A. Ramazani, A. Morsali, Ν. Noshiranzadeh
2002
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Abstract
C15H10O4, monoclinic, P\2\!c\ (No. 14), a = 12.246(2) Â, b = 10.541(2) Â, c = 8.912(2)k,ß = 96.205(4)°, V= 1143.7 Â, Ζ = 4, R&(F) = 0.058, wRretfF) = 0.152, T= 110 K. Source of material Methyl 3-oxo-3//-benzo[f]chromene-1 -carboxylate was synthesized in accordance with our new procedure [1]. The solution of title compound (0.3 g) in acetonitrile-benzene (1:1; 35 ml) left in room temperature for six days. The reddish crystals were filtered off, washed with cold acetonitrile-benzene ( 1:1 ; 9 ml) and dried in vacuum over P4O10 (mp 413 K; yield 56%). Elemental analyses were consistent with the stiochiometry C15H10O4 (found: C, 70.79%; H, 4.05%; calc.: C, 70.87%; H, 3.97%). Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. Elemental analyses were performed using a Heraeus CHN-O-Rapid analyzer. Discussion Chromene derivatives are important heterocycles in bio-organic chemistry and are present in many natural products and pharmaceuticals. There have been reported many studies on the synthesis of the heterocyclic chromene ring structure [2-8]. In the recent years there has been increasing interest in the determination of X-ray crystal structures of biologically active compounds [9,10]. In the structure of title molecule (upper figure), the covalent bonds are found to be normal (relevant bond lengths : d(01—CI) =1.372(3) Κ d(Ol—C5) = 1.376(3) Â, ¿(02—CI) = 1.212(3) Â, ¿(03—C14) = 1.203(3) Â, d(04—C14) = 1.328(3) Â, d(04—C15) = 1.457(3) Â, d(C 1—C2) = 1.443(3) Â, d(C2—C3) = 1.348(3) Â, d(C3—C4) = 1.450(3) Â, d(C3—C14) = 1.503(3) Â; angles at the O atoms: 122.44(17)° at Ol and 114.55(18)° at 04) and are almost the same as m the previous reports [10,15,16]. The methyl group at 0 4 is approximately in the 04-C14-03 plane ( ¿ C 1 5 0 4 C 1 4 0 3 = -1.7(3)°) that agree well with a participation of 0 4 in the electron donation to the carbonyl group. The torsion angle Z.C4-C3-C14-03 = 99.1(3)° shows clearly that the carbonyl group (C 14-03) is approximatly perpendicular to the C4-C3-C14 plane, probably is as a result of steric intractions. π-π-Ring stacking is observed within the crystals, probably is as a result of the presence of parallel aromatic naphthalene rings in the crystal network that stabilize the crystal packing (lower figure). Table 1. Data collection and handling. Crystal: Wavelength: μDiffiractometer, scan mode: