Selective Separation of Methylfuran and Dimethylfuran by Nonporous Adaptive Crystals of Pillararenes.
Wu, Yitao; Zhou, Jiong; Li, Errui; Wang, Mengbin; Jie, Kecheng; Zhu, Huangtianzhi; Huang, Feihe; Journal of the American Chemical Society 142 (2020) 19722–19730; doi:10.1021/jacs.0c09757

data_4135349
_publ_section_title
;
 Selective Separation of Methylfuran and Dimethylfuran by Nonporous
 Adaptive Crystals of Pillararenes.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19722
_journal_page_last               19730
_journal_paper_doi               10.1021/jacs.0c09757
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C55 H70 O10, 0.5(C10 H12 O2)'
_chemical_formula_sum            'C60 H76 O11'
_chemical_formula_weight         973.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                87.834(8)
_cell_angle_beta                 86.789(8)
_cell_angle_gamma                85.765(9)
_cell_formula_units_Z            4
_cell_length_a                   13.167(3)
_cell_length_b                   14.706(4)
_cell_length_c                   30.336(7)
_cell_measurement_reflns_used    4874
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      49.908
_cell_measurement_theta_min      7.55
_cell_volume                     5845(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21773
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.111
_diffrn_reflns_theta_min         2.953
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 101035 reflections, Rint = 0.1142
 (30641 with I > 3sig(I), Rint = 0.0870)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.788
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1412
_refine_ls_number_reflns         21773
_refine_ls_number_restraints     333
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.2040
_refine_ls_R_factor_gt           0.1337
_refine_ls_shift/su_max          0.066
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3072
_refine_ls_wR_factor_ref         0.3712
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11239
_reflns_number_total             21773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09757_si_002.cif
_cod_data_source_block           191025wyt_etp51_0m_pl
_cod_depositor_comments
'Adding full bibliography for 4135342--4135349.cif.'
_cod_original_cell_volume        5846(2)
_cod_database_code               4135349
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.538(3)
 0.462(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O6G-C5G = O6G-C2G
 1.48 with sigma of 0.02
 C4G-C5G = C3G-C2G
 1.4 with sigma of 0.02
 C4G-C3G
 1.5 with sigma of 0.02
 C1G-C2G
 1.5 with sigma of 0.02
 O11G-C8G = O11G-C10G
 1.48 with sigma of 0.02
 C10G-C9G = C8G-C0AA
 1.4 with sigma of 0.02
 C7G-C8G = C9G-C0AA
 1.5 with sigma of 0.02
 O23G-C22G = O23G-C19G
 1.48 with sigma of 0.02
 C21G-C20G
 1.5 with sigma of 0.02
 C21G-C22G
 1.4 with sigma of 0.02
 C20G-C19G
 1.4 with sigma of 0.02
 C19G-C18G
 1.5 with sigma of 0.02
 O23G-C21G
 2.4 with sigma of 0.02
 C22G-C20G
 2.4 with sigma of 0.02
 C12G-C13G
 1.4 with sigma of 0.02
 C14G-C15G
 1.4 with sigma of 0.02
 O17G-C12G = O17G-C15G
 1.48 with sigma of 0.02
 C13G-C14G = C16G-C15G
 1.5 with sigma of 0.02
 O11G-C0AA = O17G-C14G
 2.4 with sigma of 0.02
 O6G-C3G
 2.4 with sigma of 0.02
 C3G-C1G \\sim C1G-O6G
 with sigma of 0.02
 O11G-C7G \\sim C7G-C0AA
 with sigma of 0.02
 O23G-C18G \\sim C18G-C20G
 with sigma of 0.02
 O17G-C16G \\sim C16G-C14G
 with sigma of 0.02
4. Restrained planarity
 O6G, C1G, C2G, C3G, C4G, C5G
 with sigma of 0.1
 O11G, C0AA, C7G, C8G, C9G, C10G
 with sigma of 0.1
 O23G, C18G, C19G, C20G, C21G, C22G
 with sigma of 0.1
 O17G, C12G, C13G, C14G, C15G, C16G
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
O6G \\sim C1G \\sim C2G \\sim C3G \\sim C4G \\sim C5G: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
O11G \\sim C0AA \\sim C7G \\sim C8G \\sim C9G \\sim C10G: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
O23G \\sim C18G \\sim C19G \\sim C20G \\sim C21G \\sim C22G: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
O17G \\sim C12G \\sim C13G \\sim C14G \\sim C15G \\sim C16G: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C22G \\sim C21G \\sim C20G \\sim C19G \\sim C18G \\sim O23G \\sim O16 \\sim O18
\\sim O20 \\sim O12 \\sim O14: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C18G) \\sim Ueq, Uanis(O23G) \\sim Ueq, Uanis(C19G) \\sim Ueq,
Uanis(C22G) \\sim Ueq, Uanis(C20G) \\sim Ueq, Uanis(C21G) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14G) \\sim Ueq, Uanis(O17G) \\sim Ueq, Uanis(C12G) \\sim Ueq,
Uanis(C15G) \\sim Ueq, Uanis(C13G) \\sim Ueq, Uanis(C16G) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C10G) \\sim Ueq, Uanis(O11G) \\sim Ueq, Uanis(C8G) \\sim Ueq, Uanis(C0AA)
\\sim Ueq, Uanis(C7G) \\sim Ueq, Uanis(C9G) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C1G) \\sim Ueq, Uanis(O6G) \\sim Ueq, Uanis(C2G) \\sim Ueq, Uanis(C5G)
\\sim Ueq, Uanis(C3G) \\sim Ueq, Uanis(C4G) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
6. Others
 Fixed Sof: O6G(0.5) C1G(0.5) H1GA(0.5) H1GB(0.5) H1GC(0.5) C2G(0.5) C3G(0.5)
 H3G(0.5) C4G(0.5) H4G(0.5) C5G(0.5) H5G(0.5) O23G(0.5) C18G(0.5) H18D(0.5)
 H18E(0.5) H18F(0.5) C19G(0.5) C20G(0.5) H20G(0.5) C21G(0.5) H21G(0.5)
 C22G(0.5) H22G(0.5) O11G(0.5) C0AA(0.5) H0AA(0.5) C7G(0.5) H7GA(0.5) H7GB(0.5)
 H7GC(0.5) C8G(0.5) C9G(0.5) H9G(0.5) C10G(0.5) H10O(0.5) O17G(0.5) C12G(0.5)
 H12G(0.5) C13G(0.5) H13G(0.5) C14G(0.5) H14G(0.5) C15G(0.5) C16G(0.5)
 H16A(0.5) H16B(0.5) H16C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C12(H12A,H12B), C17(H17A,H17B), C20(H20A,H20B),
 C23(H23A,H23B), C28(H28A,H28B), C31(H31A,H31B), C34(H34A,H34B), C39(H39A,H39B),
  C42(H42A,H42B), C45(H45A,H45B), C50(H50A,H50B), C53(H53A,H53B), C54(H54A,
 H54B), C60(H60A,H60B), C64(H64A,H64B), C67(H67A,H67B), C72(H72A,H72B),
 C75(H75A,H75B), C78(H78A,H78B), C83(H83A,H83B), C86(H86A,H86B), C89(H89A,H89B),
  C94(H94A,H94B), C97(H97A,H97B), C100(H10A,H10B), C105(H10F,H10G), C108(H10K,
 H10L), C109(H10M,H10N)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C14(H14), C19(H19), C25(H25), C30(H30), C36(H36), C41(H41),
 C47(H47), C52(H52), C58(H58), C63(H63), C69(H69), C74(H74), C80(H80), C85(H85),
  C91(H91), C96(H96), C102(H102), C107(H107), C3G(H3G), C4G(H4G), C5G(H5G),
 C20G(H20G), C21G(H21G), C22G(H22G), C0AA(H0AA), C9G(H9G), C10G(H10O),
 C12G(H12G), C13G(H13G), C14G(H14G)
7.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C24(H24A,H24B,
 H24C), C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C46(H46A,
 H46B,H46C), C51(H51A,H51B,H51C), C55(H55A,H55B,H55C), C61(H61A,H61B,H61C),
 C68(H68A,H68B,H68C), C73(H73A,H73B,H73C), C79(H79A,H79B,H79C), C84(H84A,H84B,
 H84C), C90(H90A,H90B,H90C), C95(H95A,H95B,H95C), C101(H10C,H10D,H10E),
 C106(H10H,H10I,H10J), C110(H11A,H11B,H11C), C1G(H1GA,H1GB,H1GC), C18G(H18D,
 H18E,H18F), C7G(H7GA,H7GB,H7GC), C16G(H16A,H16B,H16C)
;
_shelx_res_checksum              24049
_shelx_hkl_checksum              71357
_olex2_submission_special_instructions 'No special instructions were received'