Ion pair extractant selective for LiCl and LiBr.
Heo, Nam Jung; Oh, Ju Hyun; Li, Aimin; Lee, Kyounghoon; He, Qing; Sessler, Jonathan L.; Kim, Sung Kuk; Chemical science 15 (2024) 13958–13965; doi:10.1039/d4sc03760j

data_1572321
_publ_section_title
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 Ion pair extractant selective for LiCl and LiBr.
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_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13958
_journal_page_last               13965
_journal_paper_doi               10.1039/d4sc03760j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'Br, 2(C H Cl3), C54 H56 Li N6 O4'
_chemical_formula_sum            'C56 H58 Br Cl6 Li N6 O4'
_chemical_formula_weight         1178.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
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2024-05-17 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.9123(13)
_cell_length_b                   14.8656(13)
_cell_length_c                   13.0840(10)
_cell_measurement_reflns_used    3303
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      21.494
_cell_measurement_theta_min      2.538
_cell_volume                     2706.0(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10438
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         1.370
_diffrn_source_current           18.0
_diffrn_source_power             0.9
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1158 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.7171.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.523
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.47(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1176P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1889
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.706
_reflns_number_gt                4305
_reflns_number_total             5505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03760j2.cif
_cod_data_source_block           ppc-libr
_cod_depositor_comments          'Adding full bibliography for 1572321.cif.'
_cod_database_code               1572321
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.719
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.53(2)
 0.47(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O1-C7 = O1-C7A = O3-C31 = O2-C30
 1.43 with sigma of 0.01
 C6-C7 = C6-C7A
 1.54 with sigma of 0.01
 C33-Cl3 = C33-Cl4 = C33-Cl5
 1.74 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7A)
Uanis(O3) = Uanis(C31)
5. Others
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=1-FVAR(1)
 Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(1)
 Fixed Sof: H2A(0.5) H21A(0.5) H21B(0.5) H21C(0.5) H28B(0.5) H28C(0.5)
 H22A(0.5) H22B(0.5) H22C(0.5) H29B(0.5) H29C(0.5) H30A(0.5) H30B(0.5)
 H30C(0.5) Li1(0.5) O3(0.5) H3A(0.5) C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5)
 C33(0.5) H33(0.5) Cl3(0.5) Cl4(0.5) Cl5(0.5)
6.a Ternary CH refined with riding coordinates:
 C32(H32), C33(H33)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7A(H7AA,H7AB)
6.c Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C22(H22A,H22B,H22C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C)
6.d Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C10(H10), C24(H24), C4(H4), C17(H17), C25(H25), C13(H13),
 C1(H1), C18(H18), C5(H5), C9(H9), C12(H12)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O3(H3A)
;
_shelx_res_checksum              133
_shelx_hkl_checksum              56628
_olex2_submission_special_instructions 'No special instructions were received'