Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4

Chintan R. Patel; Marivel Samipillai; Holger B. Friedrich; Hendrik G. Kruger; Thavendran Govender; Glenn E. M. Maguire

doi:10.1515/ncrs-2016-0286

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Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C₆₈H₁₀₄O₄

Chintan R. Patel , Marivel Samipillai , Holger B. Friedrich , Hendrik G. Kruger , Thavendran Govender and Glenn E. M. Maguire

Published/Copyright: April 10, 2017

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From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 3

Abstract

C₆₈H₁₀₄O₄, monoclinic, P2₁/n (no. 14), a = 19.4442(12) Å, b = 16.8522(11) Å, c = 38.048(3) Å, β = 92.400(1)°, V = 12456.4(14) Å³, Z = 8, R_gt(F) = 0.0488, wR_ref(F²) = 0.1326, T = 153 K.

CCDC no.:: 1533990

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:	Colourless block
Size:	0.47 × 0.46 × 0.40 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	0.6 cm⁻¹
Diffractometer, scan mode:	Bruker APEXII, 0.5° φ and ω
2θ_max, completeness:	56.8°, >99%
N(hkl)_measured, N(hkl)_unique, R_int:	159808, 31202, 0.043
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 22557
N(param)_refined:	1457
Programs:	Bruker programs [6], SHELX [7], WinGX/ORTEP [8, 9]

Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²).

Atom	x	y	z	U_iso*/U_eq
O1A	0.06287(4)	0.29691(5)	0.18781(2)	0.02302(18)
C1A	0.06099(6)	0.36101(7)	0.13129(3)	0.0210(2)
O1C	0.71749(5)	0.36851(6)	0.09858(2)	0.0290(2)
C1C	0.74227(7)	0.50158(8)	0.07935(3)	0.0262(3)
O2A	0.16287(5)	0.13563(5)	0.17197(2)	0.02673(19)
C2A	0.04048(6)	0.35956(8)	0.09570(3)	0.0235(3)
H2A	0.0480	0.4054	0.0818	0.028*
C2C	0.79101(7)	0.56173(8)	0.07648(3)	0.0277(3)
H2C	0.7773	0.6104	0.0657	0.033*
O3A	0.31708(5)	0.18583(6)	0.16256(2)	0.0276(2)
C3A	0.00958(6)	0.29379(8)	0.07987(3)	0.0243(3)
O3C	0.76612(4)	0.21885(5)	0.15459(2)	0.02462(19)
C3C	0.85900(7)	0.55312(8)	0.08881(3)	0.0268(3)
O4A	0.21752(5)	0.34080(5)	0.16378(2)	0.02407(19)
C4A	0.00352(6)	0.22609(8)	0.10062(3)	0.0237(3)
H4A	−0.0149	0.1792	0.0900	0.028*
O4C	0.60480(5)	0.29706(6)	0.15711(2)	0.0290(2)
C4C	0.87733(7)	0.48109(8)	0.10470(3)	0.0261(3)
H4C	0.9232	0.4742	0.1137	0.031*
C5A	0.02327(6)	0.22451(7)	0.13608(3)	0.0213(2)
O5C	0.55339(4)	0.41992(6)	0.09057(2)	0.0272(2)
C5C	0.83093(6)	0.41907(8)	0.10782(3)	0.0233(3)
C6A	0.04916(6)	0.29404(7)	0.15169(3)	0.0209(2)
C6C	0.76354(6)	0.42961(8)	0.09422(3)	0.0236(3)
C7A	0.00124(7)	0.31435(9)	0.20597(4)	0.0320(3)
H7AA^a	−0.0316	0.2696	0.2036	0.038*
H7AB^a	−0.0212	0.3627	0.1961	0.038*
H7AC^b	−0.014(2)	0.375(3)	0.1989(12)	0.038*
H7AD^b	−0.037(2)	0.279(3)	0.1946(12)	0.038*
C7C	0.69399(9)	0.32786(10)	0.06740(4)	0.0428(4)
H7C^c	0.6602	0.3506	0.0517	0.051*
H7CA^d	0.7155	0.3510	0.0466	0.051*
H7CB^d	0.6434	0.3332	0.0641	0.051*
C8A^a	0.0234(3)	0.3276(3)	0.24558(13)	0.0296(8)
H8AA^a	−0.0184	0.3267	0.2596	0.036*
H8AB^a	0.0528	0.2825	0.2535	0.036*
C8B^b	0.0083(5)	0.3090(6)	0.2432(3)	0.0296(8)
H8BA^b	0.0319	0.2586	0.2496	0.036*
H8BB^b	−0.0380	0.3077	0.2530	0.036*
C8C^c	0.7211(3)	0.2571(4)	0.06119(15)	0.0445(13)
H8CA^c	0.7137	0.2221	0.0816	0.053*
H8CB^c	0.7714	0.2632	0.0590	0.053*
C8D^d	0.7149(4)	0.2352(3)	0.07138(14)	0.0358(11)
H8DA^d	0.7654	0.2305	0.0699	0.043*
H8DB^d	0.7029	0.2170	0.0951	0.043*
C9A^a	0.06201(16)	0.40402(19)	0.25347(8)	0.0262(6)
H9AA^a	0.0311	0.4493	0.2478	0.031*
H9AB^a	0.1014	0.4075	0.2379	0.031*
C9B^b	0.0480(3)	0.3765(4)	0.25914(16)	0.0310(12)
H9BA^b	0.0261	0.4272	0.2518	0.037*
H9BB^b	0.0955	0.3761	0.2507	0.037*
C9C^d	0.6812(2)	0.1800(2)	0.04452(9)	0.0423(10)
H9CA^d	0.6928	0.1248	0.0514	0.051*
H9CB^d	0.6307	0.1858	0.0457	0.051*
C9D^c	0.69092(18)	0.2174(2)	0.02800(10)	0.0393(9)
H9DA^c	0.6413	0.2075	0.0311	0.047*
H9DB^c	0.6948	0.2545	0.0080	0.047*
C10A^a	0.08880(12)	0.41182(15)	0.29149(6)	0.0349(7)
H10A^a	0.1175	0.3648	0.2975	0.042*
H10B^a	0.1190	0.4591	0.2934	0.042*
C10B^b	0.0502(2)	0.3699(3)	0.29957(12)	0.0393(13)
H10C^b	0.0029	0.3606	0.3073	0.047*
H10D^b	0.0782	0.3230	0.3066	0.047*
C11B^b	0.0790(3)	0.4409(3)	0.31841(13)	0.0499(15)
H11A^b	0.0527	0.4885	0.3107	0.060*
H11B^b	0.1274	0.4485	0.3120	0.060*
C12A^a	0.0642(7)	0.4169(9)	0.3560(4)	0.0645(19)
H12A^a	0.0271	0.4219	0.3725	0.097*
H12B^a	0.0883	0.3665	0.3600	0.097*
H12C^a	0.0968	0.4609	0.3596	0.097*
C12B^b	0.0765(15)	0.4330(19)	0.3582(7)	0.0645(19)
H12D^b	0.0959	0.4808	0.3695	0.097*
H12E^b	0.0286	0.4265	0.3648	0.097*
H12F^b	0.1034	0.3866	0.3661	0.097*
C13A	−0.01401(8)	0.29183(9)	0.04105(3)	0.0318(3)
C13C	0.91069(7)	0.62162(9)	0.08838(4)	0.0336(3)
C14A	−0.00920(10)	0.37337(11)	0.02374(4)	0.0488(4)
H14D	−0.0247	0.3695	−0.0010	0.073*
H14E	−0.0384	0.4111	0.0358	0.073*
H14F	0.0386	0.3918	0.0253	0.073*
C14C	0.88838(10)	0.68571(11)	0.06182(6)	0.0603(6)
H14A	0.8851	0.6627	0.0382	0.091*
H14B	0.8434	0.7068	0.0678	0.091*
H14C	0.9224	0.7287	0.0625	0.091*
C15A	−0.08916(9)	0.26502(12)	0.03734(4)	0.0496(4)
H15D	−0.0939	0.2127	0.0482	0.074*
H15E	−0.1184	0.3033	0.0491	0.074*
H15F	−0.1033	0.2618	0.0123	0.074*
C15C	0.98183(8)	0.59239(10)	0.07860(5)	0.0457(4)
H15A	0.9789	0.5692	0.0550	0.069*
H15B	1.0141	0.6371	0.0790	0.069*
H15C	0.9981	0.5521	0.0956	0.069*
C16A	0.03190(10)	0.23373(11)	0.02195(4)	0.0501(4)
H16D	0.0292	0.1812	0.0329	0.075*
H16E	0.0163	0.2302	−0.0028	0.075*
H16F	0.0796	0.2525	0.0236	0.075*
C16C	0.91579(11)	0.65762(13)	0.12520(5)	0.0614(5)
H16A	0.8703	0.6765	0.1316	0.092*
H16B	0.9322	0.6173	0.1421	0.092*
H16C	0.9481	0.7022	0.1255	0.092*
C17A	0.01981(6)	0.14698(7)	0.15639(3)	0.0235(3)
H17C	0.0358	0.1558	0.1811	0.028*
H17D	−0.0284	0.1282	0.1563	0.028*
C17C	0.85073(6)	0.34452(8)	0.12790(3)	0.0243(3)
H17A	0.9015	0.3405	0.1302	0.029*
H17B	0.8332	0.2975	0.1147	0.029*
C18A	0.06445(6)	0.08467(7)	0.13983(3)	0.0227(2)
C18C	0.82115(6)	0.34551(7)	0.16428(3)	0.0211(2)
C19A	0.03685(7)	0.03157(8)	0.11487(3)	0.0247(3)
H19A	−0.0115	0.0315	0.1100	0.030*
C19C	0.83537(6)	0.40916(7)	0.18681(3)	0.0224(2)
H19C	0.8652	0.4499	0.1794	0.027*
C20A	0.07752(7)	−0.02133(8)	0.09686(3)	0.0263(3)
C20C	0.80742(6)	0.41513(7)	0.21974(3)	0.0223(2)
C21A	0.14851(7)	−0.01815(8)	0.10424(4)	0.0272(3)
H21A	0.1775	−0.0532	0.0920	0.033*
C21C	0.76091(6)	0.35647(7)	0.22891(3)	0.0230(2)
H21C	0.7399	0.3603	0.2509	0.028*
C22A	0.17846(6)	0.03393(7)	0.12860(3)	0.0242(3)
C22C	0.74409(6)	0.29265(7)	0.20709(3)	0.0214(2)
C23A	0.13523(6)	0.08348(7)	0.14731(3)	0.0227(2)
C23C	0.77742(6)	0.28586(7)	0.17539(3)	0.0212(2)
C24A	0.18659(7)	0.09976(8)	0.20461(4)	0.0290(3)
H24E	0.2325	0.1214	0.2116	0.035*
H24F	0.1915	0.0418	0.2012	0.035*
C25A	0.13765(7)	0.11481(8)	0.23366(4)	0.0288(3)
H25E	0.0933	0.0880	0.2278	0.035*
H25F	0.1286	0.1725	0.2352	0.035*
C26A	0.16601(8)	0.08512(9)	0.26915(4)	0.0336(3)
H26E	0.1700	0.0266	0.2683	0.040*
H26F	0.2128	0.1070	0.2735	0.040*
C27A	0.12182(7)	0.10779(9)	0.29965(4)	0.0329(3)
H27E	0.1161	0.1662	0.2998	0.039*
H27F	0.0756	0.0840	0.2957	0.039*
C28A	0.15097(8)	0.08170(11)	0.33543(4)	0.0412(4)
H28E	0.1986	0.1019	0.3387	0.049*
H28F	0.1530	0.0230	0.3361	0.049*
C29A	0.10897(9)	0.11067(12)	0.36570(4)	0.0481(4)
H29G	0.1302	0.0921	0.3880	0.072*
H29H	0.1076	0.1688	0.3656	0.072*
H29I	0.0620	0.0898	0.3630	0.072*
C30A	0.04833(7)	−0.07912(9)	0.06887(4)	0.0322(3)
C30C	0.82243(7)	0.48404(8)	0.24515(4)	0.0277(3)
C31A	−0.03011(8)	−0.07477(11)	0.06461(5)	0.0451(4)
H31D	−0.0439	−0.0207	0.0580	0.068*
H31E	−0.0462	−0.1119	0.0462	0.068*
H31F	−0.0504	−0.0889	0.0869	0.068*
C31C	0.87127(8)	0.54524(9)	0.22994(5)	0.0403(4)
H31A	0.8795	0.5882	0.2470	0.060*
H31B	0.9151	0.5196	0.2250	0.060*
H31C	0.8505	0.5671	0.2081	0.060*
C32A	0.06824(9)	−0.16415(9)	0.07921(5)	0.0457(4)
H32D	0.1184	−0.1682	0.0821	0.069*
H32E	0.0474	−0.1779	0.1014	0.069*
H32F	0.0516	−0.2008	0.0608	0.069*
C32C	0.85532(9)	0.45226(10)	0.27969(4)	0.0438(4)
H32A	0.8648	0.4965	0.2959	0.066*
H32B	0.8237	0.4149	0.2904	0.066*
H32C	0.8984	0.4250	0.2749	0.066*
C33A	0.07870(10)	−0.05853(11)	0.03336(4)	0.0496(4)
H33D	0.1291	−0.0610	0.0356	0.074*
H33E	0.0620	−0.0966	0.0155	0.074*
H33F	0.0645	−0.0049	0.0263	0.074*
C33C	0.75410(8)	0.52494(9)	0.25262(5)	0.0393(4)
H33A	0.7627	0.5693	0.2689	0.059*
H33B	0.7328	0.5449	0.2306	0.059*
H33C	0.7231	0.4867	0.2632	0.059*
C34A	0.25634(6)	0.04330(8)	0.13179(4)	0.0263(3)
H34C	0.2787	−0.0052	0.1231	0.032*
H34D	0.2711	0.0506	0.1568	0.032*
C34C	0.68623(6)	0.23732(7)	0.21708(3)	0.0235(3)
H34A	0.6792	0.1958	0.1989	0.028*
H34B	0.6983	0.2111	0.2398	0.028*
C35A	0.27857(6)	0.11481(8)	0.11045(3)	0.0249(3)
C35C	0.62071(6)	0.28566(7)	0.22017(3)	0.0219(2)
C36A	0.26847(7)	0.11342(8)	0.07405(4)	0.0278(3)
H36A	0.2518	0.0661	0.0631	0.033*
C36C	0.59977(6)	0.30909(7)	0.25320(3)	0.0235(3)
H36C	0.6219	0.2864	0.2735	0.028*
C37A	0.28192(7)	0.17887(8)	0.05292(3)	0.0272(3)
C37C	0.54770(6)	0.36445(8)	0.25754(3)	0.0245(3)
C38A	0.30485(6)	0.24739(8)	0.07004(3)	0.0263(3)
H38A	0.3132	0.2933	0.0564	0.032*
C38C	0.51615(7)	0.39631(8)	0.22710(3)	0.0257(3)
H38C	0.4808	0.4347	0.2294	0.031*
C39A	0.31608(6)	0.25143(8)	0.10641(3)	0.0237(3)
C39C	0.53449(6)	0.37404(8)	0.19357(3)	0.0234(3)
C40A	0.30469(6)	0.18367(8)	0.12641(3)	0.0236(3)
C40C	0.58592(6)	0.31679(7)	0.19045(3)	0.0222(2)
C41C^e	0.5928(3)	0.2172(7)	0.14623(17)	0.0314(9)
H41A^e	0.5754	0.1865	0.1662	0.038*
H41B^e	0.6369	0.1931	0.1397	0.038*
C41D^f	0.5839(16)	0.213(3)	0.1473(7)	0.0314(9)
H41C^f	0.6247	0.1781	0.1466	0.038*
H41D^f	0.5518	0.1912	0.1644	0.038*
C42C^e	0.5415(3)	0.2120(3)	0.11529(13)	0.0336(9)
H42A^e	0.5580	0.2447	0.0957	0.040*
H42B^e	0.4968	0.2339	0.1222	0.040*
C42D^f	0.5489(15)	0.2203(13)	0.1113(6)	0.0336(9)
H42C^f	0.5022	0.2426	0.1133	0.040*
H42D^f	0.5755	0.2565	0.0965	0.040*
C43C^e	0.53108(15)	0.12659(18)	0.10257(7)	0.0364(6)
H43A^e	0.5765	0.1035	0.0977	0.044*
H43B^e	0.5114	0.0952	0.1217	0.044*
C43D^f	0.5443(6)	0.1401(8)	0.0944(3)	0.0364(6)
H43C^f	0.5235	0.1022	0.1108	0.044*
H43D^f	0.5912	0.1210	0.0897	0.044*
C44C^f	0.5017(6)	0.1424(6)	0.0604(3)	0.0466(6)
H44A^f	0.5171	0.1880	0.0464	0.056*
H44B^f	0.4531	0.1523	0.0660	0.056*
C44D^e	0.48434(13)	0.11865(16)	0.06975(7)	0.0466(6)
H44C^e	0.4394	0.1433	0.0743	0.056*
H44D^e	0.5048	0.1486	0.0504	0.056*
C45C^f	0.5042(5)	0.0671(5)	0.0374(2)	0.0479(5)
H45A^f	0.4787	0.0770	0.0148	0.058*
H45B^f	0.5526	0.0554	0.0323	0.058*
C45D^e	0.47213(13)	0.03361(15)	0.05781(6)	0.0479(5)
H45C^e	0.4493	0.0045	0.0767	0.058*
H45D^e	0.4401	0.0340	0.0369	0.058*
C46C^f	0.4735(8)	−0.0038(7)	0.0550(4)	0.0847(10)
H46A^f	0.4761	−0.0501	0.0396	0.127*
H46B^f	0.4991	−0.0145	0.0772	0.127*
H46C^f	0.4252	0.0071	0.0597	0.127*
C46D^e	0.53634(17)	−0.01079(19)	0.04881(9)	0.0847(10)
H46D^e	0.5241	−0.0648	0.0414	0.127*
H46E^e	0.5587	0.0166	0.0296	0.127*
H46F^e	0.5679	−0.0130	0.0695	0.127*
C47A	0.27252(7)	0.17461(9)	0.01275(4)	0.0331(3)
C47C	0.52968(7)	0.39654(9)	0.29376(4)	0.0307(3)
C48A	0.20685(9)	0.12969(14)	0.00182(5)	0.0571(5)
H48D	0.1670	0.1571	0.0111	0.086*
H48E	0.2021	0.1276	−0.0239	0.086*
H48F	0.2093	0.0756	0.0113	0.086*
C48C	0.55804(11)	0.34412(13)	0.32364(4)	0.0567(5)
H48A	0.5384	0.2908	0.3212	0.085*
H48B	0.6083	0.3410	0.3227	0.085*
H48C	0.5457	0.3669	0.3462	0.085*
C49A	0.33411(9)	0.13135(13)	−0.00187(4)	0.0526(5)
H49D	0.3765	0.1598	0.0050	0.079*
H49E	0.3363	0.0773	0.0076	0.079*
H49F	0.3290	0.1292	−0.0276	0.079*
C49C	0.56067(9)	0.47977(11)	0.29776(5)	0.0484(4)
H49A	0.5426	0.5137	0.2786	0.073*
H49B	0.5484	0.5024	0.3204	0.073*
H49C	0.6109	0.4765	0.2968	0.073*
C50A	0.26875(12)	0.25732(11)	−0.00387(5)	0.0604(5)
H50D	0.2295	0.2863	0.0051	0.091*
H50E	0.3113	0.2863	0.0021	0.091*
H50F	0.2630	0.2523	−0.0295	0.091*
C50C	0.45157(8)	0.40257(10)	0.29719(4)	0.0385(4)
H50A	0.4319	0.4360	0.2783	0.058*
H50B	0.4312	0.3495	0.2955	0.058*
H50C	0.4417	0.4261	0.3200	0.058*
C51A	0.33640(6)	0.33033(8)	0.12309(3)	0.0256(3)
H51C	0.3439	0.3234	0.1488	0.031*
H51D	0.3800	0.3490	0.1134	0.031*
C51C	0.50432(6)	0.41531(8)	0.16117(3)	0.0269(3)
H51A	0.4600	0.4402	0.1667	0.032*
H51B	0.4953	0.3758	0.1423	0.032*
C52A	0.28047(6)	0.39171(7)	0.11587(3)	0.0227(2)
C52C	0.55322(6)	0.47851(8)	0.14837(3)	0.0246(3)
C53A	0.28327(7)	0.44418(8)	0.08756(3)	0.0250(3)
H53A	0.3232	0.4447	0.0740	0.030*
C53C	0.57415(7)	0.54043(8)	0.17066(4)	0.0283(3)
H53C	0.5569	0.5424	0.1936	0.034*
C54A	0.22962(7)	0.49571(8)	0.07849(3)	0.0252(3)
C54C	0.61924(7)	0.59919(8)	0.16055(4)	0.0299(3)
C55A	0.17156(7)	0.49342(8)	0.09885(3)	0.0250(3)
H55A	0.1343	0.5282	0.0931	0.030*
C55C	0.64761(7)	0.59069(8)	0.12771(4)	0.0312(3)
H55C	0.6808	0.6283	0.1207	0.037*
C56A	0.16623(6)	0.44218(7)	0.12717(3)	0.0226(2)
C56C	0.62933(7)	0.52937(8)	0.10476(4)	0.0272(3)
C57A	0.22194(6)	0.39263(7)	0.13575(3)	0.0221(2)
C57C	0.57876(6)	0.47587(8)	0.11474(3)	0.0250(3)
C58A	0.24383(7)	0.37561(8)	0.19603(3)	0.0282(3)
H58C	0.2188	0.4254	0.2007	0.034*
H58D	0.2933	0.3884	0.1942	0.034*
C58C	0.49464(7)	0.45102(10)	0.07094(4)	0.0349(3)
H58A	0.5076	0.5003	0.0587	0.042*
H58B	0.4578	0.4641	0.0872	0.042*
C59A	0.23453(7)	0.31761(8)	0.22555(3)	0.0260(3)
H59C	0.2602	0.2683	0.2208	0.031*
H59D	0.1852	0.3039	0.2267	0.031*
C59C	0.46868(7)	0.39046(11)	0.04438(4)	0.0385(4)
H59A	0.4237	0.4086	0.0342	0.046*
H59B	0.4608	0.3398	0.0568	0.046*
C60A	0.26012(7)	0.35229(9)	0.26065(3)	0.0306(3)
H60C	0.3097	0.3649	0.2594	0.037*
H60D	0.2354	0.4026	0.2647	0.037*
C60C	0.51637(7)	0.37480(10)	0.01453(4)	0.0361(3)
H60A	0.5297	0.4261	0.0041	0.043*
H60B	0.5588	0.3489	0.0242	0.043*
C61A	0.25041(8)	0.29744(9)	0.29182(4)	0.0325(3)
H61C	0.2019	0.2796	0.2915	0.039*
H61D	0.2797	0.2499	0.2892	0.039*
C61C	0.48427(9)	0.32298(11)	−0.01411(4)	0.0445(4)
H61A	0.4702	0.2722	−0.0034	0.053*
H61B	0.4421	0.3494	−0.0237	0.053*
C62A	0.26824(8)	0.33598(10)	0.32716(4)	0.0368(3)
H62C	0.3181	0.3482	0.3286	0.044*
H62D	0.2430	0.3868	0.3286	0.044*
C62C	0.52991(10)	0.30478(12)	−0.04422(5)	0.0514(4)
H62A	0.5450	0.3554	−0.0546	0.062*
H62B	0.5715	0.2766	−0.0349	0.062*
C63A	0.25095(10)	0.28455(11)	0.35830(4)	0.0486(4)
H63D	0.2636	0.3125	0.3802	0.073*
H63E	0.2015	0.2733	0.3574	0.073*
H63F	0.2766	0.2346	0.3574	0.073*
C63C	0.49542(15)	0.25489(16)	−0.07277(6)	0.0842(8)
H63A	0.5277	0.2453	−0.0914	0.126*
H63B	0.4813	0.2040	−0.0629	0.126*
H63C	0.4548	0.2829	−0.0826	0.126*
C64A	0.23090(8)	0.55123(9)	0.04651(4)	0.0338(3)
C64C	0.63471(8)	0.67352(9)	0.18291(4)	0.0390(4)
C65A	0.29984(9)	0.54828(12)	0.02865(5)	0.0527(5)
H65D	0.3090	0.4938	0.0212	0.079*
H65E	0.2981	0.5833	0.0081	0.079*
H65F	0.3366	0.5659	0.0453	0.079*
C65C	0.61086(9)	0.66491(11)	0.22064(5)	0.0490(4)
H65A	0.5616	0.6523	0.2201	0.073*
H65B	0.6368	0.6222	0.2326	0.073*
H65C	0.6189	0.7148	0.2334	0.073*
C66A	0.21781(12)	0.63673(10)	0.05789(5)	0.0586(5)
H66D	0.1737	0.6397	0.0694	0.088*
H66E	0.2549	0.6540	0.0744	0.088*
H66F	0.2164	0.6714	0.0372	0.088*
C66C	0.71189(9)	0.69333(11)	0.18440(5)	0.0481(4)
H66A	0.7278	0.6990	0.1604	0.072*
H66B	0.7196	0.7431	0.1973	0.072*
H66C	0.7375	0.6505	0.1965	0.072*
C67A	0.17447(10)	0.52519(13)	0.01953(4)	0.0548(5)
H67D	0.1297	0.5266	0.0304	0.082*
H67E	0.1738	0.5613	−0.0007	0.082*
H67F	0.1839	0.4711	0.0116	0.082*
C67C	0.59539(11)	0.74324(10)	0.16528(6)	0.0621(6)
H67A	0.6100	0.7496	0.1411	0.093*
H67B	0.5458	0.7324	0.1650	0.093*
H67C	0.6053	0.7921	0.1785	0.093*
C68A	0.09941(6)	0.43292(8)	0.14599(3)	0.0235(3)
H68C	0.0708	0.4811	0.1425	0.028*
H68D	0.1093	0.4260	0.1715	0.028*
C68C	0.66667(7)	0.51880(9)	0.07079(4)	0.0310(3)
H68A	0.6622	0.5676	0.0564	0.037*
H68B	0.6459	0.4743	0.0571	0.037*
C70^c	0.7248(3)	0.1399(3)	0.01872(12)	0.0786(17)
H70A^c	0.7746	0.1496	0.0162	0.094*
H70B^c	0.7202	0.1025	0.0386	0.094*
C71^d	0.69968(18)	0.1912(2)	0.00689(9)	0.0379(9)
H71A^d	0.7504	0.1893	0.0056	0.046*
H71B^d	0.6843	0.2446	−0.0010	0.046*
C72^d	0.6684(3)	0.1298(3)	−0.01808(13)	0.0561(13)
H72A^d	0.6809	0.0760	−0.0097	0.067*
H72B^d	0.6176	0.1344	−0.0187	0.067*
C73^c	0.6965(5)	0.1009(4)	−0.01412(18)	0.082(2)
H73A^c	0.6490	0.0844	−0.0092	0.098*
H73B^c	0.7233	0.0514	−0.0167	0.098*
C74	0.69222(18)	0.14129(18)	−0.05191(8)	0.0838(8)
H74A^d	0.6717	0.1014	−0.0679	0.126*
H74B^d	0.6792	0.1944	−0.0603	0.126*
H74C^d	0.7425	0.1361	−0.0513	0.126*
H74D^c	0.675(3)	0.098(4)	−0.0697(17)	0.126*
H74E^c	0.663(3)	0.186(4)	−0.0538(17)	0.126*
H74F^c	0.743(3)	0.153(4)	−0.0555(17)	0.126*
C77^a	0.03400(15)	0.41929(17)	0.31846(6)	0.0400(7)
H77A^a	0.0005	0.3754	0.3151	0.048*
H77B^a	0.0089	0.4699	0.3147	0.048*
C80^g	0.3981(7)	0.1642(10)	0.1672(3)	0.0308(5)
H80A^g	0.4055	0.1063	0.1651	0.037*
H80B^g	0.4250	0.1920	0.1495	0.037*
C81^h	0.3975(3)	0.1443(3)	0.32954(10)	0.0532(7)
H81A^h	0.3627	0.1122	0.3409	0.080*
H81B^h	0.4421	0.1375	0.3421	0.080*
H81C^h	0.3841	0.2004	0.3301	0.080*
C82^g	0.4185(5)	0.1938(6)	0.2053(2)	0.0367(5)
H82A^g	0.4693	0.1965	0.2081	0.044*
H82B^g	0.4002	0.2481	0.2084	0.044*
C83^h	0.38805(10)	0.17564(13)	0.21387(5)	0.0367(5)
H83A^h	0.3503	0.1441	0.2236	0.044*
H83B^h	0.3799	0.2319	0.2199	0.044*
C84^g	0.3908(4)	0.1396(5)	0.2340(2)	0.0338(4)
H84A^g	0.3400	0.1380	0.2314	0.041*
H84B^g	0.4081	0.0850	0.2304	0.041*
C85^h	0.45531(9)	0.14966(12)	0.23194(5)	0.0338(4)
H85A^h	0.4938	0.1792	0.2218	0.041*
H85B^h	0.4626	0.0924	0.2275	0.041*
C86^g	0.4109(5)	0.1653(6)	0.2706(2)	0.0407(19)
H86A^g	0.3971	0.2214	0.2733	0.049*
H86B^g	0.4617	0.1630	0.2735	0.049*
C87^h	0.45566(11)	0.16432(12)	0.27149(5)	0.0356(4)
H87A^h	0.5020	0.1513	0.2816	0.043*
H87B^h	0.4478	0.2216	0.2755	0.043*
C88^g	0.3807(7)	0.1179(9)	0.2998(3)	0.0443(6)
H88A^g	0.3890	0.0608	0.2955	0.053*
H88B^g	0.3303	0.1264	0.2993	0.053*
C89^h	0.40285(14)	0.11770(17)	0.29132(7)	0.0443(6)
H89A^h	0.4153	0.0607	0.2910	0.053*
H89B^h	0.3573	0.1236	0.2790	0.053*
C90^g	0.4105(14)	0.1395(16)	0.3360(5)	0.0532(7)
H90A^g	0.3889	0.1068	0.3538	0.080*
H90B^g	0.4603	0.1300	0.3370	0.080*
H90C^g	0.4016	0.1957	0.3407	0.080*
C91^h	0.38414(12)	0.1677(2)	0.17463(6)	0.0308(5)
H91A^h	0.4172	0.2044	0.1640	0.037*
H91B^h	0.3960	0.1128	0.1678	0.037*
C24Cⁱ	0.8249(16)	0.1651(13)	0.1588(8)	0.0332(10)
H24Aⁱ	0.8306	0.1464	0.1834	0.040*
H24Bⁱ	0.8678	0.1917	0.1521	0.040*
C25Cⁱ	0.8070(10)	0.0956(14)	0.1337(8)	0.0358(14)
H25Aⁱ	0.8136	0.1155	0.1096	0.043*
H25Bⁱ	0.8427	0.0546	0.1383	0.043*
C26Cⁱ	0.7401(4)	0.0539(6)	0.1326(3)	0.0483(9)
H26Aⁱ	0.7287	0.0420	0.1571	0.058*
H26Bⁱ	0.7048	0.0914	0.1231	0.058*
C28D^k	0.7091(11)	−0.0889(10)	0.1135(4)	0.0598(10)
H28G^k	0.7170	−0.1282	0.0948	0.072*
H28H^k	0.7152	−0.1175	0.1362	0.072*
C29D^l	0.7222(4)	−0.1694(4)	0.1013(2)	0.0764(15)
H29A^l	0.6880	−0.2086	0.1082	0.115*
H29B^l	0.7156	−0.1576	0.0762	0.115*
H29C^l	0.7685	−0.1907	0.1060	0.115*
C28Cⁱ	0.7719(3)	−0.0914(3)	0.12769(15)	0.0598(10)
H28Aⁱ	0.8211	−0.0772	0.1312	0.072*
H28Bⁱ	0.7539	−0.1035	0.1511	0.072*
C29Ek	0.6375(6)	−0.0671(5)	0.1101(3)	0.0764(15)
H29J^k	0.6089	−0.1149	0.1116	0.115*
H29K^k	0.6265	−0.0305	0.1291	0.115*
H29L^k	0.6282	−0.0413	0.0873	0.115*
C29Cⁱ	0.7666(4)	−0.1633(4)	0.10573(19)	0.0764(15)
H29Dⁱ	0.7926	−0.2064	0.1173	0.115*
H29Eⁱ	0.7181	−0.1787	0.1026	0.115*
H29Fⁱ	0.7854	−0.1524	0.0827	0.115*
C24D^m	0.8193(11)	0.1618(9)	0.1602(5)	0.0332(10)
H24C^m	0.8135	0.1355	0.1831	0.040*
H24D^m	0.8643	0.1893	0.1612	0.040*
C25D^m	0.8194(6)	0.0998(10)	0.1318(5)	0.0358(14)
H25C^m	0.8641	0.0716	0.1325	0.043*
H25D^m	0.8126	0.1251	0.1084	0.043*
C28E^l	0.7138(8)	−0.0969(6)	0.1216(2)	0.0598(10)
H28C^l	0.7194	−0.1096	0.1469	0.072*
H28D^l	0.6665	−0.0765	0.1171	0.072*
C26D^m	0.7610(2)	0.0413(4)	0.13802(18)	0.0483(9)
H26C^m	0.7160	0.0681	0.1340	0.058*
H26D^m	0.7640	0.0224	0.1627	0.058*
C27Cⁱ	0.7333(3)	−0.0203(4)	0.1123(2)	0.0614(10)
H27Aⁱ	0.7496	−0.0105	0.0883	0.074*
H27Bⁱ	0.6838	−0.0341	0.1098	0.074*
C27E^k	0.7663(2)	−0.0306(3)	0.11244(15)	0.0614(10)
H27G^k	0.805(6)	−0.074(7)	0.104(3)	0.092*
H27H^k	0.759(5)	0.000(7)	0.087(3)	0.092*
C27D^l	0.7663(2)	−0.0306(3)	0.11244(15)	0.0614(10)
H27C^l	0.8136	−0.0524	0.1141	0.074*
H27D^l	0.7569	−0.0125	0.0880	0.074*

^aOccupancy: 0.646(4); ^bOccupancy: 0.354(4); ^cOccupancy: 0.497(5); ^dOccupancy: 0.503(5); ^eOccupancy: 0.789(3); ^fOccupancy: 0.211(3); ^gOccupancy: 0.193(2); ^hOccupancy: 0.807(2); ⁱOccupancy: 0.4108; ^kOccupancy: 0.2356; ^lOccupancy: 0.3536; ^mOccupancy: 0.58920.

Source of material

The synthesis of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene was achieved by following the reported procedure [1]. Sodium hydroxide (40% water solution, 0.29 mL water, 0.114 g, 2.85 mmol NaOH) and para-t-butyl calix[4]arene (0.308 mmol, 0.2 g) were added to dimethyl sulfoxide (25 mL). The reaction mixture was warmed to 50 °C. 1-Bromohexane (1.23 mmol, 0.203 g) was added and the mixture was stirred for 6 h at 70–75 °C. After cooling to 20 °C the reaction mixture was poured into dilute hydrochloric acid. The precipitate was dried and recrystallized from acetonitrile (0.14 g, 70%). m.p. 394–396 K. Crystals were grown at room temperature from acetone:acetonitrile (3:1).

Experimental details

Anisotropical displacement parameters for certain atoms were constrained. Certain carbon atoms were disordered over two positions and their site occupancy factors were refined. All hydrogen atoms were placed in idealised positions and refined in riding models with U_iso assigned 1.2 or 1.5 times U_eq of their parent atoms and the bond distances were constrained to 0.95 Å, 0.98 Å or 0.99 Å.

Discussion

The title compound was first synthesised by Kenis et al. [1]. The tetraether compound belongs to the family of calixarenes. These molecules have been used in a wide range of applications including chromatography and sensors [2, 3] . The butyl and pentyl substituated structures have been reported [4, 5] .

In this example the calixarenes are oriented head to tail side by side rendering layers across the ac plane (see figure). This head to tail system is also seen for the butyl and pentyl derivatives. There is disorder in the alkyl chains at C10 and C11 as is the case with the pentyl example [5]. As expected there is no classical hydrogen bonding found in the crystal.

Acknowledgement

We are grateful for the financial support from DST – National Research Foundation Centre of Excellence in Catalysis, C* Change and Dr. Hong Su from the Chemistry Department of the University of Cape Town for her assistance with the data collection and refinement.

References

1 Kenis, P. J. A.; Noordman, O. F. J.; Schönherr, H.; Kerver, E. J.; Snellink-Ruël, B. H. M.; van Hummel, G. J.; Harkema, S.; van der Vorst, C. P. J. M.; Hare, J.; Picken, S. J.; Engbersen, J. F. J.; van Hulst, N. F.; Vancso, G. J.; Reinhoudt, D. N.: Supramolecular materials: molecular packing of tetranitrotetrapropoxycalix[4]arene in highly stable films with second-srder nonlinear optical properties. Chem. Eur. J. 4 (1998) 1225–1234.10.1002/(SICI)1521-3765(19980710)4:7<1225::AID-CHEM1225>3.0.CO;2-6Search in Google Scholar

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Received: 2016-12-15

Accepted: 2017-3-1

Published Online: 2017-4-10

Published in Print: 2017-5-24

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Supplementary material

Articles in the same Issue

https://doi.org/10.1515/ncrs-2016-0286

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BY-NC-ND 3.0

Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4

Article

Abstract

Source of material

Experimental details

Discussion

Acknowledgement

References

Supplementary Material

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Articles in the same Issue

Articles in the same Issue

Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C₆₈H₁₀₄O₄