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_4135348
_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 H60 Br10 O10, C5 H6 O'
_chemical_formula_sum            'C60 H66 Br10 O11'
_chemical_formula_weight         1762.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4691(9)
_cell_length_b                   20.7774(8)
_cell_length_c                   12.8545(5)
_cell_measurement_reflns_used    9354
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      52.499
_cell_measurement_theta_min      3.703
_cell_volume                     6535.3(4)
_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      169.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.1197
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            62688
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.057
_diffrn_reflns_theta_min         3.143
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.359
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1694 before and 0.1023 after correction. The Ratio of minimum to maximum transmission is 0.5942. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.334
_refine_diff_density_min         -1.762
_refine_diff_density_rms         0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6244
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2904
_refine_ls_wR_factor_ref         0.3197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4238
_reflns_number_total             6244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09757_si_006.cif
_cod_data_source_block           191024wyt_p5
_cod_depositor_comments
'Adding full bibliography for 4135342--4135349.cif.'
_cod_database_code               4135348
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.739
_shelx_estimated_absorpt_t_min   0.674
_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
 C33-O6
 1.4 with sigma of 0.02
 C30-C31
 1.48 with sigma of 0.02
 C30-C29
 1.5 with sigma of 0.02
 C30-O6 = C33-O6
 1.48 with sigma of 0.02
 C32-C31
 1.4 with sigma of 0.02
 C30-C31 = C33-C32
 1.4 with sigma of 0.02
 O6-C32
 2.4 with sigma of 0.02
 O6-C29 \\sim C29-C31
 with sigma of 0.02
3. Restrained planarity
 O6, C29, C30, C31, C33
 with sigma of 0.1
 O6, C29, C30, C31, C32, C33
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O6 \\sim C29 \\sim C30 \\sim C31 \\sim C33: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O6 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C29) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: H18A(0.5) H18B(0.5) O6(0.5) C29(0.5) H29B(0.5) H29A(0.5) H29C(0.5)
 C30(0.5) C31(0.5) H31(0.5) C32(0.5) H32(0.5) C33(0.5) H33(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C10(H10), C13(H13), C16(H16), C31(H31), C32(H32), C33(H33)
6.c Idealised Me refined as rotating group:
 C29(H29B,H29A,H29C)
;
_shelx_res_checksum              72851
_shelx_hkl_checksum              264
_olex2_submission_special_instructions 'No special instructions were received'