Theoretical Investigations on Inclusion of P-Xylylenediammonium and 1,6-Hexyldiammonium

Encapsulation of alkyl and aryl derivatives of quaternary ammonium cations within Cucurbit[n]uril(n=6,7) and their inverted diastereomers: Density Functional Investigations

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Ishita A. Rajaa, Vivekanand V. Gobreb, Rahul V. Pinjaric, Shridhar P. Gejjia,*

a Department of Chemistry, University of Pune, Ganeshkhind, Pune 411007 India.

bFritz Haber Institute of the Max Planck Society,Faradayweg 4-6, D-14195 Berlin-Dahlem,Germany.

cSchool of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded 431606 India.

Supporting Information

1)Optimized geometries of the inclusion complexes of HDA guest within the CB[n] and iCB[n] (n=6,7) host cavity. (Fig. 1S)

2)Optimized geometries of the inclusion complexes of XYL guest within the CB[n] and iCB[n] (n=6,7) host cavity. (Fig. 2S)

3)Vibrational spectra of the minimum energy host-guest(HDA) complexes. (Fig. 3S)

4)Vibrational spectra of minimum energy host-guest(XYL) complexes. (Fig. 4S)

5)1H NMR chemical shifts of the host protons in the CB[n]-HDA (Table 2S) and iCB[n]-HDA (Table 3S) complexes.

6)1H NMR chemical shifts of the host protons in the CB[n]-XYL (Table 4S) and iCB[n]-XYL (Table 5S) complexes.

7)Hydrogen bond distances (in Ǻ) from different functional in complexes of CB[6] and iCB[6] (Table 6S).

8)superimposed structures of CB[6]-HDA as well as iCB[6]-XYL from the B97D and M06-2X functionals based DFT optimizations (Fig. 5S).

Fig.1S(a) Optimized geometries of the inclusion complexes of HDA guest within the CB[6] host cavity.

CB[6]-HDA-A / CB[6]- HDA-C

Fig. 1S(b) Optimized geometries of the inclusion complexes of HDA guest within the iCB[6] host cavity.

iCB[6]- HDA-A / iCB[6]- HDA-C

Fig.1S(c) Optimized geometries of the inclusion complexes of HDA guest within the CB[7] host cavity.

CB[7]-HDA-A / CB[7]-HDA-B
CB[7]-HDA-C

Fig.1S(d) Optimized geometries of the inclusion complexes of HDA guest within the iCB[7] host cavity.

iCB[7]-HDA-A / iCB[7]-HDA-B
iCB[7]-HDA-C

Fig. 2S(a) Optimized geometries of the inclusion complexes of XYL guest within the CB[6] host cavity.

CB[6]-XYL-A / CB[6]-XYL-B

Fig. 2S(b)Optimized geometries of the inclusion complexes of XYL guest within the iCB[6] host cavity.

iCB[6]-XYL-A / iCB[6]-XYL-C

Fig. 2S(c)Optimized geometries of the inclusion complexes of XYL guest within the CB[7] host cavity.

CB[7]-XYL-A / CB[7]-XYL-C

Fig. 2S(d) Optimized geometries of the inclusion complexes of XYL guest within the iCB[7] host cavity.

iCB[7]-XYL-A / iCB[7]-XYL-C

Fig. 3S(1) Vibrational spectra of the minimum energy host-guest(HDA) complexes.

(a) /
(b) /
Fig. 3S(1) cont
(c) /
(d) /

Fig. 3S(1) cont
(e)

CB[6]-HDA-A

Fig. 3S(2) Vibrational spectra of the minimum energy host-guest(HDA) complexes.

(a)
(b)

Fig. 3S(2) cont

(e)
iCB[6]-HDA-A

Fig. 3S(3) Vibrational spectra of the minimum energy host-guest(HDA) complexes.

(a) /
(b) /
Fig. 3S(3) cont
(c) /
(d) /

Fig. 3S(3) cont

(e)

CB[7]-HDA-A

Fig. 3S(4) Vibrational spectra of the minimum energy host-guest(HDA) complexes.

(a) /
(b) /
Fig. 3S(4)cont
(c) /
(d) /
Fig. 3S(4)cont

(e)

iCB[7]-HDA-A

Fig. 4S(1) Vibrational spectra of the minimum energy host-guest(XYL) complexes.

(a) /
(b) /
Fig. 4S(1) cont
(c) /
(d) /
Fig. 4S(1) cont

(e)

CB[6]-XYL-A

Fig. 4S(2)Vibrational spectra of the minimum energy host-guest(XYL) complexes.

(a) /
(b) /

Fig. 4S(2) cont

Fig. 4S(3) Vibrational spectra of the minimum energy host-guest(XYL) complexes.

(a) /
(b) /

Fig. 4S(3) cont

CB[7]-XYL-A
Fig. 4S(4) Vibrational spectra of the minimum energy host-guest(XYL) complexes.

(a) /
(b) /
Fig. 4S(4) cont
(c) /
(d) /

Fig. 4S(4) cont

(e) /
iCB[7]-XYL-A

Table 2S NMR chemical shifts of the host protons in the CB[n]-HDA complexes and chemical shifts in water (SCRF-PCM) are given in bold.

CB[6] / CB[6]-HDA-A / CB[7] / CB[7]-HDA-A
H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3
6.3 / 5.6 / 3.4 / 3.9 / 4.7 / 5.1 / 6.1 / 5.6 / 3.6 / 4.0 / 4.9 / 5.0 / 6.3 / 5.7 / 3.5 / 3.9 / 4.8 / 5.0 / 6.2 / 5.9 / 3.6 / 3.9 / 4.9 / 5.1
6.1 / 5.8 / 3.2 / 3.7 / 4.7 / 5.0 / 5.9 / 5.8 / 3.8 / 3.9 / 4.9 / 5.1 / 6.4 / 5.7 / 3.2 / 3.7 / 4.7 / 5.0 / 6.3 / 5.9 / 3.7 / 4.0 / 4.8 / 5.2
6.3 / 5.8 / 3.2 / 3.8 / 4.7 / 5.0 / 5.9 / 5.7 / 3.7 / 4.1 / 4.9 / 5.1 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 4.9 / 5.9 / 5.6 / 3.5 / 3.8 / 4.6 / 5.2
6.3 / 5.8 / 3.5 / 3.9 / 4.8 / 5.0 / 5.9 / 5.7 / 3.8 / 4.1 / 4.9 / 5.1 / 6.3 / 5.8 / 3.3 / 3.9 / 4.6 / 4.9 / 6.2 / 5.7 / 3.6 / 3.9 / 4.7 / 5.1
6.3 / 5.8 / 3.3 / 3.8 / 4.7 / 5.1 / 5.9 / 6.0 / 3.7 / 3.9 / 4.9 / 5.1 / 6.2 / 5.8 / 3.1 / 3.8 / 4.5 / 5.0 / 6.3 / 5.7 / 3.8 / 4.1 / 5.0 / 5.2
6.3 / 5.8 / 3.3 / 4.0 / 4.7 / 5.1 / 6.1 / 5.8 / 3.6 / 4.0 / 4.9 / 5.0 / 6.2 / 5.7 / 3.5 / 3.8 / 4.6 / 5.0 / 6.0 / 5.7 / 3.4 / 3.9 / 5.0 / 5.0
6.3 / 5.8 / 3.4 / 3.7 / 4.7 / 5.1 / 6.3 / 5.8 / 3.6 / 3.9 / 4.8 / 5.0 / 6.2 / 5.8 / 3.3 / 3.8 / 4.6 / 5.2 / 6.3 / 5.7 / 3.7 / 3.8 / 4.9 / 5.2
6.1 / 5.8 / 3.2 / 3.9 / 4.7 / 5.0 / 6.2 / 5.8 / 3.7 / 3.9 / 5.0 / 5.1 / 6.4 / 5.9 / 3.4 / 4.0 / 4.6 / 5.1 / 5.8 / 5.8 / 3.7 / 4.2 / 5.0 / 5.1
6.3 / 5.6 / 3.2 / 3.7 / 4.7 / 5.0 / 6.2 / 5.8 / 3.6 / 4.0 / 5.0 / 5.1 / 6.3 / 5.8 / 3.5 / 4.0 / 4.7 / 5.1 / 6.1 / 5.7 / 3.5 / 3.8 / 4.8 / 5.2
6.3 / 5.8 / 3.5 / 3.8 / 4.8 / 5.0 / 6.2 / 6.0 / 3.6 / 3.9 / 4.8 / 5.1 / 6.4 / 5.8 / 3.3 / 3.7 / 4.7 / 5.1 / 6.0 / 5.7 / 3.9 / 4.2 / 4.8 / 5.2
6.3 / 5.8 / 3.3 / 3.9 / 4.7 / 5.1 / 6.2 / 5.8 / 3.7 / 3.9 / 4.9 / 5.1 / 6.4 / 5.7 / 3.2 / 3.9 / 4.7 / 5.0 / 6.0 / 5.8 / 3.9 / 3.9 / 4.9 / 5.2
6.3 / 5.8 / 3.3 / 3.8 / 4.7 / 5.1 / 6.3 / 5.6 / 3.6 / 4.0 / 4.9 / 5.0 / 6.3 / 5.7 / 3.5 / 3.8 / 4.7 / 5.1 / 6.0 / 5.6 / 3.4 / 3.9 / 4.7 / 5.2
6.2 / 5.8 / 3.2 / 3.7 / 4.6 / 5.2 / 5.9 / 5.8 / 3.8 / 4.1 / 5.1 / 4.9
6.3 / 5.8 / 3.4 / 4.0 / 4.6 / 5.3 / 6.2 / 5.8 / 3.6 / 3.7 / 4.8 / 4.9

Table 3SNMR chemical shifts of the host protons in the iCB[n]-HDA complexes and chemical shifts in water (SCRF-PCM) are given in bold.

iCB[6] / iCB[6]-HDA-A / iCB[7] / iCB[7]-HDA-A
H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3
i / 4.3 / 4.8 / 4.2 / 4.6 / 4.8 / 5.0 / 4.2 / 4.5
i / 4.5 / 5.0 / 5.1 / 5.0 / 4.7 / 4.9 / 4.6 / 4.8
α / 6.0 / 5.5 / 4.0 / 4.0 / 4.9 / 5.2 / 5.6 / 5.4 / 4.2 / 4.3 / 5.3 / 5.4 / 5.7 / 5.4 / 3.7 / 3.9 / 4.9 / 5.2 / 5.9 / 5.6 / 3.7 / 4.3 / 5.1 / 5.0
α / 5.6 / 5.6 / 3.9 / 4.3 / 5.1 / 5.2 / 5.6 / 5.5 / 4.2 / 4.4 / 5.1 / 5.3 / 5.9 / 5.6 / 4.1 / 4.3 / 4.7 / 5.1 / 5.5 / 5.6 / 4.4 / 4.2 / 4.9 / 5.1
α / 5.7 / 5.5 / 4.1 / 4.3 / 4.8 / 5.3 / 5.9 / 5.8 / 4.3 / 4.6 / 5.3 / 5.5 / 5.7 / 5.4 / 3.8 / 4.1 / 4.6 / 5.1 / 5.7 / 5.6 / 4.2 / 3.9 / 4.7 / 5.2
α / 5.8 / 5.4 / 3.7 / 4.0 / 4.8 / 5.4 / 5.9 / 5.7 / 4.2 / 4.5 / 5.2 / 5.4 / 5.8 / 5.6 / 3.6 / 3.8 / 4.6 / 4.9 / 6.0 / 5.4 / 4.1 / 4.4 / 5.0 / 5.0
β / 6.2 / 5.7 / 3.3 / 3.7 / 4.7 / 5.1 / 6.0 / 5.7 / 3.8 / 4.0 / 5.1 / 5.2 / 6.3 / 5.7 / 3.2 / 3.8 / 4.8 / 5.3 / 6.1 / 5.7 / 3.8 / 4.1 / 4.9 / 5.2
β / 6.2 / 5.9 / 3.5 / 4.1 / 4.7 / 5.1 / 6.1 / 5.8 / 3.9 / 4.1 / 5.1 / 5.3 / 6.3 / 5.8 / 3.5 / 4.0 / 4.9 / 5.3 / 6.0 / 5.8 / 3.6 / 3.8 / 4.7 / 5.0
β / 6.2 / 5.8 / 3.3 / 3.9 / 4.8 / 5.0 / 6.1 / 5.7 / 3.6 / 3.8 / 5.3 / 5.5 / 6.3 / 5.8 / 3.5 / 3.9 / 4.7 / 5.1 / 5.7 / 5.9 / 3.6 / 3.9 / 4.9 / 5.3
β / 6.3 / 5.8 / 3.3 / 4.0 / 4.8 / 5.0 / 6.0 / 5.6 / 3.6 / 3.7 / 5.1 / 5.3 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 5.1 / 6.2 / 5.8 / 3.7 / 3.9 / 4.8 / 5.1
γ / 6.3 / 5.9 / 3.4 / 3.9 / 4.7 / 5.1 / 5.9 / 5.7 / 3.7 / 4.1 / 4.9 / 5.2 / 6.3 / 5.8 / 3.4 / 3.9 / 4.8 / 5.2 / 6.3 / 5.5 / 3.6 / 3.9 / 5.1 / 5.3
γ / 6.4 / 5.8 / 3.3 / 3.9 / 4.7 / 5.1 / 6.3 / 5.7 / 3.5 / 3.8 / 4.9 / 5.2 / 6.4 / 5.8 / 3.4 / 4.0 / 4.8 / 5.2 / 6.0 / 5.8 / 3.6 / 4.0 / 4.9 / 5.1
γ / 6.3 / 5.7 / 3.3 / 3.9 / 6.1 / 5.8 / 3.6 / 3.9 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 5.0 / 5.9 / 5.7 / 3.8 / 4.0 / 4.8 / 5.0
γ / 6.2 / 5.9 / 3.4 / 3.8 / 6.2 / 5.7 / 3.6 / 4.0 / 6.3 / 5.7 / 3.3 / 3.8 / 4.6 / 5.0 / 6.2 / 5.8 / 3.5 / 3.9 / 4.9 / 5.1
δ / 6.2 / 5.6 / 3.3 / 3.8 / 5.9 / 5.7 / 3.5 / 3.9
δ / 6.4 / 5.8 / 3.4 / 3.9 / 5.9 / 5.6 / 4.0 / 4.3

Table 4S NMR chemical shifts of the host protons in the CB[n]-XYL complexes and chemical shifts in water (SCRF-PCM) are given in bold.

CB[6] / CB[6]-XYL-A / CB[7] / CB[7]-XYL-A
H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3
6.3 / 5.6 / 3.4 / 3.9 / 4.7 / 5.1 / 6.2 / 5.6 / 3.7 / 3.9 / 5.4 / 5.3 / 6.3 / 5.7 / 3.5 / 3.9 / 4.8 / 5.0 / 5.7 / 5.9 / 3.6 / 4.0 / 5.0 / 5.2
6.1 / 5.8 / 3.2 / 3.7 / 4.7 / 5.0 / 6.3 / 5.6 / 3.7 / 3.8 / 5.1 / 5.5 / 6.4 / 5.7 / 3.2 / 3.7 / 4.7 / 5.0 / 6.1 / 5.8 / 3.6 / 3.9 / 5.0 / 5.2
6.3 / 5.8 / 3.2 / 3.8 / 4.7 / 5.0 / 5.8 / 6.0 / 3.7 / 4.0 / 5 / 5.1 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 4.9 / 6.3 / 5.6 / 3.7 / 3.9 / 4.8 / 5.1
6.3 / 5.8 / 3.5 / 3.9 / 4.8 / 5.0 / 6.1 / 5.9 / 3.5 / 4.0 / 4.9 / 5.1 / 6.3 / 5.8 / 3.3 / 3.9 / 4.6 / 4.9 / 6.1 / 5.5 / 3.6 / 3.8 / 4.9 / 5.1
6.3 / 5.8 / 3.3 / 3.8 / 4.7 / 5.1 / 5.9 / 5.6 / 3.4 / 3.7 / 5.1 / 5.5 / 6.2 / 5.8 / 3.1 / 3.8 / 4.5 / 5.0 / 6.3 / 5.9 / 3.3 / 3.7 / 4.9 / 5.2
6.3 / 5.8 / 3.3 / 4.0 / 4.7 / 5.1 / 5.8 / 5.6 / 3.4 / 3.8 / 5.6 / 5.2 / 6.2 / 5.7 / 3.5 / 3.8 / 4.6 / 5.0 / 6.1 / 5.9 / 3.9 / 4.1 / 4.8 / 5.0
6.3 / 5.8 / 3.4 / 3.7 / 4.7 / 5.1 / 6.3 / 6.0 / 3.7 / 4.0 / 5.4 / 5.3 / 6.2 / 5.8 / 3.3 / 3.8 / 4.6 / 5.2 / 5.9 / 5.4 / 3.6 / 3.9 / 4.7 / 4.9
6.1 / 5.8 / 3.2 / 3.9 / 4.7 / 5.0 / 6.2 / 6.0 / 3.7 / 4.0 / 5.1 / 5.5 / 6.4 / 5.9 / 3.4 / 4.0 / 4.6 / 5.1 / 5.6 / 5.5 / 3.3 / 3.6 / 4.8 / 5.0
6.3 / 5.6 / 3.2 / 3.7 / 4.7 / 5.0 / 6.1 / 5.8 / 3.6 / 3.9 / 4.9 / 5.1 / 6.3 / 5.8 / 3.5 / 4.0 / 4.7 / 5.1 / 5.9 / 5.6 / 3.7 / 4.0 / 4.8 / 5.1
6.3 / 5.8 / 3.5 / 3.8 / 4.8 / 5.0 / 5.8 / 5.5 / 3.7 / 3.9 / 4.9 / 5 / 6.4 / 5.8 / 3.3 / 3.7 / 4.7 / 5.1 / 6.1 / 5.7 / 3.4 / 3.8 / 5.0 / 5.3
6.3 / 5.8 / 3.3 / 3.9 / 4.7 / 5.1 / 5.9 / 5.6 / 3.5 / 3.8 / 5.1 / 5.5 / 6.4 / 5.7 / 3.2 / 3.9 / 4.7 / 5.0 / 6.3 / 6.0 / 3.6 / 4.0 / 5.0 / 5.2
6.3 / 5.8 / 3.3 / 3.8 / 4.7 / 5.1 / 6.1 / 5.7 / 3.4 / 3.7 / 5.5 / 5.2 / 6.3 / 5.7 / 3.5 / 3.8 / 4.7 / 5.1 / 6.2 / 5.9 / 3.9 / 4.1 / 5.0 / 5.2
6.2 / 5.8 / 3.2 / 3.7 / 4.6 / 5.2 / 6.0 / 5.5 / 3.5 / 3.8 / 4.7 / 4.9
6.3 / 5.8 / 3.4 / 4.0 / 4.6 / 5.3 / 6.0 / 5.7 / 3.7 / 4.0 / 4.7 / 4.9

Table 5SNMR chemical shifts of the host protons in the iCB[n]-XYL complexes and chemical shifts in water (SCRF-PCM) are given in bold.

iCB[6] / iCB[6]-XYL-A / iCB[7] / iCB[7]-XYL-A
H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3 / H1 / H2 / H3
i / 4.3 / 4.8 / 3.6 / 3.9 / 4.8 / 5.0 / 4.3 / 4.4
i / 4.5 / 5.0 / 3.5 / 3.9 / 4.7 / 4.9 / 3.5 / 3.6
α / 6.0 / 5.5 / 4.0 / 4.0 / 4.9 / 5.2 / 5.6 / 5.3 / 4.0 / 4.1 / 5.3 / 5.5 / 5.7 / 5.4 / 3.7 / 3.9 / 4.9 / 5.2 / 5.1 / 5.1 / 3.9 / 4.0 / 4.9 / 5.1
α / 5.6 / 5.6 / 3.9 / 4.3 / 5.1 / 5.2 / 5.5 / 5.1 / 3.7 / 3.8 / 5.2 / 5.3 / 5.9 / 5.6 / 4.1 / 4.3 / 4.7 / 5.1 / 6.0 / 5.6 / 4.0 / 4.2 / 4.8 / 5.1
α / 5.7 / 5.5 / 4.1 / 4.3 / 4.8 / 5.3 / 5.6 / 5.2 / 3.6 / 3.7 / 5.0 / 5.2 / 5.7 / 5.4 / 3.8 / 4.1 / 4.6 / 5.1 / 5.9 / 5.6 / 3.8 / 3.9 / 5.0 / 5.2
α / 5.8 / 5.4 / 3.7 / 4.0 / 4.8 / 5.4 / 5.4 / 5.3 / 3.9 / 4.0 / 5.2 / 5.4 / 5.8 / 5.6 / 3.6 / 3.8 / 4.6 / 4.9 / 5.7 / 5.4 / 4.2 / 4.3 / 5.1 / 5.1
β / 6.2 / 5.7 / 3.3 / 3.7 / 4.7 / 5.1 / 6.3 / 6.0 / 4.1 / 4.4 / 4.7 / 4.9 / 6.3 / 5.7 / 3.2 / 3.8 / 4.8 / 5.3 / 6.0 / 5.7 / 3.9 / 4.2 / 5.0 / 5.2
β / 6.2 / 5.9 / 3.5 / 4.1 / 4.7 / 5.1 / 6.5 / 6.1 / 4.1 / 4.3 / 5.0 / 5.3 / 6.3 / 5.8 / 3.5 / 4.0 / 4.9 / 5.3 / 6.2 / 5.8 / 3.8 / 4.1 / 4.9 / 5.1
β / 6.2 / 5.8 / 3.3 / 3.9 / 4.8 / 5.0 / 6.5 / 6.2 / 4.0 / 4.3 / 5.1 / 5.3 / 6.3 / 5.8 / 3.5 / 3.9 / 4.7 / 5.1 / 6.4 / 5.9 / 3.8 / 4.0 / 4.9 / 5.1
β / 6.3 / 5.8 / 3.3 / 4.0 / 4.8 / 5.0 / 6.3 / 6.1 / 4.0 / 4.3 / 4.9 / 5.0 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 5.1 / 6.1 / 6.0 / 3.7 / 4.0 / 4.8 / 5.1
γ / 6.3 / 5.9 / 3.4 / 3.9 / 4.7 / 5.1 / 5.9 / 5.6 / 3.7 / 3.9 / 4.7 / 4.8 / 6.3 / 5.8 / 3.4 / 3.9 / 4.8 / 5.2 / 6.2 / 6.0 / 4.0 / 4.4 / 4.9 / 5.2
γ / 6.4 / 5.8 / 3.3 / 3.9 / 4.7 / 5.1 / 6.0 / 5.6 / 3.5 / 3.8 / 4.6 / 4.7 / 6.4 / 5.8 / 3.4 / 4.0 / 4.8 / 5.2 / 6.4 / 6.0 / 3.5 / 3.9 / 5.0 / 5.2
γ / 6.3 / 5.7 / 3.3 / 3.9 / 6.0 / 5.6 / 3.5 / 3.8 / 6.3 / 5.8 / 3.3 / 3.8 / 4.6 / 5.0 / 6.1 / 5.7 / 3.5 / 3.8 / 4.8 / 5.1
γ / 6.2 / 5.9 / 3.4 / 3.8 / 6.1 / 5.8 / 3.8 / 4.0 / 6.3 / 5.7 / 3.3 / 3.8 / 4.6 / 5.0 / 5.8 / 5.6 / 3.6 / 3.8 / 5.0 / 5.2
δ / 6.2 / 5.6 / 3.3 / 3.8 / 6.0 / 5.7 / 3.3 / 3.8
δ / 6.4 / 5.8 / 3.4 / 3.9 / 5.8 / 5.7 / 3.6 / 3.9

Table 6SHydrogen bond distances (in Ǻ) from different functional in complexes of CB[6] and iCB[6].

Atoms / B97D / M06-2X
CB6-HDA-A / H117…O17 / 2.012 / 2.035
H119…O61 / 1.974 / 1.950
H122…O58 / 2.010 / 2.032
H121…O10 / 1.977 / 1.950
iCB6-XYL-A / H130…O104 / 1.894 / 1.862
H129…O106 / 1.909 / 1.948
H129…O105 / 2.377 / 2.193
H120…O102 / 1.863 / 1.861
H121…O100 / 1.958 / 1.949
H121…O101 / 2.297 / 2.193

Fig. 5S superimposed structures of CB[6]-HDA as well as iCB[6]-XYL from the B97D and M06-2X functionals based DFT optimizations

CB[6]-HDA-A

Fig. 5S

iCB[6]-XYL-A