	177.68 (15)
N1—C2—N3—C4	−19.99 (19)	C10—C11—C12—C7	−0.3 (2)
C2—N3—C4—C5	36.47 (17)	C8—C7—C12—O2	−178.66 (14)
C2—N3—C4—C7	−88.92 (15)	C4—C7—C12—O2	−2.32 (19)
N3—C4—C5—C6	−27.05 (17)	C8—C7—C12—C11	−0.5 (2)
C7—C4—C5—C6	96.02 (15)	C4—C7—C12—C11	175.82 (13)
N3—C4—C5—C13	155.91 (12)	C6—C5—C13—O3	179.07 (16)
C7—C4—C5—C13	−81.02 (15)	C4—C5—C13—O3	−4.1 (2)
C13—C5—C6—N1	−179.52 (13)	C6—C5—C13—O4	−0.8 (2)
C4—C5—C6—N1	3.74 (19)	C4—C5—C13—O4	176.03 (12)
C13—C5—C6—C16	−1.2 (2)	O3—C13—O4—C14	0.9 (3)
C4—C5—C6—C16	−177.95 (12)	C5—C13—O4—C14	−179.27 (15)
C2—N1—C6—C5	16.6 (2)	C13—O4—C14—C15	−175.54 (17)
C2—N1—C6—C16	−161.95 (13)	C5—C6—C16—C17	71.9 (2)
N3—C4—C7—C8	93.30 (16)	N1—C6—C16—C17	−109.73 (15)
C5—C4—C7—C8	−29.33 (19)	C6—C16—C17—O5	−163.22 (15)
N3—C4—C7—C12	−82.87 (15)	C6—C16—C17—O6	18.42 (19)
C5—C4—C7—C12	154.50 (12)	O5—C17—O6—C18	−3.9 (3)
C12—C7—C8—C9	0.8 (2)	C16—C17—O6—C18	174.44 (17)
C4—C7—C8—C9	−175.40 (15)	C17—O6—C18—C19	164.6 (2)
C7—C8—C9—C10	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.788 (2)	159
O2—H2···O3ⁱⁱ	0.82	1.95	2.772 (2)	177
N3—H3···O5ⁱⁱⁱ	0.86	2.20	3.0014 (18)	155

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₆
M_r	348.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.783 (2), 9.336 (3), 11.415 (4)
α, β, γ (°)	71.47 (4), 82.78 (5), 75.05 (4)
V (Å³)	856.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5849, 4950, 3935
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.174, 1.04
No. of reflections	4950
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.32

Computer programs: XSCANS (Siemens, 1991), XSCANS (Siemens, 1991), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

N1—C6	1.3761 (18)	N3—C4	1.4733 (18)
N1—C2	1.3859 (16)	C4—C5	1.5172 (17)
C2—O1	1.2319 (17)	C5—C6	1.3553 (19)
C2—N3	1.3385 (19)

C5—C4—C7—C8	−29.33 (19)	C5—C6—C16—C17	71.9 (2)
C6—C5—C13—O3	179.07 (16)	C6—C16—C17—O6	18.42 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.788 (2)	158.6
O2—H2···O3ⁱⁱ	0.82	1.95	2.772 (2)	177.1
N3—H3···O5ⁱⁱⁱ	0.86	2.20	3.0014 (18)	154.9

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

Acknowledgements

This work was supported by the Grant Agency of the Slovak Republic, project Nos. 1/4298/07 and 1/4299/07.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Azizian, J., Mohammadi, A. A., Kohshari, M., Karimi, A. R. & Mohammadizadeh, M. R. (2007). J. Heterocycl. Chem. 44, 455–458. CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1991). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 6-eth­oxy­carbonyl­methyl-4-(2-hy­droxy­phen­yl)-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

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Experimental

Crystal data

Data collection

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Ethyl 6-ethoxycarbonylmethyl-4-(2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate