Ethyl 1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Zubatyuk, R.I.; Shishkin, O.V.; Ihmels, H.; Lebedyeva, I.A.; Povstyanoy, M.V.

doi:10.1107/S1600536810023482

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1762-o1763

doi:10.1107/S1600536810023482

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Ethyl 1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Roman I. Zubatyuk,^a ^* Oleg V. Shishkin,^a Heiko Ihmels,^b Iryna A. Lebedyeva ^c and Mykhaylo V. Povstyanoy ^c

^aSTC "Institute for Single Crystals" NAS of Ukraine, 60 Lenina Ave., Kharkiv, Ukraine, ^bUniversity of Siegen, FB 8, Adolf Reichwein Strasse 2, 57068 Siegen, Germany, and ^cDepartment of Organic and Biochemical Synthesis, Kherson National Technical University, 24 Berislavske Highway, Kherson 73008, Ukraine
^*Correspondence e-mail: roman@xray.isc.kharkov.com

(Received 12 May 2010; accepted 17 June 2010; online 23 June 2010)

In the title compound, C₁₈H₁₉N₃O₃, the tetrahydropyrimidone ring adopts a distorted boat conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked via intermolecular C—H⋯π interactions. In addition, an intramolecular C—H⋯O hydrogen bond occurs.

Related literature

It has been proposed that the combination of the biologically active dihydropyrimidine subunit with a DNA intercalator (Waring, 2006 ; Hannon, 2007 ; Ihmels & Otto, 2005 ) may lead to a new class of DNA-targeting drugs (Neidle & Thurston, 2005 ; Braña et al., 2001 ). Thus, a classical DNA intercalator, namely quinoline (Denny, 2003 ; Kharatishvili et al., 1997 ; Aislabie et al., 1990 ), was employed as quinoline-4-carbaldehyde in the Biginelli (1893 ) reaction that leads to the title compound. For the biological activity of pyrimidine-containing compounds, see: Goldmann & Stoltefuss (1991 ); McKinstry & Reading (1944 ); Kappe (2000 ); Luo et al. (2004 ). For van der Waals radii, see: Zefirov & Zorky (1989 ).

Experimental

Crystal data

C₁₈H₁₉N₃O₃
M_r = 325.36
Triclinic, $[P \overline 1]$
a = 8.5039 (10) Å
b = 9.4637 (11) Å
c = 10.7503 (11) Å
α = 110.799 (10)°
β = 95.807 (9)°
γ = 97.339 (9)°
V = 792.07 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire3 detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.975, T_max = 1
8517 measured reflections
4607 independent reflections
2810 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.117
S = 0.99
4607 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.86	2.03	2.8701 (16)	164
C17—H17A⋯O2	0.96	2.16	2.8187 (19)	124
C16—H16C⋯Cg1ⁱⁱ	0.96	2.66	3.603 (2)	168
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810023482/lx2153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023482/lx2153Isup2.hkl

checkCIF report

Comment top

Pyrimidine-containing compounds exhibit a wide spectrum of biological activity (Goldmann & Stoltefuss, 1991). For example, dihydropyrimidines derivatives (DHPMs) may be applied as antimicrobial (McKinstry & Reading, 1944), anti-inflammatory (Kappe, 2000), anticarcenogenic drugs (Luo et al., 2004). A three-component condensation of urea derivatives with aromatic aldehydes and β-ketoesters, known as Biginelli reaction allows the synthesis of the DHPM unit with a widely modified and variable substitution pattern. It was proposed that the combination of the biologically active DHPM subunit with a DNA intercalator (Waring, 2006; Hannon, 2007; Ihmels & Otto, 2005) may lead to a new class of DNA-targeting drugs (Neidle & Thurston, 2005; Braña et al., 2001). Thus, a classical DNA, namely quinoline (Denny, 2003; Kharatishvili et al., 1997; Aislabie et al., 1990), was employed as quinoline-4-carbaldehyde in the Biginelli reaction according to traditional reaction conditions in ethanol employing hydrochloric acid as catalyst (Biginelli, 1893) leading to the title compound (Fig. 1).

Tetrahydropyrimidone ring adopts a distorted boat conformation with the C1, C2, C3 and N1 atoms almost coplanar (dihedral angle of 1.47 (18)°), while the C4 and N2 atoms deviated from this plane by -0.342 (2) Å and -0.481 (2) Å, respectively. This non-planariry is probably additionally supported by steric repulsion between methyl groups at the C3 and N1 atoms (short intramolecular contacts C17···H18a 2.55 Å and C18···C17a 2.57 Å while van der Waals radii sum is 2.87 Å, Zefirov & Zorky, 1989). Quinoline substituent has axial orientation (the C4—N2—C1—C5 torsion angle of -95.03 (14)°) and rotated almost coplanar to the C1—C2 bond (dihedral angle of -13.55 (16)°) despite short intramolecular contact H6···C2 2.48 Å (van der Waals radii sum is 2.87 Å, Zefirov & Zorky, 1989). Ester substituent at the C2 atom slightly rotated with respect to C1/C2/C3/N1 fragment (the C1—C2—C14—O1 torsion angle of -24.96 (18)°) supporting formation of attractive intramolecular contact O1···H1 2.44 Å (van der Waals radii sum of 2.46 Å). The ester substituent rotation is accompanied by formation of short intramolecular C17—H17c···O2 hydrogen bond.

The crystal packing (Fig. 2) is stabilized by intramolecular C—H···O and intermolecular N—H···O hydrogen bonds between adjacent amide fragments of pyrimidine ring, with a N2—H2···O3ⁱ (Table 1). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the methyl H atom of the ethyl group and the pyridine ring of a neighbouring quinoline system, with a C16—H16C···Cg1ⁱⁱ.

(Table 1; Cg1 is the centroid of the C5/C6/C7/N3/C8/C13 pyridine ring).

Related literature top

It has been proposed that the combination of the biologically active dihydropyrimidine subunit with a DNA intercalator (Waring, 2006; Hannon, 2007; Ihmels & Otto, 2005) may lead to a new class of DNA-targeting drugs (Neidle & Thurston, 2005; Braña et al., 2001). Thus, a classical DNA, namely quinoline (Denny, 2003; Kharatishvili et al., 1997; Aislabie et al., 1990), was employed as quinoline-4-carbaldehyde in the Biginelli (1893) reaction that lead to the title compound. For the biological activity of pyrimidine-containing compounds, see: Goldmann & Stoltefuss (1991); McKinstry & Reading (1944); Kappe (2000); Luo et al. (2004). For van der Waals radii, see: Zefirov & Zorky (1989).

Experimental top

The title compound was synthesized by refluxing condition of monomethylurea (0.237 g, 3.20 mmol), 4-quinoline aldehyde (0.502 g, 3.20 mmol), acetoacetic ester (0.520 g, 4.00 mmol) with catalytic amount of HCl in 15 ml EtOH. The residue was purified by column chromatography (silica gel, hexane–acetone, 90:5 v/v) to afforded the title compound as a colorless solid (yield 48%, m.p. 472 K). The single crystals suitable for X-ray diffraction were obtained by evaporation of a solution of the title compound in acetone.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. N—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) x, - y + 1, z ; (ii) - x, - y + 1, - z. ]

Ethyl 1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetrahydropyrimidine-5- carboxylate top

Crystal data top

C₁₈H₁₉N₃O₃	Z = 2
M_r = 325.36	F(000) = 344
Triclinic, P1	D_x = 1.364 Mg m⁻³
a = 8.5039 (10) Å	Mo Kα radiation, λ = 0.7107 Å
b = 9.4637 (11) Å	Cell parameters from 3300 reflections
c = 10.7503 (11) Å	θ = 3.1–32.4°
α = 110.799 (10)°	µ = 0.10 mm⁻¹
β = 95.807 (9)°	T = 293 K
γ = 97.339 (9)°	Prism, colorless
V = 792.07 (17) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire3 detector	4607 independent reflections
Graphite monochromator	2810 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	R_int = 0.017
ω scans	θ_max = 30.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −12→12
T_min = 0.975, T_max = 1	k = −14→13
8517 measured reflections	l = −14→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
4607 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₉N₃O₃	γ = 97.339 (9)°
M_r = 325.36	V = 792.07 (17) Å³
Triclinic, P1	Z = 2
a = 8.5039 (10) Å	Mo Kα radiation
b = 9.4637 (11) Å	µ = 0.10 mm⁻¹
c = 10.7503 (11) Å	T = 293 K
α = 110.799 (10)°	0.4 × 0.3 × 0.2 mm
β = 95.807 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire3 detector	4607 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2810 reflections with I > 2σ(I)
T_min = 0.975, T_max = 1	R_int = 0.017
8517 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	Δρ_max = 0.30 e Å⁻³
4607 reflections	Δρ_min = −0.17 e Å⁻³
220 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.27163 (12)	0.04049 (12)	0.18120 (11)	0.0531 (3)
O2	0.06327 (12)	−0.03288 (11)	0.26749 (11)	0.0499 (3)
O3	−0.17806 (12)	0.43713 (11)	0.03648 (11)	0.0505 (3)
N1	−0.19236 (12)	0.24916 (11)	0.12189 (11)	0.0342 (2)
N2	0.05174 (13)	0.36177 (12)	0.09001 (11)	0.0392 (3)
H2	0.1019	0.4088	0.0464	0.047*
N3	0.34211 (15)	0.63743 (12)	0.56698 (12)	0.0471 (3)
C1	0.14609 (14)	0.29466 (13)	0.16757 (12)	0.0315 (3)
H1	0.2345	0.2599	0.1197	0.038*
C2	0.04233 (15)	0.15552 (12)	0.17321 (12)	0.0317 (3)
C3	−0.11880 (15)	0.13846 (13)	0.15232 (12)	0.0324 (3)
C4	−0.10723 (16)	0.35587 (13)	0.08131 (13)	0.0355 (3)
C5	0.21887 (13)	0.41308 (12)	0.30752 (12)	0.0297 (3)
C6	0.16516 (16)	0.40622 (14)	0.42047 (13)	0.0377 (3)
H6	0.0850	0.3261	0.4139	0.045*
C7	0.23041 (18)	0.51977 (16)	0.54688 (15)	0.0467 (3)
H7	0.1913	0.5106	0.6219	0.056*
C8	0.40063 (15)	0.64740 (14)	0.45630 (14)	0.0385 (3)
C9	0.52172 (17)	0.77391 (15)	0.47649 (16)	0.0497 (4)
H9	0.5580	0.8462	0.5631	0.060*
C10	0.58558 (18)	0.79118 (17)	0.37115 (18)	0.0562 (4)
H10	0.6645	0.8754	0.3856	0.067*
C11	0.53288 (17)	0.68249 (17)	0.24086 (17)	0.0519 (4)
H11	0.5785	0.6942	0.1693	0.062*
C12	0.41510 (15)	0.55914 (15)	0.21731 (15)	0.0390 (3)
H12	0.3810	0.4886	0.1298	0.047*
C13	0.34461 (13)	0.53745 (13)	0.32394 (13)	0.0315 (3)
C14	0.13704 (16)	0.04890 (13)	0.20431 (13)	0.0356 (3)
C15	0.14436 (18)	−0.14639 (16)	0.29605 (17)	0.0488 (4)
H15B	0.2456	−0.0972	0.3555	0.059*
H15A	0.1659	−0.2207	0.2133	0.059*
C16	0.0369 (2)	−0.2227 (2)	0.3611 (2)	0.0799 (7)
H16B	0.0163	−0.1479	0.4426	0.120*
H16C	0.0869	−0.2987	0.3820	0.120*
H16A	−0.0625	−0.2712	0.3011	0.120*
C17	−0.23434 (17)	0.00572 (15)	0.15444 (17)	0.0485 (4)
H17C	−0.2872	0.0395	0.2319	0.073*
H17A	−0.1769	−0.0738	0.1587	0.073*
H17B	−0.3128	−0.0334	0.0741	0.073*
C18	−0.36752 (16)	0.23559 (17)	0.09982 (16)	0.0475 (4)
H18B	−0.4112	0.2070	0.1682	0.071*
H18A	−0.4111	0.1585	0.0127	0.071*
H18C	−0.3949	0.3324	0.1041	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0463 (6)	0.0626 (6)	0.0668 (8)	0.0204 (5)	0.0161 (5)	0.0384 (6)
O2	0.0498 (6)	0.0499 (6)	0.0725 (8)	0.0210 (4)	0.0171 (5)	0.0433 (5)
O3	0.0463 (6)	0.0575 (6)	0.0623 (7)	0.0094 (4)	0.0002 (5)	0.0421 (5)
N1	0.0347 (6)	0.0355 (5)	0.0355 (6)	0.0048 (4)	0.0016 (5)	0.0183 (4)
N2	0.0379 (6)	0.0459 (6)	0.0416 (7)	0.0001 (4)	−0.0010 (5)	0.0301 (5)
N3	0.0521 (7)	0.0459 (6)	0.0369 (7)	0.0003 (5)	0.0004 (5)	0.0124 (5)
C1	0.0329 (6)	0.0319 (6)	0.0324 (7)	0.0051 (4)	0.0036 (5)	0.0158 (5)
C2	0.0381 (7)	0.0275 (5)	0.0289 (6)	0.0034 (4)	0.0012 (5)	0.0116 (5)
C3	0.0402 (7)	0.0296 (6)	0.0269 (6)	0.0027 (5)	0.0009 (5)	0.0121 (5)
C4	0.0411 (7)	0.0368 (6)	0.0296 (7)	0.0030 (5)	−0.0012 (5)	0.0167 (5)
C5	0.0295 (6)	0.0295 (5)	0.0328 (7)	0.0078 (4)	0.0026 (5)	0.0146 (5)
C6	0.0416 (7)	0.0358 (6)	0.0359 (7)	0.0016 (5)	0.0053 (6)	0.0157 (5)
C7	0.0571 (9)	0.0482 (8)	0.0337 (8)	0.0036 (6)	0.0072 (7)	0.0159 (6)
C8	0.0363 (7)	0.0372 (7)	0.0396 (8)	0.0042 (5)	−0.0017 (6)	0.0144 (6)
C9	0.0433 (8)	0.0428 (8)	0.0538 (10)	−0.0051 (6)	−0.0066 (7)	0.0151 (6)
C10	0.0433 (9)	0.0512 (9)	0.0716 (12)	−0.0093 (6)	−0.0034 (8)	0.0291 (8)
C11	0.0426 (8)	0.0599 (9)	0.0618 (11)	0.0003 (7)	0.0095 (7)	0.0354 (8)
C12	0.0341 (7)	0.0441 (7)	0.0423 (8)	0.0059 (5)	0.0042 (6)	0.0210 (6)
C13	0.0271 (6)	0.0326 (6)	0.0380 (7)	0.0067 (4)	0.0012 (5)	0.0174 (5)
C14	0.0416 (7)	0.0309 (6)	0.0335 (7)	0.0057 (5)	0.0023 (6)	0.0123 (5)
C15	0.0510 (8)	0.0454 (8)	0.0646 (10)	0.0194 (6)	0.0091 (7)	0.0341 (7)
C16	0.0721 (12)	0.0777 (12)	0.136 (2)	0.0347 (10)	0.0407 (13)	0.0815 (13)
C17	0.0440 (8)	0.0434 (7)	0.0608 (10)	−0.0029 (6)	−0.0011 (7)	0.0289 (7)
C18	0.0372 (8)	0.0574 (8)	0.0553 (10)	0.0096 (6)	0.0063 (7)	0.0297 (7)

Geometric parameters (Å, º) top

O1—C14	1.2018 (15)	C8—C9	1.4125 (18)
O2—C14	1.3377 (15)	C8—C13	1.4207 (18)
O2—C15	1.4504 (14)	C9—C10	1.356 (2)
O3—C4	1.2283 (14)	C9—H9	0.9300
N1—C4	1.3871 (15)	C10—C11	1.397 (2)
N1—C3	1.4019 (14)	C10—H10	0.9300
N1—C18	1.4662 (16)	C11—C12	1.3676 (18)
N2—C4	1.3380 (16)	C11—H11	0.9300
N2—C1	1.4538 (14)	C12—C13	1.4103 (18)
N2—H2	0.8600	C12—H12	0.9300
N3—C7	1.3061 (17)	C15—C16	1.471 (2)
N3—C8	1.3637 (18)	C15—H15B	0.9700
C1—C2	1.5122 (15)	C15—H15A	0.9700
C1—C5	1.5293 (17)	C16—H16B	0.9600
C1—H1	0.9800	C16—H16C	0.9600
C2—C3	1.3451 (17)	C16—H16A	0.9600
C2—C14	1.4735 (16)	C17—H17C	0.9600
C3—C17	1.5012 (16)	C17—H17A	0.9600
C5—C6	1.3591 (17)	C17—H17B	0.9600
C5—C13	1.4330 (15)	C18—H18B	0.9600
C6—C7	1.4022 (19)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—H7	0.9300

C14—O2—C15	117.81 (10)	C9—C10—H10	120.0
C4—N1—C3	121.22 (10)	C11—C10—H10	120.0
C4—N1—C18	115.73 (10)	C12—C11—C10	120.81 (14)
C3—N1—C18	121.48 (10)	C12—C11—H11	119.6
C4—N2—C1	124.96 (10)	C10—C11—H11	119.6
C4—N2—H2	117.5	C11—C12—C13	120.95 (13)
C1—N2—H2	117.5	C11—C12—H12	119.5
C7—N3—C8	116.88 (12)	C13—C12—H12	119.5
N2—C1—C2	108.97 (10)	C12—C13—C8	117.82 (11)
N2—C1—C5	111.30 (9)	C12—C13—C5	124.39 (12)
C2—C1—C5	112.65 (10)	C8—C13—C5	117.79 (11)
N2—C1—H1	107.9	O1—C14—O2	122.41 (11)
C2—C1—H1	107.9	O1—C14—C2	123.48 (11)
C5—C1—H1	107.9	O2—C14—C2	114.03 (11)
C3—C2—C14	126.27 (11)	O2—C15—C16	106.99 (11)
C3—C2—C1	120.96 (10)	O2—C15—H15B	110.3
C14—C2—C1	112.77 (10)	C16—C15—H15B	110.3
C2—C3—N1	119.79 (10)	O2—C15—H15A	110.3
C2—C3—C17	125.97 (11)	C16—C15—H15A	110.3
N1—C3—C17	114.21 (11)	H15B—C15—H15A	108.6
O3—C4—N2	122.75 (11)	C15—C16—H16B	109.5
O3—C4—N1	120.25 (12)	C15—C16—H16C	109.5
N2—C4—N1	116.98 (10)	H16B—C16—H16C	109.5
C6—C5—C13	117.48 (11)	C15—C16—H16A	109.5
C6—C5—C1	121.55 (10)	H16B—C16—H16A	109.5
C13—C5—C1	120.96 (10)	H16C—C16—H16A	109.5
C5—C6—C7	120.17 (12)	C3—C17—H17C	109.5
C5—C6—H6	119.9	C3—C17—H17A	109.5
C7—C6—H6	119.9	H17C—C17—H17A	109.5
N3—C7—C6	124.77 (13)	C3—C17—H17B	109.5
N3—C7—H7	117.6	H17C—C17—H17B	109.5
C6—C7—H7	117.6	H17A—C17—H17B	109.5
N3—C8—C9	117.53 (13)	N1—C18—H18B	109.5
N3—C8—C13	122.88 (11)	N1—C18—H18A	109.5
C9—C8—C13	119.59 (13)	H18B—C18—H18A	109.5
C10—C9—C8	120.78 (14)	N1—C18—H18C	109.5
C10—C9—H9	119.6	H18B—C18—H18C	109.5
C8—C9—H9	119.6	H18A—C18—H18C	109.5
C9—C10—C11	120.05 (13)

C4—N2—C1—C2	29.78 (16)	C8—N3—C7—C6	−1.4 (2)
C4—N2—C1—C5	−95.05 (13)	C5—C6—C7—N3	0.6 (2)
N2—C1—C2—C3	−21.57 (16)	C7—N3—C8—C9	−179.87 (13)
C5—C1—C2—C3	102.47 (13)	C7—N3—C8—C13	0.41 (19)
N2—C1—C2—C14	159.04 (10)	N3—C8—C9—C10	179.93 (13)
C5—C1—C2—C14	−76.92 (13)	C13—C8—C9—C10	−0.3 (2)
C14—C2—C3—N1	−179.22 (11)	C8—C9—C10—C11	−0.6 (2)
C1—C2—C3—N1	1.47 (18)	C9—C10—C11—C12	1.0 (2)
C14—C2—C3—C17	−1.0 (2)	C10—C11—C12—C13	−0.6 (2)
C1—C2—C3—C17	179.65 (12)	C11—C12—C13—C8	−0.31 (18)
C4—N1—C3—C2	15.51 (18)	C11—C12—C13—C5	178.85 (12)
C18—N1—C3—C2	−179.37 (12)	N3—C8—C13—C12	−179.52 (11)
C4—N1—C3—C17	−162.87 (11)	C9—C8—C13—C12	0.77 (17)
C18—N1—C3—C17	2.25 (17)	N3—C8—C13—C5	1.27 (17)
C1—N2—C4—O3	165.93 (12)	C9—C8—C13—C5	−178.45 (11)
C1—N2—C4—N1	−15.95 (18)	C6—C5—C13—C12	178.85 (11)
C3—N1—C4—O3	169.42 (12)	C1—C5—C13—C12	−2.32 (17)
C18—N1—C4—O3	3.50 (18)	C6—C5—C13—C8	−1.99 (15)
C3—N1—C4—N2	−8.75 (18)	C1—C5—C13—C8	176.84 (10)
C18—N1—C4—N2	−174.68 (12)	C15—O2—C14—O1	−6.3 (2)
N2—C1—C5—C6	109.13 (12)	C15—O2—C14—C2	176.97 (11)
C2—C1—C5—C6	−13.61 (15)	C3—C2—C14—O1	155.76 (13)
N2—C1—C5—C13	−69.65 (13)	C1—C2—C14—O1	−24.89 (18)
C2—C1—C5—C13	167.60 (10)	C3—C2—C14—O2	−27.58 (19)
C13—C5—C6—C7	1.16 (17)	C1—C2—C14—O2	151.78 (11)
C1—C5—C6—C7	−177.67 (11)	C14—O2—C15—C16	−178.22 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.86	2.03	2.8701 (16)	164
C17—H17A···O2	0.96	2.16	2.8187 (19)	124
C16—H16C···Cg1ⁱⁱ	0.96	2.66	3.603 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₃O₃
M_r	325.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5039 (10), 9.4637 (11), 10.7503 (11)
α, β, γ (°)	110.799 (10), 95.807 (9), 97.339 (9)
V (Å³)	792.07 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire3 detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.975, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	8517, 4607, 2810
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.117, 0.99
No. of reflections	4607
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), Superflip (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.86	2.03	2.8701 (16)	164
C17—H17A···O2	0.96	2.16	2.8187 (19)	124
C16—H16C···Cg1ⁱⁱ	0.96	2.66	3.603 (2)	168

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

Acknowledgements

The authors are grateful to the DAAD (Deutscher Akademischer Austausch Dienst) for a research scholarship.

References

Aislabie, J., Bej, A. K., Rothenburger, S. & Atlas, R. M. (1990). Appl. Environ. Microbiol. 56, 345–351. Google Scholar
Biginelli, P. (1893). Gazz. Chim. Ital. 23, 360–412. Google Scholar
Braña, M. F., Cacho, M., Gradillas, A., Pascual-Teresa, B. & Ramos, A. (2001). Curr. Pharm. Des. 7, 1745–1780. Web of Science PubMed Google Scholar
Denny, W. A. (2003). DNA and RNA Binders: From Small Molecules to Drugs. Weinheim: Wiley-VCH. Google Scholar
Goldmann, S. & Stoltefuss, J. (1991). Angew. Chem. Int. Ed. Engl. 30, 1559–1578. CrossRef Web of Science Google Scholar
Hannon, M. J. (2007). Chem. Soc. Rev. 36, 280–295. Web of Science CrossRef PubMed CAS Google Scholar
Ihmels, H. & Otto, D. (2005). Top. Curr. Chem. 258, 161–204. Web of Science CrossRef CAS Google Scholar
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052. Web of Science CrossRef PubMed CAS Google Scholar
Kharatishvili, M., Mathieson, M. & Farrell, N. (1997). Inorg. Chim. Acta, 255, 1–6. CrossRef CAS Web of Science Google Scholar
Luo, L., Carson, J. D., Dhanak, D., Jackson, J. R., Huang, P. S., Lee, Y., Sakowicz, R. & Copeland, R. A. (2004). Biochemistry, 43, 15258–15266. Web of Science CrossRef PubMed CAS Google Scholar
McKinstry, D. W. & Reading, E. H. (1944). J. Franklin. Inst. 237, 422–427. CAS Google Scholar
Neidle, S. & Thurston, D. E. (2005). Nat. Rev. Cancer, 5, 285–296. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Waring, M. J. (2006). Sequence-specific DNA binding agents. Cambridge: RSC Publishing. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar
Zefirov, Yu. V. & Zorky, P. M. (1989). Russ. Chem. Rev. 58, 421–440. CrossRef Google Scholar

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Volume 66| Part 7| July 2010| Pages o1762-o1763

doi:10.1107/S1600536810023482

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

Ethyl 1,6-di­methyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1,6-dimethyl-2-oxo-4-(quinolin-4-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate