5-Benzoyl-4-(4-fluoro­phen­yl)-3,4-dihydro­pyrimidin-2(1H)-one

Rajni Kant; Vivek K Gupta; Kamini Kapoor; D R Patil; Madhukar B Deshmukh

doi:10.1107/S1600536812052105

. 2013 Jan 9;69(Pt 2):o196. doi: 10.1107/S1600536812052105

5-Benzoyl-4-(4-fluorophenyl)-3,4-dihydropyrimidin-2(1H)-one

Rajni Kant ^a,^*, Vivek K Gupta ^a, Kamini Kapoor ^a, D R Patil ^b, Madhukar B Deshmukh ^b

PMCID: PMC3569257 PMID: 23424480

Abstract

In the title molecule, C₁₇H₁₃FN₂O₂, the 3,4-dihydropyrimidine ring adopts a flattened sofa conformation with the flap atom (which bears the fluorophenyl substituent) deviating from the plane defined by the remaining five ring atoms by 0.281 (2) Å. This plane forms dihedral angles of 85.98 (6) and 60.63 (6)° with the 4-fluorophenyl and benzoyl-phenyl rings, respectively. The dihedral angle between the 4-fluorophenyl group and the benzene ring is 71.78 (6)°. In the crystal, N—H⋯O hydrogen bonds link molecules into inversion dimers that are further connected by another N—H⋯O interaction into a two-dimensional supramolecular structure parallel to (101).

Related literature

For general background to and pharmaceutical applications of pyrimidinones, see: Ghorab et al. (2000 ▶); Shivarama Holla et al. (2004 ▶); Stefani et al. (2006 ▶). For related structures, see: Fun et al. (2009 ▶); Chitra et al. (2009 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C₁₇H₁₃FN₂O₂
M _r = 296.29
Monoclinic,
a = 12.7911 (5) Å
b = 8.1862 (3) Å
c = 13.7325 (5) Å
β = 98.850 (4)°
V = 1420.82 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.777, T _max = 1.000
27552 measured reflections
2786 independent reflections
1836 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.131
S = 1.04
2786 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(23KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812052105/gk2549sup1.cif

e-69-0o196-sup1.cif^{(23KB, cif)}

Click here for additional data file.^{(134KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052105/gk2549Isup2.hkl

e-69-0o196-Isup2.hkl^{(134KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812052105/gk2549Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.96	2.777 (2)	159
N3—H3⋯O1ⁱⁱ	0.86	2.12	2.937 (2)	159

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

supplementary crystallographic information

Comment

Dihydropyrimidinones exhibit a wide range of biological effects including antifungal, antiviral, anticancer, antibacterial, anti-inflammatory and antihypertensive (Ghorab et al., 2000; Shivarama Holla et al., 2004). Dihydropyrimidin-2(1H)-ones can also be used as antioxidant agents (Stefani et al., 2006). This paper reports the crystal structure of the title dihydropyrimidinone derivative.

In the title compound (Fig.1) all bond lengths and angles are normal and correspond to those observed in related structures (Fun et al., 2009; Chitra et al., 2009). The dihydropyrimidine ring adopts a sofa conformation (ΔC_s(C4) = 5.436)(Duax & Norton, 1975) and the plane of the five essentially coplanar atoms (C5/C6/N1/C2/N3) of this ring (maximum deviation -0.045 (2) Å for all atoms) forms a dihedral angle of 85.98 (6)° and 60.63 (6)° with fluorophenyl and benzene ring respectively. In the crystal, N1—H1···O2 hydrogen bonds link molecules into dimers that are further connected by N3—H3···O1 and (Table 1) interactions into two dimensional supramolecular structure (Fig. 2).

Experimental

A mixture of 3-(dimethylamino)-1-phenylprop-2-en-1-one (1mmol), 4-fluorobenzaldehyde (1mmol), urea (1.2 mmol) and PTSA (30 mol%) in 5 ml ethanol was stirred at 78 °C till the completion of the reaction monitored by TLC. Then reaction mixture was gradually cooled down to room temperature. The precipitate was filtered and washed with cold ethanol (m.p.: 555-557 K, yield: 81%). IR(KBr): 3268, 2964,1682, 1641 ,1592, 1371, 1200, 1151 cm^-1;¹H NMR(300 MHz, DMSO-d6): δ = 5.45-5.46(d,1H,CH);7.03-7.14(m,3H,Ar-H); 7.35-7.50(m,6H,Ar-H);7.86-7.87(d,1H,NH); 8.21 ( s,1H,CH ); 9.38 ( s,1H,NH );