Table 3.

Selected host–guest interactions in the β-CD–PRT and β-CD–MPL inclusion complexes deduced from X-ray analysis and DFT full-geometry optimization (Å, °).

Interaction a	D–H	H···A	D···A	∠(DHA)	Interaction a	D–H	H···A	D···A	∠(DHA)
X-ray					DFT e
β-CD–PRT HCl (1)					β-CD–PRT base
N5’P–H1···O21 i,b	0.89	2.41	3.087(10)	133.1	C52–H···Cg2 c	1.10	3.75	4.80	162.2
N5’P–H1···O31 i	0.89	2.06	2.856(11)	148.6	C55–H···Cg2	1.10	4.61	3.56	161.6
N5’P–H1···O21 i	0.89	2.41	3.087(10)	133.1	C31–H···Cg1 c	1.10	4.49	3.46	157.1
C51–H···Cg2 c	0.98	3.69	4.461	137.8
C55–H···Cg2	0.98	3.39	4.239	146.3
C32–H···Cg1	0.98	3.21	4.135	158.9
β-CD–MPL HCl (2)					β-CD–MPL base
O61–H···N5’M ii,b	0.82	2.44	3.159(12)	146.4	C51–H···Cg1 c	1.10	3.93	4.98	160.7
N5’M–H1···O52 iii	0.89	2.50	3.141(8)	129.2	C31–H···Cg2 c	1.10	3.37	4.30	143.5
N5’M–H1···O62 iii	0.89	2.10	2.930(11)	155.7
N5’M–H2···O61 iii	0.89	2.60	3.159(12)	121.7
C51–H···Cg1 d	0.98	3.577	4.515	161.1
C55–H···Cg1	0.98	3.843	4.782	161.4
C31–H···Cg2	0.98	3.018	3.903	150.9
O21–H···Cg2	0.82	4.394	4.499	92.1
O37–H···Cg2	0.82	3.930	4.520	132.0

^a For full lists of intermolecular interactions, see Table S4, Table S5 (X-ray), and Table S6 (DFT). ^b Symmetry-related molecules with equivalent positions: ⁽ⁱ⁾ −x + 1, y − 0.5, −z + 2; ⁽ⁱⁱ⁾ −x + 1, y − 0.5, −z + 1.5; ⁽ⁱⁱⁱ⁾ −x + 1, y + 0.5, −z + 1.5. ^c PRT aromatic centroids: Cg1 = A-ring (C1P−C2P−C3P−C4P−C13P−C12P), Cg2 = B-ring (C6P–C7P–C8P–C9P–C15P–C14P). ^d MPL aromatic centroids: Cg1 = A-ring (C1M−C2M−C3M−C4M−C13M−C12M), Cg2 = B-ring (C6M−C7M−C8M−C9M−C15M−C14M). ^e For stabilization and interaction energies, see Table S7.