Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins.

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3 N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology.

(2R)-2-(1,3-Dioxoisoindolin-2-yl)-3-methyl-butanoic acid.

In the title compound, C(13)H(13)NO(4), the dihedral angle between the nine-membered phthalimino ring system and the carb-oxy-lic acid group is 67.15 (9)°. An intra-molecular C-H⋯O close contact, which forms an S(6) ring, may help to establish the mol-ecular conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, thereby forming C(7) chains propagating in [010].

Methyl 2-methyl-3,5-dinitro-benzoate.

In the title compound, C(9)H(8)N(2)O(6), the methyl ester group is almost planar (r.m.s. deviation = 0.002 Å) and is oriented at a dihedral angle of 24.27 (16)° with respect to the benzene ring. The nitro groups make dihedral angles of 4.2 (5)° and 60.21 (11)° with the benzene ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, resulting in zigzag chains.

Poly[[µ(3)-chlorido-bis(µ(2)-thio-urea-κS)disilver(I)] nitrate].

The mol-ecular structure of the title polymeric complex, {[Ag(2)Cl(CH(4)N(2)S)(2)]NO(3)}(n), consists of a binuclear cationic complex and a nitrate counter-ion. The cationic complex contains two bridging thio-urea (Tu) ligands and a triply bridging µ(3)-Cl anion. The latter is probably released from 2-amino-ethane-thiol hydro-chloride during the synthesis. The coordination environment around the two Ag(I) atoms is different; one is trigonal planar, being coordinated by two thio-urea ligands through the S atoms and to one Cl(-) ion, while in the other the Ag(I) atom is tetra-hedrally coordinated by two thio-urea ligands through the S atoms and to two Cl(-) ions. These units aggregate through the Cl(-) anion and the Tu S atoms, forming a chain propagating in [100]. In the crystal structure, the polymeric chains are linked via N-H⋯O and N-H⋯Cl hydrogen bonds, forming a double layer two-dimensional network propagating in (011).

2-(2-Oxothio-lan-3-yl)isoindoline-1,3-dione.

In the title compound, C(12)H(9)NO(3)S, the isoindoline-1,3-dione group is almost planar, with an r.m.s. deviation of 0.020 Å, whereas the heterocyclic ring approximates to an envelope with the methyl-ene group not adjacent to the S atom in the flap position. A short intra-molecular C-H⋯O contact generates an S(6) ring motif. In the crystal structure, weak aromatic π-π stacking inter-actions occur between the centroids of the benzene rings at a distance of 3.558 (2) Å.

2-(1,3-Dioxoisoindolin-2-yl)propanoic acid.

The crystal structure of the title compound, C(11)H(9)NO(4), consists of infinite one-dimensional polymeric chains due to inter-molecular O-H⋯O hydrogen bonds between the carboxyl-ate and carbonyl groups. The phthalimide ring system and the C-COO group are planar, with r.m.s. deviations of 0.0253 and 0.0067 Å, respectively, from their mean square planes and the dihedral angle between them is 66.41 (7)°. The mol-ecules are stabilized by C=O⋯π inter-actions and weak intra-molecular C-H⋯O hydrogen bonds.

2-Methyl-3,5-dinitro-benzoic acid.

In the title compound, C(8)H(6)N(2)O(6), the O atoms of the nitro groups, the methyl H atoms and the carboxyl C=O and C-OH groups are disordered over two sets of sites with an occupancy ratio of 0.595 (16):0.405 (16). In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds arise for both carboxyl disorder components and C-H⋯O bonds and weak C-H⋯π inter-actions consolidate the packing.

(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methyl-sulfan-yl)butanoic acid.

The title compound, C(13)H(13)NO(4)S, the 1,3-dioxoisoindolin-2-yl unit is planar (r.m.s. deviation 0.0192 Å) and is oriented at a dihedral angle of 79.14 (18)° to the carboxyl-ate group. An intra-molecular C-H⋯O hydrogen bond leads to the formation of a planar (r.m.s. deviation 0.0419 Å)R(5) ring motif. In the crystal, mol-ecules are connected through O-H⋯O and C-H⋯O hydrogen bonds with R(2) (2)(9) ring motifs into chains extending along the b axis.