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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2913
https://doi.org/10.1107/S1600536812038093

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

Jun Hee Kim,a Il Yoon,b Wonbo Sima* and Jai Young Leea*

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

(Received 13 August 2012; accepted 5 September 2012; online 12 September 2012)

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[Weber, E. & Vögtle, F. (1976). Chem. Ber. 109, 1803-1831.], 1980[Weber, E. & Vögtle, F. (1980). Angew. Chem. 92, 1067-1068.]). For the preparation and crystal structures of related compounds, see: Lee et al. (2009[Lee, J. Y., Lee, J.-E., Sim, W. & Park, K.-M. (2009). Acta Cryst. E65, o2369-o2370.]); Beack et al. (2012[Beack, H. J., Yoo, S. M., Kim, J. E., Sim, W. & Lee, J. Y. (2012). Acta Cryst. E68, o720.]).

[Scheme 1]

Experimental

Crystal data

  • C43H45NO12

  • Mr = 767.80

  • Triclinic, [P \overline 1]

  • a = 8.5266 (4) Å

  • b = 15.2732 (7) Å

  • c = 15.5688 (8) Å

  • α = 69.752 (2)°

  • β = 88.372 (2)°

  • γ = 80.402 (2)°

  • V = 1874.64 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.25 × 0.19 × 0.13 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.988

  • 33651 measured reflections

  • 8622 independent reflections

  • 7657 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.03

  • 8622 reflections

  • 505 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2000[Bruker (2000). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038093/lx2264sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038093/lx2264Isup2.hkl

checkCIF report


Comment top

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).

Related literature top

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 top

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 eluent, and recrystallization from dichloromethane/n-hexane (1:30, v/v) gave as a crystalline solid in 24% yield (m.p. 402–404 K).

Refinement top

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.

Structure description top

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).

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).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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.]
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 top
Crystal data top
C43H45NO12Z = 2
Mr = 767.80F(000) = 812
Triclinic, P1Dx = 1.360 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5266 (4) ÅCell parameters from 9368 reflections
b = 15.2732 (7) Åθ = 2.6–27.5°
c = 15.5688 (8) ŵ = 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
Data collection top
Bruker APEXII CCD
diffractometer		8622 independent reflections
Radiation source: fine-focus sealed tube7657 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
π and ω scansθmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.975, Tmax = 0.988k = −19→19
33651 measured reflectionsl = −20→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.097H-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 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C43H45NO12γ = 80.402 (2)°
Mr = 767.80V = 1874.64 (16) Å3
Triclinic, P1Z = 2
a = 8.5266 (4) ÅMo Kα radiation
b = 15.2732 (7) ŵ = 0.10 mm−1
c = 15.5688 (8) ÅT = 296 K
α = 69.752 (2)°0.25 × 0.19 × 0.13 mm
β = 88.372 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		8622 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7657 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.988Rint = 0.024
33651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å−3
8622 reflectionsΔρmin = −0.27 e Å−3
505 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.16048 (10)0.23963 (6)0.34935 (6)0.01732 (18)
O10.42156 (9)0.02455 (5)0.36551 (5)0.02018 (16)
O20.23385 (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)
O70.06804 (10)0.47547 (5)0.34239 (6)0.02325 (17)
O80.18306 (10)0.43854 (6)0.18692 (6)0.02400 (17)
O90.25086 (11)0.45435 (6)−0.00716 (6)0.02920 (19)
O100.55737 (10)0.32192 (6)−0.01372 (6)0.02566 (18)
O110.49707 (10)0.14304 (6)0.10207 (6)0.02586 (18)
O120.31057 (10)0.14756 (5)0.23457 (5)0.02138 (16)
C10.15225 (12)0.30759 (7)0.38556 (7)0.0179 (2)
C20.26197 (14)0.30632 (8)0.45049 (8)0.0221 (2)
H2A0.25310.35560.47340.027*
C30.38433 (14)0.23023 (8)0.48010 (8)0.0234 (2)
H3A0.45870.22700.52410.028*
C40.39516 (13)0.15860 (7)0.44349 (7)0.0195 (2)
H4A0.47590.10630.46270.023*
C50.28230 (12)0.16721 (7)0.37739 (7)0.0167 (2)
C60.28892 (12)0.09688 (7)0.32825 (7)0.0173 (2)
H6A0.19030.07030.33590.021*
C70.46007 (13)−0.04066 (7)0.32113 (7)0.0194 (2)
C80.59910 (14)−0.04026 (8)0.27378 (8)0.0236 (2)
H8A0.66150.00580.26820.028*
C90.64556 (15)−0.10925 (9)0.23426 (9)0.0296 (3)
H9A0.7401−0.11000.20310.035*
C100.55131 (16)−0.17632 (9)0.24142 (9)0.0308 (3)
H10A0.5829−0.22220.21500.037*
C110.40934 (15)−0.17611 (8)0.28783 (9)0.0267 (2)
H11A0.3452−0.22080.29120.032*
C120.36402 (13)−0.10881 (8)0.32907 (8)0.0212 (2)
C130.10545 (14)−0.14958 (8)0.36882 (9)0.0273 (2)
H13A0.1333−0.21790.39590.033*
H13B0.0803−0.13300.30420.033*
C14−0.03361 (14)−0.11372 (8)0.41581 (9)0.0266 (2)
H14A−0.1254−0.14130.40970.032*
H14B−0.0081−0.13080.48050.032*
C15−0.17984 (14)0.03039 (8)0.42142 (8)0.0243 (2)
H15A−0.13980.01710.48310.029*
H15B−0.27910.00630.42530.029*
C16−0.20694 (14)0.13527 (8)0.36989 (8)0.0239 (2)
H16A−0.26530.16870.40680.029*
H16B−0.10590.15740.35510.029*
C17−0.31024 (16)0.24439 (9)0.22326 (8)0.0288 (3)
H17A−0.36070.24550.16770.035*
H17B−0.20440.25930.20820.035*
C18−0.40408 (15)0.32034 (8)0.25400 (8)0.0258 (2)
H18A−0.43970.37670.20150.031*
H18B−0.49670.29850.28660.031*
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−0.57820.45790.28850.029*
C21−0.53898 (15)0.54706 (9)0.35292 (9)0.0307 (3)
H21A−0.63860.58510.33880.037*
C22−0.42956 (16)0.56692 (10)0.40388 (10)0.0355 (3)
H22A−0.45450.61870.42320.043*
C23−0.28131 (15)0.50912 (9)0.42638 (9)0.0295 (3)
H23A−0.20770.52150.46180.035*
C24−0.24379 (13)0.43376 (8)0.39619 (8)0.0214 (2)
C250.01485 (13)0.38871 (7)0.35244 (7)0.0189 (2)
H25A−0.03190.39110.29470.023*
C260.05292 (13)0.54533 (8)0.25695 (8)0.0231 (2)
C27−0.01090 (16)0.63690 (9)0.25206 (10)0.0325 (3)
H27A−0.04700.64870.30460.039*
C28−0.02063 (18)0.71077 (9)0.16855 (11)0.0393 (3)
H28A−0.06230.77210.16540.047*
C290.03125 (16)0.69367 (9)0.09012 (10)0.0350 (3)
H29A0.02270.74320.03420.042*
C300.09607 (14)0.60270 (9)0.09464 (9)0.0283 (3)
H30A0.13130.59130.04180.034*
C310.10854 (13)0.52837 (8)0.17819 (8)0.0227 (2)
C320.11733 (14)0.39272 (8)0.13235 (8)0.0239 (2)
H32A0.02400.43410.09800.029*
H32B0.08430.33490.17260.029*
C330.23586 (15)0.36951 (8)0.06713 (8)0.0254 (2)
H33A0.33820.34120.09860.030*
H33B0.20070.32440.04400.030*
C340.32053 (15)0.43884 (9)−0.08583 (8)0.0288 (3)
H34A0.29060.4956−0.13890.035*
H34B0.27760.3881−0.09580.035*
C350.50017 (15)0.41369 (9)−0.07829 (9)0.0282 (3)
H35A0.54030.4168−0.13800.034*
H35B0.54230.4605−0.06070.034*
C360.54982 (16)0.24892 (9)−0.04898 (8)0.0286 (3)
H36A0.61990.2547−0.10010.034*
H36B0.44210.2531−0.07040.034*
C370.60036 (15)0.15579 (9)0.02652 (9)0.0289 (3)
H37A0.60100.10480.00280.035*
H37B0.70790.15270.04750.035*
C380.35459 (14)0.11590 (8)0.09707 (8)0.0215 (2)
C390.30404 (15)0.08776 (9)0.02814 (8)0.0272 (2)
H39A0.36830.0885−0.02130.033*
C400.15708 (16)0.05847 (9)0.03322 (9)0.0305 (3)
H40A0.12440.0385−0.01240.037*
C410.05942 (15)0.05870 (9)0.10527 (9)0.0294 (3)
H41A−0.03850.03880.10810.035*
C420.10706 (14)0.08869 (8)0.17370 (8)0.0246 (2)
H42A0.04000.09060.22140.029*
C430.25443 (13)0.11560 (7)0.17044 (7)0.0200 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0178 (4)0.0167 (4)0.0183 (4)−0.0034 (3)0.0012 (3)−0.0068 (3)
O10.0203 (4)0.0186 (4)0.0234 (4)0.0012 (3)−0.0028 (3)−0.0113 (3)
O20.0233 (4)0.0263 (4)0.0326 (4)−0.0074 (3)0.0036 (3)−0.0156 (4)
O30.0253 (4)0.0204 (4)0.0288 (4)−0.0022 (3)0.0060 (3)−0.0046 (3)
O40.0370 (5)0.0203 (4)0.0340 (5)−0.0065 (3)−0.0120 (4)−0.0083 (4)
O50.0252 (4)0.0253 (4)0.0392 (5)0.0001 (3)−0.0074 (4)−0.0187 (4)
O60.0182 (4)0.0241 (4)0.0211 (4)0.0004 (3)0.0008 (3)−0.0086 (3)
O70.0264 (4)0.0181 (4)0.0267 (4)−0.0032 (3)−0.0016 (3)−0.0096 (3)
O80.0226 (4)0.0212 (4)0.0273 (4)0.0023 (3)−0.0012 (3)−0.0099 (3)
O90.0335 (5)0.0239 (4)0.0270 (4)−0.0037 (3)0.0087 (3)−0.0060 (3)
O100.0277 (4)0.0261 (4)0.0241 (4)−0.0056 (3)0.0015 (3)−0.0094 (3)
O110.0278 (4)0.0291 (4)0.0229 (4)−0.0090 (3)0.0024 (3)−0.0101 (3)
O120.0294 (4)0.0203 (4)0.0171 (4)−0.0079 (3)0.0007 (3)−0.0081 (3)
C10.0178 (5)0.0172 (5)0.0193 (5)−0.0035 (4)0.0019 (4)−0.0067 (4)
C20.0261 (6)0.0200 (5)0.0230 (5)−0.0026 (4)−0.0017 (4)−0.0115 (4)
C30.0249 (6)0.0238 (5)0.0228 (5)−0.0027 (4)−0.0056 (4)−0.0099 (4)
C40.0192 (5)0.0183 (5)0.0200 (5)−0.0007 (4)−0.0011 (4)−0.0065 (4)
C50.0181 (5)0.0160 (5)0.0164 (5)−0.0045 (4)0.0031 (4)−0.0055 (4)
C60.0178 (5)0.0158 (5)0.0178 (5)−0.0017 (4)−0.0004 (4)−0.0057 (4)
C70.0217 (5)0.0170 (5)0.0195 (5)0.0019 (4)−0.0044 (4)−0.0084 (4)
C80.0231 (5)0.0232 (5)0.0252 (6)−0.0017 (4)−0.0014 (4)−0.0102 (4)
C90.0268 (6)0.0339 (6)0.0312 (6)−0.0004 (5)0.0040 (5)−0.0177 (5)
C100.0341 (7)0.0299 (6)0.0347 (7)0.0017 (5)−0.0007 (5)−0.0221 (5)
C110.0291 (6)0.0223 (5)0.0327 (6)−0.0029 (4)−0.0032 (5)−0.0146 (5)
C120.0209 (5)0.0191 (5)0.0227 (5)0.0008 (4)−0.0035 (4)−0.0078 (4)
C130.0261 (6)0.0208 (5)0.0374 (7)−0.0068 (4)0.0002 (5)−0.0118 (5)
C140.0257 (6)0.0204 (5)0.0321 (6)−0.0073 (4)0.0025 (5)−0.0057 (5)
C150.0205 (5)0.0255 (6)0.0258 (6)−0.0041 (4)0.0022 (4)−0.0077 (5)
C160.0216 (5)0.0248 (6)0.0269 (6)−0.0052 (4)−0.0010 (4)−0.0102 (5)
C170.0387 (7)0.0236 (6)0.0251 (6)−0.0061 (5)−0.0033 (5)−0.0089 (5)
C180.0281 (6)0.0224 (5)0.0273 (6)−0.0063 (4)−0.0061 (5)−0.0076 (5)
C190.0221 (5)0.0185 (5)0.0228 (5)−0.0039 (4)0.0024 (4)−0.0067 (4)
C200.0215 (5)0.0243 (5)0.0255 (6)−0.0039 (4)−0.0011 (4)−0.0059 (4)
C210.0231 (6)0.0298 (6)0.0367 (7)0.0043 (5)−0.0004 (5)−0.0121 (5)
C220.0314 (7)0.0339 (7)0.0469 (8)0.0049 (5)−0.0010 (6)−0.0257 (6)
C230.0256 (6)0.0341 (7)0.0347 (7)−0.0010 (5)−0.0013 (5)−0.0209 (5)
C240.0178 (5)0.0227 (5)0.0230 (5)−0.0011 (4)0.0023 (4)−0.0083 (4)
C250.0192 (5)0.0186 (5)0.0205 (5)−0.0026 (4)0.0012 (4)−0.0093 (4)
C260.0191 (5)0.0185 (5)0.0310 (6)−0.0027 (4)0.0009 (4)−0.0077 (4)
C270.0341 (7)0.0223 (6)0.0408 (7)−0.0005 (5)0.0065 (5)−0.0127 (5)
C280.0412 (8)0.0176 (6)0.0533 (9)0.0008 (5)0.0056 (6)−0.0081 (6)
C290.0339 (7)0.0217 (6)0.0398 (7)−0.0027 (5)0.0029 (5)0.0002 (5)
C300.0238 (6)0.0252 (6)0.0316 (6)−0.0036 (5)0.0034 (5)−0.0050 (5)
C310.0164 (5)0.0197 (5)0.0307 (6)−0.0012 (4)0.0009 (4)−0.0078 (4)
C320.0238 (5)0.0227 (5)0.0252 (6)−0.0045 (4)0.0015 (4)−0.0080 (4)
C330.0287 (6)0.0214 (5)0.0236 (6)−0.0019 (4)0.0029 (4)−0.0060 (4)
C340.0285 (6)0.0325 (6)0.0221 (6)−0.0050 (5)0.0032 (5)−0.0054 (5)
C350.0281 (6)0.0282 (6)0.0261 (6)−0.0076 (5)0.0044 (5)−0.0058 (5)
C360.0319 (6)0.0337 (6)0.0246 (6)−0.0094 (5)0.0075 (5)−0.0144 (5)
C370.0263 (6)0.0300 (6)0.0330 (6)−0.0032 (5)0.0069 (5)−0.0151 (5)
C380.0254 (5)0.0173 (5)0.0212 (5)−0.0020 (4)−0.0018 (4)−0.0064 (4)
C390.0347 (6)0.0267 (6)0.0232 (6)−0.0043 (5)0.0014 (5)−0.0128 (5)
C400.0378 (7)0.0314 (6)0.0280 (6)−0.0057 (5)−0.0067 (5)−0.0168 (5)
C410.0276 (6)0.0310 (6)0.0322 (6)−0.0061 (5)−0.0061 (5)−0.0130 (5)
C420.0241 (6)0.0258 (6)0.0241 (5)−0.0022 (4)−0.0012 (4)−0.0098 (5)
C430.0264 (5)0.0153 (5)0.0183 (5)−0.0009 (4)−0.0040 (4)−0.0067 (4)
Geometric parameters (Å, º) top
N1—C11.3336 (13)C16—H16A0.9700
N1—C51.3421 (13)C16—H16B0.9700
O1—C71.3900 (12)C17—C181.5060 (17)
O1—C61.4188 (12)C17—H17A0.9700
O2—C121.3612 (14)C17—H17B0.9700
O2—C131.4305 (14)C18—H18A0.9700
O3—C141.4189 (14)C18—H18B0.9700
O3—C151.4220 (14)C19—C201.3908 (16)
O4—C171.4144 (14)C19—C241.4002 (16)
O4—C161.4207 (14)C20—C211.3864 (17)
O5—C191.3608 (13)C20—H20A0.9300
O5—C181.4349 (14)C21—C221.3765 (19)
O6—C241.3947 (13)C21—H21A0.9300
O6—C251.4184 (13)C22—C231.3924 (18)
O7—C261.3805 (14)C22—H22A0.9300
O7—C251.4279 (13)C23—C241.3752 (16)
O8—C311.3746 (13)C23—H23A0.9300
O8—C321.4475 (14)C25—H25A0.9800
O9—C341.4219 (15)C26—C271.3903 (16)
O9—C331.4292 (14)C26—C311.3934 (17)
O10—C361.4136 (14)C27—C281.389 (2)
O10—C351.4274 (15)C27—H27A0.9300
O11—C381.3599 (14)C28—C291.381 (2)
O11—C371.4272 (14)C28—H28A0.9300
O12—C431.3807 (13)C29—C301.3853 (18)
O12—C61.4182 (13)C29—H29A0.9300
C1—C21.3899 (15)C30—C311.3920 (17)
C1—C251.5105 (14)C30—H30A0.9300
C2—C31.3798 (16)C32—C331.4998 (16)
C2—H2A0.9300C32—H32A0.9700
C3—C41.3874 (15)C32—H32B0.9700
C3—H3A0.9300C33—H33A0.9700
C4—C51.3866 (15)C33—H33B0.9700
C4—H4A0.9300C34—C351.5133 (17)
C5—C61.5127 (14)C34—H34A0.9700
C6—H6A0.9800C34—H34B0.9700
C7—C81.3779 (16)C35—H35A0.9700
C7—C121.3996 (16)C35—H35B0.9700
C8—C91.3935 (16)C36—C371.5025 (18)
C8—H8A0.9300C36—H36A0.9700
C9—C101.3777 (19)C36—H36B0.9700
C9—H9A0.9300C37—H37A0.9700
C10—C111.3922 (18)C37—H37B0.9700
C10—H10A0.9300C38—C391.3890 (16)
C11—C121.3886 (15)C38—C431.4059 (16)
C11—H11A0.9300C39—C401.3904 (19)
C13—C141.5009 (17)C39—H39A0.9300
C13—H13A0.9700C40—C411.3787 (19)
C13—H13B0.9700C40—H40A0.9300
C14—H14A0.9700C41—C421.3908 (16)
C14—H14B0.9700C41—H41A0.9300
C15—C161.5035 (16)C42—C431.3801 (16)
C15—H15A0.9700C42—H42A0.9300
C15—H15B0.9700
C1—N1—C5117.46 (9)C21—C20—H20A120.2
C7—O1—C6116.18 (8)C19—C20—H20A120.2
C12—O2—C13118.30 (9)C22—C21—C20120.95 (11)
C14—O3—C15113.10 (9)C22—C21—H21A119.5
C17—O4—C16115.62 (9)C20—C21—H21A119.5
C19—O5—C18118.56 (9)C21—C22—C23119.65 (12)
C24—O6—C25113.49 (8)C21—C22—H22A120.2
C26—O7—C25118.20 (9)C23—C22—H22A120.2
C31—O8—C32116.75 (9)C24—C23—C22119.97 (12)
C34—O9—C33114.12 (9)C24—C23—H23A120.0
C36—O10—C35112.52 (9)C22—C23—H23A120.0
C38—O11—C37119.56 (9)C23—C24—O6119.67 (10)
C43—O12—C6117.59 (8)C23—C24—C19120.52 (10)
N1—C1—C2123.34 (10)O6—C24—C19119.76 (10)
N1—C1—C25116.51 (9)O6—C25—O7107.64 (8)
C2—C1—C25120.15 (9)O6—C25—C1106.58 (8)
C3—C2—C1118.40 (10)O7—C25—C1109.53 (9)
C3—C2—H2A120.8O6—C25—H25A111.0
C1—C2—H2A120.8O7—C25—H25A111.0
C2—C3—C4119.27 (10)C1—C25—H25A111.0
C2—C3—H3A120.4O7—C26—C27117.48 (11)
C4—C3—H3A120.4O7—C26—C31122.60 (10)
C5—C4—C3118.16 (10)C27—C26—C31119.77 (11)
C5—C4—H4A120.9C28—C27—C26119.86 (13)
C3—C4—H4A120.9C28—C27—H27A120.1
N1—C5—C4123.32 (10)C26—C27—H27A120.1
N1—C5—C6113.98 (9)C29—C28—C27120.39 (12)
C4—C5—C6122.67 (9)C29—C28—H28A119.8
O12—C6—O1110.70 (8)C27—C28—H28A119.8
O12—C6—C5106.24 (8)C28—C29—C30120.03 (12)
O1—C6—C5107.54 (8)C28—C29—H29A120.0
O12—C6—H6A110.7C30—C29—H29A120.0
O1—C6—H6A110.7C29—C30—C31120.06 (12)
C5—C6—H6A110.7C29—C30—H30A120.0
C8—C7—O1118.66 (10)C31—C30—H30A120.0
C8—C7—C12120.82 (10)O8—C31—C30121.87 (11)
O1—C7—C12120.42 (10)O8—C31—C26118.16 (10)
C7—C8—C9119.56 (11)C30—C31—C26119.87 (11)
C7—C8—H8A120.2O8—C32—C33111.66 (10)
C9—C8—H8A120.2O8—C32—H32A109.3
C10—C9—C8119.97 (11)C33—C32—H32A109.3
C10—C9—H9A120.0O8—C32—H32B109.3
C8—C9—H9A120.0C33—C32—H32B109.3
C9—C10—C11120.73 (11)H32A—C32—H32B107.9
C9—C10—H10A119.6O9—C33—C32109.20 (9)
C11—C10—H10A119.6O9—C33—H33A109.8
C12—C11—C10119.61 (11)C32—C33—H33A109.8
C12—C11—H11A120.2O9—C33—H33B109.8
C10—C11—H11A120.2C32—C33—H33B109.8
O2—C12—C11125.04 (11)H33A—C33—H33B108.3
O2—C12—C7115.61 (10)O9—C34—C35113.57 (10)
C11—C12—C7119.30 (11)O9—C34—H34A108.9
O2—C13—C14106.10 (9)C35—C34—H34A108.9
O2—C13—H13A110.5O9—C34—H34B108.9
C14—C13—H13A110.5C35—C34—H34B108.9
O2—C13—H13B110.5H34A—C34—H34B107.7
C14—C13—H13B110.5O10—C35—C34113.72 (10)
H13A—C13—H13B108.7O10—C35—H35A108.8
O3—C14—C13107.63 (9)C34—C35—H35A108.8
O3—C14—H14A110.2O10—C35—H35B108.8
C13—C14—H14A110.2C34—C35—H35B108.8
O3—C14—H14B110.2H35A—C35—H35B107.7
C13—C14—H14B110.2O10—C36—C37107.99 (10)
H14A—C14—H14B108.5O10—C36—H36A110.1
O3—C15—C16108.15 (9)C37—C36—H36A110.1
O3—C15—H15A110.1O10—C36—H36B110.1
C16—C15—H15A110.1C37—C36—H36B110.1
O3—C15—H15B110.1H36A—C36—H36B108.4
C16—C15—H15B110.1O11—C37—C36111.95 (10)
H15A—C15—H15B108.4O11—C37—H37A109.2
O4—C16—C15107.35 (9)C36—C37—H37A109.2
O4—C16—H16A110.2O11—C37—H37B109.2
C15—C16—H16A110.2C36—C37—H37B109.2
O4—C16—H16B110.2H37A—C37—H37B107.9
C15—C16—H16B110.2O11—C38—C39125.83 (11)
H16A—C16—H16B108.5O11—C38—C43115.04 (10)
O4—C17—C18114.69 (10)C39—C38—C43119.12 (11)
O4—C17—H17A108.6C38—C39—C40119.85 (11)
C18—C17—H17A108.6C38—C39—H39A120.1
O4—C17—H17B108.6C40—C39—H39A120.1
C18—C17—H17B108.6C41—C40—C39120.63 (11)
H17A—C17—H17B107.6C41—C40—H40A119.7
O5—C18—C17107.36 (10)C39—C40—H40A119.7
O5—C18—H18A110.2C40—C41—C42120.11 (12)
C17—C18—H18A110.2C40—C41—H41A119.9
O5—C18—H18B110.2C42—C41—H41A119.9
C17—C18—H18B110.2C43—C42—C41119.65 (11)
H18A—C18—H18B108.5C43—C42—H42A120.2
O5—C19—C20125.28 (10)C41—C42—H42A120.2
O5—C19—C24115.47 (10)C42—C43—O12123.61 (10)
C20—C19—C24119.25 (10)C42—C43—C38120.61 (10)
C21—C20—C19119.61 (11)O12—C43—C38115.72 (10)
C5—N1—C1—C2−0.47 (15)C25—O6—C24—C1978.83 (12)
C5—N1—C1—C25179.56 (9)O5—C19—C24—C23177.31 (11)
N1—C1—C2—C3−1.01 (17)C20—C19—C24—C23−2.15 (17)
C25—C1—C2—C3178.96 (10)O5—C19—C24—O6−5.36 (15)
C1—C2—C3—C40.88 (17)C20—C19—C24—O6175.18 (10)
C2—C3—C4—C50.65 (17)C24—O6—C25—O772.70 (11)
C1—N1—C5—C42.15 (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—C1120.53 (10)
C3—C4—C5—C6175.76 (10)N1—C1—C25—O6103.06 (10)
C43—O12—C6—O190.74 (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—O739.25 (13)
C7—O1—C6—C5−172.01 (8)C25—O7—C26—C27133.16 (11)
N1—C5—C6—O1262.05 (11)C25—O7—C26—C31−51.29 (14)
C4—C5—C6—O12−116.15 (11)O7—C26—C27—C28176.45 (12)
N1—C5—C6—O1−179.39 (8)C31—C26—C27—C280.77 (19)
C4—C5—C6—O12.42 (13)C26—C27—C28—C290.7 (2)
C6—O1—C7—C8111.11 (11)C27—C28—C29—C30−1.1 (2)
C6—O1—C7—C12−72.60 (13)C28—C29—C30—C310.2 (2)
O1—C7—C8—C9175.50 (10)C32—O8—C31—C30−60.17 (14)
C12—C7—C8—C9−0.77 (17)C32—O8—C31—C26123.61 (11)
C7—C8—C9—C101.06 (18)C29—C30—C31—O8−174.92 (11)
C8—C9—C10—C110.0 (2)C29—C30—C31—C261.23 (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—O8174.58 (11)
C13—O2—C12—C7159.87 (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—C71.68 (17)C31—O8—C32—C33119.02 (11)
C8—C7—C12—O2176.86 (10)C34—O9—C33—C32−161.94 (10)
O1—C7—C12—O20.65 (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—C3479.12 (13)
C12—O2—C13—C14−165.98 (10)O9—C34—C35—O1070.00 (14)
C15—O3—C14—C13−170.45 (10)C35—O10—C36—C37−175.63 (10)
O2—C13—C14—O359.66 (12)C38—O11—C37—C3678.96 (13)
C14—O3—C15—C16−179.28 (9)O10—C36—C37—O1161.68 (13)
C17—O4—C16—C15−169.69 (10)C37—O11—C38—C398.08 (17)
O3—C15—C16—O471.86 (11)C37—O11—C38—C43−173.19 (10)
C16—O4—C17—C18−65.62 (14)O11—C38—C39—C40177.70 (11)
C19—O5—C18—C17173.18 (10)C43—C38—C39—C40−0.98 (17)
O4—C17—C18—O579.00 (13)C38—C39—C40—C411.21 (19)
C18—O5—C19—C202.43 (17)C39—C40—C41—C420.21 (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—O12179.04 (10)
C24—C19—C20—C212.34 (17)C41—C42—C43—C382.08 (17)
C19—C20—C21—C22−0.7 (2)C6—O12—C43—C4244.68 (14)
C20—C21—C22—C23−1.1 (2)C6—O12—C43—C38−138.22 (10)
C21—C22—C23—C241.3 (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—C190.35 (19)O11—C38—C43—O123.32 (14)
C25—O6—C24—C23−103.82 (12)C39—C38—C43—O12−177.86 (10)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8A···O4i0.932.443.2871 (14)151
C17—H17A···O11ii0.972.603.4207 (15)142
C3—H3A···Cg1i0.932.943.6031 (15)130
C18—H18B···Cg2i0.972.803.7531 (15)167
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC43H45NO12
Mr767.80
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.25 × 0.19 × 0.13
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.975, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		33651, 8622, 7657
Rint0.024
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.097, 1.03
No. of reflections8622
No. of parameters505
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.28, −0.27

Computer programs: APEX2 (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C7–C12 benzene ring and the N1/C1–C5 pyridine ring, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8A···O4i0.932.443.2871 (14)151.1
C17—H17A···O11ii0.972.603.4207 (15)142.1
C3—H3A···Cg1i0.932.9373.6031 (15)129.80
C18—H18B···Cg2i0.972.8013.7531 (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

First citationBeack, H. J., Yoo, S. M., Kim, J. E., Sim, W. & Lee, J. Y. (2012). Acta Cryst. E68, o720.  CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2913
https://doi.org/10.1107/S1600536812038093
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