Crystal Forms of the Antiepileptic Lamotrigine: Molecular Salts and Solvates with Fluorobenzoic Acid, Nicotinic Acid, 2-Thiobarbituric Acid, 3-Picoline and Butyl Alcohol

Author： Sridhar B. Ravikumar K.

Publisher： Springer Publishing Company

ISSN： 1074-1542

Source： Journal of Chemical Crystallography, Vol.41, Iss.9, 2011-09, pp. : 1289-1300

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Abstract

The crystal structures of three salts and two solvated multicomponent crystals of lamotrigine with 4-fluorobenzoic acid, nicotinic acid, 2-thiobarbituric acid, 3-picoline and butyl alcohol are reported. Compound 1a crystallizes in monoclinc system, space group P2₁ with a = 13.3860(5) Å, b = 8.3420(3) Å, c = 15.5200(6) Å, β = 93.524(1)°, V = 1729.78(11) Å³, and Z = 2. Compound 1b crystallizes in monoclinic system, space group P2₁/c with a = 10.6625(7) Å, b = 16.2575(11) Å, c = 13.6346(9) Å, β = 100.904(1)°, V = 2320.8(3) Å³, and Z = 4. Compound 1c crystallizes in triclinic system, space group P $$ overline{1} $$ , with a = 10.1309(7) Å, b = 12.0260(8) Å, c = 14.0826(10) Å, α = 71.783(1)°, β = 86.451(1)°, γ = 80.902(1)°, V = 1609.10(19) Å³, and Z = 1. Compound 1d crystallizes in monoclinic system, space group P2₁/c with a = 14.9570(10) Å, b = 8.0230(6) Å, c = 13.8162(10) Å, β = 102.884(1)°, V = 1616.2(2) Å³, and Z = 4. Compound 1e crystallizes in triclinic system, space group P $$ overline{1} $$ , with a = 7.5710(6) Å, b = 8.5721(7) Å, c = 13.5532(11) Å, α = 85.364(1)°, β = 79.632(1) (1)°, γ = 86.188(1)°, V = 861.19(12) Å³, and Z = 2. Characteristic R ₂² (8) dimer is observed in all five structures. A complete hydrogen bonded motif analysis is described. Lamotrigine-lamotrigine base pair is observed in all the structures, except in (1b). In (1c), the R ₂² (7) dimer is noticed while, in all other structures R ₂² (8) dimer exist between the lamotrigine-lamotrigine base pair. In all the six structures, chlorine atoms of the lamotrigine molecules are not involved in any interactions.In the present study we have described the crystal structure and conformation of lamotrigine with three salts viz., fluorobenzoic acid, nicotinic acid and 2-thiobarbituric acid and also with two solvates viz., 3-picoline and butyl alcohol.