TABLE 2.

Hydrogen bond and intermolecular interaction geometries (Å, °) for compounds 1–3

D—H···A	D—H	H···A	D···A*	∠D—H···A
1
N10—H101···O9i	0.85	1.98	2.825 (6)	172
N32—H321···O31ii	0.88	2.00	2.879 (6)	179
C20—H201···C33iii	0.93	2.79	3.620 (6)	149
C16—H161···O9i	0.92	2.65	3.370 (4)	136
C13—H131···O7iii	0.93	2.26	2.932 (6)	129
C35—H351···O29iv	0.93	2.32	2.959 (6)	126
C27—H273···π v	―	2.919	―	149
H351 … H361	―	―	2.319	―
H371 … H381	―	―	2.325	―
2
N5—H51···O14i	0.84 (1)	1.94 (1)	2.771 (2)	177 (1)
N15—H151···O26	0.85 (1)	1.99 (1)	2.819 (2)	165 (1)
C21—H211···O26	0.94	2.51	3.235 (2)	134
C22—H221···O14i	0.93	2.60	3.321 (2)	135
C10—H101···Cl2ii	0.94	2.86	3.509 (1)	128
C29—H291···N7iii	0.95	2.69	3.481 (2)	140
C20—H201···C10iv	0.95	2.78	3.636 (2)	151
C27—H271···C19v	0.94	2.71	3.623 (2)	164
C25—H251···C22vi	0.93	2.85	3.327 (1)	114
C30—H303···π i	―	2.974	―	126
π… π iv	―	―	3.7837 (8)	―
3
N9—H91···Cl2i	0.86 (2)	2.83 (2)	3.476 (2)	133 (2)
C12—H121···Cl2ii	0.92	2.942	3.638 (2)	133.3
C5—H51···π iii	―	2.814	―	135
C5—H51···π iii	―	3.401	―	126
π···π iv	―	―	3.860 (2)	―

Note: Symmetry transformations used to generate equivalent atoms for 1: (i) −x, −y + 1, −z; (ii) –x + 1, −y + 3, −z + 1; (iii) −x, −y + 2, −z; (iv) –x + 1, −y + 2, −z + 1; (v) x, y, z + 1; for 2: (i) –x + 1, −y + 1, −z + 1; (ii) –x + 2, −y, −z + 1; (iii) x, y + 1, z; (iv) –x + 2, −y + 1, −z + 1; (v) x + $\frac{1}{2}$, −y + $\frac{3}{2}$, z + $\frac{1}{2}$; (vi) −x + $\frac{3}{2}$, y − $\frac{1}{2}$, −z + $\frac{3}{2}$; for 3: (i) x – $\frac{1}{2}$, y + $\frac{1}{2}$, z; (ii) –x + 1, y, −z + $\frac{1}{2}$; (iii) x – $\frac{1}{2}$, y ‐ $\frac{1}{2}$, z; (iv) –x + 1, −y + 1, −z + 1.*For π … π interactions d(D…A) = Cg … Cg and for C–H … π interactions d(H….A) = H … Cg and ∠D—H···A = ∠D—H···Cg, where Cg = centroid of the aromatic phenyl (for 1), pyridine (for 2) or pyrazole (for 3) rings.