Highly Selective Removal of Trace Isomers by Nonporous Adaptive Pillararene Crystals for Chlorobutane Purification.
Zhou, Yujuan; Jie, Kecheng; Zhao, Run; Li, Errui; Huang, Feihe; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02684

data_4134586
_publ_section_title
;
 Highly Selective Removal of Trace Isomers by Nonporous Adaptive
 Pillararene Crystals for Chlorobutane Purification.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02684
_journal_year                    2020
_chemical_formula_moiety         'C4 H9 Cl, C66 H84 O12'
_chemical_formula_sum            'C70 H93 Cl O12'
_chemical_formula_weight         1161.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.554(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.470(2)
_cell_length_b                   13.122(4)
_cell_length_c                   22.181(4)
_cell_measurement_reflns_used    3734
_cell_measurement_temperature    298.85
_cell_measurement_theta_max      64.99
_cell_measurement_theta_min      3.91
_cell_volume                     3337.2(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      298.85
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13658
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        65.164
_diffrn_reflns_theta_max         65.164
_diffrn_reflns_theta_min         3.914
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1053 before and 0.0717 after correction. The Ratio of minimum to maximum transmission is 0.9041. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.6723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2803
_reflns_number_total             5385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02684_si_002.cif
_cod_data_source_block           t
_cod_database_code               4134586
_shelx_shelxl_version_number     2014/7
_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
 C1-C2 = C36-C37
 1.5 with sigma of 0.02
 C2-C36
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Cl1, C37, C36, C2, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl1(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5) H2A(0.5)
 H2B(0.5) C37(0.5) H37A(0.5) H37B(0.5) C36(0.5) H36A(0.5) H36B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C20(H20A,H20B), C23(H23A,H23B), C26(H26A,H26B), C31(H31A,H31B), C34(H34A,H34B),
  C37(H37A,H37B), C36(H36A,H36B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C17(H17), C22(H22), C28(H28), C33(H33)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C),
 C27(H27A,H27B,H27C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              97997
_shelx_hkl_checksum              67835
_olex2_submission_special_instructions 'No special instructions were received'