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_4127446
_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         'F6 Sb, C27 H31 N3'
_chemical_formula_sum            'C27 H31 F6 N3 Sb'
_chemical_formula_weight         633.30
_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                 108.171(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8395(6)
_cell_length_b                   18.5942(10)
_cell_length_c                   15.5356(7)
_cell_measurement_reflns_used    3287
_cell_measurement_temperature    99.97
_cell_measurement_theta_max      29.587
_cell_measurement_theta_min      2.44
_cell_volume                     2700.6(3)
_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      99.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            86535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.620
_diffrn_reflns_theta_min         2.438
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.2412
_exptl_absorpt_correction_T_min  0.1987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1149 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.8238. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       needle
_exptl_crystal_F_000             1276
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Diethylether and thf  by slow evaporation'
_exptl_crystal_size_max          0.932
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.042
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         7590
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0202P)^2^+3.4672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7153
_reflns_number_total             7590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04249_si_011.cif
_cod_data_source_block           0547_pa_0m
_cod_database_code               4127446
_shelx_shelxl_version_number     2018/3
_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
 Sb1-F4A \\sim Sb1-F4B
 with sigma of 0.02
 Sb1-F2A \\sim Sb1-F2B
 with sigma of 0.02
 Sb1-F1A \\sim Sb1-F1B
 with sigma of 0.02
 Sb1-F3A \\sim Sb1-F3B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Sb1, F1A, F2A, F3A, F4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Sb1, F1B, F2B, F3B, F4B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14), C21(H21),
 C23(H23)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              19305
_shelx_hkl_checksum              52114
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'