5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetra­kis[2-(2-chloro­ethoxy)eth­oxy]-2,8,14,20-tetra­sulfonyl­calix[4]arene

Hu, L.; Liu, Y.; Ma, J.-P.; Guo, D.-S.

doi:10.1107/S1600536809002591

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o385-o386

doi:10.1107/S1600536809002591

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5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis[2-(2-chloroethoxy)ethoxy]-2,8,14,20-tetrasulfonylcalix[4]arene

Ling Hu,^a Yang Liu,^a Jiang-Ping Ma ^a and Dian-Shun Guo ^a ^*

^aDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: chdsguo@sdnu.edu.cn

(Received 5 January 2009; accepted 21 January 2009; online 28 January 2009)

Molecules of the title compound, C₅₆H₇₆Cl₄O₁₆S₄, have crystallographic C₂ symmetry and adopt a 1,3-alternate conformation where the four –OCH₂CH₂OCH₂CH₂Cl groups are located alternately above and below the virtual plane (R) defined by the four bridging S atoms. The dihedral angles between the plane (R) and the phenolic rings are 72.85 (7) and 74.57 (7)°. An unusual 24-membered macrocyclic ring is formed in the crystal structure with an array of eight intramolecular C—H⋯O hydrogen bonds between the ether arm H atoms and the sulfonyl O atoms. In the supramolecular structure, the molecular components are linked into infinite zigzag one-dimensional chains by a combination of four intermolecular C—H⋯O hydrogen bonds, forming R₂²(13), R₂²(16), R₂²(21) and R₂²(26) ring motifs. These chains are augmented into a wave-like two-dimensional network by weak C⋯O interactions. One tert-butyl group shows rotational disorder, and one CH₂CH₂Cl group is disordered over two orientations; the site-occupation factors are 0.756 (6) and 0.244 (6) for the two tert-butyl groups, and 0.808 (3) and 0.192 (3) for the two CH₂CH₂Cl units.

Related literature

For general background on the chemistry of thiacalix[4]arene derivatives, see: Shokova & Kovalev (2003 ); Lhoták (2004 ); Morohashi et al. (2006 ). For related crystal structures, see: Mislin et al. (1998 , 1999 ); Akdas et al. (1999 , 2000 ); Lhoták et al. (2002 ); Horiuchi et al. (2007 ); Xu et al. (2008 ). For the synthesis of sulfonylcalix[4]arene derivatives, see: Iki et al. (1998 ); Guo et al. (2007 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For C⋯O short contacts, see: Manoj et al. (2007 ). For atomic radii, see: Bondi (1964 ).

Experimental

Crystal data

C₅₆H₇₆Cl₄O₁₆S₄
M_r = 1275.21
Monoclinic, C 2/c
a = 22.496 (2) Å
b = 16.0372 (15) Å
c = 19.8646 (19) Å
β = 120.355 (1)°
V = 6184.1 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 173 (2) K
0.41 × 0.28 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.856, T_max = 0.912
15381 measured reflections
5442 independent reflections
4709 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.166
S = 1.09
5442 reflections
402 parameters
27 restraints
H-atom parameters constrained
Δρ_max = 1.30 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1ⁱ	0.99	2.48	3.232 (4)	133
C11—H11B⋯O3	0.99	2.51	3.103 (4)	118
C20—H20B⋯O1ⁱⁱ	0.98	2.57	3.377 (5)	139
C21—H21C⋯O8ⁱⁱⁱ	0.98	2.60	3.462 (6)	146
C25—H25A⋯O2	0.99	2.58	3.099 (4)	113
C25—H25B⋯O4	0.99	2.45	3.217 (4)	134
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002591/zl2171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002591/zl2171Isup2.hkl

checkCIF report

Comment top

Thiacalix[4]arenes have attracted considerable interest in recent years as useful scaffolds for highly organized ionophores (Shokova & Kovalev, 2003; Lhoták, 2004; Morohashi et al., 2006; Guo et al., 2007). Compared with classical calix[4]arenes, the presence of four bridging S atoms results in a differing complexation ability, and a diverse cavity and conformational behavior. Moreover, by virtue of the sulfide function, thiacalix[4]arenes can undergo unique transformations that are not applicable to the classical calix[4]arenes, the most important of which is oxidation to sulfinyl and sulfonyl functions. All four sulfide groups of thiacalix[4]arenes, for instance, can be easily converted to sulfones by a small excess amount of an oxidant such as hydrogen peroxide or sodium perborate in an organic acid solvent (Iki et al., 1998; Mislin et al., 1998). A number of crystal stuctures of sulfonyl derivatives of thiacalix[4]arenes (Mislin et al., 1998; Akdas et al., 2000; Lhoták et al., 2002; Horiuchi et al., 2007) have been described. We now present the crystal structure of a new sulfonyl derivative thiacalix[4]arene, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[2-(2-chloroethoxy)ethoxy]-2,8,14,20-tetrasulfonylcalix[4]arene.

The title sulfonylcalix[4]arene derivative is shown in Fig. 1. It was found to adopt a 1,3-alternate conformation with O atoms of the sulfones pointing outward. The main geometric parameters of the title molecule are comparable to those reported for the similar structures (Mislin et al., 1998; Akdas et al., 2000) and most bond lengths and angles are consistent with the values presented for 1,3-alternate-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakismethyl-2,8,14,20-tetrasulfonylcalix[4]arene (Mislin et al., 1998). The sulfonylcalix[4]arene shape of the title compound can be characterized by the values of the dihedral angles between the phenolic rings and the plane (R) defined by the four bridging S atoms. The dihedral angles between the plane (R) and the aromatic rings are 74.57 (7) and 72.85 (7)°, respectively. Actually, the title molecule has a pseudo 4-fold rotation-reflection (S₄) axis. Consistent with this symmetry, the adjacent phenyl rings lie above and below the plane (R), and interplanar angles of the opposing aromatic rings are 34.31 (8) and 38.86 (14)°. The pseudo S₄ symmetry also reasonably depicts the almost parallel orientation of the four ether arms above and below the plane (R). The separations between diametrically located ethereal O5 and O5ⁱ, O7 and O7ⁱ [Symmetry code: (i) -x + 1, y, -z + 3/2] are 4.660 (4) and 4.347 (4) Å, respectively. In the crystal packing, 1,3-alternate molecules are packed along the b axis, forming a type of a beautiful nanotubular array extending in the b direction (Fig. 3). Such a packing was found in the cases of several 1,3-alternate thiaclix[4]arene derivatives (Akdas et al., 1999, 2000; Guo et al., 2007; Xu et al., 2008).

Although no conventional hydrogen bonds are found, various intra- and intermolecular C—H···O hydrogen bonds exist in the crystal structure (Table 1). Interestingly, an unusual 24-membered macrocyclic ring is formed by an array of eight intramolecular C—H···O hydrogen bonds between the sulfonyl O atoms and the ether arm protons closer the phenolic rings, which stabilize the 1,3-alternate conformation (Fig. 4). In this macrocyclic ring, both O atoms of each sulfonyl group act as a hydrogen-bond acceptor, via H, to two C atoms belonging to both adjacent ether arms, respectively. A similar hydrogen bonding array was observed in the structure of the related compound p-tert-butyltetrasulfinylcalix[4]arene, however, it is formed with only four intramolecular O—H···O hydrogen bonds between the OH and SO groups (Mislin, et al., 1999). On the other hand, in the supramolecular structure, infinite zigzag one-dimensional chains are generated by a combination of four intermolecular C—H···O hydrogen bonds, locally forming different ring motifs: two R₂²(13), one R₂²(16), two R₂²(21), and one R₂²(26) (Bernstein et al., 1995), and making a distorted capsule at each link in the chain (Fig. 4). These motifs arise from atoms C20 and C21 at (x, y, z) and (-x + 1, -y + 1, -z + 1) in neighboring molecules that act as hydrogen-bond donors, respectively, via H20B, to atoms O1 at (-x + 1, -y + 1, -z + 1) and (x, y, z), via H21C, to atoms O8 at (x, -y + 1, z - 1/2) and (-x + 1, y, -z + 3/2). The zigzag chains are linked into wave-like two-dimensional networks by the C···O weak interactions (Manoj et al., 2007) between C10^iv [symmetry code: (iv) – x + 3/2, – y + 3/2, –z + 2] and O3. The C10^iv···O3 distance is 3.143 (4) Å, less than the sum of the van der Waals radii for C and O atoms (C = 1.70 Å, O = 1.52 Å; Bondi, 1964).

Related literature top

For general background on the chemistry of thiacalix[4]arene derivatives, see: Shokova & Kovalev (2003); Lhoták (2004); Morohashi et al. (2006). For related crystal structures, see: Mislin et al. (1998, 1999); Akdas et al. (1999, 2000); Lhoták et al. (2002); Horiuchi et al. (2007); Xu et al. (2008). For the synthesis of sulfonylcalix[4]arene derivatives, see: Iki et al. (1998); Guo et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). For C···O short contacts, see: Manoj et al. (2007). For atomic radii, see: Bondi (1964).

Experimental top

For the synthesis of the title compound, to a solution of 1,3-alternate-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[2-(2-chloroethoxy)ethoxy]thiacalix[4]arene, prepared according to the published precedure (Guo et al., 2007), (0.200 g, 0.174 mmol) in CHCl₃ (10 ml) and CF₃CO₂H (1.50 ml) was added 30% H₂O₂ (0.90 ml, 7.840 mmol). The resulting mixture was stirred at 298 K for 50 h, and neutralized with a saturated aqueous solution of NaHCO₃. The organic layer was separated and washed with brine, and dried over anhydrous MgSO₄. Removal of the solvent under reduced pressure gave the title compound as a white solid (yield 95%) by recrystallization from CH₂Cl₂/CH₃OH. ¹H NMR (300 MHz, CDCl₃): δ 8.38 (s, 8H), 4.58 (t, 8H, J = 5.67 Hz), 3.84 (t, 16H, J = 5.98 Hz), 3.71 (t, 8H, J = 5.83 Hz), 1.40 (s, 36H). IR (KBr pellets, cm^-1): 1304, 1137. Single crystals of the title molecule suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution in CH₂Cl₂ and CH₃OH at 273 K.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The disordered atoms are shown, but hydrogen atoms are omitted for clarity. [Symmetry code: (i) -x + 1, y, -z + 3/2].
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen atoms and the minor disordered units are omitted for clarity.
	Fig. 3. The array of intramolecular hydrogen-bonded rings of the title molecule viewed approximatively along the c axis. The minor disordered units and some hydrogen atoms are omitted for clarity. [Symmetry code: (i) -x + 1, y, -z + 3/2].
	Fig. 4. The hydrogen-bonded zigzag one-dimensional chains of the title molecule with R₂²(13), R₂²(16), R₂²(21) and R₂²(26) motifs. The minor disordered moieties and some hydrogen atoms are omitted for clarity. [Symmetry codes: (i) -x + 1, y, -z + 3/2; (ii) -x + 1, -y + 1, -z + 1; (iii) x, -y + 1, z - 1/2].

5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis[2-(2-chloroethoxy)ethoxy]-2,8,14,20-tetrasulfonylcalix[4]arene top

Crystal data top

C₅₆H₇₆Cl₄O₁₆S₄	F(000) = 2688
M_r = 1275.21	D_x = 1.370 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.496 (2) Å	Cell parameters from 7613 reflections
b = 16.0372 (15) Å	θ = 2.2–28.1°
c = 19.8646 (19) Å	µ = 0.39 mm⁻¹
β = 120.355 (1)°	T = 173 K
V = 6184.1 (10) Å³	Block, colourless
Z = 4	0.41 × 0.28 × 0.24 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5442 independent reflections
Radiation source: fine-focus sealed tube	4709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −26→26
T_min = 0.856, T_max = 0.912	k = −16→19
15381 measured reflections	l = −23→23

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0863P)² + 20.079P] where P = (F_o² + 2F_c²)/3
5442 reflections	(Δ/σ)_max = 0.001
402 parameters	Δρ_max = 1.30 e Å⁻³
27 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₅₆H₇₆Cl₄O₁₆S₄	V = 6184.1 (10) Å³
M_r = 1275.21	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.496 (2) Å	µ = 0.39 mm⁻¹
b = 16.0372 (15) Å	T = 173 K
c = 19.8646 (19) Å	0.41 × 0.28 × 0.24 mm
β = 120.355 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5442 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4709 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.912	R_int = 0.022
15381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	27 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0863P)² + 20.079P] where P = (F_o² + 2F_c²)/3
5442 reflections	Δρ_max = 1.30 e Å⁻³
402 parameters	Δρ_min = −0.80 e Å⁻³

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	Occ. (<1)
C5	0.63360 (14)	0.93392 (17)	0.93979 (16)	0.0206 (6)
C6	0.58157 (15)	0.89626 (18)	0.94656 (16)	0.0216 (6)
H6	0.5574	0.9283	0.9653	0.026*
C7	0.56341 (14)	0.81334 (18)	0.92702 (15)	0.0206 (6)
C8	0.59817 (14)	0.76368 (17)	0.90004 (15)	0.0198 (6)
C9	0.65037 (14)	0.80187 (17)	0.89320 (15)	0.0200 (6)
C10	0.66757 (14)	0.88537 (17)	0.91240 (16)	0.0202 (6)
H10	0.7033	0.9093	0.9066	0.024*
C11	0.60405 (18)	0.61541 (18)	0.92839 (18)	0.0298 (7)
H11A	0.5787	0.6106	0.9570	0.036*
H11B	0.6537	0.6229	0.9665	0.036*
C12	0.5924 (2)	0.5401 (2)	0.8784 (2)	0.0429 (9)
H12A	0.5460	0.5428	0.8313	0.051*
H12B	0.6269	0.5386	0.8615	0.051*
C13	0.5939 (3)	0.3938 (2)	0.8805 (3)	0.0513 (10)
H13A	0.6368	0.3866	0.8787	0.062*
H13B	0.5550	0.3982	0.8262	0.062*
C14	0.5834 (2)	0.3196 (2)	0.9195 (3)	0.0529 (10)
H14A	0.5730	0.2701	0.8855	0.063*
H14B	0.5432	0.3299	0.9260	0.063*
C15	0.64816 (14)	0.70631 (17)	0.77013 (16)	0.0191 (6)
C16	0.65912 (14)	0.62388 (18)	0.75768 (17)	0.0220 (6)
H16	0.6922	0.5919	0.8006	0.026*
C17	0.62342 (15)	0.58698 (18)	0.68504 (17)	0.0242 (6)
C22	0.57340 (15)	0.63497 (18)	0.62448 (17)	0.0245 (6)
H22	0.5466	0.6110	0.5741	0.029*
C23	0.56198 (15)	0.71742 (18)	0.63650 (17)	0.0217 (6)
C24	0.60033 (14)	0.75573 (17)	0.70897 (16)	0.0196 (6)
Cl2	0.65663 (6)	0.29815 (6)	1.01204 (7)	0.0613 (3)
O1	0.46758 (12)	0.71591 (14)	0.49020 (12)	0.0331 (5)
O2	0.53371 (11)	0.84535 (14)	0.54324 (13)	0.0309 (5)
O3	0.72979 (11)	0.67345 (13)	0.91607 (12)	0.0303 (5)
O4	0.75042 (11)	0.80237 (13)	0.86416 (13)	0.0295 (5)
O7	0.57763 (11)	0.68433 (12)	0.87321 (11)	0.0252 (5)
O8	0.59813 (14)	0.46765 (14)	0.92163 (14)	0.0395 (6)
S1	0.50048 (4)	0.77435 (5)	0.55345 (4)	0.0239 (2)
S2	0.70254 (4)	0.74481 (4)	0.86614 (4)	0.0216 (2)
C1	0.7049 (3)	1.0578 (3)	0.9434 (4)	0.0496 (16)	0.756 (6)
H1A	0.7484	1.0276	0.9745	0.074*	0.756 (6)
H1B	0.7124	1.1174	0.9555	0.074*	0.756 (6)
H1C	0.6882	1.0492	0.8878	0.074*	0.756 (6)
C2	0.5861 (2)	1.0799 (3)	0.9178 (3)	0.0416 (13)	0.756 (6)
H2A	0.5975	1.1385	0.9326	0.062*	0.756 (6)
H2B	0.5518	1.0614	0.9311	0.062*	0.756 (6)
H2C	0.5672	1.0739	0.8615	0.062*	0.756 (6)
C3	0.6783 (3)	1.0349 (3)	1.0494 (3)	0.0467 (14)	0.756 (6)
H3A	0.7201	1.0013	1.0792	0.070*	0.756 (6)
H3B	0.6428	1.0156	1.0604	0.070*	0.756 (6)
H3C	0.6888	1.0936	1.0644	0.070*	0.756 (6)
C4	0.65239 (16)	1.02564 (18)	0.96255 (18)	0.0263 (7)	0.756 (6)
C1'	0.6356 (10)	1.0747 (10)	0.8892 (9)	0.056 (5)	0.244 (6)
H1E	0.5872	1.0658	0.8494	0.084*	0.244 (6)
H1F	0.6652	1.0557	0.8692	0.084*	0.244 (6)
H1D	0.6435	1.1343	0.9018	0.084*	0.244 (6)
C2'	0.7322 (6)	1.0296 (9)	1.0160 (9)	0.039 (4)	0.244 (6)
H2D	0.7461	1.0868	1.0346	0.059*	0.244 (6)
H2F	0.7540	1.0122	0.9862	0.059*	0.244 (6)
H2E	0.7467	0.9922	1.0606	0.059*	0.244 (6)
C3'	0.6215 (9)	1.0616 (10)	1.0060 (11)	0.052 (5)	0.244 (6)
H3E	0.5711	1.0590	0.9738	0.078*	0.244 (6)
H3D	0.6360	1.1198	1.0189	0.078*	0.244 (6)
H3F	0.6367	1.0298	1.0541	0.078*	0.244 (6)
C4'	0.65239 (16)	1.02564 (18)	0.96255 (18)	0.0263 (7)	0.244 (6)
C18	0.63795 (17)	0.49736 (19)	0.66984 (19)	0.0303 (7)
C19	0.6904 (2)	0.4528 (2)	0.7460 (2)	0.0483 (10)
H19A	0.6721	0.4501	0.7814	0.072*
H19B	0.7339	0.4839	0.7709	0.072*
H19C	0.6985	0.3962	0.7339	0.072*
C20	0.5723 (3)	0.4473 (3)	0.6328 (3)	0.0730 (10)
H20A	0.5541	0.4447	0.6683	0.110*
H20B	0.5817	0.3907	0.6220	0.110*
H20C	0.5383	0.4739	0.5838	0.110*
C21	0.6712 (3)	0.5009 (3)	0.6204 (3)	0.0730 (10)
H21A	0.6829	0.4443	0.6125	0.110*
H21B	0.7132	0.5347	0.6468	0.110*
H21C	0.6391	0.5259	0.5697	0.110*
O5	0.58700 (10)	0.83690 (12)	0.71892 (11)	0.0222 (4)
C25	0.63180 (16)	0.89918 (18)	0.71453 (19)	0.0285 (7)
H25A	0.6423	0.8847	0.6732	0.034*
H25B	0.6756	0.9033	0.7649	0.034*
C26	0.59268 (19)	0.9801 (2)	0.6958 (2)	0.0406 (8)
H26A	0.5534	0.9793	0.6416	0.049*
H26B	0.5745	0.9888	0.7315	0.049*
O6	0.63887 (13)	1.04475 (14)	0.70517 (16)	0.0440 (6)	0.808 (3)
C27	0.6023 (3)	1.1211 (3)	0.6756 (3)	0.0425 (13)	0.808 (3)
H27A	0.5774	1.1352	0.7033	0.051*	0.808 (3)
H27B	0.5681	1.1150	0.6194	0.051*	0.808 (3)
C28	0.6508 (5)	1.1877 (6)	0.6868 (4)	0.0571 (18)	0.808 (3)
H28A	0.6245	1.2387	0.6606	0.069*	0.808 (3)
H28B	0.6770	1.1713	0.6611	0.069*	0.808 (3)
Cl1	0.71051 (11)	1.21148 (10)	0.78691 (10)	0.0777 (6)	0.808 (3)
O6'	0.63887 (13)	1.04475 (14)	0.70517 (16)	0.0440 (6)	0.192 (3)
C27'	0.6214 (13)	1.1202 (16)	0.6602 (17)	0.0425 (13)	0.192 (3)
H27C	0.5721	1.1329	0.6394	0.051*	0.192 (3)
H27D	0.6285	1.1120	0.6154	0.051*	0.192 (3)
C28'	0.663 (3)	1.190 (3)	0.706 (2)	0.0571 (18)	0.192 (3)
H28C	0.6464	1.2395	0.6712	0.069*	0.192 (3)
H28D	0.7103	1.1793	0.7181	0.069*	0.192 (3)
Cl1'	0.6696 (5)	1.2238 (4)	0.7962 (5)	0.0777 (6)	0.192 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0221 (14)	0.0180 (14)	0.0176 (14)	−0.0005 (11)	0.0071 (12)	−0.0007 (11)
C6	0.0251 (15)	0.0190 (14)	0.0192 (14)	−0.0007 (11)	0.0100 (12)	−0.0019 (11)
C7	0.0229 (14)	0.0199 (14)	0.0151 (13)	−0.0034 (11)	0.0066 (12)	0.0010 (11)
C8	0.0243 (15)	0.0152 (14)	0.0126 (13)	−0.0018 (11)	0.0039 (11)	0.0009 (10)
C9	0.0217 (14)	0.0194 (14)	0.0138 (13)	0.0031 (11)	0.0051 (11)	−0.0002 (10)
C10	0.0213 (14)	0.0158 (14)	0.0194 (13)	−0.0008 (11)	0.0072 (11)	−0.0001 (11)
C11	0.0421 (19)	0.0162 (15)	0.0281 (16)	−0.0005 (13)	0.0156 (14)	0.0035 (12)
C12	0.077 (3)	0.0179 (17)	0.045 (2)	−0.0033 (16)	0.040 (2)	0.0011 (14)
C13	0.085 (3)	0.0215 (18)	0.056 (2)	−0.0058 (18)	0.042 (2)	−0.0071 (16)
C14	0.058 (3)	0.0266 (19)	0.071 (3)	−0.0038 (17)	0.031 (2)	−0.0027 (18)
C15	0.0207 (14)	0.0191 (14)	0.0193 (14)	−0.0015 (11)	0.0114 (12)	−0.0036 (11)
C16	0.0214 (14)	0.0183 (14)	0.0252 (15)	0.0022 (11)	0.0109 (12)	−0.0001 (11)
C17	0.0266 (15)	0.0209 (15)	0.0286 (15)	0.0021 (12)	0.0165 (13)	−0.0017 (12)
C22	0.0283 (16)	0.0217 (15)	0.0224 (15)	0.0020 (12)	0.0119 (13)	−0.0055 (11)
C23	0.0230 (14)	0.0212 (15)	0.0212 (14)	0.0051 (11)	0.0113 (12)	0.0014 (11)
C24	0.0229 (15)	0.0152 (14)	0.0239 (15)	0.0008 (11)	0.0143 (13)	−0.0003 (11)
Cl2	0.0629 (7)	0.0338 (5)	0.0756 (8)	−0.0030 (5)	0.0264 (6)	0.0063 (5)
O1	0.0391 (13)	0.0349 (13)	0.0200 (11)	0.0114 (10)	0.0110 (10)	−0.0027 (9)
O2	0.0374 (12)	0.0321 (12)	0.0307 (12)	0.0093 (10)	0.0227 (10)	0.0087 (9)
O3	0.0319 (12)	0.0228 (11)	0.0237 (11)	0.0081 (9)	0.0049 (9)	−0.0014 (8)
O4	0.0228 (11)	0.0255 (11)	0.0382 (12)	−0.0023 (9)	0.0141 (10)	−0.0090 (9)
O7	0.0332 (11)	0.0144 (10)	0.0211 (10)	−0.0039 (8)	0.0088 (9)	−0.0010 (8)
O8	0.0649 (17)	0.0150 (11)	0.0445 (14)	−0.0022 (10)	0.0321 (13)	−0.0002 (10)
S1	0.0294 (4)	0.0249 (4)	0.0178 (4)	0.0076 (3)	0.0122 (3)	0.0014 (3)
S2	0.0203 (4)	0.0175 (4)	0.0215 (4)	0.0023 (3)	0.0065 (3)	−0.0035 (3)
C1	0.057 (3)	0.025 (2)	0.089 (5)	−0.017 (2)	0.053 (3)	−0.020 (3)
C2	0.041 (3)	0.018 (2)	0.059 (3)	−0.0003 (19)	0.020 (2)	−0.003 (2)
C3	0.061 (4)	0.030 (3)	0.040 (3)	−0.013 (2)	0.018 (3)	−0.017 (2)
C4	0.0317 (16)	0.0156 (14)	0.0333 (17)	−0.0031 (12)	0.0176 (14)	−0.0046 (12)
C1'	0.065 (9)	0.034 (7)	0.052 (8)	−0.002 (6)	0.017 (6)	0.003 (6)
C2'	0.035 (7)	0.023 (6)	0.050 (7)	−0.007 (5)	0.013 (5)	−0.009 (5)
C3'	0.056 (8)	0.039 (7)	0.064 (8)	−0.007 (6)	0.033 (7)	−0.019 (6)
C4'	0.0317 (16)	0.0156 (14)	0.0333 (17)	−0.0031 (12)	0.0176 (14)	−0.0046 (12)
C18	0.0352 (17)	0.0196 (16)	0.0318 (17)	0.0063 (13)	0.0137 (14)	−0.0069 (12)
C19	0.071 (3)	0.0274 (19)	0.044 (2)	0.0165 (18)	0.027 (2)	0.0012 (16)
C20	0.086 (3)	0.0380 (18)	0.091 (3)	0.0217 (17)	0.042 (2)	−0.0082 (17)
C21	0.086 (3)	0.0380 (18)	0.091 (3)	0.0217 (17)	0.042 (2)	−0.0082 (17)
O5	0.0275 (11)	0.0138 (10)	0.0269 (11)	0.0020 (8)	0.0149 (9)	−0.0013 (8)
C25	0.0317 (17)	0.0172 (15)	0.0345 (17)	−0.0007 (12)	0.0153 (14)	0.0019 (12)
C26	0.039 (2)	0.0198 (16)	0.055 (2)	−0.0003 (14)	0.0174 (17)	0.0041 (15)
O6	0.0430 (14)	0.0185 (12)	0.0572 (16)	−0.0014 (10)	0.0157 (13)	0.0086 (11)
C27	0.042 (3)	0.0233 (19)	0.053 (3)	−0.002 (2)	0.018 (2)	0.012 (2)
C28	0.055 (5)	0.031 (2)	0.055 (5)	−0.011 (3)	0.006 (5)	0.012 (3)
Cl1	0.0839 (13)	0.0500 (8)	0.0731 (10)	−0.0158 (8)	0.0204 (9)	0.0028 (7)
O6'	0.0430 (14)	0.0185 (12)	0.0572 (16)	−0.0014 (10)	0.0157 (13)	0.0086 (11)
C27'	0.042 (3)	0.0233 (19)	0.053 (3)	−0.002 (2)	0.018 (2)	0.012 (2)
C28'	0.055 (5)	0.031 (2)	0.055 (5)	−0.011 (3)	0.006 (5)	0.012 (3)
Cl1'	0.0839 (13)	0.0500 (8)	0.0731 (10)	−0.0158 (8)	0.0204 (9)	0.0028 (7)

Geometric parameters (Å, º) top

C5—C10	1.381 (4)	C2—H2A	0.9800
C5—C6	1.383 (4)	C2—H2B	0.9800
C5—C4	1.534 (4)	C2—H2C	0.9800
C6—C7	1.388 (4)	C3—C4	1.523 (5)
C6—H6	0.9500	C3—H3A	0.9800
C7—C8	1.399 (4)	C3—H3B	0.9800
C7—S1ⁱ	1.781 (3)	C3—H3C	0.9800
C8—O7	1.367 (3)	C1'—H1E	0.9800
C8—C9	1.391 (4)	C1'—H1F	0.9800
C9—C10	1.393 (4)	C1'—H1D	0.9800
C9—S2	1.772 (3)	C2'—H2D	0.9800
C10—H10	0.9500	C2'—H2F	0.9800
C11—O7	1.455 (4)	C2'—H2E	0.9800
C11—C12	1.499 (5)	C3'—H3E	0.9800
C11—H11A	0.9900	C3'—H3D	0.9800
C11—H11B	0.9900	C3'—H3F	0.9800
C12—O8	1.411 (4)	C18—C20	1.506 (6)
C12—H12A	0.9900	C18—C21	1.507 (6)
C12—H12B	0.9900	C18—C19	1.545 (5)
C13—O8	1.414 (4)	C19—H19A	0.9800
C13—C14	1.503 (6)	C19—H19B	0.9800
C13—H13A	0.9900	C19—H19C	0.9800
C13—H13B	0.9900	C20—H20A	0.9800
C14—Cl2	1.775 (5)	C20—H20B	0.9800
C14—H14A	0.9900	C20—H20C	0.9800
C14—H14B	0.9900	C21—H21A	0.9800
C15—C16	1.390 (4)	C21—H21B	0.9800
C15—C24	1.393 (4)	C21—H21C	0.9800
C15—S2	1.777 (3)	O5—C25	1.453 (4)
C16—C17	1.381 (4)	C25—C26	1.505 (4)
C16—H16	0.9500	C25—H25A	0.9900
C17—C22	1.392 (4)	C25—H25B	0.9900
C17—C18	1.537 (4)	C26—O6	1.412 (4)
C22—C23	1.391 (4)	C26—H26A	0.9900
C22—H22	0.9500	C26—H26B	0.9900
C23—C24	1.392 (4)	O6—C27	1.425 (6)
C23—S1	1.778 (3)	C27—C28	1.461 (7)
C24—O5	1.373 (3)	C27—H27A	0.9900
O1—S1	1.437 (2)	C27—H27B	0.9900
O2—S1	1.432 (2)	C28—Cl1	1.790 (6)
O3—S2	1.433 (2)	C28—H28A	0.9900
O4—S2	1.434 (2)	C28—H28B	0.9900
S1—C7ⁱ	1.781 (3)	C27'—C28'	1.453 (18)
C1—C4	1.503 (5)	C27'—H27C	0.9900
C1—H1A	0.9800	C27'—H27D	0.9900
C1—H1B	0.9800	C28'—Cl1'	1.79 (2)
C1—H1C	0.9800	C28'—H28C	0.9900
C2—C4	1.560 (5)	C28'—H28D	0.9900

C10—C5—C6	117.1 (3)	C1—C4—C3	110.6 (4)
C10—C5—C4	122.1 (3)	C1—C4—C5	112.9 (3)
C6—C5—C4	120.7 (3)	C3—C4—C5	108.5 (3)
C5—C6—C7	122.4 (3)	C1—C4—C2	108.2 (4)
C5—C6—H6	118.8	C3—C4—C2	107.5 (3)
C7—C6—H6	118.8	C5—C4—C2	109.0 (3)
C6—C7—C8	120.7 (3)	H1E—C1'—H1F	109.5
C6—C7—S1ⁱ	115.6 (2)	H1E—C1'—H1D	109.5
C8—C7—S1ⁱ	123.5 (2)	H1F—C1'—H1D	109.5
O7—C8—C9	120.5 (3)	H2D—C2'—H2F	109.5
O7—C8—C7	122.4 (3)	H2D—C2'—H2E	109.5
C9—C8—C7	116.7 (3)	H2F—C2'—H2E	109.5
C8—C9—C10	121.9 (3)	H3E—C3'—H3D	109.5
C8—C9—S2	121.6 (2)	H3E—C3'—H3F	109.5
C10—C9—S2	116.4 (2)	H3D—C3'—H3F	109.5
C5—C10—C9	121.2 (3)	C20—C18—C21	112.8 (4)
C5—C10—H10	119.4	C20—C18—C17	110.0 (3)
C9—C10—H10	119.4	C21—C18—C17	108.5 (3)
O7—C11—C12	104.2 (2)	C20—C18—C19	107.9 (3)
O7—C11—H11A	110.9	C21—C18—C19	105.7 (3)
C12—C11—H11A	110.9	C17—C18—C19	111.9 (3)
O7—C11—H11B	110.9	C18—C19—H19A	109.5
C12—C11—H11B	110.9	C18—C19—H19B	109.5
H11A—C11—H11B	108.9	H19A—C19—H19B	109.5
O8—C12—C11	109.2 (3)	C18—C19—H19C	109.5
O8—C12—H12A	109.8	H19A—C19—H19C	109.5
C11—C12—H12A	109.8	H19B—C19—H19C	109.5
O8—C12—H12B	109.8	C18—C20—H20A	109.5
C11—C12—H12B	109.8	C18—C20—H20B	109.5
H12A—C12—H12B	108.3	H20A—C20—H20B	109.5
O8—C13—C14	110.3 (3)	C18—C20—H20C	109.5
O8—C13—H13A	109.6	H20A—C20—H20C	109.5
C14—C13—H13A	109.6	H20B—C20—H20C	109.5
O8—C13—H13B	109.6	C18—C21—H21A	109.5
C14—C13—H13B	109.6	C18—C21—H21B	109.5
H13A—C13—H13B	108.1	H21A—C21—H21B	109.5
C13—C14—Cl2	112.5 (3)	C18—C21—H21C	109.5
C13—C14—H14A	109.1	H21A—C21—H21C	109.5
Cl2—C14—H14A	109.1	H21B—C21—H21C	109.5
C13—C14—H14B	109.1	C24—O5—C25	115.8 (2)
Cl2—C14—H14B	109.1	O5—C25—C26	105.7 (2)
H14A—C14—H14B	107.8	O5—C25—H25A	110.6
C16—C15—C24	120.9 (3)	C26—C25—H25A	110.6
C16—C15—S2	115.7 (2)	O5—C25—H25B	110.6
C24—C15—S2	123.2 (2)	C26—C25—H25B	110.6
C17—C16—C15	122.1 (3)	H25A—C25—H25B	108.7
C17—C16—H16	118.9	O6—C26—C25	107.5 (3)
C15—C16—H16	118.9	O6—C26—H26A	110.2
C16—C17—C22	117.1 (3)	C25—C26—H26A	110.2
C16—C17—C18	122.5 (3)	O6—C26—H26B	110.2
C22—C17—C18	120.4 (3)	C25—C26—H26B	110.2
C23—C22—C17	121.1 (3)	H26A—C26—H26B	108.5
C23—C22—H22	119.5	C26—O6—C27	110.1 (3)
C17—C22—H22	119.5	O6—C27—C28	109.5 (6)
C22—C23—C24	121.7 (3)	O6—C27—H27A	109.8
C22—C23—S1	117.0 (2)	C28—C27—H27A	109.8
C24—C23—S1	121.2 (2)	O6—C27—H27B	109.8
O5—C24—C23	120.1 (2)	C28—C27—H27B	109.8
O5—C24—C15	122.9 (2)	H27A—C27—H27B	108.2
C23—C24—C15	116.9 (2)	C27—C28—Cl1	114.0 (5)
C8—O7—C11	119.0 (2)	C27—C28—H28A	108.7
C12—O8—C13	112.3 (3)	Cl1—C28—H28A	108.7
O2—S1—O1	118.02 (14)	C27—C28—H28B	108.7
O2—S1—C23	108.83 (14)	Cl1—C28—H28B	108.7
O1—S1—C23	106.96 (13)	H28A—C28—H28B	107.6
O2—S1—C7ⁱ	106.76 (13)	C28'—C27'—H27C	109.2
O1—S1—C7ⁱ	107.68 (13)	C28'—C27'—H27D	109.2
C23—S1—C7ⁱ	108.26 (13)	H27C—C27'—H27D	107.9
O3—S2—O4	117.92 (14)	C27'—C28'—Cl1'	124 (3)
O3—S2—C9	108.63 (13)	C27'—C28'—H28C	106.2
O4—S2—C9	107.32 (13)	Cl1'—C28'—H28C	106.2
O3—S2—C15	106.68 (13)	C27'—C28'—H28D	106.2
O4—S2—C15	108.27 (13)	Cl1'—C28'—H28D	106.2
C9—S2—C15	107.62 (13)	H28C—C28'—H28D	106.4

C10—C5—C6—C7	0.0 (4)	C14—C13—O8—C12	−166.6 (4)
C4—C5—C6—C7	−179.6 (3)	C22—C23—S1—O2	−120.7 (2)
C5—C6—C7—C8	0.7 (4)	C24—C23—S1—O2	54.8 (3)
C5—C6—C7—S1ⁱ	175.6 (2)	C22—C23—S1—O1	7.8 (3)
C6—C7—C8—O7	−173.6 (2)	C24—C23—S1—O1	−176.6 (2)
S1ⁱ—C7—C8—O7	11.9 (4)	C22—C23—S1—C7ⁱ	123.6 (2)
C6—C7—C8—C9	−0.8 (4)	C24—C23—S1—C7ⁱ	−60.9 (3)
S1ⁱ—C7—C8—C9	−175.2 (2)	C8—C9—S2—O3	−51.8 (3)
O7—C8—C9—C10	173.2 (2)	C10—C9—S2—O3	123.9 (2)
C7—C8—C9—C10	0.2 (4)	C8—C9—S2—O4	179.7 (2)
O7—C8—C9—S2	−11.4 (4)	C10—C9—S2—O4	−4.6 (3)
C7—C8—C9—S2	175.6 (2)	C8—C9—S2—C15	63.4 (3)
C6—C5—C10—C9	−0.6 (4)	C10—C9—S2—C15	−120.9 (2)
C4—C5—C10—C9	179.0 (3)	C16—C15—S2—O3	−19.6 (3)
C8—C9—C10—C5	0.5 (4)	C24—C15—S2—O3	164.5 (2)
S2—C9—C10—C5	−175.2 (2)	C16—C15—S2—O4	108.3 (2)
O7—C11—C12—O8	−164.0 (3)	C24—C15—S2—O4	−67.7 (3)
O8—C13—C14—Cl2	−67.9 (4)	C16—C15—S2—C9	−136.0 (2)
C24—C15—C16—C17	−0.3 (4)	C24—C15—S2—C9	48.1 (3)
S2—C15—C16—C17	−176.3 (2)	C10—C5—C4—C1	6.4 (5)
C15—C16—C17—C22	−2.5 (4)	C6—C5—C4—C1	−174.1 (4)
C15—C16—C17—C18	176.6 (3)	C10—C5—C4—C3	−116.7 (4)
C16—C17—C22—C23	2.3 (4)	C6—C5—C4—C3	62.9 (4)
C18—C17—C22—C23	−176.9 (3)	C10—C5—C4—C2	126.6 (3)
C17—C22—C23—C24	0.7 (5)	C6—C5—C4—C2	−53.8 (4)
C17—C22—C23—S1	176.2 (2)	C16—C17—C18—C20	125.9 (4)
C22—C23—C24—O5	−179.1 (3)	C22—C17—C18—C20	−54.9 (4)
S1—C23—C24—O5	5.6 (4)	C16—C17—C18—C21	−110.2 (4)
C22—C23—C24—C15	−3.5 (4)	C22—C17—C18—C21	68.9 (4)
S1—C23—C24—C15	−178.8 (2)	C16—C17—C18—C19	6.0 (4)
C16—C15—C24—O5	178.8 (2)	C22—C17—C18—C19	−174.9 (3)
S2—C15—C24—O5	−5.5 (4)	C23—C24—O5—C25	−98.1 (3)
C16—C15—C24—C23	3.3 (4)	C15—C24—O5—C25	86.5 (3)
S2—C15—C24—C23	179.0 (2)	C24—O5—C25—C26	158.7 (3)
C9—C8—O7—C11	99.0 (3)	O5—C25—C26—O6	169.4 (3)
C7—C8—O7—C11	−88.4 (3)	C25—C26—O6—C27	170.1 (4)
C12—C11—O7—C8	−160.8 (3)	C26—O6—C27—C28	179.1 (5)
C11—C12—O8—C13	−174.6 (3)	O6—C27—C28—Cl1	−65.1 (9)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.99	2.48	3.232 (4)	133
C11—H11B···O3	0.99	2.51	3.103 (4)	118
C20—H20B···O1ⁱⁱ	0.98	2.57	3.377 (5)	139
C21—H21C···O8ⁱⁱⁱ	0.98	2.60	3.462 (6)	146
C25—H25A···O2	0.99	2.58	3.099 (4)	113
C25—H25B···O4	0.99	2.45	3.217 (4)	134

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₅₆H₇₆Cl₄O₁₆S₄
M_r	1275.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	22.496 (2), 16.0372 (15), 19.8646 (19)
β (°)	120.355 (1)
V (Å³)	6184.1 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.41 × 0.28 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.856, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	15381, 5442, 4709
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.166, 1.09
No. of reflections	5442
No. of parameters	402
No. of restraints	27
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0863P)² + 20.079P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.30, −0.80

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.99	2.48	3.232 (4)	132.5
C11—H11B···O3	0.99	2.51	3.103 (4)	117.8
C20—H20B···O1ⁱⁱ	0.98	2.57	3.377 (5)	139.3
C21—H21C···O8ⁱⁱⁱ	0.98	2.60	3.462 (6)	146.4
C25—H25A···O2	0.99	2.58	3.099 (4)	112.7
C25—H25B···O4	0.99	2.45	3.217 (4)	134.3

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z−1/2.

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant No. 20572064) and the Natural Science Foundation of Shandong Province (grant No. Y2006B30) is gratefully acknowledged.

References

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Volume 65| Part 2| February 2009| Pages o385-o386

doi:10.1107/S1600536809002591

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

5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetra­kis[2-(2-chloro­eth­oxy)eth­­oxy]-2,8,14,20-tetra­sulfonyl­calix[4]arene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis[2-(2-chloroethoxy)ethoxy]-2,8,14,20-tetrasulfonylcalix[4]arene