Separation of pyrrolidine from tetrahydrofuran by pillar[6]arene-based nonporous adaptive crystals
Cao, Jiajun; Wu, Yitao; Li, Qi; Zhu, Weijie; Wang, Zeju; Liu, Yang; Jie, Kecheng; Zhu, Huangtianzhi; Huang, Feihe; Chemical Science  (2022) –; doi:10.1039/D2SC02494B

data_1567065
_publ_section_title
;
 Separation of pyrrolidine from tetrahydrofuran by pillar[6]arene-based
 nonporous adaptive crystals
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02494B
_journal_year                    2022
_chemical_formula_moiety         'C66 H84 O12, C4 H8 O'
_chemical_formula_sum            'C70 H92 O13'
_chemical_formula_weight         1141.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-01-03 deposited with the CCDC.	2022-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.995(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5731(4)
_cell_length_b                   22.6648(7)
_cell_length_c                   14.4358(4)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.853
_cell_measurement_theta_min      3.374
_cell_volume                     3758.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.994
_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  0.0666
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.994
_diffrn_reflns_theta_min         3.828
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1556 before and 0.0849 after correction.
The Ratio of minimum to maximum transmission is 0.6554.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.009
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7131
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2387
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4752
_reflns_number_total             7131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02494b2.cif
_cod_data_source_block           210915wyt_thf_0m
_cod_database_code               1567065
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_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
 C37-C35 = C35-O7 = C38-O7 = C37-C36
 1.48 with sigma of 0.01
 C36-C38
 1.48 with sigma of 0.01
 C37-C35 = C37-C36 = C38-C36
 1.53 with sigma of 0.02
 O7-C35 = O7-C38
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O7 \\sim C35 \\sim C36 \\sim C37 \\sim C38: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H34A(0.5) H34B(0.5) O7(0.5) C35(0.5) H35A(0.5)
 H35B(0.5) C36(0.5) H36A(0.5) H36B(0.5) C37(0.5) H37A(0.5) H37B(0.5) C38(0.5)
 H38A(0.5) H38B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C19(H19A,H19B),
 C21(H21A,H21B), C23(H23A,H23B), C30(H30A,H30B), C32(H32A,H32B), C34(H34A,H34B),
  C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C15(H15), C18(H18), C25(H25), C28(H28)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              82191
_shelx_hkl_checksum              87883
_shelx_fab_checksum              16049
_olex2_submission_special_instructions 'No special instructions were received'