Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognition
Caltagirone, Claudia; Montis, Riccardo; Lippolis, Vito; Bencini, Andrea; Conti, Luca; Giorgi, Claudia; Horton, Peter; Coles, Simon; Mapp, Lucy K.; Gale, Philip A.; Fusaro, Luca; Chemical Communications  (2019) –; doi:10.1039/C8CC09962F

data_7122834
_publ_section_title
;
 Fluoride binding by an anionic receptor: tuning the acidity of amide NH
 groups for basic anion hydrogen bonding and recognition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09962F
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C29 H25 N5 O6, H2 O'
_chemical_formula_sum            'C29 H27 N5 O7'
_chemical_formula_weight         557.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.25 svn.r3318 for OlexSys, GUI svn.r5204)
;
_audit_update_record
;
2018-07-09 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.325(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4201(16)
_cell_length_b                   13.601(2)
_cell_length_c                   10.9510(18)
_cell_measurement_reflns_used    12875
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1324.0(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_detector_type
;
'Rigaku Mercury375R (2x2 bin mode)'
;
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 195
               Slice: -75.0000 - 120.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 50.1908
              2theta: 29.8397
scan:
    Number of images: 195
               Slice: -75.0000 - 120.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 50.1908
              2theta: 29.8397
scan:
    Number of images: 117
               Slice: -75.0000 - 42.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 60.0000
                 XTD: 50.1908
              2theta: 29.8397
scan:
    Number of images: 67
               Slice: -8.0000 - 59.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 300.0000
                 XTD: 50.1908
              2theta: 29.8397
scan:
    Number of images: 45
               Slice: 37.0000 - 82.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 50.1908
              2theta: 29.8397
scan:
    Number of images: 30
               Slice: 15.0000 - 45.0000
         Image width: 1.0000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 50.1908
              2theta: 29.8397
;
_diffrn_measurement_device       'XtaLABmini: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'XtaLAB mini'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.095984
_diffrn_orient_matrix_UB_12      -0.023081
_diffrn_orient_matrix_UB_13      0.010706
_diffrn_orient_matrix_UB_21      0.030012
_diffrn_orient_matrix_UB_22      -0.069768
_diffrn_orient_matrix_UB_23      -0.006857
_diffrn_orient_matrix_UB_31      0.050410
_diffrn_orient_matrix_UB_32      -0.002411
_diffrn_orient_matrix_UB_33      0.095930
_diffrn_radiation_collimation    0.8
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.995
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed tube'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6061
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3718
_reflns_number_total             6061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09962f2.cif
_cod_data_source_block           H2L1
_cod_database_code               7122834
_olex2_refinement_description
;
1. 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 O(H) groups, All O(H,H) groups
2. Restrained distances
 H61-H1WB
 2.2 with sigma of 0.02
 H61-H1WA
 2.2 with sigma of 0.02
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C10(H10), C19(H19)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16),
 C24(H24), C25(H25), C26(H26), C27(H27), C29(H29)
;
_shelx_res_checksum              47617
_shelx_hkl_checksum              67026
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen mount'
_olex2_submission_special_instructions 'No special instructions were received'