(4-Fluoro­phen­yl)[6-(2-fur­yl)-7-nitro-2,3,4,6,7,8-hexa­hydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone

Muhammad Yaqub; Zahid Shafiq; Ashfaq M Qureshi; Muhammad Najam-ul-Haq

doi:10.1107/S1600536809026373

. 2009 Jul 15;65(Pt 8):o1869. doi: 10.1107/S1600536809026373

(4-Fluorophenyl)[6-(2-furyl)-7-nitro-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidin-9-yl]methanone

Muhammad Yaqub ^a,^*, Zahid Shafiq ^a, Ashfaq M Qureshi ^a, Muhammad Najam-ul-Haq ^a

PMCID: PMC2977271 PMID: 21583564

Abstract

In the title compound, C₁₉H₁₈FN₃O₄, the fused pyridine and pyrimidine rings adopt half-chair conformations. The structure displays intramolecular N—H⋯O and intermolecular N—H⋯F hydrogen bonding.

Related literature

For the use of cyclic 1,1-enediamines in the synthesis of a wide variety of fused heterocycles, see: Huang & Wang, (1994 ▶); Yu et al. (2006 ▶); Yaqub et al. (2008 ▶). For related structures, see: Yu et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₁₈FN₃O₄
M _r = 371.36
Orthorhombic,
a = 15.375 (3) Å
b = 7.0706 (14) Å
c = 15.255 (3) Å
V = 1658.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.38 × 0.25 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.958, T _max = 0.979
3533 measured reflections
1943 independent reflections
1657 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.066
S = 1.01
1943 reflections
244 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026373/pv2155sup1.cif

e-65-o1869-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026373/pv2155Isup2.hkl

e-65-o1869-Isup2.hkl^{(95.6KB, hkl)}

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—H1A⋯O4	0.88	1.86	2.579 (3)	138
N1—H1A⋯F1ⁱ	0.88	2.60	3.130 (3)	120

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Symmetry code: (i) Inline graphic .

Acknowledgments

The Institute of Chemistry, Chinese Academy of Science, Beijing, is thanked for providing the single-crystal facility and the Higher Education Commission, Islamabad, Pakistan, is gratefully acknowledged for providing financial support.

supplementary crystallographic information

Comment

Cyclic 1,1-enediamines known as heterocyclic ketene aminals (HKAs) have been exploited in different synthetic methodologies to build a wide variety of fused heterocycles (Huang & Wang, 1994; Yu, et al., 2006; Yaqub, et al., 2008). The title compound, (I), was prepared by treating nitro derivative of Baylis-Hillman acetates with heterocyclic ketene aminals. The structure of (I) is presented in this article.

The stucture of the title compound, (I), is shown in Fig. 1. The fused pyridyl (N2/C4—C8) and pyrimidyl (N1/N2/C1—C3/C8) rings adopt half-chair conformations, C5 and N2 atoms lie 0.596 (4) and 0.640 (5) Å, respectively, out of the planes formed by the remaining ring atoms. The structure displays an intramolecular (N—H···O) and an intermolecular (N—H···F) hydrogen bonding (details are in Table 1). The molecular dimensions in (I) are in accord with a the corrsponding dimensions reported for a structure very closely related to (I) (Yu, et al., 2007).

Experimental

(E)-2-Nitro-3-(2-furanyl)allyl acetate 2 (0.15 g, 0.71 mmol) and ketene aminal 2 (0.146 g, 0.71 mmol) were stirred in 20 ml of dichloromethane (DCM) at 273 K for one hour. Temperature was allowed to rise up to room temperature and stirring was further continued for 6 hrs. Solvent was evaporated and residue was passed through the column. The elution was carried out by petroleum ether: ethyl acetate (3:1) to get the title compound as a light yellow solid. The single crystals of (I) were grown in dichloromethane - petroleum ether (1:5) system at room temperature by slow evaporation. Yield: 62% (0.16 g), m.p. 417–418 K (lit. m.p. 418–419 K).