25-All­yloxy-5,11,17,23-tetra-tert-butyl-26,27,28-trihy­droxy­calix[4]arene chloro­form disolvate

In the title solvated calixarene, C₄₇H₆₀O₄·2CHCl₃, the host chalice displays an almost undistorted cone conformation, stabilized by three strong O—H...O hydrogen bonds at the calixarene's lower rim. One chloro­form solvent mol­ecule is fixed in the calixarene cavity by C—H...π inter­actions, while the second is accommodated in a clathrate-like mode in elliptical packing voids. These voids are spanned by six host mol­ecules connected via C—H...π contacts and van der Waals inter­actions. Within the crystal structure, one tert-butyl group of the calixarene host is disordered over two orientations, with occupancies of 0.884 (4) and 0.116 (4). Furthermore, both solvent mol­ecules show disorder, with occupancies of 0.857 (2) and 0.143 (2) for the cavitate-type, and 0.9359 (17) and 0.0641 (17) for the clathrate-type chloro­form solvent mol­ecules.

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

25-Allyloxy-5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxycalix[4]arene chloroform disolvate

Crystal data

C47H60O4·2CHCl3	F(000) = 3920
Mr = 927.69	Dx = 1.257 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8476 reflections
a = 28.8774 (7) Å	θ = 2.0–30.3°
b = 16.8275 (7) Å	µ = 0.39 mm^−1
c = 23.3186 (8) Å	T = 113 K
β = 120.068 (2)°	Irregular, colourless
V = 9806.5 (6) Å^3	0.60 × 0.37 × 0.35 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer	8635 independent reflections
Radiation source: fine-focus sealed tube	7171 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −34→34
Tmin = 0.791, Tmax = 0.875	k = −20→20
102072 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0912P)^2 + 22.0929P] where P = (Fo^2 + 2Fc^2)/3
8635 reflections	(Δ/σ)max = 0.001
586 parameters	Δρmax = 1.10 e Å^−3
11 restraints	Δρmin = −0.97 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.20967 (7)	0.92546 (10)	0.36652 (9)	0.0230 (4)
H1	0.2134	0.8767	0.3755	0.034*
O2	0.23777 (6)	0.77243 (10)	0.38783 (8)	0.0184 (4)
H2	0.2362	0.7561	0.3528	0.028*
O3	0.23630 (6)	0.75042 (9)	0.27442 (8)	0.0170 (3)
H3	0.2275	0.7952	0.2561	0.025*
O4	0.20933 (6)	0.89840 (9)	0.23504 (8)	0.0182 (4)
C1	0.25611 (9)	0.96449 (13)	0.40831 (12)	0.0167 (5)
C2	0.26959 (9)	1.03018 (14)	0.38343 (12)	0.0179 (5)
C3	0.31206 (10)	1.07801 (14)	0.42677 (12)	0.0212 (5)
H3A	0.3204	1.1236	0.4097	0.025*
C4	0.34291 (10)	1.06178 (15)	0.49417 (12)	0.0222 (5)
C5	0.33042 (10)	0.99192 (15)	0.51612 (12)	0.0215 (5)
H5	0.3521	0.9773	0.5613	0.026*
C6	0.28795 (10)	0.94307 (14)	0.47511 (12)	0.0176 (5)
C7	0.27535 (10)	0.86910 (14)	0.50236 (12)	0.0191 (5)
H7A	0.2851	0.8790	0.5489	0.023*
H7B	0.2363	0.8591	0.4767	0.023*
C8	0.28632 (9)	0.75106 (13)	0.44155 (11)	0.0156 (5)
C9	0.30467 (9)	0.79550 (13)	0.49957 (11)	0.0170 (5)
C10	0.35136 (10)	0.77067 (14)	0.55561 (11)	0.0187 (5)
H10	0.3639	0.8000	0.5955	0.022*
C11	0.38054 (9)	0.70460 (14)	0.55570 (11)	0.0177 (5)
C12	0.36155 (9)	0.66347 (13)	0.49635 (11)	0.0163 (5)
H12	0.3810	0.6188	0.4949	0.020*
C13	0.31452 (9)	0.68583 (13)	0.43858 (11)	0.0151 (5)
C14	0.29589 (9)	0.63862 (13)	0.37534 (11)	0.0159 (5)
H14A	0.2563	0.6368	0.3509	0.019*
H14B	0.3090	0.5834	0.3872	0.019*
C15	0.28491 (9)	0.72798 (13)	0.28118 (11)	0.0156 (5)
C16	0.31454 (9)	0.67186 (13)	0.32957 (11)	0.0158 (5)
C17	0.36286 (9)	0.64621 (14)	0.33614 (12)	0.0192 (5)
H17	0.3838	0.6089	0.3699	0.023*
C18	0.38144 (10)	0.67348 (15)	0.29485 (13)	0.0232 (5)
C19	0.35036 (10)	0.72951 (15)	0.24725 (13)	0.0230 (5)
H19	0.3624	0.7490	0.2188	0.028*
C20	0.30241 (10)	0.75838 (14)	0.23937 (12)	0.0190 (5)
C21	0.27204 (10)	0.82210 (14)	0.18866 (12)	0.0209 (5)
H21A	0.2332	0.8120	0.1683	0.025*
H21B	0.2813	0.8194	0.1532	0.025*
C22	0.25404 (9)	0.94009 (14)	0.24299 (11)	0.0162 (5)
C23	0.28447 (9)	0.90498 (14)	0.21883 (11)	0.0174 (5)
C24	0.32967 (10)	0.94534 (14)	0.22731 (12)	0.0194 (5)
H24	0.3511	0.9218	0.2116	0.023*
C25	0.34416 (9)	1.01916 (14)	0.25811 (11)	0.0183 (5)
C26	0.31250 (9)	1.05137 (14)	0.28186 (11)	0.0175 (5)
H26	0.3219	1.1019	0.3029	0.021*
C27	0.26789 (9)	1.01278 (14)	0.27606 (11)	0.0164 (5)
C28	0.23883 (10)	1.04753 (14)	0.30936 (12)	0.0189 (5)
H28A	0.2025	1.0243	0.2894	0.023*
H28B	0.2351	1.1057	0.3021	0.023*
C29	0.38603 (12)	1.11874 (17)	0.54313 (14)	0.0317 (6)
C30	0.44021 (14)	1.0777 (2)	0.5826 (2)	0.0532 (9)
H30A	0.4530	1.0617	0.5525	0.080*
H30B	0.4365	1.0306	0.6047	0.080*
H30C	0.4659	1.1145	0.6159	0.080*
C31	0.36912 (14)	1.14876 (19)	0.59245 (15)	0.0422 (8)
H31A	0.3655	1.1035	0.6164	0.063*
H31B	0.3348	1.1765	0.5682	0.063*
H31C	0.3963	1.1853	0.6241	0.063*
C32	0.39294 (15)	1.1916 (2)	0.50887 (16)	0.0463 (8)
H32A	0.4210	1.2260	0.5420	0.069*
H32B	0.3592	1.2211	0.4861	0.069*
H32C	0.4031	1.1745	0.4765	0.069*
C33	0.43075 (9)	0.67917 (14)	0.62025 (12)	0.0205 (5)
C34	0.46889 (10)	0.75017 (16)	0.65018 (13)	0.0266 (6)
H34A	0.5012	0.7334	0.6908	0.040*
H34B	0.4511	0.7926	0.6606	0.040*
H34C	0.4788	0.7698	0.6182	0.040*
C35	0.41358 (11)	0.65016 (17)	0.66942 (12)	0.0280 (6)
H35A	0.3895	0.6045	0.6505	0.042*
H35B	0.3950	0.6931	0.6780	0.042*
H35C	0.4453	0.6344	0.7110	0.042*
C36	0.46110 (10)	0.61225 (16)	0.60917 (14)	0.0305 (6)
H36A	0.4384	0.5649	0.5931	0.046*
H36B	0.4937	0.5999	0.6510	0.046*
H36C	0.4708	0.6290	0.5763	0.046*
C37	0.43324 (11)	0.64316 (17)	0.29929 (16)	0.0318 (6)
C38	0.46352 (12)	0.58590 (19)	0.35656 (19)	0.0445 (8)
H38A	0.4737	0.6130	0.3984	0.067*
H38B	0.4958	0.5674	0.3568	0.067*
H38C	0.4406	0.5403	0.3514	0.067*
C39	0.41869 (13)	0.5999 (2)	0.23403 (19)	0.0480 (9)
H39A	0.4513	0.5792	0.2364	0.072*
H39B	0.4013	0.6373	0.1970	0.072*
H39C	0.3943	0.5559	0.2273	0.072*
C40	0.46984 (12)	0.71373 (19)	0.30812 (17)	0.0369 (7)
H40A	0.4784	0.7424	0.3488	0.055*
H40B	0.4516	0.7496	0.2701	0.055*
H40C	0.5030	0.6943	0.3111	0.055*
C41	0.39388 (10)	1.06416 (16)	0.26833 (13)	0.0241 (5)
C42	0.43231 (13)	1.0757 (2)	0.34284 (18)	0.0427 (9)	0.884 (4)
H42A	0.4643	1.1040	0.3497	0.064*	0.884 (4)
H42B	0.4426	1.0237	0.3646	0.064*	0.884 (4)
H42C	0.4145	1.1067	0.3618	0.064*	0.884 (4)
C43	0.42394 (16)	1.0211 (3)	0.2392 (3)	0.0533 (12)	0.884 (4)
H43A	0.4367	0.9697	0.2613	0.080*	0.884 (4)
H43B	0.4545	1.0534	0.2459	0.080*	0.884 (4)
H43C	0.3999	1.0126	0.1916	0.080*	0.884 (4)
C44	0.37733 (13)	1.1466 (2)	0.23536 (17)	0.0348 (8)	0.884 (4)
H44A	0.4092	1.1755	0.2423	0.052*	0.884 (4)
H44B	0.3597	1.1766	0.2551	0.052*	0.884 (4)
H44C	0.3526	1.1402	0.1877	0.052*	0.884 (4)
C42A	0.4060 (10)	1.1343 (18)	0.3136 (14)	0.0427 (9)	0.116 (4)
H42D	0.4170	1.1155	0.3584	0.064*	0.116 (4)
H42E	0.3740	1.1675	0.2974	0.064*	0.116 (4)
H42F	0.4351	1.1655	0.3146	0.064*	0.116 (4)
C44A	0.3800 (10)	1.0939 (16)	0.2015 (13)	0.0348 (8)	0.116 (4)
H44D	0.3467	1.1246	0.1828	0.052*	0.116 (4)
H44E	0.3752	1.0487	0.1725	0.052*	0.116 (4)
H44F	0.4089	1.1279	0.2052	0.052*	0.116 (4)
C45	0.15999 (10)	0.92101 (16)	0.17606 (13)	0.0256 (6)
H45A	0.1645	0.9185	0.1367	0.031*
H45B	0.1500	0.9760	0.1805	0.031*
C46	0.11783 (11)	0.86471 (17)	0.16857 (15)	0.0326 (6)
H46	0.1094	0.8618	0.2030	0.039*
C47	0.09163 (13)	0.8189 (2)	0.1168 (2)	0.0511 (9)
H47A	0.0993	0.8208	0.0817	0.061*
H47B	0.0649	0.7838	0.1143	0.061*
C43A	0.4407 (12)	1.0086 (19)	0.298 (2)	0.0533 (12)	0.116 (4)
H43D	0.4309	0.9587	0.2735	0.080*	0.116 (4)
H43E	0.4508	0.9979	0.3446	0.080*	0.116 (4)
H43F	0.4709	1.0329	0.2970	0.080*	0.116 (4)
Cl1G	0.46677 (6)	0.75867 (8)	0.47116 (7)	0.0466 (3)	0.857 (2)
Cl2G	0.38556 (6)	0.86495 (7)	0.37731 (6)	0.0635 (4)	0.857 (2)
C1G	0.41846 (15)	0.8303 (2)	0.45832 (19)	0.0346 (8)	0.857 (2)
H1G	0.3913	0.8045	0.4668	0.042*	0.857 (2)
Cl3G	0.44711 (6)	0.90859 (8)	0.51429 (6)	0.0769 (5)	0.857 (2)
Cl1H	0.4651 (4)	0.9399 (5)	0.4872 (4)	0.0769 (5)	0.143 (2)
Cl2H	0.3685 (4)	0.8766 (5)	0.3948 (4)	0.0635 (4)	0.143 (2)
Cl3H	0.4631 (4)	0.7786 (6)	0.4816 (5)	0.0466 (3)	0.143 (2)
C1H	0.4238 (7)	0.8599 (10)	0.4695 (11)	0.0346 (8)	0.143 (2)
H1H	0.4123	0.8581	0.5034	0.042*	0.143 (2)
Cl1I	0.27372 (19)	0.4568 (2)	0.44396 (19)	0.0410 (5)	0.9359 (17)
Cl2I	0.28949 (4)	0.34195 (7)	0.54377 (6)	0.0561 (3)	0.9359 (17)
Cl3I	0.38022 (4)	0.41680 (6)	0.54780 (6)	0.0597 (3)	0.9359 (17)
C1I	0.31305 (13)	0.4289 (2)	0.52757 (18)	0.0356 (7)	0.9359 (17)
H1I	0.3114	0.4722	0.5558	0.043*	0.9359 (17)
Cl1J	0.2890 (6)	0.3124 (10)	0.5118 (10)	0.0561 (3)	0.0641 (17)
Cl2J	0.3589 (5)	0.4470 (9)	0.5712 (9)	0.0597 (3)	0.0641 (17)
Cl3J	0.268 (3)	0.460 (4)	0.441 (3)	0.0410 (5)	0.0641 (17)
C1J	0.2940 (11)	0.4142 (15)	0.517 (2)	0.0356 (7)	0.0641 (17)
H1J	0.2716	0.4322	0.5365	0.043*	0.0641 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0210 (9)	0.0190 (9)	0.0252 (9)	0.0005 (7)	0.0087 (7)	0.0063 (7)
O2	0.0180 (8)	0.0212 (9)	0.0143 (8)	0.0044 (7)	0.0069 (7)	0.0013 (7)
O3	0.0167 (8)	0.0162 (8)	0.0184 (8)	0.0002 (6)	0.0092 (7)	0.0024 (6)
O4	0.0167 (8)	0.0173 (8)	0.0191 (8)	−0.0014 (6)	0.0078 (7)	0.0035 (7)
C1	0.0186 (11)	0.0144 (11)	0.0201 (12)	0.0050 (9)	0.0119 (10)	0.0014 (9)
C2	0.0229 (12)	0.0149 (11)	0.0196 (12)	0.0064 (9)	0.0135 (10)	0.0030 (9)
C3	0.0285 (13)	0.0161 (12)	0.0221 (13)	0.0005 (10)	0.0151 (11)	0.0014 (9)
C4	0.0267 (13)	0.0193 (12)	0.0233 (13)	0.0003 (10)	0.0145 (11)	−0.0017 (10)
C5	0.0271 (13)	0.0207 (12)	0.0168 (12)	0.0041 (10)	0.0110 (10)	0.0006 (9)
C6	0.0235 (12)	0.0145 (11)	0.0197 (12)	0.0056 (9)	0.0145 (10)	0.0013 (9)
C7	0.0272 (13)	0.0166 (12)	0.0173 (12)	0.0032 (10)	0.0142 (10)	0.0021 (9)
C8	0.0164 (11)	0.0156 (11)	0.0149 (11)	−0.0002 (9)	0.0079 (9)	0.0033 (9)
C9	0.0235 (12)	0.0123 (11)	0.0177 (11)	0.0005 (9)	0.0123 (10)	0.0022 (9)
C10	0.0264 (13)	0.0147 (11)	0.0143 (11)	−0.0023 (9)	0.0097 (10)	−0.0005 (9)
C11	0.0192 (12)	0.0150 (11)	0.0168 (11)	−0.0017 (9)	0.0073 (10)	0.0012 (9)
C12	0.0178 (11)	0.0129 (11)	0.0176 (11)	0.0007 (9)	0.0084 (10)	0.0008 (9)
C13	0.0186 (11)	0.0133 (11)	0.0152 (11)	−0.0023 (9)	0.0099 (9)	0.0008 (9)
C14	0.0178 (11)	0.0124 (11)	0.0168 (11)	−0.0013 (9)	0.0081 (9)	−0.0017 (9)
C15	0.0169 (11)	0.0146 (11)	0.0157 (11)	−0.0036 (9)	0.0084 (9)	−0.0057 (9)
C16	0.0190 (11)	0.0118 (11)	0.0165 (11)	−0.0051 (9)	0.0088 (9)	−0.0062 (9)
C17	0.0209 (12)	0.0125 (11)	0.0229 (12)	−0.0027 (9)	0.0101 (10)	−0.0058 (9)
C18	0.0236 (13)	0.0171 (12)	0.0330 (14)	−0.0043 (10)	0.0173 (11)	−0.0069 (10)
C19	0.0306 (14)	0.0188 (12)	0.0297 (14)	−0.0047 (10)	0.0226 (12)	−0.0043 (10)
C20	0.0250 (12)	0.0142 (11)	0.0206 (12)	−0.0054 (9)	0.0136 (10)	−0.0064 (9)
C21	0.0287 (13)	0.0209 (13)	0.0172 (12)	−0.0041 (10)	0.0146 (11)	−0.0028 (10)
C22	0.0161 (11)	0.0166 (11)	0.0131 (11)	−0.0006 (9)	0.0052 (9)	0.0057 (9)
C23	0.0220 (12)	0.0165 (12)	0.0127 (11)	−0.0009 (9)	0.0080 (10)	0.0023 (9)
C24	0.0218 (12)	0.0207 (12)	0.0181 (12)	0.0016 (10)	0.0118 (10)	0.0026 (9)
C25	0.0174 (11)	0.0198 (12)	0.0139 (11)	−0.0006 (9)	0.0050 (9)	0.0046 (9)
C26	0.0202 (12)	0.0149 (11)	0.0131 (11)	0.0009 (9)	0.0052 (9)	0.0033 (9)
C27	0.0189 (11)	0.0161 (12)	0.0108 (10)	0.0043 (9)	0.0049 (9)	0.0063 (9)
C28	0.0231 (12)	0.0156 (12)	0.0193 (12)	0.0044 (9)	0.0115 (10)	0.0048 (9)
C29	0.0353 (15)	0.0294 (15)	0.0249 (14)	−0.0082 (12)	0.0109 (12)	−0.0039 (11)
C30	0.0357 (18)	0.048 (2)	0.057 (2)	−0.0056 (15)	0.0088 (16)	−0.0100 (17)
C31	0.061 (2)	0.0319 (16)	0.0328 (16)	−0.0113 (14)	0.0225 (15)	−0.0102 (13)
C32	0.057 (2)	0.0413 (18)	0.0392 (18)	−0.0271 (16)	0.0227 (16)	−0.0095 (14)
C33	0.0182 (12)	0.0191 (12)	0.0170 (12)	−0.0008 (9)	0.0036 (10)	0.0003 (9)
C34	0.0228 (13)	0.0260 (14)	0.0231 (13)	−0.0061 (11)	0.0056 (11)	−0.0011 (11)
C35	0.0250 (13)	0.0299 (14)	0.0178 (12)	−0.0018 (11)	0.0023 (11)	0.0075 (10)
C36	0.0221 (13)	0.0278 (14)	0.0265 (14)	0.0058 (11)	0.0008 (11)	−0.0004 (11)
C37	0.0265 (14)	0.0275 (14)	0.0498 (18)	−0.0012 (11)	0.0254 (13)	−0.0053 (13)
C38	0.0292 (16)	0.0372 (17)	0.075 (2)	0.0091 (13)	0.0315 (17)	0.0071 (16)
C39	0.0380 (17)	0.050 (2)	0.070 (2)	−0.0036 (15)	0.0374 (18)	−0.0243 (17)
C40	0.0293 (15)	0.0387 (17)	0.0508 (19)	−0.0063 (12)	0.0261 (14)	−0.0038 (14)
C41	0.0199 (12)	0.0247 (13)	0.0262 (14)	−0.0033 (10)	0.0105 (11)	0.0017 (10)
C42	0.0253 (17)	0.050 (2)	0.0358 (19)	−0.0159 (15)	0.0024 (15)	0.0047 (16)
C43	0.039 (2)	0.049 (2)	0.090 (3)	−0.0163 (17)	0.046 (2)	−0.021 (2)
C44	0.0284 (16)	0.0359 (19)	0.0408 (19)	−0.0048 (14)	0.0178 (15)	0.0131 (14)
C42A	0.0253 (17)	0.050 (2)	0.0358 (19)	−0.0159 (15)	0.0024 (15)	0.0047 (16)
C44A	0.0284 (16)	0.0359 (19)	0.0408 (19)	−0.0048 (14)	0.0178 (15)	0.0131 (14)
C45	0.0195 (12)	0.0251 (13)	0.0244 (13)	0.0009 (10)	0.0052 (11)	0.0044 (10)
C46	0.0201 (13)	0.0338 (15)	0.0410 (16)	−0.0003 (11)	0.0132 (12)	0.0038 (13)
C47	0.0271 (16)	0.044 (2)	0.069 (2)	−0.0116 (14)	0.0139 (16)	−0.0131 (17)
C43A	0.039 (2)	0.049 (2)	0.090 (3)	−0.0163 (17)	0.046 (2)	−0.021 (2)
Cl1G	0.0506 (6)	0.0437 (8)	0.0489 (7)	0.0115 (5)	0.0275 (5)	−0.0002 (5)
Cl2G	0.0819 (9)	0.0411 (6)	0.0299 (6)	−0.0034 (6)	0.0001 (5)	0.0041 (4)
C1G	0.0311 (17)	0.026 (2)	0.037 (2)	−0.0058 (15)	0.0098 (15)	0.0000 (16)
Cl3G	0.1036 (11)	0.0489 (7)	0.0458 (7)	0.0043 (7)	0.0132 (6)	−0.0152 (5)
Cl1H	0.1036 (11)	0.0489 (7)	0.0458 (7)	0.0043 (7)	0.0132 (6)	−0.0152 (5)
Cl2H	0.0819 (9)	0.0411 (6)	0.0299 (6)	−0.0034 (6)	0.0001 (5)	0.0041 (4)
Cl3H	0.0506 (6)	0.0437 (8)	0.0489 (7)	0.0115 (5)	0.0275 (5)	−0.0002 (5)
C1H	0.0311 (17)	0.026 (2)	0.037 (2)	−0.0058 (15)	0.0098 (15)	0.0000 (16)
Cl1I	0.0554 (14)	0.0369 (6)	0.0405 (6)	0.0039 (7)	0.0314 (6)	0.0012 (4)
Cl2I	0.0508 (5)	0.0547 (6)	0.0760 (8)	0.0115 (4)	0.0416 (5)	0.0267 (5)
Cl3I	0.0339 (5)	0.0563 (6)	0.0845 (8)	−0.0079 (4)	0.0264 (5)	−0.0133 (5)
C1I	0.0371 (19)	0.0322 (17)	0.0420 (19)	0.0016 (14)	0.0231 (17)	−0.0080 (14)
Cl1J	0.0508 (5)	0.0547 (6)	0.0760 (8)	0.0115 (4)	0.0416 (5)	0.0267 (5)
Cl2J	0.0339 (5)	0.0563 (6)	0.0845 (8)	−0.0079 (4)	0.0264 (5)	−0.0133 (5)
Cl3J	0.0554 (14)	0.0369 (6)	0.0405 (6)	0.0039 (7)	0.0314 (6)	0.0012 (4)
C1J	0.0371 (19)	0.0322 (17)	0.0420 (19)	0.0016 (14)	0.0231 (17)	−0.0080 (14)

Geometric parameters (Å, º)

O1—C1	1.367 (3)	C33—C36	1.527 (4)
O1—H1	0.8400	C33—C34	1.535 (3)
O2—C8	1.380 (3)	C33—C35	1.539 (4)
O2—H2	0.8400	C34—H34A	0.9800
O3—C15	1.384 (3)	C34—H34B	0.9800
O3—H3	0.8400	C34—H34C	0.9800
O4—C22	1.398 (3)	C35—H35A	0.9800
O4—C45	1.450 (3)	C35—H35B	0.9800
C1—C2	1.391 (3)	C35—H35C	0.9800
C1—C6	1.402 (3)	C36—H36A	0.9800
C2—C3	1.390 (4)	C36—H36B	0.9800
C2—C28	1.523 (3)	C36—H36C	0.9800
C3—C4	1.391 (4)	C37—C38	1.519 (5)
C3—H3A	0.9500	C37—C40	1.533 (4)
C4—C5	1.400 (4)	C37—C39	1.543 (4)
C4—C29	1.532 (4)	C38—H38A	0.9800
C5—C6	1.385 (4)	C38—H38B	0.9800
C5—H5	0.9500	C38—H38C	0.9800
C6—C7	1.522 (3)	C39—H39A	0.9800
C7—C9	1.520 (3)	C39—H39B	0.9800
C7—H7A	0.9900	C39—H39C	0.9800
C7—H7B	0.9900	C40—H40A	0.9800
C8—C13	1.389 (3)	C40—H40B	0.9800
C8—C9	1.397 (3)	C40—H40C	0.9800
C9—C10	1.391 (3)	C41—C44A	1.49 (2)
C10—C11	1.395 (3)	C41—C43A	1.50 (3)
C10—H10	0.9500	C41—C42A	1.50 (3)
C11—C12	1.391 (3)	C41—C43	1.527 (4)
C11—C33	1.537 (3)	C41—C42	1.535 (4)
C12—C13	1.403 (3)	C41—C44	1.541 (4)
C12—H12	0.9500	C42—H42A	0.9800
C13—C14	1.517 (3)	C42—H42B	0.9800
C14—C16	1.523 (3)	C42—H42C	0.9800
C14—H14A	0.9900	C43—H43A	0.9800
C14—H14B	0.9900	C43—H43B	0.9800
C15—C16	1.389 (3)	C43—H43C	0.9800
C15—C20	1.400 (3)	C44—H44A	0.9800
C16—C17	1.394 (3)	C44—H44B	0.9800
C17—C18	1.394 (4)	C44—H44C	0.9800
C17—H17	0.9500	C42A—H42D	0.9800
C18—C19	1.389 (4)	C42A—H42E	0.9800
C18—C37	1.534 (3)	C42A—H42F	0.9800
C19—C20	1.390 (4)	C44A—H44D	0.9800
C19—H19	0.9500	C44A—H44E	0.9800
C20—C21	1.509 (3)	C44A—H44F	0.9800
C21—C23	1.522 (3)	C45—C46	1.482 (4)
C21—H21A	0.9900	C45—H45A	0.9900
C21—H21B	0.9900	C45—H45B	0.9900
C22—C23	1.391 (3)	C46—C47	1.307 (5)
C22—C27	1.393 (3)	C46—H46	0.9500
C23—C24	1.395 (3)	C47—H47A	0.9500
C24—C25	1.390 (3)	C47—H47B	0.9500
C24—H24	0.9500	C43A—H43D	0.9800
C25—C26	1.394 (3)	C43A—H43E	0.9800
C25—C41	1.533 (3)	C43A—H43F	0.9800
C26—C27	1.387 (3)	Cl1G—C1G	1.752 (4)
C26—H26	0.9500	Cl2G—C1G	1.736 (4)
C27—C28	1.517 (3)	C1G—Cl3G	1.744 (4)
C28—H28A	0.9900	C1G—H1G	1.0000
C28—H28B	0.9900	Cl1H—C1H	1.706 (16)
C29—C30	1.526 (5)	Cl2H—C1H	1.695 (17)
C29—C32	1.531 (4)	Cl3H—C1H	1.709 (16)
C29—C31	1.542 (4)	C1H—H1H	1.0000
C30—H30A	0.9800	Cl1I—C1I	1.758 (4)
C30—H30B	0.9800	Cl2I—C1I	1.733 (4)
C30—H30C	0.9800	Cl3I—C1I	1.763 (3)
C31—H31A	0.9800	C1I—H1I	1.0000
C31—H31B	0.9800	Cl1J—C1J	1.72 (2)
C31—H31C	0.9800	Cl2J—C1J	1.74 (2)
C32—H32A	0.9800	Cl3J—C1J	1.73 (2)
C32—H32B	0.9800	C1J—H1J	1.0000
C32—H32C	0.9800
C1—O1—H1	109.5	C34—C33—C35	109.5 (2)
C8—O2—H2	109.5	C11—C33—C35	108.66 (19)
C15—O3—H3	109.5	C33—C34—H34A	109.5
C22—O4—C45	113.43 (17)	C33—C34—H34B	109.5
O1—C1—C2	117.6 (2)	H34A—C34—H34B	109.5
O1—C1—C6	122.1 (2)	C33—C34—H34C	109.5
C2—C1—C6	120.2 (2)	H34A—C34—H34C	109.5
C3—C2—C1	119.1 (2)	H34B—C34—H34C	109.5
C3—C2—C28	120.9 (2)	C33—C35—H35A	109.5
C1—C2—C28	119.9 (2)	C33—C35—H35B	109.5
C2—C3—C4	122.7 (2)	H35A—C35—H35B	109.5
C2—C3—H3A	118.7	C33—C35—H35C	109.5
C4—C3—H3A	118.7	H35A—C35—H35C	109.5
C3—C4—C5	116.2 (2)	H35B—C35—H35C	109.5
C3—C4—C29	122.7 (2)	C33—C36—H36A	109.5
C5—C4—C29	121.0 (2)	C33—C36—H36B	109.5
C6—C5—C4	123.2 (2)	H36A—C36—H36B	109.5
C6—C5—H5	118.4	C33—C36—H36C	109.5
C4—C5—H5	118.4	H36A—C36—H36C	109.5
C5—C6—C1	118.4 (2)	H36B—C36—H36C	109.5
C5—C6—C7	120.7 (2)	C38—C37—C40	108.6 (3)
C1—C6—C7	120.9 (2)	C38—C37—C18	112.5 (2)
C9—C7—C6	113.18 (19)	C40—C37—C18	109.6 (2)
C9—C7—H7A	108.9	C38—C37—C39	108.7 (3)
C6—C7—H7A	108.9	C40—C37—C39	109.0 (3)
C9—C7—H7B	108.9	C18—C37—C39	108.4 (2)
C6—C7—H7B	108.9	C37—C38—H38A	109.5
H7A—C7—H7B	107.8	C37—C38—H38B	109.5
O2—C8—C13	121.0 (2)	H38A—C38—H38B	109.5
O2—C8—C9	117.4 (2)	C37—C38—H38C	109.5
C13—C8—C9	121.6 (2)	H38A—C38—H38C	109.5
C10—C9—C8	117.9 (2)	H38B—C38—H38C	109.5
C10—C9—C7	120.2 (2)	C37—C39—H39A	109.5
C8—C9—C7	121.9 (2)	C37—C39—H39B	109.5
C9—C10—C11	122.8 (2)	H39A—C39—H39B	109.5
C9—C10—H10	118.6	C37—C39—H39C	109.5
C11—C10—H10	118.6	H39A—C39—H39C	109.5
C12—C11—C10	117.3 (2)	H39B—C39—H39C	109.5
C12—C11—C33	123.0 (2)	C37—C40—H40A	109.5
C10—C11—C33	119.7 (2)	C37—C40—H40B	109.5
C11—C12—C13	122.1 (2)	H40A—C40—H40B	109.5
C11—C12—H12	118.9	C37—C40—H40C	109.5
C13—C12—H12	118.9	H40A—C40—H40C	109.5
C8—C13—C12	118.3 (2)	H40B—C40—H40C	109.5
C8—C13—C14	122.1 (2)	C44A—C41—C43A	114.1 (18)
C12—C13—C14	119.6 (2)	C44A—C41—C42A	108.6 (15)
C13—C14—C16	114.29 (18)	C43A—C41—C42A	108.8 (17)
C13—C14—H14A	108.7	C44A—C41—C43	66.9 (11)
C16—C14—H14A	108.7	C43A—C41—C43	48.1 (14)
C13—C14—H14B	108.7	C42A—C41—C43	134.5 (11)
C16—C14—H14B	108.7	C44A—C41—C25	105.3 (10)
H14A—C14—H14B	107.6	C43A—C41—C25	108.6 (11)
O3—C15—C16	117.0 (2)	C42A—C41—C25	111.6 (11)
O3—C15—C20	121.3 (2)	C43—C41—C25	113.2 (2)
C16—C15—C20	121.6 (2)	C44A—C41—C42	143.7 (10)
C15—C16—C17	118.4 (2)	C43A—C41—C42	65.0 (14)
C15—C16—C14	121.9 (2)	C42A—C41—C42	47.4 (11)
C17—C16—C14	119.7 (2)	C43—C41—C42	108.3 (3)
C18—C17—C16	122.2 (2)	C25—C41—C42	109.1 (2)
C18—C17—H17	118.9	C44A—C41—C44	47.3 (11)
C16—C17—H17	118.9	C43A—C41—C44	141.0 (12)
C19—C18—C17	117.2 (2)	C42A—C41—C44	63.2 (11)
C19—C18—C37	119.8 (2)	C43—C41—C44	108.0 (3)
C17—C18—C37	122.9 (2)	C25—C41—C44	109.6 (2)
C18—C19—C20	123.0 (2)	C42—C41—C44	108.6 (3)
C18—C19—H19	118.5	C41—C42—H42A	109.5
C20—C19—H19	118.5	C41—C42—H42B	109.5
C19—C20—C15	117.6 (2)	C41—C42—H42C	109.5
C19—C20—C21	120.1 (2)	C41—C43—H43A	109.5
C15—C20—C21	122.3 (2)	C41—C43—H43B	109.5
C20—C21—C23	112.27 (19)	C41—C43—H43C	109.5
C20—C21—H21A	109.1	C41—C44—H44A	109.5
C23—C21—H21A	109.1	C41—C44—H44B	109.5
C20—C21—H21B	109.1	C41—C44—H44C	109.5
C23—C21—H21B	109.1	C41—C42A—H42D	109.5
H21A—C21—H21B	107.9	C41—C42A—H42E	109.5
C23—C22—C27	122.2 (2)	H42D—C42A—H42E	109.5
C23—C22—O4	117.5 (2)	C41—C42A—H42F	109.5
C27—C22—O4	120.2 (2)	H42D—C42A—H42F	109.5
C22—C23—C24	118.2 (2)	H42E—C42A—H42F	109.5
C22—C23—C21	121.7 (2)	C41—C44A—H44D	109.5
C24—C23—C21	119.9 (2)	C41—C44A—H44E	109.5
C25—C24—C23	121.8 (2)	H44D—C44A—H44E	109.5
C25—C24—H24	119.1	C41—C44A—H44F	109.5
C23—C24—H24	119.1	H44D—C44A—H44F	109.5
C24—C25—C26	117.7 (2)	H44E—C44A—H44F	109.5
C24—C25—C41	122.5 (2)	O4—C45—C46	107.6 (2)
C26—C25—C41	119.7 (2)	O4—C45—H45A	110.2
C27—C26—C25	122.7 (2)	C46—C45—H45A	110.2
C27—C26—H26	118.6	O4—C45—H45B	110.2
C25—C26—H26	118.6	C46—C45—H45B	110.2
C26—C27—C22	117.4 (2)	H45A—C45—H45B	108.5
C26—C27—C28	119.6 (2)	C47—C46—C45	123.2 (3)
C22—C27—C28	122.9 (2)	C47—C46—H46	118.4
C27—C28—C2	110.40 (19)	C45—C46—H46	118.4
C27—C28—H28A	109.6	C46—C47—H47A	120.0
C2—C28—H28A	109.6	C46—C47—H47B	120.0
C27—C28—H28B	109.6	H47A—C47—H47B	120.0
C2—C28—H28B	109.6	C41—C43A—H43D	109.5
H28A—C28—H28B	108.1	C41—C43A—H43E	109.5
C30—C29—C32	108.4 (3)	H43D—C43A—H43E	109.5
C30—C29—C4	111.8 (2)	C41—C43A—H43F	109.5
C32—C29—C4	112.5 (2)	H43D—C43A—H43F	109.5
C30—C29—C31	108.1 (3)	H43E—C43A—H43F	109.5
C32—C29—C31	107.4 (3)	Cl2G—C1G—Cl3G	110.9 (2)
C4—C29—C31	108.5 (2)	Cl2G—C1G—Cl1G	111.8 (2)
C29—C30—H30A	109.5	Cl3G—C1G—Cl1G	110.7 (2)
C29—C30—H30B	109.5	Cl2G—C1G—H1G	107.8
H30A—C30—H30B	109.5	Cl3G—C1G—H1G	107.8
C29—C30—H30C	109.5	Cl1G—C1G—H1G	107.8
H30A—C30—H30C	109.5	Cl2H—C1H—Cl1H	107.6 (11)
H30B—C30—H30C	109.5	Cl2H—C1H—Cl3H	120.5 (13)
C29—C31—H31A	109.5	Cl1H—C1H—Cl3H	105.3 (11)
C29—C31—H31B	109.5	Cl2H—C1H—H1H	107.6
H31A—C31—H31B	109.5	Cl1H—C1H—H1H	107.6
C29—C31—H31C	109.5	Cl3H—C1H—H1H	107.6
H31A—C31—H31C	109.5	Cl2I—C1I—Cl1I	111.1 (2)
H31B—C31—H31C	109.5	Cl2I—C1I—Cl3I	110.08 (19)
C29—C32—H32A	109.5	Cl1I—C1I—Cl3I	109.9 (3)
C29—C32—H32B	109.5	Cl2I—C1I—H1I	108.5
H32A—C32—H32B	109.5	Cl1I—C1I—H1I	108.5
C29—C32—H32C	109.5	Cl3I—C1I—H1I	108.5
H32A—C32—H32C	109.5	Cl1J—C1J—Cl3J	113 (3)
H32B—C32—H32C	109.5	Cl1J—C1J—Cl2J	112.9 (19)
C36—C33—C34	108.0 (2)	Cl3J—C1J—Cl2J	111 (2)
C36—C33—C11	112.3 (2)	Cl1J—C1J—H1J	106.7
C34—C33—C11	109.8 (2)	Cl3J—C1J—H1J	106.7
C36—C33—C35	108.6 (2)	Cl2J—C1J—H1J	106.7
O1—C1—C2—C3	170.7 (2)	C15—C20—C21—C23	82.2 (3)
C6—C1—C2—C3	−5.6 (3)	C45—O4—C22—C23	−94.5 (2)
O1—C1—C2—C28	−10.9 (3)	C45—O4—C22—C27	87.6 (3)
C6—C1—C2—C28	172.8 (2)	C27—C22—C23—C24	−1.2 (3)
C1—C2—C3—C4	1.8 (4)	O4—C22—C23—C24	−179.05 (19)
C28—C2—C3—C4	−176.5 (2)	C27—C22—C23—C21	174.1 (2)
C2—C3—C4—C5	2.8 (4)	O4—C22—C23—C21	−3.8 (3)
C2—C3—C4—C29	−173.7 (2)	C20—C21—C23—C22	−91.6 (3)
C3—C4—C5—C6	−3.9 (4)	C20—C21—C23—C24	83.6 (3)
C29—C4—C5—C6	172.6 (2)	C22—C23—C24—C25	−0.9 (3)
C4—C5—C6—C1	0.3 (4)	C21—C23—C24—C25	−176.2 (2)
C4—C5—C6—C7	−178.2 (2)	C23—C24—C25—C26	1.4 (3)
O1—C1—C6—C5	−171.6 (2)	C23—C24—C25—C41	179.6 (2)
C2—C1—C6—C5	4.5 (3)	C24—C25—C26—C27	0.2 (3)
O1—C1—C6—C7	6.9 (3)	C41—C25—C26—C27	−178.0 (2)
C2—C1—C6—C7	−177.0 (2)	C25—C26—C27—C22	−2.2 (3)
C5—C6—C7—C9	−89.5 (3)	C25—C26—C27—C28	173.7 (2)
C1—C6—C7—C9	92.1 (3)	C23—C22—C27—C26	2.7 (3)
O2—C8—C9—C10	174.9 (2)	O4—C22—C27—C26	−179.56 (19)
C13—C8—C9—C10	−2.4 (3)	C23—C22—C27—C28	−173.0 (2)
O2—C8—C9—C7	−5.4 (3)	O4—C22—C27—C28	4.8 (3)
C13—C8—C9—C7	177.2 (2)	C26—C27—C28—C2	−77.3 (3)
C6—C7—C9—C10	98.5 (3)	C22—C27—C28—C2	98.2 (3)
C6—C7—C9—C8	−81.1 (3)	C3—C2—C28—C27	83.1 (3)
C8—C9—C10—C11	1.0 (3)	C1—C2—C28—C27	−95.3 (3)
C7—C9—C10—C11	−178.7 (2)	C3—C4—C29—C30	−125.4 (3)
C9—C10—C11—C12	0.7 (3)	C5—C4—C29—C30	58.4 (4)
C9—C10—C11—C33	−177.9 (2)	C3—C4—C29—C32	−3.2 (4)
C10—C11—C12—C13	−1.1 (3)	C5—C4—C29—C32	−179.5 (3)
C33—C11—C12—C13	177.5 (2)	C3—C4—C29—C31	115.5 (3)
O2—C8—C13—C12	−175.2 (2)	C5—C4—C29—C31	−60.8 (3)
C9—C8—C13—C12	2.1 (3)	C12—C11—C33—C36	8.3 (3)
O2—C8—C13—C14	4.6 (3)	C10—C11—C33—C36	−173.1 (2)
C9—C8—C13—C14	−178.1 (2)	C12—C11—C33—C34	128.4 (2)
C11—C12—C13—C8	−0.3 (3)	C10—C11—C33—C34	−53.0 (3)
C11—C12—C13—C14	179.9 (2)	C12—C11—C33—C35	−111.8 (3)
C8—C13—C14—C16	86.2 (3)	C10—C11—C33—C35	66.8 (3)
C12—C13—C14—C16	−94.1 (2)	C19—C18—C37—C38	176.7 (3)
O3—C15—C16—C17	177.99 (19)	C17—C18—C37—C38	−4.5 (4)
C20—C15—C16—C17	0.3 (3)	C19—C18—C37—C40	55.8 (3)
O3—C15—C16—C14	−2.5 (3)	C17—C18—C37—C40	−125.4 (3)
C20—C15—C16—C14	179.9 (2)	C19—C18—C37—C39	−63.0 (3)
C13—C14—C16—C15	−89.3 (3)	C17—C18—C37—C39	115.7 (3)
C13—C14—C16—C17	90.3 (3)	C24—C25—C41—C44A	73.1 (12)
C15—C16—C17—C18	−1.7 (3)	C26—C25—C41—C44A	−108.7 (12)
C14—C16—C17—C18	178.8 (2)	C24—C25—C41—C43A	−49.4 (16)
C16—C17—C18—C19	1.6 (4)	C26—C25—C41—C43A	128.7 (15)
C16—C17—C18—C37	−177.2 (2)	C24—C25—C41—C42A	−169.3 (12)
C17—C18—C19—C20	−0.3 (4)	C26—C25—C41—C42A	8.9 (12)
C37—C18—C19—C20	178.6 (2)	C24—C25—C41—C43	2.1 (4)
C18—C19—C20—C15	−1.0 (4)	C26—C25—C41—C43	−179.7 (3)
C18—C19—C20—C21	177.1 (2)	C24—C25—C41—C42	−118.6 (3)
O3—C15—C20—C19	−176.6 (2)	C26—C25—C41—C42	59.6 (3)
C16—C15—C20—C19	0.9 (3)	C24—C25—C41—C44	122.6 (3)
O3—C15—C20—C21	5.3 (3)	C26—C25—C41—C44	−59.2 (3)
C16—C15—C20—C21	−177.1 (2)	C22—O4—C45—C46	171.8 (2)
C19—C20—C21—C23	−95.8 (3)	O4—C45—C46—C47	−119.6 (3)

Hydrogen-bond geometry (Å, º)

CgA, CgB and CgC are the centroids of the aromatic rings A (C1–C6), B (C8–C13) and C (C15–C20), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.86	2.671 (2)	162
O2—H2···O3	0.84	1.83	2.650 (2)	164
O3—H3···O4	0.84	1.81	2.633 (2)	166
C7—H7B···CgB^i	0.99	2.78	3.535 (2)	133
C28—H28B···CgC^ii	0.99	2.59	3.379 (2)	137
C30—H30A···Cl3G	0.98	2.70	3.316 (4)	121
C30—H30A···Cl1H	0.98	2.68	3.529 (9)	145
C31—H31B···Cl1J^iii	0.98	2.64	3.480 (15)	144
C32—H32B···Cl1J^iii	0.98	2.84	3.654 (17)	142
C36—H36A···Cl3I	0.98	2.89	3.869 (3)	175
C36—H36A···Cl2J	0.98	2.88	3.822 (14)	162
C1G—H1G···CgB	1.00	2.49	3.483 (4)	173
C1J—H1J···CgA^i	1.00	2.42	3.39 (5)	163

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