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_4135344
_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 H72 Br12 O12, C5 H6 O'
_chemical_formula_sum            'C71 H78 Br12 O13'
_chemical_formula_weight         2098.25
_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             2019-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.172(2)
_cell_angle_beta                 77.599(2)
_cell_angle_gamma                72.479(2)
_cell_formula_units_Z            2
_cell_length_a                   14.1746(4)
_cell_length_b                   16.4665(6)
_cell_length_c                   19.6666(6)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.894
_cell_measurement_theta_min      3.393
_cell_volume                     4237.6(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      169.97
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44643
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.974
_diffrn_reflns_theta_min         2.976
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.954
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0744 after correction. The Ratio of minimum to maximum transmission is 0.5499. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       block
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.668
_refine_diff_density_min         -2.293
_refine_diff_density_rms         0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     957
_refine_ls_number_reflns         16022
_refine_ls_number_restraints     149
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.1095
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+100.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2601
_refine_ls_wR_factor_ref         0.2756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11673
_reflns_number_total             16022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09757_si_008.cif
_cod_data_source_block           191209wyt_1_0m
_cod_depositor_comments
'Adding full bibliography for 4135342--4135349.cif.'
_cod_database_code               4135344
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.524
_shelx_estimated_absorpt_t_min   0.469
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All C(H,H,H,H,H,
  H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5AA-C1BA = C5AA-C4AA
 1.4 with sigma of 0.02
 C1BA-C0BA = O3AA-C0BA = C4AA-O3AA
 1.39 with sigma of 0.02
 C6AA-C4AA
 1.53 with sigma of 0.02
 C4AA-C1BA
 2.28 with sigma of 0.02
 C1AA-C0AA = C7AA-C1AA = C8AA-C0AA
 1.39 with sigma of 0.02
 C8AA-O2AA
 1.4 with sigma of 0.02
 C7AA-O2AA
 1.4 with sigma of 0.02
 C9AA-C8AA
 1.53 with sigma of 0.02
 O2AA-C0AA = O2AA-C1AA
 2.25 with sigma of 0.02
 Br0A-C3AA = Br9-C3AA = Br12-C53 = Br11-C53
 1.8 with sigma of 0.02
 Br2-C1 = Br1-C1
 1.8 with sigma of 0.02
 Br1A-C3AA
 1.8 with sigma of 0.02
 H41A-H43
 2 with sigma of 0.02
3. Restrained planarity
 C5AA, C1BA, C0BA, O3AA, C4AA, C6AA
 with sigma of 0.1
 C8AA, C0AA, C1AA, C7AA, O2AA, C9AA
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C6AA \\sim C5AA \\sim C4AA \\sim C1BA \\sim O3AA \\sim C0BA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
O2AA \\sim C7AA \\sim C1AA \\sim C0AA \\sim C8AA \\sim C9AA: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C41 \\sim C3AA \\sim Br0A \\sim Br9: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C2 \\sim C1 \\sim Br2 \\sim Br1: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Fixed Sof: Br1(0.5) Br2(0.5) Br9(0.5) Br11(0.75) Br12(0.25) H1A(0.5) H1B(0.5)
 H1BC(0.5) H1BD(0.5) H53A(0.75) H53B(0.75) H53C(0.25) H53D(0.25) O2AA(0.5)
 C5AA(0.5) H5AA(0.5) O3AA(0.5) C9AA(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5)
 C6AA(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5) C4AA(0.5) C1BA(0.5) H1BA(0.5)
 C0BA(0.5) H0BA(0.5) H3AA(0.5) H3AB(0.5) H3AC(0.25) H3AD(0.25) H3AE(0.25)
 H3AF(0.25) C7AA(0.5) H7AA(0.5) C0AA(0.5) H0AA(0.5) C8AA(0.5) C1AA(0.5)
 H1AC(0.5) Br0A(0.25) Br1A(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1(H1BC,H1BD), C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,
 H11B), C14(H14A,H14B), C15(H15A,H15B), C19(H19A,H19B), C20(H20A,H20B),
 C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B), C30(H30A,H30B), C31(H31A,H31B),
  C33(H33A,H33B), C36(H36A,H36B), C37(H37A,H37B), C41(H41A,H41B), C44(H44A,
 H44B), C47(H47A,H47B), C48(H48A,H48B), C52(H52A,H52B), C53(H53A,H53B),
 C53(H53C,H53D), C55(H55A,H55B), C58(H58A,H58B), C59(H59A,H59B), C63(H63A,H63B),
  C64(H64A,H64B), C66(H66A,H66B), C3AA(H3AA,H3AB), C3AA(H3AC,H3AD), C3AA(H3AE,
 H3AF)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C16(H16), C21(H21), C27(H27), C32(H32), C38(H38), C43(H43),
 C49(H49), C54(H54), C60(H60), C65(H65), C5AA(H5AA), C1BA(H1BA), C0BA(H0BA),
 C7AA(H7AA), C0AA(H0AA), C1AA(H1AC)
6.c Idealised Me refined as rotating group:
 C9AA(H9AA,H9AB,H9AC), C6AA(H6AA,H6AB,H6AC)
;
_shelx_res_checksum              48274
_shelx_hkl_checksum              8110
_olex2_submission_special_instructions 'No special instructions were received'