Highly Selective Fluoride Recognition by a Small Tris-Urea Covalent Cage.
Delecluse, Magalie; Colomban, Cédric; Chatelet, Bastien; Chevallier-Michaud, Sabine; Moraleda, Delphine; Dutasta, Jean-Pierre; Martinez, Alexandre; The Journal of organic chemistry 85 (2020) 4706–4711; doi:10.1021/acs.joc.9b03429

data_4038083
_publ_section_title
;
 Highly Selective Fluoride Recognition by a Small Tris-Urea Covalent Cage.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4706
_journal_page_last               4711
_journal_paper_doi               10.1021/acs.joc.9b03429
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety
'C H Cl3, 0.9(F), C39 H51 N7 O9, 0.1(H2 O), C16 H36 N'
_chemical_formula_sum            'C56 H88.2 Cl3 F0.9 N8 O9.1'
_chemical_formula_weight         1142.59
_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   mixed
_audit_creation_date             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.269(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1056(3)
_cell_length_b                   18.4895(5)
_cell_length_c                   27.4703(7)
_cell_measurement_reflns_used    6126
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      67.4770
_cell_measurement_theta_min      4.0270
_cell_volume                     6111.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.972
_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      1.00  38.00   1.00    7.50    --    0.00 -99.00  60.00   37
  2  \w      0.00  29.00   1.00    7.50    --    0.00  57.00-150.00   29
  3  \w     44.00  90.00   1.00    7.50    --    0.00  57.00-150.00   46
  4  \w   -139.00 -82.00   1.00   15.00    --  -53.19 -94.00-150.00   57
  5  \w   -150.00 -80.00   1.00   15.00    --  -53.19 -94.00  60.00   70
  6  \w   -152.00 -80.00   1.00   15.00    --  -53.19 -94.00   0.00   72
  7  \w   -112.00 -80.00   1.00   15.00    --  -53.19 -91.00 -52.00   32
  8  \w    -89.00 -51.00   1.00   15.00    --  -53.19 125.00-180.00   38
  9  \w   -140.00-109.00   1.00   15.00    --  -53.19 -94.00 -60.00   31
 10  \w     24.00  93.00   1.00   15.00    --   53.19 -94.00  30.00   69
 11  \w     65.00  91.00   1.00   30.00    --  106.37 178.00 -60.00   26
 12  \w    100.00 168.00   1.00   30.00    --  106.37  50.00 120.00   68
 13  \w     64.00  90.00   1.00   30.00    --  106.37 178.00  30.00   26
 14  \w    116.00 141.00   1.00   30.00    --  106.37 178.00  30.00   25
 15  \w    109.00 140.00   1.00   30.00    --  106.37  63.00 -30.00   31
 16  \w     61.00 102.00   1.00   30.00    --  106.37  63.00 -30.00   41
 17  \w     56.00 112.00   1.00   30.00    --  106.37-111.00-120.00   56
 18  \w     65.00 177.00   1.00   30.00    --  106.37  63.00 -90.00  112
 19  \w     13.00  54.00   1.00   30.00    --  106.37-111.00-120.00   41
 20  \w     72.00 140.00   1.00   30.00    --  106.37 178.00  90.00   68
 21  \w     22.00 116.00   1.00   30.00    --  106.37 -63.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0646628000
_diffrn_orient_matrix_UB_12      0.0037164000
_diffrn_orient_matrix_UB_13      -0.0514681000
_diffrn_orient_matrix_UB_21      0.0045348000
_diffrn_orient_matrix_UB_22      -0.0830495000
_diffrn_orient_matrix_UB_23      -0.0038405000
_diffrn_orient_matrix_UB_31      -0.1104215000
_diffrn_orient_matrix_UB_32      -0.0056011000
_diffrn_orient_matrix_UB_33      0.0227834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22969
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.343
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       needle
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         10919
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0894
_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^)+(0.1536P)^2^+4.5155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2549
_refine_ls_wR_factor_ref         0.2870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7299
_reflns_number_total             10919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03429_si_002.cif
_cod_data_source_block           cc1exp133
_cod_depositor_comments          'Adding full bibliography for 4038083.cif.'
_cod_original_formula_sum        'C56 H88.20 Cl3 F0.90 N8 O9.10'
_cod_database_code               4038083
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c55 h87 f1 n8 o9'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.554
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C53-C54
 1.54 with sigma of 0.01
 C51-C52
 1.54 with sigma of 0.01
 C56-C57
 1.45 with sigma of 0.01
 C56-C59
 1.45 with sigma of 0.01
 C57-C58
 1.54 with sigma of 0.01
 C59-C60
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C56 \\sim C57: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.01
C57 \\sim C58: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.01
4. Rigid body (RIGU) restrains
 C56, C57, C58, C59, C60
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: F1(0.9) O10(0.1) H10A(0.1) H10B(0.1) H50A(0.5) H50B(0.5) H50C(0.5)
 H50D(0.5) C51(0.5) H51A(0.5) H51B(0.5) C52(0.5) H52A(0.5) H52B(0.5) H52C(0.5)
 C53(0.5) H53A(0.5) H53B(0.5) C54(0.5) H54A(0.5) H54B(0.5) H54C(0.5) H56C(0.5)
 H56D(0.5) H56A(0.5) H56B(0.5) C57(0.5) H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5)
 H58B(0.5) H58C(0.5) C59(0.5) H59A(0.5) H59B(0.5) C60(0.5) H60A(0.5) H60B(0.5)
 H60C(0.5)
6.a Riding coordinates:
 O10(H10A,H10B)
6.b Ternary CH refined with riding coordinates:
 C40(H40)
6.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,H13B), C21(H21A,
 H21B), C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C29(H29A,H29B), C30(H30A,H30B), C38(H38A,H38B), C39(H39A,H39B),
  C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B), C49(H49A,H49B), C50(H50A,H50B), C50(H50C,H50D),
 C51(H51A,H51B), C53(H53A,H53B), C55(H55A,H55B), C56(H56C,H56D), C56(H56A,H56B),
  C57(H57A,H57B), C59(H59A,H59B)
6.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), N7(H7), C7(H7A), C10(H10), C15(H15),
 C18(H18), C32(H32), C35(H35)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C), C44(H44A,H44B,
 H44C), C48(H48A,H48B,H48C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C58(H58A,
 H58B,H58C), C60(H60A,H60B,H60C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.743
_oxdiff_exptl_absorpt_empirical_full_min 0.501