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_4134445
_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 H72 Br12 O12, C5 H4 Cl N'
_chemical_formula_sum            'C71 H76 Br12 Cl N O12'
_chemical_formula_weight         2129.69
_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
_audit_creation_date             2019-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                117.9100(10)
_cell_angle_beta                 100.4210(10)
_cell_angle_gamma                94.4500(10)
_cell_formula_units_Z            1
_cell_length_a                   13.3514(3)
_cell_length_b                   13.3868(3)
_cell_length_c                   13.8133(3)
_cell_measurement_reflns_used    9030
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.910
_cell_measurement_theta_min      3.832
_cell_volume                     2108.00(8)
_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      170.01
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0571
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24602
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.952
_diffrn_reflns_theta_min         4.329
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.169
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1387 before and 0.0867 after correction. The Ratio of minimum to maximum transmission is 0.6769. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       block
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.909
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         7778
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.1186
_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^)+(0.1381P)^2^+10.4643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3020
_refine_ls_wR_factor_ref         0.3048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7212
_reflns_number_total             7778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01274_si_002.cif
_cod_data_source_block           20181225sxr1_1
_cod_depositor_comments
'Adding full bibliography for 4134442--4134445.cif.'
_cod_database_code               4134445
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.358
_shelx_estimated_absorpt_t_min   0.316
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C41-C40
 1.53 with sigma of 0.02
 C45-C44
 1.53 with sigma of 0.02
 C13-C12
 1.53 with sigma of 0.02
 Br3-C13
 1.8 with sigma of 0.02
 Br9-C41
 1.8 with sigma of 0.02
 C43-C42
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim N1 \\sim C017 \\sim C019 \\sim C5AA \\sim C5BA \\sim C01D: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Br9 \\sim O9 \\sim C40 \\sim C41: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br3 \\sim C12 \\sim C13: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Br4 \\sim O1 \\sim C14 \\sim C15: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br11 \\sim C44 \\sim C45: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Br10 \\sim O11 \\sim C42 \\sim C43: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C34 \\sim Br9 \\sim O9 \\sim C40 \\sim C41: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O10 \\sim C38 \\sim C39: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C23 \\sim C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Br7(0.5) H3(0.5) H4(0.5) H6(0.5) H7(0.5) H18(0.5) H19(0.5)
 H21(0.5) H22(0.5) H33(0.5) H34(0.5) H36(0.5) H37(0.5) Br1(0.5) Br2(0.5)
 Br5(0.5) Br6(0.5) Br9(0.5) O3(0.5) O4(0.5) O7(0.5) O8(0.5) O9(0.5) O10(0.5)
 C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5)
 H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5)
 H24A(0.5) H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5)
 C38(0.5) H38A(0.5) H38B(0.5) C39(0.5) H39A(0.5) H39B(0.5) C40(0.5) H40A(0.5)
 H40B(0.5) C41(0.5) H41A(0.5) H41B(0.5) Br3(0.5) Br4(0.5) Br8(0.5) Br10(0.5)
 Br11(0.5) O1(0.5) O2(0.5) O5(0.5) O6(0.5) O11(0.5) O12(0.5) C12(0.5) H12A(0.5)
 H12B(0.5) C13(0.5) H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) C27(0.5) H27A(0.5) H27B(0.5) C28(0.5) H28A(0.5) H28B(0.5)
 C29(0.5) H29A(0.5) H29B(0.5) C30(0.5) H30A(0.5) H30B(0.5) C42(0.5) H42A(0.5)
 H42B(0.5) C43(0.5) H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5) C45(0.5)
 H45A(0.5) H45B(0.5) Cl1(0.5) C019(0.5) C017(0.5) H017(0.5) C01D(0.5) H01D(0.5)
 C5AA(0.5) H5AA(0.5) C5BA(0.5) H5BA(0.5) N1(0.5) Br7A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C16(H16A,H16B), C31(H31A,H31B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,
 H41B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C42(H42A,H42B),
  C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C18(H18), C19(H19), C21(H21), C22(H22),
 C33(H33), C34(H34), C36(H36), C37(H37), C017(H017), C01D(H01D), C5AA(H5AA),
 C5BA(H5BA)
5.c Fitted hexagon refined as free rotating group:
 C019(C017,C01D,C5AA,C5BA,N1)
;
_shelx_res_checksum              81464
_shelx_hkl_checksum              5042
_olex2_submission_special_instructions 'No special instructions were received'