Selective sodium halide over potassium halide binding and extraction by a heteroditopic halogen bonding [2]catenane.
Tay, Hui Min; Docker, Andrew; Hua, Carol; Beer, Paul D.; Chemical science 15 (2024) 13074–13081; doi:10.1039/d4sc03381g

data_1572151
_publ_section_title
;
 Selective sodium halide over potassium halide binding and extraction by a
 heteroditopic halogen bonding [2]catenane.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              13074
_journal_page_last               13081
_journal_paper_doi               10.1039/d4sc03381g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C58 H68 I2 N6 Na O9, I [+ solvents]'
_chemical_formula_sum            'C58 H68 I3 N6 Na O9'
_chemical_formula_weight         1396.87
_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
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-15 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.995(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3809(4)
_cell_length_b                   11.8823(2)
_cell_length_c                   26.6796(5)
_cell_measurement_reflns_used    22699
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.9200
_cell_measurement_theta_min      4.0380
_cell_volume                     6653.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.4102
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -3.00  26.00   1.00    4.00    --  -42.41  19.00 -90.00   29
  2  \w    -22.00   3.00   1.00    4.00    --  -42.41  38.00-150.00   25
  3  \w      2.00  35.00   1.00    4.00    --  -42.41  19.00   0.00   33
  4  \w   -112.00 -61.00   1.00    4.00    --  -42.41 178.00-180.00   51
  5  \w     -5.00  36.00   1.00    4.00    --  -42.41  19.00 -30.00   41
  6  \w    -27.00  28.00   1.00    4.00    --  -42.41  57.00-150.00   55
  7  \w     -5.00  36.00   1.00    4.00    --  -42.41  19.00 120.00   41
  8  \w     43.00  72.00   1.00   17.50    --  111.00 -45.00 -90.00   29
  9  \w     52.00  96.00   1.00   17.50    --  111.00 -77.00-150.00   44
 10  \w     40.00  69.00   1.00   17.50    --  111.00 -45.00 -60.00   29
 11  \w    121.00 152.00   1.00   17.50    --  111.00  15.00 -30.00   31
 12  \w     66.00  93.00   1.00   17.50    --  111.00  15.00  90.00   27
 13  \w     71.00  98.00   1.00   17.50    --  111.00-125.00   0.00   27
 14  \w     41.00  71.00   1.00   17.50    --  111.00 -45.00-120.00   30
 15  \w    104.00 172.00   1.00   17.50    --  111.00  77.00 -30.00   68
 16  \w     40.00  69.00   1.00   17.50    --  111.00 -45.00  30.00   29
 17  \w     49.00  74.00   1.00   17.50    --  111.00 -61.00 -90.00   25
 18  \w     40.00  69.00   1.00   17.50    --  111.00 -45.00-150.00   29
 19  \w     51.00 106.00   1.00   17.50    --  111.00 -96.00-149.00   55
 20  \w     67.00  96.00   1.00   17.50    --  111.00  15.00 -30.00   29
 21  \w     40.00  65.00   1.00   17.50    --  111.00 -45.00 -30.00   25
 22  \w     71.00 108.00   1.00   17.50    --  111.00-125.00 -30.00   37
 23  \w    136.00 161.00   1.00   17.50    --  111.00  77.00 -60.00   25
 24  \w    111.00 160.00   1.00   17.50    --  111.00  77.00-150.00   49
 25  \w     40.00  72.00   1.00   17.50    --  111.00 -45.00-180.00   32
 26  \w    137.00 169.00   1.00   17.50    --  111.00  15.00  90.00   32
 27  \w     44.00  71.00   1.00   17.50    --  111.00 -45.00 120.00   27
 28  \w     57.00  89.00   1.00   17.50    --  111.00 -61.00-150.00   32
 29  \w    112.00 175.00   1.00   17.50    --  111.00  77.00 -90.00   63
 30  \w     -4.00  31.00   1.00    4.00    --  -42.41  19.00  60.00   35
 31  \w      6.00  33.00   1.00    4.00    --  -42.41  19.00 -90.00   27
 32  \w    -22.00   3.00   1.00    4.00    --  -42.41  38.00-180.00   25
 33  \w     -1.00  24.00   1.00    4.00    --  -42.41  19.00  30.00   25
 34  \w     78.00 129.00   1.00    4.00    --   42.41 178.00  60.00   51
 35  \w    102.00 129.00   1.00    4.00    --   42.41 178.00-180.00   27
 36  \w     63.00 128.00   1.00    4.00    --   42.41-178.00-150.00   65
 37  \w     41.00  69.00   1.00   17.50    --  111.00-125.00 150.00   28
 38  \w     73.00 112.00   1.00   17.50    --  111.00-125.00 120.00   39
 39  \w     70.00 110.00   1.00   17.50    --  111.00-115.00-159.99   40
 40  \w     89.00 159.00   1.00   17.50    --  111.00  45.00-150.00   70
 41  \w    130.00 158.00   1.00   17.50    --  111.00  45.00 -90.00   28
 42  \w     53.00  92.00   1.00   17.50    --  111.00 -61.00  90.00   39
 43  \w     51.00  78.00   1.00   17.50    --  111.00-125.00 -90.00   27
 44  \w     79.00 106.00   1.00   17.50    --  111.00 -95.00   0.00   27
 45  \w     45.00  84.00   1.00   17.50    --  111.00 -77.00  90.00   39
 46  \w    132.00 161.00   1.00   17.50    --  111.00  61.00  30.00   29
 47  \w    153.00 178.00   1.00   17.50    --  111.00  30.00   0.00   25
 48  \w     52.00  90.00   1.00   17.50    --  111.00 -61.00 -30.00   38
 49  \w    102.00 127.00   1.00   17.50    --  111.00 -77.00  90.00   25
 50  \w    100.00 144.00   1.00   17.50    --  111.00  30.00 150.00   44
 51  \w     80.00 112.00   1.00   17.50    --  111.00-125.00  30.00   32
 52  \w     91.00 128.00   1.00   17.50    --  111.00  30.00   0.00   37
 53  \w     43.00 109.00   1.00   17.50    --  111.00-125.00  90.00   66
 54  \w     86.00 111.00   1.00   17.50    --  111.00-125.00 150.00   25
 55  \w     99.00 125.00   1.00   17.50    --  111.00  61.00  30.00   26
 56  \w    103.00 133.00   1.00   17.50    --  111.00  30.00-180.00   30
 57  \w     85.00 112.00   1.00   17.50    --  111.00-125.00-180.00   27
 58  \w     97.00 124.00   1.00   17.50    --  111.00-140.00 -36.17   27
 59  \w     90.00 116.00   1.00   17.50    --  111.00-129.00  -0.49   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            83698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.447
_diffrn_reflns_theta_min         3.375
_exptl_absorpt_coefficient_mu    11.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.180
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         13822
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0591P)^2^+14.4376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10393
_reflns_number_total             13822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03381g2.cif
_cod_data_source_block           011hmt23_auto
_cod_depositor_comments          'Adding full bibliography for 1572151.cif.'
_cod_database_code               1572151
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.655
_shelx_estimated_absorpt_t_min   0.119
_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
 C62-O8
 1.4 with sigma of 0.02
 C51-O11
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49) = Uanis(O9) = Uanis(C60) = Uanis(C48) = Uanis(O7) = Uanis(C47) =
Uanis(C61) = Uanis(C50) = Uanis(O8) = Uanis(O11) = Uanis(C51) = Uanis(C62) =
Uanis(C63) = Uanis(C52) = Uanis(O10) = Uanis(O15) = Uanis(C53) = Uanis(C64)
Uanis(C1) = Uanis(C2) = Uanis(C4) = Uanis(C3)
Uanis(C54) = Uanis(C55) = Uanis(C56) = Uanis(C58) = Uanis(C57) = Uanis(C59)
4. Others
 Sof(O10)=Sof(O7)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(O8)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=Sof(C50)=Sof(H50A)=Sof(H50B)=1-FVAR(1)
 Sof(O11)=Sof(O9)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(C60)=Sof(H60A)=Sof(H60B)=
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(O15)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(C63)=
 Sof(H63A)=Sof(H63B)=Sof(C49)=Sof(H49A)=Sof(H49B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,
 H24B), C39(H39A,H39B), C25(H25A,H25B), C40(H40A,H40B), C32(H32A,H32B),
 C37(H37A,H37B), C38(H38A,H38B), C36(H36A,H36B), C20(H20A,H20B), C52(H52A,H52B),
  C35(H35A,H35B), C53(H53A,H53B), C47(H47A,H47B), C48(H48A,H48B), C51(H51A,
 H51B), C50(H50A,H50B), C61(H61A,H61B), C60(H60A,H60B), C64(H64A,H64B),
 C62(H62A,H62B), C63(H63A,H63B), C49(H49A,H49B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C6(H6), C18(H18), C15(H15), C16(H16), C19(H19), C27(H27),
 C31(H31), C28(H28), C42(H42), C46(H46), C59(H59), C30(H30), C55(H55), C45(H45),
  C58(H58), C43(H43), C56(H56)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              41432
_shelx_hkl_checksum              77300
_shelx_fab_checksum              42573
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;