Structural insights into 1,4-bis­(neopent­yloxy)pillar[5]arene and the pyridine host–guest system

Vinodh, M.; Alipour, F.H.; Al-Azemi, T.F.

doi:10.1107/S2414314624010733

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 11| November 2024| x241073

https://doi.org/10.1107/S2414314624010733

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Structural insights into 1,4-bis(neopentyloxy)pillar[5]arene and the pyridine host–guest system

Mickey Vinodh,^a Fatemeh H. Alipour ^a and Talal F. Al-Azemi ^a ^*

^aDepartment of Chemistry, Kuwait University, PO Box 5969, Safat 13060, Kuwait
^*Correspondence e-mail: t.alazemi@ku.edu.kw

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 30 October 2024; accepted 5 November 2024; online 8 November 2024)

The crystal structure of 1,4-bis(neopentyloxy)pillar[5]arene, C₉₅H₁₄₀N₂O₁₀ (TbuP), featuring two encapsulated pyridine molecules, reveals significant host–guest interactions. Interestingly, the pyridine guests are positioned near the neopentyloxy substituents instead of the electron-rich aromatic core of the pillar[5]arene. This spatial arrangement suggests a preference for the pyridine molecules to engage with the aliphatic regions of the host. Detailed analysis of the structural characteristics of this host–guest system (TbuP·2Py), as well as its packing pattern within the crystal network, is presented and discussed.

Keywords: crystal structure; host–guest system; pentyloxypillar[5]arene; pyridine guest.

CCDC reference: 2393384

Structure description

The intrinsic cavity of pillar[n]arenes exhibits fascinating guest-encapsulation behavior, significantly influenced by their peripheral substitutions (Ogoshi et al., 2016 ; Li et al., 2020 ). The electron-rich cavity of pillar[5]arene tends to favor the inclusion of long aliphatic chains over aromatic guests. This limitation in encapsulating aromatic guests restricts the applications of pillararenes as functional materials. Optimizing the peripheral substituents on pillar[5]arene is therefore crucial to enhance its encapsulation performance for aromatic molecules. By carefully selecting these substituents, the interactions and selectivity for specific aromatic guests can be fine-tuned, making pillar[5]arenes valuable for various applications, including separation technologies and sensor design (Jie et al., 2018 ; Wu et al., 2020 ; Wu, Wu, Li et al., 2023 ; Wu, Tang et al., 2023 ; Zhao et al., 2024 ).

The title inclusion complex (TbuP·2Py) crystallizes in the orthorhombic crystal system, space group Fdd2. The asymmetric unit contains half of the pillar[5]arene molecule (Fig. 1), with the complete structure revealed through symmetry expansion (Fig. 2). This pillar[5]arene exhibits a pentagonal macrocyclic shape with neopentyloxy substitutions at both the top and bottom rims. Notably, one of the neopentyloxy substituents shows positional disorder within the crystal, with only the higher occupancy orientation shown. In the crystal structure of the TbuP·2Py system, two pyridine molecules are encapsulated within the cavity of the pillar[5]arene. These pyridine guests are strategically positioned adjacent to the neopentyloxy regions rather than the electron-rich core, enhancing stability through non-bonding interactions. This is illustrated in the Fig. 3, with quantitative details provided in the accompanying table (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

π denotes the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C46—H46⋯O4	0.93	2.88	3.56 (1)	131
C24—H24B⋯π	0.97	2.99	3.921 (11)	161
C19—H19B⋯N1ⁱ	0.97	2.97	3.81 (1)	145
C39—H39B⋯N1ⁱ	0.97	3.17	3.74 (1)	120
Symmetry code: (i) .

Figure 1
Symmetry-expanded crystal structure of TBuP·2Py with displacement ellipsoids (30% probability; only the symmetry independent atoms are labeled). Only the major components of the disordered moieties are shown. Hydrogen atoms are omitted for clarity.

Figure 2
Crystal structure (symmetry expanded) of TBuP·2Py. Only the major components of the disordered moieties are shown. Hydrogen atoms belonging to the pillar[5]arene are omitted for clarity.

Figure 3
Supramolecular interactions between the pillar[5]arene host and pyridine guests. π denotes the centroid of the pyridine ring. Symmetry code: (i) 1 − x, −y, z.

The neopentyloxy substitutions on the rims of the pillar[5]arene play a crucial role in accommodating aromatic guests within the intrinsic cavity, which typically favors non-aromatic linear molecules. The TbuP·2Py system exhibits a unique packing arrangement, forming one-dimensional channels along the b-axis direction in the crystal network (Fig. 4). This specific organization is crucial for facilitating guest encapsulation and removal. Such arrangements enable the use of pillar[5]arene-based nonporous adaptive crystals (NACs) in adsorption and separation processes, highlighting the potential for tuning material properties based on guest interactions and opening avenues for further research and practical applications.

Figure 4
Packing pattern of TBuP·2Py system in the crystal network showing one-dimensional channels along the b-axis direction.

Synthesis and crystallization

The synthesis and characterization of 1,2,3,4,5-(1,4-neopentyloxy)pillar[5]arene (TBuP) have been previously described (Al-Azemi et al., 2019 ). Colorless blocks of TBuP·2Py crystals, suitable for single-crystal analysis, were obtained by dissolving 25 mg of TBuP in a chloroform: pyridine solvent mixture (90:10 v/v, 1 ml) and allowing for slow solvent evaporation.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. One of the neopentyl spacers of the pillar[5]arene in the crystal was found to be disordered. The most satisfactory occupancies for these disordered neopentyloxy fractions were 0.607 (17):0.393 (17) for the major and minor components, respectively. The DELU and SIMU commands were used in the refinement to restrain the displacement factors of these disordered components. Additionally, the DELU and SIMU commands were used to restrain the displacement factors of the atoms belonging to the guest pyridine and another neopentyl moiety of the pillar[5]arene.

Table 2
Experimental details

Crystal data
Chemical formula	C₉₅H₁₄₀N₂O₁₀
M_r	1470.08
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	47.848 (5), 14.2452 (14), 27.679 (2)
V (Å³)	18866 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.17 × 0.14 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995 )
T_min, T_max	0.156, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	23011, 7942, 3988
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.192, 0.99
No. of reflections	7942
No. of parameters	526
No. of restraints	267
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16
Computer programs: CrystalClear (Rigaku, 2016 ), CrystalStructure (Rigaku, 2017 ), SHELXL2019/3 (Sheldrick, 2015 ) and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2393384

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624010733/bt4159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624010733/bt4159Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624010733/bt4159Isup3.mol

checkCIF report

Computing details top

1,4-Bis(neopentyloxy)pillar[5]arene top

Crystal data top

C₉₅H₁₄₀N₂O₁₀	D_x = 1.035 Mg m⁻³
M_r = 1470.08	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Fdd2	Cell parameters from 11195 reflections
a = 47.848 (5) Å	θ = 3.1–25.0°
b = 14.2452 (14) Å	µ = 0.07 mm⁻¹
c = 27.679 (2) Å	T = 293 K
V = 18866 (3) Å³	Block, colorless
Z = 8	0.17 × 0.14 × 0.11 mm
F(000) = 6432

Data collection top

Rigaku R-AXIS RAPID diffractometer	3988 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.087
ω scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −56→54
T_min = 0.156, T_max = 0.991	k = −16→16
23011 measured reflections	l = −31→29
7942 independent reflections

Refinement top

Refinement on F²	267 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.0931P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
7942 reflections	Δρ_max = 0.25 e Å⁻³
526 parameters	Δρ_min = −0.16 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The single-crystal data collection was performed using a Rigaku Rapid II diffractometer with Mo-Kα radiation at 293 K. The data was processed using the 'CrystalClear' software package. The structure was solved by direct methods using the 'CrystalStructure' crystallographic software package, and refinement was carried out with SHELXL2019/3. All the hydrogen atoms were positioned geometrically, with C—H distances of methyl, methylene, and aromatic groups being 0.96, 0.97, and 0.93 Å, respectively, and the displacement factors of hydrogen atoms were set to U_iso(H) = 1.2U_eq(C), for hydrogen atoms of the methyl groups the displacement parameters were set to U_iso(H) = 1.5U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.60191 (11)	−0.1383 (3)	0.65859 (15)	0.0888 (15)
N1	0.4746 (2)	0.2097 (11)	0.6285 (4)	0.180 (4)
O2	0.56089 (11)	0.1905 (3)	0.58101 (15)	0.0846 (14)
O3	0.52946 (10)	−0.1612 (3)	0.81964 (17)	0.0763 (12)
O4	0.57102 (9)	0.1804 (3)	0.75905 (14)	0.0715 (12)
O5	0.53741 (8)	−0.1469 (3)	0.51250 (16)	0.0715 (12)
C1	0.57093 (11)	0.0302 (4)	0.5724 (2)	0.0562 (15)
C2	0.58163 (13)	−0.0509 (4)	0.5915 (2)	0.0624 (16)
H2	0.582871	−0.103606	0.571735	0.075*
C3	0.59073 (13)	−0.0579 (5)	0.6391 (2)	0.0660 (17)
C4	0.58896 (12)	0.0193 (4)	0.6688 (2)	0.0553 (15)
C5	0.57858 (13)	0.1030 (4)	0.6500 (2)	0.0629 (17)
H5	0.577422	0.155837	0.669658	0.076*
C6	0.56995 (13)	0.1082 (4)	0.6022 (2)	0.0599 (16)
C7	0.59780 (13)	0.0167 (5)	0.7218 (2)	0.0659 (18)
H7A	0.609585	−0.037734	0.727080	0.079*
H7B	0.608792	0.072201	0.728921	0.079*
C8	0.57318 (12)	0.0125 (4)	0.75623 (19)	0.0578 (15)
C9	0.56235 (13)	−0.0727 (4)	0.7712 (2)	0.0627 (16)
H9	0.570529	−0.128118	0.760413	0.075*
C10	0.53970 (14)	−0.0770 (4)	0.8017 (2)	0.0612 (16)
C11	0.52636 (12)	0.0041 (5)	0.8179 (2)	0.0581 (15)
C12	0.53756 (14)	0.0891 (5)	0.8030 (2)	0.0653 (17)
H12	0.529136	0.144713	0.812916	0.078*
C13	0.56101 (14)	0.0931 (5)	0.7737 (2)	0.0656 (16)
C14	0.500000	0.000000	0.8479 (4)	0.072 (3)
H144	0.4987 (16)	0.052 (5)	0.865 (3)	0.107*
C15	0.48974 (14)	−0.0886 (4)	0.5176 (2)	0.0650 (16)
H15	0.482886	−0.149562	0.519299	0.078*
C16	0.51837 (14)	−0.0754 (5)	0.5155 (2)	0.0600 (15)
C17	0.52911 (13)	0.0152 (4)	0.51732 (19)	0.0547 (15)
C18	0.56011 (13)	0.0331 (4)	0.5206 (2)	0.0622 (16)
H18A	0.564203	0.094187	0.506801	0.075*
H18B	0.569905	−0.013711	0.501611	0.075*
C19	0.60495 (17)	−0.2178 (5)	0.6288 (3)	0.085 (2)
H19A	0.615767	−0.201267	0.600435	0.101*
H19B	0.586672	−0.238811	0.618149	0.101*
C20	0.61933 (17)	−0.2962 (5)	0.6554 (3)	0.090 (2)
C21	0.6033 (3)	−0.3219 (8)	0.7008 (4)	0.166 (5)
H21A	0.583828	−0.328691	0.693265	0.199*
H21B	0.605613	−0.273314	0.724529	0.199*
H21C	0.610332	−0.380082	0.713490	0.199*
C22	0.64888 (19)	−0.2686 (6)	0.6669 (4)	0.137 (4)
H22A	0.658865	−0.322241	0.678845	0.164*
H22B	0.648845	−0.220143	0.690960	0.164*
H22C	0.657826	−0.245838	0.638122	0.164*
C23	0.6205 (3)	−0.3799 (6)	0.6225 (4)	0.150 (4)
H23A	0.601810	−0.399755	0.614853	0.179*
H23B	0.630241	−0.430146	0.638258	0.179*
H23C	0.630090	−0.363319	0.593259	0.179*
C24	0.5605 (2)	0.2736 (5)	0.6084 (3)	0.104 (2)
H24A	0.576816	0.275167	0.629095	0.125*
H24B	0.544059	0.273307	0.629037	0.125*
C25	0.5600 (2)	0.3590 (6)	0.5781 (3)	0.104 (2)
C26A	0.5842 (5)	0.3647 (14)	0.5425 (8)	0.140 (5)	0.607 (17)
H26A	0.582707	0.421581	0.524051	0.210*	0.607 (17)
H26B	0.601579	0.364538	0.559851	0.210*	0.607 (17)
H26C	0.583575	0.311717	0.521119	0.210*	0.607 (17)
C27A	0.5326 (4)	0.3565 (10)	0.5509 (7)	0.116 (5)	0.607 (17)
H27A	0.531256	0.410814	0.530512	0.174*	0.607 (17)
H27B	0.531837	0.300797	0.531433	0.174*	0.607 (17)
H27C	0.517404	0.356308	0.573494	0.174*	0.607 (17)
C28A	0.5613 (5)	0.4454 (14)	0.6142 (8)	0.127 (5)	0.607 (17)
H28A	0.561038	0.502867	0.596054	0.191*	0.607 (17)
H28B	0.545374	0.443543	0.635328	0.191*	0.607 (17)
H28C	0.578106	0.442111	0.632928	0.191*	0.607 (17)
C26B	0.5450 (8)	0.442 (2)	0.6081 (13)	0.124 (6)	0.393 (17)
H26D	0.544557	0.498242	0.588786	0.186*	0.393 (17)
H26E	0.526200	0.423893	0.615929	0.186*	0.393 (17)
H26F	0.555180	0.454079	0.637304	0.186*	0.393 (17)
C27B	0.5906 (6)	0.383 (2)	0.5733 (13)	0.136 (6)	0.393 (17)
H27D	0.592626	0.438095	0.553948	0.203*	0.393 (17)
H27E	0.598362	0.393596	0.604791	0.203*	0.393 (17)
H27F	0.600182	0.331331	0.558197	0.203*	0.393 (17)
C28B	0.5493 (7)	0.3567 (18)	0.5249 (11)	0.124 (5)	0.393 (17)
H28D	0.550629	0.418469	0.511138	0.187*	0.393 (17)
H28E	0.560514	0.313960	0.506354	0.187*	0.393 (17)
H28F	0.530179	0.336420	0.524368	0.187*	0.393 (17)
C29	0.54706 (18)	−0.2407 (5)	0.8176 (3)	0.093 (2)
H29A	0.566269	−0.221921	0.823193	0.111*
H29B	0.545963	−0.268918	0.785706	0.111*
C30	0.5383 (2)	−0.3112 (6)	0.8551 (3)	0.104 (2)
C31	0.5083 (2)	−0.3401 (6)	0.8486 (4)	0.144 (4)
H31A	0.503887	−0.389788	0.870762	0.173*
H31B	0.505428	−0.361475	0.816096	0.173*
H31C	0.496310	−0.287286	0.854845	0.173*
C32	0.5418 (2)	−0.2685 (7)	0.9049 (3)	0.138 (3)
H32A	0.535916	−0.312969	0.928934	0.165*
H32B	0.530507	−0.212879	0.907327	0.165*
H32C	0.561026	−0.252564	0.910032	0.165*
C33	0.5569 (3)	−0.3968 (7)	0.8477 (5)	0.176 (5)
H33A	0.559224	−0.408183	0.813792	0.211*
H33B	0.548410	−0.450551	0.862607	0.211*
H33C	0.574852	−0.385573	0.862193	0.211*
C34	0.58197 (18)	0.2373 (5)	0.7962 (3)	0.089 (2)
H34A	0.597884	0.205942	0.810762	0.106*
H34B	0.567889	0.245701	0.821059	0.106*
C35	0.59094 (15)	0.3319 (5)	0.7775 (3)	0.080 (2)
C36	0.6136 (2)	0.3184 (7)	0.7402 (3)	0.132 (3)
H36A	0.619180	0.378394	0.727680	0.159*
H36B	0.606604	0.280159	0.714296	0.159*
H36C	0.629378	0.288067	0.754809	0.159*
C37	0.56685 (19)	0.3821 (6)	0.7551 (4)	0.128 (4)
H37A	0.559080	0.344121	0.729744	0.153*
H37B	0.573139	0.440705	0.741842	0.153*
H37C	0.552828	0.393729	0.779132	0.153*
C38	0.60272 (19)	0.3866 (6)	0.8202 (3)	0.117 (3)
H38A	0.617281	0.350683	0.835249	0.140*
H38B	0.588102	0.398326	0.843147	0.140*
H38C	0.610191	0.445232	0.808985	0.140*
C39	0.52736 (16)	−0.2326 (5)	0.4937 (3)	0.090 (2)
H39A	0.514780	−0.219931	0.467058	0.109*
H39B	0.516871	−0.265245	0.518591	0.109*
C40	0.55100 (17)	−0.2952 (5)	0.4763 (3)	0.089 (2)
C41	0.57107 (18)	−0.3144 (5)	0.5154 (3)	0.109 (3)
H41A	0.561516	−0.343427	0.542011	0.130*
H41B	0.579369	−0.256589	0.525946	0.130*
H41C	0.585404	−0.355806	0.503775	0.130*
C42	0.5665 (3)	−0.2467 (8)	0.4363 (4)	0.165 (4)
H42A	0.581635	−0.285762	0.425598	0.198*
H42B	0.573753	−0.188060	0.447819	0.198*
H42C	0.553978	−0.235384	0.409791	0.198*
C43	0.5379 (2)	−0.3833 (6)	0.4582 (5)	0.170 (5)
H43A	0.526347	−0.409933	0.483061	0.204*
H43B	0.552213	−0.427341	0.449472	0.204*
H43C	0.526616	−0.369519	0.430384	0.204*
C44	0.4760 (3)	0.3023 (12)	0.6497 (5)	0.172 (4)
H44	0.467544	0.355100	0.636364	0.207*
C45	0.4908 (3)	0.3035 (12)	0.6910 (5)	0.171 (4)
H45	0.492711	0.360552	0.706956	0.205*
C46	0.5034 (3)	0.2262 (13)	0.7111 (4)	0.160 (4)
H46	0.514181	0.232330	0.738975	0.191*
C47	0.5004 (3)	0.1472 (11)	0.6917 (5)	0.176 (4)
H47	0.508328	0.095312	0.706772	0.211*
C48	0.4860 (3)	0.1330 (11)	0.6498 (6)	0.183 (4)
H48	0.484166	0.073479	0.636375	0.220*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.134 (4)	0.066 (3)	0.067 (3)	0.022 (3)	−0.031 (3)	−0.005 (2)
N1	0.146 (7)	0.257 (11)	0.138 (7)	−0.022 (8)	−0.024 (6)	0.030 (7)
O2	0.126 (4)	0.061 (3)	0.067 (3)	0.009 (3)	−0.007 (3)	0.008 (2)
O3	0.080 (3)	0.057 (3)	0.092 (3)	0.005 (2)	0.010 (2)	0.016 (2)
O4	0.093 (3)	0.059 (3)	0.062 (3)	−0.011 (2)	0.001 (2)	−0.002 (2)
O5	0.065 (3)	0.064 (3)	0.086 (3)	0.013 (2)	−0.006 (2)	−0.022 (2)
C1	0.051 (4)	0.060 (4)	0.057 (4)	0.002 (3)	0.010 (3)	0.005 (3)
C2	0.070 (4)	0.058 (4)	0.059 (4)	0.008 (3)	−0.001 (3)	0.000 (3)
C3	0.077 (5)	0.059 (5)	0.062 (4)	0.002 (3)	−0.008 (3)	0.013 (4)
C4	0.058 (4)	0.057 (4)	0.050 (4)	0.002 (3)	0.005 (3)	0.004 (3)
C5	0.076 (5)	0.056 (4)	0.057 (4)	0.007 (3)	0.009 (3)	0.001 (3)
C6	0.060 (4)	0.060 (4)	0.060 (4)	0.006 (3)	0.009 (3)	0.016 (3)
C7	0.065 (5)	0.073 (5)	0.060 (4)	−0.003 (3)	−0.009 (3)	0.001 (3)
C8	0.061 (4)	0.063 (4)	0.049 (3)	0.004 (3)	−0.004 (3)	0.000 (3)
C9	0.069 (4)	0.063 (4)	0.055 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C10	0.069 (4)	0.061 (5)	0.054 (4)	0.001 (3)	−0.005 (3)	0.008 (3)
C11	0.062 (4)	0.064 (4)	0.048 (3)	0.001 (3)	−0.006 (3)	0.000 (3)
C12	0.078 (5)	0.061 (4)	0.057 (4)	0.003 (4)	0.000 (4)	−0.002 (3)
C13	0.077 (4)	0.067 (4)	0.052 (4)	−0.012 (4)	−0.006 (3)	0.005 (3)
C14	0.070 (7)	0.085 (8)	0.059 (6)	−0.001 (6)	0.000	0.000
C15	0.075 (5)	0.060 (4)	0.060 (4)	−0.006 (4)	0.000 (3)	−0.010 (3)
C16	0.063 (5)	0.065 (5)	0.052 (4)	0.011 (3)	0.004 (3)	−0.006 (3)
C17	0.061 (4)	0.061 (4)	0.042 (3)	0.011 (3)	0.002 (3)	0.005 (3)
C18	0.070 (5)	0.065 (4)	0.051 (4)	0.003 (3)	0.003 (3)	0.009 (3)
C19	0.103 (6)	0.061 (5)	0.090 (5)	0.002 (4)	−0.022 (4)	0.002 (4)
C20	0.104 (6)	0.048 (4)	0.118 (7)	0.002 (4)	−0.045 (5)	0.004 (4)
C21	0.179 (12)	0.138 (9)	0.180 (11)	0.024 (8)	−0.001 (9)	0.087 (8)
C22	0.109 (8)	0.116 (7)	0.185 (10)	0.000 (6)	−0.050 (7)	−0.018 (7)
C23	0.180 (10)	0.078 (6)	0.191 (10)	0.028 (6)	−0.069 (8)	−0.030 (7)
C24	0.145 (5)	0.073 (4)	0.095 (5)	0.000 (4)	0.001 (4)	0.012 (4)
C25	0.132 (5)	0.075 (4)	0.104 (5)	−0.008 (4)	−0.007 (4)	0.023 (4)
C26A	0.155 (9)	0.128 (9)	0.138 (10)	−0.014 (8)	0.011 (8)	0.046 (9)
C27A	0.141 (10)	0.076 (7)	0.132 (10)	0.006 (8)	−0.022 (8)	0.038 (7)
C28A	0.156 (13)	0.077 (7)	0.149 (9)	−0.011 (10)	−0.020 (10)	0.022 (7)
C26B	0.154 (13)	0.077 (9)	0.141 (11)	−0.006 (12)	−0.013 (12)	0.021 (9)
C27B	0.145 (10)	0.122 (11)	0.139 (13)	−0.027 (10)	−0.007 (11)	0.021 (11)
C28B	0.155 (11)	0.097 (9)	0.121 (9)	−0.007 (10)	−0.017 (9)	0.034 (9)
C29	0.108 (5)	0.074 (5)	0.097 (5)	0.005 (4)	0.014 (4)	0.014 (4)
C30	0.116 (6)	0.080 (5)	0.115 (5)	0.012 (4)	0.019 (5)	0.034 (4)
C31	0.148 (8)	0.109 (7)	0.176 (9)	−0.031 (6)	0.020 (7)	0.029 (6)
C32	0.153 (8)	0.157 (8)	0.103 (6)	0.002 (7)	0.008 (6)	0.041 (5)
C33	0.191 (10)	0.102 (7)	0.234 (12)	0.054 (7)	0.056 (9)	0.054 (7)
C34	0.107 (6)	0.075 (5)	0.084 (5)	−0.005 (4)	−0.001 (4)	−0.006 (4)
C35	0.078 (5)	0.068 (5)	0.094 (5)	−0.014 (4)	−0.011 (4)	0.001 (4)
C36	0.117 (8)	0.144 (8)	0.136 (8)	−0.043 (6)	0.017 (7)	0.001 (7)
C37	0.113 (7)	0.084 (6)	0.185 (10)	0.002 (5)	−0.044 (7)	0.014 (6)
C38	0.123 (7)	0.095 (6)	0.133 (7)	−0.023 (5)	−0.020 (6)	−0.025 (5)
C39	0.091 (5)	0.084 (5)	0.096 (5)	0.018 (4)	−0.010 (4)	−0.039 (4)
C40	0.095 (5)	0.086 (5)	0.086 (5)	0.032 (4)	−0.015 (4)	−0.033 (4)
C41	0.127 (6)	0.099 (6)	0.100 (6)	0.048 (5)	−0.020 (5)	−0.023 (5)
C42	0.201 (10)	0.179 (9)	0.116 (7)	0.081 (7)	0.047 (7)	0.019 (7)
C43	0.142 (9)	0.121 (7)	0.247 (12)	0.047 (6)	−0.046 (8)	−0.110 (7)
C44	0.135 (8)	0.235 (10)	0.147 (8)	0.009 (8)	0.005 (6)	0.044 (8)
C45	0.149 (9)	0.237 (10)	0.128 (8)	−0.010 (8)	0.015 (6)	−0.002 (7)
C46	0.144 (8)	0.240 (12)	0.095 (7)	−0.031 (8)	−0.021 (6)	0.006 (7)
C47	0.159 (8)	0.236 (10)	0.131 (8)	−0.037 (8)	−0.012 (6)	0.024 (8)
C48	0.165 (9)	0.238 (10)	0.147 (8)	−0.029 (8)	−0.022 (7)	0.021 (8)

Geometric parameters (Å, º) top

O1—C3	1.374 (7)	C27A—H27A	0.9600
O1—C19	1.409 (7)	C27A—H27B	0.9600
N1—C48	1.357 (16)	C27A—H27C	0.9600
N1—C44	1.445 (17)	C28A—H28A	0.9600
O2—C6	1.382 (7)	C28A—H28B	0.9600
O2—C24	1.405 (9)	C28A—H28C	0.9600
O3—C10	1.388 (7)	C26B—H26D	0.9600
O3—C29	1.412 (8)	C26B—H26E	0.9600
O4—C13	1.393 (7)	C26B—H26F	0.9600
O4—C34	1.410 (8)	C27B—H27D	0.9600
O5—C16	1.369 (7)	C27B—H27E	0.9600
O5—C39	1.412 (7)	C27B—H27F	0.9600
C1—C2	1.369 (8)	C28B—H28D	0.9600
C1—C6	1.386 (8)	C28B—H28E	0.9600
C1—C18	1.524 (8)	C28B—H28F	0.9600
C2—C3	1.392 (8)	C29—C30	1.504 (10)
C2—H2	0.9300	C29—H29A	0.9700
C3—C4	1.376 (8)	C29—H29B	0.9700
C4—C5	1.392 (8)	C30—C31	1.506 (13)
C4—C7	1.527 (8)	C30—C32	1.516 (13)
C5—C6	1.388 (8)	C30—C33	1.524 (12)
C5—H5	0.9300	C31—H31A	0.9600
C7—C8	1.516 (8)	C31—H31B	0.9600
C7—H7A	0.9700	C31—H31C	0.9600
C7—H7B	0.9700	C32—H32A	0.9600
C8—C13	1.375 (8)	C32—H32B	0.9600
C8—C9	1.384 (8)	C32—H32C	0.9600
C9—C10	1.376 (8)	C33—H33A	0.9600
C9—H9	0.9300	C33—H33B	0.9600
C10—C11	1.393 (8)	C33—H33C	0.9600
C11—C12	1.387 (8)	C34—C35	1.507 (9)
C11—C14	1.512 (8)	C34—H34A	0.9700
C12—C13	1.385 (8)	C34—H34B	0.9700
C12—H12	0.9300	C35—C37	1.492 (10)
C14—H144	0.89 (7)	C35—C36	1.510 (11)
C14—H144ⁱ	0.89 (7)	C35—C38	1.522 (10)
C15—C17ⁱ	1.380 (8)	C36—H36A	0.9600
C15—C16	1.384 (9)	C36—H36B	0.9600
C15—H15	0.9300	C36—H36C	0.9600
C16—C17	1.391 (8)	C37—H37A	0.9600
C17—C18	1.508 (9)	C37—H37B	0.9600
C18—H18A	0.9700	C37—H37C	0.9600
C18—H18B	0.9700	C38—H38A	0.9600
C19—C20	1.504 (9)	C38—H38B	0.9600
C19—H19A	0.9700	C38—H38C	0.9600
C19—H19B	0.9700	C39—C40	1.519 (10)
C20—C22	1.501 (11)	C39—H39A	0.9700
C20—C23	1.502 (11)	C39—H39B	0.9700
C20—C21	1.518 (13)	C40—C41	1.473 (10)
C21—H21A	0.9600	C40—C43	1.491 (11)
C21—H21B	0.9600	C40—C42	1.501 (12)
C21—H21C	0.9600	C41—H41A	0.9600
C22—H22A	0.9600	C41—H41B	0.9600
C22—H22B	0.9600	C41—H41C	0.9600
C22—H22C	0.9600	C42—H42A	0.9600
C23—H23A	0.9600	C42—H42B	0.9600
C23—H23B	0.9600	C42—H42C	0.9600
C23—H23C	0.9600	C43—H43A	0.9600
C24—C25	1.478 (10)	C43—H43B	0.9600
C24—H24A	0.9700	C43—H43C	0.9600
C24—H24B	0.9700	C44—C45	1.346 (18)
C25—C27B	1.50 (3)	C44—H44	0.9300
C25—C27A	1.513 (17)	C45—C46	1.374 (17)
C25—C26A	1.52 (2)	C45—H45	0.9300
C25—C28B	1.56 (3)	C46—C47	1.257 (16)
C25—C28A	1.59 (2)	C46—H46	0.9300
C25—C26B	1.62 (3)	C47—C48	1.363 (18)
C26A—H26A	0.9600	C47—H47	0.9300
C26A—H26B	0.9600	C48—H48	0.9300
C26A—H26C	0.9600

C3—O1—C19	118.7 (5)	C25—C28A—H28A	109.5
C48—N1—C44	122.6 (13)	C25—C28A—H28B	109.5
C6—O2—C24	119.3 (5)	H28A—C28A—H28B	109.5
C10—O3—C29	117.9 (5)	C25—C28A—H28C	109.5
C13—O4—C34	115.3 (5)	H28A—C28A—H28C	109.5
C16—O5—C39	116.0 (5)	H28B—C28A—H28C	109.5
C2—C1—C6	117.3 (6)	C25—C26B—H26D	109.5
C2—C1—C18	120.9 (6)	C25—C26B—H26E	109.5
C6—C1—C18	121.8 (5)	H26D—C26B—H26E	109.5
C1—C2—C3	122.9 (6)	C25—C26B—H26F	109.5
C1—C2—H2	118.6	H26D—C26B—H26F	109.5
C3—C2—H2	118.6	H26E—C26B—H26F	109.5
O1—C3—C4	117.1 (5)	C25—C27B—H27D	109.5
O1—C3—C2	123.6 (6)	C25—C27B—H27E	109.5
C4—C3—C2	119.3 (6)	H27D—C27B—H27E	109.5
C3—C4—C5	118.9 (6)	C25—C27B—H27F	109.5
C3—C4—C7	122.5 (5)	H27D—C27B—H27F	109.5
C5—C4—C7	118.6 (6)	H27E—C27B—H27F	109.5
C6—C5—C4	120.5 (6)	C25—C28B—H28D	109.5
C6—C5—H5	119.8	C25—C28B—H28E	109.5
C4—C5—H5	119.8	H28D—C28B—H28E	109.5
O2—C6—C1	116.0 (5)	C25—C28B—H28F	109.5
O2—C6—C5	122.9 (6)	H28D—C28B—H28F	109.5
C1—C6—C5	121.1 (6)	H28E—C28B—H28F	109.5
C8—C7—C4	113.0 (5)	O3—C29—C30	109.9 (6)
C8—C7—H7A	109.0	O3—C29—H29A	109.7
C4—C7—H7A	109.0	C30—C29—H29A	109.7
C8—C7—H7B	109.0	O3—C29—H29B	109.7
C4—C7—H7B	109.0	C30—C29—H29B	109.7
H7A—C7—H7B	107.8	H29A—C29—H29B	108.2
C13—C8—C9	117.9 (6)	C29—C30—C31	111.4 (8)
C13—C8—C7	121.2 (6)	C29—C30—C32	109.3 (7)
C9—C8—C7	120.9 (6)	C31—C30—C32	108.8 (8)
C10—C9—C8	121.2 (6)	C29—C30—C33	106.2 (8)
C10—C9—H9	119.4	C31—C30—C33	108.9 (9)
C8—C9—H9	119.4	C32—C30—C33	112.3 (9)
C9—C10—O3	122.4 (6)	C30—C31—H31A	109.5
C9—C10—C11	121.4 (6)	C30—C31—H31B	109.5
O3—C10—C11	116.1 (6)	H31A—C31—H31B	109.5
C12—C11—C10	116.9 (6)	C30—C31—H31C	109.5
C12—C11—C14	121.3 (5)	H31A—C31—H31C	109.5
C10—C11—C14	121.8 (5)	H31B—C31—H31C	109.5
C13—C12—C11	121.5 (6)	C30—C32—H32A	109.5
C13—C12—H12	119.3	C30—C32—H32B	109.5
C11—C12—H12	119.3	H32A—C32—H32B	109.5
C8—C13—C12	121.0 (6)	C30—C32—H32C	109.5
C8—C13—O4	119.8 (6)	H32A—C32—H32C	109.5
C12—C13—O4	119.1 (6)	H32B—C32—H32C	109.5
C11—C14—C11ⁱ	113.2 (8)	C30—C33—H33A	109.5
C11—C14—H144	109 (5)	C30—C33—H33B	109.5
C11ⁱ—C14—H144	106 (5)	H33A—C33—H33B	109.5
C11—C14—H144ⁱ	106 (5)	C30—C33—H33C	109.5
C11ⁱ—C14—H144ⁱ	109 (5)	H33A—C33—H33C	109.5
H144—C14—H144ⁱ	114 (10)	H33B—C33—H33C	109.5
C17ⁱ—C15—C16	123.0 (6)	O4—C34—C35	111.7 (6)
C17ⁱ—C15—H15	118.5	O4—C34—H34A	109.3
C16—C15—H15	118.5	C35—C34—H34A	109.3
O5—C16—C15	124.1 (6)	O4—C34—H34B	109.3
O5—C16—C17	116.5 (6)	C35—C34—H34B	109.3
C15—C16—C17	119.3 (5)	H34A—C34—H34B	108.0
C15ⁱ—C17—C16	117.5 (6)	C37—C35—C34	110.6 (7)
C15ⁱ—C17—C18	121.0 (6)	C37—C35—C36	109.3 (7)
C16—C17—C18	121.5 (5)	C34—C35—C36	109.0 (7)
C17—C18—C1	112.7 (5)	C37—C35—C38	111.3 (7)
C17—C18—H18A	109.1	C34—C35—C38	107.3 (6)
C1—C18—H18A	109.1	C36—C35—C38	109.3 (7)
C17—C18—H18B	109.1	C35—C36—H36A	109.5
C1—C18—H18B	109.1	C35—C36—H36B	109.5
H18A—C18—H18B	107.8	H36A—C36—H36B	109.5
O1—C19—C20	111.0 (6)	C35—C36—H36C	109.5
O1—C19—H19A	109.4	H36A—C36—H36C	109.5
C20—C19—H19A	109.4	H36B—C36—H36C	109.5
O1—C19—H19B	109.4	C35—C37—H37A	109.5
C20—C19—H19B	109.4	C35—C37—H37B	109.5
H19A—C19—H19B	108.0	H37A—C37—H37B	109.5
C22—C20—C23	107.6 (8)	C35—C37—H37C	109.5
C22—C20—C19	109.9 (7)	H37A—C37—H37C	109.5
C23—C20—C19	108.0 (7)	H37B—C37—H37C	109.5
C22—C20—C21	111.3 (8)	C35—C38—H38A	109.5
C23—C20—C21	109.2 (8)	C35—C38—H38B	109.5
C19—C20—C21	110.7 (7)	H38A—C38—H38B	109.5
C20—C21—H21A	109.5	C35—C38—H38C	109.5
C20—C21—H21B	109.5	H38A—C38—H38C	109.5
H21A—C21—H21B	109.5	H38B—C38—H38C	109.5
C20—C21—H21C	109.5	O5—C39—C40	111.8 (6)
H21A—C21—H21C	109.5	O5—C39—H39A	109.3
H21B—C21—H21C	109.5	C40—C39—H39A	109.3
C20—C22—H22A	109.5	O5—C39—H39B	109.3
C20—C22—H22B	109.5	C40—C39—H39B	109.3
H22A—C22—H22B	109.5	H39A—C39—H39B	107.9
C20—C22—H22C	109.5	C41—C40—C43	111.4 (7)
H22A—C22—H22C	109.5	C41—C40—C42	107.8 (8)
H22B—C22—H22C	109.5	C43—C40—C42	110.3 (8)
C20—C23—H23A	109.5	C41—C40—C39	111.2 (6)
C20—C23—H23B	109.5	C43—C40—C39	106.7 (7)
H23A—C23—H23B	109.5	C42—C40—C39	109.4 (7)
C20—C23—H23C	109.5	C40—C41—H41A	109.5
H23A—C23—H23C	109.5	C40—C41—H41B	109.5
H23B—C23—H23C	109.5	H41A—C41—H41B	109.5
O2—C24—C25	112.8 (7)	C40—C41—H41C	109.5
O2—C24—H24A	109.0	H41A—C41—H41C	109.5
C25—C24—H24A	109.0	H41B—C41—H41C	109.5
O2—C24—H24B	109.0	C40—C42—H42A	109.5
C25—C24—H24B	109.0	C40—C42—H42B	109.5
H24A—C24—H24B	107.8	H42A—C42—H42B	109.5
C24—C25—C27B	102.8 (14)	C40—C42—H42C	109.5
C24—C25—C27A	106.0 (9)	H42A—C42—H42C	109.5
C24—C25—C26A	113.7 (10)	H42B—C42—H42C	109.5
C27A—C25—C26A	109.7 (12)	C40—C43—H43A	109.5
C24—C25—C28B	121.5 (12)	C40—C43—H43B	109.5
C27B—C25—C28B	103.9 (17)	H43A—C43—H43B	109.5
C24—C25—C28A	106.4 (10)	C40—C43—H43C	109.5
C27A—C25—C28A	111.3 (12)	H43A—C43—H43C	109.5
C26A—C25—C28A	109.8 (13)	H43B—C43—H43C	109.5
C24—C25—C26B	108.6 (14)	C45—C44—N1	112.4 (15)
C27B—C25—C26B	108.3 (18)	C45—C44—H44	123.8
C28B—C25—C26B	110.6 (17)	N1—C44—H44	123.8
C25—C26A—H26A	109.5	C44—C45—C46	124.5 (16)
C25—C26A—H26B	109.5	C44—C45—H45	117.7
H26A—C26A—H26B	109.5	C46—C45—H45	117.7
C25—C26A—H26C	109.5	C47—C46—C45	119.5 (14)
H26A—C26A—H26C	109.5	C47—C46—H46	120.3
H26B—C26A—H26C	109.5	C45—C46—H46	120.3
C25—C27A—H27A	109.5	C46—C47—C48	123.8 (17)
C25—C27A—H27B	109.5	C46—C47—H47	118.1
H27A—C27A—H27B	109.5	C48—C47—H47	118.1
C25—C27A—H27C	109.5	N1—C48—C47	117.0 (16)
H27A—C27A—H27C	109.5	N1—C48—H48	121.5
H27B—C27A—H27C	109.5	C47—C48—H48	121.5

C6—C1—C2—C3	1.5 (9)	C12—C11—C14—C11ⁱ	89.1 (5)
C18—C1—C2—C3	−177.4 (6)	C10—C11—C14—C11ⁱ	−87.5 (5)
C19—O1—C3—C4	−177.8 (6)	C39—O5—C16—C15	22.9 (8)
C19—O1—C3—C2	1.3 (10)	C39—O5—C16—C17	−158.2 (6)
C1—C2—C3—O1	−179.0 (6)	C17ⁱ—C15—C16—O5	−175.5 (5)
C1—C2—C3—C4	0.2 (9)	C17ⁱ—C15—C16—C17	5.7 (8)
O1—C3—C4—C5	178.0 (5)	O5—C16—C17—C15ⁱ	176.4 (5)
C2—C3—C4—C5	−1.2 (9)	C15—C16—C17—C15ⁱ	−4.7 (7)
O1—C3—C4—C7	−2.4 (9)	O5—C16—C17—C18	−5.6 (8)
C2—C3—C4—C7	178.4 (6)	C15—C16—C17—C18	173.3 (5)
C3—C4—C5—C6	0.5 (9)	C15ⁱ—C17—C18—C1	92.8 (6)
C7—C4—C5—C6	−179.1 (5)	C16—C17—C18—C1	−85.1 (7)
C24—O2—C6—C1	−177.3 (6)	C2—C1—C18—C17	93.7 (7)
C24—O2—C6—C5	0.5 (9)	C6—C1—C18—C17	−85.2 (7)
C2—C1—C6—O2	175.6 (5)	C3—O1—C19—C20	176.0 (6)
C18—C1—C6—O2	−5.5 (8)	O1—C19—C20—C22	−65.9 (9)
C2—C1—C6—C5	−2.2 (8)	O1—C19—C20—C23	177.1 (7)
C18—C1—C6—C5	176.7 (6)	O1—C19—C20—C21	57.5 (10)
C4—C5—C6—O2	−176.4 (5)	C6—O2—C24—C25	159.9 (7)
C4—C5—C6—C1	1.2 (9)	O2—C24—C25—C27B	−92.6 (17)
C3—C4—C7—C8	−103.6 (7)	O2—C24—C25—C27A	64.5 (13)
C5—C4—C7—C8	76.0 (7)	O2—C24—C25—C26A	−56.1 (15)
C4—C7—C8—C13	−89.9 (7)	O2—C24—C25—C28B	23 (2)
C4—C7—C8—C9	90.4 (7)	O2—C24—C25—C28A	−177.0 (11)
C13—C8—C9—C10	1.5 (8)	O2—C24—C25—C26B	152.8 (15)
C7—C8—C9—C10	−178.8 (5)	C10—O3—C29—C30	156.6 (6)
C8—C9—C10—O3	−176.0 (5)	O3—C29—C30—C31	57.5 (10)
C8—C9—C10—C11	1.5 (9)	O3—C29—C30—C32	−62.7 (9)
C29—O3—C10—C9	17.8 (8)	O3—C29—C30—C33	175.9 (8)
C29—O3—C10—C11	−159.8 (6)	C13—O4—C34—C35	−177.1 (6)
C9—C10—C11—C12	−2.1 (8)	O4—C34—C35—C37	59.2 (9)
O3—C10—C11—C12	175.6 (5)	O4—C34—C35—C36	−61.0 (8)
C9—C10—C11—C14	174.7 (6)	O4—C34—C35—C38	−179.2 (6)
O3—C10—C11—C14	−7.6 (8)	C16—O5—C39—C40	161.0 (6)
C10—C11—C12—C13	−0.4 (8)	O5—C39—C40—C41	57.5 (9)
C14—C11—C12—C13	−177.2 (6)	O5—C39—C40—C43	179.2 (8)
C9—C8—C13—C12	−3.9 (8)	O5—C39—C40—C42	−61.5 (9)
C7—C8—C13—C12	176.3 (5)	C48—N1—C44—C45	2.9 (19)
C9—C8—C13—O4	−179.1 (5)	N1—C44—C45—C46	0.1 (19)
C7—C8—C13—O4	1.2 (8)	C44—C45—C46—C47	−3 (2)
C11—C12—C13—C8	3.4 (9)	C45—C46—C47—C48	3 (2)
C11—C12—C13—O4	178.7 (5)	C44—N1—C48—C47	−3 (2)
C34—O4—C13—C8	−117.8 (6)	C46—C47—C48—N1	0 (2)
C34—O4—C13—C12	66.9 (7)

Symmetry code: (i) −x+1, −y, z.

Hydrogen-bond geometry (Å, º) top

π denotes the centroid of the pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C46—H46···O4	0.93	2.88	3.56 (1)	131
C24—H24B···π	0.97	2.99	3.921 (11)	161
C19—H19B···N1ⁱ	0.97	2.97	3.81 (1)	145
C39—H39B···N1ⁱ	0.97	3.17	3.74 (1)	120

Symmetry code: (i) −x+1, −y, z.

Funding information

The support of the Kuwait University Research Administration (research grant No. SC 05/23) and the facilities of RSPU through grant Nos. GS 03/08 (Rigaku RAPID II, Japan), GS 01/01 (NMR-Bruker DPX Avance 400, Germany) and GS 01/03 (GC MS Thermo Scientific, Germany) are gratefully acknowledged.

References

Al-Azemi, T. F., Vinodh, M., Alipour, F. H. & Mohamod, A. A. (2019). RSC Adv. 9, 23295–23301. CAS PubMed Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jie, K., Zhou, Y., Li, E. & Huang, F. (2018). Acc. Chem. Res. 51, 2064–2072. CrossRef CAS PubMed Google Scholar
Li, Q., Zhu, H. & Huang, F. (2020). Trends Chem. 2, 850–864. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ogoshi, T., Yamagishi, T. & Nakamoto, Y. (2016). Chem. Rev. 116, 7937–8002. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku (2016). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2017). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wu, J.-R., Wu, G., Li, D., Li, M.-H., Wang, Y. & Yang, Y.-W. (2023). Nat. Commun. 14, 5954. CSD CrossRef PubMed Google Scholar
Wu, Y., Tang, M., Wang, Z., Shi, L., Xiong, Z., Chen, Z., Sessler, J. L. & Huang, F. (2023). Nat. Commun. 14, 4927. CSD CrossRef PubMed Google Scholar
Wu, Y., Zhou, J., Li, E., Wang, M., Jie, K., Zhu, H. & Huang, F. (2020). J. Am. Chem. Soc. 142, 19722–19730. CSD CrossRef CAS PubMed Google Scholar
Zhao, X., Hua, B. & Shao, L. (2024). Chem. Commun. 60, 1164–1167. CSD CrossRef CAS Google Scholar

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Volume 9| Part 11| November 2024| x241073

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Structural insights into 1,4-bis­­(neopent­yl­oxy)pillar[5]arene and the pyridine host–guest system

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

Structural insights into 1,4-bis(neopentyloxy)pillar[5]arene and the pyridine host–guest system