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_4127449
_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         'C45 H40 F3 N3, F6 Sb1'
_chemical_formula_sum            'C45 H40 F9 N3 Sb'
_chemical_formula_weight         915.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.746(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3070(10)
_cell_length_b                   16.3038(9)
_cell_length_c                   17.6125(12)
_cell_measurement_reflns_used    9620
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      29.588
_cell_measurement_theta_min      2.881
_cell_volume                     4070.8(5)
_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      99.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            219371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.649
_diffrn_reflns_theta_min         2.648
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.3528
_exptl_absorpt_correction_T_min  0.3026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1554 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.8577. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       plate
_exptl_crystal_F_000             1852
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of thf and Diethylether  by slow evaporation'
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         11466
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+2.5098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10785
_reflns_number_total             11466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04249_si_010.cif
_cod_data_source_block           0539_cg_0m
_cod_database_code               4127449
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.676
_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
 Sb1A-F9A \\sim Sb1B-F5B
 with sigma of 0.02
 Sb1A-F8A \\sim Sb1B-F6B
 with sigma of 0.02
 Sb1A-F6A \\sim Sb1B-F8B
 with sigma of 0.02
 Sb1A-F7A \\sim Sb1B-F7B
 with sigma of 0.02
 Sb1A-F5A \\sim Sb1B-F9B
 with sigma of 0.02
 Sb1A-F4A \\sim Sb1B-F4B
 with sigma of 0.02
 F9A-F8A \\sim F5B-F6B
 with sigma of 0.04
 F9A-F6A \\sim F5B-F8B
 with sigma of 0.04
 F9A-F7A \\sim F5B-F7B
 with sigma of 0.04
 F9A-F5A \\sim F5B-F9B
 with sigma of 0.04
 F9A-F4A \\sim F5B-F4B
 with sigma of 0.04
 F8A-F6A \\sim F6B-F8B
 with sigma of 0.04
 F8A-F7A \\sim F6B-F7B
 with sigma of 0.04
 F8A-F5A \\sim F6B-F9B
 with sigma of 0.04
 F8A-F4A \\sim F6B-F4B
 with sigma of 0.04
 F6A-F7A \\sim F8B-F7B
 with sigma of 0.04
 F6A-F5A \\sim F8B-F9B
 with sigma of 0.04
 F6A-F4A \\sim F8B-F4B
 with sigma of 0.04
 F7A-F5A \\sim F7B-F9B
 with sigma of 0.04
 F7A-F4A \\sim F7B-F4B
 with sigma of 0.04
 F5A-F4A \\sim F9B-F4B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 Sb1B, F4B, F5B, F6B, F7B, F8B, F9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Sb1B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(Sb1A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), C30(H30), C32(H32), C39(H39), C41(H41)
5.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              34273
_shelx_hkl_checksum              50344
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'