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_1567064
_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 H80 O12, C4 H9 N'
_chemical_formula_sum            'C70 H89 N O12'
_chemical_formula_weight         1136.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-03 deposited with the CCDC.	2022-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5560(3)
_cell_length_b                   26.6378(7)
_cell_length_c                   45.7727(10)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.83
_cell_measurement_theta_min      3.34
_cell_volume                     15309.3(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0588
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            50740
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.952
_diffrn_reflns_theta_min         4.222
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1378 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.7914. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.986
_exptl_crystal_description       block
_exptl_crystal_F_000             4896
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0929
_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^)+(0.1000P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2533
_refine_ls_wR_factor_ref         0.2659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2699
_reflns_number_total             3627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02494b2.cif
_cod_data_source_block           mj21308
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               1567064
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Restrained distances
 C19-C18 = C20-C19
 1.5 with sigma of 0.02
 N1-C21 = N1-C18 = C20-C21
 1.48 with sigma of 0.02
 C19-C18
 1.48 with sigma of 0.02
 N1-C20
 2.33 with sigma of 0.02
 C18-C21
 2.33 with sigma of 0.02
 N1-C21 = N1-C18
 1.48 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
N1 \\sim C21 \\sim C18 \\sim C20 \\sim C19: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(N1) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Fixed Sof: H7A(0.5) H7B(0.5) N1(0.25) H1(0.25) C18(0.25) H18A(0.25)
 H18B(0.25) C19(0.25) H19A(0.25) H19B(0.25) C20(0.25) H20A(0.25) H20B(0.25)
 C21(0.25) H21A(0.25) H21B(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C7(H7A,H7B), C8(H8A,H8B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C14(H14), C10(H10), N1(H1)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              23628
_shelx_hkl_checksum              20440
_shelx_fab_checksum              45706
_olex2_submission_special_instructions 'No special instructions were received'