Organic Redox Systems Based on Pyridinium-Carbene Hybrids.
Antoni, Patrick W.; Bruckhoff, Tim; Hansmann, Max M.; Journal of the American Chemical Society 141 (2019) 9701–9711; doi:10.1021/jacs.9b04249

data_4127452
_publ_section_title
;
 Organic Redox Systems Based on Pyridinium-Carbene Hybrids.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9701
_journal_page_last               9711
_journal_paper_doi               10.1021/jacs.9b04249
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '2(F6 Sb), 4(C4 H8 O), C29 H35 N3'
_chemical_formula_sum            'C45 H67 F12 N3 O4 Sb2'
_chemical_formula_weight         1185.51
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.3720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1588(7)
_cell_length_b                   13.8404(6)
_cell_length_c                   22.8193(12)
_cell_measurement_reflns_used    9497
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.96
_cell_volume                     5143.0(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.03
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            55169
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_min         2.405
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.136
_exptl_absorpt_correction_T_max  0.2269
_exptl_absorpt_correction_T_min  0.1878
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0773 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.8277. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_recrystallization_method
'The material was recrystallised from thf by slow evaporation'
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.313
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         7846
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+6.5380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7537
_reflns_number_total             7846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04249_si_014.cif
_cod_data_source_block           c2c
_cod_database_code               4127452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.607
_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. Rigid body (RIGU) restrains
 O2B, C21B, C22B, C23B, C24B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 Sof(O2B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22D)=Sof(H22C)=
 Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=1-FVAR(1)
 Sof(O2A)=Sof(C21A)=Sof(H21B)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=FVAR(1)
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21A(H21B,
 H21A), C22A(H22A,H22B), C23A(H23A,H23B), C24A(H24A,H24B), C21B(H21C,H21D),
 C22B(H22D,H22C), C23B(H23C,H23D), C24B(H24C,H24D)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C11(H11), C16(H16)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              49081
_shelx_hkl_checksum              21882
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'