Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Table 4

Calculated structural parameters (bond lengths in Å, angles in degree) of the dyes 3a–3f.

Parameter	Dyes
	3a	3b	3c	3d	3e	3f
Bond lengths
C2-S24	1.759	1.759	1.759	1.759	1.759	1.759
S24-C7	1.781	1.780	1.781	1.781	1.781	1.781
C7-N23	1.290	1.290	1.290	1.290	1.290	1.290
C1-N23	1.388	1.388	1.388	1.388	1.388	1.388
C7-N22	1.389	1.390	1.389	1.389	1.389	1.389
N22-N25	1.405	1.405	1.405	1.405	1.404	1.404
C13-O21	1.229	1.229	1.229	1.229	1.229	1.229
C12-N27	1.307	1.306	1.309	1.308	1.310	1.311
N27-N19	1.319	1.321	1.317	1.318	1.319	1.317
N19-C16	1.381	1.380	1.382	1.382	1.382	1.382
C16-S18(N18)	1.771	1.773	1.774	1.772	1.371	1.371
C16-N26	1.294	1.294	1.294	1.295	1.310	1.310
S18(N18)-C17	1.763	1.761	1.762	1.763	1.391	1.391
N26-C15	1.386	1.385	1.385	1.386	1.389	1.389
Bond angles
S24-C7-N23	117.5	117.5	117.5	117.5	117.5	117.5
N23-C7-N22	124.4	124.3	118.1	124.4	118.1	118.1
C7-N22-N25	118.0	118.0	118.0	118.0	118.0	118.0
N25-C14-C12	110.4	110.3	110.4	110.4	110.4	110.5
N22-C13-O21	129.8	129.8	129.7	129.7	129.7	127.6
C13-C12-N27	127.2	127.1	127.1	127.2	127.0	127.0
N27-N19-C16	120.3	120.2	120.4	120.4	119.9	120.0
N19-C16-S18	120.8	120.6	120.8	120.8	121.9	121.9
C16-N26-C15	110.1	110.1	110.1	110.0	104.1	104.0
Torsion angles
S24-C7-N22-N25	0.0	0.0	0.0	0.0	0.0	0.0
N22-N25-C14-C28	180.0	180.0	180.0	180.0	180.0	180.0
O21-C13-C12-N27	0.0	0.0	0.0	0.0	0.0	0.0
N27-N19-C16-N26	180.0	180.0	180.0	180.0	180.0	180.0
N19-C16-N26-C15	180.0	180.0	180.0	180.0	180.0	180.0