Tethered CAAC-CAAC dimers: oxidation to persistent radical cations and bridging-unit dependent reactivity/stability of the dications.
Nayak, Mithilesh Kumar; Suhr, Simon; Chrysochos, Nicolas; Rawat, Hemant; Schulzke, Carola; Chandrasekhar, Vadapalli; Sarkar, Biprajit; Jana, Anukul; Chemical communications (Cambridge, England) 57 (2021) 1210–1213; doi:10.1039/d0cc07385g

data_7127666
_publ_section_title
;
 Tethered CAAC-CAAC dimers: oxidation to persistent radical cations and
 bridging-unit dependent reactivity/stability of the dications.
;
_journal_issue                   10
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1210
_journal_page_last               1213
_journal_paper_doi               10.1039/d0cc07385g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C F3 O3 S, C19 H34 N2'
_chemical_formula_sum            'C20 H34 F3 N2 O3 S'
_chemical_formula_weight         439.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-06 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7269(5)
_cell_length_b                   16.6330(3)
_cell_length_c                   16.7087(4)
_cell_measurement_reflns_used    25604
_cell_measurement_temperature    119.98(10)
_cell_measurement_theta_max      28.7530
_cell_measurement_theta_min      2.7240
_cell_volume                     4370.75(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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      119.98(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_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    -15.00  23.00   0.50   50.00    --    7.20 -57.00 150.00   76
  2  \w    -72.00  35.00   0.50   50.00    --    7.20 -57.00 -60.00  214
  3  \w     63.00  94.00   0.50   50.00    --    7.20  77.00-150.00   62
  4  \w     50.00  83.00   0.50   50.00    --    7.20  77.00-180.00   66
  5  \w     69.00  96.00   0.50   50.00    --    7.20  77.00 -90.00   54
  6  \w     51.00  81.00   0.50   50.00    --    7.20  77.00 -60.00   60
  7  \w     46.00  87.00   0.50   50.00    --    7.20  57.00  30.00   82
  8  \w     50.00  75.00   0.50   50.00    --    7.20  77.00   0.00   50
  9  \w    -63.00  31.00   0.50   50.00    --   -7.60 -82.00 120.00  188
 10  \w    -81.00  17.00   0.50   50.00    --   -7.60 -38.00 150.00  196
 11  \w    -63.00  -1.00   0.50   50.00    --   -7.60 -82.00  30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            72306
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.957
_diffrn_reflns_theta_min         2.590
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         10578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.9664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9188
_reflns_number_total             10578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07385g2.cif
_cod_data_source_block           aj0625
_cod_depositor_comments
'Adding full bibliography for 7127659--7127670.cif.'
_cod_database_code               7127666
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8033(6)
 0.1967(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C4(H4A,H4B), C26(H26A,H26B), C23(H23A,H23B), C5(H5A,H5B),
 C3(H3A,H3B), C14(H14A,H14B), C24(H24A,H24B), C33(H33A,H33B), C7(H7A,H7B)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C18(H18A,H18B,H18C), C35(H35A,H35B,
 H35C), C30(H30A,H30B,H30C), C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C19(H19A,H19B,H19C), C36(H36A,H36B,H36C),
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              61783
_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
;