5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetra-kis[2-(2-chloro-ethoxy)eth-oxy]-2,8,14,20-tetra-sulfonyl-calix[4]arene.

Mol-ecules of the title compound, C(56)H(76)Cl(4)O(16)S(4), have crystallographic C(2) symmetry and adopt a 1,3-alternate conformation where the four -OCH(2)CH(2)OCH(2)CH(2)Cl 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 intra-molecular C-H⋯O hydrogen bonds between the ether arm H atoms and the sulfonyl O atoms. In the supra-molecular structure, the mol-ecular components are linked into infinite zigzag one-dimensional chains by a combination of four inter-molecular C-H⋯O hydrogen bonds, forming R(2) (2)(13), R(2) (2)(16), R(2) (2)(21) and R(2) (2)(26) ring motifs. These chains are augmented into a wave-like two-dimensional network by weak C⋯O inter-actions. One tert-butyl group shows rotational disorder, and one CH(2)CH(2)Cl 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 CH(2)CH(2)Cl 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 = 1275.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.166

S = 1.09

5442 reflections

402 parameters

27 restraints

H-atom parameters constrained

Δρmax = 1.30 e Å−3

Δρmin = −0.80 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C56H76Cl4O16S4	F(000) = 2688
Mr = 1275.21	Dx = 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

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

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(Fo2) + (0.0863P)2 + 20.079P] where P = (Fo2 + 2Fc2)/3
5442 reflections	(Δ/σ)max = 0.001
402 parameters	Δρmax = 1.30 e Å−3
27 restraints	Δρmin = −0.80 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) ; (iii) .