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The asymmetric unit of the title compound, C20H18N2O2, contains two independent mol­ecules in which the dihedral angles between the naphthalene ring system [r.m.s. deviations = 0.012 (1) and 0.015 (1) Å] and the benzene ring are 71.65 (6) and 74.51 (6)°. In the crystal, pairs of N—H...O hydrogen bonds form two independent inversion dimers with graph-set notation R22(14). In addition, each mol­ecule contains an intra­molecular O—H...N hydrogen bond with an S(6) motif.

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In the structure of the title compound, C12H12O3, the di­hydro­pyran ring is fused with the benzene ring. The di­hydro­pyran ring is in a half-chair conformation, with the ring O and methyl­ene C atoms positioned 1.367 (3) and 1.504 (4) Å, respectively, on either side of the mean plane formed by the other four atoms. The meth­oxy group is coplanar with the benzene ring to which it is connected [Cb—Cb—Om—Cm torsion angle = −0.2 (4)°; b = benzene and m = meth­oxy], and similarly the aldehyde is coplanar with respect to the double bond of the di­hydro­pyran ring [Cdh—Cdh—Ca—Oa = −178.1 (3)°; dh = di­hydro­pyran and a = aldehyde]. In the crystal, mol­ecules are linked by weak meth­yl–meth­oxy C—H...O hydrogen bonds into supra­molecular chains along the a-axis direction.

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In the title compound, C17H14O5, the dimeth­oxy-substituted benzene ring is twisted relative to the 4H-chromenon skeleton (r.m.s. deviation = 0.015 Å) by 5.2 (4)°. The C atoms of the meth­oxy groups lie close to the plane of their attached benzene ring [deviations = 0.036 (3) and 0.290 (3)Å for the meta and para substituents, respectively]. An intra­molecular O—H...O hydrogen bond closes an S(5) ring. In the cystal, inversion dimers linked by pairs of O—H...O hydrogen bonds generate R22(10) loops and C—H...O inter­actions connect the dimers into [010] chains.

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In the title compound, C21H18O4, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 6.60 (2)°. The meth­oxy groups on the benzene ring are essentially coplanar with the ring; the C—C—O—C torsion angles being 1.6 (2) and −177.1 (1)°. The hy­droxy group attached to the naphthalene ring is involved in an intra­molecular O—H...O hydrogen bond. The relative conformation of the two double bonds in the enone group is s-cisoid. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules into chains propagating along [010].
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