Trioxatriangulenium (TOTA+) as a robust carbon-based Lewis acid in frustrated Lewis pair chemistry
Shaikh, Aslam C.; Veleta, José M.; Moutet, Jules; Gianetti, Thomas L.; Chemical Science 12 (2021) 4841–4849; doi:10.1039/D0SC05893A

data_1560305
_publ_section_title
;
 Trioxatriangulenium (TOTA+) as a robust carbon-based Lewis acid in
 frustrated Lewis pair chemistry
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4841
_journal_page_last               4849
_journal_paper_doi               10.1039/D0SC05893A
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C32 H12 B F24, C30 H29 N2 O3'
_chemical_formula_sum            'C62 H41 B F24 N2 O3'
_chemical_formula_weight         1328.78
_chemical_name_common            11
_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     dual
_audit_creation_date             2020-07-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-10-08 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                106.612(2)
_cell_angle_beta                 101.5130(10)
_cell_angle_gamma                105.3750(10)
_cell_formula_units_Z            2
_cell_length_a                   13.4502(6)
_cell_length_b                   15.5304(7)
_cell_length_c                   16.0826(7)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.270
_cell_measurement_theta_min      2.278
_cell_volume                     2962.9(2)
_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      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.905
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            65798
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         1.384
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.319
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1059
_refine_ls_number_reflns         12267
_refine_ls_number_restraints     1680
_refine_ls_restrained_S_all      1.355
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0531P)^2^+1.5289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9790
_reflns_number_total             12267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05893a2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 1560304--1560308.cif.'
_cod_database_code               1560305
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.940
_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. Restrained distances
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F4-F5 \\sim F5-F6 \\sim F6-F4 \\sim F7-F8
\\sim F8-F9 \\sim F9-F7 \\sim F10-
 F11 \\sim F11-F12 \\sim F12-F10 \\sim F13-F14 \\sim F14-F15 \\sim F15-F13
\\sim F16-F17 \\sim F17-F18 ~
 F18-F16 \\sim F19-F20 \\sim F20-F21 \\sim F21-F19 \\sim F22-F23 \\sim F23-F24
\\sim F24-F22
 with sigma of 0.03
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
\\sim F7A-F8A \\sim F8A-F9A
 \\sim F9A-F7A \\sim F10A-F11A \\sim F11A-F12A \\sim F12A-F10A \\sim F13A-F14A
\\sim F14A-F15A \\sim F15A-
 F13A \\sim F16A-F17A \\sim F17A-F18A \\sim F18A-F16A \\sim F19A-F20A \\sim
F20A-F21A \\sim F21A-F19A ~
 F22A-F23A \\sim F23A-F24A \\sim F24A-F22A
 with sigma of 0.03
 F24-C61 \\sim F23-C61 \\sim F22-C61 \\sim F20-C62 \\sim F19-C62 \\sim F21-C62
\\sim F6-C38 \\sim F5-C38 ~
 F4-C38 \\sim F8-C45 \\sim F7-C45 \\sim F9-C45 \\sim F2-C37 \\sim F1-C37 \\sim
F3-C37 \\sim F12-C46 \\sim F10-
 C46 \\sim F11-C46 \\sim F15-C53 \\sim F14-C53 \\sim F13-C53 \\sim F18-C54
\\sim F16-C54 \\sim F17-C54
 with sigma of 0.02
 F18A-C54 \\sim F17A-C54 \\sim F16A-C54 \\sim F15A-C53 \\sim F14A-C53 \\sim
F13A-C53 \\sim F1A-C37 ~
 F2A-C37 \\sim F3A-C37 \\sim F5A-C38 \\sim F4A-C38 \\sim F6A-C38 \\sim F12A-C46
\\sim F10A-C46 \\sim F11A-
 C46 \\sim F8A-C45 \\sim F9A-C45 \\sim F7A-C45 \\sim F24A-C61 \\sim F23A-C61
\\sim F22A-C61 \\sim F21A-C62
 \\sim F19A-C62 \\sim F20A-C62
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F9A \\sim F1A \\sim F2 \\sim F17A \\sim F3 \\sim F5A \\sim F4 \\sim
F13A \\sim F5 \\sim F21A \\sim F6 \\sim F3A \\sim F7 \\sim F7A \\sim F8 \\sim
F11A \\sim F9 \\sim F15A \\sim F10 \\sim F19A \\sim F11 \\sim F24A \\sim F12
\\sim F2A \\sim F13 \\sim F4A \\sim F14 \\sim F6A \\sim F15 \\sim F8A \\sim F16
\\sim F10A \\sim F17 \\sim F12A \\sim F18 \\sim F14A \\sim F19 \\sim F16A \\sim
F20 \\sim F18A \\sim F21 \\sim F20A \\sim F22 \\sim F22A \\sim F23 \\sim F23A
\\sim F24: within 2A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 2A
C27 \\sim C28 \\sim C29 \\sim C30: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008 within 2A
Uanis(F1) \\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2)
\\sim Ueq, Uanis(F17A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F5A) \\sim Ueq,
Uanis(F4) \\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F21A)
\\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F7) \\sim Ueq,
Uanis(F7A) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F9)
\\sim Ueq, Uanis(F15A) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F19A) \\sim Ueq,
Uanis(F11) \\sim Ueq, Uanis(F24A) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F14) \\sim Ueq,
Uanis(F6A) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F16)
\\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F12A) \\sim Ueq,
Uanis(F18) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F16A)
\\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F18A) \\sim Ueq, Uanis(F21) \\sim Ueq,
Uanis(F20A) \\sim Ueq, Uanis(F22) \\sim Ueq, Uanis(F22A) \\sim Ueq, Uanis(F23)
\\sim Ueq, Uanis(F23A) \\sim Ueq, Uanis(F24) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F19A) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(3)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(4)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(4)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(5)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(5)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(6)
 Sof(F16)=Sof(F17)=Sof(F18)=FVAR(6)
 Sof(F19A)=Sof(F20A)=Sof(F21A)=1-FVAR(7)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(7)
 Sof(F22A)=Sof(F24A)=Sof(F23A)=1-FVAR(8)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(8)
5.a Aromatic/amide H refined with riding coordinates:
 C32(H32), C34(H34), C36(H36), C40(H40), C42(H42), C44(H44), C48(H48),
 C50(H50), C52(H52), C56(H56), C58(H58), C60(H60), C4(H4), C5(H5), C6(H6),
 C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22)
5.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              91124
_shelx_hkl_checksum              89442
_shelx_fab_checksum              53785
_olex2_submission_special_instructions 'No special instructions were received'