Publication Date

3-1987

Abstract

Derivatives of 2-methyl-3,4-dihydro-2H,5H-pyrano[ 3,2-c][1]benzopyran-5-one. ( l) Racemic trans- 2-methoxy-4-(2-propyl), Mr= 288·3, monoclinic, P2i/c, a = 13·737 (3), b = 13·228 (6), c = 17·229(4) Å, β = l02·93(2)° , V = 3051·4 Å3, Z = 8 (two molecules/asymmetric unit), Dx = 1·255 g cm- 3, λ(Mo Kα) = O·71073 Å, μ = 0·908 cm-1 , F(OOO) = 1232, T = 298 K, final R = 0·050 for 3988 unique intensities. Dihydropyran rings in C17H2004 are halfchairs, one being distorted toward the d,e-diplanar form. (2) Resolved trans-2-methoxy-4-cyclohexyl, Mr = 328-4, orthorhombic, P212121, a = 10·468 (5), b = 11·245 (5). c = 14·465 (4) Å, V= 1702·7 Å3, Z=4, Dx= 1·281 g cm-3, λ(Mo Kα) = 0·71073 Å, μ = 0·823 cm- 1 , F(OOO) = 704, T = 298 K, final R = 0·051 for 2481 unique intensities. Compound, C20H2404, spontaneously resolves on crystallization from methanol: acetone; data specimen determined to be 2R,4R by circular dichroism spectrum and comparison with structures of known configuration. Dihydropyran ring has a d,e-diplanar conformation. (3) Racemic trans- 2-hydroxy-4-(2-propyl). Compound crystallizes as the hemihydrate C16H1804. ½H20; Mr= 283-3, triclinic, P1, a = 9·015 (4), b = 10·216 (4), c = 16·208 (5) Å, α = 103·08 (3), β = 95·42 (3), γ = 95·28 (3)° , V = 1437·6 Å3, Z = 4 (two molecules/asymmetric unit), Dx = 1·309 g cm-3 , λ(Mo Kα) = O·71073 Å, μ = 0·890 cm-1, F(OOO) = 604, T = 298 K, final R = 0·040 for 4656 unique reflections. One dihydropyran ring is a half-chair, the other has an ef-diplanar conformation. Intermolecular hydrogen bonding occurs between the water and the hydroxyls and lactone carbonyls of each coumarin with O···O distances between 2·82 and 2·90 Å. (4) Racemic trans-2-hydroxyl-4-(2-propyl) derivative also cocrystallizes with 4-hydroxy-2H-benzopyran- 2-one (1:1), Mr = 436·4, triclinic, P1, a= 8·669 (2), b = 10·506 (4), c = 12.559 (2) Å, α = 102·98 (2), β = 107·56 (2), γ = 93·63 (2)°, V = 1052·0 Å3, Z=2, Dx= 1·378g cm-3, γ(Mo Kα) = 0·71073 Å, μ = 0·941 cm-1, F(OOO) = 460, T = 298 K, final R = 0·041 for 3322 unique reflections. Cocrystalline C16H1804C9H603 shows chains of H bonds linking the hydroxyls of the coumarins alternately with the lactone carbonyls, O···O distances 2·68 and 2·75 Å. The dihydropyran ring has a half-chair conformation.

Subjects

Anticoagulants (Medicine); Pharmaceutical chemistry

Publication Information

View original published article on publisher's site. Valente, E. J., Eggleston, D. S. and Schomaker, V. (1987), Structures of four trans-2-hydroxy- and methoxy-2-methyl-3,4-dihydro-4-alkyl-2H,5H-pyrano[3,2-c][1]benzopyran-5-ones. Acta Cryst. C, 43: 533–536. doi: 10.1107/S0108270187095131.

DOI

10.1107/S0108270187095131

Document Type

Journal Article

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