Separation of 2-Chloropyridine/3-Chloropyridine by Nonporous Adaptive Crystals of Pillararenes with Different Substituents and Cavity Sizes.
Sheng, Xinru; Li, Errui; Zhou, Yujuan; Zhao, Run; Zhu, Weijie; Huang, Feihe; Journal of the American Chemical Society 142 (2020) 6360–6364; doi:10.1021/jacs.0c01274

data_4134443
_publ_section_title
;
 Separation of 2-Chloropyridine/3-Chloropyridine by Nonporous Adaptive
 Crystals of Pillararenes with Different Substituents and Cavity Sizes.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6360
_journal_page_last               6364
_journal_paper_doi               10.1021/jacs.0c01274
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         '2(C5 H4 Cl N), C66 H84 O12'
_chemical_formula_sum            'C76 H92 Cl2 N2 O12'
_chemical_formula_weight         1296.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.0750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.5236(8)
_cell_length_b                   12.5602(4)
_cell_length_c                   25.6641(11)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    173.01
_cell_measurement_theta_max      68.316
_cell_measurement_theta_min      3.813
_cell_volume                     7472.4(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       '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      173.01
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6739
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.512
_diffrn_reflns_theta_min         3.814
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0715 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.8809. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6739
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1646P)^2^+12.7638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2842
_refine_ls_wR_factor_ref         0.2947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5633
_reflns_number_total             6739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01274_si_003.cif
_cod_data_source_block           ler190929c_tw
_cod_depositor_comments
'Adding full bibliography for 4134442--4134445.cif.'
_cod_database_code               4134443
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.864
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.791(6)
 0.209(6)
2. 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
3. Restrained distances
 Cl1-C39 = Cl2-C34
 1.75 with sigma of 0.01
 Cl1-C40 \\sim Cl1-N2
 with sigma of 0.02
 Cl2-C35 \\sim Cl2-N1
 with sigma of 0.02
4. Restrained planarity
 Cl1, N2, C39, C40, C41, C42, C43
 with sigma of 0.1
 Cl2, N1, C34, C35, C36, C37, C38
 with sigma of 0.1
5. Rigid body (RIGU) restrains
 N1, Cl2, C34, C35, C36, C38, C37
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C40, Cl1, C39, N2, C43, C41, C42
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: Cl1(0.5) C39(0.5) N2(0.5) C43(0.5) H43(0.5) C42(0.5) H42(0.5)
 C41(0.5) H41(0.5) C40(0.5) H40(0.5) Cl2(0.5) C34(0.5) C35(0.5) H35(0.5)
 C36(0.5) H36(0.5) C37(0.5) H37(0.5) C38(0.5) H38(0.5) N1(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,H18B), C20(H20A,H20B),
 C22(H22A,H22B), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B)
7.b Aromatic/amide H refined with riding coordinates:
 C43(H43), C42(H42), C41(H41), C40(H40), C35(H35), C36(H36), C37(H37),
 C38(H38), C2(H2), C5(H5), C14(H14), C17(H17), C25(H25), C28(H28)
7.c Fitted hexagon refined as free rotating group:
 C39(N2,C43,C42,C41,C40), C34(C35,C36,C37,C38,N1)
7.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              2431
_shelx_hkl_checksum              68942
_olex2_submission_special_instructions 'No special instructions were received'