Systematic crystallographic investigation of hydrogen-bonded networks involving monohydrogen tartrate-amine complexes: potential materials for nonlinear optics

Abstract

Crystal structures of six binary salts involving aromatic amines as cations and hydrogen tartrates as anions are presented. The materials are 2,6-xylidinium-L-monohydrogen tartrate monohydrate, C₁₂H₁₈O_6.5N, P22₁2₁, a = 7.283(2) Å, b = 17.030(2) Å, c = 22.196(2) Å, Z = 8; 2,6-xylidinium-D-dibenzoyl monohydrogen tartrate, C₂₆H₂₅O₈N, P2₁, a = 7.906(1) Å, b = 24.757(1) Å, c = 13.166(1) Å, β = 105.01(1)° , Z = 4; 2,3-xylidinium-D-dibenzoyl monohydrogen tartrate monohydrate, C₂₆H₂₆O_8.5N, P2₁, a = 7.837(1) Å, b = 24.488(1) Å, c = 13.763(1) Å, β = 105.69(1)°, Z = 4; 2-toluidinium-D-dibenzoyl monohydrogen tartrate, C₂₅H₂₃O₈N, P2₁2₁2₁, a = 13.553(2) Å, b = 15.869(3) Å, c = 22.123(2) Å, Z = 8; 3-toluidinium-D-dibenzoyl monohydrogen tartrate (1:1), C₂₅H₂₃O₈N, P1, a = 7.916(3) Å, b = 11.467(6) Å, c = 14.203(8) Å, α = 96.44(4)°, β = 98.20(5)°, = 110.55(5)°, Z = 2; 3-toluidinium-D-dibenzoyl tartrate dihydrate (1:2), C₃₂H₃₆O₁₀N, P1, a = 7.828(3) Å, b = 8.233(1) Å, c = 24.888(8) Å, α = 93.98° , β = 94.58(3)° , = 89.99(2)° , Z = 2. An analysis of the hydrogen-bonding schemes in terms of crystal packing, stoichiometric variations, and substitutional variations in these materials provides insights to design hydrogen-bonded networks directed toward the engineering of crystalline nonlinear optical materials.