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_1567066
_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         'C55 H70 O10, 1.5(C4 H9 N)'
_chemical_formula_sum            'C61 H83.5 N1.5 O10'
_chemical_formula_weight         997.79
_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             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-03 deposited with the CCDC.	2022-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                109.598(3)
_cell_angle_beta                 98.054(2)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            4
_cell_length_a                   14.9616(5)
_cell_length_b                   16.3732(6)
_cell_length_c                   24.4025(10)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      52.828
_cell_measurement_theta_min      3.38
_cell_volume                     5568.9(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      170.0
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_unetI/netI     0.1108
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19009
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.145
_diffrn_reflns_theta_min         2.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 59905 reflections, Rint = 0.1067
 (23979 with I > 3sig(I), Rint = 0.0868)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1327
_refine_ls_number_reflns         19009
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0990
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1809P)^2^+3.4346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2554
_refine_ls_wR_factor_ref         0.3027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12112
_reflns_number_total             19009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02494b2.cif
_cod_data_source_block           191111cjj_1
_cod_original_formula_sum        'C61 H83.50 N1.50 O10'
_cod_database_code               1567066
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5714(17)
 0.4286(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 H35C-H23
 2 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N23 \\sim C119 \\sim C122 \\sim C120 \\sim C121: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C12(H12A,H12B), C17(H17A,H17B), C20(H20A,H20B),
 C23(H23A,H23B), C28(H28A,H28B), C31(H31A,H31B), C34(H34A,H34B), C39(H39A,H39B),
  C42(H42A,H42B), C45(H45A,H45B), C50(H50A,H50B), C53(H53A,H53B), C54(H54A,
 H54B), C60(H60A,H60B), C64(H64A,H64B), C67(H67A,H67B), C72(H72A,H72B),
 C75(H75A,H75B), C78(H78A,H78B), C83(H83A,H83B), C86(H86A,H86B), C89(H89A,H89B),
  C94(H94A,H94B), C97(H97A,H97B), C100(H10A,H10B), C105(H10F,H10G), C108(H10K,
 H10L), C109(H10M,H10N), C111(H11D,H11E), C112(H11F,H11G), C113(H11H,H11I),
 C114(H11J,H11K), C115(H11L,H11M), C116(H11N,H11O), C117(H11P,H11Q), C118(H11R,
 H11S), C119(H11T,H11U), C120(H12C,H12D), C121(H12E,H12F), C122(H12G,H12H)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C14(H14), C19(H19), C25(H25), C30(H30), C36(H36), C41(H41),
 C47(H47), C52(H52), C58(H58), C63(H63), C69(H69), C74(H74), C80(H80), C85(H85),
  C91(H91), C96(H96), C102(H102), C107(H107), N21(H21), N22(H22), N23(H23)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C24(H24A,H24B,
 H24C), C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C46(H46A,
 H46B,H46C), C51(H51A,H51B,H51C), C55(H55A,H55B,H55C), C61(H61A,H61B,H61C),
 C68(H68A,H68B,H68C), C73(H73A,H73B,H73C), C79(H79A,H79B,H79C), C84(H84A,H84B,
 H84C), C90(H90A,H90B,H90C), C95(H95A,H95B,H95C), C101(H10C,H10D,H10E),
 C106(H10H,H10I,H10J), C110(H11A,H11B,H11C)
;
_shelx_res_checksum              94875
_shelx_hkl_checksum              71722
_olex2_submission_special_instructions 'No special instructions were received'