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_4135342
_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         'C66 H84 O12, C5 H6 O, C5 H5 O'
_chemical_formula_sum            'C76 H95 O14'
_chemical_formula_weight         1232.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.957(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.7857(15)
_cell_length_b                   12.5558(7)
_cell_length_c                   25.1482(14)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.815
_cell_measurement_theta_min      3.282
_cell_volume                     7400.4(7)
_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      170.02
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35533
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.309
_diffrn_reflns_theta_min         3.446
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1413 before and 0.0813 after correction. The Ratio of minimum to maximum transmission is 0.7489. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             2652
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6964
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.1408
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+100.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3477
_refine_ls_wR_factor_ref         0.3525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5831
_reflns_number_total             6964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09757_si_004.cif
_cod_data_source_block           191024wyt_etp6_0m
_cod_depositor_comments
'Adding full bibliography for 4135342--4135349.cif.'
_cod_database_code               4135342
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. 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
2. Restrained distances
 O2S-C9S = O2S-C6S
 1.48 with sigma of 0.02
 C9S-C6S
 2.4 with sigma of 0.02
 C6S-C7S
 1.4 with sigma of 0.02
 C8S-C7S = C9S-C8S
 1.4 with sigma of 0.02
 C9S-C7S
 2.4 with sigma of 0.02
 C9S-C10S
 1.5 with sigma of 0.02
 O1S-C4S = O1S-C1S
 1.48 with sigma of 0.02
 C5S-C4S
 1.5 with sigma of 0.02
 C1S-C2S = C3S-C2S = C3S-C4S
 1.4 with sigma of 0.02
 C8S-C10S \\sim C10S-O2S
 with sigma of 0.02
 C3S-C5S \\sim C5S-O1S
 with sigma of 0.02
3. Restrained planarity
 O2S, C6S, C7S, C9S
 with sigma of 0.1
 O2S, C6S, C7S, C8S, C9S
 with sigma of 0.1
 O2S, C6S, C7S, C8S, C9S, C10S
 with sigma of 0.1
 O1S, C1S, C2S, C3S, C4S, C5S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O2S \\sim C6S \\sim C7S \\sim C8S \\sim C9S: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O2S \\sim C6S \\sim C7S \\sim C8S \\sim C9S \\sim C10S: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
O1S \\sim C1S \\sim C2S \\sim C3S \\sim C4S \\sim C5S: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O1S \\sim C1S \\sim C2S
\\sim C3S \\sim C4S \\sim C5S \\sim O2S \\sim C6S \\sim C7S \\sim C8S \\sim C9S
\\sim C10S: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O1S(0.5) C1S(0.5) H1S(0.5) C2S(0.5) H2S(0.5) C3S(0.5) H3S(0.5)
 C4S(0.5) C5S(0.5) H5SA(0.5) H5SB(0.5) H5SC(0.5) O2S(0.5) C6S(0.5) H6S(0.5)
 C7S(0.5) H7S(0.5) C8S(0.5) C9S(0.5) C10S(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
 C26(H26A,H26B), C28(H28A,H28B), C30(H30A,H30B), C32(H32A,H32B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C12(H12), C16(H16), C19(H19), C1S(H1S), C2S(H2S),
 C3S(H3S), C6S(H6S), C7S(H7S)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C5S(H5SA,H5SB,H5SC),
 C10S(H10A,H10B,H10C)
;
_shelx_res_checksum              70040
_shelx_hkl_checksum              92669
_shelx_fab_checksum              89607
_olex2_submission_special_instructions 'No special instructions were received'