organic compounds
2,9,12,15,18,25,27,34,37,40,43,50-Dodecaoxa-56-azaheptacyclo[24.24.5.151,55.03,8.019,24.028,33.044,49]hexapentaconta-3,5,7,19(24),20,22,28(33),29,31,44,46,48,51,53,55-pentadecaene
aDepartment of Chemistry, Konyang University, Nonsan 320-711, Republic of Korea, and bPDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea
*Correspondence e-mail: , jylee@konyang.ac.kr
The title compound, C43H45NO12, was prepared from the reaction of 2,6-bis(dibromomethyl)pyridine and bisphenol in the presence of caesium carbonate as a base. The central ring makes dihedral angles of 64.83 (6), 13.48 (6), 56.96 (6) and 66.21 (6)° with the peripheral rings. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions, forming a folded structure.
Related literature
For background to crown ether-based macrocyclic compounds and their inclusion behaviour, see: Weber & Vögtle, (1976, 1980). For the preparation and crystal structures of related compounds, see: Lee et al. (2009); Beack et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2000); cell SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL
Supporting information
https://doi.org/10.1107/S1600536812038093/lx2264sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038093/lx2264Isup2.hkl
To a refluxing suspension of caesium carbonate (14.1 mmol) in THF under nitrogen was added dropwise a solution of 2,6-bis(dibromomethyl)pyridine (2.82 mmol) and 1,8-bis(2-hydroxyphenoxy)-3,6-dioxaoctane (6.21 mmol) in THF over a period of 1 h. The mixture was then refluxed for an additional 48 h. After cooling to room temperature, 10% aqueous hydrochloric acid was added. The solvent was removed under reduced pressure and the residual mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The crude product was chromatographed on a silica-gel column using a mixed solvent of ethyl acetate and n-hexane (1:2) as
and recrystallization from dichloromethane/n-hexane (1:30, v/v) gave as a crystalline solid in 24% yield (m.p. 402–404 K).All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aryl, 0.98 Å for methine, and 0.97 Å for methylene H atoms. Uiso(H) = 1.2Ueq(C) for all H atoms.
In our previous paper (Lee et al., 2009, Beack et al., 2012), we synthesized and reported the preparation and the solid-state structure of new crown ether bearing three aromatic subunits. As a part of our continuing interest in the development of new crown compounds, the preparation and
of new crown ether-based macrocyclic compound containing pyridine unit (Weber et al., 1976, 1980), we report herein the of the title compound.The π interactions. (Fig. 2 & Table 1; Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively).
exhibits a twisted conformation with dihedral angles of 64.83 (6) (A/B), 13.48 (6) (A/C), 56.96 (6) (A/D), 66.21 (6) (A/E), 35.31 (6) (B/E), 69.15 (6) (C/D), 80.92 (6)° (D/E). (Fig. 1. A is N1/C1-C5 pyridine ring, B, C, D, E, are C7–C12, C19–C24, C26–C31 and C38–C43 benzene rings, respectively. In the crystal, molecules are linked by weak intermolecular C—H···O and C—H···For background to crown ether-based macrocyclic compounds and their inclusion behaviour, see: Weber & Vögtle, (1976, 1980). For the preparation and crystal structures of related compounds, see: Lee et al. (2009); Beack et al. (2012).
Data collection: APEX2 (Bruker, 2000); cell
SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with the atom numbering scheme and intramolecular C—H···O and π···π interactions. Displacement ellipsoids are drawn at the 30% probability level. H atoms non-participating in hydrogen-bonding were omitted for clarity. | |
Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x+1, y, z ; (ii) x-1, y, z.] |
C43H45NO12 | Z = 2 |
Mr = 767.80 | F(000) = 812 |
Triclinic, P1 | Dx = 1.360 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5266 (4) Å | Cell parameters from 9368 reflections |
b = 15.2732 (7) Å | θ = 2.6–27.5° |
c = 15.5688 (8) Å | µ = 0.10 mm−1 |
α = 69.752 (2)° | T = 296 K |
β = 88.372 (2)° | Block, colourless |
γ = 80.402 (2)° | 0.25 × 0.19 × 0.13 mm |
V = 1874.64 (16) Å3 |
Bruker APEXII CCD diffractometer | 8622 independent reflections |
Radiation source: fine-focus sealed tube | 7657 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
π and ω scans | θmax = 27.6°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.975, Tmax = 0.988 | k = −19→19 |
33651 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0469P)2 + 0.7124P] where P = (Fo2 + 2Fc2)/3 |
8622 reflections | (Δ/σ)max = 0.001 |
505 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C43H45NO12 | γ = 80.402 (2)° |
Mr = 767.80 | V = 1874.64 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5266 (4) Å | Mo Kα radiation |
b = 15.2732 (7) Å | µ = 0.10 mm−1 |
c = 15.5688 (8) Å | T = 296 K |
α = 69.752 (2)° | 0.25 × 0.19 × 0.13 mm |
β = 88.372 (2)° |
Bruker APEXII CCD diffractometer | 8622 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7657 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.988 | Rint = 0.024 |
33651 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.28 e Å−3 |
8622 reflections | Δρmin = −0.27 e Å−3 |
505 parameters |
Experimental. IR(KBr pellet, cm-1): 2926, 1583, 1500, 1454, 1260, 1122, 1055, 973, 745. 1H NMR (CDCl3): δ 7.98 (d, 2 H, pyd-H), 7.93 (t, 1 H, pyd-H). 7.06~6.72 (m, 16 H, Ar-H), 6.86 (s, 2 H, pyd-CHOO), 3.95(t, 8 H, ArOCH2CH2O), 3.58(t, 8 H, ArOCH2CH2O), 3.39(s, 8 H, ArOCH2CH2OCH2CH2O). 13C NMR (CDCl3): d 157.443, 151.085, 146.497, 137.688, 124.763, 122.382, 121.690, 114.131, 104.316, 71.976, 70.049, 69.576 p.p.m.. |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.16048 (10) | 0.23963 (6) | 0.34935 (6) | 0.01732 (18) | |
O1 | 0.42156 (9) | 0.02455 (5) | 0.36551 (5) | 0.02018 (16) | |
O2 | 0.23385 (10) | −0.10515 (6) | 0.38118 (6) | 0.02562 (18) | |
O3 | −0.06713 (10) | −0.01380 (6) | 0.37368 (6) | 0.02620 (18) | |
O4 | −0.29589 (11) | 0.15178 (6) | 0.28839 (6) | 0.0302 (2) | |
O5 | −0.30106 (10) | 0.34100 (6) | 0.31315 (6) | 0.02827 (19) | |
O6 | −0.09806 (9) | 0.37352 (6) | 0.42255 (5) | 0.02140 (16) | |
O7 | 0.06804 (10) | 0.47547 (5) | 0.34239 (6) | 0.02325 (17) | |
O8 | 0.18306 (10) | 0.43854 (6) | 0.18692 (6) | 0.02400 (17) | |
O9 | 0.25086 (11) | 0.45435 (6) | −0.00716 (6) | 0.02920 (19) | |
O10 | 0.55737 (10) | 0.32192 (6) | −0.01372 (6) | 0.02566 (18) | |
O11 | 0.49707 (10) | 0.14304 (6) | 0.10207 (6) | 0.02586 (18) | |
O12 | 0.31057 (10) | 0.14756 (5) | 0.23457 (5) | 0.02138 (16) | |
C1 | 0.15225 (12) | 0.30759 (7) | 0.38556 (7) | 0.0179 (2) | |
C2 | 0.26197 (14) | 0.30632 (8) | 0.45049 (8) | 0.0221 (2) | |
H2A | 0.2531 | 0.3556 | 0.4734 | 0.027* | |
C3 | 0.38433 (14) | 0.23023 (8) | 0.48010 (8) | 0.0234 (2) | |
H3A | 0.4587 | 0.2270 | 0.5241 | 0.028* | |
C4 | 0.39516 (13) | 0.15860 (7) | 0.44349 (7) | 0.0195 (2) | |
H4A | 0.4759 | 0.1063 | 0.4627 | 0.023* | |
C5 | 0.28230 (12) | 0.16721 (7) | 0.37739 (7) | 0.0167 (2) | |
C6 | 0.28892 (12) | 0.09688 (7) | 0.32825 (7) | 0.0173 (2) | |
H6A | 0.1903 | 0.0703 | 0.3359 | 0.021* | |
C7 | 0.46007 (13) | −0.04066 (7) | 0.32113 (7) | 0.0194 (2) | |
C8 | 0.59910 (14) | −0.04026 (8) | 0.27378 (8) | 0.0236 (2) | |
H8A | 0.6615 | 0.0058 | 0.2682 | 0.028* | |
C9 | 0.64556 (15) | −0.10925 (9) | 0.23426 (9) | 0.0296 (3) | |
H9A | 0.7401 | −0.1100 | 0.2031 | 0.035* | |
C10 | 0.55131 (16) | −0.17632 (9) | 0.24142 (9) | 0.0308 (3) | |
H10A | 0.5829 | −0.2222 | 0.2150 | 0.037* | |
C11 | 0.40934 (15) | −0.17611 (8) | 0.28783 (9) | 0.0267 (2) | |
H11A | 0.3452 | −0.2208 | 0.2912 | 0.032* | |
C12 | 0.36402 (13) | −0.10881 (8) | 0.32907 (8) | 0.0212 (2) | |
C13 | 0.10545 (14) | −0.14958 (8) | 0.36882 (9) | 0.0273 (2) | |
H13A | 0.1333 | −0.2179 | 0.3959 | 0.033* | |
H13B | 0.0803 | −0.1330 | 0.3042 | 0.033* | |
C14 | −0.03361 (14) | −0.11372 (8) | 0.41581 (9) | 0.0266 (2) | |
H14A | −0.1254 | −0.1413 | 0.4097 | 0.032* | |
H14B | −0.0081 | −0.1308 | 0.4805 | 0.032* | |
C15 | −0.17984 (14) | 0.03039 (8) | 0.42142 (8) | 0.0243 (2) | |
H15A | −0.1398 | 0.0171 | 0.4831 | 0.029* | |
H15B | −0.2791 | 0.0063 | 0.4253 | 0.029* | |
C16 | −0.20694 (14) | 0.13527 (8) | 0.36989 (8) | 0.0239 (2) | |
H16A | −0.2653 | 0.1687 | 0.4068 | 0.029* | |
H16B | −0.1059 | 0.1574 | 0.3551 | 0.029* | |
C17 | −0.31024 (16) | 0.24439 (9) | 0.22326 (8) | 0.0288 (3) | |
H17A | −0.3607 | 0.2455 | 0.1677 | 0.035* | |
H17B | −0.2044 | 0.2593 | 0.2082 | 0.035* | |
C18 | −0.40408 (15) | 0.32034 (8) | 0.25400 (8) | 0.0258 (2) | |
H18A | −0.4397 | 0.3767 | 0.2015 | 0.031* | |
H18B | −0.4967 | 0.2985 | 0.2866 | 0.031* | |
C19 | −0.35332 (13) | 0.41479 (8) | 0.34239 (8) | 0.0212 (2) | |
C20 | −0.50285 (14) | 0.47113 (8) | 0.32230 (8) | 0.0245 (2) | |
H20A | −0.5782 | 0.4579 | 0.2885 | 0.029* | |
C21 | −0.53898 (15) | 0.54706 (9) | 0.35292 (9) | 0.0307 (3) | |
H21A | −0.6386 | 0.5851 | 0.3388 | 0.037* | |
C22 | −0.42956 (16) | 0.56692 (10) | 0.40388 (10) | 0.0355 (3) | |
H22A | −0.4545 | 0.6187 | 0.4232 | 0.043* | |
C23 | −0.28131 (15) | 0.50912 (9) | 0.42638 (9) | 0.0295 (3) | |
H23A | −0.2077 | 0.5215 | 0.4618 | 0.035* | |
C24 | −0.24379 (13) | 0.43376 (8) | 0.39619 (8) | 0.0214 (2) | |
C25 | 0.01485 (13) | 0.38871 (7) | 0.35244 (7) | 0.0189 (2) | |
H25A | −0.0319 | 0.3911 | 0.2947 | 0.023* | |
C26 | 0.05292 (13) | 0.54533 (8) | 0.25695 (8) | 0.0231 (2) | |
C27 | −0.01090 (16) | 0.63690 (9) | 0.25206 (10) | 0.0325 (3) | |
H27A | −0.0470 | 0.6487 | 0.3046 | 0.039* | |
C28 | −0.02063 (18) | 0.71077 (9) | 0.16855 (11) | 0.0393 (3) | |
H28A | −0.0623 | 0.7721 | 0.1654 | 0.047* | |
C29 | 0.03125 (16) | 0.69367 (9) | 0.09012 (10) | 0.0350 (3) | |
H29A | 0.0227 | 0.7432 | 0.0342 | 0.042* | |
C30 | 0.09607 (14) | 0.60270 (9) | 0.09464 (9) | 0.0283 (3) | |
H30A | 0.1313 | 0.5913 | 0.0418 | 0.034* | |
C31 | 0.10854 (13) | 0.52837 (8) | 0.17819 (8) | 0.0227 (2) | |
C32 | 0.11733 (14) | 0.39272 (8) | 0.13235 (8) | 0.0239 (2) | |
H32A | 0.0240 | 0.4341 | 0.0980 | 0.029* | |
H32B | 0.0843 | 0.3349 | 0.1726 | 0.029* | |
C33 | 0.23586 (15) | 0.36951 (8) | 0.06713 (8) | 0.0254 (2) | |
H33A | 0.3382 | 0.3412 | 0.0986 | 0.030* | |
H33B | 0.2007 | 0.3244 | 0.0440 | 0.030* | |
C34 | 0.32053 (15) | 0.43884 (9) | −0.08583 (8) | 0.0288 (3) | |
H34A | 0.2906 | 0.4956 | −0.1389 | 0.035* | |
H34B | 0.2776 | 0.3881 | −0.0958 | 0.035* | |
C35 | 0.50017 (15) | 0.41369 (9) | −0.07829 (9) | 0.0282 (3) | |
H35A | 0.5403 | 0.4168 | −0.1380 | 0.034* | |
H35B | 0.5423 | 0.4605 | −0.0607 | 0.034* | |
C36 | 0.54982 (16) | 0.24892 (9) | −0.04898 (8) | 0.0286 (3) | |
H36A | 0.6199 | 0.2547 | −0.1001 | 0.034* | |
H36B | 0.4421 | 0.2531 | −0.0704 | 0.034* | |
C37 | 0.60036 (15) | 0.15579 (9) | 0.02652 (9) | 0.0289 (3) | |
H37A | 0.6010 | 0.1048 | 0.0028 | 0.035* | |
H37B | 0.7079 | 0.1527 | 0.0475 | 0.035* | |
C38 | 0.35459 (14) | 0.11590 (8) | 0.09707 (8) | 0.0215 (2) | |
C39 | 0.30404 (15) | 0.08776 (9) | 0.02814 (8) | 0.0272 (2) | |
H39A | 0.3683 | 0.0885 | −0.0213 | 0.033* | |
C40 | 0.15708 (16) | 0.05847 (9) | 0.03322 (9) | 0.0305 (3) | |
H40A | 0.1244 | 0.0385 | −0.0124 | 0.037* | |
C41 | 0.05942 (15) | 0.05870 (9) | 0.10527 (9) | 0.0294 (3) | |
H41A | −0.0385 | 0.0388 | 0.1081 | 0.035* | |
C42 | 0.10706 (14) | 0.08869 (8) | 0.17370 (8) | 0.0246 (2) | |
H42A | 0.0400 | 0.0906 | 0.2214 | 0.029* | |
C43 | 0.25443 (13) | 0.11560 (7) | 0.17044 (7) | 0.0200 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0178 (4) | 0.0167 (4) | 0.0183 (4) | −0.0034 (3) | 0.0012 (3) | −0.0068 (3) |
O1 | 0.0203 (4) | 0.0186 (4) | 0.0234 (4) | 0.0012 (3) | −0.0028 (3) | −0.0113 (3) |
O2 | 0.0233 (4) | 0.0263 (4) | 0.0326 (4) | −0.0074 (3) | 0.0036 (3) | −0.0156 (4) |
O3 | 0.0253 (4) | 0.0204 (4) | 0.0288 (4) | −0.0022 (3) | 0.0060 (3) | −0.0046 (3) |
O4 | 0.0370 (5) | 0.0203 (4) | 0.0340 (5) | −0.0065 (3) | −0.0120 (4) | −0.0083 (4) |
O5 | 0.0252 (4) | 0.0253 (4) | 0.0392 (5) | 0.0001 (3) | −0.0074 (4) | −0.0187 (4) |
O6 | 0.0182 (4) | 0.0241 (4) | 0.0211 (4) | 0.0004 (3) | 0.0008 (3) | −0.0086 (3) |
O7 | 0.0264 (4) | 0.0181 (4) | 0.0267 (4) | −0.0032 (3) | −0.0016 (3) | −0.0096 (3) |
O8 | 0.0226 (4) | 0.0212 (4) | 0.0273 (4) | 0.0023 (3) | −0.0012 (3) | −0.0099 (3) |
O9 | 0.0335 (5) | 0.0239 (4) | 0.0270 (4) | −0.0037 (3) | 0.0087 (3) | −0.0060 (3) |
O10 | 0.0277 (4) | 0.0261 (4) | 0.0241 (4) | −0.0056 (3) | 0.0015 (3) | −0.0094 (3) |
O11 | 0.0278 (4) | 0.0291 (4) | 0.0229 (4) | −0.0090 (3) | 0.0024 (3) | −0.0101 (3) |
O12 | 0.0294 (4) | 0.0203 (4) | 0.0171 (4) | −0.0079 (3) | 0.0007 (3) | −0.0081 (3) |
C1 | 0.0178 (5) | 0.0172 (5) | 0.0193 (5) | −0.0035 (4) | 0.0019 (4) | −0.0067 (4) |
C2 | 0.0261 (6) | 0.0200 (5) | 0.0230 (5) | −0.0026 (4) | −0.0017 (4) | −0.0115 (4) |
C3 | 0.0249 (6) | 0.0238 (5) | 0.0228 (5) | −0.0027 (4) | −0.0056 (4) | −0.0099 (4) |
C4 | 0.0192 (5) | 0.0183 (5) | 0.0200 (5) | −0.0007 (4) | −0.0011 (4) | −0.0065 (4) |
C5 | 0.0181 (5) | 0.0160 (5) | 0.0164 (5) | −0.0045 (4) | 0.0031 (4) | −0.0055 (4) |
C6 | 0.0178 (5) | 0.0158 (5) | 0.0178 (5) | −0.0017 (4) | −0.0004 (4) | −0.0057 (4) |
C7 | 0.0217 (5) | 0.0170 (5) | 0.0195 (5) | 0.0019 (4) | −0.0044 (4) | −0.0084 (4) |
C8 | 0.0231 (5) | 0.0232 (5) | 0.0252 (6) | −0.0017 (4) | −0.0014 (4) | −0.0102 (4) |
C9 | 0.0268 (6) | 0.0339 (6) | 0.0312 (6) | −0.0004 (5) | 0.0040 (5) | −0.0177 (5) |
C10 | 0.0341 (7) | 0.0299 (6) | 0.0347 (7) | 0.0017 (5) | −0.0007 (5) | −0.0221 (5) |
C11 | 0.0291 (6) | 0.0223 (5) | 0.0327 (6) | −0.0029 (4) | −0.0032 (5) | −0.0146 (5) |
C12 | 0.0209 (5) | 0.0191 (5) | 0.0227 (5) | 0.0008 (4) | −0.0035 (4) | −0.0078 (4) |
C13 | 0.0261 (6) | 0.0208 (5) | 0.0374 (7) | −0.0068 (4) | 0.0002 (5) | −0.0118 (5) |
C14 | 0.0257 (6) | 0.0204 (5) | 0.0321 (6) | −0.0073 (4) | 0.0025 (5) | −0.0057 (5) |
C15 | 0.0205 (5) | 0.0255 (6) | 0.0258 (6) | −0.0041 (4) | 0.0022 (4) | −0.0077 (5) |
C16 | 0.0216 (5) | 0.0248 (6) | 0.0269 (6) | −0.0052 (4) | −0.0010 (4) | −0.0102 (5) |
C17 | 0.0387 (7) | 0.0236 (6) | 0.0251 (6) | −0.0061 (5) | −0.0033 (5) | −0.0089 (5) |
C18 | 0.0281 (6) | 0.0224 (5) | 0.0273 (6) | −0.0063 (4) | −0.0061 (5) | −0.0076 (5) |
C19 | 0.0221 (5) | 0.0185 (5) | 0.0228 (5) | −0.0039 (4) | 0.0024 (4) | −0.0067 (4) |
C20 | 0.0215 (5) | 0.0243 (5) | 0.0255 (6) | −0.0039 (4) | −0.0011 (4) | −0.0059 (4) |
C21 | 0.0231 (6) | 0.0298 (6) | 0.0367 (7) | 0.0043 (5) | −0.0004 (5) | −0.0121 (5) |
C22 | 0.0314 (7) | 0.0339 (7) | 0.0469 (8) | 0.0049 (5) | −0.0010 (6) | −0.0257 (6) |
C23 | 0.0256 (6) | 0.0341 (7) | 0.0347 (7) | −0.0010 (5) | −0.0013 (5) | −0.0209 (5) |
C24 | 0.0178 (5) | 0.0227 (5) | 0.0230 (5) | −0.0011 (4) | 0.0023 (4) | −0.0083 (4) |
C25 | 0.0192 (5) | 0.0186 (5) | 0.0205 (5) | −0.0026 (4) | 0.0012 (4) | −0.0093 (4) |
C26 | 0.0191 (5) | 0.0185 (5) | 0.0310 (6) | −0.0027 (4) | 0.0009 (4) | −0.0077 (4) |
C27 | 0.0341 (7) | 0.0223 (6) | 0.0408 (7) | −0.0005 (5) | 0.0065 (5) | −0.0127 (5) |
C28 | 0.0412 (8) | 0.0176 (6) | 0.0533 (9) | 0.0008 (5) | 0.0056 (6) | −0.0081 (6) |
C29 | 0.0339 (7) | 0.0217 (6) | 0.0398 (7) | −0.0027 (5) | 0.0029 (5) | 0.0002 (5) |
C30 | 0.0238 (6) | 0.0252 (6) | 0.0316 (6) | −0.0036 (5) | 0.0034 (5) | −0.0050 (5) |
C31 | 0.0164 (5) | 0.0197 (5) | 0.0307 (6) | −0.0012 (4) | 0.0009 (4) | −0.0078 (4) |
C32 | 0.0238 (5) | 0.0227 (5) | 0.0252 (6) | −0.0045 (4) | 0.0015 (4) | −0.0080 (4) |
C33 | 0.0287 (6) | 0.0214 (5) | 0.0236 (6) | −0.0019 (4) | 0.0029 (4) | −0.0060 (4) |
C34 | 0.0285 (6) | 0.0325 (6) | 0.0221 (6) | −0.0050 (5) | 0.0032 (5) | −0.0054 (5) |
C35 | 0.0281 (6) | 0.0282 (6) | 0.0261 (6) | −0.0076 (5) | 0.0044 (5) | −0.0058 (5) |
C36 | 0.0319 (6) | 0.0337 (6) | 0.0246 (6) | −0.0094 (5) | 0.0075 (5) | −0.0144 (5) |
C37 | 0.0263 (6) | 0.0300 (6) | 0.0330 (6) | −0.0032 (5) | 0.0069 (5) | −0.0151 (5) |
C38 | 0.0254 (5) | 0.0173 (5) | 0.0212 (5) | −0.0020 (4) | −0.0018 (4) | −0.0064 (4) |
C39 | 0.0347 (6) | 0.0267 (6) | 0.0232 (6) | −0.0043 (5) | 0.0014 (5) | −0.0128 (5) |
C40 | 0.0378 (7) | 0.0314 (6) | 0.0280 (6) | −0.0057 (5) | −0.0067 (5) | −0.0168 (5) |
C41 | 0.0276 (6) | 0.0310 (6) | 0.0322 (6) | −0.0061 (5) | −0.0061 (5) | −0.0130 (5) |
C42 | 0.0241 (6) | 0.0258 (6) | 0.0241 (5) | −0.0022 (4) | −0.0012 (4) | −0.0098 (5) |
C43 | 0.0264 (5) | 0.0153 (5) | 0.0183 (5) | −0.0009 (4) | −0.0040 (4) | −0.0067 (4) |
N1—C1 | 1.3336 (13) | C16—H16A | 0.9700 |
N1—C5 | 1.3421 (13) | C16—H16B | 0.9700 |
O1—C7 | 1.3900 (12) | C17—C18 | 1.5060 (17) |
O1—C6 | 1.4188 (12) | C17—H17A | 0.9700 |
O2—C12 | 1.3612 (14) | C17—H17B | 0.9700 |
O2—C13 | 1.4305 (14) | C18—H18A | 0.9700 |
O3—C14 | 1.4189 (14) | C18—H18B | 0.9700 |
O3—C15 | 1.4220 (14) | C19—C20 | 1.3908 (16) |
O4—C17 | 1.4144 (14) | C19—C24 | 1.4002 (16) |
O4—C16 | 1.4207 (14) | C20—C21 | 1.3864 (17) |
O5—C19 | 1.3608 (13) | C20—H20A | 0.9300 |
O5—C18 | 1.4349 (14) | C21—C22 | 1.3765 (19) |
O6—C24 | 1.3947 (13) | C21—H21A | 0.9300 |
O6—C25 | 1.4184 (13) | C22—C23 | 1.3924 (18) |
O7—C26 | 1.3805 (14) | C22—H22A | 0.9300 |
O7—C25 | 1.4279 (13) | C23—C24 | 1.3752 (16) |
O8—C31 | 1.3746 (13) | C23—H23A | 0.9300 |
O8—C32 | 1.4475 (14) | C25—H25A | 0.9800 |
O9—C34 | 1.4219 (15) | C26—C27 | 1.3903 (16) |
O9—C33 | 1.4292 (14) | C26—C31 | 1.3934 (17) |
O10—C36 | 1.4136 (14) | C27—C28 | 1.389 (2) |
O10—C35 | 1.4274 (15) | C27—H27A | 0.9300 |
O11—C38 | 1.3599 (14) | C28—C29 | 1.381 (2) |
O11—C37 | 1.4272 (14) | C28—H28A | 0.9300 |
O12—C43 | 1.3807 (13) | C29—C30 | 1.3853 (18) |
O12—C6 | 1.4182 (13) | C29—H29A | 0.9300 |
C1—C2 | 1.3899 (15) | C30—C31 | 1.3920 (17) |
C1—C25 | 1.5105 (14) | C30—H30A | 0.9300 |
C2—C3 | 1.3798 (16) | C32—C33 | 1.4998 (16) |
C2—H2A | 0.9300 | C32—H32A | 0.9700 |
C3—C4 | 1.3874 (15) | C32—H32B | 0.9700 |
C3—H3A | 0.9300 | C33—H33A | 0.9700 |
C4—C5 | 1.3866 (15) | C33—H33B | 0.9700 |
C4—H4A | 0.9300 | C34—C35 | 1.5133 (17) |
C5—C6 | 1.5127 (14) | C34—H34A | 0.9700 |
C6—H6A | 0.9800 | C34—H34B | 0.9700 |
C7—C8 | 1.3779 (16) | C35—H35A | 0.9700 |
C7—C12 | 1.3996 (16) | C35—H35B | 0.9700 |
C8—C9 | 1.3935 (16) | C36—C37 | 1.5025 (18) |
C8—H8A | 0.9300 | C36—H36A | 0.9700 |
C9—C10 | 1.3777 (19) | C36—H36B | 0.9700 |
C9—H9A | 0.9300 | C37—H37A | 0.9700 |
C10—C11 | 1.3922 (18) | C37—H37B | 0.9700 |
C10—H10A | 0.9300 | C38—C39 | 1.3890 (16) |
C11—C12 | 1.3886 (15) | C38—C43 | 1.4059 (16) |
C11—H11A | 0.9300 | C39—C40 | 1.3904 (19) |
C13—C14 | 1.5009 (17) | C39—H39A | 0.9300 |
C13—H13A | 0.9700 | C40—C41 | 1.3787 (19) |
C13—H13B | 0.9700 | C40—H40A | 0.9300 |
C14—H14A | 0.9700 | C41—C42 | 1.3908 (16) |
C14—H14B | 0.9700 | C41—H41A | 0.9300 |
C15—C16 | 1.5035 (16) | C42—C43 | 1.3801 (16) |
C15—H15A | 0.9700 | C42—H42A | 0.9300 |
C15—H15B | 0.9700 | ||
C1—N1—C5 | 117.46 (9) | C21—C20—H20A | 120.2 |
C7—O1—C6 | 116.18 (8) | C19—C20—H20A | 120.2 |
C12—O2—C13 | 118.30 (9) | C22—C21—C20 | 120.95 (11) |
C14—O3—C15 | 113.10 (9) | C22—C21—H21A | 119.5 |
C17—O4—C16 | 115.62 (9) | C20—C21—H21A | 119.5 |
C19—O5—C18 | 118.56 (9) | C21—C22—C23 | 119.65 (12) |
C24—O6—C25 | 113.49 (8) | C21—C22—H22A | 120.2 |
C26—O7—C25 | 118.20 (9) | C23—C22—H22A | 120.2 |
C31—O8—C32 | 116.75 (9) | C24—C23—C22 | 119.97 (12) |
C34—O9—C33 | 114.12 (9) | C24—C23—H23A | 120.0 |
C36—O10—C35 | 112.52 (9) | C22—C23—H23A | 120.0 |
C38—O11—C37 | 119.56 (9) | C23—C24—O6 | 119.67 (10) |
C43—O12—C6 | 117.59 (8) | C23—C24—C19 | 120.52 (10) |
N1—C1—C2 | 123.34 (10) | O6—C24—C19 | 119.76 (10) |
N1—C1—C25 | 116.51 (9) | O6—C25—O7 | 107.64 (8) |
C2—C1—C25 | 120.15 (9) | O6—C25—C1 | 106.58 (8) |
C3—C2—C1 | 118.40 (10) | O7—C25—C1 | 109.53 (9) |
C3—C2—H2A | 120.8 | O6—C25—H25A | 111.0 |
C1—C2—H2A | 120.8 | O7—C25—H25A | 111.0 |
C2—C3—C4 | 119.27 (10) | C1—C25—H25A | 111.0 |
C2—C3—H3A | 120.4 | O7—C26—C27 | 117.48 (11) |
C4—C3—H3A | 120.4 | O7—C26—C31 | 122.60 (10) |
C5—C4—C3 | 118.16 (10) | C27—C26—C31 | 119.77 (11) |
C5—C4—H4A | 120.9 | C28—C27—C26 | 119.86 (13) |
C3—C4—H4A | 120.9 | C28—C27—H27A | 120.1 |
N1—C5—C4 | 123.32 (10) | C26—C27—H27A | 120.1 |
N1—C5—C6 | 113.98 (9) | C29—C28—C27 | 120.39 (12) |
C4—C5—C6 | 122.67 (9) | C29—C28—H28A | 119.8 |
O12—C6—O1 | 110.70 (8) | C27—C28—H28A | 119.8 |
O12—C6—C5 | 106.24 (8) | C28—C29—C30 | 120.03 (12) |
O1—C6—C5 | 107.54 (8) | C28—C29—H29A | 120.0 |
O12—C6—H6A | 110.7 | C30—C29—H29A | 120.0 |
O1—C6—H6A | 110.7 | C29—C30—C31 | 120.06 (12) |
C5—C6—H6A | 110.7 | C29—C30—H30A | 120.0 |
C8—C7—O1 | 118.66 (10) | C31—C30—H30A | 120.0 |
C8—C7—C12 | 120.82 (10) | O8—C31—C30 | 121.87 (11) |
O1—C7—C12 | 120.42 (10) | O8—C31—C26 | 118.16 (10) |
C7—C8—C9 | 119.56 (11) | C30—C31—C26 | 119.87 (11) |
C7—C8—H8A | 120.2 | O8—C32—C33 | 111.66 (10) |
C9—C8—H8A | 120.2 | O8—C32—H32A | 109.3 |
C10—C9—C8 | 119.97 (11) | C33—C32—H32A | 109.3 |
C10—C9—H9A | 120.0 | O8—C32—H32B | 109.3 |
C8—C9—H9A | 120.0 | C33—C32—H32B | 109.3 |
C9—C10—C11 | 120.73 (11) | H32A—C32—H32B | 107.9 |
C9—C10—H10A | 119.6 | O9—C33—C32 | 109.20 (9) |
C11—C10—H10A | 119.6 | O9—C33—H33A | 109.8 |
C12—C11—C10 | 119.61 (11) | C32—C33—H33A | 109.8 |
C12—C11—H11A | 120.2 | O9—C33—H33B | 109.8 |
C10—C11—H11A | 120.2 | C32—C33—H33B | 109.8 |
O2—C12—C11 | 125.04 (11) | H33A—C33—H33B | 108.3 |
O2—C12—C7 | 115.61 (10) | O9—C34—C35 | 113.57 (10) |
C11—C12—C7 | 119.30 (11) | O9—C34—H34A | 108.9 |
O2—C13—C14 | 106.10 (9) | C35—C34—H34A | 108.9 |
O2—C13—H13A | 110.5 | O9—C34—H34B | 108.9 |
C14—C13—H13A | 110.5 | C35—C34—H34B | 108.9 |
O2—C13—H13B | 110.5 | H34A—C34—H34B | 107.7 |
C14—C13—H13B | 110.5 | O10—C35—C34 | 113.72 (10) |
H13A—C13—H13B | 108.7 | O10—C35—H35A | 108.8 |
O3—C14—C13 | 107.63 (9) | C34—C35—H35A | 108.8 |
O3—C14—H14A | 110.2 | O10—C35—H35B | 108.8 |
C13—C14—H14A | 110.2 | C34—C35—H35B | 108.8 |
O3—C14—H14B | 110.2 | H35A—C35—H35B | 107.7 |
C13—C14—H14B | 110.2 | O10—C36—C37 | 107.99 (10) |
H14A—C14—H14B | 108.5 | O10—C36—H36A | 110.1 |
O3—C15—C16 | 108.15 (9) | C37—C36—H36A | 110.1 |
O3—C15—H15A | 110.1 | O10—C36—H36B | 110.1 |
C16—C15—H15A | 110.1 | C37—C36—H36B | 110.1 |
O3—C15—H15B | 110.1 | H36A—C36—H36B | 108.4 |
C16—C15—H15B | 110.1 | O11—C37—C36 | 111.95 (10) |
H15A—C15—H15B | 108.4 | O11—C37—H37A | 109.2 |
O4—C16—C15 | 107.35 (9) | C36—C37—H37A | 109.2 |
O4—C16—H16A | 110.2 | O11—C37—H37B | 109.2 |
C15—C16—H16A | 110.2 | C36—C37—H37B | 109.2 |
O4—C16—H16B | 110.2 | H37A—C37—H37B | 107.9 |
C15—C16—H16B | 110.2 | O11—C38—C39 | 125.83 (11) |
H16A—C16—H16B | 108.5 | O11—C38—C43 | 115.04 (10) |
O4—C17—C18 | 114.69 (10) | C39—C38—C43 | 119.12 (11) |
O4—C17—H17A | 108.6 | C38—C39—C40 | 119.85 (11) |
C18—C17—H17A | 108.6 | C38—C39—H39A | 120.1 |
O4—C17—H17B | 108.6 | C40—C39—H39A | 120.1 |
C18—C17—H17B | 108.6 | C41—C40—C39 | 120.63 (11) |
H17A—C17—H17B | 107.6 | C41—C40—H40A | 119.7 |
O5—C18—C17 | 107.36 (10) | C39—C40—H40A | 119.7 |
O5—C18—H18A | 110.2 | C40—C41—C42 | 120.11 (12) |
C17—C18—H18A | 110.2 | C40—C41—H41A | 119.9 |
O5—C18—H18B | 110.2 | C42—C41—H41A | 119.9 |
C17—C18—H18B | 110.2 | C43—C42—C41 | 119.65 (11) |
H18A—C18—H18B | 108.5 | C43—C42—H42A | 120.2 |
O5—C19—C20 | 125.28 (10) | C41—C42—H42A | 120.2 |
O5—C19—C24 | 115.47 (10) | C42—C43—O12 | 123.61 (10) |
C20—C19—C24 | 119.25 (10) | C42—C43—C38 | 120.61 (10) |
C21—C20—C19 | 119.61 (11) | O12—C43—C38 | 115.72 (10) |
C5—N1—C1—C2 | −0.47 (15) | C25—O6—C24—C19 | 78.83 (12) |
C5—N1—C1—C25 | 179.56 (9) | O5—C19—C24—C23 | 177.31 (11) |
N1—C1—C2—C3 | −1.01 (17) | C20—C19—C24—C23 | −2.15 (17) |
C25—C1—C2—C3 | 178.96 (10) | O5—C19—C24—O6 | −5.36 (15) |
C1—C2—C3—C4 | 0.88 (17) | C20—C19—C24—O6 | 175.18 (10) |
C2—C3—C4—C5 | 0.65 (17) | C24—O6—C25—O7 | 72.70 (11) |
C1—N1—C5—C4 | 2.15 (15) | C24—O6—C25—C1 | −169.87 (9) |
C1—N1—C5—C6 | −176.03 (9) | C26—O7—C25—O6 | −123.97 (9) |
C3—C4—C5—N1 | −2.26 (16) | C26—O7—C25—C1 | 120.53 (10) |
C3—C4—C5—C6 | 175.76 (10) | N1—C1—C25—O6 | 103.06 (10) |
C43—O12—C6—O1 | 90.74 (11) | C2—C1—C25—O6 | −76.92 (12) |
C43—O12—C6—C5 | −152.80 (9) | N1—C1—C25—O7 | −140.77 (9) |
C7—O1—C6—O12 | −56.35 (11) | C2—C1—C25—O7 | 39.25 (13) |
C7—O1—C6—C5 | −172.01 (8) | C25—O7—C26—C27 | 133.16 (11) |
N1—C5—C6—O12 | 62.05 (11) | C25—O7—C26—C31 | −51.29 (14) |
C4—C5—C6—O12 | −116.15 (11) | O7—C26—C27—C28 | 176.45 (12) |
N1—C5—C6—O1 | −179.39 (8) | C31—C26—C27—C28 | 0.77 (19) |
C4—C5—C6—O1 | 2.42 (13) | C26—C27—C28—C29 | 0.7 (2) |
C6—O1—C7—C8 | 111.11 (11) | C27—C28—C29—C30 | −1.1 (2) |
C6—O1—C7—C12 | −72.60 (13) | C28—C29—C30—C31 | 0.2 (2) |
O1—C7—C8—C9 | 175.50 (10) | C32—O8—C31—C30 | −60.17 (14) |
C12—C7—C8—C9 | −0.77 (17) | C32—O8—C31—C26 | 123.61 (11) |
C7—C8—C9—C10 | 1.06 (18) | C29—C30—C31—O8 | −174.92 (11) |
C8—C9—C10—C11 | 0.0 (2) | C29—C30—C31—C26 | 1.23 (18) |
C9—C10—C11—C12 | −1.42 (19) | O7—C26—C31—O8 | −0.86 (16) |
C13—O2—C12—C11 | −22.83 (16) | C27—C26—C31—O8 | 174.58 (11) |
C13—O2—C12—C7 | 159.87 (10) | O7—C26—C31—C30 | −177.15 (10) |
C10—C11—C12—O2 | −175.52 (11) | C27—C26—C31—C30 | −1.71 (17) |
C10—C11—C12—C7 | 1.68 (17) | C31—O8—C32—C33 | 119.02 (11) |
C8—C7—C12—O2 | 176.86 (10) | C34—O9—C33—C32 | −161.94 (10) |
O1—C7—C12—O2 | 0.65 (15) | O8—C32—C33—O9 | −75.05 (12) |
C8—C7—C12—C11 | −0.60 (16) | C33—O9—C34—C35 | −80.07 (13) |
O1—C7—C12—C11 | −176.81 (10) | C36—O10—C35—C34 | 79.12 (13) |
C12—O2—C13—C14 | −165.98 (10) | O9—C34—C35—O10 | 70.00 (14) |
C15—O3—C14—C13 | −170.45 (10) | C35—O10—C36—C37 | −175.63 (10) |
O2—C13—C14—O3 | 59.66 (12) | C38—O11—C37—C36 | 78.96 (13) |
C14—O3—C15—C16 | −179.28 (9) | O10—C36—C37—O11 | 61.68 (13) |
C17—O4—C16—C15 | −169.69 (10) | C37—O11—C38—C39 | 8.08 (17) |
O3—C15—C16—O4 | 71.86 (11) | C37—O11—C38—C43 | −173.19 (10) |
C16—O4—C17—C18 | −65.62 (14) | O11—C38—C39—C40 | 177.70 (11) |
C19—O5—C18—C17 | 173.18 (10) | C43—C38—C39—C40 | −0.98 (17) |
O4—C17—C18—O5 | 79.00 (13) | C38—C39—C40—C41 | 1.21 (19) |
C18—O5—C19—C20 | 2.43 (17) | C39—C40—C41—C42 | 0.21 (19) |
C18—O5—C19—C24 | −176.99 (10) | C40—C41—C42—C43 | −1.85 (18) |
O5—C19—C20—C21 | −177.06 (11) | C41—C42—C43—O12 | 179.04 (10) |
C24—C19—C20—C21 | 2.34 (17) | C41—C42—C43—C38 | 2.08 (17) |
C19—C20—C21—C22 | −0.7 (2) | C6—O12—C43—C42 | 44.68 (14) |
C20—C21—C22—C23 | −1.1 (2) | C6—O12—C43—C38 | −138.22 (10) |
C21—C22—C23—C24 | 1.3 (2) | O11—C38—C43—C42 | −179.49 (10) |
C22—C23—C24—O6 | −176.99 (12) | C39—C38—C43—C42 | −0.67 (16) |
C22—C23—C24—C19 | 0.35 (19) | O11—C38—C43—O12 | 3.32 (14) |
C25—O6—C24—C23 | −103.82 (12) | C39—C38—C43—O12 | −177.86 (10) |
Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O4i | 0.93 | 2.44 | 3.2871 (14) | 151 |
C17—H17A···O11ii | 0.97 | 2.60 | 3.4207 (15) | 142 |
C3—H3A···Cg1i | 0.93 | 2.94 | 3.6031 (15) | 130 |
C18—H18B···Cg2i | 0.97 | 2.80 | 3.7531 (15) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C43H45NO12 |
Mr | 767.80 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.5266 (4), 15.2732 (7), 15.5688 (8) |
α, β, γ (°) | 69.752 (2), 88.372 (2), 80.402 (2) |
V (Å3) | 1874.64 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.19 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.975, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33651, 8622, 7657 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.097, 1.03 |
No. of reflections | 8622 |
No. of parameters | 505 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.27 |
Computer programs: APEX2 (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Sheldrick, 2008).
Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O4i | 0.93 | 2.44 | 3.2871 (14) | 151.1 |
C17—H17A···O11ii | 0.97 | 2.60 | 3.4207 (15) | 142.1 |
C3—H3A···Cg1i | 0.93 | 2.937 | 3.6031 (15) | 129.80 |
C18—H18B···Cg2i | 0.97 | 2.801 | 3.7531 (15) | 167.37 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Acknowledgements
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2011-0007756). The authors gratefully acknowledge the use of SC-XRD in the Korea Basic Science Institute (Jeonju Center).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In our previous paper (Lee et al., 2009, Beack et al., 2012), we synthesized and reported the preparation and the solid-state structure of new crown ether bearing three aromatic subunits. As a part of our continuing interest in the development of new crown compounds, the preparation and crystal structure of new crown ether-based macrocyclic compound containing pyridine unit (Weber et al., 1976, 1980), we report herein the crystal structure of the title compound.
The crystal structure exhibits a twisted conformation with dihedral angles of 64.83 (6) (A/B), 13.48 (6) (A/C), 56.96 (6) (A/D), 66.21 (6) (A/E), 35.31 (6) (B/E), 69.15 (6) (C/D), 80.92 (6)° (D/E). (Fig. 1. A is N1/C1-C5 pyridine ring, B, C, D, E, are C7–C12, C19–C24, C26–C31 and C38–C43 benzene rings, respectively. In the crystal, molecules are linked by weak intermolecular C—H···O and C—H···π interactions. (Fig. 2 & Table 1; Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively).