Stepwise Reversible Oxidation of N-Peralkyl-Substituted NHC-CAAC Derived Triazaalkenes: Isolation of Radical Cations and Dications.
Mandal, Debdeep; Dolai, Ramapada; Chrysochos, Nicolas; Kalita, Pankaj; Kumar, Ravi; Dhara, Debabrata; Maiti, Avijit; Narayanan, Ramakirushnan Suriya; Rajaraman, Gopalan; Schulzke, Carola; Chandrasekhar, Vadapalli; Jana, Anukul; Organic letters 19 (2017) 5605–5608; doi:10.1021/acs.orglett.7b02721

data_1547513
_publ_section_title
;
 Stepwise Reversible Oxidation of N-Peralkyl-Substituted NHC-CAAC Derived
 Triazaalkenes: Isolation of Radical Cations and Dications.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5605
_journal_page_last               5608
_journal_paper_doi               10.1021/acs.orglett.7b02721
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         '2(C F3 O3 S), C22 H41 N3, C2 H3 N'
_chemical_formula_sum            'C26 H44 F6 N4 O6 S2'
_chemical_formula_weight         686.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.095(2)
_cell_length_b                   13.2861(12)
_cell_length_c                   10.6916(10)
_cell_measurement_reflns_used    4390
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.76
_cell_measurement_theta_min      2.44
_cell_volume                     3280.6(5)
_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(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_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  0.0990
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34135
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.377
_diffrn_reflns_theta_max         25.377
_diffrn_reflns_theta_min         1.764
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0965 before and 0.0760 after correction.
The Ratio of minimum to maximum transmission is 0.8281.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       needle
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0491P)^2^+0.1928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                4340
_reflns_number_total             5540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02721_si_002.cif
_cod_data_source_block           vc_aj_dm_485
_cod_depositor_comments
'Adding full bibliography for 1547507--1547513.cif.'
_cod_database_code               1547513
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I), C12(H12), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C11(H11A,H11B,
 H11C), C8(H8A,H8B,H8C), C00W(H00A,H00B,H00C), C14(H14A,H14B,H14C), C10(H10A,
 H10B,H10C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C),
 C016(H01A,H01B,H01C), C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'