SYSTEMATIC CRYSTALLOGRAPHIC INVESTIGATION OF HYDROGEN-BONDED NETWORKSINVOLVING MONOHYDROGEN TARTRATE-AMINE COMPLEXES - POTENTIAL MATERIALSFOR NONLINEAR OPTICS

Crystal structures of six binary salts involving aromatic amines as ca tions and hydrogen tartrates as anions are presented. The materials ar e 2,6-xylidinium-L-monohydrogen tartrate monohydrate, C12H18O6.5N, P22 (1)2(1), a = 7.283(2) Angstrom, b = 17.030(2) Angstrom, c = 22.196(2) Angstrom, Z = 8; 2,6-xylidinium-D-dibenzoyl monohydrogen tartrate, C26 H25O8N, P2(1), a = 7.906(1) Angstrom, b = 24.757(1) Angstrom, c = 13.1 66(1) Angstrom, beta = 105.01(1)degrees, Z = 4; 2,3-xylidinium-D-diben zoyl monohydrogen tartrate monohydrate, C26H26O8.5N, P2(1), a = 7.837( 1) Angstrom, b = 24.488(1) Angstrom, c = 13.763(1) Angstrom, beta = 10 5.69(1)degrees, Z = 4; 2-toluidinium-D-dibenzoyl monohydrogen tartrate , C25H23O8N, P2(1)2(1)2(1), a = 13.553(2) Angstrom, b = 15.869(3) Angs trom, c = 22.123(2) Angstrom, Z = 8; 3-toluidinium-D-dibenzoyl monohyd rogen tartrate (1:1), C25H23O8N, P1, a = 7.916(3) Angstrom, b = 11.467 (6) Angstrom, c = 14.203(8) Angstrom, alpha = 96.44(4)degrees, beta = 98.20(5)degrees, = 110.55(5)degrees, Z = 2; 3-toluidinium-D-dibenzoyl tartrate dihydrate (1:2), C32H36O10N, P1, a = 7.828(3) Angstrom, b = 8 .233(1) Angstrom, c = 24.888(8) Angstrom, alpha = 93.98 degrees, beta = 94.58(3)degrees, = 89.99(2)degrees, Z = 2. An analysis of the hydrog en-bonding schemes in terms of crystal packing, stoichiometric variati ons, and substitutional variations in these materials provides insight s to design hydrogen-bonded networks directed toward the engineering o f crystalline nonlinear optical materials.