. 2022 Nov 8;78(Pt 12):730–742. doi: 10.1107/S2053229622010130

Table 2. Hydrogen-bond, C—H⋯(π ring) and π–π stacking interaction geometry (Å, °) for the crystal structures of p-sulfanilamide (B), o-sulfanilamide (D), o-nitrosulfonamides 1–3 and N-cycloamino-o-sulfanilamides 4–6 .

Compound	Interaction	D—H	H⋯A	D⋯A	D—H⋯A	π–π
o-Nitrosulfonamides
1	C11—H11A⋯O1ⁱ	0.99	2.56	3.398 (7)	143
	C11—H11B⋯O4	0.99	2.48	3.093 (9)	120
	C25—H25⋯O4ⁱⁱ	0.95	2.54	3.240 (2)	131
	C25—H25⋯O1ⁱⁱⁱ	0.95	2.47	3.229 (2)	137
	C26—H26⋯O2	0.95	2.49	2.860 (2)	103
	C26—H26⋯O3^iv	0.95	2.56	3.467 (2)	160
2	C11—H11A⋯O2	0.97	2.48	2.907 (2)	107
	C11—H11A⋯O2ⁱ	0.97	2.59	3.476 (2)	152
	C15—H15B⋯O1	0.97	2.51	2.943 (2)	107
	C25—H25⋯O2^v	0.93	2.57	3.334 (2)	140
	C26—H26⋯O1	0.93	2.53	2.877 (2)	103
3	C16—H16⋯O2	0.93	2.41	2.975 (2)	119
	C16—H16⋯O2^vi	0.93	2.55	3.195 (2)	127
	C23—H23⋯O1^vii	0.93	2.30	3.086 (3)	142
	C26—H26⋯N1	0.93	2.60	2.983 (2)	105
	Cg1⋯Cg2ⁱ					3.6967 (11)
	Cg2⋯Cg1ⁱ					3.6968 (11)

N-Cycloamino-o-sulfanilamides
4	N12—H12C⋯O21	0.78 (3)	2.40 (3)	3.121 (3)	155 (3)
	N12—H12D⋯O11	0.84 (3)	2.10 (3)	2.776 (3)	138 (3)
	N22—H21C⋯O11ⁱ	0.82 (3)	2.30 (3)	3.106 (2)	168 (2)
	N22—H21D⋯O21	0.87 (2)	2.07 (2)	2.783 (2)	139 (2)
	C114—H114⋯O22^viii	0.93	2.59	3.391 (3)	144
	C116—H116⋯O12	0.93	2.46	2.851 (2)	105
	C216—H216⋯O22′	0.93	2.52	2.897 (2)	105
5	N1—H1A⋯O1^ix	0.836 (19)	2.496 (19)	3.2999 (16)	161.8 (16)
	N1—H1B⋯O2	0.852 (16)	2.156 (16)	2.8240 (17)	135.1 (14)
	C16—H16⋯O1	0.95	2.48	2.8774 (15)	105
	C16—H16⋯O2^x	0.95	2.48	3.2577 (15)	139
	C21—H21A⋯O1	0.99	2.55	2.9635 (15)	105
	C25—H25B⋯O2	0.99	2.44	2.8675 (16)	106
6	N2—H2C⋯O2	0.86 (3)	2.19 (3)	2.857 (2)	134 (2)
	N2—H2D⋯O1^xi	0.89 (2)	2.22 (2)	3.098 (2)	168.8 (19)
	C15—H15⋯O2^xii	0.93	2.59	3.366 (2)	141
	C16—H16⋯O1	0.93	2.58	3.105 (2)	117
	C26—H26⋯O1	0.93	2.45	2.849 (2)	106
	C1—H1B⋯Cg1^xiii	0.97	2.97	3.817 (2)	147
	S1—O2⋯Cg2ⁱ			3.5773 (15)

Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + Inline graphic , y + , z − ; (iii) x + , −y + , z + ; (iv) x + , −y + , z − ; (v) x − , −y + , z + ; (vi) −x + 2, −y + 1, −z + 1; (vii) x + , −y + , z − ; (viii) −x + 2, y − , −z + ; (ix) x − , y, −z + Inline graphic ; (x) −x + , y − , z; (xi) x − , −y + , z − ; (xii) x − , −y + , z + . Centroids for 3: Cg1 N1/C1/C2/C12/C11; Cg2 C11–C16; Cg3 C21–C26; for 4: Cg1 C22–C27; for 5 Cg1 C11–C16; Cg2 N1/C2/C1/C12/C11; for 6 Cg1 C21–C26.

Table 2. Hydrogen-bond, C—H⋯(π ring) and π–π stacking inter­action geometry (Å, °) for the crystal structures of p-sul­fan­il­amide (B), o-sul­fan­il­amide (D), o-nitro­sul­fonamides 1–3 and N-cyclo­amino-o-sul­fan­il­amides 4–6 .

Table 2. Hydrogen-bond, C—H⋯(π ring) and π–π stacking interaction geometry (Å, °) for the crystal structures of p-sulfanilamide (B), o-sulfanilamide (D), o-nitrosulfonamides 1–3 and N-cycloamino-o-sulfanilamides 4–6 .