FT-IR, Laser-Raman, UV-Vis, and NMR Spectroscopic Studies of Antidiabetic Molecule Nateglinide

Table 3

The optimized molecular geometric parameters of nateglinide.

Bond lengths (Å)	X-ray [27]	Values	Bond lengths (Å)	X-ray [27]	Values	Bond angles (°)	Values	X-ray [27]	Bond angles (°)	Values	X-ray [27]
C11-C13	1.352	1.398	C24-C25	1.495	1.530	C11-C13-H14	120.102	119.116	C25-C38-C35	111.408	110.700
C13-C15	1.413	1.395	C25-C38	1.537	1.546	C15-C13-H14	119.705	119.160	C38-C35-C33	112.186	112.617
C9-C11	1.360	1.396	C35-C38	1.524	1.537	C9-C11-H12	120.254	120.606	C35-C33-C30	109.752	110.312
C7-C9	1.404	1.398	C33-C35	1.527	1.542	C13-C11-H12	120.199	120.467	C33-C30-C27	112.163	112.776
C7-C17	1.374	1.401	C33-C30	1.522	1.542	C13-C15-H16	119.437	120.306	H28-C27-H29	107.285	108.188
C15-C17	1.392	1.403	C27-C30	1.527	1.539	C11-C9-H10	120.189	119.550	C27-C25-H26	108.092	106.800
C17-C18	1.524	1.514	C25-C27	1.532	1.539	C17-C15-H16	119.745	120.288	H39-C38-H40	107.036	108.165
C18-C21	1.526	1.558	C33-C41	1.542	1.554	C7-C9-H10	119.774	119.650	C35-C33-H34	106.915	106.334
C21-C23	1.522	1.525	C41-C47	1.493	1.539	C17-C7-H8	119.457	119.513	H37-C35-H36	106.559	107.896
C23=O1	1.231	1.213	C41-C43	1.543	1.539	C17-C18-H20	110.141	108.536	H31-C30-H32	106.523	107.730
C23=O2	1.308	1.353	C24=O4	1.252	1.230	C17-C18-H19	109.619	108.510	C33-C41-H42	105.779	106.849
O2-H3	0.909	0.973	N5-H6	0.927	1.010	C21-C18-H19	108.662	108.488	H44-C43-H45	107.793	109.495
C21-N5	1.460	1.447	C24=N5	1.332	1.372	C21-C18-H20	107.531	108.534	C41-C43-H46	110.750	109.459
Dihedral angles (°)						C23-C21-H22	108.860	107.886	H42-C41-C47	107.149	106.767
H10-C9-C7-C17		179.820		179.844		N5-C21-H22	106.696	107.947	C41-C47-H50	111.618	109.518
H10-C9-C11-C13		−179.816		178.624		C24-N5-H6	119.107	121.393	H49-C47-H48	107.337	109.401
H16-C15-C13-C11		−179.772		178.229		C23-O2-H3	107.493	106.777	C25-C24-O4	120.642	121.732
C9-C7-C17-C18		−179.489		−179.882		O4-C24-N5	121.982	119.602	C24-C25-C27	117.171	116.594
C21-C23-O2-H3		−177.502		178.064		O1-C23-O2	122.883	124.478	C24-C25-C38	109.582	109.451
C21-N5-C24-C25		−174.757		−170.842		N5-C24-C25	117.375	118.654	C25-C27-C30	110.933	109.665
C25-C38-C35-H36		−65.703		−65.679

[27] L. Tessler, I. Goldberg., bis(nateglinide) hydronium chloride, and its unique self-assembly into extended polymeric arrays via O-H⋯O, N-H⋯Cl, and O-H⋯Cl hydrogen bonds. Acta Cryst. C61 (2005) 738–740.