2,8,15,18,21,24,31,37,44,47,50,53-Dodeca­oxahepta­cyclo­[52.4.0.04,35.06,33.09,14.025,30.038,43]octa­penta­conta-1(54),4,6(33),9(14),10,12,25(30),26,28,34,38(43),39,41,55,57-penta­deca­ene di­chloro­methane disolvate

Yun, J.Y.; Ahn, S.W.; Kim, D.H.; Sim, W.; Lee, J.Y.

doi:10.1107/S1600536814007971

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o558

doi:10.1107/S1600536814007971

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2,8,15,18,21,24,31,37,44,47,50,53-Dodecaoxaheptacyclo[52.4.0.0^4,35.0^6,33.0^9,14.0^25,30.0^38,43]octapentaconta-1(54),4,6(33),9(14),10,12,25(30),26,28,34,38(43),39,41,55,57-pentadecaene dichloromethane disolvate

Ji Ye Yun,^a Sung Wan Ahn,^a Dong Hwan Kim,^a Wonbo Sim ^a ^* and Jai Young Lee ^a ^*

^aDepartment of Chemistry, Konyang University, Nonsan 320-711, Republic of Korea
^*Correspondence e-mail: jylee@konyang.ac.kr, jylee@konyang.ac.kr

(Received 31 March 2014; accepted 10 April 2014; online 16 April 2014)

In the title compound, C₄₆H₅₀O₁₂·2CH₂Cl₂, each dual 20-crown-6 unit crystallizes with two dichloromethane solvent molecules. The crown unit molecule lies about an inversion centre located at the central benzene ring. The two crown ring groups adopt an anti conformation, stabilized by weak intramolecular C—H⋯O interactions. In the crystal, the crown unit molecules and the solvent molecules are linked by C—H⋯O interactions into a three-dimensional network.

CCDC reference: 996417

Related literature

For the preparation and crystal structures of related compounds, see: Lee et al. (2009 ); Beack et al. (2012 ). For background to dual crown ethers and their inclusion behavior, see: Lee et al. (1992 , 1997 ).

Experimental

Crystal data

C₄₆H₅₀O₁₂·2CH₂Cl₂
M_r = 964.71
Orthorhombic, P c c n
a = 23.0916 (11) Å
b = 23.9520 (11) Å
c = 8.6426 (4) Å
V = 4780.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 200 K
0.25 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.927, T_max = 0.947
26165 measured reflections
4211 independent reflections
2588 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.136
S = 1.02
4211 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O6ⁱ	0.95	2.47	2.828 (3)	103
C3—H3B⋯O4ⁱⁱ	0.99	2.59	3.457 (4)	146
C22—H22A⋯O1ⁱⁱ	0.99	2.32	3.252 (3)	156
C22—H22B⋯O1	0.99	2.53	2.909 (3)	103
C24—H24A⋯O6	0.99	2.51	3.455 (4)	160
C24—H24B⋯O3	0.99	2.36	3.331 (5)	168
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); 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

CCDC reference: 996417

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814007971/wm5018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007971/wm5018Isup2.hkl

checkCIF report

Chemical context top

In a previous article we reported the synthesis and complexation behavior of common-nuclear bis-crown ethers (Lee et al., 1992, 1997). Within this context we also reported the precursor of the common-nuclear biscrown ether, bearing three aromatic subunits (Lee et al., 2009; Beack et al., 2012). The reaction of 1,2,4,5-tetrakis(bromomethyl)benzene and bisphenol in the presence of sodium hydride afforded the title compound, C₄₆H₅₀O₁₂, that crystallizes with two molecules of dichloromethane.

Structural commentary top

In the title molecule (Fig. 1), in the A-to-B ring and A-to-C ring connectivities, the torsion angles C2–C3–O1–C4 and C23–C22–O6–C21 are -72.7 (3) ° and 99.0 (3)°, respectively. This indicates that the A ring is situated gauche to the B ring, also situated gauche to the C ring, with dihedral angles of 81.64 (14)° between A and B and 81.16 (14)° between A and C. The dihedral angle between the B and C ring is 1.92 (15)°. All C–C–O–C torsion angles in the triethylene glycol group are related to trans conformations. Weak intramolecular C—H···O hydrogen bonds (C22—H22B···O1; C1—H1A···O6) stabilize the conformation of the crown unit molecule (Fig. 1, Table 1).

Supramolecular features top

In the crystal, the crown unit molecules and the solvent molecules are linked by C—H···O interactions (Figs. 1, 2; Table 1). The C atom of the dichloromethane molecule (C24) is shifted by 2.383 Å outwards to the crown ring cavity (least squares plane defined by atoms O1–O6), and forms two C—H···O hydrogen bonds with two O atoms (O3 and O6) in the crown ring (Fig. 1, Table 1).

Synthesis and crystallization top

To a refluxing suspension of sodium hydride (10.6 mmol) in THF under nitrogen was added dropwise a solution of 1,2,4,5-tetrakis(bromomethyl)benzene (2.20 mmol) and 1,8-bis(2-hydroxyphenoxy)-3,6-dioxaoctane (4.40 mmol) in THF over a period of 3 h. The mixture was then refluxed for additional 3 days. After cooling to room temperature, 10%_wt 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 (1:1) as eluent. Recrystallization from dichloromethane/n-hexane (1:20, v/v) resulted in 53% yield (m.p. 423 K). IR (KBr pellet): 2927, 1599, 1505, 1459, 1255, 1122, 1003, and 738 cm^-1. ¹H NMR (CDCl₃): d 7.69 (s, 2 H, OCH₂Ar), 6.92~6.80 (m, 16 H, OArO), 5.29 (s, 8 H, OCH₂Ar), 4.12 (t, 8 H, ArOCH₂CH₂), 3.81 (t, 8 H, ArOCH₂CH₂) and 3.66 (t, 8 H, ArOCH₂CH₂OCH₂).

Refinement details top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H)=0.95 Å, U_iso=1.2U_eq(C) for aromatic and 0.99 Å, U_iso=1.2U_eq(C) for CH₂ atoms. Reflection (110) was affected by the beamstop and was omitted from the refinement.

Related literature top

For the preparation and crystal structures of related compounds, see: Lee et al. (2009); Beack et al. (2012). For background to dual crown ethers and their inclusion behavior, see: Lee et al. (1992, 1997).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); 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

	Fig. 1. The molecular entities of the title compound with the atom numbering scheme and C—H···O interactions (dotted lines). Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. [Symmetry code A): -x + 1, -y + 1, -z + 1].
	Fig. 2. Crystal packing of the title compound with intra- and intermolecular C—H···O hydrogen bonds shown as dashed lines. [Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 1, -y + 1, -z.]

2,8,15,18,21,24,31,37,44,47,50,53-Dodecaoxaheptacyclo[52.4.0.0^4,35.0^6,33.0^9,14.0^25,30.0^38,43]octapentaconta-1(54),4,6(33),9(14),10,12,25 (30),26,28,34,38 (43),39,41,55,57-pentadecaene dichloromethane disolvate top

Crystal data top

C₄₆H₅₀O₁₂·2CH₂Cl₂	F(000) = 2024
M_r = 964.71	D_x = 1.340 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 4261 reflections
a = 23.0916 (11) Å	θ = 2.5–22.2°
b = 23.9520 (11) Å	µ = 0.31 mm⁻¹
c = 8.6426 (4) Å	T = 200 K
V = 4780.1 (4) Å³	Block, colorless
Z = 4	0.25 × 0.24 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	4211 independent reflections
Radiation source: fine-focus sealed tube	2588 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −27→22
T_min = 0.927, T_max = 0.947	k = −28→27
26165 measured reflections	l = −10→10

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0524P)² + 2.3252P] where P = (F_o² + 2F_c²)/3
4211 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₄₆H₅₀O₁₂·2CH₂Cl₂	V = 4780.1 (4) Å³
M_r = 964.71	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 23.0916 (11) Å	µ = 0.31 mm⁻¹
b = 23.9520 (11) Å	T = 200 K
c = 8.6426 (4) Å	0.25 × 0.24 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	4211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2588 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.947	R_int = 0.077
26165 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.02	Δρ_max = 0.48 e Å⁻³
4211 reflections	Δρ_min = −0.41 e Å⁻³
289 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.54545 (8)	0.54550 (8)	0.1042 (2)	0.0372 (5)
O2	0.63386 (9)	0.52751 (8)	−0.0718 (2)	0.0451 (5)
O3	0.65434 (10)	0.42923 (8)	−0.2639 (2)	0.0527 (6)
O4	0.58731 (10)	0.32856 (8)	−0.2708 (2)	0.0542 (6)
O5	0.51826 (10)	0.31134 (8)	−0.0013 (2)	0.0492 (6)
O6	0.52007 (9)	0.37487 (7)	0.2487 (2)	0.0405 (5)
C1	0.48858 (12)	0.55573 (11)	0.4876 (3)	0.0315 (7)
H1A	0.4806	0.5945	0.4790	0.038*
C2	0.49824 (11)	0.52536 (11)	0.3538 (3)	0.0300 (6)
C3	0.49439 (12)	0.55343 (12)	0.1976 (3)	0.0353 (7)
H3A	0.4604	0.5385	0.1413	0.042*
H3B	0.4881	0.5939	0.2131	0.042*
C4	0.59462 (13)	0.57372 (11)	0.1441 (3)	0.0353 (7)
C5	0.59937 (14)	0.61083 (12)	0.2657 (3)	0.0434 (8)
H5A	0.5667	0.6184	0.3290	0.052*
C6	0.65181 (16)	0.63729 (13)	0.2960 (4)	0.0532 (9)
H6A	0.6548	0.6628	0.3799	0.064*
C7	0.69873 (15)	0.62667 (13)	0.2057 (4)	0.0567 (9)
H7A	0.7345	0.6446	0.2275	0.068*
C8	0.69505 (14)	0.58999 (13)	0.0822 (4)	0.0515 (9)
H8A	0.7281	0.5830	0.0198	0.062*
C9	0.64311 (13)	0.56349 (11)	0.0498 (3)	0.0398 (7)
C10	0.68141 (14)	0.52010 (13)	−0.1761 (4)	0.0494 (8)
H10A	0.7139	0.5015	−0.1219	0.059*
H10B	0.6951	0.5569	−0.2133	0.059*
C11	0.66245 (15)	0.48529 (13)	−0.3103 (4)	0.0530 (9)
H11A	0.6257	0.5003	−0.3525	0.064*
H11B	0.6921	0.4870	−0.3929	0.064*
C12	0.65282 (15)	0.39212 (13)	−0.3923 (4)	0.0527 (9)
H12A	0.6898	0.3944	−0.4502	0.063*
H12B	0.6210	0.4028	−0.4631	0.063*
C13	0.64360 (15)	0.33379 (14)	−0.3356 (4)	0.0572 (9)
H13A	0.6480	0.3072	−0.4226	0.069*
H13B	0.6731	0.3246	−0.2563	0.069*
C14	0.57832 (16)	0.27550 (12)	−0.2012 (4)	0.0555 (9)
H14A	0.6080	0.2690	−0.1205	0.067*
H14B	0.5820	0.2458	−0.2802	0.067*
C15	0.51951 (16)	0.27369 (13)	−0.1309 (4)	0.0539 (9)
H15A	0.4901	0.2849	−0.2083	0.065*
H15B	0.5106	0.2353	−0.0961	0.065*
C16	0.46768 (14)	0.31477 (12)	0.0792 (3)	0.0408 (7)
C17	0.41664 (16)	0.28668 (12)	0.0421 (4)	0.0525 (9)
H17A	0.4157	0.2623	−0.0446	0.063*
C18	0.36749 (16)	0.29396 (13)	0.1303 (4)	0.0557 (9)
H18A	0.3328	0.2751	0.1032	0.067*
C19	0.36849 (15)	0.32842 (14)	0.2573 (4)	0.0554 (9)
H19A	0.3347	0.3331	0.3185	0.066*
C20	0.41895 (14)	0.35637 (13)	0.2958 (4)	0.0494 (8)
H20A	0.4195	0.3805	0.3831	0.059*
C21	0.46838 (13)	0.34958 (11)	0.2089 (3)	0.0381 (7)
C22	0.52138 (13)	0.43413 (11)	0.2221 (3)	0.0384 (7)
H22A	0.4919	0.4437	0.1431	0.046*
H22B	0.5598	0.4444	0.1801	0.046*
C23	0.50998 (12)	0.46813 (11)	0.3662 (3)	0.0309 (7)
C24	0.65709 (16)	0.37292 (13)	0.0881 (4)	0.0657 (10)
H24A	0.6180	0.3635	0.1271	0.079*
H24B	0.6532	0.3846	−0.0213	0.079*
Cl1	0.68538 (5)	0.42883 (4)	0.19717 (12)	0.0760 (3)
Cl2	0.70129 (5)	0.31375 (4)	0.09828 (17)	0.1023 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0369 (12)	0.0466 (12)	0.0280 (10)	−0.0047 (9)	0.0004 (9)	0.0016 (9)
O2	0.0423 (13)	0.0467 (12)	0.0462 (12)	−0.0017 (10)	0.0089 (10)	−0.0019 (10)
O3	0.0675 (16)	0.0459 (13)	0.0448 (13)	0.0044 (11)	0.0116 (11)	−0.0022 (10)
O4	0.0609 (16)	0.0430 (13)	0.0586 (14)	0.0097 (11)	0.0076 (12)	−0.0021 (11)
O5	0.0646 (16)	0.0397 (12)	0.0433 (13)	−0.0064 (11)	0.0002 (11)	−0.0150 (10)
O6	0.0478 (13)	0.0330 (11)	0.0407 (12)	0.0052 (9)	−0.0076 (10)	−0.0096 (9)
C1	0.0347 (17)	0.0285 (14)	0.0314 (16)	0.0019 (12)	−0.0023 (13)	−0.0001 (12)
C2	0.0309 (16)	0.0350 (15)	0.0242 (15)	−0.0015 (12)	−0.0018 (12)	0.0008 (12)
C3	0.0363 (18)	0.0404 (16)	0.0293 (15)	0.0018 (13)	0.0005 (13)	0.0006 (13)
C4	0.0412 (18)	0.0330 (15)	0.0318 (16)	−0.0015 (13)	−0.0045 (14)	0.0070 (13)
C5	0.049 (2)	0.0461 (18)	0.0356 (17)	−0.0046 (15)	−0.0006 (15)	0.0023 (14)
C6	0.062 (2)	0.0460 (19)	0.052 (2)	−0.0118 (17)	−0.0069 (18)	−0.0019 (16)
C7	0.046 (2)	0.053 (2)	0.070 (2)	−0.0133 (17)	−0.0107 (19)	−0.0001 (19)
C8	0.041 (2)	0.0488 (19)	0.064 (2)	−0.0030 (16)	0.0037 (17)	0.0056 (17)
C9	0.046 (2)	0.0339 (16)	0.0397 (17)	0.0005 (14)	−0.0002 (15)	0.0047 (14)
C10	0.046 (2)	0.0490 (19)	0.054 (2)	0.0010 (16)	0.0166 (16)	0.0026 (17)
C11	0.056 (2)	0.049 (2)	0.053 (2)	0.0049 (17)	0.0181 (17)	0.0034 (17)
C12	0.054 (2)	0.060 (2)	0.0443 (19)	0.0097 (17)	0.0051 (16)	−0.0080 (17)
C13	0.058 (2)	0.054 (2)	0.060 (2)	0.0160 (17)	0.0065 (19)	−0.0147 (18)
C14	0.077 (3)	0.0380 (18)	0.051 (2)	0.0061 (17)	−0.0004 (19)	−0.0140 (16)
C15	0.077 (3)	0.0376 (17)	0.0471 (19)	−0.0057 (17)	−0.0002 (19)	−0.0130 (15)
C16	0.051 (2)	0.0325 (16)	0.0385 (17)	−0.0021 (15)	−0.0043 (16)	0.0021 (14)
C17	0.071 (3)	0.0365 (18)	0.050 (2)	−0.0106 (17)	−0.0112 (19)	−0.0001 (15)
C18	0.052 (2)	0.047 (2)	0.068 (2)	−0.0098 (17)	−0.014 (2)	0.0106 (19)
C19	0.049 (2)	0.058 (2)	0.059 (2)	0.0033 (17)	−0.0062 (18)	0.0075 (19)
C20	0.052 (2)	0.0482 (19)	0.047 (2)	0.0087 (17)	−0.0097 (17)	−0.0010 (16)
C21	0.046 (2)	0.0294 (15)	0.0389 (17)	0.0039 (14)	−0.0078 (15)	0.0012 (14)
C22	0.0486 (19)	0.0345 (16)	0.0322 (16)	−0.0012 (14)	0.0008 (14)	−0.0061 (13)
C23	0.0330 (17)	0.0345 (15)	0.0253 (15)	−0.0006 (12)	−0.0013 (12)	−0.0034 (12)
C24	0.065 (3)	0.061 (2)	0.071 (2)	−0.0013 (19)	−0.010 (2)	0.0017 (19)
Cl1	0.0777 (7)	0.0795 (7)	0.0707 (7)	−0.0151 (5)	−0.0071 (5)	−0.0053 (5)
Cl2	0.0663 (7)	0.0586 (6)	0.1820 (13)	−0.0014 (5)	−0.0233 (8)	0.0133 (7)

Geometric parameters (Å, º) top

O1—C4	1.366 (3)	C10—H10B	0.9900
O1—C3	1.441 (3)	C11—H11A	0.9900
O2—C9	1.376 (3)	C11—H11B	0.9900
O2—C10	1.432 (3)	C12—C13	1.496 (4)
O3—C11	1.414 (3)	C12—H12A	0.9900
O3—C12	1.423 (3)	C12—H12B	0.9900
O4—C13	1.421 (4)	C13—H13A	0.9900
O4—C14	1.421 (4)	C13—H13B	0.9900
O5—C16	1.362 (4)	C14—C15	1.488 (5)
O5—C15	1.438 (3)	C14—H14A	0.9900
O6—C21	1.382 (3)	C14—H14B	0.9900
O6—C22	1.438 (3)	C15—H15A	0.9900
C1—C2	1.384 (4)	C15—H15B	0.9900
C1—C23ⁱ	1.387 (4)	C16—C17	1.394 (4)
C1—H1A	0.9500	C16—C21	1.397 (4)
C2—C23	1.402 (3)	C17—C18	1.378 (5)
C2—C3	1.510 (4)	C17—H17A	0.9500
C3—H3A	0.9900	C18—C19	1.373 (5)
C3—H3B	0.9900	C18—H18A	0.9500
C4—C5	1.381 (4)	C19—C20	1.384 (4)
C4—C9	1.407 (4)	C19—H19A	0.9500
C5—C6	1.392 (4)	C20—C21	1.376 (4)
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.360 (5)	C22—C23	1.511 (4)
C6—H6A	0.9500	C22—H22A	0.9900
C7—C8	1.385 (4)	C22—H22B	0.9900
C7—H7A	0.9500	C23—C1ⁱ	1.387 (4)
C8—C9	1.386 (4)	C24—Cl2	1.749 (4)
C8—H8A	0.9500	C24—Cl1	1.763 (3)
C10—C11	1.494 (4)	C24—H24A	0.9900
C10—H10A	0.9900	C24—H24B	0.9900

C4—O1—C3	118.3 (2)	H12A—C12—H12B	108.3
C9—O2—C10	116.1 (2)	O4—C13—C12	110.0 (3)
C11—O3—C12	112.0 (2)	O4—C13—H13A	109.7
C13—O4—C14	112.3 (2)	C12—C13—H13A	109.7
C16—O5—C15	116.9 (2)	O4—C13—H13B	109.7
C21—O6—C22	114.3 (2)	C12—C13—H13B	109.7
C2—C1—C23ⁱ	122.7 (2)	H13A—C13—H13B	108.2
C2—C1—H1A	118.6	O4—C14—C15	109.4 (3)
C23ⁱ—C1—H1A	118.6	O4—C14—H14A	109.8
C1—C2—C23	118.7 (2)	C15—C14—H14A	109.8
C1—C2—C3	120.2 (2)	O4—C14—H14B	109.8
C23—C2—C3	121.0 (2)	C15—C14—H14B	109.8
O1—C3—C2	113.2 (2)	H14A—C14—H14B	108.2
O1—C3—H3A	108.9	O5—C15—C14	108.5 (3)
C2—C3—H3A	108.9	O5—C15—H15A	110.0
O1—C3—H3B	108.9	C14—C15—H15A	110.0
C2—C3—H3B	108.9	O5—C15—H15B	110.0
H3A—C3—H3B	107.8	C14—C15—H15B	110.0
O1—C4—C5	125.2 (3)	H15A—C15—H15B	108.4
O1—C4—C9	115.4 (2)	O5—C16—C17	125.4 (3)
C5—C4—C9	119.3 (3)	O5—C16—C21	115.8 (3)
C4—C5—C6	120.4 (3)	C17—C16—C21	118.8 (3)
C4—C5—H5A	119.8	C18—C17—C16	120.5 (3)
C6—C5—H5A	119.8	C18—C17—H17A	119.7
C7—C6—C5	120.0 (3)	C16—C17—H17A	119.7
C7—C6—H6A	120.0	C19—C18—C17	120.3 (3)
C5—C6—H6A	120.0	C19—C18—H18A	119.9
C6—C7—C8	120.8 (3)	C17—C18—H18A	119.9
C6—C7—H7A	119.6	C18—C19—C20	119.8 (3)
C8—C7—H7A	119.6	C18—C19—H19A	120.1
C7—C8—C9	120.0 (3)	C20—C19—H19A	120.1
C7—C8—H8A	120.0	C21—C20—C19	120.6 (3)
C9—C8—H8A	120.0	C21—C20—H20A	119.7
O2—C9—C8	125.2 (3)	C19—C20—H20A	119.7
O2—C9—C4	115.4 (3)	C20—C21—O6	121.9 (3)
C8—C9—C4	119.5 (3)	C20—C21—C16	119.9 (3)
O2—C10—C11	109.5 (3)	O6—C21—C16	118.1 (3)
O2—C10—H10A	109.8	O6—C22—C23	113.4 (2)
C11—C10—H10A	109.8	O6—C22—H22A	108.9
O2—C10—H10B	109.8	C23—C22—H22A	108.9
C11—C10—H10B	109.8	O6—C22—H22B	108.9
H10A—C10—H10B	108.2	C23—C22—H22B	108.9
O3—C11—C10	110.4 (3)	H22A—C22—H22B	107.7
O3—C11—H11A	109.6	C1ⁱ—C23—C2	118.5 (2)
C10—C11—H11A	109.6	C1ⁱ—C23—C22	121.6 (2)
O3—C11—H11B	109.6	C2—C23—C22	119.8 (2)
C10—C11—H11B	109.6	Cl2—C24—Cl1	111.9 (2)
H11A—C11—H11B	108.1	Cl2—C24—H24A	109.2
O3—C12—C13	109.3 (3)	Cl1—C24—H24A	109.2
O3—C12—H12A	109.8	Cl2—C24—H24B	109.2
C13—C12—H12A	109.8	Cl1—C24—H24B	109.2
O3—C12—H12B	109.8	H24A—C24—H24B	107.9
C13—C12—H12B	109.8

C23ⁱ—C1—C2—C23	0.0 (4)	C16—O5—C15—C14	−179.3 (3)
C23ⁱ—C1—C2—C3	178.2 (3)	O4—C14—C15—O5	−68.1 (3)
C4—O1—C3—C2	−72.7 (3)	C15—O5—C16—C17	−2.9 (4)
C1—C2—C3—O1	126.4 (3)	C15—O5—C16—C21	177.1 (2)
C23—C2—C3—O1	−55.4 (3)	O5—C16—C17—C18	−178.9 (3)
C3—O1—C4—C5	−1.8 (4)	C21—C16—C17—C18	1.2 (4)
C3—O1—C4—C9	179.1 (2)	C16—C17—C18—C19	−1.0 (5)
O1—C4—C5—C6	179.9 (3)	C17—C18—C19—C20	0.6 (5)
C9—C4—C5—C6	−0.9 (4)	C18—C19—C20—C21	−0.6 (5)
C4—C5—C6—C7	0.0 (5)	C19—C20—C21—O6	−176.9 (3)
C5—C6—C7—C8	0.5 (5)	C19—C20—C21—C16	0.9 (4)
C6—C7—C8—C9	−0.2 (5)	C22—O6—C21—C20	−72.7 (3)
C10—O2—C9—C8	−3.7 (4)	C22—O6—C21—C16	109.4 (3)
C10—O2—C9—C4	175.2 (2)	O5—C16—C21—C20	178.9 (3)
C7—C8—C9—O2	178.1 (3)	C17—C16—C21—C20	−1.1 (4)
C7—C8—C9—C4	−0.7 (4)	O5—C16—C21—O6	−3.2 (4)
O1—C4—C9—O2	1.5 (3)	C17—C16—C21—O6	176.7 (2)
C5—C4—C9—O2	−177.7 (2)	C21—O6—C22—C23	98.8 (3)
O1—C4—C9—C8	−179.5 (2)	C1—C2—C23—C1ⁱ	0.0 (4)
C5—C4—C9—C8	1.2 (4)	C3—C2—C23—C1ⁱ	−178.2 (3)
C9—O2—C10—C11	−173.6 (2)	C1—C2—C23—C22	−179.3 (3)
C12—O3—C11—C10	−163.0 (3)	C3—C2—C23—C22	2.5 (4)
O2—C10—C11—O3	−71.6 (3)	O6—C22—C23—C1ⁱ	13.6 (4)
C11—O3—C12—C13	−179.5 (3)	O6—C22—C23—C2	−167.1 (2)
C14—O4—C13—C12	−174.2 (3)	C2—C3—O1—C4	−72.7 (3)
O3—C12—C13—O4	67.2 (3)	C23—C22—O6—C21	98.8 (3)
C13—O4—C14—C15	177.9 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O6ⁱ	0.95	2.47	2.828 (3)	103
C3—H3B···O4ⁱⁱ	0.99	2.59	3.457 (4)	146
C22—H22A···O1ⁱⁱ	0.99	2.32	3.252 (3)	156
C22—H22B···O1	0.99	2.53	2.909 (3)	103
C24—H24A···O6	0.99	2.51	3.455 (4)	160
C24—H24B···O3	0.99	2.36	3.331 (5)	168

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O6ⁱ	0.95	2.47	2.828 (3)	103
C3—H3B···O4ⁱⁱ	0.99	2.59	3.457 (4)	146
C22—H22A···O1ⁱⁱ	0.99	2.32	3.252 (3)	156
C22—H22B···O1	0.99	2.53	2.909 (3)	103
C24—H24A···O6	0.99	2.51	3.455 (4)	160
C24—H24B···O3	0.99	2.36	3.331 (5)	168

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Acknowledgements

This work was supported by the Korea Foundation for the Advancement of Science & Creativity (KOFAC), and funded by Korean Government (MOE), and also by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (No. 2011–0007756). The authors gratefully acknowledge the use of the single crystal X-ray diffractometer in Korea Basic Science Institute (Jeonju Center).

References

Beack, H. J., Yoo, S. M., Kim, J. E., Sim, W. & Lee, J. Y. (2012). Acta Cryst. E68, o720. CSD CrossRef IUCr Journals Google Scholar
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, Y.-I., Kim, D.-W., Choi, K.-Y., Yoo, M., Kim, J. S., Yoo, Y.-J. & Sim, W. (1997). Bull. Korean Chem. Soc. 18, 1311–1313. CAS Google Scholar
Lee, J. Y., Lee, J.-E., Sim, W. & Park, K.-M. (2009). Acta Cryst. E65, o2369–o2370. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Lee, W. Y., Sim, W. & Park, O. S. (1992). Synlett, pp. 157–159. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2,8,15,18,21,24,31,37,44,47,50,53-Dodeca­oxahepta­cyclo­[52.4.0.04,35.06,33.09,14.025,30.038,43]octa­penta­conta-1(54),4,6(33),9(14),10,12,25(30),26,28,34,38(43),39,41,55,57-penta­deca­ene di­chloro­methane disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,8,15,18,21,24,31,37,44,47,50,53-Dodecaoxaheptacyclo[52.4.0.0^4,35.0^6,33.0^9,14.0^25,30.0^38,43]octapentaconta-1(54),4,6(33),9(14),10,12,25(30),26,28,34,38(43),39,41,55,57-pentadecaene dichloromethane disolvate