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_4134442
_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         'C66 H84 O12, C5 H4 Cl N'
_chemical_formula_sum            'C71 H88 Cl N O12'
_chemical_formula_weight         1182.87
_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             2019-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.0890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.7980(9)
_cell_length_b                   12.5063(4)
_cell_length_c                   25.5113(9)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      3.42
_cell_volume                     7471.5(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 0.978
_diffrn_measured_fraction_theta_max 0.979
_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_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            38093
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.951
_diffrn_reflns_theta_min         3.284
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.7583.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.468
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6969
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.1166
_refine_ls_shift/su_max          0.001
_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          0.2949
_refine_ls_wR_factor_ref         0.2995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5979
_reflns_number_total             6969
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01274_si_005.cif
_cod_data_source_block           191014sxr_0m
_cod_depositor_comments
'Adding full bibliography for 4134442--4134445.cif.'
_cod_database_code               4134442
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.919
_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
 Cl1-C5AA
 1.7 with sigma of 0.02
 Cl2-C0AA
 1.7 with sigma of 0.02
 C6AA-Cl1 \\sim Cl1-C1AA
 with sigma of 0.02
 C8AA-Cl2 \\sim Cl2-C4AA
 with sigma of 0.02
3. Restrained planarity
 Cl1, C5AA, C6AA, N1, C9AA, C1AA, C7AA
 with sigma of 0.1
 Cl2, C0AA, C4AA, N2, C2AA, C8AA, C3AA
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Cl1 \\sim C5AA \\sim C1AA \\sim C6AA \\sim C9AA \\sim N1 \\sim C7AA: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Cl2 \\sim C0AA \\sim C8AA \\sim C4AA \\sim C3AA \\sim N2 \\sim C2AA: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl1) \\sim Ueq, Uanis(C5AA) \\sim Ueq, Uanis(C1AA) \\sim Ueq, Uanis(C6AA)
\\sim Ueq, Uanis(C9AA) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C7AA) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl2) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C8AA) \\sim Ueq, Uanis(C4AA)
\\sim Ueq, Uanis(C3AA) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C2AA) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: Cl1(0.25) Cl2(0.25) C1AA(0.25) H1AA(0.25) C9AA(0.25) H9AA(0.25)
 C7AA(0.25) H7AA(0.25) N1(0.25) C6AA(0.25) H6AA(0.25) C5AA(0.25) C0AA(0.25)
 C8AA(0.25) H8AA(0.25) C3AA(0.25) H3AA(0.25) C2AA(0.25) H2AA(0.25) N2(0.25)
 C4AA(0.25) H4AA(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C21(H21A,H21B), C7(H7A,H7B), C22(H22A,H22B), C26(H26A,H26B),
 C32(H32A,H32B), C28(H28A,H28B), C30(H30A,H30B), C24(H24A,H24B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C16(H16), C9(H9), C3(H3), C19(H19), C1AA(H1AA), C9AA(H9AA),
 C7AA(H7AA), C6AA(H6AA), C8AA(H8AA), C3AA(H3AA), C2AA(H2AA), C4AA(H4AA)
6.c Fitted hexagon refined as free rotating group:
 C1AA(C9AA,C7AA,N1,C6AA,C5AA), C0AA(C8AA,C3AA,C2AA,N2,C4AA)
6.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              74619
_shelx_hkl_checksum              56344
_olex2_submission_special_instructions 'No special instructions were received'