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_4135345
_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, 2(C6 H8 O)'
_chemical_formula_sum            'C67 H76 Br10 O12'
_chemical_formula_weight         1872.37
_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             2019-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.6532(17)
_cell_length_b                   12.3731(8)
_cell_length_c                   44.242(3)
_cell_measurement_reflns_used    3811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.63
_cell_measurement_theta_min      3.93
_cell_volume                     14845.1(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            39826
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.520
_diffrn_reflns_theta_min         3.927
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.883
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1126 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.6102. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_description       block
_exptl_crystal_F_000             7392
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.262
_refine_diff_density_min         -2.077
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     806
_refine_ls_number_reflns         13447
_refine_ls_number_restraints     207
_refine_ls_restrained_S_all      1.639
_refine_ls_R_factor_all          0.2183
_refine_ls_R_factor_gt           0.1619
_refine_ls_shift/su_max          0.001
_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          0.3888
_refine_ls_wR_factor_ref         0.4225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6793
_reflns_number_total             13447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09757_si_007.cif
_cod_data_source_block           cu_dm19039_0m
_cod_depositor_comments
'Adding full bibliography for 4135342--4135349.cif.'
_cod_original_cell_volume        14845.0(17)
_cod_database_code               4135345
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.546
_shelx_estimated_absorpt_t_min   0.371
_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
 C47-C46
 1.53 with sigma of 0.02
 C55-C54
 1.53 with sigma of 0.02
 C45-C44 = O3-C44
 1.5 with sigma of 0.02
 C36-C37
 1.53 with sigma of 0.02
 C36-O1
 1.53 with sigma of 0.02
 C8AA-C7AA = C7AA-O6AA = O6AA-C5AA = C9AA-C5AA = C9AA-C8AA = C3AA-O2AA = C3AA-
 C1BA = C4AA-C1BA = C4AA-C1AA = O2AA-C1AA
 1.39 with sigma of 0.02
 O2AA-C1BA = C8AA-O6AA
 2.33 with sigma of 0.02
 C7AA-C5AA = C8AA-C5AA
 2.3 with sigma of 0.02
 C5AA-C2BA
 1.5 with sigma of 0.02
 Br10-C55
 1.8 with sigma of 0.02
 Br10-C54
 2.6 with sigma of 0.02
 C3BA-C3AA
 1.5 with sigma of 0.02
 C4AA-C3AA
 2.3 with sigma of 0.02
 Br3-C45
 1.8 with sigma of 0.02
 Br3-C44
 2.6 with sigma of 0.02
 H2BB-H2BB_$1 = H2BA-H2BB_$1
 2 with sigma of 0.01
 C9AA-C2BA \\sim C2BA-O6AA
 with sigma of 0.02
 C1BA-C3BA \\sim C3BA-O2AA
 with sigma of 0.02
3. Restrained planarity
 C2BA, C5AA, C9AA, O6AA, C7AA, C0BA, C8AA
 with sigma of 0.1
 C1BA, C3AA, O2AA, C3BA, C1AA, C4AA, C0AA
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C54 \\sim C55: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Br3 \\sim O3 \\sim C44 \\sim C45: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br8 \\sim O8 \\sim C46 \\sim C47: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br1 \\sim O1 \\sim C36 \\sim C37: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C1BA \\sim O2AA \\sim C1AA \\sim C3AA \\sim C4AA \\sim C0AA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C0BA \\sim C8AA \\sim C7AA \\sim O6AA \\sim C9AA \\sim C5AA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C2BA \\sim C5AA \\sim C9AA \\sim O6AA: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
O10 \\sim C54 \\sim C55 \\sim Br10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C3BA \\sim O2AA \\sim C1AA \\sim C3AA \\sim C4AA \\sim C0AA \\sim C1BA: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O3 \\sim C44 \\sim C45 \\sim Br3: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C44 \\sim C45 \\sim Br3 \\sim O3: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C45) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C39) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C28(H28A,H28B), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B),
  C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,
 H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B),
 C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B),
  C55(H55A,H55B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26),
 C30(H30), C33(H33), C8AA(H8AA), C4AA(H4AA), C9AA(H9AA), C1BA(H1BA)
5.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C0BA(H0BA,H0BB,H0BC), C2BA(H2BA,H2BB,H2BC), C3BA(H3BA,
 H3BB,H3BC)
;
_shelx_res_checksum              47276
_shelx_hkl_checksum              95942
_shelx_fab_checksum              48388
_olex2_submission_special_instructions 'No special instructions were received'