Bifunctional carbenium dications as metal-free catalysts for the reduction of oxygen.
Karimi, Mohammadjavad; Borthakur, Rosmita; Dorsey, Christopher L.; Chen, Chang-Hong; Lajeune, Sébastien; Gabbai, Francois P.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c04841

data_4135141
_publ_section_title
;
 Bifunctional carbenium dications as metal-free catalysts for the
 reduction of oxygen.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04841
_journal_year                    2020
_chemical_formula_moiety         'C38 H22 B2 F8 O2, 2(C2 H3 N)'
_chemical_formula_sum            'C42 H28 B2 F8 N2 O2'
_chemical_formula_weight         766.28
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-04-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                105.814(3)
_cell_angle_beta                 97.712(3)
_cell_angle_gamma                90.105(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4600(3)
_cell_length_b                   13.8649(4)
_cell_length_c                   15.5724(5)
_cell_measurement_reflns_used    39817
_cell_measurement_temperature    163
_cell_measurement_theta_max      30.1030
_cell_measurement_theta_min      1.6610
_cell_volume                     1740.15(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      163
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_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    -78.29 144.71   1.00    6.00    --  -30.53  73.80 -99.74  223
  2  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80  67.79  223
  3  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80 156.90  223
  4  \w    -77.20 145.80   1.00    6.00    --  -29.45  73.80  -6.36  223
  5  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80-154.80  223
  6  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80 -55.38  223
  7  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80 112.30  223
  8  \w    -51.27 171.73   1.00    6.00    --   -3.52  73.80-137.93  223
  9  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80   0.28  223
 10  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80-105.67  223
 11  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80 164.49  223
 12  \w    -78.29 144.71   1.00    6.00    --  -30.53  73.80  48.26  223
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0777515000
_diffrn_orient_matrix_UB_12      0.0140786000
_diffrn_orient_matrix_UB_13      -0.0139318000
_diffrn_orient_matrix_UB_21      0.0320710000
_diffrn_orient_matrix_UB_22      0.0263233000
_diffrn_orient_matrix_UB_23      -0.0273296000
_diffrn_orient_matrix_UB_31      -0.0098117000
_diffrn_orient_matrix_UB_32      -0.0440509000
_diffrn_orient_matrix_UB_33      -0.0366767000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            80086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_min         1.750
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0789
_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^)+(0.0290P)^2^+4.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9556
_reflns_number_total             9711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c04841_si_002.cif
_cod_data_source_block           mo_chc05242016
_cod_original_cell_volume        1740.14(10)
_cod_database_code               4135141
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10OBF4N
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F9)=Sof(F10)=Sof(F11)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
 Sof(F12)=Sof(F13)=1-FVAR(2)
 Sof(F7)=Sof(F8)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
  C31(H31), C34(H34), C35(H35), C36(H36), C37(H37)
3.b Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              94555
_shelx_hkl_checksum              24310
_olex2_exptl_crystal_mounting_method loop
_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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.655