Systematic Crystallographic Investigation of Hydrogen-Bonded Networks Involving Monohydrogen Tartrate−Amine Complexes: Potential Materials for Nonlinear Optics

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, C 12 H 18 O 6.5 N, P 22 1 2 1, a = 7.283(2) Å, b = 17.030(2) Å, c = 22.196(2) Å, Z = 8; 2,6-xylidinium- d -dibenzoyl monohydrogen tartrate, C 26 H 25 O 8 N, P 2 1, 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, C 26 H 26 O 8.5 N, P 2 1, 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, C 25 H 23 O 8 N, P 2 1 2 1 2 1, 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), C 25 H 23 O 8 N, P 1, 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), C 32 H 36 O 10 N, P 1, 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.