Guilty and charged: a stable solution of the hexamethylbenzene radical cation as a ligand forming oxidising agent.
Schorpp, Marcel; Rein, Stephan; Weber, Stefan; Scherer, Harald; Krossing, Ingo; Chemical communications (Cambridge, England) 54 (2018) 10036–10039; doi:10.1039/c8cc04690e

data_7122032
_publ_section_title
;
 Guilty and charged: a stable solution of the hexamethylbenzene radical
 cation as a ligand forming oxidising agent.
;
_journal_issue                   72
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10036
_journal_page_last               10039
_journal_paper_doi               10.1039/c8cc04690e
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Al C16 F36 O4, C9 H12 In'
_chemical_formula_sum            'C25 H12 Al F36 In O4'
_chemical_formula_weight         1202.15
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-23 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.373(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6026(6)
_cell_length_b                   17.5964(11)
_cell_length_c                   11.1567(6)
_cell_measurement_reflns_used    9329
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.24
_cell_volume                     1910.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32910
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.334
_diffrn_reflns_theta_min         1.989
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0864 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.8373. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.299
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 3127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         8220
_refine_ls_number_restraints     2911
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+2.5337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                7539
_reflns_number_total             8220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04690e2.cif
_cod_data_source_block           p21_a
_cod_depositor_comments
'Adding full bibliography for 7122030--7122033.cif.'
_cod_database_code               7122032
_shelx_shelxl_version_number     2018/1
_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
 C1_4-C2_4 \\sim C1_4-C3_4 \\sim C1_4-C4_4
 C1_3-C2_3 \\sim C1_3-C3_3 \\sim C1_3-C4_3
 C1_2-C2_2 \\sim C1_2-C3_2 \\sim C1_2-C4_2
 C1_1-C2_1 \\sim C1_1-C3_1 \\sim C1_1-C4_1
 with sigma of 0.02
 F1_4-C2_4 \\sim F2_4-C2_4 \\sim F3_4-C2_4 \\sim F4_4-C3_4 \\sim F5_4-C3_4
\\sim F6_4-C3_4 \\sim F7_4-
 C4_4 \\sim F8_4-C4_4 \\sim F9_4-C4_4
 F1_3-C2_3 \\sim F2_3-C2_3 \\sim F3_3-C2_3 \\sim F4_3-C3_3 \\sim F5_3-C3_3
\\sim F6_3-C3_3 \\sim F7_3-
 C4_3 \\sim F8_3-C4_3 \\sim F9_3-C4_3
 F1_2-C2_2 \\sim F2_2-C2_2 \\sim F3_2-C2_2 \\sim F4_2-C3_2 \\sim F5_2-C3_2
\\sim F6_2-C3_2 \\sim F7_2-
 C4_2 \\sim F8_2-C4_2 \\sim F9_2-C4_2
 F1_1-C2_1 \\sim F2_1-C2_1 \\sim F3_1-C2_1 \\sim F4_1-C3_1 \\sim F5_1-C3_1
\\sim F6_1-C3_1 \\sim F7_1-
 C4_1 \\sim F8_1-C4_1 \\sim F9_1-C4_1
 with sigma of 0.02
 C2_4-C3_4 \\sim C3_4-C4_4 \\sim C2_4-C4_4
 C2_3-C3_3 \\sim C3_3-C4_3 \\sim C2_3-C4_3
 C2_2-C3_2 \\sim C3_2-C4_2 \\sim C2_2-C4_2
 C2_1-C3_1 \\sim C3_1-C4_1 \\sim C2_1-C4_1
 with sigma of 0.04
 O1_4-C2_4 \\sim O1_4-C3_4 \\sim O1_4-C4_4
 O1_3-C2_3 \\sim O1_3-C3_3 \\sim O1_3-C4_3
 O1_2-C2_2 \\sim O1_2-C3_2 \\sim O1_2-C4_2
 O1_1-C2_1 \\sim O1_1-C3_1 \\sim O1_1-C4_1
 with sigma of 0.04
 F1_4-F2_4 \\sim F2_4-F3_4 \\sim F3_4-F1_4 \\sim F4_4-F5_4 \\sim F5_4-F6_4
\\sim F6_4-F4_4 \\sim F7_4-
 F8_4 \\sim F8_4-F9_4 \\sim F9_4-F7_4
 F1_3-F2_3 \\sim F2_3-F3_3 \\sim F3_3-F1_3 \\sim F4_3-F5_3 \\sim F5_3-F6_3
\\sim F6_3-F4_3 \\sim F7_3-
 F8_3 \\sim F8_3-F9_3 \\sim F9_3-F7_3
 F1_2-F2_2 \\sim F2_2-F3_2 \\sim F3_2-F1_2 \\sim F4_2-F5_2 \\sim F5_2-F6_2
\\sim F6_2-F4_2 \\sim F7_2-
 F8_2 \\sim F8_2-F9_2 \\sim F9_2-F7_2
 F1_1-F2_1 \\sim F2_1-F3_1 \\sim F3_1-F1_1 \\sim F4_1-F5_1 \\sim F5_1-F6_1
\\sim F6_1-F4_1 \\sim F7_1-
 F8_1 \\sim F8_1-F9_1 \\sim F9_1-F7_1
 with sigma of 0.04
 O1_4-C1_4
 O1_3-C1_3
 O1_2-C1_2
 O1_1-C1_1
 with sigma of 0.02
 F1_4-C1_4 \\sim F2_4-C1_4 \\sim F3_4-C1_4 \\sim F4_4-C1_4 \\sim F5_4-C1_4
\\sim F6_4-C1_4 \\sim F7_4-
 C1_4 \\sim F8_4-C1_4 \\sim F9_4-C1_4
 F1_3-C1_3 \\sim F2_3-C1_3 \\sim F3_3-C1_3 \\sim F4_3-C1_3 \\sim F5_3-C1_3
\\sim F6_3-C1_3 \\sim F7_3-
 C1_3 \\sim F8_3-C1_3 \\sim F9_3-C1_3
 F1_2-C1_2 \\sim F2_2-C1_2 \\sim F3_2-C1_2 \\sim F4_2-C1_2 \\sim F5_2-C1_2
\\sim F6_2-C1_2 \\sim F7_2-
 C1_2 \\sim F8_2-C1_2 \\sim F9_2-C1_2
 F1_1-C1_1 \\sim F2_1-C1_1 \\sim F3_1-C1_1 \\sim F4_1-C1_1 \\sim F5_1-C1_1
\\sim F6_1-C1_1 \\sim F7_1-
 C1_1 \\sim F8_1-C1_1 \\sim F9_1-C1_1
 with sigma of 0.1
 Al1-O1_1 \\sim Al1-O1_2 \\sim Al1-O1_3 \\sim Al1-O1_4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 O1_4, C1_4, C2_4, F1_4, F2_4, F3_4, C3_4, F4_4, F5_4, F6_4, C4_4, F7_4, F8_4,
 F9_4
 O1_3, C1_3, C2_3, F1_3, F2_3, F3_3, C3_3, F4_3, F5_3, F6_3, C4_3, F7_3, F8_3,
 F9_3
 O1_2, C1_2, C2_2, F1_2, F2_2, F3_2, C3_2, F4_2, F5_2, F6_2, C4_2, F7_2, F8_2,
 F9_2
 O1_1, C1_1, C2_1, F1_1, F2_1, F3_1, C3_1, F4_1, F5_1, F6_1, C4_1, F7_1, F8_1,
 F9_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1_3, C1_3, C2_3, F1_3, F2_3, F3_3, C3_3, F4_3, F5_3, F6_3, C4_3, F7_3, F8_3,
F9_3}
{O1_2, C1_2, C2_2, F1_2, F2_2, F3_2, C3_2, F4_2, F5_2, F6_2, C4_2, F7_2, F8_2,
F9_2}
{O1_1, C1_1, C2_1, F1_1, F2_1, F3_1, C3_1, F4_1, F5_1, F6_1, C4_1, F7_1, F8_1,
F9_1}
as
{O1_4, C1_4, C2_4, F1_4, F2_4, F3_4, C3_4, F4_4, F5_4, F6_4, C4_4, F7_4, F8_4,
F9_4} sigma for 1-2: 0.02 1-3: 0.04
6.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4)
6.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'