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_7127660
_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         'C18 H32 N2, F6 Sb'
_chemical_formula_sum            'C18 H32 F6 N2 Sb'
_chemical_formula_weight         512.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 91.44(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.286(3)
_cell_length_b                   16.169(3)
_cell_length_c                   20.044(4)
_cell_measurement_reflns_used    14895
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      59.0
_cell_measurement_theta_min      6.1
_cell_volume                     4304.5(15)
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_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      170.15
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.591
_diffrn_measured_fraction_theta_max 0.591
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1623
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_Laue_measured_fraction_full 0.591
_diffrn_reflns_Laue_measured_fraction_max 0.591
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8280
_diffrn_reflns_point_group_measured_fraction_full 0.591
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_theta_full        24.701
_diffrn_reflns_theta_max         24.701
_diffrn_reflns_theta_min         3.238
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Face indexed'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0569P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1063
_reflns_number_total             2171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07385g2.cif
_cod_data_source_block           mk0385
_cod_depositor_comments
'Adding full bibliography for 7127659--7127670.cif.'
_cod_original_cell_volume        4304.7(15)
_cod_database_code               7127660
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.867
_exptl_absorpt_special_details
;
programs X-Red32 and X-Shape by STOE & Cie GmbH 2010
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 N1-C4 \\sim N1-C4A \\sim N2-C3 \\sim N2-C3A
 with sigma of 0.02
3. Rigid bond restraints
 N1, N2, C4, C3, C4A, C3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C4 \\sim C3 \\sim C4A \\sim C3A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B), C4(H4A,H4B), C3(H3A,H3B), C4A(H4AA,H4AB),
 C3A(H3AA,H3AB)
6.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C10(H10A,H10B,
 H10C)
;
_shelx_res_checksum              38255
_olex2_submission_special_instructions 'No special instructions were received'