Synthesis, characterization, X-ray structure, computational studies, and bioassay of novel compounds combining thiophene and benzimidazole or 1,2,4-triazole moieties

Mabkhot, Yahia N.; Al-Showiman, Salim S.; Soliman, Saied M.; Ghabbour, Hazem A.; AlDamen, Murad A.; Mubarak, Mohammad S.

doi:10.1186/s13065-017-0280-6

Table 3 The geometric parameters of both disorders, 2a and 2b (calculated and experimental)

From: Synthesis, characterization, X-ray structure, computational studies, and bioassay of novel compounds combining thiophene and benzimidazole or 1,2,4-triazole moieties

	DFT		Exp.		DFT		Exp.
	2a	2b	Exp.		2a	2b	Exp.
C21Br1(a)	–	1.917	1.897	C15–C14–C19	119.2	119.1	119.9
C8–Br1(b)	1.983	–	1.573	C15–C16–C17	120.3	120.2	120.0
O2–C11	1.228	1.228	1.225	C16–C17–C18	119.7	119.7	120.4
O3–C11	1.338	1.340	1.326	C17–C18–C19	120.1	120.2	119.9
O3–C12	1.452	1.451	1.460	C1–C2–C11	119.7	119.8	120.1
O1–C20	1.224	1.224	1.231	C1–C2–C3	112.3	112.2	112.7
N1–C1	1.350	1.354	1.360	C1–N1–C5	132.5	132.6	132.5
N1–C5	1.405	1.401	1.404	C1–S1–C4	91.4	91.3	91.2
S1–C1	1.736	1.736	1.726	C2–C11–O3	114.8	114.7	114.4
S1–C4	1.769	1.768	1.749	C2–C3–C14	123.9	124.4	123.9
C1–C2	1.419	1.416	1.391	C2–C3–C4	112.8	112.9	111.8
C2–C3	1.433	1.437	1.434	C3–C14–C15	120.9	120.4	121.3
C3–C4	1.382	1.378	1.373	C3–C14–C19	119.8	120.5	118.9
C2–C11	1.467	1.465	1.467	C3–C2–C11	128.0	128.0	126.6
C3–C14	1.493	1.493	1.486	C3–C4–C20	135.6	135.2	133.8
C4–C20	1.462	1.472	1.479	C4–C20–C21	121.7	121.3	120.4
C5–C6	1.401	1.401	1.393	C4–C3–C14	123.2	122.8	124.2
C5–C10	1.404	1.405	1.410	C5–C10–C9	120.6	121.1	120.7
C6–C7	1.393	1.392	1.382	C5–C6–C7	119.8	120.4	120.4
C7–C8	1.391	1.388	1.377	C6–C5–C10	119.0	118.6	118.6
C8–C9	1.395	1.393	1.392	C6–C7–C8	121.1	120.1	120.3
C9–C10	1.388	1.387	1.372	C7–C8–C9	119.1	120.5	120.4
C12–C13	1.514	1.514	1.502	C8–C9–C10	120.4	119.4	119.7
C14–C19	1.400	1.398	1.396	N1–C1–C2	123.7	123.5	123.2
C14–C15	1.397	1.398	1.384	N1–C5–C10	116.3	116.5	115.5
C15–C16	1.393	1.393	1.392	N1–C5–C6	124.7	124.9	125.9
C16–C17	1.393	1.394	1.374	O1–C20–C21	118.5	120.3	121.1
C17–C18	1.394	1.394	1.392	O1–C20–C4	119.8	118.4	118.6
C18–C19	1.393	1.392	1.386	O2–C11–C2	123.6	123.7	123.0
C20–C21	1.521	1.514	1.501	O2–C11–O3	121.6	121.6	122.6
N1–H–O2	1.798	1.796	1.934	O3–C12–C13	107.4	107.4	106.2
C6–H–S1	2.487	2.479	2.480	S1–C1–C2	111.7	111.7	111.9
Br1a–C21C20		–	126.3	S1–C1–N1	124.7	124.8	124.9
Br1–C8–C7	–	119.8	119.8	S1–C4–C20	112.5	112.9	113.7
Br1–C8–C9	–	119.7	119.9	S1–C4–C3	111.8	111.9	112.4
C11–O3–C12	116.5	116.6	116.6	θ_p1p2	70.0	73.6	89.5
C14–C15–C16	120.3	120.5	119.6	θ_p1p3	89.1	90.5	88.1
C14–C19–C18	120.4	120.5	119.8	θ_p2p3	19.1	16.9	3.3

θ the dihedral angle between two planes, p1 C14–C15–C16–C17–C18–C19, p2 S1–C1–C2–C3–C4, p3 C5–C6–C7–C8–C9–C10

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